NP-MRD: Showing NP-Card for ent-16alpha,17-Dihydroxyatisan-3-one (NP0141064)

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Record Information

Version

2.0

Created at

2022-06-29 22:09:15 UTC

Updated at

2022-06-29 22:09:16 UTC

NP-MRD ID

NP0141064

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ent-16alpha,17-Dihydroxyatisan-3-one

Description

Ent-16alpha,17-dihydroxyatisan-3-one belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. ent-16alpha,17-Dihydroxyatisan-3-one was first documented in 2005 (PMID: 15856412). Based on a literature review a small amount of articles have been published on ent-16alpha,17-dihydroxyatisan-3-one (PMID: 16491453) (PMID: 20032393).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    3.7908    1.2417    1.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558    0.4201    0.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6174    1.0816   -0.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6787   -0.9545    0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8881   -1.1038    0.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8813   -2.1336    0.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4191   -1.9479    0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9450   -0.7596   -0.0053 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2973   -1.1500   -1.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6965    0.4178    0.5286 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1080    1.7496    0.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2590    1.7855    0.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0867    0.7452    0.1397 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4589    1.2974   -1.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6287    0.5269   -1.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171   -0.7733   -1.0511 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2942   -1.3535   -1.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5231   -0.6169    0.1046 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2277   -0.4667    0.3171 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1276   -1.6267    1.0834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6726   -0.0942    0.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1155    0.1239    1.5808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4239    0.6772    0.8971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8940    1.1038    1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5870    2.3091    1.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5297    0.8143    2.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0259    0.9070   -1.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5806    2.1956   -0.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6743    0.7969   -1.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2247   -2.4920    1.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1376   -2.9957    0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0503   -1.7385    1.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8969   -2.8809    0.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3848   -1.3827   -1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8170   -2.1640   -1.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323   -0.4267   -2.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5419    0.3812    1.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333    1.8925   -0.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7103    2.5360    0.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7337    2.7613    0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0876    1.4969    1.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7308    2.3672   -1.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388    1.2755   -1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5086    1.1598   -1.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678    0.3385   -2.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3642   -1.4530   -1.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8768   -1.1251   -2.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3344   -2.4325   -0.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8447   -1.1433    1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9141   -2.1872    0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9089    0.8082   -0.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3006   -0.9121   -0.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2397    1.0829    1.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9530    1.6378    0.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1603    0.3830    1.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 13 12  1  1
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  8  1  0
  8  9  1  6
  8  7  1  0
  7  6  1  0
  6  4  1  0
  4  5  2  0
 16 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 19 23  1  0
  4  2  1  0
  8 10  1  0
 18 13  1  0
 23 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
 10 37  1  1
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  6
 17 47  1  0
 17 48  1  0
 18 49  1  1
  9 34  1  0
  9 35  1  0
  9 36  1  0
  7 32  1  0
  7 33  1  0
  6 30  1  0
  6 31  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
M  END


  Mrv1652306302200092D          

 23 26  0  0  1  0            999 V2000
    4.0713    1.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4134    0.2862    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8950    0.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7159    0.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0553    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8762    0.0400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5737   -0.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7528   -0.4657    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3189   -1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5018   -0.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9394   -0.2714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5468    0.3664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0241    1.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1768    1.1283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4566    0.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2379   -0.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4967    0.6410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0013   -0.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8674    1.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0907    0.8962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7377    0.3177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2264   -1.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5203   -1.3711    0.0000 C   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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  1  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 21  1  6  0  0  0
  7 22  1  0  0  0  0
  7 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0141064

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@H]2CC[C@@]34CC[C@@H](C[C@H]3[C@]2(C)CCC1=O)[C@](O)(CO)C4

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-17(2)14-5-9-19-8-4-13(20(23,11-19)12-21)10-15(19)18(14,3)7-6-16(17)22/h13-15,21,23H,4-12H2,1-3H3/t13-,14+,15-,18+,19+,20+/m0/s1

> <INCHI_KEY>
GFMRAAZMCOCUCY-JTZLQOMOSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.473

> <EXACT_MASS>
320.23514489

$$$$

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       7.600   1.936   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.238   0.534   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.137   1.785   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.670   1.632   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.303   0.228   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.835   0.075   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.404  -1.023   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.872  -0.869   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.062  -2.230   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.537  -1.796   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.487  -0.507   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.621   0.684   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.645   1.997   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.063   2.106   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.586   0.609   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.177  -1.072   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.794   1.197   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.736  -0.046   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.619   2.192   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.169   1.673   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.377   0.593   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.623  -1.965   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.305  -2.559   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8   12                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   22   23                                             
CONECT    8    7    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16   18                                             
CONECT   12   11    2   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14   18   19   21                                             
CONECT   18   17   11                                                       
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   17                                                            
CONECT   22    7                                                            
CONECT   23    7                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
ent-16a,17-Dihydroxyatisan-3-one	Generator
ent-16Α,17-dihydroxyatisan-3-one	Generator

Chemical Formula

C₂₀H₃₂O₃

Average Mass

320.4730 Da

Monoisotopic Mass

320.23514 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)[C@H]2CC[C@@]34CC[C@@H](C[C@H]3[C@]2(C)CCC1=O)[C@](O)(CO)C4

InChI Identifier

InChI=1S/C20H32O3/c1-17(2)14-5-9-19-8-4-13(20(23,11-19)12-21)10-15(19)18(14,3)7-6-16(17)22/h13-15,21,23H,4-12H2,1-3H3/t13-,14+,15-,18+,19+,20+/m0/s1

InChI Key

GFMRAAZMCOCUCY-JTZLQOMOSA-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 atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Atisane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Alkaloid or derivatives
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Ketone
1,2-diol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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

10315319

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21726550

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shi HM, Williams ID, Sung HH, Zhu HX, Ip NY, Min ZD: Cytotoxic diterpenoids from the roots of Euphorbia ebracteolata. Planta Med. 2005 Apr;71(4):349-54. doi: 10.1055/s-2005-864102. [PubMed:15856412 ]
Duarte N, Gyemant N, Abreu PM, Molnar J, Ferreira MJ: New macrocyclic lathyrane diterpenes, from Euphorbia lagascae, as inhibitors of multidrug resistance of tumour cells. Planta Med. 2006 Feb;72(2):162-8. doi: 10.1055/s-2005-873196. [PubMed:16491453 ]
Duarte N, Ramalhete C, Varga A, Molnar J, Ferreira MJ: Multidrug resistance modulation and apoptosis induction of cancer cells by terpenic compounds isolated from Euphorbia species. Anticancer Res. 2009 Nov;29(11):4467-72. [PubMed:20032393 ]

Showing NP-Card for ent-16alpha,17-Dihydroxyatisan-3-one (NP0141064)

MOL for NP0141064 (ent-16alpha,17-Dihydroxyatisan-3-one)

3D MOL for NP0141064 (ent-16alpha,17-Dihydroxyatisan-3-one)

3D SDF for NP0141064 (ent-16alpha,17-Dihydroxyatisan-3-one)

3D-SDF for NP0141064 (ent-16alpha,17-Dihydroxyatisan-3-one)

PDB for NP0141064 (ent-16alpha,17-Dihydroxyatisan-3-one)

3D PDB for NP0141064 (ent-16alpha,17-Dihydroxyatisan-3-one)

SMILES for NP0141064 (ent-16alpha,17-Dihydroxyatisan-3-one)

INCHI for NP0141064 (ent-16alpha,17-Dihydroxyatisan-3-one)

Structure for NP0141064 (ent-16alpha,17-Dihydroxyatisan-3-one)

3D Structure for NP0141064 (ent-16alpha,17-Dihydroxyatisan-3-one)