NP-MRD: Showing NP-Card for Cytochalasin A (NP0058023)

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Record Information

Version

2.0

Created at

2022-04-28 03:21:29 UTC

Updated at

2022-04-28 03:21:29 UTC

NP-MRD ID

NP0058023

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cytochalasin A

Description

(9R,13S,15S,15aS,16S,18aS,18bR)-16-benzyl-13,18-dihydroxy-9,15-dimethyl-14-methylidene-2H,5H,6H,7H,8H,9H,10H,13H,14H,15H,15aH,16H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,5-dione belongs to the class of organic compounds known as cytochalasins. These are cytochalasans in which the hydrogenated isoindolone bears a benzyl group. Cytochalasin A is found in Ascochyta heteromorpha, Phoma exigua var. exigua and Helminthosporium dematioideum. Based on a literature review very few articles have been published on (9R,13S,15S,15aS,16S,18aS,18bR)-16-benzyl-13,18-dihydroxy-9,15-dimethyl-14-methylidene-2H,5H,6H,7H,8H,9H,10H,13H,14H,15H,15aH,16H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,5-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205212D          

 35 38  0  0  1  0            999 V2000
    5.4387    1.5818    0.0000 C   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


  Mrv1652304282205212D          

 35 38  0  0  1  0            999 V2000
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 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32  8  1  1  0  0  0
 12 32  1  0  0  0  0
 31 33  1  1  0  0  0
 28 34  1  6  0  0  0
 23 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0058023

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H35NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18-19,23-24,26-27,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8+,16-15+/t18-,19-,23-,24+,26+,27-,29-/m1/s1

> <INCHI_KEY>
ZMAODHOXRBLOQO-ZHOJCWIZSA-N

> <FORMULA>
C29H35NO5

> <MOLECULAR_WEIGHT>
477.601

> <EXACT_MASS>
477.251523231

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.754477450410604

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9R,13S,15S,15aS,16S,18aS,18bR)-16-benzyl-13-hydroxy-9,15-dimethyl-14-methylidene-2H,5H,6H,7H,8H,9H,10H,13H,14H,15H,15aH,16H,17H,18H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,5,18-trione

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
4.493695331333332

> <ALOGPS_LOGS>
-5.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.251430356363468

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.067214392002409

> <JCHEM_PKA_STRONGEST_BASIC>
-3.151185570807228

> <JCHEM_POLAR_SURFACE_AREA>
92.7

> <JCHEM_REFRACTIVITY>
135.5196

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R,13S,15S,15aS,16S,18aS,18bR)-16-benzyl-13-hydroxy-9,15-dimethyl-14-methylidene-6H,7H,8H,9H,10H,13H,15H,15aH,16H,17H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,5,18-trione

> <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      10.152   2.953   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.338   1.645   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.799   1.696   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.074   3.055   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.888   4.362   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.427   4.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.986   0.389   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.711  -0.970   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       9.236  -1.181   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       9.502  -2.480   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.892  -3.370   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.148  -3.423   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.628  -2.996   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.997  -1.501   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.888  -0.433   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.477  -1.074   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.587  -2.142   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.066  -1.714   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.436  -0.219   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      15.176  -2.782   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.806  -4.277   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.327  -4.704   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.957  -6.199   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.477  -6.626   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.367  -5.558   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.888  -5.986   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.778  -4.918   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.298  -5.345   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.189  -4.277   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.709  -4.704   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.559  -2.782   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.038  -2.355   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.449  -1.714   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.929  -6.840   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      14.066  -7.267   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   32                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   27   32                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   35                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   12   28                                                  
CONECT   28   27   29   34                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31    8   12                                                  
CONECT   33   31                                                            
CONECT   34   28                                                            
CONECT   35   23                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₅NO₅

Average Mass

477.6010 Da

Monoisotopic Mass

477.25152 Da

IUPAC Name

(9R,13S,15S,15aS,16S,18aS,18bR)-16-benzyl-13-hydroxy-9,15-dimethyl-14-methylidene-2H,5H,6H,7H,8H,9H,10H,13H,14H,15H,15aH,16H,17H,18H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,5,18-trione

Traditional Name

(9R,13S,15S,15aS,16S,18aS,18bR)-16-benzyl-13-hydroxy-9,15-dimethyl-14-methylidene-6H,7H,8H,9H,10H,13H,15H,15aH,16H,17H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,5,18-trione

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C29H35NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18-19,23-24,26-27,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8+,16-15+/t18-,19-,23-,24+,26+,27-,29-/m1/s1

InChI Key

ZMAODHOXRBLOQO-ZHOJCWIZSA-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
Ascochyta heteromorpha	Fungi	KNApSAcK
Boeremia exigua var. exigua	Fungi	KNApSAcK
Helminthosporium dematioideum	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cytochalasins. These are cytochalasans in which the hydrogenated isoindolone bears a benzyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cytochalasans

Sub Class

Cytochalasins

Direct Parent

Cytochalasins

Alternative Parents

Substituents

Lactone cytochalasin skeleton
Cytochalasin
Isoindolone
Isoindole or derivatives
Isoindole
Isoindoline
Benzenoid
2-pyrrolidone
Pyrrolidone
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrrolidine
Cyclic alcohol
Cyclic ketone
Secondary carboxylic acid amide
Secondary alcohol
Lactone
Lactam
Ketone
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	3.38	ALOGPS
logP	4.49	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	13.07	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	135.52 m³·mol⁻¹	ChemAxon
Polarizability	52.75 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

20126511

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20831634

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cytochalasin A (NP0058023)

MOL for NP0058023 (Cytochalasin A)

3D MOL for NP0058023 (Cytochalasin A)

3D SDF for NP0058023 (Cytochalasin A)

3D-SDF for NP0058023 (Cytochalasin A)

PDB for NP0058023 (Cytochalasin A)

3D PDB for NP0058023 (Cytochalasin A)

SMILES for NP0058023 (Cytochalasin A)

INCHI for NP0058023 (Cytochalasin A)

Structure for NP0058023 (Cytochalasin A)

3D Structure for NP0058023 (Cytochalasin A)