(1S)-1alpha-[6-O-(3,5-Dimethoxy-4-hydroxy-trans-cinnamoyl)-beta-D-glucopyranosyloxy]-6alpha-hydroxy-7-methylene-1,4aalpha,5,6,7,7aalpha-hexahydrocyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 4c0c59fe-b911-4ba6-818b-0b15b6007980
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: (1S,4aS,6S,7aS)-6-hydroxy-7-methylidene-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C=CC(=O)OCC2C(C(C(C(O2)OC3C4C(CC(C4=C)O)C(=CO3)C(=O)O)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@H]3[C@H]4[C@H](C[C@@H](C4=C)O)C(=CO3)C(=O)O)O)O)O
• InChI: InChI=1S/C27H32O14/c1-11-15(28)8-13-14(25(34)35)9-39-26(20(11)13)41-27-24(33)23(32)22(31)18(40-27)10-38-19(29)5-4-12-6-16(36-2)21(30)17(7-12)37-3/h4-7,9,13,15,18,20,22-24,26-28,30-33H,1,8,10H2,2-3H3,(H,34,35)/b5-4+/t13-,15+,18-,20-,22-,23+,24-,26+,27+/m1/s1
• InChI Key: QTVCLHJYLZANIP-QRXPZTDPSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₁₄
• Molecular Weight: 580.50 g/mol
• Exact Mass: 580.17920569 g/mol
• Topological Polar Surface Area (TPSA): 211.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.33
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

• NCGC00385466-01_C27H32O14_(1S,4aS,6S,7aS)-6-Hydroxy-1-({6-O-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-propenoyl]-beta-D-glucopyranosyl}oxy)-7-methylene-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7413	74.13%
Caco-2	-	0.8931	89.31%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5302	53.02%
OATP2B1 inhibitior	-	0.7235	72.35%
OATP1B1 inhibitior	+	0.7334	73.34%
OATP1B3 inhibitior	+	0.9585	95.85%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8598	85.98%
P-glycoprotein inhibitior	-	0.4526	45.26%
P-glycoprotein substrate	-	0.5389	53.89%
CYP3A4 substrate	+	0.6559	65.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8608	86.08%
CYP3A4 inhibition	-	0.6616	66.16%
CYP2C9 inhibition	-	0.7344	73.44%
CYP2C19 inhibition	-	0.6834	68.34%
CYP2D6 inhibition	-	0.8310	83.10%
CYP1A2 inhibition	-	0.8034	80.34%
CYP2C8 inhibition	+	0.7211	72.11%
CYP inhibitory promiscuity	-	0.7626	76.26%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6972	69.72%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9169	91.69%
Skin irritation	-	0.7667	76.67%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4399	43.99%
Micronuclear	+	0.6192	61.92%
Hepatotoxicity	-	0.7341	73.41%
skin sensitisation	-	0.7676	76.76%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7949	79.49%
Acute Oral Toxicity (c)	III	0.5034	50.34%
Estrogen receptor binding	+	0.7901	79.01%
Androgen receptor binding	+	0.6437	64.37%
Thyroid receptor binding	+	0.5282	52.82%
Glucocorticoid receptor binding	+	0.6916	69.16%
Aromatase binding	+	0.5550	55.50%
PPAR gamma	+	0.6853	68.53%
Honey bee toxicity	-	0.7548	75.48%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9452	94.52%

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	98.70%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.14%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.50%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.45%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.26%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.16%	95.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.21%	89.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.57%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.88%	96.61%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.58%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.59%	92.94%
CHEMBL3401	O75469	Pregnane X receptor	86.23%	94.73%
CHEMBL3194	P02766	Transthyretin	85.82%	90.71%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.35%	97.21%
CHEMBL5255	O00206	Toll-like receptor 4	85.19%	92.50%
CHEMBL340	P08684	Cytochrome P450 3A4	84.15%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	83.18%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.83%	95.89%
CHEMBL4208	P20618	Proteasome component C5	81.92%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.70%	90.71%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	81.36%	98.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.83%	96.95%

Plants that contains it

• Gardenia jasminoides

Cross-Links

• PubChem: 71694459
• LOTUS: LTS0226620
• wikiData: Q105227944