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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-29 22:51:16 UTC

Update Date

2021-09-29 22:51:16 UTC

HMDB ID

HMDB0304913

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-Hydroxytryptophol sulfate

Description

3-(2-hydroxyethyl)-1H-indol-5-yl sulfate belongs to the class of organic compounds known as arylsulfates. These are organic compounds containing a sulfate group that carries an aryl group through an ether group. Based on a literature review very few articles have been published on 3-(2-hydroxyethyl)-1H-indol-5-yl sulfate.

Structure

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


  Mrv1652309302100522D          

 17 18  0  0  0  0            999 V2000
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9115    2.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0865    1.2210    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1536    3.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1014    4.3727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  CHG  1  11  -1
M  END
> <DATABASE_ID>
HMDB0304913

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCC1=CNC2=C1C=C(OS([O-])(=O)=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO5S/c12-4-3-7-6-11-10-2-1-8(5-9(7)10)16-17(13,14)15/h1-2,5-6,11-12H,3-4H2,(H,13,14,15)/p-1

> <INCHI_KEY>
FOCUAJYUOXSNDS-UHFFFAOYSA-M

> <FORMULA>
C10H10NO5S

> <MOLECULAR_WEIGHT>
256.25

> <EXACT_MASS>
256.02851718

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
23.79920942093522

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2-hydroxyethyl)-1H-indol-5-yl sulfate

> <ALOGPS_LOGP>
0.40

> <JCHEM_LOGP>
-0.8603771504558582

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.805905734579007

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.7617963353501187

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4436921701957015

> <JCHEM_POLAR_SURFACE_AREA>
102.45

> <JCHEM_REFRACTIVITY>
59.56640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-hydroxyethyl)-1H-indol-5-yl sulfate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-SEP-21         0                                  
HETATM    1  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM    8  S   UNK     0       6.531   3.613   0.000  0.00  0.00           S+0
HETATM    9  O   UNK     0       7.865   2.843   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       7.301   4.947   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.761   2.279   0.000  0.00  0.00           O-1
HETATM   12  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -0.268   1.597   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -0.744   5.553   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.287   6.698   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.189   8.162   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    4   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    3                                                       
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0304913
HETATM    1  O1  UNL     1       3.810   0.539   1.751  1.00  0.00           O  
HETATM    2  S1  UNL     1       3.733   1.840   1.020  1.00  0.00           S  
HETATM    3  O2  UNL     1       3.366   2.922   2.000  1.00  0.00           O  
HETATM    4  O3  UNL     1       5.250   2.279   0.394  1.00  0.00           O1-
HETATM    5  O4  UNL     1       2.550   1.849  -0.195  1.00  0.00           O  
HETATM    6  C1  UNL     1       1.811   0.754  -0.562  1.00  0.00           C  
HETATM    7  C2  UNL     1       2.158  -0.137  -1.532  1.00  0.00           C  
HETATM    8  C3  UNL     1       1.343  -1.211  -1.827  1.00  0.00           C  
HETATM    9  C4  UNL     1       0.150  -1.424  -1.156  1.00  0.00           C  
HETATM   10  N1  UNL     1      -0.794  -2.379  -1.255  1.00  0.00           N  
HETATM   11  C5  UNL     1      -1.780  -2.169  -0.381  1.00  0.00           C  
HETATM   12  C6  UNL     1      -1.428  -1.004   0.307  1.00  0.00           C  
HETATM   13  C7  UNL     1      -2.259  -0.384   1.354  1.00  0.00           C  
HETATM   14  C8  UNL     1      -3.075   0.728   0.765  1.00  0.00           C  
HETATM   15  O5  UNL     1      -2.231   1.679   0.223  1.00  0.00           O  
HETATM   16  C9  UNL     1      -0.221  -0.539  -0.175  1.00  0.00           C  
HETATM   17  C10 UNL     1       0.607   0.540   0.116  1.00  0.00           C  
HETATM   18  H1  UNL     1       3.093   0.035  -2.054  1.00  0.00           H  
HETATM   19  H2  UNL     1       1.621  -1.921  -2.603  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.758  -3.171  -1.921  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.680  -2.759  -0.215  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.854  -1.116   1.933  1.00  0.00           H  
HETATM   23  H6  UNL     1      -1.543   0.099   2.078  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.797   1.162   1.491  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.651   0.273  -0.082  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.733   2.299  -0.367  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.310   1.214   0.891  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    3    4    5
CONECT    5    6
CONECT    6    7    7   17
CONECT    7    8   18
CONECT    8    9    9   19
CONECT    9   10   16
CONECT   10   11   20
CONECT   11   12   12   21
CONECT   12   13   16
CONECT   13   14   22   23
CONECT   14   15   24   25
CONECT   15   26
CONECT   16   17   17
CONECT   17   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(2-Hydroxyethyl)-1H-indol-5-yl sulfuric acid	Generator
3-(2-Hydroxyethyl)-1H-indol-5-yl sulphate	Generator
3-(2-Hydroxyethyl)-1H-indol-5-yl sulphuric acid	Generator
5-Hydroxytryptophol sulfuric acid	Generator
5-Hydroxytryptophol sulphate	Generator
5-Hydroxytryptophol sulphuric acid	Generator

Chemical Formula

C₁₀H₁₀NO₅S

Average Molecular Weight

256.25

Monoisotopic Molecular Weight

256.02851718

IUPAC Name

3-(2-hydroxyethyl)-1H-indol-5-yl sulfate

Traditional Name

3-(2-hydroxyethyl)-1H-indol-5-yl sulfate

CAS Registry Number

Not Available

SMILES

OCCC1=CNC2=C1C=C(OS([O-])(=O)=O)C=C2

InChI Identifier

InChI=1S/C10H11NO5S/c12-4-3-7-6-11-10-2-1-8(5-9(7)10)16-17(13,14)15/h1-2,5-6,11-12H,3-4H2,(H,13,14,15)/p-1

InChI Key

FOCUAJYUOXSNDS-UHFFFAOYSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as arylsulfates. These are organic compounds containing a sulfate group that carries an aryl group through an ether group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfuric acids and derivatives

Sub Class

Arylsulfates

Direct Parent

Arylsulfates

Alternative Parents

Substituents

Arylsulfate
3-alkylindole
Indole
Indole or derivatives
Substituted pyrrole
Sulfuric acid monoester
Sulfate-ester
Benzenoid
Sulfuric acid ester
Pyrrole
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-11674 )

Ontology

Not Available

Not Available

Not Available

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	0.4	ALOGPS
logP	-0.86	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	-1.8	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	59.57 m³·mol⁻¹	ChemAxon
Polarizability	23.8 Å³	ChemAxon
Number of Rings	2	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
AllCCS	[M+H]+	156.022	32859911
AllCCS	[M+H-H2O]+	152.238	32859911
AllCCS	[M+Na]+	160.547	32859911
AllCCS	[M+NH4]+	159.536	32859911
AllCCS	[M-H]-	150.671	32859911
AllCCS	[M+Na-2H]-	150.589	32859911
AllCCS	[M+HCOO]-	150.602	32859911
DeepCCS	[M+H]+	159.97	30932474
DeepCCS	[M-H]-	157.613	30932474
DeepCCS	[M-2H]-	190.775	30932474
DeepCCS	[M+Na]+	166.064	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxytryptophol sulfate,1TMS,isomer #1	C[Si](C)(C)OCCC1=C[NH]C2=CC=C(OS(=O)(=O)[O-])C=C12	2400.7	Semi standard non polar	33892256
5-Hydroxytryptophol sulfate,1TMS,isomer #1	C[Si](C)(C)OCCC1=C[NH]C2=CC=C(OS(=O)(=O)[O-])C=C12	2358.5	Standard non polar	33892256
5-Hydroxytryptophol sulfate,1TMS,isomer #1	C[Si](C)(C)OCCC1=C[NH]C2=CC=C(OS(=O)(=O)[O-])C=C12	3361.3	Standard polar	33892256
5-Hydroxytryptophol sulfate,1TMS,isomer #2	C[Si](C)(C)N1C=C(CCO)C2=CC(OS(=O)(=O)[O-])=CC=C21	2385.5	Semi standard non polar	33892256
5-Hydroxytryptophol sulfate,1TMS,isomer #2	C[Si](C)(C)N1C=C(CCO)C2=CC(OS(=O)(=O)[O-])=CC=C21	2358.5	Standard non polar	33892256
5-Hydroxytryptophol sulfate,1TMS,isomer #2	C[Si](C)(C)N1C=C(CCO)C2=CC(OS(=O)(=O)[O-])=CC=C21	3377.7	Standard polar	33892256
5-Hydroxytryptophol sulfate,2TMS,isomer #1	C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=C(OS(=O)(=O)[O-])C=C12	2426.4	Semi standard non polar	33892256
5-Hydroxytryptophol sulfate,2TMS,isomer #1	C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=C(OS(=O)(=O)[O-])C=C12	2489.8	Standard non polar	33892256
5-Hydroxytryptophol sulfate,2TMS,isomer #1	C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=C(OS(=O)(=O)[O-])C=C12	3024.6	Standard polar	33892256
5-Hydroxytryptophol sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCC1=C[NH]C2=CC=C(OS(=O)(=O)[O-])C=C12	2679.1	Semi standard non polar	33892256
5-Hydroxytryptophol sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCC1=C[NH]C2=CC=C(OS(=O)(=O)[O-])C=C12	2593.2	Standard non polar	33892256
5-Hydroxytryptophol sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCC1=C[NH]C2=CC=C(OS(=O)(=O)[O-])C=C12	3407.0	Standard polar	33892256
5-Hydroxytryptophol sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(CCO)C2=CC(OS(=O)(=O)[O-])=CC=C21	2664.4	Semi standard non polar	33892256
5-Hydroxytryptophol sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(CCO)C2=CC(OS(=O)(=O)[O-])=CC=C21	2553.9	Standard non polar	33892256
5-Hydroxytryptophol sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(CCO)C2=CC(OS(=O)(=O)[O-])=CC=C21	3372.6	Standard polar	33892256
5-Hydroxytryptophol sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(OS(=O)(=O)[O-])C=C12	2939.7	Semi standard non polar	33892256
5-Hydroxytryptophol sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(OS(=O)(=O)[O-])C=C12	2922.6	Standard non polar	33892256
5-Hydroxytryptophol sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(OS(=O)(=O)[O-])C=C12	3110.3	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44237265

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

Correia MSP, Jain A, Alotaibi W, Young Tie Yang P, Rodriguez-Mateos A, Globisch D: Comparative dietary sulfated metabolome analysis reveals unknown metabolic interactions of the gut microbiome and the human host. Free Radic Biol Med. 2020 Nov 20;160:745-754. doi: 10.1016/j.freeradbiomed.2020.09.006. Epub 2020 Sep 11. [PubMed:32927015 ]

Showing metabocard for 5-Hydroxytryptophol sulfate (HMDB0304913)

MOL for HMDB0304913 (5-Hydroxytryptophol sulfate)

3D MOL for HMDB0304913 (5-Hydroxytryptophol sulfate)

3D SDF for HMDB0304913 (5-Hydroxytryptophol sulfate)

3D-SDF for HMDB0304913 (5-Hydroxytryptophol sulfate)

PDB for HMDB0304913 (5-Hydroxytryptophol sulfate)

3D PDB for HMDB0304913 (5-Hydroxytryptophol sulfate)

SMILES for HMDB0304913 (5-Hydroxytryptophol sulfate)

INCHI for HMDB0304913 (5-Hydroxytryptophol sulfate)

Structure for HMDB0304913 (5-Hydroxytryptophol sulfate)

3D Structure for HMDB0304913 (5-Hydroxytryptophol sulfate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized