Prebarbigerone - Compound Card

Prebarbigerone

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Prebarbigerone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone
Canonical Smiles COc1cc(OC)c(cc1c1coc2c(c1=O)ccc(c2CC=C(C)C)OC)OC
InChI InChI=1S/C24H26O6/c1-14(2)7-8-15-19(26-3)10-9-16-23(25)18(13-30-24(15)16)17-11-21(28-5)22(29-6)12-20(17)27-4/h7,9-13H,8H2,1-6H3
InChIKey RJNWIKZTUCDSTR-UHFFFAOYSA-N
Formula C24H26O6
HBA 6
HBD 0
MW 410.47
Rotatable Bonds 7
TPSA 67.13
LogP 5.0
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 410.17
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Millettia griffoniana Leguminosae/Fabaceae Plantae 3090223
2 Millettia ferruginea Leguminosae/Fabaceae Plantae 1096003

Showing of synonyms

  • Buyinza D, Chalo DM, et al. (2020). Flavonoids and Isoflavonoids of Millettia dura and Millettia ferruginea: Phytochemical review and chemotaxonomic values. Biochemical Systematics and Ecology, 2020, 91, 104053. [View]
  • Ngamga D, Yankep E, et al. (2005). Isoflavonoids from Seeds of Millettia griffoniana (Bail). Zeitschrift für Naturforschung B. 2005, 60(9), 973-977. [View]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)occ(c2=O)-c3ccccc3

Level: 1

Mol. Weight: 410.47 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 410.47 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 410.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.560
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.420
Plasma Protein Binding
76.6
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
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.380
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
0.760
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.570
Micronucleos
Safe
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
-23.780
Rat (Acute)
2.760
Rat (Chronic Oral)
1.880
Fathead Minnow
5.960
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
483.860
Hydration Free Energy
-5.400
Log(D) at pH=7.4
3.600
Log(P)
4.94
Log S
-5.21
Log(Vapor Pressure)
-7.48
Melting Point
140.03
pKa Acid
9.6
pKa Basic
4.52
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9557
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9528
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9462
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.9390
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9294
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.9288
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9265
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9081
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9028
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8865
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8864
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8859
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8834
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8727
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8699
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8653
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8571
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8533
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8311
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.8282
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8235
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8172
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8164
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8126
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8125
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8116
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8086
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.8054
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8050
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8038
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8027
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8025
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8015
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8007
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7981
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7937
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7909
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7889
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7886
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7883
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7878
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7874
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7826
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7819
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7819
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7815
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7794
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7783
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7775
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7730
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7714
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7713
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7691
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7683
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7679
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7669
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7667
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7666
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7623
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7615
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7597
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7588
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7584
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7582
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7546
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7541
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7538
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7511
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7509
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7507
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7499
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7496
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7495
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7462
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7459
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7457
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7454
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7452
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7424
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7421
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7420
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7418
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7416
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7391
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7386
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7359
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7355
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7355
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7345
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7344
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7339
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7338
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7329
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7329
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7323
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7322
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7319
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7316
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7308
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7303
Acetolactate synthase catalytic subunit, mitochondrial P07342 ILVB_YEAST Saccharomyces cerevisiae 3 0.7300
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7297
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7257
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7257
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7247
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7244
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7214
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7213
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7208
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7207
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7196
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7190
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7185
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7182
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7181
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7176
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7175
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7175
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7169
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7168
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7164
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7156
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7145
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7124
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7120
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 2 0.7115
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 3 0.7115
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7103
Interleukin-2 P60568 IL2_HUMAN Homo sapiens 2 0.7100
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7096
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7086
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7079
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7075
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7075
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7075
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7073
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7063
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7055
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7055
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7051
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7038
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7029
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7028
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7016
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7013
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7008
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7006

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