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Details

Stereochemistry ABSOLUTE
Molecular Formula C48H78O19
Molecular Weight 959.1234
Optical Activity UNSPECIFIED
Defined Stereocenters 27 / 27
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ASIATICOSIDE

SMILES

C[C@]1([H])CC[C@@]2(CC[C@]3(C)C(=CC[C@]4([H])[C@@]5(C)C[C@]([H])([C@@]([H])([C@@](C)(CO)[C@]5([H])CC[C@]43C)O)O)[C@]2([H])[C@@]1([H])C)C(=O)O[C@@]6([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO[C@@]7([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O7)O[C@@]8([H])[C@@]([H])([C@@]([H])([C@]([H])([C@]([H])(C)O8)O)O)O)O)O)O6)O)O)O

InChI

InChIKey=WYQVAPGDARQUBT-FGWHUCSPSA-N
InChI=1S/C48H78O19/c1-20-10-13-48(15-14-46(6)23(29(48)21(20)2)8-9-28-44(4)16-24(51)39(60)45(5,19-50)27(44)11-12-47(28,46)7)43(61)67-42-36(58)33(55)31(53)26(65-42)18-62-40-37(59)34(56)38(25(17-49)64-40)66-41-35(57)32(54)30(52)22(3)63-41/h8,20-22,24-42,49-60H,9-19H2,1-7H3/t20-,21+,22+,24-,25-,26-,27-,28-,29+,30+,31-,32-,33+,34-,35-,36-,37-,38-,39+,40-,41+,42+,44+,45+,46-,47-,48+/m1/s1

HIDE SMILES / InChI

Molecular Formula C48H78O19
Molecular Weight 959.1234
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 27 / 27
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including http://www.indena.com/pdf/asiaticoside_st_pc.pdf https://www.ncbi.nlm.nih.gov/pubmed/10350364

Asiaticoside is a triterpene found in Centella that exhibits anti-inflammatory, neuroprotective, cognition enhancing, antipyretic, antioxidative, pro-angiogenic, anticancer chemotherapeutic, and chemopreventive activities. Asiaticoside inhibits melanogenesis by decreasing DNA binding by MITF; as a result, it is occasionally used in skin whitening treatments. Asiaticoside induces apoptosis, increases activation of caspase 3, decreases release of TNF-α and IL-1β, and suppresses tumor development and size in animal models of breast cancer. In animal models of cerebral ischemia/reperfusion, asiaticoside improves memory and learning deficits and decreases levels of IL-6, TNF-α, and IL-1β. Additionally, asiaticoside decreases LPS-induced inflammation and fever, suppresses activity of myeloperoxidase, and increases activity of heme oxygenase 1 (HO-1) in vivo. Asiaticoside exhibits significant wound healing activity in normal as well as delayed healing models, increasing cell migration, attachment, and growth in vitro. Asiaticoside is an active ingredient of Madecassol, marketed in Korea as wound healing agent for traumatic or surgical wounds, burns, skin grafts, fistulas, abnormal retractile or decubitus scars, cutaneomucous lesions in ENT, gynaecology, ulcerous lesions in leprosy, striae distensae, cellulitis, varicose leg ulcers, haemorrhoid..

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Madecassol

Approved Use

Wound healing agent for traumatic or surgical wounds, burns, skin grafts, fistulas, abnormal retractile or decubitus scars, cutaneomucous lesions in ENT, gynaecology, ulcerous lesions in leprosy, striae distensae, cellulitis, varicose leg ulcers, haemorrhoid.
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Anti-herpes simplex virus activities of crude water extracts of Thai medicinal plants.
2000 Jan
In vitro inhibitory effects of asiaticoside and madecassoside on human cytochrome P450.
2011 Jun
Patents

Sample Use Guides

Apply 1-2 times daily. Debride and disinfect the wound before application.
Route of Administration: Topical
A significant reduction of MMP-1 mRNA expression was noted at the highest concentration of asiaticoside (100 ug/mL) whereas a significant increase of TIMP-1 mRNA expression was observed at lower concentrations (25 and 50 ug/mL) in human periodontal ligament cells..
Substance Class Chemical
Created
by admin
on Sat Jun 26 00:26:26 UTC 2021
Edited
by admin
on Sat Jun 26 00:26:26 UTC 2021
Record UNII
PKO39VY215
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ASIATICOSIDE
INCI   MI   USP-RS   WHO-DD  
INCI  
Official Name English
(2.ALPHA.,3.BETA.,4.ALPHA.)-2,3,23-TRIHYDROXYURS-12-EN-28-OIC ACID O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->4)-O-.BETA.-D-GLUCOPYRANOSYL-(1->6)-O-.BETA.-D-GLUCOPYRANOSYL ESTER
Common Name English
CENTELASE
Common Name English
MADECASSOL
Common Name English
NSC-36002
Code English
ASIATICOSIDE [USP-RS]
Common Name English
ASIATICOSIDE [INCI]
Common Name English
ASIATICOSIDE [MI]
Common Name English
CENTELASE DERMATOLOGICO
Common Name English
URS-12-EN-28-OIC ACID, 2,3,23-TRIHYDROXY-, O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->4)-O-.BETA.-D-GLUCOPYRANOSYL-(1->6)-.BETA.-D-GLUCOPYRANOSYL ESTER, (2.ALPHA.,3.BETA.,4.ALPHA.)-
Common Name English
BA-2742
Code English
ASIATICOSIDE [WHO-DD]
Common Name English
NSC-166062
Code English
EMDECASSOL
Common Name English
ASIATICOSID
Common Name English
ASIATICOSIDE (CONSTITUENT OF CENTELLA ASIATICA) [DSC]
Common Name English
Code System Code Type Description
RXCUI
18405
Created by admin on Sat Jun 26 00:26:26 UTC 2021 , Edited by admin on Sat Jun 26 00:26:26 UTC 2021
PRIMARY RxNorm
CAS
16830-15-2
Created by admin on Sat Jun 26 00:26:26 UTC 2021 , Edited by admin on Sat Jun 26 00:26:26 UTC 2021
PRIMARY
NCI_THESAURUS
C63665
Created by admin on Sat Jun 26 00:26:26 UTC 2021 , Edited by admin on Sat Jun 26 00:26:26 UTC 2021
PRIMARY
MERCK INDEX
M2092
Created by admin on Sat Jun 26 00:26:26 UTC 2021 , Edited by admin on Sat Jun 26 00:26:26 UTC 2021
PRIMARY Merck Index
EVMPD
SUB12949MIG
Created by admin on Sat Jun 26 00:26:26 UTC 2021 , Edited by admin on Sat Jun 26 00:26:26 UTC 2021
PRIMARY
DRUG BANK
DB14081
Created by admin on Sat Jun 26 00:26:26 UTC 2021 , Edited by admin on Sat Jun 26 00:26:26 UTC 2021
PRIMARY
PUBCHEM
11954171
Created by admin on Sat Jun 26 00:26:26 UTC 2021 , Edited by admin on Sat Jun 26 00:26:26 UTC 2021
PRIMARY
USP_CATALOG
1043331
Created by admin on Sat Jun 26 00:26:26 UTC 2021 , Edited by admin on Sat Jun 26 00:26:26 UTC 2021
PRIMARY USP-RS
MESH
C004446
Created by admin on Sat Jun 26 00:26:26 UTC 2021 , Edited by admin on Sat Jun 26 00:26:26 UTC 2021
PRIMARY
FDA UNII
PKO39VY215
Created by admin on Sat Jun 26 00:26:26 UTC 2021 , Edited by admin on Sat Jun 26 00:26:26 UTC 2021
PRIMARY
ECHA (EC/EINECS)
240-851-7
Created by admin on Sat Jun 26 00:26:26 UTC 2021 , Edited by admin on Sat Jun 26 00:26:26 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
Constituent of Centella asiatica aerial parts.