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[(2S,3R,4S,5S,6R)-2-[[(1S,4aR,7S,7aS)-4-formyl-4a-hydroxy-7-[(2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoyl]oxy-7-methyl-1,5,6,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-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 332c3cb8-4bf6-4211-bd5c-e50cb4aecae1
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name [(2S,3R,4S,5S,6R)-2-[[(1S,4aR,7S,7aS)-4-formyl-4a-hydroxy-7-[(2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoyl]oxy-7-methyl-1,5,6,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoate
SMILES (Canonical) CC(=CCO)CCC=C(C)C(=O)OC1C(C(C(OC1OC2C3C(CCC3(C(=CO2)C=O)O)(C)OC(=O)C(=CCCC(=CCO)C)C)CO)O)O
SMILES (Isomeric) C/C(=C\CO)/CC/C=C(\C)/C(=O)O[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O[C@H]2[C@@H]3[C@@](CC[C@@]3(C(=CO2)C=O)O)(C)OC(=O)/C(=C/CC/C(=C/CO)/C)/C)CO)O)O
InChI InChI=1S/C36H52O14/c1-21(12-16-37)8-6-10-23(3)31(43)48-29-28(42)27(41)26(19-40)47-33(29)49-34-30-35(5,14-15-36(30,45)25(18-39)20-46-34)50-32(44)24(4)11-7-9-22(2)13-17-38/h10-13,18,20,26-30,33-34,37-38,40-42,45H,6-9,14-17,19H2,1-5H3/b21-12+,22-13+,23-10+,24-11+/t26-,27-,28+,29-,30-,33+,34+,35+,36+/m1/s1
InChI Key OGOIOIQOMMXKKU-PXZCJPHLSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C36H52O14
Molecular Weight 708.80 g/mol
Exact Mass 708.33570633 g/mol
Topological Polar Surface Area (TPSA) 219.00 Ų
XlogP 2.20
Atomic LogP (AlogP) 1.57
H-Bond Acceptor 14
H-Bond Donor 6
Rotatable Bonds 16

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2S,3R,4S,5S,6R)-2-[[(1S,4aR,7S,7aS)-4-formyl-4a-hydroxy-7-[(2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoyl]oxy-7-methyl-1,5,6,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6790 67.90%
Caco-2 - 0.8560 85.60%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.8033 80.33%
OATP2B1 inhibitior - 0.8592 85.92%
OATP1B1 inhibitior + 0.7596 75.96%
OATP1B3 inhibitior + 0.8903 89.03%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.5798 57.98%
BSEP inhibitior + 0.9561 95.61%
P-glycoprotein inhibitior + 0.7545 75.45%
P-glycoprotein substrate - 0.5572 55.72%
CYP3A4 substrate + 0.7083 70.83%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8792 87.92%
CYP3A4 inhibition - 0.8984 89.84%
CYP2C9 inhibition - 0.9204 92.04%
CYP2C19 inhibition - 0.9387 93.87%
CYP2D6 inhibition - 0.9545 95.45%
CYP1A2 inhibition - 0.9218 92.18%
CYP2C8 inhibition + 0.5389 53.89%
CYP inhibitory promiscuity - 0.9671 96.71%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6448 64.48%
Eye corrosion - 0.9914 99.14%
Eye irritation - 0.9177 91.77%
Skin irritation + 0.5261 52.61%
Skin corrosion - 0.9451 94.51%
Ames mutagenesis - 0.5870 58.70%
Human Ether-a-go-go-Related Gene inhibition - 0.3602 36.02%
Micronuclear - 0.8100 81.00%
Hepatotoxicity - 0.6513 65.13%
skin sensitisation - 0.9328 93.28%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity - 0.7002 70.02%
Acute Oral Toxicity (c) I 0.5806 58.06%
Estrogen receptor binding + 0.8068 80.68%
Androgen receptor binding + 0.6565 65.65%
Thyroid receptor binding + 0.5567 55.67%
Glucocorticoid receptor binding + 0.7278 72.78%
Aromatase binding + 0.5895 58.95%
PPAR gamma + 0.7470 74.70%
Honey bee toxicity - 0.7614 76.14%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity - 0.5855 58.55%
Fish aquatic toxicity + 0.9442 94.42%

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 97.90% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.82% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.58% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.13% 97.25%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.36% 89.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.60% 100.00%
CHEMBL218 P21554 Cannabinoid CB1 receptor 88.49% 96.61%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 87.99% 93.00%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 87.11% 94.23%
CHEMBL4227 P25090 Lipoxin A4 receptor 87.04% 100.00%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 86.55% 95.50%
CHEMBL2581 P07339 Cathepsin D 86.51% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.09% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.89% 97.09%
CHEMBL221 P23219 Cyclooxygenase-1 85.55% 90.17%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 84.34% 96.00%
CHEMBL5255 O00206 Toll-like receptor 4 84.31% 92.50%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 84.29% 91.24%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 84.18% 91.07%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 83.78% 94.33%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 83.60% 96.21%
CHEMBL3401 O75469 Pregnane X receptor 81.91% 94.73%
CHEMBL4208 P20618 Proteasome component C5 81.91% 90.00%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 80.46% 94.08%

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.
Rotheca incisa

Cross-Links

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PubChem 163016617
LOTUS LTS0127332
wikiData Q105191743