methyl 3-[(3S,3aR,4R,5aR,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]propanoate

Details

• Internal ID: e1c2c9be-2e68-44e2-b528-4c1c08bc1e0d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesterterpenoids
• IUPAC Name: methyl 3-[(3S,3aR,4R,5aR,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]propanoate
• SMILES (Canonical): CC(C)C(=C)CCC(C)(C1CCC2(C1C(CC3C2(CCC(C3(C)CCC(=O)OC)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)OC)C(=C)C)C)O[C@H]4[C@@H]([C@H]([C@@H](O4)CO)O)O)C)O
• InChI: InChI=1S/C37H62O8/c1-21(2)23(5)11-18-37(9,42)25-13-17-36(8)30(25)26(44-33-32(41)31(40)27(20-38)45-33)19-28-34(6,15-14-29(39)43-10)24(22(3)4)12-16-35(28,36)7/h21,24-28,30-33,38,40-42H,3,5,11-20H2,1-2,4,6-10H3/t24-,25-,26+,27-,28+,30-,31-,32+,33+,34-,35+,36+,37-/m0/s1
• InChI Key: QLGYYCFLHPAKBH-VSKKITLYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₆₂O₈
• Molecular Weight: 634.90 g/mol
• Exact Mass: 634.44446893 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: 7.10
• Atomic LogP (AlogP): 5.56
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9302	93.02%
Caco-2	-	0.8174	81.74%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7616	76.16%
OATP2B1 inhibitior	-	0.7140	71.40%
OATP1B1 inhibitior	+	0.8283	82.83%
OATP1B3 inhibitior	+	0.8744	87.44%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6792	67.92%
BSEP inhibitior	+	0.7487	74.87%
P-glycoprotein inhibitior	+	0.6809	68.09%
P-glycoprotein substrate	+	0.5464	54.64%
CYP3A4 substrate	+	0.7109	71.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8887	88.87%
CYP3A4 inhibition	-	0.6795	67.95%
CYP2C9 inhibition	-	0.6772	67.72%
CYP2C19 inhibition	-	0.8113	81.13%
CYP2D6 inhibition	-	0.9289	92.89%
CYP1A2 inhibition	-	0.8120	81.20%
CYP2C8 inhibition	+	0.6203	62.03%
CYP inhibitory promiscuity	-	0.8802	88.02%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6454	64.54%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9102	91.02%
Skin irritation	-	0.5274	52.74%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.6170	61.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4093	40.93%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5463	54.63%
skin sensitisation	-	0.8812	88.12%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.5255	52.55%
Acute Oral Toxicity (c)	III	0.4120	41.20%
Estrogen receptor binding	+	0.5749	57.49%
Androgen receptor binding	+	0.7199	71.99%
Thyroid receptor binding	-	0.5382	53.82%
Glucocorticoid receptor binding	+	0.6446	64.46%
Aromatase binding	+	0.6852	68.52%
PPAR gamma	+	0.6706	67.06%
Honey bee toxicity	-	0.6306	63.06%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9817	98.17%

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	99.65%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.66%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.48%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.86%	85.14%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.57%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.47%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.75%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	91.47%	97.79%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.07%	96.77%
CHEMBL2581	P07339	Cathepsin D	90.26%	98.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.96%	96.21%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.76%	91.07%
CHEMBL4227	P25090	Lipoxin A4 receptor	89.34%	100.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	89.29%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.14%	97.14%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	87.09%	97.33%
CHEMBL5255	O00206	Toll-like receptor 4	87.07%	92.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.46%	96.47%
CHEMBL5028	O14672	ADAM10	86.00%	97.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.61%	92.62%
CHEMBL220	P22303	Acetylcholinesterase	84.90%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.74%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.19%	94.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.19%	95.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.00%	91.24%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	83.74%	100.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.64%	82.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.46%	86.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.79%	95.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.17%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.78%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.65%	93.56%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.17%	97.50%

Plants that contains it

• Alnus pendula

Cross-Links

• PubChem: 21596600
• LOTUS: LTS0231213
• wikiData: Q105223577