PlantaeDB Logo
Login Sign-up

[(2S,3S,4R,4aS,5S,8R,8aR)-5-formyl-4,8-dihydroxy-3-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-2-yl] (3S)-4-acetyloxy-3-hydroxy-2-methylidenebutanoate

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

Top
Internal ID 0bff2465-def7-4ee0-adf9-915e2e7f9cba
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
IUPAC Name [(2S,3S,4R,4aS,5S,8R,8aR)-5-formyl-4,8-dihydroxy-3-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-2-yl] (3S)-4-acetyloxy-3-hydroxy-2-methylidenebutanoate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C23H32O10/c1-11(15(26)10-32-13(3)25)22(30)33-16-8-23(4)17(27)7-6-14(9-24)19(23)20(28)18(16)12(2)21(29)31-5/h9,14-20,26-28H,1-2,6-8,10H2,3-5H3/t14-,15-,16+,17-,18-,19-,20+,23+/m1/s1
InChI Key DIHJNCJEIOMBSV-KPFZLZHSSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C23H32O10
Molecular Weight 468.50 g/mol
Exact Mass 468.19954721 g/mol
Topological Polar Surface Area (TPSA) 157.00 Ų
XlogP 0.10
Atomic LogP (AlogP) 0.08
H-Bond Acceptor 10
H-Bond Donor 3
Rotatable Bonds 8

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of [(2S,3S,4R,4aS,5S,8R,8aR)-5-formyl-4,8-dihydroxy-3-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-2-yl] (3S)-4-acetyloxy-3-hydroxy-2-methylidenebutanoate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9790 97.90%
Caco-2 - 0.7767 77.67%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.8487 84.87%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8618 86.18%
OATP1B3 inhibitior + 0.8888 88.88%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.6771 67.71%
BSEP inhibitior - 0.5389 53.89%
P-glycoprotein inhibitior - 0.4742 47.42%
P-glycoprotein substrate + 0.6264 62.64%
CYP3A4 substrate + 0.7069 70.69%
CYP2C9 substrate - 0.8062 80.62%
CYP2D6 substrate - 0.8768 87.68%
CYP3A4 inhibition - 0.6920 69.20%
CYP2C9 inhibition - 0.8493 84.93%
CYP2C19 inhibition - 0.8526 85.26%
CYP2D6 inhibition - 0.9528 95.28%
CYP1A2 inhibition - 0.8256 82.56%
CYP2C8 inhibition + 0.5115 51.15%
CYP inhibitory promiscuity - 0.9519 95.19%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.7037 70.37%
Eye corrosion - 0.9921 99.21%
Eye irritation - 0.9361 93.61%
Skin irritation + 0.5268 52.68%
Skin corrosion - 0.9631 96.31%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5152 51.52%
Micronuclear - 0.8000 80.00%
Hepatotoxicity - 0.5920 59.20%
skin sensitisation - 0.8914 89.14%
Respiratory toxicity - 0.5333 53.33%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity + 0.7049 70.49%
Acute Oral Toxicity (c) III 0.4698 46.98%
Estrogen receptor binding + 0.8095 80.95%
Androgen receptor binding + 0.6169 61.69%
Thyroid receptor binding - 0.5382 53.82%
Glucocorticoid receptor binding + 0.6351 63.51%
Aromatase binding + 0.5260 52.60%
PPAR gamma - 0.5000 50.00%
Honey bee toxicity - 0.6254 62.54%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.6500 65.00%
Fish aquatic toxicity + 0.9939 99.39%

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 98.94% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.53% 91.11%
CHEMBL204 P00734 Thrombin 96.32% 96.01%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.97% 85.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.64% 94.45%
CHEMBL221 P23219 Cyclooxygenase-1 93.47% 90.17%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 93.37% 95.71%
CHEMBL340 P08684 Cytochrome P450 3A4 92.50% 91.19%
CHEMBL2581 P07339 Cathepsin D 91.84% 98.95%
CHEMBL226 P30542 Adenosine A1 receptor 90.26% 95.93%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 89.94% 95.89%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 89.85% 94.33%
CHEMBL4005 P42336 PI3-kinase p110-alpha subunit 88.71% 97.47%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 87.73% 96.47%
CHEMBL4040 P28482 MAP kinase ERK2 87.06% 83.82%
CHEMBL3437 Q16853 Amine oxidase, copper containing 86.45% 94.00%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 86.11% 92.88%
CHEMBL3060 Q9Y345 Glycine transporter 2 86.00% 99.17%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 85.87% 97.21%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 85.85% 98.75%
CHEMBL4227 P25090 Lipoxin A4 receptor 85.45% 100.00%
CHEMBL1871 P10275 Androgen Receptor 83.87% 96.43%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.83% 100.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 83.70% 96.00%
CHEMBL5028 O14672 ADAM10 83.33% 97.50%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 82.93% 91.07%
CHEMBL2001 Q9H244 Purinergic receptor P2Y12 82.77% 96.00%
CHEMBL3892 Q99500 Sphingosine 1-phosphate receptor Edg-3 82.14% 97.29%
CHEMBL253 P34972 Cannabinoid CB2 receptor 80.95% 97.25%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.79% 95.89%
CHEMBL2664 P23526 Adenosylhomocysteinase 80.28% 86.67%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 80.13% 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.
Centaurea attica

Cross-Links

Top
PubChem 163002514
LOTUS LTS0020282
wikiData Q104981349