NP-MRD: Showing NP-Card for methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate (NP0260458)

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Record Information

Version

2.0

Created at

2022-09-08 02:38:21 UTC

Updated at

2022-09-08 02:38:21 UTC

NP-MRD ID

NP0260458

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

Description

Methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate is found in Platycodon grandiflorus. Methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201505422D          

 60 66  0  0  0  0            999 V2000
   -0.5230   -6.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -3.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -3.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -2.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145   -1.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -1.6796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.9651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -0.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -0.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    0.4638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    0.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.1783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    0.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.1783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -0.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145   -0.2507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5520   -2.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645   -1.6796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645   -3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7895   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8522   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9955   -6.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9337   -6.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5657   -6.5947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6907   -6.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -6.7869    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 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
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 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  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 29 38  1  0  0  0  0
 38 39  1  0  0  0  0
 26 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 24 44  1  0  0  0  0
 44 45  1  0  0  0  0
 22 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 46 49  1  0  0  0  0
 49 50  1  0  0  0  0
 46 51  1  0  0  0  0
 17 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 16 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
 13 56  1  0  0  0  0
 56 57  1  0  0  0  0
 56 58  1  0  0  0  0
 58 59  1  0  0  0  0
  5 59  1  0  0  0  0
 59 60  1  0  0  0  0
M  END

     RDKit          3D

130136  0  0  0  0  0  0  0  0999 V2000
   -8.9606   -0.2158   -3.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5082    0.1474   -2.5394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7413   -0.6758   -1.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3953   -1.8014   -2.1424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3197   -0.2095   -0.4128 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.6482   -0.0538    0.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0990   -1.4276    0.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1636   -1.8107    1.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0878   -3.2871    2.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7455   -1.2022    3.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8006   -1.1837    1.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3895   -1.1063    0.3096 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9585   -0.6691    0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0149   -1.4501    0.8243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5664   -1.1035    0.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2237   -0.6521   -0.5883 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.4105   -0.4387   -2.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.5243   -3.8131   -0.1132 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.3467   -1.3750    2.4515 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1705    2.9541   -0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.4653    0.6137    1.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.1251   -1.3553    1.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.0952   -1.5095    4.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7366   -1.6755    3.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8220   -0.1002    3.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.5423   -2.1459   -0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3973   -2.3792    1.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2415   -0.4266    1.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2095   -1.6635   -1.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1999    0.4991   -2.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4139   -1.2063   -2.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2306   -0.9077   -2.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0065   -2.1282   -0.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
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 60130  1  0
M  END


  Mrv1533004201505422D          

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M  END
> <DATABASE_ID>
NP0260458

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C12CCC(C)(C)CC1C1=CCC3C4(C)CC(O)C(OC5OC(COC6OC(CO)C(O)C(O)C6O)C(O)C(O)C5O)C(CO)(CO)C4CCC3(C)C1(C)CC2O

> <INCHI_IDENTIFIER>
InChI=1S/C43H70O17/c1-38(2)11-12-43(37(55)56-6)21(13-38)20-7-8-25-39(3)14-22(47)34(42(18-45,19-46)26(39)9-10-40(25,4)41(20,5)15-27(43)48)60-36-33(54)31(52)29(50)24(59-36)17-57-35-32(53)30(51)28(49)23(16-44)58-35/h7,21-36,44-54H,8-19H2,1-6H3

> <INCHI_KEY>
RCKVJQIKSTUOAC-UHFFFAOYSA-N

> <FORMULA>
C43H70O17

> <MOLECULAR_WEIGHT>
859.016

> <EXACT_MASS>
858.461300794

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
130

> <JCHEM_AVERAGE_POLARIZABILITY>
91.79822892199026

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

> <ALOGPS_LOGP>
0.30

> <JCHEM_LOGP>
-1.6682007893333317

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.425869600539471

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.907524084444121

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0581178102376168

> <JCHEM_POLAR_SURFACE_AREA>
285.75

> <JCHEM_REFRACTIVITY>
209.6466000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -0.976 -12.471   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.206 -11.137   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334 -11.137   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.104 -12.471   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.883  -6.610   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.831  -5.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.114  -5.803   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.654  -8.470   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.424  -7.136   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.654  -5.803   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      14.424  -4.469   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.654  -3.135   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.114  -3.135   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.344  -1.802   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.804  -1.802   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.034  -0.468   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.494  -0.468   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.724   0.866   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.804   0.866   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.034   2.199   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.344   0.866   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      12.114   2.199   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      12.114  -0.468   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      13.654  -0.468   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      15.964  -4.469   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      16.734  -3.135   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      16.734  -5.803   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      18.274  -5.803   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      15.964  -7.136   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      16.734  -8.470   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      12.791 -10.330   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      13.058 -11.847   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      11.076 -11.320   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      12.256 -12.310   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       5.023 -11.335   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0       3.035 -12.669   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12   59                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11    5   13                                                  
CONECT   13   12   14   56                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   54                                                  
CONECT   17   16   18   19   51                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   46                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   44                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   40                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   38                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   29   39                                                  
CONECT   39   38                                                            
CONECT   40   26   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   24   45                                                  
CONECT   45   44                                                            
CONECT   46   22   47   49   51                                             
CONECT   47   46   48                                                       
CONECT   48   47                                                            
CONECT   49   46   50                                                       
CONECT   50   49                                                            
CONECT   51   46   17   52                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   16   55   56                                             
CONECT   55   54                                                            
CONECT   56   54   13   57   58                                             
CONECT   57   56                                                            
CONECT   58   56   59                                                       
CONECT   59   58    5   60                                                  
CONECT   60   59                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  132    0
END

View in JSmol

Synonyms

Value	Source
Methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid	Generator

Chemical Formula

C₄₃H₇₀O₁₇

Average Mass

859.0160 Da

Monoisotopic Mass

858.46130 Da

IUPAC Name

methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C12CCC(C)(C)CC1C1=CCC3C4(C)CC(O)C(OC5OC(COC6OC(CO)C(O)C(O)C6O)C(O)C(O)C5O)C(CO)(CO)C4CCC3(C)C1(C)CC2O

InChI Identifier

InChI=1S/C43H70O17/c1-38(2)11-12-43(37(55)56-6)21(13-38)20-7-8-25-39(3)14-22(47)34(42(18-45,19-46)26(39)9-10-40(25,4)41(20,5)15-27(43)48)60-36-33(54)31(52)29(50)24(59-36)17-57-35-32(53)30(51)28(49)23(16-44)58-35/h7,21-36,44-54H,8-19H2,1-6H3

InChI Key

RCKVJQIKSTUOAC-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
Platycodon grandiflorus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protoberberine alkaloids and derivatives

Sub Class

Not Available

Direct Parent

Protoberberine alkaloids and derivatives

Alternative Parents

Substituents

Protoberberine skeleton
Tetrahydroprotoberberine skeleton
Tetrahydroisoquinoline
Anisole
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Ether
Azacycle
Polyol
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxygen 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	0.3	ALOGPS
logP	-1.7	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	285.75 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	209.65 m³·mol⁻¹	ChemAxon
Polarizability	91.8 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate (NP0260458)

MOL for NP0260458 (methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

3D MOL for NP0260458 (methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

3D SDF for NP0260458 (methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

3D-SDF for NP0260458 (methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

PDB for NP0260458 (methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

3D PDB for NP0260458 (methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

SMILES for NP0260458 (methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

INCHI for NP0260458 (methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

Structure for NP0260458 (methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

3D Structure for NP0260458 (methyl 5,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6a,6b,12a-pentamethyl-10-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)