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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

enzymes (4) Show 4 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2013-03-04 20:26:26 UTC

Update Date

2023-02-21 17:29:24 UTC

HMDB ID

HMDB0059797

Secondary Accession Numbers

HMDB59797

Metabolite Identification

Common Name

1-Hydroxyphenanthrene

Description

1-Hydroxyphenanthrene, also known as 1-phenanthrenol, belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached. 1-Hydroxyphenanthrene is an extremely weak basic (essentially neutral) compound (based on its pKa). 1-Hydroxyphenanthrene exists in all living organisms, ranging from bacteria to humans. 1-Hydroxyphenanthrene is a potentially toxic compound. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Structure

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


  Mrv1652305261923512D          

 15 17  0  0  0  0            999 V2000
    5.4434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  3  1  0  0  0  0
  9  8  2  0  0  0  0
 10  4  2  0  0  0  0
 10  8  1  0  0  0  0
 11  5  2  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  2  0  0  0  0
 14  7  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059797

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=CC2=C1C=CC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O/c15-14-7-3-6-12-11-5-2-1-4-10(11)8-9-13(12)14/h1-9,15H

> <INCHI_KEY>
GTBXZWADMKOZQJ-UHFFFAOYSA-N

> <FORMULA>
C14H10O

> <MOLECULAR_WEIGHT>
194.2286

> <EXACT_MASS>
194.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
21.357780346490827

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
phenanthren-1-ol

> <ALOGPS_LOGP>
4.15

> <JCHEM_LOGP>
3.6486340076666663

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.56592429246752

> <JCHEM_PKA_STRONGEST_BASIC>
-5.596229125769853

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
60.93930000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.18e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxyphenanthrene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      10.161   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.391  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.231  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.391   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.851  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.771  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.461   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.541   3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.851   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.541   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.771   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.231   2.104   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.461   3.437   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    5                                                       
CONECT    3    6    7                                                       
CONECT    4    1   10                                                       
CONECT    5    2   11                                                       
CONECT    6    3   12                                                       
CONECT    7    3   14                                                       
CONECT    8    9   10                                                       
CONECT    9    8   13                                                       
CONECT   10    4    8   11                                                  
CONECT   11    5   10   12                                                  
CONECT   12    6   11   13                                                  
CONECT   13    9   12   14                                                  
CONECT   14    7   13   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Phenanthrenol	ChEBI
1-Hydroxyphenanthrene	ChEBI

Chemical Formula

C₁₄H₁₀O

Average Molecular Weight

194.2286

Monoisotopic Molecular Weight

194.073164942

IUPAC Name

phenanthren-1-ol

Traditional Name

1-hydroxyphenanthrene

CAS Registry Number

Not Available

SMILES

OC1=CC=CC2=C1C=CC1=CC=CC=C21

InChI Identifier

InChI=1S/C14H10O/c15-14-7-3-6-12-11-5-2-1-4-10(11)8-9-13(12)14/h1-9,15H

InChI Key

GTBXZWADMKOZQJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthrols

Direct Parent

Phenanthrols

Alternative Parents

Substituents

Phenanthrol
1-naphthol
Naphthalene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

phenanthrol (CHEBI:27528 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0059797)

Excreta

Biofluid or Excreta

Urine (PMID: 8282417)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

1-Hydroxyphenanthrene Exposure (MarkerDB: MDB00029784)

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
Water Solubility	0.0072 g/L	ALOGPS
logP	4.15	ALOGPS
logP	3.65	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.57	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	60.94 m³·mol⁻¹	ChemAxon
Polarizability	21.36 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	142.873	31661259
DarkChem	[M-H]-	140.345	31661259
DeepCCS	[M-2H]-	167.14	30932474
DeepCCS	[M+Na]+	142.679	30932474
AllCCS	[M+H]+	141.7	32859911
AllCCS	[M+H-H2O]+	137.2	32859911
AllCCS	[M+NH4]+	145.8	32859911
AllCCS	[M+Na]+	147.0	32859911
AllCCS	[M-H]-	144.1	32859911
AllCCS	[M+Na-2H]-	143.5	32859911
AllCCS	[M+HCOO]-	143.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Hydroxyphenanthrene	OC1=CC=CC2=C1C=CC1=CC=CC=C21	3109.2	Standard polar	33892256
1-Hydroxyphenanthrene	OC1=CC=CC2=C1C=CC1=CC=CC=C21	2018.6	Standard non polar	33892256
1-Hydroxyphenanthrene	OC1=CC=CC2=C1C=CC1=CC=CC=C21	2147.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Hydroxyphenanthrene,1TMS,isomer #1	C[Si](C)(C)OC1=CC=CC2=C1C=CC1=CC=CC=C12	2147.7	Semi standard non polar	33892256
1-Hydroxyphenanthrene,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C=CC1=CC=CC=C12	2364.6	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 - 1-Hydroxyphenanthrene GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-0900000000-b331cc0785ae2cd69f06	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Hydroxyphenanthrene GC-MS (1 TMS) - 70eV, Positive	splash10-0g4i-9780000000-2d267b2d0939fee12b16	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Hydroxyphenanthrene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Hydroxyphenanthrene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00kf-2900000000-b0f535e13822fda81197	2014-10-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxyphenanthrene 10V, Positive-QTOF	splash10-0002-0900000000-2f646c0a5bbb5cf2f0be	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxyphenanthrene 20V, Positive-QTOF	splash10-0002-0900000000-f2dc8d627b1f2598181b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxyphenanthrene 40V, Positive-QTOF	splash10-0fr2-1900000000-a78916ff2fff0b83cfe2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxyphenanthrene 10V, Negative-QTOF	splash10-0006-0900000000-9169c82deb2dce647b59	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxyphenanthrene 20V, Negative-QTOF	splash10-0006-0900000000-9169c82deb2dce647b59	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxyphenanthrene 40V, Negative-QTOF	splash10-0006-1900000000-8f4b234849fe6eb55051	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxyphenanthrene 10V, Positive-QTOF	splash10-0002-0900000000-27ce7a0a54d46fbd9a75	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxyphenanthrene 20V, Positive-QTOF	splash10-0002-0900000000-27ce7a0a54d46fbd9a75	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxyphenanthrene 40V, Positive-QTOF	splash10-0gb9-0900000000-e10cede2ea39b5e367ae	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxyphenanthrene 10V, Negative-QTOF	splash10-0006-0900000000-8d1a6691fd9f5b8c101f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxyphenanthrene 20V, Negative-QTOF	splash10-0006-0900000000-8d1a6691fd9f5b8c101f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxyphenanthrene 40V, Negative-QTOF	splash10-0006-0900000000-60f1805237ca1cb006c7	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.0000844 (0.0000786-0.0000914) umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected and Quantified	0.0000867 (0.0000768-0.0000984) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected and Quantified	0.00058-0.0104 umol/mmol creatinine	Adult (>18 years old)	Male	Workers in coking plants	8282417	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C11432

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

1-Hydroxyphenanthrene

METLIN ID

Not Available

PubChem Compound

98490

PDB ID

Not Available

ChEBI ID

27528

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029784

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. HemK methyltransferase family member 1

General function:: Not Available
Specific function:: N5-glutamine methyltransferase responsible for the methylation of the GGQ triplet of the mitochondrial translation release factor MTRF1L.
Gene Name:: HEMK1
Uniprot ID:: Q9Y5R4
Molecular weight:: Not Available

Reactions

1-Hydroxyphenanthrene + CH3-R → 1-Methoxyphenanthrene + R	details

Enzyme Details

2. Methyltransferase-like protein 2B

General function:: Not Available
Specific function:: Probable methyltransferase (By similarity).
Gene Name:: METTL2B
Uniprot ID:: Q6P1Q9
Molecular weight:: Not Available

Reactions

1-Hydroxyphenanthrene + CH3-R → 1-Methoxyphenanthrene + R	details

Enzyme Details

3. Methyltransferase-like protein 6

General function:: Not Available
Specific function:: Probable methyltransferase (By similarity).
Gene Name:: METTL6
Uniprot ID:: Q8TCB7
Molecular weight:: Not Available

Reactions

1-Hydroxyphenanthrene + CH3-R → 1-Methoxyphenanthrene + R	details

Enzyme Details

4. Uncharacterized methyltransferase WBSCR22

General function:: Not Available
Specific function:: Methyltransferase that may act on DNA.
Gene Name:: WBSCR22
Uniprot ID:: O43709
Molecular weight:: Not Available

Reactions

1-Hydroxyphenanthrene + CH3-R → 1-Methoxyphenanthrene + R	details

Showing metabocard for 1-Hydroxyphenanthrene (HMDB0059797)

MOL for HMDB0059797 (1-Hydroxyphenanthrene)

3D MOL for HMDB0059797 (1-Hydroxyphenanthrene)

3D SDF for HMDB0059797 (1-Hydroxyphenanthrene)

3D-SDF for HMDB0059797 (1-Hydroxyphenanthrene)

PDB for HMDB0059797 (1-Hydroxyphenanthrene)

3D PDB for HMDB0059797 (1-Hydroxyphenanthrene)

SMILES for HMDB0059797 (1-Hydroxyphenanthrene)

INCHI for HMDB0059797 (1-Hydroxyphenanthrene)

Structure for HMDB0059797 (1-Hydroxyphenanthrene)

3D Structure for HMDB0059797 (1-Hydroxyphenanthrene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions