protoveratrine B

Details

• Internal ID: 5bf858a0-df18-44cf-a85f-ffe0038402ea
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Cerveratrum-type alkaloids
• IUPAC Name: [(1S,2S,6S,9S,10S,11R,12R,13S,14S,15S,16S,17R,18R,19S,22S,23S,25R)-16,17-diacetyloxy-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-13-[(2R)-2-methylbutanoyl]oxy-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosan-22-yl] (2R,3R)-2,3-dihydroxy-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C(C2C(CN3CC(CCC3C2(C)O)C)C4C1(C5C(C(C6C7(C5(C4)OC6(C(CC7)OC(=O)C(C)(C(C)O)O)O)C)OC(=O)C)OC(=O)C)O)O
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@H]1[C@@H]([C@H]2[C@@H](CN3C[C@H](CC[C@H]3[C@@]2(C)O)C)[C@H]4[C@@]1([C@@H]5[C@@H]([C@@H]([C@H]6[C@]7([C@]5(C4)O[C@@]6([C@H](CC7)OC(=O)[C@@](C)([C@@H](C)O)O)O)C)OC(=O)C)OC(=O)C)O)O
• InChI: InChI=1S/C41H63NO15/c1-10-19(3)34(47)56-33-28(46)27-23(17-42-16-18(2)11-12-25(42)38(27,9)50)24-15-39-32(40(24,33)51)30(54-22(6)45)29(53-21(5)44)31-36(39,7)14-13-26(41(31,52)57-39)55-35(48)37(8,49)20(4)43/h18-20,23-33,43,46,49-52H,10-17H2,1-9H3/t18-,19+,20+,23-,24-,25-,26-,27+,28+,29-,30+,31-,32+,33-,36-,37+,38+,39+,40-,41+/m0/s1
• InChI Key: BFLXOMFFVWQPAZ-CEEVVQPDSA-N
• Popularity: 214 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₃NO₁₅
• Molecular Weight: 809.90 g/mol
• Exact Mass: 809.41977030 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.58
• H-Bond Acceptor: 16
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

• Veratetrine
• Veratetrin
• 124-97-0
• Neoprotoveratrine
• Neoprotoveratrin
• AK816144R9
• [(1S,2S,6S,9S,10S,11R,12R,13S,14S,15S,16S,17R,18R,19S,22S,23S,25R)-16,17-diacetyloxy-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-13-[(2R)-2-methylbutanoyl]oxy-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosan-22-yl] (2R,3R)-2,3-dihydroxy-2-methylbutanoate
• NSC7527
• NSC-7527
• UNII-AK816144R9
• NSC 7527
• EINECS 204-719-2
• BRN 0077630
• 4-21-00-06847 (Beilstein Handbook Reference)
• PROTOVERATRINE B [MI]
• CHEMBL2165398
• PROTOVERATRINE B [WHO-DD]
• DTXSID401043045
• Cevane-3,4,6,7,14,15,16,20-octol, 4,9-epoxy-, 6,7-diacetate 3-(2,3-dihydroxy-2-methylbutanoate) 15-(2-methylbutanoate), (3beta(2R,3R),4alpha,6alpha,7alpha,15alpha(R),16beta)-
• (3beta(2R,3R),4alpha,6alpha,7alpha,15alpha(R),16beta)-4,9-Epoxycevane-3,4,6,7,14,15,16,20-octol 6,7-diacetate 3-(2,3-dihydroxy-2-methylbutyrate) 15-(2-methylbutyrate)
• CEVANE-3,4,6,7,14,15,16,20-OCTOL, 4,9-EPOXY-, 6,7-DIACETATE 3-((2R,3R)-2,3-DIHYDROXY-2-METHYLBUTANOATE) 15-((2R)-2-METHYLBUTANOATE), (3.BETA.,4.ALPHA.,6.ALPHA.,7.ALPHA.,15.ALPHA.,16.BETA.)-
• Cevane-3-beta,4-beta,6-alpha,7-alpha,14,15-alpha-16-beta,20-octol, 4,9-epoxy-, 6,7-diacetate 3-(threo-(+)-2,3-dihydroxy-2-methylbutyrate) 15-((-)-2-methylbutyrate)
• Cevane-3beta,4beta,6alpha,7alpha,14,15alpha,16beta,20-octol, 4,9-epoxy-, 6,7-diacetate 3-(threo-(+)-2,3-dihydroxy-2-methylbutyrate) 15-((-)-2-methylbutyrate)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6249	62.49%
Caco-2	-	0.8688	86.88%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Lysosomes	0.4928	49.28%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7422	74.22%
P-glycoprotein inhibitior	+	0.7639	76.39%
P-glycoprotein substrate	+	0.6973	69.73%
CYP3A4 substrate	+	0.7369	73.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8018	80.18%
CYP3A4 inhibition	-	0.8619	86.19%
CYP2C9 inhibition	-	0.8971	89.71%
CYP2C19 inhibition	-	0.9009	90.09%
CYP2D6 inhibition	-	0.9316	93.16%
CYP1A2 inhibition	-	0.9222	92.22%
CYP2C8 inhibition	+	0.7193	71.93%
CYP inhibitory promiscuity	-	0.9592	95.92%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5268	52.68%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9078	90.78%
Skin irritation	-	0.7652	76.52%
Skin corrosion	-	0.9327	93.27%
Ames mutagenesis	-	0.6274	62.74%
Human Ether-a-go-go-Related Gene inhibition	-	0.4410	44.10%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	+	0.5541	55.41%
skin sensitisation	-	0.8819	88.19%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.4887	48.87%
Acute Oral Toxicity (c)	I	0.6759	67.59%
Estrogen receptor binding	+	0.7279	72.79%
Androgen receptor binding	+	0.7576	75.76%
Thyroid receptor binding	-	0.5507	55.07%
Glucocorticoid receptor binding	+	0.7531	75.31%
Aromatase binding	+	0.6528	65.28%
PPAR gamma	+	0.7685	76.85%
Honey bee toxicity	-	0.6713	67.13%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8107	81.07%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.96%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.70%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.20%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.29%	96.77%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	97.03%	89.05%
CHEMBL2581	P07339	Cathepsin D	96.98%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	93.53%	97.14%
CHEMBL1914	P06276	Butyrylcholinesterase	93.13%	95.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.01%	96.61%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	92.85%	87.16%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	92.56%	82.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.30%	95.89%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	91.44%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.12%	94.45%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.89%	96.47%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	89.96%	95.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.81%	86.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	89.68%	97.28%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.22%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.03%	82.69%
CHEMBL2413	P32246	C-C chemokine receptor type 1	88.70%	89.50%
CHEMBL2996	Q05655	Protein kinase C delta	87.98%	97.79%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.70%	93.56%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.20%	100.00%
CHEMBL299	P17252	Protein kinase C alpha	87.14%	98.03%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	87.10%	94.78%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	86.97%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.30%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.07%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	85.34%	92.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.65%	96.90%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.62%	95.89%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.47%	91.03%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.42%	92.62%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	84.06%	97.29%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.92%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.79%	89.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.74%	94.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.58%	98.75%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	82.15%	99.00%
CHEMBL2094135	Q96BI3	Gamma-secretase	81.72%	98.05%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.54%	95.71%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.36%	95.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.28%	91.11%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.39%	97.50%

Plants that contains it

• Veratrum viride

Cross-Links

• PubChem: 222158
• LOTUS: LTS0204194
• wikiData: Q104934436