Guttiferone E - Compound Card

Guttiferone E

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Guttiferone E

Structure
Zoomed Structure
  • Family: Plantae - Guttiferae
  • Kingdom: Plantae
  • Class: Benzophenone
    • Subclass: Prenylated Benzophenone
Canonical Smiles CC(=CC[C@@]12C(=O)/C(=C(\c3ccc(c(c3)O)O)/O)/C(=O)[C@](C1=O)(C[C@H](C(=C)C)CC=C(C)C)C[C@@H](C2(C)C)CC=C(C)C)C
InChI InChI=1S/C38H50O6/c1-22(2)11-13-27(25(7)8)20-37-21-28(15-12-23(3)4)36(9,10)38(35(37)44,18-17-24(5)6)34(43)31(33(37)42)32(41)26-14-16-29(39)30(40)19-26/h11-12,14,16-17,19,27-28,39-41H,7,13,15,18,20-21H2,1-6,8-10H3/b32-31+/t27-,28+,37+,38-/m1/s1
InChIKey DTTONLKLWRTCAB-OLPCVCRBSA-N
Formula C38H50O6
HBA 6
HBD 3
MW 602.81
Rotatable Bonds 10
TPSA 111.9
LogP 8.76
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 44
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 602.36
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Garcinia punctata Clusiaceae Plantae 469937
2 symphonia globulifera Guttiferae Plantae 156483

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: 5352088
Nmrshiftdb2: 60079201
CPRiL: 105867
Structure

SMILES: C1CCC(C2=O)C(=O)C(C(=O)C12)=Cc3ccccc3

Level: 1

Mol. Weight: 602.81 g/mol

Structure

SMILES: C12C(=O)C(=C)C(=O)C(C1=O)CCC2

Level: 0

Mol. Weight: 602.81 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 602.81 g/mol

Anti-hiv
Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.88
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.23
Plasma Protein Binding
114.91
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Inhibitor

Excretion

Clearance
7.2
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.22
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.27
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.08
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
-7282.95
Rat (Acute)
2.91
Rat (Chronic Oral)
3.3
Fathead Minnow
23.35
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
410.67
Hydration Free Energy
-2.87
Log(D) at pH=7.4
5.08
Log(P)
8.92
Log S
-6.86
Log(Vapor Pressure)
-12.18
Melting Point
164.76
pKa Acid
7.11
pKa Basic
3.01
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9167
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8964
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8754
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8628
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8612
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8425
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8378
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8375
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8369
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8304
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8302
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.8275
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8164
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8159
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8040
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8014
Catechol O-methyltransferase P21964 COMT_HUMAN Homo sapiens 3 0.7947
Serine/threonine-protein kinase N1 Q16512 PKN1_HUMAN Homo sapiens 3 0.7795
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7761
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7753
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7738
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7713
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7711
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7692
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7680
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7660
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7637
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7614
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 3 0.7600
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7569
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7540
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7532
LysR-type regulatory protein Q7WT50 Q7WT50_9BURK Burkholderia sp. DNT 3 0.7510
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7508
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7500
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7477
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7460
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7404
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7402
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7399
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7399
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7390
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7351
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7302
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7292
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7282
3-hydroxy-3-methylglutaryl-coenzyme A reductase P13702 MVAA_PSEMV Pseudomonas mevalonii 3 0.7275
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7273
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7266
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7259
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7242
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7224
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7222
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7162
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7160
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7160
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7147
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7139
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7136
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7129
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7127
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7118
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7112
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7105
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7091
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7089
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7087
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7079
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7067
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7005

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