NP-MRD: Showing NP-Card for (1s,5r,8s,9s,10r,11s,12s)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylic acid (NP0329564)

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Record Information

Version

2.0

Created at

2022-09-12 14:04:30 UTC

Updated at

2022-09-12 14:04:31 UTC

NP-MRD ID

NP0329564

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,5r,8s,9s,10r,11s,12s)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylic acid

Description

Gibberellin A88 belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (1s,5r,8s,9s,10r,11s,12s)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylic acid is found in Lygodium circinatum. Gibberellin A88 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652307272022302D          

 25 29  0  0  1  0            999 V2000
    0.1402   -0.5591    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0861    0.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    1.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1399    1.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1453    0.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8608    1.4823    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4440    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9958    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203    0.1046    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7879    0.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3958   -1.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032   -1.5143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553   -1.9571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6433    0.5212    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6433   -0.3038    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6433    1.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3619    0.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3619   -0.7261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8031   -0.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732    0.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732   -0.3038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3659   -1.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1984    0.0230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6433   -1.1253    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7901   -0.7119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  4  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9  2  1  6  0  0  0
  6  2  1  6  0  0  0
  8 10  2  0  0  0  0
  1  9  1  0  0  0  0
  1 11  1  1  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  6  0  0  0
 14 17  1  0  0  0  0
 15 18  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  1  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 18 19  1  6  0  0  0
 20 21  1  0  0  0  0
 15 24  1  1  0  0  0
 14  5  1  0  0  0  0
 15  1  1  0  0  0  0
 21 25  1  1  0  0  0
M  END

     RDKit          3D

 46 50  0  0  0  0  0  0  0  0999 V2000
   -4.3062   -0.9255    1.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3054   -0.2602    0.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8875   -0.2454    1.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1545    0.5036   -0.0456 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1812    1.5050   -0.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772    0.5670   -0.7372 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0917   -0.3432   -1.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7515   -0.9402   -1.8580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7464   -0.4092   -1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7100   -0.4735   -1.1560 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3034   -1.8149   -1.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3722   -2.1694   -0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2653   -1.0329   -0.0007 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7377   -1.2709    1.3042 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5114    0.2993    0.0773 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1198    1.2275    1.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5272    0.8651   -1.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5110    1.5032   -1.7645 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3203    0.5483   -1.9200 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0769   -0.0290    0.2674 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1422    1.1204    0.4177 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0499    1.6565    1.7882 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6325    1.2392    2.7953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7963    2.7645    1.9614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2933   -0.8822    0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1642   -1.4996    1.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5525   -1.3169    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8193    0.1844    2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9002    2.0286   -1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4455    2.1418    0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3033    1.1273   -0.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8292   -1.1929   -1.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3052    0.1749   -2.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5604   -1.8536   -2.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -1.8324   -2.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5683   -2.6431   -1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0154   -2.9732   -0.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8904   -2.5948    0.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1445   -0.9209   -0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5655   -0.7832    1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2097    0.7082    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1620    1.4415    0.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5534    2.1613    1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8897   -0.8467    0.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4232    1.9014   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7199    3.5847    1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0
 21 22  1  0
 22 24  1  0
 22 23  2  0
 21  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  2  0
 17 19  1  0
  6  2  1  0
  2  1  2  3
  2  3  1  0
 10 20  1  0
 10 19  1  6
 15 20  1  0
  9  4  1  0
  4  3  1  1
 20 44  1  1
 21 45  1  6
 24 46  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  6
  7 32  1  0
  7 33  1  0
  8 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  6
 14 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
M  END


  Mrv1652307272022302D          

 25 29  0  0  1  0            999 V2000
    0.1402   -0.5591    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0861    0.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    1.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1399    1.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1453    0.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8608    1.4823    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4440    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9958    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203    0.1046    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7879    0.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3958   -1.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032   -1.5143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553   -1.9571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6433    0.5212    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6433   -0.3038    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6433    1.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3619    0.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3619   -0.7261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8031   -0.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732    0.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732   -0.3038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3659   -1.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1984    0.0230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6433   -1.1253    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7901   -0.7119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  4  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9  2  1  6  0  0  0
  6  2  1  6  0  0  0
  8 10  2  0  0  0  0
  1  9  1  0  0  0  0
  1 11  1  1  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  6  0  0  0
 14 17  1  0  0  0  0
 15 18  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  1  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 18 19  1  6  0  0  0
 20 21  1  0  0  0  0
 15 24  1  1  0  0  0
 14  5  1  0  0  0  0
 15  1  1  0  0  0  0
 21 25  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0329564

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12[C@H](C(O)=O)[C@@]34C[C@@H](CC=C3[C@]11CC[C@H](O)[C@@]2(C)C(=O)O1)C(=C)C4

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O5/c1-9-7-18-8-10(9)3-4-11(18)19-6-5-12(20)17(2,16(23)24-19)14(19)13(18)15(21)22/h4,10,12-14,20H,1,3,5-8H2,2H3,(H,21,22)/t10-,12+,13-,14-,17-,18+,19-/m1/s1

> <INCHI_KEY>
BSBICXIQCTXPMN-OOULSYMHSA-N

> <FORMULA>
C19H22O5

> <MOLECULAR_WEIGHT>
330.375

> <EXACT_MASS>
330.146723814

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.00542290062211

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,8S,9S,10R,11S,12S)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-2-ene-9-carboxylic acid

> <ALOGPS_LOGP>
1.52

> <JCHEM_LOGP>
1.2326940340000005

> <ALOGPS_LOGS>
-2.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.444386897327597

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.251191140158928

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0424850888268233

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
84.85179999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,8S,9S,10R,11S,12S)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-2-ene-9-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-JUL-20         0                                  
HETATM    1  C   UNK     0       0.262  -1.044   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.027   1.750   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.703   2.933   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.128   3.517   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.271   1.455   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.473   2.767   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.695   0.103   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.725   1.247   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.158   0.195   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.204   0.816   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.739  -2.508   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.246  -2.827   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.290  -3.653   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.201   0.973   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.201  -0.567   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.201   2.506   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.542   1.740   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.542  -1.355   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.366  -0.134   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.870   0.973   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.870  -0.567   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.550  -2.881   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.237   0.043   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0      -1.201  -2.101   0.000  0.00  0.00           H+0
HETATM   25  O   UNK     0      -5.208  -1.329   0.000  0.00  0.00           O+0
CONECT    1    9   11   15                                                  
CONECT    2    9    6                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    9   14                                                  
CONECT    6    4    8    2                                                  
CONECT    7    8    9                                                       
CONECT    8    6    7   10                                                  
CONECT    9    5    7    2    1                                             
CONECT   10    8                                                            
CONECT   11    1   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   15   16   17    5                                             
CONECT   15   14   18   24    1                                             
CONECT   16   14   19                                                       
CONECT   17   14   20                                                       
CONECT   18   15   21   22   19                                             
CONECT   19   16   23   18                                                  
CONECT   20   17   21                                                       
CONECT   21   18   20   25                                                  
CONECT   22   18                                                            
CONECT   23   19                                                            
CONECT   24   15                                                            
CONECT   25   21                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
GA88	HMDB
Gibberellin A88	HMDB

Chemical Formula

C₁₉H₂₂O₅

Average Mass

330.3750 Da

Monoisotopic Mass

330.14672 Da

IUPAC Name

(1S,5R,8S,9S,10R,11S,12S)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-2-ene-9-carboxylic acid

Traditional Name

(1S,5R,8S,9S,10R,11S,12S)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-2-ene-9-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@]12[C@H](C(O)=O)[C@@]34C[C@@H](CC=C3[C@]11CC[C@H](O)[C@@]2(C)C(=O)O1)C(=C)C4

InChI Identifier

InChI=1S/C19H22O5/c1-9-7-18-8-10(9)3-4-11(18)19-6-5-12(20)17(2,16(23)24-19)14(19)13(18)15(21)22/h4,10,12-14,20H,1,3,5-8H2,2H3,(H,21,22)/t10-,12+,13-,14-,17-,18+,19-/m1/s1

InChI Key

BSBICXIQCTXPMN-OOULSYMHSA-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
Lygodium circinatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Caprolactone
Oxepane
Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid
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	1.52	ALOGPS
logP	1.23	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	4.25	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	84.85 m³·mol⁻¹	ChemAxon
Polarizability	34.01 Å³	ChemAxon
Number of Rings	5	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

HMDB0039240

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018777

KNApSAcK ID

C00000088

Chemspider ID

9210060

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11034886

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,5r,8s,9s,10r,11s,12s)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylic acid (NP0329564)

MOL for NP0329564 ((1s,5r,8s,9s,10r,11s,12s)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylic acid)

3D MOL for NP0329564 ((1s,5r,8s,9s,10r,11s,12s)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylic acid)

3D SDF for NP0329564 ((1s,5r,8s,9s,10r,11s,12s)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylic acid)

3D-SDF for NP0329564 ((1s,5r,8s,9s,10r,11s,12s)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylic acid)

PDB for NP0329564 ((1s,5r,8s,9s,10r,11s,12s)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylic acid)

3D PDB for NP0329564 ((1s,5r,8s,9s,10r,11s,12s)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylic acid)

SMILES for NP0329564 ((1s,5r,8s,9s,10r,11s,12s)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylic acid)

INCHI for NP0329564 ((1s,5r,8s,9s,10r,11s,12s)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylic acid)

Structure for NP0329564 ((1s,5r,8s,9s,10r,11s,12s)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylic acid)

3D Structure for NP0329564 ((1s,5r,8s,9s,10r,11s,12s)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylic acid)