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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:14:52 UTC

Update Date

2023-02-21 17:24:45 UTC

HMDB ID

HMDB0035291

Secondary Accession Numbers

HMDB35291

Metabolite Identification

Common Name

Isoplumbagin

Description

Isoplumbagin belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). Isoplumbagin has been detected, but not quantified in, nuts. This could make isoplumbagin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isoplumbagin.

Structure

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


  Mrv0541 05061308212D          

 14 15  0  0  0  0            999 V2000
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  1  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  7  2  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 11 10  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
 14 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035291

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(=O)C2=C(C(O)=CC=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H8O3/c1-6-5-9(13)7-3-2-4-8(12)10(7)11(6)14/h2-5,12H,1H3

> <INCHI_KEY>
ZMOIGGHUSNHCAB-UHFFFAOYSA-N

> <FORMULA>
C11H8O3

> <MOLECULAR_WEIGHT>
188.1794

> <EXACT_MASS>
188.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.498849094014354

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.236303118333333

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.132575243112129

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.472605245801965

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4407573510479486

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
52.52120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-2-methylnaphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

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       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   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   1.540   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  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+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   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    3    4                                                       
CONECT    3    2    7                                                       
CONECT    4    2    8                                                       
CONECT    5    6    9                                                       
CONECT    6    1    5   11                                                  
CONECT    7    3    9   10                                                  
CONECT    8    4   10   12                                                  
CONECT    9    5    7   13                                                  
CONECT   10    7    8   11                                                  
CONECT   11    6   10   14                                                  
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-Hydroxy-2-methyl-1,4-naphthalenedione, 9ci	HMDB

Chemical Formula

C₁₁H₈O₃

Average Molecular Weight

188.1794

Monoisotopic Molecular Weight

188.047344122

IUPAC Name

8-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dione

Traditional Name

8-hydroxy-2-methylnaphthalene-1,4-dione

CAS Registry Number

14777-17-4

SMILES

CC1=CC(=O)C2=C(C(O)=CC=C2)C1=O

InChI Identifier

InChI=1S/C11H8O3/c1-6-5-9(13)7-3-2-4-8(12)10(7)11(6)14/h2-5,12H,1H3

InChI Key

ZMOIGGHUSNHCAB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Organic oxygen compound
Organic oxide
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: HMDB0035291)
Cytoplasm (HMDB: HMDB0035291)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035291)

Source

Exogenous

Exogenous (HMDB: HMDB0035291)

Food

Food (HMDB: HMDB0035291)

Nut

Nuts (FooDB: FOOD00869)

Endogenous

Plant

Plant (HMDB: HMDB0035291)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035291)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	67 - 68 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1385 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	1.3 g/L	ALOGPS
logP	2.16	ALOGPS
logP	2.24	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	9.47	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	52.52 m³·mol⁻¹	ChemAxon
Polarizability	18.5 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]+	143.614	31661259
DarkChem	[M-H]-	140.893	31661259
DeepCCS	[M+H]+	139.094	30932474
DeepCCS	[M-H]-	136.699	30932474
DeepCCS	[M-2H]-	171.188	30932474
DeepCCS	[M+Na]+	145.705	30932474
AllCCS	[M+H]+	138.7	32859911
AllCCS	[M+H-H2O]+	134.3	32859911
AllCCS	[M+NH4]+	142.9	32859911
AllCCS	[M+Na]+	144.1	32859911
AllCCS	[M-H]-	138.5	32859911
AllCCS	[M+Na-2H]-	138.6	32859911
AllCCS	[M+HCOO]-	138.8	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.	6.1 minutes	32390414
Predicted by Siyang on May 30, 2022	12.6584 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.99 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1995.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	401.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	136.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	246.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	181.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	416.8 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	680.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	136.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	988.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	421.1 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	1289.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	414.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	418.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	571.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	281.2 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	141.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoplumbagin	CC1=CC(=O)C2=C(C(O)=CC=C2)C1=O	2522.8	Standard polar	33892256
Isoplumbagin	CC1=CC(=O)C2=C(C(O)=CC=C2)C1=O	1631.9	Standard non polar	33892256
Isoplumbagin	CC1=CC(=O)C2=C(C(O)=CC=C2)C1=O	1561.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoplumbagin,1TMS,isomer #1	CC1=CC(=O)C2=CC=CC(O[Si](C)(C)C)=C2C1=O	1849.2	Semi standard non polar	33892256
Isoplumbagin,1TBDMS,isomer #1	CC1=CC(=O)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	2124.1	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 - Isoplumbagin GC-MS (Non-derivatized) - 70eV, Positive	splash10-03kj-0900000000-a80f2b4a5daf6e421860	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoplumbagin GC-MS (1 TMS) - 70eV, Positive	splash10-00xs-5790000000-2150359604203bbc51e0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoplumbagin 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 - Isoplumbagin 10V, Positive-QTOF	splash10-000i-0900000000-e1fa3359c80f5ab4774a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoplumbagin 20V, Positive-QTOF	splash10-000i-2900000000-c95a4150048462ac94a1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoplumbagin 40V, Positive-QTOF	splash10-0g6v-9800000000-1af4e978b4d260668c04	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoplumbagin 10V, Negative-QTOF	splash10-000i-0900000000-0ff8a0ff7cb874e97634	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoplumbagin 20V, Negative-QTOF	splash10-000i-0900000000-cbd544ffdc8c04b45a0b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoplumbagin 40V, Negative-QTOF	splash10-000i-7900000000-da2a7c76bb6f4b746e71	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoplumbagin 10V, Negative-QTOF	splash10-000i-0900000000-d3031a961d813f4cc6d1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoplumbagin 20V, Negative-QTOF	splash10-000i-0900000000-1ca2f886b1066df47df8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoplumbagin 40V, Negative-QTOF	splash10-0a4i-1900000000-f4c750208b5cf155fd9c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoplumbagin 10V, Positive-QTOF	splash10-000i-0900000000-3cae29c633172c0bc773	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoplumbagin 20V, Positive-QTOF	splash10-0079-0900000000-995b81d3abfe39f32269	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoplumbagin 40V, Positive-QTOF	splash10-007c-4900000000-ab766bba9e873617c58a	2021-09-22	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

FDB013956

KNApSAcK ID

Not Available

Chemspider ID

332757

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

375105

PDB ID

Not Available

ChEBI ID

173524

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1848871

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 Isoplumbagin (HMDB0035291)

MOL for HMDB0035291 (Isoplumbagin)

3D MOL for HMDB0035291 (Isoplumbagin)

3D SDF for HMDB0035291 (Isoplumbagin)

3D-SDF for HMDB0035291 (Isoplumbagin)

PDB for HMDB0035291 (Isoplumbagin)

3D PDB for HMDB0035291 (Isoplumbagin)

SMILES for HMDB0035291 (Isoplumbagin)

INCHI for HMDB0035291 (Isoplumbagin)

Structure for HMDB0035291 (Isoplumbagin)

3D Structure for HMDB0035291 (Isoplumbagin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra