(Z)-5-[(1R,3R,4aS,7S,8aS)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid

Details

• Internal ID: 271e0568-0a6b-44d8-8cb5-3c4ab806fb05
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (Z)-5-[(1R,3R,4aS,7S,8aS)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid
• SMILES (Canonical): CC(=CC(=O)O)CCC1C(=C)C(CC2C1(CC(CC2(C)C)O)C)O
• SMILES (Isomeric): C/C(=C/C(=O)O)/CC[C@H]1C(=C)[C@@H](C[C@@H]2[C@@]1(C[C@H](CC2(C)C)O)C)O
• InChI: InChI=1S/C20H32O4/c1-12(8-18(23)24)6-7-15-13(2)16(22)9-17-19(3,4)10-14(21)11-20(15,17)5/h8,14-17,21-22H,2,6-7,9-11H2,1,3-5H3,(H,23,24)/b12-8-/t14-,15-,16+,17-,20+/m0/s1
• InChI Key: KJBUMDSUYZAJLW-DXCOAYDQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.50 g/mol
• Exact Mass: 336.23005950 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.54
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9886	98.86%
Caco-2	+	0.5413	54.13%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7542	75.42%
OATP2B1 inhibitior	-	0.8620	86.20%
OATP1B1 inhibitior	+	0.8435	84.35%
OATP1B3 inhibitior	-	0.2505	25.05%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.5152	51.52%
P-glycoprotein inhibitior	-	0.7951	79.51%
P-glycoprotein substrate	-	0.6850	68.50%
CYP3A4 substrate	+	0.6064	60.64%
CYP2C9 substrate	-	0.7928	79.28%
CYP2D6 substrate	-	0.9050	90.50%
CYP3A4 inhibition	-	0.6589	65.89%
CYP2C9 inhibition	-	0.9384	93.84%
CYP2C19 inhibition	-	0.9151	91.51%
CYP2D6 inhibition	-	0.9477	94.77%
CYP1A2 inhibition	-	0.9118	91.18%
CYP2C8 inhibition	-	0.6629	66.29%
CYP inhibitory promiscuity	-	0.8781	87.81%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7366	73.66%
Eye corrosion	-	0.9945	99.45%
Eye irritation	-	0.8468	84.68%
Skin irritation	+	0.6621	66.21%
Skin corrosion	-	0.9625	96.25%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4278	42.78%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7048	70.48%
skin sensitisation	+	0.5156	51.56%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6230	62.30%
Acute Oral Toxicity (c)	III	0.7257	72.57%
Estrogen receptor binding	+	0.8114	81.14%
Androgen receptor binding	+	0.6314	63.14%
Thyroid receptor binding	+	0.5510	55.10%
Glucocorticoid receptor binding	+	0.7253	72.53%
Aromatase binding	+	0.6458	64.58%
PPAR gamma	+	0.6251	62.51%
Honey bee toxicity	-	0.7583	75.83%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
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	94.01%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.36%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	90.96%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.57%	95.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.24%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.78%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.40%	91.19%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.88%	96.61%
CHEMBL2581	P07339	Cathepsin D	81.61%	98.95%
CHEMBL2061	P19793	Retinoid X receptor alpha	81.38%	91.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.90%	95.56%

Plants that contains it

• Stevia jujuyensis

Cross-Links

• PubChem: 162850754
• LOTUS: LTS0102678
• wikiData: Q105141771