NP-MRD: Showing NP-Card for Hawkinsin (NP0086956)

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Record Information

Version

2.0

Created at

2022-05-11 16:35:40 UTC

Updated at

2022-05-11 16:35:40 UTC

NP-MRD ID

NP0086956

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hawkinsin

Description

Hawkinsin belongs to the class of organic compounds known as cysteine and derivatives. Cysteine 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. Hawkinsin is ninhydrin positive (a common test to detect amino acids and proteins with a free -NH2 group). Hawkinsin is a very strong basic compound (based on its pKa). Hawkinsin is a potentially toxic compound. Hawkinsin was first documented in 2000 (PMID: 11073718). Hawkinsin, with regard to humans, has been linked to the inborn metabolic disorder hawkinsinuria.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
    3.6230    0.4429   -1.2529 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3770    0.9526    0.0513 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2046    0.3152    0.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6583    0.5465   -0.1554 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6666   -0.2605    0.8036 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4195   -1.7333    0.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6685   -2.5341    0.4948 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2516   -3.8522    0.2265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2168   -1.9924   -0.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3937   -0.6765   -0.8545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0323    0.1196    0.3470 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9139   -0.1637    1.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1414    1.5915    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5248    1.8898   -0.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3863    0.9822   -0.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    3.1876   -0.8156 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5825    0.8857    0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5798    1.2972    2.0770 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7391    0.3635    0.3645 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6313    0.2916   -1.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1154    0.9423   -2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1130    2.0451   -0.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825    0.8291    1.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4188   -0.7485    0.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5273    0.0921    1.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3082   -1.9995   -0.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0175   -2.0848    1.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4017   -2.5413    1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5815   -3.7599   -0.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4640   -2.6182   -1.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7866   -0.1910   -1.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7499   -0.5688    1.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8352    2.2453    0.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4765    1.8029   -0.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6129    3.9981   -0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4989    0.9039   -0.0391 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  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
  2 17  1  0
 17 19  1  0
 17 18  2  0
 11  5  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  3 24  1  0
  5 25  1  1
  6 26  1  0
  6 27  1  0
  7 28  1  1
  8 29  1  0
  9 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 16 35  1  0
 19 36  1  0
M  END


  Mrv0541 02231219302D          

 19 19  0  0  0  0            999 V2000
   24.0934  -14.2008    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.1099  -13.4863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5224  -16.6758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2355  -14.2008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1725  -12.7718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9500  -15.4383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1725  -14.2008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6645  -13.3757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6645  -14.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3790  -14.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9350  -13.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5224  -14.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8080  -14.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5224  -15.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8080  -15.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9500  -14.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7600  -13.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2369  -14.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2369  -15.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 13  1  0  0  0  0
  2 12  1  0  0  0  0
  3 14  1  0  0  0  0
  4 16  1  0  0  0  0
  5 17  1  0  0  0  0
  6 16  2  0  0  0  0
  7 17  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 16  1  0  0  0  0
 11 12  1  0  0  0  0
 11 17  1  0  0  0  0
 12 13  1  0  0  0  0
 12 18  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0086956

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CSC1CC(O)C=CC1(O)CC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H17NO6S/c12-7(10(16)17)5-19-8-3-6(13)1-2-11(8,18)4-9(14)15/h1-2,6-8,13,18H,3-5,12H2,(H,14,15)(H,16,17)

> <INCHI_KEY>
SPXVLTDISXZSFM-UHFFFAOYSA-N

> <FORMULA>
C11H17NO6S

> <MOLECULAR_WEIGHT>
291.321

> <EXACT_MASS>
291.077657971

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
27.82939123320438

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-{[2-(carboxymethyl)-2,5-dihydroxycyclohex-3-en-1-yl]sulfanyl}propanoic acid

> <ALOGPS_LOGP>
-3.19

> <JCHEM_LOGP>
-3.891176269736174

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.208764334719689

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.93942479227327

> <JCHEM_PKA_STRONGEST_BASIC>
9.13420766816257

> <JCHEM_POLAR_SURFACE_AREA>
141.08

> <JCHEM_REFRACTIVITY>
68.53380000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hawkinsin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      44.974 -26.508   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      46.872 -25.174   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      47.642 -31.128   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      39.640 -26.508   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      50.722 -23.841   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      40.973 -28.818   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      50.722 -26.508   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      42.307 -24.968   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      42.307 -26.508   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      43.641 -27.278   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      48.412 -25.174   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      47.642 -26.508   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      46.308 -27.278   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      47.642 -29.588   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      46.308 -28.818   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      40.973 -27.278   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      49.952 -25.174   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      48.976 -27.278   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      48.976 -28.818   0.000  0.00  0.00           C+0
CONECT    1   10   13                                                       
CONECT    2   12                                                            
CONECT    3   14                                                            
CONECT    4   16                                                            
CONECT    5   17                                                            
CONECT    6   16                                                            
CONECT    7   17                                                            
CONECT    8    9                                                            
CONECT    9    8   10   16                                                  
CONECT   10    1    9                                                       
CONECT   11   12   17                                                       
CONECT   12    2   11   13   18                                             
CONECT   13    1   12   15                                                  
CONECT   14    3   15   19                                                  
CONECT   15   13   14                                                       
CONECT   16    4    6    9                                                  
CONECT   17    5    7   11                                                  
CONECT   18   12   19                                                       
CONECT   19   14   18                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
(2-L-Cystein-S-yl-1,4-dihydroxycyclohex-5-en-1- yl)acetic acid	HMDB
2-Amino-3-{[2-(carboxymethyl)-2,5-dihydroxycyclohex-3-en-1-yl]sulfanyl}propanoate	HMDB
2-Amino-3-{[2-(carboxymethyl)-2,5-dihydroxycyclohex-3-en-1-yl]sulphanyl}propanoate	HMDB
2-Amino-3-{[2-(carboxymethyl)-2,5-dihydroxycyclohex-3-en-1-yl]sulphanyl}propanoic acid	HMDB
Hawkinsin	MeSH

Chemical Formula

C₁₁H₁₇NO₆S

Average Mass

291.3210 Da

Monoisotopic Mass

291.07766 Da

IUPAC Name

2-amino-3-{[2-(carboxymethyl)-2,5-dihydroxycyclohex-3-en-1-yl]sulfanyl}propanoic acid

Traditional Name

hawkinsin

CAS Registry Number

Not Available

SMILES

NC(CSC1CC(O)C=CC1(O)CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C11H17NO6S/c12-7(10(16)17)5-19-8-3-6(13)1-2-11(8,18)4-9(14)15/h1-2,6-8,13,18H,3-5,12H2,(H,14,15)(H,16,17)

InChI Key

SPXVLTDISXZSFM-UHFFFAOYSA-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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine 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

Cysteine and derivatives

Alternative Parents

Substituents

Cysteine or derivatives
Alpha-amino acid
Hydroxy fatty acid
Thia fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Tertiary alcohol
Amino acid
Secondary alcohol
Carboxylic acid
Dialkylthioether
Sulfenyl compound
Thioether
Organic oxide
Organopnictogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Alcohol
Carbonyl group
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	-3.2	ALOGPS
logP	-3.9	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.94	ChemAxon
pKa (Strongest Basic)	9.13	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	141.08 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	68.53 m³·mol⁻¹	ChemAxon
Polarizability	27.83 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

HMDB0002354

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022975

KNApSAcK ID

Not Available

Chemspider ID

151775

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hawkinsin

METLIN ID

6641

PubChem Compound

173909

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tomoeda K, Awata H, Matsuura T, Matsuda I, Ploechl E, Milovac T, Boneh A, Scott CR, Danks DM, Endo F: Mutations in the 4-hydroxyphenylpyruvic acid dioxygenase gene are responsible for tyrosinemia type III and hawkinsinuria. Mol Genet Metab. 2000 Nov;71(3):506-10. [PubMed:11073718 ]

Showing NP-Card for Hawkinsin (NP0086956)

MOL for NP0086956 (Hawkinsin)

3D MOL for NP0086956 (Hawkinsin)

3D SDF for NP0086956 (Hawkinsin)

3D-SDF for NP0086956 (Hawkinsin)

PDB for NP0086956 (Hawkinsin)

3D PDB for NP0086956 (Hawkinsin)

SMILES for NP0086956 (Hawkinsin)

INCHI for NP0086956 (Hawkinsin)

Structure for NP0086956 (Hawkinsin)

3D Structure for NP0086956 (Hawkinsin)