NP-MRD: Showing NP-Card for (1r,2s,3s,4s,5s,8r,9r,11s,12r)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid (NP0296656)

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Record Information

Version

2.0

Created at

2022-09-10 06:22:17 UTC

Updated at

2022-09-10 06:22:17 UTC

NP-MRD ID

NP0296656

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3s,4s,5s,8r,9r,11s,12r)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid

Description

57672-81-8 Belongs to the class of organic compounds known as c20-gibberellin 20-carboxylic acids. These are c20-gibberellins with a carboxyl group at the 6-position. (1r,2s,3s,4s,5s,8r,9r,11s,12r)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid is found in Cucurbita maxima and Cucurbita pepo. 57672-81-8 Is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652307222022412D          

 30 33  0  0  0  0            999 V2000
   -1.3586    0.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1402   -0.5590    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0860    0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    1.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1399    1.8840    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1453    0.7793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8606    1.4821    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4438    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9956    0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6202    0.1046    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7876    0.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1144   -0.0036    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6424    1.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6440    0.5209    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3958   -1.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2031   -1.5141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553   -1.9569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3561    1.7632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0728    1.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0731    0.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7875   -0.7165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3587   -0.7162    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8325   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8748   -1.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6445   -0.3041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0724   -0.3041    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6454   -1.0166    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903   -1.2346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5754   -2.1286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1893    2.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10  3  1  6  0  0  0
  7  3  1  6  0  0  0
  9 11  2  0  0  0  0
  2 10  1  0  0  0  0
  6 12  1  1  0  0  0
 14 13  1  6  0  0  0
  1 14  1  0  0  0  0
 14  6  1  0  0  0  0
  2 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 13 19  2  0  0  0  0
 13 18  1  0  0  0  0
  1 20  1  0  0  0  0
 22 25  1  0  0  0  0
 26 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  6  0  0  0
 25 27  1  1  0  0  0
 20 26  1  0  0  0  0
 26 21  1  1  0  0  0
 14 25  1  0  0  0  0
 25  2  1  0  0  0  0
 24 28  1  0  0  0  0
 24 29  2  0  0  0  0
  5 30  1  6  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -4.5231   -1.8407    0.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4302   -1.1257    0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0930   -1.4919    0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1306   -0.4540    0.5751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8518    0.0768    1.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2713    0.2117    1.2564 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3002    1.3124    0.2188 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9862    2.4310    0.7034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9134    1.7607   -0.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0064    0.6164   -0.4722 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4634    0.9803   -0.4597 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7976    2.0774    0.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978    2.0134    1.5315 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4282    3.3856    0.0577 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9283    1.3353   -1.8849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460    0.9550   -2.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1475    0.6777   -0.8985 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4011    0.1927   -1.3147 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5364   -0.4236   -0.0390 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0195   -1.7520   -0.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1131   -0.4066    1.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862    0.4400    1.6011 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7082   -1.3136    2.2595 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0806   -0.3511   -0.1732 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2423   -0.9585    0.9144 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2824   -2.4287    0.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3566   -3.2155    1.7061 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2423   -3.0290   -0.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4444   -1.4906    0.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5057   -2.8060    0.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2225   -1.4868   -1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8140   -2.5306    0.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5299    1.0604    2.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8205   -0.7088    2.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9996    0.4267    2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8891    0.9309   -0.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5179    3.2772    0.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0387    2.3574   -1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5731    2.4358    0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2543    0.2365   -1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0490    3.6376   -0.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2996    0.6570   -2.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6682    2.3551   -2.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4633    0.1086   -2.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8410    1.8256   -2.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3785    1.5918   -0.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0779    0.8926   -1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8643   -2.5185    0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1264   -1.6396   -0.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5300   -1.9575   -1.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3051   -2.0142    2.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8215   -0.9716   -1.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5065   -0.6581    1.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1945   -2.6865   -1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  7  1  0
  7  8  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  6
  3  2  1  0
  2  1  2  3
  4 25  1  0
 25 26  1  0
 26 28  1  0
 26 27  2  0
 25 24  1  0
 24 11  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  1
 21 23  1  0
 21 22  2  0
 11 12  1  1
 12 14  1  0
 12 13  2  0
  4 10  1  0
 19 24  1  0
 11 10  1  0
  2  6  1  0
 10 40  1  6
  9 38  1  0
  9 39  1  0
  7 36  1  6
  8 37  1  0
  6 35  1  1
  5 33  1  0
  5 34  1  0
  3 31  1  0
  3 32  1  0
  1 29  1  0
  1 30  1  0
 25 53  1  1
 28 54  1  0
 24 52  1  6
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  1
 18 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 23 51  1  0
 14 41  1  0
M  END


  Mrv1652307222022412D          

 30 33  0  0  0  0            999 V2000
   -1.3586    0.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1402   -0.5590    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0860    0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    1.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1399    1.8840    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1453    0.7793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8606    1.4821    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4438    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9956    0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6202    0.1046    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7876    0.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1144   -0.0036    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6424    1.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6440    0.5209    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3958   -1.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2031   -1.5141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553   -1.9569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3561    1.7632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0728    1.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0731    0.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7875   -0.7165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3587   -0.7162    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8325   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8748   -1.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6445   -0.3041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0724   -0.3041    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6454   -1.0166    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903   -1.2346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5754   -2.1286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1893    2.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10  3  1  6  0  0  0
  7  3  1  6  0  0  0
  9 11  2  0  0  0  0
  2 10  1  0  0  0  0
  6 12  1  1  0  0  0
 14 13  1  6  0  0  0
  1 14  1  0  0  0  0
 14  6  1  0  0  0  0
  2 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 13 19  2  0  0  0  0
 13 18  1  0  0  0  0
  1 20  1  0  0  0  0
 22 25  1  0  0  0  0
 26 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  6  0  0  0
 25 27  1  1  0  0  0
 20 26  1  0  0  0  0
 26 21  1  1  0  0  0
 14 25  1  0  0  0  0
 25  2  1  0  0  0  0
 24 28  1  0  0  0  0
 24 29  2  0  0  0  0
  5 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0296656

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@H](O)[C@@H]3C[C@]1(CC3=C)[C@@H](C(O)=O)[C@@]1([H])[C@]2(CC[C@H](O)[C@@]1(C)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O8/c1-8-6-19-7-9(8)10(21)5-11(19)20(17(27)28)4-3-12(22)18(2,16(25)26)14(20)13(19)15(23)24/h9-14,21-22H,1,3-7H2,2H3,(H,23,24)(H,25,26)(H,27,28)/t9-,10+,11-,12+,13-,14-,18-,19+,20-/m1/s1

> <INCHI_KEY>
LKLDZCIWUDJQCF-OZPHONOWSA-N

> <FORMULA>
C20H26O8

> <MOLECULAR_WEIGHT>
394.42

> <EXACT_MASS>
394.162767797

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.63921491535943

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3S,4S,5S,8R,9R,11S,12R)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4,8-tricarboxylic acid

> <ALOGPS_LOGP>
0.14

> <JCHEM_LOGP>
0.23812334766666643

> <ALOGPS_LOGS>
-1.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.119120137648283

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5808563385292365

> <JCHEM_PKA_STRONGEST_BASIC>
-0.867879636738555

> <JCHEM_POLAR_SURFACE_AREA>
152.35999999999999

> <JCHEM_REFRACTIVITY>
93.82770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.99e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,4S,5S,8R,9R,11S,12R)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4,8-tricarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUL-20         0                                  
HETATM    1  C   UNK     0      -2.536   1.742   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.262  -1.043   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.027   1.750   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.703   2.933   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.128   3.517   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.271   1.455   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.473   2.767   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.695   0.103   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.725   1.247   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.158   0.195   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.204   0.816   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0      -0.214  -0.007   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0      -1.199   2.519   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.202   0.972   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.739  -2.507   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.246  -2.826   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.290  -3.653   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.531   3.291   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.136   3.286   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.870   0.972   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.203  -1.337   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.536  -1.337   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.554  -2.520   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.500  -2.538   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.203  -0.568   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.868  -0.568   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0      -1.205  -1.898   0.000  0.00  0.00           H+0
HETATM   28  O   UNK     0      -5.022  -2.305   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -2.941  -3.973   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.220   5.054   0.000  0.00  0.00           O+0
CONECT    1   14   20                                                       
CONECT    2   10   15   25                                                  
CONECT    3   10    7                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7   30                                                  
CONECT    6    4   10   12   14                                             
CONECT    7    5    9    3                                                  
CONECT    8    9   10                                                       
CONECT    9    7    8   11                                                  
CONECT   10    6    8    3    2                                             
CONECT   11    9                                                            
CONECT   12    6                                                            
CONECT   13   14   19   18                                                  
CONECT   14   13    1    6   25                                             
CONECT   15    2   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13                                                            
CONECT   19   13                                                            
CONECT   20    1   26                                                       
CONECT   21   26                                                            
CONECT   22   25   26   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   28   29                                                  
CONECT   25   22   27   14    2                                             
CONECT   26   22   20   21                                                  
CONECT   27   25                                                            
CONECT   28   24                                                            
CONECT   29   24                                                            
CONECT   30    5                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
GA39	HMDB
Gibberellin A39	HMDB

Chemical Formula

C₂₀H₂₆O₈

Average Mass

394.4200 Da

Monoisotopic Mass

394.16277 Da

IUPAC Name

(1R,2S,3S,4S,5S,8R,9R,11S,12R)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4,8-tricarboxylic acid

Traditional Name

(1R,2S,3S,4S,5S,8R,9R,11S,12R)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4,8-tricarboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@H](O)[C@@H]3C[C@]1(CC3=C)[C@@H](C(O)=O)[C@@]1([H])[C@]2(CC[C@H](O)[C@@]1(C)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C20H26O8/c1-8-6-19-7-9(8)10(21)5-11(19)20(17(27)28)4-3-12(22)18(2,16(25)26)14(20)13(19)15(23)24/h9-14,21-22H,1,3-7H2,2H3,(H,23,24)(H,25,26)(H,27,28)/t9-,10+,11-,12+,13-,14-,18-,19+,20-/m1/s1

InChI Key

LKLDZCIWUDJQCF-OZPHONOWSA-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
Cucurbita maxima	LOTUS Database	35616633
Cucurbita pepo	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c20-gibberellin 20-carboxylic acids. These are c20-gibberellins with a carboxyl group at the 6-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

C20-gibberellin 20-carboxylic acids

Alternative Parents

Substituents

Gibberellane-20-carboxylic acid
Gibberellane-6-carboxylic acid
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	0.14	ALOGPS
logP	0.24	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.58	ChemAxon
pKa (Strongest Basic)	-0.87	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	152.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.83 m³·mol⁻¹	ChemAxon
Polarizability	38.64 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035045

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013662

KNApSAcK ID

C00000039

Chemspider ID

10222090

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21596346

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,3s,4s,5s,8r,9r,11s,12r)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid (NP0296656)

MOL for NP0296656 ((1r,2s,3s,4s,5s,8r,9r,11s,12r)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid)

3D MOL for NP0296656 ((1r,2s,3s,4s,5s,8r,9r,11s,12r)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid)

3D SDF for NP0296656 ((1r,2s,3s,4s,5s,8r,9r,11s,12r)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid)

3D-SDF for NP0296656 ((1r,2s,3s,4s,5s,8r,9r,11s,12r)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid)

PDB for NP0296656 ((1r,2s,3s,4s,5s,8r,9r,11s,12r)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid)

3D PDB for NP0296656 ((1r,2s,3s,4s,5s,8r,9r,11s,12r)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid)

SMILES for NP0296656 ((1r,2s,3s,4s,5s,8r,9r,11s,12r)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid)

INCHI for NP0296656 ((1r,2s,3s,4s,5s,8r,9r,11s,12r)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid)

Structure for NP0296656 ((1r,2s,3s,4s,5s,8r,9r,11s,12r)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid)

3D Structure for NP0296656 ((1r,2s,3s,4s,5s,8r,9r,11s,12r)-5,11-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylic acid)