Betulin caffeate

Details

• Internal ID: 4dc5075b-47a6-49e8-9841-bb2e79ac7739
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-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]chrysen-9-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 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)CO
• 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)CO
• InChI: InChI=1S/C39H56O5/c1-24(2)26-14-19-39(23-40)21-20-37(6)27(34(26)39)10-12-31-36(5)17-16-32(35(3,4)30(36)15-18-38(31,37)7)44-33(43)13-9-25-8-11-28(41)29(42)22-25/h8-9,11,13,22,26-27,30-32,34,40-42H,1,10,12,14-21,23H2,2-7H3/b13-9+/t26-,27+,30-,31+,32-,34+,36-,37+,38+,39+/m0/s1
• InChI Key: VOQSZICWRNPAMF-IUGYEWCASA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₅₆O₅
• Molecular Weight: 604.90 g/mol
• Exact Mass: 604.41277488 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 10.20
• Atomic LogP (AlogP): 8.67
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 89130-86-9
• [(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-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]chrysen-9-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• Betulin-3-Caffeate
• betulin-3beta-caffeate
• Betulin 3beta-caffeate
• CHEMBL502663
• SCHEMBL3960460
• SCHEMBL5448728
• AKOS040761412
• Lup-20(29)en-28-ol-3-yl caffeate
• 3-(3,4-Dihydroxyphenyl)acrylic acid 28-hydroxylup-20(29)-en-3beta-yl ester
• [(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• Betulin-3-caffeate; Betulin-3-yl caffeate; Caffeic acid betulin ester; Lup-20(29)en-28-ol 3-caffeate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9878	98.78%
Caco-2	-	0.8353	83.53%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.9032	90.32%
OATP2B1 inhibitior	-	0.5666	56.66%
OATP1B1 inhibitior	+	0.8731	87.31%
OATP1B3 inhibitior	-	0.2608	26.08%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.7526	75.26%
BSEP inhibitior	+	0.9274	92.74%
P-glycoprotein inhibitior	+	0.7006	70.06%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7160	71.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8742	87.42%
CYP3A4 inhibition	-	0.6920	69.20%
CYP2C9 inhibition	-	0.6082	60.82%
CYP2C19 inhibition	-	0.6395	63.95%
CYP2D6 inhibition	-	0.9009	90.09%
CYP1A2 inhibition	+	0.6154	61.54%
CYP2C8 inhibition	+	0.8447	84.47%
CYP inhibitory promiscuity	-	0.6999	69.99%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6870	68.70%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.9279	92.79%
Skin irritation	-	0.6417	64.17%
Skin corrosion	-	0.9541	95.41%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7680	76.80%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7571	75.71%
skin sensitisation	-	0.8580	85.80%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8934	89.34%
Acute Oral Toxicity (c)	III	0.6123	61.23%
Estrogen receptor binding	+	0.7763	77.63%
Androgen receptor binding	+	0.8313	83.13%
Thyroid receptor binding	-	0.4934	49.34%
Glucocorticoid receptor binding	+	0.7329	73.29%
Aromatase binding	+	0.7409	74.09%
PPAR gamma	+	0.7218	72.18%
Honey bee toxicity	-	0.7123	71.23%
Biodegradation	-	0.7750	77.50%
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	99.48%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.28%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.21%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.81%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	93.47%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.14%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.50%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.84%	92.94%
CHEMBL2581	P07339	Cathepsin D	89.57%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.36%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.57%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.01%	100.00%
CHEMBL3788	O00444	Serine/threonine-protein kinase PLK4	85.49%	83.65%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.72%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	84.18%	91.19%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.91%	91.03%
CHEMBL1937	Q92769	Histone deacetylase 2	82.10%	94.75%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.07%	80.78%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.05%	97.33%
CHEMBL233	P35372	Mu opioid receptor	81.75%	97.93%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.10%	96.95%

Plants that contains it

• Barbarea verna
• Betula ermanii
• Betula fruticosa
• Betula lenta
• Betula maximowicziana
• Betula pendula subsp. mandshurica
• Betula pubescens
• Ceriops tagal
• Chaenomeles sinensis
• Chenopodium foliosum
• Maytenus chiapensis
• Maytenus cuzcoina
• Orthocaulis attenuatus
• Quercus suber
• Scabiosa pyrenaica

Cross-Links

• PubChem: 10153267
• NPASS: NPC35212
• LOTUS: LTS0068179
• wikiData: Q104401712