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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-12 22:07:25 UTC

Update Date

2023-02-21 17:16:43 UTC

HMDB ID

HMDB0003503

Secondary Accession Numbers

HMDB03503

Metabolite Identification

Common Name

3-(3,4-Dihydroxyphenyl)lactic acid

Description

3-(3,4-Dihydroxyphenyl)lactic acid, also known as a-hydroxyhydrocaffeic acid or danshensu, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. 3-(3,4-Dihydroxyphenyl)lactic acid has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and rosemaries (Rosmarinus officinalis). This could make 3-(3,4-dihydroxyphenyl)lactic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-(3,4-Dihydroxyphenyl)lactic acid.

Structure

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

<string xmlns="http://www.chemspider.com/">
  Mrv1652304222011052D          

 14 14  0  0  1  0            999 V2000
    2.9501   -4.3011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5205   -3.4784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1070   -3.0621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8243   -1.0005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5366   -2.2395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6624   -2.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9501   -3.4784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2328   -3.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6624   -3.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3947   -1.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1070   -2.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9501   -1.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2328   -2.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8243   -1.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3 11  1  0  0  0  0
  4 14  2  0  0  0  0
  5 14  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 12  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 13  2  0  0  0  0
 10 11  1  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003503

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(CC1=CC=C(O)C(O)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O5/c10-6-2-1-5(3-7(6)11)4-8(12)9(13)14/h1-3,8,10-12H,4H2,(H,13,14)

> <INCHI_KEY>
PAFLSMZLRSPALU-UHFFFAOYSA-N

> <FORMULA>
C9H10O5

> <MOLECULAR_WEIGHT>
198.1727

> <EXACT_MASS>
198.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.39550967033708

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
0.5773662063333331

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.28494383013577

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.258224734768921

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8352708457687443

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
47.42060000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
danshensu

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: <string xmlns="http://www.chemspider.com/">       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-20         0                                  
HETATM    1  O   UNK     0       5.507  -8.029   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       2.838  -6.493   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.533  -5.716   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.872  -1.868   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      12.202  -4.180   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.836  -4.180   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.507  -6.493   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.168  -5.716   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.836  -5.716   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.203  -3.413   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.533  -4.180   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.507  -3.413   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.168  -4.180   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.872  -3.413   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3   11                                                            
CONECT    4   14                                                            
CONECT    5   14                                                            
CONECT    6    9   10   12                                                  
CONECT    7    1    8    9                                                  
CONECT    8    2    7   13                                                  
CONECT    9    6    7                                                       
CONECT   10    6   11                                                       
CONECT   11    3   10   14                                                  
CONECT   12    6   13                                                       
CONECT   13    8   12                                                       
CONECT   14    4    5   11                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-(3,4-Dihydroxyphenyl)lactate	ChEBI
3,4-Dihydroxyphenyllactic acid	Kegg
3,4-Dihydroxyphenyllactate	Generator
2-Hydroxy-3-(3,4-dihydroxyphenyl)propanoate	HMDB
2-Hydroxy-3-(3,4-dihydroxyphenyl)propanoic acid	HMDB
a-Hydroxyhydrocaffeic acid	HMDB
alpha-Hydroxyhydrocaffeate	HMDB
alpha-Hydroxyhydrocaffeic acid	HMDB
Danshensu	HMDB
DL-b-(3,4-Dihydroxyphenyl)lactic acid	HMDB
DL-beta-(3,4-Dihydroxyphenyl)lactic acid	HMDB
(3,4-Dihydroxyphenyl)lactic acid	HMDB
3,4-Dihydroxyphenyllactic acid, monosodium salt, (R)-isomer	HMDB
3,4-Dihydroxyphenyllactic acid, (+-)-isomer	HMDB
3,4-Dihydroxyphenyllactic acid, (R)-isomer	HMDB
3,4-Dihydroxyphenyllactic acid, monosodium salt, (+-)-isomer	HMDB
Salvianic acid a sodium	HMDB
3,4-Dihydroxyphenyllactic acid, monosodium salt	HMDB
2-Hydroxy-3-(3',4'-dihydroxyphenyl)propanoic acid	HMDB

Chemical Formula

C₉H₁₀O₅

Average Molecular Weight

198.1727

Monoisotopic Molecular Weight

198.05282343

IUPAC Name

3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid

Traditional Name

danshensu

CAS Registry Number

23028-17-3

SMILES

OC(CC1=CC=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C9H10O5/c10-6-2-1-5(3-7(6)11)4-8(12)9(13)14/h1-3,8,10-12H,4H2,(H,13,14)

InChI Key

PAFLSMZLRSPALU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alpha-hydroxy acid
Monocyclic benzene moiety
Benzenoid
Hydroxy acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:17807 )
2-hydroxy monocarboxylic acid (CHEBI:17807 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 15315771)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0003503)

Fibroblasts (HMDB: HMDB0003503)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003503)

Source

Endogenous

Endogenous (HMDB: HMDB0003503)

Plant

Plant (HMDB: HMDB0003503)

Exogenous

Food

Food (HMDB: HMDB0003503)

Animal origin

Poultry

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)

Herb and spice

Herb

Rosemary (FooDB: FOOD00159)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	480.30 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.045 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.7 g/L	ALOGPS
logP	0.77	ALOGPS
logP	0.58	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.26	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.42 m³·mol⁻¹	ChemAxon
Polarizability	18.4 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	144.397	31661259
DarkChem	[M-H]-	139.353	31661259
DeepCCS	[M+H]+	137.884	30932474
DeepCCS	[M-H]-	134.763	30932474
DeepCCS	[M-2H]-	171.453	30932474
DeepCCS	[M+Na]+	146.991	30932474
AllCCS	[M+H]+	143.8	32859911
AllCCS	[M+H-H2O]+	139.7	32859911
AllCCS	[M+NH4]+	147.6	32859911
AllCCS	[M+Na]+	148.7	32859911
AllCCS	[M-H]-	140.4	32859911
AllCCS	[M+Na-2H]-	141.0	32859911
AllCCS	[M+HCOO]-	141.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-(3,4-Dihydroxyphenyl)lactic acid	OC(CC1=CC(O)=C(O)C=C1)C(O)=O	3651.8	Standard polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid	OC(CC1=CC(O)=C(O)C=C1)C(O)=O	1924.4	Standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid	OC(CC1=CC(O)=C(O)C=C1)C(O)=O	1918.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-(3,4-Dihydroxyphenyl)lactic acid,1TMS,isomer #1	C[Si](C)(C)OC(CC1=CC=C(O)C(O)=C1)C(=O)O	2058.8	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC(CC(O)C(=O)O)=CC=C1O	1989.0	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(CC(O)C(=O)O)C=C1O	2005.7	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,1TMS,isomer #4	C[Si](C)(C)OC(=O)C(O)CC1=CC=C(O)C(O)=C1	2034.9	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CC(O[Si](C)(C)C)C(=O)O)C=C1O	2031.1	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,2TMS,isomer #2	C[Si](C)(C)OC1=CC(CC(O[Si](C)(C)C)C(=O)O)=CC=C1O	2005.3	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)C(CC1=CC=C(O)C(O)=C1)O[Si](C)(C)C	2026.4	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,2TMS,isomer #4	C[Si](C)(C)OC(=O)C(O)CC1=CC=C(O)C(O[Si](C)(C)C)=C1	1970.2	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,2TMS,isomer #5	C[Si](C)(C)OC1=CC=C(CC(O)C(=O)O)C=C1O[Si](C)(C)C	1984.3	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,2TMS,isomer #6	C[Si](C)(C)OC(=O)C(O)CC1=CC=C(O[Si](C)(C)C)C(O)=C1	1995.2	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C)C(O)=C1)O[Si](C)(C)C	2018.2	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CC(O[Si](C)(C)C)C(=O)O)C=C1O[Si](C)(C)C	2030.0	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CC1=CC=C(O)C(O[Si](C)(C)C)=C1)O[Si](C)(C)C	1990.2	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,3TMS,isomer #4	C[Si](C)(C)OC(=O)C(O)CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	2035.7	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)O[Si](C)(C)C	2072.5	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CC1=CC=C(O)C(O)=C1)C(=O)O	2327.9	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(CC(O)C(=O)O)=CC=C1O	2266.4	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(O)C(=O)O)C=C1O	2278.3	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(O)CC1=CC=C(O)C(O)=C1	2284.2	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(O[Si](C)(C)C(C)(C)C)C(=O)O)C=C1O	2544.2	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(CC(O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O	2514.9	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O)C(O)=C1)O[Si](C)(C)C(C)(C)C	2496.1	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(O)CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	2469.6	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(O)C(=O)O)C=C1O[Si](C)(C)C(C)(C)C	2494.2	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)C(O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	2506.6	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)O[Si](C)(C)C(C)(C)C	2741.6	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(O[Si](C)(C)C(C)(C)C)C(=O)O)C=C1O[Si](C)(C)C(C)(C)C	2756.1	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)O[Si](C)(C)C(C)(C)C	2693.1	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2759.7	Semi standard non polar	33892256
3-(3,4-Dihydroxyphenyl)lactic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)O[Si](C)(C)C(C)(C)C	2942.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3,4-Dihydroxyphenyl)lactic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1900000000-4429ae1d67802f77638b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3,4-Dihydroxyphenyl)lactic acid GC-MS (4 TMS) - 70eV, Positive	splash10-00xr-5039800000-242433a4eaee6ec21e37	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3,4-Dihydroxyphenyl)lactic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3,4-Dihydroxyphenyl)lactic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3,4-Dihydroxyphenyl)lactic acid 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 - 3-(3,4-Dihydroxyphenyl)lactic acid 10V, Positive-QTOF	splash10-0ff1-0900000000-c01f6f341825bf481916	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Dihydroxyphenyl)lactic acid 20V, Positive-QTOF	splash10-0fl1-0900000000-4ac5f7db2b698bf08063	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Dihydroxyphenyl)lactic acid 40V, Positive-QTOF	splash10-01bd-9600000000-384a42503ca93dcc002c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Dihydroxyphenyl)lactic acid 10V, Negative-QTOF	splash10-0002-1900000000-badce4d6b7899f8089c8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Dihydroxyphenyl)lactic acid 20V, Negative-QTOF	splash10-0fmi-2900000000-73617118e281cf2316d7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Dihydroxyphenyl)lactic acid 40V, Negative-QTOF	splash10-05fr-7900000000-e5db4da27043d9518b0e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Dihydroxyphenyl)lactic acid 10V, Positive-QTOF	splash10-0f7t-0900000000-fbdfc4bd0e0f58825d1d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Dihydroxyphenyl)lactic acid 20V, Positive-QTOF	splash10-0mbi-1900000000-af4798a182a90c46f658	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Dihydroxyphenyl)lactic acid 40V, Positive-QTOF	splash10-0a4i-8900000000-65350b26562677521a53	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Dihydroxyphenyl)lactic acid 10V, Negative-QTOF	splash10-006t-6900000000-8abbd608e7bf3e2494e3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Dihydroxyphenyl)lactic acid 20V, Negative-QTOF	splash10-00di-6900000000-6bbd4cc7c25691915147	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Dihydroxyphenyl)lactic acid 40V, Negative-QTOF	splash10-00dl-9500000000-52ad949a19acd21974d2	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Fibroblasts

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	6.2 +/- 0.25 uM	Adult (>18 years old)	Both	Normal	15315771	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6942

PubChem Compound

439435

PDB ID

Not Available

ChEBI ID

17807

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1665481

References

Synthesis Reference

Poljanac, Mirela; Vasic-Racki, Durda; Hadolin, Majda; Bauman, Davor. Enzymatic preparation of Danshensu. Slovenski Kemijski Dnevi, Maribor, Slovenia, Sept. 25-26, 2003 (2003), 239-245.

Material Safety Data Sheet (MSDS)

Not Available

General References

Li X, Yu C, Cai Y, Liu G, Jia J, Wang Y: Simultaneous determination of six phenolic constituents of danshen in human serum using liquid chromatography/tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jun 5;820(1):41-7. Epub 2005 Apr 19. [PubMed:15866491 ]
Muskiet FA, Stratingh MC, Stob GJ, Wolthers BG: Simultaneous determination of the four major catecholamine metabolites and estimation of a serotonin metabolite in urine by capillary gas chromatography of their tert-butyldimethylsilyl derivatives. Clin Chem. 1981 Feb;27(2):223-7. [PubMed:7460271 ]
Liu Q, Chao RB: [Determination of danshensu in urine and its pharmacokinetics in human]. Yao Xue Xue Bao. 2003 Oct;38(10):771-4. [PubMed:14730902 ]
Jiang H, Ha T, Wei D: [A study on the mechanism of the biological roles of danshensu on fibroblast]. Zhonghua Shao Shang Za Zhi. 2001 Feb;17(1):36-8. [PubMed:11876909 ]
Hirsimaki H, Kero P, Ekblad H, Scheinin M, Saraste M, Erkkola R: Mode of delivery, plasma catecholamines and Doppler-derived cardiac output in healthy term newborn infants. Biol Neonate. 1992;61(5):285-93. [PubMed:1391254 ]

Enzymes

Enzyme Details

1. Sulfotransferase family cytosolic 2B member 1

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:: SULT2B1
Uniprot ID:: O00204
Molecular weight:: 39598.595

Reactions

3-(3,4-Dihydroxyphenyl)lactic acid → 3-(3,4-dihydroxyphenyl)-2-(sulfooxy)propanoic acid	details

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

3-(3,4-Dihydroxyphenyl)lactic acid → 6-[4-(2-carboxy-2-hydroxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
3-(3,4-Dihydroxyphenyl)lactic acid → 6-[5-(2-carboxy-2-hydroxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
3-(3,4-Dihydroxyphenyl)lactic acid → 6-{[3-(3,4-dihydroxyphenyl)-2-hydroxypropanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

3. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

3-(3,4-Dihydroxyphenyl)lactic acid → 2-hydroxy-3-[4-hydroxy-3-(sulfooxy)phenyl]propanoic acid	details

Showing metabocard for 3-(3,4-Dihydroxyphenyl)lactic acid (HMDB0003503)

MOL for HMDB0003503 (3-(3,4-Dihydroxyphenyl)lactic acid)

3D MOL for HMDB0003503 (3-(3,4-Dihydroxyphenyl)lactic acid)

3D SDF for HMDB0003503 (3-(3,4-Dihydroxyphenyl)lactic acid)

3D-SDF for HMDB0003503 (3-(3,4-Dihydroxyphenyl)lactic acid)

PDB for HMDB0003503 (3-(3,4-Dihydroxyphenyl)lactic acid)

3D PDB for HMDB0003503 (3-(3,4-Dihydroxyphenyl)lactic acid)

SMILES for HMDB0003503 (3-(3,4-Dihydroxyphenyl)lactic acid)

INCHI for HMDB0003503 (3-(3,4-Dihydroxyphenyl)lactic acid)

Structure for HMDB0003503 (3-(3,4-Dihydroxyphenyl)lactic acid)

3D Structure for HMDB0003503 (3-(3,4-Dihydroxyphenyl)lactic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions