3-[(3S,3aR,5aS,6S,7S,9aR,9bR)-6,9a,9b-trimethyl-7-prop-1-en-2-yl-3-[(E,2S,6R)-2,6,7-trihydroxy-6-methylhept-4-en-2-yl]-1,2,3,3a,4,5,5a,7,8,9-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid

Details

• Internal ID: 9c54a9f7-fbf1-4627-a097-a7b31a9f79ac
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesterterpenoids
• IUPAC Name: 3-[(3S,3aR,5aS,6S,7S,9aR,9bR)-6,9a,9b-trimethyl-7-prop-1-en-2-yl-3-[(E,2S,6R)-2,6,7-trihydroxy-6-methylhept-4-en-2-yl]-1,2,3,3a,4,5,5a,7,8,9-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid
• SMILES (Canonical): CC(=C)C1CCC2(C(C1(C)CCC(=O)O)CCC3C2(CCC3C(C)(CC=CC(C)(CO)O)O)C)C
• SMILES (Isomeric): CC(=C)[C@@H]1CC[C@@]2([C@H]([C@@]1(C)CCC(=O)O)CC[C@H]3[C@]2(CC[C@@H]3[C@](C)(C/C=C/[C@](C)(CO)O)O)C)C
• InChI: InChI=1S/C30H50O5/c1-20(2)21-11-18-29(6)24(27(21,4)16-13-25(32)33)10-9-22-23(12-17-28(22,29)5)30(7,35)15-8-14-26(3,34)19-31/h8,14,21-24,31,34-35H,1,9-13,15-19H2,2-7H3,(H,32,33)/b14-8+/t21-,22+,23-,24-,26+,27-,28+,29+,30-/m0/s1
• InChI Key: MOVXCFOJIQLFPC-BWFKXQRPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₅₀O₅
• Molecular Weight: 490.70 g/mol
• Exact Mass: 490.36582469 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.73
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9736	97.36%
Caco-2	-	0.6418	64.18%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7630	76.30%
OATP2B1 inhibitior	-	0.5698	56.98%
OATP1B1 inhibitior	+	0.8290	82.90%
OATP1B3 inhibitior	+	0.8783	87.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5840	58.40%
BSEP inhibitior	+	0.9724	97.24%
P-glycoprotein inhibitior	-	0.5162	51.62%
P-glycoprotein substrate	-	0.5441	54.41%
CYP3A4 substrate	+	0.6828	68.28%
CYP2C9 substrate	-	0.7958	79.58%
CYP2D6 substrate	-	0.8799	87.99%
CYP3A4 inhibition	-	0.6537	65.37%
CYP2C9 inhibition	-	0.8469	84.69%
CYP2C19 inhibition	-	0.9034	90.34%
CYP2D6 inhibition	-	0.9335	93.35%
CYP1A2 inhibition	-	0.8925	89.25%
CYP2C8 inhibition	+	0.5541	55.41%
CYP inhibitory promiscuity	-	0.8824	88.24%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.7248	72.48%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9320	93.20%
Skin irritation	+	0.4910	49.10%
Skin corrosion	-	0.9621	96.21%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7988	79.88%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.6935	69.35%
skin sensitisation	-	0.8106	81.06%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.7823	78.23%
Acute Oral Toxicity (c)	III	0.6602	66.02%
Estrogen receptor binding	+	0.7469	74.69%
Androgen receptor binding	+	0.7380	73.80%
Thyroid receptor binding	+	0.6257	62.57%
Glucocorticoid receptor binding	+	0.8113	81.13%
Aromatase binding	+	0.7119	71.19%
PPAR gamma	+	0.6806	68.06%
Honey bee toxicity	-	0.7833	78.33%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9945	99.45%

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	96.28%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.56%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.10%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.97%	98.95%
CHEMBL233	P35372	Mu opioid receptor	90.27%	97.93%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.99%	96.61%
CHEMBL4040	P28482	MAP kinase ERK2	88.18%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.93%	94.45%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.87%	93.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.31%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.24%	95.56%
CHEMBL5028	O14672	ADAM10	84.93%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.79%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.89%	96.38%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	82.85%	90.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.12%	100.00%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	81.95%	94.01%
CHEMBL340	P08684	Cytochrome P450 3A4	80.63%	91.19%

Plants that contains it

• Alnus japonica

Cross-Links

• PubChem: 162879016
• LOTUS: LTS0187348
• wikiData: Q105169199