| In ZINC since | Heavy atoms | Benign functionality |
|---|---|---|
| September 26th, 2005 | 22 | No |
Popular Name: Nordihydroguaiaretic acid Nordihydroguaiaretic acid
Find On: PubMed — Wikipedia — Google
CAS Numbers: 27686-84-6 , 500-38-9 , [500-38-9]
"Nordihydroguaiaretic acid, 95%"
(R*,S*)-4,4'-(2,3-Dimethylbutane-1,4-diyl)bispyrocatechol
1,2-Benzenediol, 4,4'-((2R,3S)-2,3-dimethyl-1,4-butanediyl)bis-, rel-
1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-, (R*,S*)-
1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane
27686-84-6; Actinex (TN); D04862; Masoprocol (USAN/INN); meso-Nordihydroguaiaretic acid
4,4'-((2R,3S)-2,3-Dimethylbutane-1,4-diyl)bis(benzene-1,2-diol)
4,4'-(2,3-dimethylbutane-1,4-diyl)dibenzene-1,2-diol
4,4Õ-(2,3-Dimethyltetramethylene)dipyrocatechol
4-[(2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
500-38-9; C10719; NDGA; Nordihydroguaiaretic acid
CPD-7661; nordihydroguaiaretate; nordihydroguaiaretic acid
meso-4,4'-(2,3-Dimethyltetramethylene)dipyrocatechol
meso-Nordihydroguaiaretic acid
Nordihydroguaiaretic acid (meso-form)
Nordihydroguaiaretic acid from Larrea divaricata (creosote bush)
Nordihydroguaiaretic Acid [500-38-9]
Nordihydroguaiaretic acid, 95%
Nordihydroguaiaretic acid, 97%
| 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) | 3.48 | 2.05 | -11.23 | 4 | 4 | 0 | 81 | 302.37 | 5 | ↓ |
| Note Type | Comments | Provided By |
|---|---|---|
| ALOGPS_SOLUBILITY | 1.36e-02 g/l | DrugBank-approved |
| MP | 182-187 °C | Indofine |
| Mp [°C] | 184 - 189 | Acros Organics |
| Melting_Point | 184-188? | Alfa-Aesar |
| Melting_Point | 184-188° | Alfa-Aesar |
| MP | 185 | TCI |
| biological_use | Antioxidant | IBScreen Bioactives |
| H phrase | H319: Causes serious eye irritation | Acros Organics |
| H phrase | H319: Causes serious eye irritation; H302: Harmful if swallowed; H315: Causes skin irritation; H335: May cause respiratory irritation | Acros Organics |
| biological_source | Isol. from Guaiacum officinale and Larrea sp. | ZereneX Building Blocks |
| mechanism | Leukotriene antagonist | IBScreen Bioactives IBScreen Bioactives |
| mechanism | Leukotriene antagonist; Antioxidant | ZereneX Building Blocks |
| Therapy | lipoxygenase inhibitor, antioxidant | SMDC MicroSource |
| P phrase | P261: Avoid breathing dust/fume/gas/mist/vapors/spray | Acros Organics |
| P phrase | P261: Avoid breathing dust/fume/gas/mist/vapors/spray; P301+ P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell; P302+ P352: IF ON SKIN: Wash with plenty of soap and water; P280: Wear protective gloves/protective clothing/eye | Acros Organics |
| R phrase | R22: Harmful if swallowed. | Acros Organics |
| R phrase | R22: Harmful if swallowed.; R36/37/38: Irritating to eyes, respiratory system and skin. | Acros Organics |
| S phrase | S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. | Acros Organics |
| S phrase | S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39: Wear suitable gloves and eye/face protection. | Acros Organics |
| Hazard | XN: Harmful | Acros Organics |
| UniProt Database Links | YO087_YEAST | ChEBI |
| Code | Description | Organism Class | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| CP19A-1-E | Cytochrome P450 19A1 (cluster #1 Of 3), Eukaryotic | Eukaryotes | 11 | 0.51 | Binding ≤ 10μM |
| IGF1R-1-E | Insulin-like Growth Factor 1 Receptor (cluster #1 Of 2), Eukaryotic | Eukaryotes | 900 | 0.38 | Binding ≤ 10μM |
| LOX1-1-E | Seed Lipoxygenase-1 (cluster #1 Of 3), Eukaryotic | Eukaryotes | 180 | 0.43 | Binding ≤ 10μM |
| LOX1-1-E | Seed Lipoxygenase-1 (cluster #1 Of 3), Eukaryotic | Eukaryotes | 3500 | 0.35 | Binding ≤ 10μM |
| LOX12-1-E | Arachidonate 12-lipoxygenase (cluster #1 Of 4), Eukaryotic | Eukaryotes | 5100 | 0.34 | Binding ≤ 10μM |
| LOX12-1-E | Arachidonate 12-lipoxygenase (cluster #1 Of 4), Eukaryotic | Eukaryotes | 5900 | 0.33 | Binding ≤ 10μM |
| LOX15-1-E | Arachidonate 15-lipoxygenase (cluster #1 Of 5), Eukaryotic | Eukaryotes | 110 | 0.44 | Binding ≤ 10μM |
| LOX15-1-E | Arachidonate 15-lipoxygenase (cluster #1 Of 5), Eukaryotic | Eukaryotes | 5100 | 0.34 | Binding ≤ 10μM |
| LOX5-1-E | Arachidonate 5-lipoxygenase (cluster #1 Of 6), Eukaryotic | Eukaryotes | 5000 | 0.34 | Binding ≤ 10μM |
| LT4R1-1-E | Leukotriene B4 Receptor 1 (cluster #1 Of 2), Eukaryotic | Eukaryotes | 85 | 0.45 | Binding ≤ 10μM |
| Q9BEG3-1-E | Arachidonate 5-lipoxygenase (cluster #1 Of 1), Eukaryotic | Eukaryotes | 400 | 0.41 | Binding ≤ 10μM |
| LOX5-6-E | Arachidonate 5-lipoxygenase (cluster #6 Of 7), Eukaryotic | Eukaryotes | 5000 | 0.34 | Functional ≤ 10μM |
| Q9BEG3-1-E | Arachidonate 5-lipoxygenase (cluster #1 Of 1), Eukaryotic | Eukaryotes | 1000 | 0.38 | Functional ≤ 10μM |
| Z100274-1-O | Liposome (cluster #1 Of 1), Other | Other | 2000 | 0.36 | Functional ≤ 10μM |
| Z100751-1-O | PMNL (Polymorphonuclear Leukocytes) (cluster #1 Of 2), Other | Other | 400 | 0.41 | Functional ≤ 10μM |
| Z50425-11-O | Plasmodium Falciparum (cluster #11 Of 22), Other | Other | 7943 | 0.32 | Functional ≤ 10μM |
| Z50587-3-O | Homo Sapiens (cluster #3 Of 9), Other | Other | 8000 | 0.32 | Functional ≤ 10μM |
| Z50597-12-O | Rattus Norvegicus (cluster #12 Of 12), Other | Other | 5000 | 0.34 | Functional ≤ 10μM |
| Z80156-1-O | HL-60 (Promyeloblast Leukemia Cells) (cluster #1 Of 12), Other | Other | 2300 | 0.36 | Functional ≤ 10μM |
| Z80224-1-O | MCF7 (Breast Carcinoma Cells) (cluster #1 Of 14), Other | Other | 8500 | 0.32 | Functional ≤ 10μM |
| Uniprot | Swissprot | Description | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| LOX12_HUMAN | P18054 | Arachidonate 12-lipoxygenase, Human | 110 | 0.44 | Binding ≤ 1μM |
| LOX15_HUMAN | P16050 | Arachidonate 15-lipoxygenase, Human | 110 | 0.44 | Binding ≤ 1μM |
| LOX15_RABIT | P12530 | Arachidonate 15-lipoxygenase, Rabit | 180 | 0.43 | Binding ≤ 1μM |
| LOX5_HUMAN | P09917 | Arachidonate 5-lipoxygenase, Human | 110 | 0.44 | Binding ≤ 1μM |
| Q9BEG3_BOVIN | Q9BEG3 | Arachidonate 5-lipoxygenase, Bovin | 400 | 0.41 | Binding ≤ 1μM |
| LOX5_RAT | P12527 | Arachidonate 5-lipoxygenase, Rat | 10 | 0.51 | Binding ≤ 1μM |
| CP19A_HUMAN | P11511 | Cytochrome P450 19A1, Human | 11 | 0.51 | Binding ≤ 1μM |
| IGF1R_HUMAN | P08069 | Insulin-like Growth Factor I Receptor, Human | 900 | 0.38 | Binding ≤ 1μM |
| LT4R1_HUMAN | Q15722 | Leukotriene B4 Receptor 1, Human | 85 | 0.45 | Binding ≤ 1μM |
| LOX1_SOYBN | P08170 | Seed Lipoxygenase-1, Soybn | 180 | 0.43 | Binding ≤ 1μM |
| LOX12_HUMAN | P18054 | Arachidonate 12-lipoxygenase, Human | 5100 | 0.34 | Binding ≤ 10μM |
| LOX15_HUMAN | P16050 | Arachidonate 15-lipoxygenase, Human | 110 | 0.44 | Binding ≤ 10μM |
| LOX15_RABIT | P12530 | Arachidonate 15-lipoxygenase, Rabit | 180 | 0.43 | Binding ≤ 10μM |
| LOX5_HUMAN | P09917 | Arachidonate 5-lipoxygenase, Human | 110 | 0.44 | Binding ≤ 10μM |
| Q9BEG3_BOVIN | Q9BEG3 | Arachidonate 5-lipoxygenase, Bovin | 400 | 0.41 | Binding ≤ 10μM |
| LOX5_RAT | P12527 | Arachidonate 5-lipoxygenase, Rat | 10 | 0.51 | Binding ≤ 10μM |
| CP19A_HUMAN | P11511 | Cytochrome P450 19A1, Human | 11 | 0.51 | Binding ≤ 10μM |
| IGF1R_HUMAN | P08069 | Insulin-like Growth Factor I Receptor, Human | 900 | 0.38 | Binding ≤ 10μM |
| LT4R1_HUMAN | Q15722 | Leukotriene B4 Receptor 1, Human | 85 | 0.45 | Binding ≤ 10μM |
| LOX1_SOYBN | P08170 | Seed Lipoxygenase-1, Soybn | 180 | 0.43 | Binding ≤ 10μM |
| Q9BEG3_BOVIN | Q9BEG3 | Arachidonate 5-lipoxygenase, Bovin | 1000 | 0.38 | Functional ≤ 10μM |
| LOX5_RAT | P12527 | Arachidonate 5-lipoxygenase, Rat | 120 | 0.44 | Functional ≤ 10μM |
| LOX5_HUMAN | P09917 | Arachidonate 5-lipoxygenase, Human | 85 | 0.45 | Functional ≤ 10μM |
| Z80156 | Z80156 | HL-60 (Promyeloblast Leukemia Cells) | 2300 | 0.36 | Functional ≤ 10μM |
| Z50587 | Z50587 | Homo Sapiens | 300 | 0.42 | Functional ≤ 10μM |
| Z100274 | Z100274 | Liposome | 2000 | 0.36 | Functional ≤ 10μM |
| Z80224 | Z80224 | MCF7 (Breast Carcinoma Cells) | 8500 | 0.32 | Functional ≤ 10μM |
| Z50425 | Z50425 | Plasmodium Falciparum | 5011.87234 | 0.34 | Functional ≤ 10μM |
| Z100751 | Z100751 | PMNL (Polymorphonuclear Leukocytes) | 400 | 0.41 | Functional ≤ 10μM |
| Z50597 | Z50597 | Rattus Norvegicus | 100 | 0.45 | Functional ≤ 10μM |
| Description | Species |
|---|---|
| Endogenous sterols | |
| Estrogen biosynthesis | |
| G alpha (q) signalling events | |
| IRS-related events triggered by IGF1R | |
| Leukotriene receptors | |
| SHC-related events triggered by IGF1R | |
| Signaling by Type 1 Insulin-like Growth Factor 1 Receptor (IGF1R) | |
| Synthesis of 12-eicosatetraenoic acid derivatives | |
| Synthesis of 15-eicosatetraenoic acid derivatives | |
| Synthesis of 5-eicosatetraenoic acids | |
| Synthesis of Hepoxilins (HX) and Trioxilins (TrX) | |
| Synthesis of Leukotrienes (LT) and Eoxins (EX) | |
| Synthesis of Lipoxins (LX) |
