5-(6-hydroxy-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl)-3-methylidene-4-oxopentanoic acid

Details

• Internal ID: 9467e375-fcd0-44ec-a97c-bb9a16b74757
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: 5-(6-hydroxy-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl)-3-methylidene-4-oxopentanoic acid
• SMILES (Canonical): CC1CCC2(C(C1(C)CC(=O)C(=C)CC(=O)O)CCC(C2=C)O)C
• SMILES (Isomeric): CC1CCC2(C(C1(C)CC(=O)C(=C)CC(=O)O)CCC(C2=C)O)C
• InChI: InChI=1S/C20H30O4/c1-12(10-18(23)24)16(22)11-20(5)13(2)8-9-19(4)14(3)15(21)6-7-17(19)20/h13,15,17,21H,1,3,6-11H2,2,4-5H3,(H,23,24)
• InChI Key: AXFOKPPCLGXPNK-UHFFFAOYSA-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: 3.20
• Atomic LogP (AlogP): 3.75
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9858	98.58%
Caco-2	+	0.5634	56.34%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8187	81.87%
OATP2B1 inhibitior	-	0.8628	86.28%
OATP1B1 inhibitior	+	0.8824	88.24%
OATP1B3 inhibitior	-	0.2674	26.74%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7021	70.21%
BSEP inhibitior	-	0.7994	79.94%
P-glycoprotein inhibitior	-	0.7315	73.15%
P-glycoprotein substrate	-	0.7913	79.13%
CYP3A4 substrate	+	0.5715	57.15%
CYP2C9 substrate	-	0.7965	79.65%
CYP2D6 substrate	-	0.8831	88.31%
CYP3A4 inhibition	-	0.5719	57.19%
CYP2C9 inhibition	-	0.9505	95.05%
CYP2C19 inhibition	-	0.9401	94.01%
CYP2D6 inhibition	-	0.9526	95.26%
CYP1A2 inhibition	-	0.9453	94.53%
CYP2C8 inhibition	-	0.7463	74.63%
CYP inhibitory promiscuity	-	0.9413	94.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7244	72.44%
Eye corrosion	-	0.9946	99.46%
Eye irritation	-	0.8167	81.67%
Skin irritation	+	0.6635	66.35%
Skin corrosion	-	0.9561	95.61%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4765	47.65%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.5451	54.51%
skin sensitisation	-	0.6117	61.17%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.6147	61.47%
Acute Oral Toxicity (c)	III	0.7788	77.88%
Estrogen receptor binding	+	0.6898	68.98%
Androgen receptor binding	-	0.5108	51.08%
Thyroid receptor binding	+	0.6522	65.22%
Glucocorticoid receptor binding	+	0.6792	67.92%
Aromatase binding	+	0.6449	64.49%
PPAR gamma	-	0.4883	48.83%
Honey bee toxicity	-	0.8651	86.51%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
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
CHEMBL221	P23219	Cyclooxygenase-1	94.34%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.04%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.38%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	91.07%	91.19%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.63%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	85.75%	83.82%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.05%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.86%	95.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.61%	95.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.00%	97.25%
CHEMBL5028	O14672	ADAM10	81.26%	97.50%

Plants that contains it

• Callicarpa pentandra

Cross-Links

• PubChem: 5255938
• LOTUS: LTS0108375
• wikiData: Q104920509