Enterocin

Details

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Internal ID e49130a9-2579-4fb5-8b13-a56507b7a48d
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
IUPAC Name (1S,2S,3S,6R,8R,9S,10R)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.03,8]decan-4-one
SMILES (Canonical) COC1=CC(=O)OC(=C1)C2C3(CC4C(C2(C(C3(C(=O)O4)O)C(=O)C5=CC=CC=C5)O)O)O
SMILES (Isomeric) COC1=CC(=O)OC(=C1)[C@@H]2[C@@]3(C[C@@H]4[C@H]([C@]2([C@@H]([C@]3(C(=O)O4)O)C(=O)C5=CC=CC=C5)O)O)O
InChI InChI=1S/C22H20O10/c1-30-11-7-12(31-14(23)8-11)16-20(27)9-13-18(25)21(16,28)17(22(20,29)19(26)32-13)15(24)10-5-3-2-4-6-10/h2-8,13,16-18,25,27-29H,9H2,1H3/t13-,16-,17+,18-,20-,21+,22-/m1/s1
InChI Key CTBBEXWJRAPJIZ-VHPBLNRZSA-N
Popularity 136 references in papers

Physical and Chemical Properties

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Molecular Formula C22H20O10
Molecular Weight 444.40 g/mol
Exact Mass 444.10564683 g/mol
Topological Polar Surface Area (TPSA) 160.00 Ų
XlogP -0.90
Atomic LogP (AlogP) -0.87
H-Bond Acceptor 10
H-Bond Donor 4
Rotatable Bonds 4

Synonyms

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Vulgamycin
59678-46-5
2M8WGY5QPQ
3,6-Methanocyclopenta(c)pyran-1(3H)-one, 7-benzoylhexahydro-4a,6,7a,8-tetrahydroxy-5-(4-methoxy-2-oxo-2H-pyran-6-yl)-, (3R,4aR,5S,6S,7S,7aS,8R)-
HY-121347
(3R,4AR,5S,6S,7S,7AS,8R)-7-BENZOYLHEXAHYDRO-4A,6,7A,8-TETRAHYDROXY-5-(4-METHOXY-2-OXO-2H-PYRAN-6-YL)-3,6-METHANOCYCLOPENTA(C)PYRAN-1(3H)-ONE
3,6-METHANOCYCLOPENTA(C)PYRAN-1(3H)-ONE, 7-BENZOYLHEXAHYDRO-4A,6,7A,8-TETRAHYDROXY-5-(4-METHOXY-2-OXO-2H-PYRAN-6-YL)-, (3R-(3.ALPHA.,4A.BETA.,5.ALPHA.,6.BETA.,7.BETA.,7A.BETA.,8R*))-

2D Structure

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2D Structure of Enterocin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7091 70.91%
Caco-2 - 0.7967 79.67%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.5506 55.06%
OATP2B1 inhibitior - 0.5741 57.41%
OATP1B1 inhibitior + 0.8974 89.74%
OATP1B3 inhibitior + 0.9721 97.21%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior - 0.7586 75.86%
P-glycoprotein inhibitior - 0.4677 46.77%
P-glycoprotein substrate - 0.6287 62.87%
CYP3A4 substrate + 0.6061 60.61%
CYP2C9 substrate + 0.8041 80.41%
CYP2D6 substrate - 0.8411 84.11%
CYP3A4 inhibition - 0.5250 52.50%
CYP2C9 inhibition - 0.9341 93.41%
CYP2C19 inhibition - 0.7835 78.35%
CYP2D6 inhibition - 0.8901 89.01%
CYP1A2 inhibition - 0.9501 95.01%
CYP2C8 inhibition - 0.5694 56.94%
CYP inhibitory promiscuity - 0.9583 95.83%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4197 41.97%
Eye corrosion - 0.9893 98.93%
Eye irritation - 0.9056 90.56%
Skin irritation - 0.7447 74.47%
Skin corrosion - 0.9138 91.38%
Ames mutagenesis + 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6081 60.81%
Micronuclear + 0.7359 73.59%
Hepatotoxicity - 0.5000 50.00%
skin sensitisation - 0.9006 90.06%
Respiratory toxicity + 0.6444 64.44%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity + 0.5510 55.10%
Acute Oral Toxicity (c) III 0.4624 46.24%
Estrogen receptor binding + 0.8117 81.17%
Androgen receptor binding + 0.7814 78.14%
Thyroid receptor binding - 0.5351 53.51%
Glucocorticoid receptor binding + 0.6130 61.30%
Aromatase binding + 0.5920 59.20%
PPAR gamma + 0.7118 71.18%
Honey bee toxicity - 0.8688 86.88%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.8161 81.61%

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 95.60% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.33% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.63% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 91.43% 99.23%
CHEMBL4208 P20618 Proteasome component C5 90.16% 90.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 88.63% 97.14%
CHEMBL2535 P11166 Glucose transporter 87.57% 98.75%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 87.19% 91.07%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 86.43% 95.50%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 85.94% 96.09%
CHEMBL340 P08684 Cytochrome P450 3A4 84.47% 91.19%
CHEMBL2581 P07339 Cathepsin D 84.00% 98.95%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 83.72% 85.14%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.63% 94.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.56% 95.89%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 80.38% 93.00%

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.
Carpesium abrotanoides
Simmondsia chinensis

Cross-Links

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PubChem 23654446
NPASS NPC69989
LOTUS LTS0071771
wikiData Q105146496