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(1R,5R,6R,13R,21R)-16-[(1R,5R,6R,7R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-6,9,17,19,21-pentahydroxy-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaen-7-yl]-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol

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 8da6e785-863e-4e76-87a0-e76e71d3d2e2
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
IUPAC Name (1R,5R,6R,13R,21R)-16-[(1R,5R,6R,7R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-6,9,17,19,21-pentahydroxy-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaen-7-yl]-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
SMILES (Canonical) C1C(C(OC2=C1C(=CC3=C2C4C(C(O3)(OC5=C(C(=CC(=C45)O)O)C6C(C(OC7=C6C(=CC8=C7C9C(C(O8)(OC1=CC(=CC(=C91)O)O)C1=CC(=C(C=C1)O)O)O)O)C1=CC(=C(C=C1)O)O)O)C1=CC(=C(C=C1)O)O)O)O)C1=CC(=C(C=C1)O)O)O
SMILES (Isomeric) C1[C@H]([C@H](OC2=C1C(=CC3=C2[C@@H]4[C@H]([C@](O3)(OC5=C(C(=CC(=C45)O)O)[C@@H]6[C@H]([C@H](OC7=C6C(=CC8=C7[C@@H]9[C@H]([C@](O8)(OC1=CC(=CC(=C91)O)O)C1=CC(=C(C=C1)O)O)O)O)C1=CC(=C(C=C1)O)O)O)C1=CC(=C(C=C1)O)O)O)O)C1=CC(=C(C=C1)O)O)O
InChI InChI=1S/C60H46O24/c61-23-13-34(71)42-39(14-23)81-59(21-3-7-27(64)32(69)11-21)57(77)49(42)47-41(82-59)18-37(74)43-48(51(76)53(80-55(43)47)20-2-6-26(63)31(68)10-20)44-35(72)16-36(73)45-50-46-40(83-60(58(50)78,84-56(44)45)22-4-8-28(65)33(70)12-22)17-29(66)24-15-38(75)52(79-54(24)46)19-1-5-25(62)30(67)9-19/h1-14,16-18,38,48-53,57-58,61-78H,15H2/t38-,48-,49-,50-,51-,52-,53-,57-,58-,59+,60-/m1/s1
InChI Key DAZIDFFBBZBZJN-IOHQHECRSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C60H46O24
Molecular Weight 1151.00 g/mol
Exact Mass 1150.23790233 g/mol
Topological Polar Surface Area (TPSA) 420.00 Ų
XlogP 4.30
Atomic LogP (AlogP) 5.49
H-Bond Acceptor 24
H-Bond Donor 18
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,5R,6R,13R,21R)-16-[(1R,5R,6R,7R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-6,9,17,19,21-pentahydroxy-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaen-7-yl]-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7002 70.02%
Caco-2 - 0.8682 86.82%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.5149 51.49%
OATP2B1 inhibitior - 0.7158 71.58%
OATP1B1 inhibitior + 0.9053 90.53%
OATP1B3 inhibitior + 0.8374 83.74%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.9409 94.09%
P-glycoprotein inhibitior + 0.7346 73.46%
P-glycoprotein substrate - 0.5601 56.01%
CYP3A4 substrate + 0.6660 66.60%
CYP2C9 substrate - 0.7965 79.65%
CYP2D6 substrate + 0.3672 36.72%
CYP3A4 inhibition - 0.9095 90.95%
CYP2C9 inhibition - 0.8939 89.39%
CYP2C19 inhibition - 0.8571 85.71%
CYP2D6 inhibition - 0.9488 94.88%
CYP1A2 inhibition - 0.9758 97.58%
CYP2C8 inhibition + 0.7881 78.81%
CYP inhibitory promiscuity - 0.9554 95.54%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6019 60.19%
Eye corrosion - 0.9909 99.09%
Eye irritation - 0.8957 89.57%
Skin irritation - 0.6303 63.03%
Skin corrosion - 0.9314 93.14%
Ames mutagenesis + 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8246 82.46%
Micronuclear + 0.7759 77.59%
Hepatotoxicity - 0.7750 77.50%
skin sensitisation - 0.8144 81.44%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity + 0.4873 48.73%
Acute Oral Toxicity (c) IV 0.5178 51.78%
Estrogen receptor binding + 0.7749 77.49%
Androgen receptor binding + 0.7846 78.46%
Thyroid receptor binding + 0.5804 58.04%
Glucocorticoid receptor binding + 0.5698 56.98%
Aromatase binding + 0.5912 59.12%
PPAR gamma + 0.7560 75.60%
Honey bee toxicity - 0.6305 63.05%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.6800 68.00%
Fish aquatic toxicity + 0.7943 79.43%

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 99.73% 91.11%
CHEMBL233 P35372 Mu opioid receptor 96.29% 97.93%
CHEMBL236 P41143 Delta opioid receptor 95.19% 99.35%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.64% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.50% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.12% 89.00%
CHEMBL2581 P07339 Cathepsin D 89.51% 98.95%
CHEMBL2535 P11166 Glucose transporter 88.74% 98.75%
CHEMBL1951 P21397 Monoamine oxidase A 88.57% 91.49%
CHEMBL1929 P47989 Xanthine dehydrogenase 88.23% 96.12%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.54% 94.45%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 86.39% 99.15%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.69% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.72% 99.23%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 81.05% 94.62%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.55% 95.89%
CHEMBL2553 Q15418 Ribosomal protein S6 kinase alpha 1 80.29% 85.11%

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.
Aesculus hippocastanum

Cross-Links

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PubChem 16165526
LOTUS LTS0118448
wikiData Q104974141