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Bergenin
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Coumarin
- Subclass: Isocoumarin
| Canonical Smiles | OC[C@H]1O[C@@H]2[C@@H]([C@H]([C@@H]1O)O)OC(=O)c1c2c(O)c(c(c1)O)OC |
|---|---|
| InChI | InChI=1S/C14H16O9/c1-21-11-5(16)2-4-7(9(11)18)12-13(23-14(4)20)10(19)8(17)6(3-15)22-12/h2,6,8,10,12-13,15-19H,3H2,1H3/t6-,8-,10+,12+,13-/m1/s1 |
| InChIKey | YWJXCIXBAKGUKZ-HJJNZUOJSA-N |
| Formula | C14H16O9 |
| HBA | 9 |
| HBD | 5 |
| MW | 328.27 |
| Rotatable Bonds | 2 |
| TPSA | 145.91 |
| LogP | -1.2 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 328.08 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Antrocaryon klaineanum | Anacardiaceae | Plantae | 289695 |
| 2 | Mallotus oppositifolius | Euphorbiaceae | Plantae | 396489 |
| 3 | Anthonotha macrophylla | Leguminosae/Fabaceae | Plantae | 162653 |
| 4 | Newtonia griffoniana | Leguminosae/Fabaceae | Plantae | 148736 |
Showing of synonyms
Bergenin
477-90-7
Bergenin [JAN]
Yanbaicaisu
Bergeninum
L84RBE4IDC
Bergenin (JAN)
BERGENIN [MI]
BERGENINUM [CHP]
BERGENIN [WHO-DD]
NSC 661749
NSC-661749
NSC-757796
(2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one
DTXSID4048141
NSC 757796
3,4,4a,10b-Tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxypyrano(3,2-c)(2)benzopyran-6(H)-one
4-Methoxy-2-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)pyran-2-yl)alpha-resorcylic acid gamma lactone
PYRANO(3,2-C)(2)BENZOPYRAN-6(2H)-ONE, 3,4,4A,10B-TETRAHYDRO-3,4,8,10-TETRAHYDROXY-2-(HYDROXYMETHYL)-9-METHOXY-(2R,3S,4S,4AR,10BS)-
(2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano(3,2-c)isochromen-6-one
(-)-Bergenin
BERGENIN [INCI]
DTXCID0028113
803-760-9
Cuscutin
Bengenin
MFCD00133120
Corylopsin
CHEBI:69499
(2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one
Pyrano[3,2-c][2]benzopyran-6(2H)-one,3,4,4a,10b-tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-, (2R,3S,4S,4aR,10bS)-
Pyrano[3,2-c][2]benzopyran-6(2H)-one, 3,4,4a,10b-tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-, (2R,3S,4S,4aR,10bS)-
SR-01000789834
UNII-L84RBE4IDC
NSC661749
Bergenin, Cuscutin
Bergenin (Cuscutin)
Bergenin (Standard)
Bergenin, analytical standard
MLS001213180
SCHEMBL893721
CHEMBL273019
HY-N0017R
HMS2876J03
3,4,8,10-Tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one
ALBB-030788
HY-N0017
BDBM50349518
S2270
AKOS015896565
Bergenin, >=95% (LC/MS-ELSD)
CCG-208553
CS-4946
FB09451
NCGC00346587-01
NCGC00346587-02
NCGC00346587-16
AS-16137
SMR000542844
B4349
NS00127066
SW219117-1
C09919
D01040
EN300-19651064
Q4891580
SR-01000789834-5
SR-01000789834-6
BRD-K04176066-001-08-3
Z2037317034
(2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3 ,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one
(2S,4R,5S,6S,7R)-5,6,12,14-tetrahydroxy-4-(hydroxymethyl)-13-methoxy-3,8-dioxatricyclo[8.4.0.0,2,7]tetradeca-1(10),11,13-trien-9-one
- Kinyok MJ, Bonnet S, et al. (2017). A new flavanolignan and a new alkane from the Stem bark of Newtonia griffoniana.. Natural product research,2017, 31(19), 2233-2238. [View] [PubMed]
- Tchangoue YAN, Tchamgoue J, et al. (2020). Antibacterial phloroglucinols derivatives from the leaves of Mallotus oppositifolius (Geisler) Müll. Arg. (Euphorbiaceae).. Fitoterapia,2020, 142, 104527. [View] [PubMed]
- Kinyok MJ, Wilhelm A, et al. (2021). Chemical constituents of the leaves of Anthonotha macrophylla (Leguminosae).. Natural product research,2021, 35(21), 3865-3872. [View] [PubMed]
- Fouokeng Y, Feusso HMF, et al. (2019). In vitro antimalarial, antitrypanosomal and HIV-1 integrase inhibitory activities of two Cameroonian medicinal plants: Antrocaryon klaineanum (Anacardiaceae) and Diospyros conocarpa (Ebenaceae).. South African Journal of Botany, 2019, 122, 510-517. [View]
Pubchem:
66065
Cas:
477-90-7
Gnps:
CCMSLIB00006565064
Zinc:
ZINC000004046820
Kegg Ligand:
C09919
Chebi:
69499
Nmrshiftdb2:
60023985
Metabolights:
MTBLC69499
Chembl:
CHEMBL273019
Comptox:
DTXSID4048141
Bindingdb:
50349518
Selleck:
Bergenin-(Cuscutin)
CPRiL:
55737
SMILES: c1cccc(c12)C3C(OC2=O)CCCO3
Level: 0
Mol. Weight: 328.27 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.87
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.060
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.48
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.580
- Plasma Protein Binding
- 47.3
- 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
- 12.010
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.620
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.610
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.940
- 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
- -0.590
- Rat (Acute)
- 2.190
- Rat (Chronic Oral)
- 3.550
- Fathead Minnow
- 3.940
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 456.000
- Hydration Free Energy
- -14.530
- Log(D) at pH=7.4
- 0.100
- Log(P)
- -0.96
- Log S
- -2.32
- Log(Vapor Pressure)
- -9.19
- Melting Point
- 183.61
- pKa Acid
- 5.23
- pKa Basic
- 3.9
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8865 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8865 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8761 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8761 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8669 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8669 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8357 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8357 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8190 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8190 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7997 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7997 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 4 | 0.7810 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 4 | 0.7810 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7773 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7773 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7724 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7724 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7706 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7706 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7640 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7640 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7569 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7569 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.7548 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.7548 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7530 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7530 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7502 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7502 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7445 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7445 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7365 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7365 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7361 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7361 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7332 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7332 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7280 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7280 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7258 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7258 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7111 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7111 |
| dTDP-4-dehydrorhamnose 3,5-epimerase | A0A6L7H6N0 | A0A1S0QLH9_BACAN | Bacillus anthracis | 3 | 0.7061 |
| dTDP-4-dehydrorhamnose 3,5-epimerase | A0A6L7H6N0 | A0A1S0QLH9_BACAN | Bacillus anthracis | 3 | 0.7061 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7056 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7056 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7029 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7029 |
| Glucose-1-phosphate thymidylyltransferase | Q9AGY4 | Q9AGY4_ANETH | Aneurinibacillus thermoaerophilus | 4 | 0.7028 |
| Glucose-1-phosphate thymidylyltransferase | Q9AGY4 | Q9AGY4_ANETH | Aneurinibacillus thermoaerophilus | 4 | 0.7028 |
| Pteridine reductase 1 | Q01782 | PTR1_LEIMA | Leishmania major | 3 | 0.7015 |
| Pteridine reductase 1 | Q01782 | PTR1_LEIMA | Leishmania major | 3 | 0.7015 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 4 | 0.7011 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 4 | 0.7011 |