2-[(2S,4S)-4-{[(2R,4S,5S,6S)-4-(benzylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl]-2-oxoethyl pentanoate

• ChemBase ID: 154048
• Molecular Formular: C39H43NO12
• Molecular Mass: 717.75822
• Monoisotopic Mass: 717.27852582
• SMILES: CCCCC(=O)OCC(=O)[C@@]1(Cc2c(c(c3c(c2O)C(=O)c2cccc(c2C3=O)OC)O)[C@H](C1)O[C@H]1C[C@@H]([C@@H]([C@@H](O1)C)O)NCc1ccccc1)O
• Canonical SMILES: CCCCC(=O)OCC(=O)[C@@]1(O)C[C@H](O[C@H]2C[C@H](NCc3ccccc3)[C@@H]([C@@H](O2)C)O)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC
• InChI: InChI=1S/C39H43NO12/c1-4-5-14-28(42)50-19-27(41)39(48)16-23-31(38(47)33-32(36(23)45)35(44)22-12-9-13-25(49-3)30(22)37(33)46)26(17-39)52-29-15-24(34(43)20(2)51-29)40-18-21-10-7-6-8-11-21/h6-13,20,24,26,29,34,40,43,45,47-48H,4-5,14-19H2,1-3H3/t20-,24-,26-,29-,34+,39-/m0/s1
• InChIKey: IUKSGXMOHXEUJY-YWVRLZQXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2S,4S)-4-{[(2R,4S,5S,6S)-4-(benzylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl]-2-oxoethyl pentanoate
• IUPAC Traditional name: 2-[(2S,4S)-4-{[(2R,4S,5S,6S)-4-(benzylamino)-5-hydroxy-6-methyloxan-2-yl]oxy}-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-oxoethyl pentanoate
• Synonyms: N-Benzyladriamycin-14-valerate; AD 198

Database IDs

• CAS Number: 98983-21-2
• PubChem SID: 162248187
• PubChem CID: 127201

CALCULATED PROPERTIES

• Acid pKa: 9.400707
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): 2.6698492
• LogD (pH = 7.4): 4.158939
• Log P: 5.234552
• Molar Refractivity: 186.9613 cm^3
• Polarizability: 73.38356 Å^3
• Polar Surface Area: 198.15 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble
• Apperance: red solid

Safety Information

• RTECS: SA3697000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C39H43NO12

DETAILS

Sigma Aldrich - A9481

Biochem/physiol Actions
AD 198 is a PKC-delta activator. Phospholipid scramblase 3 (PLS3) is an enzyme that plays a critical role in mitochondrial morphology, functions, and apoptotic response. During apoptosis, activated protein kinase C-delta (PKC-delta) translocates to mitochondria and phosphorylates PLS3. Used to show that PLS3 is a critical downstream effector of PKC-delta in AD 198-induced apoptosis.