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

Details

Top
Internal ID f51d412f-4980-4c9f-b40a-f2d504603204
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name (1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbaldehyde
SMILES (Canonical) CC1(CCC2C1C(OC=C2C=O)OC3C(C(C(C(O3)CO)O)O)O)O
SMILES (Isomeric) C[C@@]1(CC[C@H]2[C@@H]1[C@@H](OC=C2C=O)O[C@H]3[C@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
InChI InChI=1S/C16H24O9/c1-16(22)3-2-8-7(4-17)6-23-14(10(8)16)25-15-13(21)12(20)11(19)9(5-18)24-15/h4,6,8-15,18-22H,2-3,5H2,1H3/t8-,9-,10-,11-,12+,13+,14+,15+,16+/m1/s1
InChI Key XQUFDDXBHJINGZ-ZAALRAECSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C16H24O9
Molecular Weight 360.36 g/mol
Exact Mass 360.14203234 g/mol
Topological Polar Surface Area (TPSA) 146.00 Ų
XlogP -2.00
Atomic LogP (AlogP) -1.98
H-Bond Acceptor 9
H-Bond Donor 5
Rotatable Bonds 4

Synonyms

Top
There are no found synonyms.

2D Structure

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

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7659 76.59%
Caco-2 - 0.8774 87.74%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.8714 87.14%
Subcellular localzation Mitochondria 0.7195 71.95%
OATP2B1 inhibitior - 0.8588 85.88%
OATP1B1 inhibitior + 0.7092 70.92%
OATP1B3 inhibitior + 0.9184 91.84%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.7879 78.79%
BSEP inhibitior - 0.9127 91.27%
P-glycoprotein inhibitior - 0.8781 87.81%
P-glycoprotein substrate - 0.8733 87.33%
CYP3A4 substrate + 0.6285 62.85%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8528 85.28%
CYP3A4 inhibition - 0.9341 93.41%
CYP2C9 inhibition - 0.8851 88.51%
CYP2C19 inhibition - 0.9071 90.71%
CYP2D6 inhibition - 0.9191 91.91%
CYP1A2 inhibition - 0.8644 86.44%
CYP2C8 inhibition - 0.6342 63.42%
CYP inhibitory promiscuity - 0.8847 88.47%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6368 63.68%
Eye corrosion - 0.9912 99.12%
Eye irritation - 0.9887 98.87%
Skin irritation - 0.5643 56.43%
Skin corrosion - 0.9285 92.85%
Ames mutagenesis - 0.7170 71.70%
Human Ether-a-go-go-Related Gene inhibition - 0.3881 38.81%
Micronuclear - 0.8600 86.00%
Hepatotoxicity - 0.8092 80.92%
skin sensitisation - 0.8894 88.94%
Respiratory toxicity - 0.5000 50.00%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity + 0.5765 57.65%
Acute Oral Toxicity (c) III 0.4596 45.96%
Estrogen receptor binding + 0.5290 52.90%
Androgen receptor binding - 0.5515 55.15%
Thyroid receptor binding - 0.5108 51.08%
Glucocorticoid receptor binding - 0.5000 50.00%
Aromatase binding - 0.5278 52.78%
PPAR gamma + 0.5672 56.72%
Honey bee toxicity - 0.8402 84.02%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.6655 66.55%
Fish aquatic toxicity + 0.7290 72.90%

Targets

Top

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 95.63% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.61% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.92% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.73% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 88.24% 97.25%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.48% 100.00%
CHEMBL226 P30542 Adenosine A1 receptor 87.35% 95.93%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.54% 95.89%
CHEMBL4208 P20618 Proteasome component C5 85.52% 90.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.83% 86.33%
CHEMBL2581 P07339 Cathepsin D 84.57% 98.95%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 83.73% 86.92%
CHEMBL218 P21554 Cannabinoid CB1 receptor 83.34% 96.61%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.56% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.65% 89.00%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 80.00% 95.83%

Plants that contains it

Top
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.
Gardenia jasminoides
Ixora chinensis
Plantago major

Cross-Links

Top
PubChem 161786273
LOTUS LTS0076589
wikiData Q105340050