5-[2-hydroxy-2,5,8a-trimethyl-5-(3-methylbut-2-enoyloxymethyl)-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpentanoic acid

Details

• Internal ID: 6c3fb1d0-716c-41fd-948b-8f922ab98feb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 5-[2-hydroxy-2,5,8a-trimethyl-5-(3-methylbut-2-enoyloxymethyl)-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpentanoic acid
• SMILES (Canonical): CC(CCC1C2(CCCC(C2CCC1(C)O)(C)COC(=O)C=C(C)C)C)CC(=O)O
• SMILES (Isomeric): CC(CCC1C2(CCCC(C2CCC1(C)O)(C)COC(=O)C=C(C)C)C)CC(=O)O
• InChI: InChI=1S/C25H42O5/c1-17(2)14-22(28)30-16-23(4)11-7-12-24(5)19(23)10-13-25(6,29)20(24)9-8-18(3)15-21(26)27/h14,18-20,29H,7-13,15-16H2,1-6H3,(H,26,27)
• InChI Key: ZQCLFYPJCVYMSK-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₄₂O₅
• Molecular Weight: 422.60 g/mol
• Exact Mass: 422.30322444 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 5.36
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9909	99.09%
Caco-2	+	0.5116	51.16%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.9229	92.29%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8703	87.03%
OATP1B3 inhibitior	+	0.8218	82.18%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6275	62.75%
BSEP inhibitior	+	0.7853	78.53%
P-glycoprotein inhibitior	-	0.4664	46.64%
P-glycoprotein substrate	-	0.6496	64.96%
CYP3A4 substrate	+	0.6617	66.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9225	92.25%
CYP3A4 inhibition	-	0.7447	74.47%
CYP2C9 inhibition	-	0.8449	84.49%
CYP2C19 inhibition	-	0.9322	93.22%
CYP2D6 inhibition	-	0.9365	93.65%
CYP1A2 inhibition	-	0.8926	89.26%
CYP2C8 inhibition	-	0.7016	70.16%
CYP inhibitory promiscuity	-	0.8555	85.55%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7030	70.30%
Eye corrosion	-	0.9943	99.43%
Eye irritation	-	0.9146	91.46%
Skin irritation	-	0.5322	53.22%
Skin corrosion	-	0.9758	97.58%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6093	60.93%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6606	66.06%
skin sensitisation	-	0.7333	73.33%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.8203	82.03%
Acute Oral Toxicity (c)	III	0.7430	74.30%
Estrogen receptor binding	+	0.8151	81.51%
Androgen receptor binding	+	0.5544	55.44%
Thyroid receptor binding	+	0.5195	51.95%
Glucocorticoid receptor binding	+	0.7628	76.28%
Aromatase binding	+	0.7020	70.20%
PPAR gamma	+	0.7396	73.96%
Honey bee toxicity	-	0.8012	80.12%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6955	69.55%
Fish aquatic toxicity	+	0.9972	99.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.40%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.81%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.61%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	94.59%	90.17%
CHEMBL2581	P07339	Cathepsin D	94.13%	98.95%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.97%	96.38%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.35%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	90.91%	91.19%
CHEMBL237	P41145	Kappa opioid receptor	87.51%	98.10%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.20%	94.62%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.15%	100.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.67%	89.05%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.23%	94.08%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.41%	97.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.08%	96.47%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.85%	95.50%
CHEMBL5255	O00206	Toll-like receptor 4	83.64%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.49%	95.89%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	83.16%	96.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.89%	82.69%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.35%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.10%	96.61%
CHEMBL268	P43235	Cathepsin K	80.82%	96.85%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.23%	96.00%

Plants that contains it

• Olearia teretifolia

Cross-Links

• PubChem: 163017774
• LOTUS: LTS0247551
• wikiData: Q105381396