(+)-tephroglabrin - Compound Card

(+)-tephroglabrin

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(+)-tephroglabrin

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Prenylated Flavone
Canonical Smiles c1(ccc2c(c1C1=COC(C1=O)(C)C)oc(cc2=O)c1ccccc1)OC
InChI InChI=1S/C22H18O5/c1-22(2)21(24)15(12-26-22)19-17(25-3)10-9-14-16(23)11-18(27-20(14)19)13-7-5-4-6-8-13/h4-12H,1-3H3
InChIKey IJRSTLGZIYDKHD-UHFFFAOYSA-N
Formula C22H18O5
HBA 5
HBD 0
MW 362.38
Rotatable Bonds 3
TPSA 65.74
LogP 4.19
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 362.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tephrosia apollinea Leguminosae/Fabaceae Plantae 1390541
2 Tephrosia purpurea Leguminosae/Fabaceae Plantae 228354

Showing of synonyms

  • Khalafalah A.K, Yousef A.H, et al. (2010). Chemical constituents of Tephrosia purpurea. Pharmacognosy research, 2010, 2(2), 72-5. [View] [PubMed]
  • Khalafallah A, Suleiman S, et al. (2009). Prenylated flavonoids from Tephrosia apollinea. Chinese Chemical Letters, 2009, 20(12), 1465-1468. [View]
Pubchem: 21721923
Nmrshiftdb2: 60070784

No compound-protein relationship available.

Structure

SMILES: O=C1COC=C1c(ccc2)c(c23)oc(cc3=O)-c4ccccc4

Level: 2

Mol. Weight: 362.38 g/mol

Structure

SMILES: O=C1COC=C1c(ccc2)c(c23)occc3=O

Level: 1

Mol. Weight: 362.38 g/mol

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 362.38 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 362.38 g/mol

Structure

SMILES: O=C1C=COC1

Level: 0

Mol. Weight: 362.38 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 362.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.69
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.54
Plasma Protein Binding
80.11
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
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
5.25
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.77
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.03
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.42
Micronucleos
Toxic
NR-AhR
Toxic
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
-4.91
Rat (Acute)
2.86
Rat (Chronic Oral)
1.8
Fathead Minnow
5.49
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
469.82
Hydration Free Energy
-7.02
Log(D) at pH=7.4
3.35
Log(P)
3.9
Log S
-5.31
Log(Vapor Pressure)
-7.97
Melting Point
173.77
pKa Acid
7.61
pKa Basic
3.06
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.9841
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9701
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9685
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.9451
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9150
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.9073
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9052
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9023
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9004
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8913
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8903
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8888
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.8803
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8717
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8714
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.8696
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8654
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8618
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8609
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.8562
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.8528
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8520
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.8411
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8344
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8336
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8329
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.8317
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8312
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8308
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8196
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8171
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.8157
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8088
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8020
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7961
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7938
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7905
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7903
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 3 0.7902
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7896
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7864
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7863
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7826
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7818
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7794
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7793
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7791
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7787
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7767
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7764
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7727
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7701
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7692
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7680
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7669
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7665
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7650
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7645
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7622
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7614
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7607
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7590
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7550
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7546
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7541
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7539
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7533
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7523
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7518
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7514
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7507
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7489
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7484
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7483
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7471
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7470
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7458
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7457
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7440
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7437
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7429
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7427
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7417
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7410
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7409
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7401
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 2 0.7384
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7371
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7367
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7364
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7359
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7352
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7348
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7330
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7321
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7319
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7312
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7312
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7304
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7304
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7303
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7283
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7281
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7277
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7271
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7264
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7240
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7236
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7233
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7226
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7189
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7178
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 2 0.7170
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7170
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7159
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7152
Cytochrome P450 3A4 P08684 CP3A4_HUMAN Homo sapiens 3 0.7151
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7146
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7144
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7135
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7133
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7131
Actin nucleation-promoting factor WAS P42768 WASP_HUMAN Homo sapiens 3 0.7110
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7105
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7102
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7100
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7090
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7073
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7072
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7059
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7054
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7049
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7041
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7034
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7032
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7021
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.7020
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7020
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7016
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7016
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7002

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