Basic information

CPKB ID	CP00047
IUPAC Name	(4S,7S,13S)-13-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-7-benzyl-3,3,14,14-tetramethyl-6,9,12-trioxo-1,2-dithia-5,8,11-triazacyclotetradecane-4-carboxylic acid
Synonyms	(4S,7S,13S)-13-((S)-2-Amino-3-(4-Hydroxyphenyl)Propanamido)-7-Benzyl-3,3,14,14-Tetramethyl-6,9,12-Trioxo-1,2-Dithia-5,8,11-Triazacyclotetradecane-4-Carboxylic-Acid (4S,7S,13S)-13-[(2S)-2-Amino-3-(4-Hydroxyphenyl)Propanamido]-7-Benzyl-3,3,14,14-Tetramethyl-6,9,12-Trioxo-1,2-Dithia-5,8,11-Triazacyclotetradecane-4-Carboxylic-Acid (4S,7S,13S)-13-[[(2S)-2-Amino-3-(4-Hydroxyphenyl)Propanoyl]Amino]-3,3,14,14-Tetramethyl-6,9,12-Trioxo-7-(Phenylmethyl)-1,2-Dithia-5,8,11-Triazacyclotetradecane-4-Carboxylic-Acid (4S,7S,13S)-13-[[(2S)-2-Amino-3-(4-Hydroxyphenyl)Propanoyl]Amino]-7-Benzyl-3,3,14,14-Tetramethyl-6,9,12-Trioxo-1,2-Dithia-5,8,11-Triazacyclotetradecane-4-Carboxylic-Acid (4S,7S,13S)-7-Benzyl-3,3,14,14-Tetramethyl-6,9,12-Trioxo-13-(L-Tyrosylamino)-1,2-Dithia-5,8,11-Triazacyclotetradecane-4-Carboxylic-Acid (D-Pen(2),D-Pen(5))Enkephalin (D-Pen2,D-Pen5)-Enkephalin [2-D-Penicillamine,-5-D-Penicillamine]Enkephalin [3H]Dpdpe [D-Pen(2)-D-Pen(5)]-Enkephaline [D-Pen2,-D-Pen5]Enkephalin [D-Pen2,5]Enkephalin [D-Pen2,5]-Enkephalin-Hydrate,->=95%-(Hplc) [D-Pen2,D-Pen5]Enkephalin [D-Pen2-D-Pen5]-Enkephaline 1,2-Dithia-5,8,11-Triazacyclotetradecane,-Cyclic-Peptide-Deriv. 1,2-Dithia-5,8,11-Triazacyclotetradecane-4-Carboxylic-Acid,-13-[[(2S)-2-Amino-3-(4-Hydroxyphenyl)-1-Oxopropyl]Amino]-3,3,14,14-Tetramethyl-6,9,12-Trioxo-7-(Phenylmethyl)-,-(4S,7S,13S)- 2,5-Pen-Enkephalin 88373-73-3 Bdbm21008 Bis-Pen-Enkephalin Bis-Penicillamine-Enkephalin C[D-Pen(2,5)]-Enkephalin C20164 Chebi:73356 Chembl31421 Cyclic-[D-Pen2,-D-Pen5]Enkephalin Cyclic-Dpdpe Cyclic(D-Penicillamine2,5)Enkephalin Cyclo-[D-Pen(2,5)]-Enkephalin Cyclo-[D-Pen2,5]-Enkephalin Db08861 Dpdpe Dpdpe(Sh)2 Dpdpe-Cl Dpdpe-Oh D-Penicillamine-(2,5)-Enkephalin Dplpe Dtxsid201008102 D-Valine,-L-Tyrosyl-3-Mercapto-D-Valylglycyl-L-Phenylalanyl-3--Mercapto-,-Cyclic-(2-5)-Disulfide D-Valine,-L-Tyrosyl-3-Mercapto-D-Valylglycyl-L-Phenylalanyl-3-Mercapto-,-Cyclic-(2>5)-Disulfide-(9Ci) D-Valine,-L-Tyrosyl-3-Mercapto-D-Valylglycyl-L-Phenylalanyl-3-Mercapto-,-Cyclic-(2-5)-Disulfide D-Valine,-L-Tyrosyl-3-Mercapto-D-Valylglycyl-L-Phenylalanyl-3-Mercapto-,-Cyclic-(2?5)-Disulfide Enkephalin,-[Tyrosyl-2,6-3H(N)]--(2-D-Penicillamine,-5-D-Penicillamine) Enkephalin,-D-Penicillamine-(2,5)- Enkephalin,-Penicillamine(2,5)- Gtpl1608 H-Tyr-C(D-Pen-Gly-Phe-D-Pen)-Oh H-Tyr-Cyclo-(D-Pen-Gly-Phe-D-Pen)-Oh H-Tyr-D-Pen-Gly-Phe-D-Pen-Oh L-Tyrosyl-3-Mercapto-D-Valylglycyl-L-Phenylalanyl-3-Mercapto-D-Valine,-Cyclic-(2-5)-Disulfide Ly-198572 Pen(2),Pen(5)-Enkephalin Q27077106 Schembl727022 Tyr-D-Pen-Gly-Phe-D-Pen-[Disulfide-Bridge:-2-5] Zinc29206920
Source	Synthetic construct [Division : Synthetic] Wikipedia: Synthetic construct DrugBank
Family	Opioids DrugBank
Function	Anti-Nociceptive PubChem
Information	DPDPE is a heterodetic cyclic peptide that is a cyclic enkephalin analogue, having D-penicillaminyl residues located at positions 2 and 5, which form the heterocycle via a disulfide bond. It has a role as a delta-opioid receptor agonist. A heterodetic cyclic peptide that is a cyclic enkephalin analogue, having D-penicillaminyl residues located at positions 2 and 5, which form the heterocycle via a disulfide bond. A disulfide opioid pentapeptide that selectively binds to the DELTA OPIOID RECEPTOR. It possesses antinociceptive activity. PubChem\|104787 DrugBank\|DB08861

Legend

Structure

Molecular Formula	C30H39N5O7S2
Molecular Weight	645.2290906 g/mol
SMILES RUN SEA Predictions	CC1(C)SSC(C)(C)[C@@H](NC(=O)[C@@H](N)Cc2ccc(O)cc2)C(=O)NCC(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@H]1C(=O)O PubChem\|104787
InChI	InChI=1S/C30H39N5O7S2/c1-29(2)23(34-25(38)20(31)14-18-10-12-19(36)13-11-18)27(40)32-16-22(37)33-21(15-17-8-6-5-7-9-17)26(39)35-24(28(41)42)30(3,4)44-43-29/h5-13,20-21,23-24,36H,14-16,31H2,1-4H3,(H,32,40)(H,33,37)(H,34,38)(H,35,39)(H,41,42)/t20-,21-,23-,24-/m0/s1
InChIKey	MCMMCRYPQBNCPH-DXLHAZHMNA-N

2D Structure PubChem\|104787
3D Structure PubChem\|104787

Sequence

IUPAC Condensed	H-Tyr-D-Pen(1)-Gly-Phe-D-Pen(1)-OH PubChem\|104787
Amino acid chain	H-Tyr--D-Pen(1)--Gly--Phe--D-Pen(1)--OH CyclicPepedia\|PP
Graph representation	H-Tyr,D-Pen,Gly,Phe,D-Pen,OH @1,4 CyclicPepedia\|PP
One letter code from Structure	YCGFC CyclicPepedia\|Struct2seq
Amino acid chain from Structure	Tyr--Pen(1)--Gly--Phe--Pen(1) CyclicPepedia\|Struct2seq
Description of the conversion sequence	The one letter code and Amino acid chain derived from the structural transformation may be inconsistent, with the Amino acid chain containing Essential Amino acid and the one letter code not.
svg Image PubChem\|104787

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + PP

Structure Properties

Property Name	Property Value
Exact Mass	645.2290906
Number of Rings	3.0
Complexity	0.931818182
XlogP3 AA	1.1121
Heavy Atom Count	44.0
Hydrogen Bond Donor Count	7.0
Hydrogen Bond Acceptor Count	9.0
Rotatable Bond Count	7.0

Property Name	Property Value
Formal Charge	0.0
Refractivity	169.7098
Rule_of_Five	0.0
Number of Atoms	44.0
Topological Polar Surface Area	199.95
Refractivity	169.7098
Veber Rule	0.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	01000110100000101110110011110000110101100111100000001010100101110110001110111111111110000100110000010101000001001011011000110010010001001000100000000110000010010100001100110110111110001110000100100100111001001000000100000001010000000101010110001110010100011111010111101010000101001001100000000010000000011010100111010000010100000011111010110110001000000010011000001101000000000010001000101010010100001100000100001100000010110010111010010011110000100010100000010110111000010000000100001010001000000101100100101111110001010110110110001001100010101101100000010110101000101100010010000011000010111000101000110000101010011000100000001111100100111100000111010101001001001110001010000001010101001000011100010001101101101000000011000010001001001100100010110010001110101011001110011000001001000101001010111000001010001011101000001101111110110000011011111101011000110011111100010001010100000111001010001001101101101010101010010110011101110110010001011111101000001011111100111010011000010111001000000001110100000001010000101101001111110010110110001001100100001010000100001110111101100001100001001001110110000011001101001010000011101001110010001001110010000110101001111010101010100100100111001001010011101010011011000000110001011101110011100100011100110111011010010001101111001110000000100000100101111000110000011101011010100001000001110111111001000011111011010000011110010011010000010000100101011000001101000101100001001110100011010101101011001000010001111000000111101011100100001110010001100001010000111001101011010001110100100111010011100000001000010100010010100100110001100000100111100101001001011110000010000001001011000001001000100101010000000010110001110010010000001001001111000100100110000100000010010001011010100000100101000001010110111100100010000011011001110101000010010111101110001000110001010011000011010010101101101100000000010010011110100111110011000101101001110000000011000000100000001101001110000100111111000111010010010101001010010111110110100011011001011001001000000011000101100111010101011100010010011000000111101100001100000100101000111011
Morgan Fingerprint	0100000000100000000000000000000001001000001000000000000000000000100000000000000110000000001000000100000000000000000100000000010010000000000000000001000000000000000000000000000100000000000000000000000000000000000000000000000000000000000000000000000010100000000000000000000000000000000000000100000000000100000000100010000000000000000000000000000000000000000010000000000000000000000000000001010000000000000000010000000000000000000000001001000010000000000000000010000000000000000000000000000000000000000000010000000000000000000000000000000000000000000000010000000000000000000001010010000000000000000000000000000000000010000000000000000000000000000100010010000000000000010000000001000000001000000000000000000000000000000000000000001000100000000000000100000000100000000000000000000000000000001000000000000000000001000010000000000001000000010000000010000001001000010000000000000000000000000000000000010100000000000000000000000000000010000000000010010000000000001001000000001000000000000000010000000000000000000000000000000001010000
MACCS Keys	00000000000000100000000000000000000010000000000000000010000000000011000000100001011010001011100100001100100000111100010011011101100111001101111101100111111111111111110

Sequence Properties

Property Name	Property Value
Boman Index	-1.268
Instability	8.0
Charge	-0.126815546676281

Binding Target

Other evidence

Property Name	Property ID
TTD	D0G4NM
DrugMAP	DMIRSNA

Manufacturers

Manufacturers Name	Value
CreativePeptides	Dpdpe
Bayer healthcare pharmaceuticals	Dpdpe
Upsher smith laboratories	Dpdpe
Merck	Dpdpe

Manufacturers Name	Value
Apotex	Dpdpe
Baxter Healthcare Corp	Dpdpe
Pharmasources	Dpdpe
Novartis	Dpdpe
AstraZeneca	Dpdpe

Forecasting tools

Forecasting tools	Value
Structure to Sequence	CC1(C)SSC(C)(C)[C@@H](NC(=O)[C@@H](N)Cc2ccc(O)cc2)C(=O)NCC(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@H]1C(=O)O
Structure Properties	CC1(C)SSC(C)(C)[C@@H](NC(=O)[C@@H](N)Cc2ccc(O)cc2)C(=O)NCC(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@H]1C(=O)O
Sequence to Structure	YCGFC
Sequence Properties	YCGFC
Expasy ProtParam Tool	YCGFC
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	MCMMCRYPQBNCPH-DXLHAZHMNA-N
pubchem	104787
Drugbank	DB08861
DRAMP3	Dpdpe
Uniprot	Dpdpe
Cybase	Dpdpe
CONOSERVER	Dpdpe
BindingDB	BDBM21008
CHEMBL	CHEMBL31421
CTD	D020881
Wikipedia	DPDPE
KEGG Compound/Drug	C20164
CHEBI	CHEBI:73356
EPA DSSTox	DTXSID201008102
FDA Global Substance Registration System (GSRS)	Dpdpe
DTP/NCI	Dpdpe
Chemspider	94592

Reference

Pubmed_ID	Title	DOI	Journal
6184702	A fragment of substance P with specific central activity: SP(1-7)	10.1016/0196-9781(82)90027-4.	Peptides
A fragment of substance P with specific central activity: SP(1-7) Abstract Amino-terminal fragments of substance P (SP), SP(1-7) and SP(1-8), were found to produce naloxone-reversible antinociception in the mouse similar to that produced by SP. Similar to SP, these peptides produce antinociception only within a narrow dose range. They have no activity on smooth muscle or blood pressure. These results suggest that contrary to peripheral effects of SP, which are mediated by receptors which recognize the carboxy-terminal part of the SP molecule, certain central actions of SP are mediated by receptors which recognize the amino-terminal part of the SP molecule. SP may be metabolized to this active fragment prior to its action at these receptors.
950660	Biological activity of C-terminal partial sequences of substance P	10.1021/jm00228a028.	J Med Chem
Biological activity of C-terminal partial sequences of substance P Abstract Substance P (Arg-Pro-Lys-Pro-Gln-Gln-Phe-Phe-Gly-Leu-Met-NH2) and the C-terminal partial sequences down to the tripeptide were synthesized by a solid-phase method. These peptides were assayed for vasodilator, spasmogenic, and venoconstrictor properties using three preparations, viz. the hind limb blood flow of the dog, isolated guinea pig ileum, and the isolated rabbit ear vein. The tripeptide and tetrapeptide possessed weak vasodilator properties only but no activity was detected on the other less sensitive preparations. The pentapeptide produced appreciable spasmogenic and vasoactive effects. Sequences of six or more C-terminal amino acids were able to elicity activity at comparable doses to that of the parent endecapeptide; however, the activity did not increase regularly with the chain length. In each assay preparation the octapeptide was the most potent peptide. It was twice as potent as substance P on a molar basis in the guinea pig ileum but the enhancement of activity beyond that of substance P was less pronounced in the vascular preparations.