NP-MRD: Showing NP-Card for catiguanin B (NP0033430)

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Record Information

Version

2.0

Created at

2021-06-19 23:58:39 UTC

Updated at

2021-06-30 00:03:12 UTC

NP-MRD ID

NP0033430

Secondary Accession Numbers

None

Natural Product Identification

Common Name

catiguanin B

Provided By

JEOL Database JEOL Logo

Description

Catiguanin B 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. Catiguanin B is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. catiguanin B is found in Trichilia catigua. catiguanin B was first documented in 2007 (PMID: 18020420). Based on a literature review very few articles have been published on catiguanin B (PMID: 30899831).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101583D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202101583D          

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   -0.1621   -2.8584   -1.8037 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0983   -2.6545   -2.4640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1434   -1.7812   -2.2631 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3940   -0.3102   -2.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7548   -0.3070   -1.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3888   -1.4554   -1.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8856    1.7410    1.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1804    2.3068    0.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835   -0.0343    2.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3007    1.1058    4.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0106    2.1299    6.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7186    4.6551    5.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5775    4.7756    2.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2561    2.6833   -1.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9583    1.4233   -3.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0289   -2.9030    0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009   -5.4426    0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7077   -7.2884    0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0221   -6.6259    1.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3890   -3.5760    1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5639   -2.6870    0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5284   -3.8372   -2.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7064   -3.3404   -2.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9802   -1.5610   -3.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1663   -2.1581   -2.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
 35 33  1  0  0  0  0
  9 11  1  0  0  0  0
 33 24  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 24 23  1  0  0  0  0
 33 34  1  0  0  0  0
 16 22  2  0  0  0  0
 24 25  1  0  0  0  0
 20 18  1  0  0  0  0
 25 32  2  0  0  0  0
 32 30  1  0  0  0  0
 18 17  2  0  0  0  0
 30 28  2  0  0  0  0
 17 16  1  0  0  0  0
 28 27  1  0  0  0  0
 16 15  1  0  0  0  0
 27 26  2  0  0  0  0
 26 25  1  0  0  0  0
 22  6  1  0  0  0  0
 28 29  1  0  0  0  0
  6  7  1  0  0  0  0
 30 31  1  0  0  0  0
 14 15  1  0  0  0  0
 18 19  1  0  0  0  0
 22 21  1  0  0  0  0
  9 10  1  0  0  0  0
 21 20  2  0  0  0  0
 11 12  1  0  0  0  0
 14  7  2  0  0  0  0
 21 23  1  0  0  0  0
  5  3  1  0  0  0  0
  7  8  1  0  0  0  0
  3  2  1  0  0  0  0
 20 35  1  0  0  0  0
  3  4  2  0  0  0  0
  8  9  2  0  0  0  0
  2  1  1  0  0  0  0
  6  5  1  0  0  0  0
 17 46  1  0  0  0  0
 35 56  1  0  0  0  0
 35 57  1  0  0  0  0
 33 54  1  1  0  0  0
 24 48  1  1  0  0  0
  6 41  1  1  0  0  0
  8 42  1  0  0  0  0
 13 45  1  0  0  0  0
 34 55  1  0  0  0  0
 32 53  1  0  0  0  0
 27 50  1  0  0  0  0
 26 49  1  0  0  0  0
 29 51  1  0  0  0  0
 31 52  1  0  0  0  0
 19 47  1  0  0  0  0
 10 43  1  0  0  0  0
 12 44  1  0  0  0  0
  5 39  1  0  0  0  0
  5 40  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033430

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C([H])=C1O[H])[C@@]([H])(C1=C(O2)C([H])=C(O[H])C2=C1O[C@]([H])(C1=C([H])C(O[H])=C(O[H])C([H])=C1[H])[C@]([H])(O[H])C2([H])[H])C([H])([H])C(=O)OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H22O10/c1-33-22(32)7-12-11-5-17(29)18(30)9-20(11)34-21-8-15(27)13-6-19(31)24(35-25(13)23(12)21)10-2-3-14(26)16(28)4-10/h2-5,8-9,12,19,24,26-31H,6-7H2,1H3/t12-,19+,24+/m0/s1

> <INCHI_KEY>
XECJBJHITROSPL-WSONZKGWSA-N

> <FORMULA>
C25H22O10

> <MOLECULAR_WEIGHT>
482.441

> <EXACT_MASS>
482.121296908

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
48.02618481719617

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(2R,3R,12S)-2-(3,4-dihydroxyphenyl)-3,5,9,10-tetrahydroxy-2,3,4,12-tetrahydro-1,7-dioxatetraphen-12-yl]acetate

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
2.6676171400000004

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.13267715401007

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.646578092250582

> <JCHEM_PKA_STRONGEST_BASIC>
-3.295277697284659

> <JCHEM_POLAR_SURFACE_AREA>
166.14000000000001

> <JCHEM_REFRACTIVITY>
121.48469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(2R,3R,12S)-2-(3,4-dihydroxyphenyl)-3,5,9,10-tetrahydroxy-2,3,4,12-tetrahydro-1,7-dioxatetraphen-12-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 61  0  0  0  0  0  0  0  0999 V2000
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    0.8895    0.9242    1.5528 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3329    1.9387    2.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6659    1.9003    3.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1823    2.8952    4.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4707    2.9124    6.0765 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0755    4.8974    5.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9524    3.9737    2.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4853    2.9711    2.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8552    3.0460    0.7220 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7542    0.6265   -1.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5687    0.5486   -2.9321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0274   -0.5095   -1.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126   -0.4403   -0.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0757    0.7608    0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911   -1.5206    0.1465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0386   -2.7918   -0.2697 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8298   -3.9187    0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3181   -5.2287    0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1047   -6.2791    0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4023   -6.0215    1.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1695   -7.0467    1.7175 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9225   -4.7341    1.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2051   -4.5332    1.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1484   -3.6872    0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1621   -2.8584   -1.8037 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0983   -2.6545   -2.4640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1434   -1.7812   -2.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3940   -0.3102   -2.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7548   -0.3070   -1.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3888   -1.4554   -1.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8856    1.7410    1.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1804    2.3068    0.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835   -0.0343    2.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3007    1.1058    4.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0106    2.1299    6.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7186    4.6551    5.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5775    4.7756    2.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2561    2.6833   -1.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9583    1.4233   -3.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0289   -2.9030    0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009   -5.4426    0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7077   -7.2884    0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0221   -6.6259    1.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3890   -3.5760    1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5639   -2.6870    0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5284   -3.8372   -2.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7064   -3.3404   -2.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9802   -1.5610   -3.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1663   -2.1581   -2.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
 35 33  1  0
  9 11  1  0
 33 24  1  0
 11 13  2  0
 13 14  1  0
 24 23  1  0
 33 34  1  0
 16 22  2  0
 24 25  1  0
 20 18  1  0
 25 32  2  0
 32 30  1  0
 18 17  2  0
 30 28  2  0
 17 16  1  0
 28 27  1  0
 16 15  1  0
 27 26  2  0
 26 25  1  0
 22  6  1  0
 28 29  1  0
  6  7  1  0
 30 31  1  0
 14 15  1  0
 18 19  1  0
 22 21  1  0
  9 10  1  0
 21 20  2  0
 11 12  1  0
 14  7  2  0
 21 23  1  0
  5  3  1  0
  7  8  1  0
  3  2  1  0
 20 35  1  0
  3  4  2  0
  8  9  2  0
  2  1  1  0
  6  5  1  0
 17 46  1  0
 35 56  1  0
 35 57  1  0
 33 54  1  1
 24 48  1  1
  6 41  1  1
  8 42  1  0
 13 45  1  0
 34 55  1  0
 32 53  1  0
 27 50  1  0
 26 49  1  0
 29 51  1  0
 31 52  1  0
 19 47  1  0
 10 43  1  0
 12 44  1  0
  5 39  1  0
  5 40  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       3.674  -0.445  -1.750  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.991   0.543  -0.978  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.046   0.355   0.367  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.654  -0.543   0.938  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.264   1.423   1.079  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.890   0.924   1.553  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.333   1.939   2.534  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.666   1.900   3.897  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.182   2.895   4.740  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.471   2.912   6.077  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.615   3.923   4.238  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.075   4.897   5.077  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.952   3.974   2.894  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.485   2.971   2.046  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.855   3.046   0.722  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.848   1.865   0.011  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.675   1.809  -1.108  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.754   0.627  -1.837  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.569   0.549  -2.932  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.027  -0.509  -1.460  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.213  -0.440  -0.320  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.076   0.761   0.395  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.491  -1.521   0.147  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.039  -2.792  -0.270  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.830  -3.919   0.277  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.318  -5.229   0.348  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.105  -6.279   0.830  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.402  -6.021   1.246  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.170  -7.047   1.718  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.922  -4.734   1.187  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.205  -4.533   1.616  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.148  -3.687   0.703  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.162  -2.858  -1.804  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.098  -2.655  -2.464  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.143  -1.781  -2.263  0.00  0.00           C+0
HETATM   36  H   UNK     0       3.394  -0.310  -2.798  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.755  -0.307  -1.655  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.389  -1.455  -1.444  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.886   1.741   1.927  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.180   2.307   0.433  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.984  -0.034   2.079  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.301   1.106   4.278  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.011   2.130   6.283  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.719   4.655   5.955  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.577   4.776   2.516  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.256   2.683  -1.384  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.958   1.423  -3.098  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.029  -2.903   0.197  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.701  -5.443   0.031  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.708  -7.288   0.885  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.022  -6.626   1.948  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.389  -3.576   1.565  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.564  -2.687   0.656  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.528  -3.837  -2.135  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.706  -3.340  -2.135  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.980  -1.561  -3.325  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.166  -2.158  -2.137  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    3    6   39   40                                             
CONECT    6   22    7    5   41                                             
CONECT    7    6   14    8                                                  
CONECT    8    7    9   42                                                  
CONECT    9   11   10    8                                                  
CONECT   10    9   43                                                       
CONECT   11    9   13   12                                                  
CONECT   12   11   44                                                       
CONECT   13   11   14   45                                                  
CONECT   14   13   15    7                                                  
CONECT   15   16   14                                                       
CONECT   16   22   17   15                                                  
CONECT   17   18   16   46                                                  
CONECT   18   20   17   19                                                  
CONECT   19   18   47                                                       
CONECT   20   18   21   35                                                  
CONECT   21   22   20   23                                                  
CONECT   22   16    6   21                                                  
CONECT   23   24   21                                                       
CONECT   24   33   23   25   48                                             
CONECT   25   24   32   26                                                  
CONECT   26   27   25   49                                                  
CONECT   27   28   26   50                                                  
CONECT   28   30   27   29                                                  
CONECT   29   28   51                                                       
CONECT   30   32   28   31                                                  
CONECT   31   30   52                                                       
CONECT   32   25   30   53                                                  
CONECT   33   35   24   34   54                                             
CONECT   34   33   55                                                       
CONECT   35   33   20   56   57                                             
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42    8                                                            
CONECT   43   10                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   17                                                            
CONECT   47   19                                                            
CONECT   48   24                                                            
CONECT   49   26                                                            
CONECT   50   27                                                            
CONECT   51   29                                                            
CONECT   52   31                                                            
CONECT   53   32                                                            
CONECT   54   33                                                            
CONECT   55   34                                                            
CONECT   56   35                                                            
CONECT   57   35                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  122    0
END

RDKit          3D

57 61  0  0  0  0  0  0  0  0999 V2000
    3.6737   -0.4449   -1.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9906    0.5426   -0.9781 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0455    0.3547    0.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -0.5427    0.9380 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2635    1.4229    1.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8895    0.9242    1.5528 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3329    1.9387    2.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6659    1.9003    3.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1823    2.8952    4.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4707    2.9124    6.0765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6150    3.9231    4.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0755    4.8974    5.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9524    3.9737    2.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4853    2.9711    2.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8552    3.0460    0.7220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8483    1.8650    0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6754    1.8091   -1.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7542    0.6265   -1.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5687    0.5486   -2.9321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0274   -0.5095   -1.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126   -0.4403   -0.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0757    0.7608    0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911   -1.5206    0.1465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0386   -2.7918   -0.2697 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8298   -3.9187    0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3181   -5.2287    0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1047   -6.2791    0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4023   -6.0215    1.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1695   -7.0467    1.7175 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9225   -4.7341    1.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2051   -4.5332    1.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1484   -3.6872    0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1621   -2.8584   -1.8037 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0983   -2.6545   -2.4640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1434   -1.7812   -2.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3940   -0.3102   -2.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7548   -0.3070   -1.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3888   -1.4554   -1.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8856    1.7410    1.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1804    2.3068    0.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835   -0.0343    2.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3007    1.1058    4.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0106    2.1299    6.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7186    4.6551    5.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5775    4.7756    2.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2561    2.6833   -1.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9583    1.4233   -3.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0289   -2.9030    0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009   -5.4426    0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7077   -7.2884    0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0221   -6.6259    1.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3890   -3.5760    1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5639   -2.6870    0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5284   -3.8372   -2.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7064   -3.3404   -2.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9802   -1.5610   -3.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1663   -2.1581   -2.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
 35 33  1  0
  9 11  1  0
 33 24  1  0
 11 13  2  0
 13 14  1  0
 24 23  1  0
 33 34  1  0
 16 22  2  0
 24 25  1  0
 20 18  1  0
 25 32  2  0
 32 30  1  0
 18 17  2  0
 30 28  2  0
 17 16  1  0
 28 27  1  0
 16 15  1  0
 27 26  2  0
 26 25  1  0
 22  6  1  0
 28 29  1  0
  6  7  1  0
 30 31  1  0
 14 15  1  0
 18 19  1  0
 22 21  1  0
  9 10  1  0
 21 20  2  0
 11 12  1  0
 14  7  2  0
 21 23  1  0
  5  3  1  0
  7  8  1  0
  3  2  1  0
 20 35  1  0
  3  4  2  0
  8  9  2  0
  2  1  1  0
  6  5  1  0
 17 46  1  0
 35 56  1  0
 35 57  1  0
 33 54  1  1
 24 48  1  1
  6 41  1  1
  8 42  1  0
 13 45  1  0
 34 55  1  0
 32 53  1  0
 27 50  1  0
 26 49  1  0
 29 51  1  0
 31 52  1  0
 19 47  1  0
 10 43  1  0
 12 44  1  0
  5 39  1  0
  5 40  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₂O₁₀

Average Mass

482.4410 Da

Monoisotopic Mass

482.12130 Da

IUPAC Name

methyl 2-[(2R,3R,12S)-2-(3,4-dihydroxyphenyl)-3,5,9,10-tetrahydroxy-2,3,4,12-tetrahydro-1,7-dioxatetraphen-12-yl]acetate

Traditional Name

methyl [(2R,3R,12S)-2-(3,4-dihydroxyphenyl)-3,5,9,10-tetrahydroxy-2,3,4,12-tetrahydro-1,7-dioxatetraphen-12-yl]acetate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C([H])=C1O[H])[C@@]([H])(C1=C(O2)C([H])=C(O[H])C2=C1O[C@]([H])(C1=C([H])C(O[H])=C(O[H])C([H])=C1[H])[C@]([H])(O[H])C2([H])[H])C([H])([H])C(=O)OC([H])([H])[H]

InChI Identifier

InChI=1S/C25H22O10/c1-33-22(32)7-12-11-5-17(29)18(30)9-20(11)34-21-8-15(27)13-6-19(31)24(35-25(13)23(12)21)10-2-3-14(26)16(28)4-10/h2-5,8-9,12,19,24,26-31H,6-7H2,1H3/t12-,19+,24+/m0/s1

InChI Key

XECJBJHITROSPL-WSONZKGWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trichilia catigua	JEOL database	Tang, W., et al, J. Nat. Prod. 70, 2010 (2007)

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
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Xanthene
Dibenzopyran
Diaryl ether
Chromane
Benzopyran
1-benzopyran
Catechol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Methyl ester
Secondary alcohol
Carboxylic acid ester
Ether
Polyol
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotetracyclic compound (CHEBI:65602 )
catechols (CHEBI:65602 )
polyphenol (CHEBI:65602 )
methyl ester (CHEBI:65602 )
extended flavonoid (CHEBI:65602 )

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	2.42	ALOGPS
logP	2.67	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.65	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	121.48 m³·mol⁻¹	ChemAxon
Polarizability	48.03 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00038714

Chemspider ID

23311393

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

65602

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 ]
Sarwar MW, Riaz A, Nahid N, Al Qahtani A, Ahmed N, Nawaz-Ul-Rehman MS, Younus A, Mubin M: Homology modeling and docking analysis of ssC1 protein encoded by Cotton leaf curl Multan betasatellite with different plant flavonoids. Heliyon. 2019 Mar 7;5(3):e01303. doi: 10.1016/j.heliyon.2019.e01303. eCollection 2019 Mar. [PubMed:30899831 ]
Tang, W., et al. (2007). Tang, W., et al, J. Nat. Prod. 70, 2010 (2007). J. Nat. Prod..

Showing NP-Card for catiguanin B (NP0033430)

MOL for NP0033430 (catiguanin B)

3D MOL for NP0033430 (catiguanin B)

3D SDF for NP0033430 (catiguanin B)

3D-SDF for NP0033430 (catiguanin B)

PDB for NP0033430 (catiguanin B)

3D PDB for NP0033430 (catiguanin B)

SMILES for NP0033430 (catiguanin B)

INCHI for NP0033430 (catiguanin B)

Structure for NP0033430 (catiguanin B)

3D Structure for NP0033430 (catiguanin B)