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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:19:19 UTC

Update Date

2022-03-07 02:53:46 UTC

HMDB ID

HMDB0033578

Secondary Accession Numbers

HMDB33578

Metabolite Identification

Common Name

Aquifoliunine EIII

Description

Aquifoliunine EIII, also known as aquifoliunine e-iii, belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Aquifoliunine EIII is a moderately basic compound (based on its pKa). Outside of the human body, aquifoliunine eiii has been detected, but not quantified in, tea. This could make aquifoliunine eiii a potential biomarker for the consumption of these foods.

Structure

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


  Mrv0541 05061307132D          

 54 58  0  0  0  0            999 V2000
    5.4027   -3.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7382   -4.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2706   -3.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2124   -5.7154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1231   -1.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8445    0.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1633   -3.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    0.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9218   -2.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1348   -0.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3740   -0.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2835   -1.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8614    0.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2140   -2.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7385   -2.7379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2599   -3.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112   -2.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5028   -4.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6203   -1.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7475   -0.7356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696   -3.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0691   -1.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0816   -3.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4480   -1.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389   -2.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5620   -3.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3155   -0.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4239   -0.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3556   -2.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0242   -2.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6714   -2.1837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8942   -1.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9152   -0.8784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1035   -2.9582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4689   -1.8446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0729   -3.0673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 15  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16 15  1  0  0  0  0
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 18  4  1  0  0  0  0
 19  5  1  0  0  0  0
 20  6  1  0  0  0  0
 21  7  1  0  0  0  0
 22 11  1  0  0  0  0
 24 15  1  0  0  0  0
 24 22  2  0  0  0  0
 25 23  1  0  0  0  0
 27 23  1  0  0  0  0
 28 26  1  0  0  0  0
 29 25  1  0  0  0  0
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 32 22  1  0  0  0  0
 33  8  1  0  0  0  0
 33 13  1  0  0  0  0
 33 23  1  0  0  0  0
 34  9  1  0  0  0  0
 34 28  1  0  0  0  0
 35 14  1  0  0  0  0
 35 29  1  0  0  0  0
 35 30  1  0  0  0  0
 36 27  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 37 12  2  0  0  0  0
 37 24  1  0  0  0  0
 38 17  2  0  0  0  0
 39 18  2  0  0  0  0
 40 19  2  0  0  0  0
 41 20  2  0  0  0  0
 42 21  2  0  0  0  0
 43 31  2  0  0  0  0
 44 32  2  0  0  0  0
 45 34  1  0  0  0  0
 46 14  1  0  0  0  0
 46 17  1  0  0  0  0
 47 13  1  0  0  0  0
 47 32  1  0  0  0  0
 48 18  1  0  0  0  0
 48 26  1  0  0  0  0
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 50 29  1  0  0  0  0
 51 21  1  0  0  0  0
 51 30  1  0  0  0  0
 52 25  1  0  0  0  0
 53 28  1  0  0  0  0
 53 31  1  0  0  0  0
 54 33  1  0  0  0  0
 54 36  1  0  0  0  0
M  END

HMDB0033578
     RDKit          3D
Aquifoliunine EIII
 99103  0  0  0  0  0  0  0  0999 V2000
   -3.8931   -2.1998   -4.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6155   -1.0403   -3.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0391    0.1270   -3.6612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8906   -1.1424   -2.1941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6282   -0.0556   -1.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8573   -0.1806   -0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6266   -1.1690    0.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5786   -0.8600    2.0893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7364   -0.6736    2.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6890   -0.3508    4.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8408   -0.7974    2.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856   -2.5863    0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9697   -3.4437    1.2134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458   -2.9006    0.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1578   -1.9812   -0.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6169   -2.2965   -1.9487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2300   -2.6596   -2.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -3.0059   -4.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4634   -2.6961   -2.7339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849   -0.6952   -0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3217   -1.0271    1.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1061   -2.2628    1.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4289   -2.6920    2.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5070   -2.6952    1.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5523   -1.8042    1.6420 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8769   -1.7887    1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8245   -2.3796    1.9416 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8882   -2.2117   -0.8924 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4731   -1.9872   -2.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7112   -0.6708   -2.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3801    0.2852   -1.5684 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7879    0.0781   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6918    1.3742    0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6877    1.1302    1.8675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7838    2.4131   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2291    3.3496    1.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7718    2.1692   -1.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9301    2.1390   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7669    3.3435    0.2629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2466    4.5730   -0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9711    5.7298    0.7971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8982    4.6616   -1.1622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8192    1.2320    0.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1363    1.7738    0.1786 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5833   -0.1727   -1.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 54 99  1  0
M  END


  Mrv0541 05061307132D          

 54 58  0  0  0  0            999 V2000
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 54 33  1  0  0  0  0
 54 36  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033578

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C(C)C(=O)OC2C(OC(C)=O)C(OC(C)=O)C3(COC(C)=O)C(OC(C)=O)C(O)C4C(OC(C)=O)C3(OC4(C)COC(=O)C3=C1N=CC=C3)C2(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C36H45NO17/c1-15-16(2)31(44)53-29-26(49-18(4)39)30(52-21(7)42)35(14-47-17(3)38)28(51-20(6)41)25(43)23-27(50-19(5)40)36(35,34(29,9)46)54-33(23,8)13-48-32(45)22-11-10-12-37-24(15)22/h10-12,15-16,23,25-30,43,46H,13-14H2,1-9H3

> <INCHI_KEY>
NLOQRURWORDOGK-UHFFFAOYSA-N

> <FORMULA>
C36H45NO17

> <MOLECULAR_WEIGHT>
763.739

> <EXACT_MASS>
763.268749019

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
73.66586231606652

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[18,19,21,24-tetrakis(acetyloxy)-22,25-dihydroxy-3,13,14,25-tetramethyl-6,15-dioxo-2,5,16-trioxa-11-azapentacyclo[15.7.1.0¹,²⁰.0³,²³.0⁷,¹²]pentacosa-7(12),8,10-trien-20-yl]methyl acetate

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
-0.6841043153333348

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.75952528764494

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.69208930042769

> <JCHEM_PKA_STRONGEST_BASIC>
2.6118354082240622

> <JCHEM_POLAR_SURFACE_AREA>
246.67999999999986

> <JCHEM_REFRACTIVITY>
173.64510000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[18,19,21,24-tetrakis(acetyloxy)-22,25-dihydroxy-3,13,14,25-tetramethyl-6,15-dioxo-2,5,16-trioxa-11-azapentacyclo[15.7.1.0¹,²⁰.0³,²³.0⁷,¹²]pentacosa-7(12),8,10-trien-20-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033578
     RDKit          3D
Aquifoliunine EIII
 99103  0  0  0  0  0  0  0  0999 V2000
   -3.8931   -2.1998   -4.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6155   -1.0403   -3.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0391    0.1270   -3.6612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8906   -1.1424   -2.1941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6282   -0.0556   -1.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8573   -0.1806   -0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6266   -1.1690    0.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5786   -0.8600    2.0893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7364   -0.6736    2.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6890   -0.3508    4.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8408   -0.7974    2.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856   -2.5863    0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9697   -3.4437    1.2134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458   -2.9006    0.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1578   -1.9812   -0.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6169   -2.2965   -1.9487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2300   -2.6596   -2.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -3.0059   -4.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4634   -2.6961   -2.7339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849   -0.6952   -0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3217   -1.0271    1.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1061   -2.2628    1.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4289   -2.6920    2.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5070   -2.6952    1.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5523   -1.8042    1.6420 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8769   -1.7887    1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8245   -2.3796    1.9416 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5229   -1.1948    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8882   -2.2117   -0.8924 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4731   -1.9872   -2.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7112   -0.6708   -2.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3801    0.2852   -1.5684 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7879    0.0781   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6918    1.3742    0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6877    1.1302    1.8675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7838    2.4131   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2291    3.3496    1.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7718    2.1692   -1.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3965    1.8111   -2.2101 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4525    2.3032   -0.9891 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2970    1.5379   -1.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9301    2.1390   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7669    3.3435    0.2629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2466    4.5730   -0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9711    5.7298    0.7971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8982    4.6616   -1.1622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8192    1.2320    0.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1363    1.7738    0.1786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8116    2.3537    1.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1863    2.8850    0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3511    2.4546    2.3949 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5978    0.3370   -0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050    0.9495    1.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6633   -0.2717   -0.7745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9235   -2.0462   -4.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9437   -3.1473   -3.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2120   -2.2227   -5.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3860    0.7953   -2.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6647    0.2560   -1.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7060   -1.1815    0.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5746    0.2619    4.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8014    0.2889    4.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5658   -2.8064   -0.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9101   -3.1990    1.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5723   -3.9403    0.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9488   -2.0441   -0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2920   -2.0620   -4.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5330   -3.6443   -4.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2163   -3.5359   -4.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4630   -1.8001    3.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3328   -3.2720    2.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3520   -3.3513    3.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6074   -3.5376    2.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7578   -3.2846   -0.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7309   -2.8023   -2.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1762   -0.4787   -3.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8003    1.8437    0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7063    0.6871    2.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6623    2.1320    2.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9819    0.4089    2.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5473    3.1998   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247    3.8394    0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9182    4.2006    1.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    2.8518    1.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0664    1.0398   -2.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5396    2.4779   -1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8718    6.6741    0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7932    5.8002    1.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326    5.5907    1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6180    1.3333    1.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5125    3.6061    1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1337    3.3478   -0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8486    1.9969    0.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9800    0.7774    1.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4464    0.4263    2.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7339    2.0171    1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5833   -0.1727   -1.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  7 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
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 16 17  1  0
 17 18  1  0
 17 19  2  0
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 53 98  1  0
 54 99  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      10.085  -6.112   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.845  -7.681   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.372  -5.651   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.263 -10.669   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.696  -1.941   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.576   0.127   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.171  -7.449   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.039   0.295   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.454  -3.834   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.452  -1.616   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.031  -1.117   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.729  -3.096   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.341   0.109   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.399  -4.307   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.845  -5.111   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.952  -6.365   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.261  -4.115   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.805  -9.227   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.758  -2.689   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.066  -1.333   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.656  -7.175   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.889  -2.097   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.950  -1.145   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.166  -3.577   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.395  -1.373   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.370  -6.596   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.862  -2.224   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.886  -6.385   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.836  -2.827   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.379  -5.451   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.649  -7.186   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.056  -0.807   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.525  -1.232   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.397  -4.952   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.912  -4.017   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.504  -3.719   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0      10.587  -4.076   0.000  0.00  0.00           N+0
HETATM   38  O   UNK     0      -3.536  -3.251   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       4.325  -8.976   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       6.893  -4.058   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -3.575  -1.640   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       0.339  -8.350   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       7.037  -8.719   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       8.833   0.593   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       5.793  -5.522   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      -0.875  -3.443   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       6.871   0.165   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       1.828  -8.037   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       5.403  -1.953   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -0.933  -2.615   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -0.136  -5.726   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       0.434  -0.170   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       5.117  -7.319   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       4.859  -2.810   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   18                                                            
CONECT    5   19                                                            
CONECT    6   20                                                            
CONECT    7   21                                                            
CONECT    8   33                                                            
CONECT    9   34                                                            
CONECT   10   11   12                                                       
CONECT   11   10   22                                                       
CONECT   12   10   37                                                       
CONECT   13   33   47                                                       
CONECT   14   35   46                                                       
CONECT   15    1   16   24                                                  
CONECT   16    2   15   31                                                  
CONECT   17    3   38   46                                                  
CONECT   18    4   39   48                                                  
CONECT   19    5   40   49                                                  
CONECT   20    6   41   50                                                  
CONECT   21    7   42   51                                                  
CONECT   22   11   24   32                                                  
CONECT   23   25   27   33                                                  
CONECT   24   15   22   37                                                  
CONECT   25   23   29   52                                                  
CONECT   26   28   30   48                                                  
CONECT   27   23   36   49                                                  
CONECT   28   26   34   53                                                  
CONECT   29   25   35   50                                                  
CONECT   30   26   35   51                                                  
CONECT   31   16   43   53                                                  
CONECT   32   22   44   47                                                  
CONECT   33    8   13   23   54                                             
CONECT   34    9   28   36   45                                             
CONECT   35   14   29   30   36                                             
CONECT   36   27   34   35   54                                             
CONECT   37   12   24                                                       
CONECT   38   17                                                            
CONECT   39   18                                                            
CONECT   40   19                                                            
CONECT   41   20                                                            
CONECT   42   21                                                            
CONECT   43   31                                                            
CONECT   44   32                                                            
CONECT   45   34                                                            
CONECT   46   14   17                                                       
CONECT   47   13   32                                                       
CONECT   48   18   26                                                       
CONECT   49   19   27                                                       
CONECT   50   20   29                                                       
CONECT   51   21   30                                                       
CONECT   52   25                                                            
CONECT   53   28   31                                                       
CONECT   54   33   36                                                       
MASTER        0    0    0    0    0    0    0    0   54    0  116    0
END

COMPND    HMDB0033578
HETATM    1  C1  UNL     1      -3.893  -2.200  -4.212  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.616  -1.040  -3.358  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.039   0.127  -3.661  1.00  0.00           O  
HETATM    4  O2  UNL     1      -2.891  -1.142  -2.194  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.628  -0.056  -1.390  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.857  -0.181  -0.158  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.627  -1.169   0.720  1.00  0.00           C  
HETATM    8  O3  UNL     1      -2.579  -0.860   2.089  1.00  0.00           O  
HETATM    9  C6  UNL     1      -3.736  -0.674   2.871  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.689  -0.351   4.302  1.00  0.00           C  
HETATM   11  O4  UNL     1      -4.841  -0.797   2.282  1.00  0.00           O  
HETATM   12  C8  UNL     1      -2.186  -2.586   0.435  1.00  0.00           C  
HETATM   13  O5  UNL     1      -2.970  -3.444   1.213  1.00  0.00           O  
HETATM   14  C9  UNL     1      -0.746  -2.901   0.396  1.00  0.00           C  
HETATM   15  C10 UNL     1      -0.158  -1.981  -0.713  1.00  0.00           C  
HETATM   16  O6  UNL     1      -0.617  -2.296  -1.949  1.00  0.00           O  
HETATM   17  C11 UNL     1       0.230  -2.660  -2.975  1.00  0.00           C  
HETATM   18  C12 UNL     1      -0.239  -3.006  -4.335  1.00  0.00           C  
HETATM   19  O7  UNL     1       1.463  -2.696  -2.734  1.00  0.00           O  
HETATM   20  C13 UNL     1      -0.485  -0.695  -0.070  1.00  0.00           C  
HETATM   21  O8  UNL     1      -0.322  -1.027   1.329  1.00  0.00           O  
HETATM   22  C14 UNL     1       0.106  -2.263   1.492  1.00  0.00           C  
HETATM   23  C15 UNL     1      -0.429  -2.692   2.884  1.00  0.00           C  
HETATM   24  C16 UNL     1       1.507  -2.695   1.351  1.00  0.00           C  
HETATM   25  O9  UNL     1       2.552  -1.804   1.642  1.00  0.00           O  
HETATM   26  C17 UNL     1       3.877  -1.789   1.227  1.00  0.00           C  
HETATM   27  O10 UNL     1       4.825  -2.380   1.942  1.00  0.00           O  
HETATM   28  C18 UNL     1       4.523  -1.195   0.033  1.00  0.00           C  
HETATM   29  C19 UNL     1       4.888  -2.212  -0.892  1.00  0.00           C  
HETATM   30  C20 UNL     1       5.473  -1.987  -2.109  1.00  0.00           C  
HETATM   31  C21 UNL     1       5.711  -0.671  -2.424  1.00  0.00           C  
HETATM   32  N1  UNL     1       5.380   0.285  -1.568  1.00  0.00           N  
HETATM   33  C22 UNL     1       4.788   0.078  -0.330  1.00  0.00           C  
HETATM   34  C23 UNL     1       4.692   1.374   0.387  1.00  0.00           C  
HETATM   35  C24 UNL     1       4.688   1.130   1.868  1.00  0.00           C  
HETATM   36  C25 UNL     1       3.784   2.413  -0.056  1.00  0.00           C  
HETATM   37  C26 UNL     1       3.229   3.350   1.000  1.00  0.00           C  
HETATM   38  C27 UNL     1       2.772   2.169  -1.125  1.00  0.00           C  
HETATM   39  O11 UNL     1       3.397   1.811  -2.210  1.00  0.00           O  
HETATM   40  O12 UNL     1       1.453   2.303  -0.989  1.00  0.00           O  
HETATM   41  C28 UNL     1       0.297   1.538  -1.010  1.00  0.00           C  
HETATM   42  C29 UNL     1      -0.930   2.139  -0.456  1.00  0.00           C  
HETATM   43  O13 UNL     1      -0.767   3.344   0.263  1.00  0.00           O  
HETATM   44  C30 UNL     1      -1.247   4.573  -0.094  1.00  0.00           C  
HETATM   45  C31 UNL     1      -0.971   5.730   0.797  1.00  0.00           C  
HETATM   46  O14 UNL     1      -1.898   4.662  -1.162  1.00  0.00           O  
HETATM   47  C32 UNL     1      -1.819   1.232   0.390  1.00  0.00           C  
HETATM   48  O15 UNL     1      -3.136   1.774   0.179  1.00  0.00           O  
HETATM   49  C33 UNL     1      -3.812   2.354   1.232  1.00  0.00           C  
HETATM   50  C34 UNL     1      -5.186   2.885   0.916  1.00  0.00           C  
HETATM   51  O16 UNL     1      -3.351   2.455   2.395  1.00  0.00           O  
HETATM   52  C35 UNL     1       0.598   0.337  -0.133  1.00  0.00           C  
HETATM   53  C36 UNL     1       0.905   0.949   1.212  1.00  0.00           C  
HETATM   54  O17 UNL     1       1.663  -0.272  -0.774  1.00  0.00           O  
HETATM   55  H1  UNL     1      -4.924  -2.046  -4.643  1.00  0.00           H  
HETATM   56  H2  UNL     1      -3.944  -3.147  -3.642  1.00  0.00           H  
HETATM   57  H3  UNL     1      -3.212  -2.223  -5.070  1.00  0.00           H  
HETATM   58  H4  UNL     1      -2.386   0.795  -2.059  1.00  0.00           H  
HETATM   59  H5  UNL     1      -3.665   0.256  -1.024  1.00  0.00           H  
HETATM   60  H6  UNL     1      -3.706  -1.181   0.448  1.00  0.00           H  
HETATM   61  H7  UNL     1      -4.575   0.262   4.566  1.00  0.00           H  
HETATM   62  H8  UNL     1      -2.801   0.289   4.474  1.00  0.00           H  
HETATM   63  H9  UNL     1      -3.687  -1.259   4.932  1.00  0.00           H  
HETATM   64  H10 UNL     1      -2.566  -2.806  -0.613  1.00  0.00           H  
HETATM   65  H11 UNL     1      -3.910  -3.199   1.020  1.00  0.00           H  
HETATM   66  H12 UNL     1      -0.572  -3.940   0.221  1.00  0.00           H  
HETATM   67  H13 UNL     1       0.949  -2.044  -0.730  1.00  0.00           H  
HETATM   68  H14 UNL     1      -0.292  -2.062  -4.915  1.00  0.00           H  
HETATM   69  H15 UNL     1       0.533  -3.644  -4.806  1.00  0.00           H  
HETATM   70  H16 UNL     1      -1.216  -3.536  -4.305  1.00  0.00           H  
HETATM   71  H17 UNL     1      -0.463  -1.800   3.564  1.00  0.00           H  
HETATM   72  H18 UNL     1      -1.333  -3.272   2.840  1.00  0.00           H  
HETATM   73  H19 UNL     1       0.352  -3.351   3.354  1.00  0.00           H  
HETATM   74  H20 UNL     1       1.607  -3.538   2.138  1.00  0.00           H  
HETATM   75  H21 UNL     1       1.712  -3.355   0.448  1.00  0.00           H  
HETATM   76  H22 UNL     1       4.758  -3.285  -0.645  1.00  0.00           H  
HETATM   77  H23 UNL     1       5.731  -2.802  -2.781  1.00  0.00           H  
HETATM   78  H24 UNL     1       6.176  -0.479  -3.395  1.00  0.00           H  
HETATM   79  H25 UNL     1       5.800   1.844   0.297  1.00  0.00           H  
HETATM   80  H26 UNL     1       5.706   0.687   2.187  1.00  0.00           H  
HETATM   81  H27 UNL     1       4.662   2.132   2.400  1.00  0.00           H  
HETATM   82  H28 UNL     1       3.982   0.409   2.255  1.00  0.00           H  
HETATM   83  H29 UNL     1       4.547   3.200  -0.560  1.00  0.00           H  
HETATM   84  H30 UNL     1       2.325   3.839   0.528  1.00  0.00           H  
HETATM   85  H31 UNL     1       3.918   4.201   1.201  1.00  0.00           H  
HETATM   86  H32 UNL     1       2.896   2.852   1.904  1.00  0.00           H  
HETATM   87  H33 UNL     1       0.066   1.040  -2.011  1.00  0.00           H  
HETATM   88  H34 UNL     1      -1.540   2.478  -1.361  1.00  0.00           H  
HETATM   89  H35 UNL     1      -0.872   6.674   0.226  1.00  0.00           H  
HETATM   90  H36 UNL     1      -1.793   5.800   1.546  1.00  0.00           H  
HETATM   91  H37 UNL     1      -0.033   5.591   1.369  1.00  0.00           H  
HETATM   92  H38 UNL     1      -1.618   1.333   1.446  1.00  0.00           H  
HETATM   93  H39 UNL     1      -5.513   3.606   1.686  1.00  0.00           H  
HETATM   94  H40 UNL     1      -5.134   3.348  -0.109  1.00  0.00           H  
HETATM   95  H41 UNL     1      -5.849   1.997   0.861  1.00  0.00           H  
HETATM   96  H42 UNL     1       1.980   0.777   1.352  1.00  0.00           H  
HETATM   97  H43 UNL     1       0.446   0.426   2.081  1.00  0.00           H  
HETATM   98  H44 UNL     1       0.734   2.017   1.300  1.00  0.00           H  
HETATM   99  H45 UNL     1       1.583  -0.173  -1.739  1.00  0.00           H  
CONECT    1    2   55   56   57
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   58   59
CONECT    6    7   20   47
CONECT    7    8   12   60
CONECT    8    9
CONECT    9   10   11   11
CONECT   10   61   62   63
CONECT   12   13   14   64
CONECT   13   65
CONECT   14   15   22   66
CONECT   15   16   20   67
CONECT   16   17
CONECT   17   18   19   19
CONECT   18   68   69   70
CONECT   20   21   52
CONECT   21   22
CONECT   22   23   24
CONECT   23   71   72   73
CONECT   24   25   74   75
CONECT   25   26
CONECT   26   27   27   28
CONECT   28   29   29   33
CONECT   29   30   76
CONECT   30   31   31   77
CONECT   31   32   78
CONECT   32   33   33
CONECT   33   34
CONECT   34   35   36   79
CONECT   35   80   81   82
CONECT   36   37   38   83
CONECT   37   84   85   86
CONECT   38   39   39   40
CONECT   40   41
CONECT   41   42   52   87
CONECT   42   43   47   88
CONECT   43   44
CONECT   44   45   46   46
CONECT   45   89   90   91
CONECT   47   48   92
CONECT   48   49
CONECT   49   50   51   51
CONECT   50   93   94   95
CONECT   52   53   54
CONECT   53   96   97   98
CONECT   54   99
END

HMDB0033578
     RDKit          3D
Aquifoliunine EIII
 99103  0  0  0  0  0  0  0  0999 V2000
   -3.8931   -2.1998   -4.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6155   -1.0403   -3.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0391    0.1270   -3.6612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8906   -1.1424   -2.1941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6282   -0.0556   -1.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8573   -0.1806   -0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6266   -1.1690    0.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5786   -0.8600    2.0893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7364   -0.6736    2.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6890   -0.3508    4.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8408   -0.7974    2.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856   -2.5863    0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9697   -3.4437    1.2134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458   -2.9006    0.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1578   -1.9812   -0.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6169   -2.2965   -1.9487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2300   -2.6596   -2.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -3.0059   -4.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4634   -2.6961   -2.7339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849   -0.6952   -0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3217   -1.0271    1.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1061   -2.2628    1.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4289   -2.6920    2.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5070   -2.6952    1.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5523   -1.8042    1.6420 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8769   -1.7887    1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8245   -2.3796    1.9416 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5229   -1.1948    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8882   -2.2117   -0.8924 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4731   -1.9872   -2.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7112   -0.6708   -2.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3801    0.2852   -1.5684 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7879    0.0781   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6918    1.3742    0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6877    1.1302    1.8675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7838    2.4131   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2291    3.3496    1.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7718    2.1692   -1.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3965    1.8111   -2.2101 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4525    2.3032   -0.9891 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2970    1.5379   -1.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9301    2.1390   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7669    3.3435    0.2629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2466    4.5730   -0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9711    5.7298    0.7971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8982    4.6616   -1.1622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8192    1.2320    0.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1363    1.7738    0.1786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8116    2.3537    1.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1863    2.8850    0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3511    2.4546    2.3949 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5978    0.3370   -0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050    0.9495    1.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6633   -0.2717   -0.7745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9235   -2.0462   -4.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9437   -3.1473   -3.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2120   -2.2227   -5.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3860    0.7953   -2.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6647    0.2560   -1.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7060   -1.1815    0.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5746    0.2619    4.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8014    0.2889    4.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6871   -1.2595    4.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5658   -2.8064   -0.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9101   -3.1990    1.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5723   -3.9403    0.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9488   -2.0441   -0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2920   -2.0620   -4.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5330   -3.6443   -4.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2163   -3.5359   -4.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4630   -1.8001    3.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3328   -3.2720    2.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3520   -3.3513    3.3536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6074   -3.5376    2.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7120   -3.3555    0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7578   -3.2846   -0.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7309   -2.8023   -2.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1762   -0.4787   -3.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8003    1.8437    0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7063    0.6871    2.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6623    2.1320    2.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9819    0.4089    2.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5473    3.1998   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247    3.8394    0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9182    4.2006    1.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    2.8518    1.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0664    1.0398   -2.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5396    2.4779   -1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8718    6.6741    0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7932    5.8002    1.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326    5.5907    1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6180    1.3333    1.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5125    3.6061    1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1337    3.3478   -0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8486    1.9969    0.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9800    0.7774    1.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4464    0.4263    2.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7339    2.0171    1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5833   -0.1727   -1.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  7 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  2  0
 38 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
 44 46  2  0
 42 47  1  0
 47 48  1  0
 48 49  1  0
 49 50  1  0
 49 51  2  0
 41 52  1  0
 52 53  1  0
 52 54  1  0
 20  6  1  0
 33 28  1  0
 47  6  1  0
 22 14  1  0
 52 20  1  0
  1 55  1  0
  1 56  1  0
  1 57  1  0
  5 58  1  0
  5 59  1  0
  7 60  1  0
 10 61  1  0
 10 62  1  0
 10 63  1  0
 12 64  1  0
 13 65  1  0
 14 66  1  0
 15 67  1  0
 18 68  1  0
 18 69  1  0
 18 70  1  0
 23 71  1  0
 23 72  1  0
 23 73  1  0
 24 74  1  0
 24 75  1  0
 29 76  1  0
 30 77  1  0
 31 78  1  0
 34 79  1  0
 35 80  1  0
 35 81  1  0
 35 82  1  0
 36 83  1  0
 37 84  1  0
 37 85  1  0
 37 86  1  0
 41 87  1  0
 42 88  1  0
 45 89  1  0
 45 90  1  0
 45 91  1  0
 47 92  1  0
 50 93  1  0
 50 94  1  0
 50 95  1  0
 53 96  1  0
 53 97  1  0
 53 98  1  0
 54 99  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Aquifoliunine e-III	HMDB
[18,19,21,24-Tetrakis(acetyloxy)-22,25-dihydroxy-3,13,14,25-tetramethyl-6,15-dioxo-2,5,16-trioxa-11-azapentacyclo[15.7.1.0¹,²⁰.0³,²³.0⁷,¹²]pentacosa-7(12),8,10-trien-20-yl]methyl acetic acid	Generator

Chemical Formula

C₃₆H₄₅NO₁₇

Average Molecular Weight

763.739

Monoisotopic Molecular Weight

763.268749019

IUPAC Name

[18,19,21,24-tetrakis(acetyloxy)-22,25-dihydroxy-3,13,14,25-tetramethyl-6,15-dioxo-2,5,16-trioxa-11-azapentacyclo[15.7.1.0¹,²⁰.0³,²³.0⁷,¹²]pentacosa-7(12),8,10-trien-20-yl]methyl acetate

Traditional Name

[18,19,21,24-tetrakis(acetyloxy)-22,25-dihydroxy-3,13,14,25-tetramethyl-6,15-dioxo-2,5,16-trioxa-11-azapentacyclo[15.7.1.0¹,²⁰.0³,²³.0⁷,¹²]pentacosa-7(12),8,10-trien-20-yl]methyl acetate

CAS Registry Number

220751-20-2

SMILES

CC1C(C)C(=O)OC2C(OC(C)=O)C(OC(C)=O)C3(COC(C)=O)C(OC(C)=O)C(O)C4C(OC(C)=O)C3(OC4(C)COC(=O)C3=C1N=CC=C3)C2(C)O

InChI Identifier

InChI=1S/C36H45NO17/c1-15-16(2)31(44)53-29-26(49-18(4)39)30(52-21(7)42)35(14-47-17(3)38)28(51-20(6)41)25(43)23-27(50-19(5)40)36(35,34(29,9)46)54-33(23,8)13-48-32(45)22-11-10-12-37-24(15)22/h10-12,15-16,23,25-30,43,46H,13-14H2,1-9H3

InChI Key

NLOQRURWORDOGK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033578)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033578)

Source

Endogenous

Endogenous (HMDB: HMDB0033578)

Plant

Plant (HMDB: HMDB0033578)

Exogenous

Food

Food (HMDB: HMDB0033578)

Tea

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0033578)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0033578)

Nutrient

Nutrient (HMDB: HMDB0033578)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033578)

Emulsifier (HMDB: HMDB0033578)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.36 g/L	ALOGPS
logP	1.74	ALOGPS
logP	-0.68	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	2.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	246.68 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	173.65 m³·mol⁻¹	ChemAxon
Polarizability	73.67 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	261.344	30932474
DeepCCS	[M-H]-	259.5	30932474
DeepCCS	[M-2H]-	293.321	30932474
DeepCCS	[M+Na]+	267.192	30932474
AllCCS	[M+H]+	256.0	32859911
AllCCS	[M+H-H2O]+	255.7	32859911
AllCCS	[M+NH4]+	256.2	32859911
AllCCS	[M+Na]+	256.3	32859911
AllCCS	[M-H]-	255.3	32859911
AllCCS	[M+Na-2H]-	259.2	32859911
AllCCS	[M+HCOO]-	263.6	32859911

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Aquifoliunine EIII GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-2000003900-013879497ba7a796ad72	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aquifoliunine EIII GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aquifoliunine EIII GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aquifoliunine EIII GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aquifoliunine EIII GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-18	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 - Aquifoliunine EIII 10V, Positive-QTOF	splash10-0ul1-0100454900-f765d10dc4f23b95bfe4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aquifoliunine EIII 20V, Positive-QTOF	splash10-0w29-0100009800-5c6c9442fc4b8e2390da	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aquifoliunine EIII 40V, Positive-QTOF	splash10-001i-2300790000-52aad1f1eaebf3c0df17	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aquifoliunine EIII 10V, Negative-QTOF	splash10-0229-2000013900-02018fd3702fdacb30cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aquifoliunine EIII 20V, Negative-QTOF	splash10-0mdi-4000009800-a8f7e37ed12e82d3da17	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aquifoliunine EIII 40V, Negative-QTOF	splash10-056r-2900005100-975239325298055469ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aquifoliunine EIII 10V, Negative-QTOF	splash10-03di-0000000900-5528ad99919ccd0a4e25	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aquifoliunine EIII 20V, Negative-QTOF	splash10-08fs-3000009200-d339d91d2e1f9d29f070	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aquifoliunine EIII 40V, Negative-QTOF	splash10-052f-9000001000-3a4a5b6d054a9176f58e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aquifoliunine EIII 10V, Positive-QTOF	splash10-03di-0000000900-eb53c9e9bc8dc225aa05	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aquifoliunine EIII 20V, Positive-QTOF	splash10-03ka-0000002900-c2f337dd7c3a7c9a3a42	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aquifoliunine EIII 40V, Positive-QTOF	splash10-0006-6000009400-1aa591cb98f9fce6f6c7	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
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

FDB011653

KNApSAcK ID

C00027889

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751458

PDB ID

Not Available

ChEBI ID

Not Available

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 Aquifoliunine EIII (HMDB0033578)

MOL for HMDB0033578 (Aquifoliunine EIII)

3D MOL for HMDB0033578 (Aquifoliunine EIII)

3D SDF for HMDB0033578 (Aquifoliunine EIII)

3D-SDF for HMDB0033578 (Aquifoliunine EIII)

PDB for HMDB0033578 (Aquifoliunine EIII)

3D PDB for HMDB0033578 (Aquifoliunine EIII)

SMILES for HMDB0033578 (Aquifoliunine EIII)

INCHI for HMDB0033578 (Aquifoliunine EIII)

Structure for HMDB0033578 (Aquifoliunine EIII)

3D Structure for HMDB0033578 (Aquifoliunine EIII)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra

NMR Spectra