NP-MRD: Showing NP-Card for hirsutellone B (NP0027838)

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Record Information

Version

2.0

Created at

2021-06-19 19:53:13 UTC

Updated at

2021-06-29 23:54:12 UTC

NP-MRD ID

NP0027838

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hirsutellone B

Provided By

JEOL Database JEOL Logo

Description

hirsutellone B is found in Hirsutella nivea and Hirsutella nivea BCC 2594. hirsutellone B was first documented in 2005 (Isaka, M., et al.). Based on a literature review very few articles have been published on (3S,4R,7R,9S,10S,13S,14S,16R,19S,27S)-13-ethenyl-17,19-dihydroxy-7-methyl-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]Heptacosa-1(23),11,17,21,24-pentaen-15-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121533D          

 66 71  0  0  0  0            999 V2000
    3.2827   -2.3385    1.7249 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


  Mrv1652306192121533D          

 66 71  0  0  0  0            999 V2000
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    2.6776   -1.3987    0.9850 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3484    1.7979    1.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0027838

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12N([H])C(=O)[C@]([H])(C(=O)[C@]3([H])[C@@]4([H])[C@@]([H])(OC5=C([H])C([H])=C(C([H])=C5[H])C1([H])[H])[C@]1([H])C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[H])C([H])([H])[C@@]1([H])[C@]4([H])C([H])=C([H])[C@]3([H])C([H])=C([H])[H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H33NO4/c1-3-17-7-11-19-21-12-15(2)4-10-20(21)26-24(19)23(17)25(30)22-14-28(32,29-27(22)31)13-16-5-8-18(33-26)9-6-16/h3,5-9,11,15,17,19-24,26,32H,1,4,10,12-14H2,2H3,(H,29,31)/t15-,17+,19+,20-,21+,22+,23+,24+,26+,28-/m1/s1

> <INCHI_KEY>
VGNDUPFGVMMKPS-KOSFCWFBSA-N

> <FORMULA>
C28H33NO4

> <MOLECULAR_WEIGHT>
447.575

> <EXACT_MASS>
447.240958547

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
49.381491446718655

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4R,7R,9S,10S,13S,14S,16S,19S,27S)-13-ethenyl-19-hydroxy-7-methyl-2-oxa-18-azahexacyclo[19.2.2.1^{3,10}.1^{16,19}.0^{4,9}.0^{14,27}]heptacosa-1(23),11,21,24-tetraene-15,17-dione

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
4.061134263666669

> <ALOGPS_LOGS>
-5.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.504110171967973

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.661011976908318

> <JCHEM_PKA_STRONGEST_BASIC>
-3.576830042361892

> <JCHEM_POLAR_SURFACE_AREA>
75.63

> <JCHEM_REFRACTIVITY>
126.9981

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4R,7R,9S,10S,13S,14S,16S,19S,27S)-13-ethenyl-19-hydroxy-7-methyl-2-oxa-18-azahexacyclo[19.2.2.1^{3,10}.1^{16,19}.0^{4,9}.0^{14,27}]heptacosa-1(23),11,21,24-tetraene-15,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 66 71  0  0  0  0  0  0  0  0999 V2000
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 23 53  1  6
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  6
 29 63  1  0
 29 64  1  0
  5 39  1  0
  4 38  1  0
  3 37  1  1
  8 42  1  1
 15 47  1  0
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 17 49  1  0
 18 50  1  0
 20 51  1  0
 21 52  1  0
  2 36  1  0
  1 34  1  0
  1 35  1  0
 14 46  1  0
 28 60  1  0
 28 61  1  0
 28 62  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       3.283  -2.338   1.725  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.678  -1.399   0.985  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.368  -0.722   1.357  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.707   0.688   1.797  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.348   1.798   1.137  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.510   1.738  -0.093  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.536   0.352  -0.793  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.277  -0.791   0.221  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.290  -2.195  -0.418  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.713  -2.343  -1.573  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.049  -3.425   0.425  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.425  -4.694  -0.376  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.860  -5.055   0.037  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.930  -6.417   0.408  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.958  -4.789  -1.031  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.984  -3.356  -1.499  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.296  -2.992  -2.662  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.950  -1.662  -2.871  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.277  -0.716  -1.906  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.156  -1.036  -0.876  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.518  -2.361  -0.673  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.742   0.532  -1.849  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.323   0.624  -2.068  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.087   2.140  -2.336  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.400   2.572  -3.709  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.500   4.109  -3.735  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.311   4.702  -2.557  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.204   6.226  -2.544  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.899   4.118  -1.184  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.926   2.601  -1.279  0.00  0.00           C+0
HETATM   31  N   UNK     0      -2.059  -4.332   1.246  0.00  0.00           N+0
HETATM   32  C   UNK     0      -1.162  -3.307   1.428  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.261  -2.475   2.314  0.00  0.00           O+0
HETATM   34  H   UNK     0       2.864  -2.686   2.664  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.227  -2.771   1.406  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.159  -1.075   0.063  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.954  -1.232   2.236  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.294   0.785   2.709  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.621   2.773   1.532  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.516   1.993   0.211  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.556   0.181  -1.179  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.711  -0.624   0.663  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.855  -3.661   0.997  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.264  -5.501  -0.092  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.315  -4.586  -1.458  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.477  -6.479   1.265  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.944  -5.054  -0.625  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.811  -5.465  -1.884  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.917  -3.747  -3.348  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.340  -1.407  -3.731  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.465  -0.273  -0.166  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.109  -2.616   0.203  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.018   0.033  -2.923  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.040   2.664  -2.162  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.378   2.130  -3.932  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.296   2.236  -4.486  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.946   4.424  -4.686  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.517   4.523  -3.715  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.366   4.445  -2.724  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.542   6.647  -3.496  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.825   6.652  -1.749  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.171   6.550  -2.377  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.102   4.470  -0.903  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.593   4.464  -0.410  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.947   2.316  -1.578  0.00  0.00           H+0
HETATM   66  H   UNK     0      -2.883  -4.414   1.828  0.00  0.00           H+0
CONECT    1    2   34   35                                                  
CONECT    2    3    1   36                                                  
CONECT    3    4    8    2   37                                             
CONECT    4    3    5   38                                                  
CONECT    5    6    4   39                                                  
CONECT    6   30    7   40    5                                             
CONECT    7    6   23   41    8                                             
CONECT    8    3    9    7   42                                             
CONECT    9    8   11   10                                                  
CONECT   10    9                                                            
CONECT   11    9   12   32   43                                             
CONECT   12   13   11   44   45                                             
CONECT   13   31   12   14   15                                             
CONECT   14   13   46                                                       
CONECT   15   16   13   47   48                                             
CONECT   16   15   17   21                                                  
CONECT   17   16   18   49                                                  
CONECT   18   17   19   50                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21   51                                                  
CONECT   21   20   16   52                                                  
CONECT   22   23   19                                                       
CONECT   23   22    7   24   53                                             
CONECT   24   25   23   30   54                                             
CONECT   25   24   26   55   56                                             
CONECT   26   25   27   57   58                                             
CONECT   27   26   29   28   59                                             
CONECT   28   27   60   61   62                                             
CONECT   29   30   27   63   64                                             
CONECT   30    6   29   65   24                                             
CONECT   31   13   32   66                                                  
CONECT   32   11   33   31                                                  
CONECT   33   32                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    2                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    6                                                            
CONECT   41    7                                                            
CONECT   42    8                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   12                                                            
CONECT   46   14                                                            
CONECT   47   15                                                            
CONECT   48   15                                                            
CONECT   49   17                                                            
CONECT   50   18                                                            
CONECT   51   20                                                            
CONECT   52   21                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
CONECT   59   27                                                            
CONECT   60   28                                                            
CONECT   61   28                                                            
CONECT   62   28                                                            
CONECT   63   29                                                            
CONECT   64   29                                                            
CONECT   65   30                                                            
CONECT   66   31                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  142    0
END

RDKit          3D

66 71  0  0  0  0  0  0  0  0999 V2000
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 28 62  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₃NO₄

Average Mass

447.5750 Da

Monoisotopic Mass

447.24096 Da

IUPAC Name

(3S,4R,7R,9S,10S,13S,14S,16S,19S,27S)-13-ethenyl-19-hydroxy-7-methyl-2-oxa-18-azahexacyclo[19.2.2.1^{3,10}.1^{16,19}.0^{4,9}.0^{14,27}]heptacosa-1(23),11,21,24-tetraene-15,17-dione

Traditional Name

(3S,4R,7R,9S,10S,13S,14S,16S,19S,27S)-13-ethenyl-19-hydroxy-7-methyl-2-oxa-18-azahexacyclo[19.2.2.1^{3,10}.1^{16,19}.0^{4,9}.0^{14,27}]heptacosa-1(23),11,21,24-tetraene-15,17-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@]12N([H])C(=O)[C@]([H])(C(=O)[C@]3([H])[C@@]4([H])[C@@]([H])(OC5=C([H])C([H])=C(C([H])=C5[H])C1([H])[H])[C@]1([H])C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[H])C([H])([H])[C@@]1([H])[C@]4([H])C([H])=C([H])[C@]3([H])C([H])=C([H])[H])C2([H])[H]

InChI Identifier

InChI=1S/C28H33NO4/c1-3-17-7-11-19-21-12-15(2)4-10-20(21)26-24(19)23(17)25(30)22-14-28(32,29-27(22)31)13-16-5-8-18(33-26)9-6-16/h3,5-9,11,15,17,19-24,26,32H,1,4,10,12-14H2,2H3,(H,29,31)/t15-,17+,19+,20-,21+,22+,23+,24+,26+,28-/m1/s1

InChI Key

VGNDUPFGVMMKPS-KOSFCWFBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hirsutella nivea	LOTUS Database	35616633
Hirsutella nivea BCC 2594	JEOL database	Isaka, M., et al, Tetrahedron 61, 5577 (2005)

Chemical Taxonomy

Classification

Not classified

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	2.64	ALOGPS
logP	4.06	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	10.66	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.63 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	127 m³·mol⁻¹	ChemAxon
Polarizability	49.38 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

9844252

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11669521

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Isaka, M., et al. (2005). Isaka, M., et al, Tetrahedron 61, 5577 (2005). Tetrahedron.

Showing NP-Card for hirsutellone B (NP0027838)

MOL for NP0027838 (hirsutellone B)

3D MOL for NP0027838 (hirsutellone B)

3D SDF for NP0027838 (hirsutellone B)

3D-SDF for NP0027838 (hirsutellone B)

PDB for NP0027838 (hirsutellone B)

3D PDB for NP0027838 (hirsutellone B)

SMILES for NP0027838 (hirsutellone B)

INCHI for NP0027838 (hirsutellone B)

Structure for NP0027838 (hirsutellone B)

3D Structure for NP0027838 (hirsutellone B)