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    Chemistry

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    Also known as: Arginine vasopressin, 113-79-1, Argipressine, Pitressin, Beta-hypophamine, 8-arginine-vasopressin
    Molecular Formula
    C46H65N15O12S2
    Molecular Weight
    1084.2  g/mol
    InChI Key
    KBZOIRJILGZLEJ-LGYYRGKSSA-N
    Arginine Vasopressin
    The predominant form of mammalian antidiuretic hormone. It is a nonapeptide containing an ARGININE at residue 8 and two disulfide-linked cysteines at residues of 1 and 6. Arg-vasopressin is used to treat DIABETES INSIPIDUS or to improve vasomotor tone and BLOOD PRESSURE.
    1 2D Structure

    Arginine Vasopressin

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]pyrrolidine-2-carboxamide
    2.1.2 InChI
    InChI=1S/C46H65N15O12S2/c47-27-22-74-75-23-33(45(73)61-17-5-9-34(61)44(72)56-28(8-4-16-53-46(51)52)39(67)54-21-37(50)65)60-43(71)32(20-36(49)64)59-40(68)29(14-15-35(48)63)55-41(69)31(18-24-6-2-1-3-7-24)58-42(70)30(57-38(27)66)19-25-10-12-26(62)13-11-25/h1-3,6-7,10-13,27-34,62H,4-5,8-9,14-23,47H2,(H2,48,63)(H2,49,64)(H2,50,65)(H,54,67)(H,55,69)(H,56,72)(H,57,66)(H,58,70)(H,59,68)(H,60,71)(H4,51,52,53)/t27-,28-,29-,30-,31-,32-,33-,34-/m0/s1
    2.1.3 InChI Key
    KBZOIRJILGZLEJ-LGYYRGKSSA-N
    2.1.4 Canonical SMILES
    C1CC(N(C1)C(=O)C2CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=C(C=C4)O)N)C(=O)NC(CCCN=C(N)N)C(=O)NCC(=O)N
    2.1.5 Isomeric SMILES
    C1C[C@H](N(C1)C(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=C(C=C4)O)N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(=O)N
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Arg Vasopressin

    2. Arg-vasopressin

    3. Arginine Vasopressin

    4. Argipressin Tannate

    5. Vasopressin, Arginine

    2.2.2 Depositor-Supplied Synonyms

    1. Arginine Vasopressin

    2. 113-79-1

    3. Argipressine

    4. Pitressin

    5. Beta-hypophamine

    6. 8-arginine-vasopressin

    7. Argipressin Tannate

    8. Vasopressin (arginine Form)

    9. Arginine-vasopressin

    10. Chebi:34543

    11. Vasophysin

    12. Arg-vasopressin

    13. Chembl373742

    14. (arg8)-vasopressin

    15. [arg8]-vasopressin

    16. (2s)-1-[(4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-n-[(2s)-1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]pyrrolidine-2-carboxamide

    17. 8-l-arginine Vasopressin

    18. Argipresina

    19. Argipressina

    20. Argipressinum

    21. Avp

    22. Arg8-vasopressin

    23. Argipressin [inn]

    24. Argipressina [dcit]

    25. Ncgc00166306-01

    26. Argipressin [inn:ban]

    27. 8-l-arginine-vasopressin

    28. Argipresina [inn-spanish]

    29. Argipressine [inn-french]

    30. Argipressinum [inn-latin]

    31. Unii-y4907o6mfd

    32. Rindervasopressin

    33. [3h]vasopressin

    34. Einecs 204-035-4

    35. 3-(phenylalanine)-8-arginineoxytocin

    36. Arg8-vasopressin;avp

    37. Arginine-8-vasopressin

    38. Argipressin Or Lypressin

    39. [8-arginine]vasopressin

    40. [3h]argipressin Tannate

    41. Antidiuretic Hormone (adh)

    42. Arginine Vasopressin (avp)

    43. Argipressin Tannate [usan]

    44. Arginine Antidiuretic Hormone

    45. Dsstox_cid_28324

    46. Dsstox_rid_82752

    47. Dsstox_gsid_48349

    48. Schembl43139

    49. Vasopressin, 8-l-arginine-

    50. [cyclo S-s]cyfqncprg-nh2

    51. Gtpl2168

    52. Y4907o6mfd

    53. Dtxsid0048349

    54. Schembl17874853

    55. Bdbm35667

    56. Tox21_113037

    57. Bdbm50044777

    58. Mfcd00076738

    59. Ncgc00166306-02

    60. Ncgc00188439-01

    61. Cas-113-79-1

    62. H-cys-tyr-phe-gln-asn-cys-pro-arg-gly-nh2

    63. Oxytocin, 3-(l-phenylalanine)-8-l-arginine-

    64. Vasopressin, 8-l-arginine- (7ci,8ci,9ci)

    65. Roxybenzyl-6,9,12,15,18-pentaoxo- (6ci)

    66. 113a791

    67. Q183011

    68. Cys-tyr-phe-gln-asn-cys-pro-arg-gly-nh2[disulfide Bridge: 1-6]

    69. (2s)-1-[(4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-13-(phenylmethyl)1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-n-[(2s)-1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]pyrrolidine-2-carboxamide

    70. 1,2-dithia-5,8,11,14,17-pentaazacycloeicosane-10-propionamide, 19-amino-13-benzyl-7-(carbamoylmethyl)-4-[2-[[1-[(carbamoylmethyl)carbamoyl]-4-guanidinobutyl]carbamoyl]-1-pyrrolidinylcarbonyl]-16-p-hyd

    71. 1-{[(4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-l-prolyl-l-arginylglycinamide

    72. Glycinamide, L-cysteinyl-l-tyrosyl-l-phenylalanyl-l-glutaminyl-l-asparaginyl-l-cysteinyl-l-prolyl-l-arginyl-, Cyclic (1>6)-disulfide

    2.3 Create Date
    2005-06-01
    3 Chemical and Physical Properties
    Molecular Weight 1084.2 g/mol
    Molecular Formula C46H65N15O12S2
    XLogP3-4.8
    Hydrogen Bond Donor Count14
    Hydrogen Bond Acceptor Count16
    Rotatable Bond Count19
    Exact Mass1083.43785492 g/mol
    Monoisotopic Mass1083.43785492 g/mol
    Topological Polar Surface Area515 Ų
    Heavy Atom Count75
    Formal Charge0
    Complexity2070
    Isotope Atom Count0
    Defined Atom Stereocenter Count8
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Vasoconstrictor Agents

    Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)

    Antidiuretic Agents

    Agents that reduce the excretion of URINE, most notably the octapeptide VASOPRESSINS. (See all compounds classified as Antidiuretic Agents.)

    Hemostatics

    Agents acting to arrest the flow of blood. Absorbable hemostatics arrest bleeding either by the formation of an artificial clot or by providing a mechanical matrix that facilitates clotting when applied directly to the bleeding surface. These agents function more at the capillary level and are not effective at stemming arterial or venous bleeding under any significant intravascular pressure. (See all compounds classified as Hemostatics.)

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