NP-MRD: Showing NP-Card for Musca-aurin VII (NP0050757)

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Record Information

Version

2.0

Created at

2022-04-27 22:05:26 UTC

Updated at

2022-04-27 22:05:26 UTC

NP-MRD ID

NP0050757

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Musca-aurin VII

Description

Musca-aurin VII, also known as muscaaurin VII, belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Musca-aurin VII is found in Amanita muscaria , Beta vulgaris and Opuntia ficus-indica . Based on a literature review very few articles have been published on Musca-aurin VII.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282200052D          

 25 26  0  0  1  0            999 V2000
   -0.6548   -0.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097   -1.4544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347   -1.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897   -0.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222   -0.1848    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -1.3222    0.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    1.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    0.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -0.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4656   -0.5973    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1801   -0.1848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1801    0.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4656    1.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8946    1.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6091    0.6402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8946    1.8777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4656   -1.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1801   -1.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -1.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2197   -2.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8841   -2.8755    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0636   -2.9617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3690   -3.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0335   -4.2966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895   -3.4567    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 10 17  1  1  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
M  CHG  2   5   1  25  -1
M  END
> <DATABASE_ID>
NP0050757

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CC1=C\[N+](=C/C=C2\C[C@H](NC(=C2)C(O)=O)C(O)=O)C=N1)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H16N4O6/c16-10(13(20)21)5-9-6-19(7-17-9)2-1-8-3-11(14(22)23)18-12(4-8)15(24)25/h1-3,6-7,10,12H,4-5,16H2,(H3,20,21,22,23,24,25)/t10-,12-/m0/s1

> <INCHI_KEY>
OROLDOQHKPWCGQ-JQWIXIFHSA-N

> <FORMULA>
C15H16N4O6

> <MOLECULAR_WEIGHT>
348.315

> <EXACT_MASS>
348.106984251

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
34.21137498473068

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1E)-4-[(2S)-2-amino-2-carboxyethyl]-1-{2-[(2S,4E)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-1H-1lambda5-imidazol-1-ylium

> <ALOGPS_LOGP>
-1.23

> <JCHEM_LOGP>
-7.676550465937782

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.5461803845772684

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0522943009494674

> <JCHEM_PKA_STRONGEST_BASIC>
9.1103834284984

> <JCHEM_POLAR_SURFACE_AREA>
168.15

> <JCHEM_REFRACTIVITY>
108.93919999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1E)-4-[(2S)-2-amino-2-carboxyethyl]-1-{2-[(2S,4E)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene}-1H-1lambda5-imidazol-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.222  -1.250   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.698  -2.715   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -3.238  -2.715   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.714  -1.250   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -2.468  -0.345   0.000  0.00  0.00           N+1
HETATM    6  C   UNK     0      -2.468   1.195   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.802   1.965   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.136   1.195   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.136  -0.345   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.469  -1.115   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -7.803  -0.345   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -7.803   1.195   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.469   1.965   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.137   1.965   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0     -10.470   1.195   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -9.137   3.505   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -6.469  -2.655   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -7.803  -3.425   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -5.136  -3.425   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.143  -3.961   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.517  -5.368   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -1.985  -5.529   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      -4.422  -6.613   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.796  -8.020   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -5.954  -6.452   0.000  0.00  0.00           O-1
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   10   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    3   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
Muscaaurin VII	Kegg

Chemical Formula

C₁₅H₁₆N₄O₆

Average Mass

348.3150 Da

Monoisotopic Mass

348.10698 Da

IUPAC Name

(1E)-4-[(2S)-2-amino-2-carboxyethyl]-1-{2-[(2S,4E)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-1H-1lambda5-imidazol-1-ylium

Traditional Name

(1E)-4-[(2S)-2-amino-2-carboxyethyl]-1-{2-[(2S,4E)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene}-1H-1lambda5-imidazol-1-ylium

CAS Registry Number

Not Available

SMILES

N[C@@H](CC1=C\[N+](=C/C=C2\C[C@H](NC(=C2)C(O)=O)C(O)=O)C=N1)C([O-])=O

InChI Identifier

InChI=1S/C15H16N4O6/c16-10(13(20)21)5-9-6-19(7-17-9)2-1-8-3-11(14(22)23)18-12(4-8)15(24)25/h1-3,6-7,10,12H,4-5,16H2,(H3,20,21,22,23,24,25)/t10-,12-/m0/s1

InChI Key

OROLDOQHKPWCGQ-JQWIXIFHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amanita muscaria	Fungi	KNApSAcK
Beta vulgaris	Plant	KNApSAcK
Opuntia ficus-indica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Histidine and derivatives

Alternative Parents

Substituents

Histidine or derivatives
Alpha-amino acid
L-alpha-amino acid
Tricarboxylic acid or derivatives
Dihydropyridine
Aralkylamine
Hydropyridine
N-substituted imidazole
Heteroaromatic compound
Azole
Imidazole
Amino acid
Carboxylic acid salt
Ketimine
Azacycle
Organoheterocyclic compound
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organonitrogen compound
Amine
Primary aliphatic amine
Organic oxide
Imine
Organic salt
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Primary amine
Organopnictogen compound
Organic zwitterion
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:7030 )
Betaxanthins (C08562 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.2	ALOGPS
logP	-7.7	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	2.05	ChemAxon
pKa (Strongest Basic)	9.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	168.15 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	108.94 m³·mol⁻¹	ChemAxon
Polarizability	34.21 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001601

Chemspider ID

30791222

KEGG Compound ID

C08562

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441632

PDB ID

Not Available

ChEBI ID

7030

Good Scents ID

Not Available

References

General References

Showing NP-Card for Musca-aurin VII (NP0050757)

MOL for NP0050757 (Musca-aurin VII)

3D MOL for NP0050757 (Musca-aurin VII)

3D SDF for NP0050757 (Musca-aurin VII)

3D-SDF for NP0050757 (Musca-aurin VII)

PDB for NP0050757 (Musca-aurin VII)

3D PDB for NP0050757 (Musca-aurin VII)

SMILES for NP0050757 (Musca-aurin VII)

INCHI for NP0050757 (Musca-aurin VII)

Structure for NP0050757 (Musca-aurin VII)

3D Structure for NP0050757 (Musca-aurin VII)