6-amino-2-(2-{2-[2-(2-{[(21Z,26E)-6-amino-12-(2-carbamoylethyl)-25,29-bis(2-carboxyethyl)-3,9,18,20,24,30,40-heptamethyl-7,10,13-trioxo-4,17-dithia-8,11,14,32,34,38,41-heptaaza-33-ferraheptacyclo[29.7.1.12,37.123,26.019,35.021,34.028,32]hentetraconta-1(39),2(40),19,21,23(41),24,26,28,30,35,37-undecaen-15-yl]formamido}-3-(1H-imidazol-5-yl)propanamido)-3-hydroxybutanamido]-3-methylbutanamido}-4-carboxybutanamido)hexanoic acid amine

• ChemBase ID: 131893
• Molecular Formular: C74H102FeN18O18S2
• Molecular Mass: 1651.68648
• Monoisotopic Mass: 1650.64102801
• SMILES: Cc1c2=CC3=NC(=Cc4c(c(c5n4[Fe]n2c2=CC4=NC(=C5)C(=C4C)C(SCC(C(=O)NC(C(=O)NC(C(=O)NC(CSC(c12)C)C(=O)NC(Cc1cnc[nH]1)C(=O)NC(C(C)O)C(=O)NC(C(C)C)C(=O)NC(CCC(=O)O)C(=O)NC(CCCCN)C(=O)O)CCC(=O)N)C)N)C)C)CCC(=O)O)C(=C3C)CCC(=O)O.N
• Canonical SMILES: NCCCCC(C(=O)O)NC(=O)C(NC(=O)C(C(C)C)NC(=O)C(C(O)C)NC(=O)C(NC(=O)C1CSC(C)c2c(C)c3=CC4=NC(=Cc5n6[Fe]n3c2=CC2=NC(=Cc6c(c5CCC(=O)O)C)C(=C2C)C(C)SCC(C(=O)NC(C(=O)NC(C(=O)N1)CCC(=O)N)C)N)C(=C4C)CCC(=O)O)Cc1[nH]cnc1)CCC(=O)O.N
• InChI: InChI=1S/C74H101N17O18S2.Fe.H3N/c1-32(2)64(72(106)86-46(17-21-61(98)99)68(102)87-47(74(108)109)13-11-12-22-75)90-73(107)65(38(8)92)91-70(104)56(23-41-28-78-31-79-41)88-71(105)57-30-111-40(10)63-35(5)50-24-48-33(3)42(14-19-59(94)95)52(81-48)27-53-43(15-20-60(96)97)34(4)49(82-53)25-54-62(36(6)51(84-54)26-55(63)83-50)39(9)110-29-44(76)67(101)80-37(7)66(100)85-45(69(103)89-57)16-18-58(77)93;;/h24-28,31-32,37-40,44-47,56-57,64-65,92H,11-23,29-30,75-76H2,1-10H3,(H17,77,78,79,80,81,82,83,84,85,86,87,88,89,90,91,93,94,95,96,97,98,99,100,101,102,103,104,105,106,107,108,109);;1H3/q;+2;/p-2/b48-24+,49-25?,50-24-,51-26?,52-27+,53-27-,54-25?,55-26?
• InChIKey: SOIPPMUJPJAVPO-BGZGEIGJSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-amino-2-(2-{2-[2-(2-{[(21Z,26E)-6-amino-12-(2-carbamoylethyl)-25,29-bis(2-carboxyethyl)-3,9,18,20,24,30,40-heptamethyl-7,10,13-trioxo-4,17-dithia-8,11,14,32,34,38,41-heptaaza-33-ferraheptacyclo[29.7.1.1^2,^3^7.1^2^3,^2^6.0^1^9,^3^5.0^2^1,^3^4.0^2^8,^3^2]hentetraconta-1(39),2(40),19,21,23(41),24,26,28,30,35,37-undecaen-15-yl]formamido}-3-(1H-imidazol-5-yl)propanamido)-3-hydroxybutanamido]-3-methylbutanamido}-4-carboxybutanamido)hexanoic acid amine
• IUPAC Traditional name: 6-amino-2-(2-{2-[2-(2-{[(21Z,26E)-6-amino-12-(2-carbamoylethyl)-25,29-bis(2-carboxyethyl)-3,9,18,20,24,30,40-heptamethyl-7,10,13-trioxo-4,17-dithia-8,11,14,32,34,38,41-heptaaza-33-ferraheptacyclo[29.7.1.1^2,^3^7.1^2^3,^2^6.0^1^9,^3^5.0^2^1,^3^4.0^2^8,^3^2]hentetraconta-1(39),2(40),19,21,23(41),24,26,28,30,35,37-undecaen-15-yl]formamido}-3-(3H-imidazol-4-yl)propanamido)-3-hydroxybutanamido]-3-methylbutanamido}-4-carboxybutanamido)hexanoic acid amine
• Synonyms: Microperoxidase (MP-9) ammonium salt from equine heart cytochrome c

Database IDs

• CAS Number: 104872-91-5
• MDL Number: MFCD00131610
• PubChem SID: 162226170; 24897345
• PubChem CID: 71308488

CALCULATED PROPERTIES

• Acid pKa: 2.8730454
• H Acceptors: 23
• H Donor: 17
• LogD (pH = 5.5): -9.85118
• LogD (pH = 7.4): -12.73313
• Log P: -7.458161
• Molar Refractivity: 408.6697 cm^3
• Polarizability: 165.32611 Å^3
• Polar Surface Area: 561.68 Å^2
• Rotatable Bonds: 31
• 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)

DETAILS

Sigma Aldrich - M9635

Application
Of possible interest as a heme tracer in electron microscopic cytochemistry.
Biochem/physiol Actions
Has peroxidase activity.
Other Notes
The proposed structure is the heme portion of cytochrome c with amino acids 14 through 22 still attached.
Preparation Note
Prepared by enzymatic degradation.