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Bigelovin

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 7417852f-fc24-45a0-988a-bd913bffc4dd
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
IUPAC Name [(3aS,5R,5aR,8aR,9S,9aR)-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] acetate
SMILES (Canonical) CC1CC2C(C(C3(C1C=CC3=O)C)OC(=O)C)C(=C)C(=O)O2
SMILES (Isomeric) C[C@@H]1C[C@H]2[C@H]([C@@H]([C@]3([C@H]1C=CC3=O)C)OC(=O)C)C(=C)C(=O)O2
InChI InChI=1S/C17H20O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h5-6,8,11-12,14-15H,2,7H2,1,3-4H3/t8-,11+,12+,14-,15+,17+/m1/s1
InChI Key DCNRYQODUSSOKC-MMLVVLEOSA-N
Popularity 16 references in papers

Physical and Chemical Properties

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Molecular Formula C17H20O5
Molecular Weight 304.34 g/mol
Exact Mass 304.13107373 g/mol
Topological Polar Surface Area (TPSA) 69.70 Ų
XlogP 2.00
Atomic LogP (AlogP) 1.82
H-Bond Acceptor 5
H-Bond Donor 0
Rotatable Bonds 1

Synonyms

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3668-14-2
CHEBI:69337
[(3aS,5R,5aR,8aR,9S,9aR)-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] acetate
(3ar,4s,4ar,7ar,8r,9as)-4a,8-Dimethyl-3-Methylidene-2,5-Dioxo-2,3,3a,4,4a,5,7a,8,9,9a-Decahydroazuleno[6,5-B]furan-4-Yl Acetate
3ozj
6-O-acetylmexicanin
CHEMBL486997
DTXSID80190130
AKOS040763664
MS-24395
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Bigelovin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9859 98.59%
Caco-2 + 0.6104 61.04%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.4760 47.60%
OATP2B1 inhibitior - 0.8608 86.08%
OATP1B1 inhibitior + 0.8966 89.66%
OATP1B3 inhibitior + 0.8659 86.59%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.8983 89.83%
P-glycoprotein inhibitior - 0.6524 65.24%
P-glycoprotein substrate - 0.7891 78.91%
CYP3A4 substrate + 0.6174 61.74%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9138 91.38%
CYP3A4 inhibition - 0.5991 59.91%
CYP2C9 inhibition - 0.8777 87.77%
CYP2C19 inhibition - 0.8422 84.22%
CYP2D6 inhibition - 0.9674 96.74%
CYP1A2 inhibition - 0.6352 63.52%
CYP2C8 inhibition - 0.6929 69.29%
CYP inhibitory promiscuity - 0.8489 84.89%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.8943 89.43%
Carcinogenicity (trinary) Non-required 0.4685 46.85%
Eye corrosion - 0.9488 94.88%
Eye irritation - 0.8123 81.23%
Skin irritation - 0.6261 62.61%
Skin corrosion - 0.8939 89.39%
Ames mutagenesis - 0.7400 74.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5652 56.52%
Micronuclear - 0.5600 56.00%
Hepatotoxicity + 0.8625 86.25%
skin sensitisation - 0.5520 55.20%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.5556 55.56%
Mitochondrial toxicity + 0.6875 68.75%
Nephrotoxicity + 0.6678 66.78%
Acute Oral Toxicity (c) II 0.4805 48.05%
Estrogen receptor binding + 0.6118 61.18%
Androgen receptor binding - 0.5291 52.91%
Thyroid receptor binding - 0.5409 54.09%
Glucocorticoid receptor binding - 0.5551 55.51%
Aromatase binding + 0.5177 51.77%
PPAR gamma - 0.5529 55.29%
Honey bee toxicity - 0.7095 70.95%
Biodegradation - 0.6500 65.00%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.9713 97.13%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL1293277 O15118 Niemann-Pick C1 protein 631 nM
 Potency
 via Super-PRED
CHEMBL2061 P19793 Retinoid X receptor alpha 4.9 nM
 ED50
 PMID: 24959987

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.40% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.78% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.94% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.88% 86.33%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.87% 85.14%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.55% 99.23%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.34% 96.09%
CHEMBL2996 Q05655 Protein kinase C delta 87.83% 97.79%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.15% 95.56%
CHEMBL221 P23219 Cyclooxygenase-1 85.36% 90.17%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 84.05% 94.80%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.58% 95.50%
CHEMBL5028 O14672 ADAM10 81.05% 97.50%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.02% 91.07%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.01% 89.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.30% 97.14%
CHEMBL340 P08684 Cytochrome P450 3A4 80.05% 91.19%

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.
Artocarpus heterophyllus
Cichorium pumilum
Dittrichia graveolens
Helenium donianum
Inula hupehensis

Cross-Links

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PubChem 3080597
NPASS NPC70595
ChEMBL CHEMBL486997
LOTUS LTS0246145
wikiData Q27137678