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Protoplumericin A
- 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)C=C(C(=O)O2)[C@@H](OC(=O)/C=C/c2ccc(cc2)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C36H42O19/c1-15(50-23(39)8-5-16-3-6-17(7-4-16)51-34-29(44)27(42)25(40)21(12-37)52-34)19-11-36(55-32(19)47)10-9-18-20(31(46)48-2)14-49-33(24(18)36)54-35-30(45)28(43)26(41)22(13-38)53-35/h3-11,14-15,18,21-22,24-30,33-35,37-38,40-45H,12-13H2,1-2H3/b8-5+/t15-,18+,21+,22+,24+,25+,26+,27-,28-,29+,30+,33-,34+,35-,36+/m0/s1 |
| InChIKey | AFYIWKNGSIYXCQ-WLJLAZGQSA-N |
| Formula | C36H42O19 |
| HBA | 19 |
| HBD | 8 |
| MW | 778.71 |
| Rotatable Bonds | 11 |
| TPSA | 286.89 |
| LogP | -2.94 |
| Number Rings | 6 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 55 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.53 |
| Exact Mass | 778.23 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Plumeria alba | Apocynaceae | Plantae | 141603 |
Showing of synonyms
Protoplumericin A
80396-57-2
HY-N1546
Methyl (1S,4aS,7aS)-5'-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4'-[(1S)-1-[(E)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]oxyethyl]spiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
AKOS040762228
FS-9250
CS-0017095
Methyl (1S,4aS,7R,7aS)-5'-oxo-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4'-((S)-1-(((E)-3-(4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)acryloyl)oxy)ethyl)-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
- 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:
102004584
Cas:
80396-57-2
Gnps:
CCMSLIB00004699226
Zinc:
ZINC000252478235
Nmrshiftdb2:
70131270
No compound-protein relationship available.
SMILES: O1CCCCC1Oc(cc2)ccc2C=CC(=O)OCC(C(=O)O3)=CC34C5C(C=C4)C=COC5OC6CCCCO6
Level: 3
Mol. Weight: 778.71 g/mol
SMILES: c1ccccc1C=CC(=O)OCC(C(=O)O2)=CC23C4C(C=C3)C=COC4OC5CCCCO5
Level: 2
Mol. Weight: 778.71 g/mol
SMILES: C1OC=CC(C=C2)C1C23C=C(C(=O)O3)COC(=O)C=Cc4ccc(cc4)OC5CCCCO5
Level: 2
Mol. Weight: 778.71 g/mol
SMILES: c1ccccc1C=CC(=O)OCC(C(=O)O2)=CC23C4C(C=C3)C=COC4
Level: 1
Mol. Weight: 778.71 g/mol
SMILES: O=C(O1)C=CC12C3C(C=C2)C=COC3OC4CCCCO4
Level: 1
Mol. Weight: 778.71 g/mol
SMILES: c1ccccc1OC2CCCCO2
Level: 1
Mol. Weight: 778.71 g/mol
SMILES: O=C(O1)C=CC12C3C(C=C2)C=COC3
Level: 0
Mol. Weight: 778.71 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 778.71 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 778.71 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.44
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 23.940
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 3879.39
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.720
- Plasma Protein Binding
- 73.02
- 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
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 4.890
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -94.680
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.790
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 8.040
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -7043287.750
- Rat (Acute)
- 3.070
- Rat (Chronic Oral)
- 5.370
- Fathead Minnow
- 8898.040
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 786561.890
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 0.580
- Log(P)
- -1.03
- Log S
- -2.52
- Log(Vapor Pressure)
- -25819.01
- Melting Point
- 236.18
- pKa Acid
- -139.79
- pKa Basic
- 1.95
| 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 | 0.8921 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8921 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8104 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8104 |
| Putative snRNP Sm-like protein | Q8ZYG5 | Q8ZYG5_PYRAE | Pyrobaculum aerophilum | 3 | 0.7870 |
| Putative snRNP Sm-like protein | Q8ZYG5 | Q8ZYG5_PYRAE | Pyrobaculum aerophilum | 3 | 0.7870 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7828 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7828 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7754 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7754 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7724 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7724 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7708 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7708 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7656 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7656 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7505 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7505 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.7496 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.7496 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7450 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7450 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7441 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7441 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7431 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7431 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7404 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7404 |
| IAG-nucleoside hydrolase | Q9GPQ4 | Q9GPQ4_TRYVI | Trypanosoma vivax | 4 | 0.7322 |
| IAG-nucleoside hydrolase | Q9GPQ4 | Q9GPQ4_TRYVI | Trypanosoma vivax | 4 | 0.7322 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7272 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7272 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.7143 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.7143 |
| 6-phosphogluconate dehydrogenase, decarboxylating | P96789 | 6PGD_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7113 |
| 6-phosphogluconate dehydrogenase, decarboxylating | P96789 | 6PGD_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7113 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7043 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7043 |
| Diamine acetyltransferase 1 | P21673 | SAT1_HUMAN | Homo sapiens | 2 | 0.7035 |
| Diamine acetyltransferase 1 | P21673 | SAT1_HUMAN | Homo sapiens | 2 | 0.7035 |