Didemnin B Analogue
AlkaPlorer ID: AK007241
Synonym: None
IUPAC Name: (2S)-N-[(2R)-1-[[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-[(2S)-2-hydroxypropanoyl]-N-methylpyrrolidine-2-carboxamide
Structure
SMILES: CC[C@H](C)[C@H]1NC(=O)[C@@H](NC(=O)[C@@H](CC(C)C)N(C)C(=O)[C@@H]2CCCN2C(=O)[C@H](C)O)[C@@H](C)OC(=O)[C@H](CC2=CC=C(OC)C=C2)N(C)C(=O)[C@@H]2CCCN2C(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)C(=O)[C@H](C(C)C)OC(=O)C[C@@H]1O
InChI: InChI=1S/C57H89N7O15/c1-15-33(8)46-44(66)29-45(67)79-49(32(6)7)48(68)34(9)50(69)58-39(26-30(2)3)54(73)64-25-17-19-41(64)56(75)62(13)43(28-37-20-22-38(77-14)23-21-37)57(76)78-36(11)47(52(71)59-46)60-51(70)42(27-31(4)5)61(12)55(74)40-18-16-24-63(40)53(72)35(10)65/h20-23,30-36,39-44,46-47,49,65-66H,15-19,24-29H2,1-14H3,(H,58,69)(H,59,71)(H,60,70)/t33-,34-,35-,36+,39-,40-,41-,42+,43-,44-,46+,47-,49-/m0/s1
InChIKey: KYHUYMLIVQFXRI-SJPGYWQQSA-N
Reference
Tyr5didemnin B and [D-Pro4]didemnin B; Two new natural didemnins with a modified macrocycle
PubChem CID: 122651
CAS: 77327-05-0
LOTUS: LTS0030187
SuperNatural Ⅲ: SN0198703-08
NPASS: NPC167763
{NPAtlas: NPA024801
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Trididemnum solidum | Trididemnum | Didemnidae | Aplousobranchia | Ascidiacea | Chordata | Metazoa | Eukaryota |
| Lyngbya majuscula | Lyngbya | Oscillatoriaceae | Oscillatoriales | Cyanophyceae | Cyanobacteriota | None | Bacteria |
| Tistrella mobilis | Tistrella | Geminicoccaceae | Geminicoccales | Alphaproteobacteria | Pseudomonadota | None | Bacteria |
Properties Information
Molecule Weight: 1112.3729999999998
TPSA？: 287.9
MolLogP？: 2.316500000000016
Number of H-Donors: 5
Number of H-Acceptors: 15
RingCount: 4
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Homo sapiens | A549 | IC50 | 2.0 | nM | 10.1021/acs.jmedchem.0c01746 |
| Homo sapiens | HT-29 | IC50 | 2.0 | nM | 10.1021/acs.jmedchem.0c01746 |
| Homo sapiens | SK-MEL-28 | IC50 | 2.0 | nM | 10.1021/acs.jmedchem.0c01746 |
| Mus musculus | P388 | IC50 | 2.0 | nM | 10.1021/acs.jmedchem.0c01746 |
| Mus musculus | P388 | IC50 | 100.0 | nM | 10.1021/acs.jmedchem.0c01746 |
| Mus musculus | P388 | IC50 | 400.0 | nM | 10.1021/acs.jmedchem.0c01746 |
| Mus musculus | P388 | IC50 | 1000.0 | nM | 10.1021/acs.jmedchem.0c01746 |
| Oryctolagus cuniculus | Oryctolagus cuniculus | IC50 | 4400.0 | nM | 10.1016/s0960-894x(98)00662-3 |
| None | Unchecked | IC50 | 100.0 | nM | 10.1021/acs.jmedchem.0c01746 |