NP-MRD: Showing NP-Card for Dehydroxypaxilline (NP0084747)

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Record Information

Version

2.0

Created at

2022-04-29 05:24:46 UTC

Updated at

2022-04-29 05:24:46 UTC

NP-MRD ID

NP0084747

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dehydroxypaxilline

Description

13-Desoxypaxilline 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. 13-Desoxypaxilline is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Dehydroxypaxilline is found in Aspergillus oryzae, Emericella striata, Epichloe festucae, Penicillium janthinellum and Penicillium miczynskii. Dehydroxypaxilline was first documented in 2015 (PMID: 26213965). Based on a literature review a small amount of articles have been published on 13-Desoxypaxilline (PMID: 28674820) (PMID: 32077051) (PMID: 29670599) (PMID: 29237259).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207242D          

 34 39  0  0  1  0            999 V2000
    0.7768   -3.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292   -4.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2816   -4.4069    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3648   -5.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1172   -5.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7865   -5.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7033   -4.2628    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9509   -3.9244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6201   -3.4420    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3725   -3.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8500   -6.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2652   -5.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304292207242D          

 34 39  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0084747

> <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([H])CC2)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C27H33NO3/c1-25(2,30)24-21(29)14-18-19-10-9-15-13-17-16-7-5-6-8-20(16)28-23(17)27(15,4)26(19,3)12-11-22(18)31-24/h5-8,14-15,19,22,24,28,30H,9-13H2,1-4H3/t15-,19-,22-,24-,26-,27+/m0/s1

> <INCHI_KEY>
GYSZYWSJZCKCBD-LXGUAGHKSA-N

> <FORMULA>
C27H33NO3

> <MOLECULAR_WEIGHT>
419.565

> <EXACT_MASS>
419.246043927

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
49.34077642136205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5S,7R,11R,14S)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{16,24}.0^{17,22}]tetracosa-9,16(24),17,19,21-pentaen-8-one

> <ALOGPS_LOGP>
5.62

> <JCHEM_LOGP>
4.626475565666666

> <ALOGPS_LOGS>
-5.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.84910562085092

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.130818406538971

> <JCHEM_PKA_STRONGEST_BASIC>
-3.17861276013896

> <JCHEM_POLAR_SURFACE_AREA>
62.32000000000001

> <JCHEM_REFRACTIVITY>
121.84239999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.32e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,7R,11R,14S)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{16,24}.0^{17,22}]tetracosa-9,16(24),17,19,21-pentaen-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       1.450  -6.963   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.855  -7.594   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.259  -8.226   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.414  -9.758   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.819 -10.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.068  -9.489   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.913  -7.957   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.508  -7.326   0.000  0.00  0.00           O+0
HETATM    9  H   UNK     0       6.758  -6.425   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       8.162  -7.057   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.567  -7.688   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.722  -9.221   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.126  -9.852   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.282 -11.384   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.787 -11.710   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.562 -10.379   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.536  -9.231   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      13.311  -7.900   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      14.816  -8.226   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.065  -7.326   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.469  -7.957   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.625  -9.489   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.375 -10.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.971  -9.758   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       9.877 -10.753   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0      10.032 -12.285   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.628 -11.653   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.473 -10.121   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0       7.223 -11.022   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0      11.132  -8.312   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.632  -7.978   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.165 -10.659   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.223  -8.999   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.486  -6.190   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33   34                                             
CONECT    3    2    4    8                                                  
CONECT    4    3    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8    9   10                                             
CONECT    8    7    3                                                       
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   28   31                                             
CONECT   13   12   14   17   30                                             
CONECT   14   13   15   25   26                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   13   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   16   19                                                  
CONECT   25   14                                                            
CONECT   26   14   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    6   12   29                                             
CONECT   29   28                                                            
CONECT   30   13                                                            
CONECT   31   12                                                            
CONECT   32    4                                                            
CONECT   33    2                                                            
CONECT   34    2                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Value	Source
13-Deoxypaxilline	Kegg

Chemical Formula

C₂₇H₃₃NO₃

Average Mass

419.5650 Da

Monoisotopic Mass

419.24604 Da

IUPAC Name

(1S,2S,5S,7R,11R,14S)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{16,24}.0^{17,22}]tetracosa-9,16(24),17,19,21-pentaen-8-one

Traditional Name

(1S,2S,5S,7R,11R,14S)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{16,24}.0^{17,22}]tetracosa-9,16(24),17,19,21-pentaen-8-one

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([H])CC2)C(C)(C)O

InChI Identifier

InChI=1S/C27H33NO3/c1-25(2,30)24-21(29)14-18-19-10-9-15-13-17-16-7-5-6-8-20(16)28-23(17)27(15,4)26(19,3)12-11-22(18)31-24/h5-8,14-15,19,22,24,28,30H,9-13H2,1-4H3/t15-,19-,22-,24-,26-,27+/m0/s1

InChI Key

GYSZYWSJZCKCBD-LXGUAGHKSA-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 oryzae	LOTUS Database	35616633
Emericella striata	-	KNApSAcK
Epichloe festucae	LOTUS Database	35616633
Penicillium janthinellum	LOTUS Database	35616633
Penicillium miczynskii	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 ketone
Ketone
Oxacycle
Azacycle
Dialkyl ether
Ether
Alcohol
Organic oxide
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Carbonyl group
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	4.63	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	14.13	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.32 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	121.84 m³·mol⁻¹	ChemAxon
Polarizability	49.34 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00054324

Chemspider ID

10270586

KEGG Compound ID

C20531

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14166134

PDB ID

Not Available

ChEBI ID

187070

Good Scents ID

Not Available

References

General References

Bauer JI, Gross M, Cramer B, Wegner S, Hausmann H, Hamscher G, Usleber E: Detection of the tremorgenic mycotoxin paxilline and its desoxy analog in ergot of rye and barley: a new class of mycotoxins added to an old problem. Anal Bioanal Chem. 2017 Aug;409(21):5101-5112. doi: 10.1007/s00216-017-0455-y. Epub 2017 Jul 4. [PubMed:28674820 ]
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 ]
Singh D, Lee CH: Volatiles Mediated Interactions Between Aspergillus oryzae Strains Modulate Morphological Transition and Exometabolomes. Front Microbiol. 2018 Apr 4;9:628. doi: 10.3389/fmicb.2018.00628. eCollection 2018. [PubMed:29670599 ]
Bauer JI, Gross M, Cramer B, Humpf HU, Hamscher G, Usleber E: Immunochemical Analysis of Paxilline and Ergot Alkaloid Mycotoxins in Grass Seeds and Plants. J Agric Food Chem. 2018 Jan 10;66(1):315-322. doi: 10.1021/acs.jafc.7b05580. Epub 2017 Dec 26. [PubMed:29237259 ]
Nicholson MJ, Eaton CJ, Starkel C, Tapper BA, Cox MP, Scott B: Molecular Cloning and Functional Analysis of Gene Clusters for the Biosynthesis of Indole-Diterpenes in Penicillium crustosum and P. janthinellum. Toxins (Basel). 2015 Jul 23;7(8):2701-22. doi: 10.3390/toxins7082701. [PubMed:26213965 ]

Showing NP-Card for Dehydroxypaxilline (NP0084747)

MOL for NP0084747 (Dehydroxypaxilline)

3D MOL for NP0084747 (Dehydroxypaxilline)

3D SDF for NP0084747 (Dehydroxypaxilline)

3D-SDF for NP0084747 (Dehydroxypaxilline)

PDB for NP0084747 (Dehydroxypaxilline)

3D PDB for NP0084747 (Dehydroxypaxilline)

SMILES for NP0084747 (Dehydroxypaxilline)

INCHI for NP0084747 (Dehydroxypaxilline)

Structure for NP0084747 (Dehydroxypaxilline)

3D Structure for NP0084747 (Dehydroxypaxilline)