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Burrodin

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 cedf566e-df05-49be-b51a-92d2b451a8c4
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
IUPAC Name (3aR,5S,5aS,6S,8aS,9aR)-6-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,6,7,9,9a-octahydroazuleno[6,7-b]furan-2,8-dione
SMILES (Canonical) CC1CC2C(CC3(C1C(CC3=O)O)C)C(=C)C(=O)O2
SMILES (Isomeric) C[C@H]1C[C@@H]2[C@H](C[C@]3([C@H]1[C@H](CC3=O)O)C)C(=C)C(=O)O2
InChI InChI=1S/C15H20O4/c1-7-4-11-9(8(2)14(18)19-11)6-15(3)12(17)5-10(16)13(7)15/h7,9-11,13,16H,2,4-6H2,1,3H3/t7-,9+,10-,11+,13+,15+/m0/s1
InChI Key HSNYUOAAQCCKRP-UGKIOTTESA-N
Popularity 3 references in papers

Physical and Chemical Properties

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Molecular Formula C15H20O4
Molecular Weight 264.32 g/mol
Exact Mass 264.13615911 g/mol
Topological Polar Surface Area (TPSA) 63.60 Ų
XlogP 1.40
Atomic LogP (AlogP) 1.47
H-Bond Acceptor 4
H-Bond Donor 1
Rotatable Bonds 0

Synonyms

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20555-02-6
CHEBI:69343
(3aR,5S,5aS,6S,8aS,9aR)-6-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,6,7,9,9a-octahydroazuleno[6,7-b]furan-2,8-dione
DTXSID40174557
10alphaH-Ambros-11(13)-en-12-oic acid, 2alpha,8beta-dihydroxy-4-oxo-, gamma-lactone
2alpha,8beta-dihydroxy-4-oxo-10alphaH-ambros-11(13)-en-12-oic acid gamma-lactone
(3aR,4aS,7S,7aS,8S,9aR)-7-hydroxy-4a,8-dimethyl-3-methylene-decahydroazuleno(6,5-b)furan-2,5-dione
(3aR,4aS,7S,7aS,8S,9aR)-7-hydroxy-4a,8-dimethyl-3-methylidenedecahydroazuleno[6,5-b]furan-2,5-dione
Azuleno(6,5-b)furan-2,5-dione, decahydro-7-hydroxy-4a,8-dimethyl-3-methylene-, (3aR,4aS,7S,7aS,8S,9aR)-
Azuleno(6,5-b)furan-2,5-dione, decahydro-7-hydroxy-4a,8-dimethyl-3-methylene-, (3aR-(3aalpha,4abeta,7alpha,7aalpha,8beta,9aalpha))-
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Burrodin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9814 98.14%
Caco-2 + 0.5864 58.64%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.5423 54.23%
OATP2B1 inhibitior - 0.8536 85.36%
OATP1B1 inhibitior + 0.8692 86.92%
OATP1B3 inhibitior + 0.9274 92.74%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior - 0.9024 90.24%
P-glycoprotein inhibitior - 0.8845 88.45%
P-glycoprotein substrate - 0.7881 78.81%
CYP3A4 substrate + 0.5975 59.75%
CYP2C9 substrate - 0.7928 79.28%
CYP2D6 substrate - 0.8748 87.48%
CYP3A4 inhibition - 0.7473 74.73%
CYP2C9 inhibition - 0.8895 88.95%
CYP2C19 inhibition - 0.8810 88.10%
CYP2D6 inhibition - 0.9598 95.98%
CYP1A2 inhibition - 0.6169 61.69%
CYP2C8 inhibition - 0.7739 77.39%
CYP inhibitory promiscuity - 0.9705 97.05%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.5466 54.66%
Eye corrosion - 0.9788 97.88%
Eye irritation - 0.7641 76.41%
Skin irritation + 0.5431 54.31%
Skin corrosion - 0.8695 86.95%
Ames mutagenesis - 0.6624 66.24%
Human Ether-a-go-go-Related Gene inhibition - 0.6674 66.74%
Micronuclear - 0.6900 69.00%
Hepatotoxicity + 0.8337 83.37%
skin sensitisation - 0.7297 72.97%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.7222 72.22%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity + 0.7457 74.57%
Acute Oral Toxicity (c) II 0.5555 55.55%
Estrogen receptor binding + 0.6681 66.81%
Androgen receptor binding + 0.6055 60.55%
Thyroid receptor binding - 0.6017 60.17%
Glucocorticoid receptor binding - 0.5086 50.86%
Aromatase binding - 0.6362 63.62%
PPAR gamma - 0.7081 70.81%
Honey bee toxicity - 0.7435 74.35%
Biodegradation - 0.5500 55.00%
Crustacea aquatic toxicity + 0.6500 65.00%
Fish aquatic toxicity + 0.9921 99.21%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL230 P35354 Cyclooxygenase-2 3800 nM
 IC50
 PMID: 16038536

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.35% 85.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.78% 91.11%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 90.58% 99.23%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.45% 97.09%
CHEMBL2996 Q05655 Protein kinase C delta 88.44% 97.79%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.28% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 87.22% 97.25%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.74% 86.33%
CHEMBL241 Q14432 Phosphodiesterase 3A 85.56% 92.94%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 83.60% 96.09%
CHEMBL299 P17252 Protein kinase C alpha 82.37% 98.03%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.99% 100.00%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 80.72% 93.03%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.30% 94.45%

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.
Inula hupehensis

Cross-Links

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PubChem 177140
NPASS NPC200237
ChEMBL CHEMBL509159
LOTUS LTS0040427
wikiData Q27137684