5,5-dimethyl-6-geranyl-3-hydroxy-2-(13,14-dihydroxybenzoyl)-4-(3,7-dimethyloct-2,7-dienyl)-8-(3-methylbut-2-enyl)-bicyclo[3.3.1]nonan-2-en-1,9-dione - Compound Card

5,5-dimethyl-6-geranyl-3-hydroxy-2-(13,14-dihydroxybenzoyl)-4-(3,7-dimethyloct-2,7-dienyl)-8-(3-methylbut-2-enyl)-bicyclo[3.3.1]nonan-2-en-1,9-dione

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5,5-dimethyl-6-geranyl-3-hydroxy-2-(13,14-dihydroxybenzoyl)-4-(3,7-dimethyloct-2,7-dienyl)-8-(3-methylbut-2-enyl)-bicyclo[3.3.1]nonan-2-en-1,9-dione

Structure
Zoomed Structure
  • Family: Plantae - Clusiaceae-Guttiferae
  • Kingdom: Plantae
  • Class: Benzophenone
    • Subclass: Polyisoprenylated Benzophenone
Canonical Smiles CC(=CC[C@]12C[C@H](C/C=C(/CCC=C(C)C)\C)C([C@@](C2=O)(C(=C(C1=O)C(=O)c1ccc(c(c1)O)O)O)C/C=C(/CCCC(=C)C)\C)(C)C)C
InChI InChI=1S/C43H58O6/c1-27(2)13-11-15-30(7)17-19-33-26-42(23-21-29(5)6)38(47)36(37(46)32-18-20-34(44)35(45)25-32)39(48)43(40(42)49,41(33,9)10)24-22-31(8)16-12-14-28(3)4/h13,17-18,20-22,25,33,44-45,48H,3,11-12,14-16,19,23-24,26H2,1-2,4-10H3/b30-17+,31-22+/t33-,42-,43+/m0/s1
InChIKey GLKCRKRBKFGORM-RPBVFHEQSA-N
Formula C43H58O6
HBA 6
HBD 3
MW 670.93
Rotatable Bonds 15
TPSA 111.9
LogP 10.79
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 Garcinia semseii Clusiaceae-Guttiferae Plantae 58227

Showing of synonyms

  • Magadula JJ, Kapingu MC, et al. (2008). Polyisoprenylated benzophenones from Garcinia semseii (Clusiaceae). Phytochemistry Letters,2008,1(4),215-218. [View] [PubMed]
Pubchem: 163131880

No compound-protein relationship available.

Structure

SMILES: C1CCC(C2=O)C=C(C(=O)C12)C(=O)c3ccccc3

Level: 1

Mol. Weight: 670.93 g/mol

Structure

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

Level: 0

Mol. Weight: 670.93 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 670.93 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.86
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
42.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.42
Plasma Protein Binding
108.28
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-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
5.77
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
0.58
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.37
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
-81930.25
Rat (Acute)
2.46
Rat (Chronic Oral)
3.52
Fathead Minnow
123.21
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
4864.02
Hydration Free Energy
-2.92
Log(D) at pH=7.4
6.06
Log(P)
11.34
Log S
-7.41
Log(Vapor Pressure)
-184.49
Melting Point
138.53
pKa Acid
7.24
pKa Basic
3.02
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8531
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8531
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8416
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8416
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8377
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8377
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8299
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8299
Catechol O-methyltransferase P21964 COMT_HUMAN Homo sapiens 3 0.8244
Catechol O-methyltransferase P21964 COMT_HUMAN Homo sapiens 3 0.8244
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8209
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8209
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8066
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8066
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7964
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7964
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7842
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7842
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7778
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7778
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7659
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7659
LysR-type regulatory protein Q7WT50 Q7WT50_9BURK Burkholderia sp. DNT 3 0.7653
LysR-type regulatory protein Q7WT50 Q7WT50_9BURK Burkholderia sp. DNT 3 0.7653
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7607
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7607
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7552
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7552
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7519
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7519
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7295
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7295
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7261
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7261
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7196
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7196
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7194
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7194
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7186
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7186
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7168
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7168
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7157
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7157
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7144
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7144
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7061
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7061
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7057
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7057
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7023
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7023
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7010
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7010

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