NP-MRD: Showing NP-Card for Cinchonain Ia (NP0051668)

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Record Information

Version

2.0

Created at

2022-04-27 22:56:54 UTC

Updated at

2022-04-27 22:56:54 UTC

NP-MRD ID

NP0051668

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cinchonain Ia

Description

Cinchonain ib belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol. Thus, cinchonain ib is considered to be a flavonoid. Cinchonain Ia is found in Anemopaegma arvense, Castanopsis hystrix, Cinchona pubescens, Cinchona succirubra , Kandelia candel, Phyllocladus trichomanoides , Polygonum bistorta , Rhaphiolepis umbellata, Rhizophora stylosa, Smilax china, Smilax corbularia, Trichilia catigua, Uncaria gambir and Uncaria rhynchophylla . Cinchonain Ia was first documented in 2006 (PMID: 16360665). Based on a literature review a significant number of articles have been published on Cinchonain ib (PMID: 18020420) (PMID: 30875889) (PMID: 30594026) (PMID: 26930981) (PMID: 23569923) (PMID: 23459662).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200562D          

 33 37  0  0  1  0            999 V2000
    2.7770    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  9  2  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 16 24  1  0  0  0  0
 23 25  1  1  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 28 31  1  0  0  0  0
 27 32  1  0  0  0  0
 22 33  1  1  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
    5.3406   -1.7600   -0.7583 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1477   -1.9225   -1.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4096   -1.0616   -2.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2022   -0.4492   -1.3260 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6473    0.4668   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9078    1.0612   -0.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3213    1.9321    0.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5163    2.2450    1.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9631    3.1204    2.7947 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2721    1.6686    1.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4379    1.9617    2.9083 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8579    0.7950    0.8376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3779   -1.5892   -0.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9761   -2.7533   -0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1715   -3.7600    0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1932   -3.6505    0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9670   -4.6761    0.8023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7918   -2.4852   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0109   -1.4652   -0.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6727   -0.3387   -1.0848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0399   -0.2081   -1.3249 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6341    0.9526   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2978    1.1396    0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8094    2.1857    1.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6751    3.0599    0.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2204    4.1258    1.5157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0273    2.8873   -0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9079    3.7832   -1.0792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5087    1.8380   -1.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8423   -1.4419   -1.0828 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1176   -1.0650   -0.6671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515   -2.3430   -0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3609   -2.9533   -0.4999 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0006   -0.3368   -2.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9874   -1.7753   -2.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6229    0.0916   -2.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5641    0.8469   -1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3182    2.3934    0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8851    3.5173    2.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7217    2.5865    3.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8598    0.3621    0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6546   -4.6782    0.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4840   -5.5246    1.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1598    0.0505   -2.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6176    0.4617    1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5539    2.3553    2.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9707    4.2636    2.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1876    3.6907   -2.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7510    1.6566   -2.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9485   -2.0509   -2.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6116   -1.8083   -0.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6995   -3.3613   -0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5727   -2.0406    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 32  1  0
 32 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 29  2  0
 29 27  1  0
 27 28  1  0
 27 25  2  0
 25 26  1  0
 25 24  1  0
 24 23  2  0
 19 13  1  0
 13 14  2  0
 14 33  1  0
 33  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5 12  2  0
 12 10  1  0
 10 11  1  0
 10  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 21 30  1  0
 23 22  1  0
  4 13  1  0
  6  5  1  0
 16 18  1  0
 31 51  1  0
 30 50  1  6
 32 52  1  0
 32 53  1  0
 21 44  1  6
 29 49  1  0
 28 48  1  0
 26 47  1  0
 24 46  1  0
 23 45  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  6
 12 41  1  0
 11 40  1  0
  9 39  1  0
  7 38  1  0
  6 37  1  0
 15 42  1  0
 17 43  1  0
M  END


  Mrv1652304282200562D          

 33 37  0  0  1  0            999 V2000
    2.7770    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  9  2  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 16 24  1  0  0  0  0
 23 25  1  1  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 28 31  1  0  0  0  0
 27 32  1  0  0  0  0
 22 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0051668

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C=C1)C1=C(OC(=O)C[C@@H]1C1=CC(O)=C(O)C=C1)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C24H20O9/c25-14-3-1-10(5-17(14)28)12-8-21(31)32-20-9-16(27)13-7-19(30)23(33-24(13)22(12)20)11-2-4-15(26)18(29)6-11/h1-6,9,12,19,23,25-30H,7-8H2/t12-,19-,23-/m1/s1

> <INCHI_KEY>
LKCOZWLUAKSRQM-UMAWSMADSA-N

> <FORMULA>
C24H20O9

> <MOLECULAR_WEIGHT>
452.415

> <EXACT_MASS>
452.110732224

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
43.843502144600635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R,5R,14R)-4,14-bis(3,4-dihydroxyphenyl)-5,8-dihydroxy-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8-trien-12-one

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
2.8252884056666665

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.19571660435244

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.713556519072469

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2981134284346734

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
115.02149999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.94e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,5R,14R)-4,14-bis(3,4-dihydroxyphenyl)-5,8-dihydroxy-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8-trien-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.184   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.104   4.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.874   6.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   6.105   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.184   7.438   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.104   7.438   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.034   0.770   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.724  -0.564   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.104  -3.231   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.206   3.437   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.746   3.437   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.516   4.771   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.746   6.105   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.206   6.105   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.564   4.771   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.516   7.438   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -4.056   4.771   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    2   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14    9   16                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18                                                            
CONECT   21   17   22                                                       
CONECT   22   21   23   33                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   16                                                       
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   28                                                            
CONECT   32   27                                                            
CONECT   33   22                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₀O₉

Average Mass

452.4150 Da

Monoisotopic Mass

452.11073 Da

IUPAC Name

(4R,5R,14R)-4,14-bis(3,4-dihydroxyphenyl)-5,8-dihydroxy-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8-trien-12-one

Traditional Name

(4R,5R,14R)-4,14-bis(3,4-dihydroxyphenyl)-5,8-dihydroxy-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),2(7),8-trien-12-one

CAS Registry Number

Not Available

SMILES

O[C@@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C=C1)C1=C(OC(=O)C[C@@H]1C1=CC(O)=C(O)C=C1)C=C2O

InChI Identifier

InChI=1S/C24H20O9/c25-14-3-1-10(5-17(14)28)12-8-21(31)32-20-9-16(27)13-7-19(30)23(33-24(13)22(12)20)11-2-4-15(26)18(29)6-11/h1-6,9,12,19,23,25-30H,7-8H2/t12-,19-,23-/m1/s1

InChI Key

LKCOZWLUAKSRQM-UMAWSMADSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anemopaegma arvense	LOTUS Database	35616633
Castanopsis hystrix	Plant	KNApSAcK
Cinchona pubescens	LOTUS Database	35616633
Cinchona succirubra	Plant	KNApSAcK
Kandelia candel	Plant	KNApSAcK
Phyllocladus trichomanoides	Plant	KNApSAcK
Polygonum bistorta	Plant	KNApSAcK
Rhaphiolepis umbellata	Plant	KNApSAcK
Rhizophora stylosa	LOTUS Database	35616633
Smilax china	LOTUS Database	35616633
Smilax corbularia	LOTUS Database	35616633
Trichilia catigua	Plant	KNApSAcK
Uncaria gambir	Plant	KNApSAcK
Uncaria rhynchophylla	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechins

Alternative Parents

Substituents

Catechin
Pyranoflavonoid
Linear 1,7-diphenylheptane skeleton
Pyranoneoflavonoid
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Neoflavan
Neoflavonoid skeleton
Angular pyranocoumarin
Pyranocoumarin
Pyranochromene
3,4-dihydrocoumarin
Chromane
Benzopyran
1-benzopyran
Catechol
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Lactone
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Ether
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

catechin (CHEBI:3702 )
Flavans, Flavanols and Leucoanthocyanidins (LMPK12020084 )

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	2.32	ALOGPS
logP	2.83	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.71	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	115.02 m³·mol⁻¹	ChemAxon
Polarizability	43.84 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00002913

Chemspider ID

391032

KEGG Compound ID

C10217

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442675

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tang W, Hioki H, Harada K, Kubo M, Fukuyama Y: Antioxidant phenylpropanoid-substituted epicatechins from Trichilia catigua. J Nat Prod. 2007 Dec;70(12):2010-3. doi: 10.1021/np0703895. Epub 2007 Nov 20. [PubMed:18020420 ]
de Carvalho Junior AR, Oliveira Ferreira R, de Souza Passos M, da Silva Boeno SI, Gloria das Virgens LL, Ventura TLB, Calixto SD, Lassounskaia E, de Carvalho MG, Braz-Filho R, Curcino Vieira IJ: Antimycobacterial and Nitric Oxide Production Inhibitory Activities of Triterpenes and Alkaloids from Psychotria nuda (Cham. & Schltdl.) Wawra. Molecules. 2019 Mar 15;24(6). pii: molecules24061026. doi: 10.3390/molecules24061026. [PubMed:30875889 ]
Yan XT, An Z, Huangfu Y, Zhang YT, Li CH, Chen X, Liu PL, Gao JM: Polycyclic polyprenylated acylphloroglucinol and phenolic metabolites from the aerial parts of Hypericum elatoides and their neuroprotective and anti-neuroinflammatory activities. Phytochemistry. 2019 Mar;159:65-74. doi: 10.1016/j.phytochem.2018.12.011. Epub 2018 Dec 26. [PubMed:30594026 ]
Xiang MX, Hu YJ, He F, Liu XQ: [Chemical Composition of n-Butanol Fraction from Polygonum amplexicaule var. sinense]. Zhong Yao Cai. 2015 Sep;38(9):1872-4. [PubMed:26930981 ]
Patel DK, Prasad SK, Kumar R, Hemalatha S: An overview on antidiabetic medicinal plants having insulin mimetic property. Asian Pac J Trop Biomed. 2012 Apr;2(4):320-30. doi: 10.1016/S2221-1691(12)60032-X. [PubMed:23569923 ]
Li J, Coleman CM, Wu H, Burandt CL Jr, Ferreira D, Zjawiony JK: Triterpenoids and flavonoids from Cecropia schreberiana Miq. (Urticaceae). Biochem Syst Ecol. 2013 Jun 1;48:96-99. doi: 10.1016/j.bse.2012.11.018. Epub 2013 Jan 16. [PubMed:23459662 ]
Qa'dan F, Verspohl EJ, Nahrstedt A, Petereit F, Matalka KZ: Cinchonain Ib isolated from Eriobotrya japonica induces insulin secretion in vitro and in vivo. J Ethnopharmacol. 2009 Jul 15;124(2):224-7. doi: 10.1016/j.jep.2009.04.023. Epub 2009 May 3. [PubMed:19397981 ]
Li DL, Li XM, Peng ZY, Wang BG: Flavanol derivatives from Rhizophora stylosa and their DPPH radical scavenging activity. Molecules. 2007 May 26;12(5):1163-9. doi: 10.3390/12051163. [PubMed:17873850 ]
Beltrame FL, Filho ER, Barros FA, Cortez DA, Cass QB: A validated higher-performance liquid chromatography method for quantification of cinchonain Ib in bark and phytopharmaceuticals of Trichilia catigua used as Catuaba. J Chromatogr A. 2006 Jun 30;1119(1-2):257-63. doi: 10.1016/j.chroma.2005.10.050. Epub 2005 Dec 19. [PubMed:16360665 ]

Showing NP-Card for Cinchonain Ia (NP0051668)

MOL for NP0051668 (Cinchonain Ia)

3D MOL for NP0051668 (Cinchonain Ia)

3D SDF for NP0051668 (Cinchonain Ia)

3D-SDF for NP0051668 (Cinchonain Ia)

PDB for NP0051668 (Cinchonain Ia)

3D PDB for NP0051668 (Cinchonain Ia)

SMILES for NP0051668 (Cinchonain Ia)

INCHI for NP0051668 (Cinchonain Ia)

Structure for NP0051668 (Cinchonain Ia)

3D Structure for NP0051668 (Cinchonain Ia)