NP-MRD: Showing NP-Card for 11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1²,⁵.0⁶,¹⁷.0¹⁰,¹⁵]octadeca-10(15),11,13-triene-3-carboxylic acid; citric acid (NP0204805)

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Record Information

Version

2.0

Created at

2022-09-05 00:34:08 UTC

Updated at

2022-09-05 00:34:08 UTC

NP-MRD ID

NP0204805

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1²,⁵.0⁶,¹⁷.0¹⁰,¹⁵]octadeca-10(15),11,13-triene-3-carboxylic acid; citric acid

Description

DC-52 citrate, also known as DC-52 citric acid, belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. 11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1²,⁵.0⁶,¹⁷.0¹⁰,¹⁵]octadeca-10(15),11,13-triene-3-carboxylic acid; citric acid is found in Streptomyces melanovinaceus. Based on a literature review very few articles have been published on DC-52 citrate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052202342D          

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M  END

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M  END


  Mrv1652309052202342D          

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 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 29 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204805

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC(O)(CC(O)=O)C(O)=O.COC1=CC=CC2=C1C1COC3C4CC(C(C(C2)N13)N4C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H22N2O4.C6H8O7/c1-19-12-7-10(18(21)22)16(19)11-6-9-4-3-5-14(23-2)15(9)13-8-24-17(12)20(11)13;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-5,10-13,16-17H,6-8H2,1-2H3,(H,21,22);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

> <INCHI_KEY>
MTZMRPGOPJFNLW-UHFFFAOYSA-N

> <FORMULA>
C24H30N2O11

> <MOLECULAR_WEIGHT>
522.507

> <EXACT_MASS>
522.184959794

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
34.509817824611176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1^{2,5}.0^{6,17}.0^{10,15}]octadeca-10(15),11,13-triene-3-carboxylic acid; 2-hydroxypropane-1,2,3-tricarboxylic acid

> <JCHEM_LOGP>
-0.9469034241096539

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.119166972053573

> <JCHEM_PKA_STRONGEST_BASIC>
7.989383942820374

> <JCHEM_POLAR_SURFACE_AREA>
62.24000000000001

> <JCHEM_REFRACTIVITY>
86.54339999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1^{2,5}.0^{6,17}.0^{10,15}]octadeca-10(15),11,13-triene-3-carboxylic acid; citric acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.574   3.327   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.190   2.653   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.081   1.117   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.357   0.255   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.249  -1.281   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.865  -1.956   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.588  -1.094   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.697   0.442   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.419   1.332   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.105   2.886   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.444   3.035   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.155   1.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.544   0.808   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.027   0.587   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.843  -1.066   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.984  -2.100   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.451  -1.630   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.659  -3.606   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.918  -1.472   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.222  -0.993   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.172  -1.759   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -0.011   0.580   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       2.773  -0.955   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       4.288  -0.680   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.751  -2.677   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.084  -1.907   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.418  -2.677   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      11.084  -0.367   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.418   0.403   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.188  -0.931   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      13.752   1.173   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.085   0.403   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      16.419   1.173   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      15.085  -1.137   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      11.648   1.737   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      12.418   3.070   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      10.108   1.737   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   15   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20    7                                                       
CONECT   22   20    9   12                                                  
CONECT   23   19   13   24                                                  
CONECT   24   23                                                            
CONECT   25   26                                                            
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31   35                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   29   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
DC-52 Citric acid	Generator

Chemical Formula

C₂₄H₃₀N₂O₁₁

Average Mass

522.5070 Da

Monoisotopic Mass

522.18496 Da

IUPAC Name

11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1^{2,5}.0^{6,17}.0^{10,15}]octadeca-10(15),11,13-triene-3-carboxylic acid; 2-hydroxypropane-1,2,3-tricarboxylic acid

Traditional Name

11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1^{2,5}.0^{6,17}.0^{10,15}]octadeca-10(15),11,13-triene-3-carboxylic acid; citric acid

CAS Registry Number

Not Available

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.COC1=CC=CC2=C1C1COC3C4CC(C(C(C2)N13)N4C)C(O)=O

InChI Identifier

InChI=1S/C18H22N2O4.C6H8O7/c1-19-12-7-10(18(21)22)16(19)11-6-9-4-3-5-14(23-2)15(9)13-8-24-17(12)20(11)13;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-5,10-13,16-17H,6-8H2,1-2H3,(H,21,22);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

InChI Key

MTZMRPGOPJFNLW-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 melanovinaceus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

Alternative Parents

Substituents

Tetrahydroisoquinoline
Tricarboxylic acid or derivatives
Anisole
Phenol ether
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Alkyl aryl ether
Azepane
Aralkylamine
N-methylpiperazine
N-alkylpiperazine
Alpha-hydroxy acid
1,4-diazinane
Hydroxy acid
Piperazine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Oxazolidine
Tertiary alcohol
Amino acid or derivatives
Tertiary aliphatic amine
Amino acid
Tertiary amine
Hemiaminal
Oxacycle
Azacycle
Ether
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Alcohol
Organonitrogen compound
Organooxygen compound
Amine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Not Available

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	-0.95	ChemAxon
pKa (Strongest Acidic)	3.12	ChemAxon
pKa (Strongest Basic)	7.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.24 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	86.54 m³·mol⁻¹	ChemAxon
Polarizability	34.51 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

5293146

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6917927

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1²,⁵.0⁶,¹⁷.0¹⁰,¹⁵]octadeca-10(15),11,13-triene-3-carboxylic acid; citric acid (NP0204805)

MOL for NP0204805 (11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1²,⁵.0⁶,¹⁷.0¹⁰,¹⁵]octadeca-10(15),11,13-triene-3-carboxylic acid; citric acid)

3D MOL for NP0204805 (11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1²,⁵.0⁶,¹⁷.0¹⁰,¹⁵]octadeca-10(15),11,13-triene-3-carboxylic acid; citric acid)

3D SDF for NP0204805 (11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1²,⁵.0⁶,¹⁷.0¹⁰,¹⁵]octadeca-10(15),11,13-triene-3-carboxylic acid; citric acid)

3D-SDF for NP0204805 (11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1²,⁵.0⁶,¹⁷.0¹⁰,¹⁵]octadeca-10(15),11,13-triene-3-carboxylic acid; citric acid)

PDB for NP0204805 (11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1²,⁵.0⁶,¹⁷.0¹⁰,¹⁵]octadeca-10(15),11,13-triene-3-carboxylic acid; citric acid)

3D PDB for NP0204805 (11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1²,⁵.0⁶,¹⁷.0¹⁰,¹⁵]octadeca-10(15),11,13-triene-3-carboxylic acid; citric acid)

SMILES for NP0204805 (11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1²,⁵.0⁶,¹⁷.0¹⁰,¹⁵]octadeca-10(15),11,13-triene-3-carboxylic acid; citric acid)

INCHI for NP0204805 (11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1²,⁵.0⁶,¹⁷.0¹⁰,¹⁵]octadeca-10(15),11,13-triene-3-carboxylic acid; citric acid)

Structure for NP0204805 (11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1²,⁵.0⁶,¹⁷.0¹⁰,¹⁵]octadeca-10(15),11,13-triene-3-carboxylic acid; citric acid)

3D Structure for NP0204805 (11-methoxy-18-methyl-7-oxa-17,18-diazapentacyclo[7.7.1.1²,⁵.0⁶,¹⁷.0¹⁰,¹⁵]octadeca-10(15),11,13-triene-3-carboxylic acid; citric acid)