NP-MRD: Showing NP-Card for Arginine vasopressin 1-8 (NP0339113)

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Record Information

Version

2.0

Created at

2024-09-11 19:44:52 UTC

Updated at

2024-09-11 19:44:53 UTC

NP-MRD ID

NP0339113

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arginine vasopressin 1-8

Description

Arginine vasopressin 1-8 belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Arginine vasopressin 1-8 is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303102016472D          

 71 74  0  0  1  0            999 V2000
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M  END


  Mrv1652303102016472D          

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 39 54  1  0  0  0  0
 39 64  2  0  0  0  0
 40 56  1  0  0  0  0
 40 65  2  0  0  0  0
 41 66  2  0  0  0  0
 41 52  1  0  0  0  0
 42 67  2  0  0  0  0
 42 57  1  0  0  0  0
 43 68  1  0  0  0  0
 43 69  2  0  0  0  0
 44 50  1  0  0  0  0
 44 48  1  0  0  0  0
 44 49  2  0  0  0  0
 70 71  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339113

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1CSSC[C@H](NC(=O)C(CC(O)=N)NC(=O)[C@@H](CCC(O)=N)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@@H](CC2=CC=C(O)C=C2)NC1=O)C(=O)N1CCC[C@@H]1C(=O)N[C@H](CCCNC(N)=N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C44H61N13O12S2/c45-26-21-70-71-22-32(42(67)57-17-5-9-33(57)41(66)52-28(43(68)69)8-4-16-50-44(48)49)56-40(65)31(20-35(47)60)55-37(62)27(14-15-34(46)59)51-38(63)30(18-23-6-2-1-3-7-23)54-39(64)29(53-36(26)61)19-24-10-12-25(58)13-11-24/h1-3,6-7,10-13,26-33,58H,4-5,8-9,14-22,45H2,(H2,46,59)(H2,47,60)(H,51,63)(H,52,66)(H,53,61)(H,54,64)(H,55,62)(H,56,65)(H,68,69)(H4,48,49,50)/t26?,27-,28-,29-,30-,31?,32+,33-/m1/s1

> <INCHI_KEY>
SXYIOPJBWYQZRQ-VMPYSSHJSA-N

> <FORMULA>
C44H61N13O12S2

> <MOLECULAR_WEIGHT>
1028.165

> <EXACT_MASS>
1027.400405861

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
132

> <JCHEM_AVERAGE_POLARIZABILITY>
102.37079928959021

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
16

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-{[(2R)-1-[(4R,10R,13R,16R)-19-amino-13-benzyl-10-[2-(C-hydroxycarbonimidoyl)ethyl]-7-[(C-hydroxycarbonimidoyl)methyl]-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid

> <ALOGPS_LOGP>
-1.72

> <JCHEM_LOGP>
-10.22020099122534

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
-0.5441693850049569

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.3410459810954496

> <JCHEM_PKA_STRONGEST_BASIC>
12.79395603434443

> <JCHEM_POLAR_SURFACE_AREA>
428.52

> <JCHEM_REFRACTIVITY>
290.1335000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-{[(2R)-1-[(4R,10R,13R,16R)-19-amino-13-benzyl-10-[2-(C-hydroxycarbonimidoyl)ethyl]-7-(C-hydroxycarbonimidoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      37.413 -31.514   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      36.768 -32.913   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      36.524 -30.256   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.036 -16.929   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.966 -25.452   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      35.235 -33.054   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      34.990 -30.398   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.042 -18.469   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.485 -23.989   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.740 -24.128   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      37.076 -25.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.482 -22.779   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      37.819 -24.065   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.484 -32.928   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.988 -33.290   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.700 -16.165   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.506 -25.446   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.812 -31.938   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      34.794 -26.795   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.810 -28.896   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.592 -22.212   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.919 -23.753   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      34.346 -31.796   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      35.537 -25.446   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      37.022 -22.748   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      30.592 -23.753   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      27.919 -31.451   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.379 -19.234   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      33.254 -26.826   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      31.923 -30.680   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      25.257 -28.368   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      26.588 -24.524   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      22.727 -23.079   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      25.553 -34.768   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      23.544 -30.413   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      31.923 -24.524   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      26.588 -30.680   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      30.592 -31.451   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      33.254 -28.368   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      25.257 -26.826   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      22.721 -21.539   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      25.439 -23.498   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      22.709 -18.459   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      17.357 -13.860   0.000  0.00  0.00           C+0
HETATM   45  N   UNK     0      29.559 -24.710   0.000  0.00  0.00           N+0
HETATM   46  N   UNK     0      24.056 -35.130   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      22.097 -30.941   0.000  0.00  0.00           N+0
HETATM   48  N   UNK     0      17.351 -12.320   0.000  0.00  0.00           N+0
HETATM   49  N   UNK     0      16.026 -14.635   0.000  0.00  0.00           N+0
HETATM   50  N   UNK     0      18.694 -14.625   0.000  0.00  0.00           N+0
HETATM   51  N   UNK     0      29.261 -30.680   0.000  0.00  0.00           N+0
HETATM   52  N   UNK     0      21.385 -20.774   0.000  0.00  0.00           N+0
HETATM   53  N   UNK     0      31.923 -26.065   0.000  0.00  0.00           N+0
HETATM   54  N   UNK     0      31.923 -29.138   0.000  0.00  0.00           N+0
HETATM   55  N   UNK     0      26.588 -29.138   0.000  0.00  0.00           N+0
HETATM   56  N   UNK     0      26.588 -26.065   0.000  0.00  0.00           N+0
HETATM   57  N   UNK     0      23.977 -23.979   0.000  0.00  0.00           N+0
HETATM   58  O   UNK     0      37.765 -21.398   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      26.615 -35.883   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      24.725 -31.401   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      33.071 -23.498   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      25.699 -31.937   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      30.593 -32.632   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      34.221 -28.925   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      24.014 -26.108   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      24.052 -20.764   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      25.754 -21.990   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0      24.046 -19.224   0.000  0.00  0.00           O+0
HETATM   69  O   UNK     0      22.704 -16.919   0.000  0.00  0.00           O+0
HETATM   70  S   UNK     0      29.261 -21.441   0.000  0.00  0.00           S+0
HETATM   71  S   UNK     0      27.919 -22.212   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    8   16                                                       
CONECT    5   17    9                                                       
CONECT    6    2   23                                                       
CONECT    7    3   23                                                       
CONECT    8    4   28                                                       
CONECT    9    5   33                                                       
CONECT   10   24   12                                                       
CONECT   11   13   24                                                       
CONECT   12   10   25                                                       
CONECT   13   11   25                                                       
CONECT   14   27   15                                                       
CONECT   15   14   34                                                       
CONECT   16    4   50                                                       
CONECT   17    5   57                                                       
CONECT   18   30   23                                                       
CONECT   19   29   24                                                       
CONECT   20   31   35                                                       
CONECT   21   26   70                                                       
CONECT   22   71   32                                                       
CONECT   23    6    7   18                                                  
CONECT   24   10   11   19                                                  
CONECT   25   12   13   58                                                  
CONECT   26   21   45   36                                                  
CONECT   27   14   37   51                                                  
CONECT   28    8   52   43                                                  
CONECT   29   19   39   53                                                  
CONECT   30   18   38   54                                                  
CONECT   31   20   40   55                                                  
CONECT   32   22   42   56                                                  
CONECT   33    9   57   41                                                  
CONECT   34   15   46   59                                                  
CONECT   35   20   47   60                                                  
CONECT   36   26   53   61                                                  
CONECT   37   27   55   62                                                  
CONECT   38   30   51   63                                                  
CONECT   39   29   54   64                                                  
CONECT   40   31   56   65                                                  
CONECT   41   33   66   52                                                  
CONECT   42   32   67   57                                                  
CONECT   43   28   68   69                                                  
CONECT   44   50   48   49                                                  
CONECT   45   26                                                            
CONECT   46   34                                                            
CONECT   47   35                                                            
CONECT   48   44                                                            
CONECT   49   44                                                            
CONECT   50   16   44                                                       
CONECT   51   27   38                                                       
CONECT   52   28   41                                                       
CONECT   53   29   36                                                       
CONECT   54   30   39                                                       
CONECT   55   31   37                                                       
CONECT   56   32   40                                                       
CONECT   57   17   33   42                                                  
CONECT   58   25                                                            
CONECT   59   34                                                            
CONECT   60   35                                                            
CONECT   61   36                                                            
CONECT   62   37                                                            
CONECT   63   38                                                            
CONECT   64   39                                                            
CONECT   65   40                                                            
CONECT   66   41                                                            
CONECT   67   42                                                            
CONECT   68   43                                                            
CONECT   69   43                                                            
CONECT   70   21   71                                                       
CONECT   71   22   70                                                       
MASTER        0    0    0    0    0    0    0    0   71    0  148    0
END

View in JSmol

Synonyms

Value	Source
Cys-tyr-phe-GLN-asn-cys-pro-arg	HMDB
Des-gly-NH(,2)('9),[arg('8)]-vasopressin	HMDB
(2R)-2-({[(2R)-1-[(4R,10R,13R,16R)-19-amino-13-benzyl-6,9,12,15,18-pentahydroxy-10-[2-(C-hydroxycarbonimidoyl)ethyl]-7-[(C-hydroxycarbonimidoyl)methyl]-16-[(4-hydroxyphenyl)methyl]-1,2-dithia-5,8,11,14,17-pentaazacycloicosa-5,8,11,14,17-pentaene-4-carbonyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-5-carbamimidamidopentanoate	Generator

Chemical Formula

C₄₄H₆₁N₁₃O₁₂S₂

Average Mass

1028.1650 Da

Monoisotopic Mass

1027.40041 Da

IUPAC Name

(2R)-2-{[(2R)-1-[(4R,10R,13R,16R)-19-amino-13-benzyl-10-[2-(C-hydroxycarbonimidoyl)ethyl]-7-[(C-hydroxycarbonimidoyl)methyl]-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid

Traditional Name

(2R)-2-{[(2R)-1-[(4R,10R,13R,16R)-19-amino-13-benzyl-10-[2-(C-hydroxycarbonimidoyl)ethyl]-7-(C-hydroxycarbonimidoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid

CAS Registry Number

Not Available

SMILES

NC1CSSC[C@H](NC(=O)C(CC(O)=N)NC(=O)[C@@H](CCC(O)=N)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@@H](CC2=CC=C(O)C=C2)NC1=O)C(=O)N1CCC[C@@H]1C(=O)N[C@H](CCCNC(N)=N)C(O)=O

InChI Identifier

InChI=1S/C44H61N13O12S2/c45-26-21-70-71-22-32(42(67)57-17-5-9-33(57)41(66)52-28(43(68)69)8-4-16-50-44(48)49)56-40(65)31(20-35(47)60)55-37(62)27(14-15-34(46)59)51-38(63)30(18-23-6-2-1-3-7-23)54-39(64)29(53-36(26)61)19-24-10-12-25(58)13-11-24/h1-3,6-7,10-13,26-33,58H,4-5,8-9,14-22,45H2,(H2,46,59)(H2,47,60)(H,51,63)(H,52,66)(H,53,61)(H,54,64)(H,55,62)(H,56,65)(H,68,69)(H4,48,49,50)/t26?,27-,28-,29-,30-,31?,32+,33-/m1/s1

InChI Key

SXYIOPJBWYQZRQ-VMPYSSHJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Cyclic alpha peptide
Proline or derivatives
N-acyl-alpha amino acid or derivatives
Macrolactam
N-acyl-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acylpyrrolidine
Pyrrolidine-2-carboxamide
Pyrrolidine carboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Fatty acyl
Fatty amide
Benzenoid
Tertiary carboxylic acid amide
Pyrrolidine
Secondary carboxylic acid amide
Lactam
Primary carboxylic acid amide
Guanidine
Carboxamide group
Amino acid
Amino acid or derivatives
Organic disulfide
Carboxylic acid
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Monocarboxylic acid or derivatives
Organopnictogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary aliphatic amine
Carbonyl group
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.7	ALOGPS
logP	-10	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	-1.3	ChemAxon
pKa (Strongest Basic)	12.79	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	16	ChemAxon
Polar Surface Area	428.52 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	290.13 m³·mol⁻¹	ChemAxon
Polarizability	102.37 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0012895

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029201

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481539

PDB ID

Not Available

ChEBI ID

89492

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Arginine vasopressin 1-8 (NP0339113)

MOL for NP0339113 (Arginine vasopressin 1-8)

3D MOL for NP0339113 (Arginine vasopressin 1-8)

3D SDF for NP0339113 (Arginine vasopressin 1-8)

3D-SDF for NP0339113 (Arginine vasopressin 1-8)

PDB for NP0339113 (Arginine vasopressin 1-8)

3D PDB for NP0339113 (Arginine vasopressin 1-8)

SMILES for NP0339113 (Arginine vasopressin 1-8)

INCHI for NP0339113 (Arginine vasopressin 1-8)

Structure for NP0339113 (Arginine vasopressin 1-8)

3D Structure for NP0339113 (Arginine vasopressin 1-8)