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Showing NP-Card for L-Dopaquinone (NP0335263)

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Record Information
Version2.0
Created at2024-09-11 00:48:19 UTC
Updated at2024-09-11 00:48:19 UTC
NP-MRD IDNP0335263
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Dopaquinone
DescriptionL-Dopaquinone belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). L-Dopaquinone was first documented in 2006 (PMID: 16784814). Based on a literature review a significant number of articles have been published on L-Dopaquinone (PMID: 39304291) (PMID: 34662013) (PMID: 35964734) (PMID: 35850043) (PMID: 33542935) (PMID: 33211468).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0335263 (L-Dopaquinone)


  Mrv2104 05262303202D          

 14 14  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  5  1  1  0  0  0  0
  5  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  3  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 13  9  2  0  0  0  0
 14  9  1  0  0  0  0
M  END
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3D MOL for NP0335263 (L-Dopaquinone)

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3D SDF for NP0335263 (L-Dopaquinone)

  Mrv2104 05262303202D          

 14 14  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  5  1  1  0  0  0  0
  5  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  3  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 13  9  2  0  0  0  0
 14  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335263

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CC1=CC(=O)C(=O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C9H9NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6H,3,10H2,(H,13,14)

> <INCHI_KEY>
AHMIDUVKSGCHAU-UHFFFAOYNA-N

> <FORMULA>
C9H9NO4

> <MOLECULAR_WEIGHT>
195.174

> <EXACT_MASS>
195.053157774

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.117838866980208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid

> <JCHEM_LOGP>
-2.099752563809541

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.869698948900208

> <JCHEM_PKA_STRONGEST_BASIC>
9.390416817355673

> <JCHEM_POLAR_SURFACE_AREA>
97.46000000000001

> <JCHEM_REFRACTIVITY>
49.478100000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0335263 (L-Dopaquinone)
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PDB for NP0335263 (L-Dopaquinone)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    7                                                       
CONECT    3    5    6                                                       
CONECT    4    5    8                                                       
CONECT    5    1    3    4                                                  
CONECT    6    3    9   10                                                  
CONECT    7    2    8   11                                                  
CONECT    8    4    7   12                                                  
CONECT    9    6   13   14                                                  
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14    9                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

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3D PDB for NP0335263 (L-Dopaquinone)
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SMILES for NP0335263 (L-Dopaquinone)
NC(CC1=CC(=O)C(=O)C=C1)C(O)=O
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INCHI for NP0335263 (L-Dopaquinone)
InChI=1/C9H9NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6H,3,10H2,(H,13,14)
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H9NO4
Average Mass195.1740 Da
Monoisotopic Mass195.05316 Da
IUPAC Name2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid
Traditional Name2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid
CAS Registry NumberNot Available
SMILES
NC(CC1=CC(=O)C(=O)C=C1)C(O)=O
InChI Identifier
InChI=1/C9H9NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6H,3,10H2,(H,13,14)
InChI KeyAHMIDUVKSGCHAU-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAlpha amino acids  
Alternative Parents
Substituents
  • Alpha-amino acid
    • 

  • O-benzoquinone
    • 

  • Quinone
    • 

  • Ketone
    • 

  • Cyclic ketone
    • 

  • Amino acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Primary aliphatic amine
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Amine
    • 

  • Organic oxide
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.1ChemAxon
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.48 m³·mol⁻¹ChemAxon
Polarizability18.12 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkL-Dopaquinone  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Di Costanzo LF: Structural characterization of tyrosinases and an update on human enzymes. Enzymes. 2024;56:55-83. doi: 10.1016/bs.enz.2024.06.004. Epub 2024 Aug 6. [PubMed:39304291  ] 
  2. Lui F, Stokkermans TJ: Heterochromia.. 2024 Jan. [PubMed:34662013  ] 
  3. Mine M, Mizuguchi H, Takayanagi T: Kinetic analyses of two-steps oxidation from l-tyrosine to l-dopaquinone with tyrosinase by capillary electrophoresis/dynamic frontal analysis. Anal Biochem. 2022 Oct 15;655:114856. doi: 10.1016/j.ab.2022.114856. Epub 2022  Aug 11. [PubMed:35964734  ] 
  4. Cao S, Wang D, Cheng R, Shi W, Zhang Q, Zeng H, Chen J: Modulation of the lipophilicity and molecular size of thiosemicarbazone inhibitors to regulate tyrosinase activity. Spectrochim Acta A Mol Biomol Spectrosc. 2022 Nov 15;281:121590. doi:  10.1016/j.saa.2022.121590. Epub 2022 Jul 6. [PubMed:35850043  ] 
  5. Shahrisa A, Nikkhah M, Shirzad H, Behzadi R, Sadeghizadeh M: Enhancing Catecholase Activity of a Recombinant Human Tyrosinase Through Multiple Strategies. Iran J Biotechnol. 2020 Apr 1;18(2):e2310. doi: 10.30498/IJB.2020.137293.2310.  eCollection 2020 Apr. [PubMed:33542935  ] 
  6. Yang SJ, Zou LY, Liu C, Zhong Q, Ma ZY, Yang J, Ji J, Muller-Buschbaum P, Xu ZK: Codeposition of Levodopa and Polyethyleneimine: Reaction Mechanism and Coating Construction. ACS Appl Mater Interfaces. 2020 Dec 2;12(48):54094-54103. doi:  10.1021/acsami.0c16142. Epub 2020 Nov 19. [PubMed:33211468  ] 
  7. Wu YC, Wang IJ: Heat-shock-induced tyrosinase gene ablation with CRISPR in zebrafish. Mol Genet Genomics. 2020 Jul;295(4):911-922. doi: 10.1007/s00438-020-01681-x.  Epub 2020 May 4. [PubMed:32367255  ] 
  8. VanArsdale E, Hornstrom D, Sjoberg G, Jarbur I, Pitzer J, Payne GF, van Maris AJA, Bentley WE: A Coculture Based Tyrosine-Tyrosinase Electrochemical Gene Circuit for Connecting Cellular Communication with Electronic Networks. ACS Synth Biol. 2020 May 15;9(5):1117-1128. doi: 10.1021/acssynbio.9b00469. Epub  2020 Apr 2. [PubMed:32208720  ] 
  9. Yu L, Chen L, Luo G, Liu L, Zhu W, Yan P, Zhang P, Zhang C, Wu W: Study on Synthesis and Biological Evaluation of 3-Aryl Substituted Xanthone Derivatives as Novel and Potent Tyrosinase Inhibitors. Chem Pharm Bull (Tokyo). 2019 Nov 1;67(11):1232-1241. doi: 10.1248/cpb.c19-00572.  Epub 2019 Sep 6. [PubMed:31495804  ] 
  10. Ochiai A, Tanaka S, Imai Y, Yoshida H, Kanaoka T, Tanaka T, Taniguchi M: New tyrosinase inhibitory decapeptide: Molecular insights into the role of tyrosine residues. J Biosci Bioeng. 2016 Jun;121(6):607-613. doi: 10.1016/j.jbiosc.2015.10.010. Epub  2015 Nov 14. [PubMed:26589783  ] 
  11. Fogal S, Carotti M, Giaretta L, Lanciai F, Nogara L, Bubacco L, Bergantino E: Human tyrosinase produced in insect cells: a landmark for the screening of new drugs addressing its activity. Mol Biotechnol. 2015 Jan;57(1):45-57. doi: 10.1007/s12033-014-9800-y. [PubMed:25189462  ] 
  12. Yi W, Dubois C, Yahiaoui S, Haudecoeur R, Belle C, Song H, Hardre R, Reglier M, Boumendjel A: Refinement of arylthiosemicarbazone pharmacophore in inhibition of mushroom tyrosinase. Eur J Med Chem. 2011 Sep;46(9):4330-5. doi: 10.1016/j.ejmech.2011.07.003. Epub  2011 Jul 8. [PubMed:21777998  ] 
  13. Gasowska B, Frackowiak B, Wojtasek H: Indirect oxidation of amino acid phenylhydrazides by mushroom tyrosinase. Biochim Biophys Acta. 2006 Sep;1760(9):1373-9. doi: 10.1016/j.bbagen.2006.05.001.  Epub 2006 May 16. [PubMed:16784814  ] 
  14. Lavado A, Jeffery G, Tovar V, de la Villa P, Montoliu L: Ectopic expression of tyrosine hydroxylase in the pigmented epithelium rescues the retinal abnormalities and visual function common in albinos in the absence of melanin. J Neurochem. 2006 Feb;96(4):1201-11. doi: 10.1111/j.1471-4159.2006.03657.x. [PubMed:16445854  ]