3-[(3S,3aS,5aR,6S,7R,9R,9aR)-9-[(2R,3R)-2-hydroxy-3-methylpentanoyl]oxy-7-(2-hydroxypropan-2-yl)-3a,6,9a-trimethyl-3-[(3S,5S)-5-(2-methylprop-1-enyl)oxolan-3-yl]-2,3,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-6-yl]propanoic acid

Details

• Internal ID: 00772a20-87c0-4b44-94dd-cf15653f45a8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: 3-[(3S,3aS,5aR,6S,7R,9R,9aR)-9-[(2R,3R)-2-hydroxy-3-methylpentanoyl]oxy-7-(2-hydroxypropan-2-yl)-3a,6,9a-trimethyl-3-[(3S,5S)-5-(2-methylprop-1-enyl)oxolan-3-yl]-2,3,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-6-yl]propanoic acid
• SMILES (Canonical): CCC(C)C(C(=O)OC1CC(C(C2C1(C3=CCC(C3(CC2)C)C4CC(OC4)C=C(C)C)C)(C)CCC(=O)O)C(C)(C)O)O
• SMILES (Isomeric): CC[C@@H](C)[C@H](C(=O)O[C@@H]1C[C@H]([C@@]([C@@H]2[C@@]1(C3=CC[C@H]([C@@]3(CC2)C)[C@@H]4C[C@H](OC4)C=C(C)C)C)(C)CCC(=O)O)C(C)(C)O)O
• InChI: InChI=1S/C36H58O7/c1-10-22(4)31(39)32(40)43-29-19-28(33(5,6)41)35(8,16-14-30(37)38)27-13-15-34(7)25(11-12-26(34)36(27,29)9)23-18-24(42-20-23)17-21(2)3/h12,17,22-25,27-29,31,39,41H,10-11,13-16,18-20H2,1-9H3,(H,37,38)/t22-,23-,24-,25+,27-,28+,29-,31-,34+,35+,36+/m1/s1
• InChI Key: YDKADZFQYAVBMO-DYRSITRKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₈O₇
• Molecular Weight: 602.80 g/mol
• Exact Mass: 602.41825418 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 6.90
• Atomic LogP (AlogP): 6.71
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9956	99.56%
Caco-2	-	0.7840	78.40%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8909	89.09%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.8264	82.64%
OATP1B3 inhibitior	+	0.9476	94.76%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7157	71.57%
BSEP inhibitior	+	0.9046	90.46%
P-glycoprotein inhibitior	+	0.7577	75.77%
P-glycoprotein substrate	+	0.6675	66.75%
CYP3A4 substrate	+	0.7241	72.41%
CYP2C9 substrate	-	0.8125	81.25%
CYP2D6 substrate	-	0.8700	87.00%
CYP3A4 inhibition	+	0.7260	72.60%
CYP2C9 inhibition	-	0.6324	63.24%
CYP2C19 inhibition	-	0.8416	84.16%
CYP2D6 inhibition	-	0.9014	90.14%
CYP1A2 inhibition	-	0.8747	87.47%
CYP2C8 inhibition	+	0.7445	74.45%
CYP inhibitory promiscuity	-	0.6348	63.48%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5205	52.05%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9256	92.56%
Skin irritation	+	0.5884	58.84%
Skin corrosion	-	0.9430	94.30%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4052	40.52%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5351	53.51%
skin sensitisation	-	0.9022	90.22%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.9400	94.00%
Acute Oral Toxicity (c)	III	0.5184	51.84%
Estrogen receptor binding	+	0.7450	74.50%
Androgen receptor binding	+	0.7093	70.93%
Thyroid receptor binding	-	0.5277	52.77%
Glucocorticoid receptor binding	+	0.7883	78.83%
Aromatase binding	+	0.7272	72.72%
PPAR gamma	+	0.6482	64.82%
Honey bee toxicity	-	0.6482	64.82%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9972	99.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.94%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.48%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.74%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.28%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.84%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.66%	91.11%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	92.31%	97.21%
CHEMBL4227	P25090	Lipoxin A4 receptor	90.94%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	90.88%	93.56%
CHEMBL5028	O14672	ADAM10	89.97%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.62%	89.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	89.43%	89.05%
CHEMBL340	P08684	Cytochrome P450 3A4	88.11%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.27%	91.07%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.97%	96.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.33%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.62%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.01%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.89%	86.33%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	83.88%	94.97%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.40%	94.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.07%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.08%	85.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.99%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.50%	99.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.46%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.10%	99.17%

Plants that contains it

• Aglaia argentea

Cross-Links

• PubChem: 163106697
• LOTUS: LTS0274894
• wikiData: Q105346775