(1S,4aR,5S,8aS)-5-[3-(carboxymethyl)but-3-enyl]-1,4a,6-trimethyl-2,3,4,5,8,8a-hexahydronaphthalene-1-carboxylic acid

Details

• Internal ID: b4c3ba13-1059-4d38-a174-be0e8e8a5549
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1S,4aR,5S,8aS)-5-[3-(carboxymethyl)but-3-enyl]-1,4a,6-trimethyl-2,3,4,5,8,8a-hexahydronaphthalene-1-carboxylic acid
• SMILES (Canonical): CC1=CCC2C(C1CCC(=C)CC(=O)O)(CCCC2(C)C(=O)O)C
• SMILES (Isomeric): CC1=CC[C@H]2[C@@]([C@H]1CCC(=C)CC(=O)O)(CCC[C@]2(C)C(=O)O)C
• InChI: InChI=1S/C20H30O4/c1-13(12-17(21)22)6-8-15-14(2)7-9-16-19(15,3)10-5-11-20(16,4)18(23)24/h7,15-16H,1,5-6,8-12H2,2-4H3,(H,21,22)(H,23,24)/t15-,16-,19+,20-/m0/s1
• InChI Key: XGTWDFNUXUTSIZ-FEHORTKBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.21440943 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.66
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9798	97.98%
Caco-2	+	0.5864	58.64%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7206	72.06%
OATP2B1 inhibitior	-	0.8640	86.40%
OATP1B1 inhibitior	+	0.7973	79.73%
OATP1B3 inhibitior	-	0.2411	24.11%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6521	65.21%
BSEP inhibitior	-	0.5742	57.42%
P-glycoprotein inhibitior	-	0.7595	75.95%
P-glycoprotein substrate	-	0.7344	73.44%
CYP3A4 substrate	+	0.5901	59.01%
CYP2C9 substrate	-	0.5859	58.59%
CYP2D6 substrate	-	0.8733	87.33%
CYP3A4 inhibition	-	0.6135	61.35%
CYP2C9 inhibition	-	0.9265	92.65%
CYP2C19 inhibition	-	0.9317	93.17%
CYP2D6 inhibition	-	0.9508	95.08%
CYP1A2 inhibition	-	0.8934	89.34%
CYP2C8 inhibition	-	0.6903	69.03%
CYP inhibitory promiscuity	-	0.9165	91.65%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.7190	71.90%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.7204	72.04%
Skin irritation	-	0.5470	54.70%
Skin corrosion	-	0.9676	96.76%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6808	68.08%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5569	55.69%
skin sensitisation	+	0.6397	63.97%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7061	70.61%
Acute Oral Toxicity (c)	III	0.7339	73.39%
Estrogen receptor binding	+	0.5767	57.67%
Androgen receptor binding	-	0.5470	54.70%
Thyroid receptor binding	+	0.6051	60.51%
Glucocorticoid receptor binding	+	0.6597	65.97%
Aromatase binding	+	0.5935	59.35%
PPAR gamma	+	0.6071	60.71%
Honey bee toxicity	-	0.9349	93.49%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
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	94.74%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	92.90%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.46%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.90%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.21%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.12%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.39%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.13%	82.69%
CHEMBL340	P08684	Cytochrome P450 3A4	82.94%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.87%	100.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.17%	93.03%

Plants that contains it

• Gutierrezia microcephala

Cross-Links

• PubChem: 163106550
• LOTUS: LTS0210451
• wikiData: Q105327812