3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.13,6.18,11.113,16]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid

• ChemBase ID: 105879
• Molecular Formular: C34H34N4O4
• Molecular Mass: 562.65816
• Monoisotopic Mass: 562.25800559
• SMILES: Cc1c2[nH]c(/C=C/3\N=C(/C=c/4\[nH]/c(=C\C5=N/C(=C\2)/C(=C5C)C=C)/c(C=C)c4C)C(=C3CCC(=O)O)C)c1CCC(=O)O
• Canonical SMILES: C=CC1=C(C)C2=N/C/1=C\c1[nH]c(c(c1C)CCC(=O)O)/C=C/1\N=C(/C=c/3\[nH]/c(=C\2)/c(C=C)c3C)C(=C1CCC(=O)O)C
• InChI: InChI=1S/C34H34N4O4/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/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-
• InChIKey: KSFOVUSSGSKXFI-UJJXFSCMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^3,^6.1^8,^1^1.1^1^3,^1^6]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid; 3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid
• IUPAC Traditional name: protoporphyrin
• Synonyms: Kammerer’s porphyrin; Ooporphyrin; Protoporphyrin IX; 3,7,12,17-Tetramethyl-8,13-divinyl-2,18-porphinedipropionic acid; PROTOPORPHYRIN IX; 3,7,12,17-四甲基-8,13-二乙烯基-2,18-卟吩二丙酸; 蛋壳卟啉; 原卟啉 IX

Database IDs

• CAS Number: 553-12-8
• EC Number: 209-033-7
• MDL Number: MFCD00151109
• Beilstein Number: 380795
• PubChem SID: 162092677
• PubChem CID: 4971

CALCULATED PROPERTIES

• Acid pKa: 3.6843598
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 5.603521
• LogD (pH = 7.4): 2.2475965
• Log P: 6.778797
• Molar Refractivity: 163.8112 cm^3
• Polarizability: 67.07024 Å^3
• Polar Surface Area: 131.96 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Fluorescence: λex 387 nm; λem 633 nm in 0.1 M phosphate pH 7.0, 0.5% triton X-100

Safety Information

• Storage Condition: 0°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: >97%; ≥95% (HPLC)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C34H34N4O4

DETAILS

MP Biomedicals - 02194896

Crystalline Purity: >97%

Sigma Aldrich - 82505

Application
Activates soluble guanylyl cyclase.
Other Notes
Photosensitzer in photodynamic cross-linking1,2; An interesting probe for fluoroimmunoassay3