NP-MRD: Showing NP-Card for (+)-Moluccensin A (NP0081645)

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Record Information

Version

2.0

Created at

2022-04-29 02:39:31 UTC

Updated at

2022-04-29 02:39:31 UTC

NP-MRD ID

NP0081645

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Moluccensin A

Description

(1S,2R,5R,6R,13R,14S,15R,17R,18S)-6-(furan-3-yl)-13-hydroxy-18-(2-methoxy-2-oxoethyl)-1,5,15-trimethyl-14-[(2-methylpropanoyl)oxy]-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]Octadec-10-en-17-yl 2-methylpropanoate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. (+)-Moluccensin A is found in Xylocarpus moluccensis . Based on a literature review very few articles have been published on (1S,2R,5R,6R,13R,14S,15R,17R,18S)-6-(furan-3-yl)-13-hydroxy-18-(2-methoxy-2-oxoethyl)-1,5,15-trimethyl-14-[(2-methylpropanoyl)oxy]-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]Octadec-10-en-17-yl 2-methylpropanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204392D          

 46 51  0  0  1  0            999 V2000
    1.8335    0.2589    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7537    0.3672    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8409    1.1993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2679    1.9713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0827    1.7669    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9320    1.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0806    2.5576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2634    0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0766    0.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6035    1.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167    1.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1034    1.8142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7031    0.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1761   -0.1348    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3629    0.0041    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8360   -0.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0228   -0.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7365    0.2819    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4929   -0.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4625   -0.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2567   -1.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2899   -1.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5162   -2.2423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0048   -1.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8385    0.9979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2516    0.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7322    1.1166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4315    1.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0839    1.4537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6912    2.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7988    3.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4099    3.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1320    2.6909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6780    2.6566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0332    3.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    2.9091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9435    4.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4111    4.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0388    1.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0159   -0.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8890   -0.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4156    0.5438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858   -0.7460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3304   -0.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8018   -0.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
  1 18  1  0  0  0  0
  8 18  1  0  0  0  0
 15 19  1  1  0  0  0
 14 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
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 23 24  1  0  0  0  0
 20 24  2  0  0  0  0
  5 25  1  0  0  0  0
  1 25  1  0  0  0  0
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  3 26  1  0  0  0  0
 25 27  1  1  0  0  0
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 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
  5 33  1  1  0  0  0
  4 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
  3 40  1  1  0  0  0
  2 41  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
  1 46  1  1  0  0  0
M  END

     RDKit          3D

 90 95  0  0  0  0  0  0  0  0999 V2000
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   -2.0959   -2.2387    3.7090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6066   -0.9242    3.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7334   -0.7863    4.1871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8299    0.1469    2.9980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6054    0.0307    1.5431 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7425    1.1820    1.0027 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.8235   -2.5228   -1.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9452   -2.1210   -2.1012 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0785   -3.9996   -2.6718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2931   -4.7011   -0.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8422    0.0353    0.7027 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.0135    1.5382    0.5639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5926    1.7707   -0.0671 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4925    3.0958   -0.3559 O   0  0  0  0  0  0  0  0  0  0  0  0
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 46 90  1  0
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 43 88  1  0
M  END


  Mrv1652304292204392D          

 46 51  0  0  1  0            999 V2000
    1.8335    0.2589    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7537    0.3672    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8409    1.1993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2679    1.9713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0827    1.7669    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9320    1.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0806    2.5576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2634    0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0766    0.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6035    1.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167    1.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1034    1.8142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7031    0.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1761   -0.1348    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3629    0.0041    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8360   -0.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0228   -0.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7365    0.2819    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4929   -0.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4625   -0.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2567   -1.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2899   -1.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5162   -2.2423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0048   -1.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8385    0.9979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2516    0.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7322    1.1166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4315    1.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0839    1.4537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6912    2.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7988    3.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4099    3.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1320    2.6909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6780    2.6566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0332    3.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    2.9091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1505    4.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9435    4.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4111    4.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0388    1.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0159   -0.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8890   -0.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4156    0.5438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858   -0.7460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3304   -0.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8018   -0.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
  1 18  1  0  0  0  0
  8 18  1  0  0  0  0
 15 19  1  1  0  0  0
 14 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 24  2  0  0  0  0
  5 25  1  0  0  0  0
  1 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
  5 33  1  1  0  0  0
  4 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
  3 40  1  1  0  0  0
  2 41  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
  1 46  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0081645

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1[C@@]2(C)C[C@@]3(OC(=O)C(C)C)[C@]1(C)[C@H]1CC[C@@]4(C)[C@@H](OC(=O)CC4=C1C(=O)[C@@]3(O)[C@H]2OC(=O)C(C)C)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C35H44O11/c1-17(2)28(39)45-30-32(6)16-34(46-29(40)18(3)4)33(7,22(32)14-23(36)42-8)20-9-11-31(5)21(25(20)26(38)35(30,34)41)13-24(37)44-27(31)19-10-12-43-15-19/h10,12,15,17-18,20,22,27,30,41H,9,11,13-14,16H2,1-8H3/t20-,22-,27-,30-,31+,32+,33+,34+,35+/m0/s1

> <INCHI_KEY>
GAOIOSVEJZALMD-USIMLTPFSA-N

> <FORMULA>
C35H44O11

> <MOLECULAR_WEIGHT>
640.726

> <EXACT_MASS>
640.288362237

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
66.07395110628627

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5R,6R,13R,14S,15R,17R,18S)-6-(furan-3-yl)-13-hydroxy-18-(2-methoxy-2-oxoethyl)-1,5,15-trimethyl-14-[(2-methylpropanoyl)oxy]-8,12-dioxo-7-oxapentacyclo[13.2.1.0^{2,11}.0^{5,10}.0^{13,17}]octadec-10-en-17-yl 2-methylpropanoate

> <ALOGPS_LOGP>
3.52

> <JCHEM_LOGP>
4.190346381666666

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.053308982253782

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8887852672143084

> <JCHEM_POLAR_SURFACE_AREA>
155.64

> <JCHEM_REFRACTIVITY>
160.13460000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5R,6R,13R,14S,15R,17R,18S)-6-(furan-3-yl)-13-hydroxy-18-(2-methoxy-2-oxoethyl)-1,5,15-trimethyl-14-[(2-methylpropanoyl)oxy]-8,12-dioxo-7-oxapentacyclo[13.2.1.0^{2,11}.0^{5,10}.0^{13,17}]octadec-10-en-17-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       3.423   0.483   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.407   0.685   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.570   2.239   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.367   3.680   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.888   3.298   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.473   3.156   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.750   4.774   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.092   1.711   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.610   1.452   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.593   2.637   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.111   2.378   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.393   3.387   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      10.646   0.933   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.662  -0.252   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.144   0.008   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.161  -1.177   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.643  -0.918   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.108   0.526   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.387  -1.580   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.197  -1.696   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.679  -2.113   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.741  -3.651   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.297  -4.186   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.342  -2.977   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.432   1.863   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.336   0.693   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.100   2.084   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.405   3.464   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.623   2.714   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.890   5.073   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.224   5.821   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.232   6.001   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.980   5.023   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       1.266   4.959   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.062   5.945   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.561   5.430   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -0.281   7.569   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.761   8.151   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.767   8.785   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.072   2.727   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -0.030  -0.201   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -1.659  -0.228   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -2.642   1.015   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -2.773  -1.393   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -4.350  -1.201   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       3.363  -1.175   0.000  0.00  0.00           C+0
CONECT    1    2   18   25   46                                             
CONECT    2    1    3   41                                                  
CONECT    3    2    4   26   40                                             
CONECT    4    3    5   34                                                  
CONECT    5    4    6   25   33                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   18                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14    9   16   19                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    1    8                                                  
CONECT   19   15                                                            
CONECT   20   14   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   20                                                       
CONECT   25    5    1   26   27                                             
CONECT   26   25    3                                                       
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    5                                                            
CONECT   34    4   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40    3                                                            
CONECT   41    2   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44                                                            
CONECT   46    1                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  102    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,5R,6R,13R,14S,15R,17R,18S)-6-(Furan-3-yl)-13-hydroxy-18-(2-methoxy-2-oxoethyl)-1,5,15-trimethyl-14-[(2-methylpropanoyl)oxy]-8,12-dioxo-7-oxapentacyclo[13.2.1.0,.0,.0,]octadec-10-en-17-yl 2-methylpropanoic acid	Generator

Chemical Formula

C₃₅H₄₄O₁₁

Average Mass

640.7260 Da

Monoisotopic Mass

640.28836 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1[C@@]2(C)C[C@@]3(OC(=O)C(C)C)[C@]1(C)[C@H]1CC[C@@]4(C)[C@@H](OC(=O)CC4=C1C(=O)[C@@]3(O)[C@H]2OC(=O)C(C)C)C1=COC=C1

InChI Identifier

InChI=1S/C35H44O11/c1-17(2)28(39)45-30-32(6)16-34(46-29(40)18(3)4)33(7,22(32)14-23(36)42-8)20-9-11-31(5)21(25(20)26(38)35(30,34)41)13-24(37)44-27(31)19-10-12-43-15-19/h10,12,15,17-18,20,22,27,30,41H,9,11,13-14,16H2,1-8H3/t20-,22-,27-,30-,31+,32+,33+,34+,35+/m0/s1

InChI Key

GAOIOSVEJZALMD-USIMLTPFSA-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
Xylocarpus moluccensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Mexicanolide
Prostaglandin skeleton
Steroid lactone
Eicosanoid
11-oxosteroid
12-hydroxysteroid
Hydroxysteroid
Oxosteroid
2-oxosteroid
12-alpha-hydroxysteroid
3-oxasteroid
Steroid
Naphthopyran
Tetracarboxylic acid or derivatives
Naphthalene
Delta valerolactone
Delta_valerolactone
Fatty acyl
Oxane
Pyran
Tertiary alcohol
Methyl ester
Cyclic alcohol
Furan
Heteroaromatic compound
Carboxylic acid ester
Lactone
Ketone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.52	ALOGPS
logP	4.19	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	11.05	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	155.64 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	160.13 m³·mol⁻¹	ChemAxon
Polarizability	66.07 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

27024490

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139038154

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Moluccensin A (NP0081645)

MOL for NP0081645 ((+)-Moluccensin A)

3D MOL for NP0081645 ((+)-Moluccensin A)

3D SDF for NP0081645 ((+)-Moluccensin A)

3D-SDF for NP0081645 ((+)-Moluccensin A)

PDB for NP0081645 ((+)-Moluccensin A)

3D PDB for NP0081645 ((+)-Moluccensin A)

SMILES for NP0081645 ((+)-Moluccensin A)

INCHI for NP0081645 ((+)-Moluccensin A)

Structure for NP0081645 ((+)-Moluccensin A)

3D Structure for NP0081645 ((+)-Moluccensin A)