5-hydroxytephroapollin F - Compound Card

5-hydroxytephroapollin F

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5-hydroxytephroapollin F

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Prenylated Flavone
Canonical Smiles CC(=O)OOC(C(O)(C)C)C1COc2c1c1oc(cc(=O)c1c(c2)O)c1ccccc1
InChI InChI=1S/C23H22O8/c1-12(24)30-31-22(23(2,3)27)14-11-28-18-10-16(26)20-15(25)9-17(29-21(20)19(14)18)13-7-5-4-6-8-13/h4-10,14,22,26-27H,11H2,1-3H3
InChIKey SEZHAMBKGXGWJB-UHFFFAOYSA-N
Formula C23H22O8
HBA 8
HBD 2
MW 426.42
Rotatable Bonds 5
TPSA 115.43
LogP 3.28
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 426.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tephrosia apollinea Leguminosae/Fabaceae Plantae 1390541

Showing of synonyms

  • Khalafallah A, Suleiman S, et al. (2009). Prenylated flavonoids from Tephrosia apollinea. Chinese Chemical Letters, 2009, 20(12), 1465-1468. [View]

No compound-protein relationship available.

Structure

SMILES: C1COc(c12)ccc3c2oc(cc3=O)-c4ccccc4

Level: 1

Mol. Weight: 426.42 g/mol

Structure

SMILES: C1COc(c12)ccc3c2occc3=O

Level: 0

Mol. Weight: 426.42 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 426.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.6
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.62
Plasma Protein Binding
67.37
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
6.8
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.87
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.69
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.58
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
-45.74
Rat (Acute)
2.66
Rat (Chronic Oral)
2.09
Fathead Minnow
5.29
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
478.12
Hydration Free Energy
-3.86
Log(D) at pH=7.4
2.61
Log(P)
3.13
Log S
-4.5
Log(Vapor Pressure)
-9.42
Melting Point
173.39
pKa Acid
7.05
pKa Basic
4.19
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 0.9365
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9283
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9268
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.9050
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8871
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8529
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8528
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8449
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8447
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8424
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8390
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8293
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8268
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8214
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8186
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8167
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.8160
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8093
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.8085
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8023
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7968
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7898
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7894
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7864
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7809
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7804
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7770
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7756
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7745
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7726
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7688
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7638
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7572
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7532
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7480
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7476
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7471
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7434
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7426
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7397
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7392
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7383
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7378
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7378
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7368
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7360
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7342
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 4 0.7334
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7325
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7307
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 4 0.7287
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7285
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7268
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7255
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7250
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7249
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7246
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7244
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7214
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7212
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7178
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7166
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7143
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7137
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7131
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7118
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7111
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7106
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7100
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7075
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7054
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7051
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7043
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7033
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7031
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7029
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7011
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7010
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7004
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7003

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