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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H48O5
Molecular Weight 488.7003
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ASIATIC ACID

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

InChI

InChIKey=JXSVIVRDWWRQRT-UYDOISQJSA-N
InChI=1S/C30H48O5/c1-17-9-12-30(25(34)35)14-13-28(5)19(23(30)18(17)2)7-8-22-26(3)15-20(32)24(33)27(4,16-31)21(26)10-11-29(22,28)6/h7,17-18,20-24,31-33H,8-16H2,1-6H3,(H,34,35)/t17-,18+,20-,21-,22-,23+,24+,26+,27+,28-,29-,30+/m1/s1

HIDE SMILES / InChI

Molecular Formula C30H48O5
Molecular Weight 488.7003
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 12 / 12
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15626723 https://www.lktlabs.com/product/asiatic-acid-95/ https://www.ncbi.nlm.nih.gov/pubmed/25520932

Asiatic acid is a triterpene aglycone originally found in Centella; it exhibits cardioprotective, hepatoprotective, anti-inflammatory, antioxidative, antihypertensive, anticancer, anti-fibrotic, and anti-osteoporotic activities. In vitro and in vivo, asiatic acid inhibits TGF-β1-induced and overload-induced cardiac hypertrophy, decreasing production of TGF-β1 and activation of NF-κB, ERK1/2, and p38 MAPK. In high fat diet-fed rats, asiatic acid decreases expression of NF-κB, p38 MAPK, IL-1β, ROS, IL-6, and TNF-α and increases activity of glutathione peroxidase and catalase, preventing hepatic steatosis. Additionally, asiatic acid inhibits L-NAME-induced hypertension, increasing levels of NO and improving vascular function. In multiple myeloma cells, this compound induces G2/M phase cell cycle arrest, decreases expression of FAK, and inhibits cell proliferation. Asiatic acid inhibits adipogenesis, suppresses activation of G3PDH, and modulates differentiation in bone marrow stromal cells. In animal models of fibrosis, this compound decreases tubular injury and fibroblast activation by suppressing activation of Smad2/3, regulating PPARγ activation, and decreasing levels of α-SMA and TGF-β1. Asiatic acid stimulates wound healing by increasing collagen production. Asiatic acid is considered to be the most therapeutically 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.

Originator

Sources: Bulletin de la Societe de Chimie Biologique (1949), 31, 46-51.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
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.
PubMed

PubMed

TitleDatePubMed
Protective effects of asiatic acid on rotenone- or H2O2-induced injury in SH-SY5Y cells.
2009 Apr
Patents

Sample Use Guides

Apply 1-2 times daily. Debride and disinfect the wound before application.
Route of Administration: Topical
Exposure of MCF-7 and MDA-MB-231 lines of breast cancer cells to 10 uM asiatic acid resulted in a rapid and sustained activation of p38 and ERK1/2.
Substance Class Chemical
Created
by admin
on Sat Jun 26 09:59:42 UTC 2021
Edited
by admin
on Sat Jun 26 09:59:42 UTC 2021
Record UNII
9PA5A687X5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ASIATIC ACID
HSDB   INCI   WHO-DD  
INCI  
Official Name English
ASIATIC ACID [INCI]
Common Name English
(2.ALPHA.,3.BETA.,4.ALPHA.)-2,3,23-TRIHYDROXYURS-12-EN-28-OIC ACID
Common Name English
ASIATIC ACID (CONSTITUENT OF HOLY BASIL LEAF) [DSC]
Common Name English
ASIATIC ACID (CONSTITUENT OF BANABA LEAF) [DSC]
Common Name English
ASIATIC ACID [WHO-DD]
Common Name English
DAMMAROLIC ACID
Common Name English
NSC-166063
Code English
ASIATIC ACID (CONSTITUENT OF CENTELLA ASIATICA) [DSC]
Common Name English
ASIATIC ACID [HSDB]
Common Name English
Code System Code Type Description
CAS
464-92-6
Created by admin on Sat Jun 26 09:59:42 UTC 2021 , Edited by admin on Sat Jun 26 09:59:42 UTC 2021
PRIMARY
RXCUI
1551574
Created by admin on Sat Jun 26 09:59:42 UTC 2021 , Edited by admin on Sat Jun 26 09:59:42 UTC 2021
PRIMARY RxNorm
PUBCHEM
119034
Created by admin on Sat Jun 26 09:59:42 UTC 2021 , Edited by admin on Sat Jun 26 09:59:42 UTC 2021
PRIMARY
HSDB
7662
Created by admin on Sat Jun 26 09:59:42 UTC 2021 , Edited by admin on Sat Jun 26 09:59:42 UTC 2021
PRIMARY
DRUG BANK
DB14054
Created by admin on Sat Jun 26 09:59:42 UTC 2021 , Edited by admin on Sat Jun 26 09:59:42 UTC 2021
PRIMARY
MESH
C017032
Created by admin on Sat Jun 26 09:59:42 UTC 2021 , Edited by admin on Sat Jun 26 09:59:42 UTC 2021
PRIMARY
EVMPD
SUB12948MIG
Created by admin on Sat Jun 26 09:59:42 UTC 2021 , Edited by admin on Sat Jun 26 09:59:42 UTC 2021
PRIMARY
NCI_THESAURUS
C63703
Created by admin on Sat Jun 26 09:59:42 UTC 2021 , Edited by admin on Sat Jun 26 09:59:42 UTC 2021
PRIMARY
FDA UNII
9PA5A687X5
Created by admin on Sat Jun 26 09:59:42 UTC 2021 , Edited by admin on Sat Jun 26 09:59:42 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Constituent of Centella asiatica aerial parts.
PARENT -> CONSTITUENT ALWAYS PRESENT
USP