5-(6,7-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: 7ce1dc4e-4b6e-4518-b836-4b533c51ad98
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 5-(6,7-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)CCC2C1(CC(C(C2(C)C)O)O)C
• SMILES (Isomeric): CC(=CC(=O)O)CCC1C(=C)CCC2C1(CC(C(C2(C)C)O)O)C
• InChI: InChI=1S/C20H32O4/c1-12(10-17(22)23)6-8-14-13(2)7-9-16-19(3,4)18(24)15(21)11-20(14,16)5/h10,14-16,18,21,24H,2,6-9,11H2,1,3-5H3,(H,22,23)
• InChI Key: QRYJHSMVZUKZQU-UHFFFAOYSA-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: 3.80
• 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	+	0.9828	98.28%
Caco-2	+	0.5821	58.21%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8146	81.46%
OATP2B1 inhibitior	-	0.8642	86.42%
OATP1B1 inhibitior	+	0.8488	84.88%
OATP1B3 inhibitior	-	0.2308	23.08%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.6943	69.43%
P-glycoprotein inhibitior	-	0.8135	81.35%
P-glycoprotein substrate	-	0.7711	77.11%
CYP3A4 substrate	+	0.6207	62.07%
CYP2C9 substrate	-	0.7939	79.39%
CYP2D6 substrate	-	0.9009	90.09%
CYP3A4 inhibition	-	0.7088	70.88%
CYP2C9 inhibition	-	0.8916	89.16%
CYP2C19 inhibition	-	0.8287	82.87%
CYP2D6 inhibition	-	0.9497	94.97%
CYP1A2 inhibition	-	0.9143	91.43%
CYP2C8 inhibition	-	0.6590	65.90%
CYP inhibitory promiscuity	-	0.9447	94.47%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7530	75.30%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.8874	88.74%
Skin irritation	+	0.6091	60.91%
Skin corrosion	-	0.9496	94.96%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4019	40.19%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.7069	70.69%
skin sensitisation	-	0.5791	57.91%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6591	65.91%
Acute Oral Toxicity (c)	III	0.7301	73.01%
Estrogen receptor binding	+	0.6370	63.70%
Androgen receptor binding	+	0.6202	62.02%
Thyroid receptor binding	+	0.6173	61.73%
Glucocorticoid receptor binding	+	0.7676	76.76%
Aromatase binding	+	0.6169	61.69%
PPAR gamma	+	0.6017	60.17%
Honey bee toxicity	-	0.8451	84.51%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
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
CHEMBL4040	P28482	MAP kinase ERK2	99.77%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.06%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	91.02%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.49%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.43%	100.00%
CHEMBL2061	P19793	Retinoid X receptor alpha	84.07%	91.67%
CHEMBL340	P08684	Cytochrome P450 3A4	84.02%	91.19%
CHEMBL2581	P07339	Cathepsin D	83.46%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.24%	95.56%

Plants that contains it

• Nolana rostrata

Cross-Links

• PubChem: 163005485
• LOTUS: LTS0104190
• wikiData: Q105226737