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Artecanin
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene
| Canonical Smiles | C=C1C(=O)O[C@H]2[C@H]1CC[C@@]([C@@]13[C@@H]2[C@@]2(C)O[C@H]2[C@H]3O1)(C)O |
|---|---|
| InChI | InChI=1S/C15H18O5/c1-6-7-4-5-13(2,17)15-9(8(7)18-12(6)16)14(3)10(19-14)11(15)20-15/h7-11,17H,1,4-5H2,2-3H3/t7-,8-,9-,10-,11+,13+,14+,15-/m0/s1 |
| InChIKey | KXLUWEYBZBGJRZ-SSISGLGMSA-N |
| Formula | C15H18O5 |
| HBA | 5 |
| HBD | 1 |
| MW | 278.3 |
| Rotatable Bonds | 0 |
| TPSA | 71.59 |
| LogP | 0.55 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.8 |
| Exact Mass | 278.12 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Pentzia monodiana | Asteraceae | Plantae | 301874 |
Showing of synonyms
Artecanin
Chrysartemin B
UNII-7U3EQ7150L
7U3EQ7150L
C09302
ARTECANIN, (+)-
(1S,2R,5S,9S,10S,11R,13S,14R)-2-hydroxy-2,11-dimethyl-6-methylidene-8,12,15-trioxapentacyclo[8.5.0.01,14.05,9.011,13]pentadecan-7-one
4H-Bisoxireno(1,8a:2,3)azuleno(4,5-b)furan-2(3H)-one, octahydro-6-hydroxy-6,8a-dimethyl-3-methylene-
J39.139E
(3AS,6AS,7A.BETA.,7B.BETA.,8B.BETA.,8C.ALPHA.)-3A,5,6,7A,7B,8A,8B,8C-OCTAHYDRO-6.BETA.-HYDROXY-6,8A.BETA.-DIMETHYL-3-METHYLENE-4H-BISOXIRENO(1,8A:2,3)AZULENO(4,5-B)FURAN-2(3H)-ONE
(3AS,6R,6AS,7AR,7BS,8AR,8BS,8CS)-6-HYDROXY-6,8A-DIMETHYL-3-METHYLENEOCTAHYDRO-4H-BISOXIRENO(2,3:1,8A)AZULENO(4,5-B)FURAN-2(3H)-ONE
(3AS,6R,6AS,7AR,7BS,8AR,8BS,8CS)-6-HYDROXY-6,8A-DIMETHYL-3-METHYLIDENEOCTAHYDRO-4H-BISOXIRENO(2,3:1,8A)AZULENO(4,5-B)FURAN-2(3H)-ONE
4H-BISOXIRENO(1,8A:2,3)AZULENO(4,5-B)FURAN-2(3H)-ONE, OCTAHYDRO-6-HYDROXY-6,8A-DIMETHYL-3-METHYLENE-, (3AS,6R,6AS,7AR,7BS,8AR,8BS,8CS)-
4H-BISOXIRENO(1,8A:2,3)AZULENO(4,5-B)FURAN-2(3H)-ONE, OCTAHYDRO-6-HYDROXY-6,8A-DIMETHYL-3-METHYLENE-, (3AS-(3A.ALPHA.,6.ALPHA.,6AR*,7A.ALPHA.,7B.ALPHA.,8A.ALPHA.,8B.ALPHA.,8C.BETA.))-
(1S,2R,5S,9S,10S,11R,13S,14R)-2-hydroxy-2,11-dimethyl-6-methylidene-8,12,15-trioxapentacyclo(8.5.0.01,14.05,9.011,13)pentadecan-7-one
(3AS,6AS,7ABETA,7BBETA,8BBETA,8CALPHA)-3A,5,6,7A,7B,8A,8B,8C-OCTAHYDRO-6BETA-HYDROXY-6,8ABETA-DIMETHYL-3-METHYLENE-4H-BISOXIRENO(1,8A:2,3)AZULENO(4,5-B)FURAN-2(3H)-ONE
4H-BISOXIRENO(1,8A:2,3)AZULENO(4,5-B)FURAN-2(3H)-ONE, OCTAHYDRO-6-HYDROXY-6,8A-DIMETHYL-3-METHYLENE-, (3AS-(3AALPHA,6ALPHA,6AR*,7AALPHA,7BALPHA,8AALPHA,8BALPHA,8CBETA))-
((1s,3ar,5r,5ar,8ar,9s,9ar)-1,5,8a-trimethyl-2,8-dioxo-3a,4,5,5a,9,9a-hexahydro-1h-azuleno(6,5-b)furan-9-yl) acetate
(2r,3ar,7s,7ar)-7,7a-dimethyl-4'-methylene-spiro(3,3a,4,5,6,7-hexahydro-1h-indene-2,3'-tetrahydrofuran)-2'-one
(2r,3ar,7s,7ar)-7,7a-dimethyl-4'-methylene-spiro[3,3a,4,5,6,7-hexahydro-1h-indene-2,3'-tetrahydrofuran]-2'-one
[(1s,3ar,5r,5ar,8ar,9s,9ar)-1,5,8a-trimethyl-2,8-dioxo-3a,4,5,5a,9,9a-hexahydro-1h-azuleno[6,5-b]furan-9-yl] acetate
29431-84-3
CHEBI:2849
(1aS,2R,4aS,7aS,7bS,7cR,8aS,8bR)-2-hydroxy-2,7c-dimethyl-5-methyleneoctahydro-2H-bis(oxireno)[2',3':1,8a
2'',3'':2,3]azuleno[4,5-b]furan-6(5H)-one
AC1L9CBW
CHEMBL467832
DTXSID501318578
NS00094042
Q27105846
CPRiL:
458445
SMILES: C1CCC(C(=C)C(=O)O2)C2C3C(O4)C4C(C135)O5
Level: 0
Mol. Weight: 278.3 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.18
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.65
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.45
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.04
- Plasma Protein Binding
- 16.29
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 14.47
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.2
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- -0.77
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.28
- Micronucleos
- Toxic
- NR-AhR
- Safe
- 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
- 1.05
- Rat (Acute)
- 4.51
- Rat (Chronic Oral)
- 1.17
- Fathead Minnow
- 3.69
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 370.12
- Hydration Free Energy
- -6.45
- Log(D) at pH=7.4
- 0.41
- Log(P)
- 0.33
- Log S
- -1.72
- Log(Vapor Pressure)
- -6.35
- Melting Point
- 101.73
- pKa Acid
- 4.88
- pKa Basic
- 3.22
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8332 |