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Xanthyletin
- Family: Plantae - Rutaceae
- Kingdom: Plantae
- Class: Coumarin
| Canonical Smiles | CC1(C)C=Cc2c(O1)cc1c(c2)ccc(=O)o1 |
|---|---|
| InChI | InChI=1S/C14H12O3/c1-14(2)6-5-10-7-9-3-4-13(15)16-11(9)8-12(10)17-14/h3-8H,1-2H3 |
| InChIKey | QOTBQNVNUBKJMS-UHFFFAOYSA-N |
| Formula | C14H12O3 |
| HBA | 3 |
| HBD | 0 |
| MW | 228.25 |
| Rotatable Bonds | 0 |
| TPSA | 39.44 |
| LogP | 2.98 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 17 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.21 |
| Exact Mass | 228.08 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Sida acuta | Malvaceae | Plantae | 108357 |
| 2 | Sida acuta | Malvaceae | Plantae | 108357 |
| 3 | Citrus aurantium | Rutaceae | Plantae | 43166 |
| 4 | Citrus clementina | Rutaceae | Plantae | 85681 |
| 5 | Citrus reticulata | Rutaceae | Plantae | 85571 |
| 6 | Citrus nobilis x Citrus deliciosa | Rutaceae | Plantae | 558547 |
Showing of synonyms
Xanthyletin
553-19-5
Xanthyletine
2,2-dimethylpyrano[3,2-g]chromen-8-one
UNII-3N789LD38N
XANTHYLETIN [MI]
DTXSID60203818
2,2-DIMETHYLCHROMENOCOUMARIN
2H,8H-Benzo[1,2-b:5,4-b']dipyran-2-one, 8,8-dimethyl-
7-HYDROXY-2,2-DIMETHYL-2H-1-BENZOPYRAN-6-ACRYLIC ACID .DELTA.-LACTONE
2,2-dimethylpyrano(3,2-g)chromen-8-one
2H,8H-Benzo(1,2-b:5,4-b')dipyran-2-one, 8,8-dimethyl-
DTXCID90126309
7-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-acrylic acid delta-lactone
Qotbqnvnubkjms-uhfffaoysa-n
Spectrum_000673
SpecPlus_000132
CHEMBL303846
CHEBI:10073
3N789LD38N
8,8-Dimethyl-2H,8H-pyrano[3,2-g]chromen-2-one
8,8-Dimethyl-8H-pyrano[3,2-g]chromen-2-one
8,8-Dimethyl-2H,8H-benzo(1,2-b:5,4-b')dipyran-2-one
8,8-dimethyl-2H,8H-benzo[1,2-b:5,4-b']dipyran-2-one
Spectrum2_000365
Spectrum3_000124
Spectrum4_001401
Spectrum5_000162
BSPBio_001768
KBioGR_001782
KBioSS_001153
SPECTRUM100609
Cid_65188
MLS000863611
DivK1c_006228
SPBio_000489
MEGxp0_000991
SCHEMBL2120500
ACon1_000507
KBio1_001172
KBio2_001153
KBio2_003721
KBio2_006289
KBio3_000928
HMS2269H15
HY-N4116
BDBM50292575
CCG-38639
AKOS000278141
SDCCGMLS-0066430.P001
NCGC00095444-01
NCGC00095444-02
NCGC00095444-03
DA-59181
SMR000440697
XX163807
CS-0032126
C09317
E88696
AN-566/21182005
SR-01000780630
SR-01000780630-2
8,8-Dimethyl-2H,8H-pyrano[3,2-g]chromen-2-one #
BRD-K28108221-001-02-3
Q27108571
- Bissim S, Kenmogne S, et al. (2019). Bioactive acridone alkaloids and their derivatives from Citrus aurantium (Rutaceae). Phytochemistry Letters, 2019, 29, 148-153. [View]
- Kamdoum BC, Simo I, et al. (2022). Chemical constituents of two Cameroonian medicinal plants: Sida rhombifolia L. and Sida acuta Burm. f. (Malvaceae) and their antiplasmodial activity.. Natural product research,2022, 36(20), 5311-5318. [View] [PubMed]
- Tahsin T, Wansi JD, et al. (2017). Cytotoxic Properties of the Stem Bark of Citrus reticulata Blanco (Rutaceae).. Phytotherapy research : PTR,2017, 31(8), 1215-1219. [View] [PubMed]
- Femoe UM, Fassi JBK, et al. (2022). In Vitro Assessment of the Cercaricidal Activity of Sida acuta Burm. F. and Sida rhombifolia Linn. (Malvaceae) Hydroethanolic Extracts, Cytotoxicity, and Phytochemical Studies.. Evidence-based complementary and alternative medicine : eCAM,2022, 2022, 7281144. [View] [PubMed]
- El-Hawary S.S, Issa M.Y, et al. (2022). Potential of (Citrus nobilis Lour x Citrus deliciosa Tenora) metabolites on COVID-19 virus main protease supported by in silico analysis. Natural product research, 2022, 36(11), 2843-2847. [View] [PubMed]
- Bissim S, Kenmogne S, et al. (2021). The chemistry and biological activities of Citrus clementina Hort. Ex Tanaka (Rutaceae), a vegetatively propagated species.. Natural product research,2021, 35(22), 4839-4842. [View] [PubMed]
Pubchem:
65188
Cas:
553-19-5
Gnps:
CCMSLIB00006405200
Zinc:
ZINC000000338304
Kegg Ligand:
C09317
Chebi:
10073
Nmrshiftdb2:
60025262
Chembl:
CHEMBL303846
Comptox:
DTXSID60203818
Bindingdb:
50292575
No compound-protein relationship available.
SMILES: c1cc(=O)oc(c12)cc3c(c2)C=CCO3
Level: 0
Mol. Weight: 228.25 g/mol
Anti-diabetic
Anti-inflammatory
Antioxidant
Cercaricidal
Absorption
- Caco-2 (logPapp)
- -4.68
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.2
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.11
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.06
- Plasma Protein Binding
- 42.82
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.43
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 1.41
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.84
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.29
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 3.86
- Rat (Acute)
- 2.55
- Rat (Chronic Oral)
- 1.66
- Fathead Minnow
- 4.33
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 369.98
- Hydration Free Energy
- -8.2
- Log(D) at pH=7.4
- 3.25
- Log(P)
- 2.92
- Log S
- -4.0
- Log(Vapor Pressure)
- -5.67
- Melting Point
- 164.51
- pKa Acid
- 6.62
- pKa Basic
- 4.63
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.9469 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9016 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8948 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.8944 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.8934 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8919 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8889 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.8844 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.8800 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 3 | 0.8762 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.8725 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8601 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.8560 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.8538 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8510 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.8411 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8406 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8390 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.8387 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.8312 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.8250 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.8184 |
| Achbp | I6L8L2 | I6L8L2_CAPTE | Capitella teleta | 3 | 0.8093 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.8057 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8057 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.8005 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7981 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7876 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7818 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7818 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7807 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7667 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 2 | 0.7665 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7658 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 3 | 0.7653 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 3 | 0.7650 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7639 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7635 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7625 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.7593 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7591 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7563 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7556 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7550 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7535 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7527 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7512 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7500 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7483 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7481 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7478 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 2 | 0.7476 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7468 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7453 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7425 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7415 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7407 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7398 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7393 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7390 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7362 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7356 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7354 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7349 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7348 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7346 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7344 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7339 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7327 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7320 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 2 | 0.7309 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7288 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 2 | 0.7281 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7279 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7270 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7266 |
| Androgen receptor | P19091 | ANDR_MOUSE | Mus musculus | 3 | 0.7260 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7254 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7250 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7245 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7243 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7231 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7205 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 3 | 0.7196 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7166 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7163 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7157 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7126 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7118 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7109 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 2 | 0.7097 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 2 | 0.7087 |
| Poly [ADP-ribose] polymerase 1 | P09874 | PARP1_HUMAN | Homo sapiens | 3 | 0.7067 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7065 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7065 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7058 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7049 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7046 |
| Acyl-coenzyme A synthetase ACSM2A, mitochondrial | Q08AH3 | ACS2A_HUMAN | Homo sapiens | 2 | 0.7043 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7002 |