NP-MRD: Showing NP-Card for Makomotine A (NP0044091)

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Record Information

Version

1.0

Created at

2021-11-12 23:49:32 UTC

Updated at

2021-11-26 17:45:20 UTC

NP-MRD ID

NP0044091

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Makomotine A

Description

Makomotine A belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Makomotine A is found in Ustilago esculenta. It was first documented in 2014 (PMID: 25419997). Based on a literature review a significant number of articles have been published on Makomotine A (PMID: 34748561) (PMID: 34746809) (PMID: 34740265) (PMID: 34728144).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100492D          

 31 33  0  0  1  0            999 V2000
    0.4280   -5.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7636   -4.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2787   -4.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6142   -3.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1293   -2.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6912   -2.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1761   -2.0052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8406   -1.2515    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3255   -0.5841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899    0.1696    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4748    0.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1393    1.5907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242    2.2581    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4492    2.2581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7041    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    3.5277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5887    4.1408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847    4.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396    4.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693    3.0428    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5846    3.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1694    0.2558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1661    1.0095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3155   -0.4116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1360   -0.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0201   -1.1653    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4648   -1.8327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0267   -3.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8472   -3.5126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828   -4.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5418   -4.0938    0.0000 C   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
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  6  0  0  0
 18 19  1  0  0  0  0
 16 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  1  0  0  0
 10 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  1  0  0  0
  6 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  2  0  0  0  0
  3 31  1  0  0  0  0
M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
    7.1926    2.4507   -1.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4379    1.4161   -2.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2588    1.1126   -1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5365   -0.0255   -1.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4062   -0.3696   -0.9582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9597    0.3786    0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8491    0.1109    0.8687 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0122   -0.9441    0.6815 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3133   -0.5935    0.4083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0616   -1.6541   -0.0129 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4687   -1.6406    0.5979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1933   -0.5230    0.2881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4419   -0.2905   -1.0342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0176    1.0273   -1.3182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8510    1.7609   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2216    1.2066   -0.7363 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9878    2.0138   -1.5560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9713    0.9517    0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2281    2.1306    1.2375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9351   -0.1492   -1.3318 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0595   -0.0430   -2.7154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4667   -3.0045    0.2047 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1834   -3.4444   -0.9727 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3842   -3.1426    1.4185 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2107   -3.9087    2.4207 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8773   -1.8303    1.9395 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0413   -1.8918    2.6516 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6828    1.5266    0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2696    2.3060    1.5461 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0346    3.4472    1.8744 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8050    1.8521   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9749    3.1264   -1.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0651    2.6606   -2.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7325    0.7747   -2.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8741   -0.6213   -2.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8727   -1.2585   -1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3230   -1.5777   -0.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115   -1.5409   -1.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2855   -1.6038    1.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9906   -2.5896    0.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0543   -1.0076   -1.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5745    1.4954    0.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7664    2.8383   -0.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6426    1.5377   -2.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4058    0.2221    1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9182    0.4250    0.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2057    2.8706    0.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5268   -0.9561   -0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9863   -0.9195   -3.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -3.7389    0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2372   -2.9682   -1.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3011   -3.7275    1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4956   -4.0813    3.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0760   -1.4093    2.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7564   -2.2460    2.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0956    3.1613    2.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5657    4.0530    2.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1091    4.0938    0.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3788    2.7508    0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 10 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
  6 28  1  0
 28 29  1  0
 29 30  1  0
 28 31  2  0
 31  3  1  0
 26  8  1  0
 20 13  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  4 35  1  0
  5 36  1  0
  8 37  1  6
 10 38  1  6
 11 39  1  0
 11 40  1  0
 13 41  1  6
 15 42  1  0
 15 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  1
 21 49  1  0
 22 50  1  1
 23 51  1  0
 24 52  1  6
 25 53  1  0
 26 54  1  1
 27 55  1  0
 30 56  1  0
 30 57  1  0
 30 58  1  0
 31 59  1  0
M  END


  Mrv1652311132100492D          

 31 33  0  0  1  0            999 V2000
    0.4280   -5.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7636   -4.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2787   -4.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6142   -3.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1293   -2.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6912   -2.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1761   -2.0052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8406   -1.2515    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3255   -0.5841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899    0.1696    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4748    0.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1393    1.5907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242    2.2581    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4492    2.2581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7041    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    3.5277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5887    4.1408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847    4.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396    4.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693    3.0428    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5846    3.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1694    0.2558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1661    1.0095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3155   -0.4116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1360   -0.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0201   -1.1653    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4648   -1.8327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0267   -3.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8472   -3.5126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828   -4.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5418   -4.0938    0.0000 C   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
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  6  0  0  0
 18 19  1  0  0  0  0
 16 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  1  0  0  0
 10 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  1  0  0  0
  6 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  2  0  0  0  0
  3 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044091

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O11/c1-3-10-4-5-11(12(6-10)27-2)30-18-16(24)15(23)14(22)13(31-18)7-28-19-17(25)20(26,8-21)9-29-19/h3-6,13-19,21-26H,1,7-9H2,2H3/t13-,14-,15+,16-,17+,18-,19-,20-/m1/s1

> <INCHI_KEY>
YCZLNSMKISKQGO-LTRJMQNCSA-N

> <FORMULA>
C20H28O11

> <MOLECULAR_WEIGHT>
444.433

> <EXACT_MASS>
444.163161722

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
43.96483662704635

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6S)-2-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(4-ethenyl-2-methoxyphenoxy)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.92

> <JCHEM_LOGP>
-1.2958558566666651

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.311646705679756

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.70170048903416

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1423790163389214

> <JCHEM_POLAR_SURFACE_AREA>
167.52999999999997

> <JCHEM_REFRACTIVITY>
103.00299999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R,6S)-2-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(4-ethenyl-2-methoxyphenoxy)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0       0.799 -10.133   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.425  -8.727   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.520  -7.481   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.147  -6.074   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.241  -4.828   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.290  -4.989   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.195  -3.743   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.569  -2.336   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.474  -1.090   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.848   0.317   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.753   1.562   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.127   2.969   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.032   4.215   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.572   4.215   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.048   5.680   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.802   6.585   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.832   7.729   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.771   7.729   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.247   9.194   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.556   5.680   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.091   6.156   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.316   0.478   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.310   1.884   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.589  -0.768   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.120  -0.607   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.037  -2.175   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.868  -3.421   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.917  -6.396   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.448  -6.557   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.075  -7.964   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.011  -7.642   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   20                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   16   13   21                                                  
CONECT   21   20                                                            
CONECT   22   10   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    8   27                                                  
CONECT   27   26                                                            
CONECT   28    6   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28    3                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₁₁

Average Mass

444.4330 Da

Monoisotopic Mass

444.16316 Da

IUPAC Name

(2R,3S,4S,5R,6S)-2-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(4-ethenyl-2-methoxyphenoxy)oxane-3,4,5-triol

Traditional Name

(2R,3S,4S,5R,6S)-2-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(4-ethenyl-2-methoxyphenoxy)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=CC(C=C)=CC=C1O[C@@H]1O[C@H](CO[C@@H]2OC[C@](O)(CO)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C20H28O11/c1-3-10-4-5-11(12(6-10)27-2)30-18-16(24)15(23)14(22)13(31-18)7-28-19-17(25)20(26,8-21)9-29-19/h3-6,13-19,21-26H,1,7-9H2,2H3/t13-,14-,15+,16-,17+,18-,19-,20-/m1/s1

InChI Key

YCZLNSMKISKQGO-LTRJMQNCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, 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
Ustilago esculenta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
O-glycosyl compound
Disaccharide
Phenoxy compound
Methoxybenzene
Styrene
Phenol ether
Anisole
Alkyl aryl ether
Benzenoid
Oxane
Monocyclic benzene moiety
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.92	ALOGPS
logP	-1.3	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	11.7	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	167.53 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	103 m³·mol⁻¹	ChemAxon
Polarizability	43.96 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78438494

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102367923

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hu ZX, Xue YB, Bi XB, Zhang JW, Luo ZW, Li XN, Yao GM, Wang JP, Zhang YH: Five new secondary metabolites produced by a marine-associated fungus, Daldinia eschscholzii. Mar Drugs. 2014 Nov 20;12(11):5563-75. doi: 10.3390/md12115563. [PubMed:25419997 ]
Rai A, Chettri M, Dewan S, Khandelwal B, Chettri B: Epidemiological study of snakebite cases in Sikkim: Risk modeling with regard to the habitat suitability of common venomous snakes. PLoS Negl Trop Dis. 2021 Nov 8;15(11):e0009800. doi: 10.1371/journal.pntd.0009800. eCollection 2021 Nov. [PubMed:34748561 ]
Parihar PS, Singh A, Karade SS, Sahasrabuddhe AA, Pratap JV: Structural insights into kinetoplastid coronin oligomerization domain and F-actin interaction. Curr Res Struct Biol. 2021 Oct 14;3:268-276. doi: 10.1016/j.crstbi.2021.10.002. eCollection 2021. [PubMed:34746809 ]
Sanjeev MN, Kaur H, Mayall SS, Rishika, Yeluri R: Resorbable Collagen Barrier Impeding the Extrusion of Obturating Material in Primary Molars Undergoing Resorption - A Randomized Clinical Trial. J Clin Pediatr Dent. 2021 Nov 1;45(5):312-316. doi: 10.17796/1053-4625-45.5.4. [PubMed:34740265 ]
Bechara R, Gaffen SL: '(m(6))A' stands for 'autoimmunity': reading, writing, and erasing RNA modifications during inflammation. Trends Immunol. 2021 Oct 30. pii: S1471-4906(21)00207-6. doi: 10.1016/j.it.2021.10.002. [PubMed:34728144 ]

Showing NP-Card for Makomotine A (NP0044091)

MOL for NP0044091 (Makomotine A)

3D MOL for NP0044091 (Makomotine A)

3D SDF for NP0044091 (Makomotine A)

3D-SDF for NP0044091 (Makomotine A)

PDB for NP0044091 (Makomotine A)

3D PDB for NP0044091 (Makomotine A)

SMILES for NP0044091 (Makomotine A)

INCHI for NP0044091 (Makomotine A)

Structure for NP0044091 (Makomotine A)

3D Structure for NP0044091 (Makomotine A)