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Damnacanthal
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Anthraquinone
| Canonical Smiles | COc1c2C(=O)c3ccccc3C(=O)c2cc(c1C=O)O |
|---|---|
| InChI | InChI=1S/C16H10O5/c1-21-16-11(7-17)12(18)6-10-13(16)15(20)9-5-3-2-4-8(9)14(10)19/h2-7,18H,1H3 |
| InChIKey | IPDMWUNUULAXLU-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 | Pentas schimperi | Rubiaceae | Plantae | 25384 |
| 2 | Pentas schimperi | Rubiaceae | Plantae | 25384 |
Showing of synonyms
Damnacanthal
477-84-9
Damnacantal
3-hydroxy-1-methoxy-9,10-dioxoanthracene-2-carbaldehyde
CCRIS 6443
2-Anthraquinonecarboxaldehyde, 3-hydroxy-1-methoxy-
DTXSID10197253
DTXCID20119744
3-Hydroxy-1-methoxyanthraquinone-2-aldehyde
WUC3CB63CD
9,10-Dihydro-3-hydroxy-1-methoxy-9,10-dioxo-2-anthracenecarboxaldehyde
3-hydroxy-1-methoxy-9,10-dioxo-9,10-dihydro-2-anthracenecarbaldehyde
BiomolKI_000022
UNII-WUC3CB63CD
3-hydroxy-1-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde
BiomolKI2_000030
CBiol_001879
BSPBio_000985
KBioGR_000325
KBioSS_000325
SCHEMBL147246
BMK1-C10
CHEMBL212948
BCBcMAP01_000230
CHEBI:93633
KBio2_000325
KBio2_002893
KBio2_005461
KBio3_000649
KBio3_000650
Bio1_000165
Bio1_000654
Bio1_001143
Bio2_000323
Bio2_000803
GLXC-02506
HMS1362A07
HMS1792A07
HMS1990A07
HMS3403A07
HMS3753K05
Damnacanthal - CAS 477-84-9
BDBM50366492
AKOS024456868
CCG-100626
IDI1_002078
QTL1_000028
NCGC00163375-01
NCGC00163375-02
NCGC00163375-03
MS-24004
HY-108485
CS-0028962
G12637
K00034
AO-229/41747043
Q5212724
BRD-K93325701-001-03-0
3-hydroxy-1-methoxy-9,10-dioxo-anthracene-2-carbaldehyde
2-Anthraldehyde, 9,10-dihydro-3-hydroxy-1-methoxy-9,10-dioxo-
3-Hydroxy-1-methoxy-9,10-dioxo-9,10-dihydro-anthracene-2-carbaldehyde
- Kuete V, Donfack AR, et al. (2015). Cytotoxicity of anthraquinones from the roots of Pentas schimperi towards multi-factorial drug-resistant cancer cells.. Investigational new drugs,2015, 33(4), 861-869. [View] [PubMed]
- Goffin E, Ziemons E, et al. (2002). In vitro antiplasmodial activity of Tithonia diversifolia and identification of its main active constituent: tagitinin C.. Planta medica,2002, 68(6), 543-545. [View] [PubMed]
Pubchem:
2948
Cas:
477-84-9
Gnps:
CCMSLIB00005724432
Zinc:
ZINC000003872206
Chebi:
93633
Nmrshiftdb2:
60066334
Chembl:
CHEMBL212948
Comptox:
DTXSID10197253
Bindingdb:
50366492
CPRiL:
66429
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 282.25 g/mol
Cancer cell growth inhibitory
Absorption
- Caco-2 (logPapp)
- -4.54
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.34
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.97
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.54
- Plasma Protein Binding
- 51.99
- 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
- 5.8
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.64
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.05
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.23
- 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
- 4.36
- Rat (Acute)
- 2.4
- Rat (Chronic Oral)
- 2.48
- Fathead Minnow
- 4.56
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 415.78
- Hydration Free Energy
- -8.22
- Log(D) at pH=7.4
- 1.64
- Log(P)
- 3.33
- Log S
- -5.19
- Log(Vapor Pressure)
- -7.29
- Melting Point
- 209.63
- pKa Acid
- 6.64
- pKa Basic
- 2.44
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.9778 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.9293 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 3 | 0.9292 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.9258 |
| Putative ketoacyl reductase | P16544 | ACT3_STRCO | Streptomyces coelicolor / M145) | 3 | 0.9021 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8944 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 4 | 0.8879 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8863 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8826 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.8722 |
| Tryptophan synthase alpha chain | P00929 | TRPA_SALTY | Salmonella typhimurium | 3 | 0.8679 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8669 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.8646 |
| Activin receptor type-1 | Q04771 | ACVR1_HUMAN | Homo sapiens | 3 | 0.8523 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.8479 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.8458 |
| Mitogen-activated protein kinase 10 | P53779 | MK10_HUMAN | Homo sapiens | 3 | 0.8450 |
| L-lactate dehydrogenase A chain | P13491 | LDHA_RABIT | Oryctolagus cuniculus | 3 | 0.8405 |
| Aklavinone 12-hydroxylase RdmE | Q54530 | DNRF_STREF | Streptomyces purpurascens | 4 | 0.8375 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8300 |
| Fatty acid-binding protein, intestinal | P12104 | FABPI_HUMAN | Homo sapiens | 3 | 0.8216 |
| Tubulin alpha-1B chain | P81947 | TBA1B_BOVIN | Bos taurus | 3 | 0.8153 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.8099 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8061 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.8027 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7959 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7903 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 2 | 0.7872 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7858 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7851 |
| Putative protease I | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron | 2 | 0.7830 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7815 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7799 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 4 | 0.7711 |
| Tubulin alpha chain | D0VWZ0 | D0VWZ0_SHEEP | Ovis aries | 3 | 0.7698 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7674 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7649 |
| Casein kinase I isoform gamma-3 | Q9Y6M4 | KC1G3_HUMAN | Homo sapiens | 3 | 0.7647 |
| Enoyl-ACP reductase | Q9BJJ9 | Q9BJJ9_PLAFA | Plasmodium falciparum | 3 | 0.7590 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7582 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7565 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7565 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7531 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.7528 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7522 |
| cGMP-dependent protein kinase, putative | A5K0N4 | A5K0N4_PLAVS | Plasmodium vivax | 3 | 0.7485 |
| Proliferating cell nuclear antigen | P12004 | PCNA_HUMAN | Homo sapiens | 3 | 0.7462 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7460 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7436 |
| Proto-oncogene tyrosine-protein kinase Src | P12931 | SRC_HUMAN | Homo sapiens | 3 | 0.7436 |
| Hematopoietic prostaglandin D synthase | O60760 | HPGDS_HUMAN | Homo sapiens | 3 | 0.7430 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 2 | 0.7423 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7396 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7370 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7366 |
| Plasma membrane ATPase | Q42932 | Q42932_NICPL | Nicotiana plumbaginifolia | 2 | 0.7316 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7281 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.7276 |
| Methionine aminopeptidase | P0AE18 | MAP1_ECOLI | Escherichia coli | 3 | 0.7256 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7248 |
| Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 3 | 0.7244 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.7237 |
| Nucleoside diphosphate kinase | Q5UQL3 | NDK_MIMIV | Acanthamoeba polyphaga mimivirus | 2 | 0.7234 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 3 | 0.7227 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7222 |
| Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 3 | 0.7211 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 2 | 0.7188 |
| Activin receptor type-1 | Q04771 | ACVR1_HUMAN | Homo sapiens | 3 | 0.7187 |
| Metallo-beta-lactamase type 2 | P26918 | BLAB_AERHY | Aeromonas hydrophila | 2 | 0.7185 |
| Proto-oncogene tyrosine-protein kinase Src | P12931 | SRC_HUMAN | Homo sapiens | 3 | 0.7175 |
| Anthranilate phosphoribosyltransferase | P9WFX5 | TRPD_MYCTU | Mycobacterium tuberculosis | 3 | 0.7175 |
| Riboflavin biosynthesis protein | Q9WZW1 | Q9WZW1_THEMA | Thermotoga maritima | 3 | 0.7166 |
| Cytohesin-2 | Q99418 | CYH2_HUMAN | Homo sapiens | 3 | 0.7163 |
| Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 3 | 0.7144 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7137 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7131 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7122 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 3 | 0.7106 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7106 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7089 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7082 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.7071 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7067 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7054 |
| Chymotrypsinogen A | P00766 | CTRA_BOVIN | Bos taurus | 3 | 0.7029 |
| NmrA-like family domain-containing protein 1 | Q9HBL8 | NMRL1_HUMAN | Homo sapiens | 2 | 0.7026 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7011 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7009 |
| Tryptophan synthase alpha chain | P00929 | TRPA_SALTY | Salmonella typhimurium | 3 | 0.7000 |