NP-MRD: Showing NP-Card for (-)-Briarlide H (NP0079811)

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Record Information

Version

2.0

Created at

2022-04-29 00:52:17 UTC

Updated at

2022-04-29 00:52:17 UTC

NP-MRD ID

NP0079811

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Briarlide H

Description

(1R,2R,3S,4S,5R,8R,9R,10R,12Z,14S,17R)-2-(acetyloxy)-4,5,9-trihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]Octadeca-6,12-dien-10-yl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (-)-Briarlide H is found in Briareum sp. Based on a literature review very few articles have been published on (1R,2R,3S,4S,5R,8R,9R,10R,12Z,14S,17R)-2-(acetyloxy)-4,5,9-trihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]Octadeca-6,12-dien-10-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292202522D          

 34 37  0  0  1  0            999 V2000
    3.4900   -0.4522    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9440    0.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5745    0.9743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7510    1.0231    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2969    0.3343    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6664   -0.4034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0539   -1.2069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2246   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    0.3463    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0193   -0.3057    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1957   -0.2569    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3952    0.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803    1.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1039    1.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5579    1.8095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3815    1.7607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6440    2.6297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2525    2.6439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5945    3.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038    4.0934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4142    3.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693    1.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0123    0.5414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6826    0.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559    1.9828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3202    0.4624    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8718   -0.0715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9578    1.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1412   -0.5566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4384   -1.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992   -1.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3428   -0.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4911    1.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1717   -1.0414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  6  0  0  0
  5  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  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  6  0  0  0
 15 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 13 22  1  0  0  0  0
 11 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 10 26  1  0  0  0  0
 26 27  1  0  0  0  0
 10 27  1  1  0  0  0
 26 28  1  1  0  0  0
  9 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  4 33  1  1  0  0  0
  1 34  1  1  0  0  0
M  END


  Mrv1652304292202522D          

 34 37  0  0  1  0            999 V2000
    3.4900   -0.4522    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9440    0.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5745    0.9743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7510    1.0231    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2969    0.3343    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6664   -0.4034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0539   -1.2069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2246   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    0.3463    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0193   -0.3057    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1957   -0.2569    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3952    0.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803    1.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1039    1.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5579    1.8095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3815    1.7607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6440    2.6297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2525    2.6439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5945    3.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038    4.0934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4142    3.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693    1.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0123    0.5414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6826    0.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559    1.9828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3202    0.4624    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8718   -0.0715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9578    1.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1412   -0.5566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4384   -1.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992   -1.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3428   -0.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4911    1.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1717   -1.0414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  6  0  0  0
  5  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  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  6  0  0  0
 15 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 13 22  1  0  0  0  0
 11 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 10 26  1  0  0  0  0
 26 27  1  0  0  0  0
 10 27  1  1  0  0  0
 26 28  1  1  0  0  0
  9 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  4 33  1  1  0  0  0
  1 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0079811

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C\C(C)=C/[C@@H]2OC(=O)[C@]3(C)O[C@@]23[C@H](OC(C)=O)[C@H]2[C@](C)(O)[C@H](O)C=C[C@@]2(C)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O10/c1-11-9-14(31-12(2)25)18(28)21(4)8-7-15(27)22(5,30)17(21)19(32-13(3)26)24-16(10-11)33-20(29)23(24,6)34-24/h7-8,10,14-19,27-28,30H,9H2,1-6H3/b11-10-/t14-,15-,16+,17-,18+,19-,21-,22-,23+,24-/m1/s1

> <INCHI_KEY>
KEYOAWSJOBZMKE-VDBQGWLWSA-N

> <FORMULA>
C24H32O10

> <MOLECULAR_WEIGHT>
480.51

> <EXACT_MASS>
480.19954723

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
89.61214170893602

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3S,4S,5R,8R,9R,10R,12Z,14S,17R)-10-(acetyloxy)-4,5,9-trihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-6,12-dien-2-yl acetate

> <ALOGPS_LOGP>
0.79

> <JCHEM_LOGP>
-0.2624614540000002

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.794375813631

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.167236818795377

> <JCHEM_PKA_STRONGEST_BASIC>
-3.38657757582071

> <JCHEM_POLAR_SURFACE_AREA>
152.12

> <JCHEM_REFRACTIVITY>
115.978

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3S,4S,5R,8R,9R,10R,12Z,14S,17R)-10-(acetyloxy)-4,5,9-trihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-6,12-dien-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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       6.515  -0.844   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.362   0.442   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.672   1.819   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.135   1.910   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.288   0.624   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.977  -0.753   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.701  -2.253   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.153  -2.246   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.957   0.646   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.903  -0.571   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.365  -0.480   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.738   1.035   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.523   2.183   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.061   2.092   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.908   3.378   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.445   3.287   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.935   4.909   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.338   4.935   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.976   6.403   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.060   7.641   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.506   6.577   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.689   3.451   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.023   1.011   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.274   1.841   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.224   3.701   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.464   0.863   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.494  -0.134   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.655   2.468   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.130  -1.039   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.818  -2.189   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.119  -3.700   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.640  -1.694   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.517   3.192   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.787  -1.944   0.000  0.00  0.00           O+0
CONECT    1    2    6   34                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   16   33                                             
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10   29                                                  
CONECT   10    9   11   26   27                                             
CONECT   11   10   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15    4   17                                                  
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   13                                                            
CONECT   23   11   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   10   27   28                                             
CONECT   27   26   10                                                       
CONECT   28   26                                                            
CONECT   29    9   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    4                                                            
CONECT   34    1                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,3S,4S,5R,8R,9R,10R,12Z,14S,17R)-2-(Acetyloxy)-4,5,9-trihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0,.0,]octadeca-6,12-dien-10-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₂O₁₀

Average Mass

480.5100 Da

Monoisotopic Mass

480.19955 Da

IUPAC Name

(1R,2R,3S,4S,5R,8R,9R,10R,12Z,14S,17R)-10-(acetyloxy)-4,5,9-trihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-6,12-dien-2-yl acetate

Traditional Name

(1R,2R,3S,4S,5R,8R,9R,10R,12Z,14S,17R)-10-(acetyloxy)-4,5,9-trihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-6,12-dien-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C\C(C)=C/[C@@H]2OC(=O)[C@]3(C)O[C@@]23[C@H](OC(C)=O)[C@H]2[C@](C)(O)[C@H](O)C=C[C@@]2(C)[C@H]1O

InChI Identifier

InChI=1S/C24H32O10/c1-11-9-14(31-12(2)25)18(28)21(4)8-7-15(27)22(5,30)17(21)19(32-13(3)26)24-16(10-11)33-20(29)23(24,6)34-24/h7-8,10,14-19,27-28,30H,9H2,1-6H3/b11-10-/t14-,15-,16+,17-,18+,19-,21-,22-,23+,24-/m1/s1

InChI Key

KEYOAWSJOBZMKE-VDBQGWLWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Briareum sp.	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Briarane diterpenoid
Diterpenoid
Diterpene lactone
Tricarboxylic acid or derivatives
Gamma butyrolactone
Para-dioxane
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	0.79	ALOGPS
logP	-0.26	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	13.17	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	152.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	115.98 m³·mol⁻¹	ChemAxon
Polarizability	89.61 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163077034

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Briarlide H (NP0079811)

MOL for NP0079811 ((-)-Briarlide H)

3D MOL for NP0079811 ((-)-Briarlide H)

3D SDF for NP0079811 ((-)-Briarlide H)

3D-SDF for NP0079811 ((-)-Briarlide H)

PDB for NP0079811 ((-)-Briarlide H)

3D PDB for NP0079811 ((-)-Briarlide H)

SMILES for NP0079811 ((-)-Briarlide H)

INCHI for NP0079811 ((-)-Briarlide H)

Structure for NP0079811 ((-)-Briarlide H)

3D Structure for NP0079811 ((-)-Briarlide H)