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Plumieride
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Plumeria-Type Iridoid
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@]2(C=C3)OC(=O)C(=C2)[C@@H](O)C)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C21H26O12/c1-8(23)10-5-21(33-18(10)28)4-3-9-11(17(27)29-2)7-30-19(13(9)21)32-20-16(26)15(25)14(24)12(6-22)31-20/h3-5,7-9,12-16,19-20,22-26H,6H2,1-2H3/t8-,9+,12+,13+,14+,15-,16+,19-,20-,21+/m0/s1 |
| InChIKey | AOPMSFXOYJXDNJ-IRFSQMTFSA-N |
| Formula | C21H26O12 |
| HBA | 12 |
| HBD | 5 |
| MW | 470.43 |
| Rotatable Bonds | 5 |
| TPSA | 181.44 |
| LogP | -2.38 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.62 |
| Exact Mass | 470.14 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Plumeria alba | Apocynaceae | Plantae | 141603 |
Showing of synonyms
Plumieride
Agoniadin
511-89-7
UNII-71A048XW8V
71A048XW8V
PLUMIERIDE [MI]
Methyl (1S,4aS,7R,7aS)-4'-[(1S)-1-hydroxyethyl]-5'-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
DTXSID40199109
NSC 609065
NSC-609065
Methyl (1S,4aS,7R,7aS)-4'-[(1S)-1-hydroxyethyl]-5'-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-spiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
(1S,2R,4AS,7AS)-1-(.BETA.-D-GLUCOPYRANOSYLOXY)-4A,7A-DIHYDRO-4-((1S)-1-HYDROXYETHYL)-5-OXOSPIRO(CYCLOPENTA(C)PYRAN-7(1H),2(5H)-FURAN)-4-CARBOXYLIC ACID METHYL ESTER
SPIRO(CYCLOPENTA(C)PYRAN-7(1H),2'(5'H)-FURAN)-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-4A,7A-DIHYDRO-4'-((1S)-1-HYDROXYETHYL)-5'-OXO-, METHYL ESTER, (1S,2'R,4AS,7AS)-
Spiro(cyclopenta(c)pyran-7(1H),2'(5'H)-furan)-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-4a,7a-dihydro-4-(1-hydroxyethyl)-5'-oxo-, methyl ester, (1S-(1alpha,4aalpha,7alpha(R*),7aalpha))-
Methyl (1S,4ar,7R,7as)-4'-((1S)-1-hydroxyethyl)-5'-oxo-1-(((2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)-4a,7a-dihydro-1H,5'H-spiro(cyclopenta(c)pyran-7,2'-furan)-4-carboxylic acid
Methyl (1S,4ar,7R,7as)-4'-[(1S)-1-hydroxyethyl]-5'-oxo-1-{[(2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylic acid
Methyl (1S,4aS,7R,7aS)-4'-((1S)-1-hydroxyethyl)-5'-oxo-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyspiro(4a,7a-dihydro-1H-cyclopenta(c)pyran-7,2'-furan)-4-carboxylate
Methyl (1S,4aS,7R,7aS)-4'-((1S)-1-hydroxyethyl)-5'-oxo-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxy-spiro(4a,7a-dihydro-1H-cyclopenta(c)pyran-7,2'-furan)-4-carboxylate
DTXCID20121600
(1S,2R,4AS,7AS)-1-(BETA-D-GLUCOPYRANOSYLOXY)-4A,7A-DIHYDRO-4-((1S)-1-HYDROXYETHYL)-5-OXOSPIRO(CYCLOPENTA(C)PYRAN-7(1H),2(5H)-FURAN)-4-CARBOXYLIC ACID METHYL ESTER
SPIRO(CYCLOPENTA(C)PYRAN-7(1H),2'(5'H)-FURAN)-4-CARBOXYLIC ACID, 1-(BETA-D-GLUCOPYRANOSYLOXY)-4A,7A-DIHYDRO-4'-((1S)-1-HYDROXYETHYL)-5'-OXO-, METHYL ESTER, (1S,2'R,4AS,7AS)-
CHEBI:8275
Methyl (1S,4aS,7R,7aS)-4'-((S)-1-hydroxyethyl)-5'-oxo-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
AC1L2HUJ
AC1Q6BJ5
SureCN419720
SCHEMBL419720
CHEMBL464470
HY-N3041
BDBM50480285
AKOS032948813
FS-9946
Plumieride, >=95% (LC/MS-ELSD)
NCGC00347624-02
DA-60849
CS-0023073
C09797
Q27108027
- Afifi MS, Salama OA, et al. (2006). Iridoids with antimicrobial activity from Plumeria alba L.. Bulletin of Pharmaceutical Science of Assiut University,2006,29(1),215-223. [View]
Pubchem:
72319
Cas:
511-89-7
Gnps:
CCMSLIB00004719451
Zinc:
ZINC000004098351
Kegg Ligand:
C09797
Chebi:
8275
Nmrshiftdb2:
60029616
Chembl:
CHEMBL464470
Comptox:
DTXSID40199109
Bindingdb:
50480285
CPRiL:
142950
SMILES: O=C(O1)C=CC12C3C(C=C2)C=COC3OC4CCCCO4
Level: 1
Mol. Weight: 470.43 g/mol
SMILES: O=C(O1)C=CC12C3C(C=C2)C=COC3
Level: 0
Mol. Weight: 470.43 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 470.43 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.67
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.910
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.05
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.720
- Plasma Protein Binding
- 53.29
- 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
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.830
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.190
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.850
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.540
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -147.650
- Rat (Acute)
- 2.990
- Rat (Chronic Oral)
- 3.540
- Fathead Minnow
- 4.070
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 502.860
- Hydration Free Energy
- -3.110
- Log(D) at pH=7.4
- 0.180
- Log(P)
- -1.05
- Log S
- -1.47
- Log(Vapor Pressure)
- -12.42
- Melting Point
- 173.89
- pKa Acid
- 4.7
- pKa Basic
- 2.52
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7949 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7949 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7097 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7097 |