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Morelloflavone
- Family: Plantae - Clusiaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Biflavonoid
| Canonical Smiles | Oc1ccc(cc1)[C@H]1Oc2cc(O)cc(c2C(=O)[C@@H]1c1c(O)cc(c2c1oc(cc2=O)c1ccc(c(c1)O)O)O)O |
|---|---|
| InChI | InChI=1S/C30H20O11/c31-14-4-1-12(2-5-14)29-27(28(39)25-18(35)8-15(32)9-23(25)41-29)26-20(37)10-19(36)24-21(38)11-22(40-30(24)26)13-3-6-16(33)17(34)7-13/h1-11,27,29,31-37H/t27-,29+/m0/s1 |
| InChIKey | GFWPWSNIXRDQJC-LMSSTIIKSA-N |
| Formula | C30H20O11 |
| HBA | 11 |
| HBD | 7 |
| MW | 556.48 |
| Rotatable Bonds | 3 |
| TPSA | 198.12 |
| LogP | 4.5 |
| Number Rings | 6 |
| Number Aromatic Rings | 5 |
| Heavy Atom Count | 41 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.07 |
| Exact Mass | 556.1 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Allanblackia gabonensis | Clusiaceae | Plantae | 469913 |
| 2 | Allanblackia floribunda | Guttiferae | Plantae | 469914 |
| 3 | Allanblackia floribunda | Guttiferae | Plantae | 469914 |
| 4 | Allanblackia floribunda | Guttiferae | Plantae | 469914 |
| 5 | Garcinia livingstonei | Clusiaceae | Plantae | 469932 |
Showing of synonyms
Morelloflavone
16851-21-1
8-[(2S,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
DTXSID60168574
(3,8'-Bi-4H-1-benzopyran)-4,4'-dione, 2'-(3,4-dihydroxyphenyl)-2,3-dihydro-5,5',7,7'-tetrahydroxy-2-(4-hydroxyphenyl)-, (2S-trans)-
8-((2S,3R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
DTXCID0091065
Morelloflavone, (-)-
XH2KXX2C5D
1414943-37-5
[3,8'-Bi-4H-1-benzopyran]-4,4'-dione, 2'-(3,4-dihydroxyphenyl)-2,3-dihydro-5,5',7,7'-tetrahydroxy-2-(4-hydroxyphenyl)-, (2S,3R)-
8-((2S,3R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxochroman-3-yl)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
AX3GA2TK7M
(2S,3R)-2'-(3,4-Dihydroxyphenyl)-2,3-dihydro-5,5',7,7'-tetrahydroxy-2-(4-hydroxyphenyl)(3,8'-bi-4H-1-benzopyran)-4,4'-dione
(2S,3R)-2'-(3,4-Dihydroxyphenyl)-2,3-dihydro-5,5',7,7'-tetrahydroxy-2-(4-hydroxyphenyl)[3,8'-bi-4H-1-benzopyran]-4,4'-dione
(3,8'-Bi-4H-1-benzopyran)-4,4'-dione, 2'-(3,4-dihydroxyphenyl)-2,3-dihydro-5,5',7,7'-tetrahydroxy-2-(4-hydroxyphenyl)-, (2S,3R)-
UNII-AX3GA2TK7M
UNII-XH2KXX2C5D
SCHEMBL2383075
CHEMBL1215433
BDBM50478419
DA-55637
FM137793
AK-693/40757284
Q15634193
8-[(2S,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-chroman-3-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one
8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
- Kuete V, Azebaze AG, et al. (2011). Antioxidant, antitumor and antimicrobial activities of the crude extract and compounds of the root bark of Allanblackia floribunda.. Pharmaceutical biology,2011, 49(1), 57-65. [View] [PubMed]
- Azebaze AG, Teinkela JE, et al. (2015). Antiplasmodial activity of some phenolic compounds from Cameroonians Allanblackia.. African health sciences,2015, 15(3), 835-840. [View] [PubMed]
- Menasria F, Azebaze AG, et al. (2008). Apoptotic effects on B-cell chronic lymphocytic leukemia (B-CLL) cells of heterocyclic compounds isolated from Guttiferaes.. Leukemia research,2008, 32(12), 1914-1926. [View] [PubMed]
- Nganou BK, Simo Konga I, et al. (2019). Guttiferone BL with antibacterial activity from the fruits of Allanblackia gabonensis.. Natural product research,2019, 33(18), 2638-2646. [View] [PubMed]
- Mulholland DA, Mwangi EM, et al. (2013). Non-toxic melanin production inhibitors from Garcinia livingstonei (Clusiaceae). Journal of ethnopharmacology, 2013, 149(2), 570–575. [View]
Pubchem:
5464454
Cas:
16851-21-1
Gnps:
CCMSLIB00005771010
Nmrshiftdb2:
60024626
Chembl:
CHEMBL1215433
Comptox:
DTXSID60168574
Bindingdb:
50478419
CPRiL:
68978
SMILES: c1ccccc1-c(cc2=O)oc(c23)c(ccc3)C(C4=O)C(c5ccccc5)Oc(c46)cccc6
Level: 3
Mol. Weight: 556.48 g/mol
SMILES: c1ccccc1-c(cc2=O)oc(c23)c(ccc3)C(C4=O)COc(c45)cccc5
Level: 2
Mol. Weight: 556.48 g/mol
SMILES: O=c1ccoc(c12)c(ccc2)C(C3=O)C(c4ccccc4)Oc(c35)cccc5
Level: 2
Mol. Weight: 556.48 g/mol
SMILES: O=c1ccoc(c12)c(ccc2)C(C3=O)COc(c34)cccc4
Level: 1
Mol. Weight: 556.48 g/mol
SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3
Level: 1
Mol. Weight: 556.48 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 556.48 g/mol
SMILES: c1cccc(c12)OCCC2=O
Level: 0
Mol. Weight: 556.48 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 556.48 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 556.48 g/mol
Anti-plasmodial
Antimicrobial
Antioxidant
Antitumor
Absorption
- Caco-2 (logPapp)
- -6.17
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.160
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 5.71
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.200
- Plasma Protein Binding
- 98.09
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-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
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.790
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.480
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.190
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.380
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Toxic
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -7920.200
- Rat (Acute)
- 2.380
- Rat (Chronic Oral)
- 3.590
- Fathead Minnow
- 23.190
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 577.650
- Hydration Free Energy
- -3.120
- Log(D) at pH=7.4
- 2.640
- Log(P)
- 5.12
- Log S
- -6.1
- Log(Vapor Pressure)
- -10.05
- Melting Point
- 360.16
- pKa Acid
- 10.19
- pKa Basic
- 7.0
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.9182 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 4 | 0.9162 |
| Protease | O38896 | O38896_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.8868 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8772 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.8604 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8495 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.8493 |
| Calmodulin | P62157 | CALM_BOVIN | Bos taurus | 3 | 0.8438 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.8416 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8375 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8321 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8315 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 4 | 0.8310 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8303 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8265 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.8201 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.8159 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8112 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8108 |
| Maltose/maltodextrin-binding periplasmic protein | P0AEX9 | MALE_ECOLI | Escherichia coli | 3 | 0.8022 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7962 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7918 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.7835 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7815 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7783 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7775 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.7754 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 4 | 0.7706 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.7657 |
| GTP 3',8-cyclase | P69848 | MOAA_STAA8 | Staphylococcus aureus | 4 | 0.7631 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7626 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7620 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 4 | 0.7572 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7570 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7550 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7540 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7530 |
| Nodulin-13 | P93330 | NOD13_MEDTR | Medicago truncatula | 3 | 0.7513 |
| Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 | Q9CCZ4 | Y2640_MYCLE | Mycobacterium leprae | 3 | 0.7463 |
| Biotin carboxylase | P24182 | ACCC_ECOLI | Escherichia coli | 5 | 0.7439 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 3 | 0.7426 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7416 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.7401 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7400 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7377 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 4 | 0.7371 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7363 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7290 |
| Genome polyprotein | Q2YHF0 | POLG_DEN4T | Dengue virus type 4 | 3 | 0.7243 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.7236 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7208 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7196 |
| Prostaglandin reductase 3 | Q8N4Q0 | PTGR3_HUMAN | Homo sapiens | 5 | 0.7167 |
| Caspase-6 | P55212 | CASP6_HUMAN | Homo sapiens | 3 | 0.7127 |
| Mitogen-activated protein kinase kinase kinase 5 | Q99683 | M3K5_HUMAN | Homo sapiens | 3 | 0.7113 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.7092 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7085 |
| Dihydrofolate reductase | P22906 | DYR_CANAX | Candida albicans | 4 | 0.7078 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 4 | 0.7053 |
| Ribonuclease I | P21338 | RNI_ECOLI | Escherichia coli | 5 | 0.7049 |
| Beta-glucuronidase | P05804 | BGLR_ECOLI | Escherichia coli | 3 | 0.7049 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7031 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7023 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 4 | 0.7016 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7010 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7008 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 4 | 0.7007 |