2-[(2R,4aR,8aS)-4a,8-dimethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,6-hexahydronaphthalen-2-yl]prop-2-enoic acid

Details

Top
Internal ID c510930f-0885-4833-b4d0-f7cf70d6859c
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
IUPAC Name 2-[(2R,4aR,8aS)-4a,8-dimethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,6-hexahydronaphthalen-2-yl]prop-2-enoic acid
SMILES (Canonical) CC1=CCCC2(C1(CC(CC2)C(=C)C(=O)O)OC3C(C(C(C(O3)CO)O)O)O)C
SMILES (Isomeric) CC1=CCC[C@]2([C@]1(C[C@@H](CC2)C(=C)C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C
InChI InChI=1S/C21H32O8/c1-11-5-4-7-20(3)8-6-13(12(2)18(26)27)9-21(11,20)29-19-17(25)16(24)15(23)14(10-22)28-19/h5,13-17,19,22-25H,2,4,6-10H2,1,3H3,(H,26,27)/t13-,14-,15-,16+,17-,19+,20-,21-/m1/s1
InChI Key MJSUVEADTASQDQ-ZEKJDWQUSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

Top
Molecular Formula C21H32O8
Molecular Weight 412.50 g/mol
Exact Mass 412.20971797 g/mol
Topological Polar Surface Area (TPSA) 137.00 Ų
XlogP 0.70
Atomic LogP (AlogP) 0.73
H-Bond Acceptor 7
H-Bond Donor 5
Rotatable Bonds 5

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of 2-[(2R,4aR,8aS)-4a,8-dimethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,6-hexahydronaphthalen-2-yl]prop-2-enoic acid

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7353 73.53%
Caco-2 - 0.7058 70.58%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.8079 80.79%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8837 88.37%
OATP1B3 inhibitior + 0.8353 83.53%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.7096 70.96%
BSEP inhibitior - 0.7778 77.78%
P-glycoprotein inhibitior - 0.7753 77.53%
P-glycoprotein substrate - 0.8152 81.52%
CYP3A4 substrate + 0.6483 64.83%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8880 88.80%
CYP3A4 inhibition - 0.8432 84.32%
CYP2C9 inhibition - 0.8688 86.88%
CYP2C19 inhibition - 0.8440 84.40%
CYP2D6 inhibition - 0.9316 93.16%
CYP1A2 inhibition - 0.7210 72.10%
CYP2C8 inhibition + 0.5596 55.96%
CYP inhibitory promiscuity - 0.8941 89.41%
UGT catelyzed - 0.8000 80.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.7502 75.02%
Eye corrosion - 0.9903 99.03%
Eye irritation - 0.9532 95.32%
Skin irritation - 0.5946 59.46%
Skin corrosion - 0.9497 94.97%
Ames mutagenesis - 0.5471 54.71%
Human Ether-a-go-go-Related Gene inhibition + 0.6692 66.92%
Micronuclear - 0.8700 87.00%
Hepatotoxicity - 0.7319 73.19%
skin sensitisation - 0.8885 88.85%
Respiratory toxicity - 0.5000 50.00%
Reproductive toxicity + 0.8333 83.33%
Mitochondrial toxicity - 0.5625 56.25%
Nephrotoxicity - 0.5652 56.52%
Acute Oral Toxicity (c) III 0.6205 62.05%
Estrogen receptor binding + 0.6260 62.60%
Androgen receptor binding + 0.6088 60.88%
Thyroid receptor binding + 0.5349 53.49%
Glucocorticoid receptor binding - 0.5651 56.51%
Aromatase binding + 0.5725 57.25%
PPAR gamma + 0.6984 69.84%
Honey bee toxicity - 0.8257 82.57%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6250 62.50%
Fish aquatic toxicity + 0.9804 98.04%

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 97.99% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.28% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.50% 97.25%
CHEMBL3714130 P46095 G-protein coupled receptor 6 93.20% 97.36%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.36% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.30% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.16% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.85% 95.89%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 86.21% 91.24%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.87% 95.56%
CHEMBL2243 O00519 Anandamide amidohydrolase 84.45% 97.53%
CHEMBL218 P21554 Cannabinoid CB1 receptor 82.57% 96.61%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.31% 95.89%
CHEMBL4208 P20618 Proteasome component C5 80.76% 90.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 80.64% 96.00%
CHEMBL5028 O14672 ADAM10 80.54% 97.50%

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.
Laggera alata
Laggera alata

Cross-Links

Top
PubChem 11026030
NPASS NPC287228
LOTUS LTS0156988
wikiData Q105165643