(1S,4aS,6R,7R,7aS)-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[3-[3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoyl]oxybenzoyl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid

Details

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Internal ID 950c5e32-9fc6-4317-ab5a-af70666137ac
Taxonomy Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
IUPAC Name (1S,4aS,6R,7R,7aS)-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[3-[3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoyl]oxybenzoyl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
SMILES (Canonical) CC1C(CC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C4=CC(=CC=C4)OC(=O)C5=CC(=CC=C5)OC6C(C(C(C(O6)CO)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC(=O)C4=CC(=CC=C4)OC(=O)C5=CC(=CC=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
InChI InChI=1S/C36H42O19/c1-14-21(10-19-20(31(45)46)13-49-34(24(14)19)55-36-30(44)28(42)26(40)23(12-38)54-36)52-33(48)16-5-2-6-17(8-16)50-32(47)15-4-3-7-18(9-15)51-35-29(43)27(41)25(39)22(11-37)53-35/h2-9,13-14,19,21-30,34-44H,10-12H2,1H3,(H,45,46)/t14-,19+,21+,22+,23+,24+,25+,26+,27-,28-,29+,30+,34-,35+,36-/m0/s1
InChI Key SPWKTWFVULCXGX-CPDJBEDISA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C36H42O19
Molecular Weight 778.70 g/mol
Exact Mass 778.23202911 g/mol
Topological Polar Surface Area (TPSA) 298.00 Ų
XlogP -0.20
Atomic LogP (AlogP) -1.98
H-Bond Acceptor 18
H-Bond Donor 9
Rotatable Bonds 11

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,4aS,6R,7R,7aS)-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[3-[3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoyl]oxybenzoyl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-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 + 0.6494 64.94%
Caco-2 - 0.8869 88.69%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.6789 67.89%
OATP2B1 inhibitior - 0.7185 71.85%
OATP1B1 inhibitior - 0.3233 32.33%
OATP1B3 inhibitior + 0.9604 96.04%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.9446 94.46%
P-glycoprotein inhibitior + 0.6966 69.66%
P-glycoprotein substrate - 0.5814 58.14%
CYP3A4 substrate + 0.6753 67.53%
CYP2C9 substrate - 0.6013 60.13%
CYP2D6 substrate - 0.8810 88.10%
CYP3A4 inhibition - 0.9374 93.74%
CYP2C9 inhibition - 0.8102 81.02%
CYP2C19 inhibition - 0.7854 78.54%
CYP2D6 inhibition - 0.9046 90.46%
CYP1A2 inhibition - 0.7909 79.09%
CYP2C8 inhibition + 0.6859 68.59%
CYP inhibitory promiscuity - 0.6563 65.63%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6431 64.31%
Eye corrosion - 0.9909 99.09%
Eye irritation - 0.9087 90.87%
Skin irritation - 0.7769 77.69%
Skin corrosion - 0.9436 94.36%
Ames mutagenesis + 0.5077 50.77%
Human Ether-a-go-go-Related Gene inhibition + 0.7589 75.89%
Micronuclear - 0.6000 60.00%
Hepatotoxicity - 0.7089 70.89%
skin sensitisation - 0.8455 84.55%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity - 0.7181 71.81%
Acute Oral Toxicity (c) III 0.5079 50.79%
Estrogen receptor binding + 0.7838 78.38%
Androgen receptor binding + 0.5608 56.08%
Thyroid receptor binding + 0.5177 51.77%
Glucocorticoid receptor binding + 0.6448 64.48%
Aromatase binding - 0.5443 54.43%
PPAR gamma + 0.7296 72.96%
Honey bee toxicity - 0.7381 73.81%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.9656 96.56%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.38% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.91% 97.09%
CHEMBL2581 P07339 Cathepsin D 94.58% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.46% 86.33%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 90.93% 91.11%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 90.48% 86.92%
CHEMBL3060 Q9Y345 Glycine transporter 2 89.89% 99.17%
CHEMBL220 P22303 Acetylcholinesterase 88.85% 94.45%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 87.91% 96.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.10% 95.89%
CHEMBL4208 P20618 Proteasome component C5 86.89% 90.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.66% 95.56%
CHEMBL3401 O75469 Pregnane X receptor 86.62% 94.73%
CHEMBL226 P30542 Adenosine A1 receptor 86.14% 95.93%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 85.41% 96.00%
CHEMBL221 P23219 Cyclooxygenase-1 85.28% 90.17%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 85.28% 81.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.61% 89.00%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 83.55% 96.09%
CHEMBL2243 O00519 Anandamide amidohydrolase 82.34% 97.53%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.41% 99.23%
CHEMBL245 P20309 Muscarinic acetylcholine receptor M3 81.21% 97.53%
CHEMBL5028 O14672 ADAM10 81.01% 97.50%
CHEMBL1811 P34995 Prostanoid EP1 receptor 80.30% 95.71%
CHEMBL209 P07477 Trypsin I 80.11% 90.00%

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.
Ophiorrhiza kuroiwai
Swertia franchetiana
Swertia japonica

Cross-Links

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PubChem 11411716
LOTUS LTS0028606
wikiData Q105257644