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enzymes (2)transporters (1) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:57 UTC

HMDB ID

HMDB0015334

Secondary Accession Numbers

HMDB15334

Metabolite Identification

Common Name

Nadolol

Description

Nadolol is only found in individuals that have used or taken this drug. It is a non-selective beta-adrenergic antagonist with a long half-life, used in cardiovascular disease to treat arrhythmias, angina pectoris, and hypertension. Nadolol is also used for migraine disorders and for tremor. [PubChem]Like other beta-adrenergic antagonists, nadolol competes with adrenergic neurotransmitters such as catecholamines for binding at sympathetic receptor sites. Like propranolol and timolol, nadolol binds at beta(1)-adrenergic receptors in the heart and vascular smooth muscle, inhibiting the effects of the catecholamines epinephrine and norepinephrine and decreasing heart rate, cardiac output, and systolic and diastolic blood pressure. It also blocks beta-2 adrenergic receptors located in bronchiole smooth muscle, causing vasoconstriction. By binding beta-2 receptors in the juxtaglomerular apparatus, nadolol inhibits the production of renin, thereby inhibiting angiotensin II and aldosterone production. Nadolol therefore inhibits the vasoconstriction and water retention due to angiotensin II and aldosterone, respectively.

Structure

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

HMDB0015334
     RDKit          3D
Nadolol
 49 50  0  0  0  0  0  0  0  0999 V2000
   -4.6175   -0.3805   -1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3113   -0.4332   -0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6789   -0.7099    0.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4708   -1.6052    0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9359    0.8434    0.1727 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8316    1.5256   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5259    0.8946    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4231    0.8579    1.5050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3695    1.7187   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8210    1.2554   -0.1686 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7010    1.0268    0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5475    1.3381    2.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5565    1.0492    3.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7282    0.4518    2.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8645    0.1525    1.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9266    0.4035    0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0627    0.0836   -1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1893   -0.8202   -1.3971 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7483   -1.8275   -2.2640 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8198   -1.4924   -0.2048 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9319   -2.4244    0.3015 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1475   -0.5037    0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6257    0.1088   -1.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8987    0.2401   -2.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7364   -1.4001   -2.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3882   -0.0054    0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5237   -0.4346    1.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9318   -1.7690    0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8717   -1.5478    0.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1624   -2.4923    0.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8299   -1.9750   -0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6300    1.4057    0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8183    1.7467   -1.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8173    2.5566    0.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4750   -0.1385   -0.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9972    1.5246    1.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5202    2.8030   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5781    1.7936   -1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6600    1.8400    2.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4299    1.2924    4.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5258    0.2140    3.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0897    1.0417   -1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694   -0.3692   -1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9677   -0.2459   -1.9548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7269   -1.5268   -3.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7735   -1.9446   -0.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3278   -3.3276    0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8318    0.2861    0.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5219   -1.0805    1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 16 11  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  6
 19 45  1  0
 20 46  1  6
 21 47  1  0
 22 48  1  0
 22 49  1  0
M  END

1203
  Mrv0541 02231215192D          

 22 23  0  0  1  0            999 V2000
    1.6500    1.1569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.8069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5214    0.3034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5023   -1.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9216   -2.1880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.5694    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645    2.3944    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0790    1.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    2.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    2.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5309    1.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6313   -2.6087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5309    2.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2215   -0.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9312   -1.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2310   -0.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784    1.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784    2.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3409   -3.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2105   -3.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0520   -1.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  6  0  0  0
  7  2  1  6  0  0  0
  3 12  1  0  0  0  0
  3 17  1  0  0  0  0
  4 15  1  0  0  0  0
  5 13  1  0  0  0  0
  5 16  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 14  1  0  0  0  0
 12 18  2  0  0  0  0
 13 20  1  0  0  0  0
 13 21  1  0  0  0  0
 13 22  1  0  0  0  0
 14 19  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015334

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C)NCC(O)COC1=CC=CC2=C1C[C@H](O)[C@H](O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C17H27NO4/c1-17(2,3)18-9-12(19)10-22-16-6-4-5-11-7-14(20)15(21)8-13(11)16/h4-6,12,14-15,18-21H,7-10H2,1-3H3/t12?,14-,15+/m1/s1

> <INCHI_KEY>
VWPOSFSPZNDTMJ-UCWKZMIHSA-N

> <FORMULA>
C17H27NO4

> <MOLECULAR_WEIGHT>
309.4006

> <EXACT_MASS>
309.194008357

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
34.6284874795157

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S)-5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol

> <ALOGPS_LOGP>
1.23

> <JCHEM_LOGP>
0.8654279130000008

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.219191149274181

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.586200504793112

> <JCHEM_PKA_STRONGEST_BASIC>
9.759478916414329

> <JCHEM_POLAR_SURFACE_AREA>
81.95

> <JCHEM_REFRACTIVITY>
85.52690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nadolol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015334
     RDKit          3D
Nadolol
 49 50  0  0  0  0  0  0  0  0999 V2000
   -4.6175   -0.3805   -1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3113   -0.4332   -0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6789   -0.7099    0.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4708   -1.6052    0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9359    0.8434    0.1727 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8316    1.5256   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5259    0.8946    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4231    0.8579    1.5050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3695    1.7187   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8210    1.2554   -0.1686 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7010    1.0268    0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5475    1.3381    2.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5565    1.0492    3.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7282    0.4518    2.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8645    0.1525    1.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9266    0.4035    0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0627    0.0836   -1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1893   -0.8202   -1.3971 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7483   -1.8275   -2.2640 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8198   -1.4924   -0.2048 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9319   -2.4244    0.3015 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1475   -0.5037    0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6257    0.1088   -1.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8987    0.2401   -2.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7364   -1.4001   -2.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3882   -0.0054    0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5237   -0.4346    1.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9318   -1.7690    0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8717   -1.5478    0.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1624   -2.4923    0.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8299   -1.9750   -0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6300    1.4057    0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8183    1.7467   -1.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8173    2.5566    0.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4750   -0.1385   -0.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9972    1.5246    1.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5202    2.8030   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5781    1.7936   -1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6600    1.8400    2.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4299    1.2924    4.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5258    0.2140    3.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0897    1.0417   -1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694   -0.3692   -1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9677   -0.2459   -1.9548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7269   -1.5268   -3.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7735   -1.9446   -0.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3278   -3.3276    0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8318    0.2861    0.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5219   -1.0805    1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 16 11  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  6
 19 45  1  0
 20 46  1  6
 21 47  1  0
 22 48  1  0
 22 49  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1203                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080   2.160   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080   5.240   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.440   0.566   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.404  -2.514   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      11.054  -4.084   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.414   2.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414   4.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.747   2.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747   5.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081   2.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   4.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.458   2.106   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.378  -4.870   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.458   5.293   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.747  -1.759   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.072  -2.544   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.765  -0.219   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.853   2.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.853   4.502   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.703  -5.655   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.593  -6.194   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.164  -3.545   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3   12   17                                                       
CONECT    4   15                                                            
CONECT    5   13   16                                                       
CONECT    6    1    7    8                                                  
CONECT    7    2    6    9                                                  
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   11   12                                                  
CONECT   11    9   10   14                                                  
CONECT   12    3   10   18                                                  
CONECT   13    5   20   21   22                                             
CONECT   14   11   19                                                       
CONECT   15    4   16   17                                                  
CONECT   16    5   15                                                       
CONECT   17    3   15                                                       
CONECT   18   12   19                                                       
CONECT   19   14   18                                                       
CONECT   20   13                                                            
CONECT   21   13                                                            
CONECT   22   13                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0015334
HETATM    1  C1  UNL     1      -4.618  -0.381  -1.750  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.311  -0.433  -0.242  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.679  -0.710   0.453  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.471  -1.605   0.079  1.00  0.00           C  
HETATM    5  N1  UNL     1      -3.936   0.843   0.173  1.00  0.00           N  
HETATM    6  C5  UNL     1      -2.832   1.526  -0.312  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.526   0.895   0.141  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.423   0.858   1.505  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.370   1.719  -0.435  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.821   1.255  -0.169  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.701   1.027   0.789  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.548   1.338   2.130  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.557   1.049   3.053  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.728   0.452   2.667  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.865   0.153   1.340  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.927   0.404   0.388  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.063   0.084  -1.055  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.189  -0.820  -1.397  1.00  0.00           C  
HETATM   19  O3  UNL     1       3.748  -1.828  -2.264  1.00  0.00           O  
HETATM   20  C16 UNL     1       4.820  -1.492  -0.205  1.00  0.00           C  
HETATM   21  O4  UNL     1       3.932  -2.424   0.302  1.00  0.00           O  
HETATM   22  C17 UNL     1       5.148  -0.504   0.888  1.00  0.00           C  
HETATM   23  H1  UNL     1      -5.626   0.109  -1.850  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.899   0.240  -2.288  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.736  -1.400  -2.167  1.00  0.00           H  
HETATM   26  H4  UNL     1      -6.388  -0.005   0.019  1.00  0.00           H  
HETATM   27  H5  UNL     1      -5.524  -0.435   1.516  1.00  0.00           H  
HETATM   28  H6  UNL     1      -5.932  -1.769   0.319  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.872  -1.548   0.991  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.162  -2.492   0.263  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.830  -1.975  -0.749  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.630   1.406   0.683  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.818   1.747  -1.400  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.817   2.557   0.159  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.475  -0.138  -0.274  1.00  0.00           H  
HETATM   36  H14 UNL     1      -1.997   1.525   1.971  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.520   2.803  -0.127  1.00  0.00           H  
HETATM   38  H16 UNL     1      -0.578   1.794  -1.560  1.00  0.00           H  
HETATM   39  H17 UNL     1       0.660   1.840   2.505  1.00  0.00           H  
HETATM   40  H18 UNL     1       2.430   1.292   4.096  1.00  0.00           H  
HETATM   41  H19 UNL     1       4.526   0.214   3.344  1.00  0.00           H  
HETATM   42  H20 UNL     1       3.090   1.042  -1.649  1.00  0.00           H  
HETATM   43  H21 UNL     1       2.069  -0.369  -1.351  1.00  0.00           H  
HETATM   44  H22 UNL     1       4.968  -0.246  -1.955  1.00  0.00           H  
HETATM   45  H23 UNL     1       3.727  -1.527  -3.208  1.00  0.00           H  
HETATM   46  H24 UNL     1       5.773  -1.945  -0.543  1.00  0.00           H  
HETATM   47  H25 UNL     1       4.328  -3.328   0.137  1.00  0.00           H  
HETATM   48  H26 UNL     1       5.832   0.286   0.541  1.00  0.00           H  
HETATM   49  H27 UNL     1       5.522  -1.080   1.744  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4    5
CONECT    3   26   27   28
CONECT    4   29   30   31
CONECT    5    6   32
CONECT    6    7   33   34
CONECT    7    8    9   35
CONECT    8   36
CONECT    9   10   37   38
CONECT   10   11
CONECT   11   12   12   16
CONECT   12   13   39
CONECT   13   14   14   40
CONECT   14   15   41
CONECT   15   16   16   22
CONECT   16   17
CONECT   17   18   42   43
CONECT   18   19   20   44
CONECT   19   45
CONECT   20   21   22   46
CONECT   21   47
CONECT   22   48   49
END

HMDB0015334
     RDKit          3D
Nadolol
 49 50  0  0  0  0  0  0  0  0999 V2000
   -4.6175   -0.3805   -1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3113   -0.4332   -0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6789   -0.7099    0.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4708   -1.6052    0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9359    0.8434    0.1727 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8316    1.5256   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5259    0.8946    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4231    0.8579    1.5050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3695    1.7187   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8210    1.2554   -0.1686 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7010    1.0268    0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5475    1.3381    2.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5565    1.0492    3.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7282    0.4518    2.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8645    0.1525    1.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9266    0.4035    0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0627    0.0836   -1.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1893   -0.8202   -1.3971 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7483   -1.8275   -2.2640 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8198   -1.4924   -0.2048 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9319   -2.4244    0.3015 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1475   -0.5037    0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6257    0.1088   -1.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8987    0.2401   -2.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7364   -1.4001   -2.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3882   -0.0054    0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5237   -0.4346    1.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9318   -1.7690    0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8717   -1.5478    0.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1624   -2.4923    0.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8299   -1.9750   -0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6300    1.4057    0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8183    1.7467   -1.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8173    2.5566    0.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4750   -0.1385   -0.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9972    1.5246    1.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5202    2.8030   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5781    1.7936   -1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6600    1.8400    2.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4299    1.2924    4.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5258    0.2140    3.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0897    1.0417   -1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694   -0.3692   -1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9677   -0.2459   -1.9548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7269   -1.5268   -3.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7735   -1.9446   -0.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3278   -3.3276    0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8318    0.2861    0.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5219   -1.0805    1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 16 11  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  6
 19 45  1  0
 20 46  1  6
 21 47  1  0
 22 48  1  0
 22 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Corgard	Kegg
Solgol	HMDB

Chemical Formula

C₁₇H₂₇NO₄

Average Molecular Weight

309.4006

Monoisotopic Molecular Weight

309.194008357

IUPAC Name

(2R,3S)-5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol

Traditional Name

nadolol

CAS Registry Number

42200-33-9

SMILES

CC(C)(C)NCC(O)COC1=CC=CC2=C1C[C@H](O)[C@H](O)C2

InChI Identifier

InChI=1S/C17H27NO4/c1-17(2,3)18-9-12(19)10-22-16-6-4-5-11-7-14(20)15(21)8-13(11)16/h4-6,12,14-15,18-21H,7-10H2,1-3H3/t12?,14-,15+/m1/s1

InChI Key

VWPOSFSPZNDTMJ-UCWKZMIHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Substituents

Tetralin
Alkyl aryl ether
1,2-aminoalcohol
Secondary alcohol
Secondary aliphatic amine
Ether
Secondary amine
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic oxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0015334)

Biofluid or Excreta

Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Nadolol Action Pathway (PathBank: SMP0000303)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	124 - 136 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.25 g/L	Not Available
LogP	1.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	172.0	30932474
[M+H]+	Not Available	171.829	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000840

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.25 g/L	ALOGPS
logP	1.23	ALOGPS
logP	0.87	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	13.59	ChemAxon
pKa (Strongest Basic)	9.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	81.95 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	85.53 m³·mol⁻¹	ChemAxon
Polarizability	34.63 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]+	174.267	31661259
DarkChem	[M-H]-	170.182	31661259
DeepCCS	[M+H]+	174.979	30932474
DeepCCS	[M-H]-	172.621	30932474
DeepCCS	[M-2H]-	207.21	30932474
DeepCCS	[M+Na]+	183.5	30932474
AllCCS	[M+H]+	175.9	32859911
AllCCS	[M+H-H2O]+	173.0	32859911
AllCCS	[M+NH4]+	178.5	32859911
AllCCS	[M+Na]+	179.2	32859911
AllCCS	[M-H]-	176.5	32859911
AllCCS	[M+Na-2H]-	177.0	32859911
AllCCS	[M+HCOO]-	177.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nadolol	CC(C)(C)NCC(O)COC1=CC=CC2=C1C[C@H](O)[C@H](O)C2	3503.4	Standard polar	33892256
Nadolol	CC(C)(C)NCC(O)COC1=CC=CC2=C1C[C@H](O)[C@H](O)C2	2593.6	Standard non polar	33892256
Nadolol	CC(C)(C)NCC(O)COC1=CC=CC2=C1C[C@H](O)[C@H](O)C2	2566.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nadolol,1TMS,isomer #1	CC(C)(C)NCC(COC1=CC=CC2=C1C[C@H](O)[C@H](O)C2)O[Si](C)(C)C	2545.5	Semi standard non polar	33892256
Nadolol,1TMS,isomer #2	CC(C)(C)NCC(O)COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C)[C@H](O)C2	2540.1	Semi standard non polar	33892256
Nadolol,1TMS,isomer #3	CC(C)(C)NCC(O)COC1=CC=CC2=C1C[C@H](O)[C@H](O[Si](C)(C)C)C2	2542.5	Semi standard non polar	33892256
Nadolol,1TMS,isomer #4	CC(C)(C)N(CC(O)COC1=CC=CC2=C1C[C@H](O)[C@H](O)C2)[Si](C)(C)C	2696.7	Semi standard non polar	33892256
Nadolol,2TMS,isomer #1	CC(C)(C)NCC(COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C)[C@H](O)C2)O[Si](C)(C)C	2475.2	Semi standard non polar	33892256
Nadolol,2TMS,isomer #2	CC(C)(C)NCC(COC1=CC=CC2=C1C[C@H](O)[C@H](O[Si](C)(C)C)C2)O[Si](C)(C)C	2468.8	Semi standard non polar	33892256
Nadolol,2TMS,isomer #3	CC(C)(C)N(CC(COC1=CC=CC2=C1C[C@H](O)[C@H](O)C2)O[Si](C)(C)C)[Si](C)(C)C	2727.5	Semi standard non polar	33892256
Nadolol,2TMS,isomer #4	CC(C)(C)NCC(O)COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C2	2518.6	Semi standard non polar	33892256
Nadolol,2TMS,isomer #5	CC(C)(C)N(CC(O)COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C)[C@H](O)C2)[Si](C)(C)C	2672.8	Semi standard non polar	33892256
Nadolol,2TMS,isomer #6	CC(C)(C)N(CC(O)COC1=CC=CC2=C1C[C@H](O)[C@H](O[Si](C)(C)C)C2)[Si](C)(C)C	2670.0	Semi standard non polar	33892256
Nadolol,3TMS,isomer #1	CC(C)(C)NCC(COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C2)O[Si](C)(C)C	2479.7	Semi standard non polar	33892256
Nadolol,3TMS,isomer #2	CC(C)(C)N(CC(COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C)[C@H](O)C2)O[Si](C)(C)C)[Si](C)(C)C	2704.4	Semi standard non polar	33892256
Nadolol,3TMS,isomer #3	CC(C)(C)N(CC(COC1=CC=CC2=C1C[C@H](O)[C@H](O[Si](C)(C)C)C2)O[Si](C)(C)C)[Si](C)(C)C	2709.1	Semi standard non polar	33892256
Nadolol,3TMS,isomer #4	CC(C)(C)N(CC(O)COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C2)[Si](C)(C)C	2675.8	Semi standard non polar	33892256
Nadolol,4TMS,isomer #1	CC(C)(C)N(CC(COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C2)O[Si](C)(C)C)[Si](C)(C)C	2720.4	Semi standard non polar	33892256
Nadolol,4TMS,isomer #1	CC(C)(C)N(CC(COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C2)O[Si](C)(C)C)[Si](C)(C)C	2819.4	Standard non polar	33892256
Nadolol,4TMS,isomer #1	CC(C)(C)N(CC(COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C2)O[Si](C)(C)C)[Si](C)(C)C	2674.0	Standard polar	33892256
Nadolol,1TBDMS,isomer #1	CC(C)(C)NCC(COC1=CC=CC2=C1C[C@H](O)[C@H](O)C2)O[Si](C)(C)C(C)(C)C	2781.0	Semi standard non polar	33892256
Nadolol,1TBDMS,isomer #2	CC(C)(C)NCC(O)COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C2	2767.4	Semi standard non polar	33892256
Nadolol,1TBDMS,isomer #3	CC(C)(C)NCC(O)COC1=CC=CC2=C1C[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C2	2770.1	Semi standard non polar	33892256
Nadolol,1TBDMS,isomer #4	CC(C)(C)N(CC(O)COC1=CC=CC2=C1C[C@H](O)[C@H](O)C2)[Si](C)(C)C(C)(C)C	2957.8	Semi standard non polar	33892256
Nadolol,2TBDMS,isomer #1	CC(C)(C)NCC(COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C2)O[Si](C)(C)C(C)(C)C	2914.5	Semi standard non polar	33892256
Nadolol,2TBDMS,isomer #2	CC(C)(C)NCC(COC1=CC=CC2=C1C[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C2)O[Si](C)(C)C(C)(C)C	2916.8	Semi standard non polar	33892256
Nadolol,2TBDMS,isomer #3	CC(C)(C)N(CC(COC1=CC=CC2=C1C[C@H](O)[C@H](O)C2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3194.7	Semi standard non polar	33892256
Nadolol,2TBDMS,isomer #4	CC(C)(C)NCC(O)COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C2	2946.5	Semi standard non polar	33892256
Nadolol,2TBDMS,isomer #5	CC(C)(C)N(CC(O)COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C2)[Si](C)(C)C(C)(C)C	3151.0	Semi standard non polar	33892256
Nadolol,2TBDMS,isomer #6	CC(C)(C)N(CC(O)COC1=CC=CC2=C1C[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C2)[Si](C)(C)C(C)(C)C	3145.6	Semi standard non polar	33892256
Nadolol,3TBDMS,isomer #1	CC(C)(C)NCC(COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C2)O[Si](C)(C)C(C)(C)C	3104.1	Semi standard non polar	33892256
Nadolol,3TBDMS,isomer #2	CC(C)(C)N(CC(COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3384.4	Semi standard non polar	33892256
Nadolol,3TBDMS,isomer #3	CC(C)(C)N(CC(COC1=CC=CC2=C1C[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3367.2	Semi standard non polar	33892256
Nadolol,3TBDMS,isomer #4	CC(C)(C)N(CC(O)COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C2)[Si](C)(C)C(C)(C)C	3335.7	Semi standard non polar	33892256
Nadolol,4TBDMS,isomer #1	CC(C)(C)N(CC(COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3557.2	Semi standard non polar	33892256
Nadolol,4TBDMS,isomer #1	CC(C)(C)N(CC(COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3578.7	Standard non polar	33892256
Nadolol,4TBDMS,isomer #1	CC(C)(C)N(CC(COC1=CC=CC2=C1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3019.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nadolol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0lyo-4490000000-f1ce44aef531d74d12ee	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nadolol GC-MS (3 TMS) - 70eV, Positive	splash10-03k9-9153380000-2521536c2b1d3ead6115	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nadolol 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 - Nadolol LC-ESI-qTof , Positive-QTOF	splash10-0k92-2920000000-2a6eb574de4bc8d52292	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nadolol LC-ESI-QFT , positive-QTOF	splash10-03di-0019000000-fdb4087c676d8d8d4a8e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nadolol LC-ESI-QFT , positive-QTOF	splash10-0udi-0092000000-e09452da687c6073a284	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nadolol LC-ESI-QFT , positive-QTOF	splash10-0uk9-4690000000-81baaf08e07647128956	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nadolol LC-ESI-QFT , positive-QTOF	splash10-0kmi-4930000000-adbaba8c066f6c5c5558	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nadolol LC-ESI-QFT , positive-QTOF	splash10-0aba-3900000000-3784678375e682bb5b2f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nadolol LC-ESI-QFT , positive-QTOF	splash10-05te-3900000000-52bc796915dc7eb2ff30	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nadolol , positive-QTOF	splash10-0ik9-0379000000-d94563052914b6b9e468	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nadolol , positive-QTOF	splash10-0k92-2920000000-2a6eb574de4bc8d52292	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nadolol 30V, Positive-QTOF	splash10-0udi-0092000000-b473fc172ac5b42242d9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nadolol 45V, Positive-QTOF	splash10-0uk9-4690000000-a0bf63af13818c7aaa53	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nadolol 60V, Positive-QTOF	splash10-0kmi-4930000000-9dd2e9e64e82c70bfe46	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nadolol 75V, Positive-QTOF	splash10-0aba-3900000000-5a12eac526fb680ed860	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nadolol 15V, Positive-QTOF	splash10-03di-0009000000-165a026a5c06abbf9c5d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nadolol 90V, Positive-QTOF	splash10-05te-3900000000-aff4be8e281f739fefb8	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nadolol 10V, Positive-QTOF	splash10-03di-2497000000-cb7ab3bdec4fd928a6f8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nadolol 20V, Positive-QTOF	splash10-000i-6491000000-e8d7e7ecf92155b5e141	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nadolol 40V, Positive-QTOF	splash10-022i-9700000000-776ddc0e9892504d78f6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nadolol 10V, Negative-QTOF	splash10-0a4i-1839000000-a1c8086c3bd17d51e494	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nadolol 20V, Negative-QTOF	splash10-01t9-0900000000-42e8fea24e6bfc13bc9e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nadolol 40V, Negative-QTOF	splash10-03fr-1900000000-ed7b5fe1e6fe690cabc7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nadolol 10V, Positive-QTOF	splash10-03di-0019000000-c97bcedcc1a631d0a91a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nadolol 20V, Positive-QTOF	splash10-0iki-1393000000-8b6d60cc09e1fa5c7582	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nadolol 40V, Positive-QTOF	splash10-0a4i-9500000000-179531439e7b92f4aef7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nadolol 10V, Negative-QTOF	splash10-0a4i-0309000000-bdfb17d488ca83f33346	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Nadolol 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 DB01203	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01203	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01203

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

35815

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nadolol

METLIN ID

Not Available

PubChem Compound

39147

PDB ID

Not Available

ChEBI ID

127570

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)

Download (PDF)

General References

Not Available

Enzymes

Enzyme Details

1. Beta-1 adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity
Gene Name:: ADRB1
Uniprot ID:: P08588
Molecular weight:: 51322.1

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Wheeldon NM, McDevitt DG, Lipworth BJ: The effects of lower than conventional doses of oral nadolol on relative beta 1/beta 2-adrenoceptor blockade. Br J Clin Pharmacol. 1994 Aug;38(2):103-8. [PubMed:7981009 ]
Koshiji M, Ito H, Minatoguchi S, Watanabe H, Imai Y, Kakami M, Hirakawa S: A comparison of guanfacine, bunazosin, atenolol and nadolol on blood pressure and plasma noradrenaline responses to cold pressor testing. Clin Exp Pharmacol Physiol. 1992 Jul;19(7):481-8. [PubMed:1354084 ]
Varma DR, Shen H, Deng XF, Peri KG, Chemtob S, Mulay S: Inverse agonist activities of beta-adrenoceptor antagonists in rat myocardium. Br J Pharmacol. 1999 Jun;127(4):895-902. [PubMed:10433496 ]
Varma DR: Ligand-independent negative chronotropic responses of rat and mouse right atria to beta-adrenoceptor antagonists. Can J Physiol Pharmacol. 1999 Dec;77(12):943-9. [PubMed:10606440 ]
Wheeldon NM, McDevitt DG, Lipworth BJ: Cardiac effects of the beta 3-adrenoceptor agonist BRL35135 in man. Br J Clin Pharmacol. 1994 Apr;37(4):363-9. [PubMed:7912539 ]

Enzyme Details

2. Beta-2 adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:: ADRB2
Uniprot ID:: P07550
Molecular weight:: 46458.3

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Wheeldon NM, McDevitt DG, Lipworth BJ: The effects of lower than conventional doses of oral nadolol on relative beta 1/beta 2-adrenoceptor blockade. Br J Clin Pharmacol. 1994 Aug;38(2):103-8. [PubMed:7981009 ]
Ozakca I, Arioglu E, Guner S, Altan VM, Ozcelikay AT: Role of beta-3-adrenoceptor in catecholamine-induced relaxations in gastric fundus from control and diabetic rats. Pharmacology. 2007;80(4):227-38. Epub 2007 Jul 6. [PubMed:17622774 ]
Liu YL, Toubro S, Astrup A, Stock MJ: Contribution of beta 3-adrenoceptor activation to ephedrine-induced thermogenesis in humans. Int J Obes Relat Metab Disord. 1995 Sep;19(9):678-85. [PubMed:8574280 ]
Wheeldon NM, McDevitt DG, Lipworth BJ: Evaluation of in vivo partial beta 1/beta 2-agonist activity: a dose-ranging study with carteolol. Br J Clin Pharmacol. 1992 Apr;33(4):411-6. [PubMed:1349493 ]
Varma DR, Shen H, Deng XF, Peri KG, Chemtob S, Mulay S: Inverse agonist activities of beta-adrenoceptor antagonists in rat myocardium. Br J Pharmacol. 1999 Jun;127(4):895-902. [PubMed:10433496 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Terao T, Hisanaga E, Sai Y, Tamai I, Tsuji A: Active secretion of drugs from the small intestinal epithelium in rats by P-glycoprotein functioning as an absorption barrier. J Pharm Pharmacol. 1996 Oct;48(10):1083-9. [PubMed:8953513 ]

Showing metabocard for Nadolol (HMDB0015334)

MOL for HMDB0015334 (Nadolol)

3D MOL for HMDB0015334 (Nadolol)

3D SDF for HMDB0015334 (Nadolol)

3D-SDF for HMDB0015334 (Nadolol)

PDB for HMDB0015334 (Nadolol)

3D PDB for HMDB0015334 (Nadolol)

SMILES for HMDB0015334 (Nadolol)

INCHI for HMDB0015334 (Nadolol)

Structure for HMDB0015334 (Nadolol)

3D Structure for HMDB0015334 (Nadolol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

Transporters

References