NP-MRD: Showing NP-Card for 16-benzyl-5,13,18-trihydroxy-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one (NP0309467)

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Record Information

Version

2.0

Created at

2022-09-11 04:05:22 UTC

Updated at

2022-09-11 04:05:22 UTC

NP-MRD ID

NP0309467

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-benzyl-5,13,18-trihydroxy-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one

Description

AC1L1ERQ belongs to the class of organic compounds known as cytochalasins. These are cytochalasans in which the hydrogenated isoindolone bears a benzyl group. 16-benzyl-5,13,18-trihydroxy-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one is found in Pyrenophora dematioidea, Boeremia exigua and Sonchus mauritanicus. AC1L1ERQ is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171512472D          

 35 38  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004171512472D          

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 22 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  1  0  0  0  0
 13 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0309467

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3=CC=CC=C3)NC(=O)C22OC(=O)C=CC(O)CCCC(C)CC=CC2C(O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C29H37NO5/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/h4-6,8,11-12,14-16,18-19,22-24,26-27,31,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)

> <INCHI_KEY>
GBOGMAARMMDZGR-UHFFFAOYSA-N

> <FORMULA>
C29H37NO5

> <MOLECULAR_WEIGHT>
479.617

> <EXACT_MASS>
479.267173295

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.50070239361685

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-benzyl-5,13-dihydroxy-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-2,18-dione

> <ALOGPS_LOGP>
4.05

> <JCHEM_LOGP>
4.082356843333333

> <ALOGPS_LOGS>
-4.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.162264371801953

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.110296765877077

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8716115820565564

> <JCHEM_POLAR_SURFACE_AREA>
95.86000000000001

> <JCHEM_REFRACTIVITY>
136.41700000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.14e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cytochalasen-B

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      12.695  -1.414   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.197  -0.827   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.666  -1.288   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.001  -2.791   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.867  -3.833   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.397  -3.371   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      14.488  -1.751   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.263  -4.413   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.027  -3.584   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.693  -2.081   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.270  -2.398   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.223  -1.619   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.655  -0.484   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.789   0.558   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.492   0.464   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.626   1.506   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.862   0.677   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.130  -0.106   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.417   0.771   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.593  -1.407   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.370  -1.981   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.330  -2.650   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.574  -4.549   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.861  -2.189   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.664  -2.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.352  -4.338   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.029  -4.878   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.821  -6.404   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.395  -6.986   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.178  -6.042   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.387  -4.516   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.813  -3.934   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       6.509  -1.751   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       7.122  -0.338   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.321   1.044   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   24   34                                             
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    2                                                       
CONECT   18   14   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   13   25                                                  
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   25   34                                                       
CONECT   34   33   13   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
Phomin	MeSH

Chemical Formula

C₂₉H₃₇NO₅

Average Mass

479.6170 Da

Monoisotopic Mass

479.26717 Da

IUPAC Name

16-benzyl-5,13-dihydroxy-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-2,18-dione

Traditional Name

cytochalasen-B

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3=CC=CC=C3)NC(=O)C22OC(=O)C=CC(O)CCCC(C)CC=CC2C(O)C1=C

InChI Identifier

InChI=1S/C29H37NO5/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/h4-6,8,11-12,14-16,18-19,22-24,26-27,31,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)

InChI Key

GBOGMAARMMDZGR-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
Helminthosporium dematioideum	LOTUS Database	35616633
Phoma exigua	LOTUS Database	35616633
Sonchus mauritanicus	LOTUS Database	35616633

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
Isoindoline
Isoindole
Isoindole or derivatives
Monocyclic benzene moiety
Pyrrolidone
Benzenoid
2-pyrrolidone
Cyclic alcohol
Pyrrolidine
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Alcohol
Organonitrogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen 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	4.05	ALOGPS
logP	4.08	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	13.11	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.86 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	136.42 m³·mol⁻¹	ChemAxon
Polarizability	53.5 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

2919

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-benzyl-5,13,18-trihydroxy-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one (NP0309467)

MOL for NP0309467 (16-benzyl-5,13,18-trihydroxy-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

3D MOL for NP0309467 (16-benzyl-5,13,18-trihydroxy-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

3D SDF for NP0309467 (16-benzyl-5,13,18-trihydroxy-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

3D-SDF for NP0309467 (16-benzyl-5,13,18-trihydroxy-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

PDB for NP0309467 (16-benzyl-5,13,18-trihydroxy-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

3D PDB for NP0309467 (16-benzyl-5,13,18-trihydroxy-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

SMILES for NP0309467 (16-benzyl-5,13,18-trihydroxy-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

INCHI for NP0309467 (16-benzyl-5,13,18-trihydroxy-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

Structure for NP0309467 (16-benzyl-5,13,18-trihydroxy-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

3D Structure for NP0309467 (16-benzyl-5,13,18-trihydroxy-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)