NP-MRD: Showing NP-Card for (11s,14r,16s,24s)-23-acetyl-10,13-dihydroxy-11-isopropyl-16-(2-methylbut-3-en-2-yl)-1,9,12,23-tetraazapentacyclo[12.10.0.0³,⁸.0¹⁶,²⁴.0¹⁷,²²]tetracosa-3,5,7,9,12,17,19,21-octaen-2-one (NP0143083)

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Record Information

Version

2.0

Created at

2022-09-01 21:45:39 UTC

Updated at

2022-09-01 21:45:39 UTC

NP-MRD ID

NP0143083

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(11s,14r,16s,24s)-23-acetyl-10,13-dihydroxy-11-isopropyl-16-(2-methylbut-3-en-2-yl)-1,9,12,23-tetraazapentacyclo[12.10.0.0³,⁸.0¹⁶,²⁴.0¹⁷,²²]tetracosa-3,5,7,9,12,17,19,21-octaen-2-one

Description

Novofumigatamide 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 Novofumigatamide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309012223452D          

 38 42  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309012223452D          

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  8  9  1  0  0  0  0
  9 10  1  4  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  4  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  8 27  1  6  0  0  0
 28 27  1  1  0  0  0
  6 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 29 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
  6 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0143083

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1N=C(O)[C@H]2C[C@]3([C@H](N(C(C)=O)C4=CC=CC=C34)N2C(=O)C2=CC=CC=C2N=C1O)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C30H34N4O4/c1-7-29(5,6)30-16-23-25(36)32-24(17(2)3)26(37)31-21-14-10-8-12-19(21)27(38)34(23)28(30)33(18(4)35)22-15-11-9-13-20(22)30/h7-15,17,23-24,28H,1,16H2,2-6H3,(H,31,37)(H,32,36)/t23-,24+,28-,30+/m1/s1

> <INCHI_KEY>
WHAGCGDAGYOTBE-VQNIMACBSA-N

> <FORMULA>
C30H34N4O4

> <MOLECULAR_WEIGHT>
514.626

> <EXACT_MASS>
514.258005591

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.7592168494174

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11S,14R,16S,24S)-23-acetyl-10,13-dihydroxy-16-(2-methylbut-3-en-2-yl)-11-(propan-2-yl)-1,9,12,23-tetraazapentacyclo[12.10.0.0^{3,8}.0^{16,24}.0^{17,22}]tetracosa-3,5,7,9,12,17,19,21-octaen-2-one

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
2.5780103010441917

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.060664210454851

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2231689319804304

> <JCHEM_PKA_STRONGEST_BASIC>
7.536348288968245

> <JCHEM_POLAR_SURFACE_AREA>
105.79999999999998

> <JCHEM_REFRACTIVITY>
146.07179999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(11S,14R,16S,24S)-23-acetyl-10,13-dihydroxy-11-isopropyl-16-(2-methylbut-3-en-2-yl)-1,9,12,23-tetraazapentacyclo[12.10.0.0^{3,8}.0^{16,24}.0^{17,22}]tetracosa-3,5,7,9,12,17,19,21-octaen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-SEP-22         0                                  
HETATM    1  C   UNK     0       4.043   9.948   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.328  10.796   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.706  10.107   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.017   8.730   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.394  11.485   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.083   9.418   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.312  10.941   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.832  11.194   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.661  12.491   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.951  13.858   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      12.199  12.422   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      12.909  11.055   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.738  12.353   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.276  12.284   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.028  13.720   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.447  10.986   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      15.881  11.549   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      15.156   9.619   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      14.327   8.321   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.037   6.955   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.207   5.657   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.669   5.726   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.960   7.093   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.789   8.391   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.079   9.757   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.987  11.295   0.000  0.00  0.00           O+0
HETATM   27  N   UNK     0      10.541   9.827   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       9.460   8.730   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       9.231   7.207   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      10.328   6.126   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.940   4.636   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.812   6.536   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.711   6.955   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.882   5.657   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.344   5.726   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.635   7.093   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.464   8.391   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.002   8.321   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   28   38                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19   25                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    8   28                                                  
CONECT   28   27    6   29                                                  
CONECT   29   28   30   33                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   29   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   33    6                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₄N₄O₄

Average Mass

514.6260 Da

Monoisotopic Mass

514.25801 Da

IUPAC Name

(11S,14R,16S,24S)-23-acetyl-10,13-dihydroxy-16-(2-methylbut-3-en-2-yl)-11-(propan-2-yl)-1,9,12,23-tetraazapentacyclo[12.10.0.0^{3,8}.0^{16,24}.0^{17,22}]tetracosa-3,5,7,9,12,17,19,21-octaen-2-one

Traditional Name

(11S,14R,16S,24S)-23-acetyl-10,13-dihydroxy-11-isopropyl-16-(2-methylbut-3-en-2-yl)-1,9,12,23-tetraazapentacyclo[12.10.0.0^{3,8}.0^{16,24}.0^{17,22}]tetracosa-3,5,7,9,12,17,19,21-octaen-2-one

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1N=C(O)[C@H]2C[C@]3([C@H](N(C(C)=O)C4=CC=CC=C34)N2C(=O)C2=CC=CC=C2N=C1O)C(C)(C)C=C

InChI Identifier

InChI=1S/C30H34N4O4/c1-7-29(5,6)30-16-23-25(36)32-24(17(2)3)26(37)31-21-14-10-8-12-19(21)27(38)34(23)28(30)33(18(4)35)22-15-11-9-13-20(22)30/h7-15,17,23-24,28H,1,16H2,2-6H3,(H,31,37)(H,32,36)/t23-,24+,28-,30+/m1/s1

InChI Key

WHAGCGDAGYOTBE-VQNIMACBSA-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
Pyrroloindole
Alpha-amino acid or derivatives
Indole
Indole or derivatives
Benzenoid
Pyrrole
Pyrrolidine
Acetamide
Vinylogous amide
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
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	3.54	ALOGPS
logP	2.58	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	7.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.8 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	146.07 m³·mol⁻¹	ChemAxon
Polarizability	54.76 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	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

28287909

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

49831387

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (11s,14r,16s,24s)-23-acetyl-10,13-dihydroxy-11-isopropyl-16-(2-methylbut-3-en-2-yl)-1,9,12,23-tetraazapentacyclo[12.10.0.0³,⁸.0¹⁶,²⁴.0¹⁷,²²]tetracosa-3,5,7,9,12,17,19,21-octaen-2-one (NP0143083)

MOL for NP0143083 ((11s,14r,16s,24s)-23-acetyl-10,13-dihydroxy-11-isopropyl-16-(2-methylbut-3-en-2-yl)-1,9,12,23-tetraazapentacyclo[12.10.0.0³,⁸.0¹⁶,²⁴.0¹⁷,²²]tetracosa-3,5,7,9,12,17,19,21-octaen-2-one)

3D MOL for NP0143083 ((11s,14r,16s,24s)-23-acetyl-10,13-dihydroxy-11-isopropyl-16-(2-methylbut-3-en-2-yl)-1,9,12,23-tetraazapentacyclo[12.10.0.0³,⁸.0¹⁶,²⁴.0¹⁷,²²]tetracosa-3,5,7,9,12,17,19,21-octaen-2-one)

3D SDF for NP0143083 ((11s,14r,16s,24s)-23-acetyl-10,13-dihydroxy-11-isopropyl-16-(2-methylbut-3-en-2-yl)-1,9,12,23-tetraazapentacyclo[12.10.0.0³,⁸.0¹⁶,²⁴.0¹⁷,²²]tetracosa-3,5,7,9,12,17,19,21-octaen-2-one)

3D-SDF for NP0143083 ((11s,14r,16s,24s)-23-acetyl-10,13-dihydroxy-11-isopropyl-16-(2-methylbut-3-en-2-yl)-1,9,12,23-tetraazapentacyclo[12.10.0.0³,⁸.0¹⁶,²⁴.0¹⁷,²²]tetracosa-3,5,7,9,12,17,19,21-octaen-2-one)

PDB for NP0143083 ((11s,14r,16s,24s)-23-acetyl-10,13-dihydroxy-11-isopropyl-16-(2-methylbut-3-en-2-yl)-1,9,12,23-tetraazapentacyclo[12.10.0.0³,⁸.0¹⁶,²⁴.0¹⁷,²²]tetracosa-3,5,7,9,12,17,19,21-octaen-2-one)

3D PDB for NP0143083 ((11s,14r,16s,24s)-23-acetyl-10,13-dihydroxy-11-isopropyl-16-(2-methylbut-3-en-2-yl)-1,9,12,23-tetraazapentacyclo[12.10.0.0³,⁸.0¹⁶,²⁴.0¹⁷,²²]tetracosa-3,5,7,9,12,17,19,21-octaen-2-one)

SMILES for NP0143083 ((11s,14r,16s,24s)-23-acetyl-10,13-dihydroxy-11-isopropyl-16-(2-methylbut-3-en-2-yl)-1,9,12,23-tetraazapentacyclo[12.10.0.0³,⁸.0¹⁶,²⁴.0¹⁷,²²]tetracosa-3,5,7,9,12,17,19,21-octaen-2-one)

INCHI for NP0143083 ((11s,14r,16s,24s)-23-acetyl-10,13-dihydroxy-11-isopropyl-16-(2-methylbut-3-en-2-yl)-1,9,12,23-tetraazapentacyclo[12.10.0.0³,⁸.0¹⁶,²⁴.0¹⁷,²²]tetracosa-3,5,7,9,12,17,19,21-octaen-2-one)

Structure for NP0143083 ((11s,14r,16s,24s)-23-acetyl-10,13-dihydroxy-11-isopropyl-16-(2-methylbut-3-en-2-yl)-1,9,12,23-tetraazapentacyclo[12.10.0.0³,⁸.0¹⁶,²⁴.0¹⁷,²²]tetracosa-3,5,7,9,12,17,19,21-octaen-2-one)

3D Structure for NP0143083 ((11s,14r,16s,24s)-23-acetyl-10,13-dihydroxy-11-isopropyl-16-(2-methylbut-3-en-2-yl)-1,9,12,23-tetraazapentacyclo[12.10.0.0³,⁸.0¹⁶,²⁴.0¹⁷,²²]tetracosa-3,5,7,9,12,17,19,21-octaen-2-one)