2-[(4S,12S,13R,14S,19R,21S)-9-nitro-7,8-dioxo-15-oxa-1,11-diazahexacyclo[16.3.1.04,12.04,21.05,10.013,19]docosa-5,9,17-trien-14-yl]acetic acid

• ChemBase ID: 126308
• Molecular Formular: C21H21N3O7
• Molecular Mass: 427.40734
• Monoisotopic Mass: 427.13795003
• SMILES: [O-][N+](=O)C1=C2C(=CC(=O)C1=O)[C@]13[C@@H](N2)[C@H]2[C@@H]4C(=CCO[C@H]2CC(=O)O)CN(CC1)[C@H]3C4
• Canonical SMILES: OC(=O)C[C@@H]1OCC=C2[C@H]3[C@@H]1[C@@H]1NC4=C([N+](=O)[O-])C(=O)C(=O)C=C4[C@@]41[C@H](C3)N(C2)CC4
• InChI: InChI=1S/C21H21N3O7/c25-12-6-11-17(18(19(12)28)24(29)30)22-20-16-10-5-14-21(11,20)2-3-23(14)8-9(10)1-4-31-13(16)7-15(26)27/h1,6,10,13-14,16,20,22H,2-5,7-8H2,(H,26,27)/t10-,13-,14-,16-,20-,21+/m0/s1
• InChIKey: IVEMPCACOMNRGI-OFDJEBHLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4S,12S,13R,14S,19R,21S)-9-nitro-7,8-dioxo-15-oxa-1,11-diazahexacyclo[16.3.1.0^4,^1^2.0^4,^2^1.0^5,^1^0.0^1^3,^1^9]docosa-5,9,17-trien-14-yl]acetic acid
• IUPAC Traditional name: cacotheline
• Synonyms: 2,3-Dihydro-4-nitro-2,3-dioxo-9,10-secostrychnidin-10-oic acid; Cacotheline

Database IDs

• CAS Number: 561-20-6
• PubChem SID: 162220647
• PubChem CID: 68413; 6841
• Chemspider ID: 61696
• Wikipedia Title: Cacotheline

CALCULATED PROPERTIES

• Acid pKa: 3.6146743
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -3.4338396
• LogD (pH = 7.4): -3.4438207
• Log P: -3.4310694
• Molar Refractivity: 108.1524 cm^3
• Polarizability: 40.42091 Å^3
• Polar Surface Area: 141.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Yellow crystals
• Flash Point: 374.6 °C
• Density: 1.62 g/cm^3

Product Information

• Classification: Derivatives & analogs of Natural Compounds