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Basic Description
| Synonyms | 4-methyl umbelliferone | Bilcolic | Cantabilin | CCRIS 5926 | LM 94 | 4 Methylumbelliferone | MFCD00006866 | MLS001074671 | CHEBI:17224 | Medilla | Prestwick1_000901 | CAS-90-33-5 | HMS1570F04 | ACon1_002401 | 7-hydroxy-4-methyl coumarin | 7-Hydroxy-4-met |
|---|---|
| Specifications & Purity | ≥98% |
| Biochemical and Physiological Mechanisms | Hyaluronic acid synthesis inhibitor. Coumarin derivative. Down-regulates hyaluronan synthase 2 and 3. Inhibits NFκB reporter activity. Inhibits proliferation, motility and invasion of cancer cell lines. |
| Shipped In | Normal |
| Note | Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details. |
| Product Description |
4-Methylumbelliferone is primarily used in synthesizing medicinal compounds and as a building block for fluorescent probes. Applications include synthesis of: · coumarin triazole derivatives as potential antimicrobial agents. · coumarin salen-based fluorescence sensors for Mg2+ detection. · pyranocoumarin derivatives as anti-hyperglycemic and anti-dyslipidemic agents. · coumarin piperazine derivatives as potential multireceptor atypical antipsychotics. · 4-methylumbelliferyl T-antigen as a substrate for endo-α-N-acetylgalactosaminidase. |
Taxonomic Classification
Taxonomy Tree
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Kingdom
Organic compounds
-
Superclass
Phenylpropanoids and polyketides
-
Class
Coumarins and derivatives
- Subclass Hydroxycoumarins
-
Class
Coumarins and derivatives
-
Superclass
Phenylpropanoids and polyketides
| Kingdom | Organic compounds |
|---|---|
| Superclass | Phenylpropanoids and polyketides |
| Class | Coumarins and derivatives |
| Subclass | Hydroxycoumarins |
| Intermediate Tree Nodes | Not available |
| Direct Parent | 7-hydroxycoumarins |
| Alternative Parents | 1-benzopyrans Pyranones and derivatives 1-hydroxy-2-unsubstituted benzenoids Heteroaromatic compounds Lactones Oxacyclic compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | 7-hydroxycoumarin - Benzopyran - 1-benzopyran - 1-hydroxy-2-unsubstituted benzenoid - Pyranone - Benzenoid - Pyran - Heteroaromatic compound - Lactone - Oxacycle - Organoheterocyclic compound - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. |
| External Descriptors | a small molecule |
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Associated Targets(Human)
HSD17B3
Tchem
Testosterone 17-beta-dehydrogenase 3 (1 Activities)
| Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
|---|
CA9
Tclin
Carbonic anhydrase 9 (1 Activities)
| Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
|---|
F2
Tclin
Thrombin (11687 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
CA2
Tclin
Carbonic anhydrase II (17698 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
ESR1
Tclin
Estrogen receptor alpha (17718 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
PGR
Tclin
Progesterone receptor (8562 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
CHRM2
Tclin
Muscarinic acetylcholine receptor M2 (10671 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
HTR1A
Tclin
Serotonin 1a (5-HT1a) receptor (14969 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
ADRA2A
Tclin
Alpha-2a adrenergic receptor (9450 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
AR
Tclin
Androgen Receptor (11781 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
CHRM1
Tclin
Muscarinic acetylcholine receptor M1 (12690 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
GABRA1
Tclin
GABA receptor alpha-1 subunit (399 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
MAOA
Tclin
Monoamine oxidase A (11911 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
DRD1
Tclin
Dopamine D1 receptor (9720 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
ACHE
Tclin
Acetylcholinesterase (18204 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
PTGS1
Tclin
Cyclooxygenase-1 (9233 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
SLC6A2
Tclin
Norepinephrine transporter (10102 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
MAOB
Tclin
Monoamine oxidase B (8835 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
SLC6A4
Tclin
Serotonin transporter (12625 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
ADRA1A
Tclin
Alpha-1a adrenergic receptor (8359 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
OPRM1
Tclin
Mu opioid receptor (19785 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
DRD3
Tclin
Dopamine D3 receptor (14368 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
SLC6A3
Tclin
Dopamine transporter (10535 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
KCNH2
Tclin
HERG (29587 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
PDE3A
Tclin
Phosphodiesterase 3A (3309 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
HTR2B
Tclin
Serotonin 2b (5-HT2b) receptor (10323 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
AKR1B1
Tclin
Aldose reductase (1404 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
TBXA2R
Tclin
Thromboxane A2 receptor (5717 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
PDE4A
Tclin
Phosphodiesterase 4A (1943 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
ADORA3
Tchem
Adenosine A3 receptor (15931 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
CA1
Tclin
Carbonic anhydrase I (13240 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
HRH3
Tclin
Histamine H3 receptor (10389 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
APP
Tclin
Amyloid-beta A4 protein (8510 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
GLA
Tclin
Alpha-galactosidase A (5444 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
GBA1
Tclin
Beta-glucocerebrosidase (14647 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
GAA
Tclin
Lysosomal alpha-glucosidase (35701 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
KDR
Tclin
Vascular endothelial growth factor receptor 2 (20924 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
ALDH1A1
Tchem
Aldehyde dehydrogenase 1A1 (77053 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
CYP2D6
Tclin
Cytochrome P450 2D6 (33882 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
SORD
Tchem
Sorbitol dehydrogenase (133 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
HSD17B3
Tchem
Estradiol 17-beta-dehydrogenase 3 (821 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
NFKB1
Tclin
Nuclear factor NF-kappa-B p105 subunit (1459 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
CASP1
Tchem
Caspase-1 (6235 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
CASP7
Tchem
Caspase-7 (3146 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
CA12
Tclin
Carbonic anhydrase XII (6231 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
CYP1A2
Tchem
Cytochrome P450 1A2 (26471 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
UGT1A4
Tbio
UDP-glucuronosyltransferase 1A4 (288 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
CYP2C9
Tchem
Cytochrome P450 2C9 (32119 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
CYP2C19
Tchem
Cytochrome P450 2C19 (29246 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
CA9
Tclin
Carbonic anhydrase IX (8255 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
CYP3A4
Tclin
Cytochrome P450 3A4 (53859 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
A498 (42825 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Associated Targets(non-human)
Hdac6
Histone deacetylase 6 (222 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Galc
Galactocerebrosidase (11 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Helicobacter pylori (3113 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Proteus vulgaris (5823 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Micrococcus luteus (7463 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Staphylococcus aureus (210822 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Escherichia coli (133304 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Salmonella typhi (4293 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Shigella dysenteriae (933 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Bacillus subtilis (32866 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Saccharomyces cerevisiae (19171 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Bacillus cereus (7522 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Kluyveromyces marxianus (909 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Aspergillus fumigatus (16427 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Cryptococcus neoformans (21258 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Candida albicans (78123 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Candida parapsilosis (8521 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Candida tropicalis (8381 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Trichophyton rubrum (3646 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Mus musculus (284745 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
B16 (5829 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
J774.A1 (2436 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
NIH3T3 (5395 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
J774 (3120 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
GCN5
Histone acetyltransferase GCN5 (89 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
rep
Replicase polyprotein 1ab (378 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Txnrd1
Thioredoxin reductase 1, cytoplasmic (45279 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
BCHE
Cholinesterase (8742 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
FTL
Ferritin light chain (43324 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
oleD
Oleandomycin glycosyltransferase (79 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
Names and Identifiers
| Pubchem Sid | 488195211 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/488195211 |
| IUPAC Name | 7-hydroxy-4-methylchromen-2-one |
| INCHI | InChI=1S/C10H8O3/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5,11H,1H3 |
| InChIKey | HSHNITRMYYLLCV-UHFFFAOYSA-N |
| Smiles | CC1=CC(=O)OC2=C1C=CC(=C2)O |
| Isomeric SMILES | CC1=CC(=O)OC2=C1C=CC(=C2)O |
| WGK Germany | 2 |
| RTECS | GN7000000 |
| Molecular Weight | 176.17 |
| Beilstein | 142217 |
| Reaxy-Rn | 142217 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=142217&ln= |
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
 F2116322 |
Certificate of Analysis | Mar 04, 2025 | M106701 |
| C2507476 |
Certificate of Analysis | Feb 18, 2025 | M106701 |
| C2507475 |
Certificate of Analysis | Feb 18, 2025 | M106701 |
| C2507536 |
Certificate of Analysis | Feb 18, 2025 | M106701 |
| C2429632 |
Certificate of Analysis | Mar 13, 2024 | M106701 |
| C2429633 |
Certificate of Analysis | Mar 13, 2024 | M106701 |
| I2221040 |
Certificate of Analysis | Sep 29, 2022 | M106701 |
| E1808148 |
Certificate of Analysis | Mar 31, 2022 | M106701 |
| B2216059 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| A2423036 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| B2216058 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| B2514088 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| K2413064 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| K2413065 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| B2216060 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| D2318275 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| B2216061 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| D2318277 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| G2327052 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| I2311018 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| G2311043 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| B2309156 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| D2303667 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| E2323036 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| J2317059 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| B2401043 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| G2408064 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| K2427188 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| B2216411 |
Certificate of Analysis | Dec 30, 2021 | M106701 |
| F2116161 |
Certificate of Analysis | Jun 21, 2021 | M106701 |
| F2116163 |
Certificate of Analysis | Jun 21, 2021 | M106701 |
| F2116162 |
Certificate of Analysis | Jun 21, 2021 | M106701 |
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Chemical and Physical Properties
| Solubility | Soluble in alcohol. Insoluble in cold water. Soluble in acetic acid, alkali and ammonium hydroxide. Slightly soluble in hot water, chloroform and diethyl ether.Solubility in hot Methanol almost transparency |
|---|---|
| Melt Point(°C) | 188.5-190°C |
| Molecular Weight | 176.170 g/mol |
| XLogP3 | 1.900 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 0 |
| Exact Mass | 176.047 Da |
| Monoisotopic Mass | 176.047 Da |
| Topological Polar Surface Area | 46.500 Ų |
| Heavy Atom Count | 13 |
| Formal Charge | 0 |
| Complexity | 257.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
Alternative Products
-
4-Methylumbelliferone (4-MU)Starting at $56.90
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