3-[(3R,3aR,4R,5aR,6S,7S,9aR,9bR)-3-[(2S)-2-hydroxy-6-methyl-5-methylideneheptan-2-yl]-6,9a,9b-trimethyl-7-prop-1-en-2-yl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,3a,4,5,5a,7,8,9-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid

Details

• Internal ID: 413f840e-39fb-4642-bdcc-0b6fd003828e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesterterpenoids
• IUPAC Name: 3-[(3R,3aR,4R,5aR,6S,7S,9aR,9bR)-3-[(2S)-2-hydroxy-6-methyl-5-methylideneheptan-2-yl]-6,9a,9b-trimethyl-7-prop-1-en-2-yl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,3a,4,5,5a,7,8,9-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid
• SMILES (Canonical): CC(C)C(=C)CCC(C)(C1CCC2(C1C(CC3C2(CCC(C3(C)CCC(=O)O)C(=C)C)C)OC4C(C(C(C(O4)CO)O)O)O)C)O
• SMILES (Isomeric): CC(C)C(=C)CC[C@@](C)([C@@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@H]([C@]3(C)CCC(=O)O)C(=C)C)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C)O
• InChI: InChI=1S/C37H62O9/c1-20(2)22(5)10-17-37(9,44)24-12-16-36(8)29(24)25(45-33-32(43)31(42)30(41)26(19-38)46-33)18-27-34(6,14-13-28(39)40)23(21(3)4)11-15-35(27,36)7/h20,23-27,29-33,38,41-44H,3,5,10-19H2,1-2,4,6-9H3,(H,39,40)/t23-,24+,25+,26+,27+,29-,30+,31-,32+,33+,34-,35+,36+,37-/m0/s1
• InChI Key: WGHKIPWWQPGCRZ-NXUXWYMKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₆₂O₉
• Molecular Weight: 650.90 g/mol
• Exact Mass: 650.43938355 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 4.83
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8577	85.77%
Caco-2	-	0.8360	83.60%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7863	78.63%
OATP2B1 inhibitior	-	0.5753	57.53%
OATP1B1 inhibitior	+	0.8329	83.29%
OATP1B3 inhibitior	+	0.8061	80.61%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7318	73.18%
BSEP inhibitior	+	0.7318	73.18%
P-glycoprotein inhibitior	+	0.6820	68.20%
P-glycoprotein substrate	-	0.5513	55.13%
CYP3A4 substrate	+	0.7017	70.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8856	88.56%
CYP3A4 inhibition	-	0.8229	82.29%
CYP2C9 inhibition	-	0.7418	74.18%
CYP2C19 inhibition	-	0.8450	84.50%
CYP2D6 inhibition	-	0.9353	93.53%
CYP1A2 inhibition	-	0.7982	79.82%
CYP2C8 inhibition	+	0.6010	60.10%
CYP inhibitory promiscuity	-	0.9145	91.45%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7335	73.35%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9110	91.10%
Skin irritation	+	0.5221	52.21%
Skin corrosion	-	0.9427	94.27%
Ames mutagenesis	-	0.6370	63.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3594	35.94%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.5237	52.37%
skin sensitisation	-	0.8895	88.95%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6616	66.16%
Acute Oral Toxicity (c)	III	0.5059	50.59%
Estrogen receptor binding	+	0.6236	62.36%
Androgen receptor binding	+	0.7128	71.28%
Thyroid receptor binding	-	0.5400	54.00%
Glucocorticoid receptor binding	+	0.6334	63.34%
Aromatase binding	+	0.6673	66.73%
PPAR gamma	+	0.6929	69.29%
Honey bee toxicity	-	0.6562	65.62%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9799	97.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.25%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.69%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.27%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.03%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.53%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.35%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.11%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.31%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.93%	85.14%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.88%	96.47%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.59%	86.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.25%	100.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	86.09%	97.33%
CHEMBL5255	O00206	Toll-like receptor 4	85.93%	92.50%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.68%	94.23%
CHEMBL5028	O14672	ADAM10	84.87%	97.50%
CHEMBL2996	Q05655	Protein kinase C delta	84.02%	97.79%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	83.81%	94.97%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.74%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.74%	93.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.36%	96.21%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.27%	97.14%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	82.58%	97.86%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	82.47%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.43%	93.56%
CHEMBL237	P41145	Kappa opioid receptor	82.33%	98.10%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.33%	82.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.05%	91.07%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.22%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.00%	100.00%

Plants that contains it

• Alnus pendula

Cross-Links

• PubChem: 163068495
• LOTUS: LTS0233396
• wikiData: Q105304491