NP-MRD: Showing NP-Card for Metternichiamide C (NP0332911)

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Record Information

Version

2.0

Created at

2024-05-02 01:55:08 UTC

Updated at

2026-02-15 04:17:46 UTC

NP-MRD ID

NP0332911

Natural Product DOI

https://doi.org/10.57994/2192

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Metternichiamide C

Description

Metternichiamide C belongs to the class of organic compounds known as 7,7'-epoxylignans. These are lignans with a structure based on a 2,5-diaryl-3, 4-dimethyltetrahydrofuran skeleton. Metternichiamide C was first documented in 2024 (PMID: 39619525). Based on a literature review very few articles have been published on Metternichiamide C.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01142304312D          

 52 56  0  0  1  0            999 V2000
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4760   -4.1974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -4.9820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2460   -5.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5815   -6.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0966   -7.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4322   -7.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9473   -8.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2761   -6.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088   -7.6518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0594   -6.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8799   -6.1445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2155   -5.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4255   -5.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -4.9820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0408   -5.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8613   -5.5632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3462   -6.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -6.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6516   -6.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4721   -6.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9570   -7.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6215   -8.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1064   -8.8142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8010   -8.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3161   -7.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7053   -6.4032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109   -4.1974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5955   -3.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7670   -3.1355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5516   -2.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7231   -2.0736    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1101   -1.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5078   -1.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6793   -1.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4639   -0.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0770   -1.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8616   -1.0538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9055   -2.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1209   -2.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2086   -4.4945    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
  3  6  2  0  0  0  0
  2  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  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
 17 20  2  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
 22 25  2  0  0  0  0
 15 25  1  0  0  0  0
 26 14  1  0  0  0  0
 26 27  1  6  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  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 31 37  1  0  0  0  0
 27 38  2  0  0  0  0
 26 39  1  0  0  0  0
 39 12  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 43 42  1  0  0  0  0
 43 44  1  1  0  0  0
 43 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  2  0  0  0  0
 45 51  1  0  0  0  0
 40 52  2  0  0  0  0
M  END


  Mrv2104 01142304312D          

 52 56  0  0  1  0            999 V2000
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4760   -4.1974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -4.9820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2460   -5.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5815   -6.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0966   -7.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4322   -7.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9473   -8.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2761   -6.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088   -7.6518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0594   -6.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8799   -6.1445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2155   -5.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4255   -5.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -4.9820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0408   -5.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8613   -5.5632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3462   -6.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -6.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6516   -6.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4721   -6.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9570   -7.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6215   -8.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1064   -8.8142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8010   -8.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3161   -7.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7053   -6.4032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109   -4.1974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5955   -3.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7670   -3.1355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5516   -2.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7231   -2.0736    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1101   -1.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5078   -1.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6793   -1.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4639   -0.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0770   -1.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8616   -1.0538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9055   -2.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1209   -2.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2086   -4.4945    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
  3  6  2  0  0  0  0
  2  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  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
 17 20  2  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
 22 25  2  0  0  0  0
 15 25  1  0  0  0  0
 26 14  1  0  0  0  0
 26 27  1  6  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  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 31 37  1  0  0  0  0
 27 38  2  0  0  0  0
 26 39  1  0  0  0  0
 39 12  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 43 42  1  0  0  0  0
 43 44  1  1  0  0  0
 43 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  2  0  0  0  0
 45 51  1  0  0  0  0
 40 52  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332911

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1O)[C@H]1O[C@@H]([C@H]([C@@H]1C(=O)NCCC1=CC=C(O)C=C1)C(=O)NC[C@@H](O)C1=CC=C(O)C=C1)C1=CC(OC)=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C38H42N2O12/c1-48-27-15-22(16-28(49-2)33(27)44)35-31(37(46)39-14-13-20-5-9-24(41)10-6-20)32(38(47)40-19-26(43)21-7-11-25(42)12-8-21)36(52-35)23-17-29(50-3)34(45)30(18-23)51-4/h5-12,15-18,26,31-32,35-36,41-45H,13-14,19H2,1-4H3,(H,39,46)(H,40,47)/t26-,31+,32+,35-,36-/m1/s1

> <INCHI_KEY>
HYOZJKFEERABJM-DHYSXTDBSA-N

> <FORMULA>
C38H42N2O12

> <MOLECULAR_WEIGHT>
718.756

> <EXACT_MASS>
718.2737748

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
74.61651020323615

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5S)-N3-[(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)-N4-[2-(4-hydroxyphenyl)ethyl]oxolane-3,4-dicarboxamide

> <JCHEM_LOGP>
2.951924275333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.215786173381781

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.783317161021602

> <JCHEM_PKA_STRONGEST_BASIC>
-2.239916430859136

> <JCHEM_POLAR_SURFACE_AREA>
205.5

> <JCHEM_REFRACTIVITY>
188.4478

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5S)-N3-[(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)-N4-[2-(4-hydroxyphenyl)ethyl]oxolane-3,4-dicarboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-JAN-23         0                                  
HETATM    1  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.755  -7.835   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.231  -9.300   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.326 -10.546   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.952 -11.953   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.047 -13.198   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.673 -14.605   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.768 -15.851   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.515 -13.037   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.390 -14.283   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.111 -11.631   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.642 -11.470   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.269 -10.063   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.794 -10.385   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.771  -9.300   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.676 -10.546   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       7.208 -10.385   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       8.113 -11.631   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.645 -11.470   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.550 -12.716   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.081 -12.555   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.986 -13.800   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.360 -15.207   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      13.265 -16.453   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.829 -15.368   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.923 -14.122   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.050 -11.953   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.247  -7.835   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.712  -7.359   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0       7.032  -5.853   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0       8.496  -5.377   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.817  -3.871   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       7.672  -2.840   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      10.281  -3.395   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      10.601  -1.888   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      12.066  -1.413   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      13.210  -2.443   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      14.675  -1.967   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      12.890  -3.949   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      11.426  -4.425   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       7.856  -8.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3   11                                                       
CONECT    7    2    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13   39                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   26                                                  
CONECT   15   14   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   15                                                       
CONECT   26   14   27   39                                                  
CONECT   27   26   28   38                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   31                                                       
CONECT   38   27                                                            
CONECT   39   26   12   40                                                  
CONECT   40   39   41   52                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46   51                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51                                                       
CONECT   51   50   45                                                       
CONECT   52   40                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  112    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₈H₄₂N₂O₁₂

Average Mass

718.7560 Da

Monoisotopic Mass

718.27377 Da

IUPAC Name

(2S,3S,4S,5S)-N3-[(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)-N4-[2-(4-hydroxyphenyl)ethyl]oxolane-3,4-dicarboxamide

Traditional Name

(2S,3S,4S,5S)-N3-[(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)-N4-[2-(4-hydroxyphenyl)ethyl]oxolane-3,4-dicarboxamide

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1O)[C@H]1O[C@@H]([C@H]([C@@H]1C(=O)NCCC1=CC=C(O)C=C1)C(=O)NC[C@@H](O)C1=CC=C(O)C=C1)C1=CC(OC)=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C38H42N2O12/c1-48-27-15-22(16-28(49-2)33(27)44)35-31(37(46)39-14-13-20-5-9-24(41)10-6-20)32(38(47)40-19-26(43)21-7-11-25(42)12-8-21)36(52-35)23-17-29(50-3)34(45)30(18-23)51-4/h5-12,15-18,26,31-32,35-36,41-45H,13-14,19H2,1-4H3,(H,39,46)(H,40,47)/t26-,31+,32+,35-,36-/m1/s1

InChI Key

HYOZJKFEERABJM-DHYSXTDBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	thiagobrito@ltf.ufpb.br	UFPB	Thiago Araújo de Medeiros Brito	2024-05-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	thiagobrito@ltf.ufpb.br	UFPB	Thiago Araújo de Medeiros Brito	2024-05-02	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	thiagobrito@ltf.ufpb.br	UFPB	Thiago Araújo de Medeiros Brito	2024-05-02	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	thiagobrito@ltf.ufpb.br	UFPB	Thiago Araújo de Medeiros Brito	2024-05-02	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	thiagobrito@ltf.ufpb.br	UFPB	Thiago Araújo de Medeiros Brito	2024-05-02	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	thiagobrito@ltf.ufpb.br	UFPB	Thiago Araújo de Medeiros Brito	2024-05-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	thiagobrito@ltf.ufpb.br	UFPB	Thiago Araújo de Medeiros Brito	2024-05-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	thiagobrito@ltf.ufpb.br	UFPB	Thiago Araújo de Medeiros Brito	2024-05-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	thiagobrito@ltf.ufpb.br	UFPB	Thiago Araújo de Medeiros Brito	2024-05-02	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400.0, Methanol-d4, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.0, Methanol-d4, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-15	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Metternichia macrocalyx		Not Available
Metternichia macrocalyx		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as 7,7'-epoxylignans. These are lignans with a structure based on a 2,5-diaryl-3, 4-dimethyltetrahydrofuran skeleton.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

7,7'-epoxylignans

Alternative Parents

Substituents

7,7p-epoxylignan
Dibenzylbutane lignan skeleton
Methoxyphenol
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Fatty acyl
Benzenoid
N-acyl-amine
Fatty amide
Monocyclic benzene moiety
Tetrahydrofuran
Secondary alcohol
Carboxamide group
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.95	ChemAxon
pKa (Strongest Acidic)	8.78	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	205.5 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	188.45 m³·mol⁻¹	ChemAxon
Polarizability	74.62 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

Brito TAM, de Albuquerque ACF, Dos Santos Junior FM, Loureiro PBA, Gadelha FAAF, Sobral MV, Cardoso DBOS, Velozo EDS, Tavares JF, Abreu LS, Silva MSD: Lignanamides from the Roots of Metternichia macrocalyx and Their Anti-inflammatory Activity. ACS Omega. 2024 Nov 13;9(47):47065-47076. doi: 10.1021/acsomega.4c07336. eCollection 2024 Nov 26. [PubMed:39619525 ]
DOI: 10.1021/acsomega.4c07336
PMID: 39619525

Showing NP-Card for Metternichiamide C (NP0332911)

MOL for NP0332911 (Metternichiamide C)

3D MOL for NP0332911 (Metternichiamide C)

3D SDF for NP0332911 (Metternichiamide C)

3D-SDF for NP0332911 (Metternichiamide C)

PDB for NP0332911 (Metternichiamide C)

3D PDB for NP0332911 (Metternichiamide C)

SMILES for NP0332911 (Metternichiamide C)

INCHI for NP0332911 (Metternichiamide C)

Structure for NP0332911 (Metternichiamide C)

3D Structure for NP0332911 (Metternichiamide C)