Mithramycin

C52H76O24CAS 18378-89-71085.16 g/mol

Open in Covalent MOL file
OOHOOHOOOHOHOOHOHOHOOOOOOHHOOHOOHOO
AcetalAlcoholEtherKetonePhenol

Properties

Molecular formula
C52H76O24
Molar mass
1085.16 g/mol
Exact mass
1084.4727 Da
Melting point
180–183 °C
logP
-0.25Crippen estimate
Polar surface area
358.2 Ų
H-bond donors / acceptors
11 / 24
Rotatable bonds
15
Stereocentres
S, S, R, S, S, R, S, R, S, R, R, R, S, S, R, S, R, S, S, R, R, S, R, R, Rin SMILES atom order

Hazards

Warning
Irritant (GHS07)

Aggregated from 45 ECHA notifications, via PubChem; a share says how many notifiers assign that statement.

Precautionary statements

P264, P270, P301+P317, P330, P501

Identifiers

CAS number
18378-89-7
SMILES
CO[C@H](C(=O)[C@@H](O)[C@@H](C)O)[C@@H]1Cc2cc3cc(O[C@H]4C[C@@H](O[C@H]5C[C@@H](O)[C@H](O)[C@@H](C)O5)[C@H](O)[C@@H](C)O4)c(C)c(O)c3c(O)c2C(=O)[C@H]1O[C@H]1C[C@@H](O[C@H]2C[C@@H](O[C@H]3C[C@](C)(O)[C@H](O)[C@@H](C)O3)[C@@H](O)[C@@H](C)O2)[C@H](O)[C@@H](C)O1
InChIKey
CFCUWKMKBJTWLW-BKHRDMLASA-N
InChI
InChI=1S/C52H76O24/c1-18-29(72-34-14-30(43(58)21(4)68-34)73-33-13-28(54)42(57)20(3)67-33)12-26-10-25-11-27(49(66-9)48(63)41(56)19(2)53)50(47(62)39(25)46(61)38(26)40(18)55)76-36-16-31(44(59)23(6)70-36)74-35-15-32(45(60)22(5)69-35)75-37-17-52(8,65)51(64)24(7)71-37/h10,12,19-24,27-28,30-37,41-45,49-51,53-61,64-65H,11,13-17H2,1-9H3/t19-,20-,21-,22-,23-,24-,27+,28-,30-,31-,32-,33+,34+,35+,36+,37+,41+,42-,43-,44-,45+,49+,50+,51-,52+/m1/s1
Characterization data

Calculated from the structure, in the form journals print them.

¹H NMR
Predicted ¹H NMR (400 MHz, CDCl₃) δ 7.39 (s, 1H), 6.80 (s, 1H), 6.60 (t, J = 7.0 Hz, 1H), 5.68 (t, J = 7.0 Hz, 1H), 5.68 (t, J = 7.0 Hz, 1H), 5.68 (t, J = 7.0 Hz, 1H), 5.68 (t, J = 7.0 Hz, 1H), 5.30 (br s, 1H), 5.30 (br s, 1H), 5.20 (d, J = 7.0 Hz, 1H), 4.75 (d, J = 7.0 Hz, 1H), 4.58 (quint, J = 7.0 Hz, 1H), 4.42 (d, J = 7.0 Hz, 1H), 4.41 (m, J = 7.0 Hz, 1H), 4.41 (d, J = 7.0 Hz, 1H), 4.38 (t, J = 7.0 Hz, 1H), 4.38 (t, J = 7.0 Hz, 1H), 4.38 (t, J = 7.0 Hz, 1H), 4.36 (m, J = 7.0 Hz, 1H), 3.99 (quint, J = 7.0 Hz, 1H), 3.99 (quint, J = 7.0 Hz, 1H), 3.99 (quint, J = 7.0 Hz, 1H), 3.99 (quint, J = 7.0 Hz, 1H), 3.99 (quint, J = 7.0 Hz, 1H), 3.94 (q, J = 7.0 Hz, 1H), 3.94 (q, J = 7.0 Hz, 1H), 3.94 (q, J = 7.0 Hz, 1H), 3.30 (s, 3H), 3.09 (m, J = 7.0 Hz, 1H), 3.06 (m, J = 7.0 Hz, 2H), 2.41 (t, J = 7.0 Hz, 2H), 2.35 (s, 3H), 2.27 (t, J = 7.0 Hz, 2H), 2.27 (d, J = 7.0 Hz, 2H), 2.24 (t, J = 7.0 Hz, 2H), 2.24 (t, J = 7.0 Hz, 2H), 2.00 (br s, 1H), 2.00 (br s, 1H), 2.00 (br s, 1H), 2.00 (br s, 1H), 2.00 (br s, 1H), 2.00 (br s, 1H), 2.00 (br s, 1H), 2.00 (br s, 1H), 2.00 (br s, 1H), 1.22 (d, J = 7.0 Hz, 3H), 1.22 (s, 3H), 1.19 (d, J = 7.0 Hz, 3H), 1.19 (d, J = 7.0 Hz, 3H), 1.19 (d, J = 7.0 Hz, 3H), 1.19 (d, J = 7.0 Hz, 3H), 1.19 (d, J = 7.0 Hz, 3H).
¹³C NMR
Predicted ¹³C NMR (101 MHz, CDCl₃) δ 208.7, 199.3, 159.4, 156.6, 154.6, 142.8, 139.0, 121.1, 120.1, 116.2, 116.2, 116.2, 115.7, 114.7, 108.0, 106.1, 97.5, 94.4, 92.4, 91.6, 89.6, 83.6, 80.6, 80.6, 80.6, 79.6, 79.6, 79.6, 78.2, 78.2, 78.2, 77.7, 76.7, 74.7, 69.6, 66.3, 54.2, 45.1, 40.5, 37.1, 34.1, 34.1, 34.1, 30.6, 22.0, 19.8, 16.3, 15.2, 14.9, 14.9, 14.9, 14.9.
[M + H]+
[M + H]+ Calcd for C52H77O24 1085.4799
[M + Na]+
[M + Na]+ Calcd for C52H76NaO24 1107.4619
[M − H]−
[M − H]− Calcd for C52H75O24 1083.4654
Elemental analysis
Anal. Calcd for C52H76O24: C, 57.56; H, 7.06.

Weigh it out

Type any one amount. The others follow from the molar mass.

Names and synonyms

12 names
  • D-Threo-2-Pentulose, 5-deoxy-1-C-[(2S,3S)-7-[[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-arabino-hexopyranosyl]oxy]-3-[(O-2,6-dideoxy-3-C-methyl-β-D-ribo-hexopyranosyl-(1→3)-O-2,6-dideoxy-β-D-lyxo-hexopyranosyl-(1→3)-2,6-dideoxy-β-D-arabino-hexopyranosyl)oxy]-1,2,3,4-tetrahydro-5,10-dihydroxy-6-methyl-4-oxo-2-anthracenyl]-1-O-methyl-, (1S)-
  • NSC 24559
  • Antibiotic LA 7017
  • Aureolic acid
  • Mitramycin
  • Mithracin
  • [1S(2S,3S)]-5-Deoxy-1-C-[7-[[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-arabino-hexopyranosyl]oxy]-3-[(O-2,6-dideoxy-3-C-methyl-β-D-ribo-hexopyranosyl-(1→3)-O-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1→3)-2,6-dideoxy-β-D-lyxo-hexopyranosyl)oxy]-1,2,3,4-tetrahydro-5,10-dihydroxy-6-methyl-4-oxo-2-anthracenyl]-1-O-methyl-D-threo-2-pentulose
  • Plicamycin
  • Plicatomycin
  • PA 144
  • A 2371
  • Mithramycin A

Work with Mithramycin

Predict the NMR spectrum1H and 13C shifts with multiplicities Make a solutionWhat to weigh for any molarity and volume Check drug-likenessLipinski, Veber and lead-likeness Isotope patternExact mass and the mass spectrum pattern

Elsewhere

PubChem CAS Common Chemistry NIST WebBook