3-[(3S,3aR,4R,5aS,6S,7S,9aR,9bR)-4-[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-[(2S)-2-hydroxy-6-methyl-5-methylideneheptan-2-yl]-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: 3313c314-2168-4d57-b98b-f1d390231898
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesterterpenoids
• IUPAC Name: 3-[(3S,3aR,4R,5aS,6S,7S,9aR,9bR)-4-[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-[(2S)-2-hydroxy-6-methyl-5-methylideneheptan-2-yl]-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)C(=C)CCC(C)(C1CCC2(C1C(CC3C2(CCC(C3(C)CCC(=O)O)C(=C)C)C)OC4C(C(C(O4)CO)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](O4)CO)O)O)C)O
• InChI: InChI=1S/C36H60O8/c1-20(2)22(5)10-17-36(9,42)24-12-16-35(8)29(24)25(43-32-31(41)30(40)26(19-37)44-32)18-27-33(6,14-13-28(38)39)23(21(3)4)11-15-34(27,35)7/h20,23-27,29-32,37,40-42H,3,5,10-19H2,1-2,4,6-9H3,(H,38,39)/t23-,24-,25+,26-,27-,29-,30-,31+,32+,33-,34+,35+,36-/m0/s1
• InChI Key: LYJUZZNOXNVGPX-NSTZHTBQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₆₀O₈
• Molecular Weight: 620.90 g/mol
• Exact Mass: 620.42881887 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: 6.80
• Atomic LogP (AlogP): 5.47
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9363	93.63%
Caco-2	-	0.8097	80.97%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7802	78.02%
OATP2B1 inhibitior	-	0.5716	57.16%
OATP1B1 inhibitior	+	0.8338	83.38%
OATP1B3 inhibitior	+	0.8617	86.17%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6792	67.92%
BSEP inhibitior	+	0.8190	81.90%
P-glycoprotein inhibitior	+	0.6683	66.83%
P-glycoprotein substrate	-	0.5526	55.26%
CYP3A4 substrate	+	0.6999	69.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8856	88.56%
CYP3A4 inhibition	-	0.7033	70.33%
CYP2C9 inhibition	-	0.6788	67.88%
CYP2C19 inhibition	-	0.8319	83.19%
CYP2D6 inhibition	-	0.9270	92.70%
CYP1A2 inhibition	-	0.8200	82.00%
CYP2C8 inhibition	+	0.5822	58.22%
CYP inhibitory promiscuity	-	0.8567	85.67%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6450	64.50%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9115	91.15%
Skin irritation	+	0.5402	54.02%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	-	0.6370	63.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3904	39.04%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5213	52.13%
skin sensitisation	-	0.8859	88.59%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.6453	64.53%
Acute Oral Toxicity (c)	III	0.4923	49.23%
Estrogen receptor binding	+	0.6037	60.37%
Androgen receptor binding	+	0.7125	71.25%
Thyroid receptor binding	-	0.5353	53.53%
Glucocorticoid receptor binding	+	0.6453	64.53%
Aromatase binding	+	0.6779	67.79%
PPAR gamma	+	0.6891	68.91%
Honey bee toxicity	-	0.6631	66.31%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9904	99.04%

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	99.24%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.69%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.22%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.01%	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%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.88%	96.47%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.61%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.26%	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%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.38%	93.00%
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	83.67%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.27%	97.14%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	82.58%	97.86%
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%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	82.32%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.12%	96.21%
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: 162974027
• LOTUS: LTS0147651
• wikiData: Q105159389