NP-MRD: Showing NP-Card for Humilixanthin (NP0049311)

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Record Information

Version

2.0

Created at

2022-03-17 21:10:27 UTC

Updated at

2022-03-17 21:10:27 UTC

NP-MRD ID

NP0049311

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Humilixanthin

Description

Humilixanthin 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). Humilixanthin is a very strong basic compound (based on its pKa). Outside of the human body, Humilixanthin has been detected, but not quantified in, common beets and root vegetables. Humilixanthin is found in Delosperma luteum, Iso. from the yellow-coloured root of beetroot, Lampranthus aurantiacus, Phytolacca acinosa and Portulaca grandiflora . This could make humilixanthin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241217592D          

 23 23  0  0  0  0            999 V2000
   -2.1240    0.2008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4025    0.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6810    0.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6810   -0.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4025   -1.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1240   -0.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7653   -1.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7653   -1.8033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0404   -1.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6810   -0.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6810    0.2008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4025    0.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0438    0.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7653    0.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4868    0.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4868   -0.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6810    1.8033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4025    1.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0438    1.8033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1240    1.8033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4025    1.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6810    1.8033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4868   -0.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  2  0  0  0  0
  2 21  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 23  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 18  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0049311

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCCC(\N=C\C=C1\CC(NC(=C1)C(O)=O)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18N2O7/c17-5-1-2-9(12(18)19)15-4-3-8-6-10(13(20)21)16-11(7-8)14(22)23/h3-4,6,9,11,16-17H,1-2,5,7H2,(H,18,19)(H,20,21)(H,22,23)/b8-3+,15-4+

> <INCHI_KEY>
RVPIQBBRHBAQKG-UMBPYZIISA-N

> <FORMULA>
C14H18N2O7

> <MOLECULAR_WEIGHT>
326.3019

> <EXACT_MASS>
326.11140094

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
31.841357788187825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4Z)-4-[(2E)-2-[(1-carboxy-4-hydroxybutyl)imino]ethylidene]-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic acid

> <ALOGPS_LOGP>
0.34

> <JCHEM_LOGP>
-3.1380869868046175

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.468888590907782

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6919107209999065

> <JCHEM_PKA_STRONGEST_BASIC>
8.670349649555195

> <JCHEM_POLAR_SURFACE_AREA>
156.51999999999998

> <JCHEM_REFRACTIVITY>
79.366

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.85e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4Z)-4-[(2E)-2-[(1-carboxy-4-hydroxybutyl)imino]ethylidene]-2,3-dihydro-1H-pyridine-2,6-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      -3.965   0.375   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -2.618   1.122   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.271   0.375   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.271  -1.122   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.618  -1.870   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.965  -1.122   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.162  -1.870   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.162  -3.366   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.075  -1.870   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.271  -1.122   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.271   0.375   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.618   1.122   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.815   0.375   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.162   1.122   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.509   0.375   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.509  -1.122   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.271   3.366   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.618   2.618   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.815   3.366   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.965   3.366   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.618   2.618   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.271   3.366   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.509  -1.122   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8   23                                                  
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   18                                                            
CONECT   18   12   17   19                                                  
CONECT   19   18                                                            
CONECT   20   21                                                            
CONECT   21    2   20   22                                                  
CONECT   22   21                                                            
CONECT   23    7                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Value	Source
(4Z)-4-[(2E)-2-[(1-Carboxy-4-hydroxybutyl)imino]ethylidene]-1,2,3,4-tetrahydropyridine-2,6-dicarboxylate	Generator

Chemical Formula

C₁₄H₁₈N₂O₇

Average Mass

326.3019 Da

Monoisotopic Mass

326.11140 Da

IUPAC Name

(4Z)-4-[(2E)-2-[(1-carboxy-4-hydroxybutyl)imino]ethylidene]-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic acid

Traditional Name

(4Z)-4-[(2E)-2-[(1-carboxy-4-hydroxybutyl)imino]ethylidene]-2,3-dihydro-1H-pyridine-2,6-dicarboxylic acid

CAS Registry Number

111534-70-4

SMILES

OCCCC(\N=C\C=C1\CC(NC(=C1)C(O)=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C14H18N2O7/c17-5-1-2-9(12(18)19)15-4-3-8-6-10(13(20)21)16-11(7-8)14(22)23/h3-4,6,9,11,16-17H,1-2,5,7H2,(H,18,19)(H,20,21)(H,22,23)/b8-3+,15-4+

InChI Key

RVPIQBBRHBAQKG-UMBPYZIISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Beta vulgaris	FooDB	KNAPSACK
Delosperma luteum	Plant	KNApSAcK
Iso. from the yellow-coloured root of beetroot	-	KNApSAcK
Lampranthus aurantiacus	Plant	KNApSAcK
Phytolacca acinosa	Plant	KNApSAcK
Portulaca grandiflora	Plant	KNApSAcK

Chemical Taxonomy

Description

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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Tricarboxylic acid or derivatives
Tetrahydropyridine
Hydropyridine
Shiff base
Amino acid
Aldimine
Carboxylic acid
Secondary aliphatic amine
Enamine
Secondary amine
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Imine
Organic oxygen compound
Primary alcohol
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	0.34	ALOGPS
logP	-3.1	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	1.69	ChemAxon
pKa (Strongest Basic)	8.67	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	156.52 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	79.37 m³·mol⁻¹	ChemAxon
Polarizability	31.84 Å³	ChemAxon
Number of Rings	1	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

HMDB0039123

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018635

KNApSAcK ID

C00001590

Chemspider ID

Not Available

KEGG Compound ID

C08548

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Humilixanthin (NP0049311)

MOL for NP0049311 (Humilixanthin)

3D MOL for NP0049311 (Humilixanthin)

3D SDF for NP0049311 (Humilixanthin)

3D-SDF for NP0049311 (Humilixanthin)

PDB for NP0049311 (Humilixanthin)

3D PDB for NP0049311 (Humilixanthin)

SMILES for NP0049311 (Humilixanthin)

INCHI for NP0049311 (Humilixanthin)

Structure for NP0049311 (Humilixanthin)

3D Structure for NP0049311 (Humilixanthin)