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[(1S,4aR,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E)-3-phenylprop-2-enoate

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 cb7a5530-0b09-4450-8ddc-7378f436556e
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name [(1S,4aR,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E)-3-phenylprop-2-enoate
SMILES (Canonical) CC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)COC4C(C(C(C(O4)CO)O)O)O)O)O)O)O)O)OC(=O)C=CC5=CC=CC=C5
SMILES (Isomeric) C[C@@]1(C[C@H]([C@@]2([C@@H]1[C@@H](OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)O)O)O)O)O)OC(=O)/C=C/C5=CC=CC=C5
InChI InChI=1S/C30H40O16/c1-29(46-18(33)8-7-14-5-3-2-4-6-14)11-17(32)30(40)9-10-41-28(25(29)30)45-27-24(39)22(37)20(35)16(44-27)13-42-26-23(38)21(36)19(34)15(12-31)43-26/h2-10,15-17,19-28,31-32,34-40H,11-13H2,1H3/b8-7+/t15-,16-,17-,19+,20-,21+,22+,23-,24-,25-,26+,27+,28+,29+,30+/m1/s1
InChI Key UWFOZHRIYIQCSM-YQJCUPFPSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C30H40O16
Molecular Weight 656.60 g/mol
Exact Mass 656.23163518 g/mol
Topological Polar Surface Area (TPSA) 255.00 Ų
XlogP -2.80
Atomic LogP (AlogP) -3.38
H-Bond Acceptor 16
H-Bond Donor 9
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,4aR,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E)-3-phenylprop-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5458 54.58%
Caco-2 - 0.8828 88.28%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8714 87.14%
Subcellular localzation Mitochondria 0.5895 58.95%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8549 85.49%
OATP1B3 inhibitior + 0.9555 95.55%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.5922 59.22%
P-glycoprotein inhibitior - 0.4615 46.15%
P-glycoprotein substrate - 0.6489 64.89%
CYP3A4 substrate + 0.6747 67.47%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8809 88.09%
CYP3A4 inhibition - 0.9285 92.85%
CYP2C9 inhibition - 0.9410 94.10%
CYP2C19 inhibition - 0.8737 87.37%
CYP2D6 inhibition - 0.9179 91.79%
CYP1A2 inhibition - 0.9062 90.62%
CYP2C8 inhibition + 0.6942 69.42%
CYP inhibitory promiscuity - 0.8716 87.16%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5743 57.43%
Eye corrosion - 0.9927 99.27%
Eye irritation - 0.9250 92.50%
Skin irritation - 0.7902 79.02%
Skin corrosion - 0.9521 95.21%
Ames mutagenesis - 0.6470 64.70%
Human Ether-a-go-go-Related Gene inhibition + 0.8301 83.01%
Micronuclear - 0.6400 64.00%
Hepatotoxicity - 0.7940 79.40%
skin sensitisation - 0.8651 86.51%
Respiratory toxicity + 0.5444 54.44%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity + 0.5875 58.75%
Nephrotoxicity - 0.7040 70.40%
Acute Oral Toxicity (c) III 0.5469 54.69%
Estrogen receptor binding + 0.7874 78.74%
Androgen receptor binding + 0.6553 65.53%
Thyroid receptor binding + 0.5574 55.74%
Glucocorticoid receptor binding + 0.6702 67.02%
Aromatase binding + 0.5645 56.45%
PPAR gamma + 0.6461 64.61%
Honey bee toxicity - 0.8157 81.57%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5155 51.55%
Fish aquatic toxicity + 0.7336 73.36%

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 98.96% 91.11%
CHEMBL221 P23219 Cyclooxygenase-1 98.07% 90.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.72% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.61% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 95.04% 96.00%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 91.88% 94.62%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.03% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.73% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.15% 97.09%
CHEMBL5028 O14672 ADAM10 85.13% 97.50%
CHEMBL226 P30542 Adenosine A1 receptor 84.94% 95.93%
CHEMBL3401 O75469 Pregnane X receptor 83.07% 94.73%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 82.02% 94.08%
CHEMBL2581 P07339 Cathepsin D 81.97% 98.95%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 81.75% 95.83%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 80.83% 94.23%

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.
Harpagophytum procumbens

Cross-Links

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PubChem 163030846
LOTUS LTS0115967
wikiData Q105280329