NP-MRD: Showing NP-Card for 6-[(1e,3e)-hepta-1,3-dien-1-yl]-4,9,10-trihydroxy-3-methylidene-2-oxaspiro[4.5]dec-7-en-1-one (NP0149777)

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Record Information

Version

2.0

Created at

2022-09-02 05:42:55 UTC

Updated at

2022-09-02 05:42:55 UTC

NP-MRD ID

NP0149777

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[(1e,3e)-hepta-1,3-dien-1-yl]-4,9,10-trihydroxy-3-methylidene-2-oxaspiro[4.5]dec-7-en-1-one

Description

Oxaspirol A belongs to the class of organic compounds known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms. 6-[(1e,3e)-hepta-1,3-dien-1-yl]-4,9,10-trihydroxy-3-methylidene-2-oxaspiro[4.5]dec-7-en-1-one is found in Rhodotorula glutinis. Based on a literature review very few articles have been published on Oxaspirol A.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -0.2521   -0.4991    3.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1790    0.1382    2.7802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5892    1.4405    3.0203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3650    1.9209    1.9763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0250    2.9885    2.0390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2265    0.9412    0.8722 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0378    1.3319    0.0309 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3560    0.1677   -0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9037   -0.0758   -0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6107   -1.2124   -0.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8703   -1.4233   -0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6556   -2.5664   -1.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8388   -2.0424   -1.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7531   -1.2110   -1.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3531    2.3636   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5551    2.6145   -1.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7359    1.8973   -0.8827 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7228    2.7741   -0.4007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4794    0.7789    0.0582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4655   -0.4677   -0.5872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9980   -0.3360    1.6358 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4089   -1.3259    0.9012 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2593   -0.0116    4.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0438   -1.5263    3.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843    1.8293    0.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8886   -0.4854   -1.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4530    0.6013    0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0861   -1.8740   -1.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518   -0.7321    0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0375   -3.1633   -0.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0368   -3.2567   -1.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479   -1.3965   -2.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330   -2.9007   -2.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3687   -0.9575   -0.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6824   -1.8144   -0.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0762   -0.2973   -1.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5187    2.9430   -1.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7307    3.3918   -2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2108    1.4300   -1.8014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5166    2.2101   -0.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3367    0.7325    0.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5746   -0.2972   -1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9964   -0.6430    2.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0021   -1.9792    1.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  6  1  0
  6 21  1  0
 21 22  1  0
 21  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  6  7  1  0
  6  4  1  1
 14 34  1  0
 14 35  1  0
 14 36  1  0
 13 32  1  0
 13 33  1  0
 12 30  1  0
 12 31  1  0
 11 29  1  0
 10 28  1  0
  9 27  1  0
  8 26  1  0
  7 25  1  1
 15 37  1  0
 16 38  1  0
 17 39  1  6
 18 40  1  0
 19 41  1  1
 20 42  1  0
 21 43  1  1
 22 44  1  0
  1 23  1  0
  1 24  1  0
M  END


  Mrv1652309022207422D          

 22 23  0  0  0  0            999 V2000
   -0.6674   -0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9195    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9195   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  4  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
  9 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  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  0  0  0  0
  6 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0149777

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC\C=C\C=C\C1C=CC(O)C(O)C11C(O)C(=C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O5/c1-3-4-5-6-7-8-12-9-10-13(18)15(20)17(12)14(19)11(2)22-16(17)21/h5-10,12-15,18-20H,2-4H2,1H3/b6-5+,8-7+

> <INCHI_KEY>
LMEOQXMUHQUZJM-BSWSSELBSA-N

> <FORMULA>
C17H22O5

> <MOLECULAR_WEIGHT>
306.358

> <EXACT_MASS>
306.146723808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.336324351725935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(1E,3E)-hepta-1,3-dien-1-yl]-4,9,10-trihydroxy-3-methylidene-2-oxaspiro[4.5]dec-7-en-1-one

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
1.1386005556666658

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.506100058006385

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.835528929513483

> <JCHEM_PKA_STRONGEST_BASIC>
-3.326299781103332

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
85.58200000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(1E,3E)-hepta-1,3-dien-1-yl]-4,9,10-trihydroxy-3-methylidene-2-oxaspiro[4.5]dec-7-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.246  -0.905   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.000   1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.465   2.016   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.465   3.556   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.140   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.370   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.140   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.370   6.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.140   7.438   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.370   8.772   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.140  10.106   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.370  11.439   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.680   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.450   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.680  -0.564   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.450  -1.897   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.140  -0.564   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.370  -1.897   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.465  -2.016   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   19   21                                             
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    7   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    6   20                                                  
CONECT   20   19                                                            
CONECT   21    6    2   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₂O₅

Average Mass

306.3580 Da

Monoisotopic Mass

306.14672 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC\C=C\C=C\C1C=CC(O)C(O)C11C(O)C(=C)OC1=O

InChI Identifier

InChI=1S/C17H22O5/c1-3-4-5-6-7-8-12-9-10-13(18)15(20)17(12)14(19)11(2)22-16(17)21/h5-10,12-15,18-20H,2-4H2,1H3/b6-5+,8-7+

InChI Key

LMEOQXMUHQUZJM-BSWSSELBSA-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
Rhodotorula glutinis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxolanes

Sub Class

Not Available

Direct Parent

Oxolanes

Alternative Parents

Substituents

Enol ester
Oxolane
1,2-diol
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

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

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

13922361

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-[(1e,3e)-hepta-1,3-dien-1-yl]-4,9,10-trihydroxy-3-methylidene-2-oxaspiro[4.5]dec-7-en-1-one (NP0149777)

MOL for NP0149777 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-4,9,10-trihydroxy-3-methylidene-2-oxaspiro[4.5]dec-7-en-1-one)

3D MOL for NP0149777 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-4,9,10-trihydroxy-3-methylidene-2-oxaspiro[4.5]dec-7-en-1-one)

3D SDF for NP0149777 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-4,9,10-trihydroxy-3-methylidene-2-oxaspiro[4.5]dec-7-en-1-one)

3D-SDF for NP0149777 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-4,9,10-trihydroxy-3-methylidene-2-oxaspiro[4.5]dec-7-en-1-one)

PDB for NP0149777 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-4,9,10-trihydroxy-3-methylidene-2-oxaspiro[4.5]dec-7-en-1-one)

3D PDB for NP0149777 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-4,9,10-trihydroxy-3-methylidene-2-oxaspiro[4.5]dec-7-en-1-one)

SMILES for NP0149777 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-4,9,10-trihydroxy-3-methylidene-2-oxaspiro[4.5]dec-7-en-1-one)

INCHI for NP0149777 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-4,9,10-trihydroxy-3-methylidene-2-oxaspiro[4.5]dec-7-en-1-one)

Structure for NP0149777 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-4,9,10-trihydroxy-3-methylidene-2-oxaspiro[4.5]dec-7-en-1-one)

3D Structure for NP0149777 (6-[(1e,3e)-hepta-1,3-dien-1-yl]-4,9,10-trihydroxy-3-methylidene-2-oxaspiro[4.5]dec-7-en-1-one)