4,4-di(3-methylbut-2-enyl)-6-geranyl-1-hydroxy-2-(10,11-dihydroxybenzoyl)-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-(10,11-dihydroxybenzoyl)-6-[2-(1-methylethenyl)-5-methylhex-5-enyl]-cyclohex-1-en-3,5-dione

Select a section from the left sidebar

4,4-di(3-methylbut-2-enyl)-6-geranyl-1-hydroxy-2-(10,11-dihydroxybenzoyl)-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)c2ccc(c(c2)O)O)C(=O)C(C1=O)(CC=C(C)C)CC=C(C)C)O)/CCC=C(C)C
InChI InChI=1S/C43H58O6/c1-27(2)13-12-14-32(11)21-24-43(26-34(31(9)10)16-15-28(3)4)40(48)37(38(46)33-17-18-35(44)36(45)25-33)39(47)42(41(43)49,22-19-29(5)6)23-20-30(7)8/h13,17-21,25,34,44-45,48H,3,9,12,14-16,22-24,26H2,1-2,4-8,10-11H3/b32-21+/t34?,43-/m1/s1
InChIKey PFAAFAGVZBXCTD-KKDNZHAUSA-N
Formula C43H58O6
HBA 6
HBD 3
MW 670.93
Rotatable Bonds 17
TPSA 111.9
LogP 10.95
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 49
Formal Charge 0
Fraction CSP3 0.47
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]

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 670.93 g/mol

Structure

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

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)
-4.86
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.95
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
32.02

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.37
Plasma Protein Binding
83.62
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
5.34
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.01
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.74
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.36
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
-63349.56
Rat (Acute)
2.43
Rat (Chronic Oral)
3.69
Fathead Minnow
103.39
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
2762.07
Hydration Free Energy
-2.92
Log(D) at pH=7.4
5.75
Log(P)
11.43
Log S
-7.39
Log(Vapor Pressure)
-118.95
Melting Point
125.0
pKa Acid
7.81
pKa Basic
2.55
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 0.8678
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8678
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8536
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8536
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8489
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8489
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8425
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8425
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8298
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8298
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8290
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8290
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8246
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8246
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.8059
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.8059
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7930
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7930
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7891
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7891
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 3 0.7881
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 3 0.7881
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7879
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7879
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7797
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7797
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7698
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7698
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7595
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7595
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7577
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7577
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7523
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7523
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7487
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7487
Catechol O-methyltransferase P21964 COMT_HUMAN Homo sapiens 3 0.7456
Catechol O-methyltransferase P21964 COMT_HUMAN Homo sapiens 3 0.7456
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7394
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7394
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.7384
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.7384
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7383
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7383
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7375
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7375
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7274
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7274
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7243
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7243
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7227
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7227
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7175
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7175
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7157
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7157
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7148
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7148
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7100
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7100
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7083
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7083
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7071
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7071
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7050
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7050
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7029
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7029
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7021
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7021
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7006
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7006

Download SDF