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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:42 UTC

HMDB ID

HMDB0014668

Secondary Accession Numbers

HMDB14668

Metabolite Identification

Common Name

Dibucaine

Description

Dibucaine, also known as cinchocainum or dibucaine base, belongs to the class of organic compounds known as quinolones and derivatives. Quinolones and derivatives are compounds containing a quinoline moiety which bears a ketone group. Dibucaine is a drug which is used for production of local or regional anesthesia by infiltration techniques such as percutaneous injection and intravenous regional anesthesia by peripheral nerve block techniques such as brachial plexus and intercostal and by central neural techniques such as lumbar and caudal epidural blocks. One of the most potent and toxic of the long-acting local anesthetics, its parenteral use was restricted to spinal anesthesia. It is now generally only used (usually as the hydrochloride) in creams and ointments and in suppositories for temporary relief of pain and itching associated with skin and anorectal conditions. Dibucaine is a very strong basic compound (based on its pKa). In humans, dibucaine is involved in dibucaine action pathway. A monocarboxylic acid amide that is the 2-(diethylamino)ethyl amide of 2-butoxyquinoline-4-carboxylic acid.

Structure

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

HMDB0014668
     RDKit          3D
Dibucaine
 54 55  0  0  0  0  0  0  0  0999 V2000
    3.9332    1.1415   -2.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3543    1.6030   -2.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9421    1.3746   -0.8913 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3064    2.0987    0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0107    1.9768    0.5789 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2410    0.9353    1.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8914    1.1946    1.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687    0.2083    1.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486    0.4642    2.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5182    1.1122    3.1881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3698   -0.1028    1.2775 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2354   -0.5767    0.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2084    0.4566   -0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2105   -0.1712   -0.9344 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1842   -0.8944   -0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2698   -1.5184   -1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6556    0.6254   -2.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3828    1.8671   -1.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.0766    1.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7236   -2.0977    2.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2520   -3.3837    2.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -3.6459    2.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3391   -2.6132    1.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8349   -1.3505    1.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6314   -0.3289    1.1096 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6231    0.9990   -3.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    0.1727   -1.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2634    1.8846   -1.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0491    1.0883   -2.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3699    2.6931   -2.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9641    0.2647   -0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0422    1.6483   -0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5816    3.2382    0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401    1.8352    1.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5655    2.2021    1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2948    0.4240    2.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8966   -1.2260   -0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9587   -1.3511    0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829    1.0374    0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613    1.1515   -0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7055   -1.8138    0.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6177   -0.3609    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8957   -0.6910   -1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8152   -2.2322   -0.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7401   -2.0749   -1.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7857    0.8169   -2.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3672   -0.0111   -2.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2820    2.6431   -2.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9925    2.3345   -0.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4879    1.6551   -1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995   -1.9490    2.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6027   -4.1659    2.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9393   -4.6490    2.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3694   -2.8621    1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  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  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
  8 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25  6  1  0
 24 19  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  7 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 18 50  1  0
 20 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  0
M  END

527
  Mrv0541 02231214452D          

 25 26  0  0  0  0            999 V2000
    3.0790    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -3.0938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    1.8563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -3.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -3.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9599    0.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9599    1.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7073    0.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7073    1.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  2 14  2  0  0  0  0
  3  6  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4  7  1  0  0  0  0
  4 14  1  0  0  0  0
  5 15  1  0  0  0  0
  5 18  2  0  0  0  0
  6  7  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  1  0  0  0  0
 10 16  2  0  0  0  0
 13 15  1  0  0  0  0
 13 21  2  0  0  0  0
 15 22  2  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 25  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014668

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC

> <INCHI_IDENTIFIER>
InChI=1S/C20H29N3O2/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24)

> <INCHI_KEY>
PUFQVTATUTYEAL-UHFFFAOYSA-N

> <FORMULA>
C20H29N3O2

> <MOLECULAR_WEIGHT>
343.4632

> <EXACT_MASS>
343.225977187

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
40.77996698487488

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide

> <ALOGPS_LOGP>
3.79

> <JCHEM_LOGP>
3.698162542000002

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.574410406507933

> <JCHEM_PKA_STRONGEST_BASIC>
9.044345732080648

> <JCHEM_POLAR_SURFACE_AREA>
54.46

> <JCHEM_REFRACTIVITY>
102.12100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dibucaine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014668
     RDKit          3D
Dibucaine
 54 55  0  0  0  0  0  0  0  0999 V2000
    3.9332    1.1415   -2.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3543    1.6030   -2.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9421    1.3746   -0.8913 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3064    2.0987    0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0107    1.9768    0.5789 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2410    0.9353    1.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8914    1.1946    1.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687    0.2083    1.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486    0.4642    2.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5182    1.1122    3.1881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3698   -0.1028    1.2775 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2354   -0.5767    0.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2084    0.4566   -0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2105   -0.1712   -0.9344 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1842   -0.8944   -0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2698   -1.5184   -1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6556    0.6254   -2.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3828    1.8671   -1.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.0766    1.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7236   -2.0977    2.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2520   -3.3837    2.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -3.6459    2.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3391   -2.6132    1.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8349   -1.3505    1.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6314   -0.3289    1.1096 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6231    0.9990   -3.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    0.1727   -1.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2634    1.8846   -1.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0491    1.0883   -2.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3699    2.6931   -2.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9641    0.2647   -0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0422    1.6483   -0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5816    3.2382    0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401    1.8352    1.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5655    2.2021    1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2948    0.4240    2.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8966   -1.2260   -0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9587   -1.3511    0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829    1.0374    0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613    1.1515   -0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7055   -1.8138    0.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6177   -0.3609    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8957   -0.6910   -1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8152   -2.2322   -0.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7401   -2.0749   -1.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7857    0.8169   -2.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3672   -0.0111   -2.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2820    2.6431   -2.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9925    2.3345   -0.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4879    1.6551   -1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995   -1.9490    2.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6027   -4.1659    2.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9393   -4.6490    2.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3694   -2.8621    1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  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  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
  8 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25  6  1  0
 24 19  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  7 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 18 50  1  0
 20 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 527                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.747   3.465   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.748  -1.925   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.747  -5.775   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       7.081  -1.925   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       8.415   3.465   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.747  -4.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081  -3.465   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -6.545   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081  -6.545   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -8.085   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081  -8.085   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748   1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415  -1.155   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748   2.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081   1.155   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414   5.775   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081   2.695   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.747   5.005   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414   7.315   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.125   0.332   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.125   3.518   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.520   1.123   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.520   2.727   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080   8.085   0.000  0.00  0.00           C+0
CONECT    1   18   19                                                       
CONECT    2   14                                                            
CONECT    3    6    8    9                                                  
CONECT    4    7   14                                                       
CONECT    5   15   18                                                       
CONECT    6    3    7                                                       
CONECT    7    4    6                                                       
CONECT    8    3   11                                                       
CONECT    9    3   12                                                       
CONECT   10   13   14   16                                                  
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13   10   15   21                                                  
CONECT   14    2    4   10                                                  
CONECT   15    5   13   22                                                  
CONECT   16   10   18                                                       
CONECT   17   19   20                                                       
CONECT   18    1    5   16                                                  
CONECT   19    1   17                                                       
CONECT   20   17   25                                                       
CONECT   21   13   23                                                       
CONECT   22   15   24                                                       
CONECT   23   21   24                                                       
CONECT   24   22   23                                                       
CONECT   25   20                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0014668
HETATM    1  C1  UNL     1       3.933   1.142  -2.333  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.354   1.603  -2.235  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.942   1.375  -0.891  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.306   2.099   0.205  1.00  0.00           C  
HETATM    5  O1  UNL     1       4.011   1.977   0.579  1.00  0.00           O  
HETATM    6  C5  UNL     1       3.241   0.935   1.002  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.891   1.195   1.377  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.069   0.208   1.812  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.349   0.464   2.186  1.00  0.00           C  
HETATM   10  O2  UNL     1      -0.518   1.112   3.188  1.00  0.00           O  
HETATM   11  N1  UNL     1      -1.370  -0.103   1.277  1.00  0.00           N  
HETATM   12  C9  UNL     1      -2.235  -0.577   0.518  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.208   0.457  -0.134  1.00  0.00           C  
HETATM   14  N2  UNL     1      -4.211  -0.171  -0.934  1.00  0.00           N  
HETATM   15  C11 UNL     1      -5.184  -0.894  -0.214  1.00  0.00           C  
HETATM   16  C12 UNL     1      -6.270  -1.518  -1.100  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.656   0.625  -2.034  1.00  0.00           C  
HETATM   18  C14 UNL     1      -5.383   1.867  -1.629  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.527  -1.077   1.900  1.00  0.00           C  
HETATM   20  C16 UNL     1       0.724  -2.098   2.343  1.00  0.00           C  
HETATM   21  C17 UNL     1       1.252  -3.384   2.416  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.542  -3.646   2.053  1.00  0.00           C  
HETATM   23  C19 UNL     1       3.339  -2.613   1.612  1.00  0.00           C  
HETATM   24  C20 UNL     1       2.835  -1.351   1.540  1.00  0.00           C  
HETATM   25  N3  UNL     1       3.631  -0.329   1.110  1.00  0.00           N  
HETATM   26  H1  UNL     1       3.623   0.999  -3.403  1.00  0.00           H  
HETATM   27  H2  UNL     1       3.859   0.173  -1.790  1.00  0.00           H  
HETATM   28  H3  UNL     1       3.263   1.885  -1.889  1.00  0.00           H  
HETATM   29  H4  UNL     1       6.049   1.088  -2.995  1.00  0.00           H  
HETATM   30  H5  UNL     1       5.370   2.693  -2.535  1.00  0.00           H  
HETATM   31  H6  UNL     1       5.964   0.265  -0.640  1.00  0.00           H  
HETATM   32  H7  UNL     1       7.042   1.648  -0.903  1.00  0.00           H  
HETATM   33  H8  UNL     1       5.582   3.238   0.137  1.00  0.00           H  
HETATM   34  H9  UNL     1       5.940   1.835   1.163  1.00  0.00           H  
HETATM   35  H10 UNL     1       1.565   2.202   1.282  1.00  0.00           H  
HETATM   36  H11 UNL     1      -2.295   0.424   2.128  1.00  0.00           H  
HETATM   37  H12 UNL     1      -1.897  -1.226  -0.409  1.00  0.00           H  
HETATM   38  H13 UNL     1      -2.959  -1.351   0.996  1.00  0.00           H  
HETATM   39  H14 UNL     1      -3.683   1.037   0.660  1.00  0.00           H  
HETATM   40  H15 UNL     1      -2.561   1.152  -0.743  1.00  0.00           H  
HETATM   41  H16 UNL     1      -4.705  -1.814   0.248  1.00  0.00           H  
HETATM   42  H17 UNL     1      -5.618  -0.361   0.665  1.00  0.00           H  
HETATM   43  H18 UNL     1      -6.896  -0.691  -1.466  1.00  0.00           H  
HETATM   44  H19 UNL     1      -6.815  -2.232  -0.435  1.00  0.00           H  
HETATM   45  H20 UNL     1      -5.740  -2.075  -1.896  1.00  0.00           H  
HETATM   46  H21 UNL     1      -3.786   0.817  -2.692  1.00  0.00           H  
HETATM   47  H22 UNL     1      -5.367  -0.011  -2.656  1.00  0.00           H  
HETATM   48  H23 UNL     1      -5.282   2.643  -2.427  1.00  0.00           H  
HETATM   49  H24 UNL     1      -4.992   2.334  -0.691  1.00  0.00           H  
HETATM   50  H25 UNL     1      -6.488   1.655  -1.503  1.00  0.00           H  
HETATM   51  H26 UNL     1      -0.299  -1.949   2.643  1.00  0.00           H  
HETATM   52  H27 UNL     1       0.603  -4.166   2.772  1.00  0.00           H  
HETATM   53  H28 UNL     1       2.939  -4.649   2.123  1.00  0.00           H  
HETATM   54  H29 UNL     1       4.369  -2.862   1.348  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6
CONECT    6    7    7   25
CONECT    7    8   35
CONECT    8    9   19   19
CONECT    9   10   10   11
CONECT   11   12   36
CONECT   12   13   37   38
CONECT   13   14   39   40
CONECT   14   15   17
CONECT   15   16   41   42
CONECT   16   43   44   45
CONECT   17   18   46   47
CONECT   18   48   49   50
CONECT   19   20   24
CONECT   20   21   21   51
CONECT   21   22   52
CONECT   22   23   23   53
CONECT   23   24   54
CONECT   24   25   25
END

HMDB0014668
     RDKit          3D
Dibucaine
 54 55  0  0  0  0  0  0  0  0999 V2000
    3.9332    1.1415   -2.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3543    1.6030   -2.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9421    1.3746   -0.8913 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3064    2.0987    0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0107    1.9768    0.5789 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2410    0.9353    1.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8914    1.1946    1.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687    0.2083    1.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486    0.4642    2.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5182    1.1122    3.1881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3698   -0.1028    1.2775 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2354   -0.5767    0.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2084    0.4566   -0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2105   -0.1712   -0.9344 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1842   -0.8944   -0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2698   -1.5184   -1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6556    0.6254   -2.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3828    1.8671   -1.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.0766    1.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7236   -2.0977    2.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2520   -3.3837    2.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -3.6459    2.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3391   -2.6132    1.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8349   -1.3505    1.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6314   -0.3289    1.1096 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6231    0.9990   -3.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    0.1727   -1.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2634    1.8846   -1.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0491    1.0883   -2.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3699    2.6931   -2.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9641    0.2647   -0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0422    1.6483   -0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5816    3.2382    0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401    1.8352    1.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5655    2.2021    1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2948    0.4240    2.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8966   -1.2260   -0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9587   -1.3511    0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829    1.0374    0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613    1.1515   -0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7055   -1.8138    0.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6177   -0.3609    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8957   -0.6910   -1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8152   -2.2322   -0.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7401   -2.0749   -1.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7857    0.8169   -2.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3672   -0.0111   -2.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2820    2.6431   -2.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9925    2.3345   -0.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4879    1.6551   -1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995   -1.9490    2.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6027   -4.1659    2.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9393   -4.6490    2.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3694   -2.8621    1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  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  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
  8 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25  6  1  0
 24 19  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  7 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 18 50  1  0
 20 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Butoxy-N-(2-(diethylamino)ethyl)cinchoninamide	ChEBI
2-Butoxy-N-(alpha-diethylaminoethyl)cinchoninamide	ChEBI
2-Butoxy-N-(beta-diethylaminoethyl)cinchoninamide	ChEBI
2-Butoxy-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide	ChEBI
2-Butoxy-quinoline-4-carboxylic acid (2-diethylamino-ethyl)-amide	ChEBI
2-Butoxyquinoline-4-carboxylic acid diethylaminoethylamide	ChEBI
2-N-Butoxy-N-(2-diethylaminoethyl)cinchoninamide	ChEBI
alpha-Butyloxycinchonic acid-gamma-diethylethylenediamine	ChEBI
alpha-Butyloxycinchoninic acid diethylethylenediamide	ChEBI
Cinchocainum	ChEBI
Cincocainio	ChEBI
Dibucaine base	ChEBI
N-(2-(Diethylamino)ethyl)-2-butoxycinchoninamide	ChEBI
Cinchocaine	Kegg
Nupercaine	Kegg
2-Butoxy-N-(a-diethylaminoethyl)cinchoninamide	Generator
2-Butoxy-N-(α-diethylaminoethyl)cinchoninamide	Generator
2-Butoxy-N-(b-diethylaminoethyl)cinchoninamide	Generator
2-Butoxy-N-(β-diethylaminoethyl)cinchoninamide	Generator
2-Butoxy-quinoline-4-carboxylate (2-diethylamino-ethyl)-amide	Generator
2-Butoxyquinoline-4-carboxylate diethylaminoethylamide	Generator
a-Butyloxycinchonate-g-diethylethylenediamine	Generator
a-Butyloxycinchonic acid-g-diethylethylenediamine	Generator
alpha-Butyloxycinchonate-gamma-diethylethylenediamine	Generator
Α-butyloxycinchonate-γ-diethylethylenediamine	Generator
Α-butyloxycinchonic acid-γ-diethylethylenediamine	Generator
a-Butyloxycinchoninate diethylethylenediamide	Generator
a-Butyloxycinchoninic acid diethylethylenediamide	Generator
alpha-Butyloxycinchoninate diethylethylenediamide	Generator
Α-butyloxycinchoninate diethylethylenediamide	Generator
Α-butyloxycinchoninic acid diethylethylenediamide	Generator
Cincain	HMDB
Nupercainal	HMDB
Sovcaine	HMDB

Chemical Formula

C₂₀H₂₉N₃O₂

Average Molecular Weight

343.4632

Monoisotopic Molecular Weight

343.225977187

IUPAC Name

2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide

Traditional Name

dibucaine

CAS Registry Number

85-79-0

SMILES

CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC

InChI Identifier

InChI=1S/C20H29N3O2/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24)

InChI Key

PUFQVTATUTYEAL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinolones and derivatives. Quinolones and derivatives are compounds containing a quinoline moiety which bears a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Quinolones and derivatives

Alternative Parents

Substituents

Quinolone
Alkyl aryl ether
Pyridine
Benzenoid
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Carboximidic acid
Carboximidic acid derivative
Ether
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:247956 )
aromatic ether (CHEBI:247956 )
monocarboxylic acid amide (CHEBI:247956 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014668)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Dibucaine Action Pathway (PathBank: SMP0000396)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	99 - 101 °C (hydrochloride salt)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.039 g/L	Not Available
LogP	4.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	196.2	30932474
[M+H]+	Not Available	195.466	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000992

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.039 g/L	ALOGPS
logP	3.79	ALOGPS
logP	3.7	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.57	ChemAxon
pKa (Strongest Basic)	9.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.46 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	102.12 m³·mol⁻¹	ChemAxon
Polarizability	40.78 Å³	ChemAxon
Number of Rings	2	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]+	181.772	31661259
DarkChem	[M-H]-	179.49	31661259
DeepCCS	[M+H]+	182.346	30932474
DeepCCS	[M-H]-	179.988	30932474
DeepCCS	[M-2H]-	213.146	30932474
DeepCCS	[M+Na]+	188.439	30932474
AllCCS	[M+H]+	185.0	32859911
AllCCS	[M+H-H2O]+	182.3	32859911
AllCCS	[M+NH4]+	187.6	32859911
AllCCS	[M+Na]+	188.3	32859911
AllCCS	[M-H]-	186.4	32859911
AllCCS	[M+Na-2H]-	187.0	32859911
AllCCS	[M+HCOO]-	187.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dibucaine	CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC	3544.0	Standard polar	33892256
Dibucaine	CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC	2776.2	Standard non polar	33892256
Dibucaine	CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC	2732.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dibucaine,1TMS,isomer #1	CCCCOC1=CC(C(=O)N(CCN(CC)CC)[Si](C)(C)C)=C2C=CC=CC2=N1	2766.2	Semi standard non polar	33892256
Dibucaine,1TMS,isomer #1	CCCCOC1=CC(C(=O)N(CCN(CC)CC)[Si](C)(C)C)=C2C=CC=CC2=N1	2824.4	Standard non polar	33892256
Dibucaine,1TMS,isomer #1	CCCCOC1=CC(C(=O)N(CCN(CC)CC)[Si](C)(C)C)=C2C=CC=CC2=N1	3505.6	Standard polar	33892256
Dibucaine,1TBDMS,isomer #1	CCCCOC1=CC(C(=O)N(CCN(CC)CC)[Si](C)(C)C(C)(C)C)=C2C=CC=CC2=N1	2995.6	Semi standard non polar	33892256
Dibucaine,1TBDMS,isomer #1	CCCCOC1=CC(C(=O)N(CCN(CC)CC)[Si](C)(C)C(C)(C)C)=C2C=CC=CC2=N1	3002.6	Standard non polar	33892256
Dibucaine,1TBDMS,isomer #1	CCCCOC1=CC(C(=O)N(CCN(CC)CC)[Si](C)(C)C(C)(C)C)=C2C=CC=CC2=N1	3573.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Dibucaine EI-B (Non-derivatized)	splash10-000i-9000000000-11b0b035aed1c901a827	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dibucaine CI-B (Non-derivatized)	splash10-0006-5009000000-4623c33d494376e699f3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dibucaine EI-B (Non-derivatized)	splash10-000i-9000000000-11b0b035aed1c901a827	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dibucaine CI-B (Non-derivatized)	splash10-0006-5009000000-4623c33d494376e699f3	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dibucaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05br-9272000000-3d2ab0479ffb92d2501b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dibucaine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine LC-ESI-QFT , positive-QTOF	splash10-0006-0009000000-396529f9f1539ca4f5d2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine LC-ESI-QFT , positive-QTOF	splash10-00di-0091000000-f6ba1af6a7e8fcdfaa16	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine LC-ESI-QFT , positive-QTOF	splash10-00xr-0190000000-9cd7408320081da0e435	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine LC-ESI-QFT , positive-QTOF	splash10-01b9-0960000000-48d5c97824dd28e11f73	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-cbd25496ff6fc8a2fa36	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-b4f898603ef48a2b9e29	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine , positive-QTOF	splash10-00xr-3980000000-e5e0b2d6136d950b770a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine 60V, Positive-QTOF	splash10-01bc-0930000000-f9d20a9fdaa804f3c0c2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine 40V, Positive-QTOF	splash10-00xr-0190000000-226cb2826cf33c4cb0bc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine 45V, Positive-QTOF	splash10-00xr-0290000000-99941cc61989e5a21fad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine 35V, Positive-QTOF	splash10-00di-0090000000-e3109e7f0063b8d26ac2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine 55V, Positive-QTOF	splash10-01b9-0960000000-48f69614630fb349afad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine 50V, Positive-QTOF	splash10-01b9-0590000000-66ea2193e7e219589c8c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine 30V, Positive-QTOF	splash10-00di-0090000000-cece5add8c5b72bebe67	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine 70V, Positive-QTOF	splash10-014i-0900000000-d7a2dd0e46b7abe92e46	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine 75V, Positive-QTOF	splash10-014i-0900000000-fb9b59d77fc5a1720e6b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine 65V, Positive-QTOF	splash10-014l-0910000000-3fbd1b08182eb4cfad02	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine 5V, Positive-QTOF	splash10-00dl-0096000000-94c62fffc37698ecddd6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dibucaine 60V, Positive-QTOF	splash10-01bc-0930000000-6e8fbc14f543ed77b645	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibucaine 10V, Positive-QTOF	splash10-0006-3559000000-63b39814c87e3867b4c8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibucaine 20V, Positive-QTOF	splash10-0zmi-8891000000-b554e300f3adf4d3ece4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibucaine 40V, Positive-QTOF	splash10-0pi0-9310000000-e2dff930dc76d5752208	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibucaine 10V, Negative-QTOF	splash10-0006-2069000000-55885f8ff7612dc6aaeb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibucaine 20V, Negative-QTOF	splash10-0006-8396000000-06d05a3147875a59f5b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibucaine 40V, Negative-QTOF	splash10-0006-5910000000-c55a93ba4d932f2362ab	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Dibucaine Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00527	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00527	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00527

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2917

KEGG Compound ID

C07879

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dibucaine

METLIN ID

Not Available

PubChem Compound

3025

PDB ID

Not Available

ChEBI ID

247956

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

Abdel-Ghani NT, Youssef AF, Awady MA: Cinchocaine hydrochloride determination by atomic absorption spectrometry and spectrophotometry. Farmaco. 2005 May;60(5):419-24. [PubMed:15910814 ]
Nounou MM, El-Khordagui LK, Khalafallah N: Effect of various formulation variables on the encapsulation and stability of dibucaine base in multilamellar vesicles. Acta Pol Pharm. 2005 Sep-Oct;62(5):369-79. [PubMed:16459486 ]
Souto-Padron T, Lima AP, Ribeiro Rde O: Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi. Parasitol Res. 2006 Sep;99(4):317-20. Epub 2006 Apr 13. [PubMed:16612626 ]

Enzymes

Enzyme Details

1. Cholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:: BCHE
Uniprot ID:: P06276
Molecular weight:: 68417.575

References

Elamin B: Dibucaine inhibition of serum cholinesterase. J Biochem Mol Biol. 2003 Mar 31;36(2):149-53. [PubMed:12689511 ]

Enzyme Details

2. Calmodulin

General function:: Involved in calcium ion binding
Specific function:: Calmodulin mediates the control of a large number of enzymes and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number of protein kinases and phosphatases. Together with CEP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis
Gene Name:: CALM1
Uniprot ID:: P62158
Molecular weight:: 16837.5

References

Muto Y, Kudo S, Nozawa Y: Effects of local anesthetics on calmodulin-dependent guanylate cyclase in the plasma membrane of Tetrahymena pyriformis. Biochem Pharmacol. 1983 Dec 1;32(23):3559-63. [PubMed:6140014 ]
Volpi M, Sha'afi RI, Epstein PM, Andrenyak DM, Feinstein MB: Local anesthetics, mepacrine, and propranolol are antagonists of calmodulin. Proc Natl Acad Sci U S A. 1981 Feb;78(2):795-9. [PubMed:6262771 ]
Liu SH, Fu WM, Lin-Shiau SY: Studies on the inhibition by chlorpromazine of myotonia induced by ion channel modulators in mouse skeletal muscle. Eur J Pharmacol. 1993 Jan 26;231(1):23-30. [PubMed:7680317 ]
Sambandam T, Gunasekaran M: Purification and properties of calmodulin from Phymatotrichum omnivorum. Microbios. 1993;73(294):61-74. [PubMed:8382768 ]

Enzyme Details

3. Sodium channel protein type 5 subunit alpha

General function:: Involved in ion channel activity
Specific function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:: SCN5A
Uniprot ID:: Q14524
Molecular weight:: 226937.5

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Oka M, Itoh Y, Fujita T: Halothane attenuates the cerebroprotective action of several Na+ and Ca2+ channel blockers via reversal of their ion channel blockade. Eur J Pharmacol. 2002 Oct 4;452(2):175-81. [PubMed:12354567 ]
Louro SR, Anteneodo C, Wajnberg E: Carboxyl groups at the membrane interface as molecular targets for local anesthetics. Biophys Chem. 1998 Aug 4;74(1):35-43. [PubMed:9742684 ]
Ryan SE, Demers CN, Chew JP, Baenziger JE: Structural effects of neutral and anionic lipids on the nicotinic acetylcholine receptor. An infrared difference spectroscopy study. J Biol Chem. 1996 Oct 4;271(40):24590-7. [PubMed:8798723 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

4. Sodium channel protein type 10 subunit alpha

General function:: Involved in ion channel activity
Specific function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms
Gene Name:: SCN10A
Uniprot ID:: Q9Y5Y9
Molecular weight:: 220623.6

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Louro SR, Anteneodo C, Wajnberg E: Carboxyl groups at the membrane interface as molecular targets for local anesthetics. Biophys Chem. 1998 Aug 4;74(1):35-43. [PubMed:9742684 ]
Ryan SE, Demers CN, Chew JP, Baenziger JE: Structural effects of neutral and anionic lipids on the nicotinic acetylcholine receptor. An infrared difference spectroscopy study. J Biol Chem. 1996 Oct 4;271(40):24590-7. [PubMed:8798723 ]

Showing metabocard for Dibucaine (HMDB0014668)

MOL for HMDB0014668 (Dibucaine)

3D MOL for HMDB0014668 (Dibucaine)

3D SDF for HMDB0014668 (Dibucaine)

3D-SDF for HMDB0014668 (Dibucaine)

PDB for HMDB0014668 (Dibucaine)

3D PDB for HMDB0014668 (Dibucaine)

SMILES for HMDB0014668 (Dibucaine)

INCHI for HMDB0014668 (Dibucaine)

Structure for HMDB0014668 (Dibucaine)

3D Structure for HMDB0014668 (Dibucaine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References