methyl 3-[(3S,3aR,5aS,6S,7S,9aR,9bR)-3-[(E,2S,6R)-7-acetyloxy-2,6-dihydroxy-6-methylhept-4-en-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: 6ff9f9da-ac82-4a42-bec0-2d96fa2511a4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesterterpenoids
• IUPAC Name: methyl 3-[(3S,3aR,5aS,6S,7S,9aR,9bR)-3-[(E,2S,6R)-7-acetyloxy-2,6-dihydroxy-6-methylhept-4-en-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)C1CCC2(C(C1(C)CCC(=O)OC)CCC3C2(CCC3C(C)(CC=CC(C)(COC(=O)C)O)O)C)C
• SMILES (Isomeric): CC(=C)[C@@H]1CC[C@@]2([C@H]([C@@]1(C)CCC(=O)OC)CC[C@H]3[C@]2(CC[C@@H]3[C@](C)(C/C=C/[C@](C)(COC(=O)C)O)O)C)C
• InChI: InChI=1S/C33H54O6/c1-22(2)24-13-20-32(7)27(30(24,5)18-15-28(35)38-9)12-11-25-26(14-19-31(25,32)6)33(8,37)17-10-16-29(4,36)21-39-23(3)34/h10,16,24-27,36-37H,1,11-15,17-21H2,2-9H3/b16-10+/t24-,25+,26-,27-,29+,30-,31+,32+,33-/m0/s1
• InChI Key: XQFCPYJFYCWSPB-ADPNPCFCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₄O₆
• Molecular Weight: 546.80 g/mol
• Exact Mass: 546.39203944 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 6.80
• Atomic LogP (AlogP): 6.39
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9791	97.91%
Caco-2	-	0.7265	72.65%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8381	83.81%
OATP2B1 inhibitior	-	0.5654	56.54%
OATP1B1 inhibitior	+	0.8355	83.55%
OATP1B3 inhibitior	+	0.8959	89.59%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6510	65.10%
BSEP inhibitior	+	0.9742	97.42%
P-glycoprotein inhibitior	+	0.6955	69.55%
P-glycoprotein substrate	+	0.5478	54.78%
CYP3A4 substrate	+	0.7218	72.18%
CYP2C9 substrate	-	0.8156	81.56%
CYP2D6 substrate	-	0.8808	88.08%
CYP3A4 inhibition	-	0.6427	64.27%
CYP2C9 inhibition	-	0.8121	81.21%
CYP2C19 inhibition	-	0.8899	88.99%
CYP2D6 inhibition	-	0.9381	93.81%
CYP1A2 inhibition	-	0.8801	88.01%
CYP2C8 inhibition	+	0.6733	67.33%
CYP inhibitory promiscuity	-	0.8105	81.05%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.7076	70.76%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9253	92.53%
Skin irritation	-	0.5447	54.47%
Skin corrosion	-	0.9672	96.72%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7076	70.76%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6560	65.60%
skin sensitisation	-	0.8310	83.10%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.5956	59.56%
Acute Oral Toxicity (c)	III	0.5122	51.22%
Estrogen receptor binding	+	0.6548	65.48%
Androgen receptor binding	+	0.7514	75.14%
Thyroid receptor binding	+	0.5466	54.66%
Glucocorticoid receptor binding	+	0.7636	76.36%
Aromatase binding	+	0.7167	71.67%
PPAR gamma	+	0.6215	62.15%
Honey bee toxicity	-	0.6552	65.52%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9960	99.60%

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	97.18%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.01%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.59%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.97%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.57%	96.95%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.11%	100.00%
CHEMBL5028	O14672	ADAM10	85.81%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.41%	91.07%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.03%	97.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.60%	94.33%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	83.96%	94.01%
CHEMBL233	P35372	Mu opioid receptor	83.12%	97.93%
CHEMBL340	P08684	Cytochrome P450 3A4	83.03%	91.19%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.37%	93.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.34%	99.17%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	82.25%	95.52%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.01%	96.90%
CHEMBL2996	Q05655	Protein kinase C delta	81.91%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.64%	95.56%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.16%	97.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.15%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.94%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.25%	100.00%

Plants that contains it

• Alnus japonica

Cross-Links

• PubChem: 162948834
• LOTUS: LTS0088722
• wikiData: Q105339656