Basic information

CPKB ID	CP00275
IUPAC Name	(10S,13S,16S,19S)-16-butan-2-yl-10,11,14-trimethyl-13-propan-2-yl-3-prop-2-enyl-4-oxa-1,8,11,14,17-pentazabicyclo[17.3.0]docosane-2,5,9,12,15,18-hexone
Synonyms	Destruxin-A Nci60_014978 Nsc644210 Nsc-644210
Source	Beauveria felina [Division : Plants and Fungi] Taxonomy :37994 (Fungi-Ascomycota-Hypocreales-Sordariomycetes-Cordycipitaceae Beauveria) Wikipedia: Beauveria felina PubChem
Information	Cyclo[N(Me)Ala-bAla-DL-OGly(allyl)-Pro-xiIle-N(Me)Val] is a natural product found in Beauveria felina with data available. PubChem\|370709

Legend

Structure

Molecular Formula	C29H47N5O7
Molecular Weight	577.3475488 g/mol
SMILES RUN SEA Predictions	C=CC[C@H]1OC(=O)CCNC(=O)[C@H](C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]2CCCN2C1=O PubChem\|370709
InChI	InChI=1S/C29H47N5O7/c1-9-12-21-27(38)34-16-11-13-20(34)26(37)31-23(18(5)10-2)28(39)33(8)24(17(3)4)29(40)32(7)19(6)25(36)30-15-14-22(35)41-21/h9,17-21,23-24H,1,10-16H2,2-8H3,(H,30,36)(H,31,37)/t18?,19-,20-,21?,23-,24-/m0/s1
InChIKey	XIYSEKITPHTMJT-NGTGZQJHNA-N

2D Structure PubChem\|370709
3D Structure PubChem\|370709

Sequence

IUPAC Condensed	cyclo[N(Me)Ala-bAla-DL-OGly(allyl)-Pro-xiIle-N(Me)Val] PubChem\|370709
Amino acid chain	N(Me)Ala(1)--bAla--DL-OGly(allyl)--Pro--xiIle--N(Me)Val(1) CyclicPepedia\|PP
Graph representation	N(Me)Ala,bAla,DL-OGly(allyl),Pro,xiIle,N(Me)Val @0,5 CyclicPepedia\|PP
One letter code from Structure	PIVA CyclicPepedia\|Struct2seq
Amino acid chain from Structure	Ac-Pro(1)--Ile--NMe-Val--NMe-bAla(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\|370709

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + PP

Structure Properties

Property Name	Property Value
Exact Mass	577.3475488
Number of Rings	2.0
Complexity	1.0
XlogP3 AA	0.846
Heavy Atom Count	41.0
Hydrogen Bond Donor Count	2.0
Hydrogen Bond Acceptor Count	7.0
Rotatable Bond Count	5.0

Property Name	Property Value
Formal Charge	0.0
Refractivity	152.0694
Rule_of_Five	0.0
Number of Atoms	41.0
Topological Polar Surface Area	145.43
Refractivity	152.0694
Veber Rule	0.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	01100001000010000100100001111001010001000111110000100010100101010000100111101100100000001010110011000111000101011101001001111000010000100011110000011101100110010100001010110110010111000111100100000100011011001000010101001010000111000100011111000010011101101111000100001000000010001001001100000111011010010110101111000011110100010000001011010000100000100011001001001000001010000000011000110011000101000010000100001100001010001000100100111001101111100000000100000010011110001000010000001010000110010100110000100100110101000000010010010101100100000000100010000100001001010100010111101011010010110100111000100101000010011010000000001101000100101000000011100111010000000110001000100001000101000100011100100000000101100000000100110011001000010101000000010010001100101010001110010000000001111001001010001000001010001000000000111011110001000000110010000110001000101011000000000011000100000000111001011011001100100000111001000111011010111110000001010111100000001000011001010110011000010011001000010001010100000010010000010000001100000011000100010011110000100011010001110000101011100001010000001001110010001001011001010010000000100000000110001001010100000100001001101000101110100110101101010001011000011111100101100011110001000100000110100000011101010010010111000010100100001010001000010000100010100001010001101001010111100001000001101101100010010001110100001001010101110111010000110010100100000010001100000111011001011100000000100001100011000000010010001010001000011011101101000100010011100001000000011011011100000010100100101110000001100000001000010110001000100000010010100000101100100011001001101111100010000001000001000011111000001110111000100110000000010000010000001101000010000100000010010001000001010000011100000100100001000011010111000000100000100011101000010001000011010100101010000000100000010011000010001001111101001100000011010000011010110110010001000100100000000000110010100000010100001001101100101101101101001010010100010101001010000111010111000010010011111010000001000101001001100010110101001000100100010010000011101011100100101110010001010011
Morgan Fingerprint	0100110000100000000100000000000001000010001000000000000000000000000000000000000010000000001000000000000000000100000000100100000000000000000000000000000000000000100000100000000000000000000000000000000000000000000000000001001000000001000000000000000000000100100000000000010000000000000101001000001000000100010000000010000000000001000000010000101000000000000010000000000000100000000000000000000000000000000000000000000000000000000000000000000000000010000000001000000000000000000010000010000000001000000000000001000000000000100000000000000000000000000000001000000000000000000010000001000000000000000001000000000000000000000001000000000000100000000000000010000010000000000001000000000000001000000000100000000000000000001000000000000000000000000000000000001000000000000000000000000000000000100000000000000000000000000000000000000000000000000000000010001000000000000000000000000000100010000000000000000000000000000000000000000000000010000000010000100000000000000000000000000010100000000000000000000000000000000000000000000000010000
MACCS Keys	00000000000000000000000000000000001000000000000000000000010000000000000010110001001101000011110111011000110010110011011011110001110110001110111100111111111111111100110

Sequence Properties

Property Name	Property Value
Boman Index	-2.6925
Instability	-13.725
Charge	-0.00201570060725275
Aliphatic Index	195.0

Manufacturers

Manufacturers Name	Value
CreativePeptides	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
Bayer healthcare pharmaceuticals	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
Upsher smith laboratories	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
Merck	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]

Manufacturers Name	Value
Apotex	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
Baxter Healthcare Corp	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
Pharmasources	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
Novartis	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
AstraZeneca	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]

Forecasting tools

Forecasting tools	Value
Structure to Sequence	C=CC[C@H]1OC(=O)CCNC(=O)[C@H](C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]2CCCN2C1=O
Structure Properties	C=CC[C@H]1OC(=O)CCNC(=O)[C@H](C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]2CCCN2C1=O
Sequence to Structure	PIVA
Sequence Properties	PIVA
Expasy ProtParam Tool	PIVA
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	XIYSEKITPHTMJT-NGTGZQJHNA-N
pubchem	370709
Drugbank	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
DRAMP3	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
Uniprot	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
Cybase	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
CONOSERVER	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
BindingDB	C=CC[C@H]1OC(=O)CCNC(=O)[C@H](C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]2CCCN2C1=O
CHEMBL	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
CTD	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
Wikipedia	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
KEGG Compound/Drug	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
CHEBI	XIYSEKITPHTMJT-NGTGZQJHNA-N
EPA DSSTox	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
FDA Global Substance Registration System (GSRS)	Cyclo[N(Me)Ala-Bala-Dl-Ogly(Allyl)-Pro-Xiile-N(Me)Val]
DTP/NCI
Chemspider	XIYSEKITPHTMJT-NGTGZQJHNA-N

Reference

Pubmed_ID	Title	DOI	Journal
12350163	Hirsutellide A, a new antimycobacterial cyclohexadepsipeptide from the entomopathogenic fungus Hirsutella kobayasii	10.1021/np020055+.	J Nat Prod
Hirsutellide A, a new antimycobacterial cyclohexadepsipeptide from the entomopathogenic fungus Hirsutella kobayasii Abstract A new cyclohexadepsipeptide, named hirsutellide A (1), was isolated from a cell extract of the entomopathogenic fungus Hirsutella kobayasii BCC 1660. The structure of 1 was elucidated by analyses of spectroscopic data, and its absolute stereochemistry was addressed by the use of Marfey's method. Hirsutellide A (1) exhibited antimycobacterial and antimalarial activities, but was inactive toward the Vero cell line (at 50 microg/mL).
18007294	Synthesis of the key precursor of Hirsutellide A	10.3390/10010259.	Molecules
Synthesis of the key precursor of Hirsutellide A Abstract Hexadepsipeptide 2, the precursor of Hirsutellide A (1), was synthesized in an overall yield of 45% from N-Boc-Me-Gly via three coupling reactions using dicyclohexylcarbodiimide (DCC), O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyl- uronium hexafluorophosphate (HATU) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl), respectively.