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1H-4,6:16,19-Dietheno-21,25-metheno-12H-[1,3]dioxolo[4,5-g]pyrido[2',3':17,18][1,10]dioxacycloeicosino[2,3,4-ij]isoquinoline,2,3,13,14,14a,15,26,26a-octahydro-22,30-dimethoxy-1,14-dimethyl-,(14aS,26aR)-

HCID 360849
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Basic information

CAS
481-49-2
Standard SMILES
COc1ccc2cc1Oc1ccc(cc1)CC1c3c(cc4c(c3Oc3cc5c(cc3OC)CCN(C)C5C2)OCO4)CCN1C
InChIKey
YVPXVXANRNDGTA-UHFFFAOYSA-N
Molecular formula
C37H38N2O6
Average molar mass
606.7 g/mol
Monoisotopic mass
606.27298694

Overview

1H-4,6:16,19-Dietheno-21,25-metheno-12H-[1,3]dioxolo[4,5-g]pyrido[2',3':17,18][1,10]dioxacycloeicosino[2,3,4-ij]isoquinoline,2,3,13,14,14a,15,26,26a-octahydro-22,30-dimethoxy-1,14-dimethyl-,(14aS,26aR)- has been reported in Stephania delavayi, Stephania cephalantha, and other organisms with data available.

Names & identifiers

Preferred name
1H-4,6:16,19-Dietheno-21,25-metheno-12H-[1,3]dioxolo[4,5-g]pyrido[2',3':17,18][1,10]dioxacycloeicosino[2,3,4-ij]isoquinoline,2,3,13,14,14a,15,26,26a-octahydro-22,30-dimethoxy-1,14-dimethyl-,(14aS,26aR)-
IUPAC
22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.216,19.13,10.121,25.04,8.031,35.014,39]nonatriaconta-1(33),3(39),4(8),9,16(38),17,19(37),21,23,25(36),31,34-dodecaene
English name
Cepharanthine
Molecular formula
C37H38N2O6
Molecular weight
606.71

Names & synonyms

1H-4,6:16,19-Dietheno-21,25-metheno-12H-[1,3]dioxolo[4,5-g]pyrido[2',3':17,18][1,10]dioxacycloeicosino[2,3,4-ij]isoquinoline,2,3,13,14,14a,15,26,26a-octahydro-22,30-dimethoxy-1,14-dimethyl-,(14aS,26aR)-C37H38N2O6NCGC00095194-0122,33-Dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.216,19.13,10.121,25.04,8.031,35.014,39]nonatriaconta-1(33),3(39),4(8),9,16(38),17,19(37),21,23,25(36),31,34-dodecaeneCepharanthine [M+H]+CHEMBL1473842HMS3370G06HMS5082L16s4238NCGC00095194-02NCGC00095194-03NCGC00095194-04
Show more names
CEPHARANTHINcepharantinCepharanthine, >=98%(15S,31R)-36,54-Dimethoxy-16,32-dimethyl-15,16,17,18,31,32,33,34-octahydro-2,6-dioxa-1(4,5)-[1,3]dioxolo[4,5-g]isoquinolina-3(7,1)-isoquinolina-5(1,3),7(1,4)-dibenzenacyclooctaphaneNSC-623442Stephanotis

Properties

Computed structural properties

XLogP
6.5
Topological polar surface area
61.9 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
8
Rotatable bonds
2
Heavy atoms
45
Formal charge
0
Complexity
994

Physicochemical properties

Melting point
145 · 145-155°
alpha
20 · D20 +277° (c = 2 in chloroform)
Boiling point
654.03 °C · 654.03°C (rough estimate)
Density
1.1761 · 1.1761 (rough estimate)
refractive index
1.53 · 1.5300 (estimate)
storage temp.
2 · under inert gas (nitrogen or Argon) at 2-8°C
solubility
Soluble in DMSO (35 mg/mL) or ethanol (20 mg/mL)
form
solid
pka
7.61 · 7.61±0.20(Predicted)
color
Pale yellow
Stability
2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.
Major Application
metabolomicsvitamins, nutraceuticals, and natural products
InChIKey
YVPXVXANRNDGTA-WDYNHAJCSA-N
SMILES
C1CC2C=C3OCOC3=C3OC4C(OC)=CC5CCN(C)[C@]([H])(CC6=CC(=C(OC)C=C6)OC6C=CC(C[C@@]([H])(C=23)N1C)=CC=6)C=5C=4

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
WGK 1
Signal word
Warning
Symbol(GHS)
GHS07
Storage Class
11 - Combustible Solids
Hazard statements
H302
Hazard Classifications
Acute Tox. 4 Oral
Precautionary statements
P264-P270-P301+P312-P330-P501

Chemistry & industry

Applications · 3 items

DescriptionCepharanthine is diclofenac quinoline alkaloid isolated from rhizome of Stephania japonica, which was first recorded in “Bencao shiyi” and functions as clearing heat, promoting diuresis and detumescence in traditional Chinese medicine. Cepharanthine is a pure and natural extract of the Stephania cepharantha Hayata plant, a rare species that is native to Kotosho Island, southeast of Taiwan. In 1914, the renowned botanist, Bunzo Hayata reported the plant for the first time. Two decades later, Dr. Heisaburo Kondo purified its active ingredient and named it “Cepharanthine.” Stephania japonica was used to treat tuberculosis and other consumptive diseases which provided a clue for its development on lung disease.

HistoryPromoting leukocytosis of cepharanthine in tuberculosis patients was first recorded in the proceeding Institute of Chemotherapy by the Japanese scholar Yamaguchi in 1946. In 1948, Chinese scholar Yuhuang Zhao also received this compound and published it in D.M.Med.It is thought that cepharanthine may stimulate the reticuloendothelial system, then activate hematopoietic tissue, and promote myeloproliferation. Therefore, the number of white blood cells in the peripheral blood increased significantly. Due to its good safety, cepharanthine is currently widely used in cancer patients with granulocytopenia or leukopenia embolism after radiotherapy and chemotherapy and so on.In addition, Chinese scientists extracted five kinds of dibenzylisoquinoline alkaloids from Chinese herbal medicine in 1977, which could significantly improve the silicosis symptoms in rat . In 1993, it was issued as anti-pneumoconiosis drug by CFDA and is used for delaying the progress of pneumoconiosis in clinic.

UsesCepharanthine is a biscoclaurine alkaloid that has antiinflammatory, antineoplastic, hepatoprotectant, radiopropective and other biological functions. It is used to treat many acute and chronic diseases, including pit viper bites, alopecia areata, and leucopenia in radiation therapy.

Upstream & downstream products

Upstream raw materials

Lonicerae Japonicae Caulis
Additional notes · 1 item

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Compound notes

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Stephanolin
CEPHARANTHINE
CEPHARANTHINUM
SinoInterme? CPHE
Oxyacanthan,12'-dimethoxy-2,2'-dimethyl-6,7- [methylenebis(oxy)]-6',12'-Dimethoxy-2,2'-dimethyl-6,7-[methylenebis-(oxy)]oxyacanthan(14S,27R)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.2^{16,19.1^{3,10.1^{21,25.0^{4,8.0^{31,35.0^{14,39]nonatriaconta-1(33),3(39),4(8),9,16(38),17,19(37),21,23,25(36),31,34-dodecaene

Database identifiers

CAS
481-49-2
PubChem CID
360849
ChEMBL
CHEMBL1473842
Nikkaji
J3.216.172C
EWG's Food Scores
1 · 1
FDA UNII
7592 YJ0J6T · 7592YJ0J6T
UNSPSC Code
12352205 · 12352205
NACRES
25 · NA.25
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
264 · P264-P270-P301+P312-P330-P501
WGK Germany
1 · WGK 1
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 Oral · Acute Tox. 4 Oral

DefinitionChEBI: Cepharanthine is a bisbenzylisoquinoline alkaloid from tubers of Stephania; stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation. It is a member of isoquinolines and a bisbenzylisoquinoline alkaloid.