NP-MRD: Showing NP-Card for α-amyrenone (NP0169239)

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Record Information

Version

1.0

Created at

2022-09-03 05:09:38 UTC

Updated at

2022-09-03 05:09:38 UTC

NP-MRD ID

NP0169239

Secondary Accession Numbers

None

Natural Product Identification

Common Name

α-amyrenone

Description

Alpha-Amyrenone, also known as α-amyrenone, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. α-amyrenone is found in Alibertia macrophylla, Artemisia annua, Bambusa chungii, Boswellia sacra, Buddleja officinalis, Canarium zeylanicum, Centaurea benedicta, Diospyros ebenum, Festuca argentina, Ixeris chinensis, Lasiocephalus ovatus, Marsdenia oreophila, Marsdenia tinctoria, Packera hartiana, Picris hieracioides, Plumeria obtusa, Shorea robusta and Viburnum opulus. It was first documented in 2013 (PMID: 23776030). Based on a literature review a significant number of articles have been published on alpha-Amyrenone (PMID: 25058466) (PMID: 34736355) (PMID: 28212341) (PMID: 23148482).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032207092D          

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M  END

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 28 29  1  0  0  0  0
 16 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  6  0  0  0
 31 13  1  1  0  0  0
  2 31  1  0  0  0  0
  7 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0169239

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2[C@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h9,19-20,22-23,25H,10-18H2,1-8H3/t19-,20+,22+,23-,25+,27-,28+,29-,30-/m1/s1

> <INCHI_KEY>
DIFWJJFSELKWGA-IPQOMUISSA-N

> <FORMULA>
C30H48O

> <MOLECULAR_WEIGHT>
424.713

> <EXACT_MASS>
424.370516166

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
53.0032541678808

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-one

> <ALOGPS_LOGP>
7.30

> <JCHEM_LOGP>
7.953640516333333

> <ALOGPS_LOGS>
-7.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.958292729750507

> <JCHEM_PKA_STRONGEST_BASIC>
-7.4708850131330315

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
131.15849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.50e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydropicen-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       2.874  -5.803   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.206  -5.803   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334 -11.137   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.654  -8.470   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.791 -10.330   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.076 -11.320   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.885 -11.335   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   31                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   29                                             
CONECT   12   11                                                            
CONECT   13   11   14   31                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   29                                                  
CONECT   17   16   18   19   26                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   17   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   16   11   30                                             
CONECT   30   29                                                            
CONECT   31   13    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
a-Amyrenone	Generator
Α-amyrenone	Generator

Chemical Formula

C₃₀H₄₈O

Average Mass

424.7130 Da

Monoisotopic Mass

424.37052 Da

IUPAC Name

(4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-one

Traditional Name

(4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydropicen-3-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2[C@H]1C

InChI Identifier

InChI=1S/C30H48O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h9,19-20,22-23,25H,10-18H2,1-8H3/t19-,20+,22+,23-,25+,27-,28+,29-,30-/m1/s1

InChI Key

DIFWJJFSELKWGA-IPQOMUISSA-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
Alibertia macrophylla	LOTUS Database	35616633
Artemisia annua	LOTUS Database	35616633
Bambusa chungii	LOTUS Database	35616633
Boswellia sacra	LOTUS Database	35616633
Buddleja officinalis	LOTUS Database	35616633
Canarium zeylanicum	LOTUS Database	35616633
Centaurea benedicta	LOTUS Database	35616633
Diospyros ebenum	LOTUS Database	35616633
Festuca argentina	LOTUS Database	35616633
Ixeris chinensis	LOTUS Database	35616633
Lasiocephalus ovatus	LOTUS Database	35616633
Marsdenia oreophila	LOTUS Database	35616633
Marsdenia tinctoria	LOTUS Database	35616633
Packera hartiana	LOTUS Database	35616633
Picris hieracioides	LOTUS Database	35616633
Plumeria obtusa	LOTUS Database	35616633
Shorea robusta	LOTUS Database	35616633
Viburnum opulus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	7.3	ALOGPS
logP	7.95	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	19.96	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	131.16 m³·mol⁻¹	ChemAxon
Polarizability	53 Å³	ChemAxon
Number of Rings	5	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

19980585

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12306155

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pensec F, Paczkowski C, Grabarczyk M, Wozniak A, Benard-Gellon M, Bertsch C, Chong J, Szakiel A: Changes in the triterpenoid content of cuticular waxes during fruit ripening of eight grape (Vitis vinifera) cultivars grown in the Upper Rhine Valley. J Agric Food Chem. 2014 Aug 13;62(32):7998-8007. doi: 10.1021/jf502033s. Epub 2014 Jul 30. [PubMed:25058466 ]
Korkmaz B, Renda G, Erik I, Kilic G, Coskuncelebi K, Yayli N: Two new dihydroisocoumarins and terpenoids from Scorzonera longiana Sumbul an endemic species to Turkey and their antimicrobial activity. Nat Prod Res. 2021 Nov 5:1-14. doi: 10.1080/14786419.2021.2000410. [PubMed:34736355 ]
Rudiger AL, Veiga-Junior VF: Chemodiversity of ursane- and oleanane-type triterpenes in Amazonian Burseraceae oleoresins. Chem Biodivers. 2013 Jun;10(6):1142-53. doi: 10.1002/cbdv.201200315. [PubMed:23776030 ]
Ferreira RG, Silva Junior WF, Veiga Junior VF, Lima AA, Lima ES: Physicochemical Characterization and Biological Activities of the Triterpenic Mixture alpha,beta-Amyrenone. Molecules. 2017 Feb 16;22(2):298. doi: 10.3390/molecules22020298. [PubMed:28212341 ]
Szakiel A, Nizynski B, Paczkowski C: Triterpenoid profile of flower and leaf cuticular waxes of heather Calluna vulgaris. Nat Prod Res. 2013 Aug;27(15):1404-7. doi: 10.1080/14786419.2012.742083. Epub 2012 Nov 13. [PubMed:23148482 ]
LOTUS database [Link]

Showing NP-Card for α-amyrenone (NP0169239)

MOL for NP0169239 (α-amyrenone)

3D MOL for NP0169239 (α-amyrenone)

3D SDF for NP0169239 (α-amyrenone)

3D-SDF for NP0169239 (α-amyrenone)

PDB for NP0169239 (α-amyrenone)

3D PDB for NP0169239 (α-amyrenone)

SMILES for NP0169239 (α-amyrenone)

INCHI for NP0169239 (α-amyrenone)

Structure for NP0169239 (α-amyrenone)

3D Structure for NP0169239 (α-amyrenone)