Deacetylprotoveratrine A

Details

• Internal ID: 0781dc53-f666-401d-bcc0-093491440489
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Cerveratrum-type alkaloids
• IUPAC Name: [(1S,2S,6S,9S,11R,12R,13S,14S,15S,16S,17R,18R,19S,22S,23S,25R)-17-acetyloxy-10,12,14,16,23-pentahydroxy-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] (2S)-2-hydroxy-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)(CC)O)O)C)OC(=O)C)O)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]3C2(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)(CC)O)O)C)OC(=O)C)O)O)O
• InChI: InChI=1S/C39H61NO13/c1-9-19(4)32(44)52-31-26(42)25-21(17-40-16-18(3)11-12-23(40)36(25,8)47)22-15-37-29(38(22,31)48)27(43)28(50-20(5)41)30-34(37,6)14-13-24(39(30,49)53-37)51-33(45)35(7,46)10-2/h18-19,21-31,42-43,46-49H,9-17H2,1-8H3/t18-,19+,21-,22-,23-,24-,25+,26+,27+,28-,29+,30-,31-,34-,35-,36?,37+,38-,39+/m0/s1
• InChI Key: TWZQQKSYGPDWKZ-BRNBNTERSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₆₁NO₁₃
• Molecular Weight: 751.90 g/mol
• Exact Mass: 751.41429100 g/mol
• Topological Polar Surface Area (TPSA): 213.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.04
• H-Bond Acceptor: 14
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6715	67.15%
Caco-2	-	0.8634	86.34%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Lysosomes	0.6149	61.49%
OATP2B1 inhibitior	-	0.7379	73.79%
OATP1B1 inhibitior	+	0.9305	93.05%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6554	65.54%
P-glycoprotein inhibitior	+	0.7569	75.69%
P-glycoprotein substrate	+	0.7016	70.16%
CYP3A4 substrate	+	0.7439	74.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7867	78.67%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9078	90.78%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9308	93.08%
CYP1A2 inhibition	-	0.9425	94.25%
CYP2C8 inhibition	+	0.7364	73.64%
CYP inhibitory promiscuity	-	0.9613	96.13%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5302	53.02%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9118	91.18%
Skin irritation	-	0.7598	75.98%
Skin corrosion	-	0.9349	93.49%
Ames mutagenesis	-	0.6274	62.74%
Human Ether-a-go-go-Related Gene inhibition	-	0.4602	46.02%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	+	0.5666	56.66%
skin sensitisation	-	0.8817	88.17%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.5177	51.77%
Acute Oral Toxicity (c)	I	0.8149	81.49%
Estrogen receptor binding	+	0.6941	69.41%
Androgen receptor binding	+	0.7601	76.01%
Thyroid receptor binding	-	0.5803	58.03%
Glucocorticoid receptor binding	+	0.7265	72.65%
Aromatase binding	+	0.6636	66.36%
PPAR gamma	+	0.7353	73.53%
Honey bee toxicity	-	0.6679	66.79%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.7302	73.02%

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	99.95%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.25%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.02%	96.77%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.82%	85.14%
CHEMBL1914	P06276	Butyrylcholinesterase	97.78%	95.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	97.21%	89.05%
CHEMBL2581	P07339	Cathepsin D	96.16%	98.95%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	92.21%	96.47%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.97%	82.69%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.96%	97.14%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	90.77%	95.36%
CHEMBL3922	P50579	Methionine aminopeptidase 2	90.74%	97.28%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.09%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.96%	86.33%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	89.61%	82.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.50%	100.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	89.22%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.21%	96.61%
CHEMBL2413	P32246	C-C chemokine receptor type 1	88.63%	89.50%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	88.47%	87.16%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.70%	93.56%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	87.31%	94.78%
CHEMBL2996	Q05655	Protein kinase C delta	87.22%	97.79%
CHEMBL5255	O00206	Toll-like receptor 4	86.87%	92.50%
CHEMBL299	P17252	Protein kinase C alpha	86.79%	98.03%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	86.76%	98.75%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	86.53%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.12%	95.89%
CHEMBL2094135	Q96BI3	Gamma-secretase	85.06%	98.05%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.73%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.64%	96.90%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.34%	97.09%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.14%	95.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.04%	89.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.78%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.22%	94.45%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.78%	91.03%
CHEMBL204	P00734	Thrombin	82.74%	96.01%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.98%	94.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.37%	91.11%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.22%	93.04%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	81.20%	99.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.17%	99.23%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.14%	95.71%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	80.68%	97.29%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.36%	97.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	80.29%	95.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.16%	93.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.14%	92.62%

Plants that contains it

• Veratrum nigrum

Cross-Links

• PubChem: 102093842
• NPASS: NPC47762
• LOTUS: LTS0053746
• wikiData: Q104395511