CAS 13137-64-9|Periplocin

Introduction：Basic information about CAS 13137-64-9|Periplocin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Periplocin BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Synonyms

Common Name	Periplocin
CAS Number	13137-64-9	Molecular Weight	682.795
Density	1.4±0.1 g/cm3	Boiling Point	877.4±65.0 °C at 760 mmHg
Molecular Formula	C₃₆H₅₆O₁₃	Melting Point	205°C
MSDS	/	Flash Point	272.8±27.8 °C

Names

Name	3-[(3S,5S,10R,13R,14S,17R)-3-[(2R,5R)-6-[[(3R,6S)-4,6-dihydroxy-2-methyloxan-3-yl]oxymethyl]-3,5-dihydroxy-4-methoxyoxan-2-yl]oxy-5,14-dihydroxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonym	More Synonyms

Periplocin BiologicalActivity

Description	Periplocin is a cardiotonic steroid isolated from Periploca forrestii. Periplocin promotes tumor cell apoptosis and inhibits tumor growth. Periplocin has the potential to facilitate wound healing through the activation of Src/ERK and PI3K/Akt pathways mediated by Na/K-ATPase[1][2].
Related Catalog	Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>CancerResearch Areas >>Inflammation/Immunology
Target	Apoptosis[2]
In Vitro	Periplocin (5-20 μM; 48 hours; L929 cells) treatment shows increased proliferation up to 131% at 20 μM[1]. Periplocin (5-20 μM; 30-120 minutes; L929 cells) increases phosphorylation of Src, ERK, PI3K and Akt at active sites in a dosedependent and time-dependent manner.Periplocin (5-20 μM; 48 hours) significantly promotes migration of fibroblast cell[1]. Periplocin (5-20 μM; 48 hours) increases collagen production in L929 fibroblast[1]. Periplocin induces Na/KATPase mediates the activation of Src/ERK and PI3K/Akt pathways[1]. Cell Viability Assay[1] Cell Line: L929 cells Concentration: 5 μM, 10 μM, 20 μM Incubation Time: 48 hours Result: Showed increased proliferation up to 131% at 20 μM. Western Blot Analysis[1] Cell Line: L929 cells Concentration: 5 μM, 10 μM, 20 μM Incubation Time: 30 minutes, 60 minutes, 120 minutes Result: Increased phosphorylation of Src, ERK, PI3K and Akt at active sites in a dosedependent and time-dependent manner.
In Vivo	Periplocin (5-20 mg/kg; intraperitoneal injection; daily; for 14 days; female SCID mice) treatment represses the growth of hepatocellular carcinoma (HCC) in xenograft tumor model in mice[2]. Animal Model: Female SCID mice (6-8 weeks old) injected with Huh-7 cells[2] Dosage: 5 mg/kg, 20 mg/kg Administration: Intraperitoneal injection; daily; for 14 days Result: Repressed the growth of hepatocellular carcinoma (HCC) in xenograft tumor model in mice.
References	[1]. Chen L, et al. Periplocin promotes wound healing through the activation of Src/ERK and PI3K/Akt pathways mediated by Na/K-ATPase. Phytomedicine. 2019 Apr;57:72-83. [2]. Cheng CF, et al. Antitumor Effect of Periplocin in TRAIL-Resistant Human Hepatocellular Carcinoma Cells through Downregulation of IAPs. Evid Based Complement Alternat Med. 2013;2013:958025.

Chemical & Physical Properties

Density	1.4±0.1 g/cm3
Boiling Point	877.4±65.0 °C at 760 mmHg
Melting Point	205°C
Molecular Formula	C₃₆H₅₆O₁₃
Molecular Weight	682.795
Flash Point	272.8±27.8 °C
Exact Mass	682.356445
PSA	193.83000
LogP	-1.36
Vapour Pressure	0.0±0.6 mmHg at 25°C
Index of Refraction	1.624
InChIKey	KWBPKUMWVXUSCA-AXQDKOMKSA-N
SMILES	COC1CC(OC2CCC3(C)C4CCC5(C)C(C6=CC(=O)OC6)CCC5(O)C4CCC3(O)C2)OC(C)C1OC1OC(CO)C(O)C(O)C1O
Storage condition	2-8C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FH4919700

CHEMICAL NAME :: Card-20(22)-enolide, 3-((2,6-dideoxy-4-O-beta-D-glucopyranosyl-3-O-methyl- beta-D-ribo- hexopyranosyl)oxy)-5,14-dihydroxy-, (3-beta,5-beta)-

CAS REGISTRY NUMBER :: 13137-64-9

BEILSTEIN REFERENCE NO. :: 0075742

LAST UPDATED :: 199612

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C36-H56-O13

MOLECULAR WEIGHT :: 696.92

WISWESSER LINE NOTATION :: L E5 B666TJ A1 E1 IQ MQ F- DT5OV EHJ& OO- FT6OTJ B1 CQ DO- BT6OTJ CQ DQ EQ F1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 480 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 27,449,1926

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 2500 ug/kg

TOXIC EFFECTS :: Behavioral - muscle weakness Cardiac - arrhythmias (including changes in conduction) Gastrointestinal - nausea or vomiting

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 27,449,1926

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 120 ug/kg

TOXIC EFFECTS :: Behavioral - muscle weakness Cardiac - arrhythmias (including changes in conduction) Gastrointestinal - nausea or vomiting

REFERENCE :: 85ELDJ "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963 Volume(issue)/page/year: -,193,1963

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 121 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85ELDJ "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963 Volume(issue)/page/year: -,151,1963

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 10 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Cardiac - arrhythmias (including changes in conduction) Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 27,449,1926

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 34 mg/kg

TOXIC EFFECTS :: Cardiac - pulse rate Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 27,449,1926

Synonyms

Card-20(22)-enolide, 3-[(2,6-dideoxy-4-O-β-D-glucopyranosyl-β-D-ribo-hexopyranosyl)oxy]-5,14-dihydroxy-, (3β,5β)-

Glucoperiplocymarin

corchorusoside C

(3β,5β)-3-{[2,6-Dideoxy-4-O-(β-D-glucopyranosyl)-β-D-ribo-hexopyranosyl]oxy}-5,14-dihydroxycard-20(22)-enolide

(3β,5β)-3-{[2,6-Dideoxy-4-O-(β-D-glucopyranosyl)-β-D-ribo-hexopyranosyl]oxy}-5,14-dihydroxycard-20(22)-enolido(2-)

Periplogenin + D-cymarose + D-glucose [German]

periplocin

Periplogenin + D-cymarose + D-glucose

Periplocoside

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