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5-Hydroxycastavinol

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 ab9d367d-5b59-4a39-9cb9-4b884a67ca74
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins > Epigallocatechins
IUPAC Name 1-[(1S,9S,12R)-9-(3,4-dihydroxy-5-methoxyphenyl)-3,5-dihydroxy-11-methyl-12-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8,10-dioxatricyclo[7.2.1.02,7]dodeca-2,4,6-trien-11-yl]ethanone
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C26H30O14/c1-9(28)25(2)18-17-12(30)6-11(29)7-14(17)39-26(40-25,10-4-13(31)19(32)15(5-10)36-3)23(18)38-24-22(35)21(34)20(33)16(8-27)37-24/h4-7,16,18,20-24,27,29-35H,8H2,1-3H3/t16-,18+,20-,21+,22-,23-,24+,25?,26+/m1/s1
InChI Key ADFRCNLBRJARNV-MHDKHVFCSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C26H30O14
Molecular Weight 566.50 g/mol
Exact Mass 566.16355563 g/mol
Topological Polar Surface Area (TPSA) 225.00 Ų
XlogP -0.90
Atomic LogP (AlogP) -0.59
H-Bond Acceptor 14
H-Bond Donor 8
Rotatable Bonds 6

Synonyms

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ZHZ5SCW9G9
Castavinol C3
183607-17-2
UNII-ZHZ5SCW9G9
1-((2S,5S,10R)-2-(3,4-DIHYDROXY-5-METHOXYPHENYL)-10-(.BETA.-D-GLUCOPYRANOSYLOXY)-4,5-DIHYDRO-6,8-DIHYDROXY-4-METHYL-2,5-METHANO-1,3-BENZODIOXEPIN-4-YL)ETHANONE
1-((2S,5S,10R)-2-(3,4-Dihydroxy-5-methoxyphenyl)-10-(beta-D-glucopyranosyloxy)-4,5-dihydro-6,8-dihydroxy-4-methyl-2,5-methano-1,3-benzodioxepin-4-yl)ethanone
ETHANONE, 1-((2S,5S,10R)-2-(3,4-DIHYDROXY-5-METHOXYPHENYL)-10-(.BETA.-D-GLUCOPYRANOSYLOXY)-4,5-DIHYDRO-6,8-DIHYDROXY-4-METHYL-2,5-METHANO-1,3-BENZODIOXEPIN-4-YL)-
Ethanone, 1-((2S,5S,10R)-2-(3,4-dihydroxy-5-methoxyphenyl)-10-(beta-D-glucopyranosyloxy)-4,5-dihydro-6,8-dihydroxy-4-methyl-2,5-methano-1,3-benzodioxepin-4-yl)-
ETHANONE, 1-(2-(3,4-DIHYDROXY-5-METHOXYPHENYL)-10-(.BETA.-D-GLUCOPYRANOSYLOXY)-4,5-DIHYDRO-6,8-DIHYDROXY-4-METHYL-2,5-METHANO-1,3-BENZODIOXEPIN-4-YL)-, (2S,5S,10R)-
Ethanone, 1-(2-(3,4-dihydroxy-5-methoxyphenyl)-10-(beta-D-glucopyranosyloxy)-4,5-dihydro-6,8-dihydroxy-4-methyl-2,5-methano-1,3-benzodioxepin-4-yl)-, (2S,5S,10R)-

2D Structure

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2D Structure of 5-Hydroxycastavinol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6667 66.67%
Caco-2 - 0.8443 84.43%
Blood Brain Barrier - 0.7500 75.00%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.6449 64.49%
OATP2B1 inhibitior - 0.8514 85.14%
OATP1B1 inhibitior + 0.8316 83.16%
OATP1B3 inhibitior + 0.9391 93.91%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.8581 85.81%
P-glycoprotein inhibitior - 0.4901 49.01%
P-glycoprotein substrate - 0.6077 60.77%
CYP3A4 substrate + 0.6741 67.41%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8354 83.54%
CYP3A4 inhibition - 0.7725 77.25%
CYP2C9 inhibition - 0.8879 88.79%
CYP2C19 inhibition - 0.8056 80.56%
CYP2D6 inhibition - 0.9335 93.35%
CYP1A2 inhibition - 0.8870 88.70%
CYP2C8 inhibition + 0.7177 71.77%
CYP inhibitory promiscuity - 0.6674 66.74%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5906 59.06%
Eye corrosion - 0.9892 98.92%
Eye irritation - 0.8967 89.67%
Skin irritation - 0.8135 81.35%
Skin corrosion - 0.9445 94.45%
Ames mutagenesis + 0.5009 50.09%
Human Ether-a-go-go-Related Gene inhibition + 0.6677 66.77%
Micronuclear + 0.6533 65.33%
Hepatotoxicity - 0.7000 70.00%
skin sensitisation - 0.8941 89.41%
Respiratory toxicity + 0.5111 51.11%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity + 0.6464 64.64%
Acute Oral Toxicity (c) III 0.5677 56.77%
Estrogen receptor binding + 0.7312 73.12%
Androgen receptor binding + 0.7044 70.44%
Thyroid receptor binding + 0.5470 54.70%
Glucocorticoid receptor binding + 0.6882 68.82%
Aromatase binding + 0.6529 65.29%
PPAR gamma + 0.6992 69.92%
Honey bee toxicity - 0.7092 70.92%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.8358 83.58%

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 99.76% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.62% 96.09%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 91.79% 94.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.33% 86.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.41% 99.17%
CHEMBL2581 P07339 Cathepsin D 89.96% 98.95%
CHEMBL4208 P20618 Proteasome component C5 87.67% 90.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 87.19% 96.00%
CHEMBL3401 O75469 Pregnane X receptor 86.70% 94.73%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 86.25% 92.62%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.30% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.24% 89.00%
CHEMBL3194 P02766 Transthyretin 82.72% 90.71%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.27% 97.14%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.82% 95.50%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 80.73% 95.56%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.47% 91.07%

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.
Vitis vinifera

Cross-Links

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PubChem 102002905
LOTUS LTS0247444
wikiData Q104909546