7-[(3,4-dihydroxybenzoyl)oxymethyl]-5-oxo-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylic acid

Details

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Internal ID 46457d40-27a1-4050-9b7f-d854ca404d99
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name 7-[(3,4-dihydroxybenzoyl)oxymethyl]-5-oxo-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylic acid
SMILES (Canonical) C1=CC(=C(C=C1C(=O)OCC2=CC(=O)C3C2C(OC=C3C(=O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O
SMILES (Isomeric) C1=CC(=C(C=C1C(=O)OCC2=CC(=O)C3C2C(OC=C3C(=O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O
InChI InChI=1S/C23H24O14/c24-5-14-17(28)18(29)19(30)23(36-14)37-22-15-9(4-13(27)16(15)10(7-35-22)20(31)32)6-34-21(33)8-1-2-11(25)12(26)3-8/h1-4,7,14-19,22-26,28-30H,5-6H2,(H,31,32)
InChI Key SVQMRBGQJXPRDR-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C23H24O14
Molecular Weight 524.40 g/mol
Exact Mass 524.11660544 g/mol
Topological Polar Surface Area (TPSA) 230.00 Ų
XlogP -2.00
Atomic LogP (AlogP) -1.86
H-Bond Acceptor 13
H-Bond Donor 7
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 7-[(3,4-dihydroxybenzoyl)oxymethyl]-5-oxo-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[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 + 0.5933 59.33%
Caco-2 - 0.9450 94.50%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.5554 55.54%
OATP2B1 inhibitior - 0.8414 84.14%
OATP1B1 inhibitior + 0.7909 79.09%
OATP1B3 inhibitior + 0.9691 96.91%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior - 0.5192 51.92%
P-glycoprotein inhibitior - 0.6097 60.97%
P-glycoprotein substrate - 0.7589 75.89%
CYP3A4 substrate + 0.6090 60.90%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8775 87.75%
CYP3A4 inhibition - 0.8942 89.42%
CYP2C9 inhibition - 0.7734 77.34%
CYP2C19 inhibition - 0.6638 66.38%
CYP2D6 inhibition - 0.8758 87.58%
CYP1A2 inhibition - 0.8269 82.69%
CYP2C8 inhibition + 0.7037 70.37%
CYP inhibitory promiscuity - 0.6621 66.21%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6830 68.30%
Eye corrosion - 0.9895 98.95%
Eye irritation - 0.9198 91.98%
Skin irritation - 0.7976 79.76%
Skin corrosion - 0.9503 95.03%
Ames mutagenesis + 0.5100 51.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5329 53.29%
Micronuclear + 0.5233 52.33%
Hepatotoxicity - 0.6467 64.67%
skin sensitisation - 0.7816 78.16%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.8222 82.22%
Mitochondrial toxicity + 0.6875 68.75%
Nephrotoxicity + 0.6576 65.76%
Acute Oral Toxicity (c) III 0.4020 40.20%
Estrogen receptor binding + 0.7666 76.66%
Androgen receptor binding + 0.6863 68.63%
Thyroid receptor binding - 0.5114 51.14%
Glucocorticoid receptor binding - 0.5254 52.54%
Aromatase binding - 0.5926 59.26%
PPAR gamma + 0.6542 65.42%
Honey bee toxicity - 0.7448 74.48%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.7250 72.50%
Fish aquatic toxicity + 0.8958 89.58%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.46% 91.11%
CHEMBL3194 P02766 Transthyretin 94.20% 90.71%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.32% 86.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 92.97% 99.17%
CHEMBL220 P22303 Acetylcholinesterase 90.90% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.60% 89.00%
CHEMBL2581 P07339 Cathepsin D 87.16% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 84.91% 95.56%
CHEMBL1951 P21397 Monoamine oxidase A 83.12% 91.49%
CHEMBL5255 O00206 Toll-like receptor 4 82.12% 92.50%
CHEMBL340 P08684 Cytochrome P450 3A4 81.73% 91.19%
CHEMBL3401 O75469 Pregnane X receptor 81.71% 94.73%
CHEMBL3891 P07384 Calpain 1 81.52% 93.04%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.32% 97.09%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 81.05% 85.00%
CHEMBL4208 P20618 Proteasome component C5 80.87% 90.00%
CHEMBL226 P30542 Adenosine A1 receptor 80.49% 95.93%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.08% 99.23%

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.
Vitex negundo

Cross-Links

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PubChem 162885553
LOTUS LTS0191463
wikiData Q105262376