ID: ALA501143
PubChem CID: 11169896
Max Phase: Preclinical
Molecular Formula: C43H55NO6
Molecular Weight: 681.91
Molecule Type: Small molecule
Associated Items:
Synonyms: Nodulisporic Acid A4 | Nodulisporic Acid A4|CHEMBL501143|CHEBI:207059|(E)-5-[(3S,4S,7S,8S,9R,12S,23R,24S,28S)-7,24-dihydroxy-3,4,8,20,20,22,22-heptamethyl-27-oxo-28-prop-1-en-2-yl-21-oxa-1-azaoctacyclo[13.13.1.02,14.03,12.04,9.017,25.018,23.026,29]nonacosa-2(14),15,17(25),18,26(29)-pentaen-8-yl]-2-methylpent-2-enoic acid
Canonical SMILES: C=C(C)[C@H]1C(=O)c2c3c(cc4c5c(n1c24)[C@@]1(C)[C@@H](CC[C@H]2[C@](C)(CC/C=C(\C)C(=O)O)[C@@H](O)CC[C@@]21C)C5)C1=CC(C)(C)OC(C)(C)[C@H]1[C@@H]3O
Standard InChI: InChI=1S/C43H55NO6/c1-21(2)33-36(47)31-30-24(27-20-39(4,5)50-40(6,7)32(27)35(30)46)19-25-26-18-23-13-14-28-41(8,16-11-12-22(3)38(48)49)29(45)15-17-42(28,9)43(23,10)37(26)44(33)34(25)31/h12,19-20,23,28-29,32-33,35,45-46H,1,11,13-18H2,2-10H3,(H,48,49)/b22-12+/t23-,28-,29-,32+,33-,35+,41-,42-,43+/m0/s1
Standard InChI Key: RQRLQCQHVHFUJZ-QGLQQYJRSA-N
Molfile:
RDKit 2D
53 60 0 0 0 0 0 0 0 0999 V2000
-4.1551 -20.9194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.6269 -21.5979 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-4.2741 -22.3451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.3307 -20.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.9810 -21.7373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.4482 -22.4152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.9481 -23.0667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.1930 -21.9676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.1700 -22.7920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.4490 -23.1828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.4969 -21.5408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7752 -21.9258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7495 -22.7513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.0433 -22.9806 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-3.5917 -23.1289 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
-5.0283 -22.6879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.3498 -23.1638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.0867 -20.0892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.9372 -20.6354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.0026 -21.6446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.5050 -22.2961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.4704 -20.9645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2611 -21.1996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2769 -22.0238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.6780 -21.1675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.9561 -20.7723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2516 -20.3694 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
1.2687 -22.8458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.6979 -21.9916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.9996 -22.4098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0120 -23.2239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.7246 -23.6209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.9924 -21.5798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.6905 -22.8181 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
3.4057 -21.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.4157 -22.3832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.4273 -23.1980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1871 -22.1203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.4259 -24.0095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.0293 -24.0097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6100 -24.5986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.3905 -25.3960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.4103 -24.3901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.0026 -24.6024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.1502 -23.5999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.8096 -22.6650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.5924 -22.3983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.2149 -22.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.9977 -22.6762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.0544 -23.7543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.6226 -23.2212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
7.1606 -21.8652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-3.1833 -23.8596 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
20 12 1 0
6 15 1 1
3 16 1 0
3 17 1 0
1 18 1 0
1 19 1 0
20 21 2 0
21 24 1 0
23 22 1 0
22 20 1 0
23 24 1 0
23 26 1 0
24 30 1 0
29 25 1 0
25 26 1 0
23 27 1 1
24 28 1 6
29 30 1 0
29 36 1 0
30 31 1 0
31 32 1 0
32 37 1 0
30 33 1 1
29 34 1 6
36 35 1 1
36 37 1 0
1 2 1 0
1 4 1 0
38 36 1 0
2 3 1 0
10 39 1 0
3 6 1 0
14 40 1 0
39 40 1 0
5 4 2 0
40 41 1 1
5 6 1 0
41 42 2 0
6 7 1 0
41 43 1 0
7 9 1 0
39 44 2 0
8 5 1 0
37 45 1 1
8 9 2 0
38 46 1 0
9 10 1 0
46 47 1 0
10 13 2 0
47 48 2 0
12 11 2 0
48 49 1 0
11 8 1 0
48 50 1 0
12 13 1 0
13 14 1 0
49 51 1 0
49 52 2 0
14 21 1 0
7 53 1 1
M END| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| 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 |
| 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: 681.91 | Molecular Weight (Monoisotopic): 681.4029 | AlogP: 8.41 | #Rotatable Bonds: 5 |
| Polar Surface Area: 108.99 | Molecular Species: ACID | HBA: 6 | HBD: 3 |
| #RO5 Violations: 2 | HBA (Lipinski): 7 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): 2 |
| CX Acidic pKa: 4.56 | CX Basic pKa: ┄ | CX LogP: 6.96 | CX LogD: 4.16 |
| Aromatic Rings: 2 | Heavy Atoms: 50 | QED Weighted: 0.22 | Np Likeness Score: 3.04 |
| 1. Singh SB, Ondeyka JG, Jayasuriya H, Zink DL, Ha SN, Dahl-Roshak A, Greene J, Kim JA, Smith MM, Shoop W, Tkacz JS.. (2004) Nodulisporic acids D-F: structure, biological activities, and biogenetic relationships., 67 (9): [PMID:15387649] [10.1021/np0498455] |
Source(1):