NP-MRD: Showing NP-Card for ethyl (1r,9r)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate (NP0246811)

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Record Information

Version

2.0

Created at

2022-09-07 08:23:50 UTC

Updated at

2022-09-07 08:23:50 UTC

NP-MRD ID

NP0246811

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ethyl (1r,9r)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate

Description

Goupiolone B belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring. ethyl (1r,9r)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate is found in Goupia glabra. ethyl (1r,9r)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate was first documented in 2017 (PMID: 28742264). Based on a literature review very few articles have been published on Goupiolone B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072210232D          

 28 31  0  0  1  0            999 V2000
    0.8393   -2.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6193   -1.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1793   -1.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3992   -0.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1978   -0.3794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    0.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0994    0.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3339    1.4802    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1107    2.1751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1529    1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4191    2.3601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7410    1.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6552    0.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3230   -0.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0764    0.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1622    0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9156    1.1881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4944    1.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5802    2.1571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9603   -0.2645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8969    0.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3638   -0.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4480   -0.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7268    0.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5386    0.8097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1938    1.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4725    2.0690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6181    1.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 13  1  6  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 21 28  1  0  0  0  0
  8 28  1  0  0  0  0
M  END

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
    5.1663   -0.4114    1.7348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4248   -1.7016    1.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0396   -1.4848    1.4411 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4954   -0.5561    0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2742    0.0331   -0.2179 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0700   -0.2772    0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2479   -0.9030    1.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2406   -0.7026    1.3214 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8606   -1.1650    2.4201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7121   -1.3507    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6093   -2.1998    0.0757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0998   -0.9694   -1.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0970   -0.0732   -1.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3438    0.1515   -2.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2505   -0.5602   -3.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2790   -1.4921   -3.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8313   -2.1729   -4.6749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6902   -1.6830   -2.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6825   -2.5685   -1.9846 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867    0.7326   -0.4847 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5426    1.4322    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926    2.7806   -0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7184    3.4867    0.6179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5889    2.8254    1.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6191    3.5249    2.1024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209    1.4750    1.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2875    0.8134    2.5402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4066    0.7745    1.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5975    0.0366    0.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4874    0.3548    2.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9765   -0.5831    2.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6742   -2.4965    2.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7898   -2.0498    0.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6097   -1.6221    2.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3176   -0.9881    3.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1312    0.8694   -2.9748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0800   -0.4017   -4.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5597   -2.8342   -4.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1447   -3.1080   -2.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    1.4086   -0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0501    3.3547   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8643    4.5513    0.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7208    4.5115    1.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0448    1.2384    3.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  1
  8 28  1  0
 28 26  2  0
 26 27  1  0
 26 24  1  0
 24 25  1  0
 24 23  2  0
 23 22  1  0
 22 21  2  0
 21 20  1  0
 20 13  1  0
 13 12  2  0
 12 18  1  0
 18 19  1  0
 18 16  2  0
 16 17  1  0
 16 15  1  0
 15 14  2  0
 12 10  1  0
 10 11  2  0
 20  6  1  0
 14 13  1  0
 10  8  1  0
 21 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  7 34  1  0
  9 35  1  0
 27 44  1  0
 25 43  1  0
 23 42  1  0
 22 41  1  0
 20 40  1  6
 19 39  1  0
 17 38  1  0
 15 37  1  0
 14 36  1  0
M  END


  Mrv1652309072210232D          

 28 31  0  0  1  0            999 V2000
    0.8393   -2.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6193   -1.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1793   -1.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3992   -0.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1978   -0.3794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    0.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0994    0.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3339    1.4802    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1107    2.1751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1529    1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4191    2.3601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7410    1.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6552    0.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3230   -0.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0764    0.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1622    0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9156    1.1881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4944    1.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5802    2.1571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9603   -0.2645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8969    0.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3638   -0.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4480   -0.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7268    0.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5386    0.8097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1938    1.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4725    2.0690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6181    1.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 13  1  6  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 21 28  1  0  0  0  0
  8 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0246811

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)C1=C[C@@]2(O)C3=C(O)C(O)=CC=C3[C@@H]1C1=C(C(O)=C(O)C=C1)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O8/c1-2-28-19(26)10-7-20(27)15-9(4-6-12(22)17(15)24)13(10)8-3-5-11(21)16(23)14(8)18(20)25/h3-7,13,21-24,27H,2H2,1H3/t13-,20+/m0/s1

> <INCHI_KEY>
JAWVRPBRKAVFRI-RNODOKPDSA-N

> <FORMULA>
C20H16O8

> <MOLECULAR_WEIGHT>
384.34

> <EXACT_MASS>
384.084517475

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
36.81239839687188

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl (1R,9R)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0^{2,7}.0^{10,15}]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate

> <JCHEM_LOGP>
2.5034494456666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.345584783604597

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.583312978376512

> <JCHEM_PKA_STRONGEST_BASIC>
-4.325432571940371

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
97.98589999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
ethyl (1R,9R)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0^{2,7}.0^{10,15}]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       1.567  -4.450   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.156  -2.965   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.335  -2.579   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.745  -1.095   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.236  -0.708   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.335   0.003   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.186   1.452   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.623   2.763   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.207   4.060   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.152   2.948   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.649   4.405   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.250   1.868   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.090   0.336   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.336  -0.568   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.743   0.059   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.903   1.591   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.309   2.218   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.656   2.495   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.816   4.027   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.792  -0.494   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.674   0.689   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.679  -0.486   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.836  -0.212   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.357   1.237   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.872   1.511   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.362   2.413   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.882   3.862   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.154   2.139   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   28                                             
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12   19                                                  
CONECT   19   18                                                            
CONECT   20   13    6   21                                                  
CONECT   21   20   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21    8                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₆O₈

Average Mass

384.3400 Da

Monoisotopic Mass

384.08452 Da

IUPAC Name

ethyl (1R,9R)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0^{2,7}.0^{10,15}]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate

Traditional Name

ethyl (1R,9R)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0^{2,7}.0^{10,15}]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate

CAS Registry Number

Not Available

SMILES

CCOC(=O)C1=C[C@@]2(O)C3=C(O)C(O)=CC=C3[C@@H]1C1=C(C(O)=C(O)C=C1)C2=O

InChI Identifier

InChI=1S/C20H16O8/c1-2-28-19(26)10-7-20(27)15-9(4-6-12(22)17(15)24)13(10)8-3-5-11(21)16(23)14(8)18(20)25/h3-7,13,21-24,27H,2H2,1H3/t13-,20+/m0/s1

InChI Key

JAWVRPBRKAVFRI-RNODOKPDSA-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
Goupia glabra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Dibenzocycloheptenes

Sub Class

Not Available

Direct Parent

Dibenzocycloheptenes

Alternative Parents

Substituents

Dibenzocycloheptene
2-naphthalenecarboxylic acid or derivatives
2-naphthalenecarboxylic acid
Naphthalene
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Ketone
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.5	ChemAxon
pKa (Strongest Acidic)	8.58	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.99 m³·mol⁻¹	ChemAxon
Polarizability	36.81 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

132472785

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Matsuo Y, Yoshida A, Saito Y, Tanaka T: Structural Revision and Biomimetic Synthesis of Goupiolone B. Angew Chem Int Ed Engl. 2017 Sep 18;56(39):11855-11859. doi: 10.1002/anie.201706532. Epub 2017 Aug 18. [PubMed:28742264 ]
LOTUS database [Link]

Showing NP-Card for ethyl (1r,9r)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate (NP0246811)

MOL for NP0246811 (ethyl (1r,9r)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate)

3D MOL for NP0246811 (ethyl (1r,9r)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate)

3D SDF for NP0246811 (ethyl (1r,9r)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate)

3D-SDF for NP0246811 (ethyl (1r,9r)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate)

PDB for NP0246811 (ethyl (1r,9r)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate)

3D PDB for NP0246811 (ethyl (1r,9r)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate)

SMILES for NP0246811 (ethyl (1r,9r)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate)

INCHI for NP0246811 (ethyl (1r,9r)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate)

Structure for NP0246811 (ethyl (1r,9r)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate)

3D Structure for NP0246811 (ethyl (1r,9r)-5,6,9,11,12-pentahydroxy-8-oxotetracyclo[7.6.2.0²,⁷.0¹⁰,¹⁵]heptadeca-2(7),3,5,10,12,14,16-heptaene-16-carboxylate)