NP-MRD: Showing NP-Card for farobin A (NP0035513)

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Record Information

Version

2.0

Created at

2021-06-20 18:56:16 UTC

Updated at

2021-06-30 00:06:32 UTC

NP-MRD ID

NP0035513

Secondary Accession Numbers

None

Natural Product Identification

Common Name

farobin A

Provided By

JEOL Database JEOL Logo

Description

FAROBIN A belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. farobin A is found in Fargesia robusta. farobin A was first documented in 2010 (PMID: 20863141). FAROBIN A is an essentially neutral compound (based on its pKa) (PMID: 25424560).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120563D          

 71 75  0  0  0  0            999 V2000
   -0.0028    4.6579   -1.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155    5.2425   -1.4488 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9856    4.3724   -0.5196 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566    3.2166   -1.0755 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.7947    1.7022   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839    2.4910    0.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6896    1.0111    2.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939    0.4918    3.8532 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4898   -0.5717    4.4893 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8062   -0.0328    4.7561 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7374    1.6126    4.8453 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.3797   -5.2786   -0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0340   -5.5364   -4.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6441   -2.9642   -4.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1 42  1  0  0  0  0
  1 43  1  0  0  0  0
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M  END

     RDKit          3D

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 37 67  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  1
M  END


  Mrv1652306202120563D          

 71 75  0  0  0  0            999 V2000
   -0.0028    4.6579   -1.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155    5.2425   -1.4488 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9856    4.3724   -0.5196 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566    3.2166   -1.0755 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7068    2.0328   -1.2671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947    1.7022   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839    2.4910    0.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4523    1.9807    1.9857 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6896    1.0111    2.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939    0.4918    3.8532 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4898   -0.5717    4.4893 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8062   -0.0328    4.7561 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7374    1.6126    4.8453 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5493    1.1098    5.9109 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5104    2.7216    4.1297 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7079    3.8189    5.0358 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7725    3.1929    2.8805 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6040    4.1564    2.2122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1063    0.6375   -0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0924   -0.1667   -1.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9923   -1.2002   -1.5077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0141   -2.0193   -2.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0213   -3.0981   -2.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2635   -3.7646   -1.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2200   -4.7830   -1.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9433   -5.1335   -2.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8914   -6.1176   -2.3640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7193   -4.4765   -3.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4392   -4.8222   -4.6998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7728   -3.4642   -3.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1876   -1.8804   -3.6720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7959   -0.7890   -3.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5777   -0.6222   -4.5912 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8117    0.0997   -2.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7077    1.1853   -2.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6001    1.4270   -3.4008 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6419    3.6786   -2.1581 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9639    4.5295   -3.2211 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9244    5.0339   -4.1612 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2567    5.7168   -2.5632 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5738    6.4876   -3.5523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5991    4.2759   -1.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1514    3.8316   -2.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5951    5.4193   -2.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0355    6.1280   -0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3105    2.8685   -0.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3857    1.5278    1.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3120   -0.0072    3.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3482   -1.4070    3.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9076   -0.9643    5.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0832    0.4077    3.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8282    2.0331    5.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8086    1.9003    6.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5182    2.3733    3.8696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0371    4.5535    4.4783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8522    3.7184    3.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1627    4.3573    1.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8194    0.4470    0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6997   -3.4964   -0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3797   -5.2786   -0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9417   -6.4720   -1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0340   -5.5364   -4.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6441   -2.9642   -4.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1861   -2.5314   -4.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4717    0.7662   -4.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4018    4.3093   -1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2198    2.8602   -2.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2492    3.9469   -3.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6889    5.3746   -3.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187    6.3760   -2.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549    6.4838   -4.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0  0  0  0
 34 32  1  0  0  0  0
 32 31  1  0  0  0  0
 31 22  2  0  0  0  0
 22 21  1  0  0  0  0
 22 23  1  0  0  0  0
 32 33  2  0  0  0  0
 11 12  1  0  0  0  0
 35 36  1  0  0  0  0
  8 17  1  0  0  0  0
 23 30  2  0  0  0  0
 17 15  1  0  0  0  0
 30 28  1  0  0  0  0
  6  5  2  0  0  0  0
 28 26  2  0  0  0  0
 15 13  1  0  0  0  0
 26 25  1  0  0  0  0
  5 35  1  0  0  0  0
 25 24  2  0  0  0  0
 24 23  1  0  0  0  0
 35 34  2  0  0  0  0
 26 27  1  0  0  0  0
 13 10  1  0  0  0  0
 28 29  1  0  0  0  0
  6  7  1  0  0  0  0
 20 19  2  0  0  0  0
 19  6  1  0  0  0  0
 20 34  1  0  0  0  0
 10  9  1  0  0  0  0
  9  8  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
  4 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 40  1  0  0  0  0
 40  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
 40 41  1  0  0  0  0
 38 39  1  0  0  0  0
 10 11  1  0  0  0  0
  8  7  1  0  0  0  0
  2  1  1  0  0  0  0
  4  5  1  0  0  0  0
  8 47  1  6  0  0  0
 13 52  1  1  0  0  0
 14 53  1  0  0  0  0
 15 54  1  6  0  0  0
 16 55  1  0  0  0  0
 17 56  1  1  0  0  0
 18 57  1  0  0  0  0
 11 49  1  0  0  0  0
 11 50  1  0  0  0  0
 10 48  1  6  0  0  0
 12 51  1  0  0  0  0
 19 58  1  0  0  0  0
 31 64  1  0  0  0  0
 36 65  1  0  0  0  0
 30 63  1  0  0  0  0
 25 60  1  0  0  0  0
 24 59  1  0  0  0  0
 27 61  1  0  0  0  0
 29 62  1  0  0  0  0
  4 46  1  1  0  0  0
 40 70  1  1  0  0  0
 41 71  1  0  0  0  0
 38 68  1  6  0  0  0
 39 69  1  0  0  0  0
 37 66  1  0  0  0  0
 37 67  1  0  0  0  0
  1 42  1  0  0  0  0
  1 43  1  0  0  0  0
  1 44  1  0  0  0  0
  2 45  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0035513

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(O[H])C([H])=C(C([H])=C1[H])C1=C([H])C(=O)C2=C(O[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])C([H])=C2O1)[C@]1([H])O[C@]([H])(C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O14/c1-9-22(33)14(32)6-16(38-9)21-18(40-27-26(37)25(36)23(34)19(8-28)41-27)7-17-20(24(21)35)13(31)5-15(39-17)10-2-3-11(29)12(30)4-10/h2-5,7,9,14,16,19,22-23,25-30,32-37H,6,8H2,1H3/t9-,14+,16-,19-,22+,23-,25+,26-,27-/m1/s1

> <INCHI_KEY>
UKNXXFWLEJRJCY-NCJQNZQYSA-N

> <FORMULA>
C27H30O14

> <MOLECULAR_WEIGHT>
578.523

> <EXACT_MASS>
578.163555646

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
57.17785702361576

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[(2R,4S,5R,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

> <ALOGPS_LOGP>
-0.19

> <JCHEM_LOGP>
-0.8850605386666667

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.710401964518098

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.896800800344294

> <JCHEM_PKA_STRONGEST_BASIC>
-3.222723438017855

> <JCHEM_POLAR_SURFACE_AREA>
236.05999999999997

> <JCHEM_REFRACTIVITY>
137.51669999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(2R,4S,5R,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 71 75  0  0  0  0  0  0  0  0999 V2000
   -0.0028    4.6579   -1.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155    5.2425   -1.4488 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9856    4.3724   -0.5196 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566    3.2166   -1.0755 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7068    2.0328   -1.2671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947    1.7022   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839    2.4910    0.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4523    1.9807    1.9857 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6896    1.0111    2.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939    0.4918    3.8532 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4898   -0.5717    4.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8062   -0.0328    4.7561 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7374    1.6126    4.8453 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5493    1.1098    5.9109 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5104    2.7216    4.1297 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7079    3.8189    5.0358 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7725    3.1929    2.8805 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6040    4.1564    2.2122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1063    0.6375   -0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0924   -0.1667   -1.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9923   -1.2002   -1.5077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0141   -2.0193   -2.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0213   -3.0981   -2.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2635   -3.7646   -1.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2200   -4.7830   -1.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9433   -5.1335   -2.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8914   -6.1176   -2.3640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7193   -4.4765   -3.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4392   -4.8222   -4.6998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7728   -3.4642   -3.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1876   -1.8804   -3.6720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7959   -0.7890   -3.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5777   -0.6222   -4.5912 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8117    0.0997   -2.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7077    1.1853   -2.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6001    1.4270   -3.4008 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6419    3.6786   -2.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9639    4.5295   -3.2211 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9244    5.0339   -4.1612 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2567    5.7168   -2.5632 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5738    6.4876   -3.5523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5991    4.2759   -1.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1514    3.8316   -2.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5951    5.4193   -2.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0355    6.1280   -0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3105    2.8685   -0.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3857    1.5278    1.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3120   -0.0072    3.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3482   -1.4070    3.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9076   -0.9643    5.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0832    0.4077    3.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8282    2.0331    5.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8086    1.9003    6.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5182    2.3733    3.8696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0371    4.5535    4.4783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8522    3.7184    3.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1627    4.3573    1.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8194    0.4470    0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6997   -3.4964   -0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3797   -5.2786   -0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9417   -6.4720   -1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0340   -5.5364   -4.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6441   -2.9642   -4.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1861   -2.5314   -4.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4717    0.7662   -4.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4018    4.3093   -1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2198    2.8602   -2.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2492    3.9469   -3.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6889    5.3746   -3.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187    6.3760   -2.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549    6.4838   -4.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0
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  2 45  1  1
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      -0.003   4.658  -1.955  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.315   5.242  -1.449  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.986   4.372  -0.520  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.657   3.217  -1.075  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.707   2.033  -1.267  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.795   1.702  -0.234  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.684   2.491   0.883  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.452   1.981   1.986  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.690   1.011   2.710  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.394   0.492   3.853  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.490  -0.572   4.489  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.806  -0.033   4.756  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.737   1.613   4.845  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.549   1.110   5.911  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.510   2.722   4.130  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.708   3.819   5.036  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.773   3.193   2.881  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.604   4.156   2.212  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.106   0.638  -0.340  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.092  -0.167  -1.469  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.992  -1.200  -1.508  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.014  -2.019  -2.626  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.021  -3.098  -2.564  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.264  -3.765  -1.347  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.220  -4.783  -1.255  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.943  -5.133  -2.386  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.891  -6.118  -2.364  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.719  -4.476  -3.592  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.439  -4.822  -4.700  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.773  -3.464  -3.691  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.188  -1.880  -3.672  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.796  -0.789  -3.661  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.578  -0.622  -4.591  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.812   0.100  -2.489  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.708   1.185  -2.391  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.600   1.427  -3.401  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.642   3.679  -2.158  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.964   4.529  -3.221  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.924   5.034  -4.161  0.00  0.00           O+0
HETATM   40  C   UNK     0       2.257   5.717  -2.563  0.00  0.00           C+0
HETATM   41  O   UNK     0       1.574   6.488  -3.552  0.00  0.00           O+0
HETATM   42  H   UNK     0      -0.599   4.276  -1.120  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.151   3.832  -2.653  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.595   5.419  -2.473  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.036   6.128  -0.864  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.311   2.869  -0.263  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.386   1.528   1.621  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.312  -0.007   3.516  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.348  -1.407   3.795  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.908  -0.964   5.421  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.083   0.408   3.930  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.828   2.033   5.292  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.809   1.900   6.427  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.518   2.373   3.870  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.037   4.553   4.478  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.852   3.718   3.164  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.163   4.357   1.355  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.819   0.447   0.458  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.700  -3.496  -0.455  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.380  -5.279  -0.303  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.942  -6.472  -1.459  0.00  0.00           H+0
HETATM   62  H   UNK     0      -5.034  -5.536  -4.394  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.644  -2.964  -4.647  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.186  -2.531  -4.537  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.472   0.766  -4.121  0.00  0.00           H+0
HETATM   66  H   UNK     0       4.402   4.309  -1.673  0.00  0.00           H+0
HETATM   67  H   UNK     0       4.220   2.860  -2.597  0.00  0.00           H+0
HETATM   68  H   UNK     0       2.249   3.947  -3.810  0.00  0.00           H+0
HETATM   69  H   UNK     0       4.689   5.375  -3.665  0.00  0.00           H+0
HETATM   70  H   UNK     0       3.019   6.376  -2.128  0.00  0.00           H+0
HETATM   71  H   UNK     0       2.155   6.484  -4.339  0.00  0.00           H+0
CONECT    1    2   42   43   44                                             
CONECT    2   40    3    1   45                                             
CONECT    3    2    4                                                       
CONECT    4   37    3    5   46                                             
CONECT    5    6   35    4                                                  
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8   17    9    7   47                                             
CONECT    9   10    8                                                       
CONECT   10   13    9   11   48                                             
CONECT   11   12   10   49   50                                             
CONECT   12   11   51                                                       
CONECT   13   15   10   14   52                                             
CONECT   14   13   53                                                       
CONECT   15   17   13   16   54                                             
CONECT   16   15   55                                                       
CONECT   17    8   15   18   56                                             
CONECT   18   17   57                                                       
CONECT   19   20    6   58                                                  
CONECT   20   21   19   34                                                  
CONECT   21   20   22                                                       
CONECT   22   31   21   23                                                  
CONECT   23   22   30   24                                                  
CONECT   24   25   23   59                                                  
CONECT   25   26   24   60                                                  
CONECT   26   28   25   27                                                  
CONECT   27   26   61                                                       
CONECT   28   30   26   29                                                  
CONECT   29   28   62                                                       
CONECT   30   23   28   63                                                  
CONECT   31   32   22   64                                                  
CONECT   32   34   31   33                                                  
CONECT   33   32                                                            
CONECT   34   32   35   20                                                  
CONECT   35   36    5   34                                                  
CONECT   36   35   65                                                       
CONECT   37    4   38   66   67                                             
CONECT   38   37   40   39   68                                             
CONECT   39   38   69                                                       
CONECT   40   38    2   41   70                                             
CONECT   41   40   71                                                       
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    1                                                            
CONECT   45    2                                                            
CONECT   46    4                                                            
CONECT   47    8                                                            
CONECT   48   10                                                            
CONECT   49   11                                                            
CONECT   50   11                                                            
CONECT   51   12                                                            
CONECT   52   13                                                            
CONECT   53   14                                                            
CONECT   54   15                                                            
CONECT   55   16                                                            
CONECT   56   17                                                            
CONECT   57   18                                                            
CONECT   58   19                                                            
CONECT   59   24                                                            
CONECT   60   25                                                            
CONECT   61   27                                                            
CONECT   62   29                                                            
CONECT   63   30                                                            
CONECT   64   31                                                            
CONECT   65   36                                                            
CONECT   66   37                                                            
CONECT   67   37                                                            
CONECT   68   38                                                            
CONECT   69   39                                                            
CONECT   70   40                                                            
CONECT   71   41                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  150    0
END

RDKit          3D

71 75  0  0  0  0  0  0  0  0999 V2000
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   -0.8062   -0.0328    4.7561 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5493    1.1098    5.9109 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5738    6.4876   -3.5523 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3105    2.8685   -0.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3797   -5.2786   -0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9417   -6.4720   -1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6441   -2.9642   -4.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0187    6.3760   -2.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
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 20 21  1  0
 34 32  1  0
 32 31  1  0
 31 22  2  0
 22 21  1  0
 22 23  1  0
 32 33  2  0
 11 12  1  0
 35 36  1  0
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₀O₁₄

Average Mass

578.5230 Da

Monoisotopic Mass

578.16356 Da

IUPAC Name

6-[(2R,4S,5R,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

6-[(2R,4S,5R,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C(O[H])C([H])=C(C([H])=C1[H])C1=C([H])C(=O)C2=C(O[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])C([H])=C2O1)[C@]1([H])O[C@]([H])(C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])C1([H])[H]

InChI Identifier

InChI=1S/C27H30O14/c1-9-22(33)14(32)6-16(38-9)21-18(40-27-26(37)25(36)23(34)19(8-28)41-27)7-17-20(24(21)35)13(31)5-15(39-17)10-2-3-11(29)12(30)4-10/h2-5,7,9,14,16,19,22-23,25-30,32-37H,6,8H2,1H3/t9-,14+,16-,19-,22+,23-,25+,26-,27-/m1/s1

InChI Key

UKNXXFWLEJRJCY-NCJQNZQYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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
Fargesia robusta	JEOL database	Hoyweghen, L. V., et al, J. Nat. Prod. 73, 1575 (2010)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
Flavonoid c-glycoside
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Benzopyran
Catechol
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Monosaccharide
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-0.19	ALOGPS
logP	-0.89	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	6.9	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	236.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	137.52 m³·mol⁻¹	ChemAxon
Polarizability	57.18 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

Not Available

Chemspider ID

25054667

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46938449

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Luo GY, Luo YG, Zhou R, Zhou M, Gu J, Ye Q, Dai Y, Zhang GL: Antioxidant compounds from ethanol extracts of bamboo (Neosinocalamus affinis) leaves. J Asian Nat Prod Res. 2015;17(3):248-55. doi: 10.1080/10286020.2014.981164. Epub 2014 Nov 26. [PubMed:25424560 ]
Van Hoyweghen L, Karalic I, Van Calenbergh S, Deforce D, Heyerick A: Antioxidant flavone glycosides from the leaves of Fargesia robusta. J Nat Prod. 2010 Sep 24;73(9):1573-7. doi: 10.1021/np100220g. [PubMed:20863141 ]
Hoyweghen, L. V., et al. (2010). Hoyweghen, L. V., et al, J. Nat. Prod. 73, 1575 (2010). J. Nat. Prod..

Showing NP-Card for farobin A (NP0035513)

MOL for NP0035513 (farobin A)

3D MOL for NP0035513 (farobin A)

3D SDF for NP0035513 (farobin A)

3D-SDF for NP0035513 (farobin A)

PDB for NP0035513 (farobin A)

3D PDB for NP0035513 (farobin A)

SMILES for NP0035513 (farobin A)

INCHI for NP0035513 (farobin A)

Structure for NP0035513 (farobin A)

3D Structure for NP0035513 (farobin A)