NP-MRD: Showing NP-Card for (5r,5as,7as,7br,9as,13as,13bs,15ar,15bs)-9a-(hydroxymethyl)-5,5a,7b,12,12,13b,15a-heptamethyl-tetradecahydro-1h-chryseno[2,1-c]oxepin-3-one (NP0207445)

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Record Information

Version

2.0

Created at

2022-09-05 04:03:39 UTC

Updated at

2022-09-05 04:03:39 UTC

NP-MRD ID

NP0207445

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r,5as,7as,7br,9as,13as,13bs,15ar,15bs)-9a-(hydroxymethyl)-5,5a,7b,12,12,13b,15a-heptamethyl-tetradecahydro-1h-chryseno[2,1-c]oxepin-3-one

Description

Apetalactone belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. (5r,5as,7as,7br,9as,13as,13bs,15ar,15bs)-9a-(hydroxymethyl)-5,5a,7b,12,12,13b,15a-heptamethyl-tetradecahydro-1h-chryseno[2,1-c]oxepin-3-one was first documented in 2012 (PMID: 22445651). Based on a literature review very few articles have been published on Apetalactone (PMID: 23577701).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052206032D          

 33 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309052206032D          

 33 37  0  0  1  0            999 V2000
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    7.9730    1.4640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3755    2.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 13 32  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0207445

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1OC(=O)CC[C@H]2[C@]3(C)CC[C@@]4(C)[C@@H]5CC(C)(C)CC[C@]5(CO)CC[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O3/c1-20-26(4)11-10-22-27(5,21(26)8-9-24(32)33-20)13-14-29(7)23-18-25(2,3)12-16-30(23,19-31)17-15-28(22,29)6/h20-23,31H,8-19H2,1-7H3/t20-,21-,22+,23+,26-,27+,28-,29+,30-/m1/s1

> <INCHI_KEY>
BWYZTOBVTZACSG-QOAFEPIISA-N

> <FORMULA>
C30H50O3

> <MOLECULAR_WEIGHT>
458.727

> <EXACT_MASS>
458.37599547

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
55.89101076215799

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,14R,15S,20R,21S)-5-(hydroxymethyl)-2,8,8,11,14,20,21-heptamethyl-19-oxapentacyclo[12.9.0.0^{2,11}.0^{5,10}.0^{15,21}]tricosan-18-one

> <JCHEM_LOGP>
6.415500260000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.886000683761825

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0990628059103718

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
132.93679999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10S,11S,14R,15S,20R,21S)-5-(hydroxymethyl)-2,8,8,11,14,20,21-heptamethyl-19-oxapentacyclo[12.9.0.0^{2,11}.0^{5,10}.0^{15,21}]tricosan-18-one

> <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      21.455   4.526   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.022   3.048   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      22.165   2.017   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      22.072   0.480   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      23.416  -0.272   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      20.812  -0.406   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.334   0.028   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.751   1.453   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.503   2.798   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.151   4.194   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.714   4.120   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.174   4.099   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.423   2.754   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.211   1.432   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.000   0.109   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.460   0.087   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.920   0.066   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.132   1.389   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.381   0.044   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.592   1.367   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.841   0.023   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.301   0.001   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.589  -1.512   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.861  -0.546   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.512   1.324   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.263   2.668   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.803   2.690   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.015   4.013   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.766   5.357   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.555   4.034   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.094   4.056   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.883   2.733   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.634   4.077   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8    2   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   32                                                  
CONECT   14   13    8   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   32                                             
CONECT   19   18                                                            
CONECT   20   18   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   20   28   30                                             
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   13   18   33                                             
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₀O₃

Average Mass

458.7270 Da

Monoisotopic Mass

458.37600 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1OC(=O)CC[C@H]2[C@]3(C)CC[C@@]4(C)[C@@H]5CC(C)(C)CC[C@]5(CO)CC[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C30H50O3/c1-20-26(4)11-10-22-27(5,21(26)8-9-24(32)33-20)13-14-29(7)23-18-25(2,3)12-16-30(23,19-31)17-15-28(22,29)6/h20-23,31H,8-19H2,1-7H3/t20-,21-,22+,23+,26-,27+,28-,29+,30-/m1/s1

InChI Key

BWYZTOBVTZACSG-QOAFEPIISA-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 lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Not Available

Direct Parent

Lactones

Alternative Parents

Substituents

Caprolactone
Oxepane
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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

10297513

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12306723

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Joshi SP, Kulkarni SR, Phalgune UD, Puranik VG: New dipyranocoumarin from the leaves of Calophyllum apetalum Willd. Nat Prod Res. 2013 Oct;27(20):1896-901. doi: 10.1080/14786419.2013.784869. Epub 2013 Apr 11. [PubMed:23577701 ]
Ferchichi L, Derbre S, Mahmood K, Toure K, Guilet D, Litaudon M, Awang K, Hadi AH, Le Ray AM, Richomme P: Bioguided fractionation and isolation of natural inhibitors of advanced glycation end-products (AGEs) from Calophyllum flavoramulum. Phytochemistry. 2012 Jun;78:98-106. doi: 10.1016/j.phytochem.2012.02.006. Epub 2012 Mar 23. [PubMed:22445651 ]
LOTUS database [Link]

Showing NP-Card for (5r,5as,7as,7br,9as,13as,13bs,15ar,15bs)-9a-(hydroxymethyl)-5,5a,7b,12,12,13b,15a-heptamethyl-tetradecahydro-1h-chryseno[2,1-c]oxepin-3-one (NP0207445)

MOL for NP0207445 ((5r,5as,7as,7br,9as,13as,13bs,15ar,15bs)-9a-(hydroxymethyl)-5,5a,7b,12,12,13b,15a-heptamethyl-tetradecahydro-1h-chryseno[2,1-c]oxepin-3-one)

3D MOL for NP0207445 ((5r,5as,7as,7br,9as,13as,13bs,15ar,15bs)-9a-(hydroxymethyl)-5,5a,7b,12,12,13b,15a-heptamethyl-tetradecahydro-1h-chryseno[2,1-c]oxepin-3-one)

3D SDF for NP0207445 ((5r,5as,7as,7br,9as,13as,13bs,15ar,15bs)-9a-(hydroxymethyl)-5,5a,7b,12,12,13b,15a-heptamethyl-tetradecahydro-1h-chryseno[2,1-c]oxepin-3-one)

3D-SDF for NP0207445 ((5r,5as,7as,7br,9as,13as,13bs,15ar,15bs)-9a-(hydroxymethyl)-5,5a,7b,12,12,13b,15a-heptamethyl-tetradecahydro-1h-chryseno[2,1-c]oxepin-3-one)

PDB for NP0207445 ((5r,5as,7as,7br,9as,13as,13bs,15ar,15bs)-9a-(hydroxymethyl)-5,5a,7b,12,12,13b,15a-heptamethyl-tetradecahydro-1h-chryseno[2,1-c]oxepin-3-one)

3D PDB for NP0207445 ((5r,5as,7as,7br,9as,13as,13bs,15ar,15bs)-9a-(hydroxymethyl)-5,5a,7b,12,12,13b,15a-heptamethyl-tetradecahydro-1h-chryseno[2,1-c]oxepin-3-one)

SMILES for NP0207445 ((5r,5as,7as,7br,9as,13as,13bs,15ar,15bs)-9a-(hydroxymethyl)-5,5a,7b,12,12,13b,15a-heptamethyl-tetradecahydro-1h-chryseno[2,1-c]oxepin-3-one)

INCHI for NP0207445 ((5r,5as,7as,7br,9as,13as,13bs,15ar,15bs)-9a-(hydroxymethyl)-5,5a,7b,12,12,13b,15a-heptamethyl-tetradecahydro-1h-chryseno[2,1-c]oxepin-3-one)

Structure for NP0207445 ((5r,5as,7as,7br,9as,13as,13bs,15ar,15bs)-9a-(hydroxymethyl)-5,5a,7b,12,12,13b,15a-heptamethyl-tetradecahydro-1h-chryseno[2,1-c]oxepin-3-one)

3D Structure for NP0207445 ((5r,5as,7as,7br,9as,13as,13bs,15ar,15bs)-9a-(hydroxymethyl)-5,5a,7b,12,12,13b,15a-heptamethyl-tetradecahydro-1h-chryseno[2,1-c]oxepin-3-one)