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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7)transporters (5) Show 12 proteins XML

enzymes (7)transporters (5) Show 12 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:40 UTC

HMDB ID

HMDB0014600

Secondary Accession Numbers

HMDB14600

Metabolite Identification

Common Name

Prazosin

Description

Prazosin is a selective α-₁-adrenergic receptor antagonist used to treat hypertension. It has also been used to decrease urinary obstruction and relieve symptoms associated with symptomatic benign prostatic hyperplasia. α₁-Receptors mediate contraction and hypertrophic growth of smooth muscle cells. Antagonism of these receptors leads to smooth muscle relaxation in the peripheral vasculature and prostate gland. Prazosin has also been used in conjunction with cardiac glycosides and diuretics in the management of severe congestive heart failure. It has also been used alone or in combination with β-blockers in the preoperative management of signs and symptoms of pheochromocytoma.

Structure

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

457
  Mrv0541 02231214412D          

 28 31  0  0  0  0            999 V2000
    3.6702    2.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695    0.3387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1550    0.3540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1550   -1.3358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8137    0.3341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847    1.1591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2426    0.3341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5281   -0.9034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2426   -2.1409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8137    1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5281   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9571   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558    1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9571   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2426   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6946    0.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6946   -1.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2020    1.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4421   -0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4421   -0.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1518    1.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8711   -0.9261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  2  0  0  0  0
  2 17  1  0  0  0  0
  2 26  1  0  0  0  0
  3 23  1  0  0  0  0
  3 27  1  0  0  0  0
  4 24  1  0  0  0  0
  4 28  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 14  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  6 15  1  0  0  0  0
  7 14  2  0  0  0  0
  7 16  1  0  0  0  0
  8 14  1  0  0  0  0
  8 19  2  0  0  0  0
  9 19  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 20  2  0  0  0  0
 17 22  2  0  0  0  0
 18 19  1  0  0  0  0
 18 21  2  0  0  0  0
 20 23  1  0  0  0  0
 21 24  1  0  0  0  0
 22 25  1  0  0  0  0
 23 24  2  0  0  0  0
 25 26  2  0  0  0  0
M  END

HMDB0014600
     RDKit          3D
Prazosin
 49 52  0  0  0  0  0  0  0  0999 V2000
   -5.3404    0.8460    3.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5935    0.8368    1.9961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6527    0.5386    1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3662    0.2194    1.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4021   -0.0841    0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1332   -0.3985    0.7504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2265   -0.6867   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207   -1.0235    0.1004 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0441   -1.3214   -0.9581 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4132   -0.6489   -0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8124   -0.9268    0.6748 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9596   -0.4439    1.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1455   -0.8098    2.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9410    0.4082    0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0193    0.9451   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1964    1.7013   -0.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7747    1.5796    0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0213    0.8282    1.3028 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9147   -1.7966    1.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5863   -1.0710    1.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6272   -0.6512   -1.4671 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8641   -0.3490   -1.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2201   -0.3299   -3.2310 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8037   -0.0509   -0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1026    0.2695   -1.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0228    0.5635   -0.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3251    0.8860   -0.6256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7024    0.9117   -1.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3499   -0.2060    3.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0746    1.4472    3.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3275    1.2621    3.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0486    0.1921    2.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2581   -2.3870   -1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7016   -0.8444   -1.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0991   -1.0144   -1.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2355    0.4344   -0.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3732    0.8738   -1.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5768    2.2663   -1.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7009    2.0184    0.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7625   -2.7518    0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3223   -1.9933    2.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202   -0.0095    1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8483   -1.5253    2.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696   -1.2220   -3.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3388    0.5686   -3.7431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3718    0.2838   -2.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3810   -0.0601   -2.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7988    0.9895   -2.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2045    1.7358   -2.4957 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 11 19  1  0
 19 20  1  0
  7 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 26  3  1  0
 24  5  1  0
 20  8  1  0
 18 14  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 23 44  1  0
 23 45  1  0
 25 46  1  0
 28 47  1  0
 28 48  1  0
 28 49  1  0
M  END

457
  Mrv0541 02231214412D          

 28 31  0  0  0  0            999 V2000
    3.6702    2.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695    0.3387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1550    0.3540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1550   -1.3358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8137    0.3341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847    1.1591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2426    0.3341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5281   -0.9034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2426   -2.1409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8137    1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5281   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9571   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558    1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9571   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2426   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6946    0.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6946   -1.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2020    1.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4421   -0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4421   -0.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1518    1.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8711   -0.9261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  2  0  0  0  0
  2 17  1  0  0  0  0
  2 26  1  0  0  0  0
  3 23  1  0  0  0  0
  3 27  1  0  0  0  0
  4 24  1  0  0  0  0
  4 28  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 14  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  6 15  1  0  0  0  0
  7 14  2  0  0  0  0
  7 16  1  0  0  0  0
  8 14  1  0  0  0  0
  8 19  2  0  0  0  0
  9 19  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 20  2  0  0  0  0
 17 22  2  0  0  0  0
 18 19  1  0  0  0  0
 18 21  2  0  0  0  0
 20 23  1  0  0  0  0
 21 24  1  0  0  0  0
 22 25  1  0  0  0  0
 23 24  2  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014600

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1=CC=CO1

> <INCHI_IDENTIFIER>
InChI=1S/C19H21N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h3-4,9-11H,5-8H2,1-2H3,(H2,20,21,22)

> <INCHI_KEY>
IENZQIKPVFGBNW-UHFFFAOYSA-N

> <FORMULA>
C19H21N5O4

> <MOLECULAR_WEIGHT>
383.4011

> <EXACT_MASS>
383.159354185

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
40.488823493372315

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[4-(furan-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
1.6505164626666664

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.2429429338165505

> <JCHEM_POLAR_SURFACE_AREA>
106.95

> <JCHEM_REFRACTIVITY>
104.4981

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
prazosin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014600
     RDKit          3D
Prazosin
 49 52  0  0  0  0  0  0  0  0999 V2000
   -5.3404    0.8460    3.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5935    0.8368    1.9961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6527    0.5386    1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3662    0.2194    1.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4021   -0.0841    0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1332   -0.3985    0.7504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2265   -0.6867   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207   -1.0235    0.1004 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0441   -1.3214   -0.9581 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4132   -0.6489   -0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8124   -0.9268    0.6748 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9596   -0.4439    1.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1455   -0.8098    2.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9410    0.4082    0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0193    0.9451   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1964    1.7013   -0.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7747    1.5796    0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0213    0.8282    1.3028 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9147   -1.7966    1.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5863   -1.0710    1.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6272   -0.6512   -1.4671 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8641   -0.3490   -1.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2201   -0.3299   -3.2310 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8037   -0.0509   -0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1026    0.2695   -1.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0228    0.5635   -0.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3251    0.8860   -0.6256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7024    0.9117   -1.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3499   -0.2060    3.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0746    1.4472    3.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3275    1.2621    3.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0486    0.1921    2.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2581   -2.3870   -1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7016   -0.8444   -1.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0991   -1.0144   -1.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2355    0.4344   -0.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3732    0.8738   -1.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5768    2.2663   -1.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7009    2.0184    0.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7625   -2.7518    0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3223   -1.9933    2.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202   -0.0095    1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8483   -1.5253    2.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696   -1.2220   -3.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3388    0.5686   -3.7431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3718    0.2838   -2.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3810   -0.0601   -2.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7988    0.9895   -2.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2045    1.7358   -2.4957 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 11 19  1  0
 19 20  1  0
  7 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 26  3  1  0
 24  5  1  0
 20  8  1  0
 18 14  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 23 44  1  0
 23 45  1  0
 25 46  1  0
 28 47  1  0
 28 48  1  0
 28 49  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 457                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.851   4.474   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.356   0.632   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      18.956   0.661   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      18.956  -2.493   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      10.852   0.624   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       8.185   2.164   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      13.520   0.624   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      12.186  -1.686   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      13.520  -3.996   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       9.519  -0.146   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.852   2.164   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.185   0.624   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.519   2.934   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.186  -0.146   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.851   2.934   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.853  -0.146   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.517   2.164   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.853  -1.686   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.520  -2.456   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.230   0.677   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.230  -2.510   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.110   2.790   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.625  -0.114   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.625  -1.718   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080   1.646   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.850   0.312   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.950   2.201   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.293  -1.729   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   17   26                                                       
CONECT    3   23   27                                                       
CONECT    4   24   28                                                       
CONECT    5   10   11   14                                                  
CONECT    6   12   13   15                                                  
CONECT    7   14   16                                                       
CONECT    8   14   19                                                       
CONECT    9   19                                                            
CONECT   10    5   12                                                       
CONECT   11    5   13                                                       
CONECT   12    6   10                                                       
CONECT   13    6   11                                                       
CONECT   14    5    7    8                                                  
CONECT   15    1    6   17                                                  
CONECT   16    7   18   20                                                  
CONECT   17    2   15   22                                                  
CONECT   18   16   19   21                                                  
CONECT   19    8    9   18                                                  
CONECT   20   16   23                                                       
CONECT   21   18   24                                                       
CONECT   22   17   25                                                       
CONECT   23    3   20   24                                                  
CONECT   24    4   21   23                                                  
CONECT   25   22   26                                                       
CONECT   26    2   25                                                       
CONECT   27    3                                                            
CONECT   28    4                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0014600
HETATM    1  C1  UNL     1      -5.340   0.846   3.381  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.593   0.837   1.996  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.653   0.539   1.040  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.366   0.219   1.367  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.402  -0.084   0.425  1.00  0.00           C  
HETATM    6  N1  UNL     1      -1.133  -0.399   0.750  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.226  -0.687  -0.188  1.00  0.00           C  
HETATM    8  N2  UNL     1       1.121  -1.023   0.100  1.00  0.00           N  
HETATM    9  C6  UNL     1       2.044  -1.321  -0.958  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.413  -0.649  -0.675  1.00  0.00           C  
HETATM   11  N3  UNL     1       3.812  -0.927   0.675  1.00  0.00           N  
HETATM   12  C8  UNL     1       4.960  -0.444   1.270  1.00  0.00           C  
HETATM   13  O2  UNL     1       5.145  -0.810   2.503  1.00  0.00           O  
HETATM   14  C9  UNL     1       5.941   0.408   0.655  1.00  0.00           C  
HETATM   15  C10 UNL     1       6.019   0.945  -0.592  1.00  0.00           C  
HETATM   16  C11 UNL     1       7.196   1.701  -0.650  1.00  0.00           C  
HETATM   17  C12 UNL     1       7.775   1.580   0.582  1.00  0.00           C  
HETATM   18  O3  UNL     1       7.021   0.828   1.303  1.00  0.00           O  
HETATM   19  C13 UNL     1       2.915  -1.797   1.473  1.00  0.00           C  
HETATM   20  C14 UNL     1       1.586  -1.071   1.486  1.00  0.00           C  
HETATM   21  N4  UNL     1      -0.627  -0.651  -1.467  1.00  0.00           N  
HETATM   22  C15 UNL     1      -1.864  -0.349  -1.863  1.00  0.00           C  
HETATM   23  N5  UNL     1      -2.220  -0.330  -3.231  1.00  0.00           N  
HETATM   24  C16 UNL     1      -2.804  -0.051  -0.901  1.00  0.00           C  
HETATM   25  C17 UNL     1      -4.103   0.270  -1.263  1.00  0.00           C  
HETATM   26  C18 UNL     1      -5.023   0.564  -0.285  1.00  0.00           C  
HETATM   27  O4  UNL     1      -6.325   0.886  -0.626  1.00  0.00           O  
HETATM   28  C19 UNL     1      -6.702   0.912  -1.973  1.00  0.00           C  
HETATM   29  H1  UNL     1      -5.350  -0.206   3.732  1.00  0.00           H  
HETATM   30  H2  UNL     1      -6.075   1.447   3.946  1.00  0.00           H  
HETATM   31  H3  UNL     1      -4.328   1.262   3.570  1.00  0.00           H  
HETATM   32  H4  UNL     1      -3.049   0.192   2.400  1.00  0.00           H  
HETATM   33  H5  UNL     1       2.258  -2.387  -1.078  1.00  0.00           H  
HETATM   34  H6  UNL     1       1.702  -0.844  -1.905  1.00  0.00           H  
HETATM   35  H7  UNL     1       4.099  -1.014  -1.434  1.00  0.00           H  
HETATM   36  H8  UNL     1       3.235   0.434  -0.758  1.00  0.00           H  
HETATM   37  H9  UNL     1       5.373   0.874  -1.439  1.00  0.00           H  
HETATM   38  H10 UNL     1       7.577   2.266  -1.488  1.00  0.00           H  
HETATM   39  H11 UNL     1       8.701   2.018   0.936  1.00  0.00           H  
HETATM   40  H12 UNL     1       2.763  -2.752   0.943  1.00  0.00           H  
HETATM   41  H13 UNL     1       3.322  -1.993   2.463  1.00  0.00           H  
HETATM   42  H14 UNL     1       1.820  -0.009   1.761  1.00  0.00           H  
HETATM   43  H15 UNL     1       0.848  -1.525   2.159  1.00  0.00           H  
HETATM   44  H16 UNL     1      -2.370  -1.222  -3.749  1.00  0.00           H  
HETATM   45  H17 UNL     1      -2.339   0.569  -3.743  1.00  0.00           H  
HETATM   46  H18 UNL     1      -4.372   0.284  -2.299  1.00  0.00           H  
HETATM   47  H19 UNL     1      -6.381  -0.060  -2.432  1.00  0.00           H  
HETATM   48  H20 UNL     1      -7.799   0.989  -2.105  1.00  0.00           H  
HETATM   49  H21 UNL     1      -6.205   1.736  -2.496  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3
CONECT    3    4    4   26
CONECT    4    5   32
CONECT    5    6    6   24
CONECT    6    7
CONECT    7    8   21   21
CONECT    8    9   20
CONECT    9   10   33   34
CONECT   10   11   35   36
CONECT   11   12   19
CONECT   12   13   13   14
CONECT   14   15   15   18
CONECT   15   16   37
CONECT   16   17   17   38
CONECT   17   18   39
CONECT   19   20   40   41
CONECT   20   42   43
CONECT   21   22
CONECT   22   23   24   24
CONECT   23   44   45
CONECT   24   25
CONECT   25   26   26   46
CONECT   26   27
CONECT   27   28
CONECT   28   47   48   49
END

HMDB0014600
     RDKit          3D
Prazosin
 49 52  0  0  0  0  0  0  0  0999 V2000
   -5.3404    0.8460    3.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5935    0.8368    1.9961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6527    0.5386    1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3662    0.2194    1.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4021   -0.0841    0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1332   -0.3985    0.7504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2265   -0.6867   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207   -1.0235    0.1004 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0441   -1.3214   -0.9581 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4132   -0.6489   -0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8124   -0.9268    0.6748 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9596   -0.4439    1.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1455   -0.8098    2.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9410    0.4082    0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0193    0.9451   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1964    1.7013   -0.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7747    1.5796    0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0213    0.8282    1.3028 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9147   -1.7966    1.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5863   -1.0710    1.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6272   -0.6512   -1.4671 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8641   -0.3490   -1.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2201   -0.3299   -3.2310 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8037   -0.0509   -0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1026    0.2695   -1.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0228    0.5635   -0.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3251    0.8860   -0.6256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7024    0.9117   -1.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3499   -0.2060    3.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0746    1.4472    3.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3275    1.2621    3.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0486    0.1921    2.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2581   -2.3870   -1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7016   -0.8444   -1.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0991   -1.0144   -1.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2355    0.4344   -0.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3732    0.8738   -1.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5768    2.2663   -1.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7009    2.0184    0.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7625   -2.7518    0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3223   -1.9933    2.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202   -0.0095    1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8483   -1.5253    2.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696   -1.2220   -3.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3388    0.5686   -3.7431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3718    0.2838   -2.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3810   -0.0601   -2.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7988    0.9895   -2.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2045    1.7358   -2.4957 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 11 19  1  0
 19 20  1  0
  7 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 26  3  1  0
 24  5  1  0
 20  8  1  0
 18 14  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 23 44  1  0
 23 45  1  0
 25 46  1  0
 28 47  1  0
 28 48  1  0
 28 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furanylcarbonyl)piperazine	ChEBI
2-(4-(2-Furoyl)piperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline	ChEBI
Prazosina	ChEBI
Prazosine	ChEBI
Prazosinum	ChEBI
Minipress	Kegg
Prazocin	HMDB
Furazosin	HMDB
Hydrochloride, prazosin	HMDB
Pfizer brand OF prazosin hydrochloride	HMDB
Douglas brand OF prazosin hydrochloride	HMDB
Prazosin HCL	HMDB
HCL, Prazosin	HMDB
Pratsiol	HMDB
Prazosin hydrochloride	HMDB

Chemical Formula

C₁₉H₂₁N₅O₄

Average Molecular Weight

383.4011

Monoisotopic Molecular Weight

383.159354185

IUPAC Name

2-[4-(furan-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine

Traditional Name

prazosin

CAS Registry Number

19216-56-9

SMILES

COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1=CC=CO1

InChI Identifier

InChI=1S/C19H21N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h3-4,9-11H,5-8H2,1-2H3,(H2,20,21,22)

InChI Key

IENZQIKPVFGBNW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

N-arylpiperazines

Alternative Parents

Substituents

N-arylpiperazine
Quinazolinamine
Diazanaphthalene
Quinazoline
2-heteroaryl carboxamide
Furoic acid or derivatives
Anisole
Dialkylarylamine
Alkyl aryl ether
Aminopyrimidine
Benzenoid
Pyrimidine
Imidolactam
Tertiary carboxylic acid amide
Heteroaromatic compound
Furan
Carboxamide group
Amino acid or derivatives
Carboxylic acid derivative
Ether
Oxacycle
Azacycle
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Primary amine
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:8364 )
monocarboxylic acid amide (CHEBI:8364 )
furans (CHEBI:8364 )
quinazolines (CHEBI:8364 )
piperazines (CHEBI:8364 )

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

Extracellular (HMDB: HMDB0014600)
Membrane (HMDB: HMDB0014600)

Source

Exogenous

Exogenous (HMDB: HMDB0014600)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	279 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.69 g/L	Not Available
LogP	1.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	192.7	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.69 g/L	ALOGPS
logP	1.93	ALOGPS
logP	1.65	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	7.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	106.95 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.5 m³·mol⁻¹	ChemAxon
Polarizability	40.49 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	190.369	31661259
DarkChem	[M-H]-	189.158	31661259
DeepCCS	[M+H]+	186.309	30932474
DeepCCS	[M-H]-	183.951	30932474
DeepCCS	[M-2H]-	218.225	30932474
DeepCCS	[M+Na]+	193.352	30932474
AllCCS	[M+H]+	191.0	32859911
AllCCS	[M+H-H2O]+	188.4	32859911
AllCCS	[M+NH4]+	193.5	32859911
AllCCS	[M+Na]+	194.2	32859911
AllCCS	[M-H]-	190.7	32859911
AllCCS	[M+Na-2H]-	190.7	32859911
AllCCS	[M+HCOO]-	190.8	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.	2.92 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3322 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.37 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	51.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	834.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	203.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	134.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	73.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	288.3 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	418.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	526.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	699.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	292.9 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	1280.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	266.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	289.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	417.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	293.6 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	34.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prazosin	COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1=CC=CO1	4098.7	Standard polar	33892256
Prazosin	COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1=CC=CO1	3412.8	Standard non polar	33892256
Prazosin	COC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1=CC=CO1	3750.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prazosin,1TMS,isomer #1	COC1=CC2=NC(N3CCN(C(=O)C4=CC=CO4)CC3)=NC(N[Si](C)(C)C)=C2C=C1OC	3744.7	Semi standard non polar	33892256
Prazosin,1TMS,isomer #1	COC1=CC2=NC(N3CCN(C(=O)C4=CC=CO4)CC3)=NC(N[Si](C)(C)C)=C2C=C1OC	3249.2	Standard non polar	33892256
Prazosin,1TMS,isomer #1	COC1=CC2=NC(N3CCN(C(=O)C4=CC=CO4)CC3)=NC(N[Si](C)(C)C)=C2C=C1OC	5301.9	Standard polar	33892256
Prazosin,2TMS,isomer #1	COC1=CC2=NC(N3CCN(C(=O)C4=CC=CO4)CC3)=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2C=C1OC	3648.7	Semi standard non polar	33892256
Prazosin,2TMS,isomer #1	COC1=CC2=NC(N3CCN(C(=O)C4=CC=CO4)CC3)=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2C=C1OC	3198.7	Standard non polar	33892256
Prazosin,2TMS,isomer #1	COC1=CC2=NC(N3CCN(C(=O)C4=CC=CO4)CC3)=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2C=C1OC	4866.5	Standard polar	33892256
Prazosin,1TBDMS,isomer #1	COC1=CC2=NC(N3CCN(C(=O)C4=CC=CO4)CC3)=NC(N[Si](C)(C)C(C)(C)C)=C2C=C1OC	3913.4	Semi standard non polar	33892256
Prazosin,1TBDMS,isomer #1	COC1=CC2=NC(N3CCN(C(=O)C4=CC=CO4)CC3)=NC(N[Si](C)(C)C(C)(C)C)=C2C=C1OC	3416.9	Standard non polar	33892256
Prazosin,1TBDMS,isomer #1	COC1=CC2=NC(N3CCN(C(=O)C4=CC=CO4)CC3)=NC(N[Si](C)(C)C(C)(C)C)=C2C=C1OC	5207.1	Standard polar	33892256
Prazosin,2TBDMS,isomer #1	COC1=CC2=NC(N3CCN(C(=O)C4=CC=CO4)CC3)=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2C=C1OC	3997.7	Semi standard non polar	33892256
Prazosin,2TBDMS,isomer #1	COC1=CC2=NC(N3CCN(C(=O)C4=CC=CO4)CC3)=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2C=C1OC	3623.3	Standard non polar	33892256
Prazosin,2TBDMS,isomer #1	COC1=CC2=NC(N3CCN(C(=O)C4=CC=CO4)CC3)=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2C=C1OC	4763.0	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB00457	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00457	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00457

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4724

KEGG Compound ID

C07368

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Prazosin

METLIN ID

Not Available

PubChem Compound

4893

PDB ID

XRA

ChEBI ID

8364

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

Hiraoka Y, Taniguchi T, Tanaka T, Okada K, Kanamaru H, Muramatsu I: Pharmacological characterization of unique prazosin-binding sites in human kidney. Naunyn Schmiedebergs Arch Pharmacol. 2003 Jul;368(1):49-56. Epub 2003 Jun 25. [PubMed:12827214 ]
Cushman WC, Ford CE, Cutler JA, Margolis KL, Davis BR, Grimm RH, Black HR, Hamilton BP, Holland J, Nwachuku C, Papademetriou V, Probstfield J, Wright JT Jr, Alderman MH, Weiss RJ, Piller L, Bettencourt J, Walsh SM: Success and predictors of blood pressure control in diverse North American settings: the antihypertensive and lipid-lowering treatment to prevent heart attack trial (ALLHAT). J Clin Hypertens (Greenwich). 2002 Nov-Dec;4(6):393-404. [PubMed:12461301 ]
Bawaskar HS, Bawaskar PH: Utility of scorpion antivenin vs prazosin in the management of severe Mesobuthus tamulus (Indian red scorpion) envenoming at rural setting. J Assoc Physicians India. 2007 Jan;55:14-21. [PubMed:17444339 ]
Sigma Aldrich [Link]

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 1A1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Potassium voltage-gated channel subfamily H member 2

General function:: Involved in ion channel activity
Specific function:: Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoform 3 has no channel activity by itself, but modulates channel characteristics when associated with isoform 1
Gene Name:: KCNH2
Uniprot ID:: Q12809
Molecular weight:: 126653.5

References

Thomas D, Wimmer AB, Wu K, Hammerling BC, Ficker EK, Kuryshev YA, Kiehn J, Katus HA, Schoels W, Karle CA: Inhibition of human ether-a-go-go-related gene potassium channels by alpha 1-adrenoceptor antagonists prazosin, doxazosin, and terazosin. Naunyn Schmiedebergs Arch Pharmacol. 2004 May;369(5):462-72. Epub 2004 Apr 20. [PubMed:15098086 ]

Enzyme Details

3. Potassium voltage-gated channel subfamily H member 6

General function:: Involved in ion channel activity
Specific function:: Pore-forming (alpha) subunit of voltage-gated potassium channel. Elicits a slowly activating, rectifying current. Channel properties may be modulated by cAMP and subunit assembly
Gene Name:: KCNH6
Uniprot ID:: Q9H252
Molecular weight:: 109923.7

References

Thomas D, Wimmer AB, Wu K, Hammerling BC, Ficker EK, Kuryshev YA, Kiehn J, Katus HA, Schoels W, Karle CA: Inhibition of human ether-a-go-go-related gene potassium channels by alpha 1-adrenoceptor antagonists prazosin, doxazosin, and terazosin. Naunyn Schmiedebergs Arch Pharmacol. 2004 May;369(5):462-72. Epub 2004 Apr 20. [PubMed:15098086 ]

Enzyme Details

4. Alpha-1A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular weight:: 51486.0

References

Chang HK, Hsu FL, Liu IM, Cheng JT: Stimulatory effect of cinnamic acid analogues on alpha1A-adrenoceptors in-vitro. J Pharm Pharmacol. 2003 Jun;55(6):833-7. [PubMed:12841945 ]
Eltze M: In functional experiments, risperidone is selective, not for the B, but for the A subtype of alpha 1-adrenoceptors. Eur J Pharmacol. 1996 Jan 4;295(1):69-73. [PubMed:8925876 ]
Morris DP, Price RR, Smith MP, Lei B, Schwinn DA: Cellular trafficking of human alpha1a-adrenergic receptors is continuous and primarily agonist-independent. Mol Pharmacol. 2004 Oct;66(4):843-54. Epub 2004 Jul 16. [PubMed:15258254 ]
Sleight AJ, Koek W, Bigg DC: Binding of antipsychotic drugs at alpha 1A- and alpha 1B-adrenoceptors: risperidone is selective for the alpha 1B-adrenoceptors. Eur J Pharmacol. 1993 Jul 20;238(2-3):407-10. [PubMed:7691623 ]
Suzuki Y, Kanada A, Okaya Y, Aisaka K: Effect of JTH-601, a novel alpha(1)-adrenoceptor antagonist, on prostate function in dogs. Eur J Pharmacol. 2000 Apr 7;394(1):123-30. [PubMed:10771044 ]
Tomiyama Y, Kobayashi K, Tadachi M, Kobayashi S, Inada Y, Kobayashi M, Yamazaki Y: Expressions and mechanical functions of alpha1-adrenoceptor subtypes in hamster ureter. Eur J Pharmacol. 2007 Nov 14;573(1-3):201-5. Epub 2007 Jul 6. [PubMed:17658513 ]
Zacharia J, Hillier C, MacDonald A: Alpha1-adrenoceptor subtypes involved in vasoconstrictor responses to exogenous and neurally released noradrenaline in rat femoral resistance arteries. Br J Pharmacol. 2004 Mar;141(6):915-24. Epub 2004 Feb 23. [PubMed:14980979 ]
Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]

Enzyme Details

5. Alpha-1B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:: ADRA1B
Uniprot ID:: P35368
Molecular weight:: 56835.4

References

Al-Damluji S, Shen WB, White S, Barnard EA: alpha(1B) adrenergic receptors in gonadotrophin-releasing hormone neurones: relation to Transport-P. Br J Pharmacol. 2001 Jan;132(1):336-44. [PubMed:11156594 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Eltze M: In functional experiments, risperidone is selective, not for the B, but for the A subtype of alpha 1-adrenoceptors. Eur J Pharmacol. 1996 Jan 4;295(1):69-73. [PubMed:8925876 ]
Ishiguro M, Futabayashi Y, Ohnuki T, Ahmed M, Muramatsu I, Nagatomo T: Identification of binding sites of prazosin, tamsulosin and KMD-3213 with alpha(1)-adrenergic receptor subtypes by molecular modeling. Life Sci. 2002 Oct 11;71(21):2531-41. [PubMed:12270758 ]
Sharpe IA, Thomas L, Loughnan M, Motin L, Palant E, Croker DE, Alewood D, Chen S, Graham RM, Alewood PF, Adams DJ, Lewis RJ: Allosteric alpha 1-adrenoreceptor antagonism by the conopeptide rho-TIA. J Biol Chem. 2003 Sep 5;278(36):34451-7. Epub 2003 Jun 24. [PubMed:12824165 ]
Sleight AJ, Koek W, Bigg DC: Binding of antipsychotic drugs at alpha 1A- and alpha 1B-adrenoceptors: risperidone is selective for the alpha 1B-adrenoceptors. Eur J Pharmacol. 1993 Jul 20;238(2-3):407-10. [PubMed:7691623 ]
Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]

Enzyme Details

6. Alpha-1D adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium
Gene Name:: ADRA1D
Uniprot ID:: P25100
Molecular weight:: 60462.2

References

Nagaoka Y, Ahmed M, Hossain M, Bhuiyan MA, Ishiguro M, Nakamura T, Watanabe M, Nagatomo T: Amino acids of the human alpha1d-adrenergic receptor involved in antagonist binding. J Pharmacol Sci. 2008 Jan;106(1):114-20. Epub 2008 Jan 11. [PubMed:18187928 ]
Yamamoto Y, Koike K: alpha(1)-Adrenoceptor subtypes in the mouse mesenteric artery and abdominal aorta. Br J Pharmacol. 2001 Nov;134(5):1045-54. [PubMed:11682453 ]
Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]

Enzyme Details

7. Potassium voltage-gated channel subfamily H member 7

General function:: Involved in ion channel activity
Specific function:: Pore-forming (alpha) subunit of voltage-gated potassium channel. Channel properties may be modulated by cAMP and subunit assembly
Gene Name:: KCNH7
Uniprot ID:: Q9NS40
Molecular weight:: 134998.5

References

Thomas D, Wimmer AB, Wu K, Hammerling BC, Ficker EK, Kuryshev YA, Kiehn J, Katus HA, Schoels W, Karle CA: Inhibition of human ether-a-go-go-related gene potassium channels by alpha 1-adrenoceptor antagonists prazosin, doxazosin, and terazosin. Naunyn Schmiedebergs Arch Pharmacol. 2004 May;369(5):462-72. Epub 2004 Apr 20. [PubMed:15098086 ]

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

Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]
Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]
Takara K, Sakaeda T, Kakumoto M, Tanigawara Y, Kobayashi H, Okumura K, Ohnishi N, Yokoyama T: Effects of alpha-adrenoceptor antagonist doxazosin on MDR1-mediated multidrug resistance and transcellular transport. Oncol Res. 2009;17(11-12):527-33. [PubMed:19806783 ]
Dohse M, Scharenberg C, Shukla S, Robey RW, Volkmann T, Deeken JF, Brendel C, Ambudkar SV, Neubauer A, Bates SE: Comparison of ATP-binding cassette transporter interactions with the tyrosine kinase inhibitors imatinib, nilotinib, and dasatinib. Drug Metab Dispos. 2010 Aug;38(8):1371-80. doi: 10.1124/dmd.109.031302. Epub 2010 Apr 27. [PubMed:20423956 ]
Dey S, Ramachandra M, Pastan I, Gottesman MM, Ambudkar SV: Evidence for two nonidentical drug-interaction sites in the human P-glycoprotein. Proc Natl Acad Sci U S A. 1997 Sep 30;94(20):10594-9. [PubMed:9380680 ]

Enzyme Details

2. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

Dohse M, Scharenberg C, Shukla S, Robey RW, Volkmann T, Deeken JF, Brendel C, Ambudkar SV, Neubauer A, Bates SE: Comparison of ATP-binding cassette transporter interactions with the tyrosine kinase inhibitors imatinib, nilotinib, and dasatinib. Drug Metab Dispos. 2010 Aug;38(8):1371-80. doi: 10.1124/dmd.109.031302. Epub 2010 Apr 27. [PubMed:20423956 ]
Ozvegy C, Litman T, Szakacs G, Nagy Z, Bates S, Varadi A, Sarkadi B: Functional characterization of the human multidrug transporter, ABCG2, expressed in insect cells. Biochem Biophys Res Commun. 2001 Jul 6;285(1):111-7. [PubMed:11437380 ]

Enzyme Details

3. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607 ]

Enzyme Details

4. Solute carrier family 22 member 2

General function:: Involved in ion transmembrane transporter activity
Specific function:: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:: SLC22A2
Uniprot ID:: O15244
Molecular weight:: 62564.0

References

Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607 ]
Pan G, Winter TN, Roberts JC, Fairbanks CA, Elmquist WF: Organic cation uptake is enhanced in bcrp1-transfected MDCKII cells. Mol Pharm. 2010 Feb 1;7(1):138-45. doi: 10.1021/mp900177r. [PubMed:19886673 ]

Enzyme Details

5. Solute carrier family 22 member 3

General function:: Involved in transmembrane transport
Specific function:: Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:: SLC22A3
Uniprot ID:: O75751
Molecular weight:: 61279.5

References

Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607 ]

Only showing the first 10 proteins. There are 12 proteins in total.

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Showing metabocard for Prazosin (HMDB0014600)

MOL for HMDB0014600 (Prazosin)

3D MOL for HMDB0014600 (Prazosin)

3D SDF for HMDB0014600 (Prazosin)

3D-SDF for HMDB0014600 (Prazosin)

PDB for HMDB0014600 (Prazosin)

3D PDB for HMDB0014600 (Prazosin)

SMILES for HMDB0014600 (Prazosin)

INCHI for HMDB0014600 (Prazosin)

Structure for HMDB0014600 (Prazosin)

3D Structure for HMDB0014600 (Prazosin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

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Transporters

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