4,4-di(3-methylbut-2-enyl)-6-geranyl-1-hydroxy-2-(10-hydroxybenzoyl)-6-[2-(1-methylethenyl)-5-methylhex-5-enyl]-cyclohex-1-en-3,5-dione - Compound Card

4,4-di(3-methylbut-2-enyl)-6-geranyl-1-hydroxy-2-(10-hydroxybenzoyl)-6-[2-(1-methylethenyl)-5-methylhex-5-enyl]-cyclohex-1-en-3,5-dione

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4,4-di(3-methylbut-2-enyl)-6-geranyl-1-hydroxy-2-(10-hydroxybenzoyl)-6-[2-(1-methylethenyl)-5-methylhex-5-enyl]-cyclohex-1-en-3,5-dione

Structure
Zoomed Structure
  • Family: Plantae - Clusiaceae-Guttiferae
  • Kingdom: Plantae
  • Class: Benzophenone
    • Subclass: Polyisoprenylated Benzophenone
Canonical Smiles C/C(=C\C[C@@]1(CC(C(=C)C)CCC(=C)C)C(=C(C(=O)c2cccc(c2)O)C(=O)C(C1=O)(CC=C(C)C)CC=C(C)C)O)/CCC=C(C)C
InChI InChI=1S/C43H58O5/c1-28(2)14-12-15-33(11)22-25-43(27-35(32(9)10)19-18-29(3)4)40(47)37(38(45)34-16-13-17-36(44)26-34)39(46)42(41(43)48,23-20-30(5)6)24-21-31(7)8/h13-14,16-17,20-22,26,35,44,47H,3,9,12,15,18-19,23-25,27H2,1-2,4-8,10-11H3/b33-22+/t35?,43-/m1/s1
InChIKey VWWWXPOEFKPTRF-IXINVBECSA-N
Formula C43H58O5
HBA 5
HBD 2
MW 654.93
Rotatable Bonds 17
TPSA 91.67
LogP 11.25
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 48
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 654.43
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]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)C2=CCC(=O)CC2=O

Level: 1

Mol. Weight: 654.93 g/mol

Structure

SMILES: O=C1C=CCC(=O)C1

Level: 0

Mol. Weight: 654.93 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 654.93 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.96
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
20.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.73
Plasma Protein Binding
79.21
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
3.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.04
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.83
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.7
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
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
-42757.81
Rat (Acute)
2.63
Rat (Chronic Oral)
3.57
Fathead Minnow
79.35
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
1272.1
Hydration Free Energy
-2.92
Log(D) at pH=7.4
6.3
Log(P)
11.9
Log S
-7.37
Log(Vapor Pressure)
-55.32
Melting Point
106.68
pKa Acid
8.65
pKa Basic
1.74
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8871
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8871
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8554
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8554
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8408
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8408
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7929
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7929
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7848
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7848
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7841
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7841
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7823
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7823
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7779
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7779
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7755
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7755
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7741
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7741
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7736
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7736
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7645
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7645
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7641
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7641
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7541
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7541
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7539
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7539
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7517
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7517
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7408
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7408
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7407
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7407
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7385
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7385
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7365
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7365
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7308
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7308
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7278
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7278
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7235
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7235
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7208
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7208
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7187
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7187
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7186
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7186
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7174
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7174
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7162
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7162
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7158
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7158
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7147
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7147
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7146
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7146
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7107
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7107
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7044
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7044
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7042
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7042
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7040
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7040
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7039
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7039
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7030
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7030
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7014
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7014
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7008
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7008
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7006
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7006

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