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Licoagroisoflavone

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Isoflavonoid

Canonical Smiles	CC(=C)[C@@H]1Oc2c(C1)c(O)c1c(c2)occ(c1=O)c1ccc(cc1)O
InChI	InChI=1S/C20H16O5/c1-10(2)15-7-13-16(25-15)8-17-18(19(13)22)20(23)14(9-24-17)11-3-5-12(21)6-4-11/h3-6,8-9,15,21-22H,1,7H2,2H3/t15-/m1/s1
InChIKey	CQXOSSCKEFRIBR-OAHLLOKOSA-N
Formula	C₂₀H₁₆O₅
HBA	5
HBD	2
MW	336.34
Rotatable Bonds	2
TPSA	79.9
LogP	3.75
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.15
Exact Mass	336.1
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: 636883

Cas: 382137-37-3

Zinc: ZINC000032296427

Chebi: 70035

Nmrshiftdb2: 3410

Metabolights: MTBLC70035

Chembl: CHEMBL1689288

No compound-protein relationship available.

SMILES: C1COc(c12)cc3c(c2)c(=O)c(co3)-c4ccccc4

Level: 1

Mol. Weight: 336.34 g/mol

SMILES: C1COc(c12)cc3c(c2)c(=O)cco3

Level: 0

Mol. Weight: 336.34 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 336.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.71
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.81
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.61

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.05
Plasma Protein Binding: 89.06
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: Non-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: 3.72
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.56
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.4
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.34
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Toxic
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: 0.14
Rat (Acute): 2.72
Rat (Chronic Oral): 2.19
Fathead Minnow: 4.87
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 474.08
Hydration Free Energy: -10.73
Log(D) at pH=7.4: 3.98
Log(P): 4.62
Log S: -5.7
Log(Vapor Pressure): -10.11
Melting Point: 261.32
pKa Acid: 7.21
pKa Basic: 4.98

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9696
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9496
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.9265
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.9263
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	5	0.9185
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.9167
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.9093
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8877
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.8845
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8779
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8771
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8771
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.8762
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8756
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8660
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8414
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8395
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8365
Isoflavone-7-O-methyltransferase 8	O24529	7OMT8_MEDSA	Medicago sativa	5	0.8338
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8279
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8278
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.8237
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8231
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.8161
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8161
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8154
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8104
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.8096
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.8067
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7961
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7945
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7916
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7887
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7841
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7839
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7790
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7762
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7745
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7707
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7704
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7685
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7661
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7639
Bifunctional dihydrofolate reductase-thymidylate synthase	A7UD81	A7UD81_PLAFA	Plasmodium falciparum	4	0.7628
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7566
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7564
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7561
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7556
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7538
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7530
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7523
Tau-tubulin kinase 1	Q5TCY1	TTBK1_HUMAN	Homo sapiens	3	0.7518
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7513
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7479
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7469
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	2	0.7437
Reductase homolog	Q9ZGC1	Q9ZGC1_STRCY	Streptomyces cyanogenus	3	0.7434
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7433
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7424
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7414
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7401
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7391
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7384
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7381
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7355
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7315
Gag-Pol polyprotein	O12158	POL_HV192	Human immunodeficiency virus type 1 group M subtype C	3	0.7266
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7265
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7234
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7230
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7227
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7223
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7197
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7188
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7172
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7151
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7131
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7110
Ribonuclease TTHA0252	Q5SLP1	RNSE_THET8	Thermus thermophilus	3	0.7109
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7105
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7102
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7098
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7096
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7085
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7081
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7056
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7042
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7031
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7028
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7026
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7025
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	2	0.7025

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