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

Details

• Internal ID: 2a5d4e9d-099c-4761-a19b-588bab1ad4b5
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Cerveratrum-type alkaloids
• IUPAC Name: (1R,2S,6S,9S,11S,14S,15S,18S,20S,23R,24S)-20-hydroxy-6,10,23-trimethyl-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacosan-17-one
• SMILES (Canonical): CC1CCC2C(C3CCC4C(C3CN2C1)CC5C4CC(=O)C6C5(CCC(C6)O)C)C
• SMILES (Isomeric): C[C@H]1CC[C@H]2C([C@H]3CC[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)C
• InChI: InChI=1S/C27H43NO2/c1-15-4-7-25-16(2)18-5-6-19-20(22(18)14-28(25)13-15)11-23-21(19)12-26(30)24-10-17(29)8-9-27(23,24)3/h15-25,29H,4-14H2,1-3H3/t15-,16?,17-,18+,19+,20+,21-,22+,23-,24+,25-,27+/m0/s1
• InChI Key: MWBJDDYEYGDWCZ-PZCFKJIRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₃NO₂
• Molecular Weight: 413.60 g/mol
• Exact Mass: 413.329379614 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 4.77
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9924	99.24%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.8879	88.79%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Lysosomes	0.5639	56.39%
OATP2B1 inhibitior	-	0.7176	71.76%
OATP1B1 inhibitior	+	0.8805	88.05%
OATP1B3 inhibitior	+	0.9499	94.99%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.5889	58.89%
P-glycoprotein inhibitior	-	0.7726	77.26%
P-glycoprotein substrate	+	0.5376	53.76%
CYP3A4 substrate	+	0.7080	70.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4564	45.64%
CYP3A4 inhibition	-	0.5703	57.03%
CYP2C9 inhibition	-	0.8845	88.45%
CYP2C19 inhibition	-	0.9345	93.45%
CYP2D6 inhibition	+	0.5262	52.62%
CYP1A2 inhibition	-	0.9239	92.39%
CYP2C8 inhibition	-	0.8489	84.89%
CYP inhibitory promiscuity	-	0.9923	99.23%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6098	60.98%
Eye corrosion	-	0.9859	98.59%
Eye irritation	-	0.9214	92.14%
Skin irritation	-	0.6941	69.41%
Skin corrosion	-	0.7945	79.45%
Ames mutagenesis	-	0.7985	79.85%
Human Ether-a-go-go-Related Gene inhibition	-	0.6283	62.83%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5128	51.28%
skin sensitisation	-	0.8129	81.29%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.5768	57.68%
Acute Oral Toxicity (c)	III	0.6846	68.46%
Estrogen receptor binding	+	0.6824	68.24%
Androgen receptor binding	+	0.7875	78.75%
Thyroid receptor binding	+	0.5739	57.39%
Glucocorticoid receptor binding	+	0.7099	70.99%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.5300	53.00%
Honey bee toxicity	-	0.8108	81.08%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	-	0.8114	81.14%

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	96.13%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.48%	97.25%
CHEMBL325	Q13547	Histone deacetylase 1	91.03%	95.92%
CHEMBL238	Q01959	Dopamine transporter	90.88%	95.88%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.24%	97.09%
CHEMBL1871	P10275	Androgen Receptor	89.00%	96.43%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	88.87%	89.05%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.42%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.08%	95.56%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	87.91%	94.78%
CHEMBL1902	P62942	FK506-binding protein 1A	87.28%	97.05%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.63%	89.00%
CHEMBL2581	P07339	Cathepsin D	85.97%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.53%	82.69%
CHEMBL299	P17252	Protein kinase C alpha	85.50%	98.03%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.93%	96.61%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.93%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	83.91%	94.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.42%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.05%	96.77%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.03%	97.14%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.74%	93.00%
CHEMBL4506	Q96EB6	NAD-dependent deacetylase sirtuin 1	80.56%	88.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.41%	95.89%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	80.20%	98.46%
CHEMBL5255	O00206	Toll-like receptor 4	80.06%	92.50%

Plants that contains it

• Duguetia glabriuscula
• Fritillaria cirrhosa
• Fritillaria delavayi
• Fritillaria ebeiensis
• Fritillaria monantha
• Fritillaria pallidiflora
• Fritillaria przewalskii
• Fritillaria taipaiensis
• Fritillaria thunbergii
• Fritillaria unibracteata
• Fritillaria verticillata
• Fritillaria walujewii

Cross-Links

• PubChem: 102062796
• NPASS: NPC23733
• LOTUS: LTS0212408
• wikiData: Q104997848