(1R,3S,4R,5R,11S,13R,15S,17R,19Z,21S,22R,24S)-22-(hydroxymethyl)-2,6,12,16,23-pentaoxapentacyclo[13.11.0.0^{3,13}.0^{5,11}.0^{17,24}]hexacosa-8,19,25-triene-4,21-diol

• ChemBase ID: 5354
• Molecular Formular: C22H30O8
• Molecular Mass: 422.4688
• Monoisotopic Mass: 422.19406792
• SMILES: O[C@H]1C=CC[C@H]2O[C@H]3C[C@H]4O[C@H]5CC=CCO[C@@H]5[C@@H](O)[C@@H]4O[C@@H]3C=C[C@@H]2O[C@@H]1CO
• Canonical SMILES: OC[C@H]1O[C@H]2C=C[C@@H]3[C@@H](O[C@@H]2CC=C[C@@H]1O)C[C@@H]1[C@@H](O3)[C@H](O)[C@@H]2[C@@H](O1)CC=CCO2
• InChI: InChI=1S/C22H30O8/c23-11-19-12(24)4-3-6-13-14(28-19)7-8-15-17(27-13)10-18-22(30-15)20(25)21-16(29-18)5-1-2-9-26-21/h1-4,7-8,12-25H,5-6,9-11H2/b4-3-/t12-,13+,14-,15+,16-,17-,18+,19+,20+,21-,22+/m0/s1
• InChIKey: VDRIXSJOPKVWKM-HXGIDPQASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,4R,5R,11S,13R,15S,17R,19Z,21S,22R,24S)-22-(hydroxymethyl)-2,6,12,16,23-pentaoxapentacyclo[13.11.0.0^{3,13}.0^{5,11}.0^{17,24}]hexacosa-8,19,25-triene-4,21-diol
• IUPAC Traditional name: (1R,3S,4R,5R,11S,13R,15S,17R,19Z,21S,22R,24S)-22-(hydroxymethyl)-2,6,12,16,23-pentaoxapentacyclo[13.11.0.0^{3,13}.0^{5,11}.0^{17,24}]hexacosa-8,19,25-triene-4,21-diol
• Synonyms: (4Z)-2,8:7,12:11,15:14,18:17,22-PENTAANHYDRO-4,5,6,9,10,13,19,20,21-NONADEOXY-D-ARABINO-D-ALLO-D-ALLO-DOCOSA-4,9,20-TRIENITOL

Database IDs

• PubChem SID: 99444187; 160968783
• PubChem CID: 45480632

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.96193
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -0.11491643
• LogD (pH = 7.4): -0.1149176
• Log P: -0.114916414
• Molar Refractivity: 107.9218 cm^3
• Polarizability: 42.308453 Å^3
• Polar Surface Area: 106.84 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.36
• LOG S: -2.29
• Solubility (Water): 2.19e+00 g/l

DETAILS

DrugBank - DB07716

Drug information: experimental