9,11a-Methano-11aH-cyclohepta[a]naphthalene-4-carboxylic acid, 5-(benzoyloxy)tetradecahydro-4-(hydroxymethyl)-11b-methyl-8-methylene-, (4S,4aR,5R,11bS)-

Details

• Internal ID: 6dc09eff-ea17-41e6-b2af-51b99843a30a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Villanovane, atisane, trachylobane or helvifulvane diterpenoids > Stemarane diterpenoids
• IUPAC Name: (2S,6S,7R,8R)-8-benzoyloxy-6-(hydroxymethyl)-2-methyl-12-methylidenetetracyclo[11.2.1.01,10.02,7]hexadecane-6-carboxylic acid
• SMILES (Canonical): CC12CCCC(C1C(CC3C24CCC(C4)C(=C)C3)OC(=O)C5=CC=CC=C5)(CO)C(=O)O
• SMILES (Isomeric): C[C@]12CCC[C@]([C@@H]1[C@@H](CC3C24CCC(C4)C(=C)C3)OC(=O)C5=CC=CC=C5)(CO)C(=O)O
• InChI: InChI=1S/C27H34O5/c1-17-13-20-14-21(32-23(29)18-7-4-3-5-8-18)22-25(2,27(20)12-9-19(17)15-27)10-6-11-26(22,16-28)24(30)31/h3-5,7-8,19-22,28H,1,6,9-16H2,2H3,(H,30,31)/t19?,20?,21-,22-,25+,26-,27?/m1/s1
• InChI Key: FKABAWURBLBFLT-DZHOZBSLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₅
• Molecular Weight: 438.60 g/mol
• Exact Mass: 438.24062418 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.85
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 9,11a-Methano-11aH-cyclohepta[a]naphthalene-4-carboxylic acid, 5-(benzoyloxy)tetradecahydro-4-(hydroxymethyl)-11b-methyl-8-methylene-, (4S,4aR,5R,11bS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9731	97.31%
Caco-2	-	0.6557	65.57%
Blood Brain Barrier	-	0.5223	52.23%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7572	75.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8031	80.31%
OATP1B3 inhibitior	+	0.8972	89.72%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6764	67.64%
BSEP inhibitior	-	0.5497	54.97%
P-glycoprotein inhibitior	-	0.6010	60.10%
P-glycoprotein substrate	+	0.5710	57.10%
CYP3A4 substrate	+	0.6857	68.57%
CYP2C9 substrate	-	0.8129	81.29%
CYP2D6 substrate	-	0.8775	87.75%
CYP3A4 inhibition	-	0.8078	80.78%
CYP2C9 inhibition	-	0.6715	67.15%
CYP2C19 inhibition	-	0.7509	75.09%
CYP2D6 inhibition	-	0.9061	90.61%
CYP1A2 inhibition	-	0.7259	72.59%
CYP2C8 inhibition	+	0.7119	71.19%
CYP inhibitory promiscuity	-	0.7564	75.64%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7019	70.19%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9339	93.39%
Skin irritation	-	0.6601	66.01%
Skin corrosion	-	0.9555	95.55%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8296	82.96%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5303	53.03%
skin sensitisation	-	0.8775	87.75%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6648	66.48%
Acute Oral Toxicity (c)	III	0.5925	59.25%
Estrogen receptor binding	+	0.8822	88.22%
Androgen receptor binding	+	0.7048	70.48%
Thyroid receptor binding	+	0.5633	56.33%
Glucocorticoid receptor binding	+	0.6870	68.70%
Aromatase binding	+	0.6998	69.98%
PPAR gamma	-	0.5131	51.31%
Honey bee toxicity	-	0.8949	89.49%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	97.53%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.76%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.27%	86.33%
CHEMBL2581	P07339	Cathepsin D	94.19%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.51%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.44%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.21%	97.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.65%	94.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.04%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.01%	95.56%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	88.28%	92.67%
CHEMBL340	P08684	Cytochrome P450 3A4	88.18%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.55%	96.95%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.28%	93.03%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.84%	94.08%
CHEMBL5028	O14672	ADAM10	83.61%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.56%	95.89%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	83.55%	94.23%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	81.87%	97.53%

Plants that contains it

• Scoparia dulcis

Cross-Links

• PubChem: 512742
• LOTUS: LTS0127560
• wikiData: Q104996444