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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015267

Secondary Accession Numbers

HMDB15267

Metabolite Identification

Common Name

Carvedilol

Description

Carvedilol is only found in individuals that have used or taken this drug. It is a non-selective beta blocker indicated in the treatment of mild to moderate congestive heart failure (CHF).Carvedilol is a racemic mixture in which nonselective beta-adrenoreceptor blocking activity is present in the S(-) enantiomer and alpha-adrenergic blocking activity is present in both R(+) and S(-) enantiomers at equal potency. Carvedilol's beta-adrenergic receptor blocking ability decreases the heart rate, myocardial contractility, and myocardial oxygen demand. Carvedilol also decreases systemic vascular resistance via its alpha adrenergic receptor blocking properties. Carvedilol and its metabolite BM-910228 (a less potent beta blocker, but more potent antioxidant) have been shown to restore the inotropic responsiveness to Ca²⁺ in OH^- free radical-treated myocardium. Carvedilol and its metabolites also prevent OH^- radical-induced decrease in sarcoplasmic reticulum Ca²⁺-ATPase activity. Therefore, carvedilol and its metabolites may be beneficial in chronic heart failure by preventing free radical damage.

Structure

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

1136
  Mrv0541 02231215162D          

 30 33  0  0  1  0            999 V2000
    4.4487    1.9787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9207    0.4155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8364   -2.8440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2186   -3.1683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7352    4.6773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0106   -0.8234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1477    3.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3227    3.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4026    4.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0676    4.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7127    2.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7296    0.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9936    1.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2746   -0.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403    4.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7575    2.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5547    2.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2299    4.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8202    3.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5555   -1.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156    2.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2915   -2.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5724   -3.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7635   -3.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1173   -4.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4995   -4.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8533   -5.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0444   -5.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4097   -3.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 13  1  0  0  0  0
  2 12  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  4 25  1  0  0  0  0
  4 30  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 14  1  0  0  0  0
  6 20  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 11  1  0  0  0  0
  8 10  1  0  0  0  0
  8 16  2  0  0  0  0
  9 15  1  0  0  0  0
 10 18  2  0  0  0  0
 11 17  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 15 19  2  0  0  0  0
 16 21  1  0  0  0  0
 17 19  1  0  0  0  0
 18 22  1  0  0  0  0
 20 23  1  0  0  0  0
 21 22  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 25 27  2  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 29  2  0  0  0  0
M  END

HMDB0015267
     RDKit          3D
Carvedilol
 56 59  0  0  0  0  0  0  0  0999 V2000
    6.4513    2.7582   -1.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6806    1.6084   -1.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1810    0.5198   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4619    0.5041   -0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9018   -0.6148    0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0384   -1.6609    0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7314   -1.6536    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -0.5596   -0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0591   -0.3628   -0.8248 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8877   -0.9978   -0.9303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2839   -1.3516    0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0111   -2.0010    0.3226 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0051   -1.0058   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3170   -0.1039    1.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8709   -0.8836    2.1517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2686    1.0240    0.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5137    0.8004    0.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1865    0.4148   -0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6221    0.1215   -1.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4345   -0.2545   -2.9401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7967   -0.3527   -2.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3464   -0.0583   -1.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6392   -0.0753   -1.1856 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7049    0.2785    0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7378    0.4282    1.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4916    0.8139    2.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2052    1.0631    2.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1549    0.9198    1.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4287    0.5347    0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5924    0.3221   -0.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7807    3.4883   -1.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9174    3.1928   -0.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2078    2.4280   -2.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1130    1.3318   -0.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9036   -0.6494    0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3837   -2.5330    1.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0935   -2.5214    0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1379   -0.3253   -1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9647   -1.9394   -1.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9370   -2.0531    0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2870   -0.4064    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7515   -2.5733    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9117   -1.6023   -0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3533   -0.4642   -0.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6228    0.3444    1.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3701   -1.6626    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7382    1.8835    0.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3767    1.5025    1.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5644    0.2151   -2.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9640   -0.4784   -3.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4166   -0.6434   -3.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4900   -0.3184   -1.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7337    0.2232    0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3340    0.9177    3.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0452    1.3604    3.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1480    1.1080    2.1449 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
  8  3  1  0
 30 18  1  0
 30 22  2  0
 29 24  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 23 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
M  END

1136
  Mrv0541 02231215162D          

 30 33  0  0  1  0            999 V2000
    4.4487    1.9787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9207    0.4155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8364   -2.8440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2186   -3.1683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7352    4.6773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0106   -0.8234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1477    3.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3227    3.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4026    4.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0676    4.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7127    2.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7296    0.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9936    1.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2746   -0.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403    4.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7575    2.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5547    2.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2299    4.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8202    3.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5555   -1.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156    2.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2915   -2.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5724   -3.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7635   -3.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1173   -4.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4995   -4.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8533   -5.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0444   -5.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4097   -3.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 13  1  0  0  0  0
  2 12  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  4 25  1  0  0  0  0
  4 30  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 14  1  0  0  0  0
  6 20  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 11  1  0  0  0  0
  8 10  1  0  0  0  0
  8 16  2  0  0  0  0
  9 15  1  0  0  0  0
 10 18  2  0  0  0  0
 11 17  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 15 19  2  0  0  0  0
 16 21  1  0  0  0  0
 17 19  1  0  0  0  0
 18 22  1  0  0  0  0
 20 23  1  0  0  0  0
 21 22  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 25 27  2  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015267

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2

> <INCHI_IDENTIFIER>
InChI=1S/C24H26N2O4/c1-28-21-10-4-5-11-22(21)29-14-13-25-15-17(27)16-30-23-12-6-9-20-24(23)18-7-2-3-8-19(18)26-20/h2-12,17,25-27H,13-16H2,1H3

> <INCHI_KEY>
OGHNVEJMJSYVRP-UHFFFAOYSA-N

> <FORMULA>
C24H26N2O4

> <MOLECULAR_WEIGHT>
406.4742

> <EXACT_MASS>
406.18925733

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
45.03274967939157

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
3.424854408

> <ALOGPS_LOGS>
-4.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.002539856351024

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.03043132112937

> <JCHEM_PKA_STRONGEST_BASIC>
8.741556967442913

> <JCHEM_POLAR_SURFACE_AREA>
75.74

> <JCHEM_REFRACTIVITY>
115.63770000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.44e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015267
     RDKit          3D
Carvedilol
 56 59  0  0  0  0  0  0  0  0999 V2000
    6.4513    2.7582   -1.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6806    1.6084   -1.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1810    0.5198   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4619    0.5041   -0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9018   -0.6148    0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0384   -1.6609    0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7314   -1.6536    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -0.5596   -0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0591   -0.3628   -0.8248 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8877   -0.9978   -0.9303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2839   -1.3516    0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0111   -2.0010    0.3226 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0051   -1.0058   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3170   -0.1039    1.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8709   -0.8836    2.1517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2686    1.0240    0.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5137    0.8004    0.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1865    0.4148   -0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6221    0.1215   -1.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4345   -0.2545   -2.9401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7967   -0.3527   -2.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3464   -0.0583   -1.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6392   -0.0753   -1.1856 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7049    0.2785    0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7378    0.4282    1.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4916    0.8139    2.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2052    1.0631    2.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1549    0.9198    1.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4287    0.5347    0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5924    0.3221   -0.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7807    3.4883   -1.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9174    3.1928   -0.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2078    2.4280   -2.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1130    1.3318   -0.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9036   -0.6494    0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3837   -2.5330    1.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0935   -2.5214    0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1379   -0.3253   -1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9647   -1.9394   -1.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9370   -2.0531    0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2870   -0.4064    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7515   -2.5733    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9117   -1.6023   -0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3533   -0.4642   -0.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6228    0.3444    1.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3701   -1.6626    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7382    1.8835    0.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3767    1.5025    1.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5644    0.2151   -2.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9640   -0.4784   -3.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4166   -0.6434   -3.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4900   -0.3184   -1.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7337    0.2232    0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3340    0.9177    3.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0452    1.3604    3.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1480    1.1080    2.1449 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
  8  3  1  0
 30 18  1  0
 30 22  2  0
 29 24  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 23 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1136                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.304   3.694   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.319   0.776   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      10.895  -5.309   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.875  -5.914   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       6.972   8.731   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       9.353  -1.537   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.742   6.361   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.202   6.361   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.218   7.826   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.726   7.826   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.797   5.153   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.829   1.078   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.321   2.537   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.846  -0.078   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.782   8.183   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.147   5.153   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.369   5.474   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.162   8.183   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.864   7.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.370  -2.693   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.576   5.474   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080   7.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.877  -4.152   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.402  -6.768   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.892  -7.071   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.419  -7.924   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.399  -8.530   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.926  -9.383   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.416  -9.686   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.365  -6.217   0.000  0.00  0.00           C+0
CONECT    1   11   13                                                       
CONECT    2   12                                                            
CONECT    3   23   24                                                       
CONECT    4   25   30                                                       
CONECT    5    9   10                                                       
CONECT    6   14   20                                                       
CONECT    7    8    9   11                                                  
CONECT    8    7   10   16                                                  
CONECT    9    5    7   15                                                  
CONECT   10    5    8   18                                                  
CONECT   11    1    7   17                                                  
CONECT   12    2   13   14                                                  
CONECT   13    1   12                                                       
CONECT   14    6   12                                                       
CONECT   15    9   19                                                       
CONECT   16    8   21                                                       
CONECT   17   11   19                                                       
CONECT   18   10   22                                                       
CONECT   19   15   17                                                       
CONECT   20    6   23                                                       
CONECT   21   16   22                                                       
CONECT   22   18   21                                                       
CONECT   23    3   20                                                       
CONECT   24    3   25   26                                                  
CONECT   25    4   24   27                                                  
CONECT   26   24   28                                                       
CONECT   27   25   29                                                       
CONECT   28   26   29                                                       
CONECT   29   27   28                                                       
CONECT   30    4                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0015267
HETATM    1  C1  UNL     1       6.451   2.758  -1.466  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.681   1.608  -1.189  1.00  0.00           O  
HETATM    3  C2  UNL     1       6.181   0.520  -0.502  1.00  0.00           C  
HETATM    4  C3  UNL     1       7.462   0.504  -0.048  1.00  0.00           C  
HETATM    5  C4  UNL     1       7.902  -0.615   0.626  1.00  0.00           C  
HETATM    6  C5  UNL     1       7.038  -1.661   0.811  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.731  -1.654   0.351  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.267  -0.560  -0.318  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.059  -0.363  -0.825  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.888  -0.998  -0.930  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.284  -1.352   0.420  1.00  0.00           C  
HETATM   12  N1  UNL     1       1.011  -2.001   0.323  1.00  0.00           N  
HETATM   13  C10 UNL     1      -0.005  -1.006  -0.045  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.317  -0.104   1.095  1.00  0.00           C  
HETATM   15  O3  UNL     1      -0.871  -0.884   2.152  1.00  0.00           O  
HETATM   16  C12 UNL     1      -1.269   1.024   0.872  1.00  0.00           C  
HETATM   17  O4  UNL     1      -2.514   0.800   0.416  1.00  0.00           O  
HETATM   18  C13 UNL     1      -3.187   0.415  -0.670  1.00  0.00           C  
HETATM   19  C14 UNL     1      -2.622   0.122  -1.893  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.434  -0.255  -2.940  1.00  0.00           C  
HETATM   21  C16 UNL     1      -4.797  -0.353  -2.821  1.00  0.00           C  
HETATM   22  C17 UNL     1      -5.346  -0.058  -1.598  1.00  0.00           C  
HETATM   23  N2  UNL     1      -6.639  -0.075  -1.186  1.00  0.00           N  
HETATM   24  C18 UNL     1      -6.705   0.278   0.101  1.00  0.00           C  
HETATM   25  C19 UNL     1      -7.738   0.428   1.032  1.00  0.00           C  
HETATM   26  C20 UNL     1      -7.492   0.814   2.337  1.00  0.00           C  
HETATM   27  C21 UNL     1      -6.205   1.063   2.755  1.00  0.00           C  
HETATM   28  C22 UNL     1      -5.155   0.920   1.838  1.00  0.00           C  
HETATM   29  C23 UNL     1      -5.429   0.535   0.548  1.00  0.00           C  
HETATM   30  C24 UNL     1      -4.592   0.322  -0.517  1.00  0.00           C  
HETATM   31  H1  UNL     1       5.781   3.488  -1.981  1.00  0.00           H  
HETATM   32  H2  UNL     1       6.917   3.193  -0.585  1.00  0.00           H  
HETATM   33  H3  UNL     1       7.208   2.428  -2.228  1.00  0.00           H  
HETATM   34  H4  UNL     1       8.113   1.332  -0.202  1.00  0.00           H  
HETATM   35  H5  UNL     1       8.904  -0.649   1.000  1.00  0.00           H  
HETATM   36  H6  UNL     1       7.384  -2.533   1.342  1.00  0.00           H  
HETATM   37  H7  UNL     1       5.094  -2.521   0.514  1.00  0.00           H  
HETATM   38  H8  UNL     1       2.138  -0.325  -1.463  1.00  0.00           H  
HETATM   39  H9  UNL     1       2.965  -1.939  -1.563  1.00  0.00           H  
HETATM   40  H10 UNL     1       2.937  -2.053   1.000  1.00  0.00           H  
HETATM   41  H11 UNL     1       2.287  -0.406   0.994  1.00  0.00           H  
HETATM   42  H12 UNL     1       0.752  -2.573   1.137  1.00  0.00           H  
HETATM   43  H13 UNL     1      -0.912  -1.602  -0.364  1.00  0.00           H  
HETATM   44  H14 UNL     1       0.353  -0.464  -0.908  1.00  0.00           H  
HETATM   45  H15 UNL     1       0.623   0.344   1.527  1.00  0.00           H  
HETATM   46  H16 UNL     1      -1.370  -1.663   1.797  1.00  0.00           H  
HETATM   47  H17 UNL     1      -0.738   1.884   0.326  1.00  0.00           H  
HETATM   48  H18 UNL     1      -1.377   1.502   1.918  1.00  0.00           H  
HETATM   49  H19 UNL     1      -1.564   0.215  -2.014  1.00  0.00           H  
HETATM   50  H20 UNL     1      -2.964  -0.478  -3.886  1.00  0.00           H  
HETATM   51  H21 UNL     1      -5.417  -0.643  -3.637  1.00  0.00           H  
HETATM   52  H22 UNL     1      -7.490  -0.318  -1.752  1.00  0.00           H  
HETATM   53  H23 UNL     1      -8.734   0.223   0.663  1.00  0.00           H  
HETATM   54  H24 UNL     1      -8.334   0.918   3.024  1.00  0.00           H  
HETATM   55  H25 UNL     1      -6.045   1.360   3.772  1.00  0.00           H  
HETATM   56  H26 UNL     1      -4.148   1.108   2.145  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   34
CONECT    5    6    6   35
CONECT    6    7   36
CONECT    7    8    8   37
CONECT    8    9
CONECT    9   10
CONECT   10   11   38   39
CONECT   11   12   40   41
CONECT   12   13   42
CONECT   13   14   43   44
CONECT   14   15   16   45
CONECT   15   46
CONECT   16   17   47   48
CONECT   17   18
CONECT   18   19   19   30
CONECT   19   20   49
CONECT   20   21   21   50
CONECT   21   22   51
CONECT   22   23   30   30
CONECT   23   24   52
CONECT   24   25   25   29
CONECT   25   26   53
CONECT   26   27   27   54
CONECT   27   28   55
CONECT   28   29   29   56
CONECT   29   30
END

HMDB0015267
     RDKit          3D
Carvedilol
 56 59  0  0  0  0  0  0  0  0999 V2000
    6.4513    2.7582   -1.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6806    1.6084   -1.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1810    0.5198   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4619    0.5041   -0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9018   -0.6148    0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0384   -1.6609    0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7314   -1.6536    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -0.5596   -0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0591   -0.3628   -0.8248 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8877   -0.9978   -0.9303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2839   -1.3516    0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0111   -2.0010    0.3226 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0051   -1.0058   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3170   -0.1039    1.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8709   -0.8836    2.1517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2686    1.0240    0.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5137    0.8004    0.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1865    0.4148   -0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6221    0.1215   -1.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4345   -0.2545   -2.9401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7967   -0.3527   -2.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3464   -0.0583   -1.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6392   -0.0753   -1.1856 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7049    0.2785    0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7378    0.4282    1.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4916    0.8139    2.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2052    1.0631    2.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1549    0.9198    1.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4287    0.5347    0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5924    0.3221   -0.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7807    3.4883   -1.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9174    3.1928   -0.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2078    2.4280   -2.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1130    1.3318   -0.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9036   -0.6494    0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3837   -2.5330    1.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0935   -2.5214    0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1379   -0.3253   -1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9647   -1.9394   -1.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9370   -2.0531    0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2870   -0.4064    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7515   -2.5733    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9117   -1.6023   -0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3533   -0.4642   -0.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6228    0.3444    1.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3701   -1.6626    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7382    1.8835    0.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3767    1.5025    1.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5644    0.2151   -2.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9640   -0.4784   -3.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4166   -0.6434   -3.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4900   -0.3184   -1.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7337    0.2232    0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3340    0.9177    3.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0452    1.3604    3.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1480    1.1080    2.1449 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
  8  3  1  0
 30 18  1  0
 30 22  2  0
 29 24  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 23 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-1-(Carbazol-4-yloxy)-3-((2-(O-methoxyphenoxy)ethyl)amino)-2-propanol	ChEBI
Carvedilolum	ChEBI
SKF 105517	ChEBI
Artist	Kegg
Coreg	Kegg
Dilatrend	HMDB
Kredex	HMDB
Carvedilol, (R)-isomer	HMDB
Carvedilol, 14C-labeled	HMDB
Coropres	HMDB
Eucardic	HMDB
Carvedilol hydrochloride	HMDB
Carvedilol, (+-)-isomer	HMDB
Querto	HMDB
Carvedilol, (S)-isomer	HMDB
Carvedilol, (-)	HMDB
Carvedilol, 14C labeled	HMDB
Carvedilol, (-)-isomer	HMDB
14C-Labeled carvedilol	HMDB
Carvedilol, (+)	HMDB
Carvedilol, (+)-isomer	HMDB

Chemical Formula

C₂₄H₂₆N₂O₄

Average Molecular Weight

406.4742

Monoisotopic Molecular Weight

406.18925733

IUPAC Name

1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol

Traditional Name

1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol

CAS Registry Number

72956-09-3

SMILES

COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2

InChI Identifier

InChI=1S/C24H26N2O4/c1-28-21-10-4-5-11-22(21)29-14-13-25-15-17(27)16-30-23-12-6-9-20-24(23)18-7-2-3-8-19(18)26-20/h2-12,17,25-27H,13-16H2,1H3

InChI Key

OGHNVEJMJSYVRP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Indole
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Pyrrole
Heteroaromatic compound
Secondary alcohol
1,2-aminoalcohol
Secondary amine
Azacycle
Secondary aliphatic amine
Ether
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

secondary alcohol (CHEBI:3441 )
secondary amino compound (CHEBI:3441 )
carbazoles (CHEBI:3441 )

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: HMDB0015267)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Carvedilol Action Pathway (PathBank: SMP0000367)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	114 - 115 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0044 g/L	Not Available
LogP	3.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	190.0	30932474
[M+H]+	Not Available	189.08	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001030

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0044 g/L	ALOGPS
logP	3.05	ALOGPS
logP	3.42	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	14.03	ChemAxon
pKa (Strongest Basic)	8.74	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	75.74 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	115.64 m³·mol⁻¹	ChemAxon
Polarizability	45.03 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	194.283	31661259
DarkChem	[M-H]-	193.807	31661259
DeepCCS	[M+H]+	185.365	30932474
DeepCCS	[M-H]-	183.007	30932474
DeepCCS	[M-2H]-	217.334	30932474
DeepCCS	[M+Na]+	193.395	30932474
AllCCS	[M+H]+	201.5	32859911
AllCCS	[M+H-H2O]+	198.9	32859911
AllCCS	[M+NH4]+	203.9	32859911
AllCCS	[M+Na]+	204.6	32859911
AllCCS	[M-H]-	199.3	32859911
AllCCS	[M+Na-2H]-	199.3	32859911
AllCCS	[M+HCOO]-	199.5	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.	5.54 minutes	32390414
Predicted by Siyang on May 30, 2022	13.3487 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.46 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	45.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2104.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	280.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	202.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	206.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	223.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	548.4 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	466.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	116.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	984.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	566.0 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	1427.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	404.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	365.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	340.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	186.0 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	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Carvedilol	COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2	4685.1	Standard polar	33892256
Carvedilol	COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2	3553.6	Standard non polar	33892256
Carvedilol	COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2	3815.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Carvedilol,1TMS,isomer #1	COC1=CC=CC=C1OCCNCC(COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)O[Si](C)(C)C	3724.9	Semi standard non polar	33892256
Carvedilol,1TMS,isomer #2	COC1=CC=CC=C1OCCN(CC(O)COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)[Si](C)(C)C	3763.0	Semi standard non polar	33892256
Carvedilol,1TMS,isomer #3	COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C	3749.0	Semi standard non polar	33892256
Carvedilol,2TMS,isomer #1	COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)O[Si](C)(C)C)[Si](C)(C)C	3781.2	Semi standard non polar	33892256
Carvedilol,2TMS,isomer #1	COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)O[Si](C)(C)C)[Si](C)(C)C	3546.1	Standard non polar	33892256
Carvedilol,2TMS,isomer #1	COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)O[Si](C)(C)C)[Si](C)(C)C	4541.5	Standard polar	33892256
Carvedilol,2TMS,isomer #2	COC1=CC=CC=C1OCCNCC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)O[Si](C)(C)C	3669.4	Semi standard non polar	33892256
Carvedilol,2TMS,isomer #2	COC1=CC=CC=C1OCCNCC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)O[Si](C)(C)C	3397.3	Standard non polar	33892256
Carvedilol,2TMS,isomer #2	COC1=CC=CC=C1OCCNCC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)O[Si](C)(C)C	4300.7	Standard polar	33892256
Carvedilol,2TMS,isomer #3	COC1=CC=CC=C1OCCN(CC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)[Si](C)(C)C	3715.0	Semi standard non polar	33892256
Carvedilol,2TMS,isomer #3	COC1=CC=CC=C1OCCN(CC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)[Si](C)(C)C	3472.2	Standard non polar	33892256
Carvedilol,2TMS,isomer #3	COC1=CC=CC=C1OCCN(CC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)[Si](C)(C)C	4495.5	Standard polar	33892256
Carvedilol,3TMS,isomer #1	COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)O[Si](C)(C)C)[Si](C)(C)C	3742.9	Semi standard non polar	33892256
Carvedilol,3TMS,isomer #1	COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)O[Si](C)(C)C)[Si](C)(C)C	3443.8	Standard non polar	33892256
Carvedilol,3TMS,isomer #1	COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)O[Si](C)(C)C)[Si](C)(C)C	4170.4	Standard polar	33892256
Carvedilol,1TBDMS,isomer #1	COC1=CC=CC=C1OCCNCC(COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)O[Si](C)(C)C(C)(C)C	3937.6	Semi standard non polar	33892256
Carvedilol,1TBDMS,isomer #2	COC1=CC=CC=C1OCCN(CC(O)COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)[Si](C)(C)C(C)(C)C	4015.0	Semi standard non polar	33892256
Carvedilol,1TBDMS,isomer #3	COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C	3888.2	Semi standard non polar	33892256
Carvedilol,2TBDMS,isomer #1	COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4219.5	Semi standard non polar	33892256
Carvedilol,2TBDMS,isomer #1	COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3904.1	Standard non polar	33892256
Carvedilol,2TBDMS,isomer #1	COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4569.6	Standard polar	33892256
Carvedilol,2TBDMS,isomer #2	COC1=CC=CC=C1OCCNCC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4001.0	Semi standard non polar	33892256
Carvedilol,2TBDMS,isomer #2	COC1=CC=CC=C1OCCNCC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3776.6	Standard non polar	33892256
Carvedilol,2TBDMS,isomer #2	COC1=CC=CC=C1OCCNCC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4339.3	Standard polar	33892256
Carvedilol,2TBDMS,isomer #3	COC1=CC=CC=C1OCCN(CC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4086.7	Semi standard non polar	33892256
Carvedilol,2TBDMS,isomer #3	COC1=CC=CC=C1OCCN(CC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3808.7	Standard non polar	33892256
Carvedilol,2TBDMS,isomer #3	COC1=CC=CC=C1OCCN(CC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4501.1	Standard polar	33892256
Carvedilol,3TBDMS,isomer #1	COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4280.5	Semi standard non polar	33892256
Carvedilol,3TBDMS,isomer #1	COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3952.6	Standard non polar	33892256
Carvedilol,3TBDMS,isomer #1	COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4245.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Carvedilol GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-2930000000-265c376e802c07cf1f2d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carvedilol GC-MS (1 TMS) - 70eV, Positive	splash10-001i-5911100000-80d7548a1e9097537fe6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carvedilol 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 - Carvedilol , positive-QTOF	splash10-0a4i-1662900000-f901a62f255da92e9a09	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carvedilol , positive-QTOF	splash10-0a4i-0220900000-5821022307fc5077033b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carvedilol 35V, Negative-QTOF	splash10-0a59-0700900000-db48a63e0af377a4fd9a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carvedilol 35V, Positive-QTOF	splash10-05gi-0590400000-262b3137ced7d5771dd1	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carvedilol 10V, Positive-QTOF	splash10-0a4i-0641900000-b122718c07e709b6e644	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carvedilol 20V, Positive-QTOF	splash10-001i-2970100000-e3a225c7d81ac86276be	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carvedilol 40V, Positive-QTOF	splash10-0pvi-5900000000-8e6d7ab1b80d6492009d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carvedilol 10V, Negative-QTOF	splash10-0a59-0920700000-a59fa070af5b3d3fc223	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carvedilol 20V, Negative-QTOF	splash10-001i-0900000000-3815ea3eac5b157a1da0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carvedilol 40V, Negative-QTOF	splash10-001i-1900000000-1853ce1e2c70f7955fbe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carvedilol 10V, Positive-QTOF	splash10-0a59-0371900000-e534eced6a6fe12ecec4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carvedilol 20V, Positive-QTOF	splash10-0kcr-0981300000-ba8dc2f3b7ba5097647c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carvedilol 40V, Positive-QTOF	splash10-0udi-2910000000-f102425e265c4b7f8845	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carvedilol 10V, Negative-QTOF	splash10-0a4i-0400900000-d652673d45eb1d8b982c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carvedilol 20V, Negative-QTOF	splash10-053r-2941300000-60c60407d2e97777ae0b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carvedilol 40V, Negative-QTOF	splash10-001i-0900000000-dcfc85c30b0adee491ca	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Carvedilol 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 DB01136	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01136	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01136

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2487

KEGG Compound ID

C06875

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Carvedilol

METLIN ID

Not Available

PubChem Compound

2585

PDB ID

Not Available

ChEBI ID

3441

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

Vanderhoff BT, Ruppel HM, Amsterdam PB: Carvedilol: the new role of beta blockers in congestive heart failure. Am Fam Physician. 1998 Nov 1;58(7):1627-34, 1641-2. [PubMed:9824960 ]
Packer M, Coats AJ, Fowler MB, Katus HA, Krum H, Mohacsi P, Rouleau JL, Tendera M, Castaigne A, Roecker EB, Schultz MK, DeMets DL: Effect of carvedilol on survival in severe chronic heart failure. N Engl J Med. 2001 May 31;344(22):1651-8. [PubMed:11386263 ]
Packer M, Fowler MB, Roecker EB, Coats AJ, Katus HA, Krum H, Mohacsi P, Rouleau JL, Tendera M, Staiger C, Holcslaw TL, Amann-Zalan I, DeMets DL: Effect of carvedilol on the morbidity of patients with severe chronic heart failure: results of the carvedilol prospective randomized cumulative survival (COPERNICUS) study. Circulation. 2002 Oct 22;106(17):2194-9. [PubMed:12390947 ]

Showing metabocard for Carvedilol (HMDB0015267)

MOL for HMDB0015267 (Carvedilol)

3D MOL for HMDB0015267 (Carvedilol)

3D SDF for HMDB0015267 (Carvedilol)

3D-SDF for HMDB0015267 (Carvedilol)

PDB for HMDB0015267 (Carvedilol)

3D PDB for HMDB0015267 (Carvedilol)

SMILES for HMDB0015267 (Carvedilol)

INCHI for HMDB0015267 (Carvedilol)

Structure for HMDB0015267 (Carvedilol)

3D Structure for HMDB0015267 (Carvedilol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra