(4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1,2-dicarbamoylethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}pentyl]carbamoyl}-3-carboxypropyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-2-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-carboxypropyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-2-carbamoylethyl]carbamoyl}-3-carboxypropyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-carboxypropyl]carbamoyl}-3-carboxypropyl]carbamoyl}-4-(2-aminoacetamido)butanoic acid

• ChemBase ID: 155607
• Molecular Formular: C83H138N26O34
• Molecular Mass: 2044.13762
• Monoisotopic Mass: 2042.98687563
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(=O)N)C(=O)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)CN
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)CC(=O)N)CO)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CN)CCC(=O)O)CCC(=O)O)CCC(=O)O)CC(C)C)CCC(=O)N)CCC(=O)O)CC(=O)N)CCC(=O)N)CCC(=O)O)CC(C)C)CCCNC(=N)N)CCC(=O)O
• InChI: InChI=1S/C83H138N26O34/c1-7-39(6)66(82(143)103-41(12-10-30-93-83(91)92)68(129)96-45(16-24-61(118)119)73(134)95-40(11-8-9-29-84)69(130)108-54(36-110)81(142)104-50(67(90)128)33-57(88)113)109-80(141)52(32-38(4)5)106-76(137)48(19-27-64(124)125)98-72(133)44(14-22-56(87)112)102-79(140)53(34-58(89)114)107-77(138)49(20-28-65(126)127)99-71(132)43(13-21-55(86)111)101-78(139)51(31-37(2)3)105-75(136)47(18-26-63(122)123)100-74(135)46(17-25-62(120)121)97-70(131)42(15-23-60(116)117)94-59(115)35-85/h37-54,66,110H,7-36,84-85H2,1-6H3,(H2,86,111)(H2,87,112)(H2,88,113)(H2,89,114)(H2,90,128)(H,94,115)(H,95,134)(H,96,129)(H,97,131)(H,98,133)(H,99,132)(H,100,135)(H,101,139)(H,102,140)(H,103,143)(H,104,142)(H,105,136)(H,106,137)(H,107,138)(H,108,130)(H,109,141)(H,116,117)(H,118,119)(H,120,121)(H,122,123)(H,124,125)(H,126,127)(H4,91,92,93)/t39-,40-,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,66-/m0/s1
• InChIKey: YFBZGQOQRLPNSP-ASYOLOJGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1,2-dicarbamoylethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}pentyl]carbamoyl}-3-carboxypropyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-2-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-carboxypropyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-2-carbamoylethyl]carbamoyl}-3-carboxypropyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-carboxypropyl]carbamoyl}-3-carboxypropyl]carbamoyl}-4-(2-aminoacetamido)butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1,2-dicarbamoylethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}pentyl]carbamoyl}-3-carboxypropyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-2-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-carboxypropyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-2-carbamoylethyl]carbamoyl}-3-carboxypropyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-3-methylbutyl]carbamoyl}-3-carboxypropyl]carbamoyl}-3-carboxypropyl]carbamoyl}-4-(2-aminoacetamido)butanoic acid
• Synonyms: [Glu3,4,7,10,14]-Conantokin G

Database IDs

• MDL Number: MFCD00236929
• PubChem SID: 162249745
• PubChem CID: 71312169

CALCULATED PROPERTIES

• Acid pKa: 2.8206725
• H Acceptors: 39
• H Donor: 33
• LogD (pH = 5.5): -26.437002
• LogD (pH = 7.4): -33.01686
• Log P: -20.525099
• Molar Refractivity: 493.4923 cm^3
• Polarizability: 190.19844 Å^3
• Polar Surface Area: 1039.02 Å^2
• Rotatable Bonds: 76
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: >90% (HPLC)
• Empirical Formula (Hill Notation): C83H138N26O34

DETAILS

Sigma Aldrich - C1733

Amino Acid Sequence
Gly-Glu-Glu-Glu-Leu-Gln-Glu-Asn-Gln-Glu-Leu-Ile-Arg-Glu-Lys-Ser-Asn
Biochem/physiol Actions
Highly conserved polypeptide NMDA glutamate receptor antagonist; acts through a potent noncompetitive inhibition of polyamine responses; approximately 7-fold more potent than spermine