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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2013-03-04 20:32:09 UTC

Update Date

2023-02-21 17:29:25 UTC

HMDB ID

HMDB0059800

Secondary Accession Numbers

HMDB59800

Metabolite Identification

Common Name

4-Hydroxyphenanthrene

Description

4-Hydroxyphenanthrene, also known as 4-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. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. 4-Hydroxyphenanthrene is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Hydroxyphenanthrene is a potentially toxic compound.

Structure

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


  Mrv1652305261923592D          

 15 17  0  0  0  0            999 V2000
    5.4537    0.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0412   -0.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7412   -0.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0412    1.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -0.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5662   -0.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3287    0.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    1.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9787    1.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162    1.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    0.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9787    0.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5662    1.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7412    1.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9787   -1.0135    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
  6 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059800

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=CC2=C1C1=CC=CC=C1C=C2

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

> <INCHI_KEY>
SIMYIUXARJLHEA-UHFFFAOYSA-N

> <FORMULA>
C14H10O

> <MOLECULAR_WEIGHT>
194.2286

> <EXACT_MASS>
194.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
21.263299621806176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
phenanthren-4-ol

> <ALOGPS_LOGP>
4.12

> <JCHEM_LOGP>
3.6486340076666663

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.438945525851224

> <JCHEM_PKA_STRONGEST_BASIC>
-5.612070287479651

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
60.9393

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.68e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-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      10.180   0.775   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.410  -0.558   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.250  -0.558   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.410   2.109   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.870  -0.558   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.790  -0.558   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.480   0.775   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.100   3.443   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.560   3.443   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.870   2.109   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.100   0.775   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.560   0.775   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.790   2.109   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.250   2.109   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.560  -1.892   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   15                                                  
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                                                       
CONECT   15    6                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Phenanthrenol	ChEBI
4-Hydroxyphenanthrene	ChEBI

Chemical Formula

C₁₄H₁₀O

Average Molecular Weight

194.2286

Monoisotopic Molecular Weight

194.073164942

IUPAC Name

phenanthren-4-ol

Traditional Name

4-hydroxyphenanthrene

CAS Registry Number

Not Available

SMILES

OC1=CC=CC2=C1C1=CC=CC=C1C=C2

InChI Identifier

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

InChI Key

SIMYIUXARJLHEA-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:20469 )

Ontology

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
Water Solubility	0.0087 g/L	ALOGPS
logP	4.12	ALOGPS
logP	3.65	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.44	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	21.26 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]+	141.76	31661259
DarkChem	[M-H]-	139.404	31661259
DeepCCS	[M+H]+	140.904	30932474
DeepCCS	[M-H]-	138.509	30932474
DeepCCS	[M-2H]-	173.231	30932474
DeepCCS	[M+Na]+	147.698	30932474
AllCCS	[M+H]+	141.5	32859911
AllCCS	[M+H-H2O]+	137.0	32859911
AllCCS	[M+NH4]+	145.6	32859911
AllCCS	[M+Na]+	146.8	32859911
AllCCS	[M-H]-	143.8	32859911
AllCCS	[M+Na-2H]-	143.2	32859911
AllCCS	[M+HCOO]-	142.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.94 minutes	32390414
Predicted by Siyang on May 30, 2022	19.796 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.05 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2570.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	714.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	282.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	474.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	512.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	888.8 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	983.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	131.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1516.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	719.7 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	2056.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	569.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	655.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	782.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	465.3 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	83.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyphenanthrene	OC1=CC=CC2=C1C1=CC=CC=C1C=C2	3156.9	Standard polar	33892256
4-Hydroxyphenanthrene	OC1=CC=CC2=C1C1=CC=CC=C1C=C2	2001.7	Standard non polar	33892256
4-Hydroxyphenanthrene	OC1=CC=CC2=C1C1=CC=CC=C1C=C2	2089.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyphenanthrene,1TMS,isomer #1	C[Si](C)(C)OC1=CC=CC2=CC=C3C=CC=CC3=C12	2108.9	Semi standard non polar	33892256
4-Hydroxyphenanthrene,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC2=CC=C3C=CC=CC3=C12	2308.0	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 - 4-Hydroxyphenanthrene GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-0900000000-71237c34affa09894781	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyphenanthrene GC-MS (1 TMS) - 70eV, Positive	splash10-0g4i-9770000000-07655c8fe4049f35e4f4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyphenanthrene 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-Hydroxyphenanthrene 10V, Positive-QTOF	splash10-0002-0900000000-59a331161edbe67eee74	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenanthrene 20V, Positive-QTOF	splash10-0002-0900000000-dc59fd653e3f99d7d631	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenanthrene 40V, Positive-QTOF	splash10-00or-0900000000-3c0fc714d528f19a8c60	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenanthrene 10V, Negative-QTOF	splash10-0006-0900000000-9bfbb18d23435bcfaedc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenanthrene 20V, Negative-QTOF	splash10-0006-0900000000-0896fac27e4f6fb8a9bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenanthrene 40V, Negative-QTOF	splash10-0006-1900000000-382fb34e0222293f124f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenanthrene 10V, Positive-QTOF	splash10-0002-0900000000-27ce7a0a54d46fbd9a75	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenanthrene 20V, Positive-QTOF	splash10-0002-0900000000-27ce7a0a54d46fbd9a75	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenanthrene 40V, Positive-QTOF	splash10-014i-0900000000-3de0b163ac1c311cde55	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenanthrene 10V, Negative-QTOF	splash10-0006-0900000000-8d1a6691fd9f5b8c101f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenanthrene 20V, Negative-QTOF	splash10-0006-0900000000-8d1a6691fd9f5b8c101f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyphenanthrene 40V, Negative-QTOF	splash10-014l-0900000000-0d9e2219853132a9b2d5	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	0.000058-0.00015 umol/mmol creatinine	Adult (>18 years old)	Male	Workers in coking plants	8282417	details
Urine	Detected and Quantified	0.0000183 (0.0000169-0.0000199) umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected and Quantified	0.0000133 (0.0000116-0.0000154) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	National Health a...	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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenanthrenoid

METLIN ID

Not Available

PubChem Compound

82105

PDB ID

Not Available

ChEBI ID

20469

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

Not Available

Showing metabocard for 4-Hydroxyphenanthrene (HMDB0059800)

MOL for HMDB0059800 (4-Hydroxyphenanthrene)

3D MOL for HMDB0059800 (4-Hydroxyphenanthrene)

3D SDF for HMDB0059800 (4-Hydroxyphenanthrene)

3D-SDF for HMDB0059800 (4-Hydroxyphenanthrene)

PDB for HMDB0059800 (4-Hydroxyphenanthrene)

3D PDB for HMDB0059800 (4-Hydroxyphenanthrene)

SMILES for HMDB0059800 (4-Hydroxyphenanthrene)

INCHI for HMDB0059800 (4-Hydroxyphenanthrene)

Structure for HMDB0059800 (4-Hydroxyphenanthrene)

3D Structure for HMDB0059800 (4-Hydroxyphenanthrene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra