NP-MRD: Showing NP-Card for ent-Abieta-7,13-diene (NP0050547)

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Record Information

Version

2.0

Created at

2022-04-27 21:56:31 UTC

Updated at

2022-04-27 21:56:31 UTC

NP-MRD ID

NP0050547

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ent-Abieta-7,13-diene

Description

Entabietic acid, also known as entabietate, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. ent-Abieta-7,13-diene is found in Helichrysum chionosphaerum and Solidago rugosa. Based on a literature review very few articles have been published on Entabietic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272223562D          

 20 22  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  2  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  1  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  1  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
    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  1  1  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  5 18  1  1  0  0  0
  3 19  1  0  0  0  0
  3 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050547

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC2=CC[C@@H]3C(C)(C)CCC[C@@]3(C)[C@@H]2CC1

> <INCHI_IDENTIFIER>
InChI=1S/C20H32/c1-14(2)15-7-9-17-16(13-15)8-10-18-19(3,4)11-6-12-20(17,18)5/h8,13-14,17-18H,6-7,9-12H2,1-5H3/t17-,18-,20+/m1/s1

> <INCHI_KEY>
BBPXZLJCPUPNGH-GGPKGHCWSA-N

> <FORMULA>
C20H32

> <MOLECULAR_WEIGHT>
272.476

> <EXACT_MASS>
272.25040103

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
35.257208357628244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aR,4bS,10aR)-1,1,4a-trimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene

> <ALOGPS_LOGP>
6.91

> <JCHEM_LOGP>
5.760872461333333

> <ALOGPS_LOGS>
-5.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
89.497

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.08e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,4bS,10aR)-7-isopropyl-1,1,4a-trimethyl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-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  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.746   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.516  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.516   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.030  -1.380   0.000  0.00  0.00           C+0
HETATM   20  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   19   20                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   18                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    5                                                            
CONECT   19    3                                                            
CONECT   20    3                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
Entabietate	Generator

Chemical Formula

C₂₀H₃₂

Average Mass

272.4760 Da

Monoisotopic Mass

272.25040 Da

IUPAC Name

(4aR,4bS,10aR)-1,1,4a-trimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene

Traditional Name

(4aR,4bS,10aR)-7-isopropyl-1,1,4a-trimethyl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC2=CC[C@@H]3C(C)(C)CCC[C@@]3(C)[C@@H]2CC1

InChI Identifier

InChI=1S/C20H32/c1-14(2)15-7-9-17-16(13-15)8-10-18-19(3,4)11-6-12-20(17,18)5/h8,13-14,17-18H,6-7,9-12H2,1-5H3/t17-,18-,20+/m1/s1

InChI Key

BBPXZLJCPUPNGH-GGPKGHCWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.16420112 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Helichrysum chionosphaerum	Plant	KNApSAcK
Solidago rugosa	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
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
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	6.91	ALOGPS
logP	5.76	ChemAxon
logS	-5.7	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.5 m³·mol⁻¹	ChemAxon
Polarizability	35.26 Å³	ChemAxon
Number of Rings	3	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

421104

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

479912

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for ent-Abieta-7,13-diene (NP0050547)

MOL for NP0050547 (ent-Abieta-7,13-diene)

3D MOL for NP0050547 (ent-Abieta-7,13-diene)

3D SDF for NP0050547 (ent-Abieta-7,13-diene)

3D-SDF for NP0050547 (ent-Abieta-7,13-diene)

PDB for NP0050547 (ent-Abieta-7,13-diene)

3D PDB for NP0050547 (ent-Abieta-7,13-diene)

SMILES for NP0050547 (ent-Abieta-7,13-diene)

INCHI for NP0050547 (ent-Abieta-7,13-diene)

Structure for NP0050547 (ent-Abieta-7,13-diene)

3D Structure for NP0050547 (ent-Abieta-7,13-diene)