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(1R,2S,3R,6R,8S,9S,13S,14R,15R,16S,17R)-15,16-dihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,10-dioxo-11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-11-ene-17-carboxylic acid

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 52123b45-c322-4472-ad1f-2ac506541778
Taxonomy Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones > Naphthopyranone glycosides
IUPAC Name (1R,2S,3R,6R,8S,9S,13S,14R,15R,16S,17R)-15,16-dihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,10-dioxo-11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-11-ene-17-carboxylic acid
SMILES (Canonical) CC1C2CC3C45COC(C4C(C(=O)O3)OC(=O)C=C(C)C)(C(C(C5C2(C=C(C1=O)OC6C(C(C(C(O6)CO)O)O)O)C)O)O)C(=O)O
SMILES (Isomeric) C[C@H]1[C@@H]2C[C@@H]3[C@@]45CO[C@]([C@@H]4[C@H](C(=O)O3)OC(=O)C=C(C)C)([C@H]([C@@H]([C@@H]5[C@]2(C=C(C1=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)O)O)C(=O)O
InChI InChI=1S/C31H40O16/c1-10(2)5-16(33)47-22-24-30-9-43-31(24,28(41)42)25(39)21(38)23(30)29(4)7-13(17(34)11(3)12(29)6-15(30)46-26(22)40)44-27-20(37)19(36)18(35)14(8-32)45-27/h5,7,11-12,14-15,18-25,27,32,35-39H,6,8-9H2,1-4H3,(H,41,42)/t11-,12-,14+,15+,18+,19-,20+,21+,22+,23+,24+,25-,27+,29-,30+,31+/m0/s1
InChI Key CXVWQUMYRFPSCJ-SJULGOEYSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C31H40O16
Molecular Weight 668.60 g/mol
Exact Mass 668.23163518 g/mol
Topological Polar Surface Area (TPSA) 256.00 Ų
XlogP -0.20
Atomic LogP (AlogP) -2.46
H-Bond Acceptor 15
H-Bond Donor 7
Rotatable Bonds 6

Synonyms

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(1R,2S,3R,6R,8S,9S,13S,14R,15R,16S,17R)-15,16-dihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,10-dioxo-11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-11-ene-17-carboxylic acid

2D Structure

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2D Structure of (1R,2S,3R,6R,8S,9S,13S,14R,15R,16S,17R)-15,16-dihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,10-dioxo-11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-11-ene-17-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 + 0.7113 71.13%
Caco-2 - 0.8767 87.67%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.7832 78.32%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8242 82.42%
OATP1B3 inhibitior + 0.9267 92.67%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.7858 78.58%
P-glycoprotein inhibitior + 0.6674 66.74%
P-glycoprotein substrate + 0.6991 69.91%
CYP3A4 substrate + 0.7035 70.35%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8904 89.04%
CYP3A4 inhibition - 0.9007 90.07%
CYP2C9 inhibition - 0.8272 82.72%
CYP2C19 inhibition - 0.8543 85.43%
CYP2D6 inhibition - 0.9341 93.41%
CYP1A2 inhibition - 0.8829 88.29%
CYP2C8 inhibition + 0.6439 64.39%
CYP inhibitory promiscuity - 0.8456 84.56%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6074 60.74%
Eye corrosion - 0.9876 98.76%
Eye irritation - 0.9183 91.83%
Skin irritation - 0.6909 69.09%
Skin corrosion - 0.9328 93.28%
Ames mutagenesis - 0.6200 62.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6853 68.53%
Micronuclear - 0.7500 75.00%
Hepatotoxicity - 0.6500 65.00%
skin sensitisation - 0.8500 85.00%
Respiratory toxicity + 0.7667 76.67%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity + 0.6756 67.56%
Acute Oral Toxicity (c) III 0.6314 63.14%
Estrogen receptor binding + 0.7759 77.59%
Androgen receptor binding + 0.7216 72.16%
Thyroid receptor binding - 0.5420 54.20%
Glucocorticoid receptor binding + 0.6521 65.21%
Aromatase binding + 0.6858 68.58%
PPAR gamma + 0.7263 72.63%
Honey bee toxicity - 0.6501 65.01%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.9520 95.20%

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 98.03% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.90% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 96.39% 96.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.73% 85.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.81% 86.33%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 92.55% 89.34%
CHEMBL2581 P07339 Cathepsin D 89.28% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.72% 89.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.04% 100.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.14% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.28% 97.09%
CHEMBL1951 P21397 Monoamine oxidase A 85.77% 91.49%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.91% 91.07%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.40% 99.23%
CHEMBL3922 P50579 Methionine aminopeptidase 2 82.02% 97.28%
CHEMBL5028 O14672 ADAM10 81.98% 97.50%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 81.60% 96.95%
CHEMBL2996 Q05655 Protein kinase C delta 80.82% 97.79%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.11% 95.89%

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.
Brucea javanica

Cross-Links

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PubChem 10484578
LOTUS LTS0207707
wikiData Q104972162