Xanthopurpurin-1-methylether - Compound Card

Xanthopurpurin-1-methylether

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Xanthopurpurin-1-methylether

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1cc(C)cc2c1C(=O)c1ccccc1C2=O
InChI InChI=1S/C16H12O3/c1-9-7-12-14(13(8-9)19-2)16(18)11-6-4-3-5-10(11)15(12)17/h3-8H,1-2H3
InChIKey GFFXQCNUEYZFQH-UHFFFAOYSA-N
Formula C16H12O3
HBA 3
HBD 0
MW 252.27
Rotatable Bonds 1
TPSA 43.37
LogP 2.78
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 252.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Morinda lucida Rubiaceae Plantae 339305

Showing of synonyms

  • Longue Ekon J, Zra T, et al. (2020). New anthraquinone derivatives from the stem barks of Morinda lucida Benth. Phytochemistry Letters, 2020, 39, 94-98. [View]
Pubchem: 13412788
Nmrshiftdb2: 60079115

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 252.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.320
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.020
Plasma Protein Binding
59.31
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
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.470
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.870
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.960
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.060
Micronucleos
Safe
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
4.520
Rat (Acute)
2.260
Rat (Chronic Oral)
2.110
Fathead Minnow
4.670
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
392.540
Hydration Free Energy
-7.260
Log(D) at pH=7.4
2.220
Log(P)
3.59
Log S
-5.41
Log(Vapor Pressure)
-6.04
Melting Point
158.32
pKa Acid
8.45
pKa Basic
3.54
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9735
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9689
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9349
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9263
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8974
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8932
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.8919
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8826
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8722
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.8666
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8660
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8653
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8646
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.8610
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8607
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8573
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8478
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.8461
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8377
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 2 0.8337
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8329
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8293
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8290
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.8242
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8238
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.8231
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 4 0.8221
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.8167
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.8133
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.8130
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.8128
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.8112
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8067
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8065
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8041
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.8001
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7958
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7880
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7849
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7814
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7811
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7769
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7768
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7762
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7756
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7749
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7726
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7705
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7701
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7692
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7668
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7660
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7656
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7629
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7613
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7607
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7602
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7601
Tyrosine-protein kinase Lyn P25911 LYN_MOUSE Mus musculus 3 0.7580
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7577
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7572
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7564
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7562
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7553
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7549
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7537
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7471
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7469
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7447
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7441
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7432
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7428
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7397
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7397
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7389
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7387
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7384
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7338
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7336
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 2 0.7332
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7328
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7306
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7303
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7303
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7301
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7294
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7286
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7276
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7260
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7248
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7238
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7237
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7221
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7214
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7213
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7212
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7211
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7208
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7206
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7203
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7187
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7160
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7149
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7146
2-Hydroxyacid oxidase 1 Q9UJM8 HAOX1_HUMAN Homo sapiens 3 0.7144
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7126
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7126
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 3 0.7125
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7117
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7102
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7095
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7080
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7073
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7068
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7065
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7055
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7040
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7028
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7027
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7019
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 4 0.7016
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7014
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7002

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