Didemnin B
AlkaPlorer ID: AK007242
Synonym: 'Didemnin B', '', '77327-05-0', 'L-Tyrosine, N-1-N-4-3-hydroxy-4-N-N-1-(2-hydroxy-1-oxopropyl)- L-prolyl-N-methyl-L-leucyl-L-threonylamino-5-methyl- 1-oxoheptyloxy-2,5-dimethyl-1,3-dioxohexyl-L-leucyl- L-prolyl-N,O-dimethyl-, .phi.-lactone', 'Didemnin A, N-(1-(2-hydroxy-1-oxopropyl)-L-prolyl)-, (S)-', 'DIDEMNIN B', '15H-Pyrrolo2,1-f1,15,4,7,10,20dioxatetraazacyclotri- cosine, cyclic peptide deriv.'
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-(2-hydroxypropanoyl)-N-methylpyrrolidine-2-carboxamide
Structure
SMILES: CC[C@H](C)[C@H]1N=C(O)[C@@H](N=C(O)[C@@H](CC(C)C)N(C)C(=O)[C@@H]2CCCN2C(=O)C(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)N=C(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-XYUQHQMCSA-N
Reference
Didemnins and Tunichlorin: Novel Natural Products from the Marine Tunicate Trididemnum solidum
PubChem CID: 13895197
LOTUS: LTS0213524
NPASS: NPC470903
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Trididemnum solidum | Trididemnum | Didemnidae | Aplousobranchia | Ascidiacea | Chordata | Metazoa | Eukaryota |
Properties Information
Molecule Weight: 1112.3729999999998
TPSA？: 298.37
MolLogP？: 4.837400000000014
Number of H-Donors: 5
Number of H-Acceptors: 15
RingCount: 4
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Agrobacterium tumefaciens | Agrobacterium tumefaciens | Inhibition | 100.0 | % | 10.1021/np50073a029 |
| Canis lupus familiaris | Canis familiaris | Activity | nan | None | 10.1021/np50055a001 |
| Homo sapiens | A549 | IC50 | 0.002 | ug.mL-1 | 10.1021/np200543z |
| Homo sapiens | A549 | IC50 | 2.0 | nM | 10.1021/jm040788m |
| Homo sapiens | HCT-116 | IC50 | 9.0 | nM | 10.1021/np100846s |
| Homo sapiens | HT-29 | IC50 | 0.002 | ug.mL-1 | 10.1021/np200543z |
| Homo sapiens | HT-29 | IC50 | 2.0 | nM | 10.1021/jm040788m |
| Homo sapiens | LNCaP | IC50 | 2.8 | nM | 10.1021/jm100729b |
| Homo sapiens | MCF7 | IC50 | 12.0 | nM | 10.1021/jm000168v |
| Homo sapiens | MCF7 | IC50 | 200.0 | nM | 10.1021/jm000168v |
| Homo sapiens | MCF7 | Inhibition | 51.0 | % | 10.1021/jm000168v |
| Homo sapiens | MCF7 | Inhibition | 68.0 | % | 10.1021/jm000168v |
| Homo sapiens | MCF7 | Inhibition | 76.0 | % | 10.1021/jm000168v |
| Homo sapiens | T-24 | IC50 | 0.046 | ug.mL-1 | 10.1021/jm00168a016 |
| Human alphaherpesvirus 2 | Human alphaherpesvirus 2 | Survival | 85.0 | % | 10.1021/np50055a001 |
| Human immunodeficiency virus 1 | Human immunodeficiency virus type 1 reverse transcriptase | IC50 | 200.0 | ug.mL-1 | 10.1021/np50073a012 |
| Mus musculus | B16 | T/C | 135.0 | % | 10.1021/np50055a001 |
| Mus musculus | B16 | T/C | 139.0 | % | 10.1021/np50055a001 |
| Mus musculus | B16 | T/C | 144.0 | % | 10.1021/np50055a001 |
| Mus musculus | B16 | T/C | 146.0 | % | 10.1021/np50055a001 |
| Mus musculus | B16 | T/C | 155.0 | % | 10.1021/np50055a001 |
| Mus musculus | B16 | T/C | 157.0 | % | 10.1021/np50055a001 |
| Mus musculus | B16 | T/C | 160.0 | % | 10.1021/np50055a001 |
| Mus musculus | L1210 | IC50 | 0.0025 | ug.mL-1 | 10.1021/np50070a001 |
| Mus musculus | L1210 | ID50 | 0.002 | ug ml-1 | 10.1021/np50055a001 |
| Mus musculus | L1210 | ID50 | 1.2 | ng ml-1 | 10.1021/jm00106a002 |
| Mus musculus | L1210 | ID50 | 3.7 | ng ml-1 | 10.1021/jm00106a002 |
| Mus musculus | Mus musculus | AC50 | 1.6 | g | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | -4.5 | g | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | -3.8 | g | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | -3.4 | g | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | -3.3 | g | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | -3.2 | g | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | -2.2 | g | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | -1.7 | g | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | -1.3 | g | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | -0.5 | g | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | -0.4 | g | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | 0.1 | g | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | 0.3 | g | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | 0.8 | g | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | 1.2 | g | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | 29.0 | % | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | 40.0 | % | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | 49.0 | % | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | 58.0 | % | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Activity | nan | None | 10.1021/np50055a001 |
| Mus musculus | Mus musculus | Inhibition | nan | % | 10.1021/np50055a001 |
| Mus musculus | P388 | Activity | 100.0 | % | 10.1021/np50055a001 |
| Mus musculus | P388 | T/C | 125.0 | % | 10.1021/np50055a001 |
| Mus musculus | P388 | T/C | 138.0 | % | 10.1021/np50055a001 |
| Mus musculus | P388 | T/C | 140.0 | % | 10.1021/np50055a001 |
| Mus musculus | P388 | T/C | 143.0 | % | 10.1021/np50055a001 |
| Mus musculus | P388 | T/C | 157.0 | % | 10.1021/np50055a001 |
| Mus musculus | P388 | T/C | 176.0 | % | 10.1021/np50055a001 |
| Mus musculus | P388 | T/C | 199.0 | % | 10.1021/np50055a001 |
| Mus musculus | RAW264.7 | IC50 | 562.0 | nM | 10.1016/j.bmcl.2011.10.042 |
| Mus musculus | RAW264.7 | IC50 | 692.0 | nM | 10.1016/j.bmcl.2011.10.042 |
| Oryctolagus cuniculus | Oryctolagus cuniculus | IC50 | 890.0 | nM | 10.1021/jm000168v |
| Oryctolagus cuniculus | Oryctolagus cuniculus | IC50 | 2000.0 | nM | 10.1021/jm000168v |
| Rattus norvegicus | Rattus norvegicus | Activity | 80.0 | % | 10.1021/np50055a001 |
| Rattus norvegicus | Rattus norvegicus | Activity | nan | None | 10.1021/np50055a001 |
| Rift Valley fever virus | Rift Valley fever virus | Activity | nan | None | 10.1021/np50055a001 |
| Rift Valley fever virus | Rift Valley fever virus | Survival | 90.0 | % | 10.1021/np50055a001 |
| Sandfly fever Sicilian virus | Sandfly fever Sicilian virus | Activity | nan | None | 10.1021/np50055a001 |
| Venezuelan equine encephalitis virus | Venezuelan equine encephalitis virus | Activity | nan | None | 10.1021/np50055a001 |
| Yellow fever virus | Yellow fever virus | Activity | nan | None | 10.1021/np50055a001 |
| None | Lymphocyte | IC50 | 1e-05 | ug.mL-1 | 10.1021/np50055a001 |
| None | Lymphocyte | IC50 | 0.19 | ug.mL-1 | 10.1021/np50055a001 |
| None | Molecular identity unknown | IC50 | 3000.0 | nM | 10.1016/s0960-894x(00)00585-0 |
| None | NON-PROTEIN TARGET | GI50 | 13.0 | nM | 10.1016/s0960-894x(00)00585-0 |
| None | NON-PROTEIN TARGET | Hepatotoxicity (acute) | 5.3 | % | 10.1016/s0399-8320(04)95062-2 |
| None | NON-PROTEIN TARGET | Hepatotoxicity (animal toxicity known) | nan | None | 10.1016/s0399-8320(04)95062-2 |
| None | NON-PROTEIN TARGET | Hepatotoxicity (benign tumour) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | NON-PROTEIN TARGET | Hepatotoxicity (granulomatous hepatitis) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | NON-PROTEIN TARGET | Hepatotoxicity (mechanism) | nan | None | 10.1016/s0399-8320(04)95062-2 |
| None | NON-PROTEIN TARGET | Hepatotoxicity (moderate) | 3.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | NON-PROTEIN TARGET | Hepatotoxicity (moderate) | 32.0 | % | 10.1016/s0399-8320(04)95062-2 |
| None | NON-PROTEIN TARGET | Hepatotoxicity (time to onset) | nan | None | 10.1016/s0399-8320(04)95062-2 |
| None | NON-PROTEIN TARGET | LC50 | 3800.0 | nM | 10.1016/s0960-894x(00)00585-0 |
| None | T-cell | IC50 | 5e-05 | ug.mL-1 | 10.1021/np50055a001 |
| None | Unchecked | Hepatotoxicity (acute) | 2.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (association with vascular disease) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (choleostasis) | 1.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (chronic liver disease) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (cirrhosis) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (comment) | nan | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (cytolytic) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (malignant tumour) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (severe hepatitis) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (steatosis) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (successful reintroduction) | nan | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | IC50 | 0.0001 | ug.mL-1 | 10.1021/np50055a001 |
| None | Unchecked | TGI | 66.0 | nM | 10.1016/s0960-894x(00)00585-0 |