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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:24 UTC

Update Date

2022-03-07 02:52:43 UTC

HMDB ID

HMDB0030849

Secondary Accession Numbers

HMDB30849

Metabolite Identification

Common Name

Artocarpin

Description

Artocarpin, also known as artocarpin lectin, belongs to the class of organic compounds known as 3-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3-position. Artocarpin has been detected, but not quantified in, a few different foods, such as breadfruits (Artocarpus altilis), fruits, and jackfruits (Artocarpus heterophyllus). This could make artocarpin a potential biomarker for the consumption of these foods. Artocarpin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Artocarpin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061305332D          

 32 34  0  0  0  0            999 V2000
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  8  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  6  1  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15  7  2  0  0  0  0
 16  8  1  0  0  0  0
 16 12  2  0  0  0  0
 17 11  1  0  0  0  0
 18  9  1  0  0  0  0
 19 10  1  0  0  0  0
 20 12  1  0  0  0  0
 20 17  2  0  0  0  0
 21 13  2  0  0  0  0
 21 18  1  0  0  0  0
 22 13  1  0  0  0  0
 23 22  2  0  0  0  0
 24 18  2  0  0  0  0
 24 23  1  0  0  0  0
 25 19  1  0  0  0  0
 25 23  1  0  0  0  0
 26 17  1  0  0  0  0
 26 19  2  0  0  0  0
 27 16  1  0  0  0  0
 28 20  1  0  0  0  0
 29 24  1  0  0  0  0
 30 25  2  0  0  0  0
 31  5  1  0  0  0  0
 31 21  1  0  0  0  0
 32 22  1  0  0  0  0
 32 26  1  0  0  0  0
M  END

HMDB0030849
     RDKit          3D
Artocarpin
 60 62  0  0  0  0  0  0  0  0999 V2000
    3.7827   -1.4193    3.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8898   -0.6839    1.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7743   -0.5215    1.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5626   -1.0923    1.4805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4141   -0.9451    0.6969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6974   -1.4828    1.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8355   -1.3662    0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0119   -2.0006    0.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1695   -2.3596    0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2623   -2.9092    0.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2062   -3.1207    2.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3076   -3.6725    2.9555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0561   -2.7779    2.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911   -2.2354    2.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8668   -1.9169    3.0340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7982   -0.6648   -0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9463   -0.4283   -1.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9241    0.5660   -1.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2785    1.6758   -1.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2597    2.5887   -1.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7166    2.0296   -3.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5954   -0.0806   -1.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5295    0.5628   -2.2882 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5311   -0.2270   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7269    0.3464   -0.8734 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6896    1.0331   -2.0508 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8677    0.1925   -0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0680    0.8068   -0.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2640    0.8215   -0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4050    1.5424   -0.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9830    2.5484    0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9396    2.1795   -2.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1562   -0.8790    3.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7882   -1.5289    3.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3043   -2.4104    2.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4950   -1.6481    2.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2932   -2.2616   -0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1575   -3.1722    0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3431   -3.8571    3.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0128   -2.9453    4.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7896   -2.0566    4.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5565    0.1522   -2.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4504   -1.2389   -2.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3613    0.3748   -0.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8406    3.6321   -1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4237    2.3056   -0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1858    2.6039   -1.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0060    1.2282   -3.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1531    2.9690   -3.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6224    2.1589   -3.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3561    1.5208   -2.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086    1.3633   -1.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4324    0.3182    0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1963    0.8127   -0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1673    3.1258    0.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5935    2.1181    1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5515    3.2928   -0.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8527    2.6635   -2.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2004    2.9764   -1.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6478    1.3929   -2.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
  7 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 16 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 27  3  1  0
 24  5  2  0
 14  8  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  9 37  1  0
 10 38  1  0
 12 39  1  0
 13 40  1  0
 15 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 26 51  1  0
 28 52  1  0
 29 53  1  0
 30 54  1  0
 31 55  1  0
 31 56  1  0
 31 57  1  0
 32 58  1  0
 32 59  1  0
 32 60  1  0
M  END


  Mrv0541 05061305332D          

 32 34  0  0  0  0            999 V2000
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  8  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  6  1  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15  7  2  0  0  0  0
 16  8  1  0  0  0  0
 16 12  2  0  0  0  0
 17 11  1  0  0  0  0
 18  9  1  0  0  0  0
 19 10  1  0  0  0  0
 20 12  1  0  0  0  0
 20 17  2  0  0  0  0
 21 13  2  0  0  0  0
 21 18  1  0  0  0  0
 22 13  1  0  0  0  0
 23 22  2  0  0  0  0
 24 18  2  0  0  0  0
 24 23  1  0  0  0  0
 25 19  1  0  0  0  0
 25 23  1  0  0  0  0
 26 17  1  0  0  0  0
 26 19  2  0  0  0  0
 27 16  1  0  0  0  0
 28 20  1  0  0  0  0
 29 24  1  0  0  0  0
 30 25  2  0  0  0  0
 31  5  1  0  0  0  0
 31 21  1  0  0  0  0
 32 22  1  0  0  0  0
 32 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030849

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(O)=C1\C=C\C(C)C)C(=O)C(CC=C(C)C)=C(O2)C1=C(O)C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O6/c1-14(2)6-9-18-21(31-5)13-22-23(24(18)29)25(30)19(10-7-15(3)4)26(32-22)17-11-8-16(27)12-20(17)28/h6-9,11-14,27-29H,10H2,1-5H3/b9-6+

> <INCHI_KEY>
KRGDFVQWQJIMEK-RMKNXTFCSA-N

> <FORMULA>
C26H28O6

> <MOLECULAR_WEIGHT>
436.4969

> <EXACT_MASS>
436.188588628

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
48.59407995718779

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(1E)-3-methylbut-1-en-1-yl]-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

> <ALOGPS_LOGP>
5.18

> <JCHEM_LOGP>
6.014638791333333

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.622941975386514

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.980628695188043

> <JCHEM_PKA_STRONGEST_BASIC>
-4.759493519460069

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
127.44519999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(1E)-3-methylbut-1-en-1-yl]-3-(3-methylbut-2-en-1-yl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030849
     RDKit          3D
Artocarpin
 60 62  0  0  0  0  0  0  0  0999 V2000
    3.7827   -1.4193    3.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8898   -0.6839    1.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7743   -0.5215    1.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5626   -1.0923    1.4805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4141   -0.9451    0.6969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6974   -1.4828    1.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8355   -1.3662    0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0119   -2.0006    0.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1695   -2.3596    0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2623   -2.9092    0.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2062   -3.1207    2.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3076   -3.6725    2.9555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0561   -2.7779    2.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911   -2.2354    2.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8668   -1.9169    3.0340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7982   -0.6648   -0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9463   -0.4283   -1.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9241    0.5660   -1.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2785    1.6758   -1.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2597    2.5887   -1.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7166    2.0296   -3.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5954   -0.0806   -1.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5295    0.5628   -2.2882 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5311   -0.2270   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7269    0.3464   -0.8734 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6896    1.0331   -2.0508 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8677    0.1925   -0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0680    0.8068   -0.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2640    0.8215   -0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4050    1.5424   -0.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9830    2.5484    0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9396    2.1795   -2.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1562   -0.8790    3.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7882   -1.5289    3.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3043   -2.4104    2.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4950   -1.6481    2.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2932   -2.2616   -0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1575   -3.1722    0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3431   -3.8571    3.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0128   -2.9453    4.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7896   -2.0566    4.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5565    0.1522   -2.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4504   -1.2389   -2.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3613    0.3748   -0.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8406    3.6321   -1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4237    2.3056   -0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1858    2.6039   -1.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0060    1.2282   -3.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1531    2.9690   -3.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6224    2.1589   -3.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3561    1.5208   -2.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086    1.3633   -1.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4324    0.3182    0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1963    0.8127   -0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1673    3.1258    0.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5935    2.1181    1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5515    3.2928   -0.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8527    2.6635   -2.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2004    2.9764   -1.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6478    1.3929   -2.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
  7 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 16 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 27  3  1  0
 24  5  2  0
 14  8  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  9 37  1  0
 10 38  1  0
 12 39  1  0
 13 40  1  0
 15 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 26 51  1  0
 28 52  1  0
 29 53  1  0
 30 54  1  0
 31 55  1  0
 31 56  1  0
 31 57  1  0
 32 58  1  0
 32 59  1  0
 32 60  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5   31                                                            
CONECT    6    9   14                                                       
CONECT    7   10   15                                                       
CONECT    8   11   16                                                       
CONECT    9    6   18                                                       
CONECT   10    7   19                                                       
CONECT   11    8   17                                                       
CONECT   12   16   20                                                       
CONECT   13   21   22                                                       
CONECT   14    1    2    6                                                  
CONECT   15    3    4    7                                                  
CONECT   16    8   12   27                                                  
CONECT   17   11   20   26                                                  
CONECT   18    9   21   24                                                  
CONECT   19   10   25   26                                                  
CONECT   20   12   17   28                                                  
CONECT   21   13   18   31                                                  
CONECT   22   13   23   32                                                  
CONECT   23   22   24   25                                                  
CONECT   24   18   23   29                                                  
CONECT   25   19   23   30                                                  
CONECT   26   17   19   32                                                  
CONECT   27   16                                                            
CONECT   28   20                                                            
CONECT   29   24                                                            
CONECT   30   25                                                            
CONECT   31    5   21                                                       
CONECT   32   22   26                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

COMPND    HMDB0030849
HETATM    1  C1  UNL     1       3.783  -1.419   3.067  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.890  -0.684   1.874  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.774  -0.521   1.081  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.563  -1.092   1.481  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.414  -0.945   0.697  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.697  -1.483   1.086  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.836  -1.366   0.358  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.012  -2.001   0.891  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.170  -2.360   0.295  1.00  0.00           C  
HETATM   10  C8  UNL     1      -5.262  -2.909   0.955  1.00  0.00           C  
HETATM   11  C9  UNL     1      -5.206  -3.121   2.303  1.00  0.00           C  
HETATM   12  O3  UNL     1      -6.308  -3.673   2.955  1.00  0.00           O  
HETATM   13  C10 UNL     1      -4.056  -2.778   2.966  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.991  -2.235   2.288  1.00  0.00           C  
HETATM   15  O4  UNL     1      -1.867  -1.917   3.034  1.00  0.00           O  
HETATM   16  C12 UNL     1      -1.798  -0.665  -0.807  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.946  -0.428  -1.670  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.924   0.566  -1.134  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.278   1.676  -1.772  1.00  0.00           C  
HETATM   20  C16 UNL     1      -5.260   2.589  -1.139  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.717   2.030  -3.108  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.595  -0.081  -1.233  1.00  0.00           C  
HETATM   23  O5  UNL     1      -0.529   0.563  -2.288  1.00  0.00           O  
HETATM   24  C19 UNL     1       0.531  -0.227  -0.462  1.00  0.00           C  
HETATM   25  C20 UNL     1       1.727   0.346  -0.873  1.00  0.00           C  
HETATM   26  O6  UNL     1       1.690   1.033  -2.051  1.00  0.00           O  
HETATM   27  C21 UNL     1       2.868   0.192  -0.082  1.00  0.00           C  
HETATM   28  C22 UNL     1       4.068   0.807  -0.561  1.00  0.00           C  
HETATM   29  C23 UNL     1       5.264   0.821  -0.032  1.00  0.00           C  
HETATM   30  C24 UNL     1       6.405   1.542  -0.718  1.00  0.00           C  
HETATM   31  C25 UNL     1       6.983   2.548   0.221  1.00  0.00           C  
HETATM   32  C26 UNL     1       5.940   2.179  -2.006  1.00  0.00           C  
HETATM   33  H1  UNL     1       3.156  -0.879   3.829  1.00  0.00           H  
HETATM   34  H2  UNL     1       4.788  -1.529   3.568  1.00  0.00           H  
HETATM   35  H3  UNL     1       3.304  -2.410   2.938  1.00  0.00           H  
HETATM   36  H4  UNL     1       1.495  -1.648   2.389  1.00  0.00           H  
HETATM   37  H5  UNL     1      -4.293  -2.262  -0.754  1.00  0.00           H  
HETATM   38  H6  UNL     1      -6.158  -3.172   0.416  1.00  0.00           H  
HETATM   39  H7  UNL     1      -6.343  -3.857   3.937  1.00  0.00           H  
HETATM   40  H8  UNL     1      -4.013  -2.945   4.032  1.00  0.00           H  
HETATM   41  H9  UNL     1      -1.790  -2.057   4.013  1.00  0.00           H  
HETATM   42  H10 UNL     1      -2.556   0.152  -2.614  1.00  0.00           H  
HETATM   43  H11 UNL     1      -3.450  -1.239  -2.152  1.00  0.00           H  
HETATM   44  H12 UNL     1      -4.361   0.375  -0.167  1.00  0.00           H  
HETATM   45  H13 UNL     1      -4.841   3.632  -1.137  1.00  0.00           H  
HETATM   46  H14 UNL     1      -5.424   2.306  -0.068  1.00  0.00           H  
HETATM   47  H15 UNL     1      -6.186   2.604  -1.725  1.00  0.00           H  
HETATM   48  H16 UNL     1      -4.006   1.228  -3.821  1.00  0.00           H  
HETATM   49  H17 UNL     1      -4.153   2.969  -3.477  1.00  0.00           H  
HETATM   50  H18 UNL     1      -2.622   2.159  -3.085  1.00  0.00           H  
HETATM   51  H19 UNL     1       2.356   1.521  -2.565  1.00  0.00           H  
HETATM   52  H20 UNL     1       4.009   1.363  -1.526  1.00  0.00           H  
HETATM   53  H21 UNL     1       5.432   0.318   0.894  1.00  0.00           H  
HETATM   54  H22 UNL     1       7.196   0.813  -0.996  1.00  0.00           H  
HETATM   55  H23 UNL     1       6.167   3.126   0.717  1.00  0.00           H  
HETATM   56  H24 UNL     1       7.594   2.118   1.019  1.00  0.00           H  
HETATM   57  H25 UNL     1       7.551   3.293  -0.392  1.00  0.00           H  
HETATM   58  H26 UNL     1       6.853   2.664  -2.449  1.00  0.00           H  
HETATM   59  H27 UNL     1       5.200   2.976  -1.870  1.00  0.00           H  
HETATM   60  H28 UNL     1       5.648   1.393  -2.732  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3
CONECT    3    4    4   27
CONECT    4    5   36
CONECT    5    6   24   24
CONECT    6    7
CONECT    7    8   16   16
CONECT    8    9    9   14
CONECT    9   10   37
CONECT   10   11   11   38
CONECT   11   12   13
CONECT   12   39
CONECT   13   14   14   40
CONECT   14   15
CONECT   15   41
CONECT   16   17   22
CONECT   17   18   42   43
CONECT   18   19   19   44
CONECT   19   20   21
CONECT   20   45   46   47
CONECT   21   48   49   50
CONECT   22   23   23   24
CONECT   24   25
CONECT   25   26   27   27
CONECT   26   51
CONECT   27   28
CONECT   28   29   29   52
CONECT   29   30   53
CONECT   30   31   32   54
CONECT   31   55   56   57
CONECT   32   58   59   60
END

HMDB0030849
     RDKit          3D
Artocarpin
 60 62  0  0  0  0  0  0  0  0999 V2000
    3.7827   -1.4193    3.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8898   -0.6839    1.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7743   -0.5215    1.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5626   -1.0923    1.4805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4141   -0.9451    0.6969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6974   -1.4828    1.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8355   -1.3662    0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0119   -2.0006    0.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1695   -2.3596    0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2623   -2.9092    0.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2062   -3.1207    2.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3076   -3.6725    2.9555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0561   -2.7779    2.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911   -2.2354    2.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8668   -1.9169    3.0340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7982   -0.6648   -0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9463   -0.4283   -1.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9241    0.5660   -1.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2785    1.6758   -1.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2597    2.5887   -1.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7166    2.0296   -3.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5954   -0.0806   -1.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5295    0.5628   -2.2882 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5311   -0.2270   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7269    0.3464   -0.8734 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6896    1.0331   -2.0508 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8677    0.1925   -0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0680    0.8068   -0.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2640    0.8215   -0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4050    1.5424   -0.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9830    2.5484    0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9396    2.1795   -2.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1562   -0.8790    3.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7882   -1.5289    3.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3043   -2.4104    2.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4950   -1.6481    2.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2932   -2.2616   -0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1575   -3.1722    0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3431   -3.8571    3.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0128   -2.9453    4.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7896   -2.0566    4.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5565    0.1522   -2.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4504   -1.2389   -2.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3613    0.3748   -0.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8406    3.6321   -1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4237    2.3056   -0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1858    2.6039   -1.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0060    1.2282   -3.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1531    2.9690   -3.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6224    2.1589   -3.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3561    1.5208   -2.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0086    1.3633   -1.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4324    0.3182    0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1963    0.8127   -0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1673    3.1258    0.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5935    2.1181    1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5515    3.2928   -0.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8527    2.6635   -2.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2004    2.9764   -1.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6478    1.3929   -2.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
  7 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 16 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 27  3  1  0
 24  5  2  0
 14  8  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  9 37  1  0
 10 38  1  0
 12 39  1  0
 13 40  1  0
 15 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 26 51  1  0
 28 52  1  0
 29 53  1  0
 30 54  1  0
 31 55  1  0
 31 56  1  0
 31 57  1  0
 32 58  1  0
 32 59  1  0
 32 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2',4',5-Trihydroxy-7-methoxy-6-(3-methyl-1-butenyl)-3-(3-methyl-2-butenyl)flavone	ChEBI
5-Hydroxy-7-methoxy-3-(3-methyl-2-butenyl)-6-(3-methyl-1-butenyl)-2-(2,4-dihydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
Artocarpin lectin	MeSH
2-(2,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-6-(3-methyl-1-butenyl)-3-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9ci	HMDB

Chemical Formula

C₂₆H₂₈O₆

Average Molecular Weight

436.4969

Monoisotopic Molecular Weight

436.188588628

IUPAC Name

2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(1E)-3-methylbut-1-en-1-yl]-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Traditional Name

2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(1E)-3-methylbut-1-en-1-yl]-3-(3-methylbut-2-en-1-yl)chromen-4-one

CAS Registry Number

7608-44-8

SMILES

COC1=CC2=C(C(O)=C1\C=C\C(C)C)C(=O)C(CC=C(C)C)=C(O2)C1=C(O)C=C(O)C=C1

InChI Identifier

InChI=1S/C26H28O6/c1-14(2)6-9-18-21(31-5)13-22-23(24(18)29)25(30)19(10-7-15(3)4)26(32-22)17-11-8-16(27)12-20(17)28/h6-9,11-14,27-29H,10H2,1-5H3/b9-6+

InChI Key

KRGDFVQWQJIMEK-RMKNXTFCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

3-prenylated flavones

Alternative Parents

Substituents

3-prenylated flavone
7-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Anisole
Styrene
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxyflavone (CHEBI:65439 )
trihydroxyflavone (CHEBI:65439 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030849)

Cellular substructure

Membrane (HMDB: HMDB0030849)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030849)

Source

Endogenous

Endogenous (HMDB: HMDB0030849)

Plant

Plant (HMDB: HMDB0030849)

Exogenous

Food

Food (HMDB: HMDB0030849)

Fruit

Tropical fruit

Breadfruit (FooDB: FOOD00309)
Jackfruit (FooDB: FOOD00384)

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	174 - 175 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0027 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0026 g/L	ALOGPS
logP	5.18	ALOGPS
logP	6.01	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	7.98	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	127.45 m³·mol⁻¹	ChemAxon
Polarizability	48.59 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	208.824	30932474
DeepCCS	[M-H]-	206.429	30932474
DeepCCS	[M-2H]-	239.312	30932474
DeepCCS	[M+Na]+	214.737	30932474
AllCCS	[M+H]+	207.5	32859911
AllCCS	[M+H-H2O]+	204.9	32859911
AllCCS	[M+NH4]+	209.8	32859911
AllCCS	[M+Na]+	210.5	32859911
AllCCS	[M-H]-	205.5	32859911
AllCCS	[M+Na-2H]-	205.7	32859911
AllCCS	[M+HCOO]-	206.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Artocarpin	COC1=CC2=C(C(O)=C1\C=C\C(C)C)C(=O)C(CC=C(C)C)=C(O2)C1=C(O)C=C(O)C=C1	5464.1	Standard polar	33892256
Artocarpin	COC1=CC2=C(C(O)=C1\C=C\C(C)C)C(=O)C(CC=C(C)C)=C(O2)C1=C(O)C=C(O)C=C1	3539.4	Standard non polar	33892256
Artocarpin	COC1=CC2=C(C(O)=C1\C=C\C(C)C)C(=O)C(CC=C(C)C)=C(O2)C1=C(O)C=C(O)C=C1	3698.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Artocarpin,1TMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O)C=C1O)O2	3591.7	Semi standard non polar	33892256
Artocarpin,1TMS,isomer #2	COC1=CC2=C(C(O)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O)C=C1O[Si](C)(C)C)O2	3561.9	Semi standard non polar	33892256
Artocarpin,1TMS,isomer #3	COC1=CC2=C(C(O)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O[Si](C)(C)C)C=C1O)O2	3594.8	Semi standard non polar	33892256
Artocarpin,2TMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O[Si](C)(C)C)C=C1O)O2	3500.4	Semi standard non polar	33892256
Artocarpin,2TMS,isomer #2	COC1=CC2=C(C(O[Si](C)(C)C)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O)C=C1O[Si](C)(C)C)O2	3475.5	Semi standard non polar	33892256
Artocarpin,2TMS,isomer #3	COC1=CC2=C(C(O)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)O2	3498.9	Semi standard non polar	33892256
Artocarpin,3TMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)O2	3470.4	Semi standard non polar	33892256
Artocarpin,1TBDMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O)C=C1O)O2	3839.9	Semi standard non polar	33892256
Artocarpin,1TBDMS,isomer #2	COC1=CC2=C(C(O)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)O2	3807.2	Semi standard non polar	33892256
Artocarpin,1TBDMS,isomer #3	COC1=CC2=C(C(O)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)O2	3854.9	Semi standard non polar	33892256
Artocarpin,2TBDMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)O2	3948.7	Semi standard non polar	33892256
Artocarpin,2TBDMS,isomer #2	COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)O2	3911.2	Semi standard non polar	33892256
Artocarpin,2TBDMS,isomer #3	COC1=CC2=C(C(O)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)O2	3970.8	Semi standard non polar	33892256
Artocarpin,3TBDMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1/C=C/C(C)C)C(=O)C(CC=C(C)C)=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)O2	4066.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Artocarpin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0016900000-b6a66201932d08b82d02	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artocarpin GC-MS (3 TMS) - 70eV, Positive	splash10-000i-1000029000-6e75e6ccb1941c992db7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artocarpin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin ESI-TOF 10V, Negative-QTOF	splash10-0159-0590000000-6545d7dadecee8a4f74f	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin ESI-TOF 30V, Negative-QTOF	splash10-03di-0029100000-b05a8e20e23cb267e253	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin ESI-TOF , Negative-QTOF	splash10-000i-0002900010-8da91c9103874a49a7fa	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin ESI-TOF 50V, Negative-QTOF	splash10-0a4i-0191000000-bd435bd5fa1fd964bc2a	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin ESI-TOF 20V, Negative-QTOF	splash10-01p9-0007900000-e9660f3601ab50e32862	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin ESI-TOF 40V, Negative-QTOF	splash10-0bt9-0095000000-af0abacc4b61c8c1f999	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin ESI-TOF 10V, Negative-QTOF	splash10-000i-0000900000-0edef93ed272697afd8a	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin ESI-TOF 30V, Negative-QTOF	splash10-03di-0029100000-b05a8e20e23cb267e253	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin ESI-TOF , Negative-QTOF	splash10-000i-0002900010-8da91c9103874a49a7fa	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin ESI-TOF 50V, Negative-QTOF	splash10-0a4i-0191000000-bd435bd5fa1fd964bc2a	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin ESI-TOF 20V, Negative-QTOF	splash10-01p9-0007900000-e9660f3601ab50e32862	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin ESI-TOF 40V, Negative-QTOF	splash10-0bt9-0095000000-af0abacc4b61c8c1f999	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin LC-ESI-TOF , negative-QTOF	splash10-000i-0000900000-0edef93ed272697afd8a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin LC-ESI-TOF , negative-QTOF	splash10-03di-0029100000-b05a8e20e23cb267e253	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin LC-ESI-TOF , negative-QTOF	splash10-0a4i-0191000000-bd435bd5fa1fd964bc2a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin LC-ESI-TOF , negative-QTOF	splash10-01p9-0007900000-e9660f3601ab50e32862	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin LC-ESI-TOF , negative-QTOF	splash10-0bt9-0095000000-af0abacc4b61c8c1f999	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin 50V, Positive-QTOF	splash10-0a4i-0191000000-bd435bd5fa1fd964bc2a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Artocarpin 40V, Positive-QTOF	splash10-0bt9-0095000000-c149b87b1a12b52906eb	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artocarpin 10V, Positive-QTOF	splash10-000i-1005900000-d8d4a3082742081f6e69	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artocarpin 20V, Positive-QTOF	splash10-017r-4009300000-cb731e983db7d2669e38	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artocarpin 40V, Positive-QTOF	splash10-06dr-6393100000-9fca685296e8905c5773	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artocarpin 10V, Negative-QTOF	splash10-000i-0000900000-dd022c2539a92356788e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artocarpin 20V, Negative-QTOF	splash10-000i-0014900000-bfa7024d47d949dc121b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artocarpin 40V, Negative-QTOF	splash10-0a4i-2925100000-b56b4bc0809997d590ad	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002808

KNApSAcK ID

C00004032

Chemspider ID

4572407

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5458461

PDB ID

Not Available

ChEBI ID

65439

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1823161

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Artocarpin (HMDB0030849)

MOL for HMDB0030849 (Artocarpin)

3D MOL for HMDB0030849 (Artocarpin)

3D SDF for HMDB0030849 (Artocarpin)

3D-SDF for HMDB0030849 (Artocarpin)

PDB for HMDB0030849 (Artocarpin)

3D PDB for HMDB0030849 (Artocarpin)

SMILES for HMDB0030849 (Artocarpin)

INCHI for HMDB0030849 (Artocarpin)

Structure for HMDB0030849 (Artocarpin)

3D Structure for HMDB0030849 (Artocarpin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra