Pyracrenic acid

Details

• Internal ID: 65b32367-40c2-47a6-971a-d6a6efae77f2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• SMILES (Canonical): CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)OC(=O)C=CC6=CC(=C(C=C6)O)O)C)C(=O)O
• SMILES (Isomeric): CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)OC(=O)/C=C/C6=CC(=C(C=C6)O)O)C)C(=O)O
• InChI: InChI=1S/C39H54O6/c1-23(2)25-14-19-39(34(43)44)21-20-37(6)26(33(25)39)10-12-30-36(5)17-16-31(35(3,4)29(36)15-18-38(30,37)7)45-32(42)13-9-24-8-11-27(40)28(41)22-24/h8-9,11,13,22,25-26,29-31,33,40-41H,1,10,12,14-21H2,2-7H3,(H,43,44)/b13-9+/t25-,26+,29-,30+,31-,33+,36-,37+,38+,39-/m0/s1
• InChI Key: MNUNUJQYFJZRHQ-VZLLCJDWSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₅₄O₆
• Molecular Weight: 618.80 g/mol
• Exact Mass: 618.39203944 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 10.20
• Atomic LogP (AlogP): 8.77
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 80832-44-6
• CHEBI:70671
• 3beta-O-trans-caffeoylbetulinic acid
• Lup-20(29)-en-28-oic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (3beta(E))-
• Pyracenic acid
• (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• Betulinic Acid 3Beta-Caffeate
• CHEMBL1077309
• SCHEMBL14374258
• betulinic acid 3beta-transcaffeate
• AKOS040762251
• HY-130294
• CS-0106550
• Q27139003

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9879	98.79%
Caco-2	-	0.8363	83.63%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8722	87.22%
OATP2B1 inhibitior	-	0.5668	56.68%
OATP1B1 inhibitior	+	0.8618	86.18%
OATP1B3 inhibitior	-	0.5000	50.00%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.7571	75.71%
BSEP inhibitior	+	0.9151	91.51%
P-glycoprotein inhibitior	+	0.7214	72.14%
P-glycoprotein substrate	-	0.5606	56.06%
CYP3A4 substrate	+	0.7053	70.53%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.8847	88.47%
CYP3A4 inhibition	-	0.7711	77.11%
CYP2C9 inhibition	-	0.6281	62.81%
CYP2C19 inhibition	-	0.5390	53.90%
CYP2D6 inhibition	-	0.9183	91.83%
CYP1A2 inhibition	+	0.7156	71.56%
CYP2C8 inhibition	+	0.8452	84.52%
CYP inhibitory promiscuity	-	0.8616	86.16%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6371	63.71%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.9265	92.65%
Skin irritation	-	0.5667	56.67%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7089	70.89%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.7640	76.40%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.9203	92.03%
Acute Oral Toxicity (c)	III	0.4711	47.11%
Estrogen receptor binding	+	0.7712	77.12%
Androgen receptor binding	+	0.8229	82.29%
Thyroid receptor binding	+	0.5155	51.55%
Glucocorticoid receptor binding	+	0.7664	76.64%
Aromatase binding	+	0.7158	71.58%
PPAR gamma	+	0.7188	71.88%
Honey bee toxicity	-	0.6933	69.33%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	99.17%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.65%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	95.80%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.31%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.96%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.97%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.73%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.93%	89.00%
CHEMBL2581	P07339	Cathepsin D	88.76%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	88.61%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.63%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.40%	97.09%
CHEMBL3194	P02766	Transthyretin	82.88%	90.71%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.86%	97.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.37%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.72%	100.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.44%	80.78%

Plants that contains it

• Acer triflorum
• Berberis koreana
• Betula maximowicziana
• Betula pubescens
• Ceriops tagal
• Chamaecrista greggii
• Durio carinatus
• Helicteres angustifolia
• Melaleuca leucadendra
• Pyracantha crenulata
• Salacia cordata

Cross-Links

• PubChem: 6439576
• NPASS: NPC66894
• ChEMBL: CHEMBL1077309
• LOTUS: LTS0254633
• wikiData: Q27139003