NP-MRD: Showing NP-Card for 14-(1-hydroxyethyl)-17-isopropyl-11-methyl-4-(sec-butyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol (NP0302663)

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Record Information

Version

2.0

Created at

2022-09-10 16:23:49 UTC

Updated at

2022-09-10 16:23:49 UTC

NP-MRD ID

NP0302663

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-(1-hydroxyethyl)-17-isopropyl-11-methyl-4-(sec-butyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol

Description

4-(Butan-2-yl)-14-(1-hydroxyethyl)-11-methyl-17-(propan-2-yl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]Docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone. Based on a literature review very few articles have been published on 4-(butan-2-yl)-14-(1-hydroxyethyl)-11-methyl-17-(propan-2-yl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]Docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102218232D          

 37 39  0  0  0  0            999 V2000
    2.7538   -0.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7470    0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8802    1.7967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8870    0.9718    0.0000 O   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


  Mrv1652309102218232D          

 37 39  0  0  0  0            999 V2000
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 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  9 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 18 14  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 25 21  1  4  0  0  0
 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
 30 28  1  4  0  0  0
 30 31  2  0  0  0  0
 31 32  1  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>
NP0302663

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C1N=C(O)C2=COC(=N2)C(N=C(O)C(N=C(O)C(C)N=C(O)C2=CSC1=N2)C(C)O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C24H34N6O6S/c1-7-11(4)17-24-27-15(9-37-24)21(34)25-12(5)19(32)30-18(13(6)31)22(35)28-16(10(2)3)23-26-14(8-36-23)20(33)29-17/h8-13,16-18,31H,7H2,1-6H3,(H,25,34)(H,28,35)(H,29,33)(H,30,32)

> <INCHI_KEY>
QZBXXIUSHVFCNF-UHFFFAOYSA-N

> <FORMULA>
C24H34N6O6S

> <MOLECULAR_WEIGHT>
534.63

> <EXACT_MASS>
534.226054013

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
55.07959413896519

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(butan-2-yl)-14-(1-hydroxyethyl)-11-methyl-17-(propan-2-yl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1^{5,8}]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol

> <JCHEM_LOGP>
0.9271972591458478

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.0824078057672466

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.0648460097188526

> <JCHEM_PKA_STRONGEST_BASIC>
5.064178263338963

> <JCHEM_POLAR_SURFACE_AREA>
189.51

> <JCHEM_REFRACTIVITY>
135.2273

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
14-(1-hydroxyethyl)-17-isopropyl-11-methyl-4-(sec-butyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1^{5,8}]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       5.140  -0.529   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.128   1.011   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       7.795   1.033   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  C   UNK     0      11.946   3.827   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.705   5.167   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.752   6.456   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      10.424   5.675   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      11.739   7.996   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.066   8.777   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.054  10.316   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.406   8.018   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      10.399   8.755   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      10.386  10.295   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.714  11.076   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.047  11.054   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.034  12.594   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.694  13.353   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.361  13.375   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       7.719  10.273   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       6.379  11.032   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.367  12.572   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.052  10.251   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.712  11.010   0.000  0.00  0.00           C+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                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    9                                                       
CONECT   14   12   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   21   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   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   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₄N₆O₆S

Average Mass

534.6300 Da

Monoisotopic Mass

534.22605 Da

IUPAC Name

4-(butan-2-yl)-14-(1-hydroxyethyl)-11-methyl-17-(propan-2-yl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1^{5,8}]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol

Traditional Name

14-(1-hydroxyethyl)-17-isopropyl-11-methyl-4-(sec-butyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1^{5,8}]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol

CAS Registry Number

Not Available

SMILES

CCC(C)C1N=C(O)C2=COC(=N2)C(N=C(O)C(N=C(O)C(C)N=C(O)C2=CSC1=N2)C(C)O)C(C)C

InChI Identifier

InChI=1S/C24H34N6O6S/c1-7-11(4)17-24-27-15(9-37-24)21(34)25-12(5)19(32)30-18(13(6)31)22(35)28-16(10(2)3)23-26-14(8-36-23)20(33)29-17/h8-13,16-18,31H,7H2,1-6H3,(H,25,34)(H,28,35)(H,29,33)(H,30,32)

InChI Key

QZBXXIUSHVFCNF-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 cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cyclic peptides

Alternative Parents

Substituents

Alpha-dipeptide
Cyclic alpha peptide
Macrolactam
Alpha-amino acid or derivatives
2-heteroaryl carboxamide
Thiazolecarboxylic acid or derivatives
Azole
Oxazole
Thiazole
Heteroaromatic compound
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Lactam
Organoheterocyclic compound
Oxacycle
Azacycle
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
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	0.93	ChemAxon
pKa (Strongest Acidic)	1.06	ChemAxon
pKa (Strongest Basic)	5.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.51 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	135.23 m³·mol⁻¹	ChemAxon
Polarizability	55.08 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

152772185

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 14-(1-hydroxyethyl)-17-isopropyl-11-methyl-4-(sec-butyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol (NP0302663)

MOL for NP0302663 (14-(1-hydroxyethyl)-17-isopropyl-11-methyl-4-(sec-butyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

3D MOL for NP0302663 (14-(1-hydroxyethyl)-17-isopropyl-11-methyl-4-(sec-butyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

3D SDF for NP0302663 (14-(1-hydroxyethyl)-17-isopropyl-11-methyl-4-(sec-butyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

3D-SDF for NP0302663 (14-(1-hydroxyethyl)-17-isopropyl-11-methyl-4-(sec-butyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

PDB for NP0302663 (14-(1-hydroxyethyl)-17-isopropyl-11-methyl-4-(sec-butyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

3D PDB for NP0302663 (14-(1-hydroxyethyl)-17-isopropyl-11-methyl-4-(sec-butyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

SMILES for NP0302663 (14-(1-hydroxyethyl)-17-isopropyl-11-methyl-4-(sec-butyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

INCHI for NP0302663 (14-(1-hydroxyethyl)-17-isopropyl-11-methyl-4-(sec-butyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

Structure for NP0302663 (14-(1-hydroxyethyl)-17-isopropyl-11-methyl-4-(sec-butyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

3D Structure for NP0302663 (14-(1-hydroxyethyl)-17-isopropyl-11-methyl-4-(sec-butyl)-19-oxa-6-thia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)