NP-MRD: Showing NP-Card for 9-amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid (NP0267592)

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Record Information

Version

2.0

Created at

2022-09-08 12:25:06 UTC

Updated at

2022-09-08 12:25:06 UTC

NP-MRD ID

NP0267592

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid

Description

9-Amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]Docosa-1(19),3,5,7(22),10,13,17,20-octaene-15-carboxylic acid belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. 9-Amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]Docosa-1(19),3,5,7(22),10,13,17,20-octaene-15-carboxylic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251511192D          

 38 40  0  0  0  0            999 V2000
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   -0.3199   -3.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004251511192D          

 38 40  0  0  0  0            999 V2000
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 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  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
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 16 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 14 36  1  0  0  0  0
 36 37  2  0  0  0  0
 11 37  1  0  0  0  0
  9 38  2  0  0  0  0
  4 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0267592

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1CC2=CC=C(O)C(OC3=CC=C(CC(NC(=O)C(NC1=O)C(O)C(O)CNC(N)=N)C(O)=O)C=C3)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C24H30N6O8/c25-14-7-12-3-6-16(31)18(9-12)38-13-4-1-11(2-5-13)8-15(23(36)37)29-22(35)19(30-21(14)34)20(33)17(32)10-28-24(26)27/h1-6,9,14-15,17,19-20,31-33H,7-8,10,25H2,(H,29,35)(H,30,34)(H,36,37)(H4,26,27,28)

> <INCHI_KEY>
WGXANKDMVJQLAR-UHFFFAOYSA-N

> <FORMULA>
C24H30N6O8

> <MOLECULAR_WEIGHT>
530.538

> <EXACT_MASS>
530.21251195

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
51.758373313618236

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4-hydroxy-10,13-dioxo-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,17,20-hexaene-15-carboxylic acid

> <ALOGPS_LOGP>
-2.26

> <JCHEM_LOGP>
-3.819848103144991

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.49415855281047

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.006591772511582

> <JCHEM_PKA_STRONGEST_BASIC>
11.31359647728482

> <JCHEM_POLAR_SURFACE_AREA>
253.33999999999997

> <JCHEM_REFRACTIVITY>
142.33459999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4-hydroxy-10,13-dioxo-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,17,20-hexaene-15-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  N   UNK     0      -0.650  -7.818   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -0.597  -6.279   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.173  -5.987   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.260  -4.794   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.828  -4.193   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.502  -2.708   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.727  -1.783   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.591  -0.744   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.223  -2.155   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.210  -0.493   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.158   0.799   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.621   2.284   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.103   2.699   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.040   1.591   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.596   1.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.963   0.328   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       3.799  -1.034   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.952  -2.637   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.482  -2.813   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.431  -4.181   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       2.372  -5.384   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       0.979  -6.098   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.426  -7.572   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.765  -4.951   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.765  -6.491   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.099  -4.181   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.099  -2.641   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.433  -4.951   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       8.766  -4.181   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      10.100  -4.951   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      11.434  -4.181   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0      10.100  -6.491   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       4.043   1.425   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.534   1.039   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       3.632   2.910   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -0.449   0.115   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.965  -0.175   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.459  -3.743   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   38                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   38                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   37                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   36                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   33                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21    2   23                                                  
CONECT   23   22                                                            
CONECT   24   20   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   16   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   14   37                                                       
CONECT   37   36   11                                                       
CONECT   38    9    4                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Value	Source
9-Amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1,]docosa-1(19),3,5,7(22),10,13,17,20-octaene-15-carboxylate	Generator
9-Amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3,5,7(22),10,13,17,20-octaene-15-carboxylate	Generator

Chemical Formula

C₂₄H₃₀N₆O₈

Average Mass

530.5380 Da

Monoisotopic Mass

530.21251 Da

IUPAC Name

9-amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4-hydroxy-10,13-dioxo-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,17,20-hexaene-15-carboxylic acid

Traditional Name

9-amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4-hydroxy-10,13-dioxo-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,17,20-hexaene-15-carboxylic acid

CAS Registry Number

Not Available

SMILES

NC1CC2=CC=C(O)C(OC3=CC=C(CC(NC(=O)C(NC1=O)C(O)C(O)CNC(N)=N)C(O)=O)C=C3)=C2

InChI Identifier

InChI=1S/C24H30N6O8/c25-14-7-12-3-6-16(31)18(9-12)38-13-4-1-11(2-5-13)8-15(23(36)37)29-22(35)19(30-21(14)34)20(33)17(32)10-28-24(26)27/h1-6,9,14-15,17,19-20,31-33H,7-8,10,25H2,(H,29,35)(H,30,34)(H,36,37)(H4,26,27,28)

InChI Key

WGXANKDMVJQLAR-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Cyclic alpha peptide
Oxyneolignan skeleton
Macrolactam
Alpha-amino acid amide
Diaryl ether
Alpha-amino acid or derivatives
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Carboxamide group
Amino acid or derivatives
1,2-diol
Guanidine
Lactam
Secondary carboxylic acid amide
Secondary alcohol
Amino acid
Carboxylic acid
Oxacycle
Azacycle
Ether
Organoheterocyclic compound
Carboximidamide
Monocarboxylic acid or derivatives
Amine
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Imine
Organic oxide
Primary amine
Organooxygen compound
Primary aliphatic amine
Organonitrogen compound
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	-2.3	ALOGPS
logP	-3.8	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.01	ChemAxon
pKa (Strongest Basic)	11.31	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	253.34 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	142.33 m³·mol⁻¹	ChemAxon
Polarizability	51.76 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

72808487

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid (NP0267592)

MOL for NP0267592 (9-amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

3D MOL for NP0267592 (9-amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

3D SDF for NP0267592 (9-amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

3D-SDF for NP0267592 (9-amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

PDB for NP0267592 (9-amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

3D PDB for NP0267592 (9-amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

SMILES for NP0267592 (9-amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

INCHI for NP0267592 (9-amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

Structure for NP0267592 (9-amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)

3D Structure for NP0267592 (9-amino-12-(3-carbamimidamido-1,2-dihydroxypropyl)-4,10,13-trihydroxy-2-oxa-11,14-diazatricyclo[15.2.2.1³,⁷]docosa-1(19),3(22),4,6,10,13,17,20-octaene-15-carboxylic acid)