NP-MRD: Showing NP-Card for (1r,4ar,7s)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid (NP0258919)

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Record Information

Version

2.0

Created at

2022-09-08 00:36:42 UTC

Updated at

2022-09-08 00:36:42 UTC

NP-MRD ID

NP0258919

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4ar,7s)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid

Description

Acanthoic acid, also known as acanthoate, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (1r,4ar,7s)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid is found in Coleonema pulchellum, Eleutherococcus koreanus and Plagiochila deltoidea. (1r,4ar,7s)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid was first documented in 2019 (PMID: 31421115). Based on a literature review a small amount of articles have been published on acanthoic acid (PMID: 35958135) (PMID: 35597316) (PMID: 34779075) (PMID: 33290909).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    4.0962    1.0094    1.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0230   -0.1594    0.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2081   -0.4311   -0.5262 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1932   -0.9521   -1.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2635   -1.5749   -0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0278   -1.1197    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5231    0.0846    0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1943    1.0985   -0.5572 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1780    1.4779   -1.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0952    0.6868   -1.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7375    0.7358   -0.1456 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8770   -0.2203   -0.1616 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5567   -1.4825   -0.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0718    0.3779   -0.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9898    1.5525   -1.2643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2708   -0.2739   -0.9806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3268   -0.6923    1.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328   -1.3150    1.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0851   -0.2740    2.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7356    0.5609    0.9348 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3647    1.9497    1.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5210    0.7564   -1.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5603    1.8872    0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7159    1.1134    2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5841   -1.0045    1.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8043   -0.7986   -2.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0909   -0.2915   -1.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4878   -1.9990   -1.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7947   -2.2545    0.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0398   -2.1613   -1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4970   -1.8556    1.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3314    2.0171    0.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0391    2.5573   -1.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    1.1822   -2.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8173    1.1623   -2.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9227   -0.3585   -1.8556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1721    1.7644   -0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3577   -2.2252   -0.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5918   -1.9115   -0.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7149   -1.3099   -2.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7534   -0.7818   -0.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7601    0.1363    1.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0591   -1.5176    1.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8455   -2.1964    1.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4895   -1.6710    2.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155   -0.7644    2.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4969    0.3690    2.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6099    1.9372    1.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4801    2.7114    0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1529    2.2070    2.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3974    0.6355   -2.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2414    1.6258   -1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 12 14  1  6
 14 16  1  0
 14 15  2  0
  8 22  1  0
  3  2  1  1
  2  1  2  3
 22  3  1  0
 20  7  1  0
 20 11  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  8 32  1  1
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  1
 13 38  1  0
 13 39  1  0
 13 40  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 16 41  1  0
 22 51  1  0
 22 52  1  0
  2 25  1  0
  1 23  1  0
  1 24  1  0
M  END


  Mrv1652309082202362D          

 22 24  0  0  1  0            999 V2000
    4.5032    1.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6465   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  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
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    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
    1.5395   -1.0164    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
    0.3020   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4452   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6165   -1.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1053   -0.0538    0.0000 O   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
    1.5395    0.4125    0.0000 C   0  0  1  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
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  6  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  6  0  0  0
  8 22  1  0  0  0  0
  3 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0258919

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]1(CC=C2C(CCC3[C@@](C)(CCC[C@@]23C)C(O)=O)C1)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,9,14,16H,1,6-8,10-13H2,2-4H3,(H,21,22)/t14?,16?,18-,19-,20+/m0/s1

> <INCHI_KEY>
TVHDZSRRHQKNEZ-BDAJPOSXSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.458

> <EXACT_MASS>
302.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
35.53033377230066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4aR,7S)-7-ethenyl-1,4a,7-trimethyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid

> <JCHEM_LOGP>
5.067184579000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.804501600423035

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
90.33479999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aR,7S)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       8.406   3.276   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.673   1.760   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.673  -0.220   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724   2.104   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       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.104  -0.564   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       0.831  -2.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.883  -1.090   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.151  -2.607   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.063  -0.100   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   22                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13   14   17                                             
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    7   11   21                                             
CONECT   21   20                                                            
CONECT   22    8    3                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
Acanthoate	Generator
Pimara-9(11),15-dien-19-Oic acid	MeSH

Chemical Formula

C₂₀H₃₀O₂

Average Mass

302.4580 Da

Monoisotopic Mass

302.22458 Da

IUPAC Name

(1R,4aR,7S)-7-ethenyl-1,4a,7-trimethyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid

Traditional Name

(1R,4aR,7S)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@]1(CC=C2C(CCC3[C@@](C)(CCC[C@@]23C)C(O)=O)C1)C=C

InChI Identifier

InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,9,14,16H,1,6-8,10-13H2,2-4H3,(H,21,22)/t14?,16?,18-,19-,20+/m0/s1

InChI Key

TVHDZSRRHQKNEZ-BDAJPOSXSA-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
Coleonema pulchellum	LOTUS Database	35616633
Eleutherococcus koreanus	LOTUS Database	35616633
Plagiochila deltoidea	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

Pimarane diterpenoid
Diterpenoid
Phenanthrene
Hydrophenanthrene
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
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	5.07	ChemAxon
pKa (Strongest Acidic)	4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	90.33 m³·mol⁻¹	ChemAxon
Polarizability	35.53 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

C00035989

Chemspider ID

8036915

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9861219

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Moon K, Hwang S, Lee HJ, Jo E, Kim JN, Cha J: Identification of the antibacterial action mechanism of diterpenoids through transcriptome profiling. Front Microbiol. 2022 Jul 26;13:945023. doi: 10.3389/fmicb.2022.945023. eCollection 2022. [PubMed:35958135 ]
Dou JY, Jiang YC, Cui ZY, Lian LH, Nan JX, Wu YL: Acanthoic acid, unique potential pimaradiene diterpene isolated from Acanthopanax koreanum Nakai (Araliaceae): A review on its pharmacology, molecular mechanism, and structural modification. Phytochemistry. 2022 Aug;200:113247. doi: 10.1016/j.phytochem.2022.113247. Epub 2022 May 18. [PubMed:35597316 ]
Sittithumcharee G, Kariya R, Kasemsuk T, Saeeng R, Okada S: Antitumor effect of acanthoic acid against primary effusion lymphoma via inhibition of c-FLIP. Phytother Res. 2021 Dec;35(12):7018-7026. doi: 10.1002/ptr.7322. Epub 2021 Nov 15. [PubMed:34779075 ]
Kasemsuk T, Saehlim N, Arsakhant P, Sittithumcharee G, Okada S, Saeeng R: A novel synthetic acanthoic acid analogues and their cytotoxic activity in cholangiocarcinoma cells. Bioorg Med Chem. 2021 Jan 1;29:115886. doi: 10.1016/j.bmc.2020.115886. Epub 2020 Dec 1. [PubMed:33290909 ]
Han X, Cui ZY, Song J, Piao HQ, Lian LH, Hou LS, Wang G, Zheng S, Dong XX, Nan JX, Wu YL: Acanthoic acid modulates lipogenesis in nonalcoholic fatty liver disease via FXR/LXRs-dependent manner. Chem Biol Interact. 2019 Sep 25;311:108794. doi: 10.1016/j.cbi.2019.108794. Epub 2019 Aug 14. [PubMed:31421115 ]
LOTUS database [Link]

Showing NP-Card for (1r,4ar,7s)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid (NP0258919)

MOL for NP0258919 ((1r,4ar,7s)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

3D MOL for NP0258919 ((1r,4ar,7s)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

3D SDF for NP0258919 ((1r,4ar,7s)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

3D-SDF for NP0258919 ((1r,4ar,7s)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

PDB for NP0258919 ((1r,4ar,7s)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

3D PDB for NP0258919 ((1r,4ar,7s)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

SMILES for NP0258919 ((1r,4ar,7s)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

INCHI for NP0258919 ((1r,4ar,7s)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

Structure for NP0258919 ((1r,4ar,7s)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)

3D Structure for NP0258919 ((1r,4ar,7s)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylic acid)