NP-MRD: Showing NP-Card for Aculeapyridone O (NP0341971)

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Record Information

Version

2.0

Created at

2024-11-13 13:15:01 UTC

Updated at

2026-02-04 13:16:00 UTC

NP-MRD ID

NP0341971

Natural Product DOI

https://doi.org/10.57994/3461

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aculeapyridone O

Description

Aculeapyridone O was first documented in 2025 (PMID: 39874532). Based on a literature review very few articles have been published on Aculeapyridone O.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02102313252D          

 30 31  0  0  1  0            999 V2000
    5.2816   -4.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8691   -4.2651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0441   -4.2651    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6316   -4.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441   -5.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -4.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941   -5.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691   -5.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1566   -6.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316   -6.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0809   -7.1230    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9059   -7.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -7.1230    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -8.5520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0809   -8.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6316   -3.5507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441   -2.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6316   -2.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441   -1.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8691   -1.4073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2816   -0.6928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8691    0.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2816   -2.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1066   -2.1217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8691   -2.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2816   -3.5507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1066   -3.5507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 10  1  1  0  0  0
 11 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
 14 16  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 20 28  2  0  0  0  0
 26 28  1  0  0  0  0
 29 28  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END


  Mrv2104 02102313252D          

 30 31  0  0  1  0            999 V2000
    5.2816   -4.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8691   -4.2651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0441   -4.2651    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6316   -4.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441   -5.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -4.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941   -5.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691   -5.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1566   -6.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316   -6.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0809   -7.1230    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9059   -7.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -7.1230    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -8.5520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0809   -8.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6316   -3.5507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441   -2.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6316   -2.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441   -1.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8691   -1.4073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2816   -0.6928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8691    0.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2816   -2.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1066   -2.1217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8691   -2.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2816   -3.5507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1066   -3.5507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 10  1  1  0  0  0
 11 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
 14 16  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 20 28  2  0  0  0  0
 26 28  1  0  0  0  0
 29 28  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0341971

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(=O)OC[C@H](CC)\C=C\C=C\C=C(/C)[C@@H]1OC2=C([C@@H](O)[C@H]1C)C(=O)N(OC)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C22H29NO6/c1-5-17(13-28-14-24)10-8-6-7-9-15(2)21-16(3)20(25)19-18(29-21)11-12-23(27-4)22(19)26/h6-12,14,16-17,20-21,25H,5,13H2,1-4H3/b7-6+,10-8+,15-9+/t16-,17-,20+,21+/m1/s1

> <INCHI_KEY>
WJMHLXDLSILOJA-CZAWIACOSA-N

> <FORMULA>
C22H29NO6

> <MOLECULAR_WEIGHT>
403.475

> <EXACT_MASS>
403.199487658

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
44.4166838353782

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3E,5E,7E)-2-ethyl-8-[(2R,3R,4S)-4-hydroxy-6-methoxy-3-methyl-5-oxo-2H,3H,4H,5H,6H-pyrano[3,2-c]pyridin-2-yl]nona-3,5,7-trien-1-yl formate

> <JCHEM_LOGP>
2.3330622263333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.91192932062959

> <JCHEM_PKA_STRONGEST_BASIC>
-3.274722115156616

> <JCHEM_POLAR_SURFACE_AREA>
85.3

> <JCHEM_REFRACTIVITY>
113.7394

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3E,5E,7E)-2-ethyl-8-[(2R,3R,4S)-4-hydroxy-6-methoxy-3-methyl-5-oxo-2H,3H,4H-pyrano[3,2-c]pyridin-2-yl]nona-3,5,7-trien-1-yl formate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-FEB-23         0                                  
HETATM    1  C   UNK     0       9.859  -9.295   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.089  -7.962   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.549  -7.962   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.779  -9.295   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.549 -10.629   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.239  -9.295   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.469 -10.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.929 -10.629   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.159 -11.963   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.619 -11.963   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.151 -13.296   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.691 -13.296   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.461 -14.630   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0      -4.771 -13.296   0.000  0.00  0.00           H+0
HETATM   16  O   UNK     0      -4.771 -15.964   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.619 -14.630   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.151 -15.964   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.779  -6.628   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.549  -5.294   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.779  -3.961   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.549  -2.627   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       9.089  -2.627   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0       9.859  -1.293   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.089   0.040   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.859  -3.961   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.399  -3.961   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.089  -5.294   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.859  -6.628   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.399  -6.628   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   11   18                                                       
CONECT   18   17                                                            
CONECT   19    3   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   20   26   29                                                  
CONECT   29   28    2   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₉NO₆

Average Mass

403.4750 Da

Monoisotopic Mass

403.19949 Da

IUPAC Name

(2R,3E,5E,7E)-2-ethyl-8-[(2R,3R,4S)-4-hydroxy-6-methoxy-3-methyl-5-oxo-2H,3H,4H,5H,6H-pyrano[3,2-c]pyridin-2-yl]nona-3,5,7-trien-1-yl formate

Traditional Name

(2R,3E,5E,7E)-2-ethyl-8-[(2R,3R,4S)-4-hydroxy-6-methoxy-3-methyl-5-oxo-2H,3H,4H-pyrano[3,2-c]pyridin-2-yl]nona-3,5,7-trien-1-yl formate

CAS Registry Number

Not Available

SMILES

[H]C(=O)OC[C@H](CC)\C=C\C=C\C=C(/C)[C@@H]1OC2=C([C@@H](O)[C@H]1C)C(=O)N(OC)C=C2

InChI Identifier

InChI=1S/C22H29NO6/c1-5-17(13-28-14-24)10-8-6-7-9-15(2)21-16(3)20(25)19-18(29-21)11-12-23(27-4)22(19)26/h6-12,14,16-17,20-21,25H,5,13H2,1-4H3/b7-6+,10-8+,15-9+/t16-,17-,20+,21+/m1/s1

InChI Key

WJMHLXDLSILOJA-CZAWIACOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl3, experimental)	[email protected]	Wuhan university	Chen Weichen	2024-11-13	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, CDCl3, experimental)	[email protected]	Wuhan university	Chen Weichen	2024-11-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CDCl3, experimental)	[email protected]	Wuhan university	Chen Weichen	2024-11-13	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, CDCl3, experimental)	[email protected]	Wuhan university	Chen Weichen	2024-11-13	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, CDCl3, experimental)	[email protected]	Wuhan university	Chen Weichen	2024-11-13	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, CDCl3, experimental)	[email protected]	Wuhan university	Chen Weichen	2024-11-13	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.0, Methanol-d4, simulated)	[email protected]	Not Available	Not Available	2026-02-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200.0, Methanol-d4, simulated)	[email protected]	Not Available	Not Available	2026-02-04	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Aspergillus aculeatinus		Not Available
Aspergillus aculeatinus		Not Available

Chemical Taxonomy

Classification

Not classified

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	2.33	ChemAxon
pKa (Strongest Acidic)	13.91	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.3 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	113.74 m³·mol⁻¹	ChemAxon
Polarizability	44.42 Å³	ChemAxon
Number of Rings	2	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen WC, Song X, Wu J, Zhong YT, Edjah PP, Zhang QY, Li M, Zhu KK, Tian C, Yuan RY, Wu XY, Gao P, Hong K, Zhang MK, Ping J, Cai YS: Aculeapyridones A-Q, Pyranopyridone Alkaloids with Protective Effects against Acetaminophen-Induced Acute Liver Injury Discovered from a Coculture of Aspergillus aculeatinus WHUF0198 and a Penicillium sp. J Nat Prod. 2025 Feb 28;88(2):336-348. doi: 10.1021/acs.jnatprod.4c01049. Epub 2025 Jan 28. [PubMed:39874532 ]
DOI: 10.1021/acs.jnatprod.4c01049
PMID: 39874532

Showing NP-Card for Aculeapyridone O (NP0341971)

MOL for NP0341971 (Aculeapyridone O)

3D MOL for NP0341971 (Aculeapyridone O)

3D SDF for NP0341971 (Aculeapyridone O)

3D-SDF for NP0341971 (Aculeapyridone O)

PDB for NP0341971 (Aculeapyridone O)

3D PDB for NP0341971 (Aculeapyridone O)

SMILES for NP0341971 (Aculeapyridone O)

INCHI for NP0341971 (Aculeapyridone O)

Structure for NP0341971 (Aculeapyridone O)

3D Structure for NP0341971 (Aculeapyridone O)