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

Details

• Internal ID: 5c4a66e1-1b09-4fbb-a6a0-d09f26ef5752
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesterterpenoids
• IUPAC Name: 3-[(3S,3aS,4R,5aR,6S,7S,9aR,9bR)-3-[(E,2S)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-4-hydroxy-6,9a,9b-trimethyl-7-prop-1-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)CC(C3C2(CCC3C(C)(CC=CC(C)(C)O)O)C)O)C
• SMILES (Isomeric): CC(=C)[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CCC(=O)O)C[C@H]([C@@H]3[C@]2(CC[C@@H]3[C@](C)(C/C=C/C(C)(C)O)O)C)O)C
• InChI: InChI=1S/C30H50O5/c1-19(2)20-10-16-28(6)23(27(20,5)15-12-24(32)33)18-22(31)25-21(11-17-29(25,28)7)30(8,35)14-9-13-26(3,4)34/h9,13,20-23,25,31,34-35H,1,10-12,14-18H2,2-8H3,(H,32,33)/b13-9+/t20-,21-,22+,23+,25+,27-,28+,29+,30-/m0/s1
• InChI Key: IVWHYNKOPOPMJS-NIWGLMRLSA-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: 5.60
• Atomic LogP (AlogP): 5.73
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9930	99.30%
Caco-2	-	0.6602	66.02%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7864	78.64%
OATP2B1 inhibitior	-	0.7150	71.50%
OATP1B1 inhibitior	+	0.8242	82.42%
OATP1B3 inhibitior	-	0.5000	50.00%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9777	97.77%
P-glycoprotein inhibitior	-	0.5326	53.26%
P-glycoprotein substrate	+	0.5280	52.80%
CYP3A4 substrate	+	0.6879	68.79%
CYP2C9 substrate	-	0.8098	80.98%
CYP2D6 substrate	-	0.8680	86.80%
CYP3A4 inhibition	-	0.7863	78.63%
CYP2C9 inhibition	-	0.9271	92.71%
CYP2C19 inhibition	-	0.9311	93.11%
CYP2D6 inhibition	-	0.9590	95.90%
CYP1A2 inhibition	-	0.9427	94.27%
CYP2C8 inhibition	+	0.5438	54.38%
CYP inhibitory promiscuity	-	0.8526	85.26%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7141	71.41%
Eye corrosion	-	0.9954	99.54%
Eye irritation	-	0.9227	92.27%
Skin irritation	+	0.7017	70.17%
Skin corrosion	-	0.9563	95.63%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6821	68.21%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5959	59.59%
skin sensitisation	-	0.5795	57.95%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.6470	64.70%
Acute Oral Toxicity (c)	I	0.5836	58.36%
Estrogen receptor binding	+	0.7795	77.95%
Androgen receptor binding	+	0.7306	73.06%
Thyroid receptor binding	+	0.5584	55.84%
Glucocorticoid receptor binding	+	0.7933	79.33%
Aromatase binding	+	0.7402	74.02%
PPAR gamma	+	0.6270	62.70%
Honey bee toxicity	-	0.6855	68.55%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.69%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.73%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.59%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.85%	82.69%
CHEMBL2581	P07339	Cathepsin D	91.61%	98.95%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.73%	94.62%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.43%	93.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.31%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.32%	86.33%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	83.58%	95.52%
CHEMBL5028	O14672	ADAM10	83.44%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	82.92%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.39%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.92%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.66%	89.34%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.14%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.87%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.52%	95.56%

Plants that contains it

• Alnus japonica

Cross-Links

• PubChem: 162884645
• LOTUS: LTS0037106
• wikiData: Q105121338