NP-MRD: Showing NP-Card for 16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione (NP0152490)

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Record Information

Version

2.0

Created at

2022-09-02 08:58:50 UTC

Updated at

2022-09-02 08:58:50 UTC

NP-MRD ID

NP0152490

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione

Description

16-Acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]Tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. 16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione is found in Aspergillus fumigatus. Based on a literature review very few articles have been published on 16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]Tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022210582D          

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M  END

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M  END


  Mrv1652309022210582D          

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 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  2  0  0  0  0
 24 34  1  0  0  0  0
 18 34  1  0  0  0  0
 34 35  1  0  0  0  0
  6 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0152490

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1N2C(=NC3=CC=CC=C3C2=O)C2C(O)C3(C(N2C1=O)N(C(C)=O)C1=CC=CC=C31)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C28H28N4O4/c1-6-27(4,5)28-18-12-8-10-14-20(18)31(16(3)33)26(28)32-21(22(28)34)23-29-19-13-9-7-11-17(19)25(36)30(23)15(2)24(32)35/h6-15,21-22,26,34H,1H2,2-5H3

> <INCHI_KEY>
NZEBQKVTPTVMHB-UHFFFAOYSA-N

> <FORMULA>
C28H28N4O4

> <MOLECULAR_WEIGHT>
484.556

> <EXACT_MASS>
484.211055398

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
51.113803682011536

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0^{2,11}.0^{4,9}.0^{15,23}.0^{17,22}]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
2.389483037333333

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.0682811417285

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.698866880858478

> <JCHEM_PKA_STRONGEST_BASIC>
1.9401184940346927

> <JCHEM_POLAR_SURFACE_AREA>
93.52000000000001

> <JCHEM_REFRACTIVITY>
134.3974

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0^{2,11}.0^{4,9}.0^{15,23}.0^{17,22}]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       3.299  -6.798   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.676  -7.488   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.767  -9.025   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.229  -9.116   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.304  -8.934   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.858 -10.562   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.368 -10.174   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.659  -8.806   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.121  -8.736   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.291 -10.034   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.999 -11.401   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.538 -11.471   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.515 -12.661   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       3.126 -14.151   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.223 -15.233   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.642 -14.560   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.949 -12.099   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       6.439 -12.488   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       7.148 -13.855   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.318 -15.152   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.686 -13.925   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.394 -15.293   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       9.516 -12.628   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       8.807 -11.261   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       9.637  -9.963   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      11.176 -10.034   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.006  -8.736   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.544  -8.806   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.252 -10.174   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.423 -11.471   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.884 -11.401   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.054 -12.698   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      11.763 -14.066   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.269 -11.191   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.292 -10.000   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.122  -8.703   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   17   35                                             
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13    6   18                                                  
CONECT   18   17   19   34                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   32                                                  
CONECT   24   23   25   34                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26   32                                                  
CONECT   32   31   23   33                                                  
CONECT   33   32                                                            
CONECT   34   24   18   35                                                  
CONECT   35   34    6   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₈N₄O₄

Average Mass

484.5560 Da

Monoisotopic Mass

484.21106 Da

IUPAC Name

16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0^{2,11}.0^{4,9}.0^{15,23}.0^{17,22}]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione

Traditional Name

16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0^{2,11}.0^{4,9}.0^{15,23}.0^{17,22}]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione

CAS Registry Number

Not Available

SMILES

CC1N2C(=NC3=CC=CC=C3C2=O)C2C(O)C3(C(N2C1=O)N(C(C)=O)C1=CC=CC=C31)C(C)(C)C=C

InChI Identifier

InChI=1S/C28H28N4O4/c1-6-27(4,5)28-18-12-8-10-14-20(18)31(16(3)33)26(28)32-21(22(28)34)23-29-19-13-9-7-11-17(19)25(36)30(23)15(2)24(32)35/h6-15,21-22,26,34H,1H2,2-5H3

InChI Key

NZEBQKVTPTVMHB-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
Aspergillus fumigatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Quinazoline
Indole
Pyrimidone
Pyrimidine
Benzenoid
Pyrrole
Pyrrolidine
Heteroaromatic compound
Tertiary carboxylic acid amide
Acetamide
Tertiary amine
Secondary alcohol
Carboxamide group
Lactam
Amino acid or derivatives
Carboxylic acid derivative
Azacycle
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Alcohol
Amine
Hydrocarbon derivative
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	2.61	ALOGPS
logP	2.39	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.7	ChemAxon
pKa (Strongest Basic)	1.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	93.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	134.4 m³·mol⁻¹	ChemAxon
Polarizability	51.11 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

22369875

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45359360

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione (NP0152490)

MOL for NP0152490 (16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione)

3D MOL for NP0152490 (16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione)

3D SDF for NP0152490 (16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione)

3D-SDF for NP0152490 (16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione)

PDB for NP0152490 (16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione)

3D PDB for NP0152490 (16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione)

SMILES for NP0152490 (16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione)

INCHI for NP0152490 (16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione)

Structure for NP0152490 (16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione)

3D Structure for NP0152490 (16-acetyl-24-hydroxy-12-methyl-23-(2-methylbut-3-en-2-yl)-3,11,14,16-tetraazahexacyclo[12.10.0.0²,¹¹.0⁴,⁹.0¹⁵,²³.0¹⁷,²²]tetracosa-2,4,6,8,17,19,21-heptaene-10,13-dione)