NP-MRD: Showing NP-Card for 9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate (NP0142030)

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Record Information

Version

2.0

Created at

2022-09-01 20:28:56 UTC

Updated at

2022-09-01 20:28:56 UTC

NP-MRD ID

NP0142030

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate

Description

9-Methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. 9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate is found in Ixeris repens. 9-Methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241507182D          

 42 46  0  0  0  0            999 V2000
    1.6592    0.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9491    0.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7444    1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7814    1.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0090    2.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4946    1.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6696    1.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2151    0.8690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802    1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2252    0.5741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    1.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057    2.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1552    2.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3388    3.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821    3.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8254    3.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4704    3.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    3.5213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833    4.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847    4.6385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8283    4.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5962    4.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7053    5.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1183    5.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7633    6.3946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6403    7.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2854    7.7247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8724    7.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274    6.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3894    0.5741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2664   -0.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4984   -0.5430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755   -1.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6075   -1.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9625   -1.1459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0205   -1.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8975   -2.6890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7885   -1.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4335   -2.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9114   -0.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6794   -0.4546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  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
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 24 30  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 32 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END

     RDKit          3D

 80 84  0  0  0  0  0  0  0  0999 V2000
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    1.9517   -0.8026    0.3884 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3217   -0.7115    0.6056 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2892   -1.2226   -0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8744   -1.8051   -1.2713 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7104   -1.0680    0.1053 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4785   -1.7473   -0.8793 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2191    0.3360    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6770    0.2538    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9961    0.3199    1.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3127    0.2518    2.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3294    0.1140    1.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4040   -0.5340   -0.7668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3575    0.3020   -0.1896 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9779    1.0554   -1.1432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0834    1.7720   -0.7827 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6832    2.8684    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7630    3.6790   -0.4983 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.3329    1.0219   -0.6716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6588   -0.5583   -0.1827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5899   -0.9325   -1.5191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3241   -0.6003    0.5103 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5777   -0.1567    1.8311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1163   -0.0376   -1.4047 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2925   -0.7324   -2.7108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8001   -3.1643    1.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4525   -2.3924   -0.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4263   -1.8278   -2.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0636   -0.2741   -3.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
 42 41  1  0
 41 28  1  0
 28 27  1  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 21  1  0
 21 22  2  0
 21 19  1  0
 19 20  2  3
 19 18  1  0
 18  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
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  6  7  2  0
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 34 70  1  0
 35 71  1  1
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 37 73  1  1
 38 74  1  0
 39 75  1  1
 40 76  1  0
M  END


  Mrv1533004241507182D          

 42 46  0  0  0  0            999 V2000
    1.6592    0.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9491    0.8690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6696    1.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2252    0.5741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1833    4.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847    4.6385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8283    4.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5962    4.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7053    5.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3503    6.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1183    5.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7633    6.3946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6403    7.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2854    7.7247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8724    7.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274    6.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3894    0.5741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2664   -0.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4984   -0.5430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755   -1.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6075   -1.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9625   -1.1459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0205   -1.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8975   -2.6890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7885   -1.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4335   -2.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9114   -0.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6794   -0.4546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  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
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 24 30  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 32 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0142030

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(CC2C1C1OC(=O)C(=C)C1C(CC2=C)OC(=O)C(O)CC1=CC=C(O)C=C1)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O12/c1-12-8-20(39-29(38)18(33)9-15-4-6-16(32)7-5-15)23-14(3)28(37)42-27(23)22-13(2)19(10-17(12)22)40-30-26(36)25(35)24(34)21(11-31)41-30/h4-7,13,17-27,30-36H,1,3,8-11H2,2H3

> <INCHI_KEY>
ADEUTDBYJNLORF-UHFFFAOYSA-N

> <FORMULA>
C30H38O12

> <MOLECULAR_WEIGHT>
590.622

> <EXACT_MASS>
590.236326664

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
60.7789833772314

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate

> <ALOGPS_LOGP>
0.18

> <JCHEM_LOGP>
0.5435414383333337

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.08259943640441

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.50191491576299

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083542786669

> <JCHEM_POLAR_SURFACE_AREA>
192.43999999999997

> <JCHEM_REFRACTIVITY>
143.71790000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3aH-azuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       3.097   0.180   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.638   1.622   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.123   2.032   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.192   3.570   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.750   4.111   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.790   2.907   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.250   2.907   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.402   1.622   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.083   2.032   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.287   1.072   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.152   3.570   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.437   4.419   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.290   4.111   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.632   5.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.020   6.281   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.407   5.613   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.611   6.573   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.572   6.573   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.342   8.096   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.091   8.658   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.546   9.056   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.980   8.493   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.317  10.579   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.521  11.539   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.954  10.976   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.158  11.937   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.929  13.459   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -6.133  14.420   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.495  14.022   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.291  13.062   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.327   1.072   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.097  -0.451   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.664  -1.014   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.434  -2.536   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.001  -3.099   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.797  -2.139   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.638  -3.497   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.409  -5.019   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       7.072  -2.934   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       8.276  -3.894   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       7.301  -1.411   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       8.735  -0.849   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7   14                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15    5   17                                                  
CONECT   17   16                                                            
CONECT   18   14   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   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   30                                                       
CONECT   30   29   24                                                       
CONECT   31    3   32                                                       
CONECT   32   31   33   41                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   34   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   32   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
9-Methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoic acid	Generator

Chemical Formula

C₃₀H₃₈O₁₂

Average Mass

590.6220 Da

Monoisotopic Mass

590.23633 Da

IUPAC Name

9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate

Traditional Name

9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3aH-azuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate

CAS Registry Number

Not Available

SMILES

CC1C(CC2C1C1OC(=O)C(=C)C1C(CC2=C)OC(=O)C(O)CC1=CC=C(O)C=C1)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C30H38O12/c1-12-8-20(39-29(38)18(33)9-15-4-6-16(32)7-5-15)23-14(3)28(37)42-27(23)22-13(2)19(10-17(12)22)40-30-26(36)25(35)24(34)21(11-31)41-30/h4-7,13,17-27,30-36H,1,3,8-11H2,2H3

InChI Key

ADEUTDBYJNLORF-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
Ixeris repens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Terpene glycoside
Guaiane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Monosaccharide
Oxane
Benzenoid
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Oxacycle
Polyol
Organooxygen compound
Alcohol
Organic oxygen compound
Primary alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	0.18	ALOGPS
logP	0.54	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	143.72 m³·mol⁻¹	ChemAxon
Polarizability	60.78 Å³	ChemAxon
Number of Rings	5	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 9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate (NP0142030)

MOL for NP0142030 (9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate)

3D MOL for NP0142030 (9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate)

3D SDF for NP0142030 (9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate)

3D-SDF for NP0142030 (9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate)

PDB for NP0142030 (9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate)

3D PDB for NP0142030 (9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate)

SMILES for NP0142030 (9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate)

INCHI for NP0142030 (9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate)

Structure for NP0142030 (9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate)

3D Structure for NP0142030 (9-methyl-3,6-dimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3ah-azuleno[4,5-b]furan-4-yl 2-hydroxy-3-(4-hydroxyphenyl)propanoate)