N-formyl-7-hydroxyglaucine - Compound Card

N-formyl-7-hydroxyglaucine

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N-formyl-7-hydroxyglaucine

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles COc1cc2c(cc1OC)c(O)c1c3c2c(OC)c(OC)cc3ccn1C=O
InChI InChI=1S/C21H19NO6/c1-25-14-8-12-13(9-15(14)26-2)20(24)19-17-11(5-6-22(19)10-23)7-16(27-3)21(28-4)18(12)17/h5-10,24H,1-4H3
InChIKey REPDLRAALJHCGP-UHFFFAOYSA-N
Formula C21H19NO6
HBA 6
HBD 1
MW 381.38
Rotatable Bonds 5
TPSA 77.46
LogP 3.68
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.19
Exact Mass 381.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Friesodielsia obovata Annonaceae Plantae 1202418

Showing of synonyms

  • Joseph CC, Magadula JJ, et al. (2007). A novel antiplasmodial 3',5'-diformylchalcone and other constituents of Friesodielsia obovata. Natural Product Research,2007,21(11),1009-1015. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1c2c34)cc4[nH]ccc3ccc2

Level: 0

Mol. Weight: 381.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.59
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.700
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.520
Plasma Protein Binding
63.5
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.570
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.660
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.190
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.820
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
-11.200
Rat (Acute)
2.820
Rat (Chronic Oral)
2.180
Fathead Minnow
5.280
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
513.020
Hydration Free Energy
-6.350
Log(D) at pH=7.4
2.930
Log(P)
3.14
Log S
-4.94
Log(Vapor Pressure)
-7.93
Melting Point
195.67
pKa Acid
8.51
pKa Basic
2.05
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9459
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9459
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9254
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9254
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.9205
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.9205
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.9181
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.9181
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9131
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9131
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9067
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9067
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9022
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9022
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8902
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8902
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8872
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8872
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8847
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8847
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8757
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8757
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8723
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8723
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8706
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8706
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8661
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8661
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8571
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8571
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8528
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8528
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8498
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8498
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8495
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8495
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8464
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8464
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8359
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8359
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8267
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8267
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8220
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8220
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8194
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8194
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8170
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8170
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8136
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8136
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8070
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8070
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7929
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7929
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7908
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7908
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7884
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7884
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7872
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7872
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7866
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7866
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7828
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7828
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7766
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7766
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7730
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7730
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7705
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7705
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7665
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7665
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7654
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7654
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7639
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7639
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.7618
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.7618
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7613
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7613
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7595
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7595
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7576
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7576
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7574
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7574
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7567
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7567
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7552
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7552
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7535
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7535
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7524
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7524
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7512
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7512
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7505
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7505
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7474
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7474
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7438
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7438
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7410
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7410
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7389
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7389
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7369
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7369
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7365
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7365
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.7350
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.7350
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7348
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7348
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7313
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7313
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7311
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7311
Prostaglandin reductase 3 Q8N4Q0 PTGR3_HUMAN Homo sapiens 3 0.7307
Prostaglandin reductase 3 Q8N4Q0 PTGR3_HUMAN Homo sapiens 3 0.7307
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7290
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7290
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7290
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7290
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7287
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7287
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7286
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7286
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7285
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7285
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7236
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7236
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7234
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7234
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 4 0.7230
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 4 0.7230
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7208
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7208
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7186
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7186
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7185
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7185
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7176
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7176
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7171
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7171
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7146
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7146
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7142
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7142
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7138
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7138
Mitogen-activated protein kinase kinase kinase 14 Q99558 M3K14_HUMAN Homo sapiens 3 0.7132
Mitogen-activated protein kinase kinase kinase 14 Q99558 M3K14_HUMAN Homo sapiens 3 0.7132
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7110
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7110
High affinity nerve growth factor receptor P04629 NTRK1_HUMAN Homo sapiens 3 0.7094
High affinity nerve growth factor receptor P04629 NTRK1_HUMAN Homo sapiens 3 0.7094
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7093
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7093
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7084
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7084
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7079
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7079
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7052
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7052
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7042
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7042
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7021
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7021

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