NP-MRD: Showing NP-Card for Pyrichalasin H (NP0058036)

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Record Information

Version

1.0

Created at

2022-04-28 03:22:11 UTC

Updated at

2022-04-28 03:22:11 UTC

NP-MRD ID

NP0058036

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pyrichalasin H

Description

(3S,4S,6S,6aR,10S,12R,15R,15aR,15bR)-1,6,12-trihydroxy-3-[(4-methoxyphenyl)methyl]-4,10,12-trimethyl-5-methylidene-3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate belongs to the class of organic compounds known as pyrichalasins. These are cytochalasans with a structure in which the hydrogenated isoindole bears p-methoxybenzyl group. Pyrichalasin H is found in Magnaporthe grisea. Based on a literature review very few articles have been published on (3S,4S,6S,6aR,10S,12R,15R,15aR,15bR)-1,6,12-trihydroxy-3-[(4-methoxyphenyl)methyl]-4,10,12-trimethyl-5-methylidene-3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205222D          

 38 41  0  0  1  0            999 V2000
   -0.1483   -3.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5800   -3.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2798   -3.9218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2511   -4.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5228   -5.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1769   -4.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053   -5.0842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339   -5.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0081   -3.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -2.7098    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3865   -2.2020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6685   -1.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
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 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  1  0  0  0
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 22 23  1  0  0  0  0
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 31 33  1  0  0  0  0
 26 34  1  6  0  0  0
 26 35  1  1  0  0  0
 24 36  1  1  0  0  0
 19 37  1  6  0  0  0
 16 38  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282205222D          

 38 41  0  0  1  0            999 V2000
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    2.2242   -2.9618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4656   -3.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2695   -3.9361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9031   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1225   -4.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3779   -4.2472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7312   -2.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4395   -0.4676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1714   -2.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 12  1  6  0  0  0
 15 14  1  1  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  1  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
 14 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 26 34  1  6  0  0  0
 26 35  1  1  0  0  0
 24 36  1  1  0  0  0
 19 37  1  6  0  0  0
 16 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0058036

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C[C@@H]2NC(=O)[C@]34[C@H]2[C@H](C)C(=C)[C@@H](O)[C@@H]3\C=C\C[C@H](C)C[C@@](C)(O)\C=C\[C@H]4OC(C)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H41NO6/c1-18-8-7-9-24-28(34)20(3)19(2)27-25(16-22-10-12-23(37-6)13-11-22)32-29(35)31(24,27)26(38-21(4)33)14-15-30(5,36)17-18/h7,9-15,18-19,24-28,34,36H,3,8,16-17H2,1-2,4-6H3,(H,32,35)/b9-7+,15-14+/t18-,19+,24-,25-,26+,27-,28+,30-,31+/m0/s1

> <INCHI_KEY>
AECZOENDDUTONS-AGCUOWGBSA-N

> <FORMULA>
C31H41NO6

> <MOLECULAR_WEIGHT>
523.67

> <EXACT_MASS>
523.293388044

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
57.09475016398534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S,6S,6aR,10S,12R,15R,15aR,15bR)-6,12-dihydroxy-3-[(4-methoxyphenyl)methyl]-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>
3.60

> <JCHEM_LOGP>
3.212977743333333

> <ALOGPS_LOGS>
-5.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.396608682928711

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.876397671804941

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3728023665650534

> <JCHEM_POLAR_SURFACE_AREA>
105.09

> <JCHEM_REFRACTIVITY>
147.42090000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.32e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,6S,6aR,10S,12R,15R,15aR,15bR)-6,12-dihydroxy-3-[(4-methoxyphenyl)methyl]-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                                 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      -0.277  -7.228   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.083  -6.505   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.389  -7.321   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.335  -8.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.976  -9.583   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.330  -8.767   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.690  -9.490   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.743 -11.029   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.748  -6.597   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.802  -5.058   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.588  -4.110   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.115  -2.663   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.253  -1.387   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.654  -2.717   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.854  -3.824   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.348  -4.196   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.642  -3.461   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.949  -4.277   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.844  -2.205   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.723  -1.609   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.375  -1.945   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.734  -1.221   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.842  -2.291   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.167  -3.675   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.561  -5.314   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.492  -6.422   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.998  -6.049   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.696  -4.774   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.202  -4.402   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.152  -5.529   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.603  -7.001   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.103  -7.347   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.553  -8.128   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.562  -7.529   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.172  -7.928   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.698  -3.842   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.287  -0.873   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       7.787  -5.517   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    3   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20   29                                             
CONECT   15   14   10   16                                                  
CONECT   16   15   17   38                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   37                                                  
CONECT   20   19   14   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   36                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   34   35                                             
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   14   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   26                                                            
CONECT   35   26                                                            
CONECT   36   24                                                            
CONECT   37   19                                                            
CONECT   38   16                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
(3S,4S,6S,6AR,10S,12R,15R,15ar,15BR)-1,6,12-trihydroxy-3-[(4-methoxyphenyl)methyl]-4,10,12-trimethyl-5-methylidene-3H,4H,5H,6H,6ah,9H,10H,11H,12H,15H,15BH-cycloundeca[e]isoindol-15-yl acetic acid	Generator

Chemical Formula

C₃₁H₄₁NO₆

Average Mass

523.6700 Da

Monoisotopic Mass

523.29339 Da

IUPAC Name

(3S,4S,6S,6aR,10S,12R,15R,15aR,15bR)-6,12-dihydroxy-3-[(4-methoxyphenyl)methyl]-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

(3S,4S,6S,6aR,10S,12R,15R,15aR,15bR)-6,12-dihydroxy-3-[(4-methoxyphenyl)methyl]-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

COC1=CC=C(C[C@@H]2NC(=O)[C@]34[C@H]2[C@H](C)C(=C)[C@@H](O)[C@@H]3\C=C\C[C@H](C)C[C@@](C)(O)\C=C\[C@H]4OC(C)=O)C=C1

InChI Identifier

InChI=1S/C31H41NO6/c1-18-8-7-9-24-28(34)20(3)19(2)27-25(16-22-10-12-23(37-6)13-11-22)32-29(35)31(24,27)26(38-21(4)33)14-15-30(5,36)17-18/h7,9-15,18-19,24-28,34,36H,3,8,16-17H2,1-2,4-6H3,(H,32,35)/b9-7+,15-14+/t18-,19+,24-,25-,26+,27-,28+,30-,31+/m0/s1

InChI Key

AECZOENDDUTONS-AGCUOWGBSA-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
Magnaporthe grisea	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrichalasins. These are cytochalasans with a structure in which the hydrogenated isoindole bears p-methoxybenzyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cytochalasans

Sub Class

Pyrichalasins

Direct Parent

Pyrichalasins

Alternative Parents

Substituents

Carbocyclic pyrichalasin skeleton
Isoindolone
Isoindoline
Isoindole
Isoindole or derivatives
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Pyrrolidone
2-pyrrolidone
Cyclic alcohol
Tertiary alcohol
Pyrrolidine
Secondary alcohol
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Lactam
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Azacycle
Organoheterocyclic compound
Alcohol
Organooxygen compound
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organopnictogen 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	3.6	ALOGPS
logP	3.21	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	13.88	ChemAxon
pKa (Strongest Basic)	-0.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.09 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	147.42 m³·mol⁻¹	ChemAxon
Polarizability	57.09 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

163076042

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Pyrichalasin H (NP0058036)

MOL for NP0058036 (Pyrichalasin H)

3D MOL for NP0058036 (Pyrichalasin H)

3D SDF for NP0058036 (Pyrichalasin H)

3D-SDF for NP0058036 (Pyrichalasin H)

PDB for NP0058036 (Pyrichalasin H)

3D PDB for NP0058036 (Pyrichalasin H)

SMILES for NP0058036 (Pyrichalasin H)

INCHI for NP0058036 (Pyrichalasin H)

Structure for NP0058036 (Pyrichalasin H)

3D Structure for NP0058036 (Pyrichalasin H)