2-hydroxy-1,11-dimethoxycanthin-6-one - Compound Card

2-hydroxy-1,11-dimethoxycanthin-6-one

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2-hydroxy-1,11-dimethoxycanthin-6-one

Structure
Zoomed Structure
  • Family: Plantae - Simaroubaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Canthinone Alkaloid
Canonical Smiles COc1cccc2c1c1c(OC)c(O)nc3c1n2c(=O)cc3
InChI InChI=1S/C16H12N2O4/c1-21-10-5-3-4-9-12(10)13-14-8(6-7-11(19)18(9)14)17-16(20)15(13)22-2/h3-7H,1-2H3,(H,17,20)
InChIKey BODDKJXAAKFSPL-UHFFFAOYSA-N
Formula C16H12N2O4
HBA 6
HBD 1
MW 296.28
Rotatable Bonds 2
TPSA 73.06
LogP 2.16
Number Rings 4
Number Aromatic Rings 4
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 296.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Brucea antidysenterica Simaroubaceae Plantae 459111

Showing of synonyms

  • Makong YS, Mouthé Happi G, et al. (2019). Cytotoxic Stilbenes and Canthinone Alkaloids from Brucea antidysenterica (Simaroubaceae). Molecules, 2019, 24(23), 4412. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1c23)n4c2c(ccc4=O)ncc3

Level: 0

Mol. Weight: 296.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.400
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.95

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.590
Plasma Protein Binding
82.57
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
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.820
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.170
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.480
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.930
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Toxic
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
3.190
Rat (Acute)
2.120
Rat (Chronic Oral)
1.750
Fathead Minnow
4.790
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
492.640
Hydration Free Energy
-11.980
Log(D) at pH=7.4
1.890
Log(P)
1.26
Log S
-4.95
Log(Vapor Pressure)
-7.72
Melting Point
260.85
pKa Acid
8.86
pKa Basic
4.62
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.9607
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.9470
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.9390
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 4 0.9303
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 4 0.9282
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9265
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9188
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8971
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8962
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8914
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8858
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8855
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8854
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8829
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8796
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8779
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8770
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8764
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8763
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8706
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8656
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.8589
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8588
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8562
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8522
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8520
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8515
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8508
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8499
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8469
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8447
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8412
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8331
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8321
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8312
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8280
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8256
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.8199
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8187
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8177
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8137
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8123
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.8083
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8070
Serine/threonine-protein kinase N1 Q16512 PKN1_HUMAN Homo sapiens 3 0.8068
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8039
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.8004
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7954
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7947
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7939
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7938
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7849
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7828
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7828
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7806
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7779
Thymidylate synthase P04818 TYSY_HUMAN Homo sapiens 3 0.7755
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7731
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7719
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7706
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7690
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7681
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7679
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7678
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7653
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7643
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7640
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7600
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7575
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7573
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7561
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7549
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7534
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7531
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7530
D(3) dopamine receptor P35462 DRD3_HUMAN Homo sapiens 3 0.7509
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7501
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7467
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7467
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7466
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7417
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7402
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7395
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 3 0.7379
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7371
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7371
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7361
dTDP-4-dehydro-6-deoxyglucose 3-epimerase Q5SFD1 CHMJ_STRBI Streptomyces bikiniensis 3 0.7356
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7346
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7330
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.7330
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7326
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7306
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7294
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7292
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7287
Exotoxin A P11439 TOXA_PSEAE Pseudomonas aeruginosa 3 0.7269
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7268
Purine phosphoribosyltransferase (GpT-1) Q97W95 Q97W95_SACS2 Saccharolobus solfataricus 3 0.7267
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7265
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7255
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7250
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7245
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7231
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7201
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7199
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7198
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7195
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7194
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7189
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7186
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7180
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7175
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7172
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7135
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7123
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7119
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7118
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7112
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7107
Beta-1,4-galactosyltransferase 1 P08037 B4GT1_BOVIN Bos taurus 3 0.7105
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial P08559 ODPA_HUMAN Homo sapiens 3 0.7097
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7076
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7076
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7070
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7069
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7065
Elongation factor 1-alpha O59153 EF1A_PYRHO Pyrococcus horikoshii 3 0.7051
Ribosome biogenesis GTPase YqeH D0VWU7 D0VWU7_GEOSE Geobacillus stearothermophilus 3 0.7051
Elongation factor 1-alpha P02994 EF1A_YEAST Saccharomyces cerevisiae 3 0.7051
CalS13 Q8KND8 Q8KND8_MICEC Micromonospora echinospora 3 0.7049
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7048
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7046
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 3 0.7045
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7042
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7037
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7034
Activated CDC42 kinase 1 Q07912 ACK1_HUMAN Homo sapiens 4 0.7025
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7024
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7012

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