(2S,3R,4S,5S,6R)-2-[[(1S,4aR,5R,7R,7aR)-4a,5-dihydroxy-4,7-dimethyl-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

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Internal ID ac645bc3-ec2a-4c6d-b8b1-e12c49e0baac
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name (2S,3R,4S,5S,6R)-2-[[(1S,4aR,5R,7R,7aR)-4a,5-dihydroxy-4,7-dimethyl-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES (Canonical) CC1CC(C2(C1C(OC=C2C)OC3C(C(C(C(O3)CO)O)O)O)O)O
SMILES (Isomeric) C[C@@H]1C[C@H]([C@]2([C@@H]1[C@@H](OC=C2C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
InChI InChI=1S/C16H26O9/c1-6-3-9(18)16(22)7(2)5-23-14(10(6)16)25-15-13(21)12(20)11(19)8(4-17)24-15/h5-6,8-15,17-22H,3-4H2,1-2H3/t6-,8-,9-,10+,11-,12+,13-,14+,15+,16-/m1/s1
InChI Key PTAMXMVHYDHPMO-NKFHIRRBSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C16H26O9
Molecular Weight 362.37 g/mol
Exact Mass 362.15768240 g/mol
Topological Polar Surface Area (TPSA) 149.00 Ų
XlogP -2.10
Atomic LogP (AlogP) -2.19
H-Bond Acceptor 9
H-Bond Donor 6
Rotatable Bonds 3

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,5R,7R,7aR)-4a,5-dihydroxy-4,7-dimethyl-5,6,7,7a-tetrahydro-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 + 0.5635 56.35%
Caco-2 - 0.8410 84.10%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.5450 54.50%
OATP2B1 inhibitior - 0.8576 85.76%
OATP1B1 inhibitior + 0.8347 83.47%
OATP1B3 inhibitior + 0.9406 94.06%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.8916 89.16%
P-glycoprotein inhibitior - 0.8762 87.62%
P-glycoprotein substrate - 0.8714 87.14%
CYP3A4 substrate + 0.5816 58.16%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8354 83.54%
CYP3A4 inhibition - 0.8983 89.83%
CYP2C9 inhibition - 0.8949 89.49%
CYP2C19 inhibition - 0.8933 89.33%
CYP2D6 inhibition - 0.9228 92.28%
CYP1A2 inhibition - 0.8698 86.98%
CYP2C8 inhibition - 0.7546 75.46%
CYP inhibitory promiscuity - 0.8169 81.69%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6123 61.23%
Eye corrosion - 0.9914 99.14%
Eye irritation - 0.9851 98.51%
Skin irritation - 0.7128 71.28%
Skin corrosion - 0.9465 94.65%
Ames mutagenesis - 0.6154 61.54%
Human Ether-a-go-go-Related Gene inhibition - 0.5133 51.33%
Micronuclear - 0.7600 76.00%
Hepatotoxicity - 0.8052 80.52%
skin sensitisation - 0.8665 86.65%
Respiratory toxicity - 0.5667 56.67%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity - 0.7208 72.08%
Acute Oral Toxicity (c) III 0.4235 42.35%
Estrogen receptor binding - 0.6323 63.23%
Androgen receptor binding + 0.6101 61.01%
Thyroid receptor binding + 0.6179 61.79%
Glucocorticoid receptor binding - 0.6766 67.66%
Aromatase binding + 0.6345 63.45%
PPAR gamma + 0.6285 62.85%
Honey bee toxicity - 0.8769 87.69%
Biodegradation - 0.6500 65.00%
Crustacea aquatic toxicity - 0.6200 62.00%
Fish aquatic toxicity - 0.3656 36.56%

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 94.47% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.78% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 90.90% 91.11%
CHEMBL4208 P20618 Proteasome component C5 87.68% 90.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.49% 86.33%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 86.99% 85.14%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 85.04% 96.95%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 84.30% 97.21%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.55% 89.00%
CHEMBL241 Q14432 Phosphodiesterase 3A 82.41% 92.94%
CHEMBL218 P21554 Cannabinoid CB1 receptor 82.20% 96.61%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.66% 100.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.53% 94.00%
CHEMBL3714130 P46095 G-protein coupled receptor 6 81.20% 97.36%
CHEMBL2581 P07339 Cathepsin D 80.66% 98.95%

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 amplexicaule

Cross-Links

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PubChem 102479107
LOTUS LTS0270028
wikiData Q105214522