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Ferrugone

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

Canonical Smiles	COc1c2OCOc2c(cc1c1coc2c(c1=O)ccc1c2C=CC(O1)(C)C)OC
InChI	InChI=1S/C23H20O7/c1-23(2)8-7-12-16(30-23)6-5-13-18(24)15(10-27-19(12)13)14-9-17(25-3)21-22(20(14)26-4)29-11-28-21/h5-10H,11H2,1-4H3
InChIKey	RSVWXUPJBWWEJY-UHFFFAOYSA-N
Formula	C₂₃H₂₀O₇
HBA	7
HBD	0
MW	408.41
Rotatable Bonds	3
TPSA	76.36
LogP	4.39
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	30
Formal Charge	0
Fraction CSP3	0.26
Exact Mass	408.12
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Millettia dura	Leguminosae/Fabaceae	Plantae	62119

Showing of synonyms

Yenesew A, Midiwo JO, et al. (1997). 6-Methoxycalpogonium Isoflavone A: A New Isoflavone from the Seed Pods of Millettia dura.. Journal of Natural Products,1997,60(8),806–807. [View] [PubMed]

Pubchem: 324529

Cas: 7731-08-0

Nmrshiftdb2: 70009533

Comptox: DTXSID60314958

CPRiL: 415358

SMILES: O1COc(c12)ccc(c2)-c(c3=O)coc(c34)c5c(cc4)OCC=C5

Level: 1

Mol. Weight: 408.41 g/mol

SMILES: O=c1ccoc(c12)c3c(cc2)OCC=C3

Level: 0

Mol. Weight: 408.41 g/mol

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 408.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.87
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.540
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.96

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.590
Plasma Protein Binding: 77.52
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: Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.280
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.060
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.980
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.200
Micronucleos: Toxic
NR-AhR: Toxic
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: -51.110
Rat (Acute): 3.570
Rat (Chronic Oral): 1.410
Fathead Minnow: 5.730
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 497.340
Hydration Free Energy: -3.850
Log(D) at pH=7.4: 3.050
Log(P): 4.73
Log S: -4.86
Log(Vapor Pressure): -8.52
Melting Point: 175.93
pKa Acid: 8.89
pKa Basic: 0.58

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9473
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9473
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.9266
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.9266
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.9218
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.9218
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9182
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9182
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8870
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8870
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8764
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8764
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8750
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8750
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8630
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8630
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8374
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8374
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7896
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7896
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7875
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7875
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7825
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7825
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7801
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7801
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7800
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7800
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7794
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7794
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7645
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7645
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7636
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7636
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7608
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7608
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7602
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7602
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7600
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7600
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.7579
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.7579
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	3	0.7512
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	3	0.7512
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7469
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7469
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7464
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7464
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7426
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7426
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7410
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7410
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7405
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7405
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7402
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7402
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7368
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7368
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7365
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7365
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7358
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7358
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7350
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7350
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7345
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7345
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7343
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7343
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7337
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7337
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7319
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7319
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7306
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7306
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7169
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7169
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7162
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7162
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7116
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7116
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	4	0.7103
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	4	0.7103
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7098
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7098
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7097
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7097
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7078
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7078
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7075
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7075
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7063
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7063
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7052
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7052
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7046
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7046
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7021
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7021

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