NP-MRD: Showing NP-Card for 5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methylpyridin-2-one (NP0304511)

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Record Information

Version

2.0

Created at

2022-09-10 19:39:26 UTC

Updated at

2022-09-10 19:39:26 UTC

NP-MRD ID

NP0304511

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methylpyridin-2-one

Description

Oxysporidinone belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. 5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methylpyridin-2-one was first documented in 2007 (PMID: 17286429). Based on a literature review a small amount of articles have been published on Oxysporidinone (PMID: 29915912) (PMID: 21497643) (PMID: 21419624).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102221392D          

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  Mrv1652309102221392D          

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 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 17 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 14 30  1  0  0  0  0
 30 31  2  0  0  0  0
 13 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 11 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304511

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)CC(C)\C=C(\C)C1OC(CCC1C)C1=C(O)C(=CN(C)C1=O)C1(O)CCC(=O)CC1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H43NO6/c1-7-16(2)12-17(3)13-19(5)26-18(4)8-9-22(35-26)24-25(32)21(15-29(6)27(24)33)28(34)11-10-20(30)14-23(28)31/h13,15-18,22-23,26,31-32,34H,7-12,14H2,1-6H3/b19-13-

> <INCHI_KEY>
CYNJYGDSSURTLH-UYRXBGFRSA-N

> <FORMULA>
C28H43NO6

> <MOLECULAR_WEIGHT>
489.653

> <EXACT_MASS>
489.309038109

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
55.07013462376912

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2Z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methyl-1,2-dihydropyridin-2-one

> <JCHEM_LOGP>
3.2352777659999976

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.012913249728335

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.602608166693258

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5536506644602768

> <JCHEM_POLAR_SURFACE_AREA>
107.29999999999998

> <JCHEM_REFRACTIVITY>
137.10009999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2Z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methylpyridin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.570   0.082   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.570   1.622   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.236   2.392   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.236   3.932   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.097   1.622   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.431   2.392   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.431   3.932   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.765   1.622   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.098   2.392   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.432   1.622   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.098   3.932   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.765   4.702   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.765   6.242   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.431   7.012   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.097   6.242   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.097   4.702   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.236   7.012   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.570   6.242   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.097   7.689   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.580   5.062   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.107   3.615   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.623   3.347   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.150   1.900   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.613   4.527   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.087   5.974   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.077   7.154   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.236   8.552   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       0.097   9.322   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       0.097  10.862   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.431   8.552   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.765   9.322   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.098   7.012   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.432   6.242   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.432   4.702   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.766   3.932   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   34                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   32                                                  
CONECT   14   13   15   30                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   27                                                  
CONECT   18   17   19   20   25                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   18   26                                                  
CONECT   26   25                                                            
CONECT   27   17   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   14   31                                                  
CONECT   31   30                                                            
CONECT   32   13   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   11   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₃NO₆

Average Mass

489.6530 Da

Monoisotopic Mass

489.30904 Da

IUPAC Name

5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2Z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methyl-1,2-dihydropyridin-2-one

Traditional Name

5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2Z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methylpyridin-2-one

CAS Registry Number

Not Available

SMILES

CCC(C)CC(C)\C=C(\C)C1OC(CCC1C)C1=C(O)C(=CN(C)C1=O)C1(O)CCC(=O)CC1O

InChI Identifier

InChI=1S/C28H43NO6/c1-7-16(2)12-17(3)13-19(5)26-18(4)8-9-22(35-26)24-25(32)21(15-29(6)27(24)33)28(34)11-10-20(30)14-23(28)31/h13,15-18,22-23,26,31-32,34H,7-12,14H2,1-6H3/b19-13-

InChI Key

CYNJYGDSSURTLH-UYRXBGFRSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Monoterpenoid
Monocyclic monoterpenoid
Aromatic monoterpenoid
Hydroxypyridine
Pyridinone
Dihydropyridine
Pyridine
Oxane
Hydropyridine
Heteroaromatic compound
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Lactam
Ketone
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	3.24	ChemAxon
pKa (Strongest Acidic)	9.6	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	107.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	137.1 m³·mol⁻¹	ChemAxon
Polarizability	55.07 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00038043

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

102062538

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhan J, Burns AM, Liu MX, Faeth SH, Gunatilaka AA: Search for cell motility and angiogenesis inhibitors with potential anticancer activity: beauvericin and other constituents of two endophytic strains of Fusarium oxysporum. J Nat Prod. 2007 Feb;70(2):227-32. doi: 10.1021/np060394t. Epub 2007 Feb 8. [PubMed:17286429 ]
Sun WJ, Zhu HT, Zhang TY, Zhang MY, Wang D, Yang CR, Zhang YX, Zhang YJ: Two New Alkaloids from Fusarium tricinctum SYPF 7082, an Endophyte from the Root of Panax notoginseng. Nat Prod Bioprospect. 2018 Oct;8(5):391-396. doi: 10.1007/s13659-018-0171-0. Epub 2018 Jun 18. [PubMed:29915912 ]
Wang QX, Li SF, Zhao F, Dai HQ, Bao L, Ding R, Gao H, Zhang LX, Wen HA, Liu HW: Chemical constituents from endophytic fungus Fusarium oxysporum. Fitoterapia. 2011 Jul;82(5):777-81. doi: 10.1016/j.fitote.2011.04.002. Epub 2011 Apr 9. [PubMed:21497643 ]
Wijeratne EM, Gunatilaka AA: Biomimetic conversion of (-)-fusoxypyridone and (-)-oxysporidinone to (-)-sambutoxin: further evidence for the structure of the tricyclic pyridone alkaloid, (-)-fusoxypyridone. Bioorg Med Chem Lett. 2011 Apr 15;21(8):2327-9. doi: 10.1016/j.bmcl.2011.02.091. Epub 2011 Mar 16. [PubMed:21419624 ]
LOTUS database [Link]

Showing NP-Card for 5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methylpyridin-2-one (NP0304511)

MOL for NP0304511 (5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methylpyridin-2-one)

3D MOL for NP0304511 (5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methylpyridin-2-one)

3D SDF for NP0304511 (5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methylpyridin-2-one)

3D-SDF for NP0304511 (5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methylpyridin-2-one)

PDB for NP0304511 (5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methylpyridin-2-one)

3D PDB for NP0304511 (5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methylpyridin-2-one)

SMILES for NP0304511 (5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methylpyridin-2-one)

INCHI for NP0304511 (5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methylpyridin-2-one)

Structure for NP0304511 (5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methylpyridin-2-one)

3D Structure for NP0304511 (5-(1,2-dihydroxy-4-oxocyclohexyl)-3-{6-[(2z)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl}-4-hydroxy-1-methylpyridin-2-one)