Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-29 23:07:14 UTC

Update Date

2022-09-22 18:34:38 UTC

HMDB ID

HMDB0304928

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3- Hydroxyindolin-2-one-sulfate

Description

3- Hydroxyindolin-2-one-sulfate belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole. Based on a literature review very few articles have been published on 3- Hydroxyindolin-2-one-sulfate.

Structure

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


  Mrv1652309302101082D          

 15 16  0  0  0  0            999 V2000
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9878   -1.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8227   -1.0942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0489    0.0098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 14  7  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  2  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0304928

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=NC2=CC=CC=C2C1OS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H7NO5S/c10-8-7(14-15(11,12)13)5-3-1-2-4-6(5)9-8/h1-4,7H,(H,9,10)(H,11,12,13)

> <INCHI_KEY>
HLYCAHONCGGOOJ-UHFFFAOYSA-N

> <FORMULA>
C8H7NO5S

> <MOLECULAR_WEIGHT>
229.21

> <EXACT_MASS>
229.004493503

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
20.208804349208762

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2-hydroxy-3H-indol-3-yl)oxidanesulfonic acid

> <ALOGPS_LOGP>
-1.26

> <JCHEM_LOGP>
0.31687242520671105

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.0896717647292906

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.2339013253706

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9128024048150863

> <JCHEM_POLAR_SURFACE_AREA>
96.19000000000001

> <JCHEM_REFRACTIVITY>
51.67

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.87e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-hydroxy-3H-indol-3-yl)oxidanesulfonic acid

> <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       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      -0.320   2.843   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.711  -2.157   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.536  -2.043   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.825   0.018   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.650   0.132   0.000  0.00  0.00           O+0
HETATM   15  S   UNK     0       2.680  -1.012   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6    7                                                  
CONECT    6    4    5    9                                                  
CONECT    7    5    8   14                                                  
CONECT    8    7    9   10                                                  
CONECT    9    6    8                                                       
CONECT   10    8                                                            
CONECT   11   15                                                            
CONECT   12   15                                                            
CONECT   13   15                                                            
CONECT   14    7   15                                                       
CONECT   15   11   12   13   14                                             
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3- Hydroxyindolin-2-one-sulfuric acid	Generator
3- Hydroxyindolin-2-one-sulphate	Generator
3- Hydroxyindolin-2-one-sulphuric acid	Generator
(2-Hydroxy-3H-indol-3-yl)oxidanesulfonate	HMDB
(2-Hydroxy-3H-indol-3-yl)oxidanesulphonate	HMDB
(2-Hydroxy-3H-indol-3-yl)oxidanesulphonic acid	HMDB

Chemical Formula

C₈H₇NO₅S

Average Molecular Weight

229.21

Monoisotopic Molecular Weight

229.004493503

IUPAC Name

(2-hydroxy-3H-indol-3-yl)oxidanesulfonic acid

Traditional Name

(2-hydroxy-3H-indol-3-yl)oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

OC1=NC2=CC=CC=C2C1OS(O)(=O)=O

InChI Identifier

InChI=1S/C8H7NO5S/c10-8-7(14-15(11,12)13)5-3-1-2-4-6(5)9-8/h1-4,7H,(H,9,10)(H,11,12,13)

InChI Key

HLYCAHONCGGOOJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolines

Direct Parent

Indolines

Alternative Parents

Substituents

Dihydroindole
Sulfuric acid monoester
Sulfate-ester
Alkyl sulfate
Sulfuric acid ester
Benzenoid
Organic sulfuric acid or derivatives
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	-1.3	ALOGPS
logP	0.32	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	-2.2	ChemAxon
pKa (Strongest Basic)	-0.91	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.19 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	51.67 m³·mol⁻¹	ChemAxon
Polarizability	20.21 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
AllCCS	[M+H]+	149.016	32859911
AllCCS	[M+H-H2O]+	144.971	32859911
AllCCS	[M+Na]+	153.862	32859911
AllCCS	[M+NH4]+	152.779	32859911
AllCCS	[M-H]-	141.874	32859911
AllCCS	[M+Na-2H]-	141.937	32859911
AllCCS	[M+HCOO]-	142.095	32859911
DeepCCS	[M+H]+	140.106	30932474
DeepCCS	[M-H]-	136.558	30932474
DeepCCS	[M-2H]-	173.74	30932474
DeepCCS	[M+Na]+	149.278	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.3733 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.93 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1215.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	310.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	82.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	179.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	284.6 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	350.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	151.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	685.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	192.6 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	1028.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	193.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	228.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	559.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	205.6 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	213.4 seconds	40023050

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3- Hydroxyindolin-2-one-sulfate,1TMS,isomer #1	C[Si](C)(C)OC1=NC2=CC=CC=C2C1OS(=O)(=O)O	2089.4	Semi standard non polar	33892256
3- Hydroxyindolin-2-one-sulfate,1TMS,isomer #1	C[Si](C)(C)OC1=NC2=CC=CC=C2C1OS(=O)(=O)O	2071.9	Standard non polar	33892256
3- Hydroxyindolin-2-one-sulfate,1TMS,isomer #1	C[Si](C)(C)OC1=NC2=CC=CC=C2C1OS(=O)(=O)O	3558.9	Standard polar	33892256
3- Hydroxyindolin-2-one-sulfate,1TMS,isomer #2	C[Si](C)(C)OS(=O)(=O)OC1C(O)=NC2=CC=CC=C21	2124.9	Semi standard non polar	33892256
3- Hydroxyindolin-2-one-sulfate,1TMS,isomer #2	C[Si](C)(C)OS(=O)(=O)OC1C(O)=NC2=CC=CC=C21	1977.0	Standard non polar	33892256
3- Hydroxyindolin-2-one-sulfate,1TMS,isomer #2	C[Si](C)(C)OS(=O)(=O)OC1C(O)=NC2=CC=CC=C21	3396.2	Standard polar	33892256
3- Hydroxyindolin-2-one-sulfate,2TMS,isomer #1	C[Si](C)(C)OC1=NC2=CC=CC=C2C1OS(=O)(=O)O[Si](C)(C)C	2113.5	Semi standard non polar	33892256
3- Hydroxyindolin-2-one-sulfate,2TMS,isomer #1	C[Si](C)(C)OC1=NC2=CC=CC=C2C1OS(=O)(=O)O[Si](C)(C)C	2187.1	Standard non polar	33892256
3- Hydroxyindolin-2-one-sulfate,2TMS,isomer #1	C[Si](C)(C)OC1=NC2=CC=CC=C2C1OS(=O)(=O)O[Si](C)(C)C	3184.2	Standard polar	33892256
3- Hydroxyindolin-2-one-sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC2=CC=CC=C2C1OS(=O)(=O)O	2336.5	Semi standard non polar	33892256
3- Hydroxyindolin-2-one-sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC2=CC=CC=C2C1OS(=O)(=O)O	2316.2	Standard non polar	33892256
3- Hydroxyindolin-2-one-sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC2=CC=CC=C2C1OS(=O)(=O)O	3570.3	Standard polar	33892256
3- Hydroxyindolin-2-one-sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1C(O)=NC2=CC=CC=C21	2355.7	Semi standard non polar	33892256
3- Hydroxyindolin-2-one-sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1C(O)=NC2=CC=CC=C21	2270.9	Standard non polar	33892256
3- Hydroxyindolin-2-one-sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1C(O)=NC2=CC=CC=C21	3407.2	Standard polar	33892256
3- Hydroxyindolin-2-one-sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC2=CC=CC=C2C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	2561.1	Semi standard non polar	33892256
3- Hydroxyindolin-2-one-sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC2=CC=CC=C2C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	2725.0	Standard non polar	33892256
3- Hydroxyindolin-2-one-sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC2=CC=CC=C2C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	3213.9	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3- Hydroxyindolin-2-one-sulfate 10V, Positive-QTOF	splash10-001i-0190000000-b6b74b56fc7362ba1947	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3- Hydroxyindolin-2-one-sulfate 20V, Positive-QTOF	splash10-0089-0900000000-696289f3053b73dbbbc8	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3- Hydroxyindolin-2-one-sulfate 40V, Positive-QTOF	splash10-014i-9500000000-9dd7256bc3d43c9c1396	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3- Hydroxyindolin-2-one-sulfate 10V, Negative-QTOF	splash10-004i-0090000000-fdc8cd6c0cbaa877719b	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3- Hydroxyindolin-2-one-sulfate 20V, Negative-QTOF	splash10-004i-0290000000-42c20822b796b805fd45	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3- Hydroxyindolin-2-one-sulfate 40V, Negative-QTOF	splash10-00lr-9300000000-9389db6a8c034f251727	2021-10-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

157010389

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 3- Hydroxyindolin-2-one-sulfate (HMDB0304928)

MOL for HMDB0304928 (3- Hydroxyindolin-2-one-sulfate)

3D MOL for HMDB0304928 (3- Hydroxyindolin-2-one-sulfate)

3D SDF for HMDB0304928 (3- Hydroxyindolin-2-one-sulfate)

3D-SDF for HMDB0304928 (3- Hydroxyindolin-2-one-sulfate)

PDB for HMDB0304928 (3- Hydroxyindolin-2-one-sulfate)

3D PDB for HMDB0304928 (3- Hydroxyindolin-2-one-sulfate)

SMILES for HMDB0304928 (3- Hydroxyindolin-2-one-sulfate)

INCHI for HMDB0304928 (3- Hydroxyindolin-2-one-sulfate)

Structure for HMDB0304928 (3- Hydroxyindolin-2-one-sulfate)

3D Structure for HMDB0304928 (3- Hydroxyindolin-2-one-sulfate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra