(1R)-15,19-bis(2-carboxyethyl)-5,10-diethenyl-4,9,14,20-tetramethyl-2$l^{5},22,23$l^{5},25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)

• ChemBase ID: 2306
• Molecular Formular: C34H32FeN4O4++
• Molecular Mass: 616.48728
• Monoisotopic Mass: 616.17729302
• SMILES: Cc1c(CCC(=O)O)c2=CC3=[N+]4C(=Cc5c(C=C)c(C)c6C=C7C(=C(C)C8=[N+]7[Fe@]4(n2c1=C8)n56)C=C)C(=C3CCC(=O)O)C
• Canonical SMILES: C=Cc1c(C)c2n3c1C=C1C(=C(C4=[N+]1[Fe@@]13[N+]3=C(C(=C(C3=C2)C=C)C)C=c2n1c(=C4)c(c2C)CCC(=O)O)CCC(=O)O)C
• InChI: InChI=1S/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+4/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-
• InChIKey: YHLKGEDAGPGZPN-RGGAHWMASA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-15,19-bis(2-carboxyethyl)-5,10-diethenyl-4,9,14,20-tetramethyl-2$l^{5},22,23$l^{5},25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)
• IUPAC Traditional name: mesoheme
• Synonyms: Mesoheme

Database IDs

• PubChem SID: 160965758; 46508983
• PubChem CID: 4973

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.2814512
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.4171183
• LogD (pH = 7.4): 3.4249468
• Log P: 2.1870515
• Molar Refractivity: 169.7694 cm^3
• Polarizability: 69.02759 Å^3
• Polar Surface Area: 92.22 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.29
• LOG S: -5.63
• Solubility (Water): 1.61e-03 g/l

DETAILS

DrugBank - DB02577

• Drug Groups: experimental
• Description: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins. [PubChem]