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Cinchonain A
- Family: Plantae - Bombacaceae
- Kingdom: Plantae
-
Class: Lignan
- Subclass: Flavonolignan
| Canonical Smiles | O=C1Oc2cc(O)c3c(c2[C@H](C1)c1ccc(c(c1)O)O)O[C@@H]([C@@H](C3)O)c1ccc(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C24H20O9/c25-14-3-1-10(5-17(14)28)12-8-21(31)32-20-9-16(27)13-7-19(30)23(33-24(13)22(12)20)11-2-4-15(26)18(29)6-11/h1-6,9,12,19,23,25-30H,7-8H2/t12-,19-,23-/m1/s1 |
| InChIKey | LKCOZWLUAKSRQM-UMAWSMADSA-N |
| Formula | C24H20O9 |
| HBA | 9 |
| HBD | 6 |
| MW | 452.42 |
| Rotatable Bonds | 2 |
| TPSA | 156.91 |
| LogP | 2.69 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.21 |
| Exact Mass | 452.11 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Trichilia gilgiana | Meliaceae | Plantae | 2709000 |
| 2 | Ceiba pentandra | Bombacaceae | Plantae | 193163 |
Showing of synonyms
Cinchonain A
Cinchonain Ia
85081-24-9
(-)-Cinchonain IA
XAW49PG8E7
(2R,3R,10R)-2,10-Bis(3,4-dihydroxyphenyl)-3,4,9,10-tetrahydro-3,5-dihydroxy-2H,8H-benzo(1,2-b:3,4-b')dipyran-8-one
2H,8H-Benzo(1,2-b:3,4-b')dipyran-8-one, 2,10-bis(3,4-dihydroxyphenyl)-3,4,9,10-tetrahydro-3,5-dihydroxy-, (2R-(2alpha,3alpha,10alpha))-
DTXSID00440220
DTXCID60391042
Cinchonain 1a
(2R,3R,10R)-2,10-bis(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4,9,10-tetrahydro-2H-pyrano[2,3-f]chromen-8-one
UNII-XAW49PG8E7
CHEBI:3702
2H,8H-Benzo[1,2-b:3,4-b']dipyran-8-one, 2,10-bis(3,4-dihydroxyphenyl)-3,4,9,10-tetrahydro-3,5-dihydroxy-, (2R,3R,10R)-
C24H20O9
CHEMBL251476
SCHEMBL1769333
Cinchona-1a\, (-)-Chinchonain IA
LMPK12020084
AKOS040762687
2H,8H-BENZO(1,2-B:3,4-B')DIPYRAN-8-ONE, 2,10-BIS(3,4-DIHYDROXYPHENYL)-3,4,9,10-TETRAHYDRO-3,5-DIHYDROXY-, (2R-(2.ALPHA.,3.ALPHA.,10.ALPHA.))-
2H,8H-Benzo[1,2-b:3,4-b?]dipyran-8-one, 2,10-bis(3,4-dihydroxyphenyl)-3,4,9,10-tetrahydro-3,5-dihydroxy-, (2R,3R,10R)-
- Abouelela M.E, Orabi M.A.A, et al. (2020). Anti-Alzheimer's flavanolignans from Ceiba pentandra aerial parts. Fitoterapia, 2020, 143, 104541. [View] [PubMed]
- Kowa TK, Tchokouaha LRY, et al. (2020). Antileishmanial and cytotoxic activities of a new limonoid and a new phenyl alkene from the stem bark of Trichilia gilgiana (Meliaceae).. Natural product research,2020, 34(22), 3182-3188. [View] [PubMed]
Pubchem:
442675
Cas:
85081-24-9
Kegg Ligand:
C10217
Chebi:
3702
Nmrshiftdb2:
60067489
Chembl:
CHEMBL251476
Comptox:
DTXSID40331901
No compound-protein relationship available.
SMILES: c1ccccc1C(O2)CCc(c2c34)ccc3OC(=O)CC4c5ccccc5
Level: 2
Mol. Weight: 452.42 g/mol
SMILES: O1CCCc(c1c23)ccc2OC(=O)CC3c4ccccc4
Level: 1
Mol. Weight: 452.42 g/mol
SMILES: C1CC(=O)Oc2ccc(c3c12)CCC(O3)c4ccccc4
Level: 1
Mol. Weight: 452.42 g/mol
SMILES: O1CCCc(c1c23)ccc2OC(=O)CC3
Level: 0
Mol. Weight: 452.42 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 452.42 g/mol
Anti-alzheimer
Absorption
- Caco-2 (logPapp)
- -6.96
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.13
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -0.06
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.99
- Plasma Protein Binding
- 87.48
- 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
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.29
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.28
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.26
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.33
- 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
- -154.9
- Rat (Acute)
- 2.42
- Rat (Chronic Oral)
- 3.32
- Fathead Minnow
- 4.64
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 605.51
- Hydration Free Energy
- -3.7
- Log(D) at pH=7.4
- 1.58
- Log(P)
- 1.06
- Log S
- -3.71
- Log(Vapor Pressure)
- -11.73
- Melting Point
- 291.07
- pKa Acid
- 6.38
- pKa Basic
- 6.43
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Multidrug-efflux transporter 1 regulator | P39075 | BMRR_BACSU | Bacillus subtilis | 3 | 0.9239 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9060 |
| HTH-type transcriptional regulator QacR | P0A0N3 | QACR_STAAM | Staphylococcus aureus | 3 | 0.9001 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.8954 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8917 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.8798 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8649 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8643 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8584 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.8498 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 4 | 0.8454 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.8223 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8166 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8158 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8146 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8086 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8011 |
| Gag-Pol polyprotein | P03369 | POL_HV1A2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7985 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7951 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7909 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 4 | 0.7887 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q4WP27 | Q4WP27_ASPFU | Aspergillus fumigatus | 3 | 0.7885 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7877 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.7877 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7870 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7831 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7829 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.7708 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7699 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 4 | 0.7693 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7657 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7644 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7613 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7612 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7607 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7598 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7567 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7464 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7427 |
| High affinity 3',5'-cyclic-AMP phosphodiesterase 7A | Q13946 | PDE7A_HUMAN | Homo sapiens | 4 | 0.7417 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7405 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7401 |
| Bromodomain-containing protein 9 | Q9H8M2 | BRD9_HUMAN | Homo sapiens | 3 | 0.7374 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7372 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7321 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7275 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.7251 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7239 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7230 |
| High affinity nerve growth factor receptor | P04629 | NTRK1_HUMAN | Homo sapiens | 3 | 0.7225 |
| 3'-5' exoribonuclease Rv2179c | P9WJ73 | EXRBN_MYCTU | Mycobacterium tuberculosis | 3 | 0.7224 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 4 | 0.7202 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7200 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.7192 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7188 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.7184 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7173 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7170 |
| Thymidine phosphorylase | P07650 | TYPH_ECOLI | Escherichia coli | 4 | 0.7154 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7149 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7145 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7132 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7127 |
| Corticosteroid-binding globulin | P31211 | CBG_RAT | Rattus norvegicus | 3 | 0.7119 |
| Thymidylate synthase | P0A886 | TYSY_ECO57 | Escherichia coli O157:H7 | 3 | 0.7112 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7093 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7072 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7065 |
| Cytochrome P450 2C8 | P10632 | CP2C8_HUMAN | Homo sapiens | 4 | 0.7053 |
| Ephrin type-B receptor 4 | P54760 | EPHB4_HUMAN | Homo sapiens | 3 | 0.7048 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7035 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7035 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7033 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7012 |
| Orotidine 5'-phosphate decarboxylase | Q5L0U0 | PYRF_GEOKA | Geobacillus kaustophilus | 3 | 0.7007 |
| Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.7000 |