NP-MRD: Showing NP-Card for Lentinic acid (NP0049091)

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Record Information

Version

2.0

Created at

2022-03-17 21:06:59 UTC

Updated at

2022-03-17 21:06:59 UTC

NP-MRD ID

NP0049091

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lentinic acid

Description

Lentinic acid, also known as lentinate, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Lentinic acid is a very strong basic compound (based on its pKa). Outside of the human body, Lentinic acid has been detected, but not quantified in, mushrooms. Lentinic acid is found in Lentinus edodes . This could make lentinic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310252D          

 28 27  0  0  0  0            999 V2000
    3.3235    1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3179   -2.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5078   -2.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8073   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4571   -1.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8931   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2433   -0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8580   -3.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6175   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9677   -1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6681   -2.8972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5879   -3.8327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1575   -2.1177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2377   -1.1822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2082   -3.5209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9382   -2.1177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6976   -0.5586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474   -0.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5373   -0.2467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1871    0.2210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1632    0.6887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1598    0.9170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4071   -0.1632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2672   -1.0263    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0830   -0.5586    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332   -0.0908    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7834    0.3769    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  8  2  1  0  0  0  0
  9  4  1  0  0  0  0
 10  3  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
 16 11  2  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
 25  4  1  0  0  0  0
 25  5  1  0  0  0  0
 25 20  2  0  0  0  0
 26  5  1  0  0  0  0
 26  6  1  0  0  0  0
 26 21  2  0  0  0  0
 27  6  1  0  0  0  0
 27  7  1  0  0  0  0
 27 22  2  0  0  0  0
 28  1  1  0  0  0  0
 28  7  1  0  0  0  0
 28 23  2  0  0  0  0
 28 24  2  0  0  0  0
M  END


  Mrv0541 05061310252D          

 28 27  0  0  0  0            999 V2000
    3.3235    1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3179   -2.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5078   -2.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8073   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4571   -1.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8931   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2433   -0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8580   -3.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6175   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9677   -1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6681   -2.8972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5879   -3.8327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1575   -2.1177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2377   -1.1822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2082   -3.5209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9382   -2.1177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6976   -0.5586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474   -0.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5373   -0.2467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1871    0.2210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1632    0.6887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1598    0.9170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4071   -0.1632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2672   -1.0263    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0830   -0.5586    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332   -0.0908    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7834    0.3769    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  8  2  1  0  0  0  0
  9  4  1  0  0  0  0
 10  3  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
 16 11  2  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
 25  4  1  0  0  0  0
 25  5  1  0  0  0  0
 25 20  2  0  0  0  0
 26  5  1  0  0  0  0
 26  6  1  0  0  0  0
 26 21  2  0  0  0  0
 27  6  1  0  0  0  0
 27  7  1  0  0  0  0
 27 22  2  0  0  0  0
 28  1  1  0  0  0  0
 28  7  1  0  0  0  0
 28 23  2  0  0  0  0
 28 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0049091

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CS(=O)(=O)CS(=O)CS(=O)CS(=O)CC(\N=C(/O)CCC(N)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H22N2O10S4/c1-28(23,24)7-27(22)6-26(21)5-25(20)4-9(12(18)19)14-10(15)3-2-8(13)11(16)17/h8-9H,2-7,13H2,1H3,(H,14,15)(H,16,17)(H,18,19)

> <INCHI_KEY>
YJXVNZXKWINDJO-UHFFFAOYSA-N

> <FORMULA>
C12H22N2O10S4

> <MOLECULAR_WEIGHT>
482.57

> <EXACT_MASS>
482.015727694

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
44.8351234281879

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-[(Z)-(1-carboxy-2-methanesulfonylmethanesulfinylmethanesulfinylmethanesulfinylethyl)-C-hydroxycarbonimidoyl]butanoic acid

> <ALOGPS_LOGP>
-0.85

> <JCHEM_LOGP>
-7.743896253373163

> <ALOGPS_LOGS>
-1.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.003896701934281

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3924020434868565

> <JCHEM_PKA_STRONGEST_BASIC>
9.337024086481978

> <JCHEM_POLAR_SURFACE_AREA>
218.55999999999997

> <JCHEM_REFRACTIVITY>
103.6813

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.06e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-[(Z)-(1-carboxy-2-methanesulfonylmethanesulfinylmethanesulfinylmethanesulfinylethyl)-C-hydroxycarbonimidoyl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.204   1.868   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.927  -4.535   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.415  -4.826   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.374  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.853  -2.207   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.667  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.187  -0.461   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.935  -5.699   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.886  -2.789   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.406  -3.662   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -12.447  -5.408   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.390  -1.334   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0     -10.431  -7.154   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      -5.894  -3.953   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      -7.910  -2.207   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0     -13.455  -6.572   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0     -12.951  -3.953   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -6.902  -1.043   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.382  -0.169   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.870  -0.461   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.349   0.413   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.171   1.286   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.032   1.712   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.360  -0.305   0.000  0.00  0.00           O+0
HETATM   25  S   UNK     0      -2.365  -1.916   0.000  0.00  0.00           S+0
HETATM   26  S   UNK     0       0.155  -1.043   0.000  0.00  0.00           S+0
HETATM   27  S   UNK     0       2.675  -0.169   0.000  0.00  0.00           S+0
HETATM   28  S   UNK     0       5.196   0.704   0.000  0.00  0.00           S+0
CONECT    1   28                                                            
CONECT    2    3    8                                                       
CONECT    3    2   10                                                       
CONECT    4    9   25                                                       
CONECT    5   25   26                                                       
CONECT    6   26   27                                                       
CONECT    7   27   28                                                       
CONECT    8    2   11   13                                                  
CONECT    9    4   12   14                                                  
CONECT   10    3   14   15                                                  
CONECT   11    8   16   17                                                  
CONECT   12    9   18   19                                                  
CONECT   13    8                                                            
CONECT   14    9   10                                                       
CONECT   15   10                                                            
CONECT   16   11                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   12                                                            
CONECT   20   25                                                            
CONECT   21   26                                                            
CONECT   22   27                                                            
CONECT   23   28                                                            
CONECT   24   28                                                            
CONECT   25    4    5   20                                                  
CONECT   26    5    6   21                                                  
CONECT   27    6    7   22                                                  
CONECT   28    1    7   23   24                                             
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

View in JSmol

Synonyms

Value	Source
Lentinate	Generator
(Lentinic acid)	HMDB
2-Amino-4-[(1-carboxy-2-methanesulfonylmethanesulfinylmethanesulfinylmethanesulfinylethyl)-C-hydroxycarbonimidoyl]butanoate	Generator
2-Amino-4-[(1-carboxy-2-methanesulphonylmethanesulphinylmethanesulphinylmethanesulphinylethyl)-C-hydroxycarbonimidoyl]butanoate	Generator
2-Amino-4-[(1-carboxy-2-methanesulphonylmethanesulphinylmethanesulphinylmethanesulphinylethyl)-C-hydroxycarbonimidoyl]butanoic acid	Generator

Chemical Formula

C₁₂H₂₂N₂O₁₀S₄

Average Mass

482.5700 Da

Monoisotopic Mass

482.01573 Da

IUPAC Name

2-amino-4-[(Z)-(1-carboxy-2-methanesulfonylmethanesulfinylmethanesulfinylmethanesulfinylethyl)-C-hydroxycarbonimidoyl]butanoic acid

Traditional Name

2-amino-4-[(Z)-(1-carboxy-2-methanesulfonylmethanesulfinylmethanesulfinylmethanesulfinylethyl)-C-hydroxycarbonimidoyl]butanoic acid

CAS Registry Number

12705-98-5

SMILES

CS(=O)(=O)CS(=O)CS(=O)CS(=O)CC(\N=C(/O)CCC(N)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C12H22N2O10S4/c1-28(23,24)7-27(22)6-26(21)5-25(20)4-9(12(18)19)14-10(15)3-2-8(13)11(16)17/h8-9H,2-7,13H2,1H3,(H,14,15)(H,16,17)(H,18,19)

InChI Key

YJXVNZXKWINDJO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Lentinus edodes	Fungi	KNApSAcK
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Gamma-glutamyl alpha-amino acid
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
Dicarboxylic acid or derivatives
Fatty amide
N-acyl-amine
Fatty acid
Fatty acyl
Sulfonyl
Sulfone
Secondary carboxylic acid amide
Amino acid or derivatives
Sulfoxide
Carboxamide group
Amino acid
Sulfinyl compound
Carboxylic acid
Hydrocarbon derivative
Organic oxygen compound
Primary aliphatic amine
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organosulfur compound
Amine
Primary amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-0.85	ALOGPS
logP	-7.7	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.39	ChemAxon
pKa (Strongest Basic)	9.34	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	218.56 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	103.68 m³·mol⁻¹	ChemAxon
Polarizability	44.84 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038385

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017735

KNApSAcK ID

Not Available

Chemspider ID

297389

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

335576

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lentinic acid (NP0049091)

MOL for NP0049091 (Lentinic acid)

3D MOL for NP0049091 (Lentinic acid)

3D SDF for NP0049091 (Lentinic acid)

3D-SDF for NP0049091 (Lentinic acid)

PDB for NP0049091 (Lentinic acid)

3D PDB for NP0049091 (Lentinic acid)

SMILES for NP0049091 (Lentinic acid)

INCHI for NP0049091 (Lentinic acid)

Structure for NP0049091 (Lentinic acid)

3D Structure for NP0049091 (Lentinic acid)