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Showing NP-Card for Adrenochrome (NP0339111)

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Record Information
Version2.0
Created at2024-09-11 19:44:19 UTC
Updated at2024-09-11 19:44:19 UTC
NP-MRD IDNP0339111
Secondary Accession NumbersNone
Natural Product Identification
Common NameAdrenochrome
Description Adrenochrome was first documented in 2019 (PMID: 32489514). Based on a literature review a significant number of articles have been published on Adrenochrome (PMID: 35852683) (PMID: 35597283) (PMID: 34884863) (PMID: 33222134) (PMID: 33101292) (PMID: 33012730).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0339111 (Adrenochrome)


  Mrv2104 05262322162D          

 13 14  0  0  0  0            999 V2000
   14.9403  -18.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3272  -19.2896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4134  -20.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6598  -20.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4883  -21.2526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1078  -19.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2827  -19.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8702  -19.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0452  -19.1181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2827  -18.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8702  -17.6892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1078  -18.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5203  -19.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
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3D MOL for NP0339111 (Adrenochrome)

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3D SDF for NP0339111 (Adrenochrome)

  Mrv2104 05262322162D          

 13 14  0  0  0  0            999 V2000
   14.9403  -18.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3272  -19.2896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4134  -20.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6598  -20.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4883  -21.2526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1078  -19.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2827  -19.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8702  -19.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0452  -19.1181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2827  -18.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8702  -17.6892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1078  -18.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5203  -19.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339111

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CC(O)C2=CC(=O)C(=O)C=C12

> <INCHI_IDENTIFIER>
InChI=1/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3

> <INCHI_KEY>
RPHLQSHHTJORHI-UHFFFAOYNA-N

> <FORMULA>
C9H9NO3

> <MOLECULAR_WEIGHT>
179.175

> <EXACT_MASS>
179.058243154

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.251574738834343

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-1-methyl-2,3,5,6-tetrahydro-1H-indole-5,6-dione

> <JCHEM_LOGP>
-0.31307499066666655

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.092169029015633

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6240891513198132

> <JCHEM_POLAR_SURFACE_AREA>
57.61

> <JCHEM_REFRACTIVITY>
48.556000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
adrenochrome

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0339111 (Adrenochrome)
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PDB for NP0339111 (Adrenochrome)
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      27.889 -34.977   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      26.744 -36.007   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      26.905 -37.539   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.498 -38.165   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      25.178 -39.672   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      24.468 -37.021   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.928 -37.021   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.158 -35.687   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      20.618 -35.687   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      22.928 -34.353   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      22.158 -33.020   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      24.468 -34.353   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.238 -35.687   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13    2    6   12                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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3D PDB for NP0339111 (Adrenochrome)
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SMILES for NP0339111 (Adrenochrome)
CN1CC(O)C2=CC(=O)C(=O)C=C12
Download
INCHI for NP0339111 (Adrenochrome)
InChI=1/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H9NO3
Average Mass179.1750 Da
Monoisotopic Mass179.05824 Da
IUPAC Name3-hydroxy-1-methyl-2,3,5,6-tetrahydro-1H-indole-5,6-dione
Traditional Nameadrenochrome
CAS Registry NumberNot Available
SMILES
CN1CC(O)C2=CC(=O)C(=O)C=C12
InChI Identifier
InChI=1/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3
InChI KeyRPHLQSHHTJORHI-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
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-0.31ChemAxon
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.61 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity48.56 m³·mol⁻¹ChemAxon
Polarizability17.25 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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 LinkAdrenochrome  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Tapbergenov SO, Sovetov BS, Smailova ZK: Adrenergic Receptors in the Mechanism of Regulation of Mitochondrial and Cytoplasmic Enzymes of Cardiomyocytes by Catecholamines. Bull Exp Biol Med. 2022 Jul;173(3):330-334. doi: 10.1007/s10517-022-05544-w. Epub  2022 Jul 19. [PubMed:35852683  ] 
  2. Zhang Y, Martin JE, Edmonds KA, Winkler ME, Giedroc DP: SifR is an Rrf2-family quinone sensor associated with catechol iron uptake in Streptococcus pneumoniae D39. J Biol Chem. 2022 Jul;298(7):102046. doi: 10.1016/j.jbc.2022.102046. Epub 2022  May 18. [PubMed:35597283  ] 
  3. Voronin MV, Kadnikov IA, Zainullina LF, Logvinov IO, Verbovaya ER, Antipova TA, Vakhitova YV, Seredenin SB: Neuroprotective Properties of Quinone Reductase 2 Inhibitor M-11, a 2-Mercaptobenzimidazole Derivative. Int J Mol Sci. 2021 Dec 2;22(23):13061. doi: 10.3390/ijms222313061. [PubMed:34884863  ] 
  4. Thahouly T, Tanguy E, Raherindratsara J, Bader MF, Chasserot-Golaz S, Gasman S, Vitale N: Bovine Chromaffin Cells: Culture and Fluorescence Assay for Secretion. Methods Mol Biol. 2021;2233:169-179. doi: 10.1007/978-1-0716-1044-2_11. [PubMed:33222134  ] 
  5. Reiske L, Schmucker SS, Steuber J, Toulouse C, Pfaffinger B, Stefanski V: Interkingdom Cross-Talk in Times of Stress: Salmonella Typhimurium Grown in the Presence of Catecholamines Inhibits Porcine Immune Functionality in vitro. Front Immunol. 2020 Sep 30;11:572056. doi: 10.3389/fimmu.2020.572056. eCollection  2020. [PubMed:33101292  ] 
  6. Ueda K, Okamoto Y, Aoki A, Jinno H: Catecholamine oxidation-mediated transcriptional inhibition in Mn neurotoxicity. J Toxicol Sci. 2020;45(10):619-624. doi: 10.2131/jts.45.619. [PubMed:33012730  ] 
  7. Hollett G, Roberts DS, Sewell M, Wensley E, Wagner J, Murray W, Krotz A, Toth B, Vijayakumar V, Sailor MJ: Quantum Ensembles of Silicon Nanoparticles: Discrimination of Static and Dynamic Photoluminescence Quenching Processes. J Phys Chem C Nanomater Interfaces. 2019 Jul 25;123(29):17976-17986. doi:  10.1021/acs.jpcc.9b04334. Epub 2019 Jul 1. [PubMed:32489514  ] 
  8. Wang J, Yan W, Zhou X, Liu Y, Tang C, Peng Y, Liu H, Sun L, Xiao L, He L: Metabolomics window into the role of acute kidney injury after coronary artery bypass grafting in diabetic nephropathy progression. PeerJ. 2020 May 14;8:e9111. doi: 10.7717/peerj.9111. eCollection 2020. [PubMed:32461830  ] 
  9. Isoyan AS, Simonyan KV, Simonyan RM, Babayan MA, Simonyan GM, Chavushyan VA, Simonyan MA: Superoxide-producing lipoprotein fraction from Stevia leaves: definition of specific activity. BMC Complement Altern Med. 2019 Apr 25;19(1):88. doi: 10.1186/s12906-019-2500-1. [PubMed:31023287  ] 
  10. Toulouse C, Schmucker S, Metesch K, Pfannstiel J, Michel B, Starke I, Moller HM, Stefanski V, Steuber J: Mechanism and impact of catecholamine conversion by Vibrio cholerae. Biochim Biophys Acta Bioenerg. 2019 Jun 1;1860(6):478-487. doi:  10.1016/j.bbabio.2019.04.003. Epub 2019 Apr 12. [PubMed:30986392  ]