NP-MRD: Showing NP-Card for (1e,5z,9e,12r,13r)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene (NP0328301)

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Record Information

Version

1.0

Created at

2022-09-12 11:38:58 UTC

Updated at

2022-09-12 11:38:58 UTC

NP-MRD ID

NP0328301

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1e,5z,9e,12r,13r)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene

Description

(1E,5Z,9E,12R,13R)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. (1e,5z,9e,12r,13r)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene is found in Ceroplastes ceriferus. It was first documented in 2022 (PMID: 36130844). Based on a literature review a significant number of articles have been published on (1E,5Z,9E,12R,13R)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene (PMID: 36130843) (PMID: 36130842) (PMID: 36130841) (PMID: 36130840).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122213382D          

 28 28  0  0  1  0            999 V2000
    2.5302    3.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8146    3.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1012    3.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1035    4.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3901    4.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3924    5.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3210    6.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1080    6.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8123    2.2873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6162    2.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721    1.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6157    0.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3600    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6135    0.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2535   -0.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6071   -1.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8023   -1.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000   -2.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985   -1.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3548   -0.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3571    0.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0012    0.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8238    0.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3611    1.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0075    2.1059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6516    2.8502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1709    2.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5269    3.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9 10  1  0  0  0  0
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  9 25  1  0  0  0  0
 25 26  1  1  0  0  0
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 27 28  1  0  0  0  0
M  END

     RDKit          3D

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    0.2557    2.3662    2.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7984   -3.0369   -2.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309122213382D          

 28 28  0  0  1  0            999 V2000
    2.5302    3.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8146    3.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1035    4.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0328301

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCO[C@@H]1C\C(C)=C\CC\C(C)=C/CC\C(C)=C\C[C@@H]1C(=C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O/c1-8-28-27-20-24(6)16-11-14-22(4)13-10-15-23(5)18-19-26(27)25(7)17-9-12-21(2)3/h12-13,16,18,26-27H,7-11,14-15,17,19-20H2,1-6H3/b22-13-,23-18+,24-16+/t26-,27-/m1/s1

> <INCHI_KEY>
WMCFQVVNOGHBSE-CLRKCOOUSA-N

> <FORMULA>
C27H44O

> <MOLECULAR_WEIGHT>
384.648

> <EXACT_MASS>
384.339216037

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
48.96619916829995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1E,5Z,9E,12R,13R)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene

> <JCHEM_LOGP>
7.890125137999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.149039827094135

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
128.9804

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1E,5Z,9E,12R,13R)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene

> <JCHEM_VEBER_RULE>
1

$$$$

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       4.723   6.576   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.387   5.810   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.056   6.583   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.060   8.123   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.728   8.897   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.732  10.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.599  11.210   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.068  11.203   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.383   4.270   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.883   3.923   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.548   2.534   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.749   1.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.139   2.235   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.745   0.030   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.073  -1.356   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.867  -2.312   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.364  -2.651   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.360  -4.191   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.864  -2.304   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.662  -1.341   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.667   0.199   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.002   1.588   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.538   1.593   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.674   2.974   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.881   3.931   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.216   5.320   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.319   5.440   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.983   6.829   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10   25                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24    9   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₄O

Average Mass

384.6480 Da

Monoisotopic Mass

384.33922 Da

IUPAC Name

(1E,5Z,9E,12R,13R)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene

Traditional Name

(1E,5Z,9E,12R,13R)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene

CAS Registry Number

Not Available

SMILES

CCO[C@@H]1C\C(C)=C\CC\C(C)=C/CC\C(C)=C\C[C@@H]1C(=C)CCC=C(C)C

InChI Identifier

InChI=1S/C27H44O/c1-8-28-27-20-24(6)16-11-14-22(4)13-10-15-23(5)18-19-26(27)25(7)17-9-12-21(2)3/h12-13,16,18,26-27H,7-11,14-15,17,19-20H2,1-6H3/b22-13-,23-18+,24-16+/t26-,27-/m1/s1

InChI Key

WMCFQVVNOGHBSE-CLRKCOOUSA-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
Ceroplastes ceriferus	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
Cericerane sesterterpenoid
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	7.89	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	128.98 m³·mol⁻¹	ChemAxon
Polarizability	48.97 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

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

162955790

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cani I, Righini M, Cenni P, Foschi M: Teaching NeuroImage: Partially Reversible Widespread Leukoencephalopathy Associated With Atypical Hemolytic Uremic Syndrome. Neurology. 2022 Sep 21. pii: WNL.0000000000201378. doi: 10.1212/WNL.0000000000201378. [PubMed:36130844 ]
Sasaki R, Morimoto S, Ozawa F, Okano H, Yoshida M, Ishiura H, Tsuji S, Kuzuhara S, Kokubo Y: APOE Alleles With Tau and Abeta Pathology In Patients With Amyotrophic Lateral Sclerosis and Parkinsonism-Dementia Complex in the Kii Peninsula. Neurology. 2022 Sep 21. pii: WNL.0000000000201156. doi: 10.1212/WNL.0000000000201156. [PubMed:36130843 ]
Zhang Z, Wang M, Gill D, Liu X: Genetically Predicted Smoking and Alcohol Consumption and Functional Outcome After Ischemic Stroke. Neurology. 2022 Sep 21. pii: WNL.0000000000201291. doi: 10.1212/WNL.0000000000201291. [PubMed:36130842 ]
Khamis S, Mitakidou MR, Champion M, Goyal S, Jones RL, Siddiqui A, Sabanathan S, Hedderly T, Lin JP, Jungbluth H, Papandreou A: Clinical Reasoning: A Teenage Girl With Progressive Hyperkinetic Movements, Seizures, and Encephalopathy. Neurology. 2022 Sep 21. pii: WNL.0000000000201385. doi: 10.1212/WNL.0000000000201385. [PubMed:36130841 ]
Rosenberg A, Ohlund-Wistbacka U, Hall A, Bonnard A, Hagman G, Ryden M, Thunborg C, Wiggenraad F, Sandebring-Matton A, Solomon A, Kivipelto M: beta-Amyloid, Tau, Neurodegeneration Classification and Eligibility for Anti-amyloid Treatment in a Memory Clinic Population. Neurology. 2022 Sep 21. pii: WNL.0000000000201043. doi: 10.1212/WNL.0000000000201043. [PubMed:36130840 ]
LOTUS database [Link]

Showing NP-Card for (1e,5z,9e,12r,13r)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene (NP0328301)

MOL for NP0328301 ((1e,5z,9e,12r,13r)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene)

3D MOL for NP0328301 ((1e,5z,9e,12r,13r)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene)

3D SDF for NP0328301 ((1e,5z,9e,12r,13r)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene)

3D-SDF for NP0328301 ((1e,5z,9e,12r,13r)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene)

PDB for NP0328301 ((1e,5z,9e,12r,13r)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene)

3D PDB for NP0328301 ((1e,5z,9e,12r,13r)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene)

SMILES for NP0328301 ((1e,5z,9e,12r,13r)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene)

INCHI for NP0328301 ((1e,5z,9e,12r,13r)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene)

Structure for NP0328301 ((1e,5z,9e,12r,13r)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene)

3D Structure for NP0328301 ((1e,5z,9e,12r,13r)-13-ethoxy-1,5,9-trimethyl-12-(6-methylhepta-1,5-dien-2-yl)cyclotetradeca-1,5,9-triene)