(1S,2R,18R,19R,22S,25R,28R,40S)-2-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-(carbamoylmethyl)-47-chloro-18,32,35,37-tetrahydroxy-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(48),9,11,14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid

• ChemBase ID: 179759
• Molecular Formular: C73H89ClN10O26
• Molecular Mass: 1557.99216
• Monoisotopic Mass: 1556.5638007
• SMILES: [C@@H]12NC(=O)[C@H](NC(=O)[C@@H]3NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](CC(C)C)NC)[C@@H](c4cc(c(Oc5c(c(Oc6ccc([C@H]2O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(N)C)cc6)cc3c5)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(N)C)cc4)Cl)O)CC(=O)N)c2cc(c3c([C@H](NC1=O)C(=O)O)cc(cc3O)O)c(cc2)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2c3Oc4ccc(cc4)[C@@H](O[C@@H]4O[C@@H](C)[C@@H]([C@@](C4)(C)N)O)[C@@H]4NC(=O)[C@H](NC(=O)[C@H]5c(c3)cc2Oc2ccc(cc2Cl)[C@@H](O)[C@H](C(=O)N[C@H](C(=O)N5)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)c2ccc(c(c2)c2c([C@H](NC4=O)C(=O)O)cc(cc2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@@](C1)(C)N)O
• InChI: InChI=1S/C73H89ClN10O26/c1-27(2)16-39(78-7)64(95)83-54-56(90)32-11-15-43(38(74)18-32)106-45-20-33-19-44(60(45)110-71-61(58(92)57(91)46(26-85)107-71)109-49-25-73(6,77)63(94)29(4)104-49)105-35-12-8-30(9-13-35)59(108-48-24-72(5,76)62(93)28(3)103-48)55-69(100)82-53(70(101)102)37-21-34(86)22-42(88)50(37)36-17-31(10-14-41(36)87)51(66(97)84-55)81-67(98)52(33)80-65(96)40(23-47(75)89)79-68(54)99/h8-15,17-22,27-29,39-40,46,48-49,51-59,61-63,71,78,85-88,90-94H,16,23-26,76-77H2,1-7H3,(H2,75,89)(H,79,99)(H,80,96)(H,81,98)(H,82,100)(H,83,95)(H,84,97)(H,101,102)/t28-,29-,39+,40-,46+,48-,49-,51?,52+,53-,54+,55?,56+,57+,58-,59+,61+,62-,63-,71-,72-,73-/m0/s1
• InChIKey: UECIPBUIMXSXEI-RNWFWEKMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,18R,19R,22S,25R,28R,40S)-2-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-(carbamoylmethyl)-47-chloro-18,32,35,37-tetrahydroxy-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(48),9,11,14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid
• IUPAC Traditional name: (1S,2R,18R,19R,22S,25R,28R,40S)-2-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-(carbamoylmethyl)-47-chloro-18,32,35,37-tetrahydroxy-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(48),9,11,14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid
• Synonyms: Orienticin C

Database IDs

• CAS Number: 112848-47-2
• PubChem SID: 164235669
• PubChem CID: 122131

CALCULATED PROPERTIES

• Acid pKa: 2.8319132
• H Acceptors: 27
• H Donor: 20
• LogD (pH = 5.5): -9.657688
• LogD (pH = 7.4): -7.261977
• Log P: -5.347076
• Molar Refractivity: 377.4583 cm^3
• Polarizability: 151.9218 Å^3
• Polar Surface Area: 574.97 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Product Information

• Biological Source: Isol. from Actinomycete no. INA 238 and Nocardia orientalis
• Application(s): Antibiotic

REFERENCES

• Tsuji, N. et al., J. Antibiot., 1988, 41, 819; 1506, (isol, struct)
• Nagarajan, R. et al., J. Antibiot., 1989, 42, 1438, (struct)
• Nagarajan, R. et al., J.O.C., 1989, 54, 983
• Skelton, N.J. et al., J.C.S. Perkin 1, 1990, 77, (pmr, ms)