Select a section from the left sidebar
1,8-dihydroxyanthraquinone
- Family: Plantae - Liliaceae
- Kingdom: Plantae
-
Class: Anthracene
- Subclass: Anthraquinone
| Canonical Smiles | Oc1cccc2c1C(=O)c1c(C2=O)cccc1O |
|---|---|
| InChI | InChI=1S/C14H8O4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6,15-16H |
| InChIKey | QBPFLULOKWLNNW-UHFFFAOYSA-N |
| Formula | C14H8O4 |
| HBA | 4 |
| HBD | 2 |
| MW | 240.21 |
| Rotatable Bonds | 0 |
| TPSA | 74.6 |
| LogP | 1.87 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.0 |
| Exact Mass | 240.04 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Asphodelus microcarpus | Liliaceae | Plantae | 49697 |
Showing of synonyms
1,8-dihydroxyanthraquinone
Danthron
117-10-2
Chrysazin
Dantron
Dorbane
Istizin
1,8-Dihydroxyanthracene-9,10-dione
9,10-Anthracenedione, 1,8-dihydroxy-
Laxipur
Danthrone
Dantrone
1,8-Dihydroxy-9,10-anthraquinone
Dioxyanthrachinonum
Usaf nd-59
1,8-Dihydroxyanthrachinon
Dantronum
1,8-Dihydroxyanthra-9,10-quinone
1,8-Dihydroxy-9,10-anthracenedione
Dantron [INN]
1,8-Dihydroxyanthrachinon [Czech]
Pilules Vinchy N.F.
1,8-dioxyanthraquinone
Laxapur
NSC7210
Z4XE6IBF3V
NSC-38626
Dantron (INN)
NSC-646568
CHEBI:3682
DTXSID9020328
DANTHRON [HSDB]
DANTHRON [MI]
DANTRON [IARC]
DANTHRON [VANDF]
DANTRON [MART.]
NSC646568
DANTRON [WHO-DD]
Pilules Vinchy N.F. (TN)
DTXCID10328
NSC38626
DITHRANOL IMPURITY B [EP IMPURITY]
DANTRON (IARC)
DANTRON (MART.)
Dianthon
1,8-Dihydroxyanthrachinon (Czech)
Danthro-lax
DITHRANOL IMPURITY B (EP IMPURITY)
A06AB03
204-173-5
Inchi=1/c14h8o4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6,15-16
Antrapurol
Laxanthreen
Diaquone
Laxanorm
Altan
Laxipurin
Zwitsalax
Danivac
Dionone
Duolax
Prugol
Roydan
Chrysazine
Dorbanex
Criasazin
Dantrona
LTAN
Anthraquinone, 1,8-dihydroxy-
1,8-Dihydroanthraquinone
1,8-dihydroxy-anthraquinone
MFCD00001211
NSC 38626
NSC 646568
1,8-dihydroxy-9,10-dihydroanthracene-9,10-dione
CHEMBL53418
Pastomin
Bancon
Istan
Component of Doxan
Neokutin S
Component of Modane
Scatron D
Component of Doxidan
Component of Dorbantyl
NCGC00091367-01
NCGC00091367-05
9, 1,8-dihydroxy-
Anthraquinone,8-dihydroxy-
Dantrone [INN-French]
Dantronum [INN-Latin]
Dantrona [INN-Spanish]
1,4,5,8-Tetroxyantraquinone
WLN: L C666 BV IVJ DQ NQ
Danthron [USP]
CAS-117-10-2
CCRIS 3529
EINECS 204-173-5
UNII-Z4XE6IBF3V
Istizine
AI3-38117
HSDB 7764
3nsq
Danthron, BAN
Dantron, INN
Danthron (Standard)
Dorbanex (Salt/Mix)
Dorbantyl (Salt/Mix)
Spectrum_001750
Dihyanthraquin_P41_LT
Spectrum2_000603
Spectrum3_000650
Spectrum4_001682
Spectrum5_000324
Dihyanthraquin_P21/n_LT
NCIMech_000114
1,8-Dihydroxyanthracene-9,10-dione (Danthron)
Dihyanthraquin_P41212_RT
SCHEMBL83688
BSPBio_002259
KBioGR_001944
KBioSS_002230
SPECTRUM211468
MLS000069608
DivK1c_000284
SPBio_000506
1,8-DHAQ
MEGxp0_001693
ACon1_000135
BDBM11316
HMS500O06
HY-B0923R
KBio1_000284
KBio2_002230
KBio2_004798
KBio2_007366
KBio3_001479
NINDS_000284
1,8-Dihydroxyanthraquinone, 96%
HMS2091A09
HMS3715F08
Pharmakon1600-00211468
8,9-dihydroxy-1,10-anthraquinone
BCP31079
HY-B0923
NSC-7210
Tox21_111122
Tox21_200986
BBL013161
CCG-35470
NSC755828
S4561
STK238373
AKOS001583216
Tox21_111122_1
1,8-Dihydroxyanthra-9,10-quinone #
9,10-Antiraquinone, 1,8-dihydroxy-
CS-4392
DB04816
FD22098
HS-1003
NSC-755828
IDI1_000284
NCGC00091367-02
NCGC00091367-03
NCGC00091367-04
NCGC00091367-06
NCGC00091367-07
NCGC00091367-08
NCGC00258539-01
1,8-bis(oxidanyl)anthracene-9,10-dione
DA-72552
NCI60_041443
SMR000059018
SY011288
SBI-0051330.P003
1,8-Dihydroxy-9,10-anthracenedione, 9CI
D0563
EU-0099935
NS00015698
D07107
F17670
AB00051961_09
Danthron (1,8-Dihydroxyanthracene-9,10-dione)
EN300-1693514
A803710
SR-01000721864
Q5221244
SR-01000721864-2
BRD-K10065684-001-02-5
BRD-K10065684-001-03-3
BRD-K10065684-001-06-6
BRD-K10065684-001-07-4
1,8-Dihydroxyanthraquinone, Vetec(TM) reagent grade, 96%
CHZ
- Rizk A, Hammouda F, et al. (1972). Anthraquinones of Asphodelus microcarpus. Phytochemistry, 1972, 11(6), 2122-2125. [View]
Pubchem:
2950
Cas:
117-10-2
Gnps:
CCMSLIB00004719141
Zinc:
ZINC000003860369
Kegg Ligand:
C10312
Chebi:
3682
Nmrshiftdb2:
30100963
Metabolights:
MTBLC3682
Chembl:
CHEMBL53418
Comptox:
DTXSID9020328
Drugbank:
DB04816
Pdb Ligand:
CHZ
Bindingdb:
11316
CPRiL:
23711
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 240.21 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.6
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.460
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.14
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.780
- Plasma Protein Binding
- 59.07
- 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
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.820
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 1.270
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.160
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.500
- Micronucleos
- Toxic
- 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
- 4.680
- Rat (Acute)
- 2.700
- Rat (Chronic Oral)
- 3.100
- Fathead Minnow
- 4.280
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 402.140
- Hydration Free Energy
- -9.820
- Log(D) at pH=7.4
- 2.090
- Log(P)
- 3.74
- Log S
- -5.39
- Log(Vapor Pressure)
- -7.94
- Melting Point
- 223.15
- pKa Acid
- 6.49
- pKa Basic
- 6.51
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.9516 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.9510 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9497 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9388 |
| Fatty acid-binding protein, intestinal | P12104 | FABPI_HUMAN | Homo sapiens | 3 | 0.9046 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.8868 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8823 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8721 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.8607 |
| ActVA 6 protein | Q53908 | Q53908_STRCH | Streptomyces coelicolor | 4 | 0.8599 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8497 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 4 | 0.8463 |
| Proto-oncogene tyrosine-protein kinase Src | P12931 | SRC_HUMAN | Homo sapiens | 3 | 0.8456 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8429 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.8386 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.8292 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.8281 |
| Ceramide transfer protein | Q9Y5P4 | CERT_HUMAN | Homo sapiens | 3 | 0.8251 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8219 |
| Aklavinone 12-hydroxylase RdmE | Q54530 | DNRF_STREF | Streptomyces purpurascens | 4 | 0.8018 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7985 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7934 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7927 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7922 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7886 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7801 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7755 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7742 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7700 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 4 | 0.7696 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7689 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7674 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7656 |
| Catalase-peroxidase | Q3JNW6 | KATG_BURP1 | Burkholderia pseudomallei | 3 | 0.7599 |
| Mitogen-activated protein kinase 10 | P53779 | MK10_HUMAN | Homo sapiens | 3 | 0.7578 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7522 |
| Reaction center protein L chain | P0C0Y8 | RCEL_RHOSH | Rhodobacter sphaeroides | 3 | 0.7517 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7484 |
| Dihydrofolate reductase | P00374 | DYR_HUMAN | Homo sapiens | 3 | 0.7462 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7442 |
| Biphenyl dioxygenase subunit alpha | P37333 | BPHA_PARXL | Paraburkholderia xenovorans | 3 | 0.7439 |
| Enoyl-ACP reductase | Q9BJJ9 | Q9BJJ9_PLAFA | Plasmodium falciparum | 3 | 0.7439 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7410 |
| Peptidyl-prolyl cis-trans isomerase FKBP5 | Q13451 | FKBP5_HUMAN | Homo sapiens | 3 | 0.7408 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7385 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 2 | 0.7377 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7376 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7350 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7347 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7338 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7332 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7325 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 3 | 0.7304 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7251 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7241 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7234 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.7232 |
| Pyridoxal kinase | P82197 | PDXK_SHEEP | Ovis aries | 3 | 0.7228 |
| UTP-monosaccharide-1-phosphate uridylyltransferase | D3G6S4 | D3G6S4_LEIMA | Leishmania major | 3 | 0.7218 |
| Pteridine reductase 1 | Q01782 | PTR1_LEIMA | Leishmania major | 3 | 0.7214 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7213 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 2 | 0.7212 |
| EbrA repressor | Q79SH7 | Q79SH7_STRLI | Streptomyces lividans | 2 | 0.7185 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7163 |
| Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial | P08559 | ODPA_HUMAN | Homo sapiens | 3 | 0.7151 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7119 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7102 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 4 | 0.7091 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7091 |
| Dihydrofolate reductase | Q83AB2 | Q83AB2_COXBU | Coxiella burnetii | 3 | 0.7090 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7066 |
| Dihydrofolate reductase | P00381 | DYR_LACCA | Lacticaseibacillus casei | 3 | 0.7058 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7053 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7052 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 2 | 0.7048 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7038 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7025 |