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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:33:24 UTC

Update Date

2022-03-07 02:52:20 UTC

HMDB ID

HMDB0029905

Secondary Accession Numbers

HMDB29905

Metabolite Identification

Common Name

Artonin T

Description

Lucuminoside, also known as lucumin or vicianin, belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Lucuminoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Lucuminoside has been detected, but not quantified in, fruits and mamey sapotes. This could make lucuminoside a potential biomarker for the consumption of these foods.

Structure

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


  Mrv0541 05061304542D          

 33 37  0  0  0  0            999 V2000
    4.8722   -0.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1584   -2.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6329    1.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2638    1.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8460   -5.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4432   -0.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7290   -1.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2730   -3.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8440   -3.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1579   -1.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5590   -3.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2720   -2.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430   -2.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5570   -2.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560   -1.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1271   -1.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9860   -2.2153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3031   -2.2179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -0.9786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7290    0.2567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5600   -4.6920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281   -2.2187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  6  2  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 15 10  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  2  0  0  0  0
 18 15  1  0  0  0  0
 19 16  2  0  0  0  0
 19 17  1  0  0  0  0
 20 18  2  0  0  0  0
 21 13  2  0  0  0  0
 21 20  1  0  0  0  0
 22 14  1  0  0  0  0
 22 19  1  0  0  0  0
 23 13  1  0  0  0  0
 24 14  2  0  0  0  0
 24 20  1  0  0  0  0
 25 18  1  0  0  0  0
 25 23  2  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 15  1  0  0  0  0
 27 16  1  0  0  0  0
 28 21  1  0  0  0  0
 29 22  2  0  0  0  0
 30 23  1  0  0  0  0
 31  5  1  0  0  0  0
 31 12  1  0  0  0  0
 32 17  1  0  0  0  0
 32 24  1  0  0  0  0
 33 25  1  0  0  0  0
 33 26  1  0  0  0  0
M  END

HMDB0029905
     RDKit          3D
Artonin T
 59 63  0  0  0  0  0  0  0  0999 V2000
   -4.0076   -5.1336    0.8544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8860   -4.0418    0.7663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4811   -2.7388    0.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4373   -1.7395    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0277   -0.4631    0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9697    0.5406    0.0250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7040   -0.1301   -0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2971    1.1641   -0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1711    2.0529   -0.4762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9483    1.4038   -0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0967    0.3341   -0.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4790   -0.8881   -0.2442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7619   -1.1330   -0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1601   -2.4373    0.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    0.5962   -0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3037   -0.3799   -0.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -1.6377   -0.2332 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202    0.0092   -0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7276   -0.9954   -0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356   -1.2487    1.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9811   -2.4351    1.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8363   -3.6674    0.7809 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1925   -2.5549    3.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9920    1.3273   -0.9385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936    1.7251   -1.0391 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042    2.2890   -1.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142    1.8572   -1.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1890    2.9745   -1.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5264    2.8132   -0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6505    4.1401   -1.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2748    5.3351   -1.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577    4.3796    0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9620    3.6447   -1.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8575   -5.5262   -0.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0565   -4.8114    1.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4238   -5.9086    1.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4731   -2.0120    0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9483    0.4496    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3802   -3.1817    0.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3340   -2.4622   -0.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6416   -0.6880   -0.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3699   -1.9426   -0.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0529   -0.3400    1.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2931   -3.5700   -0.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8125   -4.0751    0.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5015   -4.4360    1.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4221   -3.5860    3.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3009   -2.1589    3.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0394   -1.8567    3.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1364    1.2327   -0.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1922    2.9535   -2.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2757    3.2857   -1.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454    3.3410    0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3579    5.0504   -2.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9204    6.2163   -1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7594    5.5995   -1.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4440    3.6185    0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1857    4.4787    0.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2897    5.3671    0.5562 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  3
 21 22  1  0
 21 23  1  0
 18 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
 14  3  1  0
 27 15  1  0
 13  7  1  0
 33 26  1  0
 29 10  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  6 38  1  0
 14 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 25 50  1  0
 28 51  1  0
 29 52  1  0
 29 53  1  0
 31 54  1  0
 31 55  1  0
 31 56  1  0
 32 57  1  0
 32 58  1  0
 32 59  1  0
M  END


  Mrv0541 05061304542D          

 33 37  0  0  0  0            999 V2000
    4.8722   -0.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1584   -2.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6329    1.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2638    1.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8460   -5.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4432   -0.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7290   -1.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2730   -3.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8440   -3.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1579   -1.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5590   -3.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2720   -2.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430   -2.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5570   -2.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560   -1.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1271   -1.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9860   -2.2153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3031   -2.2179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -0.9786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7290    0.2567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5600   -4.6920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281   -2.2187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  6  2  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 15 10  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  2  0  0  0  0
 18 15  1  0  0  0  0
 19 16  2  0  0  0  0
 19 17  1  0  0  0  0
 20 18  2  0  0  0  0
 21 13  2  0  0  0  0
 21 20  1  0  0  0  0
 22 14  1  0  0  0  0
 22 19  1  0  0  0  0
 23 13  1  0  0  0  0
 24 14  2  0  0  0  0
 24 20  1  0  0  0  0
 25 18  1  0  0  0  0
 25 23  2  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 15  1  0  0  0  0
 27 16  1  0  0  0  0
 28 21  1  0  0  0  0
 29 22  2  0  0  0  0
 30 23  1  0  0  0  0
 31  5  1  0  0  0  0
 31 12  1  0  0  0  0
 32 17  1  0  0  0  0
 32 24  1  0  0  0  0
 33 25  1  0  0  0  0
 33 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029905

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=C2C(=O)C3=C(OC2=C1)C1=C2C(C3)C(C)(C)OC2=C(O)C(CC=C(C)C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H26O7/c1-11(2)6-7-13-21(28)20-18-15(26(3,4)33-25(18)23(13)30)10-14-22(29)19-16(27)8-12(31-5)9-17(19)32-24(14)20/h6,8-9,15,27-28,30H,7,10H2,1-5H3

> <INCHI_KEY>
WGHQJSXSGKUCQL-UHFFFAOYSA-N

> <FORMULA>
C26H26O7

> <MOLECULAR_WEIGHT>
450.4804

> <EXACT_MASS>
450.167853186

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
48.9971112743079

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8,17,19-trihydroxy-6-methoxy-14,14-dimethyl-18-(3-methylbut-2-en-1-yl)-3,15-dioxapentacyclo[11.6.1.0²,¹¹.0⁴,⁹.0¹⁶,²⁰]icosa-1(20),2(11),4,6,8,16,18-heptaen-10-one

> <ALOGPS_LOGP>
4.66

> <JCHEM_LOGP>
4.709182548999999

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
6.257059990071021

> <JCHEM_PKA_STRONGEST_ACIDIC>
-8.208804163884341

> <JCHEM_PKA_STRONGEST_BASIC>
10.70316672948425

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
124.87519999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8,17,19-trihydroxy-6-methoxy-14,14-dimethyl-18-(3-methylbut-2-en-1-yl)-3,15-dioxapentacyclo[11.6.1.0²,¹¹.0⁴,⁹.0¹⁶,²⁰]icosa-1(20),2(11),4,6,8,16,18-heptaen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029905
     RDKit          3D
Artonin T
 59 63  0  0  0  0  0  0  0  0999 V2000
   -4.0076   -5.1336    0.8544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8860   -4.0418    0.7663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4811   -2.7388    0.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4373   -1.7395    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0277   -0.4631    0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9697    0.5406    0.0250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7040   -0.1301   -0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2971    1.1641   -0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1711    2.0529   -0.4762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9483    1.4038   -0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0967    0.3341   -0.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4790   -0.8881   -0.2442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7619   -1.1330   -0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1601   -2.4373    0.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    0.5962   -0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3037   -0.3799   -0.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -1.6377   -0.2332 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202    0.0092   -0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7276   -0.9954   -0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356   -1.2487    1.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9811   -2.4351    1.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8363   -3.6674    0.7809 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1925   -2.5549    3.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9920    1.3273   -0.9385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936    1.7251   -1.0391 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042    2.2890   -1.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142    1.8572   -1.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1890    2.9745   -1.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5264    2.8132   -0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6505    4.1401   -1.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2748    5.3351   -1.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577    4.3796    0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9620    3.6447   -1.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8575   -5.5262   -0.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0565   -4.8114    1.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4238   -5.9086    1.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4731   -2.0120    0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9483    0.4496    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3802   -3.1817    0.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3340   -2.4622   -0.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6416   -0.6880   -0.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3699   -1.9426   -0.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0529   -0.3400    1.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2931   -3.5700   -0.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8125   -4.0751    0.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5015   -4.4360    1.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4221   -3.5860    3.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3009   -2.1589    3.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0394   -1.8567    3.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1364    1.2327   -0.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1922    2.9535   -2.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2757    3.2857   -1.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454    3.3410    0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3579    5.0504   -2.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9204    6.2163   -1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7594    5.5995   -1.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4440    3.6185    0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1857    4.4787    0.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2897    5.3671    0.5562 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  3
 21 22  1  0
 21 23  1  0
 18 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
 14  3  1  0
 27 15  1  0
 13  7  1  0
 33 26  1  0
 29 10  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  6 38  1  0
 14 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 25 50  1  0
 28 51  1  0
 29 52  1  0
 29 53  1  0
 31 54  1  0
 31 55  1  0
 31 56  1  0
 32 57  1  0
 32 58  1  0
 32 59  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       9.095  -1.827   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.762  -4.138   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.181   2.423   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.492   3.610   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.579  -9.530   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.427  -1.828   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.094  -2.599   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.243  -6.447   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.575  -6.450   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.570  -0.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.761  -2.598   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.910  -7.218   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.760  -1.830   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.570  -1.830   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.240   0.480   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.241  -4.907   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.574  -4.910   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.906  -4.138   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.430  -2.600   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.905  -2.598   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.237  -2.602   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.320   2.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.574  -4.135   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.432  -4.140   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -4.237  -1.827   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.094   0.479   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.912  -8.758   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -0.239  -4.142   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.860   2.080   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   26                                                            
CONECT    4   26                                                            
CONECT    5   31                                                            
CONECT    6    7   11                                                       
CONECT    7    6   13                                                       
CONECT    8   12   16                                                       
CONECT    9   12   17                                                       
CONECT   10   14   15                                                       
CONECT   11    1    2    6                                                  
CONECT   12    8    9   31                                                  
CONECT   13    7   21   23                                                  
CONECT   14   10   22   24                                                  
CONECT   15   10   18   26                                                  
CONECT   16    8   19   27                                                  
CONECT   17    9   19   32                                                  
CONECT   18   15   20   25                                                  
CONECT   19   16   17   22                                                  
CONECT   20   18   21   24                                                  
CONECT   21   13   20   28                                                  
CONECT   22   14   19   29                                                  
CONECT   23   13   25   30                                                  
CONECT   24   14   20   32                                                  
CONECT   25   18   23   33                                                  
CONECT   26    3    4   15   33                                             
CONECT   27   16                                                            
CONECT   28   21                                                            
CONECT   29   22                                                            
CONECT   30   23                                                            
CONECT   31    5   12                                                       
CONECT   32   17   24                                                       
CONECT   33   25   26                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

COMPND    HMDB0029905
HETATM    1  C1  UNL     1      -4.008  -5.134   0.854  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.886  -4.042   0.766  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.481  -2.739   0.468  1.00  0.00           C  
HETATM    4  C3  UNL     1      -5.437  -1.740   0.394  1.00  0.00           C  
HETATM    5  C4  UNL     1      -5.028  -0.463   0.102  1.00  0.00           C  
HETATM    6  O2  UNL     1      -5.970   0.541   0.025  1.00  0.00           O  
HETATM    7  C5  UNL     1      -3.704  -0.130  -0.121  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.297   1.164  -0.412  1.00  0.00           C  
HETATM    9  O3  UNL     1      -4.171   2.053  -0.476  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.948   1.404  -0.617  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.097   0.334  -0.519  1.00  0.00           C  
HETATM   12  O4  UNL     1      -1.479  -0.888  -0.244  1.00  0.00           O  
HETATM   13  C9  UNL     1      -2.762  -1.133  -0.045  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.160  -2.437   0.250  1.00  0.00           C  
HETATM   15  C11 UNL     1       0.327   0.596  -0.745  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.304  -0.380  -0.527  1.00  0.00           C  
HETATM   17  O5  UNL     1       0.851  -1.638  -0.233  1.00  0.00           O  
HETATM   18  C13 UNL     1       2.620   0.009  -0.629  1.00  0.00           C  
HETATM   19  C14 UNL     1       3.728  -0.995  -0.393  1.00  0.00           C  
HETATM   20  C15 UNL     1       3.936  -1.249   1.043  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.981  -2.435   1.558  1.00  0.00           C  
HETATM   22  C17 UNL     1       3.836  -3.667   0.781  1.00  0.00           C  
HETATM   23  C18 UNL     1       4.192  -2.555   3.048  1.00  0.00           C  
HETATM   24  C19 UNL     1       2.992   1.327  -0.938  1.00  0.00           C  
HETATM   25  O6  UNL     1       4.294   1.725  -1.039  1.00  0.00           O  
HETATM   26  C20 UNL     1       2.004   2.289  -1.156  1.00  0.00           C  
HETATM   27  C21 UNL     1       0.714   1.857  -1.047  1.00  0.00           C  
HETATM   28  C22 UNL     1      -0.189   2.975  -1.430  1.00  0.00           C  
HETATM   29  C23 UNL     1      -1.526   2.813  -0.865  1.00  0.00           C  
HETATM   30  C24 UNL     1       0.651   4.140  -1.041  1.00  0.00           C  
HETATM   31  C25 UNL     1       0.275   5.335  -1.852  1.00  0.00           C  
HETATM   32  C26 UNL     1       0.758   4.380   0.425  1.00  0.00           C  
HETATM   33  O7  UNL     1       1.962   3.645  -1.467  1.00  0.00           O  
HETATM   34  H1  UNL     1      -3.857  -5.526  -0.178  1.00  0.00           H  
HETATM   35  H2  UNL     1      -3.057  -4.811   1.304  1.00  0.00           H  
HETATM   36  H3  UNL     1      -4.424  -5.909   1.534  1.00  0.00           H  
HETATM   37  H4  UNL     1      -6.473  -2.012   0.571  1.00  0.00           H  
HETATM   38  H5  UNL     1      -6.948   0.450   0.160  1.00  0.00           H  
HETATM   39  H6  UNL     1      -2.380  -3.182   0.296  1.00  0.00           H  
HETATM   40  H7  UNL     1       1.334  -2.462  -0.023  1.00  0.00           H  
HETATM   41  H8  UNL     1       4.642  -0.688  -0.921  1.00  0.00           H  
HETATM   42  H9  UNL     1       3.370  -1.943  -0.871  1.00  0.00           H  
HETATM   43  H10 UNL     1       4.053  -0.340   1.665  1.00  0.00           H  
HETATM   44  H11 UNL     1       4.293  -3.570  -0.234  1.00  0.00           H  
HETATM   45  H12 UNL     1       2.812  -4.075   0.778  1.00  0.00           H  
HETATM   46  H13 UNL     1       4.502  -4.436   1.305  1.00  0.00           H  
HETATM   47  H14 UNL     1       4.422  -3.586   3.329  1.00  0.00           H  
HETATM   48  H15 UNL     1       3.301  -2.159   3.563  1.00  0.00           H  
HETATM   49  H16 UNL     1       5.039  -1.857   3.270  1.00  0.00           H  
HETATM   50  H17 UNL     1       5.136   1.233  -0.926  1.00  0.00           H  
HETATM   51  H18 UNL     1      -0.192   2.953  -2.562  1.00  0.00           H  
HETATM   52  H19 UNL     1      -2.276   3.286  -1.568  1.00  0.00           H  
HETATM   53  H20 UNL     1      -1.645   3.341   0.104  1.00  0.00           H  
HETATM   54  H21 UNL     1       0.358   5.050  -2.927  1.00  0.00           H  
HETATM   55  H22 UNL     1       0.920   6.216  -1.699  1.00  0.00           H  
HETATM   56  H23 UNL     1      -0.759   5.600  -1.635  1.00  0.00           H  
HETATM   57  H24 UNL     1       1.444   3.618   0.849  1.00  0.00           H  
HETATM   58  H25 UNL     1      -0.186   4.479   0.962  1.00  0.00           H  
HETATM   59  H26 UNL     1       1.290   5.367   0.556  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3
CONECT    3    4    4   14
CONECT    4    5   37
CONECT    5    6    7    7
CONECT    6   38
CONECT    7    8   13
CONECT    8    9    9   10
CONECT   10   11   11   29
CONECT   11   12   15
CONECT   12   13
CONECT   13   14   14
CONECT   14   39
CONECT   15   16   16   27
CONECT   16   17   18
CONECT   17   40
CONECT   18   19   24   24
CONECT   19   20   41   42
CONECT   20   21   21   43
CONECT   21   22   23
CONECT   22   44   45   46
CONECT   23   47   48   49
CONECT   24   25   26
CONECT   25   50
CONECT   26   27   27   33
CONECT   27   28
CONECT   28   29   30   51
CONECT   29   52   53
CONECT   30   31   32   33
CONECT   31   54   55   56
CONECT   32   57   58   59
END

HMDB0029905
     RDKit          3D
Artonin T
 59 63  0  0  0  0  0  0  0  0999 V2000
   -4.0076   -5.1336    0.8544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8860   -4.0418    0.7663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4811   -2.7388    0.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4373   -1.7395    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0277   -0.4631    0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9697    0.5406    0.0250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7040   -0.1301   -0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2971    1.1641   -0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1711    2.0529   -0.4762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9483    1.4038   -0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0967    0.3341   -0.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4790   -0.8881   -0.2442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7619   -1.1330   -0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1601   -2.4373    0.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    0.5962   -0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3037   -0.3799   -0.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -1.6377   -0.2332 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202    0.0092   -0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7276   -0.9954   -0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356   -1.2487    1.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9811   -2.4351    1.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8363   -3.6674    0.7809 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1925   -2.5549    3.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9920    1.3273   -0.9385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936    1.7251   -1.0391 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042    2.2890   -1.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142    1.8572   -1.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1890    2.9745   -1.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5264    2.8132   -0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6505    4.1401   -1.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2748    5.3351   -1.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577    4.3796    0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9620    3.6447   -1.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8575   -5.5262   -0.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0565   -4.8114    1.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4238   -5.9086    1.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4731   -2.0120    0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9483    0.4496    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3802   -3.1817    0.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3340   -2.4622   -0.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6416   -0.6880   -0.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3699   -1.9426   -0.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0529   -0.3400    1.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2931   -3.5700   -0.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8125   -4.0751    0.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5015   -4.4360    1.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4221   -3.5860    3.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3009   -2.1589    3.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0394   -1.8567    3.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1364    1.2327   -0.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1922    2.9535   -2.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2757    3.2857   -1.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454    3.3410    0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3579    5.0504   -2.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9204    6.2163   -1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7594    5.5995   -1.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4440    3.6185    0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1857    4.4787    0.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2897    5.3671    0.5562 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  3
 21 22  1  0
 21 23  1  0
 18 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
 14  3  1  0
 27 15  1  0
 13  7  1  0
 33 26  1  0
 29 10  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  6 38  1  0
 14 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 25 50  1  0
 28 51  1  0
 29 52  1  0
 29 53  1  0
 31 54  1  0
 31 55  1  0
 31 56  1  0
 32 57  1  0
 32 58  1  0
 32 59  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Lucumin	HMDB
Lucumine	HMDB
Vicianin	HMDB
5a,6-dihydro-1,3,8-Trihydroxy-10-methoxy-5,5-dimethyl-2-(3-methyl-2-butenyl)-5H,7H-benzofuro[3,4-BC]xanthen-7-one	HMDB

Chemical Formula

C₂₆H₂₆O₇

Average Molecular Weight

450.4804

Monoisotopic Molecular Weight

450.167853186

IUPAC Name

8,17,19-trihydroxy-6-methoxy-14,14-dimethyl-18-(3-methylbut-2-en-1-yl)-3,15-dioxapentacyclo[11.6.1.0²,¹¹.0⁴,⁹.0¹⁶,²⁰]icosa-1(20),2(11),4,6,8,16,18-heptaen-10-one

Traditional Name

8,17,19-trihydroxy-6-methoxy-14,14-dimethyl-18-(3-methylbut-2-en-1-yl)-3,15-dioxapentacyclo[11.6.1.0²,¹¹.0⁴,⁹.0¹⁶,²⁰]icosa-1(20),2(11),4,6,8,16,18-heptaen-10-one

CAS Registry Number

161017-03-4

SMILES

COC1=CC(O)=C2C(=O)C3=C(OC2=C1)C1=C2C(C3)C(C)(C)OC2=C(O)C(CC=C(C)C)=C1O

InChI Identifier

InChI=1S/C26H26O7/c1-11(2)6-7-13-21(28)20-18-15(26(3,4)33-25(18)23(13)30)10-14-22(29)19-16(27)8-12(31-5)9-17(19)32-24(14)20/h6,8-9,15,27-28,30H,7,10H2,1-5H3

InChI Key

WGHQJSXSGKUCQL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Cyanogenic glycosides

Alternative Parents

Substituents

Cyanogenic glycoside
Disaccharide
O-glycosyl compound
Monocyclic benzene moiety
Oxane
Benzenoid
Secondary alcohol
Polyol
Nitrile
Carbonitrile
Acetal
Organoheterocyclic compound
Oxacycle
Alcohol
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a small molecule (R-VICIANIN )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0029905)

Cellular substructure

Membrane (HMDB: HMDB0029905)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029905)

Source

Endogenous

Endogenous (HMDB: HMDB0029905)

Plant

Plant (HMDB: HMDB0029905)

Exogenous

Food

Food (HMDB: HMDB0029905)

Fruit

Tropical fruit

Jackfruit (FooDB: FOOD00384)

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	252 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	4.66	ALOGPS
logP	4.71	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	-8.2	ChemAxon
pKa (Strongest Basic)	10.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	124.88 m³·mol⁻¹	ChemAxon
Polarizability	49 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	204.483	31661259
DarkChem	[M-H]-	202.224	31661259
DeepCCS	[M+H]+	203.704	30932474
DeepCCS	[M-H]-	201.308	30932474
DeepCCS	[M-2H]-	234.197	30932474
DeepCCS	[M+Na]+	209.616	30932474
AllCCS	[M+H]+	208.4	32859911
AllCCS	[M+H-H2O]+	206.0	32859911
AllCCS	[M+NH4]+	210.6	32859911
AllCCS	[M+Na]+	211.2	32859911
AllCCS	[M-H]-	208.7	32859911
AllCCS	[M+Na-2H]-	208.7	32859911
AllCCS	[M+HCOO]-	208.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Artonin T	COC1=CC(O)=C2C(=O)C3=C(OC2=C1)C1=C2C(C3)C(C)(C)OC2=C(O)C(CC=C(C)C)=C1O	5473.1	Standard polar	33892256
Artonin T	COC1=CC(O)=C2C(=O)C3=C(OC2=C1)C1=C2C(C3)C(C)(C)OC2=C(O)C(CC=C(C)C)=C1O	3665.1	Standard non polar	33892256
Artonin T	COC1=CC(O)=C2C(=O)C3=C(OC2=C1)C1=C2C(C3)C(C)(C)OC2=C(O)C(CC=C(C)C)=C1O	3984.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Artonin T,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(OC2=C1)C1=C(O)C(CC=C(C)C)=C(O)C2=C1C(C3)C(C)(C)O2	3657.7	Semi standard non polar	33892256
Artonin T,1TMS,isomer #2	COC1=CC(O)=C2C(=O)C3=C(OC2=C1)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C2=C1C(C3)C(C)(C)O2	3655.8	Semi standard non polar	33892256
Artonin T,1TMS,isomer #3	COC1=CC(O)=C2C(=O)C3=C(OC2=C1)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O)C2=C1C(C3)C(C)(C)O2	3695.1	Semi standard non polar	33892256
Artonin T,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(OC2=C1)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O)C2=C1C(C3)C(C)(C)O2	3636.3	Semi standard non polar	33892256
Artonin T,2TMS,isomer #2	COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(OC2=C1)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C2=C1C(C3)C(C)(C)O2	3572.2	Semi standard non polar	33892256
Artonin T,2TMS,isomer #3	COC1=CC(O)=C2C(=O)C3=C(OC2=C1)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C2=C1C(C3)C(C)(C)O2	3609.3	Semi standard non polar	33892256
Artonin T,3TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(OC2=C1)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C2=C1C(C3)C(C)(C)O2	3574.3	Semi standard non polar	33892256
Artonin T,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(OC2=C1)C1=C(O)C(CC=C(C)C)=C(O)C2=C1C(C3)C(C)(C)O2	3857.6	Semi standard non polar	33892256
Artonin T,1TBDMS,isomer #2	COC1=CC(O)=C2C(=O)C3=C(OC2=C1)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=C1C(C3)C(C)(C)O2	3865.3	Semi standard non polar	33892256
Artonin T,1TBDMS,isomer #3	COC1=CC(O)=C2C(=O)C3=C(OC2=C1)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O)C2=C1C(C3)C(C)(C)O2	3908.4	Semi standard non polar	33892256
Artonin T,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(OC2=C1)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O)C2=C1C(C3)C(C)(C)O2	4062.7	Semi standard non polar	33892256
Artonin T,2TBDMS,isomer #2	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(OC2=C1)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=C1C(C3)C(C)(C)O2	4002.2	Semi standard non polar	33892256
Artonin T,2TBDMS,isomer #3	COC1=CC(O)=C2C(=O)C3=C(OC2=C1)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=C1C(C3)C(C)(C)O2	4036.4	Semi standard non polar	33892256
Artonin T,3TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(OC2=C1)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=C1C(C3)C(C)(C)O2	4162.3	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 - Artonin T GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fki-1501900000-6f9cf24db5274650ce3a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artonin T GC-MS (3 TMS) - 70eV, Positive	splash10-0udi-2040039000-ad7a1b05bf5caaa3cfbe	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artonin T 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonin T 10V, Positive-QTOF	splash10-0udi-0000900000-92e28237fa21684f56c7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonin T 20V, Positive-QTOF	splash10-1001-3006900000-027115007919a9c9cc01	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonin T 40V, Positive-QTOF	splash10-0gb9-6029000000-aaee99bed3b80c3320d0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonin T 10V, Negative-QTOF	splash10-0002-0000900000-7370bf497529ff50463b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonin T 20V, Negative-QTOF	splash10-0002-0002900000-00af76bfe01942b096cf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonin T 40V, Negative-QTOF	splash10-0fry-3109600000-d2d6a3bf5aeade020b6a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonin T 10V, Positive-QTOF	splash10-0udi-0000900000-30d6dbec2c40cf11fac9	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonin T 20V, Positive-QTOF	splash10-0udi-0000900000-30d6dbec2c40cf11fac9	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonin T 40V, Positive-QTOF	splash10-0uxr-0720900000-22ad40f6f394f4a7bd4c	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonin T 10V, Negative-QTOF	splash10-0002-0000900000-158c2738b67dc7435f5a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonin T 20V, Negative-QTOF	splash10-0002-0000900000-158c2738b67dc7435f5a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artonin T 40V, Negative-QTOF	splash10-00or-0609300000-573313be7bf62e44a428	2021-09-25	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4475723

PDB ID

Not Available

ChEBI ID

6559

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 Artonin T (HMDB0029905)

MOL for HMDB0029905 (Artonin T)

3D MOL for HMDB0029905 (Artonin T)

3D SDF for HMDB0029905 (Artonin T)

3D-SDF for HMDB0029905 (Artonin T)

PDB for HMDB0029905 (Artonin T)

3D PDB for HMDB0029905 (Artonin T)

SMILES for HMDB0029905 (Artonin T)

INCHI for HMDB0029905 (Artonin T)

Structure for HMDB0029905 (Artonin T)

3D Structure for HMDB0029905 (Artonin T)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra