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Tephrowatsin A

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

Canonical Smiles	COc1cc(OC)c2c(c1CC=C(C)C)O[C@@H](C[C@H]2O)c1ccccc1
InChI	InChI=1S/C22H26O4/c1-14(2)10-11-16-19(24-3)13-20(25-4)21-17(23)12-18(26-22(16)21)15-8-6-5-7-9-15/h5-10,13,17-18,23H,11-12H2,1-4H3/t17-,18+/m1/s1
InChIKey	ADIMMCHZVYYGPW-MSOLQXFVSA-N
Formula	C₂₂H₂₆O₄
HBA	4
HBD	1
MW	354.45
Rotatable Bonds	5
TPSA	47.92
LogP	4.77
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.36
Exact Mass	354.18
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Tephrosia rhodesica	Leguminosae/Fabaceae	Plantae	556521

Showing of synonyms

Atilaw Y, Muiva-Mutisya L, et al. (2020). Prenylated Flavonoids from the Roots of Tephrosia rhodesica. Journal of natural products, 2020, 83(8), 2390–2398. [View]

Pubchem: 442542

Cas: 97640-79-4

Zinc: ZINC000004098457

Kegg Ligand: C09970

Chebi: 9443

Nmrshiftdb2: 60069174

Metabolights: MTBLC9443

Chembl: CHEMBL4798009

Comptox: DTXSID90331870

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 354.45 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 354.45 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 354.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.77
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.450
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.57

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.160
Plasma Protein Binding: 91.15
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: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 7.770
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.110
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.290
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.520
Micronucleos: Safe
NR-AhR: Safe
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: -3.470
Rat (Acute): 2.030
Rat (Chronic Oral): 2.190
Fathead Minnow: 5.040
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 415.120
Hydration Free Energy: -7.150
Log(D) at pH=7.4: 3.270
Log(P): 5.1
Log S: -5.06
Log(Vapor Pressure): -7.42
Melting Point: 110.18
pKa Acid: 12.18
pKa Basic: 4.91

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.9501
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9451
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.9317
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9083
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.9005
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8976
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.8926
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.8856
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8796
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8775
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8745
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	3	0.8690
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8684
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8662
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.8636
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8634
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8597
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8591
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8564
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8548
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8449
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8442
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8409
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8400
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8377
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.8373
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8356
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.8326
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8321
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8297
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8288
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8226
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8191
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8155
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8113
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.8084
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8058
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.8025
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7992
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7986
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7986
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7985
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7982
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7961
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7945
Phosphatidylinositol 3-kinase catalytic subunit type 3	Q8NEB9	PK3C3_HUMAN	Homo sapiens	3	0.7928
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7918
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7888
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7865
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7861
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7855
Flavonoid 3-O-glucosyltransferase	A6XNC6	UGFGT_MEDTR	Medicago truncatula	3	0.7819
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7770
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.7759
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7741
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	3	0.7722
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7718
Methionine--tRNA ligase	P00959	SYM_ECOLI	Escherichia coli	3	0.7713
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	4	0.7708
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7708
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7698
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7696
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7690
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7688
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7686
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7685
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7671
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7670
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7626
Quercetin 2,3-dioxygenase	Q7SIC2	QDOI_ASPJA	Aspergillus japonicus	4	0.7612
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7610
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	3	0.7608
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.7602
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7585
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7583
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7578
Histidine kinase 4	Q9C5U0	AHK4_ARATH	Arabidopsis thaliana	4	0.7569
Thymidine phosphorylase	P07650	TYPH_ECOLI	Escherichia coli	4	0.7565
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7522
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7512
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7509
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7509
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7506
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7501
Sulfotransferase 1E1	P49888	ST1E1_HUMAN	Homo sapiens	3	0.7481
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7437
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7434
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7431
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7422
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7420
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7405
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7405
Glutathione S-transferase	Q8ILQ7	GST_PLAFA	Plasmodium falciparum	3	0.7397
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7388
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	3	0.7363
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7362
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7354
3',5'-cyclic-AMP phosphodiesterase 4A	P27815	PDE4A_HUMAN	Homo sapiens	3	0.7353
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7341
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7336
SRSF protein kinase 1	Q96SB4	SRPK1_HUMAN	Homo sapiens	3	0.7329
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7321
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7320
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7316
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7291
Glycylpeptide N-tetradecanoyltransferase	Q4Q5S8	Q4Q5S8_LEIMA	Leishmania major	3	0.7268
DNA adenine methylase	P0AEE8	DMA_ECOLI	Escherichia coli	3	0.7268
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7259
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7239
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7239
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7216
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7213
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7211
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7210
Metallo-beta-lactamase type 2	P52699	BLAB_SERMA	Serratia marcescens	3	0.7197
Type II methyltransferase M.RsrI	P14751	MTR1_RHOSH	Cereibacter sphaeroides	3	0.7197
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7195
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7193
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7187
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7183
Angiopoietin-1 receptor	Q02763	TIE2_HUMAN	Homo sapiens	3	0.7182
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7178
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7176
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	3	0.7154
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7146
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7143
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7138
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7138
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7132
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7127
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7121
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.7116
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7113
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7099
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7096
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7088
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7086
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7084
Rifampin ADP-ribosyl transferase	A0QRS5	A0QRS5_MYCS2	Mycolicibacterium smegmatis155)	3	0.7084
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7072
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7071
Activated CDC42 kinase 1	Q07912	ACK1_HUMAN	Homo sapiens	3	0.7067
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7065
Cyclic nucleotide-binding protein	B8FW11	B8FW11_DESHD	Desulfitobacterium hafniense	3	0.7060
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7052
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7049
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7049
Tyrosine-protein kinase ABL1	P00519	ABL1_HUMAN	Homo sapiens	3	0.7044
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7041
Collagenase 3	P45452	MMP13_HUMAN	Homo sapiens	3	0.7040
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	2	0.7035
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7033
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7031
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7029
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	4	0.7016
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7016
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7006
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	4	0.7001

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