NP-MRD: Showing NP-Card for 4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1h-picen-3-one (NP0317713)

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Record Information

Version

2.0

Created at

2022-09-11 17:44:47 UTC

Updated at

2022-09-11 17:44:47 UTC

NP-MRD ID

NP0317713

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1h-picen-3-one

Description

Beta-Amyrenone, also known as β-amyrenone, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1h-picen-3-one is found in Adiantum capillus-veneris, Aglaia lawii, Alibertia macrophylla, Alstonia boonei, Arabidopsis thaliana, Bambusa chungii, Canarium zeylanicum, Cyclocarya paliurus, Drypetes gossweileri, Ekebergia pterophylla, Erythrophleum fordii, Euphorbia bivonae, Euphorbia drupifera, Excoecaria agallocha, Ficus pandurata, Ixeris chinensis, Lophanthera lactescens, Macaranga tanarius, Manihot esculenta, Muntingia calabura, Picris hieracioides, Pterocarpus santalinus, Salacia chinensis, Senecio crassissimus, Solidago nemoralis, Trattinnickia burserifolia, Tridax procumbens, Viburnum opulus and Zanthoxylum beecheyanum. Beta-Amyrenone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241223402D          

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  Mrv0541 02241223402D          

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  8  9  1  0  0  0  0
  8 29  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 23  1  0  0  0  0
 18 26  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 26  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0317713

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC2(C)CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C2C1

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

> <INCHI_KEY>
LIIFBMGUDSHTOU-UHFFFAOYSA-N

> <FORMULA>
C30H48O

> <MOLECULAR_WEIGHT>
424.7015

> <EXACT_MASS>
424.370516158

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
53.522130228759416

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,4,6a,6b,8a,11,11,14b-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>
7.66

> <JCHEM_LOGP>
7.966668539999999

> <ALOGPS_LOGS>
-6.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.95829272986144

> <JCHEM_PKA_STRONGEST_BASIC>
-7.4708850131330315

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
131.08499999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.15e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1H-picen-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.335   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.001   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.666   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.666   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.666  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.666  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.002   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.667   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.002   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.667  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.335  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.666  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.666  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.001  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.002  -3.850   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.667  -1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.333  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.001  -1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.001   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.323  -5.030   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.333  -3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.344  -5.030   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.679   5.030   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.667   3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.658   5.030   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.436  -2.874   0.000  0.00  0.00           C+0
CONECT    1    2   29                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6   14   16   31                                             
CONECT    8    9   29                                                       
CONECT    9    8   10                                                       
CONECT   10    2    9   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14    3    7   13   15                                             
CONECT   15   14                                                            
CONECT   16    7   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   23   26                                                  
CONECT   19   20                                                            
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23    6   18   22   24                                             
CONECT   24   23                                                            
CONECT   25   26                                                            
CONECT   26   18   20   25   27                                             
CONECT   27   26                                                            
CONECT   28   29                                                            
CONECT   29    1    8   28   30                                             
CONECT   30   29                                                            
CONECT   31    7                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
b-Amyrenone	Generator
Β-amyrenone	Generator

Chemical Formula

C₃₀H₄₈O

Average Mass

424.7015 Da

Monoisotopic Mass

424.37052 Da

IUPAC Name

4,4,6a,6b,8a,11,11,14b-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

4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1H-picen-3-one

CAS Registry Number

Not Available

SMILES

CC1(C)CCC2(C)CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C2C1

InChI Identifier

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

InChI Key

LIIFBMGUDSHTOU-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
Adiantum capillus-veneris	LOTUS Database	35616633
Aglaia lawii	LOTUS Database	35616633
Alibertia macrophylla	LOTUS Database	35616633
Alstonia boonei	LOTUS Database	35616633
Arabidopsis thaliana	LOTUS Database	35616633
Bambusa chungii	LOTUS Database	35616633
Canarium zeylanicum	LOTUS Database	35616633
Cyclocarya paliurus	LOTUS Database	35616633
Drypetes gossweileri	LOTUS Database	35616633
Ekebergia pterophylla	LOTUS Database	35616633
Erythrophleum fordii	LOTUS Database	35616633
Euphorbia bivonae	LOTUS Database	35616633
Euphorbia drupifera	LOTUS Database	35616633
Excoecaria agallocha	LOTUS Database	35616633
Ficus pandurata	LOTUS Database	35616633
Ixeris chinensis	LOTUS Database	35616633
Lophanthera lactescens	LOTUS Database	35616633
Macaranga tanarius	LOTUS Database	35616633
Manihot esculenta	LOTUS Database	35616633
Muntingia calabura	LOTUS Database	35616633
Picris hieracioides	LOTUS Database	35616633
Pterocarpus santalinus	LOTUS Database	35616633
Salacia chinensis	LOTUS Database	35616633
Senecio crassissimus	LOTUS Database	35616633
Solidago nemoralis	LOTUS Database	35616633
Trattinnickia burserifolia	LOTUS Database	35616633
Tridax procumbens	LOTUS Database	35616633
Viburnum opulus	LOTUS Database	35616633
Zanthoxylum beecheyanum	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	7.66	ALOGPS
logP	7.97	ChemAxon
logS	-6.8	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	131.08 m³·mol⁻¹	ChemAxon
Polarizability	53.52 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

FDB006919

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

612782

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1h-picen-3-one (NP0317713)

MOL for NP0317713 (4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1h-picen-3-one)

3D MOL for NP0317713 (4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1h-picen-3-one)

3D SDF for NP0317713 (4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1h-picen-3-one)

3D-SDF for NP0317713 (4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1h-picen-3-one)

PDB for NP0317713 (4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1h-picen-3-one)

3D PDB for NP0317713 (4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1h-picen-3-one)

SMILES for NP0317713 (4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1h-picen-3-one)

INCHI for NP0317713 (4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1h-picen-3-one)

Structure for NP0317713 (4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1h-picen-3-one)

3D Structure for NP0317713 (4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1h-picen-3-one)