Cheilanthone A

Details

• Internal ID: b815693e-67e4-4611-a404-edfa5f4d7ee7
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives > Pentahydroxy bile acids, alcohols and derivatives
• IUPAC Name: (2S,3R,5R,8R,9S,10R,13R,14R,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one
• SMILES (Canonical): CC(C1CCC2(C1(CCC3C2CC(=O)C4C3(CC(C(C4)O)O)C)C)O)C(CCC(C)(C)O)O
• SMILES (Isomeric): C[C@@H]([C@H]1CC[C@@]2([C@@]1(CC[C@H]3[C@H]2CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)C)O)[C@@H](CCC(C)(C)O)O
• InChI: InChI=1S/C27H46O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h15-20,22-23,28,30-33H,6-14H2,1-5H3/t15-,16+,17-,18+,19-,20+,22+,23-,25+,26+,27+/m0/s1
• InChI Key: MSFNGOWODGGQNW-YZENLCTGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₆O₆
• Molecular Weight: 466.60 g/mol
• Exact Mass: 466.32943918 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.82
• H-Bond Acceptor: 6
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• 26152-93-2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9868	98.68%
Caco-2	-	0.6345	63.45%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8074	80.74%
OATP2B1 inhibitior	-	0.5742	57.42%
OATP1B1 inhibitior	+	0.8823	88.23%
OATP1B3 inhibitior	+	0.9630	96.30%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.4868	48.68%
P-glycoprotein inhibitior	-	0.6344	63.44%
P-glycoprotein substrate	+	0.6141	61.41%
CYP3A4 substrate	+	0.6785	67.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7939	79.39%
CYP3A4 inhibition	-	0.8032	80.32%
CYP2C9 inhibition	-	0.8825	88.25%
CYP2C19 inhibition	-	0.8852	88.52%
CYP2D6 inhibition	-	0.9713	97.13%
CYP1A2 inhibition	-	0.8470	84.70%
CYP2C8 inhibition	-	0.7011	70.11%
CYP inhibitory promiscuity	-	0.9563	95.63%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7527	75.27%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.9560	95.60%
Skin irritation	+	0.6440	64.40%
Skin corrosion	-	0.9372	93.72%
Ames mutagenesis	-	0.8078	80.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.4196	41.96%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.5402	54.02%
skin sensitisation	-	0.7238	72.38%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.8213	82.13%
Acute Oral Toxicity (c)	III	0.6433	64.33%
Estrogen receptor binding	+	0.7303	73.03%
Androgen receptor binding	+	0.8242	82.42%
Thyroid receptor binding	+	0.5577	55.77%
Glucocorticoid receptor binding	+	0.7248	72.48%
Aromatase binding	+	0.6508	65.08%
PPAR gamma	-	0.5559	55.59%
Honey bee toxicity	-	0.7738	77.38%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9774	97.74%

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	99.79%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.13%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.51%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.82%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.71%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.32%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	95.02%	97.79%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.65%	96.61%
CHEMBL1902	P62942	FK506-binding protein 1A	90.38%	97.05%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.88%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.14%	100.00%
CHEMBL2094135	Q96BI3	Gamma-secretase	87.78%	98.05%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.72%	89.34%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.16%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.58%	97.14%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.90%	93.04%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.76%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.93%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.89%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.57%	89.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.58%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	82.45%	95.93%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	82.14%	94.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.99%	90.71%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.32%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.16%	86.33%

Plants that contains it

• Sophora tonkinensis

Cross-Links

• PubChem: 101297731
• NPASS: NPC34797