NP-MRD: Showing NP-Card for {7-hydroxy-4-oxo-2-[(1e)-pent-1-en-1-yl]-2,3-dihydro-1-benzopyran-5-yl}acetic acid (NP0256047)

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Record Information

Version

1.0

Created at

2022-09-07 20:45:26 UTC

Updated at

2022-09-07 20:45:27 UTC

NP-MRD ID

NP0256047

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{7-hydroxy-4-oxo-2-[(1e)-pent-1-en-1-yl]-2,3-dihydro-1-benzopyran-5-yl}acetic acid

Description

Aposphaerin C belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety. {7-hydroxy-4-oxo-2-[(1e)-pent-1-en-1-yl]-2,3-dihydro-1-benzopyran-5-yl}acetic acid is found in Neophaeosphaeria quadriseptata. It was first documented in 2007 (PMID: 18052326). Based on a literature review very few articles have been published on Aposphaerin C.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    5.6887    1.1515    0.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1451   -0.1854    1.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8077    0.0099    1.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8775    0.6661    0.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7610    0.0480    0.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8114    0.6954   -0.5144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1542    1.5096    0.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5260    1.4680   -0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2542    2.4752   -0.2248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0448    0.2478   -0.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4017   -0.0263   -0.9184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3418    0.9709   -0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3428    0.9828    1.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0777    1.7953    1.7238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5559    0.1229    1.8621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8265   -1.2240   -1.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8738   -2.0801   -2.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2905   -3.2755   -2.5959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5322   -1.8239   -1.9592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0940   -0.6379   -1.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2243   -0.2995   -1.2833 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6865    0.9619    0.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7459    1.8503    1.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0405    1.5282   -0.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8562   -0.6966    1.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0118   -0.7886    0.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4526   -1.0134    1.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038    0.6221    2.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0869    1.6321    0.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4882   -0.9253    0.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3774    1.3872   -1.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2431    2.5415    0.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2373    1.1383    1.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3712    0.5481   -0.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3529    1.9426   -0.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8758   -0.7401    2.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8862   -1.4274   -1.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3843   -4.0910   -2.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7850   -2.4983   -2.3528 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
 11 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21  6  1  0
 20 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  6
  7 32  1  0
  7 33  1  0
 12 34  1  0
 12 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
 19 39  1  0
M  END


  Mrv1652309072222452D          

 21 22  0  0  0  0            999 V2000
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  0  0  0  0
  6 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256047

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC\C=C\C1CC(=O)C2=C(CC(O)=O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O5/c1-2-3-4-5-12-9-13(18)16-10(7-15(19)20)6-11(17)8-14(16)21-12/h4-6,8,12,17H,2-3,7,9H2,1H3,(H,19,20)/b5-4+

> <INCHI_KEY>
ARPNPDSBSVFTDI-SNAWJCMRSA-N

> <FORMULA>
C16H18O5

> <MOLECULAR_WEIGHT>
290.315

> <EXACT_MASS>
290.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
30.607062370071276

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{7-hydroxy-4-oxo-2-[(1E)-pent-1-en-1-yl]-3,4-dihydro-2H-1-benzopyran-5-yl}acetic acid

> <JCHEM_LOGP>
2.712536013666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.747266192976016

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4646857963597615

> <JCHEM_PKA_STRONGEST_BASIC>
-4.938699348780573

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
78.0612

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
{7-hydroxy-4-oxo-2-[(1E)-pent-1-en-1-yl]-2,3-dihydro-1-benzopyran-5-yl}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   20                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   10   21                                                  
CONECT   21   20    6                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₈O₅

Average Mass

290.3150 Da

Monoisotopic Mass

290.11542 Da

IUPAC Name

2-{7-hydroxy-4-oxo-2-[(1E)-pent-1-en-1-yl]-3,4-dihydro-2H-1-benzopyran-5-yl}acetic acid

Traditional Name

{7-hydroxy-4-oxo-2-[(1E)-pent-1-en-1-yl]-2,3-dihydro-1-benzopyran-5-yl}acetic acid

CAS Registry Number

Not Available

SMILES

CCC\C=C\C1CC(=O)C2=C(CC(O)=O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C16H18O5/c1-2-3-4-5-12-9-13(18)16-10(7-15(19)20)6-11(17)8-14(16)21-12/h4-6,8,12,17H,2-3,7,9H2,1H3,(H,19,20)/b5-4+

InChI Key

ARPNPDSBSVFTDI-SNAWJCMRSA-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
Neophaeosphaeria quadriseptata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Chromones

Alternative Parents

Substituents

Chromone
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Ketone
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
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	2.71	ChemAxon
pKa (Strongest Acidic)	3.46	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	78.06 m³·mol⁻¹	ChemAxon
Polarizability	30.61 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

C00038481

Chemspider ID

78435984

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101402553

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Paranagama PA, Wijeratne EM, Gunatilaka AA: Uncovering biosynthetic potential of plant-associated fungi: effect of culture conditions on metabolite production by Paraphaeosphaeria quadriseptata and Chaetomium chiversii. J Nat Prod. 2007 Dec;70(12):1939-45. doi: 10.1021/np070504b. Epub 2007 Dec 6. [PubMed:18052326 ]
LOTUS database [Link]

Showing NP-Card for {7-hydroxy-4-oxo-2-[(1e)-pent-1-en-1-yl]-2,3-dihydro-1-benzopyran-5-yl}acetic acid (NP0256047)

MOL for NP0256047 ({7-hydroxy-4-oxo-2-[(1e)-pent-1-en-1-yl]-2,3-dihydro-1-benzopyran-5-yl}acetic acid)

3D MOL for NP0256047 ({7-hydroxy-4-oxo-2-[(1e)-pent-1-en-1-yl]-2,3-dihydro-1-benzopyran-5-yl}acetic acid)

3D SDF for NP0256047 ({7-hydroxy-4-oxo-2-[(1e)-pent-1-en-1-yl]-2,3-dihydro-1-benzopyran-5-yl}acetic acid)

3D-SDF for NP0256047 ({7-hydroxy-4-oxo-2-[(1e)-pent-1-en-1-yl]-2,3-dihydro-1-benzopyran-5-yl}acetic acid)

PDB for NP0256047 ({7-hydroxy-4-oxo-2-[(1e)-pent-1-en-1-yl]-2,3-dihydro-1-benzopyran-5-yl}acetic acid)

3D PDB for NP0256047 ({7-hydroxy-4-oxo-2-[(1e)-pent-1-en-1-yl]-2,3-dihydro-1-benzopyran-5-yl}acetic acid)

SMILES for NP0256047 ({7-hydroxy-4-oxo-2-[(1e)-pent-1-en-1-yl]-2,3-dihydro-1-benzopyran-5-yl}acetic acid)

INCHI for NP0256047 ({7-hydroxy-4-oxo-2-[(1e)-pent-1-en-1-yl]-2,3-dihydro-1-benzopyran-5-yl}acetic acid)

Structure for NP0256047 ({7-hydroxy-4-oxo-2-[(1e)-pent-1-en-1-yl]-2,3-dihydro-1-benzopyran-5-yl}acetic acid)

3D Structure for NP0256047 ({7-hydroxy-4-oxo-2-[(1e)-pent-1-en-1-yl]-2,3-dihydro-1-benzopyran-5-yl}acetic acid)