NP-MRD: Showing NP-Card for [2,9,16-trihydroxy-4,7-dimethyl-11-(sec-butyl)-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetic acid (NP0185632)

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Record Information

Version

1.0

Created at

2022-09-04 01:07:02 UTC

Updated at

2022-09-04 01:07:02 UTC

NP-MRD ID

NP0185632

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[2,9,16-trihydroxy-4,7-dimethyl-11-(sec-butyl)-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetic acid

Description

2-[11-(Butan-2-yl)-2,9,16-trihydroxy-4,7-dimethyl-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]Tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetic acid belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. 2-[11-(Butan-2-yl)-2,9,16-trihydroxy-4,7-dimethyl-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]Tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161523152D          

 37 40  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1533004161523152D          

 37 40  0  0  0  0            999 V2000
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 27 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  2  0  0  0  0
 33 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185632

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C1NC(=O)C2=C(C)OC(=N2)C(C)NC(=O)C2=CSC(=N2)C(CC(O)=O)NC(=O)C2=CSC1=N2

> <INCHI_IDENTIFIER>
InChI=1S/C23H26N6O6S2/c1-5-9(2)16-23-27-14(8-37-23)19(33)25-12(6-15(30)31)22-26-13(7-36-22)18(32)24-10(3)21-29-17(11(4)35-21)20(34)28-16/h7-10,12,16H,5-6H2,1-4H3,(H,24,32)(H,25,33)(H,28,34)(H,30,31)

> <INCHI_KEY>
SWMDBTHOKJGFQB-UHFFFAOYSA-N

> <FORMULA>
C23H26N6O6S2

> <MOLECULAR_WEIGHT>
546.62

> <EXACT_MASS>
546.135524929

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
53.98684004442444

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[11-(butan-2-yl)-4,7-dimethyl-2,9,16-trioxo-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),5(24),7,12(23),14,19(22)-hexaen-18-yl]acetic acid

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
1.6290017366666665

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.381935767325846

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2867868286878106

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8282608509450721

> <JCHEM_POLAR_SURFACE_AREA>
176.40999999999997

> <JCHEM_REFRACTIVITY>
132.01769999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[4,7-dimethyl-2,9,16-trioxo-11-(sec-butyl)-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),5(24),7,12(23),14,19(22)-hexaen-18-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       7.808  -0.507   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.795   1.033   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.455   1.792   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.128   1.011   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.442   3.332   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       7.770   4.113   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       9.110   3.354   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.122   1.814   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.437   4.135   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      10.424   5.675   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      11.752   6.456   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.705   5.167   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.946   3.827   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.584   2.425   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.739   7.996   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.066   8.777   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      10.399   8.755   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      10.386  10.295   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.714  11.076   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.047  11.054   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.559  12.514   0.000  0.00  0.00           C+0
HETATM   22  S   UNK     0       7.019  12.502   0.000  0.00  0.00           S+0
HETATM   23  C   UNK     0       6.379  11.032   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       7.719  10.273   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       5.052  10.251   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.712  11.010   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.699  12.550   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.359  13.309   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.027  13.331   0.000  0.00  0.00           O+0
HETATM   30  N   UNK     0       5.065   8.711   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       3.737   7.930   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.397   8.689   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.750   6.390   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.729   5.237   0.000  0.00  0.00           C+0
HETATM   35  S   UNK     0       3.510   3.910   0.000  0.00  0.00           S+0
HETATM   36  C   UNK     0       5.102   4.091   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0       5.090   5.631   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   36                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12    9   14                                                  
CONECT   14   13                                                            
CONECT   15   11   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   20                                                       
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   37                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35    5   37                                                  
CONECT   37   36   33                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
2-[11-(Butan-2-yl)-2,9,16-trihydroxy-4,7-dimethyl-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1,.1,]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetate	Generator
2-[11-(Butan-2-yl)-2,9,16-trihydroxy-4,7-dimethyl-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetate	Generator

Chemical Formula

C₂₃H₂₆N₆O₆S₂

Average Mass

546.6200 Da

Monoisotopic Mass

546.13552 Da

IUPAC Name

2-[11-(butan-2-yl)-4,7-dimethyl-2,9,16-trioxo-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),5(24),7,12(23),14,19(22)-hexaen-18-yl]acetic acid

Traditional Name

[4,7-dimethyl-2,9,16-trioxo-11-(sec-butyl)-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),5(24),7,12(23),14,19(22)-hexaen-18-yl]acetic acid

CAS Registry Number

Not Available

SMILES

CCC(C)C1NC(=O)C2=C(C)OC(=N2)C(C)NC(=O)C2=CSC(=N2)C(CC(O)=O)NC(=O)C2=CSC1=N2

InChI Identifier

InChI=1S/C23H26N6O6S2/c1-5-9(2)16-23-27-14(8-37-23)19(33)25-12(6-15(30)31)22-26-13(7-36-22)18(32)24-10(3)21-29-17(11(4)35-21)20(34)28-16/h7-10,12,16H,5-6H2,1-4H3,(H,24,32)(H,25,33)(H,28,34)(H,30,31)

InChI Key

SWMDBTHOKJGFQB-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 macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolactams

Sub Class

Not Available

Direct Parent

Macrolactams

Alternative Parents

Substituents

Macrolactam
2-heteroaryl carboxamide
Thiazolecarboxylic acid or derivatives
Azole
Oxazole
Thiazole
Heteroaromatic compound
Carboxamide group
Lactam
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Oxacycle
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen 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	2.06	ALOGPS
logP	1.63	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.29	ChemAxon
pKa (Strongest Basic)	-0.83	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	176.41 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	132.02 m³·mol⁻¹	ChemAxon
Polarizability	53.99 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

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 [2,9,16-trihydroxy-4,7-dimethyl-11-(sec-butyl)-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetic acid (NP0185632)

MOL for NP0185632 ([2,9,16-trihydroxy-4,7-dimethyl-11-(sec-butyl)-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetic acid)

3D MOL for NP0185632 ([2,9,16-trihydroxy-4,7-dimethyl-11-(sec-butyl)-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetic acid)

3D SDF for NP0185632 ([2,9,16-trihydroxy-4,7-dimethyl-11-(sec-butyl)-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetic acid)

3D-SDF for NP0185632 ([2,9,16-trihydroxy-4,7-dimethyl-11-(sec-butyl)-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetic acid)

PDB for NP0185632 ([2,9,16-trihydroxy-4,7-dimethyl-11-(sec-butyl)-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetic acid)

3D PDB for NP0185632 ([2,9,16-trihydroxy-4,7-dimethyl-11-(sec-butyl)-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetic acid)

SMILES for NP0185632 ([2,9,16-trihydroxy-4,7-dimethyl-11-(sec-butyl)-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetic acid)

INCHI for NP0185632 ([2,9,16-trihydroxy-4,7-dimethyl-11-(sec-butyl)-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetic acid)

Structure for NP0185632 ([2,9,16-trihydroxy-4,7-dimethyl-11-(sec-butyl)-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetic acid)

3D Structure for NP0185632 ([2,9,16-trihydroxy-4,7-dimethyl-11-(sec-butyl)-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetic acid)