NP-MRD: Showing NP-Card for (-)-Monatin (NP0068688)

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Record Information

Version

2.0

Created at

2022-04-28 13:57:24 UTC

Updated at

2022-04-28 13:57:24 UTC

NP-MRD ID

NP0068688

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Monatin

Description

Monatin belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. (-)-Monatin is found in Schlerochiton ilicifolius and Sclerochiton ilicifolius. (-)-Monatin was first documented in 2016 (PMID: 27477667). Based on a literature review a small amount of articles have been published on Monatin (PMID: 34940636) (PMID: 27477656) (PMID: 26747978) (PMID: 26747976).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.8423    1.1426    0.9851 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0494    0.6762    0.4098 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8666   -0.4022   -0.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0427   -0.1166   -1.7910 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5814    1.0118   -2.4090 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3748   -0.3270   -1.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3652    0.2544   -0.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1278    1.4152   -1.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9291    1.6005   -0.1120 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7265    0.6249    0.7811 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2957    0.3617    2.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440   -0.7159    2.7897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9763   -1.5753    2.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4053   -1.3145    1.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7534   -0.2321    0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5461   -1.2471   -2.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2340   -2.4057   -2.5095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2843   -0.8713   -3.8257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9366    0.1759    1.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0571   -0.2749    1.2081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5466    0.2059    2.8371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5672    0.6432    1.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8215    2.1807    1.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5595    1.5741   -0.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4614   -1.3447   -0.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9019   -0.7344   -0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0520    1.2420   -3.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7926   -0.2083   -2.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413   -1.4773   -1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0915    2.0607   -2.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6294    2.3789    0.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0630    1.0194    2.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3797   -0.9345    3.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6887   -2.4200    2.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564   -2.0114    0.7273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1949   -0.3919   -3.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1955    0.4372    3.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  4 16  1  0
 16 18  1  0
 16 17  2  0
  2 19  1  0
 19 21  1  0
 19 20  2  0
 15  7  1  0
 15 10  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  6
  3 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  8 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 18 36  1  0
 21 37  1  0
M  END


  Mrv1652304282215572D          

 21 22  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2483   -0.9076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0330   -1.1626    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2045   -1.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891   -2.2245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5914   -2.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6461   -0.6105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7302   -0.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    0.3409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -1.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0947    0.7063    0.0000 O   0  0  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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  6  0  0  0
 11 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 11 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0068688

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](C[C@@](O)(CC1=CNC2=CC=CC=C12)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16N2O5/c15-10(12(17)18)6-14(21,13(19)20)5-8-7-16-11-4-2-1-3-9(8)11/h1-4,7,10,16,21H,5-6,15H2,(H,17,18)(H,19,20)/t10-,14-/m0/s1

> <INCHI_KEY>
RMLYXMMBIZLGAQ-HZMBPMFUSA-N

> <FORMULA>
C14H16N2O5

> <MOLECULAR_WEIGHT>
292.291

> <EXACT_MASS>
292.105921623

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.415520445118265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4S)-4-amino-2-hydroxy-2-[(1H-indol-3-yl)methyl]pentanedioic acid

> <ALOGPS_LOGP>
-1.87

> <JCHEM_LOGP>
-2.032467337769578

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.9460107364966066

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0842550971447458

> <JCHEM_PKA_STRONGEST_BASIC>
9.152046810941407

> <JCHEM_POLAR_SURFACE_AREA>
136.64000000000001

> <JCHEM_REFRACTIVITY>
73.1551

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S)-4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic acid

> <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       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.143  -0.188   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.464  -1.694   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.928  -2.170   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.248  -3.676   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.713  -4.152   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.104  -4.707   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       3.073  -1.140   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -1.363  -0.508   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.393   0.636   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.839  -1.973   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.177   1.318   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18   21                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13                                                            
CONECT   18   11   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   11                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
(2S,4S)-4-Hydroxy-4-(indol-3-ylmethyl)glutamic acid	MeSH
2-Amino-4-carboxy-4-hydroxy-5-(3-indolyl)pentanoic acid	MeSH
4-Hydroxy-4-(indol-3-ylmethyl)glutamic acid	MeSH

Chemical Formula

C₁₄H₁₆N₂O₅

Average Mass

292.2910 Da

Monoisotopic Mass

292.10592 Da

IUPAC Name

(2S,4S)-4-amino-2-hydroxy-2-[(1H-indol-3-yl)methyl]pentanedioic acid

Traditional Name

(2S,4S)-4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](C[C@@](O)(CC1=CNC2=CC=CC=C12)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C14H16N2O5/c15-10(12(17)18)6-14(21,13(19)20)5-8-7-16-11-4-2-1-3-9(8)11/h1-4,7,10,16,21H,5-6,15H2,(H,17,18)(H,19,20)/t10-,14-/m0/s1

InChI Key

RMLYXMMBIZLGAQ-HZMBPMFUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Schlerochiton ilicifolius	-	KNApSAcK
Sclerochiton ilicifolius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
3-alkylindole
Indole
Indole or derivatives
Medium-chain hydroxy acid
Medium-chain fatty acid
Amino fatty acid
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Aralkylamine
Alpha-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Substituted pyrrole
Fatty acyl
Fatty acid
Benzenoid
Tertiary alcohol
Pyrrole
Heteroaromatic compound
1,3-aminoalcohol
Amino acid
Organoheterocyclic compound
Carboxylic acid
Azacycle
Primary amine
Hydrocarbon derivative
Organic oxide
Alcohol
Primary aliphatic amine
Carbonyl group
Organonitrogen compound
Amine
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-1.9	ALOGPS
logP	-2	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.08	ChemAxon
pKa (Strongest Basic)	9.15	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.64 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	73.16 m³·mol⁻¹	ChemAxon
Polarizability	28.42 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

C00004819

Chemspider ID

8036546

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Monatin

METLIN ID

Not Available

PubChem Compound

9860847

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Amino Y: Concise Synthesis of (2R,4R)-Monatin. Chem Pharm Bull (Tokyo). 2016;64(8):1242-7. doi: 10.1248/cpb.c16-00358. [PubMed:27477667 ]
Jibrin MO, Liu Q, Guingab-Cagmat J, Jones JB, Garrett TJ, Zhang S: Metabolomics Insights into Chemical Convergence in Xanthomonas perforans and Metabolic Changes Following Treatment with the Small Molecule Carvacrol. Metabolites. 2021 Dec 16;11(12):879. doi: 10.3390/metabo11120879. [PubMed:34940636 ]
Amino Y, Kawahara S, Mori K, Hirasawa K, Sakata H, Kashiwagi T: Preparation and Characterization of Four Stereoisomers of Monatin. Chem Pharm Bull (Tokyo). 2016;64(8):1161-71. doi: 10.1248/cpb.c16-00286. [PubMed:27477656 ]
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Showing NP-Card for (-)-Monatin (NP0068688)

MOL for NP0068688 ((-)-Monatin)

3D MOL for NP0068688 ((-)-Monatin)

3D SDF for NP0068688 ((-)-Monatin)

3D-SDF for NP0068688 ((-)-Monatin)

PDB for NP0068688 ((-)-Monatin)

3D PDB for NP0068688 ((-)-Monatin)

SMILES for NP0068688 ((-)-Monatin)

INCHI for NP0068688 ((-)-Monatin)

Structure for NP0068688 ((-)-Monatin)

3D Structure for NP0068688 ((-)-Monatin)