Monomethylauristatin F

C₃₉H₆₅N₅O₈CAS 745017-94-1731.98 g/mol

Open in Covalent MOL file

Amide Carboxylic acid Ether Secondary amine

Properties

Molecular formula: C₃₉H₆₅N₅O₈
Molar mass: 731.98 g/mol
Exact mass: 731.4833 Da
logP: 3.10Crippen estimate
Polar surface area: 166.6 Å²
H-bond donors / acceptors: 4 / 8
Rotatable bonds: 21
Stereocentres: S, S, R, S, R, R, S, S, Sin SMILES atom order

Hazards

No GHS classification is on file for this compound. That is not evidence that it is harmless.

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Identifiers

CAS number

745017-94-1

SMILES

CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@@H]([C@@H](C)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)O)OC)OC)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC

InChIKey

MFRNYXJJRJQHNW-DEMKXPNLSA-N

InChI

InChI=1S/C39H65N5O8/c1-12-25(6)34(43(9)38(48)33(24(4)5)42-37(47)32(40-8)23(2)3)30(51-10)22-31(45)44-20-16-19-29(44)35(52-11)26(7)36(46)41-28(39(49)50)21-27-17-14-13-15-18-27/h13-15,17-18,23-26,28-30,32-35,40H,12,16,19-22H2,1-11H3,(H,41,46)(H,42,47)(H,49,50)/t25-,26+,28-,29-,30+,32-,33-,34-,35+/m0/s1

Characterization data

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

¹H NMR

Predicted ¹H NMR (400 MHz, CDCl₃) δ 11.50 (br s, 1H), 7.30 (m, J = 7.7 Hz, 2H), 7.22 (m, J = 7.7, 1.6 Hz, 2H), 7.19 (m, J = 7.7, 1.6 Hz, 1H), 5.90 (br d, J = 5.0 Hz, 1H), 5.90 (br d, J = 5.0 Hz, 1H), 5.22 (td, J = 7.0, 5.0 Hz, 1H), 4.73 (dd, J = 7.0, 5.0 Hz, 1H), 4.38 (t, J = 7.0 Hz, 1H), 4.13 (q, J = 7.0 Hz, 1H), 4.13 (t, J = 7.0 Hz, 1H), 3.74 (q, J = 7.0 Hz, 1H), 3.58 (d, J = 7.0 Hz, 1H), 3.41 (t, J = 7.0 Hz, 2H), 3.30 (s, 3H), 3.30 (s, 3H), 3.21 (d, J = 7.0 Hz, 2H), 2.85 (s, 3H), 2.73 (quint, J = 7.0 Hz, 1H), 2.55 (d, J = 7.0 Hz, 2H), 2.43 (s, 3H), 2.08 (m, J = 7.0 Hz, 1H), 2.04 (m, J = 7.0 Hz, 1H), 1.91 (m, J = 7.0 Hz, 2H), 1.91 (m, J = 7.0 Hz, 2H), 1.83 (sept, J = 7.0 Hz, 1H), 1.27 (quint, J = 7.0 Hz, 2H), 1.20 (br s, 1H), 1.11 (d, J = 7.0 Hz, 3H), 0.86 (t, J = 7.0 Hz, 3H), 0.86 (d, J = 7.0 Hz, 3H), 0.86 (d, J = 7.0 Hz, 6H), 0.86 (d, J = 7.0 Hz, 6H).

¹³C NMR

Predicted ¹³C NMR (101 MHz, CDCl₃) δ 178.0, 177.1, 173.9, 172.1, 171.6, 144.1, 128.3, 127.8, 125.6, 83.6, 77.2, 72.5, 64.7, 64.0, 63.1, 57.8, 51.7, 51.4, 44.0, 39.7, 38.4, 36.6, 33.5, 31.3, 30.6, 29.4, 28.3, 26.9, 25.5, 22.3, 16.5, 16.2, 15.3, 11.5, 9.6.

[M + H]+

[M + H]+ Calcd for C39H66N5O8 732.4906

[M + Na]+

[M + Na]+ Calcd for C39H65N5NaO8 754.4725

[M − H]−

[M − H]− Calcd for C39H64N5O8 730.4760

Elemental analysis

Anal. Calcd for C39H65N5O8: C, 64.00; H, 8.95; N, 9.57.