(1S,2R,18R,22S,25R,28R,40S)-48-{[(2S,3R,4S,6R)-3-{[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-(carbamoylmethyl)-2,18,32,35,37-pentahydroxy-19-[(2R)-4-methyl-2-(methylamino)pentanamido]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8,10,12(48),14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid

• ChemBase ID: 167225
• Molecular Formular: C66H77N9O24
• Molecular Mass: 1380.36348
• Monoisotopic Mass: 1379.50814439
• SMILES: c1c2ccc(c1)Oc1cc3cc(c1O[C@@H]1O[C@H](C([C@@H]([C@@H]1O[C@@H]1O[C@H]([C@H]([C@](C1)(N)C)O)C)O)O)CO)Oc1ccc(cc1)[C@H](C(C(=O)N[C@H](C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(=O)N[C@H](c3c(c4cc1ccc4O)c(cc(c3)O)O)C(=O)O)[C@@H]2O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O
• Canonical SMILES: OC[C@@H]1O[C@@H](Oc2c3Oc4ccc(cc4)[C@@H](O)C(NC(=O)[C@@H](CC(C)C)NC)C(=O)N[C@H](C(=O)N[C@@H]4c(c3)cc2Oc2ccc(cc2)[C@@H](O)[C@@H]2NC(=O)[C@H](NC4=O)c3ccc(c(c3)c3c(O)cc(cc3[C@@H](NC2=O)C(=O)O)O)O)CC(=O)N)[C@H]([C@H](C1O)O)O[C@@H]1O[C@@H](C)[C@H]([C@@](C1)(C)N)O
• InChI: InChI=1S/C66H77N9O24/c1-25(2)16-36(69-5)58(86)74-49-51(81)27-6-11-32(12-7-27)95-40-18-30-19-41(55(40)99-65-56(54(84)53(83)42(24-76)97-65)98-44-23-66(4,68)57(85)26(3)94-44)96-33-13-8-28(9-14-33)52(82)50-63(91)73-48(64(92)93)35-20-31(77)21-39(79)45(35)34-17-29(10-15-38(34)78)46(60(88)75-50)72-61(89)47(30)71-59(87)37(22-43(67)80)70-62(49)90/h6-15,17-21,25-26,36-37,42,44,46-54,56-57,65,69,76-79,81-85H,16,22-24,68H2,1-5H3,(H2,67,80)(H,70,90)(H,71,87)(H,72,89)(H,73,91)(H,74,86)(H,75,88)(H,92,93)/t26-,36+,37-,42+,44-,46?,47+,48-,49?,50?,51+,52+,53?,54-,56+,57+,65-,66-/m0/s1
• InChIKey: IOXLZCMWALOQAE-GFNWHXECSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,18R,22S,25R,28R,40S)-48-{[(2S,3R,4S,6R)-3-{[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-(carbamoylmethyl)-2,18,32,35,37-pentahydroxy-19-[(2R)-4-methyl-2-(methylamino)pentanamido]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2^3,^6.2^1^4,^1^7.1^8,^1^2.1^2^9,^3^3.0^1^0,^2^5.0^3^4,^3^9]pentaconta-3,5,8,10,12(48),14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid
• IUPAC Traditional name: (1S,2R,18R,22S,25R,28R,40S)-48-{[(2S,3R,4S,6R)-3-{[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-(carbamoylmethyl)-2,18,32,35,37-pentahydroxy-19-[(2R)-4-methyl-2-(methylamino)pentanamido]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2^3,^6.2^1^4,^1^7.1^8,^1^2.1^2^9,^3^3.0^1^0,^2^5.0^3^4,^3^9]pentaconta-3,5,8,10,12(48),14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid
• Synonyms: Vancomycin Impurity; Didechloro Vancomycin•xHCl, Technical Grade(Vancomycin Impurity)

Database IDs

• PubChem SID: 162261358
• PubChem CID: 71316021

CALCULATED PROPERTIES

• H Acceptors: 24
• H Donor: 19
• LogD (pH = 5.5): -7.6054535
• LogD (pH = 7.4): -6.062235
• Log P: -5.599613
• Molar Refractivity: 336.9989 cm^3
• Polarizability: 134.88513 Å^3
• Polar Surface Area: 530.49 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false
• Acid pKa: 2.8762813

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: >190°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D440958

An impurity in Vancomycin.A representative lot was 75% by HPLC with less than 0.1% vancomycin.

REFERENCES

• Marshall, F.J., et al.: J. Med. Chem., 8, 18 (1965)
• Sheldrick, G.M., et al.: Nature, 271, 223 (1965)
• Dutca-Melan, S., et al.: J. Clin. Microbiol., 33, 24 (1965)