Basic information

CPKB ID	CP00514
IUPAC Name	(3S,6R,10R,13E,16S)-10-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-16-[(1S)-1-[(2R,3R)-3-phenyloxiran-2-yl]ethyl]-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone
Synonyms	(3S,6R,10R,13E,16S)-10-[(3-Chloro-4-Methoxyphenyl)Methyl]-6-Methyl-3-(2-Methylpropyl)-16-[(1S)-1-[(2R,3R)-3-Phenyloxiran-2-Yl]Ethyl]-1,4-Dioxa-8,11-Diazacyclohexadec-13-Ene-2,5,9,12-Tetrone .Beta.-Alanine,-N-(3-Chloro-N-(5-((2-Hydroxy-4-Methyl-1-Oxopentyl)Oxy)-1-Oxo-6-(3-Phenyloxiranyl)-2-Heptenyl)-O-Methyl-D-Tyrosyl)-2-Methyl-,-.Xi.-Lactone,-(2R-(2.Alpha.(1(R),2E,5S(S),6S),3.Beta.))- 1,4-Dioxa-8,11-Diazacyclohexadec-13-Ene-2,5,9,12-Tetrone,-10-((3-Chloro-4-Methoxyphenyl)Methyl)-6-Methyl-3-(2-Methylpropyl)-16-(1-(3-Phenyloxiranyl)Ethyl)- 10-((3-Chloro-4-Methoxyphenyl)Methyl)-6-Methyl-3-(2-Methylpropyl)-16-(1-(3-Phenyloxiranyl)Ethyl)-1,4-Dioxa-8,11-Diazacyclohexadec-13-Ene-2,5,9,12-Tetrone 124689-65-2 C16877 Chembl441018 Cryptophycin Cryptophycin-A Cryptophycin-1 Cryptophycin-1-[Mi] Cyclo((2R)-2-Methyl-.Beta.-Alanyl-(2S)-2-Hydroxy-4-Methylpentanoyl-(2E,5S,6S)-5-Hydroxy-6-((2R,3R)-3-Phenyl-2-Oxiranyl)-2-Heptenoyl-3-Chloro-O-Methyl-D-Tyrosyl) Cyclo((2R)-2-Methyl-.Beta.-Alanyl-(2S)-2-Hydroxy-4-Methylpentanoyl-(2E,5S,6S)-5-Hydroxy-6-((2R,3R)-3-Phenyloxiranyl)-2-Heptenoyl-3-Chloro-O-Methyl-D-Tyrosyl) Dtxsid901046187 Q27293933 Schembl1346966 Unii-Xo974V2M5T Xo974V2M5T
Source	Nostoc [Division : Bacteria] Taxonomy :1177 (Unassigned-Cyanobacteriota-Nostocales-Cyanophyceae-Nostocaceae Unassigned) Wikipedia: Nostoc PubChem
Function	Anti-Cancer PubChem
Information	Cryptophycin 1 is a natural product found in Nostoc with data available. Curacomycin is a homodetic cyclic peptide found in several Streptomyces species, consisting of 3-hydroxyasparagine, L-ornithine, L-isoleucine, D-leucine, D-valine and 5-chloro-L-tryptophan joined in sequence in a cyclic arrangement by peptide linkages. It exhibits antibacterial properties. It has a role as a bacterial metabolite and an antibacterial agent. It is a homodetic cyclic peptide and a chloroindole. PubChem\|6438401

Legend

Structure

Molecular Formula	C35H43CLN2O8
Molecular Weight	654.270794 g/mol
SMILES RUN SEA Predictions	COc1ccc(C[C@H]2NC(=O)C=CC[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl PubChem\|6438401
InChI	InChI=1S/C35H43ClN2O8/c1-20(2)16-29-35(42)44-27(22(4)31-32(46-31)24-10-7-6-8-11-24)12-9-13-30(39)38-26(33(40)37-19-21(3)34(41)45-29)18-23-14-15-28(43-5)25(36)17-23/h6-11,13-15,17,20-22,26-27,29,31-32H,12,16,18-19H2,1-5H3,(H,37,40)(H,38,39)/b13-9+/t21-,22+,26-,27+,29+,31-,32-/m1/s1
InChIKey	PSNOPSMXOBPNNV-SEYVRMDENA-N

2D Structure PubChem\|6438401
3D Structure PubChem\|6438401

Sequence

IUPAC Condensed	cyclo[OLeu-Unk-D-Phe(3-Cl,4-OMe)-bAib(R)] PubChem\|6438401
Amino acid chain	OLeu(1)--Unk--D-Phe(3-Cl,4-OMe)--bAib(R)(1) CyclicPepedia\|PP
Graph representation	OLeu,Unk,D-Phe(3-Cl,4-OMe),bAib(R) @0,3 CyclicPepedia\|PP
One letter code from Structure	Y CyclicPepedia\|Struct2seq
Amino acid chain from Structure	NMe-OMe-TyrC 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.

Chemical and Physical Properties

Structure Properties

Property Name	Property Value
Exact Mass	654.270794
Number of Rings	4.0
Complexity	1.0
XlogP3 AA	4.734
Heavy Atom Count	46.0
Hydrogen Bond Donor Count	2.0
Hydrogen Bond Acceptor Count	8.0
Rotatable Bond Count	8.0

Property Name	Property Value
Formal Charge	0.0
Refractivity	172.0044
Rule_of_Five	0.0
Number of Atoms	46.0
Topological Polar Surface Area	132.56
Refractivity	172.0044
Veber Rule	1.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	11100110100010110100110111110001001001111111110010101011100101110111001110111101100110010011110111010101110101001111001101111010001001001011101011001110000011110111101010100110110111001110000110110110011011101000110111000111011001110111000111101101111101101111011110001001100001000001111100000111100111010010100011011101100100111011111111101110001011100001111001101011110000000011001001100011010011100110000100001100001010010000101110011111111110101100001010111111111011011001010000111110001110000110110001001100110000101110110010100111110011101101101110011110001110111111110110101100110110011100111101110101101010111111111100001001101001111110100010001111110001000111101010101001000101001100011011111000100111000010011001010010000011111101110110011010011111010110111110011010001001010010011010111001001110001101100100111111111110110100111011101010010000111001011111011011111100011100001001111001001111101011100101010111011101110111000101111110001011111110010110011010111100001111011001010001110100111000001010111101101111100110110010101001111001101111110011111010111111101101010011011111101110101101011101011010000110111000001011000011100010010101101001111001111111100000100111111001111011011011111101001111010001101101010110100110011011110111011111110011101101110010000100010001111010010001111101111001111011100111000111101111100101101011111010011101000111110101111010110110100101101010111110100101101111011110000101111101100110101010000001111001100101011111101101011110101010110000010101111001101101001010101111110011000100110100000001010010011010110110000011111110100110110100000111111110101000101011000110101001001100100001110011010011100100110110010001000001110101010110110110010100010110011111011010001100001101000111000110111000100100001011011011010100010011010110101010110110100001111111000010001110101001101110101000010010011111110111101011100011100001000110110011010101100001011111011100001100011111110011010100110011101000110111110001010101111010011011011010011111001011101101110110001011001011010110101101000100110101111111111001010011
Morgan Fingerprint	0100000100100100000000000000000001000000000000000000000000000000100000000001000010000010001000100000000010000000000100100000000000000000000000000000000000000000000000000000000100000000000000000000000000000000000000000000000000000000000000000000000001000001000000000000000000000000001101000010000000000100000000100010000000000000000000010000000000000000000010000000001000000000000000000000010000001000000000000000000000000000001000000000000000000000000000000010000000000010000000000000000000000000000000000000000010000000000000000000000000000000000100000000000011000000000000010000000000000000010000100000000000000000000000000000000000000001000000000010000010010000010000000000000000100000000000110000000000000000000000000000001000100000000000000000001000000010000000000000000000000100000010010000000000010000000010000000000100000000010000000110000001000001000000000001000000010000000000000000000001000000000000000000000000000010100000000000010000100010000001000000000000000000100000010000000000000000000100000000000000011100
MACCS Keys	00000000000000001000001000000000000000000000000000000010010000100000000010100001001000010111110101011001100100110101110011010111100110101100111111100111111111111111110

Binding Target

Other evidence

Property Name	Property ID
TTD	D0LI3C
DrugMAP	DM73C4K

Manufacturers

Manufacturers Name	Value
CreativePeptides	Cryptophycin 1
Bayer healthcare pharmaceuticals	Cryptophycin 1
Upsher smith laboratories	Cryptophycin 1
Merck	Cryptophycin 1

Manufacturers Name	Value
Apotex	Cryptophycin 1
Baxter Healthcare Corp	Cryptophycin 1
Pharmasources	Cryptophycin 1
Novartis	Cryptophycin 1
AstraZeneca	Cryptophycin 1

Forecasting tools

Forecasting tools	Value
Structure to Sequence	COc1ccc(C[C@H]2NC(=O)C=CC[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Structure Properties	COc1ccc(C[C@H]2NC(=O)C=CC[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
Expasy ProtParam Tool
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	PSNOPSMXOBPNNV-SEYVRMDENA-N
pubchem	6438401
Drugbank	Cryptophycin 1
DRAMP3	Cryptophycin 1
Uniprot	Cryptophycin 1
Cybase	Cryptophycin 1
CONOSERVER	Cryptophycin 1
BindingDB	COc1ccc(C[C@H]2NC(=O)C=CC[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)[C@H](C)CNC2=O)cc1Cl
CHEMBL	CHEMBL441018
CTD	Cryptophycin 1
Wikipedia	Cryptophycin 1
KEGG Compound/Drug	Cryptophycin 1
CHEBI	PSNOPSMXOBPNNV-SEYVRMDENA-N
EPA DSSTox	DTXSID901046187
FDA Global Substance Registration System (GSRS)	XO974V2M5T
DTP/NCI	Cryptophycin 1
Chemspider	PSNOPSMXOBPNNV-SEYVRMDENA-N

Reference

Pubmed_ID	Title	DOI	Journal
17786911	Numerical characterization of the conformation of cyclic peptides and its application	10.1002/jcc.20744.	J Comput Chem
Numerical characterization of the conformation of cyclic peptides and its application Abstract Many classes of functional cyclic peptide molecules are determined by experimental techniques, but few similarities of cyclic peptides are detectable. We propose three numerical characterizations of conformations of cyclic peptides. By incorporating the information on atomic coordinates of cyclic peptides, the coordinates are transformed into a characteristic sequence. Then we calculate its center of gravity, the eigenvalues of its Euclidean and L/L matrices, and regard them as descriptors to numerically characterize the conformations of cyclic peptides. Finally, the method is tested by analyzing the similarities of cyclic peptides presented in Table 1.
8824953	Estrogen-like activity of cyclic peptides from Vaccaria segetalis extracts	10.1055/s-2006-959373.	Planta Med
Estrogen-like activity of cyclic peptides from Vaccaria segetalis extracts Abstract Methanol and ethyl acetate extracts of Wang Bu Liu Xing (seeds of Vaccaria segetalis, Caryophyllaceae) and cyclic peptides (named segetalins A and B) obtained from the extracts were shown to have an estrogen-like activity.
9113340	Thionation of segetalins A and B, cyclic peptides with estrogen-like activity from seeds of Vaccaria segetalis	10.1016/s0968-0896(97)00001-1.	Bioorg Med Chem
Thionation of segetalins A and B, cyclic peptides with estrogen-like activity from seeds of Vaccaria segetalis Abstract Thionation of estrogen-like active cyclic peptides, segetalins A (1) and B (2), with Lawesson's reagent provided each two thiosegetalins; thiosegetalin A1 Gly-1-psi(CS-NH)-Val-2; Trp-5-psi (CS-NH)-Ala-6segetalin A, thiosegetalin A2 Gly-1-psi(CS-NH)-Val-2; Ala-6-psi(CS-NH)-Gly-1segetalin A, thiosegetalin B1 Gly-1-psi (CS-NH)-Val-2; Ala-3-psi(CS-NH)-Trp-4segetalin B, and thiosegetalin B2 Gly-1-psi(CS-NH)-Val-2; Trp-4-psi(CS-NH)-Ala-1segetalin B. Thiosegetalin A2 only showed estrogen-like activity against ovariectomized rats. On the basis of their conformations analysed by NMR experiments, the backbone conformation was considered to play an important role in estrogen-like activity for segetalins."