[(1R,2S,6S,9S,10S,11R,12S,14S,15S,20S,23R,24S)-10,12-dihydroxy-6,10,23-trimethyl-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacos-17-en-20-yl] formate

Details

• Internal ID: e608cd7a-299c-4aab-b4e6-1d855580b8ea
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Cerveratrum-type alkaloids
• IUPAC Name: [(1R,2S,6S,9S,10S,11R,12S,14S,15S,20S,23R,24S)-10,12-dihydroxy-6,10,23-trimethyl-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacos-17-en-20-yl] formate
• SMILES (Canonical): CC1CCC2C(C3C(CC4C5CC=C6CC(CCC6(C5CC4C3CN2C1)C)OC=O)O)(C)O
• SMILES (Isomeric): C[C@H]1CC[C@H]2[C@@]([C@H]3[C@H](C[C@H]4[C@@H]5CC=C6C[C@H](CC[C@@]6([C@H]5C[C@H]4[C@@H]3CN2C1)C)OC=O)O)(C)O
• InChI: InChI=1S/C28H43NO4/c1-16-4-7-25-28(3,32)26-22(14-29(25)13-16)20-11-23-19(21(20)12-24(26)31)6-5-17-10-18(33-15-30)8-9-27(17,23)2/h5,15-16,18-26,31-32H,4,6-14H2,1-3H3/t16-,18-,19-,20+,21-,22-,23-,24-,25-,26+,27-,28+/m0/s1
• InChI Key: VNWXSCOWIQXPES-GFDBUZCFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₃NO₄
• Molecular Weight: 457.60 g/mol
• Exact Mass: 457.31920885 g/mol
• Topological Polar Surface Area (TPSA): 70.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.78
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• BDBM50090180

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9023	90.23%
Caco-2	-	0.6905	69.05%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4859	48.59%
OATP2B1 inhibitior	-	0.5743	57.43%
OATP1B1 inhibitior	+	0.9192	91.92%
OATP1B3 inhibitior	+	0.9343	93.43%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8817	88.17%
P-glycoprotein inhibitior	-	0.5894	58.94%
P-glycoprotein substrate	+	0.5661	56.61%
CYP3A4 substrate	+	0.7244	72.44%
CYP2C9 substrate	-	0.8086	80.86%
CYP2D6 substrate	+	0.3587	35.87%
CYP3A4 inhibition	-	0.9524	95.24%
CYP2C9 inhibition	-	0.9046	90.46%
CYP2C19 inhibition	-	0.9177	91.77%
CYP2D6 inhibition	-	0.7927	79.27%
CYP1A2 inhibition	-	0.9102	91.02%
CYP2C8 inhibition	+	0.5622	56.22%
CYP inhibitory promiscuity	-	0.9636	96.36%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4778	47.78%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.9722	97.22%
Skin irritation	-	0.7036	70.36%
Skin corrosion	-	0.9180	91.80%
Ames mutagenesis	-	0.8578	85.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7278	72.78%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8342	83.42%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5805	58.05%
Acute Oral Toxicity (c)	III	0.6019	60.19%
Estrogen receptor binding	+	0.7172	71.72%
Androgen receptor binding	+	0.7413	74.13%
Thyroid receptor binding	-	0.4876	48.76%
Glucocorticoid receptor binding	+	0.5608	56.08%
Aromatase binding	+	0.5808	58.08%
PPAR gamma	+	0.6048	60.48%
Honey bee toxicity	-	0.7186	71.86%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6345	63.45%
Fish aquatic toxicity	+	0.7373	73.73%

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	98.47%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.50%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.27%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.98%	97.25%
CHEMBL2581	P07339	Cathepsin D	89.70%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.27%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.81%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.99%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.54%	95.89%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	87.52%	91.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.29%	94.45%
CHEMBL4660	P28907	Lymphocyte differentiation antigen CD38	86.88%	95.27%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.17%	95.89%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.83%	89.05%
CHEMBL238	Q01959	Dopamine transporter	85.50%	95.88%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.14%	85.14%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.37%	94.08%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.29%	97.09%
CHEMBL1871	P10275	Androgen Receptor	82.49%	96.43%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.53%	91.11%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.25%	91.07%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.13%	90.71%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.87%	96.90%

Plants that contains it

• Veratrum nigrum

Cross-Links

• PubChem: 122178947
• LOTUS: LTS0061233
• wikiData: Q105290000