NP-MRD: Showing NP-Card for 1,3-bis[(4r,4as,6r,7s,7ar)-2,4,7-trimethyl-octahydrocyclopenta[c]pyridin-6-yl] 2,4-bis(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylate (NP0286448)

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Record Information

Version

1.0

Created at

2022-09-09 15:02:00 UTC

Updated at

2022-09-09 15:02:00 UTC

NP-MRD ID

NP0286448

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,3-bis[(4r,4as,6r,7s,7ar)-2,4,7-trimethyl-octahydrocyclopenta[c]pyridin-6-yl] 2,4-bis(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylate

Description

Incarvillateine belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 1,3-bis[(4r,4as,6r,7s,7ar)-2,4,7-trimethyl-octahydrocyclopenta[c]pyridin-6-yl] 2,4-bis(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylate is found in Incarvillea sinensis. It was first documented in 2015 (PMID: 26527075). Based on a literature review a significant number of articles have been published on Incarvillateine (PMID: 31242440) (PMID: 31237895) (PMID: 29922083) (PMID: 27022999).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092217022D          

 52 58  0  0  1  0            999 V2000
   -3.4210   -3.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4210   -3.0418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7065   -2.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7065   -1.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921   -1.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921   -0.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5754    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4004    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8129   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8129    0.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6379    0.7310    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1229    0.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9075    0.3185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6219   -0.0940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6219   -0.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3364    0.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1513    2.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9921   -3.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921   -3.8668    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
  4  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  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 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
 20 19  1  1  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  6  0  0  0
  7 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  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  2  0  0  0  0
 24 32  1  0  0  0  0
 23 33  1  0  0  0  0
  6 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 37 36  1  6  0  0  0
 37 38  1  0  0  0  0
 39 38  1  1  0  0  0
 39 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 46 45  1  1  0  0  0
 39 46  1  0  0  0  0
 46 47  1  0  0  0  0
 37 47  1  0  0  0  0
 47 48  1  6  0  0  0
  5 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
  3 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END

     RDKit          3D

110116  0  0  0  0  0  0  0  0999 V2000
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   -5.4724   -0.9980    1.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6265    0.3949    0.9281 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0441    0.9047    1.0341 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7142    0.5320    2.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0576    2.3600    0.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1755    3.1815    1.4639 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7869    4.2777    2.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6361    1.2759    1.6129 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0764    0.3913    2.7302 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6487    0.7695    2.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9832   -2.9340   -0.7368 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.5943   -3.4399   -3.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1209   -3.0270   -4.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3905    2.1625   -0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7568    0.8251   -0.4526 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.1438   -1.2016    2.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3202    1.8115   -1.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9335    1.1699    1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6265    0.3587    0.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8449    2.1299    0.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1239   -0.8786    2.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4594   -0.8465    3.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 11 59  1  1
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 18 69  1  0
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 14 63  1  6
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 15 65  1  0
 15 66  1  0
 21 75  1  1
 22 76  1  0
 22 77  1  0
 22 78  1  0
M  END


  Mrv1652309092217022D          

 52 58  0  0  1  0            999 V2000
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   -3.4004    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8129   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6379    0.7310    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1229    0.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6219   -0.0940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -7.3364    0.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3364    1.1435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9921    0.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7065    1.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7065    2.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921    3.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921    3.8999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776    2.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5631    3.0749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1513    2.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776    1.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776   -1.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776   -2.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921   -3.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921   -3.8668    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
  4  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  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 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
 20 19  1  1  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  6  0  0  0
  7 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  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  2  0  0  0  0
 24 32  1  0  0  0  0
 23 33  1  0  0  0  0
  6 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 37 36  1  6  0  0  0
 37 38  1  0  0  0  0
 39 38  1  1  0  0  0
 39 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 46 45  1  1  0  0  0
 39 46  1  0  0  0  0
 46 47  1  0  0  0  0
 37 47  1  0  0  0  0
 47 48  1  6  0  0  0
  5 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
  3 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286448

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1C(C(C1C(=O)O[C@@H]1C[C@@H]2[C@@H](CN(C)C[C@@H]2C)[C@@H]1C)C1=CC=C(O)C(OC)=C1)C(=O)O[C@@H]1C[C@@H]2[C@@H](CN(C)C[C@@H]2C)[C@@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C42H58N2O8/c1-21-17-43(5)19-29-23(3)33(15-27(21)29)51-41(47)39-37(25-9-11-31(45)35(13-25)49-7)40(38(39)26-10-12-32(46)36(14-26)50-8)42(48)52-34-16-28-22(2)18-44(6)20-30(28)24(34)4/h9-14,21-24,27-30,33-34,37-40,45-46H,15-20H2,1-8H3/t21-,22-,23-,24-,27-,28-,29-,30-,33+,34+,37?,38?,39?,40?/m0/s1

> <INCHI_KEY>
VQKTZIKAARDZIA-ZDYZRSSRSA-N

> <FORMULA>
C42H58N2O8

> <MOLECULAR_WEIGHT>
718.932

> <EXACT_MASS>
718.419316836

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
80.71268304221013

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-bis[(4R,4aS,6R,7S,7aR)-2,4,7-trimethyl-octahydro-1H-cyclopenta[c]pyridin-6-yl] 2,4-bis(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylate

> <JCHEM_LOGP>
4.360578752724076

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
10.122998298041628

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.344794199971815

> <JCHEM_PKA_STRONGEST_BASIC>
10.548993451745622

> <JCHEM_POLAR_SURFACE_AREA>
118.00000000000001

> <JCHEM_REFRACTIVITY>
199.19840000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1,3-bis[(4R,4aS,6R,7S,7aR)-2,4,7-trimethyl-octahydrocyclopenta[c]pyridin-6-yl] 2,4-bis(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.386  -7.218   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.386  -5.678   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.052  -4.908   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.052  -3.368   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.719  -2.598   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.719  -1.058   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.807   0.031   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.347   0.031   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -7.117  -1.303   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -7.117   1.365   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -8.657   1.365   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.563   0.119   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -11.027   0.595   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -12.361  -0.175   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -12.361  -1.715   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -13.695   0.595   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0     -13.695   2.135   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0     -15.028   2.905   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -12.361   2.905   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -11.027   2.135   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -9.563   2.610   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.087   4.075   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.719   1.120   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.719   2.660   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.052   3.430   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.052   4.970   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.719   5.740   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.719   7.280   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.385   4.970   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.051   5.740   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.283   4.970   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.385   3.430   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.320   1.365   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0       6.258  -2.073   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -2.385  -3.368   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -2.385  -4.908   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -3.719  -5.678   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -3.719  -7.218   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   51                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   49                                                  
CONECT    6    5    7   33                                                  
CONECT    7    6    8   23                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   13   21                                                  
CONECT   21   20   11   22                                                  
CONECT   22   21                                                            
CONECT   23    7   24   33                                                  
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   24                                                       
CONECT   33   23    6   34                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38   47                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   46                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45   39   47                                                  
CONECT   47   46   37   48                                                  
CONECT   48   47                                                            
CONECT   49    5   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50    3   52                                                  
CONECT   52   51                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  116    0
END

View in JSmol

Synonyms

Value	Source
7-Epi-incarvilline	MeSH
Incarvilline	MeSH

Chemical Formula

C₄₂H₅₈N₂O₈

Average Mass

718.9320 Da

Monoisotopic Mass

718.41932 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1C(C(C1C(=O)O[C@@H]1C[C@@H]2[C@@H](CN(C)C[C@@H]2C)[C@@H]1C)C1=CC=C(O)C(OC)=C1)C(=O)O[C@@H]1C[C@@H]2[C@@H](CN(C)C[C@@H]2C)[C@@H]1C

InChI Identifier

InChI=1S/C42H58N2O8/c1-21-17-43(5)19-29-23(3)33(15-27(21)29)51-41(47)39-37(25-9-11-31(45)35(13-25)49-7)40(38(39)26-10-12-32(46)36(14-26)50-8)42(48)52-34-16-28-22(2)18-44(6)20-30(28)24(34)4/h9-14,21-24,27-30,33-34,37-40,45-46H,15-20H2,1-8H3/t21-,22-,23-,24-,27-,28-,29-,30-,33+,34+,37?,38?,39?,40?/m0/s1

InChI Key

VQKTZIKAARDZIA-ZDYZRSSRSA-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
Incarvillea sinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Piperidine
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Amine
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00031880

Chemspider ID

8050784

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Incarvillateine

METLIN ID

Not Available

PubChem Compound

9875096

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bian X, Zhang Y, Huang B, Wang X, Wang G, Zhu Y, Liu Y, Liang J, Jia Y, Wang K: Natural product incarvillateine aggravates epileptic seizures by inhibiting GABA(A) currents. Eur J Pharmacol. 2019 Sep 5;858:172496. doi: 10.1016/j.ejphar.2019.172496. Epub 2019 Jun 23. [PubMed:31242440 ]
Kim J, Bogdan DM, Elmes MW, Awwa M, Yan S, Che J, Lee G, Deutsch DG, Rizzo RC, Kaczocha M, Ojima I: Incarvillateine produces antinociceptive and motor suppressive effects via adenosine receptor activation. PLoS One. 2019 Jun 25;14(6):e0218619. doi: 10.1371/journal.pone.0218619. eCollection 2019. [PubMed:31237895 ]
Priebe A, Hunke M, Tonello R, Sonawane Y, Berta T, Natarajan A, Bhuvanesh N, Pattabiraman M, Chandra S: Ferulic acid dimer as a non-opioid therapeutic for acute pain. J Pain Res. 2018 Jun 6;11:1075-1085. doi: 10.2147/JPR.S161161. eCollection 2018. [PubMed:29922083 ]
Huang B, Zhang F, Yu G, Song Y, Wang X, Wang M, Gong Z, Su R, Jia Y: Gram Scale Syntheses of (-)-Incarvillateine and Its Analogs. Discovery of Potent Analgesics for Neuropathic Pain. J Med Chem. 2016 Apr 28;59(8):3953-63. doi: 10.1021/acs.jmedchem.6b00132. Epub 2016 Apr 8. [PubMed:27022999 ]
Wang ML, Yu G, Yi SP, Zhang FY, Wang ZT, Huang B, Su RB, Jia YX, Gong ZH: Antinociceptive effects of incarvillateine, a monoterpene alkaloid from Incarvillea sinensis, and possible involvement of the adenosine system. Sci Rep. 2015 Nov 3;5:16107. doi: 10.1038/srep16107. [PubMed:26527075 ]
LOTUS database [Link]

Showing NP-Card for 1,3-bis[(4r,4as,6r,7s,7ar)-2,4,7-trimethyl-octahydrocyclopenta[c]pyridin-6-yl] 2,4-bis(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylate (NP0286448)

MOL for NP0286448 (1,3-bis[(4r,4as,6r,7s,7ar)-2,4,7-trimethyl-octahydrocyclopenta[c]pyridin-6-yl] 2,4-bis(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylate)

3D MOL for NP0286448 (1,3-bis[(4r,4as,6r,7s,7ar)-2,4,7-trimethyl-octahydrocyclopenta[c]pyridin-6-yl] 2,4-bis(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylate)

3D SDF for NP0286448 (1,3-bis[(4r,4as,6r,7s,7ar)-2,4,7-trimethyl-octahydrocyclopenta[c]pyridin-6-yl] 2,4-bis(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylate)

3D-SDF for NP0286448 (1,3-bis[(4r,4as,6r,7s,7ar)-2,4,7-trimethyl-octahydrocyclopenta[c]pyridin-6-yl] 2,4-bis(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylate)

PDB for NP0286448 (1,3-bis[(4r,4as,6r,7s,7ar)-2,4,7-trimethyl-octahydrocyclopenta[c]pyridin-6-yl] 2,4-bis(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylate)

3D PDB for NP0286448 (1,3-bis[(4r,4as,6r,7s,7ar)-2,4,7-trimethyl-octahydrocyclopenta[c]pyridin-6-yl] 2,4-bis(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylate)

SMILES for NP0286448 (1,3-bis[(4r,4as,6r,7s,7ar)-2,4,7-trimethyl-octahydrocyclopenta[c]pyridin-6-yl] 2,4-bis(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylate)

INCHI for NP0286448 (1,3-bis[(4r,4as,6r,7s,7ar)-2,4,7-trimethyl-octahydrocyclopenta[c]pyridin-6-yl] 2,4-bis(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylate)

Structure for NP0286448 (1,3-bis[(4r,4as,6r,7s,7ar)-2,4,7-trimethyl-octahydrocyclopenta[c]pyridin-6-yl] 2,4-bis(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylate)

3D Structure for NP0286448 (1,3-bis[(4r,4as,6r,7s,7ar)-2,4,7-trimethyl-octahydrocyclopenta[c]pyridin-6-yl] 2,4-bis(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylate)