NP-MRD: Showing NP-Card for (1r,2r,5s,6r)-5-{5-[(1r,2r,4as,6r,8ar)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxopyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate (NP0262598)

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Record Information

Version

2.0

Created at

2022-09-08 05:28:28 UTC

Updated at

2022-09-08 05:28:28 UTC

NP-MRD ID

NP0262598

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,5s,6r)-5-{5-[(1r,2r,4as,6r,8ar)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxopyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate

Description

23-O-acetyl-N-hydroxyapiosporamide belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. (1r,2r,5s,6r)-5-{5-[(1r,2r,4as,6r,8ar)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxopyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate is found in Arthrinium arundinis. Based on a literature review very few articles have been published on 23-O-acetyl-N-hydroxyapiosporamide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082207282D          

 35 39  0  0  1  0            999 V2000
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    5.3409    3.1636    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


  Mrv1652309082207282D          

 35 39  0  0  1  0            999 V2000
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 19 30  1  0  0  0  0
 16 31  2  0  0  0  0
 10 31  1  0  0  0  0
 31 32  1  0  0  0  0
  8 33  1  0  0  0  0
 33 34  1  6  0  0  0
 35 34  1  6  0  0  0
  5 35  1  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0262598

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@H]2[C@@H](C1)C=C[C@@H](C)[C@H]2C(=O)C1=C(O)C(=CN(O)C1=O)[C@@]1(O)CC[C@@H](OC(C)=O)[C@H]2O[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C26H33NO8/c1-12-4-7-16-15(10-12)6-5-13(2)19(16)22(30)20-21(29)17(11-27(33)25(20)31)26(32)9-8-18(34-14(3)28)23-24(26)35-23/h5-6,11-13,15-16,18-19,23-24,29,32-33H,4,7-10H2,1-3H3/t12-,13-,15-,16-,18-,19-,23-,24-,26+/m1/s1

> <INCHI_KEY>
XJGASSGRQMFKDJ-RYRIJOLQSA-N

> <FORMULA>
C26H33NO8

> <MOLECULAR_WEIGHT>
487.549

> <EXACT_MASS>
487.220617027

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
50.31687964872488

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,6R)-5-{5-[(1R,2R,4aS,6R,8aR)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxo-1,6-dihydropyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate

> <JCHEM_LOGP>
1.9203511149999992

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.738152918712688

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.149059561667888

> <JCHEM_PKA_STRONGEST_BASIC>
-3.682019465401381

> <JCHEM_POLAR_SURFACE_AREA>
136.9

> <JCHEM_REFRACTIVITY>
125.92699999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,6R)-5-{5-[(1R,2R,4aS,6R,8aR)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxopyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       9.970   7.445   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.970   5.905   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.636   5.135   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.303   5.135   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.303   3.595   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.637   2.825   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.637   1.285   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.303   0.515   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.293  -0.664   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.313  -0.664   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.840  -2.112   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       9.850  -3.291   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0      10.377  -4.738   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.334  -3.024   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.344  -4.204   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.807  -1.577   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.290  -1.309   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.764   0.138   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.300  -2.489   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.827  -3.936   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.897  -5.044   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.837  -5.116   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.321  -4.848   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.794  -3.401   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.277  -3.134   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.751  -1.687   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.766  -1.419   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.741  -0.507   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.257  -0.774   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.784  -2.222   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.797  -0.397   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.270   1.050   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.970   1.285   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.636   2.055   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.970   2.825   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   33                                             
CONECT    9    8                                                            
CONECT   10    8   11   31                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   31                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   30                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   24   19                                                  
CONECT   31   16   10   32                                                  
CONECT   32   31                                                            
CONECT   33    8   34   35                                                  
CONECT   34   33   35                                                       
CONECT   35   34    5   33                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₃NO₈

Average Mass

487.5490 Da

Monoisotopic Mass

487.22062 Da

IUPAC Name

(1R,2R,5S,6R)-5-{5-[(1R,2R,4aS,6R,8aR)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxo-1,6-dihydropyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate

Traditional Name

(1R,2R,5S,6R)-5-{5-[(1R,2R,4aS,6R,8aR)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxopyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@H]2[C@@H](C1)C=C[C@@H](C)[C@H]2C(=O)C1=C(O)C(=CN(O)C1=O)[C@@]1(O)CC[C@@H](OC(C)=O)[C@H]2O[C@@H]12

InChI Identifier

InChI=1S/C26H33NO8/c1-12-4-7-16-15(10-12)6-5-13(2)19(16)22(30)20-21(29)17(11-27(33)25(20)31)26(32)9-8-18(34-14(3)28)23-24(26)35-23/h5-6,11-13,15-16,18-19,23-24,29,32-33H,4,7-10H2,1-3H3/t12-,13-,15-,16-,18-,19-,23-,24-,26+/m1/s1

InChI Key

XJGASSGRQMFKDJ-RYRIJOLQSA-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

Species Name	Source	Reference
Arthrinium arundinis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl alkyl ketones

Alternative Parents

Substituents

Aryl alkyl ketone
Hydroxypyridine
Pyridinone
Oxepane
Dihydropyridine
Pyridine
Hydropyridine
Heteroaromatic compound
Vinylogous amide
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
Lactam
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Alcohol
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	1.92	ChemAxon
pKa (Strongest Acidic)	6.15	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	136.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	125.93 m³·mol⁻¹	ChemAxon
Polarizability	50.32 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

78439382

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132504558

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,5s,6r)-5-{5-[(1r,2r,4as,6r,8ar)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxopyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate (NP0262598)

MOL for NP0262598 ((1r,2r,5s,6r)-5-{5-[(1r,2r,4as,6r,8ar)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxopyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate)

3D MOL for NP0262598 ((1r,2r,5s,6r)-5-{5-[(1r,2r,4as,6r,8ar)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxopyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate)

3D SDF for NP0262598 ((1r,2r,5s,6r)-5-{5-[(1r,2r,4as,6r,8ar)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxopyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate)

3D-SDF for NP0262598 ((1r,2r,5s,6r)-5-{5-[(1r,2r,4as,6r,8ar)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxopyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate)

PDB for NP0262598 ((1r,2r,5s,6r)-5-{5-[(1r,2r,4as,6r,8ar)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxopyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate)

3D PDB for NP0262598 ((1r,2r,5s,6r)-5-{5-[(1r,2r,4as,6r,8ar)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxopyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate)

SMILES for NP0262598 ((1r,2r,5s,6r)-5-{5-[(1r,2r,4as,6r,8ar)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxopyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate)

INCHI for NP0262598 ((1r,2r,5s,6r)-5-{5-[(1r,2r,4as,6r,8ar)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxopyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate)

Structure for NP0262598 ((1r,2r,5s,6r)-5-{5-[(1r,2r,4as,6r,8ar)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxopyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate)

3D Structure for NP0262598 ((1r,2r,5s,6r)-5-{5-[(1r,2r,4as,6r,8ar)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-1,4-dihydroxy-6-oxopyridin-3-yl}-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl acetate)