(1R,2S,6S,9S,10R,11S,12S,14S,15S,18S,20S,23R,24S)-12,20-dihydroxy-6,10,23-trimethyl-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacosan-17-one

Details

• Internal ID: d08ce93a-c6b6-435e-8a9c-b9f3868014f4
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Cerveratrum-type alkaloids
• IUPAC Name: (1R,2S,6S,9S,10R,11S,12S,14S,15S,18S,20S,23R,24S)-12,20-dihydroxy-6,10,23-trimethyl-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacosan-17-one
• SMILES (Canonical): CC1CCC2C(C3C(CC4C(C3CN2C1)CC5C4CC(=O)C6C5(CCC(C6)O)C)O)C
• SMILES (Isomeric): C[C@H]1CC[C@H]2[C@@H]([C@H]3[C@H](C[C@@H]4[C@H]([C@@H]3CN2C1)C[C@H]5[C@H]4CC(=O)[C@@H]6[C@@]5(CC[C@@H](C6)O)C)O)C
• InChI: InChI=1S/C27H43NO3/c1-14-4-5-23-15(2)26-20(13-28(23)12-14)17-9-21-19(18(17)10-25(26)31)11-24(30)22-8-16(29)6-7-27(21,22)3/h14-23,25-26,29,31H,4-13H2,1-3H3/t14-,15-,16-,17+,18+,19-,20-,21-,22+,23-,25-,26+,27+/m0/s1
• InChI Key: FJICWUQZALKVOT-NAAHGQHNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₃NO₃
• Molecular Weight: 429.60 g/mol
• Exact Mass: 429.32429423 g/mol
• Topological Polar Surface Area (TPSA): 60.80 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.74
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9785	97.85%
Caco-2	-	0.5768	57.68%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Lysosomes	0.5529	55.29%
OATP2B1 inhibitior	-	0.7173	71.73%
OATP1B1 inhibitior	+	0.8543	85.43%
OATP1B3 inhibitior	+	0.9494	94.94%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.4794	47.94%
P-glycoprotein inhibitior	-	0.8074	80.74%
P-glycoprotein substrate	+	0.5477	54.77%
CYP3A4 substrate	+	0.7130	71.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4564	45.64%
CYP3A4 inhibition	-	0.7616	76.16%
CYP2C9 inhibition	-	0.8903	89.03%
CYP2C19 inhibition	-	0.9331	93.31%
CYP2D6 inhibition	-	0.6493	64.93%
CYP1A2 inhibition	-	0.9112	91.12%
CYP2C8 inhibition	-	0.8370	83.70%
CYP inhibitory promiscuity	-	0.9896	98.96%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6137	61.37%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9461	94.61%
Skin irritation	-	0.7278	72.78%
Skin corrosion	-	0.8841	88.41%
Ames mutagenesis	-	0.7196	71.96%
Human Ether-a-go-go-Related Gene inhibition	-	0.6107	61.07%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.5253	52.53%
skin sensitisation	-	0.8470	84.70%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.5327	53.27%
Acute Oral Toxicity (c)	III	0.6701	67.01%
Estrogen receptor binding	+	0.6289	62.89%
Androgen receptor binding	+	0.7435	74.35%
Thyroid receptor binding	+	0.5553	55.53%
Glucocorticoid receptor binding	+	0.5837	58.37%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	-	0.5309	53.09%
Honey bee toxicity	-	0.8225	82.25%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	-	0.6777	67.77%

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	96.48%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.41%	97.25%
CHEMBL325	Q13547	Histone deacetylase 1	92.34%	95.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.78%	97.09%
CHEMBL1902	P62942	FK506-binding protein 1A	90.61%	97.05%
CHEMBL238	Q01959	Dopamine transporter	90.04%	95.88%
CHEMBL299	P17252	Protein kinase C alpha	89.01%	98.03%
CHEMBL2581	P07339	Cathepsin D	89.00%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.85%	100.00%
CHEMBL1871	P10275	Androgen Receptor	88.56%	96.43%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.99%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.77%	95.56%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	86.52%	89.05%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	86.49%	94.78%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.81%	93.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.11%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.03%	82.69%
CHEMBL1937	Q92769	Histone deacetylase 2	83.91%	94.75%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.65%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.17%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.91%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.90%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	81.68%	92.50%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	80.70%	95.58%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	80.67%	98.46%

Plants that contains it

• Fritillaria delavayi

Cross-Links

• PubChem: 14287373
• LOTUS: LTS0221062
• wikiData: Q104996069