ID: ALA499936

Max Phase: Preclinical

Molecular Formula: C75H124N14O16

Molecular Weight: 1477.90

Molecule Type: Small molecule

Representations

Synonyms (1): Kahalalide F
Synonyms from Alternative Forms(1):

Canonical SMILES:  C/C=C1\NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](C(C)C)NC(=O)[C@@H]([C@H](C)CC)NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](CCCN)NC(=O)[C@H]2CCCN2C(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)CCCC(C)C)C(C)C)[C@@H](C)O)C(C)C)C(C)C)[C@H](C)CC)[C@H](C)OC(=O)[C@H](C(C)C)NC1=O

Standard InChI:  InChI=1S/C75H124N14O16/c1-20-44(16)59(71(100)88-62-47(19)105-75(104)58(43(14)15)84-63(92)49(22-3)77-65(94)51(37-48-30-24-23-25-31-48)79-67(96)55(40(8)9)81-70(99)60(45(17)21-2)86-73(62)102)85-64(93)50(32-27-35-76)78-66(95)52-33-28-36-89(52)74(103)57(42(12)13)83-69(98)56(41(10)11)82-72(101)61(46(18)90)87-68(97)54(39(6)7)80-53(91)34-26-29-38(4)5/h22-25,30-31,38-47,50-52,54-62,90H,20-21,26-29,32-37,76H2,1-19H3,(H,77,94)(H,78,95)(H,79,96)(H,80,91)(H,81,99)(H,82,101)(H,83,98)(H,84,92)(H,85,93)(H,86,102)(H,87,97)(H,88,100)/b49-22-/t44-,45-,46-,47+,50+,51+,52-,54-,55-,56+,57-,58+,59-,60-,61+,62-/m1/s1

Standard InChI Key:  RCGXNDQKCXNWLO-WLEIXIPESA-N

Molecule Features

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

Properties

Molecular Weight: 1477.90

Molecular Weight (Monoisotopic): 1476.9320

AlogP:

#Rotatable Bonds:

Polar Surface Area:

Molecular Species:

HBA:

HBD:

#RO5 Violations:

HBA (Lipinski):

HBD (Lipinski):

#RO5 Violations (Lipinski):

CX Acidic pKa:

CX Basic pKa:

CX LogP:

CX LogD:

Aromatic Rings:

Heavy Atoms:

QED Weighted:

Np Likeness Score:

References

1. Shilabin AG, Kasanah N, Wedge DE, Hamann MT..  (2007)  Lysosome and HER3 (ErbB3) selective anticancer agent kahalalide F: semisynthetic modifications and antifungal lead-exploration studies.,  50  (18): [PMID:17696332] [10.1021/jm061288r]

2. Ashour M, Edrada R, Ebel R, Wray V, Wätjen W, Padmakumar K, Müller WE, Lin WH, Proksch P..  (2006)  Kahalalide derivatives from the Indian sacoglossan mollusk Elysia grandifolia.,  69  (11): [PMID:17125219] [10.1021/np060172v]

3. Rao KV, Na MK, Cook JC, Peng J, Matsumoto R, Hamann MT..  (2008)  Kahalalides V-Y isolated from a Hawaiian collection of the sacoglossan mollusk Elysia rufescens.,  71  (5): [PMID:18407693] [10.1021/np070508g]

4. Aly AH, Edrada-Ebel R, Indriani ID, Wray V, Müller WE, Totzke F, Zirrgiebel U, Schächtele C, Kubbutat MH, Lin WH, Proksch P, Ebel R..  (2008)  Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detection in its host plant Polygonum senegalense.,  71  (6): [PMID:18494522] [10.1021/np070447m]

5. Jiménez JC, López-Macià A, Gracia C, Varón S, Carrascal M, Caba JM, Royo M, Francesch AM, Cuevas C, Giralt E, Albericio F..  (2008)  Structure-activity relationship of kahalalide F synthetic analogues.,  51  (16): [PMID:18672864] [10.1021/jm8000828]

6. Debbab A, Aly AH, Edrada-Ebel R, Wray V, Müller WE, Totzke F, Zirrgiebel U, Schächtele C, Kubbutat MH, Lin WH, Mosaddak M, Hakiki A, Proksch P, Ebel R..  (2009)  Bioactive metabolites from the endophytic fungus Stemphylium globuliferum isolated from Mentha pulegium.,  72  (4): [PMID:19271717] [10.1021/np8004997]

7. Liu H, Edrada-Ebel R, Ebel R, Wang Y, Schulz B, Draeger S, Müller WE, Wray V, Lin W, Proksch P..  (2009)  Drimane sesquiterpenoids from the fungus Aspergillus ustus isolated from the marine sponge Suberites domuncula.,  72  (9): [PMID:19778087] [10.1021/np900220r]

8. Ebada SS, Schulz B, Wray V, Totzke F, Kubbutat MH, Müller WE, Hamacher A, Kassack MU, Lin W, Proksch P..  (2011)  Arthrinins A-D: novel diterpenoids and further constituents from the sponge derived fungus Arthrinium sp.,  19  (15): [PMID:21741249] [10.1016/j.bmc.2011.06.013]

9. Shilabin AG, Hamann MT..  (2011)  In vitro and in vivo evaluation of select kahalalide F analogs with antitumor and antifungal activities.,  19  (22): [PMID:21839640] [10.1016/j.bmc.2011.06.050]

10. Pham CD, Hartmann R, Müller WE, de Voogd N, Lai D, Proksch P..  (2013)  Aaptamine derivatives from the Indonesian sponge Aaptos suberitoides.,  76  (1): [PMID:23282083] [10.1021/np300794b]

11. El-Neketi M, Ebrahim W, Lin W, Gedara S, Badria F, Saad HE, Lai D, Proksch P..  (2013)  Alkaloids and polyketides from Penicillium citrinum, an endophyte isolated from the Moroccan plant Ceratonia siliqua.,  76  (6): [PMID:23713692] [10.1021/np4001366]

12. Daletos G, de Voogd NJ, Müller WE, Wray V, Lin W, Feger D, Kubbutat M, Aly AH, Proksch P..  (2014)  Cytotoxic and protein kinase inhibiting nakijiquinones and nakijiquinols from the sponge Dactylospongia metachromia.,  77  (2): [PMID:24479418] [10.1021/np400633m]

13. Liu Y, Wray V, Abdel-Aziz MS, Wang CY, Lai D, Proksch P..  (2014)  Trimeric anthracenes from the endophytic fungus Stemphylium globuliferum.,  77  (7): [PMID:25010124] [10.1021/np500113r]

14. Hammerschmidt L, Aly AH, Abdel-Aziz M, Müller WE, Lin W, Daletos G, Proksch P..  (2015)  Cytotoxic acyl amides from the soil fungus Gymnascella dankaliensis.,  23  (4): [PMID:25600409] [10.1016/j.bmc.2014.12.068]

Source

Source(1):

• Scientific Literature