1-[4a,5,7-Trihydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl]propan-2-one

Details

Top
Internal ID 91528c83-803f-4eeb-a080-ab4feeacfbba
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name 1-[4a,5,7-trihydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl]propan-2-one
SMILES (Canonical) CC(=O)CC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)O
SMILES (Isomeric) CC(=O)CC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)O
InChI InChI=1S/C17H26O11/c1-7(19)4-16(24)5-9(20)17(25)2-3-26-15(13(16)17)28-14-12(23)11(22)10(21)8(6-18)27-14/h2-3,8-15,18,20-25H,4-6H2,1H3
InChI Key JXRURJXEYMRHCO-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C17H26O11
Molecular Weight 406.40 g/mol
Exact Mass 406.14751164 g/mol
Topological Polar Surface Area (TPSA) 186.00 Ų
XlogP -3.40
Atomic LogP (AlogP) -3.50
H-Bond Acceptor 11
H-Bond Donor 7
Rotatable Bonds 5

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of 1-[4a,5,7-Trihydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl]propan-2-one

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5575 55.75%
Caco-2 - 0.8758 87.58%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.8429 84.29%
Subcellular localzation Mitochondria 0.6013 60.13%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8806 88.06%
OATP1B3 inhibitior + 0.9461 94.61%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.9261 92.61%
P-glycoprotein inhibitior - 0.8538 85.38%
P-glycoprotein substrate - 0.8309 83.09%
CYP3A4 substrate + 0.6391 63.91%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8645 86.45%
CYP3A4 inhibition - 0.8998 89.98%
CYP2C9 inhibition - 0.9415 94.15%
CYP2C19 inhibition - 0.9258 92.58%
CYP2D6 inhibition - 0.9465 94.65%
CYP1A2 inhibition - 0.9058 90.58%
CYP2C8 inhibition - 0.7528 75.28%
CYP inhibitory promiscuity - 0.9051 90.51%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6023 60.23%
Eye corrosion - 0.9922 99.22%
Eye irritation - 0.9656 96.56%
Skin irritation - 0.7394 73.94%
Skin corrosion - 0.9409 94.09%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5146 51.46%
Micronuclear - 0.7300 73.00%
Hepatotoxicity - 0.8199 81.99%
skin sensitisation - 0.8813 88.13%
Respiratory toxicity - 0.5333 53.33%
Reproductive toxicity + 0.7444 74.44%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity + 0.4696 46.96%
Acute Oral Toxicity (c) III 0.5243 52.43%
Estrogen receptor binding + 0.5720 57.20%
Androgen receptor binding - 0.5000 50.00%
Thyroid receptor binding + 0.5636 56.36%
Glucocorticoid receptor binding - 0.5946 59.46%
Aromatase binding + 0.6504 65.04%
PPAR gamma + 0.5609 56.09%
Honey bee toxicity - 0.8003 80.03%
Biodegradation - 0.5750 57.50%
Crustacea aquatic toxicity - 0.7055 70.55%
Fish aquatic toxicity - 0.4183 41.83%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.14% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.89% 91.11%
CHEMBL4040 P28482 MAP kinase ERK2 93.87% 83.82%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.50% 89.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 86.88% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.61% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.00% 97.09%
CHEMBL226 P30542 Adenosine A1 receptor 83.98% 95.93%
CHEMBL218 P21554 Cannabinoid CB1 receptor 82.42% 96.61%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.22% 100.00%
CHEMBL221 P23219 Cyclooxygenase-1 81.16% 90.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.69% 86.33%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 80.20% 96.00%

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.
Ajuga pyramidalis

Cross-Links

Top
PubChem 162903007
LOTUS LTS0248054
wikiData Q105136751