NP-MRD: Showing NP-Card for methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-1(24),5-dien-23-ylidene}propanoate (NP0243781)

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Record Information

Version

2.0

Created at

2022-09-07 04:24:28 UTC

Updated at

2022-09-07 04:24:28 UTC

NP-MRD ID

NP0243781

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-1(24),5-dien-23-ylidene}propanoate

Description

Methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]Tetracosa-1(24),5-dien-23-ylidene}propanoate belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-1(24),5-dien-23-ylidene}propanoate is found in Chloranthus spicatus. Methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]Tetracosa-1(24),5-dien-23-ylidene}propanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171515222D          

 44 51  0  0  0  0            999 V2000
    3.2798   -7.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4289   -6.3945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8007   -5.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0235   -6.1363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9602   -4.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3557   -4.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429   -4.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8515   -4.8996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0142   -3.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1690   -3.7453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2984   -2.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4605   -2.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0614   -1.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0060   -1.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7466   -1.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3954   -1.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082   -1.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7369   -2.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497   -2.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5533   -1.4676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9887   -1.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5633   -1.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7887   -1.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8441   -2.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6155   -3.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3713   -2.6868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7962   -2.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4551   -1.0252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0622   -0.2446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9412   -4.9189    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 24 30  1  0  0  0  0
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 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 18 39  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  0  0  0  0
  6 40  1  0  0  0  0
 40 41  2  0  0  0  0
 11 41  1  0  0  0  0
 16 41  1  0  0  0  0
 16 42  1  0  0  0  0
 42 43  1  0  0  0  0
  5 44  1  4  0  0  0
M  END

     RDKit          3D

 82 89  0  0  0  0  0  0  0  0999 V2000
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    3.8684    1.4162    2.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7935    0.6649    0.8736 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.7596    2.7108    0.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1742    1.2281    1.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6067    2.1372   -1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1910    4.7564    1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5598    4.5039   -1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8040    3.6142   -3.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5375    1.8432   -2.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
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 25 61  1  6
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 24 60  1  0
 21 56  1  0
 21 57  1  0
 22 58  1  0
 41 78  1  0
M  END


  Mrv1533004171515222D          

 44 51  0  0  0  0            999 V2000
    3.2798   -7.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4289   -6.3945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8007   -5.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0235   -6.1363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9602   -4.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3557   -4.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429   -4.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8515   -4.8996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0142   -3.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1690   -3.7453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2984   -2.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4605   -2.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0614   -1.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0060   -1.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7466   -1.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3954   -1.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082   -1.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7369   -2.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497   -2.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5533   -1.4676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9887   -1.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5633   -1.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7887   -1.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8441   -2.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6155   -3.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3713   -2.6868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0525   -3.1523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7962   -2.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9899   -3.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0784   -2.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7942   -3.7359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9814   -3.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4262   -4.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7524   -5.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5311   -5.9827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7424   -4.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1454   -5.0755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765   -3.6670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4527   -3.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6399   -3.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1112   -2.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4551   -1.0252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0622   -0.2446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9412   -4.9189    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  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
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 24 30  1  0  0  0  0
 19 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 18 39  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  0  0  0  0
  6 40  1  0  0  0  0
 40 41  2  0  0  0  0
 11 41  1  0  0  0  0
 16 41  1  0  0  0  0
 16 42  1  0  0  0  0
 42 43  1  0  0  0  0
  5 44  1  4  0  0  0
M  END
> <DATABASE_ID>
NP0243781

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(C)=C1C(=O)C(O)C2(C)C3CC3C3(CC4C5(C)C6CC6C(COC(C)=O)C5CC5=C(CO)C(=O)OC45C1=C23)OO

> <INCHI_IDENTIFIER>
InChI=1S/C33H38O11/c1-12(28(38)41-5)23-24-26-31(4,27(37)25(23)36)20-8-21(20)32(26,44-40)9-22-30(3)17-6-14(17)16(11-42-13(2)35)18(30)7-19-15(10-34)29(39)43-33(19,22)24/h14,16-18,20-22,27,34,37,40H,6-11H2,1-5H3

> <INCHI_KEY>
VCRQYSYGSKXUQD-UHFFFAOYSA-N

> <FORMULA>
C33H38O11

> <MOLECULAR_WEIGHT>
610.656

> <EXACT_MASS>
610.241412044

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
62.58227645278533

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-1(24),5-dien-23-ylidene}propanoate

> <ALOGPS_LOGP>
1.75

> <JCHEM_LOGP>
0.7617622163333319

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.887654091106974

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.666058815019575

> <JCHEM_PKA_STRONGEST_BASIC>
-2.860928783672441

> <JCHEM_POLAR_SURFACE_AREA>
165.89

> <JCHEM_REFRACTIVITY>
151.4434

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-1(24),5-dien-23-ylidene}propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       6.122 -13.451   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.401 -11.936   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.228 -10.938   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.777 -11.454   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.526  -9.318   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.397  -7.764   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.880  -8.028   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.589  -9.146   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.893  -6.846   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.316  -6.991   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.424  -5.400   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.860  -4.800   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.981  -3.597   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.878  -2.061   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.260  -2.739   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.471  -3.690   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.989  -3.427   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.976  -4.609   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.493  -4.346   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.500  -2.740   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.312  -3.042   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.385  -1.937   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.806  -3.418   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.909  -4.955   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.349  -5.693   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      13.760  -5.015   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      15.031  -5.884   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.420  -5.218   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.915  -7.420   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.480  -5.528   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.949  -6.974   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.432  -7.237   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.396  -8.522   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.004 -10.302   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.458 -11.168   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.119  -8.165   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.005  -9.474   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       4.996  -6.845   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       6.445  -6.055   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.928  -6.318   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.941  -5.136   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       4.583  -1.914   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       3.849  -0.457   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       7.357  -9.182   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   44                                                  
CONECT    6    5    7   40                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   41                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13   15                                                       
CONECT   15   14   13   16                                                  
CONECT   16   15   17   41   42                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   39                                                  
CONECT   19   18   20   21   30                                             
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21   23                                                       
CONECT   23   22   21   24                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   24   19   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   18   32   40                                             
CONECT   40   39    6   41                                                  
CONECT   41   40   11   16                                                  
CONECT   42   16   43                                                       
CONECT   43   42                                                            
CONECT   44    5                                                            
MASTER        0    0    0    0    0    0    0    0   44    0  102    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0,.0,.0,.0,.0,.0,]tetracosa-1(24),5-dien-23-ylidene}propanoic acid	Generator
Methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-1(24),5-dien-23-ylidene}propanoic acid	Generator

Chemical Formula

C₃₃H₃₈O₁₁

Average Mass

610.6560 Da

Monoisotopic Mass

610.24141 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C(C)=C1C(=O)C(O)C2(C)C3CC3C3(CC4C5(C)C6CC6C(COC(C)=O)C5CC5=C(CO)C(=O)OC45C1=C23)OO

InChI Identifier

InChI=1S/C33H38O11/c1-12(28(38)41-5)23-24-26-31(4,27(37)25(23)36)20-8-21(20)32(26,44-40)9-22-30(3)17-6-14(17)16(11-42-13(2)35)18(30)7-19-15(10-34)29(39)43-33(19,22)24/h14,16-18,20-22,27,34,37,40H,6-11H2,1-5H3

InChI Key

VCRQYSYGSKXUQD-UHFFFAOYSA-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
Chloranthus spicatus	LOTUS Database	35616633

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

Triterpenoid
Steroid ester
Naphthofuran
Tricarboxylic acid or derivatives
Cyclohexenone
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Ketone
Lactone
Hydroperoxide
Secondary alcohol
Cyclic ketone
Peroxol
Alkyl hydroperoxide
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Primary alcohol
Hydrocarbon derivative
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	1.75	ALOGPS
logP	0.76	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	11.67	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	165.89 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	151.44 m³·mol⁻¹	ChemAxon
Polarizability	62.58 Å³	ChemAxon
Number of Rings	8	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

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References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-1(24),5-dien-23-ylidene}propanoate (NP0243781)

MOL for NP0243781 (methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-1(24),5-dien-23-ylidene}propanoate)

3D MOL for NP0243781 (methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-1(24),5-dien-23-ylidene}propanoate)

3D SDF for NP0243781 (methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-1(24),5-dien-23-ylidene}propanoate)

3D-SDF for NP0243781 (methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-1(24),5-dien-23-ylidene}propanoate)

PDB for NP0243781 (methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-1(24),5-dien-23-ylidene}propanoate)

3D PDB for NP0243781 (methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-1(24),5-dien-23-ylidene}propanoate)

SMILES for NP0243781 (methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-1(24),5-dien-23-ylidene}propanoate)

INCHI for NP0243781 (methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-1(24),5-dien-23-ylidene}propanoate)

Structure for NP0243781 (methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-1(24),5-dien-23-ylidene}propanoate)

3D Structure for NP0243781 (methyl 2-{9-[(acetyloxy)methyl]-16-hydroperoxy-21-hydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-1(24),5-dien-23-ylidene}propanoate)