((1S,5R,6S)-5-(Benzoyloxy)-1,6-dihydroxy-2-oxocyclohex-3-en-1-yl)methyl benzoate

Details

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Internal ID a9fcb3fb-6d49-4421-af5c-50d2fb62a953
Taxonomy Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Benzoic acid esters
IUPAC Name [(1S,5R,6S)-5-benzoyloxy-1,6-dihydroxy-2-oxocyclohex-3-en-1-yl]methyl benzoate
SMILES (Canonical) C1=CC=C(C=C1)C(=O)OCC2(C(C(C=CC2=O)OC(=O)C3=CC=CC=C3)O)O
SMILES (Isomeric) C1=CC=C(C=C1)C(=O)OC[C@@]2([C@H]([C@@H](C=CC2=O)OC(=O)C3=CC=CC=C3)O)O
InChI InChI=1S/C21H18O7/c22-17-12-11-16(28-20(25)15-9-5-2-6-10-15)18(23)21(17,26)13-27-19(24)14-7-3-1-4-8-14/h1-12,16,18,23,26H,13H2/t16-,18+,21-/m1/s1
InChI Key UUNZIGRBVXAOSR-PLMTUMEDSA-N
Popularity 14 references in papers

Physical and Chemical Properties

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Molecular Formula C21H18O7
Molecular Weight 382.40 g/mol
Exact Mass 382.10525291 g/mol
Topological Polar Surface Area (TPSA) 110.00 Ų
XlogP 1.90
Atomic LogP (AlogP) 1.30
H-Bond Acceptor 7
H-Bond Donor 2
Rotatable Bonds 5

Synonyms

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193410-84-3
((1S,5R,6S)-5-(Benzoyloxy)-1,6-dihydroxy-2-oxocyclohex-3-en-1-yl)methyl benzoate
(4R,5S,6S)-4-(Benzoyloxy)-6-[(benzoyloxy)methyl]-5,6-dihydroxy-,2-cyclohexen-1-one
[(1S,5R,6S)-5-benzoyloxy-1,6-dihydroxy-2-oxocyclohex-3-en-1-yl]methyl benzoate
[(1S,5R,6S)-5-(Benzoyloxy)-1,6-dihydroxy-2-oxocyclohex-3-en-1-yl]methyl benzoate
CHEMBL4468212
DTXSID90441923
HY-N2051
AKOS016010697
MS-26261
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of ((1S,5R,6S)-5-(Benzoyloxy)-1,6-dihydroxy-2-oxocyclohex-3-en-1-yl)methyl benzoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9113 91.13%
Caco-2 - 0.8332 83.32%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.8790 87.90%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9227 92.27%
OATP1B3 inhibitior + 0.9341 93.41%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior - 0.6870 68.70%
P-glycoprotein inhibitior - 0.5990 59.90%
P-glycoprotein substrate - 0.8770 87.70%
CYP3A4 substrate + 0.5408 54.08%
CYP2C9 substrate - 0.8019 80.19%
CYP2D6 substrate - 0.8775 87.75%
CYP3A4 inhibition - 0.9315 93.15%
CYP2C9 inhibition - 0.8938 89.38%
CYP2C19 inhibition - 0.8930 89.30%
CYP2D6 inhibition - 0.9384 93.84%
CYP1A2 inhibition - 0.8566 85.66%
CYP2C8 inhibition - 0.5732 57.32%
CYP inhibitory promiscuity - 0.9564 95.64%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.8632 86.32%
Carcinogenicity (trinary) Non-required 0.6557 65.57%
Eye corrosion - 0.9939 99.39%
Eye irritation - 0.7045 70.45%
Skin irritation - 0.8177 81.77%
Skin corrosion - 0.9540 95.40%
Ames mutagenesis - 0.8200 82.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7369 73.69%
Micronuclear + 0.5851 58.51%
Hepatotoxicity - 0.6250 62.50%
skin sensitisation - 0.6288 62.88%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.5667 56.67%
Mitochondrial toxicity - 0.5500 55.00%
Nephrotoxicity - 0.6345 63.45%
Acute Oral Toxicity (c) III 0.7497 74.97%
Estrogen receptor binding + 0.6482 64.82%
Androgen receptor binding + 0.5720 57.20%
Thyroid receptor binding - 0.6123 61.23%
Glucocorticoid receptor binding - 0.4825 48.25%
Aromatase binding - 0.5518 55.18%
PPAR gamma - 0.5488 54.88%
Honey bee toxicity - 0.8948 89.48%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9763 97.63%

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
CHEMBL221 P23219 Cyclooxygenase-1 96.96% 90.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.18% 86.33%
CHEMBL2581 P07339 Cathepsin D 90.19% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 89.89% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.22% 95.56%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 89.03% 94.62%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.23% 96.09%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 87.48% 94.23%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.97% 99.23%
CHEMBL5028 O14672 ADAM10 80.62% 97.50%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 80.02% 83.00%

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.
Uvaria grandiflora

Cross-Links

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PubChem 10571940
LOTUS LTS0254099
wikiData Q72516831