Macedonic acid

Details

• Internal ID: eb7f057f-5120-4ef7-87f6-c2b0e984e81c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,3R,4aS,6aR,6aS,6bR,8aR,10S,12aS)-3,10-dihydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12-dodecahydropicene-2-carboxylic acid
• SMILES (Canonical): CC1(C2CCC3(C(C2(CCC1O)C)C=CC4=C5CC(C(CC5(CCC43C)C)O)(C)C(=O)O)C)C
• SMILES (Isomeric): C[C@@]12CC[C@@]3(C(=C1C[C@]([C@@H](C2)O)(C)C(=O)O)C=C[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)C
• InChI: InChI=1S/C30H46O4/c1-25(2)20-10-13-30(7)21(27(20,4)12-11-22(25)31)9-8-18-19-16-28(5,24(33)34)23(32)17-26(19,3)14-15-29(18,30)6/h8-9,20-23,31-32H,10-17H2,1-7H3,(H,33,34)/t20-,21+,22-,23+,26-,27-,28-,29+,30+/m0/s1
• InChI Key: QWQDOXKORDLUFG-JKBYBQJKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₆O₄
• Molecular Weight: 470.70 g/mol
• Exact Mass: 470.33960994 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 6.60
• Atomic LogP (AlogP): 6.12
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 26553-68-4
• 39022-00-9
• (2S,3R,4aS,6aR,6aS,6bR,8aR,10S,12aS)-3,10-dihydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12-dodecahydropicene-2-carboxylic acid
• DTXSID40949404
• AKOS040763092
• 3,19-Dihydroxy-oleana-11,13(18)dien-28-oic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9902	99.02%
Caco-2	-	0.5943	59.43%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8089	80.89%
OATP2B1 inhibitior	-	0.7176	71.76%
OATP1B1 inhibitior	+	0.8700	87.00%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6071	60.71%
BSEP inhibitior	+	0.8139	81.39%
P-glycoprotein inhibitior	-	0.6807	68.07%
P-glycoprotein substrate	-	0.7652	76.52%
CYP3A4 substrate	+	0.6804	68.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8746	87.46%
CYP3A4 inhibition	-	0.8467	84.67%
CYP2C9 inhibition	-	0.8530	85.30%
CYP2C19 inhibition	-	0.9058	90.58%
CYP2D6 inhibition	-	0.9544	95.44%
CYP1A2 inhibition	-	0.8713	87.13%
CYP2C8 inhibition	-	0.6413	64.13%
CYP inhibitory promiscuity	-	0.9263	92.63%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6445	64.45%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.9229	92.29%
Skin irritation	+	0.6229	62.29%
Skin corrosion	-	0.9486	94.86%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5175	51.75%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.6081	60.81%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5139	51.39%
Acute Oral Toxicity (c)	I	0.7720	77.20%
Estrogen receptor binding	+	0.6947	69.47%
Androgen receptor binding	+	0.6758	67.58%
Thyroid receptor binding	+	0.7199	71.99%
Glucocorticoid receptor binding	+	0.8209	82.09%
Aromatase binding	+	0.6847	68.47%
PPAR gamma	+	0.6540	65.40%
Honey bee toxicity	-	0.8634	86.34%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9948	99.48%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	97.80%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.83%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.03%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.14%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.36%	100.00%
CHEMBL2581	P07339	Cathepsin D	84.74%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.59%	93.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.53%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.40%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.48%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.58%	91.07%
CHEMBL5028	O14672	ADAM10	80.32%	97.50%

Plants that contains it

• Asplenium normale
• Brucea javanica
• Carpobrotus edulis
• Castanea crenata
• Centrolobium tomentosum
• Ceratophyllum submersum
• Dracocephalum kotschyi
• Glycyrrhiza yunnanensis
• Lippia carviodora
• Myrica nana
• Psilostrophe cooperi
• Sideritis tragoriganum
• Solanum jamaicense
• Trifolium alexandrinum

Cross-Links

• PubChem: 193076
• NPASS: NPC30678
• LOTUS: LTS0000095
• wikiData: Q82927313