Terminolic acid

Details

• Internal ID: 859792cc-380c-4eec-84ae-33230cb1fff8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CC(C5C4(CC(C(C5(C)CO)O)O)C)O)C)C2C1)C)C(=O)O)C
• SMILES (Isomeric): C[C@@]12CC[C@]3(CCC(C[C@H]3C1=CC[C@H]4[C@]2(C[C@H]([C@@H]5[C@@]4(C[C@H]([C@@H]([C@@]5(C)CO)O)O)C)O)C)(C)C)C(=O)O
• InChI: InChI=1S/C30H48O6/c1-25(2)9-11-30(24(35)36)12-10-28(5)17(18(30)13-25)7-8-21-26(3)14-20(33)23(34)27(4,16-31)22(26)19(32)15-29(21,28)6/h7,18-23,31-34H,8-16H2,1-6H3,(H,35,36)/t18-,19+,20+,21+,22+,23-,26+,27-,28+,29+,30-/m0/s1
• InChI Key: IDQVFXZQPGAVAM-GGVBUJAJSA-N
• Popularity: 3 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: 4.50
• Atomic LogP (AlogP): 4.15
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

• 564-13-6
• UNII-9Z1542R0IT
• 9Z1542R0IT
• 2,3,6,23-Tetrahydroxyolean-12-en-28-oic acid (2alpha,3beta,4alpha,6beta)-
• Olean-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, (2alpha,3beta,4alpha,6beta)-
• CHEMBL518567
• SCHEMBL2099327
• C3H48O6
• (4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• HY-N7652
• C3-H48-O6
• 2a,6b,23-trihydroxyl oleanolic acid
• MS-29377
• CS-0134972
• D85111
• Q27273401
• TERMINOLIC ACID (CONSTITUENT OF CENTELLA ASIATICA)
• TERMINOLIC ACID (CONSTITUENT OF CENTELLA ASIATICA) [DSC]
• 2| inverted exclamation mark,6| cent,23-TRIHYDROXYL OLEANOLIC ACID
• OLEAN-12-EN-28-OIC ACID, 2,3,6,23-TETRAHYDROXY-, (2.ALPHA.,3.BETA.,4.ALPHA.,6.BETA.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9687	96.87%
Caco-2	-	0.6304	63.04%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8659	86.59%
OATP2B1 inhibitior	-	0.5721	57.21%
OATP1B1 inhibitior	+	0.8549	85.49%
OATP1B3 inhibitior	-	0.6510	65.10%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6199	61.99%
BSEP inhibitior	+	0.7717	77.17%
P-glycoprotein inhibitior	-	0.7830	78.30%
P-glycoprotein substrate	-	0.7145	71.45%
CYP3A4 substrate	+	0.6261	62.61%
CYP2C9 substrate	-	0.8196	81.96%
CYP2D6 substrate	-	0.8603	86.03%
CYP3A4 inhibition	-	0.9038	90.38%
CYP2C9 inhibition	-	0.8439	84.39%
CYP2C19 inhibition	-	0.9006	90.06%
CYP2D6 inhibition	-	0.9447	94.47%
CYP1A2 inhibition	-	0.9008	90.08%
CYP2C8 inhibition	-	0.6561	65.61%
CYP inhibitory promiscuity	-	0.9508	95.08%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.9286	92.86%
Skin irritation	-	0.5137	51.37%
Skin corrosion	-	0.9578	95.78%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4815	48.15%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.7710	77.10%
skin sensitisation	-	0.8540	85.40%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.5592	55.92%
Acute Oral Toxicity (c)	III	0.8032	80.32%
Estrogen receptor binding	+	0.7521	75.21%
Androgen receptor binding	+	0.7277	72.77%
Thyroid receptor binding	+	0.5559	55.59%
Glucocorticoid receptor binding	+	0.7394	73.94%
Aromatase binding	+	0.6714	67.14%
PPAR gamma	+	0.5538	55.38%
Honey bee toxicity	-	0.8884	88.84%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9863	98.63%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.56%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.71%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.15%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.29%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.11%	95.56%
CHEMBL2581	P07339	Cathepsin D	86.73%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.35%	96.77%
CHEMBL221	P23219	Cyclooxygenase-1	83.87%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.43%	100.00%

Plants that contains it

• Achillea clypeolata
• Athanasia crithmifolia
• Berberis julianae
• Bridelia ferruginea
• Bystropogon origanifolius
• Cardamine heptaphylla
• Centella asiatica
• Cerbera odollam
• Cneorum pulverulentum
• Codonocarpus attenuatus
• Crateva magna
• Cupressus pendula
• 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
• Terminalia complanata
• Terminalia elliptica
• Terminalia macroptera
• Tetraneuris acaulis
• Unonopsis glaucopetala
• Zieria smithii

Cross-Links

• PubChem: 12314613
• NPASS: NPC307282
• LOTUS: LTS0274412
• wikiData: Q27273401