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Cleomiscosin A
- Family: Plantae - Simaroubaceae
- Kingdom: Plantae
-
Class: Coumarin
- Subclass: Coumarinolignan
| Canonical Smiles | OC[C@H]1Oc2c(O[C@@H]1c1ccc(c(c1)OC)O)c(OC)cc1c2oc(=O)cc1 |
|---|---|
| InChI | InChI=1S/C20H18O8/c1-24-13-7-10(3-5-12(13)22)17-15(9-21)26-20-18-11(4-6-16(23)27-18)8-14(25-2)19(20)28-17/h3-8,15,17,21-22H,9H2,1-2H3/t15-,17-/m1/s1 |
| InChIKey | OCBGWPJNUZMLCA-NVXWUHKLSA-N |
| Formula | C20H18O8 |
| HBA | 8 |
| HBD | 2 |
| MW | 386.36 |
| Rotatable Bonds | 4 |
| TPSA | 107.59 |
| LogP | 2.39 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.25 |
| Exact Mass | 386.1 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Turraeanthus mannii | Meliaceae | Plantae | 1317901 |
| 2 | Pentas schimperi | Rubiaceae | Plantae | 25384 |
| 3 | Pentas schimperi | Rubiaceae | Plantae | 25384 |
| 4 | Brucea antidysenterica | Simaroubaceae | Plantae | 459111 |
Showing of synonyms
Cleomiscosin A
76948-72-6
CHEBI:3740
(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydro-9H-[1,4]dioxino[2,3-h]chromen-9-one
NSC 346197
(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydro-9H-(1,4)dioxino(2,3-h)chromen-9-one
9H-Pyrano(2,3-f)-1,4-benzodioxin-9-one, 2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-, trans-(+-)-
1482512-83-3
(2R,3R)-rel-2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-9H-pyrano[2,3-f]-1,4-benzodioxin-9-one
Trans-(+/-)-2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-9H-pyrano[2,3-f]-1,4-benzodioxin-9-one
CHEMBL510091
SCHEMBL2727534
DTXSID701317390
HY-N3595
MSK190090
AKOS032948582
MS-26372
CS-0023911
C09922
Q27106181
(2R,3R)-3-(4-hydroxy-3-methoxy-phenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[2,3-f][1,4]benzodioxin-9-one
9H-pyrano[2,3-f]-1,4-benzodioxin-9-one, 2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-, (2R,3R)-
- Makong YS, Mouthé Happi G, et al. (2019). Cytotoxic Stilbenes and Canthinone Alkaloids from Brucea antidysenterica (Simaroubaceae). Molecules, 2019, 24(23), 4412. [View] [PubMed]
- Goffin E, Ziemons E, et al. (2002). In vitro antiplasmodial activity of Tithonia diversifolia and identification of its main active constituent: tagitinin C.. Planta medica,2002, 68(6), 543-545. [View] [PubMed]
- Sielinou V, Vardamides J, et al. (2012). Phenolic derivatives and an antifungal and cytototoxic labdane diterpenoid from the root bark of Turraeanthus mannii. Phytochemistry Letters, 2012, 5(3), 409-413. [View]
- Donfack A, Tala M, et al. (2014). Two new anthraquinone dimers from the stem bark of Pentas schimperi (Rubiaceae). Phytochemistry Letters, 2014, 8, 55-58. [View]
Pubchem:
442510
Cas:
76948-72-6
Zinc:
ZINC000001580260
Kegg Ligand:
C09922
Chebi:
3740
Nmrshiftdb2:
60027366
Metabolights:
MTBLC3740
Chembl:
CHEMBL510091
CPRiL:
83708
SMILES: O=c(o1)ccc2ccc(c3c12)OC(CO3)c4ccccc4
Level: 1
Mol. Weight: 386.36 g/mol
SMILES: O1CCOc(c1c23)ccc2ccc(=O)o3
Level: 0
Mol. Weight: 386.36 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 386.36 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.61
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.740
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.9
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.540
- Plasma Protein Binding
- 87.56
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.210
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.600
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.240
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.790
- 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
- -12.030
- Rat (Acute)
- 2.070
- Rat (Chronic Oral)
- 2.160
- Fathead Minnow
- 4.630
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 475.930
- Hydration Free Energy
- -7.850
- Log(D) at pH=7.4
- 2.200
- Log(P)
- 1.22
- Log S
- -4.35
- Log(Vapor Pressure)
- -8.62
- Melting Point
- 192.64
- pKa Acid
- 7.21
- pKa Basic
- 0.94
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.9355 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.9228 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9113 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8884 |
| Serine/threonine-protein kinase 10 | O94804 | STK10_HUMAN | Homo sapiens | 3 | 0.8827 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8796 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.8761 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.8730 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.8711 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 3 | 0.8544 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8541 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.8468 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8436 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.8350 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 4 | 0.8341 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.8284 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.8254 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8197 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.8112 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.8057 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7997 |
| GTPase KRas | P01116 | RASK_HUMAN | Homo sapiens | 3 | 0.7924 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7912 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 3 | 0.7898 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7880 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.7813 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 5 | 0.7805 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.7776 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7766 |
| Tau-tubulin kinase 1 | Q5TCY1 | TTBK1_HUMAN | Homo sapiens | 3 | 0.7722 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7665 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 4 | 0.7649 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7645 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7615 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.7594 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7587 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7564 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7511 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7500 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.7481 |
| Pol protein | Q000H7 | Q000H7_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.7478 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7467 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 4 | 0.7434 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7426 |
| Proliferating cell nuclear antigen | P12004 | PCNA_HUMAN | Homo sapiens | 3 | 0.7416 |
| Dihydrofolate reductase | P00374 | DYR_HUMAN | Homo sapiens | 3 | 0.7415 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7393 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7384 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7361 |
| Thymidylate synthase | P0A886 | TYSY_ECO57 | Escherichia coli O157:H7 | 3 | 0.7356 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 4 | 0.7322 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7321 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7287 |
| [LysW]-aminoadipate kinase | O50147 | LYSZ_THET2 | Thermus thermophilus | 3 | 0.7275 |
| Nodulin-13 | P93330 | NOD13_MEDTR | Medicago truncatula | 3 | 0.7255 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7220 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7205 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7202 |
| Uncharacterized protein MJ1225 | Q58622 | Y1225_METJA | Methanocaldococcus jannaschii | 4 | 0.7187 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7186 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7185 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7166 |
| Genome polyprotein | C0LMU0 | C0LMU0_9FLAV | dengue virus type 3 | 3 | 0.7164 |
| O-methyltransferase family 2 | D5STZ7 | D5STZ7_PLAL2 | Planctopirus limnophila | 4 | 0.7162 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7153 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7130 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7118 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7109 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 2 | 0.7099 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7096 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7092 |
| Glycerol kinase | P0A6F3 | GLPK_ECOLI | Escherichia coli | 4 | 0.7080 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7064 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7063 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7061 |
| Anthocyanidin 3-O-glucosyltransferase UFGT | P51094 | UFOG_VITVI | Vitis vinifera | 4 | 0.7052 |
| Chalcone--flavanone isomerase 1 | P28012 | CFI1_MEDSA | Medicago sativa | 3 | 0.7043 |
| dTDP-4-dehydrorhamnose 3,5-epimerase | A0A6L7H6N0 | A0A1S0QLH9_BACAN | Bacillus anthracis | 3 | 0.7040 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7035 |
| Phosphoglycerate kinase | Q83AU6 | PGK_COXBU | Coxiella burnetii | 3 | 0.7033 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7026 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7024 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7018 |
| Transthyretin | P02767 | TTHY_RAT | Rattus norvegicus | 3 | 0.7017 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 3 | 0.7008 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7007 |