Veratrine

Details

• Internal ID: f0bf960a-0c99-4f5d-9350-6e4f37d903b7
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Cerveratrum-type alkaloids
• IUPAC Name: [(1R,2S,6S,9S,10R,11S,12S,14R,15S,18S,19S,22S,23S,25R)-1,10,11,12,14,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosan-22-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCC2(C3C1(OC24CC5(C6CN7CC(CCC7C(C6(C(CC5(C4CC3)O)O)O)(C)O)C)O)O)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1CC[C@]2([C@H]3[C@@]1(O[C@@]24C[C@]5([C@@H]6CN7C[C@H](CC[C@H]7[C@@]([C@]6([C@H](C[C@]5([C@@H]4CC3)O)O)O)(C)O)C)O)O)C
• InChI: InChI=1S/C32H49NO9/c1-6-18(3)25(35)41-24-11-12-26(4)19-8-9-20-28(37)13-23(34)31(39)21(29(28,38)16-30(20,26)42-32(19,24)40)15-33-14-17(2)7-10-22(33)27(31,5)36/h6,17,19-24,34,36-40H,7-16H2,1-5H3/b18-6-/t17-,19-,20-,21-,22-,23-,24-,26-,27+,28+,29+,30+,31-,32-/m0/s1
• InChI Key: DBUCFOVFALNEOO-HWBIYQLFSA-N
• Popularity: 1,304 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₉NO₉
• Molecular Weight: 591.70 g/mol
• Exact Mass: 591.34073214 g/mol
• Topological Polar Surface Area (TPSA): 160.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.99
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 2

Synonyms

• veratrine
• Cevadin
• 62-59-9
• Cevadene
• ERQ7M6C50B
• Veratrine (crystallized)
• NSC 93767
• 8051-02-3
• [(1R,2S,6S,9S,10R,11S,12S,14R,15S,18S,19S,22S,23S,25R)-1,10,11,12,14,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosan-22-yl] (Z)-2-methylbut-2-enoate
• Veratrine (crystallized) (VAN)
• EINECS 200-545-6
• BRN 0072445
• NSC93767
• NSC-93767
• Cevane-3,4,12,14,16,17,20-heptol, 4,9-epoxy-, 3-((2Z)-2-methyl-2-butenoate), (3.beta.,4.alpha.,16.beta.)-
• CEVADINE [MI]
• Spectrum5_000608
• Spectrum5_000732
• CEVADINE [WHO-DD]
• UNII-ERQ7M6C50B
• (Z)-4-alpha,9-Epoxycevane-3-beta,4,12,14,16-beta,17,20-heptol 3-(2-methyl-2-butenoate)
• BSPBio_002258
• BSPBio_003121
• 4-21-00-06820 (Beilstein Handbook Reference)
• Cevane-3,4,12,14,16,17,20-heptol, 4,9-epoxy-, 3-(2-methyl-2-butenoate), (3beta(Z),4alpha,16beta)-
• SCHEMBL117846
• CHEMBL2163790
• CHEBI:184034
• CEVANE-3,4,12,14,16,17,20-HEPTOL, 4,9-EPOXY-, 3-(2-METHYL-2-BUTENOATE), (3.BETA.(Z),4.ALPHA.,16.BETA.)-
• Cevane-3.beta.,4.beta.,12,14,16.beta.,17,20-heptol, 4,9-epoxy-, 3-(2-methylcrotonate), (Z)-
• HY-N12093
• s3250
• AKOS040734629
• Cevane-3beta,4beta,12,14,16beta,17,20-heptol, 4,9-epoxy-, 3-(2-methylcrotonate), (Z)-
• IDI1_000856
• NCGC00178282-01
• NCGC00178282-02
• Cevane-3-beta,4-beta,12,14,16-beta,17,20-heptol, 4,9-epoxy-, 3-(2-methylcrotonate), (Z)-
• CS-0891660
• Q27277329
• (3.BETA.,4.ALPHA.,16.BETA.)-4,9-EPOXYCEVANE-3,4,12,14,16,17,20-HEPTOL 3-((2Z)-2-METHYL-2-BUTENOATE)
• Cevane-3,4,12,14,16,17,20-heptol, 4,9-epoxy-, 3-((2Z)-2-methyl-2-butenoate), (3beta,4alpha,16beta)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6499	64.99%
Caco-2	-	0.7929	79.29%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Lysosomes	0.4981	49.81%
OATP2B1 inhibitior	-	0.5760	57.60%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9488	94.88%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7887	78.87%
P-glycoprotein inhibitior	+	0.6197	61.97%
P-glycoprotein substrate	+	0.5534	55.34%
CYP3A4 substrate	+	0.7160	71.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8289	82.89%
CYP3A4 inhibition	-	0.9779	97.79%
CYP2C9 inhibition	-	0.9153	91.53%
CYP2C19 inhibition	-	0.9178	91.78%
CYP2D6 inhibition	-	0.9518	95.18%
CYP1A2 inhibition	-	0.9272	92.72%
CYP2C8 inhibition	+	0.4752	47.52%
CYP inhibitory promiscuity	-	0.9816	98.16%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Danger	0.4836	48.36%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9320	93.20%
Skin irritation	-	0.7245	72.45%
Skin corrosion	-	0.9262	92.62%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4392	43.92%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.8352	83.52%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.7838	78.38%
Acute Oral Toxicity (c)	III	0.4734	47.34%
Estrogen receptor binding	+	0.7202	72.02%
Androgen receptor binding	+	0.7483	74.83%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5994	59.94%
Aromatase binding	+	0.7223	72.23%
PPAR gamma	+	0.6709	67.09%
Honey bee toxicity	-	0.6952	69.52%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.8200	82.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.34%	96.09%
CHEMBL284	P27487	Dipeptidyl peptidase IV	97.20%	95.69%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	96.38%	89.05%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.32%	97.25%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.17%	96.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.36%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.15%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.70%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.01%	95.89%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.00%	97.21%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.30%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.29%	97.14%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.51%	96.38%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.39%	93.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.29%	86.33%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	83.82%	94.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.55%	95.56%
CHEMBL1871	P10275	Androgen Receptor	82.89%	96.43%
CHEMBL2581	P07339	Cathepsin D	82.01%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.62%	82.69%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.31%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.11%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.93%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	80.65%	83.82%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.48%	95.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.18%	93.04%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	80.10%	99.17%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.05%	91.03%

Plants that contains it

• Schoenocaulon officinale
• Veratrum oblongum

Cross-Links

• PubChem: 5380394
• LOTUS: LTS0011150
• wikiData: Q27277329