NP-MRD: Showing NP-Card for (+)-Malacitanolide (NP0075550)

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Record Information

Version

2.0

Created at

2022-04-28 20:49:16 UTC

Updated at

2022-04-28 20:49:16 UTC

NP-MRD ID

NP0075550

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Malacitanolide

Description

Malacitanolide belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. (+)-Malacitanolide is found in Centaurea attica ssp.attica, Centaurea malacitana and Centaurea spinosa. (+)-Malacitanolide was first documented in 2005 (PMID: 16180824). Based on a literature review very few articles have been published on Malacitanolide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222492D          

 28 30  0  0  1  0            999 V2000
   -2.1434   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6005   -3.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0484   -3.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209   -3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8334   -4.0827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7565   -2.6145    0.0000 O   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
  5  6  1  0  0  0  0
  6  1  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  1  0  0  0
  7 12  1  1  0  0  0
 12 13  2  0  0  0  0
  5 14  1  1  0  0  0
  3 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  1  0  0  0
  2 24  1  1  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  1 28  1  6  0  0  0
M  END

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
    3.0991    1.7395   -0.7872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4906    0.5115   -0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4848   -0.5073   -0.3263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8602   -1.6825   -0.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362   -0.2740   -0.3208 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -1.3156   -0.0832 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4568   -1.0052    1.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4624    0.1006    1.1992 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4251   -0.1532    2.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1380    0.1017   -0.1606 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3871    0.9008   -0.1879 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5448    0.3102    0.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1689   -0.6297    0.0787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0382    2.2697    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5740    2.5045    0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8622    1.4476    1.3843 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8976    1.8392    2.7374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1694   -1.2848   -0.6198 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8852   -1.6038   -1.7828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3389   -2.8668   -2.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9161   -3.7688   -2.8277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9883   -2.9488   -1.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2150   -4.0063   -1.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7420   -1.5611   -1.1533 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9188    0.1344   -0.5454 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0778   -0.8004   -1.5963 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8513    1.2842   -0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7891    2.2575    0.1764 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7858    2.5344   -0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0414    2.0101   -0.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8120   -2.2479    0.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3106   -0.7300    1.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9288   -1.9395    1.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8756    0.7427    2.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8009   -0.5866    3.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1741   -0.9294    2.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140    0.6768   -0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6761    1.0102   -1.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8730    0.7493    1.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6151    2.4734    1.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3964    3.0389   -0.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0422    2.6392   -0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4555    3.4581    1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2021    1.4743    1.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5801    2.5437    2.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4421   -2.0438    0.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5036   -4.9857   -1.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7821   -3.9573   -1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6799   -0.8547   -2.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1765   -0.3435    0.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0216   -0.2564   -2.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8761    0.8814   -0.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6617    1.7688   -1.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0744    1.8806    1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  1
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
  6 24  1  0
 24 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  3
 18 10  1  0
 10 11  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 11 12  1  0
 12 13  2  0
 10  8  1  0
 16  8  1  0
 22 24  1  0
  9 34  1  0
  9 35  1  0
  9 36  1  0
  7 32  1  0
  7 33  1  0
  6 31  1  1
  1 29  1  0
  1 30  1  0
 25 50  1  1
 26 51  1  0
 27 52  1  0
 27 53  1  0
 28 54  1  0
 24 49  1  6
 18 46  1  1
 23 47  1  0
 23 48  1  0
 10 37  1  6
 11 38  1  6
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  6
 17 45  1  0
 12 39  1  0
M  END


  Mrv1652304282222492D          

 28 30  0  0  1  0            999 V2000
   -2.1434   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6005   -3.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0484   -3.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209   -3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8334   -4.0827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7565   -2.6145    0.0000 O   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
  5  6  1  0  0  0  0
  6  1  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  1  0  0  0
  7 12  1  1  0  0  0
 12 13  2  0  0  0  0
  5 14  1  1  0  0  0
  3 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  1  0  0  0
  2 24  1  1  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  1 28  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0075550

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12C[C@H](OC(=O)C(=C)[C@@H](O)CO)[C@@H]3[C@H](OC(=O)C3=C)[C@H]1[C@H](CC[C@H]2O)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O8/c1-9(12(23)8-22)18(25)27-13-6-20(3)14(24)5-4-11(7-21)16(20)17-15(13)10(2)19(26)28-17/h7,11-17,22-24H,1-2,4-6,8H2,3H3/t11-,12+,13+,14-,15-,16-,17+,20+/m1/s1

> <INCHI_KEY>
OZJAAHIGUMFSHY-MYBIUHGVSA-N

> <FORMULA>
C20H26O8

> <MOLECULAR_WEIGHT>
394.42

> <EXACT_MASS>
394.162767797

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.318238396974046

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,5aR,6R,9S,9aS,9bR)-9-formyl-6-hydroxy-5a-methyl-3-methylidene-2-oxo-dodecahydronaphtho[1,2-b]furan-4-yl (3R)-3,4-dihydroxy-2-methylidenebutanoate

> <ALOGPS_LOGP>
0.04

> <JCHEM_LOGP>
-0.10009269799999912

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.65083034910204

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.501755907224496

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9334101980486755

> <JCHEM_POLAR_SURFACE_AREA>
130.35999999999999

> <JCHEM_REFRACTIVITY>
96.08849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,5aR,6R,9S,9aS,9bR)-9-formyl-6-hydroxy-5a-methyl-3-methylidene-2-oxo-octahydro-3aH-naphtho[1,2-b]furan-4-yl (3R)-3,4-dihydroxy-2-methylidenebutanoate

> <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      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -8.002  -1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.988  -6.126   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.957  -7.271   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.519  -6.287   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.289  -7.621   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -5.145  -4.880   0.000  0.00  0.00           O+0
CONECT    1    2    6   28                                                  
CONECT    2    1    3   24                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10   14                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10                                                            
CONECT   12    7   13                                                       
CONECT   13   12                                                            
CONECT   14    5                                                            
CONECT   15    3   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20                                                            
CONECT   24    2   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    1                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₈

Average Mass

394.4200 Da

Monoisotopic Mass

394.16277 Da

IUPAC Name

(3aR,4S,5aR,6R,9S,9aS,9bR)-9-formyl-6-hydroxy-5a-methyl-3-methylidene-2-oxo-dodecahydronaphtho[1,2-b]furan-4-yl (3R)-3,4-dihydroxy-2-methylidenebutanoate

Traditional Name

(3aR,4S,5aR,6R,9S,9aS,9bR)-9-formyl-6-hydroxy-5a-methyl-3-methylidene-2-oxo-octahydro-3aH-naphtho[1,2-b]furan-4-yl (3R)-3,4-dihydroxy-2-methylidenebutanoate

CAS Registry Number

Not Available

SMILES

C[C@@]12C[C@H](OC(=O)C(=C)[C@@H](O)CO)[C@@H]3[C@H](OC(=O)C3=C)[C@H]1[C@H](CC[C@H]2O)C=O

InChI Identifier

InChI=1S/C20H26O8/c1-9(12(23)8-22)18(25)27-13-6-20(3)14(24)5-4-11(7-21)16(20)17-15(13)10(2)19(26)28-17/h7,11-17,22-24H,1-2,4-6,8H2,3H3/t11-,12+,13+,14-,15-,16-,17+,20+/m1/s1

InChI Key

OZJAAHIGUMFSHY-MYBIUHGVSA-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
Centaurea attica ssp.attica	Plant	KNApSAcK
Centaurea malacitana	Plant	KNApSAcK
Centaurea spinosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Beta-hydroxy acid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Gamma butyrolactone
Hydroxy acid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Aldehyde
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
Organic oxygen compound
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	0.04	ALOGPS
logP	-0.1	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	13.5	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	96.09 m³·mol⁻¹	ChemAxon
Polarizability	39.32 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00037470

Chemspider ID

8914723

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10739390

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Saroglou V, Karioti A, Demetzos C, Dimas K, Skaltsa H: Sesquiterpene lactones from Centaurea spinosa and their antibacterial and cytotoxic activities. J Nat Prod. 2005 Sep;68(9):1404-7. doi: 10.1021/np058042u. [PubMed:16180824 ]

Showing NP-Card for (+)-Malacitanolide (NP0075550)

MOL for NP0075550 ((+)-Malacitanolide)

3D MOL for NP0075550 ((+)-Malacitanolide)

3D SDF for NP0075550 ((+)-Malacitanolide)

3D-SDF for NP0075550 ((+)-Malacitanolide)

PDB for NP0075550 ((+)-Malacitanolide)

3D PDB for NP0075550 ((+)-Malacitanolide)

SMILES for NP0075550 ((+)-Malacitanolide)

INCHI for NP0075550 ((+)-Malacitanolide)

Structure for NP0075550 ((+)-Malacitanolide)

3D Structure for NP0075550 ((+)-Malacitanolide)