Jervine
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Basic Info
| Common Name | Jervine(F05225) |
| 2D Structure | |
| Description | Jervine is a steroidal alkaloid with molecular formula C27H39NO3 which is derived from the Veratrum plant genus. Similar to cyclopamine, which also occurs in the Veratrum genus, it is a teratogen implicated in birth defects when consumed by animals during a certain period of their gestation. |
| FRCD ID | F05225 |
| CAS Number | 469-59-0 |
| PubChem CID | 10098 |
| Formula | C27H39NO3 |
| IUPAC Name | (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethylspiro[1,2,3,4,6,6a,6b,7,8,11a-decahydrobenzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-11-one |
| InChI Key | CLEXYFLHGFJONT-DNMILWOZSA-N |
| InChI | InChI=1S/C27H39NO3/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3/t14-,16+,18-,19-,20-,21+,23+,24-,26-,27-/m0/s1 |
| Canonical SMILES | CC1CC2C(C(C3(O2)CCC4C5CC=C6CC(CCC6(C5C(=O)C4=C3C)C)O)C)NC1 |
| Isomeric SMILES | C[C@H]1C[C@@H]2[C@H]([C@H]([C@]3(O2)CC[C@H]4[C@@H]5CC=C6C[C@H](CC[C@@]6([C@H]5C(=O)C4=C3C)C)O)C)NC1 |
| Wikipedia | Jervine |
| Synonyms |
EINECS 207-417-9
JERVINE
469-59-0
Iervin
Jerwiny [Polish]
11-Ketocyclopamine
UNII-19V3ECX465
HSDB 3502
NSC 7520
BRN 0059109
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Steroids and steroid derivatives |
| Subclass | Steroidal alkaloids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Jerveratrum-type alkaloids |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Substituents | Jerveratrum-type alkaloid - Azasteroid - Alkaloid or derivatives - Piperidine - Cyclic alcohol - Tetrahydrofuran - Ketone - Secondary alcohol - Dialkyl ether - Secondary aliphatic amine - Ether - Oxacycle - Secondary amine - Azacycle - Organoheterocyclic compound - Organic oxide - Organopnictogen compound - Amine - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic nitrogen compound - Carbonyl group - Organic oxygen compound - Alcohol - Aliphatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as jerveratrum-type alkaloids. These are steroidal alkaloids with a structure that is based on the jervane ring system. Jerveratrum alkaloids have alkamines with 1-3 oxygen atoms, and occur as such or as monoglycosides. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 425.613 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 0 |
| Complexity | 876 |
| Monoisotopic Mass | 425.293 |
| Exact Mass | 425.293 |
| XLogP | 2.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 31 |
| Defined Atom Stereocenter Count | 10 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9284 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.5211 |
| P-glycoprotein Substrate | Substrate | 0.8129 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6621 |
| Non-inhibitor | 0.7522 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7326 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6033 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8614 |
| CYP450 2D6 Substrate | Non-substrate | 0.7120 |
| CYP450 3A4 Substrate | Substrate | 0.6659 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9045 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9101 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9230 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9121 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9521 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9087 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8813 |
| Non-inhibitor | 0.8777 | |
| AMES Toxicity | Non AMES toxic | 0.7863 |
| Carcinogens | Non-carcinogens | 0.9650 |
| Fish Toxicity | High FHMT | 0.8687 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9483 |
| Honey Bee Toxicity | High HBT | 0.6611 |
| Biodegradation | Not ready biodegradable | 0.9907 |
| Acute Oral Toxicity | III | 0.6302 |
| Carcinogenicity (Three-class) | Non-required | 0.4961 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.9988 | LogS |
| Caco-2 Permeability | 1.1465 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.3742 | LD50, mol/kg |
| Fish Toxicity | 1.2600 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4036 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| A preliminary assessment of the toxic and mutagenic potential of steroidal alkaloids in transgenic mice. | Food Chem Toxicol | 1995 Mar | 7896228 |
Targets
- General Function:
- Transmembrane signaling receptor activity
- Specific Function:
- Catalyzes the conversion of Delta(8)-sterols to their corresponding Delta(7)-isomers.
- Gene Name:
- EBP
- Uniprot ID:
- Q15125
- Molecular Weight:
- 26352.615 Da
References
- Laggner C, Schieferer C, Fiechtner B, Poles G, Hoffmann RD, Glossmann H, Langer T, Moebius FF: Discovery of high-affinity ligands of sigma1 receptor, ERG2, and emopamil binding protein by pharmacophore modeling and virtual screening. J Med Chem. 2005 Jul 28;48(15):4754-64. [16033255 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Intercellular signal essential for a variety of patterning events during development: signal produced by the notochord that induces ventral cell fate in the neural tube and somites, and the polarizing signal for patterning of the anterior-posterior axis of the developing limb bud. Displays both floor plate- and motor neuron-inducing activity. The threshold concentration of N-product required for motor neuron induction is 5-fold lower than that required for floor plate induction. Activates the transcription of target genes by interacting with its receptor PTCH1 to prevent normal inhibition by PTCH1 on the constitutive signaling activity of SMO (By similarity).
- Gene Name:
- SHH
- Uniprot ID:
- Q15465
- Molecular Weight:
- 49606.685 Da
References
- Mahindroo N, Punchihewa C, Fujii N: Hedgehog-Gli signaling pathway inhibitors as anticancer agents. J Med Chem. 2009 Jul 9;52(13):3829-45. doi: 10.1021/jm801420y. [19309080 ]
- General Function:
- Opioid receptor activity
- Specific Function:
- Functions in lipid transport from the endoplasmic reticulum and is involved in a wide array of cellular functions probably through regulation of the biogenesis of lipid microdomains at the plasma membrane. Involved in the regulation of different receptors it plays a role in BDNF signaling and EGF signaling. Also regulates ion channels like the potassium channel and could modulate neurotransmitter release. Plays a role in calcium signaling through modulation together with ANK2 of the ITP3R-dependent calcium efflux at the endoplasmic reticulum. Plays a role in several other cell functions including proliferation, survival and death. Originally identified for its ability to bind various psychoactive drugs it is involved in learning processes, memory and mood alteration (PubMed:16472803, PubMed:9341151). Necessary for proper mitochondrial axonal transport in motor neurons, in particular the retrograde movement of mitochondria (By similarity).
- Gene Name:
- SIGMAR1
- Uniprot ID:
- Q99720
- Molecular Weight:
- 25127.52 Da
References
- Laggner C, Schieferer C, Fiechtner B, Poles G, Hoffmann RD, Glossmann H, Langer T, Moebius FF: Discovery of high-affinity ligands of sigma1 receptor, ERG2, and emopamil binding protein by pharmacophore modeling and virtual screening. J Med Chem. 2005 Jul 28;48(15):4754-64. [16033255 ]