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Cajanol

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

Canonical Smiles	COc1cc(O)c2c(c1)OCC(C2=O)c1ccc(cc1OC)O
InChI	InChI=1S/C17H16O6/c1-21-10-6-13(19)16-15(7-10)23-8-12(17(16)20)11-4-3-9(18)5-14(11)22-2/h3-7,12,18-19H,8H2,1-2H3
InChIKey	RYYWWFXWFMYKJM-UHFFFAOYSA-N
Formula	C₁₇H₁₆O₆
HBA	6
HBD	2
MW	316.31
Rotatable Bonds	3
TPSA	85.22
LogP	2.47
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.24
Exact Mass	316.09
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: 442670

Cas: 61020-70-0

Kegg Ligand: C10204

Nmrshiftdb2: 70023871

CPRiL: 214659

SMILES: c1cccc(c12)OCC(C2=O)c3ccccc3

Level: 1

Mol. Weight: 316.31 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 316.31 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 316.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.51
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.730
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.08

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.120
Plasma Protein Binding: 46.75
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 10.230
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.360
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.820
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.130
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: 3.730
Rat (Acute): 1.890
Rat (Chronic Oral): 2.500
Fathead Minnow: 4.580
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 421.270
Hydration Free Energy: -9.900
Log(D) at pH=7.4: 2.610
Log(P): 2.99
Log S: -5.31
Log(Vapor Pressure): -7.64
Melting Point: 157.05
pKa Acid: 7.82
pKa Basic: 4.22

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.9557
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.9545
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.9520
Isoflavone-7-O-methyltransferase 8	O24529	7OMT8_MEDSA	Medicago sativa	5	0.9505
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9265
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.9200
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9186
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9167
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.9123
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9089
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.9071
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8989
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8976
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8907
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8863
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8841
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8768
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8702
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8552
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	3	0.8549
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.8537
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.8525
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.8516
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.8503
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8479
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8438
RNA polymerase sigma factor SigA	Q5SKW1	Q5SKW1_THET8	Thermus thermophilus	3	0.8438
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	4	0.8405
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.8359
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8326
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.8308
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8305
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8282
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.8279
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8275
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.8260
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.8250
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.8238
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8231
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8180
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8162
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8159
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.8083
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8072
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8066
Gag-Pol polyprotein	O12158	POL_HV192	Human immunodeficiency virus type 1 group M subtype C	3	0.8061
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8048
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7999
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	4	0.7997
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7983
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7975
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7946
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7941
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7935
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7933
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7928
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7919
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7909
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7896
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7876
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7869
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.7850
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7843
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7824
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7812
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7812
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7809
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7793
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7775
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	4	0.7772
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7756
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7751
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7743
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7736
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7692
Acetolactate synthase catalytic subunit, mitochondrial	P07342	ILVB_YEAST	Saccharomyces cerevisiae	3	0.7670
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7663
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	4	0.7658
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7638
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7629
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7617
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7615
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7610
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7607
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7568
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7562
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7559
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	4	0.7557
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7543
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7528
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7497
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7485
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7474
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7473
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7469
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7469
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7466
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7450
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7419
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7387
Uridine phosphorylase	Q5XA29	Q5XA29_STRP6	Streptococcus pyogenes serotype M6	3	0.7380
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2	O88703	HCN2_MOUSE	Mus musculus	3	0.7365
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7355
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7347
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	3	0.7344
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7339
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7336
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	3	0.7335
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7326
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7321
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7320
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7312
Serine hydroxymethyltransferase	Q7SIB6	Q7SIB6_GEOSE	Geobacillus stearothermophilus	3	0.7310
Putative cytochrome P450	Q70AS3	Q70AS3_STRPE	Streptomyces peucetius	4	0.7308
Dihydrofolate reductase	P16184	DYR_PNECA	Pneumocystis carinii	3	0.7306
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7306
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7300
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	2	0.7293
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7285
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7265
Dihydrofolate reductase	P16184	DYR_PNECA	Pneumocystis carinii	3	0.7265
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7263
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.7261
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7250
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7240
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7236
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7230
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7222
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7221
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7216
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7213
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7202
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7200
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7190
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.7189
Oxygen-insensitive NAD(P)H nitroreductase	P38489	NFSB_ECOLI	Escherichia coli	3	0.7181
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7180
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7175
Dihydrofolate reductase	O30463	O30463_MYCAV	Mycobacterium avium	3	0.7170
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7165
Cytidylate kinase	B1MB31	B1MB31_MYCA9	Mycobacteroides abscessus	4	0.7161
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7148
YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein	Q5SHN1	Q5SHN1_THET8	Thermus thermophilus	3	0.7141
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7141
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7141
Proto-oncogene tyrosine-protein kinase receptor Ret	P07949	RET_HUMAN	Homo sapiens	3	0.7134
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7127
dTDP-fucosamine acetyltransferase	Q8FBQ3	WECD_ECOL6	Escherichia coli O6:H1	3	0.7107
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7103
GTPase IMAP family member 2	Q9UG22	GIMA2_HUMAN	Homo sapiens	3	0.7092
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7090
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7089
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	4	0.7083
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7064
Calmodulin-like domain protein kinase isoenzyme gamma, related	F0V9W9	F0V9W9_NEOCL	Neospora caninum	3	0.7063
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.7058
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7035
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7030
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7025
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7019
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7014
Cytochrome P450 130	P9WPN5	CP130_MYCTU	Mycobacterium tuberculosis	3	0.7014

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