NP-MRD: Showing NP-Card for (8e,10e,12e,15e,18e)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione (NP0324493)

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Record Information

Version

2.0

Created at

2022-09-12 04:36:36 UTC

Updated at

2022-09-12 04:36:36 UTC

NP-MRD ID

NP0324493

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8e,10e,12e,15e,18e)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione

Description

(8E,10E,12E,15E,18E)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. (8e,10e,12e,15e,18e)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione is found in Smaragdinella calyculata. Based on a literature review very few articles have been published on (8E,10E,12E,15E,18E)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122206362D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309122206362D          

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M  END
> <DATABASE_ID>
NP0324493

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)C(C)C(=O)C(C)C\C(C)=C\C(\C)=C\C(\C)=C\C(C)\C=C(/C)C(O)C(\C)=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O3/c1-11-22(7)27(30)23(8)16-20(5)14-18(3)13-19(4)15-21(6)17-24(9)28(31)25(10)26(29)12-2/h11,13-16,20,24-25,27,30H,12,17H2,1-10H3/b18-14+,19-13+,21-15+,22-11+,23-16+

> <INCHI_KEY>
OPBJITJQJWANRV-MHTLXNHPSA-N

> <FORMULA>
C28H44O3

> <MOLECULAR_WEIGHT>
428.657

> <EXACT_MASS>
428.329045277

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.293829840748096

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8E,10E,12E,15E,18E)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione

> <JCHEM_LOGP>
7.213884236999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.152678461633517

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.519176410921375

> <JCHEM_PKA_STRONGEST_BASIC>
-1.419817837977373

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
137.2089

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(8E,10E,12E,15E,18E)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -7.383   9.597   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.383   8.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.717   7.287   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.050   8.057   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.717   5.747   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0     -10.050   4.977   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -7.383   4.977   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.049   5.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.383   3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.049   2.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.049   1.127   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.716   3.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.382   2.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.382   1.127   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.048   3.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.715   2.667   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.715   1.127   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.619   3.437   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.953   2.667   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.953   1.127   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.620   1.127   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.954   4.977   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.287   1.127   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.621   4.977   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.288   3.437   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₄O₃

Average Mass

428.6570 Da

Monoisotopic Mass

428.32905 Da

IUPAC Name

(8E,10E,12E,15E,18E)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione

Traditional Name

(8E,10E,12E,15E,18E)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione

CAS Registry Number

Not Available

SMILES

CCC(=O)C(C)C(=O)C(C)C\C(C)=C\C(\C)=C\C(\C)=C\C(C)\C=C(/C)C(O)C(\C)=C\C

InChI Identifier

InChI=1S/C28H44O3/c1-11-22(7)27(30)23(8)16-20(5)14-18(3)13-19(4)15-21(6)17-24(9)28(31)25(10)26(29)12-2/h11,13-16,20,24-25,27,30H,12,17H2,1-10H3/b18-14+,19-13+,21-15+,22-11+,23-16+

InChI Key

OPBJITJQJWANRV-MHTLXNHPSA-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
Smaragdinella calyculata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Acyclic diterpenoids

Alternative Parents

Substituents

Acyclic diterpenoid
Long chain fatty alcohol
Fatty alcohol
1,3-diketone
Fatty acyl
1,3-dicarbonyl compound
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	7.21	ChemAxon
pKa (Strongest Acidic)	9.52	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	137.21 m³·mol⁻¹	ChemAxon
Polarizability	52.29 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

8540754

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10365305

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (8e,10e,12e,15e,18e)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione (NP0324493)

MOL for NP0324493 ((8e,10e,12e,15e,18e)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione)

3D MOL for NP0324493 ((8e,10e,12e,15e,18e)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione)

3D SDF for NP0324493 ((8e,10e,12e,15e,18e)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione)

3D-SDF for NP0324493 ((8e,10e,12e,15e,18e)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione)

PDB for NP0324493 ((8e,10e,12e,15e,18e)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione)

3D PDB for NP0324493 ((8e,10e,12e,15e,18e)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione)

SMILES for NP0324493 ((8e,10e,12e,15e,18e)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione)

INCHI for NP0324493 ((8e,10e,12e,15e,18e)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione)

Structure for NP0324493 ((8e,10e,12e,15e,18e)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione)

3D Structure for NP0324493 ((8e,10e,12e,15e,18e)-17-hydroxy-4,6,8,10,12,14,16,18-octamethylicosa-8,10,12,15,18-pentaene-3,5-dione)