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Basic Description
| Synonyms | monocrotaline | Crotaline | 315-22-0 | Monocrotalin | (-)-Monocrotaline | CHEBI:6980 | Retronecine cyclic 2,3-dihydroxy-2,3,4-trimethylglutarate | (13-alpha,14-alpha)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione | MLS002153902 | DTXSID9020902 | NCI-C56462 | 14,19 |
|---|---|
| Specifications & Purity | 10mM in DMSO |
| Biochemical and Physiological Mechanisms | Rotaline can induce pulmonary vascular syndrome in rats. This component is known to be toxic and can cause cirrhosis, liver enlargement, sinus syndrome, and right ventricular hypertrophy |
| Storage Temp | Store at -80°C |
| Shipped In |
Ice chest + Ice pads This product requires cold chain shipping. Ground and other economy services are not available. |
| Product Description |
Monocrotaline is a toxic, pyrrolizidine alkaloid. It is used for inducing pulmonary diseases in rats. The alkaloid causes pulmonary artery hypertension, right ventricular hypertrophy, and pathological changes in the pulmonary vasculature. |
Taxonomic Classification
Taxonomy Tree
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Kingdom
Organic compounds
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Superclass
Organoheterocyclic compounds
- Class Pyrrolizines
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Superclass
Organoheterocyclic compounds
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Pyrrolizines |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Pyrrolizines |
| Alternative Parents | N-alkylpyrrolidines Dicarboxylic acids and derivatives Tertiary alcohols Pyrrolines Trialkylamines Lactones Carboxylic acid esters Amino acids and derivatives 1,2-diols Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Substituents | Pyrrolizine - Dicarboxylic acid or derivatives - N-alkylpyrrolidine - Pyrrolidine - Pyrroline - Tertiary alcohol - 1,2-diol - Amino acid or derivatives - Carboxylic acid ester - Lactone - Tertiary aliphatic amine - Tertiary amine - Carboxylic acid derivative - Oxacycle - Azacycle - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic nitrogen compound - Carbonyl group - Organic oxygen compound - Amine - Organooxygen compound - Alcohol - Aliphatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as pyrrolizines. These are compounds containing a pyrrolizine moiety, which consists of a pyrrole ring fused to a pyrrolidine ring. |
| External Descriptors | Pyrrolizidine alkaloids |
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Associated Targets(Human)
ACHE
Tclin
Acetylcholinesterase (18204 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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THRB
Tclin
Thyroid hormone receptor beta-1 (7926 Activities)
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TP53
Tchem
Cellular tumor antigen p53 (48468 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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A204 (242 Activities)
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KB (17409 Activities)
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TDP1
Tchem
Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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GMNN
Tbio
Geminin (128009 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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SLCO1B1
Tchem
Solute carrier organic anion transporter family member 1B1 (2672 Activities)
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SLCO1B3
Tchem
Solute carrier organic anion transporter family member 1B3 (2517 Activities)
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Associated Targets(non-human)
pol
Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)
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ampC
Beta-lactamase AmpC (62480 Activities)
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Pseudomonas aeruginosa (123386 Activities)
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Escherichia coli (133304 Activities)
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Spodoptera littoralis (798 Activities)
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Meloidogyne incognita (862 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Rattus norvegicus (775804 Activities)
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Myzus persicae (1112 Activities)
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CHO (4503 Activities)
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Lactuca sativa (1092 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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BCHE
Cholinesterase (8742 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Leptinotarsa decemlineata (1161 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Rhopalosiphum padi (121 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Pratylenchus penetrans (14 Activities)
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Heterodera schachtii (22 Activities)
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Phasmarhabditis hermaphrodita (5 Activities)
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Rhabditis sp. (25 Activities)
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Names and Identifiers
| IUPAC Name | (1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione |
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| INCHI | InChI=1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-/m0/s1 |
| InChIKey | QVCMHGGNRFRMAD-XFGHUUIASA-N |
| Smiles | CC1C(=O)OC2CCN3C2C(=CC3)COC(=O)C(C1(C)O)(C)O |
| Isomeric SMILES | C[C@H]1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]1(C)O)(C)O |
| WGK Germany | 3 |
| RTECS | QB3140000 |
| UN Number | 1544 |
| Molecular Weight | 325.36 |
| Beilstein | 48732 |
| Reaxy-Rn | 628332 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=628332&ln= |
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
| Sensitivity | Light sensitive |
|---|---|
| Melt Point(°C) | 204°C |
| Molecular Weight | 325.360 g/mol |
| XLogP3 | -0.700 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 0 |
| Exact Mass | 325.153 Da |
| Monoisotopic Mass | 325.153 Da |
| Topological Polar Surface Area | 96.300 Ų |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Complexity | 575.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 5 |
| 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 |
Citations of This Product
| 1. Haixia Che, Jie Yi, Xiaoting Zhao, Hong Yu, Xianyao Wang, Rui Zhang, Xin Li, Jia Fu, Qian Li. (2023) Characterization of PKCα-rutin interactions and its application as a treatment strategy for PAH by inhibiting ferroptosis. Food & Function, |
| 2. Yanhui Ge, Shuchang Zhao, Boyi Yuan, Yuan Gao, Ruilin Liu. (2023) In-situ growth of metal coordination-synergistic imprinted polymer onto shrimp shell-derived magnetic FeNi biochar for specific recognition of monocrotaline in herbal medicine. Materials Today Sustainability, 24 (100599). |
| 3. Yang Zhong, Jiayu Gu, Yaoquan Su, Lingzhi Zhao, Yunyun Zhou, Juanjuan Peng. (2022) Real-time screening of hepatotoxins in natural medicine by peroxynitrite responsive lanthanide-based NIR-II luminescent probes. CHEMICAL ENGINEERING JOURNAL, 433 (133263). |
| 4. Mingyan Ji, Yun Chen, Yifan Ma, Dongping Li, Jin Ren, Hongyue Jiang, Sinuo Chen, Xiaoqing Zeng, Hong Gao. (2024) ADAMTS13 Improves Hepatic Platelet Accumulation in Pyrrolizidine Alkaloids-induced Liver Injury. Journal of Clinical and Translational Hepatology, 13 (1): (25). |
| 5. Min Fu, Yuan Li, Jingjing Liu, Junjie Liu, Jiaoxia Wei, Yuxin Qiao, Hanxin Zhong, Dongyang Han, Haitao Lu, Li Yao. (2024) Zhishi Xiebai Guizhi Decoction modulates hypoxia and lipid toxicity to alleviate pulmonary vascular remodeling of pulmonary hypertension in rats. Chinese Medicine, 19 (173). |
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