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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:07:30 UTC

Update Date

2022-03-07 02:57:01 UTC

HMDB ID

HMDB0041437

Secondary Accession Numbers

HMDB41437

Metabolite Identification

Common Name

Citbismine D

Description

Citbismine D belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety. Citbismine D has been detected, but not quantified in, citrus. This could make citbismine D a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Citbismine D.

Structure

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


  Mrv0541 02241216362D          

 53 60  0  0  0  0            999 V2000
   -1.7702   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0616   -0.7079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0616   -1.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3536   -1.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3536   -2.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0616   -3.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7702   -2.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7702   -1.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6997   -3.8946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 52 53  1  0  0  0  0
M  END

HMDB0041437
     RDKit          3D
Citbismine D
 91 98  0  0  0  0  0  0  0  0999 V2000
    7.0863    2.3393    1.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241216362D          

 53 60  0  0  0  0            999 V2000
   -1.7702   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0616   -0.7079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0616   -1.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3536   -1.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7702   -2.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3536   -0.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9911   -2.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3536   -3.8946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1156    0.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6909    0.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4699    0.7784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1860    3.6114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4781    3.1860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8406    1.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4241    1.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0534    3.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  4 12  1  0  0  0  0
  5  6  1  0  0  0  0
  5 22  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 20  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 21  2  0  0  0  0
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 15 40  1  0  0  0  0
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 25 26  1  0  0  0  0
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 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 35  2  0  0  0  0
 31 32  2  0  0  0  0
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 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
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 38 39  1  0  0  0  0
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 39 40  1  0  0  0  0
 39 48  2  0  0  0  0
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 41 42  1  0  0  0  0
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 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
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 50 52  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041437

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC2=C1N(C)C1=C(C(O)=CC3=C1C(C(O3)C(C)(C)O)C1=C(O)C3=C(N(C)C4=C(C=CC(O)=C4OC)C3=O)C3=C1OC(C)(C)C=C3)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C40H38N2O11/c1-39(2)14-13-18-28-27(33(47)17-10-12-19(43)36(50-7)29(17)41(28)5)34(48)26(35(18)53-39)25-24-22(52-38(25)40(3,4)49)15-21(45)23-31(24)42(6)30-16(32(23)46)9-11-20(44)37(30)51-8/h9-15,25,38,43-45,48-49H,1-8H3

> <INCHI_KEY>
YDFOOKXFYDNPMQ-UHFFFAOYSA-N

> <FORMULA>
C40H38N2O11

> <MOLECULAR_WEIGHT>
722.7365

> <EXACT_MASS>
722.247560068

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
74.8940926784978

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-[5,9-dihydroxy-2-(2-hydroxypropan-2-yl)-10-methoxy-11-methyl-6-oxo-1H,2H,6H,11H-furo[2,3-c]acridin-1-yl]-7,11-dihydroxy-6-methoxy-2,2,5-trimethyl-5,10-dihydro-2H-1-oxa-5-azatetraphen-10-one

> <ALOGPS_LOGP>
5.04

> <JCHEM_LOGP>
6.391494315333334

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.571033601595262

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.911829554021867

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1155127255612802

> <JCHEM_POLAR_SURFACE_AREA>
178.68999999999997

> <JCHEM_REFRACTIVITY>
196.46110000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-[5,9-dihydroxy-2-(2-hydroxypropan-2-yl)-10-methoxy-11-methyl-6-oxo-1H,2H-furo[2,3-c]acridin-1-yl]-7,11-dihydroxy-6-methoxy-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041437
     RDKit          3D
Citbismine D
 91 98  0  0  0  0  0  0  0  0999 V2000
    7.0863    2.3393    1.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9919    0.9044    1.6469 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1275    0.2467    2.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6077   -0.0557    3.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8999    0.3079    4.0985 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8035   -0.6904    4.7239 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5129   -1.0499    4.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592   -0.7512    3.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -1.1040    2.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0548   -1.6880    3.7004 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2505   -0.8348    1.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9506   -1.1937    1.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1525   -1.8291    2.1987 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121   -0.9120    0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9876   -1.3545   -0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8408   -0.7101   -1.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5557   -1.2648   -2.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1998   -0.8799   -3.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1672    0.0780   -3.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8388    0.4882   -4.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4826    0.6544   -2.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5025    1.5825   -2.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0550    1.8937   -3.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8645    2.1125   -1.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8886    3.0208   -0.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3219    3.5849    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6967    3.2103    1.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6599    2.2938    1.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1004    1.9684    2.5253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7957    0.9193    3.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2093    1.7250    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2041    0.8229    0.1101 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4344    0.5320    1.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8185    0.2628   -1.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430   -2.2476   -2.2499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7406   -2.7118   -0.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9255   -3.6051   -0.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6675   -4.7683   -1.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0662   -4.1781    0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1115   -2.9845   -1.2341 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2125   -0.2808   -0.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5442    0.1095   -0.5751 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0673   -0.1871    0.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3374    0.1454    0.9593 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2780    0.3965   -0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8429   -0.1182    2.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2227    0.9940   -1.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5727    1.4131   -2.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001    1.0176   -2.9090 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0176    0.7117   -4.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3168    2.2475   -2.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7238    0.0051   -2.0882 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2139   -0.9014    5.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8582   -1.5465    5.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6731    0.1272   -5.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1485    4.3151    0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8544    4.4210    2.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3066    0.6144    1.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1436   -3.2128   -0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4760   -5.5346   -1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6293   -4.3429   -2.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9068   -3.7205    1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2433   -5.2855    0.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0950   -4.0561    1.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7871   -3.6933   -1.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0869   -0.2863   -1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1836   -0.3257    0.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7608    1.2815   -0.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1432    1.4405   -1.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0693    2.0851   -3.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486   -0.3474   -4.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5985    1.4418   -4.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0544    0.8635   -4.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6776    1.9867   -3.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7431    3.1131   -3.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2215    2.3925   -1.5503 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 29 32  2  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 17 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 38 40  1  0
 38 41  1  0
 14 42  2  0
 42 43  1  0
 43 44  2  0
 44 45  1  0
 45 46  1  0
 45 47  1  0
 43 48  1  0
 48 49  2  0
 49 50  1  0
 50 51  1  0
 50 52  1  0
 50 53  1  0
 47  3  1  0
 47  8  2  0
 44 11  1  0
 37 15  1  0
 53 42  1  0
 35 16  2  0
 35 21  1  0
 32 24  1  0
  1 54  1  0
  1 55  1  0
  1 56  1  0
  5 57  1  0
  6 58  1  0
  7 59  1  0
 13 60  1  0
 15 61  1  0
 18 62  1  0
 20 63  1  0
 25 64  1  0
 26 65  1  0
 28 66  1  0
 31 67  1  0
 31 68  1  0
 31 69  1  0
 34 70  1  0
 34 71  1  0
 34 72  1  0
 37 73  1  0
 39 74  1  0
 39 75  1  0
 39 76  1  0
 40 77  1  0
 40 78  1  0
 40 79  1  0
 41 80  1  0
 46 81  1  0
 46 82  1  0
 46 83  1  0
 48 84  1  0
 49 85  1  0
 51 86  1  0
 51 87  1  0
 51 88  1  0
 52 89  1  0
 52 90  1  0
 52 91  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.304  -0.529   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.982  -1.321   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.982  -2.776   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.660  -3.569   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.660  -5.023   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.982  -5.816   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.304  -5.023   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.304  -3.569   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.626  -2.776   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.173  -7.270   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.660  -1.321   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       0.660  -2.776   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.850  -3.569   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.173  -2.776   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.569  -1.321   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.023  -1.189   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.551  -2.511   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.494  -3.569   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.494  -5.023   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.173  -5.816   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.850  -5.023   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.660  -5.816   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.660  -7.270   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.270   0.133   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.816   0.133   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.023   1.453   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.477   1.453   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -5.947   6.741   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.626   5.947   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.626   4.494   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.436   3.700   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.436   2.246   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.626   1.453   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.947   2.246   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.947   3.700   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -7.270   4.494   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.529   0.000   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       3.173   4.494   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       1.850   3.700   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.850   2.246   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.529   1.453   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -0.792   2.246   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -2.114   1.453   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -2.114   0.000   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -2.114   5.947   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      -2.114   4.494   0.000  0.00  0.00           N+0
HETATM   47  C   UNK     0      -0.792   3.700   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       0.529   4.494   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       0.529   5.947   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       1.850   6.741   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       4.627   5.947   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       3.173   5.947   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       3.833   7.270   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    3    7    9                                                  
CONECT    9    8                                                            
CONECT   10   20                                                            
CONECT   11   12                                                            
CONECT   12    4   11   13                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   40                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   14   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   10   19   21                                                  
CONECT   21   13   20   22                                                  
CONECT   22    5   21   23                                                  
CONECT   23   22                                                            
CONECT   24   25                                                            
CONECT   25   16   24   26   27                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   29                                                            
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32   46                                                  
CONECT   32   31   33   43                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   30   34   36                                                  
CONECT   36   35                                                            
CONECT   37   41                                                            
CONECT   38   39   52                                                       
CONECT   39   38   40   48                                                  
CONECT   40   15   39   41                                                  
CONECT   41   37   40   42                                                  
CONECT   42   41   43   47                                                  
CONECT   43   32   42   44                                                  
CONECT   44   43                                                            
CONECT   45   46                                                            
CONECT   46   31   45   47                                                  
CONECT   47   42   46   48                                                  
CONECT   48   39   47   49                                                  
CONECT   49   48   50                                                       
CONECT   50   49   52                                                       
CONECT   51   52                                                            
CONECT   52   38   50   51   53                                             
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  120    0
END

COMPND    HMDB0041437
HETATM    1  C1  UNL     1       7.086   2.339   1.717  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.992   0.904   1.647  1.00  0.00           O  
HETATM    3  C2  UNL     1       6.128   0.247   2.509  1.00  0.00           C  
HETATM    4  C3  UNL     1       6.608  -0.056   3.805  1.00  0.00           C  
HETATM    5  O2  UNL     1       7.900   0.308   4.098  1.00  0.00           O  
HETATM    6  C4  UNL     1       5.804  -0.690   4.724  1.00  0.00           C  
HETATM    7  C5  UNL     1       4.513  -1.050   4.410  1.00  0.00           C  
HETATM    8  C6  UNL     1       4.059  -0.751   3.137  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.772  -1.104   2.835  1.00  0.00           C  
HETATM   10  O3  UNL     1       2.055  -1.688   3.700  1.00  0.00           O  
HETATM   11  C8  UNL     1       2.250  -0.835   1.613  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.951  -1.194   1.292  1.00  0.00           C  
HETATM   13  O4  UNL     1       0.153  -1.829   2.199  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.412  -0.912   0.015  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.988  -1.354  -0.166  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.841  -0.710  -1.135  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.556  -1.265  -2.367  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.200  -0.880  -3.504  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.167   0.078  -3.477  1.00  0.00           C  
HETATM   20  O5  UNL     1      -3.839   0.488  -4.625  1.00  0.00           O  
HETATM   21  C16 UNL     1      -3.483   0.654  -2.257  1.00  0.00           C  
HETATM   22  C17 UNL     1      -4.503   1.583  -2.218  1.00  0.00           C  
HETATM   23  O6  UNL     1      -5.055   1.894  -3.317  1.00  0.00           O  
HETATM   24  C18 UNL     1      -4.865   2.113  -1.033  1.00  0.00           C  
HETATM   25  C19 UNL     1      -5.889   3.021  -0.985  1.00  0.00           C  
HETATM   26  C20 UNL     1      -6.322   3.585   0.187  1.00  0.00           C  
HETATM   27  C21 UNL     1      -5.697   3.210   1.335  1.00  0.00           C  
HETATM   28  O7  UNL     1      -6.115   3.762   2.534  1.00  0.00           O  
HETATM   29  C22 UNL     1      -4.660   2.294   1.309  1.00  0.00           C  
HETATM   30  O8  UNL     1      -4.100   1.968   2.525  1.00  0.00           O  
HETATM   31  C23 UNL     1      -4.796   0.919   3.244  1.00  0.00           C  
HETATM   32  C24 UNL     1      -4.209   1.725   0.141  1.00  0.00           C  
HETATM   33  N1  UNL     1      -3.204   0.823   0.110  1.00  0.00           N  
HETATM   34  C25 UNL     1      -2.434   0.532   1.263  1.00  0.00           C  
HETATM   35  C26 UNL     1      -2.819   0.263  -1.078  1.00  0.00           C  
HETATM   36  O9  UNL     1      -0.543  -2.248  -2.250  1.00  0.00           O  
HETATM   37  C27 UNL     1      -0.741  -2.712  -0.923  1.00  0.00           C  
HETATM   38  C28 UNL     1      -1.925  -3.605  -0.845  1.00  0.00           C  
HETATM   39  C29 UNL     1      -1.667  -4.768  -1.789  1.00  0.00           C  
HETATM   40  C30 UNL     1      -2.066  -4.178   0.546  1.00  0.00           C  
HETATM   41  O10 UNL     1      -3.111  -2.984  -1.234  1.00  0.00           O  
HETATM   42  C31 UNL     1       1.213  -0.281  -0.855  1.00  0.00           C  
HETATM   43  C32 UNL     1       2.544   0.110  -0.575  1.00  0.00           C  
HETATM   44  C33 UNL     1       3.067  -0.187   0.665  1.00  0.00           C  
HETATM   45  N2  UNL     1       4.337   0.145   0.959  1.00  0.00           N  
HETATM   46  C34 UNL     1       5.278   0.397  -0.092  1.00  0.00           C  
HETATM   47  C35 UNL     1       4.843  -0.118   2.194  1.00  0.00           C  
HETATM   48  C36 UNL     1       3.223   0.994  -1.489  1.00  0.00           C  
HETATM   49  C37 UNL     1       2.573   1.413  -2.587  1.00  0.00           C  
HETATM   50  C38 UNL     1       1.200   1.018  -2.909  1.00  0.00           C  
HETATM   51  C39 UNL     1       1.018   0.712  -4.387  1.00  0.00           C  
HETATM   52  C40 UNL     1       0.317   2.247  -2.645  1.00  0.00           C  
HETATM   53  O11 UNL     1       0.724   0.005  -2.088  1.00  0.00           O  
HETATM   54  H1  UNL     1       7.792   2.637   0.916  1.00  0.00           H  
HETATM   55  H2  UNL     1       7.356   2.676   2.715  1.00  0.00           H  
HETATM   56  H3  UNL     1       6.054   2.749   1.535  1.00  0.00           H  
HETATM   57  H4  UNL     1       8.488   0.751   3.431  1.00  0.00           H  
HETATM   58  H5  UNL     1       6.214  -0.901   5.705  1.00  0.00           H  
HETATM   59  H6  UNL     1       3.858  -1.547   5.112  1.00  0.00           H  
HETATM   60  H7  UNL     1       0.144  -2.161   3.071  1.00  0.00           H  
HETATM   61  H8  UNL     1      -1.434  -1.751   0.727  1.00  0.00           H  
HETATM   62  H9  UNL     1      -1.953  -1.335  -4.494  1.00  0.00           H  
HETATM   63  H10 UNL     1      -3.673   0.127  -5.533  1.00  0.00           H  
HETATM   64  H11 UNL     1      -6.395   3.320  -1.912  1.00  0.00           H  
HETATM   65  H12 UNL     1      -7.149   4.315   0.189  1.00  0.00           H  
HETATM   66  H13 UNL     1      -6.854   4.421   2.594  1.00  0.00           H  
HETATM   67  H14 UNL     1      -5.135   0.155   2.508  1.00  0.00           H  
HETATM   68  H15 UNL     1      -5.658   1.327   3.792  1.00  0.00           H  
HETATM   69  H16 UNL     1      -4.121   0.462   3.971  1.00  0.00           H  
HETATM   70  H17 UNL     1      -1.307   0.614   1.034  1.00  0.00           H  
HETATM   71  H18 UNL     1      -2.667  -0.234   1.944  1.00  0.00           H  
HETATM   72  H19 UNL     1      -2.384   1.511   1.868  1.00  0.00           H  
HETATM   73  H20 UNL     1       0.144  -3.213  -0.573  1.00  0.00           H  
HETATM   74  H21 UNL     1      -2.476  -5.535  -1.717  1.00  0.00           H  
HETATM   75  H22 UNL     1      -1.629  -4.343  -2.812  1.00  0.00           H  
HETATM   76  H23 UNL     1      -0.731  -5.287  -1.514  1.00  0.00           H  
HETATM   77  H24 UNL     1      -2.907  -3.720   1.106  1.00  0.00           H  
HETATM   78  H25 UNL     1      -2.243  -5.285   0.500  1.00  0.00           H  
HETATM   79  H26 UNL     1      -1.095  -4.056   1.053  1.00  0.00           H  
HETATM   80  H27 UNL     1      -3.787  -3.693  -1.314  1.00  0.00           H  
HETATM   81  H28 UNL     1       5.087  -0.286  -1.020  1.00  0.00           H  
HETATM   82  H29 UNL     1       6.184  -0.326   0.199  1.00  0.00           H  
HETATM   83  H30 UNL     1       5.761   1.281  -0.293  1.00  0.00           H  
HETATM   84  H31 UNL     1       4.143   1.440  -1.362  1.00  0.00           H  
HETATM   85  H32 UNL     1       3.069   2.085  -3.298  1.00  0.00           H  
HETATM   86  H33 UNL     1       1.249  -0.347  -4.617  1.00  0.00           H  
HETATM   87  H34 UNL     1       1.599   1.442  -4.952  1.00  0.00           H  
HETATM   88  H35 UNL     1      -0.054   0.863  -4.655  1.00  0.00           H  
HETATM   89  H36 UNL     1      -0.678   1.987  -3.066  1.00  0.00           H  
HETATM   90  H37 UNL     1       0.743   3.113  -3.170  1.00  0.00           H  
HETATM   91  H38 UNL     1       0.221   2.393  -1.550  1.00  0.00           H  
CONECT    1    2   54   55   56
CONECT    2    3
CONECT    3    4    4   47
CONECT    4    5    6
CONECT    5   57
CONECT    6    7    7   58
CONECT    7    8   59
CONECT    8    9   47   47
CONECT    9   10   10   11
CONECT   11   12   12   44
CONECT   12   13   14
CONECT   13   60
CONECT   14   15   42   42
CONECT   15   16   37   61
CONECT   16   17   35   35
CONECT   17   18   18   36
CONECT   18   19   62
CONECT   19   20   21   21
CONECT   20   63
CONECT   21   22   35
CONECT   22   23   23   24
CONECT   24   25   25   32
CONECT   25   26   64
CONECT   26   27   27   65
CONECT   27   28   29
CONECT   28   66
CONECT   29   30   32   32
CONECT   30   31
CONECT   31   67   68   69
CONECT   32   33
CONECT   33   34   35
CONECT   34   70   71   72
CONECT   36   37
CONECT   37   38   73
CONECT   38   39   40   41
CONECT   39   74   75   76
CONECT   40   77   78   79
CONECT   41   80
CONECT   42   43   53
CONECT   43   44   44   48
CONECT   44   45
CONECT   45   46   47
CONECT   46   81   82   83
CONECT   48   49   49   84
CONECT   49   50   85
CONECT   50   51   52   53
CONECT   51   86   87   88
CONECT   52   89   90   91
END

HMDB0041437
     RDKit          3D
Citbismine D
 91 98  0  0  0  0  0  0  0  0999 V2000
    7.0863    2.3393    1.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9919    0.9044    1.6469 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1275    0.2467    2.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6077   -0.0557    3.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8999    0.3079    4.0985 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8035   -0.6904    4.7239 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5129   -1.0499    4.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592   -0.7512    3.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -1.1040    2.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0548   -1.6880    3.7004 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2505   -0.8348    1.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9506   -1.1937    1.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1525   -1.8291    2.1987 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121   -0.9120    0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9876   -1.3545   -0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8408   -0.7101   -1.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5557   -1.2648   -2.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1998   -0.8799   -3.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1672    0.0780   -3.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8388    0.4882   -4.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4826    0.6544   -2.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5025    1.5825   -2.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0550    1.8937   -3.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8645    2.1125   -1.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8886    3.0208   -0.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3219    3.5849    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6967    3.2103    1.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1146    3.7617    2.5338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6599    2.2938    1.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1004    1.9684    2.5253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7957    0.9193    3.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2093    1.7250    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2041    0.8229    0.1101 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4344    0.5320    1.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8185    0.2628   -1.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430   -2.2476   -2.2499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7406   -2.7118   -0.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9255   -3.6051   -0.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6675   -4.7683   -1.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0662   -4.1781    0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1115   -2.9845   -1.2341 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2125   -0.2808   -0.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5442    0.1095   -0.5751 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0673   -0.1871    0.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3374    0.1454    0.9593 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2780    0.3965   -0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8429   -0.1182    2.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2227    0.9940   -1.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5727    1.4131   -2.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001    1.0176   -2.9090 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0176    0.7117   -4.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3168    2.2475   -2.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7238    0.0051   -2.0882 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7924    2.6373    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3557    2.6762    2.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0544    2.7490    1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4877    0.7509    3.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2139   -0.9014    5.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8582   -1.5465    5.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1438   -2.1607    3.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4337   -1.7513    0.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.8544    4.4210    2.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1349    0.1547    2.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6581    1.3269    3.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1209    0.4623    3.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3066    0.6144    1.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6672   -0.2341    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3840    1.5112    1.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1436   -3.2128   -0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4760   -5.5346   -1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6293   -4.3429   -2.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7308   -5.2868   -1.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9068   -3.7205    1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2433   -5.2855    0.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0950   -4.0561    1.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7871   -3.6933   -1.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0869   -0.2863   -1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1836   -0.3257    0.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7608    1.2815   -0.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1432    1.4405   -1.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0693    2.0851   -3.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486   -0.3474   -4.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5985    1.4418   -4.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0544    0.8635   -4.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6776    1.9867   -3.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7431    3.1131   -3.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2215    2.3925   -1.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₄₀H₃₈N₂O₁₁

Average Molecular Weight

722.7365

Monoisotopic Molecular Weight

722.247560068

IUPAC Name

12-[5,9-dihydroxy-2-(2-hydroxypropan-2-yl)-10-methoxy-11-methyl-6-oxo-1H,2H,6H,11H-furo[2,3-c]acridin-1-yl]-7,11-dihydroxy-6-methoxy-2,2,5-trimethyl-5,10-dihydro-2H-1-oxa-5-azatetraphen-10-one

Traditional Name

12-[5,9-dihydroxy-2-(2-hydroxypropan-2-yl)-10-methoxy-11-methyl-6-oxo-1H,2H-furo[2,3-c]acridin-1-yl]-7,11-dihydroxy-6-methoxy-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one

CAS Registry Number

173429-81-7

SMILES

COC1=C(O)C=CC2=C1N(C)C1=C(C(O)=CC3=C1C(C(O3)C(C)(C)O)C1=C(O)C3=C(N(C)C4=C(C=CC(O)=C4OC)C3=O)C3=C1OC(C)(C)C=C3)C2=O

InChI Identifier

InChI=1S/C40H38N2O11/c1-39(2)14-13-18-28-27(33(47)17-10-12-19(43)36(50-7)29(17)41(28)5)34(48)26(35(18)53-39)25-24-22(52-38(25)40(3,4)49)15-21(45)23-31(24)42(6)30-16(32(23)46)9-11-20(44)37(30)51-8/h9-15,25,38,43-45,48-49H,1-8H3

InChI Key

YDFOOKXFYDNPMQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridones

Alternative Parents

Substituents

Acridone
Chromenopyridine
2,2-dimethyl-1-benzopyran
Dihydroquinolone
Benzopyran
Dihydroquinoline
1-benzopyran
Coumaran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyridine
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Vinylogous amide
Vinylogous acid
Oxacycle
Ether
Azacycle
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041437)
Cell membrane (HMDB: HMDB0041437)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041437)

Source

Exogenous

Exogenous (HMDB: HMDB0041437)

Food

Food (HMDB: HMDB0041437)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0041437)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041437)

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	0.0021 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
logP	5.04	ALOGPS
logP	6.39	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	7.91	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	178.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	196.46 m³·mol⁻¹	ChemAxon
Polarizability	74.89 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	258.06	31661259
DarkChem	[M-H]-	251.31	31661259
DeepCCS	[M+H]+	261.687	30932474
DeepCCS	[M-H]-	259.792	30932474
DeepCCS	[M-2H]-	293.825	30932474
DeepCCS	[M+Na]+	267.715	30932474
AllCCS	[M+H]+	260.7	32859911
AllCCS	[M+H-H2O]+	259.9	32859911
AllCCS	[M+NH4]+	261.5	32859911
AllCCS	[M+Na]+	261.7	32859911
AllCCS	[M-H]-	260.3	32859911
AllCCS	[M+Na-2H]-	263.5	32859911
AllCCS	[M+HCOO]-	267.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.57 minutes	32390414
Predicted by Siyang on May 30, 2022	11.8572 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.16 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3156.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	156.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	161.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	149.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	94.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	599.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	479.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	677.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	788.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	336.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	953.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	270.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	378.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	329.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	667.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	12.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citbismine D	COC1=C(O)C=CC2=C1N(C)C1=C(C(O)=CC3=C1C(C(O3)C(C)(C)O)C1=C(O)C3=C(N(C)C4=C(C=CC(O)=C4OC)C3=O)C3=C1OC(C)(C)C=C3)C2=O	6624.6	Standard polar	33892256
Citbismine D	COC1=C(O)C=CC2=C1N(C)C1=C(C(O)=CC3=C1C(C(O3)C(C)(C)O)C1=C(O)C3=C(N(C)C4=C(C=CC(O)=C4OC)C3=O)C3=C1OC(C)(C)C=C3)C2=O	4623.1	Standard non polar	33892256
Citbismine D	COC1=C(O)C=CC2=C1N(C)C1=C(C(O)=CC3=C1C(C(O3)C(C)(C)O)C1=C(O)C3=C(N(C)C4=C(C=CC(O)=C4OC)C3=O)C3=C1OC(C)(C)C=C3)C2=O	6123.8	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 - Citbismine D GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citbismine D GC-MS (TBDMS_1_5) - 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 - Citbismine D 10V, Positive-QTOF	splash10-05fr-0000003900-945bdf558a15901a04bf	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citbismine D 20V, Positive-QTOF	splash10-0abi-0001009500-8c819043da595f1ba923	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citbismine D 40V, Positive-QTOF	splash10-0ar1-1000039000-8770697cc6c4638eb8cb	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citbismine D 10V, Negative-QTOF	splash10-00di-0000000900-85a3168985be72fbc991	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citbismine D 20V, Negative-QTOF	splash10-0uk9-0008009800-5b131697c9da64a8da32	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citbismine D 40V, Negative-QTOF	splash10-0udr-0003019100-a4457e3762f86316b53b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citbismine D 10V, Negative-QTOF	splash10-00di-0000000900-62cd36c0c7d0a59d18bb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citbismine D 20V, Negative-QTOF	splash10-05fs-0000005900-14acdb0268e7262a6548	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citbismine D 40V, Negative-QTOF	splash10-000b-0003009100-640794aa55813c351576	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citbismine D 10V, Positive-QTOF	splash10-00di-0000000900-402dccd3eb41411fc88a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citbismine D 20V, Positive-QTOF	splash10-00di-0000000900-7952f06e2042454da226	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citbismine D 40V, Positive-QTOF	splash10-0pba-2000009200-471819008633a8acbc74	2021-09-24	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

FDB021388

KNApSAcK ID

C00052238

Chemspider ID

35015189

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131753144

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1892451

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 Citbismine D (HMDB0041437)

MOL for HMDB0041437 (Citbismine D)

3D MOL for HMDB0041437 (Citbismine D)

3D SDF for HMDB0041437 (Citbismine D)

3D-SDF for HMDB0041437 (Citbismine D)

PDB for HMDB0041437 (Citbismine D)

3D PDB for HMDB0041437 (Citbismine D)

SMILES for HMDB0041437 (Citbismine D)

INCHI for HMDB0041437 (Citbismine D)

Structure for HMDB0041437 (Citbismine D)

3D Structure for HMDB0041437 (Citbismine D)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra