NP-MRD: Showing NP-Card for (-)-Briarlide F (NP0079810)

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Record Information

Version

2.0

Created at

2022-04-29 00:52:13 UTC

Updated at

2022-04-29 00:52:13 UTC

NP-MRD ID

NP0079810

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Briarlide F

Description

(1R,2R,3S,4S,5R,8R,9S,11S,12Z,14S,17R)-2,5,9-tris(acetyloxy)-4,11-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]Octadeca-6,12-dien-11-yl octanoate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (-)-Briarlide F is found in Briareum sp. Based on a literature review very few articles have been published on (1R,2R,3S,4S,5R,8R,9S,11S,12Z,14S,17R)-2,5,9-tris(acetyloxy)-4,11-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0¹,¹⁷.0³,⁸]Octadeca-6,12-dien-11-yl octanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292202522D          

 47 50  0  0  1  0            999 V2000
   -1.5914    0.1428    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9979   -0.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2049   -0.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0053    0.5976    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5988    1.1707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3918    0.9433    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1848    1.1707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6467    1.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4557    1.8691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9926    2.5443    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7930    3.3448    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1131    3.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5935    2.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3939    2.1986    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9873    1.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7877    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3812    0.2519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742    0.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3738    1.2798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7677   -0.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1649    2.7131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8228    2.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8228    1.3736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5373    2.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2518    2.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9662    2.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6807    2.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3952    2.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1096    2.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8241    2.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3204    2.1708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3865    3.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0299    3.4023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3390    2.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1395    2.4378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2930    2.1071    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9194    1.6632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1683    1.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1922    1.7438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857    2.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5787    2.0895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5861    3.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5882    0.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3844   -0.0846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5840   -0.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9906   -1.4582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3771   -1.1125    0.0000 C   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
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 14 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 14 31  1  6  0  0  0
 13 32  1  0  0  0  0
 11 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 10 36  1  0  0  0  0
 36 37  1  0  0  0  0
 10 37  1  1  0  0  0
 36 38  1  1  0  0  0
  9 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
  4 43  1  1  0  0  0
  1 44  1  1  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
M  END


  Mrv1652304292202522D          

 47 50  0  0  1  0            999 V2000
   -1.5914    0.1428    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9979   -0.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2049   -0.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0053    0.5976    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5988    1.1707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3918    0.9433    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1848    1.1707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6467    1.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4557    1.8691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9926    2.5443    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7930    3.3448    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1131    3.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5935    2.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3939    2.1986    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9873    1.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7877    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3812    0.2519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742    0.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3738    1.2798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7677   -0.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1649    2.7131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8228    2.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8228    1.3736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5373    2.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2518    2.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9662    2.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6807    2.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3952    2.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1096    2.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8241    2.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3204    2.1708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3865    3.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0299    3.4023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3390    2.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1395    2.4378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2930    2.1071    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9194    1.6632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1683    1.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1922    1.7438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857    2.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5787    2.0895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5861    3.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5882    0.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3844   -0.0846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5840   -0.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9906   -1.4582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3771   -1.1125    0.0000 C   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
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 14 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 14 31  1  6  0  0  0
 13 32  1  0  0  0  0
 11 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 10 36  1  0  0  0  0
 36 37  1  0  0  0  0
 10 37  1  1  0  0  0
 36 38  1  1  0  0  0
  9 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
  4 43  1  1  0  0  0
  1 44  1  1  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079810

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC(=O)O[C@@]1(O)C[C@H](OC(C)=O)[C@]2(C)C=C[C@@H](OC(C)=O)[C@@](C)(O)[C@@H]2[C@@H](OC(C)=O)[C@@]23O[C@@]2(C)C(=O)O[C@H]3\C=C1\C

> <INCHI_IDENTIFIER>
InChI=1S/C34H48O13/c1-9-10-11-12-13-14-26(38)46-33(41)18-25(43-21(4)36)30(6)16-15-23(42-20(3)35)31(7,40)27(30)28(44-22(5)37)34-24(17-19(33)2)45-29(39)32(34,8)47-34/h15-17,23-25,27-28,40-41H,9-14,18H2,1-8H3/b19-17-/t23-,24+,25+,27-,28-,30+,31-,32+,33+,34-/m1/s1

> <INCHI_KEY>
ADXUQEXAZJOSIH-IYZRQVSESA-N

> <FORMULA>
C34H48O13

> <MOLECULAR_WEIGHT>
664.745

> <EXACT_MASS>
664.309491606

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
74.98367411831379

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3S,4S,5R,8R,9S,11S,12Z,14S,17R)-2,5,9-tris(acetyloxy)-4,11-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-6,12-dien-11-yl octanoate

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
3.335126412999998

> <ALOGPS_LOGS>
-4.95

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.624385537702445

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.260495792036776

> <JCHEM_PKA_STRONGEST_BASIC>
-3.401322354389139

> <JCHEM_POLAR_SURFACE_AREA>
184.48999999999998

> <JCHEM_REFRACTIVITY>
163.07700000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.52e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3S,4S,5R,8R,9S,11S,12Z,14S,17R)-2,5,9-tris(acetyloxy)-4,11-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-6,12-dien-11-yl octanoate

> <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      -2.971   0.267   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.863  -0.803   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.382  -0.379   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.010   1.116   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.118   2.185   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.598   1.761   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.078   2.185   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.074   3.225   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.851   3.489   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.853   4.749   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.480   6.244   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.211   7.049   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.108   5.598   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.735   4.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.843   3.034   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.470   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.578   0.470   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.059   0.895   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.431   2.389   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.166  -0.175   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.174   5.065   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.403   4.104   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.403   2.564   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.736   4.874   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.070   4.104   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.404   4.874   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.737   4.104   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.071   4.874   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.405   4.104   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.738   4.874   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.465   4.052   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.588   6.023   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.056   6.351   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.633   4.923   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.127   4.551   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -0.547   3.933   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -1.716   3.105   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.314   2.657   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -2.225   3.255   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -3.333   4.325   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -4.814   3.900   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -2.961   5.819   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.098   0.046   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -4.451  -0.158   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -4.823  -1.652   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -3.716  -2.722   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -6.304  -2.077   0.000  0.00  0.00           C+0
CONECT    1    2    6   44                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   16   43                                             
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10   39                                                  
CONECT   10    9   11   36   37                                             
CONECT   11   10   12   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   32                                                  
CONECT   14   13   15   21   31                                             
CONECT   15   14   16                                                       
CONECT   16   15    4   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   14   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   14                                                            
CONECT   32   13                                                            
CONECT   33   11   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   10   37   38                                             
CONECT   37   36   10                                                       
CONECT   38   36                                                            
CONECT   39    9   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43    4                                                            
CONECT   44    1   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  100    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,3S,4S,5R,8R,9S,11S,12Z,14S,17R)-2,5,9-Tris(acetyloxy)-4,11-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0,.0,]octadeca-6,12-dien-11-yl octanoic acid	Generator

Chemical Formula

C₃₄H₄₈O₁₃

Average Mass

664.7450 Da

Monoisotopic Mass

664.30949 Da

IUPAC Name

(1R,2R,3S,4S,5R,8R,9S,11S,12Z,14S,17R)-2,5,9-tris(acetyloxy)-4,11-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-6,12-dien-11-yl octanoate

Traditional Name

(1R,2R,3S,4S,5R,8R,9S,11S,12Z,14S,17R)-2,5,9-tris(acetyloxy)-4,11-dihydroxy-4,8,12,17-tetramethyl-16-oxo-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-6,12-dien-11-yl octanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCC(=O)O[C@@]1(O)C[C@H](OC(C)=O)[C@]2(C)C=C[C@@H](OC(C)=O)[C@@](C)(O)[C@@H]2[C@@H](OC(C)=O)[C@@]23O[C@@]2(C)C(=O)O[C@H]3\C=C1\C

InChI Identifier

InChI=1S/C34H48O13/c1-9-10-11-12-13-14-26(38)46-33(41)18-25(43-21(4)36)30(6)16-15-23(42-20(3)35)31(7,40)27(30)28(44-22(5)37)34-24(17-19(33)2)45-29(39)32(34,8)47-34/h15-17,23-25,27-28,40-41H,9-14,18H2,1-8H3/b19-17-/t23-,24+,25+,27-,28-,30+,31-,32+,33+,34-/m1/s1

InChI Key

ADXUQEXAZJOSIH-IYZRQVSESA-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
Pentacarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Gamma butyrolactone
Para-dioxane
Tetrahydrofuran
Tertiary alcohol
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
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	3.1	ALOGPS
logP	3.34	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	11.26	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	184.49 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	163.08 m³·mol⁻¹	ChemAxon
Polarizability	74.98 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

163103328

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Briarlide F (NP0079810)

MOL for NP0079810 ((-)-Briarlide F)

3D MOL for NP0079810 ((-)-Briarlide F)

3D SDF for NP0079810 ((-)-Briarlide F)

3D-SDF for NP0079810 ((-)-Briarlide F)

PDB for NP0079810 ((-)-Briarlide F)

3D PDB for NP0079810 ((-)-Briarlide F)

SMILES for NP0079810 ((-)-Briarlide F)

INCHI for NP0079810 ((-)-Briarlide F)

Structure for NP0079810 ((-)-Briarlide F)

3D Structure for NP0079810 ((-)-Briarlide F)