NP-MRD: Showing NP-Card for Paspalinine (NP0066231)

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Record Information

Version

2.0

Created at

2022-04-28 10:24:02 UTC

Updated at

2022-04-28 10:24:02 UTC

NP-MRD ID

NP0066231

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Paspalinine

Description

Paspalinine 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. Paspalinine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Paspalinine is found in Aspergillus flavus sclerotia, Claviceps paspali, Penicillium janthinellum, Penicillium miczynskii and Penicillium simplicissimum. Paspalinine was first documented in 2014 (PMID: 24983640). Based on a literature review a small amount of articles have been published on Paspalinine (PMID: 32077051) (PMID: 34784090) (PMID: 33577667) (PMID: 32702474).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212242D          

 32 38  0  0  1  0            999 V2000
    8.0960    1.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2782    0.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6724   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8845    0.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7023    1.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3081    1.6089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8808    1.1242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5552    0.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1755   -0.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8500   -0.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0284   -0.8604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8463   -0.0558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0583    0.1888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4526   -0.3713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6348   -1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4227   -1.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6541   -0.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0847   -0.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2583   -0.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6785   -1.1479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245    0.2744    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7408    0.4647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4170    0.7246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0880    1.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8833    0.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8441    1.4177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0154    1.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6647    1.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1950    1.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8473   -0.9319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6669    0.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0071    0.7534    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
  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
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 14 30  1  6  0  0  0
 13 31  1  1  0  0  0
 12 32  1  6  0  0  0
M  END

     RDKit          3D

 63 69  0  0  0  0  0  0  0  0999 V2000
    4.6823   -0.7912    1.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5487   -1.2235    0.0486 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4788   -2.3944   -0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7291    2.3124   -0.4686 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6888    1.4302    1.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490    2.1985    1.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6468    1.2684    1.2132 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0737    1.7405    1.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6129    0.5112    0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6033   -0.0362   -0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0391   -1.1370   -1.0547 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3269   -1.2917   -0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2448   -2.2465   -1.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5376   -2.2123   -0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8977   -1.1981    0.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0126   -0.2309    0.6753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7244   -0.2950    0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4225    0.8410   -0.2203 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5581    2.0591   -1.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2978    0.6892   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3100    1.4154    0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6812    1.1655   -0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6373    1.9498    0.0383 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8273   -0.0977   -0.9271 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7335   -0.1563   -1.8073 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3145    0.1361    1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2684   -1.5439    2.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7277   -0.6704    2.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4177   -2.0609   -0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9673   -3.1972   -0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7775   -2.8386    0.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8260   -1.0702   -2.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3141   -2.0615   -1.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188    0.8076   -2.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4875   -0.6659   -2.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9889   -1.2894    1.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7481   -1.4768    0.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3752   -1.9912   -0.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1636    3.0608    0.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4748    0.4625    2.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4920    1.9973    2.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5738    3.1871    1.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8254    2.3398    2.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7150    0.4078    1.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5393    1.8434    2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028    2.6340    0.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5249   -1.7771   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0101   -3.0571   -1.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2612   -2.9812   -0.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9000   -1.1427    0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  1
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  5  4  1  1
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 27  5  1  0
 32  5  1  0
 10  8  1  0
 17 25  1  0
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 13 49  1  0
 13 50  1  0
 12 47  1  0
 12 48  1  0
 11 46  1  0
 28 62  1  0
 31 63  1  6
M  END


  Mrv1652304282212242D          

 32 38  0  0  1  0            999 V2000
    8.0960    1.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2782    0.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6724   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8845    0.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7023    1.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3081    1.6089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8808    1.1242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5552    0.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1755   -0.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8500   -0.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2583   -0.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6785   -1.1479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7408    0.4647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4170    0.7246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0880    1.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8833    0.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8441    1.4177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0154    1.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6647    1.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1950    1.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8473   -0.9319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6669    0.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0071    0.7534    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
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  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
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 26 27  1  0  0  0  0
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 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
M  END
> <DATABASE_ID>
NP0066231

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)O[C@@]23CC[C@]4(C)[C@]5(C)[C@H](CC6=C5NC5=CC=CC=C65)CC[C@@]4(O)C2=CC(=O)[C@@H]1O3

> <INCHI_IDENTIFIER>
InChI=1S/C27H31NO4/c1-23(2)22-19(29)14-20-26(30)10-9-15-13-17-16-7-5-6-8-18(16)28-21(17)25(15,4)24(26,3)11-12-27(20,31-22)32-23/h5-8,14-15,22,28,30H,9-13H2,1-4H3/t15-,22-,24+,25+,26+,27-/m0/s1

> <INCHI_KEY>
BPTIXFRJAOKMRK-SAMRHTEJSA-N

> <FORMULA>
C27H31NO4

> <MOLECULAR_WEIGHT>
433.548

> <EXACT_MASS>
433.225308482

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
48.77603380505568

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4R,5S,16S,19S,23R)-19-hydroxy-4,5,24,24-tetramethyl-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>
4.24

> <JCHEM_LOGP>
4.366401325333333

> <ALOGPS_LOGS>
-5.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.86287261197894

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.617551094451656

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4033673270946103

> <JCHEM_POLAR_SURFACE_AREA>
71.55000000000001

> <JCHEM_REFRACTIVITY>
121.28409999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.43e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,5S,16S,19S,23R)-19-hydroxy-4,5,24,24-tetramethyl-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
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
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                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₁NO₄

Average Mass

433.5480 Da

Monoisotopic Mass

433.22531 Da

IUPAC Name

(1S,4R,5S,16S,19S,23R)-19-hydroxy-4,5,24,24-tetramethyl-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

(1S,4R,5S,16S,19S,23R)-19-hydroxy-4,5,24,24-tetramethyl-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

CAS Registry Number

Not Available

SMILES

CC1(C)O[C@@]23CC[C@]4(C)[C@]5(C)[C@H](CC6=C5NC5=CC=CC=C65)CC[C@@]4(O)C2=CC(=O)[C@@H]1O3

InChI Identifier

InChI=1S/C27H31NO4/c1-23(2)22-19(29)14-20-26(30)10-9-15-13-17-16-7-5-6-8-18(16)28-21(17)25(15,4)24(26,3)11-12-27(20,31-22)32-23/h5-8,14-15,22,28,30H,9-13H2,1-4H3/t15-,22-,24+,25+,26+,27-/m0/s1

InChI Key

BPTIXFRJAOKMRK-SAMRHTEJSA-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
Aspergillus flavus sclerotia	Fungi	KNApSAcK
Claviceps paspali	Fungi	KNApSAcK
Penicillium janthinellum	Fungi	KNApSAcK
Penicillium miczynskii	LOTUS Database	35616633
Penicillium simplicissimum	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
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	4.24	ALOGPS
logP	4.37	ChemAxon
logS	-5.8	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	0	ChemAxon
Refractivity	121.28 m³·mol⁻¹	ChemAxon
Polarizability	48.78 Å³	ChemAxon
Number of Rings	7	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

C00023581

Chemspider ID

8043222

KEGG Compound ID

C20554

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9867531

PDB ID

Not Available

ChEBI ID

138862

Good Scents ID

Not Available

References

General References

Sun K, Li Y, Guo L, Wang Y, Liu P, Zhu W: Indole diterpenoids and isocoumarin from the fungus, Aspergillus flavus, isolated from the prawn, Penaeus vannamei. Mar Drugs. 2014 Jun 30;12(7):3970-81. doi: 10.3390/md12073970. [PubMed:24983640 ]
Kozak L, Szilagyi Z, Toth L, Pocsi I, Molnar I: Functional characterization of the idtF and idtP genes in the Claviceps paspali indole diterpene biosynthetic gene cluster. Folia Microbiol (Praha). 2020 Jun;65(3):605-613. doi: 10.1007/s12223-020-00777-6. Epub 2020 Feb 19. [PubMed:32077051 ]
Guo LD, Xu Z, Tong R: Asymmetric Total Synthesis of Indole Diterpenes Paspalicine, Paspalinine, and Paspalinine-13-ene. Angew Chem Int Ed Engl. 2022 Jan 17;61(3):e202115384. doi: 10.1002/anie.202115384. Epub 2021 Nov 27. [PubMed:34784090 ]
Enomoto M: Recent advances in the total syntheses of indole diterpenoids. Biosci Biotechnol Biochem. 2021 Jan 7;85(1):13-23. doi: 10.1093/bbb/zbaa061. [PubMed:33577667 ]
Gilchrist CLM, Lacey HJ, Vuong D, Pitt JI, Lange L, Lacey E, Pilgaard B, Chooi YH, Piggott AM: Comprehensive chemotaxonomic and genomic profiling of a biosynthetically talented Australian fungus, Aspergillus burnettii sp. nov. Fungal Genet Biol. 2020 Oct;143:103435. doi: 10.1016/j.fgb.2020.103435. Epub 2020 Jul 20. [PubMed:32702474 ]

Showing NP-Card for Paspalinine (NP0066231)

MOL for NP0066231 (Paspalinine)

3D MOL for NP0066231 (Paspalinine)

3D SDF for NP0066231 (Paspalinine)

3D-SDF for NP0066231 (Paspalinine)

PDB for NP0066231 (Paspalinine)

3D PDB for NP0066231 (Paspalinine)

SMILES for NP0066231 (Paspalinine)

INCHI for NP0066231 (Paspalinine)

Structure for NP0066231 (Paspalinine)

3D Structure for NP0066231 (Paspalinine)