NP-MRD: Showing NP-Card for Oxytocin 1-8 (NP0339159)

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Record Information

Version

2.0

Created at

2024-09-11 19:58:26 UTC

Updated at

2024-09-11 19:58:27 UTC

NP-MRD ID

NP0339159

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oxytocin 1-8

Description

Oxytocin 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. Also known as alpha-hypophamine (α-hypophamine), oxytocin has the distinction of being the very first polypeptide hormone to be sequenced and synthesized biochemically by Vincent du Vigneaud et al. In 1953. Oxytocin (sold as Pitocin, Syntocinon) is a mammalian hormone that acts primarily as a neurotransmitter in the brain. Oxytocin 1-8 is the fraction of Oxytocin which contains only Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu amino acid peptide. Oxytocin 1-8 is a very strong basic compound (based on its pKa). Recent studies have begun to investigate oxytocin's role in various behaviors, including orgasm, social recognition, pair bonding, anxiety, trust, love, and maternal behaviors. 1) It is released in large amounts after distension of the cervix and vagina during labor, and. 2) After stimulation of the nipples, facilitating birth and breastfeeding, respectively.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303102016492D          

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M  END


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M  END
> <DATABASE_ID>
NP0339159

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C40H60N10O12S2/c1-5-20(4)31-37(58)44-23(12-13-29(41)52)33(54)45-25(17-30(42)53)34(55)48-27(39(60)50-14-6-7-28(50)36(57)47-26(40(61)62)15-19(2)3)18-63-64-32(43)38(59)46-24(35(56)49-31)16-21-8-10-22(51)11-9-21/h8-11,19-20,23-28,31-32,51H,5-7,12-18,43H2,1-4H3,(H2,41,52)(H2,42,53)(H,44,58)(H,45,54)(H,46,59)(H,47,57)(H,48,55)(H,49,56)(H,61,62)/t20-,23+,24+,25?,26-,27-,28-,31+,32?/m1/s1

> <INCHI_KEY>
XGKIWGGRSRCBRX-YOKTWZFESA-N

> <FORMULA>
C40H60N10O12S2

> <MOLECULAR_WEIGHT>
937.094

> <EXACT_MASS>
936.383358814

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
124

> <JCHEM_AVERAGE_POLARIZABILITY>
93.6529433185486

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-{[(2R)-1-[(4S,10S,13S,16S)-19-amino-13-[(2R)-butan-2-yl]-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-pentaazacyclononadecane-4-carbonyl]pyrrolidin-2-yl]formamido}-4-methylpentanoic acid

> <ALOGPS_LOGP>
-1.82

> <JCHEM_LOGP>
-8.255460948771434

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
-0.48836816062588717

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.329552863319405

> <JCHEM_PKA_STRONGEST_BASIC>
12.79237282625857

> <JCHEM_POLAR_SURFACE_AREA>
366.61999999999995

> <JCHEM_REFRACTIVITY>
254.35370000000023

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-{[(2R)-1-[(4S,10S,13S,16S)-19-amino-13-[(2R)-butan-2-yl]-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-pentaazacyclononadecane-4-carbonyl]pyrrolidin-2-yl]formamido}-4-methylpentanoic 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      12.274 -35.652   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      34.814 -31.405   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      36.173 -29.110   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.853 -37.337   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.649 -34.957   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.524 -27.152   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.027 -27.489   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.767 -27.573   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.435 -27.573   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.767 -26.033   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.435 -26.033   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.802 -39.172   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.043 -40.084   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.739 -28.477   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      33.505 -29.081   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.101 -29.883   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.286 -36.945   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.255 -30.221   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      34.831 -29.865   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.938 -35.799   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.101 -28.343   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.101 -25.263   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.971 -37.641   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.435 -30.653   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      24.097 -35.966   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      32.163 -29.836   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      24.951 -31.595   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      28.171 -29.022   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.873 -41.615   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      25.032 -38.464   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.312 -35.104   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      20.228 -28.321   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      21.509 -37.557   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      24.867 -34.632   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.894 -32.095   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      29.496 -29.806   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      17.224 -36.345   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      18.725 -28.657   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      26.421 -31.135   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      32.146 -31.376   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0      19.463 -42.233   0.000  0.00  0.00           N+0
HETATM   42  N   UNK     0      23.590 -39.004   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      20.143 -26.783   0.000  0.00  0.00           N+0
HETATM   44  N   UNK     0      18.489 -37.222   0.000  0.00  0.00           N+0
HETATM   45  N   UNK     0      22.936 -36.977   0.000  0.00  0.00           N+0
HETATM   46  N   UNK     0      17.414 -29.464   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      30.838 -29.051   0.000  0.00  0.00           N+0
HETATM   48  N   UNK     0      25.162 -33.120   0.000  0.00  0.00           N+0
HETATM   49  N   UNK     0      15.852 -33.634   0.000  0.00  0.00           N+0
HETATM   50  N   UNK     0      26.757 -29.633   0.000  0.00  0.00           N+0
HETATM   51  O   UNK     0      15.101 -23.723   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      22.114 -42.527   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      26.221 -39.443   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      21.846 -39.059   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      26.309 -35.172   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      14.383 -31.799   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      29.479 -31.346   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      16.150 -37.449   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      18.146 -27.230   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      27.554 -32.178   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      30.804 -32.131   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      33.471 -32.160   0.000  0.00  0.00           O+0
HETATM   63  S   UNK     0      23.152 -29.147   0.000  0.00  0.00           S+0
HETATM   64  S   UNK     0      21.759 -28.490   0.000  0.00  0.00           S+0
CONECT    1    5                                                            
CONECT    2   19                                                            
CONECT    3   19                                                            
CONECT    4   20                                                            
CONECT    5    1   20                                                       
CONECT    6   14    7                                                       
CONECT    7    6   28                                                       
CONECT    8   21   10                                                       
CONECT    9   11   21                                                       
CONECT   10    8   22                                                       
CONECT   11    9   22                                                       
CONECT   12   23   13                                                       
CONECT   13   12   29                                                       
CONECT   14    6   50                                                       
CONECT   15   26   19                                                       
CONECT   16   24   21                                                       
CONECT   17   25   30                                                       
CONECT   18   27   63                                                       
CONECT   19    2    3   15                                                  
CONECT   20    4    5   31                                                  
CONECT   21    8    9   16                                                  
CONECT   22   10   11   51                                                  
CONECT   23   12   44   33                                                  
CONECT   24   16   46   35                                                  
CONECT   25   17   45   34                                                  
CONECT   26   15   47   40                                                  
CONECT   27   18   48   39                                                  
CONECT   28    7   50   36                                                  
CONECT   29   13   41   52                                                  
CONECT   30   17   42   53                                                  
CONECT   31   20   37   49                                                  
CONECT   32   64   43   38                                                  
CONECT   33   23   54   45                                                  
CONECT   34   25   55   48                                                  
CONECT   35   24   56   49                                                  
CONECT   36   28   57   47                                                  
CONECT   37   31   58   44                                                  
CONECT   38   32   59   46                                                  
CONECT   39   27   60   50                                                  
CONECT   40   26   61   62                                                  
CONECT   41   29                                                            
CONECT   42   30                                                            
CONECT   43   32                                                            
CONECT   44   23   37                                                       
CONECT   45   25   33                                                       
CONECT   46   24   38                                                       
CONECT   47   26   36                                                       
CONECT   48   27   34                                                       
CONECT   49   31   35                                                       
CONECT   50   14   28   39                                                  
CONECT   51   22                                                            
CONECT   52   29                                                            
CONECT   53   30                                                            
CONECT   54   33                                                            
CONECT   55   34                                                            
CONECT   56   35                                                            
CONECT   57   36                                                            
CONECT   58   37                                                            
CONECT   59   38                                                            
CONECT   60   39                                                            
CONECT   61   40                                                            
CONECT   62   40                                                            
CONECT   63   18   64                                                       
CONECT   64   32   63                                                       
MASTER        0    0    0    0    0    0    0    0   64    0  132    0
END

View in JSmol

Synonyms

Value	Source
Cys-tyr-ile-GLN-asn-cys-pro-leu	HMDB
(2R)-2-({[(2R)-1-[(4S,10S,13S,16S)-19-amino-13-[(2R)-butan-2-yl]-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-pentaazacyclononadeca-5,8,11,14,17-pentaene-4-carbonyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-4-methylpentanoate	Generator

Chemical Formula

C₄₀H₆₀N₁₀O₁₂S₂

Average Mass

937.0940 Da

Monoisotopic Mass

936.38336 Da

IUPAC Name

(2R)-2-{[(2R)-1-[(4S,10S,13S,16S)-19-amino-13-[(2R)-butan-2-yl]-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-pentaazacyclononadecane-4-carbonyl]pyrrolidin-2-yl]formamido}-4-methylpentanoic acid

Traditional Name

(2R)-2-{[(2R)-1-[(4S,10S,13S,16S)-19-amino-13-[(2R)-butan-2-yl]-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-pentaazacyclononadecane-4-carbonyl]pyrrolidin-2-yl]formamido}-4-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C40H60N10O12S2/c1-5-20(4)31-37(58)44-23(12-13-29(41)52)33(54)45-25(17-30(42)53)34(55)48-27(39(60)50-14-6-7-28(50)36(57)47-26(40(61)62)15-19(2)3)18-63-64-32(43)38(59)46-24(35(56)49-31)16-21-8-10-22(51)11-9-21/h8-11,19-20,23-28,31-32,51H,5-7,12-18,43H2,1-4H3,(H2,41,52)(H2,42,53)(H,44,58)(H,45,54)(H,46,59)(H,47,57)(H,48,55)(H,49,56)(H,61,62)/t20-,23+,24+,25?,26-,27-,28-,31+,32?/m1/s1

InChI Key

XGKIWGGRSRCBRX-YOKTWZFESA-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
Leucine or derivatives
Macrolactam
Proline or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Primary carboxylic acid amide
Secondary carboxylic acid amide
Organic disulfide
Carboxamide group
Lactam
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Organooxygen compound
Organic oxide
Organic oxygen compound
Organopnictogen compound
Primary aliphatic amine
Hydrocarbon derivative
Carbonyl group
Organic nitrogen 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	-1.8	ALOGPS
logP	-8.3	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	-1.3	ChemAxon
pKa (Strongest Basic)	12.79	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	366.62 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	254.35 m³·mol⁻¹	ChemAxon
Polarizability	93.65 Å³	ChemAxon
Number of Rings	3	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

HMDB0013033

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029259

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

53481590

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Oxytocin 1-8 (NP0339159)

MOL for NP0339159 (Oxytocin 1-8)

3D MOL for NP0339159 (Oxytocin 1-8)

3D SDF for NP0339159 (Oxytocin 1-8)

3D-SDF for NP0339159 (Oxytocin 1-8)

PDB for NP0339159 (Oxytocin 1-8)

3D PDB for NP0339159 (Oxytocin 1-8)

SMILES for NP0339159 (Oxytocin 1-8)

INCHI for NP0339159 (Oxytocin 1-8)

Structure for NP0339159 (Oxytocin 1-8)

3D Structure for NP0339159 (Oxytocin 1-8)