Guttiferone C - Compound Card

Guttiferone C

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Guttiferone C

Structure
Zoomed Structure
  • Family: Plantae - Guttiferae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles CC(=CC[C@@]12C(=O)/C(=C(\c3ccc(c(c3)O)O)/O)/C(=O)[C@](C1=O)(CC(C(=C)C)CCC(=C)C)C[C@@H]([C@@]2(C)CCC=C(C)C)CC=C(C)C)C
InChI InChI=1S/C43H58O6/c1-26(2)13-12-21-41(11)33(18-15-28(5)6)25-42(24-32(30(9)10)16-14-27(3)4)38(47)36(37(46)31-17-19-34(44)35(45)23-31)39(48)43(41,40(42)49)22-20-29(7)8/h13,15,17,19-20,23,32-33,44-46H,3,9,12,14,16,18,21-22,24-25H2,1-2,4-8,10-11H3/b37-36+/t32?,33-,41+,42-,43+/m0/s1
InChIKey NFQCORXWZVREFM-JYCBUDTGSA-N
Formula C43H58O6
HBA 6
HBD 3
MW 670.93
Rotatable Bonds 14
TPSA 111.9
LogP 10.48
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 49
Formal Charge 0
Fraction CSP3 0.51
Exact Mass 670.42
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 symphonia globulifera Guttiferae Plantae 156483

Showing of synonyms

  • 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: 5469793
Nmrshiftdb2: 70001216

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 670.93 g/mol

Structure

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

Level: 0

Mol. Weight: 670.93 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 670.93 g/mol

Anti-hiv

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.93
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
39.14

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.37
Plasma Protein Binding
107.15
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
7.24
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.09
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.51
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.69
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
-74644.5
Rat (Acute)
2.6
Rat (Chronic Oral)
3.77
Fathead Minnow
114.2
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
4188.3
Hydration Free Energy
-2.92
Log(D) at pH=7.4
5.81
Log(P)
10.55
Log S
-7.91
Log(Vapor Pressure)
-156.01
Melting Point
189.82
pKa Acid
6.94
pKa Basic
2.36
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 0.8692
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8664
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8385
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8322
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8231
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.8193
Catechol O-methyltransferase P21964 COMT_HUMAN Homo sapiens 3 0.8129
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8123
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8060
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8039
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7967
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7929
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7865
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7819
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7595
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7504
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7482
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7342
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7330
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7313
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7278
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7263
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7251
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7162
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7161
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7115
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7095
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7081
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7075
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7033
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7021

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