NP-MRD: Showing NP-Card for Paxilline (NP0066232)

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Record Information

Version

2.0

Created at

2022-04-28 10:24:05 UTC

Updated at

2025-07-23 20:01:21 UTC

NP-MRD ID

NP0066232

Natural Product DOI

https://doi.org/10.57994/4382

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Paxilline

Description

Paxilline 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. Paxilline is an extremely weak basic (essentially neutral) compound (based on its pKa). Tremorgenic agent from Penicillium paxilli, Acremonium lorii, Emericella foveolata, Emericella desertorum and Emericella striata Paxilline is a potassium channel blocker. Paxilline is a toxic, tremorgenic indole alkaloid produced by Penicillium paxilli. Paxilline is found in Acremonium lorii, Chaunopycnis alba, Claviceps paspali, Emericella desertorum, Emericella foreolata, Emericella foveolata, Emericella striata, Lolium perenne, Lolium perenne L. , Penicillium miczynskii, Penicillium paxilli and Penicillium thiersii. Paxilline is a potassium channel blocker.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 01111302282D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 01111302282D          

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M  END
> <DATABASE_ID>
NP0066232

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC3=C(NC4=CC=CC=C34)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@H](C(=O)C=C3[C@]1(O)CC2)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C27H33NO4/c1-24(2,30)23-20(29)14-18-21(32-23)10-11-25(3)26(4)15(9-12-27(18,25)31)13-17-16-7-5-6-8-19(16)28-22(17)26/h5-8,14-15,21,23,28,30-31H,9-13H2,1-4H3/t15-,21-,23-,25+,26+,27+/m0/s1

> <INCHI_KEY>
ACNHBCIZLNNLRS-UBGQALKQSA-N

> <FORMULA>
C27H33NO4

> <MOLECULAR_WEIGHT>
435.5552

> <EXACT_MASS>
435.240958549

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
50.073463997706895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

> <ALOGPS_LOGP>
4.38

> <JCHEM_LOGP>
3.6230832606666667

> <ALOGPS_LOGS>
-5.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.266006219827634

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.55890296680625

> <JCHEM_PKA_STRONGEST_BASIC>
-3.178614806490442

> <JCHEM_POLAR_SURFACE_AREA>
82.55000000000001

> <JCHEM_REFRACTIVITY>
123.2165

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
paxilline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-JAN-13         0                                  
HETATM    1  C   UNK     0     -13.053 -22.973   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -14.387 -22.203   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.387 -20.662   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -13.053 -19.892   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -11.720 -20.662   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -11.720 -22.203   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0     -10.386 -19.892   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -7.719 -22.972   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.385 -22.202   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.385 -20.662   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.052 -20.662   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.052 -22.202   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.051 -22.972   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.051 -19.892   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.718 -20.662   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.718 -22.202   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.051 -18.352   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.718 -17.582   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.384 -18.352   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.384 -19.892   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.050 -20.662   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.050 -17.582   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.283 -18.352   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.283 -19.892   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.617 -20.662   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.617 -17.582   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.951 -18.352   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.617 -16.042   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.951 -16.812   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      -6.385 -23.742   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0      -5.051 -21.432   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.385 -19.122   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.718 -19.122   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0      -2.384 -16.812   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    7    6                                                  
CONECT    6    1    5   12                                                  
CONECT    7    5   11                                                       
CONECT    8    9   12                                                       
CONECT    9    8   13   10   30                                             
CONECT   10   11    9   14   32                                             
CONECT   11    7   10   12                                                  
CONECT   12    6    8   11                                                  
CONECT   13    9   16                                                       
CONECT   14   10   15   17   31                                             
CONECT   15   16   20   14   33                                             
CONECT   16   15   13                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22   34                                             
CONECT   20   15   21   19                                                  
CONECT   21   20   24                                                       
CONECT   22   19   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   21   25                                                  
CONECT   25   24                                                            
CONECT   26   23   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26                                                            
CONECT   30    9                                                            
CONECT   31   14                                                            
CONECT   32   10                                                            
CONECT   33   15                                                            
CONECT   34   19                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₃NO₄

Average Mass

435.5552 Da

Monoisotopic Mass

435.24096 Da

IUPAC Name

(1S,2R,5S,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

Traditional Name

paxilline

CAS Registry Number

Not Available

SMILES

[H][C@]12CC3=C(NC4=CC=CC=C34)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@H](C(=O)C=C3[C@]1(O)CC2)C(C)(C)O

InChI Identifier

InChI=1S/C27H33NO4/c1-24(2,30)23-20(29)14-18-21(32-23)10-11-25(3)26(4)15(9-12-27(18,25)31)13-17-16-7-5-6-8-19(16)28-22(17)26/h5-8,14-15,21,23,28,30-31H,9-13H2,1-4H3/t15-,21-,23-,25+,26+,27+/m0/s1

InChI Key

ACNHBCIZLNNLRS-UBGQALKQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

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
Acremonium lorii	Fungi	KNApSAcK
Chaunopycnis alba	-	KNApSAcK
Claviceps paspali	Fungi	KNApSAcK
Emericella desertorum	-	KNApSAcK
Emericella foreolata	-	KNApSAcK
Emericella foveolata	-	KNApSAcK
Emericella striata	-	KNApSAcK
Lolium perenne	LOTUS Database	35616633
Lolium perenne L.	Plant	KNApSAcK
Penicillium miczynskii	LOTUS Database	35616633
Penicillium paxilli	Fungi	KNApSAcK
Penicillium thiersii	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
Pyran
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Pyrrole
Cyclic alcohol
Cyclic ketone
Ketone
Oxacycle
Azacycle
Dialkyl ether
Ether
Alcohol
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:34907 )
organooxygen compound (CHEBI:34907 )

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	4.38	ALOGPS
logP	3.62	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	13.56	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.55 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	123.22 m³·mol⁻¹	ChemAxon
Polarizability	50.07 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