NP-MRD: Showing NP-Card for tepuazine D (NP0332704)

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Record Information

Version

2.0

Created at

2024-03-21 17:27:51 UTC

Updated at

2025-12-21 21:41:03 UTC

NP-MRD ID

NP0332704

Natural Product DOI

https://doi.org/10.57994/1964

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tepuazine D

Description

Tepuazine D belongs to the class of organic compounds known as phenazines and derivatives. These are polycyclic aromatic compounds containing a phenazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a pyrazine ring. Based on a literature review very few articles have been published on tepuazine D.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03212417272D          

 25 28  0  0  1  0            999 V2000
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    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    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 13 18  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 10 19  1  0  0  0  0
 11 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
  9 22  1  0  0  0  0
  7 23  1  0  0  0  0
 24 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0332704

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](OC2=C3N=C4C=CC=CC4=NC3=CC=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H18N2O5/c1-9-15(21)16(22)17(23)18(24-9)25-13-8-4-7-12-14(13)20-11-6-3-2-5-10(11)19-12/h2-9,15-18,21-23H,1H3/t9-,15-,16+,17+,18-/m0/s1

> <INCHI_KEY>
PSESCIGPEKVLRV-MHUIHPTQSA-N

> <FORMULA>
C18H18N2O5

> <MOLECULAR_WEIGHT>
342.351

> <EXACT_MASS>
342.121571688

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
34.72627405027197

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4R,5R,6S)-2-methyl-6-(phenazin-1-yloxy)oxane-3,4,5-triol

> <JCHEM_LOGP>
1.5355323296666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.26863524029927

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.213515051772363

> <JCHEM_PKA_STRONGEST_BASIC>
2.5387881125588203

> <JCHEM_POLAR_SURFACE_AREA>
104.93

> <JCHEM_REFRACTIVITY>
85.73820000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5R,6S)-2-methyl-6-(phenazin-1-yloxy)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-MAR-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-MAR-24         0                                  
HETATM    1  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   13   17   19                                                  
CONECT   19   18   10                                                       
CONECT   20   11   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    9                                                       
CONECT   23    7   24                                                       
CONECT   24   23    2   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₈N₂O₅

Average Mass

342.3510 Da

Monoisotopic Mass

342.12157 Da

IUPAC Name

(2S,3R,4R,5R,6S)-2-methyl-6-(phenazin-1-yloxy)oxane-3,4,5-triol

Traditional Name

(2S,3R,4R,5R,6S)-2-methyl-6-(phenazin-1-yloxy)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](OC2=C3N=C4C=CC=CC4=NC3=CC=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C18H18N2O5/c1-9-15(21)16(22)17(23)18(24-9)25-13-8-4-7-12-14(13)20-11-6-3-2-5-10(11)19-12/h2-9,15-18,21-23H,1H3/t9-,15-,16+,17+,18-/m0/s1

InChI Key

PSESCIGPEKVLRV-MHUIHPTQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	[email protected]	The University of Queensland	Sarani Kankanamge	2024-03-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	[email protected]	The University of Queensland	Sarani Kankanamge	2024-03-21	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	[email protected]	The University of Queensland	Sarani Kankanamge	2024-03-21	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	[email protected]	The University of Queensland	Sarani Kankanamge	2024-03-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	[email protected]	The University of Queensland	Sarani Kankanamge	2024-03-21	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	[email protected]	The University of Queensland	Sarani Kankanamge	2024-03-21	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces virginiae		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as phenazines and derivatives. These are polycyclic aromatic compounds containing a phenazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a pyrazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Phenazines and derivatives

Alternative Parents

Substituents

Phenazine
Quinonimine
O-quinonimine
Benzenoid
Pyrazine
Oxane
Monosaccharide
Heteroaromatic compound
Secondary ketimine
Secondary alcohol
Ketimine
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	1.54	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	2.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.93 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.74 m³·mol⁻¹	ChemAxon
Polarizability	34.73 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for tepuazine D (NP0332704)

MOL for NP0332704 (tepuazine D)

3D MOL for NP0332704 (tepuazine D)

3D SDF for NP0332704 (tepuazine D)

3D-SDF for NP0332704 (tepuazine D)

PDB for NP0332704 (tepuazine D)

3D PDB for NP0332704 (tepuazine D)

SMILES for NP0332704 (tepuazine D)

INCHI for NP0332704 (tepuazine D)

Structure for NP0332704 (tepuazine D)

3D Structure for NP0332704 (tepuazine D)