NP-MRD: Showing NP-Card for 12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]heptacos-3-ene-7,24-dione (NP0215478)

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Record Information

Version

2.0

Created at

2022-09-05 15:06:52 UTC

Updated at

2022-09-05 15:06:52 UTC

NP-MRD ID

NP0215478

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]heptacos-3-ene-7,24-dione

Description

12-Hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]Heptacos-3-ene-7,24-dione belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. 12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]heptacos-3-ene-7,24-dione is found in Ptilostemon gnaphaloides. Based on a literature review very few articles have been published on 12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]Heptacos-3-ene-7,24-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052217062D          

 36 43  0  0  0  0            999 V2000
    3.3645   -0.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2441   -0.3424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6232    0.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8481    1.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309052217062D          

 36 43  0  0  0  0            999 V2000
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    2.3655    2.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0285    3.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729    2.0868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5906    1.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3952    0.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2698    0.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9301    0.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  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
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 27 33  1  0  0  0  0
 33 34  1  0  0  0  0
 20 34  1  0  0  0  0
 34 35  1  0  0  0  0
  2 35  1  0  0  0  0
 17 35  1  0  0  0  0
 34 36  1  0  0  0  0
 18 36  1  0  0  0  0
 23 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0215478

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2CCC(C)(O)C3C4C5CC6(C)OC7(C)CCC8C(C)C(=O)OC8C6(C4C(C)=C3C2OC1=O)C57

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O6/c1-12-15-7-9-27(4,33)21-18(22(15)34-25(12)31)14(3)20-19(21)17-11-29(6)30(20)23(17)28(5,36-29)10-8-16-13(2)26(32)35-24(16)30/h12-13,15-17,19-24,33H,7-11H2,1-6H3

> <INCHI_KEY>
XDKZYFZYOVAAKJ-UHFFFAOYSA-N

> <FORMULA>
C30H40O6

> <MOLECULAR_WEIGHT>
496.644

> <EXACT_MASS>
496.282489008

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
54.70519355229469

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0^{1,17}.0^{2,14}.0^{4,13}.0^{5,9}.0^{19,27}.0^{22,26}]heptacos-3-ene-7,24-dione

> <JCHEM_LOGP>
2.713867995000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.703904761630387

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9283120572628683

> <JCHEM_POLAR_SURFACE_AREA>
82.06000000000002

> <JCHEM_REFRACTIVITY>
131.22709999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0^{1,17}.0^{2,14}.0^{4,13}.0^{5,9}.0^{19,27}.0^{22,26}]heptacos-3-ene-7,24-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       6.280  -1.583   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.725  -0.146   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.561   1.147   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.101   1.162   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.962  -0.115   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.442   0.309   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.656  -0.639   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.497   1.848   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.774   2.709   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.050   2.375   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.693   3.873   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.299   4.528   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.918   3.847   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.561   5.345   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.663   4.740   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.590   2.342   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.153   1.787   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.153   0.213   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.183  -1.027   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.272   0.117   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.457  -1.189   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.217   0.446   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.092   1.919   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.444   1.807   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.445   3.380   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.494   4.607   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.053   4.644   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.947   5.898   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.458   7.358   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.416   5.435   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.653   6.352   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       4.429   3.895   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.969   3.406   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.604   1.676   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.237   0.249   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.736   1.422   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4   16                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13    3   17                                                  
CONECT   17   16   18   35                                                  
CONECT   18   17   19   36                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22   34                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25   36                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   27   34                                                  
CONECT   34   33   20   35   36                                             
CONECT   35   34    2   17                                                  
CONECT   36   34   18   23                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₀O₆

Average Mass

496.6440 Da

Monoisotopic Mass

496.28249 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1C2CCC(C)(O)C3C4C5CC6(C)OC7(C)CCC8C(C)C(=O)OC8C6(C4C(C)=C3C2OC1=O)C57

InChI Identifier

InChI=1S/C30H40O6/c1-12-15-7-9-27(4,33)21-18(22(15)34-25(12)31)14(3)20-19(21)17-11-29(6)30(20)23(17)28(5,36-29)10-8-16-13(2)26(32)35-24(16)30/h12-13,15-17,19-24,33H,7-11H2,1-6H3

InChI Key

XDKZYFZYOVAAKJ-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, 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
Ptilostemon gnaphaloides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Oxane
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
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

73157934

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]heptacos-3-ene-7,24-dione (NP0215478)

MOL for NP0215478 (12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]heptacos-3-ene-7,24-dione)

3D MOL for NP0215478 (12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]heptacos-3-ene-7,24-dione)

3D SDF for NP0215478 (12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]heptacos-3-ene-7,24-dione)

3D-SDF for NP0215478 (12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]heptacos-3-ene-7,24-dione)

PDB for NP0215478 (12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]heptacos-3-ene-7,24-dione)

3D PDB for NP0215478 (12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]heptacos-3-ene-7,24-dione)

SMILES for NP0215478 (12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]heptacos-3-ene-7,24-dione)

INCHI for NP0215478 (12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]heptacos-3-ene-7,24-dione)

Structure for NP0215478 (12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]heptacos-3-ene-7,24-dione)

3D Structure for NP0215478 (12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]heptacos-3-ene-7,24-dione)