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1,3,6-trihydroxy-7-methoxy-2,8-diprenylxanthone
- Family: Plantae - Guttiferae
- Kingdom: Plantae
- Class: Xanthone
| Canonical Smiles | COc1c(O)cc2c(c1CC=C(C)C)c(=O)c1c(o2)cc(c(c1O)CC=C(C)C)O |
|---|---|
| InChI | InChI=1S/C24H26O6/c1-12(2)6-8-14-16(25)10-19-21(22(14)27)23(28)20-15(9-7-13(3)4)24(29-5)17(26)11-18(20)30-19/h6-7,10-11,25-27H,8-9H2,1-5H3 |
| InChIKey | GNRIZKKCNOBBMO-UHFFFAOYSA-N |
| Formula | C24H26O6 |
| HBA | 6 |
| HBD | 3 |
| MW | 410.47 |
| Rotatable Bonds | 5 |
| TPSA | 100.13 |
| LogP | 5.09 |
| Number Rings | 3 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.29 |
| Exact Mass | 410.17 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Pentadesma butyracea | Clusiaceae | Plantae | 198785 |
| 2 | Pentadesma butyracea | Clusiaceae | Plantae | 198785 |
| 3 | Allanblackia monticola | Guttiferae | Plantae | 1508190 |
| 4 | Allanblackia floribunda | Guttiferae | Plantae | 469914 |
Showing of synonyms
1,3,6-trihydroxy-7-methoxy-2,8-diprenylxanthone
Alpha-Mangostin
Mangostin
6147-11-1
1,3,6-Trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
NSC-30552
U6RIV93RU1
7-o-methyl-4-desprenylcostatin
CHEBI:67547
NSC 27593
NSC 30552
NSC-27593
1,3,6-Trihydroxy-7-methoxy-2,8-bis(3,3-dimethylallyl)xanthone
UNII-U6RIV93RU1
NSC 139154
NSC-139154
1,3,6-Trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthen-9-one
HSDB 8103
DTXSID00210420
9H-Xanthen-9-one, 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-
Xanthen-9-one, 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-
Alpha-mangosten
1,3,6-Trihydroxy-7-methoxy-2,8-di(3-methyl-2-butenyl)xanthone
1,3,6-TRIHYDROXY-7-METHOXY-2,8-BIS-(3-METHYL-2-BUTEN-1-YL)-9H-XANTHEN-9-ONE
7-O-methyl-gamma-mangostin
Delta-mangostin
DTXCID00132911
448-420-7
Mangostine
Alpha-Mangostin, 95%
A-Mangostin
1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
NSC27593
NSC30552
MFCD00135200
9H-Xanthen-9-one,1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-
CHEMBL323197
TNP00140
3,6,8-trihydroxy-2-methoxy-1,7-bis(3-methylbut-2-enyl)xanthen-9-one
1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-enyl)-9H-xanthen-9-one
Alpha-mangostin?
9H-Xanthen-9-one,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-
Xanthen-9-one,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-
.Alpha.-mangosten
.Alpha.-mangostin
Spectrum_001726
SpecPlus_000574
MANGOSTIN [MI]
Spectrum2_001620
Spectrum3_001297
Spectrum4_001911
Spectrum5_000622
1,3,6-Trihydroxy-7-methoxy-2,8-bis(3-methyl-2-buten-1-yl)-9H-xanthen-9-one
Alpha-Mangostin (Standard)
BSPBio_002933
KBioGR_002529
KBioSS_002206
BIDD:ER0576
DivK1c_006670
SCHEMBL354735
SPECTRUM1504015
SPECTRUM1505128
7-o-methyl-.gamma.-mangostin
SPBio_001659
GTPL13469
HY-N0328R
KBio1_001614
KBio2_002206
KBio2_004774
KBio2_007342
KBio3_002153
BCP13253
HY-N0328
KXB04773
Alpha-Mangostin, >=98% (HPLC)
1,7-bis(3-methylbut-2-enyl)-3,6,8-trihydroxy-2-methoxyxanthen-9-one
BDBM50214969
CCG-36465
MSK181798
NSC139154
S3804
AKOS015912806
AC-6089
CS-6435
DS-3359
FM25010
SDCCGMLS-0066796.P001
NCGC00017251-01
NCGC00017251-02
NCGC00017251-03
NCGC00017251-04
NCGC00017251-05
NCGC00017251-06
NCGC00095730-01
NCGC00095730-02
NCGC00095730-03
NCGC00178385-01
DB-053898
M2793
AK-693/21096021
Q909638
SR-05000002649
SR-05000002649-1
BRD-K11991978-001-02-6
BRD-K11991978-001-03-4
1,3,6-Trihydroxy-7-methoxy-2,8-bis-(3-methyl-but-2-enyl)-xanthen-9-one
(c) paragraph sign-mangostin pound>>alpha-Mangostin
9H-Xanthen-9-one, 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-buten-1-yl)-
Alpha-Mangostin1,3,6-Trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
- 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]
- Lenta BN, Kamdem LM, et al. (2011). Antiplasmodial constituents from the fruit pericarp of Pentadesma butyracea.. Planta medica,2011, 77(4), 377-379. [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]
- Zelefack F, Guilet D, et al. (2009). Cytotoxic and antiplasmodial xanthones from Pentadesma butyracea.. Journal of natural products,2009, 72(5), 954-957. [View] [PubMed]
Pubchem:
5281650
Cas:
6147-11-1
Gnps:
CCMSLIB00005771965
Zinc:
ZINC000005430812
Kegg Ligand:
C10080
Chebi:
67547
Nmrshiftdb2:
60025318
Metabolights:
MTBLC67547
Chembl:
CHEMBL323197
Comptox:
DTXSID00210420
Pdb Ligand:
MKS
Bindingdb:
50214969
CPRiL:
55355
SMILES: c1cccc(c12)oc3c(c2=O)cccc3
Level: 0
Mol. Weight: 410.47 g/mol
Anti-plasmodial
Absorption
- Caco-2 (logPapp)
- -5.26
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.870
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -0.96
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.090
- Plasma Protein Binding
- 56.73
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- 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
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.350
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.040
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.700
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.540
- 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
- -13.200
- Rat (Acute)
- 2.160
- Rat (Chronic Oral)
- 3.260
- Fathead Minnow
- 5.740
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 491.950
- Hydration Free Energy
- -7.280
- Log(D) at pH=7.4
- 3.340
- Log(P)
- 6.73
- Log S
- -5.8
- Log(Vapor Pressure)
- -8.65
- Melting Point
- 204.18
- pKa Acid
- 8.54
- pKa Basic
- 7.4
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.9195 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9168 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9074 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.8692 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.8642 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8640 |
| 3'-5' exoribonuclease Rv2179c | P9WJ73 | EXRBN_MYCTU | Mycobacterium tuberculosis | 3 | 0.8640 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8619 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.8496 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8382 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.8343 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.8276 |
| Protein S100-A13 | Q99584 | S10AD_HUMAN | Homo sapiens | 3 | 0.8263 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8254 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8249 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8228 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8189 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8159 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8028 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 4 | 0.8008 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7967 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7951 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7943 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7913 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7837 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7832 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7774 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7715 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7663 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 3 | 0.7662 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7624 |
| Nucleoside permease | Q9KPL5 | Q9KPL5_VIBCH | Vibrio cholerae serotype O1 | 4 | 0.7611 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7597 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7580 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7566 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7545 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 4 | 0.7517 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.7476 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.7473 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7463 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7459 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7435 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7424 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7416 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 4 | 0.7386 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7383 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.7380 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7317 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7301 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7298 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7284 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7234 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7219 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7194 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7190 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7190 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7184 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7178 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7177 |
| Methionine aminopeptidase 2 | P50579 | MAP2_HUMAN | Homo sapiens | 3 | 0.7170 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 4 | 0.7152 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 4 | 0.7136 |
| Streptogramin A acetyltransferase | P50870 | VATD_ENTFC | Enterococcus faecium | 3 | 0.7112 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7109 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7072 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 2 | 0.7070 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7068 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 3 | 0.7065 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.7063 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7061 |
| Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.7046 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.7033 |
| NAD(P)H dehydrogenase (quinone) | Q9I509 | NQOR_PSEAE | Pseudomonas aeruginosa | 5 | 0.7010 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7007 |