Isoxanthochymol - Compound Card

Isoxanthochymol

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Isoxanthochymol

Structure
Zoomed Structure
  • Family: Guttiferae, Clusiaceae
  • Kingdom: Plantae
  • Class: Benzophenone
    • Subclass: Prenylated 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+/m0/s1
InChIKey KXTNVBQRLRYVCO-MWVHARJDSA-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 Garcinia punctata Clusiaceae Plantae 469937
2 Garcinia ovalifolia Guttiferae Plantae 469935

Showing of synonyms

  • Dzoyem J, Lannang A, et al. (2015). Anti-inflammatory activity of benzophenone and xanthone derivatives isolated from Garcinia (Clusiaceae) species. Phytochemistry Letters, 2015, 14, 153-158. [View]
  • Gustafson KR, Blunt JW, et al. (1992). The guttiferones, HIV-inhibitory benzophenones from Symphonia globulifera, Garcinia livingstonei, Garcinia ovalifolia and Clusia rosea. Tetrahedron, 1992, 48(46), 10093-10192. [View]
Pubchem: 10461245
Nmrshiftdb2: 60079208
CPRiL: 206765
Structure

SMILES: C1CCC(C2=O)C(=O)C(=C(C123)OCCC3)C(=O)c4ccccc4

Level: 1

Mol. Weight: 310.35 g/mol

Structure

SMILES: C1CCC(C2=O)C(=O)C=C(C123)OCCC3

Level: 0

Mol. Weight: 206.24 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.71
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
111.34
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
0.34
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
7.25
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
-8873.92
Rat (Acute)
2.56
Rat (Chronic Oral)
2.95
Fathead Minnow
26.7
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
369.48
Hydration Free Energy
-2.91
Log(D) at pH=7.4
5.71
Log(P)
9.22
Log S
-7.41
Log(Vapor Pressure)
-14.12
Melting Point
200.6
pKa Acid
6.97
pKa Basic
2.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8478
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8421
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8412
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8293
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8283
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.8261
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8232
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8164
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8150
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.8012
Catechol O-methyltransferase P21964 COMT_HUMAN Homo sapiens 3 0.7961
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 3 0.7881
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7869
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7709
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.7700
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7699
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7696
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7687
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7653
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7637
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7593
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7572
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7525
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7525
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7463
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7462
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7443
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7422
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7411
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7388
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7379
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7376
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7348
LysR-type regulatory protein Q7WT50 Q7WT50_9BURK Burkholderia sp. DNT 3 0.7345
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7313
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7287
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7280
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7261
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7251
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7236
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7210
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7188
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7155
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.7113
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7113
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7108
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7104
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7085
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7064
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7064
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7043
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7036
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7030
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7029
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7026
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7003

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