3-[(3S,3aS,4R,5aR,6S,7S,9aR,9bR)-4-[(2S,3R,4S,5R)-3-acetyloxy-4,5-dihydroxyoxan-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: 4ea6466d-1706-4d9c-b5f0-da97e7c3d6a0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesterterpenoids
• IUPAC Name: 3-[(3S,3aS,4R,5aR,6S,7S,9aR,9bR)-4-[(2S,3R,4S,5R)-3-acetyloxy-4,5-dihydroxyoxan-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(CO4)O)O)OC(=O)C)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](CO4)O)O)OC(=O)C)C)O
• InChI: InChI=1S/C38H62O9/c1-21(2)23(5)11-18-38(10,44)26-13-17-37(9)31(26)28(47-34-33(46-24(6)39)32(43)27(40)20-45-34)19-29-35(7,15-14-30(41)42)25(22(3)4)12-16-36(29,37)8/h21,25-29,31-34,40,43-44H,3,5,11-20H2,1-2,4,6-10H3,(H,41,42)/t25-,26-,27+,28+,29+,31+,32-,33+,34-,35-,36+,37+,38-/m0/s1
• InChI Key: QEJCHDFPOLIOOM-HKHMYXDBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₆₂O₉
• Molecular Weight: 662.90 g/mol
• Exact Mass: 662.43938355 g/mol
• Topological Polar Surface Area (TPSA): 143.00 Ų
• XlogP: 6.80
• Atomic LogP (AlogP): 6.04
• 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	+	0.9295	92.95%
Caco-2	-	0.8376	83.76%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8592	85.92%
OATP2B1 inhibitior	-	0.7166	71.66%
OATP1B1 inhibitior	+	0.8348	83.48%
OATP1B3 inhibitior	+	0.8757	87.57%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6850	68.50%
BSEP inhibitior	+	0.8572	85.72%
P-glycoprotein inhibitior	+	0.7160	71.60%
P-glycoprotein substrate	+	0.6417	64.17%
CYP3A4 substrate	+	0.7185	71.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8927	89.27%
CYP3A4 inhibition	-	0.7167	71.67%
CYP2C9 inhibition	-	0.7140	71.40%
CYP2C19 inhibition	-	0.8195	81.95%
CYP2D6 inhibition	-	0.9476	94.76%
CYP1A2 inhibition	-	0.7380	73.80%
CYP2C8 inhibition	+	0.6478	64.78%
CYP inhibitory promiscuity	-	0.9415	94.15%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6986	69.86%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9096	90.96%
Skin irritation	+	0.5910	59.10%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4770	47.70%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.5031	50.31%
skin sensitisation	-	0.8824	88.24%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.8544	85.44%
Acute Oral Toxicity (c)	I	0.4147	41.47%
Estrogen receptor binding	+	0.6472	64.72%
Androgen receptor binding	+	0.6922	69.22%
Thyroid receptor binding	-	0.5743	57.43%
Glucocorticoid receptor binding	+	0.6879	68.79%
Aromatase binding	+	0.6991	69.91%
PPAR gamma	+	0.6892	68.92%
Honey bee toxicity	-	0.6429	64.29%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9937	99.37%

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	99.31%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.78%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.50%	96.77%
CHEMBL2581	P07339	Cathepsin D	97.22%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.95%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.91%	95.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.79%	97.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.25%	91.07%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.12%	96.47%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	87.07%	97.33%
CHEMBL5028	O14672	ADAM10	86.75%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	86.28%	90.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.04%	93.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.95%	86.33%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	85.42%	94.97%
CHEMBL340	P08684	Cytochrome P450 3A4	85.41%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.94%	85.14%
CHEMBL2996	Q05655	Protein kinase C delta	84.87%	97.79%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.64%	82.69%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.48%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.13%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.74%	100.00%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	82.84%	97.86%
CHEMBL1951	P21397	Monoamine oxidase A	82.79%	91.49%
CHEMBL5255	O00206	Toll-like receptor 4	82.45%	92.50%
CHEMBL5285	Q99683	Mitogen-activated protein kinase kinase kinase 5	82.28%	92.26%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.18%	95.89%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.11%	82.50%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	81.96%	92.50%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.55%	95.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.47%	100.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.94%	94.08%
CHEMBL2179	P04062	Beta-glucocerebrosidase	80.69%	85.31%

Plants that contains it

• Alnus serrulatoides

Cross-Links

• PubChem: 162959265
• LOTUS: LTS0064512
• wikiData: Q105219236