Guttiferone A - Compound Card

Guttiferone A

Select a section from the left sidebar

Guttiferone A

Structure
Zoomed Structure
  • Family: Plantae - Clusiaceae
  • Kingdom: Plantae
  • Class: Benzophenone
    • Subclass: Prenylated Benzophenone
Canonical Smiles CC(=CC[C@]12C[C@H](CC=C(C)C)[C@@]([C@@](C2=O)(C(=O)/C(=C(\c2ccc(c(c2)O)O)/O)/C1=O)CC=C(C)C)(C)CCC=C(C)C)C
InChI InChI=1S/C38H50O6/c1-23(2)11-10-18-36(9)28(14-12-24(3)4)22-37(19-16-25(5)6)33(42)31(32(41)27-13-15-29(39)30(40)21-27)34(43)38(36,35(37)44)20-17-26(7)8/h11-13,15-17,21,28,39-41H,10,14,18-20,22H2,1-9H3/b32-31+/t28-,36+,37-,38+/m0/s1
InChIKey SHBMQWRFQJLYJU-UGUZKGPTSA-N
Formula C38H50O6
HBA 6
HBD 3
MW 602.81
Rotatable Bonds 10
TPSA 111.9
LogP 8.9
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 Symphonia globulifera Clusiaceae Plantae 156483
2 symphonia globulifera Guttiferae Plantae 156483
3 Symphonia globulifera Guttiferae Plantae 156483
4 Garcinia livingstonei Clusiaceae Plantae 469932

Showing of synonyms

  • Ngouela S, Lenta BN, et al. (2006). Anti-plasmodial and antioxidant activities of constituents of the seed shells of Symphonia globulifera Linn f.. Phytochemistry,2006, 67(3), 302-306. [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]
  • Mulholland DA, Mwangi EM, et al. (2013). Non-toxic melanin production inhibitors from Garcinia livingstonei (Clusiaceae). Journal of ethnopharmacology, 2013, 149(2), 570–575. [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: 5352090
Nmrshiftdb2: 60079141
CPRiL: 68977
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-plasmodial

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.91
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
2.16

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.26
Plasma Protein Binding
109.96
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
Inhibitor

Excretion

Clearance
7.62
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.74
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.13
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.11
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
-8135.45
Rat (Acute)
2.55
Rat (Chronic Oral)
3.82
Fathead Minnow
25.9
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
391.53
Hydration Free Energy
-2.86
Log(D) at pH=7.4
5.16
Log(P)
8.58
Log S
-7.38
Log(Vapor Pressure)
-13.46
Melting Point
205.26
pKa Acid
7.33
pKa Basic
2.62
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8894
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8764
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8524
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8511
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8429
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8416
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8296
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8010
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7929
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7894
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.7884
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7883
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7828
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7756
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7754
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7715
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7674
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7557
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7554
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7530
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7514
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7471
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7463
LysR-type regulatory protein Q7WT50 Q7WT50_9BURK Burkholderia sp. DNT 3 0.7458
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7437
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7419
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7404
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7389
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7386
Catechol O-methyltransferase P21964 COMT_HUMAN Homo sapiens 3 0.7375
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7356
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7328
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7273
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7260
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7241
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7225
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7205
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7147
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7109
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7100
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7085
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7074
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7060
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7054

Download SDF