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Cambogin
- Family: Plantae - Guttiferae
- Kingdom: Plantae
- Class: Benzophenone
| Canonical Smiles | CC(=CC[C@]12C(=O)C(=C3[C@@](C1=O)(C[C@@H](C(O3)(C)C)CC=C(C)C)C[C@H](C2(C)C)CC=C(C)C)C(=O)c1ccc(c(c1)O)O)C |
|---|---|
| InChI | InChI=1S/C38H50O6/c1-22(2)11-14-26-20-37-21-27(15-12-23(3)4)36(9,10)44-33(37)30(31(41)25-13-16-28(39)29(40)19-25)32(42)38(34(37)43,35(26,7)8)18-17-24(5)6/h11-13,16-17,19,26-27,39-40H,14-15,18,20-21H2,1-10H3/t26-,27+,37+,38+/m1/s1 |
| InChIKey | KXTNVBQRLRYVCO-LPSZMIQCSA-N |
| Formula | C38H50O6 |
| HBA | 6 |
| HBD | 2 |
| MW | 602.81 |
| Rotatable Bonds | 8 |
| TPSA | 100.9 |
| LogP | 8.59 |
| Number Rings | 4 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 44 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.55 |
| Exact Mass | 602.36 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Allanblackia monticola | Clusiaceae | Plantae | 1508190 |
| 2 | Garcinia nobilis | Guttiferae | Plantae | 469933 |
Showing of synonyms
Cambogin
Isogarcinol
71117-97-0
(1S,3S,9R,11R)-7-(3,4-dihydroxybenzoyl)-4,4,10,10-tetramethyl-3,9,11-tris(3-methylbut-2-enyl)-5-oxatricyclo[7.3.1.01,6]tridec-6-ene-8,13-dione
(3S,4aS,6R,8R)-2,2,7,7-Tetramethyl-3,6,8-tris(3-methyl-2-butenyl)-10-(3,4-dihydroxybenzoyl)-3,4,6,7-tetrahydro-5H-4a,8-methano-2H-cycloocta[b]pyran-9,11(8H)-dione
CHEMBL458934
SCHEMBL14865599
KXTNVBQRLRYVCO-LPSZMIQCSA-N
DTXSID801318189
BDBM50377962
AKOS040755482
DA-74558
HY-127087
CS-0092954
E80627
- Fouotsa H, Dzoyem JP, et al. (2021). Antiproliferative activity of a new xanthone derivative from leaves of Garcinia nobilis Engl.. Natural product research,2021, 35(24), 5604-5611. [View] [PubMed]
- Lenta BN, Vonthron-Sénécheau C, et al. (2007). Leishmanicidal and cholinesterase inhibiting activities of phenolic compounds from Allanblackia monticola and Symphonia globulifera.. Molecules (Basel, Switzerland),2007, 12(8), 1548-1557. [View] [PubMed]
Pubchem:
11135781
Cas:
71117-97-0
Zinc:
ZINC000044361207
Nmrshiftdb2:
60025310
Chembl:
CHEMBL458934
Bindingdb:
50377962
CPRiL:
59492
SMILES: C1CCC(C2=O)C(=O)C(=C(C123)OCCC3)C(=O)c4ccccc4
Level: 1
Mol. Weight: 602.81 g/mol
SMILES: C1CCC(C2=O)C(=O)C=C(C123)OCCC3
Level: 0
Mol. Weight: 602.81 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 602.81 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.77
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.87
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 3.11
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.27
- Plasma Protein Binding
- 111.4
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- 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
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.63
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.33
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.09
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.26
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Toxic
- 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
- -8873.76
- Rat (Acute)
- 2.55
- Rat (Chronic Oral)
- 2.95
- Fathead Minnow
- 26.69
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 369.81
- Hydration Free Energy
- -2.91
- Log(D) at pH=7.4
- 5.7
- Log(P)
- 9.07
- Log S
- -7.41
- Log(Vapor Pressure)
- -14.04
- Melting Point
- 200.47
- pKa Acid
- 6.96
- pKa Basic
- 2.85
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.9110 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 3 | 0.8498 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8377 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8289 |
| prolyl oligopeptidase | Q9X6R4 | Q9X6R4_AERCA | Aeromonas caviae | 3 | 0.8145 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8100 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.8082 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.8048 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.8007 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7916 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7883 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7848 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7847 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7816 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7815 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7809 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7715 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7690 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7679 |
| Multidrug transporter MdfA | P0AEY8 | MDFA_ECOLI | Escherichia coli | 3 | 0.7632 |
| Prostaglandin F2a synthase | Q8I6L9 | Q8I6L9_TRYCR | Trypanosoma cruzi | 3 | 0.7598 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7575 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7558 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7548 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 2 | 0.7539 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7479 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7439 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 3 | 0.7431 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7419 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7411 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7411 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7395 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7363 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7336 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7322 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7282 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7272 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7192 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7181 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7102 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7095 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7079 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7033 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7030 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7018 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 3 | 0.7013 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7000 |