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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:05:50 UTC

Update Date

2022-03-07 02:54:03 UTC

HMDB ID

HMDB0034291

Secondary Accession Numbers

HMDB34291

Metabolite Identification

Common Name

Sampangine

Description

Sampangine belongs to the class of organic compounds known as 1-azaoxoaporphines. These are analogues of Aporphines, where a nitrogen atom replaces the carbon atom at position 1, and a keto group at C7. Sampangine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Sampangine.

Structure

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

  Mrv0541 05061307422D          

 18 21  0  0  0  0            999 V2000
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    2.1434   -0.4125    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
    1.4289    0.8250    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
    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
    2.8579    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 N   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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  3  2  0  0  0  0
 11  4  2  0  0  0  0
 11 10  1  0  0  0  0
 12  9  2  0  0  0  0
 13 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 12  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  1  0  0  0  0
 16  7  1  0  0  0  0
 16 13  2  0  0  0  0
 17  8  1  0  0  0  0
 17 14  2  0  0  0  0
 18 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034291

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1C2=CC=CC=C2C2=NC=CC3=C2C1=NC=C3

> <INCHI_IDENTIFIER>
InChI=1S/C15H8N2O/c18-15-11-4-2-1-3-10(11)13-12-9(5-7-16-13)6-8-17-14(12)15/h1-8H

> <INCHI_KEY>
BWQKHOMAOVUASZ-UHFFFAOYSA-N

> <FORMULA>
C15H8N2O

> <MOLECULAR_WEIGHT>
232.2368

> <EXACT_MASS>
232.063662888

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.884837371630766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10,16-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9,11,13(17),14-octaen-8-one

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
2.4324109533333336

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.9416170883232824

> <JCHEM_POLAR_SURFACE_AREA>
42.85

> <JCHEM_REFRACTIVITY>
67.1041

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10,16-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9,11,13(17),14-octaen-8-one

> <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       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       5.335   0.000   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       2.667   4.620   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   10                                                       
CONECT    4    2   11                                                       
CONECT    5    7    9                                                       
CONECT    6    8    9                                                       
CONECT    7    5   16                                                       
CONECT    8    6   17                                                       
CONECT    9    5    6   12                                                  
CONECT   10    3   11   13                                                  
CONECT   11    4   10   15                                                  
CONECT   12    9   13   14                                                  
CONECT   13   10   12   16                                                  
CONECT   14   12   15   17                                                  
CONECT   15   11   14   18                                                  
CONECT   16    7   13                                                       
CONECT   17    8   14                                                       
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

COMPND    HMDB0034291
HETATM    1  O1  UNL     1       0.810  -3.092  -0.343  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.536  -1.871  -0.209  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.612  -0.886  -0.157  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.958  -1.243  -0.250  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.959  -0.297  -0.199  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.669   1.040  -0.053  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.321   1.397   0.040  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.318   0.455  -0.011  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.109   0.825   0.087  1.00  0.00           C  
HETATM   10  N1  UNL     1      -0.370   2.137   0.229  1.00  0.00           N  
HETATM   11  C9  UNL     1      -1.664   2.503   0.320  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.714   1.614   0.277  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.436   0.263   0.130  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.463  -0.662   0.082  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.180  -2.001  -0.064  1.00  0.00           C  
HETATM   16  N2  UNL     1      -1.884  -2.353  -0.154  1.00  0.00           N  
HETATM   17  C14 UNL     1      -0.870  -1.470  -0.109  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.114  -0.118   0.036  1.00  0.00           C  
HETATM   19  H1  UNL     1       3.174  -2.302  -0.365  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.997  -0.578  -0.271  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.448   1.797  -0.011  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.094   2.435   0.153  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.885   3.569   0.436  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.743   1.925   0.352  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.486  -0.332   0.158  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.979  -2.756  -0.105  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   17
CONECT    3    4    4    8
CONECT    4    5   19
CONECT    5    6    6   20
CONECT    6    7   21
CONECT    7    8    8   22
CONECT    8    9
CONECT    9   10   18   18
CONECT   10   11   11
CONECT   11   12   23
CONECT   12   13   13   24
CONECT   13   14   18
CONECT   14   15   15   25
CONECT   15   16   26
CONECT   16   17   17
CONECT   17   18
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,6-Diaza-benzo[de]anthracen-7-one	ChEBI
Sampangin	ChEBI
1,6-Diaza-benzo(de)anthracen-7-one	HMDB
7H-naphtho[1,2,3,-Ij][2,7]naphthyridin-7-one, 9ci	HMDB
Sampangine	MeSH

Chemical Formula

C₁₅H₈N₂O

Average Molecular Weight

232.2368

Monoisotopic Molecular Weight

232.063662888

IUPAC Name

10,16-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9,11,13(17),14-octaen-8-one

Traditional Name

10,16-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,9,11,13(17),14-octaen-8-one

CAS Registry Number

116664-93-8

SMILES

O=C1C2=CC=CC=C2C2=NC=CC3=C2C1=NC=C3

InChI Identifier

InChI=1S/C15H8N2O/c18-15-11-4-2-1-3-10(11)13-12-9(5-7-16-13)6-8-17-14(12)15/h1-8H

InChI Key

BWQKHOMAOVUASZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-azaoxoaporphines. These are analogues of Aporphines, where a nitrogen atom replaces the carbon atom at position 1, and a keto group at C7.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

1-azaoxoaporphines

Sub Class

Not Available

Direct Parent

1-azaoxoaporphines

Alternative Parents

Substituents

1-azaoxoaporphine
Benzoquinoline
Diazanaphthalene
Naphthalene
Naphthyridine
Quinoline
Aryl ketone
Pyridine
Benzenoid
Heteroaromatic compound
Ketone
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

alkaloid (CHEBI:67606 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034291)
Cytoplasm (HMDB: HMDB0034291)

Source

Exogenous

Exogenous (HMDB: HMDB0034291)

Food

Food (HMDB: HMDB0034291)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034291)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	210 °C	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	0.076 g/L	ALOGPS
logP	2.24	ALOGPS
logP	2.43	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	2.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	42.85 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.1 m³·mol⁻¹	ChemAxon
Polarizability	23.88 Å³	ChemAxon
Number of Rings	4	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]+	150.172	31661259
DarkChem	[M-H]-	150.006	31661259
DeepCCS	[M+H]+	153.351	30932474
DeepCCS	[M-H]-	150.993	30932474
DeepCCS	[M-2H]-	184.63	30932474
DeepCCS	[M+Na]+	159.621	30932474
AllCCS	[M+H]+	151.3	32859911
AllCCS	[M+H-H2O]+	147.1	32859911
AllCCS	[M+NH4]+	155.2	32859911
AllCCS	[M+Na]+	156.3	32859911
AllCCS	[M-H]-	155.9	32859911
AllCCS	[M+Na-2H]-	154.9	32859911
AllCCS	[M+HCOO]-	153.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sampangine	O=C1C2=CC=CC=C2C2=NC=CC3=C2C1=NC=C3	3361.7	Standard polar	33892256
Sampangine	O=C1C2=CC=CC=C2C2=NC=CC3=C2C1=NC=C3	2169.3	Standard non polar	33892256
Sampangine	O=C1C2=CC=CC=C2C2=NC=CC3=C2C1=NC=C3	2585.8	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 - Sampangine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0090000000-8d57e4de6b7954539ab7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sampangine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sampangine 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 - Sampangine 10V, Positive-QTOF	splash10-001i-0090000000-3bd6c44698131f1472d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sampangine 20V, Positive-QTOF	splash10-001i-0090000000-bfb90d92cca71133850b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sampangine 40V, Positive-QTOF	splash10-001i-3090000000-231ce19292e56e59ddd1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sampangine 10V, Negative-QTOF	splash10-001i-0090000000-d6a136efeeec2a33ab99	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sampangine 20V, Negative-QTOF	splash10-001i-0090000000-d6a136efeeec2a33ab99	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sampangine 40V, Negative-QTOF	splash10-001i-0090000000-1dcdf30dfd527f9d2fd6	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sampangine 10V, Positive-QTOF	splash10-001i-0090000000-236d9b81f746fdd5060e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sampangine 20V, Positive-QTOF	splash10-001i-0090000000-236d9b81f746fdd5060e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sampangine 40V, Positive-QTOF	splash10-001i-0090000000-5707e75c6aaa4c1af895	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sampangine 10V, Negative-QTOF	splash10-001i-0090000000-ac763b917f9a2b8564e5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sampangine 20V, Negative-QTOF	splash10-001i-0090000000-ac763b917f9a2b8564e5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sampangine 40V, Negative-QTOF	splash10-001i-0090000000-ac763b917f9a2b8564e5	2021-09-24	Wishart 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

FDB012630

KNApSAcK ID

Not Available

Chemspider ID

343168

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

387195

PDB ID

Not Available

ChEBI ID

67606

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

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

Showing metabocard for Sampangine (HMDB0034291)

MOL for HMDB0034291 (Sampangine)

3D MOL for HMDB0034291 (Sampangine)

3D SDF for HMDB0034291 (Sampangine)

3D-SDF for HMDB0034291 (Sampangine)

PDB for HMDB0034291 (Sampangine)

3D PDB for HMDB0034291 (Sampangine)

SMILES for HMDB0034291 (Sampangine)

INCHI for HMDB0034291 (Sampangine)

Structure for HMDB0034291 (Sampangine)

3D Structure for HMDB0034291 (Sampangine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra