Mangostanin - Compound Card

Mangostanin

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Mangostanin

Structure
Zoomed Structure
  • Family: Plantae - Clusiaceae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles COc1c(O)cc2c(c1CC=C(C)C)c(=O)c1c(o2)cc2c(c1O)C=CC(O2)(C)C
InChI InChI=1S/C24H24O6/c1-12(2)6-7-14-19-17(10-15(25)23(14)28-5)29-18-11-16-13(8-9-24(3,4)30-16)21(26)20(18)22(19)27/h6,8-11,25-26H,7H2,1-5H3
InChIKey HQWHKELJHUFLGD-UHFFFAOYSA-N
Formula C24H24O6
HBA 6
HBD 2
MW 408.45
Rotatable Bonds 3
TPSA 89.13
LogP 5.06
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 408.16
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Pentadesma butyracea Clusiaceae Plantae 198785

Showing of synonyms

  • 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: 5495929
Chebi: 190826
Nmrshiftdb2: 60080167
Bindingdb: 50311741
CPRiL: 413402
Structure

SMILES: O1CC=Cc(c2)c1cc(c23)oc4c(c3=O)cccc4

Level: 0

Mol. Weight: 408.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.710
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.94

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.310
Plasma Protein Binding
58.61
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
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.490
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.560
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.620
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.960
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-17.410
Rat (Acute)
2.410
Rat (Chronic Oral)
2.680
Fathead Minnow
5.560
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
493.590
Hydration Free Energy
-6.060
Log(D) at pH=7.4
3.610
Log(P)
6.18
Log S
-5.8
Log(Vapor Pressure)
-8.92
Melting Point
214.11
pKa Acid
7.99
pKa Basic
6.87
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 0.9295
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9126
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8820
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8700
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8655
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8565
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8510
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8416
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8350
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.8344
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8229
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8167
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8000
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7950
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7938
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7897
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7827
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7718
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7670
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7574
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7502
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7431
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7430
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7372
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7328
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7296
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 4 0.7240
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7192
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7190
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7180
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7176
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7079
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7077
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7040
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7036
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7028

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