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(S) -Seco-Duocarmycin SA

CAT: 0804-HY-129356A-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-129356A-01Size:1 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
(S) -Seco-Duocarmycin SA is the S-enantiomer of Seco-Duocarmycin SA. Seco-Duocarmycin SA is a DNA alkylating agent. Seco-Duocarmycin SA is an antitumor antibiotic (IC50 = 10 pM). Seco-Duocarmycin SA can induce a concentration-dependent increase in apoptotic cell death. Seco-Duocarmycin SA can lead to significant cell cycle arrest in S and G2/M phases. Seco-Duocarmycin SA acts as an ADC cytotoxin for antibody-drug conjugates[1][2][3].
CAS Number
152785-82-5
UNSPSC
12352203
Target
ADC Payload; Antibiotic; Apoptosis; DNA Alkylator/Crosslinker
Type
ADC Related
Related Pathways
Antibody-drug Conjugate/ADC Related; Anti-infection; Apoptosis; Cell Cycle/DNA Damage
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/s-seco-duocarmycin-sa.html
Purity
99.0
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
ClC[C@H]1C2=C(C=C(O)C3=C2C=C(C(OC)=O)N3)N(C(C4=CC5=CC(OC)=C(OC)C(OC)=C5N4)=O)C1
Molecular Formula
C25H24ClN3O7
Molecular Weight
513.93
References & Citations
[1]Tichenor MS, et al. Systematic exploration of the structural features of yatakemycin impacting DNA alkylation and biological activity. J Am Chem Soc. 2007 Sep 5;129 (35) :10858-69.|[2]Morcos, A., et al., (2025) . Seco-Duocarmycin SA in Aggressive Glioblastoma Cell Lines. International journal of molecular sciences, 26 (6), 2766.|[3]Lutz F. Tietze, et al. A Concise and Efficient Synthesis of seco-Duocarmycin SA. European Journal of Organic Chemistry 2003 (3), 562-566.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
ADC Related
Clinical Information
No Development Reported

Chemical Information

(S)-Seco-Duocarmycin SA
CAS Number152785-82-5
PubChem CID11005763
IUPAC Namemethyl (8S)-8-(chloromethyl)-4-hydroxy-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-2-carboxylate
Molecular FormulaC25H24ClN3O7
Molecular Weight513.9
XLogP3.7
Topological Polar Surface Area126
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count7
Rotatable Bond Count7
Heavy Atom Count36
Formal Charge0
Complexity835
SMILES
COC1=C(C(=C2C(=C1)C=C(N2)C(=O)N3C[C@H](C4=C5C=C(NC5=C(C=C43)O)C(=O)OC)CCl)OC)OC
InChI
InChI=1S/C25H24ClN3O7/c1-33-18-6-11-5-14(27-20(11)23(35-3)22(18)34-2)24(31)29-10-12(9-26)19-13-7-15(25(32)36-4)28-21(13)17(30)8-16(19)29/h5-8,12,27-28,30H,9-10H2,1-4H3/t12-/m1/s1
InChIKey
SDJNZXKVYYJDDM-GFCCVEGCSA-N
Chemical Structure
2D Structure
2D structure of (S)-Seco-Duocarmycin SA
CAS: 152785-82-5
CID: 11005763
Formula: C25H24ClN3O7
MW: 513.9
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight513.9
XLogP33.7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count7
Rotatable Bond Count7
Exact Mass513.1302778
Monoisotopic Mass513.1302778
Topological Polar Surface Area126 Ų
Heavy Atom Count36
Formal Charge0
Complexity835
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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