[(1S,3S,8aS)-5-hydroxy-8a-(3-methoxy-3-oxoprop-1-en-2-yl)-3,6-dimethyl-4,8-dioxo-2,3-dihydro-1H-naphthalen-1-yl] 2-(hydroxymethyl)prop-2-enoate

Details

• Internal ID: 53879640-4ce6-4a31-8c32-08681af1690f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1S,3S,8aS)-5-hydroxy-8a-(3-methoxy-3-oxoprop-1-en-2-yl)-3,6-dimethyl-4,8-dioxo-2,3-dihydro-1H-naphthalen-1-yl] 2-(hydroxymethyl)prop-2-enoate
• SMILES (Canonical): CC1CC(C2(C(=O)C=C(C(=C2C1=O)O)C)C(=C)C(=O)OC)OC(=O)C(=C)CO
• SMILES (Isomeric): C[C@H]1C[C@@H]([C@@]2(C(=O)C=C(C(=C2C1=O)O)C)C(=C)C(=O)OC)OC(=O)C(=C)CO
• InChI: InChI=1S/C20H22O8/c1-9-6-13(22)20(12(4)19(26)27-5)14(28-18(25)11(3)8-21)7-10(2)17(24)15(20)16(9)23/h6,10,14,21,23H,3-4,7-8H2,1-2,5H3/t10-,14-,20-/m0/s1
• InChI Key: XJLPDLMDYAPGTC-YOKVUHJFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₈
• Molecular Weight: 390.40 g/mol
• Exact Mass: 390.13146766 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.11
• H-Bond Acceptor: 8
• 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	+	0.9846	98.46%
Caco-2	-	0.6241	62.41%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7829	78.29%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8705	87.05%
OATP1B3 inhibitior	+	0.8748	87.48%
MATE1 inhibitior	-	0.6600	66.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7053	70.53%
P-glycoprotein inhibitior	-	0.7226	72.26%
P-glycoprotein substrate	+	0.5430	54.30%
CYP3A4 substrate	+	0.6496	64.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9016	90.16%
CYP3A4 inhibition	-	0.6509	65.09%
CYP2C9 inhibition	-	0.8447	84.47%
CYP2C19 inhibition	-	0.7902	79.02%
CYP2D6 inhibition	-	0.9209	92.09%
CYP1A2 inhibition	-	0.7426	74.26%
CYP2C8 inhibition	-	0.6925	69.25%
CYP inhibitory promiscuity	-	0.8187	81.87%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8613	86.13%
Carcinogenicity (trinary)	Non-required	0.6020	60.20%
Eye corrosion	-	0.9820	98.20%
Eye irritation	-	0.8790	87.90%
Skin irritation	-	0.6968	69.68%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7638	76.38%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.5139	51.39%
skin sensitisation	-	0.7237	72.37%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.5370	53.70%
Acute Oral Toxicity (c)	III	0.6212	62.12%
Estrogen receptor binding	+	0.6005	60.05%
Androgen receptor binding	+	0.5421	54.21%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6672	66.72%
Aromatase binding	-	0.5322	53.22%
PPAR gamma	+	0.6030	60.30%
Honey bee toxicity	-	0.8168	81.68%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9668	96.68%

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	97.90%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.93%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.79%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.20%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	86.76%	91.19%
CHEMBL2581	P07339	Cathepsin D	86.70%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.32%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.27%	96.95%
CHEMBL3437	Q16853	Amine oxidase, copper containing	83.00%	94.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.81%	97.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.47%	86.33%

Plants that contains it

• Ambassa hochstetteri

Cross-Links

• PubChem: 15109142
• LOTUS: LTS0003809
• wikiData: Q105329027