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Showing metabocard for (S)-Propane-1,2-diol (HMDB0006213)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-05-22 17:39:54 UTC
Update Date2021-09-14 15:20:06 UTC
HMDB IDHMDB0006213
Secondary Accession Numbers
  • HMDB06213
Metabolite Identification
Common Name(S)-Propane-1,2-diol
Description(S)-Propane-1,2-diol, also known as (S)-1,2-propanediol or (S)-propylene glycol, belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions. (S)-Propane-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa). (S)-Propane-1,2-diol has been detected, but not quantified in, several different foods, such as common buckwheats, mustard spinach, sugar apples, black crowberries, and bayberries. This could make (S)-propane-1,2-diol a potential biomarker for the consumption of these foods. (S)-Propane-1,2-diol is a clear, colourless, viscous organic solvent and diluent used in pharmaceutical preparations.
Structure
Data?1589400063
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006213 ((S)-Propane-1,2-diol)


  Mrv1652303262021412D          

  5  4  0  0  1  0            999 V2000
    1.0717    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2061    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3572   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
Download

3D MOL for HMDB0006213 ((S)-Propane-1,2-diol)

HMDB0006213
     RDKit          3D
(S)-Propane-1,2-diol
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.1710    0.7684    0.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2444   -0.3194   -0.3542 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8426   -1.5362   -0.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0851   -0.2420    0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7541    0.9357    0.1103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6419    1.7219    0.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4573    0.4393    1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377    0.8697   -0.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1115   -0.1780   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1909   -1.9735   -0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8095   -0.1991    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6829   -1.1491    0.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658    0.8624   -0.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  6
  3 10  1  0
  4 11  1  0
  4 12  1  0
  5 13  1  0
M  END
Download

3D SDF for HMDB0006213 ((S)-Propane-1,2-diol)


  Mrv1652303262021412D          

  5  4  0  0  1  0            999 V2000
    1.0717    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2061    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3572   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006213

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3/t3-/m0/s1

> <INCHI_KEY>
DNIAPMSPPWPWGF-VKHMYHEASA-N

> <FORMULA>
C3H8O2

> <MOLECULAR_WEIGHT>
76.0944

> <EXACT_MASS>
76.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
8.010010240779765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-propane-1,2-diol

> <ALOGPS_LOGP>
-1.10

> <JCHEM_LOGP>
-0.7921040560000001

> <ALOGPS_LOGS>
1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.996044021064442

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.470762978766011

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8584492517004216

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
18.9724

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.52e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-1,2-propanediol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0006213 ((S)-Propane-1,2-diol)

HMDB0006213
     RDKit          3D
(S)-Propane-1,2-diol
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.1710    0.7684    0.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2444   -0.3194   -0.3542 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8426   -1.5362   -0.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0851   -0.2420    0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7541    0.9357    0.1103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6419    1.7219    0.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4573    0.4393    1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377    0.8697   -0.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1115   -0.1780   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1909   -1.9735   -0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8095   -0.1991    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6829   -1.1491    0.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658    0.8624   -0.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  6
  3 10  1  0
  4 11  1  0
  4 12  1  0
  5 13  1  0
M  END
Download

PDB for HMDB0006213 ((S)-Propane-1,2-diol)

HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  C   UNK     0       2.001   1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.667   0.385   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.667  -1.155   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.667   1.155   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.001   0.385   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0006213 ((S)-Propane-1,2-diol)

COMPND    HMDB0006213
HETATM    1  C1  UNL     1      -1.171   0.768   0.172  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.244  -0.319  -0.354  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.843  -1.536  -0.019  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.085  -0.242   0.383  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.754   0.936   0.110  1.00  0.00           O  
HETATM    6  H1  UNL     1      -0.642   1.722   0.239  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.457   0.439   1.204  1.00  0.00           H  
HETATM    8  H3  UNL     1      -2.038   0.870  -0.501  1.00  0.00           H  
HETATM    9  H4  UNL     1      -0.112  -0.178  -1.430  1.00  0.00           H  
HETATM   10  H5  UNL     1      -1.191  -1.973  -0.854  1.00  0.00           H  
HETATM   11  H6  UNL     1       0.809  -0.199   1.476  1.00  0.00           H  
HETATM   12  H7  UNL     1       1.683  -1.149   0.257  1.00  0.00           H  
HETATM   13  H8  UNL     1       2.366   0.862  -0.682  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    4    9
CONECT    3   10
CONECT    4    5   11   12
CONECT    5   13
END
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SMILES for HMDB0006213 ((S)-Propane-1,2-diol)

C[C@H](O)CO
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INCHI for HMDB0006213 ((S)-Propane-1,2-diol)

InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3/t3-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(S)-1,2-PropanediolChEBI
(S)-Propylene glycolChEBI
(2S)-Propane-1,2-diolHMDB
(+)-(S)-1,2-PropanediolHMDB
(+)-1,2-PropanediolHMDB
(2S)-1,2-PropanediolHMDB
(S)-(+)-Propane-1,2-diolHMDB
(S)-(+)-Propylene glycolHMDB
(S)-2-Hydroxy-1-propanolHMDB
(S)-2-HydroxypropanolHMDB
(S)-Propane-1,2-diolHMDB
1,2(S)-PropanediolHMDB
1,2-(RS)-PropanediolHMDB
1,2-DihydroxypropaneHMDB
1,2-PropanediolHMDB
1,2-Propylene glycolHMDB
2,3-PropanediolHMDB
2-HydroxypropanolHMDB
3-Deoxy-sn-glycerolHMDB
Isopropylene glycolHMDB
L-(+)-PropanediolHMDB
L-(+)-Propylene glycolHMDB
L-1,2-PropanediolHMDB
Methylethyl glycolHMDB
Methylethylene glycolHMDB
Monopropylene glycolHMDB
Propylene glycolHMDB
alpha-Propylene glycolHMDB
α-Propylene glycolHMDB
Chemical FormulaC3H8O2
Average Molecular Weight76.0944
Monoisotopic Molecular Weight76.0524295
IUPAC Name(2S)-propane-1,2-diol
Traditional Name(S)-1,2-propanediol
CAS Registry Number4254-15-3
SMILES
C[C@H](O)CO
InChI Identifier
InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3/t3-/m0/s1
InChI KeyDNIAPMSPPWPWGF-VKHMYHEASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct Parent1,2-diols
Alternative Parents
Substituents
  • Secondary alcohol
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility952 g/LALOGPS
logP-1.1ALOGPS
logP-0.79ChemAxon
logS1.1ALOGPS
pKa (Strongest Acidic)14.47ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity18.97 m³·mol⁻¹ChemAxon
Polarizability8.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+112.47831661259
DarkChem[M-H]-107.34431661259
DeepCCS[M+H]+120.93730932474
DeepCCS[M-H]-118.49830932474
DeepCCS[M-2H]-154.6230932474
DeepCCS[M+Na]+129.19430932474
AllCCS[M+H]+123.032859911
AllCCS[M+H-H2O]+118.632859911
AllCCS[M+NH4]+127.232859911
AllCCS[M+Na]+128.432859911
AllCCS[M-H]-131.232859911
AllCCS[M+Na-2H]-136.832859911
AllCCS[M+HCOO]-143.032859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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. 0.39 minutes32390414
Predicted by Siyang on May 30, 20228.8419 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.42 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid178.4 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid822.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid344.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid67.6 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid232.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid60.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid270.0 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid255.0 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)303.1 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid587.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid64.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid761.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid206.1 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid261.3 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate557.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA304.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water235.0 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-Propane-1,2-diolC[C@H](O)CO1505.0Standard polar33892256
(S)-Propane-1,2-diolC[C@H](O)CO711.0Standard non polar33892256
(S)-Propane-1,2-diolC[C@H](O)CO735.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-Propane-1,2-diol,1TMS,isomer #1C[C@@H](CO)O[Si](C)(C)C848.9Semi standard non polar33892256
(S)-Propane-1,2-diol,1TMS,isomer #2C[C@H](O)CO[Si](C)(C)C857.7Semi standard non polar33892256
(S)-Propane-1,2-diol,2TMS,isomer #1C[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C999.7Semi standard non polar33892256
(S)-Propane-1,2-diol,1TBDMS,isomer #1C[C@@H](CO)O[Si](C)(C)C(C)(C)C1082.8Semi standard non polar33892256
(S)-Propane-1,2-diol,1TBDMS,isomer #2C[C@H](O)CO[Si](C)(C)C(C)(C)C1081.2Semi standard non polar33892256
(S)-Propane-1,2-diol,2TBDMS,isomer #1C[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1427.3Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04349
Phenol Explorer Compound IDNot Available
FooDB IDFDB023838
KNApSAcK IDC00007410
Chemspider ID388890
KEGG Compound IDC02917
BioCyc IDPROPANE-1-2-DIOL
BiGG ID40815
Wikipedia LinkPropylene_glycol
METLIN ID3220
PubChem Compound439846
PDB IDPGO
ChEBI ID29002
Food Biomarker OntologyNot Available
VMH ID12PPD_S
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMelchiorre, Carlo. A convenient synthesis of S(+)-propane-1,2-diol. Chemistry & Industry (London, United Kingdom) (1976), (5), 218.
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

Enzyme Details
1. Aldose reductase
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:
AKR1B1
Uniprot ID:
P15121
Molecular weight:
35853.125