Genipin 10-acetate

Details

• Internal ID: 1ad5ce03-7ea1-47fd-a14b-23189f514e41
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: methyl (1R,4aS,7aS)-7-(acetyloxymethyl)-1-hydroxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC(=O)OCC1=CCC2C1C(OC=C2C(=O)OC)O
• SMILES (Isomeric): CC(=O)OCC1=CC[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O
• InChI: InChI=1S/C13H16O6/c1-7(14)18-5-8-3-4-9-10(12(15)17-2)6-19-13(16)11(8)9/h3,6,9,11,13,16H,4-5H2,1-2H3/t9-,11-,13-/m1/s1
• InChI Key: WPMOWKGFSAAGQM-IRUJWGPZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₆O₆
• Molecular Weight: 268.26 g/mol
• Exact Mass: 268.09468823 g/mol
• Topological Polar Surface Area (TPSA): 82.10 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.52
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• CHEMBL449456
• SCHEMBL10042296

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9687	96.87%
Caco-2	-	0.6041	60.41%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7020	70.20%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8590	85.90%
OATP1B3 inhibitior	+	0.9583	95.83%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7917	79.17%
P-glycoprotein inhibitior	-	0.9253	92.53%
P-glycoprotein substrate	-	0.7584	75.84%
CYP3A4 substrate	+	0.5903	59.03%
CYP2C9 substrate	-	0.8065	80.65%
CYP2D6 substrate	-	0.8813	88.13%
CYP3A4 inhibition	-	0.7855	78.55%
CYP2C9 inhibition	-	0.8201	82.01%
CYP2C19 inhibition	-	0.7984	79.84%
CYP2D6 inhibition	-	0.8811	88.11%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	-	0.6153	61.53%
CYP inhibitory promiscuity	-	0.8202	82.02%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.7845	78.45%
Eye corrosion	-	0.9285	92.85%
Eye irritation	-	0.7580	75.80%
Skin irritation	-	0.6970	69.70%
Skin corrosion	-	0.9518	95.18%
Ames mutagenesis	-	0.5337	53.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6011	60.11%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.5466	54.66%
skin sensitisation	-	0.8037	80.37%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.8838	88.38%
Acute Oral Toxicity (c)	III	0.4424	44.24%
Estrogen receptor binding	-	0.4902	49.02%
Androgen receptor binding	-	0.5227	52.27%
Thyroid receptor binding	-	0.6614	66.14%
Glucocorticoid receptor binding	-	0.5411	54.11%
Aromatase binding	-	0.6778	67.78%
PPAR gamma	-	0.8216	82.16%
Honey bee toxicity	-	0.8659	86.59%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9707	97.07%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.76%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.09%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.04%	99.17%
CHEMBL4040	P28482	MAP kinase ERK2	88.84%	83.82%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.20%	96.95%
CHEMBL3401	O75469	Pregnane X receptor	86.06%	94.73%
CHEMBL2581	P07339	Cathepsin D	84.18%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.18%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.51%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.29%	94.45%
CHEMBL4208	P20618	Proteasome component C5	82.23%	90.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.99%	97.21%
CHEMBL340	P08684	Cytochrome P450 3A4	80.62%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.22%	86.33%

Plants that contains it

• Apodytes dimidiata

Cross-Links

• PubChem: 15139573
• LOTUS: LTS0169074
• wikiData: Q105310045