Lachnoisoflavone B - Compound Card

Lachnoisoflavone B

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Lachnoisoflavone B

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavonoid
Canonical Smiles CC(=C)C1Oc2c(C1)c(O)c1c(c2)oc2c(c1=O)c1c(o2)cc(cc1)O
InChI InChI=1S/C20H14O6/c1-8(2)12-6-11-14(24-12)7-15-17(18(11)22)19(23)16-10-4-3-9(21)5-13(10)25-20(16)26-15/h3-5,7,12,21-22H,1,6H2,2H3
InChIKey UVJBSWKDLJKBCL-UHFFFAOYSA-N
Formula C20H14O6
HBA 6
HBD 2
MW 350.33
Rotatable Bonds 1
TPSA 93.04
LogP 3.98
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.15
Exact Mass 350.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Crotalaria lachnophora Leguminosae/Fabaceae Plantae 1237651

Showing of synonyms

  • Awouafack MD, Spiteller P, et al. (2011). Antimicrobial isopropenyl-dihydrofuranoisoflavones from Crotalaria lachnophora.. Journal of natural products,2011, 74(2), 272-278. [View] [PubMed]
Pubchem: 51041994
Chebi: 70029
Nmrshiftdb2: 70059829
Metabolights: MTBLC70029

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1c23)oc2oc4c(c3=O)cc5c(c4)OCC5

Level: 0

Mol. Weight: 350.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.23

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.22
Plasma Protein Binding
82.26
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-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
9.31
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.57
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.13
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.21
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
-2.05
Rat (Acute)
2.74
Rat (Chronic Oral)
2.31
Fathead Minnow
5.24
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
544.0
Hydration Free Energy
-7.69
Log(D) at pH=7.4
3.76
Log(P)
5.18
Log S
-5.67
Log(Vapor Pressure)
-12.18
Melting Point
347.11
pKa Acid
5.46
pKa Basic
6.36
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9391
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9354
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.9299
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9163
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.9154
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9138
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9051
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.8986
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8969
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8967
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8856
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8784
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8719
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8652
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8641
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8566
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8456
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8361
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8330
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.8328
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8312
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 4 0.8218
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8127
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.8089
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.8053
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8034
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7977
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7971
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7932
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7875
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7844
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7840
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7839
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7829
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7799
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7798
Transthyretin P02766 TTHY_HUMAN Homo sapiens 4 0.7787
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7775
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7747
Gag-Pol polyprotein O12158 POL_HV192 Human immunodeficiency virus type 1 group M subtype C 3 0.7744
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7738
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7685
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7671
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7641
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7637
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7604
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7578
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7569
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7558
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7550
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 3 0.7545
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7542
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7529
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7515
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7506
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7500
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7487
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7482
Bromodomain protein, putative Q8I240 Q8I240_PLAF7 Plasmodium falciparum 4 0.7476
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7452
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7443
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7438
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7416
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7412
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7402
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7391
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7380
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7359
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7347
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7332
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7332
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7327
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7323
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7304
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7304
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7304
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 3 0.7301
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7291
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7291
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 4 0.7259
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7256
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7248
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7244
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7234
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7225
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7217
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7205
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7205
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 4 0.7195
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7193
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7178
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7173
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7173
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7143
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7143
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7128
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7125
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7123
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7103
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7102
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7089
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7078
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7074
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7073
Putative N-acetyl glucosaminyl transferase Q6U8B0 Q6U8B0_RAOTE Raoultella terrigena 3 0.7069
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7061
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7060
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7051
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7030
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7020
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7004

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