Lachnoisoflavone A - Compound Card

Lachnoisoflavone A

Select a section from the left sidebar

Lachnoisoflavone A

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavonoid
Canonical Smiles CC(=C)C1Cc2c(O1)c1c(cc2O)occ(c1=O)c1ccc(cc1O)O
InChI InChI=1S/C20H16O6/c1-9(2)16-6-12-15(23)7-17-18(20(12)26-16)19(24)13(8-25-17)11-4-3-10(21)5-14(11)22/h3-5,7-8,16,21-23H,1,6H2,2H3
InChIKey HHQAAUSMOBNXFL-UHFFFAOYSA-N
Formula C20H16O6
HBA 6
HBD 3
MW 352.34
Rotatable Bonds 2
TPSA 100.13
LogP 3.46
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.15
Exact Mass 352.09
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: 51041993
Chebi: 70028
Nmrshiftdb2: 70120043
Metabolights: MTBLC70028

No compound-protein relationship available.

Structure

SMILES: C1COc(c12)c3c(cc2)occ(c3=O)-c4ccccc4

Level: 1

Mol. Weight: 352.34 g/mol

Structure

SMILES: C1COc(c12)c3c(cc2)occc3=O

Level: 0

Mol. Weight: 352.34 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 352.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.92
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.88
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.05
Plasma Protein Binding
78.83
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-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
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.24
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.41
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.18
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.16
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-0.17
Rat (Acute)
2.48
Rat (Chronic Oral)
2.6
Fathead Minnow
4.88
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
492.96
Hydration Free Energy
-10.66
Log(D) at pH=7.4
3.2
Log(P)
3.61
Log S
-5.84
Log(Vapor Pressure)
-10.13
Melting Point
272.41
pKa Acid
7.05
pKa Basic
5.95
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9573
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9266
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9164
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 5 0.9117
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9092
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9092
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.9012
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8922
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8891
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8838
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8802
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.8732
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.8663
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8599
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8501
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8461
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8452
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8424
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8365
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8347
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8303
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8274
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8250
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8177
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8171
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8165
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8156
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.8134
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8131
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 4 0.8123
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8075
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8063
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8056
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.8014
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.8004
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7880
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7878
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7774
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7770
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7736
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7713
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7667
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7634
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7620
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7620
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7600
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7561
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7535
Nucleoside diphosphate kinase P15266 NDK_MYXXA Myxococcus xanthus 3 0.7532
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7524
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7513
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7509
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7507
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7489
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7469
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7452
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7450
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7447
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7439
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7438
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7431
Bromodomain protein, putative Q8I240 Q8I240_PLAF7 Plasmodium falciparum 5 0.7406
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7348
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7345
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7328
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7327
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7322
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.7313
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7305
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7302
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7292
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7291
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7282
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7275
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7266
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 4 0.7259
Phosphodiesterase Q53I60 Q53I60_TRYCR Trypanosoma cruzi 3 0.7259
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7244
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7241
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7208
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7202
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7200
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7196
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7182
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7149
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7148
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7147
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7104
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7087
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7081
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7064
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7062
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7059
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7053
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 4 0.7041
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7039

Download SDF