(3S,6S,9S,12S,15S,18S,21S,24S,27R,30S,33S)-12-ethyl-15-((1R,2R,E)-1-hydroxy-2-methylhex-4-enyl)-6,21,24,33-tetraisobutyl-3,18-diisopropyl-1,7,9,10,16,19,22,25,27,30-decamethyl-4-(3-methylbut-2-enyl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone

ID: ALA3327189

PubChem CID: 118712124

Max Phase: Preclinical

Molecular Formula: C68H121N11O12

Molecular Weight: 1284.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C=C/C[C@@H](C)[C@@H](O)[C@H]1C(=O)N[C@@H](CC)C(=O)N(C)[C@@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N(CC=C(C)C)[C@@H](C(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)N1C

Standard InChI:  InChI=1S/C68H121N11O12/c1-28-30-31-45(17)57(80)56-60(83)71-49(29-2)63(86)72(21)48(20)62(85)75(24)53(37-42(11)12)66(89)79(33-32-38(3)4)55(44(15)16)68(91)73(22)50(34-39(5)6)59(82)69-46(18)58(81)70-47(19)61(84)74(23)51(35-40(7)8)64(87)76(25)52(36-41(9)10)65(88)77(26)54(43(13)14)67(90)78(56)27/h28,30,32,39-57,80H,29,31,33-37H2,1-27H3,(H,69,82)(H,70,81)(H,71,83)/b30-28+/t45-,46+,47-,48+,49+,50+,51+,52+,53+,54+,55+,56+,57-/m1/s1

Standard InChI Key:  XNWZBIZXSXENSJ-CXUAMOJJSA-N

Molfile:  

     RDKit          2D

 92 92  0  0  0  0  0  0  0  0999 V2000
    6.6405  -22.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145  -22.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9957  -22.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145  -20.9387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409  -18.5231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596  -18.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1747  -18.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409  -21.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2244  -18.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596  -17.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409  -16.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409  -16.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2244  -17.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1747  -19.3082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5090  -18.1307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1896  -18.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5090  -17.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1896  -19.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8683  -18.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5090  -19.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8683  -19.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532  -18.5231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8683  -17.3502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532  -19.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2341  -18.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9085  -18.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2341  -17.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9085  -16.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5894  -17.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9085  -16.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9085  -19.3082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2341  -15.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2341  -14.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532  -14.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2745  -18.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9513  -18.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2745  -19.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6405  -18.5231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9513  -17.3502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6405  -19.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145  -18.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145  -19.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9957  -19.3082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6805  -22.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3550  -22.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6805  -21.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9513  -22.3584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6405  -23.5317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2745  -22.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5894  -22.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2745  -23.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5894  -23.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9513  -23.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5894  -21.5737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9085  -22.7508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2341  -22.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9085  -23.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2341  -21.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532  -22.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532  -21.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532  -20.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8683  -22.3584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532  -23.5317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8683  -21.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1896  -22.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5090  -22.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1896  -23.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5090  -21.5737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1747  -22.7508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596  -22.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409  -22.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596  -21.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2244  -22.3584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409  -23.5317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2244  -21.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955  -22.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8587  -20.8313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8924  -21.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8646  -20.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5353  -19.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1767  -19.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1018  -20.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4583  -17.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5935  -18.1348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5649  -19.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9481  -21.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2388  -21.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356  -20.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5234  -20.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3423  -18.8945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6469  -19.6120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3683  -17.6304    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  5  9  1  0
  6 10  1  1
 10 11  1  0
 11 12  1  0
 11 13  1  0
  7 14  2  0
  7 15  1  0
 15 16  1  0
 15 17  1  0
 16 18  1  6
 16 19  1  0
 18 20  1  0
 18 21  1  0
 19 22  1  0
 19 23  2  0
 22 24  1  0
 25 22  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  1
 28 30  1  0
 26 31  2  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 35 36  1  0
 35 37  1  6
 36 38  1  0
 36 39  2  0
 38 40  1  0
 38 41  1  0
 40 42  1  0
 42  4  1  0
 42 43  2  0
  3 44  1  0
 44 45  1  0
 44 46  1  0
  1 47  1  0
  1 48  2  0
 47 49  1  0
 49 50  1  0
 49 51  1  1
 51 52  1  0
 51 53  1  0
 50 54  2  0
 50 55  1  0
 55 56  1  0
 55 57  1  0
 56 58  1  6
 56 59  1  0
 58 60  1  0
 60 61  1  0
 60 64  1  0
 59 62  1  0
 59 63  2  0
 62 65  1  0
 65 66  1  0
 65 67  1  1
 66 68  2  0
 66 69  1  0
 69 70  1  0
 70 71  1  0
 70 72  1  1
 71 73  1  0
 71 74  2  0
 73 75  1  0
 73 76  1  0
 75  8  1  0
  8 77  2  0
 75 78  1  1
 78 79  1  0
 79 80  1  0
 79 81  1  0
  4 82  1  0
 27 83  1  6
 26 84  1  0
 84 35  1  0
 37 85  1  0
 47 86  1  0
 86 87  1  0
 87 88  2  0
 88 89  1  0
 40 90  1  6
 88 91  1  0
 25 92  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3327189

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 1284.78

Molecular Weight (Monoisotopic): 1283.9196

AlogP: ┄

#Rotatable Bonds: ┄

Polar Surface Area: ┄

Molecular Species: ┄

HBA: ┄

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): ┄

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: ┄

CX LogD: ┄

Aromatic Rings: ┄

Heavy Atoms: ┄

QED Weighted: ┄

Np Likeness Score: ┄

References

1. Sweeney ZK, Fu J, Wiedmann B..  (2014)  From chemical tools to clinical medicines: nonimmunosuppressive cyclophilin inhibitors derived from the cyclosporin and sanglifehrin scaffolds.,  57  (17): [PMID:24831536] [10.1021/jm500223x]

Source

Source(1):

• Scientific Literature