NP-MRD: Showing NP-Card for ent-9-Hydroxy-15-oxo-16-kauren-19-oic acid (NP0141237)

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Record Information

Version

1.0

Created at

2022-06-29 22:19:09 UTC

Updated at

2022-06-29 22:19:09 UTC

NP-MRD ID

NP0141237

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ent-9-Hydroxy-15-oxo-16-kauren-19-oic acid

Description

Ent-9-Hydroxy-15-oxo-16-kauren-19-oic acid belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. It was first documented in 2022 (PMID: 35868842). Based on a literature review a significant number of articles have been published on ent-9-Hydroxy-15-oxo-16-kauren-19-oic acid (PMID: 35868820) (PMID: 35868806) (PMID: 35868798) (PMID: 35868796) (PMID: 35868785) (PMID: 35868778).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          2D

 52 55  0  0  0  0  0  0  0  0999 V2000
   -2.2458   -1.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3442    1.4772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3557    2.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    3.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8943    3.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443    5.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9048    6.5879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2348    5.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962    7.0581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0857    4.6595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1443    5.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8943    3.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1443    2.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443    2.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3943    1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8943    1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3943    1.2135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443   -0.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8943   -1.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943   -1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2760    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6161   -1.0216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0890   -3.1235    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6137    1.6956    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5048    3.4767    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0673    4.1490    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2398    5.1710    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9915    5.0095    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1652    8.0651    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027    6.5094    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4703    7.0264    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2508    5.3405    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0658    6.6086    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5538    5.6237    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0434    4.7758    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0434    2.8474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6059    2.1752    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7784    1.1532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804   -0.1672    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8758    1.4481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7606   -0.1460    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2971    0.0156    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1386    0.0450    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.0497    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3038   -1.8976    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8158   -2.8825    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6805   -2.6860    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6764    0.5374    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6004   -0.7041    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5 24  1  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 19  1  0
 19 20  1  1
 23  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  9 11  1  6
 11 13  1  0
 11 12  2  0
  8  9  1  0
 19  5  1  0
 19 17  1  0
  5  3  1  1
 10 32  1  0
 10 33  1  0
 10 34  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
  8 31  1  1
  7 29  1  0
  7 30  1  0
  6 27  1  0
  6 28  1  0
 24 51  1  0
 24 52  1  0
 23 50  1  1
 22 48  1  0
 22 49  1  0
 21 46  1  0
 21 47  1  0
 20 45  1  0
  1 25  1  0
  1 26  1  0
 13 35  1  0
M  END


  Mrv1652306302200192D          

 24 27  0  0  1  0            999 V2000
    4.4434    1.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7601    0.5959    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3183   -0.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0712   -0.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2660   -0.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7079   -0.3708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9549    0.4163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4013    1.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5923    0.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2888    0.0848    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8891   -0.5680    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6457   -1.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8005   -1.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -0.9158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8145   -0.4488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8565   -0.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431   -0.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4780    0.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3404    1.2794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4595   -1.1641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9773   -1.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4554    1.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4183    1.8643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1876    0.6601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 10 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 20  1  1  0  0  0
  6 21  1  6  0  0  0
  2 22  1  6  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0141237

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(CCC[C@]2(C)[C@@H]1CC[C@@]13C[C@H](CC[C@@]21O)C(=C)C3=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/c1-12-13-5-10-20(24)18(3)8-4-7-17(2,16(22)23)14(18)6-9-19(20,11-13)15(12)21/h13-14,24H,1,4-11H2,2-3H3,(H,22,23)/t13-,14+,17+,18+,19-,20+/m0/s1

> <INCHI_KEY>
AURKCYFYZBQUIZ-LJIVFDACSA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.44

> <EXACT_MASS>
332.198759382

$$$$

HEADER    PROTEIN                                 30-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-22         0                                  
HETATM    1  C   UNK     0       8.294   2.534   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.886   1.112   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.927  -0.022   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.466  -1.491   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.963  -1.826   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.921  -0.692   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.383   0.777   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.349   1.942   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.839   1.628   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.272   0.158   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.393  -1.060   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.939  -2.638   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.361  -2.938   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.313  -1.709   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.387  -0.838   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.599  -0.265   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.081  -0.007   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.759   0.870   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.502   2.388   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.458  -2.173   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.424  -2.148   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.183   1.942   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.114   3.480   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      11.550   1.232   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   22                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11   21                                             
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15   18                                             
CONECT   11   10    6   12   20                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   10   19                                                  
CONECT   19   18                                                            
CONECT   20   11                                                            
CONECT   21    6                                                            
CONECT   22    2   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Value	Source
ent-9-Hydroxy-15-oxo-16-kauren-19-Oate	Generator

Chemical Formula

C₂₀H₂₈O₄

Average Mass

332.4400 Da

Monoisotopic Mass

332.19876 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@]1(CCC[C@]2(C)[C@@H]1CC[C@@]13C[C@H](CC[C@@]21O)C(=C)C3=O)C(O)=O

InChI Identifier

InChI=1S/C20H28O4/c1-12-13-5-10-20(24)18(3)8-4-7-17(2,16(22)23)14(18)6-9-19(20,11-13)15(12)21/h13-14,24H,1,4-11H2,2-3H3,(H,22,23)/t13-,14+,17+,18+,19-,20+/m0/s1

InChI Key

AURKCYFYZBQUIZ-LJIVFDACSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Tertiary alcohol
Cyclic alcohol
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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

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

57256929

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101786565

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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Showing NP-Card for ent-9-Hydroxy-15-oxo-16-kauren-19-oic acid (NP0141237)

MOL for NP0141237 (ent-9-Hydroxy-15-oxo-16-kauren-19-oic acid)

3D MOL for NP0141237 (ent-9-Hydroxy-15-oxo-16-kauren-19-oic acid)

3D SDF for NP0141237 (ent-9-Hydroxy-15-oxo-16-kauren-19-oic acid)

3D-SDF for NP0141237 (ent-9-Hydroxy-15-oxo-16-kauren-19-oic acid)

PDB for NP0141237 (ent-9-Hydroxy-15-oxo-16-kauren-19-oic acid)

3D PDB for NP0141237 (ent-9-Hydroxy-15-oxo-16-kauren-19-oic acid)

SMILES for NP0141237 (ent-9-Hydroxy-15-oxo-16-kauren-19-oic acid)

INCHI for NP0141237 (ent-9-Hydroxy-15-oxo-16-kauren-19-oic acid)

Structure for NP0141237 (ent-9-Hydroxy-15-oxo-16-kauren-19-oic acid)

3D Structure for NP0141237 (ent-9-Hydroxy-15-oxo-16-kauren-19-oic acid)