(1R,2R)-2-[(2S,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid

• ChemBase ID: 153918
• Molecular Formular: C28H43NO6
• Molecular Mass: 489.64412
• Monoisotopic Mass: 489.3090381
• SMILES: C[C@H]1C[C@H](C[C@@H]([C@H](/C(=C\C=C\C[C@H](OC(=O)C[C@@H]([C@H](C1)C)O)[C@@H]1CCC[C@H]1C(=O)O)/C#N)O)C)C
• Canonical SMILES: N#C/C/1=C/C=C/C[C@H](OC(=O)C[C@@H]([C@H](C[C@H](C[C@H](C[C@@H]([C@H]1O)C)C)C)C)O)[C@@H]1CCC[C@H]1C(=O)O
• InChI: InChI=1S/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/t17-,18+,19-,20-,22+,23+,24-,25-,27+/m0/s1
• InChIKey: OJCKRNPLOZHAOU-HBJZAWFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R)-2-[(2S,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid
• IUPAC Traditional name: (1R,2R)-2-[(2S,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid
• Synonyms: 2-(7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl)-cyclopentanecarboxylic acid; Borrelidine; Cyclopentanecarboxylic acid; NSC 216128; Treponemycin; Borrelidin

Database IDs

• CAS Number: 7184-60-3
• MDL Number: MFCD01740784
• PubChem SID: 24724413; 24724417; 162248057
• PubChem CID: 5459085

CALCULATED PROPERTIES

• Acid pKa: 3.8741593
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 3.0287466
• LogD (pH = 7.4): 1.432608
• Log P: 4.659358
• Molar Refractivity: 135.4583 cm^3
• Polarizability: 52.73697 Å^3
• Polar Surface Area: 127.85 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble; DMSO: soluble1 mg/mL; ethanol: soluble; ethyl acetate: soluble; methanol: soluble; methanol: soluble1 mg/mL
• Apperance: lyophilized powder

Safety Information

• RTECS: ED8750000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥95% (HPLC); ≥98% (HPLC)
• Biological Source: from Streptomyces parvulus; from Streptomyces sp.
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C28H43NO6

DETAILS

Sigma Aldrich - B1936

Biochem/physiol Actions
Borrelidin is a potent angiogenesis inhibitor that induces apoptosis in capillary tube-forming cells. Also displays antimalarial activity against drug-resistant Plasmodia. Antimicrobial and selective threonyl t-RNA synthetase inhibitor.

Sigma Aldrich - B3061

Biochem/physiol Actions
Borrelidin is a potent angiogenesis inhibitor that induces apoptosis in capillary tube-forming cells. Also displays antimalarial activity against drug-resistant Plasmodia. Antimicrobial and selective threonyl t-RNA synthetase inhibitor.