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[(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] (2S)-2-methyloxirane-2-carboxylate

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

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Internal ID 302c5ef1-74f9-4607-8335-fd7584574aa6
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] (2S)-2-methyloxirane-2-carboxylate
SMILES (Canonical) CC12CC(C3C(C1C4(CCC2OC(=O)C5(CO5)C)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@@]5(CO5)C)CO4)OC(=O)C3=C)O
InChI InChI=1S/C19H24O7/c1-9-12-10(20)6-17(2)11(25-16(22)18(3)7-23-18)4-5-19(8-24-19)14(17)13(12)26-15(9)21/h10-14,20H,1,4-8H2,2-3H3/t10-,11-,12+,13-,14+,17-,18-,19-/m0/s1
InChI Key HEQDIEIDUUANIO-FHMCGTCESA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C19H24O7
Molecular Weight 364.40 g/mol
Exact Mass 364.15220310 g/mol
Topological Polar Surface Area (TPSA) 97.90 Ų
XlogP 0.90
Atomic LogP (AlogP) 0.73
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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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] (2S)-2-methyloxirane-2-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9775 97.75%
Caco-2 + 0.5112 51.12%
Blood Brain Barrier + 0.7500 75.00%
Human oral bioavailability + 0.5429 54.29%
Subcellular localzation Mitochondria 0.7813 78.13%
OATP2B1 inhibitior - 0.8627 86.27%
OATP1B1 inhibitior + 0.8903 89.03%
OATP1B3 inhibitior + 0.9519 95.19%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.5021 50.21%
BSEP inhibitior - 0.7378 73.78%
P-glycoprotein inhibitior - 0.6912 69.12%
P-glycoprotein substrate - 0.7068 70.68%
CYP3A4 substrate + 0.6927 69.27%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8492 84.92%
CYP3A4 inhibition - 0.6451 64.51%
CYP2C9 inhibition - 0.8466 84.66%
CYP2C19 inhibition - 0.8967 89.67%
CYP2D6 inhibition - 0.9290 92.90%
CYP1A2 inhibition - 0.8087 80.87%
CYP2C8 inhibition - 0.7545 75.45%
CYP inhibitory promiscuity - 0.9580 95.80%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4891 48.91%
Eye corrosion - 0.9861 98.61%
Eye irritation - 0.9381 93.81%
Skin irritation - 0.5327 53.27%
Skin corrosion - 0.9107 91.07%
Ames mutagenesis - 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6343 63.43%
Micronuclear - 0.6300 63.00%
Hepatotoxicity + 0.6264 62.64%
skin sensitisation - 0.8191 81.91%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity + 0.7925 79.25%
Acute Oral Toxicity (c) III 0.3534 35.34%
Estrogen receptor binding + 0.8242 82.42%
Androgen receptor binding + 0.6597 65.97%
Thyroid receptor binding + 0.5337 53.37%
Glucocorticoid receptor binding + 0.7694 76.94%
Aromatase binding + 0.6446 64.46%
PPAR gamma + 0.6626 66.26%
Honey bee toxicity - 0.6927 69.27%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5450 54.50%
Fish aquatic toxicity + 0.9910 99.10%

Targets

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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 97.68% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.98% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.64% 94.45%
CHEMBL4040 P28482 MAP kinase ERK2 91.67% 83.82%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 91.56% 99.23%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.53% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.81% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.23% 89.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 87.62% 85.14%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 86.42% 82.69%
CHEMBL2581 P07339 Cathepsin D 86.21% 98.95%
CHEMBL241 Q14432 Phosphodiesterase 3A 86.10% 92.94%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.78% 95.89%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.67% 97.09%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.58% 97.14%
CHEMBL3922 P50579 Methionine aminopeptidase 2 83.51% 97.28%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 83.11% 98.75%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.93% 91.07%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 81.02% 93.03%
CHEMBL340 P08684 Cytochrome P450 3A4 80.66% 91.19%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.53% 92.62%
CHEMBL1871 P10275 Androgen Receptor 80.33% 96.43%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.26% 100.00%

Plants that contains it

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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

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PubChem 162981181
LOTUS LTS0261207
wikiData Q105026980