NP-MRD: Showing NP-Card for Abieta-8,11,13-trien-7-one (NP0081227)

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Record Information

Version

2.0

Created at

2022-04-29 02:11:34 UTC

Updated at

2022-04-29 02:11:34 UTC

NP-MRD ID

NP0081227

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Abieta-8,11,13-trien-7-one

Description

7-Dehydroabietanone belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Abieta-8,11,13-trien-7-one is found in Callicarpa pilosissima, Cryptomeria japonica, Fraxinus sieboldiana, Juniperus chinensis, Picea glehni and Salvia broussonetii. Based on a literature review very few articles have been published on 7-dehydroabietanone.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
    5.3026    1.1458   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7669   -0.1660    0.1296 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1172   -0.3888    1.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2850   -0.2504   -0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7377   -1.2299   -0.8556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3694   -1.2682   -1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5033   -0.3690   -0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725    0.6143    0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4511    0.6493    0.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2311    1.5990    1.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7268    2.2883    1.9886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719    1.7119    0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6576    0.2844    0.4746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1562    0.2600    0.4244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7423    1.2574   -0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6182    0.6881    1.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7150   -1.1138    0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9107   -1.9881   -0.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4376   -1.9151   -0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9793   -0.4804   -0.6067 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2717    0.0158   -1.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4142    1.0766   -0.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9844    1.2615   -1.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0187    2.0003    0.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2261   -0.9764   -0.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1430   -0.8375    1.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4170   -1.1303    2.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1420    0.5630    2.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4045   -1.9346   -1.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9605   -2.0628   -1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595    1.4341    1.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8162    2.2029    1.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422    2.2532   -0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3730   -0.2203    1.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9881    1.8331   -1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3889    2.0205   -0.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4548    0.7445   -1.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8560    1.7895    1.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5189    0.1333    2.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8325    0.5441    2.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9259   -1.6460    1.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7252   -0.9821   -0.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1674   -1.8743   -1.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159   -3.0546   -0.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990   -2.2931    0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9620   -2.5419   -1.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9756    1.0603   -2.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6329   -0.5944   -2.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2983   -0.1132   -2.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  9  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  7 20  1  0
 20 21  1  6
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 14  1  0
 14 15  1  6
 14 16  1  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  2  0
  5  4  1  0
 13 20  1  0
 10  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  6
  3 26  1  0
  3 27  1  0
  3 28  1  0
  9 31  1  0
  6 30  1  0
  5 29  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 19 45  1  0
 19 46  1  0
 18 43  1  0
 18 44  1  0
 17 41  1  0
 17 42  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 13 34  1  1
 12 32  1  0
 12 33  1  0
M  END


  Mrv1652304292204112D          

 21 23  0  0  1  0            999 V2000
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3016   -0.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6308   -1.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  6  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  5 19  1  6  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0081227

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC2=C(C=C1)[C@@]1(C)CCCC(C)(C)[C@@H]1CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O/c1-13(2)14-7-8-16-15(11-14)17(21)12-18-19(3,4)9-6-10-20(16,18)5/h7-8,11,13,18H,6,9-10,12H2,1-5H3/t18-,20+/m0/s1

> <INCHI_KEY>
ISHVJVXYPLFKAL-AZUAARDMSA-N

> <FORMULA>
C20H28O

> <MOLECULAR_WEIGHT>
284.443

> <EXACT_MASS>
284.214015522

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.981667351404596

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,10aS)-1,1,4a-trimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-9-one

> <ALOGPS_LOGP>
5.69

> <JCHEM_LOGP>
5.412696775333333

> <ALOGPS_LOGS>
-6.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.451418424254502

> <JCHEM_PKA_STRONGEST_BASIC>
-7.477003637789814

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
88.5133

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.73e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,10aS)-7-isopropyl-1,1,4a-trimethyl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.104  -3.231   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.746   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.516  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.516   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.030  -1.380   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.777  -2.103   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20   21                                             
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7   19                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4                                                       
CONECT   12    8   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14    7                                                       
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    5                                                            
CONECT   20    3                                                            
CONECT   21    3                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O

Average Mass

284.4430 Da

Monoisotopic Mass

284.21402 Da

IUPAC Name

(4aS,10aS)-1,1,4a-trimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-9-one

Traditional Name

(4aS,10aS)-7-isopropyl-1,1,4a-trimethyl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC2=C(C=C1)[C@@]1(C)CCCC(C)(C)[C@@H]1CC2=O

InChI Identifier

InChI=1S/C20H28O/c1-13(2)14-7-8-16-15(11-14)17(21)12-18-19(3,4)9-6-10-20(16,18)5/h7-8,11,13,18H,6,9-10,12H2,1-5H3/t18-,20+/m0/s1

InChI Key

ISHVJVXYPLFKAL-AZUAARDMSA-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
Callicarpa pilosissima	Plant	KNApSAcK
Cryptomeria japonica	LOTUS Database	35616633
Fraxinus sieboldiana	LOTUS Database	35616633
Juniperus chinensis	LOTUS Database	35616633
Picea glehni	Plant	KNApSAcK
Salvia broussonetii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Abietane diterpenoid
Phenanthrene
Hydrophenanthrene
Tetralin
Aryl alkyl ketone
Aryl ketone
Benzenoid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

abietane diterpenoid (CHEBI:70574 )
tricyclic diterpenoid (CHEBI:70574 )

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	5.69	ALOGPS
logP	5.41	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	16.45	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	1	ChemAxon
Refractivity	88.51 m³·mol⁻¹	ChemAxon
Polarizability	34.98 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

9464105

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11289118

PDB ID

Not Available

ChEBI ID

70574

Good Scents ID

Not Available

References

General References

Showing NP-Card for Abieta-8,11,13-trien-7-one (NP0081227)

MOL for NP0081227 (Abieta-8,11,13-trien-7-one)

3D MOL for NP0081227 (Abieta-8,11,13-trien-7-one)

3D SDF for NP0081227 (Abieta-8,11,13-trien-7-one)

3D-SDF for NP0081227 (Abieta-8,11,13-trien-7-one)

PDB for NP0081227 (Abieta-8,11,13-trien-7-one)

3D PDB for NP0081227 (Abieta-8,11,13-trien-7-one)

SMILES for NP0081227 (Abieta-8,11,13-trien-7-one)

INCHI for NP0081227 (Abieta-8,11,13-trien-7-one)

Structure for NP0081227 (Abieta-8,11,13-trien-7-one)

3D Structure for NP0081227 (Abieta-8,11,13-trien-7-one)