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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (22) Show 22 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 19:36:23 UTC

Update Date

2021-10-01 23:09:13 UTC

HMDB ID

HMDB0258272

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Shikimate-3-phosphate

Description

4,5-dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Based on a literature review very few articles have been published on 4,5-dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Shikimate-3-phosphate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Shikimate-3-phosphate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

Structure #1
  Mrv0541 02241207032D          

 16 16  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  3  2  0  0  0  0
  2  5  1  0  0  0  0
  3  7  1  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5 15  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  2  0  0  0  0
  7 11  1  0  0  0  0
 12 16  1  0  0  0  0
 13 16  1  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258272

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1CC(=CC(OP(O)(O)=O)C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H11O8P/c8-4-1-3(7(10)11)2-5(6(4)9)15-16(12,13)14/h2,4-6,8-9H,1H2,(H,10,11)(H2,12,13,14)

> <INCHI_KEY>
QYOJSKGCWNAKGW-UHFFFAOYSA-N

> <FORMULA>
C7H11O8P

> <MOLECULAR_WEIGHT>
254.1312

> <EXACT_MASS>
254.01915384

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
20.345428817916567

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5-dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid

> <ALOGPS_LOGP>
-2.07

> <JCHEM_LOGP>
-1.7636401083333335

> <ALOGPS_LOGS>
-1.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.1018283495734575

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3157644234401227

> <JCHEM_PKA_STRONGEST_BASIC>
-3.225778459939349

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
49.8332

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.10e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
shikimate 3-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.874  -2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.206  -2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  P   UNK     0      -1.334  -2.310   0.000  0.00  0.00           P+0
CONECT    1    3    4                                                       
CONECT    2    3    5                                                       
CONECT    3    1    2    7                                                  
CONECT    4    1    6    8                                                  
CONECT    5    2    6   15                                                  
CONECT    6    4    5    9                                                  
CONECT    7    3   10   11                                                  
CONECT    8    4                                                            
CONECT    9    6                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
CONECT   12   16                                                            
CONECT   13   16                                                            
CONECT   14   16                                                            
CONECT   15    5   16                                                       
CONECT   16   12   13   14   15                                             
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0258272
HETATM    1  O1  UNL     1       3.830   1.087   0.807  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.817   1.498   0.198  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.857   2.754  -0.394  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.621   0.716   0.092  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.525   1.090  -0.532  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.615   0.137  -0.532  1.00  0.00           C  
HETATM    7  O3  UNL     1      -1.185   0.168   0.741  1.00  0.00           O  
HETATM    8  P1  UNL     1      -2.808   0.626   0.686  1.00  0.00           P  
HETATM    9  O4  UNL     1      -3.370   0.465   2.082  1.00  0.00           O  
HETATM   10  O5  UNL     1      -3.010   2.210   0.188  1.00  0.00           O  
HETATM   11  O6  UNL     1      -3.701  -0.421  -0.328  1.00  0.00           O  
HETATM   12  C5  UNL     1      -0.157  -1.254  -0.899  1.00  0.00           C  
HETATM   13  O7  UNL     1      -1.084  -2.139  -0.322  1.00  0.00           O  
HETATM   14  C6  UNL     1       1.198  -1.595  -0.374  1.00  0.00           C  
HETATM   15  O8  UNL     1       1.180  -2.874   0.202  1.00  0.00           O  
HETATM   16  C7  UNL     1       1.582  -0.635   0.729  1.00  0.00           C  
HETATM   17  H1  UNL     1       3.723   3.116  -0.781  1.00  0.00           H  
HETATM   18  H2  UNL     1       0.489   2.042  -1.008  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.373   0.426  -1.313  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.211   2.836   0.923  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.592   0.020  -0.434  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.140  -1.410  -2.000  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.803  -3.068  -0.373  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.988  -1.518  -1.148  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.792  -2.746   1.116  1.00  0.00           H  
HETATM   26  H10 UNL     1       2.575  -0.935   1.122  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.872  -0.597   1.553  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5    5   16
CONECT    5    6   18
CONECT    6    7   12   19
CONECT    7    8
CONECT    8    9    9   10   11
CONECT   10   20
CONECT   11   21
CONECT   12   13   14   22
CONECT   13   23
CONECT   14   15   16   24
CONECT   15   25
CONECT   16   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,5-Dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylate	Generator
Shikimate-3-phosphate	MeSH, Generator
Shikimic acid-3-phosphoric acid	Generator

Chemical Formula

C₇H₁₁O₈P

Average Molecular Weight

254.1312

Monoisotopic Molecular Weight

254.01915384

IUPAC Name

4,5-dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid

Traditional Name

shikimate 3-phosphate

CAS Registry Number

Not Available

SMILES

OC1CC(=CC(OP(O)(O)=O)C1O)C(O)=O

InChI Identifier

InChI=1S/C7H11O8P/c8-4-1-3(7(10)11)2-5(6(4)9)15-16(12,13)14/h2,4-6,8-9H,1H2,(H,10,11)(H2,12,13,14)

InChI Key

QYOJSKGCWNAKGW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Monoalkyl phosphates

Alternative Parents

Substituents

Monoalkyl phosphate
Cyclitol or derivatives
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	-2.1	ALOGPS
logP	-1.8	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.32	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.83 m³·mol⁻¹	ChemAxon
Polarizability	20.35 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
DeepCCS	[M+H]+	143.765	30932474
DeepCCS	[M-H]-	141.407	30932474
DeepCCS	[M-2H]-	176.057	30932474
DeepCCS	[M+Na]+	151.675	30932474
AllCCS	[M+H]+	155.4	32859911
AllCCS	[M+H-H2O]+	151.8	32859911
AllCCS	[M+NH4]+	158.8	32859911
AllCCS	[M+Na]+	159.7	32859911
AllCCS	[M-H]-	145.9	32859911
AllCCS	[M+Na-2H]-	146.2	32859911
AllCCS	[M+HCOO]-	146.7	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.	2.35 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9547 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.84 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	525.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	299.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	34.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	71.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	301.0 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	243.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	811.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	597.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	42.8 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	704.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	188.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	285.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	774.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	426.9 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	531.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Shikimate-3-phosphate	OC1CC(=CC(OP(O)(O)=O)C1O)C(O)=O	3957.4	Standard polar	33892256
Shikimate-3-phosphate	OC1CC(=CC(OP(O)(O)=O)C1O)C(O)=O	1949.3	Standard non polar	33892256
Shikimate-3-phosphate	OC1CC(=CC(OP(O)(O)=O)C1O)C(O)=O	2288.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Shikimate-3-phosphate,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1	2301.7	Semi standard non polar	33892256
Shikimate-3-phosphate,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1	2258.9	Standard non polar	33892256
Shikimate-3-phosphate,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1	2655.8	Standard polar	33892256
Shikimate-3-phosphate,4TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1	2293.4	Semi standard non polar	33892256
Shikimate-3-phosphate,4TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1	2335.5	Standard non polar	33892256
Shikimate-3-phosphate,4TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1	2766.2	Standard polar	33892256
Shikimate-3-phosphate,4TMS,isomer #3	C[Si](C)(C)OC1CC(C(=O)O)=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C1O[Si](C)(C)C	2365.7	Semi standard non polar	33892256
Shikimate-3-phosphate,4TMS,isomer #3	C[Si](C)(C)OC1CC(C(=O)O)=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C1O[Si](C)(C)C	2315.6	Standard non polar	33892256
Shikimate-3-phosphate,4TMS,isomer #3	C[Si](C)(C)OC1CC(C(=O)O)=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C1O[Si](C)(C)C	2646.6	Standard polar	33892256
Shikimate-3-phosphate,4TMS,isomer #4	C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1	2329.7	Semi standard non polar	33892256
Shikimate-3-phosphate,4TMS,isomer #4	C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1	2316.5	Standard non polar	33892256
Shikimate-3-phosphate,4TMS,isomer #4	C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1	2636.5	Standard polar	33892256
Shikimate-3-phosphate,5TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1	2318.5	Semi standard non polar	33892256
Shikimate-3-phosphate,5TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1	2353.9	Standard non polar	33892256
Shikimate-3-phosphate,5TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1	2481.8	Standard polar	33892256
Shikimate-3-phosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1	3130.9	Semi standard non polar	33892256
Shikimate-3-phosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1	2978.4	Standard non polar	33892256
Shikimate-3-phosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1	2988.5	Standard polar	33892256
Shikimate-3-phosphate,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1	3119.1	Semi standard non polar	33892256
Shikimate-3-phosphate,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1	3029.5	Standard non polar	33892256
Shikimate-3-phosphate,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1	3094.1	Standard polar	33892256
Shikimate-3-phosphate,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1CC(C(=O)O)=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3207.6	Semi standard non polar	33892256
Shikimate-3-phosphate,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1CC(C(=O)O)=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3036.3	Standard non polar	33892256
Shikimate-3-phosphate,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1CC(C(=O)O)=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	2995.4	Standard polar	33892256
Shikimate-3-phosphate,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1	3168.2	Semi standard non polar	33892256
Shikimate-3-phosphate,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1	2998.4	Standard non polar	33892256
Shikimate-3-phosphate,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1	2975.5	Standard polar	33892256
Shikimate-3-phosphate,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1	3292.0	Semi standard non polar	33892256
Shikimate-3-phosphate,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1	3165.0	Standard non polar	33892256
Shikimate-3-phosphate,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1	2937.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Shikimate-3-phosphate GC-MS (5 TMS)	splash10-0w34-2982100000-7a121ca2be86ffd45cae	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9430000000-6f27ce1e9eabc07dd402	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TMS_3_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Shikimate-3-phosphate GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1064

KEGG Compound ID

Not Available

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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Only showing the first 10 proteins. There are 22 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 3-phosphoshikimate 1-carboxyvinyltransferase

General function:: Not Available
Specific function:: Catalyzes the transfer of the enolpyruvyl moiety of phosphoenolpyruvate (PEP) to the 5-hydroxyl of shikimate-3-phosphate (S3P) to produce enolpyruvyl shikimate-3-phosphate and inorganic phosphate.
Gene Name:: AROA
Uniprot ID:: C0MA42
Molecular weight:: 46061.81

Enzyme Details

2. 3-phosphoshikimate 1-carboxyvinyltransferase

General function:: Not Available
Specific function:: Catalyzes the transfer of the enolpyruvyl moiety of phosphoenolpyruvate (PEP) to the 5-hydroxyl of shikimate-3-phosphate (S3P) to produce enolpyruvyl shikimate-3-phosphate and inorganic phosphate.
Gene Name:: AROA
Uniprot ID:: Q6G0X3
Molecular weight:: 47537.905

Enzyme Details

3. 3-phosphoshikimate 1-carboxyvinyltransferase

General function:: Not Available
Specific function:: Catalyzes the transfer of the enolpyruvyl moiety of phosphoenolpyruvate (PEP) to the 5-hydroxyl of shikimate-3-phosphate (S3P) to produce enolpyruvyl shikimate-3-phosphate and inorganic phosphate.
Gene Name:: AROA
Uniprot ID:: Q1JL87
Molecular weight:: 46671.915

Enzyme Details

4. 3-phosphoshikimate 1-carboxyvinyltransferase

General function:: Not Available
Specific function:: Catalyzes the transfer of the enolpyruvyl moiety of phosphoenolpyruvate (PEP) to the 5-hydroxyl of shikimate-3-phosphate (S3P) to produce enolpyruvyl shikimate-3-phosphate and inorganic phosphate.
Gene Name:: AROA
Uniprot ID:: Q9ZKF7
Molecular weight:: 47167.17

Enzyme Details

5. 3-phosphoshikimate 1-carboxyvinyltransferase

General function:: Not Available
Specific function:: Catalyzes the transfer of the enolpyruvyl moiety of phosphoenolpyruvate (PEP) to the 5-hydroxyl of shikimate-3-phosphate (S3P) to produce enolpyruvyl shikimate-3-phosphate and inorganic phosphate.
Gene Name:: AROA
Uniprot ID:: Q4L6G8
Molecular weight:: 46878.675

Enzyme Details

6. 3-phosphoshikimate 1-carboxyvinyltransferase

General function:: Not Available
Specific function:: Catalyzes the transfer of the enolpyruvyl moiety of phosphoenolpyruvate (PEP) to the 5-hydroxyl of shikimate-3-phosphate (S3P) to produce enolpyruvyl shikimate-3-phosphate and inorganic phosphate.
Gene Name:: AROA
Uniprot ID:: Q1J633
Molecular weight:: 46256.36

Enzyme Details

7. 3-phosphoshikimate 1-carboxyvinyltransferase

General function:: Not Available
Specific function:: Catalyzes the transfer of the enolpyruvyl moiety of phosphoenolpyruvate (PEP) to the 5-hydroxyl of shikimate-3-phosphate (S3P) to produce enolpyruvyl shikimate-3-phosphate and inorganic phosphate.
Gene Name:: AROA
Uniprot ID:: A1A9I5
Molecular weight:: 46221.42

Enzyme Details

8. 3-phosphoshikimate 1-carboxyvinyltransferase

General function:: Not Available
Specific function:: Catalyzes the transfer of the enolpyruvyl moiety of phosphoenolpyruvate (PEP) to the 5-hydroxyl of shikimate-3-phosphate (S3P) to produce enolpyruvyl shikimate-3-phosphate and inorganic phosphate.
Gene Name:: AROA
Uniprot ID:: Q5PGG5
Molecular weight:: 46197.51

Enzyme Details

9. 3-phosphoshikimate 1-carboxyvinyltransferase

General function:: Not Available
Specific function:: Catalyzes the transfer of the enolpyruvyl moiety of phosphoenolpyruvate (PEP) to the 5-hydroxyl of shikimate-3-phosphate (S3P) to produce enolpyruvyl shikimate-3-phosphate and inorganic phosphate.
Gene Name:: AROA
Uniprot ID:: Q1JB43
Molecular weight:: 46671.915

Enzyme Details

10. 3-phosphoshikimate 1-carboxyvinyltransferase

General function:: Not Available
Specific function:: Catalyzes the transfer of the enolpyruvyl moiety of phosphoenolpyruvate (PEP) to the 5-hydroxyl of shikimate-3-phosphate (S3P) to produce enolpyruvyl shikimate-3-phosphate and inorganic phosphate.
Gene Name:: AROA
Uniprot ID:: Q6G545
Molecular weight:: 47514.785

Only showing the first 10 proteins. There are 22 proteins in total.

Show all enzymes and transporters

Showing metabocard for Shikimate-3-phosphate (HMDB0258272)

MOL for HMDB0258272 (Shikimate-3-phosphate)

3D MOL for HMDB0258272 (Shikimate-3-phosphate)

3D SDF for HMDB0258272 (Shikimate-3-phosphate)

3D-SDF for HMDB0258272 (Shikimate-3-phosphate)

PDB for HMDB0258272 (Shikimate-3-phosphate)

3D PDB for HMDB0258272 (Shikimate-3-phosphate)

SMILES for HMDB0258272 (Shikimate-3-phosphate)

INCHI for HMDB0258272 (Shikimate-3-phosphate)

Structure for HMDB0258272 (Shikimate-3-phosphate)

3D Structure for HMDB0258272 (Shikimate-3-phosphate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

Enzymes