(2S,3R,4S,5S,6R)-2-[[(1S,4aS,5R,7aR)-5-hydroxy-7-methyl-4a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,7a-dihydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

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Internal ID 6b1afc88-b703-4e4b-88e6-ab8bb82f9c9f
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name (2S,3R,4S,5S,6R)-2-[[(1S,4aS,5R,7aR)-5-hydroxy-7-methyl-4a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,7a-dihydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES (Canonical) CC1=CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)OC4C(C(C(C(O4)CO)O)O)O)O
SMILES (Isomeric) CC1=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)O)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
InChI InChI=1S/C21H32O14/c1-7-4-10(24)21(35-20-17(30)15(28)13(26)9(6-23)33-20)2-3-31-18(11(7)21)34-19-16(29)14(27)12(25)8(5-22)32-19/h2-4,8-20,22-30H,5-6H2,1H3/t8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18+,19+,20+,21-/m1/s1
InChI Key GEKIUWZJPXHAEB-GVKBFFPQSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H32O14
Molecular Weight 508.50 g/mol
Exact Mass 508.17920569 g/mol
Topological Polar Surface Area (TPSA) 228.00 Ų
XlogP -4.40
Atomic LogP (AlogP) -4.83
H-Bond Acceptor 14
H-Bond Donor 9
Rotatable Bonds 6

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,4aS,5R,7aR)-5-hydroxy-7-methyl-4a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,7a-dihydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.6299 62.99%
Caco-2 - 0.8615 86.15%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.6451 64.51%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8493 84.93%
OATP1B3 inhibitior + 0.9589 95.89%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.9114 91.14%
P-glycoprotein inhibitior - 0.7125 71.25%
P-glycoprotein substrate - 0.8378 83.78%
CYP3A4 substrate + 0.6007 60.07%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8403 84.03%
CYP3A4 inhibition - 0.9686 96.86%
CYP2C9 inhibition - 0.8948 89.48%
CYP2C19 inhibition - 0.8055 80.55%
CYP2D6 inhibition - 0.9149 91.49%
CYP1A2 inhibition - 0.8762 87.62%
CYP2C8 inhibition - 0.6432 64.32%
CYP inhibitory promiscuity - 0.6861 68.61%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6089 60.89%
Eye corrosion - 0.9897 98.97%
Eye irritation - 0.9366 93.66%
Skin irritation - 0.8003 80.03%
Skin corrosion - 0.9529 95.29%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7095 70.95%
Micronuclear - 0.7441 74.41%
Hepatotoxicity - 0.8875 88.75%
skin sensitisation - 0.8706 87.06%
Respiratory toxicity - 0.5111 51.11%
Reproductive toxicity + 0.7000 70.00%
Mitochondrial toxicity - 0.5625 56.25%
Nephrotoxicity + 0.4626 46.26%
Acute Oral Toxicity (c) III 0.3767 37.67%
Estrogen receptor binding + 0.5608 56.08%
Androgen receptor binding + 0.5659 56.59%
Thyroid receptor binding + 0.5508 55.08%
Glucocorticoid receptor binding + 0.5512 55.12%
Aromatase binding + 0.6661 66.61%
PPAR gamma + 0.6276 62.76%
Honey bee toxicity - 0.7904 79.04%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.6650 66.50%
Fish aquatic toxicity - 0.5565 55.65%

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 94.31% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.23% 91.11%
CHEMBL3401 O75469 Pregnane X receptor 90.59% 94.73%
CHEMBL226 P30542 Adenosine A1 receptor 89.51% 95.93%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.41% 94.00%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 84.92% 86.92%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.19% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.05% 89.00%

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.
Lamium galeobdolon

Cross-Links

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PubChem 162985783
LOTUS LTS0124601
wikiData Q105007204