[(2S,3S,4aS,5R,8aS)-5-[(3S)-5-hydroxy-3-methylpentyl]-1,1,4a,6-tetramethyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3,4,5,8,8a-hexahydronaphthalen-2-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: fcdb2c3e-41dc-4db1-bc70-32f50d2a0a87
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2S,3S,4aS,5R,8aS)-5-[(3S)-5-hydroxy-3-methylpentyl]-1,1,4a,6-tetramethyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-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(C)CCO)C)C)OC3C(C(C(CO3)O)O)O
• 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@H](C)CCO)C)C)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O
• InChI: InChI=1S/C30H50O8/c1-8-18(3)27(35)38-26-22(37-28-25(34)24(33)21(32)16-36-28)15-30(7)20(11-9-17(2)13-14-31)19(4)10-12-23(30)29(26,5)6/h8,10,17,20-26,28,31-34H,9,11-16H2,1-7H3/b18-8-/t17-,20+,21+,22-,23+,24-,25+,26+,28-,30-/m0/s1
• InChI Key: NWFSDHZPEKQVFJ-NZIRIMHQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₅₀O₈
• Molecular Weight: 538.70 g/mol
• Exact Mass: 538.35056855 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.51
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7768	77.68%
Caco-2	-	0.7604	76.04%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8337	83.37%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	+	0.8503	85.03%
OATP1B3 inhibitior	-	0.3365	33.65%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.7224	72.24%
P-glycoprotein inhibitior	+	0.6804	68.04%
P-glycoprotein substrate	+	0.5492	54.92%
CYP3A4 substrate	+	0.6962	69.62%
CYP2C9 substrate	-	0.8033	80.33%
CYP2D6 substrate	-	0.8830	88.30%
CYP3A4 inhibition	-	0.9021	90.21%
CYP2C9 inhibition	-	0.8375	83.75%
CYP2C19 inhibition	-	0.8403	84.03%
CYP2D6 inhibition	-	0.9362	93.62%
CYP1A2 inhibition	-	0.8126	81.26%
CYP2C8 inhibition	-	0.5712	57.12%
CYP inhibitory promiscuity	-	0.9527	95.27%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7155	71.55%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9399	93.99%
Skin irritation	-	0.6357	63.57%
Skin corrosion	-	0.9537	95.37%
Ames mutagenesis	-	0.5470	54.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7097	70.97%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.6802	68.02%
skin sensitisation	-	0.8817	88.17%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.7204	72.04%
Acute Oral Toxicity (c)	III	0.7381	73.81%
Estrogen receptor binding	+	0.6906	69.06%
Androgen receptor binding	+	0.5526	55.26%
Thyroid receptor binding	-	0.5483	54.83%
Glucocorticoid receptor binding	+	0.6863	68.63%
Aromatase binding	+	0.6806	68.06%
PPAR gamma	+	0.6195	61.95%
Honey bee toxicity	-	0.6651	66.51%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9438	94.38%

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	98.01%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.36%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.60%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	93.59%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.64%	97.25%
CHEMBL2581	P07339	Cathepsin D	92.25%	98.95%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.57%	96.47%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.46%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.04%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	87.98%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.78%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.39%	91.07%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.19%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.14%	97.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.62%	93.56%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.13%	91.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.74%	99.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.53%	93.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.55%	97.21%
CHEMBL340	P08684	Cytochrome P450 3A4	82.20%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.09%	90.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.84%	94.33%
CHEMBL1937	Q92769	Histone deacetylase 2	80.77%	94.75%

Plants that contains it

• Gymnosperma glutinosum

Cross-Links

• PubChem: 102060698
• LOTUS: LTS0238428
• wikiData: Q105186588