NP-MRD: Showing NP-Card for 3-benzyl-1,6,12-trihydroxy-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate (NP0303645)

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Record Information

Version

2.0

Created at

2022-09-10 18:11:13 UTC

Updated at

2022-09-10 18:11:14 UTC

NP-MRD ID

NP0303645

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-benzyl-1,6,12-trihydroxy-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate

Description

Cytochalasin H 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. Cytochalasin H is an extremely weak basic (essentially neutral) compound (based on its pKa). Once bound, cytochalasin essentially caps the end of the new actin filament. By blocking the polymerization and elongation of actin, cytochalasins can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. Cytochalasin H is a potentially toxic compound. As a result, they can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. It also regulates plant growth and has shown CNS activity. Anticoagulant therapy with intravenous heparin is also recommended. Some cytochalasins have been shown to have developmental effects. Cytochalasin H is has been isolated from the fungus Phomopsis paspali. Cytochalasins are mycotoxins that have the ability to bind to actin filaments and block polymerization and the elongation of actin. Major biological effects of cytochalasins include inhibition of the division of cytoplasm, reversible inhibition of cell movement, induction of nuclear extrusion, inhibition of such processes as phagocytosis, platelet aggregation and clot retraction, glucose transport, thyroid secretion, and release of growth hormone. Cytochalasins also have the ability to permeate cell membranes, prevent cellular translocation, cause cells to enucleate, and affect other aspects of biological processes unrelated to actin polymerization. 3-benzyl-1,6,12-trihydroxy-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate is found in Phaeohelotium epiphyllum. One cytochalasin will bind to one actin filament.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241212132D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 02241212132D          

 36 39  0  0  0  0            999 V2000
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   10.5547   -2.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2692   -5.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9836   -5.2975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1257   -6.1225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7091   -6.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7091   -7.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2925   -6.1225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  6  4  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10  7  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
  5 13  2  0  0  0  0
  6 14  1  0  0  0  0
  1 15  1  0  0  0  0
 20 15  2  0  0  0  0
 16 15  1  0  0  0  0
 16 17  2  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
  8 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 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
  7 29  1  0  0  0  0
 24 30  1  0  0  0  0
 26 31  1  0  0  0  0
 26 32  1  0  0  0  0
 29 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0303645

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3=CC=CC=C3)NC(=O)C22C(\C=C\CC(C)CC(C)(O)\C=C\C2OC(C)=O)C(O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C30H39NO5/c1-18-10-9-13-23-27(33)20(3)19(2)26-24(16-22-11-7-6-8-12-22)31-28(34)30(23,26)25(36-21(4)32)14-15-29(5,35)17-18/h6-9,11-15,18-19,23-27,33,35H,3,10,16-17H2,1-2,4-5H3,(H,31,34)/b13-9+,15-14+

> <INCHI_KEY>
NAEWXXDGBKTIMN-BBXOWAOSSA-N

> <FORMULA>
C30H39NO5

> <MOLECULAR_WEIGHT>
493.6344

> <EXACT_MASS>
493.282823363

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
54.766007233689244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-benzyl-6,12-dihydroxy-4,10,12-trimethyl-5-methylidene-1-oxo-1H,2H,3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
3.3706490089999996

> <ALOGPS_LOGS>
-5.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.458515862324262

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.927667781508635

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3728177062485397

> <JCHEM_POLAR_SURFACE_AREA>
95.86000000000001

> <JCHEM_REFRACTIVITY>
140.95770000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-benzyl-6,12-dihydroxy-4,10,12-trimethyl-5-methylidene-1-oxo-2H,3H,4H,6H,6aH,9H,10H,11H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       9.033  -6.809   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.366  -7.579   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      10.366  -9.119   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      11.700  -6.809   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.034  -4.499   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.700  -5.269   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.034  -7.579   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.367  -6.809   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.367  -5.269   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.700  -9.889   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.700 -11.429   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      15.701  -4.499   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.034  -2.959   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.366  -4.499   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.699  -7.579   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.365  -6.809   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.032  -7.579   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.032  -9.119   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.365  -9.889   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.699  -9.119   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.701  -7.579   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.035  -6.809   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.368  -7.579   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.702  -6.809   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.036  -7.579   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      21.036  -9.119   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.702  -9.889   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.368  -9.119   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.035  -9.889   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      19.702  -5.269   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      21.036 -10.659   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      22.369  -9.889   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      17.035 -11.429   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      18.124 -12.518   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      18.124 -14.058   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      19.213 -11.429   0.000  0.00  0.00           O+0
CONECT    1    2   15                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2   10                                                       
CONECT    4    2    6    7                                                  
CONECT    5    6    9   13                                                  
CONECT    6    4    5   14                                                  
CONECT    7    4    8   10   29                                             
CONECT    8    7    9   21                                                  
CONECT    9    8    5   12                                                  
CONECT   10    3    7   11                                                  
CONECT   11   10                                                            
CONECT   12    9                                                            
CONECT   13    5                                                            
CONECT   14    6                                                            
CONECT   15    1   20   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   15   19                                                       
CONECT   21    8   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   31   32                                             
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    7   33                                                  
CONECT   30   24                                                            
CONECT   31   26                                                            
CONECT   32   26                                                            
CONECT   33   29   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₉NO₅

Average Mass

493.6344 Da

Monoisotopic Mass

493.28282 Da

IUPAC Name

3-benzyl-6,12-dihydroxy-4,10,12-trimethyl-5-methylidene-1-oxo-1H,2H,3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate

Traditional Name

3-benzyl-6,12-dihydroxy-4,10,12-trimethyl-5-methylidene-1-oxo-2H,3H,4H,6H,6aH,9H,10H,11H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3=CC=CC=C3)NC(=O)C22C(\C=C\CC(C)CC(C)(O)\C=C\C2OC(C)=O)C(O)C1=C

InChI Identifier

InChI=1S/C30H39NO5/c1-18-10-9-13-23-27(33)20(3)19(2)26-24(16-22-11-7-6-8-12-22)31-28(34)30(23,26)25(36-21(4)32)14-15-29(5,35)17-18/h6-9,11-15,18-19,23-27,33,35H,3,10,16-17H2,1-2,4-5H3,(H,31,34)/b13-9+,15-14+

InChI Key

NAEWXXDGBKTIMN-BBXOWAOSSA-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
Phaeohelotium epiphyllum	LOTUS Database	35616633

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

Carbocyclic cytochalasan skeleton
Cytochalasan
Isoindolone
Isoindoline
Isoindole
Isoindole or derivatives
Monocyclic benzene moiety
Pyrrolidone
2-pyrrolidone
Benzenoid
Tertiary alcohol
Pyrrolidine
Cyclic alcohol
Secondary alcohol
Secondary carboxylic acid amide
Carboxamide group
Lactam
Carboxylic acid ester
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Azacycle
Carboxylic acid derivative
Alcohol
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Carbonyl group
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	3.54	ALOGPS
logP	3.37	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	13.93	ChemAxon
pKa (Strongest Basic)	-0.37	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	4	ChemAxon
Refractivity	140.96 m³·mol⁻¹	ChemAxon
Polarizability	54.77 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

5351303

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-benzyl-1,6,12-trihydroxy-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate (NP0303645)

MOL for NP0303645 (3-benzyl-1,6,12-trihydroxy-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate)

3D MOL for NP0303645 (3-benzyl-1,6,12-trihydroxy-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate)

3D SDF for NP0303645 (3-benzyl-1,6,12-trihydroxy-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate)

3D-SDF for NP0303645 (3-benzyl-1,6,12-trihydroxy-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate)

PDB for NP0303645 (3-benzyl-1,6,12-trihydroxy-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate)

3D PDB for NP0303645 (3-benzyl-1,6,12-trihydroxy-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate)

SMILES for NP0303645 (3-benzyl-1,6,12-trihydroxy-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate)

INCHI for NP0303645 (3-benzyl-1,6,12-trihydroxy-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate)

Structure for NP0303645 (3-benzyl-1,6,12-trihydroxy-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate)

3D Structure for NP0303645 (3-benzyl-1,6,12-trihydroxy-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate)