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(1S,4aS,6S,7R,7aS)-1-[(2S,3R,4S,5S,6R)-3-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 692e0b11-aa3e-4bc4-bfae-acda30ccdca7
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name (1S,4aS,6S,7R,7aS)-1-[(2S,3R,4S,5S,6R)-3-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
SMILES (Canonical) CC1C(CC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)OC(=O)C=CC4=CC(=C(C=C4)OC)OC)O
SMILES (Isomeric) C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC(=O)/C=C/C4=CC(=C(C=C4)OC)OC)O
InChI InChI=1S/C27H34O13/c1-12-16(29)9-14-15(25(33)34)11-37-26(21(12)14)40-27-24(23(32)22(31)19(10-28)38-27)39-20(30)7-5-13-4-6-17(35-2)18(8-13)36-3/h4-8,11-12,14,16,19,21-24,26-29,31-32H,9-10H2,1-3H3,(H,33,34)/b7-5+/t12-,14+,16-,19+,21+,22+,23-,24+,26-,27-/m0/s1
InChI Key KVCCHIDBNDFTEZ-NPDXYTPCSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C27H34O13
Molecular Weight 566.50 g/mol
Exact Mass 566.19994113 g/mol
Topological Polar Surface Area (TPSA) 191.00 Ų
XlogP 0.90
Atomic LogP (AlogP) 0.04
H-Bond Acceptor 12
H-Bond Donor 5
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,4aS,6S,7R,7aS)-1-[(2S,3R,4S,5S,6R)-3-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8132 81.32%
Caco-2 - 0.8691 86.91%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.4452 44.52%
OATP2B1 inhibitior - 0.8620 86.20%
OATP1B1 inhibitior - 0.3598 35.98%
OATP1B3 inhibitior + 0.9431 94.31%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.5834 58.34%
P-glycoprotein inhibitior - 0.5000 50.00%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.6555 65.55%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8725 87.25%
CYP3A4 inhibition - 0.8627 86.27%
CYP2C9 inhibition - 0.8422 84.22%
CYP2C19 inhibition - 0.8710 87.10%
CYP2D6 inhibition - 0.8792 87.92%
CYP1A2 inhibition - 0.7430 74.30%
CYP2C8 inhibition + 0.6840 68.40%
CYP inhibitory promiscuity - 0.8424 84.24%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7068 70.68%
Eye corrosion - 0.9901 99.01%
Eye irritation - 0.9417 94.17%
Skin irritation - 0.7587 75.87%
Skin corrosion - 0.9457 94.57%
Ames mutagenesis - 0.5523 55.23%
Human Ether-a-go-go-Related Gene inhibition + 0.7137 71.37%
Micronuclear - 0.5600 56.00%
Hepatotoxicity - 0.6716 67.16%
skin sensitisation - 0.8415 84.15%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity - 0.9688 96.88%
Acute Oral Toxicity (c) III 0.4738 47.38%
Estrogen receptor binding + 0.7846 78.46%
Androgen receptor binding + 0.5618 56.18%
Thyroid receptor binding + 0.5254 52.54%
Glucocorticoid receptor binding + 0.6400 64.00%
Aromatase binding - 0.5509 55.09%
PPAR gamma + 0.6254 62.54%
Honey bee toxicity - 0.7798 77.98%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.7000 70.00%
Fish aquatic toxicity + 0.9001 90.01%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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 98.46% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 97.43% 96.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.05% 86.33%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.43% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.88% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.64% 97.09%
CHEMBL4208 P20618 Proteasome component C5 92.69% 90.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.65% 95.56%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.75% 99.17%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 89.16% 86.92%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 88.46% 93.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 87.09% 95.50%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 86.75% 89.62%
CHEMBL241 Q14432 Phosphodiesterase 3A 85.87% 92.94%
CHEMBL3401 O75469 Pregnane X receptor 85.53% 94.73%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 82.71% 96.95%
CHEMBL3194 P02766 Transthyretin 80.12% 90.71%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Chiococca alba

Cross-Links

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PubChem 10721690
LOTUS LTS0090611
wikiData Q105146453