NP-MRD: Showing NP-Card for 15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindole-5-carboxylic acid (NP0324032)

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Record Information

Version

2.0

Created at

2022-09-12 03:50:38 UTC

Updated at

2022-09-12 03:50:38 UTC

NP-MRD ID

NP0324032

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindole-5-carboxylic acid

Description

15-(Acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3H,4H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindole-5-carboxylic acid belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D, H, and K. Based on a literature review very few articles have been published on 15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3H,4H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindole-5-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122205502D          

 37 40  0  0  0  0            999 V2000
    2.3984    0.6332    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


  Mrv1652309122205502D          

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    1.4760   -1.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  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
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 26 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 17 37  1  0  0  0  0
  5 37  1  0  0  0  0
 25 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324032

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3=CC=CC=C3)N=C(O)C22C(C=C1C(O)=O)C=CCC(C)CC(C)(O)C=CC2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H37NO6/c1-18-9-8-12-22-16-23(27(33)34)19(2)26-24(15-21-10-6-5-7-11-21)31-28(35)30(22,26)25(37-20(3)32)13-14-29(4,36)17-18/h5-8,10-14,16,18-19,22,24-26,36H,9,15,17H2,1-4H3,(H,31,35)(H,33,34)

> <INCHI_KEY>
XOAQRSFHWAISAM-UHFFFAOYSA-N

> <FORMULA>
C30H37NO6

> <MOLECULAR_WEIGHT>
507.627

> <EXACT_MASS>
507.262087915

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.942087363340235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3H,4H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindole-5-carboxylic acid

> <JCHEM_LOGP>
3.4911840371037233

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.494452478127214

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.142641288746886

> <JCHEM_PKA_STRONGEST_BASIC>
5.555812994474475

> <JCHEM_POLAR_SURFACE_AREA>
116.42

> <JCHEM_REFRACTIVITY>
142.8306

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3H,4H,6aH,9H,10H,11H,15H,15bH-cycloundeca[e]isoindole-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       4.477   1.182   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.782  -0.097   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.425   0.829   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.846  -1.916   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.482  -2.625   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.941  -1.151   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.468  -1.349   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.752  -2.862   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.937  -1.595   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.497  -2.657   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.046  -3.942   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.848  -5.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.934  -6.656   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.427  -6.062   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.203  -5.127   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.781  -5.720   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.557  -4.785   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.136  -5.377   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.088  -4.442   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.588  -5.147   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.121  -4.690   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.176  -6.622   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.110  -2.915   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.324  -2.202   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.531  -2.323   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.042  -0.870   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.740   0.257   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.827   1.789   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.107   3.150   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.926   4.454   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.464   4.397   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.185   3.036   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.366   1.732   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       3.582  -0.907   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       4.022  -2.383   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.531  -3.107   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.755  -3.258   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   37                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   37                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   37                                                  
CONECT   26   25   27   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   26   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   17    5   25                                             
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
15-(Acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3H,4H,6ah,9H,10H,11H,12H,15H,15BH-cycloundeca[e]isoindole-5-carboxylate	Generator

Chemical Formula

C₃₀H₃₇NO₆

Average Mass

507.6270 Da

Monoisotopic Mass

507.26209 Da

IUPAC Name

15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3H,4H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindole-5-carboxylic acid

Traditional Name

15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3H,4H,6aH,9H,10H,11H,15H,15bH-cycloundeca[e]isoindole-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3=CC=CC=C3)N=C(O)C22C(C=C1C(O)=O)C=CCC(C)CC(C)(O)C=CC2OC(C)=O

InChI Identifier

InChI=1S/C30H37NO6/c1-18-9-8-12-22-16-23(27(33)34)19(2)26-24(15-21-10-6-5-7-11-21)31-28(35)30(22,26)25(37-20(3)32)13-14-29(4,36)17-18/h5-8,10-14,16,18-19,22,24-26,36H,9,15,17H2,1-4H3,(H,31,35)(H,33,34)

InChI Key

XOAQRSFHWAISAM-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D, H, and K.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cytochalasans

Sub Class

Not Available

Direct Parent

Cytochalasans

Alternative Parents

Substituents

Cytochalasan
Carbocyclic cytochalasan skeleton
Isoindolone
Isoindole or derivatives
Isoindole
Isoindoline
Benzenoid
2-pyrrolidone
Pyrrolidone
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Tertiary alcohol
Pyrrolidine
Secondary carboxylic acid amide
Lactam
Carboxylic acid ester
Carboxamide group
Azacycle
Organoheterocyclic compound
Carboxylic acid
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	3.49	ChemAxon
pKa (Strongest Acidic)	3.14	ChemAxon
pKa (Strongest Basic)	5.56	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	116.42 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	142.83 m³·mol⁻¹	ChemAxon
Polarizability	54.94 Å³	ChemAxon
Number of Rings	4	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

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

163048634

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindole-5-carboxylic acid (NP0324032)

MOL for NP0324032 (15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindole-5-carboxylic acid)

3D MOL for NP0324032 (15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindole-5-carboxylic acid)

3D SDF for NP0324032 (15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindole-5-carboxylic acid)

3D-SDF for NP0324032 (15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindole-5-carboxylic acid)

PDB for NP0324032 (15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindole-5-carboxylic acid)

3D PDB for NP0324032 (15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindole-5-carboxylic acid)

SMILES for NP0324032 (15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindole-5-carboxylic acid)

INCHI for NP0324032 (15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindole-5-carboxylic acid)

Structure for NP0324032 (15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindole-5-carboxylic acid)

3D Structure for NP0324032 (15-(acetyloxy)-3-benzyl-1,12-dihydroxy-4,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindole-5-carboxylic acid)