NP-MRD: Showing NP-Card for Paspaline (NP0066229)

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Record Information

Version

2.0

Created at

2022-04-28 10:23:50 UTC

Updated at

2024-09-03 04:15:01 UTC

NP-MRD ID

NP0066229

Natural Product DOI

https://doi.org/10.57994/0125

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Paspaline

Description

2-[(1S,2S,5S,7S,10S,11R,14S)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]Tetracosa-16(24),17,19,21-tetraen-7-yl]propan-2-ol 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. 2-[(1S,2S,5S,7S,10S,11R,14S)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]Tetracosa-16(24),17,19,21-tetraen-7-yl]propan-2-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). Paspaline is found in Albophoma yamanashiensis, Aspergillus alliaceus, Aspergillus flavus, Aspergillus oryzae, Chaunopycnis alba, Claviceps paspali, Aspergillus striatus, Neotyphodium lolii, Epichloe festucae Fg1, Epichloe festucae Fl1, Epicholoe festucae, Lolium perenne, Neotyphodium coenophialum e822, Neotyphodium coenophialum Tf28, Neotyphodium festucae Frc7, Neotyphodium funkii e4096, Neotyphodium lolii AR1, Neotyphodium lolii Lp14, Neotyphodium lolii Lp19, Neotyphodium siegelii e915, Neotyphodium tembladerae e1169, Neotyphodium tembladerae e4055, Penicillium crustosum, Penicillium janthinellum, Penicillium paxilli and Penicillium thiersii. 2-[(1S,2S,5S,7S,10S,11R,14S)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]Tetracosa-16(24),17,19,21-tetraen-7-yl]propan-2-ol is a potentially toxic compound.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 08291401162D          

 35 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 08291401162D          

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  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 11 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 17 10  1  0  0  0  0
 17 16  1  0  0  0  0
 18  8  2  0  0  0  0
 19 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20  9  2  0  0  0  0
 20 18  1  0  0  0  0
 21 11  1  0  0  0  0
 22 12  1  0  0  0  0
 23 13  1  0  0  0  0
 24 19  2  0  0  0  0
 25  1  1  0  0  0  0
 25  2  1  0  0  0  0
 22 25  1  6  0  0  0
 26  3  1  6  0  0  0
 26 14  1  0  0  0  0
 26 21  1  0  0  0  0
 26 23  1  0  0  0  0
 27  4  1  6  0  0  0
 27 15  1  0  0  0  0
 27 21  1  0  0  0  0
 28  5  1  1  0  0  0
 28 17  1  0  0  0  0
 28 24  1  0  0  0  0
 28 27  1  0  0  0  0
 29 20  1  0  0  0  0
 29 24  1  0  0  0  0
 30 25  1  0  0  0  0
 31 22  1  0  0  0  0
 31 23  1  0  0  0  0
 17 32  1  6  0  0  0
 21 33  1  1  0  0  0
 22 34  1  1  0  0  0
 23 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0066229

> <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])(CC[C@@]3(C)[C@]1([H])CC2)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C28H39NO2/c1-25(2,30)22-12-14-26(3)21-11-10-17-16-19-18-8-6-7-9-20(18)29-24(19)28(17,5)27(21,4)15-13-23(26)31-22/h6-9,17,21-23,29-30H,10-16H2,1-5H3/t17-,21-,22-,23-,26-,27-,28+/m0/s1

> <INCHI_KEY>
WLAIEIMDXUAGPY-HSECPPETSA-N

> <FORMULA>
C28H39NO2

> <MOLECULAR_WEIGHT>
421.6148

> <EXACT_MASS>
421.298079497

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.52545461834933

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1S,2S,5S,7S,10S,11R,14S)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-16(24),17,19,21-tetraen-7-yl]propan-2-ol

> <ALOGPS_LOGP>
6.30

> <JCHEM_LOGP>
5.6359221396666666

> <ALOGPS_LOGS>
-7.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.860463551856473

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.324846174098045

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0935564409641225

> <JCHEM_POLAR_SURFACE_AREA>
45.25

> <JCHEM_REFRACTIVITY>
125.02669999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.02e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1S,2S,5S,7S,10S,11R,14S)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-16(24),17,19,21-tetraen-7-yl]propan-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0      20.170  -5.625   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.943  -3.589   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.170  -7.647   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.422  -4.946   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.785  -5.015   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.768  -6.115   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924  -4.583   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.018  -7.016   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.328  -3.952   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.361  -8.911   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.765  -8.279   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.979  -6.384   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.231  -3.683   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.574  -7.016   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.827  -4.314   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.606  -8.336   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.112  -8.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.422  -6.384   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.831  -7.005   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.577  -4.852   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.921  -6.747   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.134  -4.852   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.480  -4.583   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.858  -5.857   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.539  -4.220   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.325  -6.115   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.671  -5.846   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.267  -6.478   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       9.083  -4.526   0.000  0.00  0.00           N+0
HETATM   30  O   UNK     0      18.907  -2.816   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      16.885  -3.952   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0      12.516  -7.379   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      14.076  -5.215   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      18.289  -3.320   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      16.730  -5.484   0.000  0.00  0.00           H+0
CONECT    1   25                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6    7    8                                                       
CONECT    7    6    9                                                       
CONECT    8    6   18                                                       
CONECT    9    7   20                                                       
CONECT   10   11   17                                                       
CONECT   11   10   21                                                       
CONECT   12   14   22                                                       
CONECT   13   15   23                                                       
CONECT   14   12   26                                                       
CONECT   15   13   27                                                       
CONECT   16   17   19                                                       
CONECT   17   10   16   28   32                                             
CONECT   18    8   19   20                                                  
CONECT   19   16   18   24                                                  
CONECT   20    9   18   29                                                  
CONECT   21   11   26   27   33                                             
CONECT   22   12   25   31   34                                             
CONECT   23   13   26   31   35                                             
CONECT   24   19   28   29                                                  
CONECT   25    1    2   22   30                                             
CONECT   26    3   14   21   23                                             
CONECT   27    4   15   21   28                                             
CONECT   28    5   17   24   27                                             
CONECT   29   20   24                                                       
CONECT   30   25                                                            
CONECT   31   22   23                                                       
CONECT   32   17                                                            
CONECT   33   21                                                            
CONECT   34   22                                                            
CONECT   35   23                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₉NO₂

Average Mass

421.6148 Da

Monoisotopic Mass

421.29808 Da

IUPAC Name

2-[(1S,2S,5S,7S,10S,11R,14S)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-16(24),17,19,21-tetraen-7-yl]propan-2-ol

Traditional Name

2-[(1S,2S,5S,7S,10S,11R,14S)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-16(24),17,19,21-tetraen-7-yl]propan-2-ol

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])(CC[C@@]3(C)[C@]1([H])CC2)C(C)(C)O

InChI Identifier

InChI=1S/C28H39NO2/c1-25(2,30)22-12-14-26(3)21-11-10-17-16-19-18-8-6-7-9-20(18)29-24(19)28(17,5)27(21,4)15-13-23(26)31-22/h6-9,17,21-23,29-30H,10-16H2,1-5H3/t17-,21-,22-,23-,26-,27-,28+/m0/s1

InChI Key

WLAIEIMDXUAGPY-HSECPPETSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Merangelgri			2022-10-12	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 126 MHz, CDCl3, experimental)	merangelgri@uncg.edu	Not Available	Not Available	2023-01-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	merangelgri@uncg.edu	Not Available	Not Available	2023-01-12	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 126 MHz, CDCl3, experimental)	merangelgri@uncg.edu	Not Available	Not Available	2023-01-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	merangelgri@uncg.edu	Not Available	Not Available	2023-01-12	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 126 MHz, CDCl3, experimental)	merangelgri@uncg.edu	Not Available	Not Available	2022-12-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	merangelgri@uncg.edu	Not Available	Not Available	2022-12-21	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 126 MHz, CDCl3, experimental)	merangelgri@uncg.edu	Not Available	Not Available	2022-12-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	merangelgri@uncg.edu	Not Available	Not Available	2022-12-21	View Spectrum

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
Albophoma yamanashiensis	LOTUS Database	35616633
Aspergillus alliaceus	LOTUS Database	35616633
Aspergillus flavus	Fungi	KNApSAcK
Aspergillus oryzae	Fungi	KNApSAcK
Chaunopycnis alba	-	KNApSAcK
Claviceps paspali	Fungi	KNApSAcK
Emericella striata	LOTUS Database	35616633
Epichloe festucae	-	KNApSAcK
Epichloe festucae Fg1	Fungi	KNApSAcK
Epichloe festucae Fl1	Fungi	KNApSAcK
Epicholoe festucae	-	KNApSAcK
Lolium perenne	LOTUS Database	35616633
Neotyphodium coenophialum e822	-	KNApSAcK
Neotyphodium coenophialum Tf28	-	KNApSAcK
Neotyphodium festucae Frc7	-	KNApSAcK
Neotyphodium funkii e4096	-	KNApSAcK
Neotyphodium lolii AR1	-	KNApSAcK
Neotyphodium lolii Lp14	-	KNApSAcK
Neotyphodium lolii Lp19	-	KNApSAcK
Neotyphodium siegelii e915	-	KNApSAcK
Neotyphodium tembladerae e1169	-	KNApSAcK
Neotyphodium tembladerae e4055	-	KNApSAcK
Penicillium crustosum	LOTUS Database	35616633
Penicillium janthinellum	Fungi	KNApSAcK
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
Oxane
Pyran
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Pyrrole
Ether
Dialkyl ether
Azacycle
Oxacycle
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	6.3	ALOGPS
logP	5.64	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	14.32	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	45.25 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	125.03 m³·mol⁻¹	ChemAxon
Polarizability	51.53 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C20530

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

115028

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Paspaline (NP0066229)

MOL for NP0066229 (Paspaline)

3D MOL for NP0066229 (Paspaline)

3D SDF for NP0066229 (Paspaline)

3D-SDF for NP0066229 (Paspaline)

PDB for NP0066229 (Paspaline)

3D PDB for NP0066229 (Paspaline)

SMILES for NP0066229 (Paspaline)

INCHI for NP0066229 (Paspaline)

Structure for NP0066229 (Paspaline)

3D Structure for NP0066229 (Paspaline)