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[(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] (2E,4E)-3-methyl-5-[(1R,2R,3R)-1,2,3-trihydroxy-2,6,6-trimethylcyclohexyl]penta-2,4-dienoate

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 f2e93a4c-1a63-423d-b67a-d07d89b6d35d
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name [(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] (2E,4E)-3-methyl-5-[(1R,2R,3R)-1,2,3-trihydroxy-2,6,6-trimethylcyclohexyl]penta-2,4-dienoate
SMILES (Canonical) CC(=CC(=O)OC1CC(C2C1C=COC2OC3C(C(C(C(O3)CO)O)O)O)(C)O)C=CC4(C(CCC(C4(C)O)O)(C)C)O
SMILES (Isomeric) C/C(=C\C(=O)O[C@@H]1C[C@]([C@@H]2[C@H]1C=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)(C)O)/C=C/[C@@]4([C@]([C@@H](CCC4(C)C)O)(C)O)O
InChI InChI=1S/C30H46O13/c1-15(6-10-30(39)27(2,3)9-7-19(32)29(30,5)38)12-20(33)41-17-13-28(4,37)21-16(17)8-11-40-25(21)43-26-24(36)23(35)22(34)18(14-31)42-26/h6,8,10-12,16-19,21-26,31-32,34-39H,7,9,13-14H2,1-5H3/b10-6+,15-12+/t16-,17+,18+,19+,21+,22+,23-,24+,25-,26-,28-,29+,30+/m0/s1
InChI Key XAFIIDRISREJRR-JBWCCNGXSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C30H46O13
Molecular Weight 614.70 g/mol
Exact Mass 614.29384152 g/mol
Topological Polar Surface Area (TPSA) 216.00 Ų
XlogP -0.30
Atomic LogP (AlogP) -0.86
H-Bond Acceptor 13
H-Bond Donor 8
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] (2E,4E)-3-methyl-5-[(1R,2R,3R)-1,2,3-trihydroxy-2,6,6-trimethylcyclohexyl]penta-2,4-dienoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8201 82.01%
Caco-2 - 0.8673 86.73%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8714 87.14%
Subcellular localzation Mitochondria 0.7565 75.65%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8377 83.77%
OATP1B3 inhibitior + 0.8315 83.15%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.7776 77.76%
BSEP inhibitior + 0.8583 85.83%
P-glycoprotein inhibitior + 0.6208 62.08%
P-glycoprotein substrate - 0.5191 51.91%
CYP3A4 substrate + 0.7328 73.28%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8935 89.35%
CYP3A4 inhibition - 0.8973 89.73%
CYP2C9 inhibition - 0.8076 80.76%
CYP2C19 inhibition - 0.9170 91.70%
CYP2D6 inhibition - 0.9246 92.46%
CYP1A2 inhibition - 0.8709 87.09%
CYP2C8 inhibition + 0.5888 58.88%
CYP inhibitory promiscuity - 0.8853 88.53%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6421 64.21%
Eye corrosion - 0.9909 99.09%
Eye irritation - 0.9263 92.63%
Skin irritation - 0.5391 53.91%
Skin corrosion - 0.9310 93.10%
Ames mutagenesis - 0.7000 70.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3840 38.40%
Micronuclear - 0.8600 86.00%
Hepatotoxicity - 0.6925 69.25%
skin sensitisation - 0.8763 87.63%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.5125 51.25%
Nephrotoxicity - 0.8118 81.18%
Acute Oral Toxicity (c) III 0.6272 62.72%
Estrogen receptor binding + 0.7944 79.44%
Androgen receptor binding + 0.6607 66.07%
Thyroid receptor binding + 0.5666 56.66%
Glucocorticoid receptor binding + 0.6201 62.01%
Aromatase binding + 0.6208 62.08%
PPAR gamma + 0.6458 64.58%
Honey bee toxicity - 0.6281 62.81%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5255 52.55%
Fish aquatic toxicity + 0.8176 81.76%

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 97.65% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.06% 91.11%
CHEMBL221 P23219 Cyclooxygenase-1 94.24% 90.17%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.95% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.82% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.53% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.31% 89.00%
CHEMBL226 P30542 Adenosine A1 receptor 87.04% 95.93%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 86.66% 91.24%
CHEMBL5255 O00206 Toll-like receptor 4 86.08% 92.50%
CHEMBL1937 Q92769 Histone deacetylase 2 84.00% 94.75%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.87% 100.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.24% 95.89%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 82.77% 95.50%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 82.32% 96.00%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 82.20% 96.95%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 81.55% 95.83%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 81.06% 97.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.93% 95.89%
CHEMBL3401 O75469 Pregnane X receptor 80.01% 94.73%

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.
Rehmannia glutinosa

Cross-Links

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PubChem 71460782
NPASS NPC233500
LOTUS LTS0118863
wikiData Q105323895