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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-05-23 10:41:20 UTC

Update Date

2023-02-21 17:17:19 UTC

HMDB ID

HMDB0006468

Secondary Accession Numbers

HMDB06468

Metabolite Identification

Common Name

4-Hydroxydebrisoquine

Description

4-Hydroxydebrisoquine belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. 4-Hydroxydebrisoquine 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 4-hydroxydebrisoquine a potential biomarker for the consumption of these foods. 4-Hydroxydebrisoquine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 4-Hydroxydebrisoquine.

Structure

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


  Mrv0541 02231220392D          

 14 15  0  0  0  0            999 V2000
   14.7344  -11.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7344  -10.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4489  -10.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1634  -10.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1634  -11.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4489  -11.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4489  -12.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1634  -12.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8779  -12.4988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8779  -11.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7344  -12.9112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5924  -12.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5924  -13.7362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3068  -12.4988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 10  5  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13 12  2  0  0  0  0
 14 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006468

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=N)N1CC(O)C2=C(C1)C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H13N3O/c11-10(12)13-5-7-3-1-2-4-8(7)9(14)6-13/h1-4,9,14H,5-6H2,(H3,11,12)

> <INCHI_KEY>
AKFURXZANOMQBD-UHFFFAOYSA-N

> <FORMULA>
C10H13N3O

> <MOLECULAR_WEIGHT>
191.2297

> <EXACT_MASS>
191.105862053

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
20.080777484710485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboximidamide

> <ALOGPS_LOGP>
-0.27

> <JCHEM_LOGP>
0.05965590167281229

> <ALOGPS_LOGS>
-2.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.04029777171078

> <JCHEM_PKA_STRONGEST_BASIC>
12.087959589142267

> <JCHEM_POLAR_SURFACE_AREA>
73.34

> <JCHEM_REFRACTIVITY>
65.05780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxydebrisoquine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      27.504 -21.021   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.504 -19.481   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.838 -18.711   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.172 -19.481   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.172 -21.021   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.838 -21.791   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.838 -23.331   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.172 -24.101   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      31.505 -23.331   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      31.505 -21.791   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      27.504 -24.101   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      32.839 -24.101   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      32.839 -25.641   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      34.173 -23.331   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9    5                                                       
CONECT   11    7                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0006468
HETATM    1  N1  UNL     1       3.576  -1.209   0.020  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.804  -0.242  -0.351  1.00  0.00           C  
HETATM    3  N2  UNL     1       3.362   0.804  -1.130  1.00  0.00           N  
HETATM    4  N3  UNL     1       1.431  -0.158  -0.028  1.00  0.00           N  
HETATM    5  C2  UNL     1       0.519  -0.943  -0.826  1.00  0.00           C  
HETATM    6  C3  UNL     1      -0.893  -0.541  -0.611  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.786  -0.830  -1.640  1.00  0.00           C  
HETATM    8  C5  UNL     1      -3.104  -0.461  -1.456  1.00  0.00           C  
HETATM    9  C6  UNL     1      -3.514   0.176  -0.283  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.614   0.452   0.720  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.290   0.086   0.547  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.311   0.375   1.619  1.00  0.00           C  
HETATM   13  O1  UNL     1      -0.734   1.459   2.386  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.053   0.696   1.063  1.00  0.00           C  
HETATM   15  H1  UNL     1       3.169  -1.984   0.597  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.853   0.539  -2.011  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.323   1.813  -0.896  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.759  -0.738  -1.890  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.657  -2.022  -0.631  1.00  0.00           H  
HETATM   20  H6  UNL     1      -1.442  -1.329  -2.547  1.00  0.00           H  
HETATM   21  H7  UNL     1      -3.848  -0.655  -2.214  1.00  0.00           H  
HETATM   22  H8  UNL     1      -4.551   0.463  -0.148  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.897   0.949   1.653  1.00  0.00           H  
HETATM   24  H10 UNL     1      -0.240  -0.516   2.282  1.00  0.00           H  
HETATM   25  H11 UNL     1      -0.185   1.525   3.206  1.00  0.00           H  
HETATM   26  H12 UNL     1       1.074   1.740   0.706  1.00  0.00           H  
HETATM   27  H13 UNL     1       1.828   0.551   1.863  1.00  0.00           H  
CONECT    1    2    2   15
CONECT    2    3    4
CONECT    3   16   17
CONECT    4    5   14
CONECT    5    6   18   19
CONECT    6    7    7   11
CONECT    7    8   20
CONECT    8    9    9   21
CONECT    9   10   22
CONECT   10   11   11   23
CONECT   11   12
CONECT   12   13   14   24
CONECT   13   25
CONECT   14   26   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3,4-Dihydro-4-hydroxy-2(1H)-isoquinolinecarboximidamide	ChEBI
4 Hydroxy debrisoquine	HMDB
4-Hydroxydebrisoquin sulfate (2:1)	MeSH, HMDB
4-Hydroxydebrisoquin	MeSH, HMDB
4-Hydroxydebrisoquine	MeSH

Chemical Formula

C₁₀H₁₃N₃O

Average Molecular Weight

191.2297

Monoisotopic Molecular Weight

191.105862053

IUPAC Name

4-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboximidamide

Traditional Name

4-hydroxydebrisoquine

CAS Registry Number

59333-79-8

SMILES

NC(=N)N1CC(O)C2=C(C1)C=CC=C2

InChI Identifier

InChI=1S/C10H13N3O/c11-10(12)13-5-7-3-1-2-4-8(7)9(14)6-13/h1-4,9,14H,5-6H2,(H3,11,12)

InChI Key

AKFURXZANOMQBD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

Alternative Parents

Substituents

Tetrahydroisoquinoline
Benzenoid
Secondary alcohol
Guanidine
Azacycle
Carboximidamide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

secondary alcohol (CHEBI:63800 )
carboxamidine (CHEBI:63800 )
isoquinolines (CHEBI:63800 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0006468)
Extracellular (HMDB: HMDB0006468)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0006468)

Source

Endogenous

Endogenous (HMDB: HMDB0006468)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

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	1.06 g/L	ALOGPS
logP	-0.27	ALOGPS
logP	0.06	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	14.04	ChemAxon
pKa (Strongest Basic)	12.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.34 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	65.06 m³·mol⁻¹	ChemAxon
Polarizability	20.08 Å³	ChemAxon
Number of Rings	2	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]+	142.297	31661259
DarkChem	[M-H]-	139.316	31661259
DeepCCS	[M+H]+	141.715	30932474
DeepCCS	[M-H]-	139.32	30932474
DeepCCS	[M-2H]-	174.044	30932474
DeepCCS	[M+Na]+	148.784	30932474
AllCCS	[M+H]+	142.8	32859911
AllCCS	[M+H-H2O]+	138.5	32859911
AllCCS	[M+NH4]+	146.7	32859911
AllCCS	[M+Na]+	147.8	32859911
AllCCS	[M-H]-	143.5	32859911
AllCCS	[M+Na-2H]-	143.9	32859911
AllCCS	[M+HCOO]-	144.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxydebrisoquine	NC(=N)N1CC(O)C2=C(C1)C=CC=C2	3499.9	Standard polar	33892256
4-Hydroxydebrisoquine	NC(=N)N1CC(O)C2=C(C1)C=CC=C2	1989.8	Standard non polar	33892256
4-Hydroxydebrisoquine	NC(=N)N1CC(O)C2=C(C1)C=CC=C2	2116.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxydebrisoquine,1TMS,isomer #1	C[Si](C)(C)OC1CN(C(=N)N)CC2=CC=CC=C21	2130.2	Semi standard non polar	33892256
4-Hydroxydebrisoquine,1TMS,isomer #2	C[Si](C)(C)NC(=N)N1CC2=CC=CC=C2C(O)C1	2197.0	Semi standard non polar	33892256
4-Hydroxydebrisoquine,1TMS,isomer #3	C[Si](C)(C)N=C(N)N1CC2=CC=CC=C2C(O)C1	2096.0	Semi standard non polar	33892256
4-Hydroxydebrisoquine,2TMS,isomer #1	C[Si](C)(C)NC(=N)N1CC2=CC=CC=C2C(O[Si](C)(C)C)C1	2194.6	Semi standard non polar	33892256
4-Hydroxydebrisoquine,2TMS,isomer #1	C[Si](C)(C)NC(=N)N1CC2=CC=CC=C2C(O[Si](C)(C)C)C1	1963.1	Standard non polar	33892256
4-Hydroxydebrisoquine,2TMS,isomer #1	C[Si](C)(C)NC(=N)N1CC2=CC=CC=C2C(O[Si](C)(C)C)C1	2845.6	Standard polar	33892256
4-Hydroxydebrisoquine,2TMS,isomer #2	C[Si](C)(C)N=C(N)N1CC2=CC=CC=C2C(O[Si](C)(C)C)C1	2058.9	Semi standard non polar	33892256
4-Hydroxydebrisoquine,2TMS,isomer #2	C[Si](C)(C)N=C(N)N1CC2=CC=CC=C2C(O[Si](C)(C)C)C1	1909.2	Standard non polar	33892256
4-Hydroxydebrisoquine,2TMS,isomer #2	C[Si](C)(C)N=C(N)N1CC2=CC=CC=C2C(O[Si](C)(C)C)C1	3078.0	Standard polar	33892256
4-Hydroxydebrisoquine,2TMS,isomer #3	C[Si](C)(C)N(C(=N)N1CC2=CC=CC=C2C(O)C1)[Si](C)(C)C	2211.5	Semi standard non polar	33892256
4-Hydroxydebrisoquine,2TMS,isomer #3	C[Si](C)(C)N(C(=N)N1CC2=CC=CC=C2C(O)C1)[Si](C)(C)C	2162.9	Standard non polar	33892256
4-Hydroxydebrisoquine,2TMS,isomer #3	C[Si](C)(C)N(C(=N)N1CC2=CC=CC=C2C(O)C1)[Si](C)(C)C	3009.4	Standard polar	33892256
4-Hydroxydebrisoquine,2TMS,isomer #4	C[Si](C)(C)N=C(N[Si](C)(C)C)N1CC2=CC=CC=C2C(O)C1	2145.5	Semi standard non polar	33892256
4-Hydroxydebrisoquine,2TMS,isomer #4	C[Si](C)(C)N=C(N[Si](C)(C)C)N1CC2=CC=CC=C2C(O)C1	2027.3	Standard non polar	33892256
4-Hydroxydebrisoquine,2TMS,isomer #4	C[Si](C)(C)N=C(N[Si](C)(C)C)N1CC2=CC=CC=C2C(O)C1	2929.5	Standard polar	33892256
4-Hydroxydebrisoquine,3TMS,isomer #1	C[Si](C)(C)OC1CN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)CC2=CC=CC=C21	2144.6	Semi standard non polar	33892256
4-Hydroxydebrisoquine,3TMS,isomer #1	C[Si](C)(C)OC1CN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)CC2=CC=CC=C21	2148.9	Standard non polar	33892256
4-Hydroxydebrisoquine,3TMS,isomer #1	C[Si](C)(C)OC1CN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)CC2=CC=CC=C21	2726.0	Standard polar	33892256
4-Hydroxydebrisoquine,3TMS,isomer #2	C[Si](C)(C)N=C(N[Si](C)(C)C)N1CC2=CC=CC=C2C(O[Si](C)(C)C)C1	2105.9	Semi standard non polar	33892256
4-Hydroxydebrisoquine,3TMS,isomer #2	C[Si](C)(C)N=C(N[Si](C)(C)C)N1CC2=CC=CC=C2C(O[Si](C)(C)C)C1	2014.6	Standard non polar	33892256
4-Hydroxydebrisoquine,3TMS,isomer #2	C[Si](C)(C)N=C(N[Si](C)(C)C)N1CC2=CC=CC=C2C(O[Si](C)(C)C)C1	2705.8	Standard polar	33892256
4-Hydroxydebrisoquine,3TMS,isomer #3	C[Si](C)(C)N=C(N1CC2=CC=CC=C2C(O)C1)N([Si](C)(C)C)[Si](C)(C)C	2147.9	Semi standard non polar	33892256
4-Hydroxydebrisoquine,3TMS,isomer #3	C[Si](C)(C)N=C(N1CC2=CC=CC=C2C(O)C1)N([Si](C)(C)C)[Si](C)(C)C	2196.4	Standard non polar	33892256
4-Hydroxydebrisoquine,3TMS,isomer #3	C[Si](C)(C)N=C(N1CC2=CC=CC=C2C(O)C1)N([Si](C)(C)C)[Si](C)(C)C	2689.1	Standard polar	33892256
4-Hydroxydebrisoquine,4TMS,isomer #1	C[Si](C)(C)N=C(N1CC2=CC=CC=C2C(O[Si](C)(C)C)C1)N([Si](C)(C)C)[Si](C)(C)C	2133.8	Semi standard non polar	33892256
4-Hydroxydebrisoquine,4TMS,isomer #1	C[Si](C)(C)N=C(N1CC2=CC=CC=C2C(O[Si](C)(C)C)C1)N([Si](C)(C)C)[Si](C)(C)C	2193.7	Standard non polar	33892256
4-Hydroxydebrisoquine,4TMS,isomer #1	C[Si](C)(C)N=C(N1CC2=CC=CC=C2C(O[Si](C)(C)C)C1)N([Si](C)(C)C)[Si](C)(C)C	2464.5	Standard polar	33892256
4-Hydroxydebrisoquine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CN(C(=N)N)CC2=CC=CC=C21	2375.8	Semi standard non polar	33892256
4-Hydroxydebrisoquine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=N)N1CC2=CC=CC=C2C(O)C1	2451.9	Semi standard non polar	33892256
4-Hydroxydebrisoquine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(N)N1CC2=CC=CC=C2C(O)C1	2350.4	Semi standard non polar	33892256
4-Hydroxydebrisoquine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=N)N1CC2=CC=CC=C2C(O[Si](C)(C)C(C)(C)C)C1	2643.4	Semi standard non polar	33892256
4-Hydroxydebrisoquine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=N)N1CC2=CC=CC=C2C(O[Si](C)(C)C(C)(C)C)C1	2458.8	Standard non polar	33892256
4-Hydroxydebrisoquine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=N)N1CC2=CC=CC=C2C(O[Si](C)(C)C(C)(C)C)C1	2982.8	Standard polar	33892256
4-Hydroxydebrisoquine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(N)N1CC2=CC=CC=C2C(O[Si](C)(C)C(C)(C)C)C1	2498.5	Semi standard non polar	33892256
4-Hydroxydebrisoquine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(N)N1CC2=CC=CC=C2C(O[Si](C)(C)C(C)(C)C)C1	2392.0	Standard non polar	33892256
4-Hydroxydebrisoquine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(N)N1CC2=CC=CC=C2C(O[Si](C)(C)C(C)(C)C)C1	3232.7	Standard polar	33892256
4-Hydroxydebrisoquine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=N)N1CC2=CC=CC=C2C(O)C1)[Si](C)(C)C(C)(C)C	2613.1	Semi standard non polar	33892256
4-Hydroxydebrisoquine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=N)N1CC2=CC=CC=C2C(O)C1)[Si](C)(C)C(C)(C)C	2651.2	Standard non polar	33892256
4-Hydroxydebrisoquine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=N)N1CC2=CC=CC=C2C(O)C1)[Si](C)(C)C(C)(C)C	3029.2	Standard polar	33892256
4-Hydroxydebrisoquine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N=C(N[Si](C)(C)C(C)(C)C)N1CC2=CC=CC=C2C(O)C1	2582.2	Semi standard non polar	33892256
4-Hydroxydebrisoquine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N=C(N[Si](C)(C)C(C)(C)C)N1CC2=CC=CC=C2C(O)C1	2549.5	Standard non polar	33892256
4-Hydroxydebrisoquine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N=C(N[Si](C)(C)C(C)(C)C)N1CC2=CC=CC=C2C(O)C1	2987.9	Standard polar	33892256
4-Hydroxydebrisoquine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CN(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC2=CC=CC=C21	2786.3	Semi standard non polar	33892256
4-Hydroxydebrisoquine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CN(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC2=CC=CC=C21	2816.1	Standard non polar	33892256
4-Hydroxydebrisoquine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CN(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC2=CC=CC=C21	2921.4	Standard polar	33892256
4-Hydroxydebrisoquine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(N[Si](C)(C)C(C)(C)C)N1CC2=CC=CC=C2C(O[Si](C)(C)C(C)(C)C)C1	2721.5	Semi standard non polar	33892256
4-Hydroxydebrisoquine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(N[Si](C)(C)C(C)(C)C)N1CC2=CC=CC=C2C(O[Si](C)(C)C(C)(C)C)C1	2684.3	Standard non polar	33892256
4-Hydroxydebrisoquine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(N[Si](C)(C)C(C)(C)C)N1CC2=CC=CC=C2C(O[Si](C)(C)C(C)(C)C)C1	2921.4	Standard polar	33892256
4-Hydroxydebrisoquine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(N1CC2=CC=CC=C2C(O)C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2774.8	Semi standard non polar	33892256
4-Hydroxydebrisoquine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(N1CC2=CC=CC=C2C(O)C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2890.6	Standard non polar	33892256
4-Hydroxydebrisoquine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(N1CC2=CC=CC=C2C(O)C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2864.8	Standard polar	33892256
4-Hydroxydebrisoquine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(N1CC2=CC=CC=C2C(O[Si](C)(C)C(C)(C)C)C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2945.6	Semi standard non polar	33892256
4-Hydroxydebrisoquine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(N1CC2=CC=CC=C2C(O[Si](C)(C)C(C)(C)C)C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3018.1	Standard non polar	33892256
4-Hydroxydebrisoquine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(N1CC2=CC=CC=C2C(O[Si](C)(C)C(C)(C)C)C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2782.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxydebrisoquine GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-2900000000-65d9860661c52fc43fed	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxydebrisoquine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-7930000000-6c547ba47e9a793be64a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxydebrisoquine 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 - 4-Hydroxydebrisoquine 10V, Positive-QTOF	splash10-00dl-0900000000-d27d767387884b5344ee	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydebrisoquine 20V, Positive-QTOF	splash10-00di-0900000000-b4e6a4b85e95d2cd1a4d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydebrisoquine 40V, Positive-QTOF	splash10-0kfx-9700000000-746c466d9e27ab653e6a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydebrisoquine 10V, Negative-QTOF	splash10-0007-0900000000-4a585452b243c3fa4da6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydebrisoquine 20V, Negative-QTOF	splash10-001j-0900000000-b7230e5ec4140e46052d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydebrisoquine 40V, Negative-QTOF	splash10-0006-9100000000-0a94add8e365b703b0d3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydebrisoquine 10V, Negative-QTOF	splash10-006x-0900000000-3e730cd5607d9222d8e2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydebrisoquine 20V, Negative-QTOF	splash10-000t-0900000000-457a2f2c96a4c0185715	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydebrisoquine 40V, Negative-QTOF	splash10-001i-1900000000-65c31420b1e8b7d91d1c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydebrisoquine 10V, Positive-QTOF	splash10-00di-0900000000-b4234df44cdc9ae7eb0d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydebrisoquine 20V, Positive-QTOF	splash10-001i-0900000000-c646f107e3db6aef76a2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxydebrisoquine 40V, Positive-QTOF	splash10-000x-6900000000-6b6670295b89ecb7441a	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

Cytoplasm
Extracellular

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 and Quantified	0.217 +/- 0.021 uM	Adult (>18 years old)	Both	Normal	12814461	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

FDB023927

KNApSAcK ID

Not Available

Chemspider ID

96842

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2299987

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

107669

PDB ID

Not Available

ChEBI ID

63800

Food Biomarker Ontology

Not Available

VMH ID

4HDEBRISOQUINE

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Ram, Siya; Saxena, Anil K.; Jain, Padam C. 2-Substituted 4-hydroxy-1,2,3,4-tetrahydroisoquinolines. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1978), 16B(11), 1019-22.

Material Safety Data Sheet (MSDS)

Not Available

General References

Dorado P, Berecz R, Caceres MC, Gonzalez I, Cobaleda J, Llerena A: Determination of debrisoquine and 4-hydroxydebrisoquine by high-performance liquid chromatography: application to the evaluation of CYP2D6 genotype and debrisoquine metabolic ratio relationship. Clin Chem Lab Med. 2005;43(3):275-9. [PubMed:15843230 ]

Showing metabocard for 4-Hydroxydebrisoquine (HMDB0006468)

MOL for HMDB0006468 (4-Hydroxydebrisoquine)

3D MOL for HMDB0006468 (4-Hydroxydebrisoquine)

3D SDF for HMDB0006468 (4-Hydroxydebrisoquine)

3D-SDF for HMDB0006468 (4-Hydroxydebrisoquine)

PDB for HMDB0006468 (4-Hydroxydebrisoquine)

3D PDB for HMDB0006468 (4-Hydroxydebrisoquine)

SMILES for HMDB0006468 (4-Hydroxydebrisoquine)

INCHI for HMDB0006468 (4-Hydroxydebrisoquine)

Structure for HMDB0006468 (4-Hydroxydebrisoquine)

3D Structure for HMDB0006468 (4-Hydroxydebrisoquine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra