NP-MRD: Showing NP-Card for Deacetylzygosporin A (NP0058029)

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Record Information

Version

2.0

Created at

2022-04-28 03:21:48 UTC

Updated at

2022-04-28 03:21:48 UTC

NP-MRD ID

NP0058029

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Deacetylzygosporin A

Description

NSC785137 belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. Deacetylzygosporin A is found in Hetarrhizium anisopliae, Metarrhizium anisopliae and Zygosporium masonii. Based on a literature review very few articles have been published on NSC785137.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205212D          

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M  END

     RDKit          3D

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  Mrv1652304282205212D          

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M  END
> <DATABASE_ID>
NP0058029

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@H](CC3=CC=CC=C3)NC(=O)[C@@]22[C@@H](\C=C\C[C@H](C)C(=O)[C@](C)(O)\C=C\[C@@H]2O)[C@H](O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C28H35NO5/c1-16-9-8-12-20-24(31)18(3)17(2)23-21(15-19-10-6-5-7-11-19)29-26(33)28(20,23)22(30)13-14-27(4,34)25(16)32/h5-8,10-14,16-17,20-24,30-31,34H,3,9,15H2,1-2,4H3,(H,29,33)/b12-8+,14-13+/t16-,17+,20-,21-,22-,23-,24+,27+,28+/m0/s1

> <INCHI_KEY>
DMUBZPWTFAPROZ-SYCLLRKHSA-N

> <FORMULA>
C28H35NO5

> <MOLECULAR_WEIGHT>
465.59

> <EXACT_MASS>
465.251523231

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
50.837278895844044

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S,6S,6aR,10S,12R,15S,15aR,15bR)-3-benzyl-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylidene-1H,2H,3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindole-1,11-dione

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
2.6741148793333336

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.7857855420656

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.825551364298004

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3330961391549664

> <JCHEM_POLAR_SURFACE_AREA>
106.86000000000001

> <JCHEM_REFRACTIVITY>
132.37130000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,6S,6aR,10S,12R,15S,15aR,15bR)-3-benzyl-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylidene-2H,3H,4H,6H,6aH,9H,10H,15H,15bH-cycloundeca[e]isoindole-1,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.249  -6.749   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.217  -6.276   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.359  -7.309   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.036  -8.815   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.571  -9.288   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.572  -8.255   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.747  -6.861   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.791  -5.058   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.585  -4.100   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.123  -2.658   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.206  -1.354   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.661  -2.724   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.853  -3.832   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.344  -4.217   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.312  -2.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.630  -4.407   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.856  -2.230   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.740  -1.624   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.389  -1.974   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.754  -1.262   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.853  -2.340   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.167  -3.719   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.548  -5.361   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.051  -5.935   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.469  -6.460   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.541  -5.743   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.687  -4.798   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.196  -4.414   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.448  -5.888   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.519  -7.774   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.688  -8.144   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.616  -4.422   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.595  -0.654   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.335  -6.007   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    3    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18   28                                             
CONECT   13   12    8   14                                                  
CONECT   14   13   15   34                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   33                                                  
CONECT   18   17   12   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   32                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30   31                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   12   29                                                  
CONECT   29   28                                                            
CONECT   30   25                                                            
CONECT   31   25                                                            
CONECT   32   22                                                            
CONECT   33   17                                                            
CONECT   34   14                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₅NO₅

Average Mass

465.5900 Da

Monoisotopic Mass

465.25152 Da

IUPAC Name

(3S,4S,6S,6aR,10S,12R,15S,15aR,15bR)-3-benzyl-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylidene-1H,2H,3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindole-1,11-dione

Traditional Name

(3S,4S,6S,6aR,10S,12R,15S,15aR,15bR)-3-benzyl-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylidene-2H,3H,4H,6H,6aH,9H,10H,15H,15bH-cycloundeca[e]isoindole-1,11-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@H](CC3=CC=CC=C3)NC(=O)[C@@]22[C@@H](\C=C\C[C@H](C)C(=O)[C@](C)(O)\C=C\[C@@H]2O)[C@H](O)C1=C

InChI Identifier

InChI=1S/C28H35NO5/c1-16-9-8-12-20-24(31)18(3)17(2)23-21(15-19-10-6-5-7-11-19)29-26(33)28(20,23)22(30)13-14-27(4,34)25(16)32/h5-8,10-14,16-17,20-24,30-31,34H,3,9,15H2,1-2,4H3,(H,29,33)/b12-8+,14-13+/t16-,17+,20-,21-,22-,23-,24+,27+,28+/m0/s1

InChI Key

DMUBZPWTFAPROZ-SYCLLRKHSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Hetarrhizium anisopliae	-	KNApSAcK
Metarhizium anisopliae	-	KNApSAcK
Zygosporium masonii	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Isoindolones

Alternative Parents

Substituents

Isoindolone
Isoindole
Acyloin
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Pyrroline
Tertiary alcohol
Cyclic carboximidic acid
Cyclic ketone
Secondary alcohol
Ketone
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Alcohol
Organic oxygen 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	2.29	ALOGPS
logP	2.67	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	12.83	ChemAxon
pKa (Strongest Basic)	-0.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	132.37 m³·mol⁻¹	ChemAxon
Polarizability	50.84 Å³	ChemAxon
Number of Rings	4	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

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

155807627

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Deacetylzygosporin A (NP0058029)

MOL for NP0058029 (Deacetylzygosporin A)

3D MOL for NP0058029 (Deacetylzygosporin A)

3D SDF for NP0058029 (Deacetylzygosporin A)

3D-SDF for NP0058029 (Deacetylzygosporin A)

PDB for NP0058029 (Deacetylzygosporin A)

3D PDB for NP0058029 (Deacetylzygosporin A)

SMILES for NP0058029 (Deacetylzygosporin A)

INCHI for NP0058029 (Deacetylzygosporin A)

Structure for NP0058029 (Deacetylzygosporin A)

3D Structure for NP0058029 (Deacetylzygosporin A)