NP-MRD: Showing NP-Card for (4s,5z,10r)-4-hydroxy-10-methyl-4,8,9,10-tetrahydro-3h-oxecine-2,7-dione (NP0214268)

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Record Information

Version

2.0

Created at

2022-09-05 13:31:27 UTC

Updated at

2022-09-05 13:31:27 UTC

NP-MRD ID

NP0214268

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,5z,10r)-4-hydroxy-10-methyl-4,8,9,10-tetrahydro-3h-oxecine-2,7-dione

Description

Cephalosporolide B belongs to the class of organic compounds known as oxocins. Oxocins are compounds containing an oxocin ring, which is a eight-member unsaturated aromatic ring containing one oxygen atom and seven carbon atoms. (4s,5z,10r)-4-hydroxy-10-methyl-4,8,9,10-tetrahydro-3h-oxecine-2,7-dione was first documented in 2012 (PMID: 22201477). Based on a literature review a small amount of articles have been published on Cephalosporolide B (PMID: 24195739) (PMID: 23650094).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 28  0  0  0  0  0  0  0  0999 V2000
    2.6944   -1.7947    0.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5290   -0.9299   -0.2811 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8058    0.4633    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7113    1.3237    0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0915    2.0394   -0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5928    2.5241   -1.4090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5107    2.2535   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3607    1.2578   -0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0600   -0.1595   -0.6006 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9400   -0.4638   -1.3702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0058   -0.9320    0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6251   -1.4965    0.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5550   -1.9380    2.1639 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3634   -1.5270    0.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186   -2.8254   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6463   -1.7101    1.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6627   -1.3265   -0.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7001   -1.0403   -1.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6959    0.5047    0.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2279    1.0344   -0.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1365    0.7440    1.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2048    2.1141    1.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9109    3.3146   -0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4370    1.5592   -0.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9113   -0.6074   -1.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1313   -0.4118   -2.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2822   -0.2321    1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7679   -1.7375    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14  2  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  6
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  6
 10 26  1  0
 11 27  1  0
 11 28  1  0
M  END


  Mrv1652309052215312D          

 14 14  0  0  1  0            999 V2000
    1.9690    2.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.5039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6990    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5091    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5893   -0.3671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589    0.1007    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2293    0.9227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3488    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7314    1.1921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  2 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0214268

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CCC(=O)\C=C/[C@@H](O)CC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O4/c1-7-2-3-8(11)4-5-9(12)6-10(13)14-7/h4-5,7,9,12H,2-3,6H2,1H3/b5-4-/t7-,9-/m1/s1

> <INCHI_KEY>
OYHHNJLVXIIQGO-LEZDYHIDSA-N

> <FORMULA>
C10H14O4

> <MOLECULAR_WEIGHT>
198.218

> <EXACT_MASS>
198.089208931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
19.561928246009913

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,10R)-4-hydroxy-10-methyl-3,4,7,8,9,10-hexahydro-2H-oxecine-2,7-dione

> <JCHEM_LOGP>
0.5326718126666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.71472759484895

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.586060461488668

> <JCHEM_PKA_STRONGEST_BASIC>
-2.977228225847581

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
50.828100000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,10R)-4-hydroxy-10-methyl-4,8,9,10-tetrahydro-3H-oxecine-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       3.676   3.971   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   2.807   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.171   1.352   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.684   1.061   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.188  -0.394   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.700  -0.685   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.180  -1.558   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -1.267   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.163   0.188   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.295   1.722   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.651   0.479   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.147   1.934   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.365   2.225   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.155   3.098   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    2                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₄O₄

Average Mass

198.2180 Da

Monoisotopic Mass

198.08921 Da

IUPAC Name

(4S,10R)-4-hydroxy-10-methyl-3,4,7,8,9,10-hexahydro-2H-oxecine-2,7-dione

Traditional Name

(4S,10R)-4-hydroxy-10-methyl-4,8,9,10-tetrahydro-3H-oxecine-2,7-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1CCC(=O)\C=C/[C@@H](O)CC(=O)O1

InChI Identifier

InChI=1S/C10H14O4/c1-7-2-3-8(11)4-5-9(12)6-10(13)14-7/h4-5,7,9,12H,2-3,6H2,1H3/b5-4-/t7-,9-/m1/s1

InChI Key

OYHHNJLVXIIQGO-LEZDYHIDSA-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 oxocins. Oxocins are compounds containing an oxocin ring, which is a eight-member unsaturated aromatic ring containing one oxygen atom and seven carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxocins

Sub Class

Not Available

Direct Parent

Oxocins

Alternative Parents

Substituents

Oxocin
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	0.53	ChemAxon
pKa (Strongest Acidic)	14.59	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	50.83 m³·mol⁻¹	ChemAxon
Polarizability	19.56 Å³	ChemAxon
Number of Rings	1	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

30829974

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72793049

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Asai T, Chung YM, Sakurai H, Ozeki T, Chang FR, Yamashita K, Oshima Y: Tenuipyrone, a novel skeletal polyketide from the entomopathogenic fungus, Isaria tenuipes, cultivated in the presence of epigenetic modifiers. Org Lett. 2012 Jan 20;14(2):513-5. doi: 10.1021/ol203097b. Epub 2011 Dec 27. [PubMed:22201477 ]
Song L, Liu Y, Tong R: Cephalosporolide B serving as a versatile synthetic precursor: asymmetric biomimetic total syntheses of cephalosporolides C, E, F, G, and (4-OMe-)G. Org Lett. 2013 Nov 15;15(22):5850-3. doi: 10.1021/ol402913m. Epub 2013 Nov 6. [PubMed:24195739 ]
Ma B, Zhong Z, Hu H, Li H, Zhao C, Xie X, She X: Concise enantioselective synthesis of cephalosporolide B, (4R)-4-OMe-cephalosporolide C, and (4S)-4-OMe-cephalosporolide C. Chem Asian J. 2013 Jul;8(7):1391-4. doi: 10.1002/asia.201300332. Epub 2013 May 3. [PubMed:23650094 ]
LOTUS database [Link]

Showing NP-Card for (4s,5z,10r)-4-hydroxy-10-methyl-4,8,9,10-tetrahydro-3h-oxecine-2,7-dione (NP0214268)

MOL for NP0214268 ((4s,5z,10r)-4-hydroxy-10-methyl-4,8,9,10-tetrahydro-3h-oxecine-2,7-dione)

3D MOL for NP0214268 ((4s,5z,10r)-4-hydroxy-10-methyl-4,8,9,10-tetrahydro-3h-oxecine-2,7-dione)

3D SDF for NP0214268 ((4s,5z,10r)-4-hydroxy-10-methyl-4,8,9,10-tetrahydro-3h-oxecine-2,7-dione)

3D-SDF for NP0214268 ((4s,5z,10r)-4-hydroxy-10-methyl-4,8,9,10-tetrahydro-3h-oxecine-2,7-dione)

PDB for NP0214268 ((4s,5z,10r)-4-hydroxy-10-methyl-4,8,9,10-tetrahydro-3h-oxecine-2,7-dione)

3D PDB for NP0214268 ((4s,5z,10r)-4-hydroxy-10-methyl-4,8,9,10-tetrahydro-3h-oxecine-2,7-dione)

SMILES for NP0214268 ((4s,5z,10r)-4-hydroxy-10-methyl-4,8,9,10-tetrahydro-3h-oxecine-2,7-dione)

INCHI for NP0214268 ((4s,5z,10r)-4-hydroxy-10-methyl-4,8,9,10-tetrahydro-3h-oxecine-2,7-dione)

Structure for NP0214268 ((4s,5z,10r)-4-hydroxy-10-methyl-4,8,9,10-tetrahydro-3h-oxecine-2,7-dione)

3D Structure for NP0214268 ((4s,5z,10r)-4-hydroxy-10-methyl-4,8,9,10-tetrahydro-3h-oxecine-2,7-dione)