PlantaeDB Logo
Login Sign-up

[(3aR,4S,5aR,6S,9R,9aS,9bS)-4-hydroxy-5a-methyl-3-methylidene-2-oxospiro[3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-9,2'-oxirane]-6-yl] 2-(hydroxymethyl)prop-2-enoate

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 c48554e2-3f23-4175-8635-ebdc5eec7561
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name [(3aR,4S,5aR,6S,9R,9aS,9bS)-4-hydroxy-5a-methyl-3-methylidene-2-oxospiro[3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-9,2'-oxirane]-6-yl] 2-(hydroxymethyl)prop-2-enoate
SMILES (Canonical) CC12CC(C3C(C1C4(CCC2OC(=O)C(=C)CO)CO4)OC(=O)C3=C)O
SMILES (Isomeric) C[C@@]12C[C@@H]([C@@H]3[C@@H]([C@H]1[C@]4(CC[C@@H]2OC(=O)C(=C)CO)CO4)OC(=O)C3=C)O
InChI InChI=1S/C19H24O7/c1-9(7-20)16(22)25-12-4-5-19(8-24-19)15-14-13(10(2)17(23)26-14)11(21)6-18(12,15)3/h11-15,20-21H,1-2,4-8H2,3H3/t11-,12-,13+,14-,15+,18-,19-/m0/s1
InChI Key GWKXLGULTGZWQO-HZBHIOGJSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C19H24O7
Molecular Weight 364.40 g/mol
Exact Mass 364.15220310 g/mol
Topological Polar Surface Area (TPSA) 106.00 Ų
XlogP 0.70
Atomic LogP (AlogP) 0.49
H-Bond Acceptor 7
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of [(3aR,4S,5aR,6S,9R,9aS,9bS)-4-hydroxy-5a-methyl-3-methylidene-2-oxospiro[3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-9,2'-oxirane]-6-yl] 2-(hydroxymethyl)prop-2-enoate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9701 97.01%
Caco-2 - 0.5728 57.28%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.5000 50.00%
Subcellular localzation Mitochondria 0.7479 74.79%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8897 88.97%
OATP1B3 inhibitior + 0.9538 95.38%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior + 0.5229 52.29%
BSEP inhibitior - 0.8670 86.70%
P-glycoprotein inhibitior - 0.6897 68.97%
P-glycoprotein substrate - 0.5522 55.22%
CYP3A4 substrate + 0.6893 68.93%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8530 85.30%
CYP3A4 inhibition - 0.5810 58.10%
CYP2C9 inhibition - 0.8473 84.73%
CYP2C19 inhibition - 0.8639 86.39%
CYP2D6 inhibition - 0.9227 92.27%
CYP1A2 inhibition - 0.8005 80.05%
CYP2C8 inhibition - 0.7156 71.56%
CYP inhibitory promiscuity - 0.9041 90.41%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4469 44.69%
Eye corrosion - 0.9856 98.56%
Eye irritation - 0.9317 93.17%
Skin irritation - 0.5623 56.23%
Skin corrosion - 0.9198 91.98%
Ames mutagenesis - 0.6240 62.40%
Human Ether-a-go-go-Related Gene inhibition - 0.6440 64.40%
Micronuclear - 0.6700 67.00%
Hepatotoxicity - 0.5301 53.01%
skin sensitisation - 0.8369 83.69%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.7778 77.78%
Mitochondrial toxicity + 0.8375 83.75%
Nephrotoxicity + 0.8859 88.59%
Acute Oral Toxicity (c) III 0.4771 47.71%
Estrogen receptor binding + 0.8444 84.44%
Androgen receptor binding + 0.6307 63.07%
Thyroid receptor binding + 0.5587 55.87%
Glucocorticoid receptor binding + 0.7318 73.18%
Aromatase binding + 0.6598 65.98%
PPAR gamma + 0.6949 69.49%
Honey bee toxicity - 0.7551 75.51%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.6250 62.50%
Fish aquatic toxicity + 0.9867 98.67%

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 98.68% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.21% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.19% 94.45%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.63% 99.23%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.24% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.49% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.19% 95.56%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 85.99% 82.69%
CHEMBL253 P34972 Cannabinoid CB2 receptor 85.15% 97.25%
CHEMBL2581 P07339 Cathepsin D 85.06% 98.95%
CHEMBL2996 Q05655 Protein kinase C delta 84.01% 97.79%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.63% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.52% 86.33%
CHEMBL3922 P50579 Methionine aminopeptidase 2 83.16% 97.28%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.86% 100.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.00% 92.62%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.73% 97.14%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 80.73% 85.14%

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.
Dimerostemma brasilianum

Cross-Links

Top
PubChem 163019197
LOTUS LTS0265161
wikiData Q105022474