NP-MRD: Showing NP-Card for (1r,2s,4s,6s,7s,8r,9s,11s,13r,14r,15s,17r,18r,21r)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0²,⁹.0⁴,⁸.0⁹,¹³.0¹⁸,²¹]henicosan-11-yl acetate (NP0219574)

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Record Information

Version

2.0

Created at

2022-09-05 20:37:14 UTC

Updated at

2022-09-05 20:37:14 UTC

NP-MRD ID

NP0219574

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4s,6s,7s,8r,9s,11s,13r,14r,15s,17r,18r,21r)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0²,⁹.0⁴,⁸.0⁹,¹³.0¹⁸,²¹]henicosan-11-yl acetate

Description

(1R,2S,4S,6S,7S,8R,9S,11S,13R,14R,15S,17R,18R,21R)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0²,⁹.0⁴,⁸.0⁹,¹³.0¹⁸,²¹]Henicosan-11-yl acetate belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (1r,2s,4s,6s,7s,8r,9s,11s,13r,14r,15s,17r,18r,21r)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0²,⁹.0⁴,⁸.0⁹,¹³.0¹⁸,²¹]henicosan-11-yl acetate is found in Melia volkensii. Based on a literature review very few articles have been published on (1R,2S,4S,6S,7S,8R,9S,11S,13R,14R,15S,17R,18R,21R)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0²,⁹.0⁴,⁸.0⁹,¹³.0¹⁸,²¹]Henicosan-11-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052222372D          

 43 49  0  0  1  0            999 V2000
    5.6285    3.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0936    3.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2822    3.2191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3701    2.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8352    1.6646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0126    1.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6980    0.9655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3261    0.4306    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0289    0.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1769   -0.3808    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9025   -0.7735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5001   -0.2047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3179   -0.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4671    0.7155    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2112    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3604    1.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1782    1.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5344    1.2479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9368    0.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7415    1.1082    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2078    1.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1134    1.6431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1439    0.5394    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7876    1.2835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3996   -0.6573    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0850   -1.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2624   -1.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942   -0.3989    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2993   -0.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3661    0.1360    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5888   -0.1405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0393    0.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165    0.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1099    1.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5153    0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2926    1.2239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4418    2.0353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8137    2.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0364    2.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9629    3.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9207    0.6890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0699    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7715   -0.1224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  1  0  0  0
 20 23  1  0  0  0  0
 12 23  1  0  0  0  0
  8 23  1  0  0  0  0
 23 24  1  1  0  0  0
 10 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 36 41  1  0  0  0  0
  7 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 43 25  1  1  0  0  0
 28 43  1  0  0  0  0
M  END


  Mrv1652309052222372D          

 43 49  0  0  1  0            999 V2000
    5.6285    3.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0936    3.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2822    3.2191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3701    2.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8352    1.6646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0126    1.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6980    0.9655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3261    0.4306    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0289    0.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1769   -0.3808    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9025   -0.7735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5001   -0.2047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3179   -0.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4671    0.7155    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2112    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3604    1.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1782    1.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5344    1.2479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9368    0.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7415    1.1082    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2078    1.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1134    1.6431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1439    0.5394    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7876    1.2835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3996   -0.6573    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0850   -1.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2624   -1.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942   -0.3989    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2993   -0.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3661    0.1360    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5888   -0.1405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0393    0.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165    0.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1099    1.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5153    0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2926    1.2239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4418    2.0353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8137    2.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0364    2.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9629    3.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9207    0.6890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0699    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7715   -0.1224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  1  0  0  0
 20 23  1  0  0  0  0
 12 23  1  0  0  0  0
  8 23  1  0  0  0  0
 23 24  1  1  0  0  0
 10 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 36 41  1  0  0  0  0
  7 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 43 25  1  1  0  0  0
 28 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219574

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@H]2[C@@]3(C1)[C@H](O[C@H]1C[C@@H](C4=COC=C4)[C@](C)(O)[C@@]31O)[C@@H]1OC[C@@]3(C)[C@H]1[C@]2(C)[C@H](C[C@H]3OC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H42O11/c1-15(33)40-19-9-21-29(5)23(42-17(3)35)11-22(41-16(2)34)28(4)14-39-25(26(28)29)27-31(21,12-19)32(37)24(43-27)10-20(30(32,6)36)18-7-8-38-13-18/h7-8,13,19-27,36-37H,9-12,14H2,1-6H3/t19-,20-,21+,22+,23-,24-,25+,26-,27+,28+,29-,30-,31-,32+/m0/s1

> <INCHI_KEY>
JONMXIRCXHOXRE-RRIGIPFXSA-N

> <FORMULA>
C32H42O11

> <MOLECULAR_WEIGHT>
602.677

> <EXACT_MASS>
602.272712172

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
60.886770089546886

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,4S,6S,7S,8R,9S,11S,13R,14R,15S,17R,18R,21R)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0^{2,9}.0^{4,8}.0^{9,13}.0^{18,21}]henicosan-11-yl acetate

> <JCHEM_LOGP>
0.3935108266666668

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.188860105796607

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.367450578531695

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7873561585387914

> <JCHEM_POLAR_SURFACE_AREA>
150.96

> <JCHEM_REFRACTIVITY>
146.15750000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4S,6S,7S,8R,9S,11S,13R,14R,15S,17R,18R,21R)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0^{2,9}.0^{4,8}.0^{9,13}.0^{18,21}]henicosan-11-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      10.507   6.903   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.508   5.731   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       7.993   6.009   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.024   4.280   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.026   3.107   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.490   3.226   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.903   1.802   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.075   0.804   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.387   1.610   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.797  -0.711   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.151  -1.444   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.267  -0.382   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.793  -0.179   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.072   1.336   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.461   2.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.739   3.515   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.266   3.718   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      15.931   2.329   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.815   1.268   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.717   2.069   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.588   3.339   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.545   3.067   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.602   1.007   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.937   2.396   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.346  -1.227   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.759  -2.651   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.223  -2.532   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.723  -0.745   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.425  -1.575   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.550   0.254   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.099  -0.262   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.073   0.736   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.524   0.220   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.205   2.251   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.829   1.768   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.280   2.285   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.558   3.799   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.386   4.798   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.935   4.282   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       3.664   6.312   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       5.452   1.286   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.730   2.801   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.173  -0.228   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   41                                                  
CONECT    8    7    9   10   23                                             
CONECT    9    8    5                                                       
CONECT   10    8   11   25                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
CONECT   20   14   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   12    8   24                                             
CONECT   24   23                                                            
CONECT   25   10   26   43                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30   43                                             
CONECT   29   28                                                            
CONECT   30   28   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   30   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   36    7   42   43                                             
CONECT   42   41                                                            
CONECT   43   41   25   28                                                  
MASTER        0    0    0    0    0    0    0    0   43    0   98    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,4S,6S,7S,8R,9S,11S,13R,14R,15S,17R,18R,21R)-15,17-Bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0,.0,.0,.0,]henicosan-11-yl acetic acid	Generator

Chemical Formula

C₃₂H₄₂O₁₁

Average Mass

602.6770 Da

Monoisotopic Mass

602.27271 Da

IUPAC Name

(1R,2S,4S,6S,7S,8R,9S,11S,13R,14R,15S,17R,18R,21R)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0^{2,9}.0^{4,8}.0^{9,13}.0^{18,21}]henicosan-11-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@H]2[C@@]3(C1)[C@H](O[C@H]1C[C@@H](C4=COC=C4)[C@](C)(O)[C@@]31O)[C@@H]1OC[C@@]3(C)[C@H]1[C@]2(C)[C@H](C[C@H]3OC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C32H42O11/c1-15(33)40-19-9-21-29(5)23(42-17(3)35)11-22(41-16(2)34)28(4)14-39-25(26(28)29)27-31(21,12-19)32(37)24(43-27)10-20(30(32,6)36)18-7-8-38-13-18/h7-8,13,19-27,36-37H,9-12,14H2,1-6H3/t19-,20-,21+,22+,23-,24-,25+,26-,27+,28+,29-,30-,31-,32+/m0/s1

InChI Key

JONMXIRCXHOXRE-RRIGIPFXSA-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
Melia volkensii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Aromatic monoterpenoid
Monoterpenoid
Tricarboxylic acid or derivatives
Tetrahydrofuran
Tertiary alcohol
Heteroaromatic compound
Furan
Cyclic alcohol
1,2-diol
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Ether
Dialkyl ether
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	0.39	ChemAxon
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	150.96 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	146.16 m³·mol⁻¹	ChemAxon
Polarizability	60.89 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	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

162876252

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,4s,6s,7s,8r,9s,11s,13r,14r,15s,17r,18r,21r)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0²,⁹.0⁴,⁸.0⁹,¹³.0¹⁸,²¹]henicosan-11-yl acetate (NP0219574)

MOL for NP0219574 ((1r,2s,4s,6s,7s,8r,9s,11s,13r,14r,15s,17r,18r,21r)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0²,⁹.0⁴,⁸.0⁹,¹³.0¹⁸,²¹]henicosan-11-yl acetate)

3D MOL for NP0219574 ((1r,2s,4s,6s,7s,8r,9s,11s,13r,14r,15s,17r,18r,21r)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0²,⁹.0⁴,⁸.0⁹,¹³.0¹⁸,²¹]henicosan-11-yl acetate)

3D SDF for NP0219574 ((1r,2s,4s,6s,7s,8r,9s,11s,13r,14r,15s,17r,18r,21r)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0²,⁹.0⁴,⁸.0⁹,¹³.0¹⁸,²¹]henicosan-11-yl acetate)

3D-SDF for NP0219574 ((1r,2s,4s,6s,7s,8r,9s,11s,13r,14r,15s,17r,18r,21r)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0²,⁹.0⁴,⁸.0⁹,¹³.0¹⁸,²¹]henicosan-11-yl acetate)

PDB for NP0219574 ((1r,2s,4s,6s,7s,8r,9s,11s,13r,14r,15s,17r,18r,21r)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0²,⁹.0⁴,⁸.0⁹,¹³.0¹⁸,²¹]henicosan-11-yl acetate)

3D PDB for NP0219574 ((1r,2s,4s,6s,7s,8r,9s,11s,13r,14r,15s,17r,18r,21r)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0²,⁹.0⁴,⁸.0⁹,¹³.0¹⁸,²¹]henicosan-11-yl acetate)

SMILES for NP0219574 ((1r,2s,4s,6s,7s,8r,9s,11s,13r,14r,15s,17r,18r,21r)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0²,⁹.0⁴,⁸.0⁹,¹³.0¹⁸,²¹]henicosan-11-yl acetate)

INCHI for NP0219574 ((1r,2s,4s,6s,7s,8r,9s,11s,13r,14r,15s,17r,18r,21r)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0²,⁹.0⁴,⁸.0⁹,¹³.0¹⁸,²¹]henicosan-11-yl acetate)

Structure for NP0219574 ((1r,2s,4s,6s,7s,8r,9s,11s,13r,14r,15s,17r,18r,21r)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0²,⁹.0⁴,⁸.0⁹,¹³.0¹⁸,²¹]henicosan-11-yl acetate)

3D Structure for NP0219574 ((1r,2s,4s,6s,7s,8r,9s,11s,13r,14r,15s,17r,18r,21r)-15,17-bis(acetyloxy)-6-(furan-3-yl)-7,8-dihydroxy-7,14,18-trimethyl-3,20-dioxahexacyclo[12.6.1.0²,⁹.0⁴,⁸.0⁹,¹³.0¹⁸,²¹]henicosan-11-yl acetate)