Cafestol

Details

• Internal ID: cd005ccd-02c0-49f6-b9df-e0cf77b04ccc
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (1S,4S,12S,13R,16R,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6-dien-17-ol
• SMILES (Canonical): CC12CCC3=C(C1CCC45C2CCC(C4)C(C5)(CO)O)C=CO3
• SMILES (Isomeric): C[C@@]12CCC3=C([C@H]1CC[C@]45[C@H]2CC[C@H](C4)[C@](C5)(CO)O)C=CO3
• InChI: InChI=1S/C20H28O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h6,9,13,15,17,21-22H,2-5,7-8,10-12H2,1H3/t13-,15-,17+,18-,19+,20+/m1/s1
• InChI Key: DNJVYWXIDISQRD-HWUKTEKMSA-N
• Popularity: 123 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.20384475 g/mol
• Topological Polar Surface Area (TPSA): 53.60 Ų
• XlogP: 3.30

Synonyms

• 469-83-0
• cafesterol
• CCRIS 1518
• AC465T6Q6W
• CHEBI:3291
• (3bS,5aS,7R,8R,10aR,10bS)-7-(hydroxymethyl)-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-ol
• UNII-AC465T6Q6W
• SR-05000002204
• (-)-cafestol
• CAFESTOL [MI]
• SCHEMBL93865
• CHEMBL1407645
• DTXSID3040986
• HY-N6257
• MFCD01075769
• AKOS032949533
• CCG-208556
• 5a,8-Methano-5aH-cyclohepta(5,6)naphtho(2,1-b)furan-7-methanol, 3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-7-hydroxy-10b-methyl-, (3bS,5aS,7R,8R,10aR,10bS)-
• 5a,8-Methano-5aH-cyclohepta(5,6)naphtho(2,1-b)furan-7-methanol, 3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-7-hydroxy-10b-methyl-, (3bS-(3balpha,5abeta,7beta,8beta,10aalpha,10bbeta))-
• MS-24668
• CS-0032793
• C09066
• E80644
• Q423829
• SR-05000002204-2
• SR-05000002204-3
• (1S,4S,12S,13R,16R,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0(1,13).0(4,12).0(5,9)]nonadeca-5(9),6-dien-17-ol
• (1S,4S,12S,13R,16R,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6-dien-17-ol
• 5A,8-METHANO-5AH-CYCLOHEPTA(5,6)NAPHTHO(2,1-B)FURAN-7-METHANOL, 3B,4,5,6,7,8,9,10,10A,10B,11,12-DODECAHYDRO-7-HYDROXY-10B-METHYL-, (3BS-(3B.ALPHA.,5A.BETA.,7.BETA.,8.BETA.,10A.ALPHA.,10B.BETA.))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

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	98.45%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.13%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.89%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.68%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.05%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.35%	92.62%
CHEMBL226	P30542	Adenosine A1 receptor	88.30%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.65%	94.45%
CHEMBL2581	P07339	Cathepsin D	87.60%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.48%	100.00%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	86.12%	87.16%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.11%	86.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.39%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.36%	95.50%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.15%	90.24%

Plants that contains it

• Coffea arabica
• Coffea racemosa
• Diplospora dubia

Cross-Links

• PubChem: 108052
• LOTUS: LTS0149261
• wikiData: Q423829