NP-MRD: Showing NP-Card for Paspalitrem C (NP0066237)

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Record Information

Version

2.0

Created at

2022-04-28 10:24:39 UTC

Updated at

2022-04-28 10:24:40 UTC

NP-MRD ID

NP0066237

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Paspalitrem C

Description

Paspalitrem C 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. Paspalitrem C is found in Claviceps paspali sclerotia. Based on a literature review very few articles have been published on Paspalitrem C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212242D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282212242D          

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  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 12 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
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 23 22  1  6  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 14 30  1  6  0  0  0
 13 31  1  1  0  0  0
 12 32  1  6  0  0  0
  3 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066237

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2C3=C(NC2=CC=C1)[C@@]1(C)[C@H](C3)CC[C@@]2(O)C3=CC(=O)[C@@H]4O[C@@]3(CC[C@]12C)OC4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H39NO4/c1-18(2)10-11-19-8-7-9-22-25(19)21-16-20-12-13-31(35)24-17-23(34)27-28(3,4)37-32(24,36-27)15-14-29(31,5)30(20,6)26(21)33-22/h7-10,17,20,27,33,35H,11-16H2,1-6H3/t20-,27-,29+,30+,31+,32-/m0/s1

> <INCHI_KEY>
MXOIVWLOTRYIQC-TZHHUJIHSA-N

> <FORMULA>
C32H39NO4

> <MOLECULAR_WEIGHT>
501.667

> <EXACT_MASS>
501.28790874

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
58.114551521009275

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4R,5S,16S,19S,23R)-19-hydroxy-4,5,24,24-tetramethyl-12-(3-methylbut-2-en-1-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0^{1,20}.0^{4,19}.0^{5,16}.0^{6,14}.0^{8,13}]hexacosa-6(14),8,10,12,20-pentaen-22-one

> <ALOGPS_LOGP>
5.62

> <JCHEM_LOGP>
6.094968324666665

> <ALOGPS_LOGS>
-6.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.80162399253323

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.617510988356354

> <JCHEM_PKA_STRONGEST_BASIC>
-3.403367327719624

> <JCHEM_POLAR_SURFACE_AREA>
71.55000000000001

> <JCHEM_REFRACTIVITY>
145.5269

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.11e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,5S,16S,19S,23R)-19-hydroxy-4,5,24,24-tetramethyl-12-(3-methylbut-2-en-1-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0^{1,20}.0^{4,19}.0^{5,16}.0^{6,14}.0^{8,13}]hexacosa-6(14),8,10,12,20-pentaen-22-one

> <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      15.113   2.547   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.453   1.045   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.322  -0.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.851   0.456   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.511   1.958   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.642   3.003   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      10.977   2.098   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      10.370   0.683   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.528  -0.332   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.920  -1.747   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.386  -1.606   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.046  -0.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.576   0.352   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.445  -0.693   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.785  -2.195   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.256  -2.652   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.954  -0.233   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.891  -1.459   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.349  -1.047   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.267  -2.143   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.912   0.512   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.249   0.867   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.512   1.353   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.764   2.335   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.249   1.866   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.442   2.646   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.895   2.128   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.241   3.522   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.364   2.289   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.315  -1.739   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.711   1.392   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.347   1.406   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.662  -1.503   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.133  -1.959   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.473  -3.461   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      17.944  -3.918   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      15.342  -4.507   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11    8   13   32                                             
CONECT   13   12   14   25   31                                             
CONECT   14   13   15   17   30                                             
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   17   24   26                                             
CONECT   24   23   25                                                       
CONECT   25   24   13                                                       
CONECT   26   23   27                                                       
CONECT   27   26   21   28   29                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   14                                                            
CONECT   31   13                                                            
CONECT   32   12                                                            
CONECT   33    3   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₉NO₄

Average Mass

501.6670 Da

Monoisotopic Mass

501.28791 Da

IUPAC Name

(1S,4R,5S,16S,19S,23R)-19-hydroxy-4,5,24,24-tetramethyl-12-(3-methylbut-2-en-1-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.0^{1,20}.0^{4,19}.0^{5,16}.0^{6,14}.0^{8,13}]hexacosa-6(14),8,10,12,20-pentaen-22-one

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2C3=C(NC2=CC=C1)[C@@]1(C)[C@H](C3)CC[C@@]2(O)C3=CC(=O)[C@@H]4O[C@@]3(CC[C@]12C)OC4(C)C

InChI Identifier

InChI=1S/C32H39NO4/c1-18(2)10-11-19-8-7-9-22-25(19)21-16-20-12-13-31(35)24-17-23(34)27-28(3,4)37-32(24,36-27)15-14-29(31,5)30(20,6)26(21)33-22/h7-10,17,20,27,33,35H,11-16H2,1-6H3/t20-,27-,29+,30+,31+,32-/m0/s1

InChI Key

MXOIVWLOTRYIQC-TZHHUJIHSA-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
Claviceps paspali sclerotia	Fungi	KNApSAcK

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
3-alkylindole
Indole
Indole or derivatives
Dihydropyranone
Ketal
Pyran
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Pyrrole
Meta-dioxolane
Cyclic alcohol
Ketone
Acetal
Oxacycle
Azacycle
Organooxygen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organonitrogen 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	5.62	ALOGPS
logP	6.09	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	71.55 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	145.53 m³·mol⁻¹	ChemAxon
Polarizability	58.11 Å³	ChemAxon
Number of Rings	7	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

C00023589

Chemspider ID

8024594

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9848881

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Paspalitrem C (NP0066237)

MOL for NP0066237 (Paspalitrem C)

3D MOL for NP0066237 (Paspalitrem C)

3D SDF for NP0066237 (Paspalitrem C)

3D-SDF for NP0066237 (Paspalitrem C)

PDB for NP0066237 (Paspalitrem C)

3D PDB for NP0066237 (Paspalitrem C)

SMILES for NP0066237 (Paspalitrem C)

INCHI for NP0066237 (Paspalitrem C)

Structure for NP0066237 (Paspalitrem C)

3D Structure for NP0066237 (Paspalitrem C)