NP-MRD: Showing NP-Card for (+)-Myricalactone (NP0073080)

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Record Information

Version

2.0

Created at

2022-04-28 18:20:30 UTC

Updated at

2022-04-28 18:20:31 UTC

NP-MRD ID

NP0073080

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Myricalactone

Description

Myricalactone belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. (+)-Myricalactone is found in Morella cerifera, Myrica cerifera L. and Myrica gale. Based on a literature review very few articles have been published on Myricalactone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220202D          

 34 39  0  0  1  0            999 V2000
    6.1319   -0.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5740    0.2297    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


  Mrv1652304282220202D          

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  6 32  1  1  0  0  0
  4 33  1  0  0  0  0
  4 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073080

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@]23CC[C@]4(C)C(C=C[C@H]5[C@@]4(C)CC[C@H]4C(C)(C)C(=O)CC(=O)[C@]54C)=C2[C@H]1OC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O4/c1-25(2)12-14-30-15-13-27(5)17(22(30)23(25)34-24(30)33)8-9-19-28(27,6)11-10-18-26(3,4)20(31)16-21(32)29(18,19)7/h8-9,18-19,23H,10-16H2,1-7H3/t18-,19-,23+,27+,28+,29-,30-/m0/s1

> <INCHI_KEY>
NNYQTGAHXKZEPT-YBVGXSOASA-N

> <FORMULA>
C30H40O4

> <MOLECULAR_WEIGHT>
464.646

> <EXACT_MASS>
464.292659768

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
52.77076193847472

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4S,5R,8S,13S,14S,19S)-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[17.3.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosa-15,17-diene-10,12,23-trione

> <ALOGPS_LOGP>
4.81

> <JCHEM_LOGP>
6.187000178000001

> <ALOGPS_LOGS>
-5.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.455788525085536

> <JCHEM_PKA_STRONGEST_BASIC>
-6.946031188322775

> <JCHEM_POLAR_SURFACE_AREA>
60.440000000000005

> <JCHEM_REFRACTIVITY>
132.26649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,5R,8S,13S,14S,19S)-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[17.3.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosa-15,17-diene-10,12,23-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      11.446  -0.871   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.271   0.429   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.810   0.364   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.558   1.794   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.019   1.858   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.194   0.558   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.908  -0.807   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.082  -2.107   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.655   0.622   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.942   1.987   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.767   3.287   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.306   3.223   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.403   2.052   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.578   0.751   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.040   0.816   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.326   2.181   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.151   3.481   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.690   3.416   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.834   1.711   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.510   0.206   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.485  -0.986   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.025  -0.967   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.970   0.248   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.609   1.745   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.746   2.784   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.271  -1.934   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.538  -2.525   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.292  -0.613   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.830  -0.678   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.229   3.352   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.167   3.511   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.369  -0.742   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.897   2.554   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.676   3.329   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   33   34                                             
CONECT    5    4    6   12                                                  
CONECT    6    5    7    9   32                                             
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10   29                                                  
CONECT   10    9   11   13   31                                             
CONECT   11   10   12                                                       
CONECT   12   11    5                                                       
CONECT   13   10   14   18   30                                             
CONECT   14   13   15   28                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   19   24                                             
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26   27                                             
CONECT   22   21   15   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   16   25                                                  
CONECT   25   24                                                            
CONECT   26   21                                                            
CONECT   27   21                                                            
CONECT   28   14   29                                                       
CONECT   29   28    9                                                       
CONECT   30   13                                                            
CONECT   31   10                                                            
CONECT   32    6                                                            
CONECT   33    4                                                            
CONECT   34    4                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₀O₄

Average Mass

464.6460 Da

Monoisotopic Mass

464.29266 Da

IUPAC Name

(1R,4S,5R,8S,13S,14S,19S)-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[17.3.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosa-15,17-diene-10,12,23-trione

Traditional Name

(1R,4S,5R,8S,13S,14S,19S)-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[17.3.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosa-15,17-diene-10,12,23-trione

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@]23CC[C@]4(C)C(C=C[C@H]5[C@@]4(C)CC[C@H]4C(C)(C)C(=O)CC(=O)[C@]54C)=C2[C@H]1OC3=O

InChI Identifier

InChI=1S/C30H40O4/c1-25(2)12-14-30-15-13-27(5)17(22(30)23(25)34-24(30)33)8-9-19-28(27,6)11-10-18-26(3,4)20(31)16-21(32)29(18,19)7/h8-9,18-19,23H,10-16H2,1-7H3/t18-,19-,23+,27+,28+,29-,30-/m0/s1

InChI Key

NNYQTGAHXKZEPT-YBVGXSOASA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Morella cerifera	LOTUS Database	35616633
Myrica cerifera L.	Plant	KNApSAcK
Myrica gale	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Oxepane
1,3-diketone
1,3-dicarbonyl compound
Gamma butyrolactone
Oxolane
Cyclic ketone
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxide
Organic oxygen compound
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
logP	4.81	ALOGPS
logP	6.19	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	8.46	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	132.27 m³·mol⁻¹	ChemAxon
Polarizability	52.77 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

C00033232

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

101699415

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Myricalactone (NP0073080)

MOL for NP0073080 ((+)-Myricalactone)

3D MOL for NP0073080 ((+)-Myricalactone)

3D SDF for NP0073080 ((+)-Myricalactone)

3D-SDF for NP0073080 ((+)-Myricalactone)

PDB for NP0073080 ((+)-Myricalactone)

3D PDB for NP0073080 ((+)-Myricalactone)

SMILES for NP0073080 ((+)-Myricalactone)

INCHI for NP0073080 ((+)-Myricalactone)

Structure for NP0073080 ((+)-Myricalactone)

3D Structure for NP0073080 ((+)-Myricalactone)