NP-MRD: Showing NP-Card for 6-({[2-(dimethylamino)-3-hydroxypropanoyl]oxy}methyl)-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)-9-methoxyphenazine-1-carboximidic acid (NP0212774)

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Record Information

Version

2.0

Created at

2022-09-05 11:32:31 UTC

Updated at

2022-09-05 11:32:31 UTC

NP-MRD ID

NP0212774

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-({[2-(dimethylamino)-3-hydroxypropanoyl]oxy}methyl)-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)-9-methoxyphenazine-1-carboximidic acid

Description

6-({[2-(Dimethylamino)-3-hydroxypropanoyl]oxy}methyl)-N-(2-hydroxy-5-oxocyclopent-1-en-1-yl)-9-methoxyphenazine-1-carboximidic acid belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. 6-({[2-(dimethylamino)-3-hydroxypropanoyl]oxy}methyl)-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)-9-methoxyphenazine-1-carboximidic acid is found in Streptomyces aureus. 6-({[2-(Dimethylamino)-3-hydroxypropanoyl]oxy}methyl)-N-(2-hydroxy-5-oxocyclopent-1-en-1-yl)-9-methoxyphenazine-1-carboximidic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241516242D          

 36 39  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241516242D          

 36 39  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0212774

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2N=C3C(C=CC=C3C(=O)NC3=C(O)CCC3=O)=NC2=C(COC(=O)C(CO)N(C)C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H26N4O7/c1-29(2)16(11-30)25(34)36-12-13-7-10-19(35-3)23-20(13)26-15-6-4-5-14(21(15)27-23)24(33)28-22-17(31)8-9-18(22)32/h4-7,10,16,30-31H,8-9,11-12H2,1-3H3,(H,28,33)

> <INCHI_KEY>
BIVSRYXMBIOALO-UHFFFAOYSA-N

> <FORMULA>
C25H26N4O7

> <MOLECULAR_WEIGHT>
494.504

> <EXACT_MASS>
494.180149193

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
51.3606030658716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)carbamoyl]-4-methoxyphenazin-1-yl}methyl 2-(dimethylamino)-3-hydroxypropanoate

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
0.7483442826666669

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.66032208050159

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.584440231355378

> <JCHEM_PKA_STRONGEST_BASIC>
6.383759332416546

> <JCHEM_POLAR_SURFACE_AREA>
151.18

> <JCHEM_REFRACTIVITY>
129.52099999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)carbamoyl]-4-methoxyphenazin-1-yl}methyl 2-(dimethylamino)-3-hydroxypropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -3.286  -0.055   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.746  -0.055   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.976  -1.389   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.564  -1.389   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.723   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.564  -4.056   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.874  -5.390   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.644  -6.724   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.874  -8.057   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.184  -6.724   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.954  -8.057   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.494  -8.057   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       5.954  -5.390   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       5.184  -4.056   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.494  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.976  -4.056   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -1.746  -5.390   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -3.286  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.056  -6.724   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.596  -6.724   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.366  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.596  -4.056   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.366  -2.723   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.596  -1.389   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0      -7.906  -2.723   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      -8.676  -1.389   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -10.208  -1.228   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -11.238  -2.372   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -10.528   0.278   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -9.194   1.048   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.050   0.018   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -6.544   0.338   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -4.056  -4.056   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      -3.286  -2.723   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0      -1.746  -2.723   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    6   18   36                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   34                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   34                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27   33                                                  
CONECT   33   32                                                            
CONECT   34   23   19   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35    3   17                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
6-({[2-(dimethylamino)-3-hydroxypropanoyl]oxy}methyl)-N-(2-hydroxy-5-oxocyclopent-1-en-1-yl)-9-methoxyphenazine-1-carboximidate	Generator

Chemical Formula

C₂₅H₂₆N₄O₇

Average Mass

494.5040 Da

Monoisotopic Mass

494.18015 Da

IUPAC Name

{6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)carbamoyl]-4-methoxyphenazin-1-yl}methyl 2-(dimethylamino)-3-hydroxypropanoate

Traditional Name

{6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)carbamoyl]-4-methoxyphenazin-1-yl}methyl 2-(dimethylamino)-3-hydroxypropanoate

CAS Registry Number

Not Available

SMILES

COC1=C2N=C3C(C=CC=C3C(=O)NC3=C(O)CCC3=O)=NC2=C(COC(=O)C(CO)N(C)C)C=C1

InChI Identifier

InChI=1S/C25H26N4O7/c1-29(2)16(11-30)25(34)36-12-13-7-10-19(35-3)23-20(13)26-15-6-4-5-14(21(15)27-23)24(33)28-22-17(31)8-9-18(22)32/h4-7,10,16,30-31H,8-9,11-12H2,1-3H3,(H,28,33)

InChI Key

BIVSRYXMBIOALO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces aureus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Cyclohexanol
Tertiary alcohol
Cyclic alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	1.53	ALOGPS
logP	0.75	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.58	ChemAxon
pKa (Strongest Basic)	6.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	151.18 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	129.52 m³·mol⁻¹	ChemAxon
Polarizability	51.36 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

LOTUS database [Link]

Showing NP-Card for 6-({[2-(dimethylamino)-3-hydroxypropanoyl]oxy}methyl)-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)-9-methoxyphenazine-1-carboximidic acid (NP0212774)

MOL for NP0212774 (6-({[2-(dimethylamino)-3-hydroxypropanoyl]oxy}methyl)-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)-9-methoxyphenazine-1-carboximidic acid)

3D MOL for NP0212774 (6-({[2-(dimethylamino)-3-hydroxypropanoyl]oxy}methyl)-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)-9-methoxyphenazine-1-carboximidic acid)

3D SDF for NP0212774 (6-({[2-(dimethylamino)-3-hydroxypropanoyl]oxy}methyl)-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)-9-methoxyphenazine-1-carboximidic acid)

3D-SDF for NP0212774 (6-({[2-(dimethylamino)-3-hydroxypropanoyl]oxy}methyl)-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)-9-methoxyphenazine-1-carboximidic acid)

PDB for NP0212774 (6-({[2-(dimethylamino)-3-hydroxypropanoyl]oxy}methyl)-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)-9-methoxyphenazine-1-carboximidic acid)

3D PDB for NP0212774 (6-({[2-(dimethylamino)-3-hydroxypropanoyl]oxy}methyl)-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)-9-methoxyphenazine-1-carboximidic acid)

SMILES for NP0212774 (6-({[2-(dimethylamino)-3-hydroxypropanoyl]oxy}methyl)-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)-9-methoxyphenazine-1-carboximidic acid)

INCHI for NP0212774 (6-({[2-(dimethylamino)-3-hydroxypropanoyl]oxy}methyl)-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)-9-methoxyphenazine-1-carboximidic acid)

Structure for NP0212774 (6-({[2-(dimethylamino)-3-hydroxypropanoyl]oxy}methyl)-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)-9-methoxyphenazine-1-carboximidic acid)

3D Structure for NP0212774 (6-({[2-(dimethylamino)-3-hydroxypropanoyl]oxy}methyl)-n-(2-hydroxy-5-oxocyclopent-1-en-1-yl)-9-methoxyphenazine-1-carboximidic acid)