NP-MRD: Showing NP-Card for (1r,6r,7e,9s,11e,13r,16r,27s,30r)-6,29-dihydroxy-7,9,16,30-tetramethyl-18,28-diazahexacyclo[14.13.1.0¹,¹³.0¹⁷,²⁵.0¹⁹,²⁴.0²⁷,³⁰]triaconta-3,7,11,17(25),19,21,23,28-octaene-2,5-dione (NP0231755)

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Record Information

Version

2.0

Created at

2022-09-06 12:45:06 UTC

Updated at

2022-09-06 12:45:07 UTC

NP-MRD ID

NP0231755

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,6r,7e,9s,11e,13r,16r,27s,30r)-6,29-dihydroxy-7,9,16,30-tetramethyl-18,28-diazahexacyclo[14.13.1.0¹,¹³.0¹⁷,²⁵.0¹⁹,²⁴.0²⁷,³⁰]triaconta-3,7,11,17(25),19,21,23,28-octaene-2,5-dione

Description

Penochalasin I belongs to the class of organic compounds known as pyrrolocarbazoles. Pyrrolocarbazoles are compounds containing a pyrrolocarbazole moiety, which is a tetracyclic heterocycle which consists of a pyrrole ring fused to a carbazole. (1r,6r,7e,9s,11e,13r,16r,27s,30r)-6,29-dihydroxy-7,9,16,30-tetramethyl-18,28-diazahexacyclo[14.13.1.0¹,¹³.0¹⁷,²⁵.0¹⁹,²⁴.0²⁷,³⁰]triaconta-3,7,11,17(25),19,21,23,28-octaene-2,5-dione is found in Penicillium chrysogenum. Based on a literature review very few articles have been published on Penochalasin I.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062214452D          

 38 43  0  0  1  0            999 V2000
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 37 38  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309062214452D          

 38 43  0  0  1  0            999 V2000
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    2.4448   -2.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8379   -1.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1587   -0.7511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9364   -1.4620    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5007   -2.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2522   -0.0699    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0716   -0.1652    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
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  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
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 14 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 28 26  1  1  0  0  0
  9 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 31 29  1  4  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  1  6  0  0  0
 28 37  1  0  0  0  0
 24 37  1  0  0  0  0
 12 37  1  0  0  0  0
 37 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0231755

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C\C=C\[C@H]2CC[C@@]3(C)C4=C(C[C@@H]5N=C(O)[C@]2(C(=O)C=CC(=O)[C@H](O)\C(C)=C\1)[C@@]35C)C1=CC=CC=C1N4

> <INCHI_IDENTIFIER>
InChI=1S/C32H36N2O4/c1-18-8-7-9-20-14-15-30(3)28-22(21-10-5-6-11-23(21)33-28)17-25-31(30,4)32(20,29(38)34-25)26(36)13-12-24(35)27(37)19(2)16-18/h5-7,9-13,16,18,20,25,27,33,37H,8,14-15,17H2,1-4H3,(H,34,38)/b9-7+,13-12?,19-16+/t18-,20-,25-,27+,30-,31+,32-/m0/s1

> <INCHI_KEY>
CNOXPHKUUAMNSN-VXHPOFCZSA-N

> <FORMULA>
C32H36N2O4

> <MOLECULAR_WEIGHT>
512.65

> <EXACT_MASS>
512.267507647

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
57.70712444803841

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,6R,7E,9S,11E,13R,16R,27S,30R)-6,29-dihydroxy-7,9,16,30-tetramethyl-18,28-diazahexacyclo[14.13.1.0^{1,13}.0^{17,25}.0^{19,24}.0^{27,30}]triaconta-3,7,11,17(25),19,21,23,28-octaene-2,5-dione

> <JCHEM_LOGP>
4.666317084550298

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.826332279217318

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.747151064704646

> <JCHEM_PKA_STRONGEST_BASIC>
5.376779938648101

> <JCHEM_POLAR_SURFACE_AREA>
102.75

> <JCHEM_REFRACTIVITY>
150.14909999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,6R,7E,9S,11E,13R,16R,27S,30R)-6,29-dihydroxy-7,9,16,30-tetramethyl-18,28-diazahexacyclo[14.13.1.0^{1,13}.0^{17,25}.0^{19,24}.0^{27,30}]triaconta-3,7,11,17(25),19,21,23,28-octaene-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.547  -1.370   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.993  -1.387   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.778  -0.062   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.023   1.280   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.517   1.298   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.807   2.605   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.347   2.588   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.102   1.246   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.642   1.229   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.427   2.554   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.967   2.537   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.722   1.195   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.685   2.397   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.483   0.666   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      11.739   1.557   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      12.975   0.638   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.485   0.941   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.502  -0.215   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.010  -1.674   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.500  -1.977   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.483  -0.821   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.943  -0.804   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.900  -1.937   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.397  -1.600   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       7.141  -2.492   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       6.116  -1.518   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.435  -2.032   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.397  -0.113   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.602  -1.599   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.712  -1.212   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.906  -3.109   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.564  -3.864   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.431  -2.821   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.030  -1.402   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.748  -2.729   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.935  -4.037   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.937  -0.130   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.467  -0.308   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   28                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   37                                             
CONECT   13   12                                                            
CONECT   14   12   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21   14   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   37                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    9   29   37                                             
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    2   36                                                  
CONECT   36   35                                                            
CONECT   37   28   24   12   38                                             
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₆N₂O₄

Average Mass

512.6500 Da

Monoisotopic Mass

512.26751 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1C\C=C\[C@H]2CC[C@@]3(C)C4=C(C[C@@H]5N=C(O)[C@]2(C(=O)C=CC(=O)[C@H](O)\C(C)=C\1)[C@@]35C)C1=CC=CC=C1N4

InChI Identifier

InChI=1S/C32H36N2O4/c1-18-8-7-9-20-14-15-30(3)28-22(21-10-5-6-11-23(21)33-28)17-25-31(30,4)32(20,29(38)34-25)26(36)13-12-24(35)27(37)19(2)16-18/h5-7,9-13,16,18,20,25,27,33,37H,8,14-15,17H2,1-4H3,(H,34,38)/b9-7+,13-12?,19-16+/t18-,20-,25-,27+,30-,31+,32-/m0/s1

InChI Key

CNOXPHKUUAMNSN-VXHPOFCZSA-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
Penicillium chrysogenum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolocarbazoles. Pyrrolocarbazoles are compounds containing a pyrrolocarbazole moiety, which is a tetracyclic heterocycle which consists of a pyrrole ring fused to a carbazole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Pyrrolocarbazoles

Alternative Parents

Substituents

Pyrrolocarbazole
3-alkylindole
Isoindole or derivatives
Indole
Benzenoid
Heteroaromatic compound
Cyclic carboximidic acid
Pyrroline
Pyrrole
Cyclic ketone
Secondary alcohol
Ketone
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
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

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

139590394

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,6r,7e,9s,11e,13r,16r,27s,30r)-6,29-dihydroxy-7,9,16,30-tetramethyl-18,28-diazahexacyclo[14.13.1.0¹,¹³.0¹⁷,²⁵.0¹⁹,²⁴.0²⁷,³⁰]triaconta-3,7,11,17(25),19,21,23,28-octaene-2,5-dione (NP0231755)

MOL for NP0231755 ((1r,6r,7e,9s,11e,13r,16r,27s,30r)-6,29-dihydroxy-7,9,16,30-tetramethyl-18,28-diazahexacyclo[14.13.1.0¹,¹³.0¹⁷,²⁵.0¹⁹,²⁴.0²⁷,³⁰]triaconta-3,7,11,17(25),19,21,23,28-octaene-2,5-dione)

3D MOL for NP0231755 ((1r,6r,7e,9s,11e,13r,16r,27s,30r)-6,29-dihydroxy-7,9,16,30-tetramethyl-18,28-diazahexacyclo[14.13.1.0¹,¹³.0¹⁷,²⁵.0¹⁹,²⁴.0²⁷,³⁰]triaconta-3,7,11,17(25),19,21,23,28-octaene-2,5-dione)

3D SDF for NP0231755 ((1r,6r,7e,9s,11e,13r,16r,27s,30r)-6,29-dihydroxy-7,9,16,30-tetramethyl-18,28-diazahexacyclo[14.13.1.0¹,¹³.0¹⁷,²⁵.0¹⁹,²⁴.0²⁷,³⁰]triaconta-3,7,11,17(25),19,21,23,28-octaene-2,5-dione)

3D-SDF for NP0231755 ((1r,6r,7e,9s,11e,13r,16r,27s,30r)-6,29-dihydroxy-7,9,16,30-tetramethyl-18,28-diazahexacyclo[14.13.1.0¹,¹³.0¹⁷,²⁵.0¹⁹,²⁴.0²⁷,³⁰]triaconta-3,7,11,17(25),19,21,23,28-octaene-2,5-dione)

PDB for NP0231755 ((1r,6r,7e,9s,11e,13r,16r,27s,30r)-6,29-dihydroxy-7,9,16,30-tetramethyl-18,28-diazahexacyclo[14.13.1.0¹,¹³.0¹⁷,²⁵.0¹⁹,²⁴.0²⁷,³⁰]triaconta-3,7,11,17(25),19,21,23,28-octaene-2,5-dione)

3D PDB for NP0231755 ((1r,6r,7e,9s,11e,13r,16r,27s,30r)-6,29-dihydroxy-7,9,16,30-tetramethyl-18,28-diazahexacyclo[14.13.1.0¹,¹³.0¹⁷,²⁵.0¹⁹,²⁴.0²⁷,³⁰]triaconta-3,7,11,17(25),19,21,23,28-octaene-2,5-dione)

SMILES for NP0231755 ((1r,6r,7e,9s,11e,13r,16r,27s,30r)-6,29-dihydroxy-7,9,16,30-tetramethyl-18,28-diazahexacyclo[14.13.1.0¹,¹³.0¹⁷,²⁵.0¹⁹,²⁴.0²⁷,³⁰]triaconta-3,7,11,17(25),19,21,23,28-octaene-2,5-dione)

INCHI for NP0231755 ((1r,6r,7e,9s,11e,13r,16r,27s,30r)-6,29-dihydroxy-7,9,16,30-tetramethyl-18,28-diazahexacyclo[14.13.1.0¹,¹³.0¹⁷,²⁵.0¹⁹,²⁴.0²⁷,³⁰]triaconta-3,7,11,17(25),19,21,23,28-octaene-2,5-dione)

Structure for NP0231755 ((1r,6r,7e,9s,11e,13r,16r,27s,30r)-6,29-dihydroxy-7,9,16,30-tetramethyl-18,28-diazahexacyclo[14.13.1.0¹,¹³.0¹⁷,²⁵.0¹⁹,²⁴.0²⁷,³⁰]triaconta-3,7,11,17(25),19,21,23,28-octaene-2,5-dione)

3D Structure for NP0231755 ((1r,6r,7e,9s,11e,13r,16r,27s,30r)-6,29-dihydroxy-7,9,16,30-tetramethyl-18,28-diazahexacyclo[14.13.1.0¹,¹³.0¹⁷,²⁵.0¹⁹,²⁴.0²⁷,³⁰]triaconta-3,7,11,17(25),19,21,23,28-octaene-2,5-dione)