Madecassic Acid

Details

• Internal ID: 8bad71f6-c8a9-4117-af82-3668bd107f94
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1S,2R,4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
• SMILES (Canonical): CC1CCC2(CCC3(C(=CCC4C3(CC(C5C4(CC(C(C5(C)CO)O)O)C)O)C)C2C1C)C)C(=O)O
• SMILES (Isomeric): C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(C[C@H]([C@@H]5[C@@]4(C[C@H]([C@@H]([C@@]5(C)CO)O)O)C)O)C)[C@@H]2[C@H]1C)C)C(=O)O
• InChI: InChI=1S/C30H48O6/c1-16-9-10-30(25(35)36)12-11-28(5)18(22(30)17(16)2)7-8-21-26(3)13-20(33)24(34)27(4,15-31)23(26)19(32)14-29(21,28)6/h7,16-17,19-24,31-34H,8-15H2,1-6H3,(H,35,36)/t16-,17+,19-,20-,21-,22+,23-,24+,26-,27+,28-,29-,30+/m1/s1
• InChI Key: PRAUVHZJPXOEIF-AOLYGAPISA-N
• Popularity: 47 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₈O₆
• Molecular Weight: 504.70 g/mol
• Exact Mass: 504.34508925 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.00
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

• Brahmic acid
• 18449-41-7
• 6beta-hydroxyasiatic acid
• UNII-M7O1N24J82
• ORISTRACT MDA
• CHEBI:73058
• M7O1N24J82
• NSC 88135
• CHEMBL481854
• NSC-88135
• (2alpha,3beta,6beta)-2,3,6,23-tetrahydroxyurs-12-en-28-oic acid
• Urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, (2.alpha.,3.beta.,4.alpha.,6.beta.)-
• (1S,2R,4aS,6aS,6bR,8R,8aR,9R,10R,11R,12aR,12bR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
• SR-05000002181
• 6-Hydroxyasiatic acid
• SCHEMBL153239
• MADECASSIC ACID [INCI]
• DTXSID70939838
• MADECASSIC ACID [WHO-DD]
• 6.BETA.-HYDROXYASIATIC ACID
• HY-N0569
• BDBM50244879
• s9502
• AKOS015896782
• AC-6055
• CCG-208587
• DB14037
• (1S,2R,4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
• CS-0009106
• SR-05000002181-2
• SR-05000002181-3
• 2alpha,3beta,6beta,23-Tetrahydroxyurs-12-en-28-oic Acid
• MADECASSIC ACID (CONSTITUENT OF CENTELLA ASIATICA)
• 2alpha,3beta,6beta,23-TETRAHYDROXY-URS-12-EN-28-OIC ACID
• MADECASSIC ACID (CONSTITUENT OF CENTELLA ASIATICA) [DSC]
• URS-12-EN-28-OIC ACID, 2alpha,3beta,6beta,23-TETRAHYDROXY-
• 2.ALPHA.,3.BETA.,6.BETA.,23-TETRAHYDROXY-URS-12-EN-28-OIC ACID
• Urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, (2a,3b,4a,6b)-
• Urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, (2alpha,3beta,4alpha,6beta)-
• URS-12-EN-28-OIC ACID, 2.ALPHA.,3.BETA.,6.BETA.,23-TETRAHYDROXY-
• (1S,2R,4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylicacid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9593	95.93%
Caco-2	-	0.6147	61.47%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8349	83.49%
OATP2B1 inhibitior	-	0.5713	57.13%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	-	0.5699	56.99%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6449	64.49%
BSEP inhibitior	+	0.5964	59.64%
P-glycoprotein inhibitior	-	0.7868	78.68%
P-glycoprotein substrate	-	0.5846	58.46%
CYP3A4 substrate	+	0.6669	66.69%
CYP2C9 substrate	-	0.8196	81.96%
CYP2D6 substrate	-	0.8603	86.03%
CYP3A4 inhibition	-	0.8895	88.95%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9444	94.44%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.5380	53.80%
CYP inhibitory promiscuity	-	0.9619	96.19%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7225	72.25%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.9387	93.87%
Skin irritation	+	0.5559	55.59%
Skin corrosion	-	0.9587	95.87%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4269	42.69%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.6585	65.85%
skin sensitisation	-	0.8957	89.57%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.5922	59.22%
Acute Oral Toxicity (c)	III	0.7783	77.83%
Estrogen receptor binding	+	0.6655	66.55%
Androgen receptor binding	+	0.7562	75.62%
Thyroid receptor binding	+	0.5682	56.82%
Glucocorticoid receptor binding	+	0.7064	70.64%
Aromatase binding	+	0.6447	64.47%
PPAR gamma	-	0.4940	49.40%
Honey bee toxicity	-	0.8623	86.23%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9813	98.13%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	12380 nM; 12380 nM	IC50; IC50	PMID: 18707891; DOI: 10.1007/s00044-010-9529-5

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.48%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.20%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.96%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.92%	97.09%
CHEMBL2581	P07339	Cathepsin D	87.95%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.53%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.06%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.26%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.58%	94.45%

Plants that contains it

• Achillea clypeolata
• Athanasia crithmifolia
• Berberis julianae
• Bridelia ferruginea
• Bystropogon origanifolius
• Cardamine heptaphylla
• Centella asiatica
• Centella erecta
• Cerbera odollam
• Cneorum pulverulentum
• Codonocarpus attenuatus
• Crateva magna
• Diospyros verrucosa
• Euonymus nanoides
• Jacobaea subalpina
• Nepeta multifida
• Pleogyne australis
• Polygala amara
• Pyrola decorata
• Quercus serrata
• Rubus allegheniensis
• Salvia abrotanoides
• Siphoneugena densiflora
• Stephania sutchuenensis
• Swertia japonica
• Tetraneuris acaulis
• Unonopsis glaucopetala
• Zieria smithii

Cross-Links

• PubChem: 73412
• NPASS: NPC305464
• ChEMBL: CHEMBL481854
• LOTUS: LTS0164623
• wikiData: Q27140267