Auristatin E

C₄₀H₆₉N₅O₇CAS 160800-57-7732.02 g/mol

Open in Covalent MOL file

Alcohol Amide Ether Tertiary amine

Properties

Molecular formula: C₄₀H₆₉N₅O₇
Molar mass: 732.02 g/mol
Exact mass: 731.5197 Da
logP: 3.87Crippen estimate
Polar surface area: 140.8 Å²
H-bond donors / acceptors: 3 / 8
Rotatable bonds: 20
Stereocentres: S, S, R, S, R, R, R, S, S, Sin SMILES atom order

Hazards

Danger

H341 Suspected of causing genetic defects100% of notifiers
H361 Suspected of damaging fertility or the unborn child100% of notifiers
H372 Causes damage to organs through prolonged or repeated exposure100% of notifiers

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

Precautionary statements

P203, P260, P264, P270, P280, P318, P319, P405, P501

Identifiers

CAS number

160800-57-7

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

InChIKey

WOWDZACBATWTAU-FEFUEGSOSA-N

InChI

InChI=1S/C40H69N5O7/c1-14-26(6)35(44(11)40(50)33(24(2)3)42-39(49)34(25(4)5)43(9)10)31(51-12)23-32(46)45-22-18-21-30(45)37(52-13)27(7)38(48)41-28(8)36(47)29-19-16-15-17-20-29/h15-17,19-20,24-28,30-31,33-37,47H,14,18,21-23H2,1-13H3,(H,41,48)(H,42,49)/t26-,27+,28+,30-,31+,33-,34-,35-,36+,37+/m0/s1

Characterization data

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

¹H NMR

Predicted ¹H NMR (400 MHz, CDCl₃) δ 7.29 (m, J = 7.7, 1.6 Hz, 2H), 7.29 (m, J = 7.7 Hz, 2H), 7.29 (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), 5.37 (d, J = 7.0 Hz, 1H), 4.76 (m, 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), 3.48 (d, J = 7.0 Hz, 1H), 3.41 (t, J = 7.0 Hz, 2H), 3.30 (s, 3H), 3.30 (s, 3H), 2.85 (s, 3H), 2.73 (quint, J = 7.0 Hz, 1H), 2.55 (d, J = 7.0 Hz, 2H), 2.22 (s, 6H), 2.08 (m, J = 7.0 Hz, 1H), 2.00 (br s, 1H), 1.97 (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), 1.14 (d, J = 7.0 Hz, 3H), 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 177.1, 173.9, 172.1, 171.6, 140.8, 128.5, 127.5, 126.9, 85.8, 83.6, 81.9, 77.2, 64.7, 64.0, 63.1, 54.1, 51.7, 51.4, 44.0, 42.9, 38.4, 36.6, 31.3, 30.6, 29.4, 28.3, 25.5, 24.4, 22.3, 17.6, 16.8, 16.2, 15.3, 11.5, 9.6.

[M + H]+

[M + H]+ Calcd for C40H70N5O7 732.5270

[M + Na]+

[M + Na]+ Calcd for C40H69N5NaO7 754.5089

[M − H]−

[M − H]− Calcd for C40H68N5O7 730.5124

Elemental analysis

Anal. Calcd for C40H69N5O7: C, 65.63; H, 9.50; N, 9.57.