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Barbourgenin

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 6e3a368e-50d4-4fc8-a67b-ed2ad9077286
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S,16S,18S)-5'-(hydroxymethyl)-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-ol
SMILES (Canonical) CC1C2C(CC3C2(CCC4C3CCC5C4(CCC(C5)O)C)C)OC16CCC(CO6)CO
SMILES (Isomeric) C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC[C@@H]5[C@@]4(CC[C@@H](C5)O)C)C)O[C@]16CC[C@H](CO6)CO
InChI InChI=1S/C27H44O4/c1-16-24-23(31-27(16)11-6-17(14-28)15-30-27)13-22-20-5-4-18-12-19(29)7-9-25(18,2)21(20)8-10-26(22,24)3/h16-24,28-29H,4-15H2,1-3H3/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1
InChI Key VMVODFKYINXZDT-PUHUBZITSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C27H44O4
Molecular Weight 432.60 g/mol
Exact Mass 432.32395988 g/mol
Topological Polar Surface Area (TPSA) 58.90 Ų
XlogP 5.30
Atomic LogP (AlogP) 4.77
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 1

Synonyms

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105815-87-0
Spirostane-3,27-diol
Spirostan-3,27-diol
DTXSID10909752
Spirostan-3,27-diol, (3beta,5alpha,25S)-
(1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S,16S,18S)-5'-(hydroxymethyl)-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-ol

2D Structure

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2D Structure of Barbourgenin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9034 90.34%
Caco-2 - 0.5950 59.50%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.5481 54.81%
OATP2B1 inhibitior - 0.5705 57.05%
OATP1B1 inhibitior + 0.8918 89.18%
OATP1B3 inhibitior + 0.8592 85.92%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.5102 51.02%
BSEP inhibitior - 0.5887 58.87%
P-glycoprotein inhibitior - 0.6471 64.71%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.7201 72.01%
CYP2C9 substrate - 0.8086 80.86%
CYP2D6 substrate - 0.7483 74.83%
CYP3A4 inhibition - 0.9251 92.51%
CYP2C9 inhibition - 0.9151 91.51%
CYP2C19 inhibition - 0.8960 89.60%
CYP2D6 inhibition - 0.9482 94.82%
CYP1A2 inhibition - 0.9150 91.50%
CYP2C8 inhibition + 0.5155 51.55%
CYP inhibitory promiscuity - 0.9624 96.24%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5690 56.90%
Eye corrosion - 0.9900 99.00%
Eye irritation - 0.9366 93.66%
Skin irritation - 0.7422 74.22%
Skin corrosion - 0.9576 95.76%
Ames mutagenesis - 0.7079 70.79%
Human Ether-a-go-go-Related Gene inhibition - 0.4787 47.87%
Micronuclear - 0.9200 92.00%
Hepatotoxicity - 0.7390 73.90%
skin sensitisation - 0.9268 92.68%
Respiratory toxicity + 0.8111 81.11%
Reproductive toxicity + 0.7111 71.11%
Mitochondrial toxicity + 0.5625 56.25%
Nephrotoxicity - 0.7106 71.06%
Acute Oral Toxicity (c) I 0.4525 45.25%
Estrogen receptor binding + 0.6467 64.67%
Androgen receptor binding + 0.5429 54.29%
Thyroid receptor binding + 0.6682 66.82%
Glucocorticoid receptor binding + 0.7949 79.49%
Aromatase binding + 0.6980 69.80%
PPAR gamma + 0.5625 56.25%
Honey bee toxicity - 0.6940 69.40%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.6850 68.50%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.82% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.25% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 92.12% 100.00%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 90.51% 89.05%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 90.33% 91.11%
CHEMBL237 P41145 Kappa opioid receptor 89.95% 98.10%
CHEMBL218 P21554 Cannabinoid CB1 receptor 87.35% 96.61%
CHEMBL3045 P05771 Protein kinase C beta 85.16% 97.63%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 84.89% 95.50%
CHEMBL253 P34972 Cannabinoid CB2 receptor 84.67% 97.25%
CHEMBL2996 Q05655 Protein kinase C delta 84.42% 97.79%
CHEMBL2140 P48775 Tryptophan 2,3-dioxygenase 83.09% 98.46%
CHEMBL4523377 Q86WV6 Stimulator of interferon genes protein 82.81% 95.48%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.54% 95.89%
CHEMBL1871 P10275 Androgen Receptor 82.47% 96.43%

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.
There are no matching plants.

Cross-Links

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PubChem 129125
LOTUS LTS0217371
wikiData Q82879413