Hiravanone - Compound Card

Hiravanone

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Hiravanone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles COc1cc(ccc1O)C1CC(=O)c2c(O1)c(CC=C(C)C)c(c(c2O)CC=C(C)C)O
InChI InChI=1S/C26H30O6/c1-14(2)6-9-17-24(29)18(10-7-15(3)4)26-23(25(17)30)20(28)13-21(32-26)16-8-11-19(27)22(12-16)31-5/h6-8,11-12,21,27,29-30H,9-10,13H2,1-5H3
InChIKey JBDKVARPSUMQCX-UHFFFAOYSA-N
Formula C26H30O6
HBA 6
HBD 3
MW 438.52
Rotatable Bonds 6
TPSA 96.22
LogP 5.54
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 438.2
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Pseudarthria hookeri Leguminosae/Fabaceae Plantae 992776

Showing of synonyms

  • Tchamgoue J, Hafizur R, et al. (2016). Flavonoids and other constituents with insulin secretion activity from Pseudarthria hookeri. Phytochemistry Letters, 2016, 17, 181-186. [View]
Pubchem: 14542255
Nmrshiftdb2: 60081111

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 438.52 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 438.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 438.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.04
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.850
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.98

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.120
Plasma Protein Binding
64.48
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
8.690
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.400
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.520
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.200
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-45.680
Rat (Acute)
2.070
Rat (Chronic Oral)
3.190
Fathead Minnow
5.370
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
475.180
Hydration Free Energy
-4.130
Log(D) at pH=7.4
3.840
Log(P)
6.04
Log S
-6.93
Log(Vapor Pressure)
-8.78
Melting Point
158.63
pKa Acid
8.0
pKa Basic
6.05
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9464
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9421
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9399
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9348
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9270
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9135
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9072
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9067
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8807
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8721
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8686
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8677
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8669
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8477
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.8461
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8438
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.8424
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8391
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8348
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.8312
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8267
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8251
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8207
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8187
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8187
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8163
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8083
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8036
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7993
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7991
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7984
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7953
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7921
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7871
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7859
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7853
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7852
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7837
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7832
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7828
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7824
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7796
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7794
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7782
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7729
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 4 0.7726
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7724
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7715
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7699
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7690
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7672
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7669
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7665
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7566
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7564
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7560
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7536
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7531
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7511
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7496
Uridine kinase Q5SKR5 URK_THET8 Thermus thermophilus 5 0.7487
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7485
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7478
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7473
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7464
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7454
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7444
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7422
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7418
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7414
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7399
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7398
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7394
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7391
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7379
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7379
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7347
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.7345
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7333
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7329
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7318
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7317
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7288
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7280
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7252
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7251
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7238
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7237
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7236
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7196
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7166
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7163
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7162
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7158
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7155
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7154
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7152
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7145
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7138
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 2 0.7137
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7133
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7132
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7130
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7130
Histone-lysine N-methyltransferase 2C Q8NEZ4 KMT2C_HUMAN Homo sapiens 3 0.7129
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7118
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7113
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7112
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 4 0.7106
Rho family GTPase C4M4W4 C4M4W4_ENTHI Entamoeba histolytica 4 0.7105
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7092
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7088
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7081
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7070
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7057
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7055
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7037
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7023
DNA-(apurinic or apyrimidinic site) lyase Q97FM4 Q97FM4_CLOAB Clostridium acetobutylicum 4 0.7022
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7016
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7015
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7009
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7005

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