NP-MRD: Showing NP-Card for (+)-6alpha-Malonyloxymanoyl oxide (NP0076079)

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Record Information

Version

2.0

Created at

2022-04-28 21:15:25 UTC

Updated at

2022-04-28 21:15:25 UTC

NP-MRD ID

NP0076079

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-6alpha-Malonyloxymanoyl oxide

Description

6Alpha-malonyloxymanoyl oxide belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (+)-6alpha-Malonyloxymanoyl oxide is found in Stemodia foliosa. (+)-6alpha-Malonyloxymanoyl oxide was first documented in 2008 (PMID: 18582112). Based on a literature review very few articles have been published on 6alpha-malonyloxymanoyl oxide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223152D          

 28 30  0  0  1  0            999 V2000
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  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
    0.0000   -1.6500    0.0000 O   0  0  0  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
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6044   -4.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1673   -4.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918   -5.6496    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
   -3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8995   -1.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6741   -1.7466    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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  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
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  7 21  1  6  0  0  0
 19 22  1  1  0  0  0
 22 23  2  0  0  0  0
 19 24  1  6  0  0  0
  8 25  1  6  0  0  0
  5 26  1  6  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
M  END

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
   -4.9725    2.8041   -0.7516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7311    1.5089   -0.7559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7376    0.9689    0.2056 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2143    1.4516    1.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8833   -0.5275    0.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6771   -1.1273    0.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4878   -0.6167    0.1708 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2343   -1.4030    0.3745 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1741   -1.5119    1.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5326   -2.8160   -0.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4116   -3.2445   -1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8014   -3.0705   -0.7035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0800   -1.5856   -0.6359 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7065   -1.2097   -1.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1129   -1.3503    0.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8263   -0.7924   -0.5051 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0639    0.6370   -0.1241 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0307    1.1726   -1.0291 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1563    1.8180   -0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2749    1.9039    0.7147 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1955    2.3941   -1.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2581    3.0088   -0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2506    3.5635   -1.1553 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1789    2.9839    0.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2281    1.3908   -0.4630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3981    0.8506    0.3767 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1793    1.3136    1.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5239    1.4510   -0.1354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7052    3.2426   -1.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4951    3.5177   -0.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2433    0.8721   -1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1746    2.5411    1.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3147    1.1908    1.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7705    0.8882    2.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8174   -0.8734   -0.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8302   -0.7897    0.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7289   -0.8121    1.9763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8058   -2.2169    0.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7618   -0.7624   -0.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6351   -0.6226    2.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8600   -2.3573    1.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7452   -1.7515    2.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5487   -2.9281   -0.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4287   -3.5676    0.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2384   -4.3225   -1.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2714   -2.7009   -2.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9791   -3.5972    0.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4935   -3.5574   -1.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9271   -2.1127   -2.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6889   -0.7081   -1.8537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0366   -0.5659   -2.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8169   -0.7464    1.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -2.3225    0.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0564   -0.8799   -0.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3634   -0.7588   -1.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3630    0.8080    0.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7418    3.2272   -2.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5885    1.6631   -2.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0142    2.8467    1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1296    2.4545   -0.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4381    1.2051   -1.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3947    0.6063    2.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1350    1.7038    1.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8198    2.2207    1.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  6
 13 15  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  1
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  1
  3 28  1  0
 28 26  1  0
 26 27  1  1
 26 25  1  0
 25 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 24  1  0
 22 23  2  0
 17 16  1  0
  3  2  1  0
  2  1  2  3
 16 13  1  0
 16  8  1  0
 26  7  1  0
 14 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 15 54  1  0
 12 47  1  0
 12 48  1  0
 11 45  1  0
 11 46  1  0
 10 43  1  0
 10 44  1  0
  9 40  1  0
  9 41  1  0
  9 42  1  0
  7 39  1  6
  6 37  1  0
  6 38  1  0
  5 35  1  0
  5 36  1  0
  4 32  1  0
  4 33  1  0
  4 34  1  0
 27 62  1  0
 27 63  1  0
 27 64  1  0
 25 60  1  0
 25 61  1  0
 17 56  1  1
 21 57  1  0
 21 58  1  0
 24 59  1  0
 16 55  1  6
  2 31  1  0
  1 29  1  0
  1 30  1  0
M  END


  Mrv1652304282223152D          

 28 30  0  0  1  0            999 V2000
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  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
    0.0000   -1.6500    0.0000 O   0  0  0  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
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6044   -4.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1673   -4.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918   -5.6496    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
   -3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8995   -1.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6741   -1.7466    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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  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
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  7 21  1  6  0  0  0
 19 22  1  1  0  0  0
 22 23  2  0  0  0  0
 19 24  1  6  0  0  0
  8 25  1  6  0  0  0
  5 26  1  6  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076079

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@]2(C)[C@H]3CC[C@@](C)(O[C@]3(C)C[C@H](OC(=O)CC(O)=O)[C@@H]12)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C23H36O5/c1-7-21(4)12-9-16-22(5)11-8-10-20(2,3)19(22)15(14-23(16,6)28-21)27-18(26)13-17(24)25/h7,15-16,19H,1,8-14H2,2-6H3,(H,24,25)/t15-,16+,19-,21-,22+,23+/m0/s1

> <INCHI_KEY>
JZRGFUZJIZSKTF-ALFLKXBZSA-N

> <FORMULA>
C23H36O5

> <MOLECULAR_WEIGHT>
392.536

> <EXACT_MASS>
392.256274259

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
44.16526766427165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(3R,4aR,6S,6aS,10aS,10bR)-3-ethenyl-3,4a,7,7,10a-pentamethyl-dodecahydro-1H-naphtho[2,1-b]pyran-6-yl]oxy}-3-oxopropanoic acid

> <ALOGPS_LOGP>
4.58

> <JCHEM_LOGP>
4.450356814666665

> <ALOGPS_LOGS>
-5.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.229614560552305

> <JCHEM_PKA_STRONGEST_BASIC>
-4.23556115465236

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
106.51730000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.01e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(3R,4aR,6S,6aS,10aS,10bR)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1H-naphtho[2,1-b]pyran-6-yl]oxy}-3-oxopropanoic acid

> <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      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.128  -9.294   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.312  -7.988   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.851 -10.546   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.279  -3.260   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.725  -3.260   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   27   28                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   26                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   21                                                  
CONECT    8    7    9   18   25                                             
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    8   19                                                       
CONECT   19   18   20   22   24                                             
CONECT   20   19   21                                                       
CONECT   21   20    7                                                       
CONECT   22   19   23                                                       
CONECT   23   22                                                            
CONECT   24   19                                                            
CONECT   25    8                                                            
CONECT   26    5                                                            
CONECT   27    3                                                            
CONECT   28    3                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
6a-Malonyloxymanoyl oxide	Generator
6Α-malonyloxymanoyl oxide	Generator

Chemical Formula

C₂₃H₃₆O₅

Average Mass

392.5360 Da

Monoisotopic Mass

392.25627 Da

IUPAC Name

3-{[(3R,4aR,6S,6aS,10aS,10bR)-3-ethenyl-3,4a,7,7,10a-pentamethyl-dodecahydro-1H-naphtho[2,1-b]pyran-6-yl]oxy}-3-oxopropanoic acid

Traditional Name

3-{[(3R,4aR,6S,6aS,10aS,10bR)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1H-naphtho[2,1-b]pyran-6-yl]oxy}-3-oxopropanoic acid

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@]2(C)[C@H]3CC[C@@](C)(O[C@]3(C)C[C@H](OC(=O)CC(O)=O)[C@@H]12)C=C

InChI Identifier

InChI=1S/C23H36O5/c1-7-21(4)12-9-16-22(5)11-8-10-20(2,3)19(22)15(14-23(16,6)28-21)27-18(26)13-17(24)25/h7,15-16,19H,1,8-14H2,2-6H3,(H,24,25)/t15-,16+,19-,21-,22+,23+/m0/s1

InChI Key

JZRGFUZJIZSKTF-ALFLKXBZSA-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
Stemodia foliosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Polycyclic triterpenoid
Triterpenoid
Naphthopyran
Naphthalene
Dicarboxylic acid or derivatives
Oxane
1,3-dicarbonyl compound
Pyran
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

cyclic ether (CHEBI:66662 )
labdane diterpenoid (CHEBI:66662 )
malonate ester (CHEBI:66662 )

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	4.58	ALOGPS
logP	4.45	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.23	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	106.52 m³·mol⁻¹	ChemAxon
Polarizability	44.17 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00038300

Chemspider ID

23341191

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24970705

PDB ID

Not Available

ChEBI ID

66662

Good Scents ID

Not Available

References

General References

da Silva LL, Nascimento MS, Cavalheiro AJ, Silva DH, Castro-Gamboa I, Furlan M, Bolzani Vda S: Antibacterial activity of labdane diterpenoids from Stemodia foliosa. J Nat Prod. 2008 Jul;71(7):1291-3. doi: 10.1021/np800106x. Epub 2008 Jun 27. [PubMed:18582112 ]

Showing NP-Card for (+)-6alpha-Malonyloxymanoyl oxide (NP0076079)

MOL for NP0076079 ((+)-6alpha-Malonyloxymanoyl oxide)

3D MOL for NP0076079 ((+)-6alpha-Malonyloxymanoyl oxide)

3D SDF for NP0076079 ((+)-6alpha-Malonyloxymanoyl oxide)

3D-SDF for NP0076079 ((+)-6alpha-Malonyloxymanoyl oxide)

PDB for NP0076079 ((+)-6alpha-Malonyloxymanoyl oxide)

3D PDB for NP0076079 ((+)-6alpha-Malonyloxymanoyl oxide)

SMILES for NP0076079 ((+)-6alpha-Malonyloxymanoyl oxide)

INCHI for NP0076079 ((+)-6alpha-Malonyloxymanoyl oxide)

Structure for NP0076079 ((+)-6alpha-Malonyloxymanoyl oxide)

3D Structure for NP0076079 ((+)-6alpha-Malonyloxymanoyl oxide)