NP-MRD: Showing NP-Card for Nigrosporapyrone (NP0007875)

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Record Information

Version

2.0

Created at

2020-12-09 05:26:47 UTC

Updated at

2021-07-15 16:58:48 UTC

NP-MRD ID

NP0007875

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nigrosporapyrone

Provided By

NPAtlas

Description

Nigrosporapyrone is found in Nigrospora, Nigrospora sp. PSU-F5 and Rhizophora mucronata. Nigrosporapyrone was first documented in 2008 (PMID: 18646829). Based on a literature review very few articles have been published on Nigrosporapyrone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106043D          

 22 22  0  0  0  0            999 V2000
    2.9878    0.7918    0.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -0.0657   -0.1341 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5200   -0.4849   -0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3597   -0.1127    0.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8718   -0.5719   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0830   -0.1322    0.5165 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5138    1.2392    0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8663   -0.2263    1.8917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9789   -1.3693   -1.2848 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0872   -1.7517   -1.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0088   -2.5276   -2.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431   -1.3261   -1.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8723    0.2196    1.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0068    1.2219    0.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2070    1.6031    0.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.5417    1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9160   -0.8548    0.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6824    1.8639   -0.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0125    1.7352    0.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2787    1.2058   -0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6052    0.6720    2.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1920   -1.6710   -2.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12  3  2  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  4 16  1  0  0  0  0
  6 17  1  6  0  0  0
  7 18  1  0  0  0  0
  7 19  1  0  0  0  0
  7 20  1  0  0  0  0
  8 21  1  0  0  0  0
 12 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0007875

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]([H])(C1=C([H])C(OC([H])([H])[H])=C([H])C(=O)O1)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O4/c1-5(9)7-3-6(11-2)4-8(10)12-7/h3-5,9H,1-2H3/t5-/m0/s1

> <INCHI_KEY>
ZNHXQNPNLZSOHO-UHFFFAOYSA-N

> <FORMULA>
C8H10O4

> <MOLECULAR_WEIGHT>
170.164

> <EXACT_MASS>
170.057908802

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.527090284943775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(1S)-1-hydroxyethyl]-4-methoxy-2H-pyran-2-one

> <ALOGPS_LOGP>
0.75

> <JCHEM_LOGP>
0.03157409699999994

> <ALOGPS_LOGS>
-0.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.165252133645094

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1639187167436367

> <JCHEM_POLAR_SURFACE_AREA>
55.76

> <JCHEM_REFRACTIVITY>
44.5206

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.56e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(1S)-1-hydroxyethyl]-4-methoxypyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       2.988   0.792   0.965  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.772  -0.066  -0.134  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.520  -0.485  -0.497  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.360  -0.113   0.171  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.872  -0.572  -0.248  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.083  -0.132   0.517  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.514   1.239   0.085  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.866  -0.226   1.892  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.979  -1.369  -1.285  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.087  -1.752  -1.952  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.009  -2.528  -2.962  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.343  -1.326  -1.581  0.00  0.00           C+0
HETATM   13  H   UNK     0       2.872   0.220   1.920  0.00  0.00           H+0
HETATM   14  H   UNK     0       4.007   1.222   0.977  0.00  0.00           H+0
HETATM   15  H   UNK     0       2.207   1.603   0.900  0.00  0.00           H+0
HETATM   16  H   UNK     0       0.470   0.542   1.018  0.00  0.00           H+0
HETATM   17  H   UNK     0      -2.916  -0.855   0.272  0.00  0.00           H+0
HETATM   18  H   UNK     0      -1.682   1.864  -0.305  0.00  0.00           H+0
HETATM   19  H   UNK     0      -3.013   1.735   0.955  0.00  0.00           H+0
HETATM   20  H   UNK     0      -3.279   1.206  -0.746  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.605   0.672   2.206  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.192  -1.671  -2.165  0.00  0.00           H+0
CONECT    1    2   13   14   15                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8   17                                             
CONECT    7    6   18   19   20                                             
CONECT    8    6   21                                                       
CONECT    9    5   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    3   22                                                  
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15    1                                                            
CONECT   16    4                                                            
CONECT   17    6                                                            
CONECT   18    7                                                            
CONECT   19    7                                                            
CONECT   20    7                                                            
CONECT   21    8                                                            
CONECT   22   12                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₈H₁₀O₄

Average Mass

170.1640 Da

Monoisotopic Mass

170.05791 Da

IUPAC Name

6-[(1S)-1-hydroxyethyl]-4-methoxy-2H-pyran-2-one

Traditional Name

6-[(1S)-1-hydroxyethyl]-4-methoxypyran-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC(=C1)C(C)O

InChI Identifier

InChI=1S/C8H10O4/c1-5(9)7-3-6(11-2)4-8(10)12-7/h3-5,9H,1-2H3

InChI Key

ZNHXQNPNLZSOHO-UHFFFAOYSA-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
Nigrospora	NPAtlas	18646829
Nigrospora sp. PSU-F5	-	KNApSAcK
Rhizophora mucronata	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as pyranones and derivatives. These are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Pyranone
Alkyl aryl ether
Heteroaromatic compound
Vinylogous ester
Secondary alcohol
Lactone
Oxacycle
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
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	0.75	ALOGPS
logP	0.032	ChemAxon
logS	-0.68	ALOGPS
pKa (Strongest Acidic)	14.17	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.52 m³·mol⁻¹	ChemAxon
Polarizability	16.53 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

NPAtlas ID

NPA003097

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00039848

Chemspider ID

27026270

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102476173

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Trisuwan K, Rukachaisirikul V, Sukpondma Y, Preedanon S, Phongpaichit S, Rungjindamai N, Sakayaroj J: Epoxydons and a pyrone from the marine-derived fungus Nigrospora sp. PSU-F5. J Nat Prod. 2008 Aug;71(8):1323-6. doi: 10.1021/np8002595. Epub 2008 Jul 23. [PubMed:18646829 ]

Showing NP-Card for Nigrosporapyrone (NP0007875)

MOL for NP0007875 (Nigrosporapyrone)

3D MOL for NP0007875 (Nigrosporapyrone)

3D SDF for NP0007875 (Nigrosporapyrone)

3D-SDF for NP0007875 (Nigrosporapyrone)

PDB for NP0007875 (Nigrosporapyrone)

3D PDB for NP0007875 (Nigrosporapyrone)

SMILES for NP0007875 (Nigrosporapyrone)

INCHI for NP0007875 (Nigrosporapyrone)

Structure for NP0007875 (Nigrosporapyrone)

3D Structure for NP0007875 (Nigrosporapyrone)