| In ZINC since | Heavy atoms | Benign functionality |
|---|---|---|
| October 4th, 2005 | 25 | Yes |
Popular Name: Dicumarol Dicumarol
Methylenebis(4-hydroxycoumarin)
2-hydroxy-3-[(2-hydroxy-4-oxochromen-3-yl)methyl]chromen-4-one
2H-1-Benzopyran-2-one), 3,3'-methylenebis(4-hydroxy-
2H-1-Benzopyran-2-one, 3,3'-methylenebis(4-hydroxy)-
2H-1-Benzopyran-2-one, 3,3'-methylenebis(4-hydroxy-
2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy-
2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy- (9CI)
2H-1-Benzopyran-2-one], 3,3'-methylenebis[4-hydroxy-
3,3 -Methylene-bis[4-hydroxycoumarin]
3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one)
3,3'-Methyleen-bis(4-hydroxy-cumarine)
3,3'-Methyleen-bis(4-hydroxy-cumarine) [Dutch]
3,3'-Methylen-bis(4-hydroxy-cumarin)
3,3'-Methylen-bis(4-hydroxy-cumarin) [German]
3,3'-Methylene-bis(4-hydroxycoumarin)
3,3'-Methylene-bis(4-hydroxycoumarine)
3,3'-Methylene-bis(4-hydroxycoumarine) [French]
3,3'-methylenebis(2-hydroxy-4h-chromen-4-one)
3,3'-Methylenebis(4-hydroxy-1,2-benzopyrone)
3,3'-Methylenebis(4-hydroxy-2H-1-benzopyran-2-one)
3,3'-methylenebis(4-hydroxy-2H-chromen-2-one)
3,3'-Methylenebis(4-hydroxycoumarin)
3,3'-Methylenebis[4-hydroxy-1,2-benzopyrone]
3,3'-Methylenebis[4-hydroxy-2H-1-benzopyran-2-one]
3,3'-Methylenebis[4-hydroxycoumarin]
3,3'-Metilen-bis(4-idrossi-cumarina)
3,3'-Metilen-bis(4-idrossi-cumarina) [Italian]
4,4'-Dihydroxy-3,3'-methylene bis coumarin
4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one
5-19-06-00682 (Beilstein Handbook Reference)
66-76-2; bis-hydroxycoumarin; dicoumarin; dicoumarol; dicumarol; melitoxin
66-76-2; C00796; Dicoumarol; Dicumarol
66-76-2; D03798; Dicoumarol (INN); Dicumarol (TN); Dicumarol (USAN)
66-76-2; Dicumarol; Prestwick_90
Bis(4-hydroxycoumarin-3-yl)methane
Bis-3,3'-(4-hydroxycoumarinyl)methane
Bis-3,3'-(4-oxycoumarinyl)ethylacetate
Bis-Hydroxycoumarin;Bishydroxycoumarin;Dicoumarin;Dicoumarol
Coumarin, 3,3'-methylenebis(4-hydroxy-
Coumarin, 3,3'-methylenebis[4-hydroxy-
Coumarin, 3,3'-methylenebis[4-hydroxy- (8CI)
Di-(4-hydroxy-3-coumarinyl)methane
Di-4-hydroxy-3,3'-methylenedicoumarin
Dicoumarol [66-76-2]; (3,3'-Methylene-bis(4-hydroxycoumarin))
dicoumarol; dicoumarolum; dicumarol
Dicoumarol;Bis-Hydroxycoumarin;Bishydroxycoumarin;Dicoumarin
Dicumarol [66-76-2]; (3,3'-Methylene-bis(4-hydroxycoumarin))
symmetric dicoumarol analogue, 1
uncoupler of oxidative respiration
| Type pH range | xlogP | Des A‑Pol Apolar desolvation (kcal/mol) | Des Pol Polar desolvation (kcal/mol) | H Don H-bond donors | H Acc H-bond acceptors | Chg Net charge | tPSA (Ų) | MWT Molecular weight (g/mol) | RB Rotatable bonds | DL |
|---|---|---|---|---|---|---|---|---|---|---|
| Ref Reference (pH 7) | 3.33 | 9.94 | -141.69 | 0 | 6 | -2 | 107 | 334.283 | 2 | ↓ |
| Ref Reference (pH 7) | 3.33 | 8.89 | -64.51 | 1 | 6 | -1 | 104 | 335.291 | 2 | ↓ |
| Mid Mid (pH 6-8) | 3.33 | 7.78 | -16.67 | 2 | 6 | 0 | 101 | 336.299 | 2 | ↓ |
| Mid Mid (pH 6-8) | 3.33 | 9.99 | -143.4 | 0 | 6 | -2 | 107 | 334.283 | 2 | ↓ |
| Mid Mid (pH 6-8) | 3.33 | 8.03 | -18.7 | 2 | 6 | 0 | 101 | 336.299 | 2 | ↓ |
| Mid Mid (pH 6-8) | 3.33 | 10.46 | -142.62 | 0 | 6 | -2 | 107 | 334.283 | 2 | ↓ |
| Mid Mid (pH 6-8) | 3.33 | 9.14 | -66.5 | 1 | 6 | -1 | 104 | 335.291 | 2 | ↓ |
| Mid Mid (pH 6-8) | 3.33 | 9.16 | -65.12 | 1 | 6 | -1 | 104 | 335.291 | 2 | ↓ |
| Lo Low (pH 4.5-6) | 3.33 | 8.37 | -20.79 | 2 | 6 | 0 | 101 | 336.299 | 2 | ↓ |
| Note Type | Comments | Provided By |
|---|---|---|
| Molecular_Solubility | 3.526 | Bitter DB |
| M.P | 286-289 C | Indofine |
| MP | 286-289o C | Indofine |
| Mp [°C] | 290 - 292 | Acros Organics |
| MP | 290...292 | Enamine Building Blocks |
| ALOGPS_SOLUBILITY | 6.39e-02 g/l | DrugBank-approved |
| ALOGPS_SOLUBILITY | 6.62e-02 g/l | DrugBank-approved |
| purity | 9.500000000000000e+001 | Enamine Building Blocks Enamine Building Blocks |
| UniProt Database Links | ALDX_SPOSA; NFNB_ECOLI; NQO1_HUMAN; NQO1_RAT | ChEBI |
| biological_use | Antibacterial agent | IBScreen Bioactives |
| biological_use | Anticoagulant | IBScreen Bioactives |
| mechanism | Depletes clotting factor-IX | IBScreen Bioactives |
| mechanism | Depletes clotting factor-VII | IBScreen Bioactives |
| mechanism | depletes clotting factor-X | IBScreen Bioactives |
| mechanism | Depletes prothrombin | IBScreen Bioactives |
| H phrase | H302: Harmful if swallowed | Acros Organics |
| H phrase | H302: Harmful if swallowed; H411: Toxic to aquatic life with long lasting effects; H372: Causes damage to organs through prolonged or repeated exposure if swallowed | Acros Organics |
| biological_use | Haemorrhagic agent causing ``sweet clover'' disease in cattle | IBScreen Bioactives |
| mechanism | Interferes with synthesis of vitamin K dependent clotting-factors | IBScreen Bioactives |
| biological_source | Isol. from Melilotus alba and Anthoxanthum spp. | ZereneX Building Blocks |
| biological_use | Orally active anticoagulant | IBScreen Bioactives IBScreen Bioactives |
| Target | Others | Selleck Chemicals |
| P phrase | P301 + P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician | Acros Organics |
| P phrase | P301 + P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician; P260: Do not breathe dust/fume/gas/mist/vapors/spray; P273: Avoid release to the environment | Acros Organics |
| APPEARANCE | Powder | Indofine |
| R phrase | R22: Harmful if swallowed. | Acros Organics |
| R phrase | R22: Harmful if swallowed.; R48/25: Toxic : danger of serious damage to health by prolonged exposure if swallowed.; R51/53: Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. | Acros Organics |
| S phrase | S37: Wear suitable gloves. | Acros Organics |
| S phrase | S37: Wear suitable gloves.; S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).; S61: Avoid release to the environment. Refer to special instructions / safety data sheets. | Acros Organics |
| Hazard | T: Toxic | Acros Organics |
| Hazard | T: Toxic; N: Dangerous for the environment | Acros Organics |
| mechanism | Vitamin K antagonist | IBScreen Bioactives IBScreen Bioactives |
| Code | Description | Organism Class | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| NQO1-1-E | Quinone Reductase 1) (cluster #1 Of 3), Eukaryotic | Eukaryotes | 5 | 0.46 | Binding ≤ 10μM |
| PCSK7-1-E | Subtilisin/kexin Type 7 (cluster #1 Of 3), Eukaryotic | Eukaryotes | 1300 | 0.33 | Binding ≤ 10μM |
| CP2C9-1-E | Cytochrome P450 2C9 (cluster #1 Of 3), Eukaryotic | Eukaryotes | 600 | 0.35 | ADME/T ≤ 10μM |
| Uniprot | Swissprot | Description | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| NQO1_HUMAN | P15559 | Quinone Reductase 1), Human | 2.6 | 0.48 | Binding ≤ 1μM |
| NQO1_HUMAN | P15559 | Quinone Reductase 1), Human | 2.6 | 0.48 | Binding ≤ 10μM |
| PCSK7_HUMAN | Q16549 | Subtilisin/kexin Type 7, Human | 1300 | 0.33 | Binding ≤ 10μM |
| CP2C9_HUMAN | P11712 | Cytochrome P450 2C9, Human | 1900 | 0.32 | ADME/T ≤ 10μM |
| Description | Species |
|---|---|
| CYP2E1 reactions | |
| Regulation of ornithine decarboxylase (ODC) | |
| Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE) | |
| Synthesis of epoxy (EET) and dihydroxyeicosatrienoic acids (DHET) | |
| Xenobiotics |
