NP-MRD: Showing NP-Card for (+)-Gagunin O (NP0076579)

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Record Information

Version

2.0

Created at

2022-04-28 21:46:23 UTC

Updated at

2022-04-28 21:46:23 UTC

NP-MRD ID

NP0076579

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Gagunin O

Description

(1R,2R,3R,3aR,4S,5aR,6S,7S,8S,10aS,10bR)-8-(acetyloxy)-3,4,6-tris(butanoyloxy)-7-hydroxy-3a,5a,9-trimethyl-1-(propan-2-yl)-1H,2H,3H,3aH,4H,5H,5aH,6H,7H,8H,10aH,10bH-cyclohepta[e]inden-2-yl butanoate belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. (+)-Gagunin O is found in Phorbas sp. Based on a literature review very few articles have been published on (1R,2R,3R,3aR,4S,5aR,6S,7S,8S,10aS,10bR)-8-(acetyloxy)-3,4,6-tris(butanoyloxy)-7-hydroxy-3a,5a,9-trimethyl-1-(propan-2-yl)-1H,2H,3H,3aH,4H,5H,5aH,6H,7H,8H,10aH,10bH-cyclohepta[e]inden-2-yl butanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223462D          

 49 51  0  0  1  0            999 V2000
   -3.7039    2.2272    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9155    2.4704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7320    3.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3367    3.8358    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1251    3.5927    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3087    2.7884    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1303    2.7144    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4546    3.4730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8333    4.0158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9072    4.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2326    5.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3066    6.1341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4841    4.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8094    5.4405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8834    6.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2589    3.6566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5021    4.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3064    4.6285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9409    5.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1841    5.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6230    6.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5535    2.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3784    2.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1517    1.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0266    4.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1531    4.6402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3648    4.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1812    5.6876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7600    4.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9717    4.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669    4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339    2.0056    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1722    1.1830    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7770    0.6218    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5928    0.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0053    1.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0575    0.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5338   -0.1665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7295   -0.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1684    0.2547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4863   -1.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4043    0.8815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5194    2.4181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8050    2.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8050    1.1806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0905    2.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6240    2.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385    2.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1476    2.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  7 22  1  1  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  5 25  1  6  0  0  0
  4 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
  1 36  1  1  0  0  0
 35 37  1  0  0  0  0
 34 38  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 33 42  1  1  0  0  0
 32 43  1  6  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
  2 49  1  6  0  0  0
M  END

     RDKit          3D

109111  0  0  0  0  0  0  0  0999 V2000
    7.6187   -1.1916   -1.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667   -2.4678   -1.3537 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8825   -2.4560   -0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0163   -1.2598   -0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0824   -0.5034   -1.1866 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1182   -0.9163    0.8086 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2897    0.2497    0.7211 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7031    1.0974    1.9374 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.2146    3.2738   -0.1406 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2940    3.3452   -1.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3103    4.1460    0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6061    1.2119    0.1804 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -5.4191    2.5196   -2.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0438   -2.0071    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6114   -0.6511   -1.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3015   -1.6896    2.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3854   -0.0602    3.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8575   -0.9615    2.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  1  0
 29 28  1  0
 28 26  1  0
 26 27  2  0
 26 25  1  0
 25 24  1  0
 24 20  1  0
 20 21  1  0
 21 22  1  0
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 37 93  1  0
M  END


  Mrv1652304282223462D          

 49 51  0  0  1  0            999 V2000
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   -7.3064    4.6285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1841    5.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6230    6.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3784    2.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1517    1.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0266    4.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1531    4.6402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3648    4.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1812    5.6876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7600    4.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9717    4.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669    4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339    2.0056    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1722    1.1830    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7770    0.6218    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5928    0.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0053    1.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0575    0.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5338   -0.1665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7295   -0.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4863   -1.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4043    0.8815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5194    2.4181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8050    2.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8050    1.1806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0905    2.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6240    2.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385    2.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1476    2.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  7 22  1  1  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  5 25  1  6  0  0  0
  4 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
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 29 30  1  0  0  0  0
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  2 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
  1 36  1  1  0  0  0
 35 37  1  0  0  0  0
 34 38  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 33 42  1  1  0  0  0
 32 43  1  6  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
  2 49  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0076579

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)O[C@@H]1[C@H](C(C)C)[C@H]2[C@@H]3C=C(C)[C@H](OC(C)=O)[C@H](O)[C@@H](OC(=O)CCC)[C@]3(C)C[C@H](OC(=O)CCC)[C@]2(C)[C@H]1OC(=O)CCC

> <INCHI_IDENTIFIER>
InChI=1S/C38H60O11/c1-11-15-26(40)46-25-20-37(9)24(19-22(7)33(45-23(8)39)32(44)35(37)48-28(42)17-13-3)31-30(21(5)6)34(47-27(41)16-12-2)36(38(25,31)10)49-29(43)18-14-4/h19,21,24-25,30-36,44H,11-18,20H2,1-10H3/t24-,25-,30+,31+,32-,33-,34+,35+,36-,37+,38-/m0/s1

> <INCHI_KEY>
MIKVSZXTTYIXJT-XUKVQKKQSA-N

> <FORMULA>
C38H60O11

> <MOLECULAR_WEIGHT>
692.887

> <EXACT_MASS>
692.413562752

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
109

> <JCHEM_AVERAGE_POLARIZABILITY>
76.58832979115327

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3R,3aR,4S,5aR,6S,7S,8S,10aS,10bR)-8-(acetyloxy)-3,4,6-tris(butanoyloxy)-7-hydroxy-3a,5a,9-trimethyl-1-(propan-2-yl)-1H,2H,3H,3aH,4H,5H,5aH,6H,7H,8H,10aH,10bH-cyclohepta[e]inden-2-yl butanoate

> <ALOGPS_LOGP>
5.27

> <JCHEM_LOGP>
6.269214210333332

> <ALOGPS_LOGS>
-5.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.0830639758559

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6372678169606294

> <JCHEM_POLAR_SURFACE_AREA>
151.73000000000002

> <JCHEM_REFRACTIVITY>
179.71610000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.77e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3R,3aR,4S,5aR,6S,7S,8S,10aS,10bR)-8-(acetyloxy)-3,4,6-tris(butanoyloxy)-7-hydroxy-1-isopropyl-3a,5a,9-trimethyl-1H,2H,3H,4H,5H,6H,7H,8H,10aH,10bH-cyclohepta[e]inden-2-yl butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -6.914   4.157   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.442   4.611   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.100   6.113   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.229   7.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.700   6.706   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.043   5.205   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.577   5.067   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.182   6.483   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.022   7.496   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -9.160   9.030   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -7.901   9.916   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -8.039  11.450   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -6.504   9.269   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.244  10.156   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.382  11.689   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0     -11.683   6.826   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0     -12.137   8.297   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0     -13.639   8.640   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0     -11.090   9.426   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -11.544  10.898   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -10.496  12.027   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -10.366   3.745   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -11.906   3.768   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.617   2.400   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.516   8.235   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.886   8.662   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.414   9.116   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.072  10.617   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.285   8.068   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.814   8.522   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.685   7.475   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.170   3.744   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.055   2.208   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.184   1.161   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -6.707   1.390   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -7.477   2.724   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -7.574   0.118   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -4.730  -0.311   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -3.228  -0.654   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -2.181   0.475   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -2.775  -2.125   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -2.621   1.646   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -2.836   4.514   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -1.503   3.744   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -1.503   2.204   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -0.169   4.514   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       1.165   3.744   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       2.498   4.514   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -4.009   5.174   0.000  0.00  0.00           C+0
CONECT    1    2    6   36                                                  
CONECT    2    1    3   32   49                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   26                                                  
CONECT    5    4    6    9   25                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8   22                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    8   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22    7   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    5                                                            
CONECT   26    4   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32    2   33   43                                                  
CONECT   33   32   34   42                                                  
CONECT   34   33   35   38                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35    1                                                       
CONECT   37   35                                                            
CONECT   38   34   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   33                                                            
CONECT   43   32   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47                                                            
CONECT   49    2                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  102    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,3R,3AR,4S,5ar,6S,7S,8S,10as,10BR)-8-(acetyloxy)-3,4,6-tris(butanoyloxy)-7-hydroxy-3a,5a,9-trimethyl-1-(propan-2-yl)-1H,2H,3H,3ah,4H,5H,5ah,6H,7H,8H,10ah,10BH-cyclohepta[e]inden-2-yl butanoic acid	Generator

Chemical Formula

C₃₈H₆₀O₁₁

Average Mass

692.8870 Da

Monoisotopic Mass

692.41356 Da

IUPAC Name

(1R,2R,3R,3aR,4S,5aR,6S,7S,8S,10aS,10bR)-8-(acetyloxy)-3,4,6-tris(butanoyloxy)-7-hydroxy-3a,5a,9-trimethyl-1-(propan-2-yl)-1H,2H,3H,3aH,4H,5H,5aH,6H,7H,8H,10aH,10bH-cyclohepta[e]inden-2-yl butanoate

Traditional Name

(1R,2R,3R,3aR,4S,5aR,6S,7S,8S,10aS,10bR)-8-(acetyloxy)-3,4,6-tris(butanoyloxy)-7-hydroxy-1-isopropyl-3a,5a,9-trimethyl-1H,2H,3H,4H,5H,6H,7H,8H,10aH,10bH-cyclohepta[e]inden-2-yl butanoate

CAS Registry Number

Not Available

SMILES

CCCC(=O)O[C@@H]1[C@H](C(C)C)[C@H]2[C@@H]3C=C(C)[C@H](OC(C)=O)[C@H](O)[C@@H](OC(=O)CCC)[C@]3(C)C[C@H](OC(=O)CCC)[C@]2(C)[C@H]1OC(=O)CCC

InChI Identifier

InChI=1S/C38H60O11/c1-11-15-26(40)46-25-20-37(9)24(19-22(7)33(45-23(8)39)32(44)35(37)48-28(42)17-13-3)31-30(21(5)6)34(47-27(41)16-12-2)36(38(25,31)10)49-29(43)18-14-4/h19,21,24-25,30-36,44H,11-18,20H2,1-10H3/t24-,25-,30+,31+,32-,33-,34+,35+,36-,37+,38-/m0/s1

InChI Key

MIKVSZXTTYIXJT-XUKVQKKQSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Phorbas sp.	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Sesquiterpenoid
Fatty acid ester
Fatty acyl
Secondary alcohol
Carboxylic acid ester
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
logP	5.27	ALOGPS
logP	6.27	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	13.08	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	151.73 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	179.72 m³·mol⁻¹	ChemAxon
Polarizability	76.59 Å³	ChemAxon
Number of Rings	3	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

162819072

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Gagunin O (NP0076579)

MOL for NP0076579 ((+)-Gagunin O)

3D MOL for NP0076579 ((+)-Gagunin O)

3D SDF for NP0076579 ((+)-Gagunin O)

3D-SDF for NP0076579 ((+)-Gagunin O)

PDB for NP0076579 ((+)-Gagunin O)

3D PDB for NP0076579 ((+)-Gagunin O)

SMILES for NP0076579 ((+)-Gagunin O)

INCHI for NP0076579 ((+)-Gagunin O)

Structure for NP0076579 ((+)-Gagunin O)

3D Structure for NP0076579 ((+)-Gagunin O)