[(2S,3S,4aS,5R,8aS)-5-[(E)-5-acetyloxy-3-methylpent-3-enyl]-1,1,4a,6-tetramethyl-3-[(2R,3S,4R,5S)-3,4,5-triacetyloxyoxan-2-yl]oxy-2,3,4,5,8,8a-hexahydronaphthalen-2-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 044492c7-e1b3-411f-be32-0df60180280a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2S,3S,4aS,5R,8aS)-5-[(E)-5-acetyloxy-3-methylpent-3-enyl]-1,1,4a,6-tetramethyl-3-[(2R,3S,4R,5S)-3,4,5-triacetyloxyoxan-2-yl]oxy-2,3,4,5,8,8a-hexahydronaphthalen-2-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(CC2(C(C1(C)C)CC=C(C2CCC(=CCOC(=O)C)C)C)C)OC3C(C(C(CO3)OC(=O)C)OC(=O)C)OC(=O)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1[C@H](C[C@@]2([C@@H](C1(C)C)CC=C([C@H]2CC/C(=C/COC(=O)C)/C)C)C)O[C@@H]3[C@H]([C@@H]([C@H](CO3)OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C38H56O12/c1-12-22(3)35(43)50-34-29(49-36-33(48-27(8)42)32(47-26(7)41)30(20-45-36)46-25(6)40)19-38(11)28(15-13-21(2)17-18-44-24(5)39)23(4)14-16-31(38)37(34,9)10/h12,14,17,28-34,36H,13,15-16,18-20H2,1-11H3/b21-17+,22-12-/t28-,29+,30+,31-,32-,33+,34-,36-,38+/m1/s1
• InChI Key: VBQGWBRRDXZVFW-YXAHLESGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₅₆O₁₂
• Molecular Weight: 704.80 g/mol
• Exact Mass: 704.37717722 g/mol
• Topological Polar Surface Area (TPSA): 150.00 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.71
• H-Bond Acceptor: 12
• H-Bond Donor: 0
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9669	96.69%
Caco-2	-	0.8221	82.21%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8281	82.81%
OATP2B1 inhibitior	-	0.5693	56.93%
OATP1B1 inhibitior	+	0.8049	80.49%
OATP1B3 inhibitior	+	0.8835	88.35%
MATE1 inhibitior	-	0.6600	66.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.9904	99.04%
P-glycoprotein inhibitior	+	0.8622	86.22%
P-glycoprotein substrate	-	0.5220	52.20%
CYP3A4 substrate	+	0.7163	71.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9031	90.31%
CYP3A4 inhibition	-	0.9022	90.22%
CYP2C9 inhibition	-	0.8742	87.42%
CYP2C19 inhibition	-	0.7717	77.17%
CYP2D6 inhibition	-	0.9459	94.59%
CYP1A2 inhibition	-	0.7342	73.42%
CYP2C8 inhibition	+	0.6536	65.36%
CYP inhibitory promiscuity	-	0.8539	85.39%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6131	61.31%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9153	91.53%
Skin irritation	-	0.6663	66.63%
Skin corrosion	-	0.9535	95.35%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4169	41.69%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5222	52.22%
skin sensitisation	-	0.8109	81.09%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.6221	62.21%
Acute Oral Toxicity (c)	III	0.5474	54.74%
Estrogen receptor binding	+	0.8247	82.47%
Androgen receptor binding	+	0.6471	64.71%
Thyroid receptor binding	+	0.5259	52.59%
Glucocorticoid receptor binding	+	0.8391	83.91%
Aromatase binding	+	0.7038	70.38%
PPAR gamma	+	0.7819	78.19%
Honey bee toxicity	-	0.6592	65.92%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9881	98.81%

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	96.52%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.79%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.55%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.24%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.74%	97.25%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.66%	95.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	89.53%	93.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.49%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.71%	91.07%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.69%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.91%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.62%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.30%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.75%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	84.19%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	84.18%	94.73%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.35%	91.24%
CHEMBL1937	Q92769	Histone deacetylase 2	82.18%	94.75%
CHEMBL5255	O00206	Toll-like receptor 4	81.58%	92.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.50%	99.23%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	80.16%	91.65%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.08%	92.62%

Plants that contains it

• Gymnosperma glutinosum

Cross-Links

• PubChem: 163017670
• LOTUS: LTS0033328
• wikiData: Q105283428