(3S)-5-[(1R,4aS,5S,8aS)-5-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpentanoic acid

Details

• Internal ID: dd06659b-dcc3-4d27-93b1-43158ff14a7c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (3S)-5-[(1R,4aS,5S,8aS)-5-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpentanoic acid
• SMILES (Canonical): CC(CCC1C(=C)CCC2C1(CCCC2(C)COC(=O)C=CC3=CC=C(C=C3)O)C)CC(=O)O
• SMILES (Isomeric): C[C@@H](CC[C@@H]1C(=C)CC[C@H]2[C@]1(CCC[C@]2(C)COC(=O)/C=C/C3=CC=C(C=C3)O)C)CC(=O)O
• InChI: InChI=1S/C29H40O5/c1-20(18-26(31)32)6-13-24-21(2)7-14-25-28(3,16-5-17-29(24,25)4)19-34-27(33)15-10-22-8-11-23(30)12-9-22/h8-12,15,20,24-25,30H,2,5-7,13-14,16-19H2,1,3-4H3,(H,31,32)/b15-10+/t20-,24+,25+,28+,29-/m0/s1
• InChI Key: YCHBREPSJXLSOJ-HAFCEMPDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₀O₅
• Molecular Weight: 468.60 g/mol
• Exact Mass: 468.28757437 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 7.10
• Atomic LogP (AlogP): 6.62
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9891	98.91%
Caco-2	-	0.7241	72.41%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8775	87.75%
OATP2B1 inhibitior	-	0.7162	71.62%
OATP1B1 inhibitior	+	0.8380	83.80%
OATP1B3 inhibitior	+	0.8616	86.16%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7064	70.64%
BSEP inhibitior	+	0.9592	95.92%
P-glycoprotein inhibitior	+	0.6535	65.35%
P-glycoprotein substrate	-	0.5690	56.90%
CYP3A4 substrate	+	0.6782	67.82%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8877	88.77%
CYP3A4 inhibition	+	0.5519	55.19%
CYP2C9 inhibition	-	0.8064	80.64%
CYP2C19 inhibition	-	0.7310	73.10%
CYP2D6 inhibition	-	0.8991	89.91%
CYP1A2 inhibition	-	0.5338	53.38%
CYP2C8 inhibition	+	0.7482	74.82%
CYP inhibitory promiscuity	-	0.7571	75.71%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6854	68.54%
Eye corrosion	-	0.9951	99.51%
Eye irritation	-	0.8973	89.73%
Skin irritation	-	0.5472	54.72%
Skin corrosion	-	0.9703	97.03%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6921	69.21%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.6519	65.19%
skin sensitisation	-	0.8193	81.93%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.8643	86.43%
Acute Oral Toxicity (c)	III	0.7483	74.83%
Estrogen receptor binding	+	0.7894	78.94%
Androgen receptor binding	+	0.8301	83.01%
Thyroid receptor binding	+	0.5208	52.08%
Glucocorticoid receptor binding	+	0.7499	74.99%
Aromatase binding	+	0.6451	64.51%
PPAR gamma	+	0.6550	65.50%
Honey bee toxicity	-	0.7791	77.91%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5755	57.55%
Fish aquatic toxicity	+	1.0000	100.00%

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	97.39%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.34%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	94.93%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.16%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.01%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.56%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.12%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.55%	94.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.92%	96.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	88.09%	94.08%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.87%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.06%	96.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.55%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.38%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.20%	97.25%
CHEMBL206	P03372	Estrogen receptor alpha	84.60%	97.64%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.32%	91.71%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.74%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.14%	90.71%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.96%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.55%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	81.43%	91.19%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.12%	94.23%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	81.06%	89.33%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	80.90%	94.97%

Plants that contains it

• Nuxia sphaerocephala

Cross-Links

• PubChem: 11554552
• LOTUS: LTS0267143
• wikiData: Q105346256