Propanamide,N-[(1S,2R,3E,5E,7S,9E,11E,13S,15R,19R)-7,13-dihydroxy-1,4,10,19-tetramethyl-17,18-dioxo-16-oxabicyclo[13.2.2]nonadeca-3,5,9,11-tetraen-2-yl]-2-oxo-

Modify Date: 2024-03-26 15:44:58

Propanamide,N-[(1S,2R,3E,5E,7S,9E,11E,13S,15R,19R)-7,13-dihydroxy-1,4,10,19-tetramethyl-17,18-dioxo-16-oxabicyclo[13.2.2]nonadeca-3,5,9,11-tetraen-2-yl]-2-oxo- Structure
Propanamide,N-[(1S,2R,3E,5E,7S,9E,11E,13S,15R,19R)-7,13-dihydroxy-1,4,10,19-tetramethyl-17,18-dioxo-16-oxabicyclo[13.2.2]nonadeca-3,5,9,11-tetraen-2-yl]-2-oxo- structure
Common Name Propanamide,N-[(1S,2R,3E,5E,7S,9E,11E,13S,15R,19R)-7,13-dihydroxy-1,4,10,19-tetramethyl-17,18-dioxo-16-oxabicyclo[13.2.2]nonadeca-3,5,9,11-tetraen-2-yl]-2-oxo-
CAS Number 23623-31-6 Molecular Weight 459.53200
Density 1.23g/cm3 Boiling Point N/A
Molecular Formula C25H33NO7 Melting Point N/A
MSDS N/A Flash Point N/A

 Use of Propanamide,N-[(1S,2R,3E,5E,7S,9E,11E,13S,15R,19R)-7,13-dihydroxy-1,4,10,19-tetramethyl-17,18-dioxo-16-oxabicyclo[13.2.2]nonadeca-3,5,9,11-tetraen-2-yl]-2-oxo-


Lankacidin C is an inhibitor of protein synthesis in vitro. Lankacidin C inhibits the activity of L1210 leukemia, B16 melanoma and 6C3 HED/OG lymphosarcoma cell lines. Lankacidin C has antibacterial activity and antitumor activity[1][2].

 Names

Name Lankacidin C
Synonym More Synonyms

  Biological Activity

Description Lankacidin C is an inhibitor of protein synthesis in vitro. Lankacidin C inhibits the activity of L1210 leukemia, B16 melanoma and 6C3 HED/OG lymphosarcoma cell lines. Lankacidin C has antibacterial activity and antitumor activity[1][2].
Related Catalog
In Vivo Lankacidin C (75-1000 mg/kg;腹腔注射;一天一次持续 5 天) 以剂量依赖性方式延长了 (C57BL/6×DBA/2) F1 (BDF1) 小鼠的平均生存时间。Lankacidin C (1000 mg/kg) 在植入 B-16 黑色素瘤的 C57BL/6 小鼠中显著抑制了 B-16 黑色素瘤的生长[2]。 Lankacidin C (300 mg/kg;腹腔注射;一天一次持续 6 天) 在含有L-1210/6-巯基嘌呤或 L-1210/阿糖胞苷的 BDF1 小鼠中,抑制对 6-巯基嘌呤 (6-Mercaptopurine,HY-13677) 或阿糖胞苷 (Cytosine Arabinoside,HY-13605) 耐药的 L-1210 细胞活性[2]。 Lankacidin C (10-100 mg/kg;腹腔注射;一天一次持续 5 天) 显著延长了含有 6C3 HED/OG 或 6C3 HED/RG 淋巴肉瘤的 C3H/He 小鼠平均生存时间[2]。 Lankacidin C (500 mg/kg;腹腔注射;一天一次持续 3 或 4 天) 在抗原刺激前后抑制 ICR 小鼠抗绵羊红细胞抗体的产生[2]。 Animal Model: C57BL/6, C3H/He, ICR and (C57BL/6×DBA/2) F1 (BDF1) mice[2]. Dosage: 10, 20, 25, 30, 40, 50, 100, 150, 250, 300, 500, 600 or 1000 mg/kg Administration: Intraperitoneal injection; once daily for 3, 4, 5 or 6 days Result: Inhibited the growth of L1210 leukemia, B16 melanoma and 6C3 HED/OG or 6C3 HED/RG lymphosarcoma cells.
References

[1]. Cai L, et al. Modular Approaches to Lankacidin Antibiotics. J Am Chem Soc. 2020 Sep 2;142(35):15116-15126.  

[2]. Ootsu K, et al. Effects of Lankacidin group (T2636) antibiotics on the tumor growth and immune response against sheep erythrocytes in mice. Gan. 1973 Oct;64(5):481-92.  

 Chemical & Physical Properties

Density 1.23g/cm3
Molecular Formula C25H33NO7
Molecular Weight 459.53200
Exact Mass 459.22600
PSA 130.00000
LogP 2.10860
Index of Refraction 1.566

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UZ0780000
CHEMICAL NAME :
Pyruvamide, N-(7,13-dihydroxy-1,4,10,19-tetramethyl-17,18-dioxo-1 6-oxabicyclo(13.2.2) nonadeca-3,5,9,11-tetraen-2-yl)-, (all-E)-(1S,2R,7S,13S,15R,19R)-(-)-
CAS REGISTRY NUMBER :
23623-31-6
LAST UPDATED :
199112
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C25-H33-N-O7
MOLECULAR WEIGHT :
459.59
WISWESSER LINE NOTATION :
T6-17- A B AOV DV IU KU OU QUTJ C1 E1 HQ K1 NQ Q1 SMVV1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85FZAT "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967 Volume(issue)/page/year: -,184,1967
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 26,647,1973

 Synthetic Route

~%

Propanamide,N-[(1S,2R,3E,5E,7S,9E,11E,13S,15R,19R)-7,13-dihydroxy-1,4,10,19-tetramethyl-17,18-dioxo-16-oxabicyclo[13.2.2]nonadeca-3,5,9,11-tetraen-2-yl]-2-oxo- Structure

Propanamide,N-[...

CAS#:23623-31-6

Literature: Kakinuma, Katsumi; Uzawa, Jun; Uramoto, Masakazu Tetrahedron Letters, 1982 , vol. 23, # 50 p. 5303 - 5306

 Precursor & DownStream

Precursor  1

DownStream  0

 Synonyms

Bundlin A
(-)-lankacidin C
Antibiotic T-2636C
N-[(1S,2R,3E,5E,7S,9E,11E,13S,15R,19R)-7,13-Dihydroxy-1,4,10,19-tetramethyl-17,18-dioxo-16-oxabicyclo[13.2.2]nonadeca-3,5,9,11-tetraen-2-yl]-2-oxopropanamide
lankacidins
Lankacidin