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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:40 UTC

Update Date

2021-09-14 15:39:04 UTC

HMDB ID

HMDB0002184

Secondary Accession Numbers

HMDB02184

Metabolite Identification

Common Name

L-Threo-3-Phenylserine

Description

L-Threo-3-Phenylserine belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Threo-3-Phenylserine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make L-threo-3-phenylserine a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on L-Threo-3-Phenylserine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Glycylprolylhydroxyproline.mol
  Mrv0541 02231219242D          

 13 13  0  0  0  0            999 V2000
   -1.4289    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.0312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.8562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.0312    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
  6  1  1  0  0  0  0
  7  3  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  1  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  8 10  1  0  0  0  0
  7 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002184

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](C(O)C1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H11NO3/c10-7(9(12)13)8(11)6-4-2-1-3-5-6/h1-5,7-8,11H,10H2,(H,12,13)/t7-,8?/m0/s1

> <INCHI_KEY>
VHVGNTVUSQUXPS-JAMMHHFISA-N

> <FORMULA>
C9H11NO3

> <MOLECULAR_WEIGHT>
181.1885

> <EXACT_MASS>
181.073893223

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
17.771915368720986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-hydroxy-3-phenylpropanoic acid

> <ALOGPS_LOGP>
-1.75

> <JCHEM_LOGP>
-2.1032060924352725

> <ALOGPS_LOGS>
-1.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.905417655935008

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.160609590222362

> <JCHEM_PKA_STRONGEST_BASIC>
8.879865581564687

> <JCHEM_POLAR_SURFACE_AREA>
83.55

> <JCHEM_REFRACTIVITY>
46.3238

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-phenyl-L-serine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Glycylprolylhydroxyproline.mol                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.667   2.695   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   1.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   2.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   3.465   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -1.925   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000  -3.465   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.334  -1.155   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -1.925   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334   0.385   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.667  -1.925   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    3    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10   11   12    8                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
L-threo-b-Phenylserine	HMDB
L-threo-beta-Phenylserine	HMDB
threo-b-Hydroxy-L-phenylalanine	HMDB
threo-beta-Hydroxy-L-phenylalanine	HMDB
beta-Phenylserine	MeSH, HMDB
threo-beta-Phenylserine	MeSH, HMDB
beta-Hydroxyphenylalanine, erythro-(DL)-isomer	MeSH, HMDB
beta-Hydroxyphenylalanine, threo-(DL)-isomer	MeSH, HMDB
beta-Hydroxyphenylalanine	MeSH, HMDB
beta-Hydroxyphenylalanine, threo-(L)-isomer	MeSH, HMDB
(2Rs,3Sr)-2-amino-3-Hydroxy-3-phenylpropanoic acid	MeSH, HMDB
beta-Hydroxyphenylalanine, (DL)-isomer	MeSH, HMDB
(2S)-2-Amino-3-hydroxy-3-phenylpropanoate	Generator, HMDB
3-Phenylserine	MeSH, HMDB
Phenylserine	MeSH, HMDB
Threo-DL-phenyl-serine	MeSH, HMDB
DL-3-Phenylserine	MeSH, HMDB

Chemical Formula

C₉H₁₁NO₃

Average Molecular Weight

181.1885

Monoisotopic Molecular Weight

181.073893223

IUPAC Name

(2S)-2-amino-3-hydroxy-3-phenylpropanoic acid

Traditional Name

3-phenyl-L-serine

CAS Registry Number

6254-48-4

SMILES

N[C@@H](C(O)C1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C9H11NO3/c10-7(9(12)13)8(11)6-4-2-1-3-5-6/h1-5,7-8,11H,10H2,(H,12,13)/t7-,8?/m0/s1

InChI Key

VHVGNTVUSQUXPS-JAMMHHFISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine 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

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
3-phenylpropanoic-acid
Alpha-amino acid
L-alpha-amino acid
Beta-hydroxy acid
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Hydroxy acid
Amino acid
Secondary alcohol
Carboxylic acid
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Primary amine
Primary aliphatic amine
Aromatic alcohol
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Amine
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0002184)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.1 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-2.1	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	2.16	ChemAxon
pKa (Strongest Basic)	8.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.32 m³·mol⁻¹	ChemAxon
Polarizability	17.77 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	141.988	31661259
DarkChem	[M-H]-	138.668	31661259
DeepCCS	[M+H]+	136.792	30932474
DeepCCS	[M-H]-	134.396	30932474
DeepCCS	[M-2H]-	169.638	30932474
DeepCCS	[M+Na]+	144.097	30932474
AllCCS	[M+H]+	141.2	32859911
AllCCS	[M+H-H2O]+	137.0	32859911
AllCCS	[M+NH4]+	145.2	32859911
AllCCS	[M+Na]+	146.3	32859911
AllCCS	[M-H]-	137.6	32859911
AllCCS	[M+Na-2H]-	138.5	32859911
AllCCS	[M+HCOO]-	139.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.55 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8731 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.5 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	336.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	546.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	303.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	72.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	84.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	259.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	270.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	755.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	652.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	56.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	696.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	170.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	234.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	520.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	418.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	244.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Threo-3-Phenylserine	N[C@@H](C(O)C1=CC=CC=C1)C(O)=O	2879.9	Standard polar	33892256
L-Threo-3-Phenylserine	N[C@@H](C(O)C1=CC=CC=C1)C(O)=O	1650.2	Standard non polar	33892256
L-Threo-3-Phenylserine	N[C@@H](C(O)C1=CC=CC=C1)C(O)=O	2032.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Threo-3-Phenylserine,1TMS,isomer #1	C[Si](C)(C)OC(C1=CC=CC=C1)[C@H](N)C(=O)O	1668.2	Semi standard non polar	33892256
L-Threo-3-Phenylserine,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)C(O)C1=CC=CC=C1	1654.9	Semi standard non polar	33892256
L-Threo-3-Phenylserine,1TMS,isomer #3	C[Si](C)(C)N[C@H](C(=O)O)C(O)C1=CC=CC=C1	1744.2	Semi standard non polar	33892256
L-Threo-3-Phenylserine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)C(O[Si](C)(C)C)C1=CC=CC=C1	1668.5	Semi standard non polar	33892256
L-Threo-3-Phenylserine,2TMS,isomer #2	C[Si](C)(C)N[C@H](C(=O)O)C(O[Si](C)(C)C)C1=CC=CC=C1	1729.4	Semi standard non polar	33892256
L-Threo-3-Phenylserine,2TMS,isomer #3	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)C(O)C1=CC=CC=C1	1731.8	Semi standard non polar	33892256
L-Threo-3-Phenylserine,2TMS,isomer #4	C[Si](C)(C)N([C@H](C(=O)O)C(O)C1=CC=CC=C1)[Si](C)(C)C	1893.6	Semi standard non polar	33892256
L-Threo-3-Phenylserine,3TMS,isomer #1	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C1=CC=CC=C1	1723.4	Semi standard non polar	33892256
L-Threo-3-Phenylserine,3TMS,isomer #1	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C1=CC=CC=C1	1811.7	Standard non polar	33892256
L-Threo-3-Phenylserine,3TMS,isomer #1	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C1=CC=CC=C1	2041.3	Standard polar	33892256
L-Threo-3-Phenylserine,3TMS,isomer #2	C[Si](C)(C)OC(C1=CC=CC=C1)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1916.9	Semi standard non polar	33892256
L-Threo-3-Phenylserine,3TMS,isomer #2	C[Si](C)(C)OC(C1=CC=CC=C1)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1858.6	Standard non polar	33892256
L-Threo-3-Phenylserine,3TMS,isomer #2	C[Si](C)(C)OC(C1=CC=CC=C1)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2145.4	Standard polar	33892256
L-Threo-3-Phenylserine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](C(O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1917.7	Semi standard non polar	33892256
L-Threo-3-Phenylserine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](C(O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1881.4	Standard non polar	33892256
L-Threo-3-Phenylserine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](C(O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	2171.7	Standard polar	33892256
L-Threo-3-Phenylserine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](C(O[Si](C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1973.6	Semi standard non polar	33892256
L-Threo-3-Phenylserine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](C(O[Si](C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1948.7	Standard non polar	33892256
L-Threo-3-Phenylserine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](C(O[Si](C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	2028.6	Standard polar	33892256
L-Threo-3-Phenylserine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(C1=CC=CC=C1)[C@H](N)C(=O)O	1930.0	Semi standard non polar	33892256
L-Threo-3-Phenylserine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)C(O)C1=CC=CC=C1	1911.2	Semi standard non polar	33892256
L-Threo-3-Phenylserine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@H](C(=O)O)C(O)C1=CC=CC=C1	1979.8	Semi standard non polar	33892256
L-Threo-3-Phenylserine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2160.2	Semi standard non polar	33892256
L-Threo-3-Phenylserine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@H](C(=O)O)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2183.2	Semi standard non polar	33892256
L-Threo-3-Phenylserine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(O)C1=CC=CC=C1	2185.7	Semi standard non polar	33892256
L-Threo-3-Phenylserine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@H](C(=O)O)C(O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2336.1	Semi standard non polar	33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2370.7	Semi standard non polar	33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2390.4	Standard non polar	33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2445.1	Standard polar	33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(C1=CC=CC=C1)[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2575.4	Semi standard non polar	33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(C1=CC=CC=C1)[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2435.8	Standard non polar	33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(C1=CC=CC=C1)[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2478.5	Standard polar	33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C(O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2568.0	Semi standard non polar	33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C(O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2466.5	Standard non polar	33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C(O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2493.9	Standard polar	33892256
L-Threo-3-Phenylserine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2797.9	Semi standard non polar	33892256
L-Threo-3-Phenylserine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2681.5	Standard non polar	33892256
L-Threo-3-Phenylserine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2464.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - L-Threo-3-Phenylserine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9800000000-ac17c8cf04308cfbf46e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Threo-3-Phenylserine GC-MS (2 TMS) - 70eV, Positive	splash10-004i-5920000000-af65a901a0e2ee257a0f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Threo-3-Phenylserine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Threo-3-Phenylserine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 10V, Positive-QTOF	splash10-01qi-0900000000-23514fbcf274c89d0cb7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 20V, Positive-QTOF	splash10-00kr-0900000000-f372732e79c55b239dd9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 40V, Positive-QTOF	splash10-05r0-9300000000-ba241a9d0d7acb3fad1f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 10V, Negative-QTOF	splash10-001i-0900000000-efa96cba215699148b92	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 20V, Negative-QTOF	splash10-0aei-4900000000-d1f163f6dba4af36de4e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 40V, Negative-QTOF	splash10-00di-9000000000-b1e85af153ad7acb90ff	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 10V, Negative-QTOF	splash10-03e9-1900000000-6a8534e62614caf02826	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 20V, Negative-QTOF	splash10-062a-9700000000-111064f1b9bd7957351e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 40V, Negative-QTOF	splash10-016r-9800000000-097aee8d9061f5e463d5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 10V, Positive-QTOF	splash10-02mi-0900000000-61f6d72660986df76164	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 20V, Positive-QTOF	splash10-00xr-0900000000-60667427da53fcb17439	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 40V, Positive-QTOF	splash10-004i-9000000000-3052f2cb9b8f0395cd33	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022892

KNApSAcK ID

Not Available

Chemspider ID

13628311

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6532

PubChem Compound

12314153

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Bruns, Friedrich H.; Fiedler, Liselore. Enzymic cleavage and synthesis of L-threo-b-phenylserine and L-erythro-b-phenylserine. Biochemische Zeitschrift (1958), 330 324-41.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

BRUNS FH, FIEDLER L: Enzymatic cleavage and synthesis of L-threo-beta-phenylserine and L-erythro-beta-Phenyldrine. Nature. 1958 May 31;181(4622):1533-4. [PubMed:13566053 ]

Showing metabocard for L-Threo-3-Phenylserine (HMDB0002184)

MOL for HMDB0002184 (L-Threo-3-Phenylserine)

3D MOL for HMDB0002184 (L-Threo-3-Phenylserine)

3D SDF for HMDB0002184 (L-Threo-3-Phenylserine)

3D-SDF for HMDB0002184 (L-Threo-3-Phenylserine)

PDB for HMDB0002184 (L-Threo-3-Phenylserine)

3D PDB for HMDB0002184 (L-Threo-3-Phenylserine)

SMILES for HMDB0002184 (L-Threo-3-Phenylserine)

INCHI for HMDB0002184 (L-Threo-3-Phenylserine)

Structure for HMDB0002184 (L-Threo-3-Phenylserine)

3D Structure for HMDB0002184 (L-Threo-3-Phenylserine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra