ID: ALA1077642
PubChem CID: 46882879
Max Phase: Preclinical
Molecular Formula: C30H32O15
Molecular Weight: 632.57
Molecule Type: Small molecule
Associated Items:
Synonyms: Galloylpaeoniflorin | galloylpaeoniflorin|CHEMBL1077642|BDBM50378695|NS00093953
Canonical SMILES: C[C@@]12C[C@@]3(O)O[C@@H](O1)[C@]1(COC(=O)c4ccccc4)[C@@H]3C[C@]12O[C@@H]1O[C@H](COC(=O)c2cc(O)c(O)c(O)c2)[C@@H](O)[C@H](O)[C@H]1O
Standard InChI: InChI=1S/C30H32O15/c1-27-11-29(39)18-9-30(27,28(18,26(44-27)45-29)12-41-23(37)13-5-3-2-4-6-13)43-25-22(36)21(35)20(34)17(42-25)10-40-24(38)14-7-15(31)19(33)16(32)8-14/h2-8,17-18,20-22,25-26,31-36,39H,9-12H2,1H3/t17-,18+,20-,21+,22-,25+,26-,27+,28+,29-,30-/m1/s1
Standard InChI Key: KLFIUQCKSSAFFU-ANNBSXMPSA-N
Molfile:
RDKit 2D
47 53 0 0 0 0 0 0 0 0999 V2000
0.4351 -12.3903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.4366 -13.2308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.1645 -13.6455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.8869 -13.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.8854 -12.3878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.1616 -11.9646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.1601 -11.1241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.9685 -11.7424 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.1638 -12.8072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.3455 -12.5080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.2942 -11.9717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.4378 -13.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7596 -14.5463 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.3789 -14.4538 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
-3.1653 -11.2274 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-3.1406 -12.0528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.4146 -12.4441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.3962 -13.2678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.6744 -13.6590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.9701 -13.2293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.9924 -12.4041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.7189 -12.0084 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-3.0999 -13.6976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-1.6533 -14.4833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.2457 -13.6232 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.3713 -15.1421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6932 -15.7763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.3387 -15.1037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.3030 -16.3700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6242 -17.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3351 -17.0425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7235 -16.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.4000 -15.8111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.8824 -14.0516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.9278 -13.0895 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.0568 -12.0900 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
-3.8914 -10.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.9160 -10.0124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.5929 -11.2701 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-3.2133 -9.5799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.2376 -8.7564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.9642 -8.3648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.6680 -8.8028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.6402 -9.6248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.5358 -8.3233 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-3.9899 -7.5406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-5.3954 -8.4146 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
6 8 1 0
18 23 1 6
1 9 1 0
19 24 1 1
3 9 1 0
20 25 1 6
21 11 1 1
9 10 1 0
13 26 1 0
8 10 1 0
26 27 1 0
1 11 1 6
26 28 2 0
9 12 1 1
27 29 2 0
12 13 1 0
29 30 1 0
3 14 1 6
30 31 2 0
31 32 1 0
1 2 1 0
32 33 2 0
33 27 1 0
15 16 1 0
4 34 1 6
1 6 1 0
10 35 1 0
4 35 1 0
17 16 1 1
10 36 1 1
17 18 1 0
15 37 1 0
2 3 1 0
37 38 1 0
3 4 1 0
37 39 2 0
4 5 1 0
38 40 2 0
5 6 1 0
40 41 1 0
6 7 1 6
41 42 2 0
17 22 1 0
42 43 1 0
18 19 1 0
43 44 2 0
44 38 1 0
19 20 1 0
41 45 1 0
20 21 1 0
42 46 1 0
21 22 1 0
43 47 1 0
M END| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| 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 |
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
| Molecular Weight: 632.57 | Molecular Weight (Monoisotopic): 632.1741 | AlogP: -0.38 | #Rotatable Bonds: 8 |
| Polar Surface Area: 231.13 | Molecular Species: NEUTRAL | HBA: 15 | HBD: 7 |
| #RO5 Violations: 3 | HBA (Lipinski): 15 | HBD (Lipinski): 7 | #RO5 Violations (Lipinski): 3 |
| CX Acidic pKa: 8.11 | CX Basic pKa: ┄ | CX LogP: 1.20 | CX LogD: 1.12 |
| Aromatic Rings: 2 | Heavy Atoms: 45 | QED Weighted: 0.15 | Np Likeness Score: 1.94 |
| 1. Duan WJ, Yang JY, Chen LX, Zhang LJ, Jiang ZH, Cai XD, Zhang X, Qiu F.. (2009) Monoterpenes from Paeonia albiflora and their inhibitory activity on nitric oxide production by lipopolysaccharide-activated microglia., 72 (9): [PMID:19691309] [10.1021/np9001898] |
| 2. Ha do T, Ngoc TM, Lee I, Lee YM, Kim JS, Jung H, Lee S, Na M, Bae K.. (2009) Inhibitors of aldose reductase and formation of advanced glycation end-products in moutan cortex (Paeonia suffruticosa)., 72 (8): [PMID:19670875] [10.1021/np9002004] |
| 3. Ding L, Zhao F, Chen L, Jiang Z, Liu Y, Li Z, Qiu F, Yao X.. (2012) New monoterpene glycosides from Paeonia suffruticosa Andrews and their inhibition on NO production in LPS-induced RAW 264.7 cells., 22 (23): [PMID:23067550] [10.1016/j.bmcl.2012.09.034] |
| 4. Song WH, Cheng ZH, Chen DF.. (2014) Anticomplement monoterpenoid glucosides from the root bark of Paeonia suffruticosa., 77 (1): [PMID:24377852] [10.1021/np400571x] |
Source(1):