Barbigerone - Compound Card

Barbigerone

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Barbigerone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Pyranoisoflavone
Canonical Smiles COc1cc(OC)c(cc1c1coc2c(c1=O)ccc1c2C=CC(O1)(C)C)OC
InChI InChI=1S/C23H22O6/c1-23(2)9-8-13-17(29-23)7-6-14-21(24)16(12-28-22(13)14)15-10-19(26-4)20(27-5)11-18(15)25-3/h6-12H,1-5H3
InChIKey OBIUGMGQVQMVSK-UHFFFAOYSA-N
Formula C23H22O6
HBA 6
HBD 0
MW 394.42
Rotatable Bonds 4
TPSA 67.13
LogP 4.67
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.26
Exact Mass 394.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Millettia usaramensis usaramensis Leguminosae/Fabaceae Plantae 53625
2 Millettia usaramensis usaramensis Leguminosae/Fabaceae Plantae 53625

Showing of synonyms

  • Yenesew A, Derese S, et al. (2003). Anti-plasmodial activities and X-ray crystal structures of rotenoids from Millettia usaramensis subspecies usaramensis.. Phytochemistry,2003,64(3),773-779. [View] [PubMed]
  • Yenesew A, Midiwo JO, et al. (1998). Rotenoids, isoflavones and chalcones from the stem bark of Millettia usaramensis subspecies usaramensis. Phytochemistry,1998,47(2),295-300. [View] [PubMed]
Pubchem: 156793
Nmrshiftdb2: 60069151
Pdb Ligand: J6L
Bindingdb: 50505210
CPRiL: 141946
Structure

SMILES: C1=CCOc(cc2)c1c(c23)occ(c3=O)-c4ccccc4

Level: 1

Mol. Weight: 394.42 g/mol

Structure

SMILES: O=c1ccoc(c12)c3c(cc2)OCC=C3

Level: 0

Mol. Weight: 394.42 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 394.42 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.540
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.1

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.510
Plasma Protein Binding
70.01
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.580
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.250
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.870
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.210
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-15.670
Rat (Acute)
3.620
Rat (Chronic Oral)
1.740
Fathead Minnow
5.650
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
484.430
Hydration Free Energy
-6.370
Log(D) at pH=7.4
3.380
Log(P)
4.34
Log S
-4.98
Log(Vapor Pressure)
-7.79
Melting Point
172.21
pKa Acid
9.3
pKa Basic
3.12
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9492
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9492
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.9311
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.9311
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9309
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9309
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9225
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9225
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9214
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9214
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8759
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8759
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8708
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8708
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8672
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8672
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8606
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8606
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8547
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8547
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8474
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8474
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.8207
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.8207
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8075
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8075
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8057
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8057
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8035
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8035
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8011
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8011
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8003
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8003
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7993
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7993
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7964
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7964
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7880
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7880
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7850
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7850
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7832
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7832
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7810
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7810
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7805
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7805
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7788
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7788
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7727
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7727
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7665
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7665
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7618
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7618
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7616
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7616
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7572
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7572
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7558
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7558
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7557
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7557
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7537
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7537
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7511
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7511
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7499
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7499
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7484
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7484
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7475
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7475
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7462
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7462
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7443
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7443
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7440
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7440
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7418
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7418
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7402
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7402
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7399
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7399
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7391
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7391
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7391
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7391
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7378
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7378
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7358
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7358
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7346
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7346
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7341
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7341
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7329
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7329
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7327
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7327
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7321
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7321
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7320
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7320
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7317
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7317
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7314
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7314
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7310
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7310
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7310
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7310
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7304
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7304
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7288
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7288
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7282
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7282
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7281
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7281
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7249
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7249
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7242
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7242
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7221
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7221
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7209
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7209
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7198
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7198
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7185
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7185
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7178
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7178
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7174
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7174
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7167
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7167
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7160
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7160
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7156
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7156
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7138
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7138
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7121
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7121
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7092
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7092
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7088
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7088
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7085
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7085
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7085
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7085
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7076
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7076
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7071
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7071
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7054
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7054
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7053
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7053
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7003
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7003

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