2-hydroxy-3-methoxy-9,10-dioxo-9,10-dihydroanthracene-1-carbaldehyde - Compound Card

2-hydroxy-3-methoxy-9,10-dioxo-9,10-dihydroanthracene-1-carbaldehyde

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2-hydroxy-3-methoxy-9,10-dioxo-9,10-dihydroanthracene-1-carbaldehyde

Structure
Zoomed Structure
  • Family: Plantae - Bignoniaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
Canonical Smiles O=Cc1c(O)c(OC)cc2c1C(=O)c1ccccc1C2=O
InChI InChI=1S/C16H10O5/c1-21-12-6-10-13(11(7-17)15(12)19)16(20)9-5-3-2-4-8(9)14(10)18/h2-7,19H,1H3
InChIKey HVUGIQFJZPPVFK-UHFFFAOYSA-N
Formula C16H10O5
HBA 5
HBD 1
MW 282.25
Rotatable Bonds 2
TPSA 80.67
LogP 1.99
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.06
Exact Mass 282.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Newbouldia laevis Bignoniaceae Plantae 211924

Showing of synonyms

  • Kuete V, Eyong KO, et al. (2007). Antimicrobial activity of the methanolic extract and of the chemical constituents isolated from Newbouldia laevis. Die Pharmazie - An International Journal of Pharmaceutical Sciences, 2007, 62(7), 552-556. [View]
Pubchem: 11550926
Nmrshiftdb2: 70064672

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 282.25 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.63
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.4
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.03

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.65
Plasma Protein Binding
53.68
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-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
6.76
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.92
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.23
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.07
Micronucleos
Toxic
NR-AhR
Safe
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
4.33
Rat (Acute)
2.34
Rat (Chronic Oral)
2.52
Fathead Minnow
4.51
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
412.78
Hydration Free Energy
-7.89
Log(D) at pH=7.4
1.61
Log(P)
2.92
Log S
-5.31
Log(Vapor Pressure)
-7.68
Melting Point
204.3
pKa Acid
5.37
pKa Basic
2.77
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.9512
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.9255
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9211
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9204
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9150
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.9088
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 4 0.9060
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8960
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8868
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 3 0.8773
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8732
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 4 0.8669
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8605
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8513
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8485
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8450
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8439
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8369
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8347
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8312
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8227
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8208
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8143
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8071
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7945
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7924
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7677
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7660
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7625
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7561
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.7493
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7428
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7385
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7380
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.7365
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7347
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7346
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7342
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7337
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7333
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7319
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7300
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7297
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7293
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7292
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7291
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7290
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7281
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7278
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7266
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7262
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7258
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7237
Aklanonic acid methyl ester cyclase AcmA O52646 DNRD_STRGJ Streptomyces galilaeus 3 0.7225
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7224
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7186
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7185
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7164
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7155
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7151
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 3 0.7147
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7130
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7079
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7068
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7066
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7059

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