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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:28 UTC

Update Date

2023-02-21 17:22:43 UTC

HMDB ID

HMDB0032883

Secondary Accession Numbers

HMDB32883

Metabolite Identification

Common Name

1,4,5-Naphthalenetriol

Description

1,4,5-Naphthalenetriol belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. 1,4,5-Naphthalenetriol has been detected, but not quantified in, nuts. This could make 1,4,5-naphthalenetriol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1,4,5-Naphthalenetriol.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    8                                                       
CONECT    4    5    7                                                       
CONECT    5    4    9                                                       
CONECT    6    2    7   10                                                  
CONECT    7    4    6   11                                                  
CONECT    8    3   10   12                                                  
CONECT    9    5   10   13                                                  
CONECT   10    6    8    9                                                  
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,4,5-Trihydroxynaphthalene	HMDB
a-Hydrojuglone	HMDB
alpha-Hydrojuglone	HMDB

Chemical Formula

C₁₀H₈O₃

Average Molecular Weight

176.1687

Monoisotopic Molecular Weight

176.047344122

IUPAC Name

naphthalene-1,4,5-triol

Traditional Name

naphthalene-1,4,5-triol

CAS Registry Number

481-40-3

SMILES

OC1=CC=CC2=C(O)C=CC(O)=C12

InChI Identifier

InChI=1S/C10H8O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,11-13H

InChI Key

NHEVNUARLCWEED-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthols and derivatives

Direct Parent

Naphthols and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032883)
Cytoplasm (HMDB: HMDB0032883)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032883)

Source

Exogenous

Food

Food (HMDB: HMDB0032883)

Nut

Nuts (FooDB: FOOD00869)

Endogenous

Plant

Plant (HMDB: HMDB0032883)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032883)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	168 - 170 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	7300 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.5 g/L	ALOGPS
logP	1.34	ALOGPS
logP	2.05	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	8.78	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	48.45 m³·mol⁻¹	ChemAxon
Polarizability	17.21 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
DarkChem	[M+H]+	137.633	31661259
DarkChem	[M-H]-	134.122	31661259
DeepCCS	[M-2H]-	170.172	30932474
DeepCCS	[M+Na]+	145.71	30932474
AllCCS	[M+H]+	136.5	32859911
AllCCS	[M+H-H2O]+	132.0	32859911
AllCCS	[M+NH4]+	140.7	32859911
AllCCS	[M+Na]+	142.0	32859911
AllCCS	[M-H]-	132.5	32859911
AllCCS	[M+Na-2H]-	132.8	32859911
AllCCS	[M+HCOO]-	133.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,4,5-Naphthalenetriol	OC1=CC=CC2=C(O)C=CC(O)=C12	3748.9	Standard polar	33892256
1,4,5-Naphthalenetriol	OC1=CC=CC2=C(O)C=CC(O)=C12	1901.2	Standard non polar	33892256
1,4,5-Naphthalenetriol	OC1=CC=CC2=C(O)C=CC(O)=C12	2084.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,4,5-Naphthalenetriol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=CC2=C(O)C=CC(O)=C12	2045.9	Semi standard non polar	33892256
1,4,5-Naphthalenetriol,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(O)C2=C(O)C=CC=C12	2070.6	Semi standard non polar	33892256
1,4,5-Naphthalenetriol,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(O)C2=CC=CC(O)=C12	2039.7	Semi standard non polar	33892256
1,4,5-Naphthalenetriol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(O)C2=C(O[Si](C)(C)C)C=CC=C12	2028.6	Semi standard non polar	33892256
1,4,5-Naphthalenetriol,2TMS,isomer #2	C[Si](C)(C)OC1=CC=CC2=C(O)C=CC(O[Si](C)(C)C)=C12	2032.5	Semi standard non polar	33892256
1,4,5-Naphthalenetriol,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(O[Si](C)(C)C)C2=C(O)C=CC=C12	2033.2	Semi standard non polar	33892256
1,4,5-Naphthalenetriol,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(O[Si](C)(C)C)C2=C(O[Si](C)(C)C)C=CC=C12	2089.5	Semi standard non polar	33892256
1,4,5-Naphthalenetriol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C(O)C=CC(O)=C12	2313.7	Semi standard non polar	33892256
1,4,5-Naphthalenetriol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(O)C2=C(O)C=CC=C12	2326.2	Semi standard non polar	33892256
1,4,5-Naphthalenetriol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(O)C2=CC=CC(O)=C12	2312.3	Semi standard non polar	33892256
1,4,5-Naphthalenetriol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC=C12	2573.1	Semi standard non polar	33892256
1,4,5-Naphthalenetriol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C(O)C=CC(O[Si](C)(C)C(C)(C)C)=C12	2577.1	Semi standard non polar	33892256
1,4,5-Naphthalenetriol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(O[Si](C)(C)C(C)(C)C)C2=C(O)C=CC=C12	2564.3	Semi standard non polar	33892256
1,4,5-Naphthalenetriol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(O[Si](C)(C)C(C)(C)C)C2=C(O[Si](C)(C)C(C)(C)C)C=CC=C12	2798.6	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 - 1,4,5-Naphthalenetriol GC-MS (Non-derivatized) - 70eV, Positive	splash10-002b-0900000000-b44abf62c3fced73e0cf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,4,5-Naphthalenetriol GC-MS (3 TMS) - 70eV, Positive	splash10-00bc-6149000000-83795c55d79a7b667d80	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,4,5-Naphthalenetriol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,4,5-Naphthalenetriol 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 - 1,4,5-Naphthalenetriol 10V, Positive-QTOF	splash10-004i-0900000000-4df897ced39fd43a156a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Naphthalenetriol 20V, Positive-QTOF	splash10-004i-0900000000-0b86df1f65fa4edf1643	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Naphthalenetriol 40V, Positive-QTOF	splash10-0a4i-2900000000-b857d525e402d7bbc0ba	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Naphthalenetriol 10V, Negative-QTOF	splash10-004i-0900000000-d1ac96333f15f2a6f5e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Naphthalenetriol 20V, Negative-QTOF	splash10-004i-0900000000-8d79760b38be3fce502c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Naphthalenetriol 40V, Negative-QTOF	splash10-056v-3900000000-fcdd97ca94e1556df4b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Naphthalenetriol 10V, Negative-QTOF	splash10-004i-0900000000-e8f23b5d4cdbbb9787c4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Naphthalenetriol 20V, Negative-QTOF	splash10-004i-0900000000-b8c9969fb744fb6a726a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Naphthalenetriol 40V, Negative-QTOF	splash10-0005-3900000000-57b1f4c5511e0dcf3647	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Naphthalenetriol 10V, Positive-QTOF	splash10-004i-0900000000-00ffe2c25b8beb0eeaa0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Naphthalenetriol 20V, Positive-QTOF	splash10-004i-0900000000-af285c8324717a01d916	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4,5-Naphthalenetriol 40V, Positive-QTOF	splash10-052e-9800000000-32eb831c891a119c9770	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]-)	2023-02-04	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

Cytoplasm
Extracellular

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

FDB010865

KNApSAcK ID

C00057402

Chemspider ID

2340766

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3083585

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1832301

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 1,4,5-Naphthalenetriol (HMDB0032883)

MOL for HMDB0032883 (1,4,5-Naphthalenetriol)

3D MOL for HMDB0032883 (1,4,5-Naphthalenetriol)

3D SDF for HMDB0032883 (1,4,5-Naphthalenetriol)

3D-SDF for HMDB0032883 (1,4,5-Naphthalenetriol)

PDB for HMDB0032883 (1,4,5-Naphthalenetriol)

3D PDB for HMDB0032883 (1,4,5-Naphthalenetriol)

SMILES for HMDB0032883 (1,4,5-Naphthalenetriol)

INCHI for HMDB0032883 (1,4,5-Naphthalenetriol)

Structure for HMDB0032883 (1,4,5-Naphthalenetriol)

3D Structure for HMDB0032883 (1,4,5-Naphthalenetriol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra