NP-MRD: Showing NP-Card for Penitrem D (NP0066224)

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Record Information

Version

2.0

Created at

2022-04-28 10:23:30 UTC

Updated at

2022-04-28 10:23:30 UTC

NP-MRD ID

NP0066224

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Penitrem D

Description

Penitrem D, also known as tremortin, belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Penitrem D is found in Penicillium crustosum, Penicillium solitum and Penicillium verrucosum. Based on a literature review very few articles have been published on penitrem D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212232D          

 42 50  0  0  1  0            999 V2000
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    1.0530   -0.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1212    0.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2365    1.1033    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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 14 42  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282212232D          

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    1.6433    0.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2132   -0.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8221   -0.8779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9778    0.4147    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7407    1.2049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3065    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1094    1.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3465    0.8253    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7807    0.2249    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0177   -0.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8206   -0.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3864   -0.1547    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1493    0.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7151    1.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5180    1.0461    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7551    0.2559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1893   -0.3445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5579    0.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1238    0.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7950   -0.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0838    1.6465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149   -0.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9123    1.4257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8860   -0.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739    2.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1026    2.9988    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
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  1 11  1  0  0  0  0
  8 12  1  1  0  0  0
 13 12  1  6  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
  5 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  4 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 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  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  1  0  0  0
 32 34  1  1  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 31 37  1  1  0  0  0
 25 38  1  1  0  0  0
 24 39  1  6  0  0  0
 20 40  1  6  0  0  0
 14 41  1  0  0  0  0
 14 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066224

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@H]1O[C@H]2CC[C@]3(C)[C@]4(C)[C@@H](CC[C@@]3(O)C2=C[C@H]1O)[C@@H]1OC(C)(C)[C@H]2C[C@H]3[C@@H]2C2=C5C(NC4=C15)=CC=C2CC3=C

> <INCHI_IDENTIFIER>
InChI=1S/C37H45NO4/c1-17(2)31-25(39)16-22-26(41-31)11-12-35(6)36(7)21(10-13-37(22,35)40)32-30-29-24(38-33(30)36)9-8-19-14-18(3)20-15-23(28(20)27(19)29)34(4,5)42-32/h8-9,16,20-21,23,25-26,28,31-32,38-40H,1,3,10-15H2,2,4-7H3/t20-,21+,23+,25-,26+,28+,31-,32+,35-,36-,37-/m1/s1

> <INCHI_KEY>
XOASTWITKYDKAJ-PPQPEBMASA-N

> <FORMULA>
C37H45NO4

> <MOLECULAR_WEIGHT>
567.77

> <EXACT_MASS>
567.334858933

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
66.5139288207263

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,8R,9R,11S,14R,15S,24S,26S,27S)-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0^{2,15}.0^{5,14}.0^{6,11}.0^{16,30}.0^{18,29}.0^{21,28}.0^{24,27}]dotriaconta-6,16(30),18(29),19,21(28)-pentaene-5,8-diol

> <ALOGPS_LOGP>
5.17

> <JCHEM_LOGP>
5.111700419666668

> <ALOGPS_LOGS>
-6.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.036356181799423

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.423976272998328

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3536229414809915

> <JCHEM_POLAR_SURFACE_AREA>
74.71000000000001

> <JCHEM_REFRACTIVITY>
164.5676

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.17e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,8R,9R,11S,14R,15S,24S,26S,27S)-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0^{2,15}.0^{5,14}.0^{6,11}.0^{16,30}.0^{18,29}.0^{21,28}.0^{24,27}]dotriaconta-6,16(30),18(29),19,21(28)-pentaene-5,8-diol

> <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      -0.941  -0.332   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.655  -1.846   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.798  -2.355   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.966  -1.350   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.680   0.163   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.226   0.672   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.442   2.059   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.977   2.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.845   0.903   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.381   1.018   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.177  -0.485   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.386   4.022   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.067   3.513   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.455   4.181   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.909   3.672   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.576   2.284   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.067   0.831   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.131  -0.283   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.401  -1.639   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       5.559   0.774   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.116   2.249   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.172   3.370   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.671   3.016   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.113   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.057   0.420   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.500  -1.055   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.998  -1.410   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.055  -0.289   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.612   1.186   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.668   2.307   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.167   1.953   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.609   0.478   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      11.553  -0.643   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.108   0.123   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.164   1.244   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.551  -1.352   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      13.223   3.073   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.001  -0.701   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       9.170   2.661   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.387  -0.756   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.698   5.522   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.058   5.598   0.000  0.00  0.00           C+0
CONECT    1    2    6   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6   17                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    1                                                       
CONECT   12    8   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15   41   42                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16    5   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18    4                                                       
CONECT   20   18   21   25   40                                             
CONECT   21   20   16   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29   39                                             
CONECT   25   24   20   26   38                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   24   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32   28                                                       
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   31                                                            
CONECT   38   25                                                            
CONECT   39   24                                                            
CONECT   40   20                                                            
CONECT   41   14                                                            
CONECT   42   14                                                            
MASTER        0    0    0    0    0    0    0    0   42    0  100    0
END

View in JSmol

Synonyms

Value	Source
Penitrem a	MeSH
Penitrem b	MeSH
Penitrem e	MeSH
Penitrems	MeSH
Tremortin	MeSH
Tremortin a	MeSH
Tremortin b	MeSH

Chemical Formula

C₃₇H₄₅NO₄

Average Mass

567.7700 Da

Monoisotopic Mass

567.33486 Da

IUPAC Name

(1S,2R,5S,8R,9R,11S,14R,15S,24S,26S,27S)-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0^{2,15}.0^{5,14}.0^{6,11}.0^{16,30}.0^{18,29}.0^{21,28}.0^{24,27}]dotriaconta-6,16(30),18(29),19,21(28)-pentaene-5,8-diol

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=C)[C@H]1O[C@H]2CC[C@]3(C)[C@]4(C)[C@@H](CC[C@@]3(O)C2=C[C@H]1O)[C@@H]1OC(C)(C)[C@H]2C[C@H]3[C@@H]2C2=C5C(NC4=C15)=CC=C2CC3=C

InChI Identifier

InChI=1S/C37H45NO4/c1-17(2)31-25(39)16-22-26(41-31)11-12-35(6)36(7)21(10-13-37(22,35)40)32-30-29-24(38-33(30)36)9-8-19-14-18(3)20-15-23(28(20)27(19)29)34(4,5)42-32/h8-9,16,20-21,23,25-26,28,31-32,38-40H,1,3,10-15H2,2,4-7H3/t20-,21+,23+,25-,26+,28+,31-,32+,35-,36-,37-/m1/s1

InChI Key

XOASTWITKYDKAJ-PPQPEBMASA-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
Penicillium crustosum	Fungi	KNApSAcK
Penicillium solitum	LOTUS Database	35616633
Penicillium verrucosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Tetralin
3-alkylindole
Indole
Indole or derivatives
Pyran
Benzenoid
Cyclic alcohol
Heteroaromatic compound
Pyrrole
Tertiary alcohol
Secondary alcohol
Ether
Dialkyl ether
Oxacycle
Azacycle
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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	5.17	ALOGPS
logP	5.11	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	13.42	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	74.71 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	164.57 m³·mol⁻¹	ChemAxon
Polarizability	66.51 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	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

C00023572

Chemspider ID

2299505

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3035208

PDB ID

Not Available

ChEBI ID

138854

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Penitrem D (NP0066224)

MOL for NP0066224 (Penitrem D)

3D MOL for NP0066224 (Penitrem D)

3D SDF for NP0066224 (Penitrem D)

3D-SDF for NP0066224 (Penitrem D)

PDB for NP0066224 (Penitrem D)

3D PDB for NP0066224 (Penitrem D)

SMILES for NP0066224 (Penitrem D)

INCHI for NP0066224 (Penitrem D)

Structure for NP0066224 (Penitrem D)

3D Structure for NP0066224 (Penitrem D)