NP-MRD: Showing NP-Card for JBIR-37 (NP0008708)

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Record Information

Version

2.0

Created at

2020-12-09 06:14:11 UTC

Updated at

2021-07-15 17:01:11 UTC

NP-MRD ID

NP0008708

Secondary Accession Numbers

None

Natural Product Identification

Common Name

JBIR-37

Provided By

NPAtlas

Description

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(2-methylbut-3-en-2-yl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenoxy]oxane-3,4,5-triol 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. JBIR-37 is found in Acremonium. JBIR-37 was first documented in 2009 (PMID: 19734652). Based on a literature review very few articles have been published on (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(2-methylbut-3-en-2-yl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenoxy]oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106123D          

 69 71  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 69 71  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242106123D          

 69 71  0  0  0  0            999 V2000
   -1.3999   -4.9720   -1.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5663   -4.5097    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9442   -3.0861    0.1900 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5141   -2.9201    1.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9563   -2.7489   -0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7204   -2.2708    0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4800   -2.8919   -0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6819   -2.2277   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6755   -0.8650    0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8607   -0.1610   -0.0220 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1461   -0.6617   -0.1899 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0001   -0.3194    0.8654 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7060    0.8382    0.6398 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1128    1.4685    1.9569 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8306    2.6463    1.6669 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8582    1.8690   -0.0953 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4862    3.1010   -0.0613 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6308    1.4029   -1.5151 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4470    1.9021   -2.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6699   -0.1029   -1.5064 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9221   -0.6176   -1.8238 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4708   -0.2199    0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401   -0.8855    0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8641   -0.2642    0.4285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9845    0.3549    0.5917 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3002    1.2239   -0.5059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5184    1.8053   -0.1980 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2653    2.2434   -1.4420 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5235    1.1806   -2.2807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1915    3.0351    0.6503 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2848    3.3335    1.4750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9857    2.6560    1.4900 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7891    2.8765    0.8445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0937    1.2047    1.8583 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2756    0.9874    2.5371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1211   -6.0210   -1.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5127   -4.3997   -2.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306   -5.1486    0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6052   -2.9976    1.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1038   -3.7407    2.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345   -1.9817    2.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2683   -3.6611   -1.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9065   -2.4620   -0.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6315   -2.0124   -1.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5495   -3.9920   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5858   -2.8103   -0.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2287   -1.7575   -0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6483    0.6168    0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7227    0.7647    2.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2158    1.7604    2.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5159    2.4296    0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8776    1.9024    0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8284    3.7949   -0.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4758    1.7893   -2.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4924    2.0341   -3.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9734   -0.4593   -2.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0327   -1.4438   -1.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    0.8755    0.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9348   -0.2865    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1597    1.0974    0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6898    3.0007   -2.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2255    2.7142   -1.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3485    1.3669   -2.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0064    3.9207    0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9400    3.4319    2.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9901    3.2508    2.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9092    3.0900   -0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2507    0.8890    2.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5531    0.0401    2.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 23  6  1  0  0  0  0
 34 25  1  0  0  0  0
 20 11  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  2 38  1  0  0  0  0
  4 39  1  0  0  0  0
  4 40  1  0  0  0  0
  4 41  1  0  0  0  0
  5 42  1  0  0  0  0
  5 43  1  0  0  0  0
  5 44  1  0  0  0  0
  7 45  1  0  0  0  0
  8 46  1  0  0  0  0
 11 47  1  6  0  0  0
 13 48  1  6  0  0  0
 14 49  1  0  0  0  0
 14 50  1  0  0  0  0
 15 51  1  0  0  0  0
 16 52  1  1  0  0  0
 17 53  1  0  0  0  0
 18 54  1  6  0  0  0
 19 55  1  0  0  0  0
 20 56  1  6  0  0  0
 21 57  1  0  0  0  0
 22 58  1  0  0  0  0
 25 59  1  1  0  0  0
 27 60  1  1  0  0  0
 28 61  1  0  0  0  0
 28 62  1  0  0  0  0
 29 63  1  0  0  0  0
 30 64  1  6  0  0  0
 31 65  1  0  0  0  0
 32 66  1  1  0  0  0
 33 67  1  0  0  0  0
 34 68  1  1  0  0  0
 35 69  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0008708

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(OC2=C([H])C([H])=C(C(O[C@]3([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])=C2[H])C(C([H])=C([H])[H])(C([H])([H])[H])C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O12/c1-4-23(2,3)11-6-5-10(32-21-19(30)17(28)15(26)13(8-24)34-21)7-12(11)33-22-20(31)18(29)16(27)14(9-25)35-22/h4-7,13-22,24-31H,1,8-9H2,2-3H3/t13-,14-,15-,16-,17+,18+,19-,20-,21-,22-/m1/s1

> <INCHI_KEY>
VWNIXYVUBPRGGF-OALZDZJCSA-N

> <FORMULA>
C23H34O12

> <MOLECULAR_WEIGHT>
502.513

> <EXACT_MASS>
502.205026535

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
50.29166696230834

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(2-methylbut-3-en-2-yl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenoxy]oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.75

> <JCHEM_LOGP>
-1.4843840646666657

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.42130503027543

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.899103052778894

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923437225645

> <JCHEM_POLAR_SURFACE_AREA>
198.76

> <JCHEM_REFRACTIVITY>
117.61960000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(2-methylbut-3-en-2-yl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenoxy]oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 69 71  0  0  0  0  0  0  0  0999 V2000
   -1.3999   -4.9720   -1.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5663   -4.5097    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9442   -3.0861    0.1900 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5141   -2.9201    1.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9563   -2.7489   -0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7204   -2.2708    0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4800   -2.8919   -0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6819   -2.2277   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6755   -0.8650    0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8607   -0.1610   -0.0220 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1461   -0.6617   -0.1899 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0001   -0.3194    0.8654 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7060    0.8382    0.6398 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1128    1.4685    1.9569 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8306    2.6463    1.6669 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8582    1.8690   -0.0953 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4862    3.1010   -0.0613 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6308    1.4029   -1.5151 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4470    1.9021   -2.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6699   -0.1029   -1.5064 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9221   -0.6176   -1.8238 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4708   -0.2199    0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401   -0.8855    0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8641   -0.2642    0.4285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9845    0.3549    0.5917 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3002    1.2239   -0.5059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5184    1.8053   -0.1980 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2653    2.2434   -1.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5235    1.1806   -2.2807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1915    3.0351    0.6503 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2848    3.3335    1.4750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9857    2.6560    1.4900 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7891    2.8765    0.8445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0937    1.2047    1.8583 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2756    0.9874    2.5371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1211   -6.0210   -1.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5127   -4.3997   -2.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306   -5.1486    0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6052   -2.9976    1.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1038   -3.7407    2.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345   -1.9817    2.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2683   -3.6611   -1.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9065   -2.4620   -0.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6315   -2.0124   -1.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5495   -3.9920   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5858   -2.8103   -0.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2287   -1.7575   -0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6483    0.6168    0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7227    0.7647    2.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2158    1.7604    2.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5159    2.4296    0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8776    1.9024    0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8284    3.7949   -0.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4758    1.7893   -2.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4924    2.0341   -3.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9734   -0.4593   -2.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0327   -1.4438   -1.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    0.8755    0.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9348   -0.2865    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1597    1.0974    0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6898    3.0007   -2.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2255    2.7142   -1.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3485    1.3669   -2.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0064    3.9207    0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9400    3.4319    2.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9901    3.2508    2.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9092    3.0900   -0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2507    0.8890    2.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5531    0.0401    2.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  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
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  9 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
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 27 28  1  0
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 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 23  6  1  0
 34 25  1  0
 20 11  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  4 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
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  7 45  1  0
  8 46  1  0
 11 47  1  6
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 29 63  1  0
 30 64  1  6
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 32 66  1  1
 33 67  1  0
 34 68  1  1
 35 69  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.400  -4.972  -1.208  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.566  -4.510   0.026  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.944  -3.086   0.190  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.514  -2.920   1.589  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.956  -2.749  -0.869  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.720  -2.271   0.142  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.480  -2.892  -0.029  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.682  -2.228  -0.088  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.676  -0.865   0.032  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.861  -0.161  -0.022  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.146  -0.662  -0.190  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.000  -0.319   0.865  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.706   0.838   0.640  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.113   1.468   1.957  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.831   2.646   1.667  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.858   1.869  -0.095  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.486   3.101  -0.061  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.631   1.403  -1.515  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.447   1.902  -2.041  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.670  -0.103  -1.506  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.922  -0.618  -1.824  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.471  -0.220   0.205  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.740  -0.886   0.265  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.864  -0.264   0.429  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.985   0.355   0.592  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.300   1.224  -0.506  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.518   1.805  -0.198  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.265   2.243  -1.442  0.00  0.00           C+0
HETATM   29  O   UNK     0      -5.524   1.181  -2.281  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.191   3.035   0.650  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.285   3.333   1.475  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.986   2.656   1.490  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.789   2.877   0.845  0.00  0.00           O+0
HETATM   34  C   UNK     0      -3.094   1.205   1.858  0.00  0.00           C+0
HETATM   35  O   UNK     0      -4.276   0.987   2.537  0.00  0.00           O+0
HETATM   36  H   UNK     0      -1.121  -6.021  -1.346  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.513  -4.400  -2.111  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.431  -5.149   0.881  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.605  -2.998   1.585  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.104  -3.741   2.211  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.135  -1.982   2.067  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.268  -3.661  -1.441  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.906  -2.462  -0.329  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.632  -2.012  -1.600  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.550  -3.992  -0.128  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.586  -2.810  -0.227  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.229  -1.758  -0.287  0.00  0.00           H+0
HETATM   48  H   UNK     0       6.648   0.617   0.079  0.00  0.00           H+0
HETATM   49  H   UNK     0       6.723   0.765   2.552  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.216   1.760   2.518  0.00  0.00           H+0
HETATM   51  H   UNK     0       7.516   2.430   0.995  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.878   1.902   0.411  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.828   3.795  -0.255  0.00  0.00           H+0
HETATM   54  H   UNK     0       5.476   1.789  -2.147  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.492   2.034  -3.028  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.973  -0.459  -2.295  0.00  0.00           H+0
HETATM   57  H   UNK     0       6.033  -1.444  -1.297  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.514   0.876   0.297  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.935  -0.287   0.638  0.00  0.00           H+0
HETATM   60  H   UNK     0      -5.160   1.097   0.352  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.690   3.001  -2.017  0.00  0.00           H+0
HETATM   62  H   UNK     0      -6.226   2.714  -1.171  0.00  0.00           H+0
HETATM   63  H   UNK     0      -6.348   1.367  -2.794  0.00  0.00           H+0
HETATM   64  H   UNK     0      -4.006   3.921   0.025  0.00  0.00           H+0
HETATM   65  H   UNK     0      -4.940   3.432   2.394  0.00  0.00           H+0
HETATM   66  H   UNK     0      -2.990   3.251   2.427  0.00  0.00           H+0
HETATM   67  H   UNK     0      -1.909   3.090  -0.113  0.00  0.00           H+0
HETATM   68  H   UNK     0      -2.251   0.889   2.503  0.00  0.00           H+0
HETATM   69  H   UNK     0      -4.553   0.040   2.429  0.00  0.00           H+0
CONECT    1    2   36   37                                                  
CONECT    2    1    3   38                                                  
CONECT    3    2    4    5    6                                             
CONECT    4    3   39   40   41                                             
CONECT    5    3   42   43   44                                             
CONECT    6    3    7   23                                                  
CONECT    7    6    8   45                                                  
CONECT    8    7    9   46                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   20   47                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   16   48                                             
CONECT   14   13   15   49   50                                             
CONECT   15   14   51                                                       
CONECT   16   13   17   18   52                                             
CONECT   17   16   53                                                       
CONECT   18   16   19   20   54                                             
CONECT   19   18   55                                                       
CONECT   20   18   21   11   56                                             
CONECT   21   20   57                                                       
CONECT   22    9   23   58                                                  
CONECT   23   22   24    6                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   34   59                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   30   60                                             
CONECT   28   27   29   61   62                                             
CONECT   29   28   63                                                       
CONECT   30   27   31   32   64                                             
CONECT   31   30   65                                                       
CONECT   32   30   33   34   66                                             
CONECT   33   32   67                                                       
CONECT   34   32   35   25   68                                             
CONECT   35   34   69                                                       
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    2                                                            
CONECT   39    4                                                            
CONECT   40    4                                                            
CONECT   41    4                                                            
CONECT   42    5                                                            
CONECT   43    5                                                            
CONECT   44    5                                                            
CONECT   45    7                                                            
CONECT   46    8                                                            
CONECT   47   11                                                            
CONECT   48   13                                                            
CONECT   49   14                                                            
CONECT   50   14                                                            
CONECT   51   15                                                            
CONECT   52   16                                                            
CONECT   53   17                                                            
CONECT   54   18                                                            
CONECT   55   19                                                            
CONECT   56   20                                                            
CONECT   57   21                                                            
CONECT   58   22                                                            
CONECT   59   25                                                            
CONECT   60   27                                                            
CONECT   61   28                                                            
CONECT   62   28                                                            
CONECT   63   29                                                            
CONECT   64   30                                                            
CONECT   65   31                                                            
CONECT   66   32                                                            
CONECT   67   33                                                            
CONECT   68   34                                                            
CONECT   69   35                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  142    0
END

RDKit          3D

69 71  0  0  0  0  0  0  0  0999 V2000
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 34 68  1  1
 35 69  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Di-O-glucopyranosyloxy-4-(1,1-dimethyl-2-propenyl)benzene	MeSH

Chemical Formula

C₂₃H₃₄O₁₂

Average Mass

502.5130 Da

Monoisotopic Mass

502.20503 Da

IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(2-methylbut-3-en-2-yl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenoxy]oxane-3,4,5-triol

Traditional Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(2-methylbut-3-en-2-yl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenoxy]oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

CC(C)(C=C)C1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1

InChI Identifier

InChI=1S/C23H34O12/c1-4-23(2,3)11-6-5-10(32-21-19(30)17(28)15(26)13(8-24)34-21)7-12(11)33-22-20(31)18(29)16(27)14(9-25)35-22/h4-7,13-22,24-31H,1,8-9H2,2-3H3/t13-,14-,15-,16-,17+,18+,19-,20-,21-,22-/m1/s1

InChI Key

VWNIXYVUBPRGGF-OALZDZJCSA-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
Acremonium	NPAtlas	19734652

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
Phenylpropane
Phenoxy compound
Phenol ether
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Primary alcohol
Hydrocarbon derivative
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	-0.75	ALOGPS
logP	-1.5	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	11.9	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	198.76 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	117.62 m³·mol⁻¹	ChemAxon
Polarizability	50.29 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

NPAtlas ID

NPA014113

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28286751

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101489525

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Izumikawa M, Khan ST, Komaki H, Nagai A, Inaba S, Takagi M, Shin-Ya K: JBIR-37 and -38, novel glycosyl benzenediols, isolated from the sponge-derived fungus, Acremonium sp. SpF080624G1f01. Biosci Biotechnol Biochem. 2009 Sep;73(9):2138-40. doi: 10.1271/bbb.90346. Epub 2009 Sep 7. [PubMed:19734652 ]

Showing NP-Card for JBIR-37 (NP0008708)

MOL for NP0008708 (JBIR-37)

3D MOL for NP0008708 (JBIR-37)

3D SDF for NP0008708 (JBIR-37)

3D-SDF for NP0008708 (JBIR-37)

PDB for NP0008708 (JBIR-37)

3D PDB for NP0008708 (JBIR-37)

SMILES for NP0008708 (JBIR-37)

INCHI for NP0008708 (JBIR-37)

Structure for NP0008708 (JBIR-37)

3D Structure for NP0008708 (JBIR-37)