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Kahalalide F

CAT: 0013-GTR19273882-01Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19273882-01Size:10 mg
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Description
Kahalalide F is a novel marine-derived antitumor agent known for inhibiting DNA synthesis. It exhibits cytotoxicity that is not correlated with the expression levels of the multidrug resistance gene MDR1 or the tyrosine kinase HER2/NEU, and is only slightly related to the expression of the anti-apoptotic protein BCL-2. Kahalalide F hinders the PI3K-Akt signaling pathway by depleting ErbB3. Its effects are rapidly activated with short pulse treatments. The compound primarily induces cell death through oncosis (cellular swelling) in tumor cells. Kahalalide F can be utilized in studies of prostate cancer, breast cancer, vulvar cancer, and non-small cell lung cancer.
CAS Number
149204-42-2
Smiles
C ([C@H] (NC ([C@@H] (NC ([C@@H] (NC ([C@H] (NC (CCCC (C) C) =O) [C@@H] (C) C) =O) [C@@H] (C) O) =O) C (C) C) =O) [C@@H] (C) C) (=O) N1[C@@H] (C (N[C@H] (C (N[C@@H] (C (N[C@H]2C (=O) N[C@] ([C@H] (CC) C) (C (=O) N[C@H] (C (C) C) C (=O) N[C@@H] (CC3=CC=CC=C3) C (=O) N/C (=C\C) /C (=O) N[C@@H] (C (C) C) C (=O) O[C@@H]2C) [H]) =O) [C@H] (CC) C) =O) CCCN) =O) CCC1
Molecular Formula
C75H124N14O16
Molecular Weight
1477.9
Storage Conditions
-20°C
Notes
For research use only.

Chemical Information

Kahalalide F

Kahalalide F is a cyclodepsipeptide.

CAS Number149204-42-2
PubChem CID9898671
IUPAC Name(2R)-N-[(2S)-5-amino-1-[[(2R,3S)-1-[[(3S,6Z,9S,12R,15R,18R,19R)-9-benzyl-15-[(2S)-butan-2-yl]-6-ethylidene-19-methyl-2,5,8,11,14,17-hexaoxo-3,12-di(propan-2-yl)-1-oxa-4,7,10,13,16-pentazacyclononadec-18-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]-1-[(2R)-2-[[(2S)-2-[[(2S,3R)-3-hydroxy-2-[[(2R)-3-methyl-2-(5-methylhexanoylamino)butanoyl]amino]butanoyl]amino]-3-methylbutanoyl]amino]-3-methylbutanoyl]pyrrolidine-2-carboxamide
Molecular FormulaC75H124N14O16
Molecular Weight1477.9
XLogP7.4
Topological Polar Surface Area442
Hydrogen Bond Donor Count14
Hydrogen Bond Acceptor Count17
Rotatable Bond Count33
Heavy Atom Count105
Formal Charge0
Complexity2990
SMILES
CC[C@H](C)[C@@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N/C(=C\C)/C(=O)N[C@H](C(=O)O[C@@H]([C@H](C(=O)N1)NC(=O)[C@@H]([C@@H](C)CC)NC(=O)[C@H](CCCN)NC(=O)[C@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](C(C)C)NC(=O)CCCC(C)C)C)C(C)C)CC3=CC=CC=C3)C(C)C
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+/m0/s1
InChIKey
RCGXNDQKCXNWLO-YUHQQKLOSA-N
Chemical Structure
2D Structure
2D structure of Kahalalide F
CAS: 149204-42-2
CID: 9898671
Formula: C75H124N14O16
MW: 1477.9
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1477.9
XLogP37.4
Hydrogen Bond Donor Count14
Hydrogen Bond Acceptor Count17
Rotatable Bond Count33
Exact Mass1476.93197392
Monoisotopic Mass1476.93197392
Topological Polar Surface Area442 Ų
Heavy Atom Count105
Formal Charge0
Complexity2990
Isotope Atom Count0
Defined Atom Stereocenter Count16
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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