(Z)-5-[(1R,4aR,7R,8aR)-7-methoxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid

Details

• Internal ID: cbe8d3d5-ecf3-48c6-bf2b-9aa85ef4f487
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (Z)-5-[(1R,4aR,7R,8aR)-7-methoxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid
• SMILES (Canonical): CC(=O)OCC(=CC(=O)O)CCC1C(=C)CCC2C1(CC(CC2(C)C)OC)C
• SMILES (Isomeric): CC(=O)OC/C(=C\C(=O)O)/CC[C@@H]1C(=C)CC[C@H]2[C@]1(C[C@@H](CC2(C)C)OC)C
• InChI: InChI=1S/C23H36O5/c1-15-7-10-20-22(3,4)12-18(27-6)13-23(20,5)19(15)9-8-17(11-21(25)26)14-28-16(2)24/h11,18-20H,1,7-10,12-14H2,2-6H3,(H,25,26)/b17-11-/t18-,19-,20-,23+/m1/s1
• InChI Key: DJQKFSICWYZNNP-QBNDNERMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₆O₅
• Molecular Weight: 392.50 g/mol
• Exact Mass: 392.25627424 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.76
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9814	98.14%
Caco-2	-	0.5303	53.03%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8992	89.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8510	85.10%
OATP1B3 inhibitior	+	0.7891	78.91%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.7492	74.92%
P-glycoprotein inhibitior	+	0.5854	58.54%
P-glycoprotein substrate	-	0.6575	65.75%
CYP3A4 substrate	+	0.6533	65.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9125	91.25%
CYP3A4 inhibition	-	0.6044	60.44%
CYP2C9 inhibition	-	0.7772	77.72%
CYP2C19 inhibition	-	0.8349	83.49%
CYP2D6 inhibition	-	0.9342	93.42%
CYP1A2 inhibition	-	0.7232	72.32%
CYP2C8 inhibition	+	0.5880	58.80%
CYP inhibitory promiscuity	-	0.8599	85.99%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9120	91.20%
Carcinogenicity (trinary)	Non-required	0.6949	69.49%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.8441	84.41%
Skin irritation	-	0.5768	57.68%
Skin corrosion	-	0.9756	97.56%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3973	39.73%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.6976	69.76%
skin sensitisation	-	0.7523	75.23%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.4620	46.20%
Acute Oral Toxicity (c)	III	0.8376	83.76%
Estrogen receptor binding	+	0.7486	74.86%
Androgen receptor binding	+	0.6537	65.37%
Thyroid receptor binding	+	0.6769	67.69%
Glucocorticoid receptor binding	+	0.8096	80.96%
Aromatase binding	+	0.7487	74.87%
PPAR gamma	+	0.6767	67.67%
Honey bee toxicity	-	0.7943	79.43%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6555	65.55%
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	96.60%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.27%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.28%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.64%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	90.11%	91.49%
CHEMBL340	P08684	Cytochrome P450 3A4	86.58%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.33%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.61%	100.00%
CHEMBL5028	O14672	ADAM10	82.16%	97.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.80%	94.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.28%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.59%	86.33%

Plants that contains it

• Leiocarpa semicalva

Cross-Links

• PubChem: 162889072
• LOTUS: LTS0198642
• wikiData: Q104982635