SID17389200

ID: ALA3391990

Cas Number: 18642-44-9

PubChem CID: 10032468

Product Number: A350893, Order Now?

Max Phase: Preclinical

Molecular Formula: C37H56O11

Molecular Weight: 676.84

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Actein | Actein|18642-44-9|UNII-I14QO4LW9V|I14QO4LW9V|26S-ACTEIN|Shengmating|ACTEIN, (-)-|DTXSID7033153|CHEBI:70241|ACTEIN (USP-RS)|ACTEIN [USP-RS]|[(1S,1'R,2S,3'R,4R,4'R,5R,5'R,6'R,10'S,12'S,13'S,16'R,18'S,21'R)-2-hydroxy-1,4',6',12',17',17'-hexamethyl-18'-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyspiro[3,6-dioxabicyclo[3.1.0]hexane-4,8'-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosane]-3'-yl] acetate|beta-D-Xylopyranoside, (3beta,12beta)-12-(acetyloxy)-16,23:23,26:24,25-triepoxy-26-hyShow More⌵

Canonical SMILES:  CC(=O)O[C@@H]1C[C@@]23C[C@@]24CC[C@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)C(C)(C)[C@@H]4CC[C@H]3[C@]2(C)C[C@@H]3O[C@]4(C[C@@H](C)[C@@H]3[C@@]12C)O[C@H](O)[C@@]1(C)O[C@@H]41

Standard InChI:  InChI=1S/C37H56O11/c1-17-12-37(29-34(7,47-29)30(42)48-37)46-20-13-32(5)22-9-8-21-31(3,4)23(45-28-27(41)26(40)19(39)15-43-28)10-11-35(21)16-36(22,35)14-24(44-18(2)38)33(32,6)25(17)20/h17,19-30,39-42H,8-16H2,1-7H3/t17-,19-,20+,21+,22+,23+,24-,25+,26+,27-,28+,29-,30+,32+,33-,34+,35-,36+,37-/m1/s1

Standard InChI Key:  NEWMWGLPJQHSSQ-PSDKAYTQSA-N

Molfile:  

     RDKit          2D

 54 62  0  0  0  0  0  0  0  0999 V2000
    6.2307    0.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1483   -1.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4514    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4270   -1.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9415    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0856    1.1815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5577   -1.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -0.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4395   -0.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8530   -1.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4057   -0.6882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2016   -0.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4228   -2.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6098   -0.7420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1423   -2.8480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8572    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3330   -0.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8014   -0.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4334   -2.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1524   -0.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2860   -2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3206   -1.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8636   -2.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6646    0.5845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4771    0.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991   -2.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4334   -1.6085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7162   -2.8438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2860   -1.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8572   -2.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1359   -2.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8655    0.8374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8636   -1.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1524    1.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1464   -1.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991   -1.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0557    0.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1566    2.0811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1423   -3.6770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8525   -0.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5537   -2.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5537    0.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5808   -2.8438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5766   -1.1897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7047   -3.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1244   -3.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    1.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311    0.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0410    1.3680    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2202   -1.5339    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4376   -3.2584    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4146   -3.2542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8448   -0.7877    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1247    0.0580    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 10  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  1  1  0
  7 22  1  0
  8 17  1  0
  9  2  1  0
 10  7  1  0
 11 12  1  0
 12  1  1  0
 13  4  1  0
 14  5  1  0
 15 19  1  0
 16  8  1  0
 17 24  1  0
 18 14  1  0
 19 28  1  0
 20 16  1  0
 21 13  1  0
 22 18  1  0
 23 15  1  0
 24 25  1  0
 25  5  1  0
 26 21  1  0
 27 19  1  0
 26 28  1  1
 29  4  1  0
 30 10  1  0
 31 30  1  0
 16 32  1  1
 33 23  1  0
 34 32  1  0
 35 27  1  0
 36 29  1  0
  1 37  1  1
 38 34  2  0
 15 39  1  6
 12 40  1  1
  7 41  1  6
  8 42  1  1
 23 43  1  1
 33 44  1  6
 45 21  1  0
 46 21  1  0
 24 47  1  6
 48 34  1  0
  3 49  1  1
 18 50  1  6
 19 51  1  6
 13 52  1  6
 10 53  1  1
  6  3  1  0
  5 11  1  6
 18 17  1  0
  7  8  1  0
  2 20  1  6
  4  9  1  1
 31 13  1  0
 26 36  1  0
 33 35  1  0
 17 54  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3391990

   Actein

Molecule Features

Natural Product: Yes

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: 676.84

Molecular Weight (Monoisotopic): 676.3823

AlogP: 3.03

#Rotatable Bonds: 3

Polar Surface Area: 156.67

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.07

CX Basic pKa: ┄

CX LogP: 2.75

CX LogD: 2.75

Aromatic Rings: ┄

Heavy Atoms: 48

QED Weighted: 0.20

Np Likeness Score: 3.32

References

1. PubChem BioAssay data set, 

2. Cicek SS, Khom S, Taferner B, Hering S, Stuppner H..  (2010)  Bioactivity-guided isolation of GABA(A) receptor modulating constituents from the rhizomes of Actaea racemosa.,  73  (12): [PMID:21082802] [10.1021/np100479w]

3. Chen JY, Li PL, Tang XL, Wang SJ, Jiang YT, Shen L, Xu BM, Shao YL, Li GQ..  (2014)  Cycloartane triterpenoids and their glycosides from the rhizomes of Cimicifuga foetida.,  77  (9): [PMID:25136911] [10.1021/np500249v]

4. Zhang H, Chen Y, Huang S, Xiao WW, Qiu MH, Shao LD, Chen CH, Li D..  (2023)  Development of actein derivatives as potent anti-triple negative breast cancer agents.,  89  [PMID:37121522] [10.1016/j.bmcl.2023.129307]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays