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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:10:51 UTC

Update Date

2022-03-07 02:53:42 UTC

HMDB ID

HMDB0033446

Secondary Accession Numbers

HMDB33446

Metabolite Identification

Common Name

Rutagravine

Description

Rutagravine 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. Rutagravine is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, rutagravine has been detected, but not quantified in, herbs and spices. This could make rutagravine a potential biomarker for the consumption of these foods.

Structure

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


  Mrv0541 05061307082D          

 25 29  0  0  0  0            999 V2000
    2.4245    0.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5822    1.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5082    1.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0526    1.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1405    0.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2291    1.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9347   -1.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3055    1.6049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3170    0.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8614    0.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7581   -1.2837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4790   -0.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1259   -0.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8467    0.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6702    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9493   -0.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2580    0.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5264    0.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9377    0.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0379    0.8810    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2138   -1.9714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4050   -1.1822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417    1.3093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1215    1.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6630   -0.5252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 10  9  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  2  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 17  1  0  0  0  0
 19  1  1  0  0  0  0
 19  8  1  0  0  0  0
 19 18  1  0  0  0  0
 20  2  1  0  0  0  0
 20 10  1  0  0  0  0
 20 15  1  0  0  0  0
 21 11  1  0  0  0  0
 22 16  2  0  0  0  0
 23 19  1  0  0  0  0
 24  8  1  0  0  0  0
 24 17  1  0  0  0  0
 25 12  1  0  0  0  0
 25 18  1  0  0  0  0
M  END

HMDB0033446
     RDKit          3D
Rutagravine
 42 46  0  0  0  0  0  0  0  0999 V2000
   -0.7698    1.8455    0.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4339    0.6121    0.1207 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006    0.5302    0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5639    1.5571    0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9684    1.4508    0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6130    0.3230    0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8280   -0.7072   -0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4559   -0.6004   -0.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7539   -1.6697   -0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3545   -2.7075   -1.1577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3556   -1.6055   -0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6515   -2.6830   -1.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2029   -3.8243   -1.7432 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355   -2.5628   -1.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845   -1.4558   -0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362   -0.3687   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7560   -0.4371   -0.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6132    0.5571    0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2345   -0.2165    1.1843 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4582    0.4301    1.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119    0.8695   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2464    0.3181   -0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8468    2.2566   -0.0951 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7859    0.3315   -0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7563   -1.1143   -0.8006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4586    1.9939    1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1343    2.2249   -0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5839    2.6472    0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1236    2.4493    1.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5239    2.2915    1.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6894    0.2477    0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3132   -1.6121   -0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0460   -4.2273   -1.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3191   -3.3997   -1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5619    1.4762    0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1858   -0.3356    1.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4389    1.2506    2.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0867    1.0351   -0.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3112    0.0518   -1.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5230   -0.6111    0.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7010    2.6612    0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6440    0.7281   -1.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  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  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 17  2  1  0
 24 18  1  0
  8  3  1  0
 17 11  1  0
 25 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
 13 33  1  0
 14 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 22 38  1  0
 22 39  1  0
 22 40  1  0
 23 41  1  0
 24 42  1  0
M  END


  Mrv0541 05061307082D          

 25 29  0  0  0  0            999 V2000
    2.4245    0.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5822    1.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5082    1.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0526    1.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1405    0.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2291    1.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9347   -1.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3055    1.6049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3170    0.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8614    0.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7581   -1.2837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4790   -0.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1259   -0.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8467    0.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6702    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9493   -0.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2580    0.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5264    0.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9377    0.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0379    0.8810    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2138   -1.9714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4050   -1.1822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417    1.3093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1215    1.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6630   -0.5252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 10  9  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  2  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 17  1  0  0  0  0
 19  1  1  0  0  0  0
 19  8  1  0  0  0  0
 19 18  1  0  0  0  0
 20  2  1  0  0  0  0
 20 10  1  0  0  0  0
 20 15  1  0  0  0  0
 21 11  1  0  0  0  0
 22 16  2  0  0  0  0
 23 19  1  0  0  0  0
 24  8  1  0  0  0  0
 24 17  1  0  0  0  0
 25 12  1  0  0  0  0
 25 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033446

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=CC=CC=C2C(=O)C2=C1C1=C(OC3C1OCC3(C)O)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C19H17NO5/c1-19(23)8-24-17-14-12(25-18(17)19)7-11(21)13-15(14)20(2)10-6-4-3-5-9(10)16(13)22/h3-7,17-18,21,23H,8H2,1-2H3

> <INCHI_KEY>
SWALXCKAJQTSAC-UHFFFAOYSA-N

> <FORMULA>
C19H17NO5

> <MOLECULAR_WEIGHT>
339.342

> <EXACT_MASS>
339.110672659

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
34.9864272249543

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,11-dihydroxy-6,20-dimethyl-4,8-dioxa-20-azapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),10,14,16,18-hexaen-13-one

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
2.6142210069999994

> <ALOGPS_LOGS>
-2.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.181530603776356

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.961612033479478

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5943146777169606

> <JCHEM_POLAR_SURFACE_AREA>
79.23

> <JCHEM_REFRACTIVITY>
89.9727

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,11-dihydroxy-6,20-dimethyl-4,8-dioxa-20-azapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),10,14,16,18-hexaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033446
     RDKit          3D
Rutagravine
 42 46  0  0  0  0  0  0  0  0999 V2000
   -0.7698    1.8455    0.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4339    0.6121    0.1207 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006    0.5302    0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5639    1.5571    0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9684    1.4508    0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6130    0.3230    0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8280   -0.7072   -0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4559   -0.6004   -0.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7539   -1.6697   -0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3545   -2.7075   -1.1577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3556   -1.6055   -0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6515   -2.6830   -1.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2029   -3.8243   -1.7432 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355   -2.5628   -1.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845   -1.4558   -0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362   -0.3687   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7560   -0.4371   -0.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6132    0.5571    0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2345   -0.2165    1.1843 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4582    0.4301    1.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119    0.8695   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2464    0.3181   -0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8468    2.2566   -0.0951 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7859    0.3315   -0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7563   -1.1143   -0.8006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4586    1.9939    1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1343    2.2249   -0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5839    2.6472    0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1236    2.4493    1.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5239    2.2915    1.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6894    0.2477    0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3132   -1.6121   -0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0460   -4.2273   -1.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3191   -3.3997   -1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5619    1.4762    0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1858   -0.3356    1.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4389    1.2506    2.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0867    1.0351   -0.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3112    0.0518   -1.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5230   -0.6111    0.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7010    2.6612    0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6440    0.7281   -1.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  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  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 17  2  1  0
 24 18  1  0
  8  3  1  0
 17 11  1  0
 25 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
 13 33  1  0
 14 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 22 38  1  0
 22 39  1  0
 22 40  1  0
 23 41  1  0
 24 42  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       4.526   0.412   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.420   2.928   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.882   1.929   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.032   3.213   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.196   0.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.494   3.118   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.211  -2.491   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.170   2.996   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.658   0.456   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.808   1.739   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.748  -2.396   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.361  -1.207   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.435  -1.018   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.047   0.171   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.584   0.266   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.972  -0.923   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.948   1.250   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.583   0.538   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.484   1.617   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      11.271   1.645   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      11.599  -3.680   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      13.823  -2.207   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.185   2.444   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.693   2.769   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.838  -0.980   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    9                                                       
CONECT    6    4   10                                                       
CONECT    7   11   12                                                       
CONECT    8   19   24                                                       
CONECT    9    5   10   16                                                  
CONECT   10    6    9   20                                                  
CONECT   11    7   13   21                                                  
CONECT   12    7   14   25                                                  
CONECT   13   11   15   16                                                  
CONECT   14   12   15   17                                                  
CONECT   15   13   14   20                                                  
CONECT   16    9   13   22                                                  
CONECT   17   14   18   24                                                  
CONECT   18   17   19   25                                                  
CONECT   19    1    8   18   23                                             
CONECT   20    2   10   15                                                  
CONECT   21   11                                                            
CONECT   22   16                                                            
CONECT   23   19                                                            
CONECT   24    8   17                                                       
CONECT   25   12   18                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

COMPND    HMDB0033446
HETATM    1  C1  UNL     1      -0.770   1.845   0.458  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.434   0.612   0.121  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.801   0.530   0.175  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.564   1.557   0.681  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.968   1.451   0.746  1.00  0.00           C  
HETATM    6  C5  UNL     1      -5.613   0.323   0.308  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.828  -0.707  -0.199  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.456  -0.600  -0.260  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.754  -1.670  -0.755  1.00  0.00           C  
HETATM   10  O1  UNL     1      -3.355  -2.708  -1.158  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.356  -1.605  -0.813  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.652  -2.683  -1.294  1.00  0.00           C  
HETATM   13  O2  UNL     1      -1.203  -3.824  -1.743  1.00  0.00           O  
HETATM   14  C11 UNL     1       0.735  -2.563  -1.307  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.385  -1.456  -0.874  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.636  -0.369  -0.385  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.756  -0.437  -0.358  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.613   0.557   0.086  1.00  0.00           C  
HETATM   19  O3  UNL     1       2.235  -0.217   1.184  1.00  0.00           O  
HETATM   20  C16 UNL     1       3.458   0.430   1.336  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.912   0.869  -0.047  1.00  0.00           C  
HETATM   22  C18 UNL     1       5.246   0.318  -0.424  1.00  0.00           C  
HETATM   23  O4  UNL     1       3.847   2.257  -0.095  1.00  0.00           O  
HETATM   24  C19 UNL     1       2.786   0.331  -0.878  1.00  0.00           C  
HETATM   25  O5  UNL     1       2.756  -1.114  -0.801  1.00  0.00           O  
HETATM   26  H1  UNL     1      -0.459   1.994   1.467  1.00  0.00           H  
HETATM   27  H2  UNL     1      -0.134   2.225  -0.383  1.00  0.00           H  
HETATM   28  H3  UNL     1      -1.584   2.647   0.343  1.00  0.00           H  
HETATM   29  H4  UNL     1      -3.124   2.449   1.059  1.00  0.00           H  
HETATM   30  H5  UNL     1      -5.524   2.292   1.153  1.00  0.00           H  
HETATM   31  H6  UNL     1      -6.689   0.248   0.359  1.00  0.00           H  
HETATM   32  H7  UNL     1      -5.313  -1.612  -0.552  1.00  0.00           H  
HETATM   33  H8  UNL     1      -2.046  -4.227  -1.872  1.00  0.00           H  
HETATM   34  H9  UNL     1       1.319  -3.400  -1.684  1.00  0.00           H  
HETATM   35  H10 UNL     1       1.562   1.476   0.525  1.00  0.00           H  
HETATM   36  H11 UNL     1       4.186  -0.336   1.687  1.00  0.00           H  
HETATM   37  H12 UNL     1       3.439   1.251   2.061  1.00  0.00           H  
HETATM   38  H13 UNL     1       6.087   1.035  -0.261  1.00  0.00           H  
HETATM   39  H14 UNL     1       5.311   0.052  -1.516  1.00  0.00           H  
HETATM   40  H15 UNL     1       5.523  -0.611   0.120  1.00  0.00           H  
HETATM   41  H16 UNL     1       3.701   2.661   0.796  1.00  0.00           H  
HETATM   42  H17 UNL     1       2.644   0.728  -1.858  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   17
CONECT    3    4    4    8
CONECT    4    5   29
CONECT    5    6    6   30
CONECT    6    7   31
CONECT    7    8    8   32
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   17
CONECT   12   13   14
CONECT   13   33
CONECT   14   15   15   34
CONECT   15   16   25
CONECT   16   17   17   18
CONECT   18   19   24   35
CONECT   19   20
CONECT   20   21   36   37
CONECT   21   22   23   24
CONECT   22   38   39   40
CONECT   23   41
CONECT   24   25   42
END

HMDB0033446
     RDKit          3D
Rutagravine
 42 46  0  0  0  0  0  0  0  0999 V2000
   -0.7698    1.8455    0.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4339    0.6121    0.1207 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006    0.5302    0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5639    1.5571    0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9684    1.4508    0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6130    0.3230    0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8280   -0.7072   -0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4559   -0.6004   -0.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7539   -1.6697   -0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3545   -2.7075   -1.1577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3556   -1.6055   -0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6515   -2.6830   -1.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2029   -3.8243   -1.7432 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355   -2.5628   -1.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845   -1.4558   -0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362   -0.3687   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7560   -0.4371   -0.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6132    0.5571    0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2345   -0.2165    1.1843 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4582    0.4301    1.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119    0.8695   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2464    0.3181   -0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8468    2.2566   -0.0951 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7859    0.3315   -0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7563   -1.1143   -0.8006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4586    1.9939    1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1343    2.2249   -0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5839    2.6472    0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1236    2.4493    1.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5239    2.2915    1.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6894    0.2477    0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3132   -1.6121   -0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0460   -4.2273   -1.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3191   -3.3997   -1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5619    1.4762    0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1858   -0.3356    1.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4389    1.2506    2.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0867    1.0351   -0.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3112    0.0518   -1.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5230   -0.6111    0.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7010    2.6612    0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6440    0.7281   -1.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  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  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 17  2  1  0
 24 18  1  0
  8  3  1  0
 17 11  1  0
 25 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
 13 33  1  0
 14 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 22 38  1  0
 22 39  1  0
 22 40  1  0
 23 41  1  0
 24 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₁₇NO₅

Average Molecular Weight

339.342

Monoisotopic Molecular Weight

339.110672659

IUPAC Name

6,11-dihydroxy-6,20-dimethyl-4,8-dioxa-20-azapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),10,14,16,18-hexaen-13-one

Traditional Name

6,11-dihydroxy-6,20-dimethyl-4,8-dioxa-20-azapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),10,14,16,18-hexaen-13-one

CAS Registry Number

101330-60-3

SMILES

CN1C2=CC=CC=C2C(=O)C2=C1C1=C(OC3C1OCC3(C)O)C=C2O

InChI Identifier

InChI=1S/C19H17NO5/c1-19(23)8-24-17-14-12(25-18(17)19)7-11(21)13-15(14)20(2)10-6-4-3-5-9(10)16(13)22/h3-7,17-18,21,23H,8H2,1-2H3

InChI Key

SWALXCKAJQTSAC-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
Dihydroquinolone
Dihydroquinoline
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyridine
Benzenoid
Vinylogous amide
Vinylogous acid
Heteroaromatic compound
Tetrahydrofuran
Tertiary alcohol
Oxacycle
Azacycle
Dialkyl ether
Ether
Hydrocarbon derivative
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033446)
Cytoplasm (HMDB: HMDB0033446)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033446)

Source

Exogenous

Food

Food (HMDB: HMDB0033446)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033446)

Not Available

Nutrient (HMDB: HMDB0033446)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	209 - 212 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.06 g/L	ALOGPS
logP	2.3	ALOGPS
logP	2.61	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.96	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	89.97 m³·mol⁻¹	ChemAxon
Polarizability	34.99 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	175.053	31661259
DarkChem	[M-H]-	174.344	31661259
DeepCCS	[M+H]+	171.446	30932474
DeepCCS	[M-H]-	169.089	30932474
DeepCCS	[M-2H]-	202.328	30932474
DeepCCS	[M+Na]+	177.555	30932474
AllCCS	[M+H]+	179.9	32859911
AllCCS	[M+H-H2O]+	176.6	32859911
AllCCS	[M+NH4]+	183.0	32859911
AllCCS	[M+Na]+	183.9	32859911
AllCCS	[M-H]-	186.1	32859911
AllCCS	[M+Na-2H]-	185.5	32859911
AllCCS	[M+HCOO]-	185.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rutagravine	CN1C2=CC=CC=C2C(=O)C2=C1C1=C(OC3C1OCC3(C)O)C=C2O	4102.6	Standard polar	33892256
Rutagravine	CN1C2=CC=CC=C2C(=O)C2=C1C1=C(OC3C1OCC3(C)O)C=C2O	2728.6	Standard non polar	33892256
Rutagravine	CN1C2=CC=CC=C2C(=O)C2=C1C1=C(OC3C1OCC3(C)O)C=C2O	3374.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rutagravine,1TMS,isomer #1	CN1C2=CC=CC=C2C(=O)C2=C(O)C=C3OC4C(OCC4(C)O[Si](C)(C)C)C3=C21	3146.9	Semi standard non polar	33892256
Rutagravine,1TMS,isomer #2	CN1C2=CC=CC=C2C(=O)C2=C(O[Si](C)(C)C)C=C3OC4C(OCC4(C)O)C3=C21	3216.4	Semi standard non polar	33892256
Rutagravine,2TMS,isomer #1	CN1C2=CC=CC=C2C(=O)C2=C(O[Si](C)(C)C)C=C3OC4C(OCC4(C)O[Si](C)(C)C)C3=C21	3196.0	Semi standard non polar	33892256
Rutagravine,1TBDMS,isomer #1	CN1C2=CC=CC=C2C(=O)C2=C(O)C=C3OC4C(OCC4(C)O[Si](C)(C)C(C)(C)C)C3=C21	3368.7	Semi standard non polar	33892256
Rutagravine,1TBDMS,isomer #2	CN1C2=CC=CC=C2C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C3OC4C(OCC4(C)O)C3=C21	3412.4	Semi standard non polar	33892256
Rutagravine,2TBDMS,isomer #1	CN1C2=CC=CC=C2C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C3OC4C(OCC4(C)O[Si](C)(C)C(C)(C)C)C3=C21	3621.9	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 - Rutagravine GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9075000000-1244bc096e5f3575fd7a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rutagravine GC-MS (2 TMS) - 70eV, Positive	splash10-01bi-1405900000-a0d6661f995064d02fbf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rutagravine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rutagravine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutagravine 10V, Positive-QTOF	splash10-0006-0019000000-ed52f50c2b07a3d1f971	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutagravine 20V, Positive-QTOF	splash10-006x-0019000000-2b7ea94dbdd073dfb457	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutagravine 40V, Positive-QTOF	splash10-00di-1291000000-d9095fe856a3e7305e0e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutagravine 10V, Negative-QTOF	splash10-000i-0009000000-d44b2dffae980b7968fa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutagravine 20V, Negative-QTOF	splash10-0079-0009000000-3b56b5084e958f3f9884	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutagravine 40V, Negative-QTOF	splash10-00di-1191000000-1cee95f0ff64b4a02461	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutagravine 10V, Negative-QTOF	splash10-000i-0009000000-44ba58366199301e50a3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutagravine 20V, Negative-QTOF	splash10-000i-0098000000-d3e1c79e6464aab68036	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutagravine 40V, Negative-QTOF	splash10-053i-0059000000-19966651bdec8b6213bc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutagravine 10V, Positive-QTOF	splash10-0006-0009000000-ad69679611f6ad4c80b6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutagravine 20V, Positive-QTOF	splash10-0006-0019000000-edca42c96fe11fcc7e8b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutagravine 40V, Positive-QTOF	splash10-006x-1196000000-113443014424f72386ab	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB011484

KNApSAcK ID

Not Available

Chemspider ID

4577337

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5465778

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 Rutagravine (HMDB0033446)

MOL for HMDB0033446 (Rutagravine)

3D MOL for HMDB0033446 (Rutagravine)

3D SDF for HMDB0033446 (Rutagravine)

3D-SDF for HMDB0033446 (Rutagravine)

PDB for HMDB0033446 (Rutagravine)

3D PDB for HMDB0033446 (Rutagravine)

SMILES for HMDB0033446 (Rutagravine)

INCHI for HMDB0033446 (Rutagravine)

Structure for HMDB0033446 (Rutagravine)

3D Structure for HMDB0033446 (Rutagravine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra