Cystophloroketal A - Compound Card

Cystophloroketal A

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Cystophloroketal A

Structure
Zoomed Structure
  • Family: Plantae - Sargassaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Meroditerpenoid
Canonical Smiles COc1cc(C/C=C(/CC(=O)C[C@]2(C)CCC[C@]2(C)[C@]23Oc4cc(O)cc(c4[C@H](C2)C(O3)(C)C)O)\C)c(c(c1)C)O
InChI InChI=1S/C34H44O7/c1-20(9-10-22-15-25(39-7)14-21(2)30(22)38)13-24(36)18-32(5)11-8-12-33(32,6)34-19-26(31(3,4)41-34)29-27(37)16-23(35)17-28(29)40-34/h9,14-17,26,35,37-38H,8,10-13,18-19H2,1-7H3/b20-9+/t26-,32-,33-,34-/m0/s1
InChIKey VXQJPLFMJDLQGJ-ZVVBYUNRSA-N
Formula C34H44O7
HBA 7
HBD 3
MW 564.72
Rotatable Bonds 8
TPSA 105.45
LogP 7.23
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 41
Formal Charge 0
Fraction CSP3 0.56
Exact Mass 564.31
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Cystoseira tamariscifolia Sargassaceae Plantae 2771340

Showing of synonyms

  • El Hattab M, Genta-Jouve G, et al. (2015). Cystophloroketals A−E, Unusual Phloroglucinol−Meroterpenoid Hybrids from the Brown Alga Cystoseira tamariscifolia. Journal of natural products, 2015, 78(7), 1663-70. [View] [PubMed]
Pubchem: 132556020

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CC=CCC(=O)CC2C(CCC2)C34CC(CO3)c5c(O4)cccc5

Level: 2

Mol. Weight: 564.72 g/mol

Structure

SMILES: C1CCCC1CC(=O)CC=CCc2ccccc2

Level: 1

Mol. Weight: 564.72 g/mol

Structure

SMILES: C1CCCC1C23CC(CO2)c4c(O3)cccc4

Level: 1

Mol. Weight: 564.72 g/mol

Structure

SMILES: c1cccc(c1C23)OC(C2)OC3

Level: 0

Mol. Weight: 564.72 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 564.72 g/mol

Structure

SMILES: C1CCCC1

Level: 0

Mol. Weight: 564.72 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.16
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.750
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.61

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.240
Plasma Protein Binding
100.43
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
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
Non-Inhibitor

Excretion

Clearance
10.870
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.730
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.850
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.170
Micronucleos
Toxic
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
Toxic
T. Pyriformis
-4379.300
Rat (Acute)
2.330
Rat (Chronic Oral)
1.980
Fathead Minnow
17.370
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
465.420
Hydration Free Energy
-2.960
Log(D) at pH=7.4
5.170
Log(P)
6.17
Log S
-6.94
Log(Vapor Pressure)
-8.32
Melting Point
203.4
pKa Acid
8.54
pKa Basic
5.05
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9646
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9389
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.9311
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9123
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.9008
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.8962
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.8805
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8794
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.8669
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8612
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8577
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8490
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8433
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8286
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8266
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.8230
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8185
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8144
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.8137
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8133
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8123
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.8119
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8112
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 4 0.8073
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8064
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8034
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8013
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8007
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7983
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7934
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7909
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7854
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7821
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7804
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7782
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7777
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7765
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7735
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7727
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7726
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7698
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7696
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7675
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 2 0.7674
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7661
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7657
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7649
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7613
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7595
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7586
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7571
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7548
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7544
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7533
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7508
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7507
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7504
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7492
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7491
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7491
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7481
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7472
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7455
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7419
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7418
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7411
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7406
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.7403
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7393
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7377
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7375
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7372
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7356
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7348
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7332
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7322
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7322
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7315
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7314
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 2 0.7313
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7306
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7304
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase Q9WY79 MURE_THEMA Thermotoga maritima 3 0.7287
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7287
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7286
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7284
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7283
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7270
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7267
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7265
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7230
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7227
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7223
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7222
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7221
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7221
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7220
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7217
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7207
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7202
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7201
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7196
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7194
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7186
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7174
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7173
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7158
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7155
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7148
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7134
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7134
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7122
Aromatic/aminoadipate aminotransferase 1 P53090 ARO8_YEAST Saccharomyces cerevisiae 3 0.7118
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7116
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 2 0.7114
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7112
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7109
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7109
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7105
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7097
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7092
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7083
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7069
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7061
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7061
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7054
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7053
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7050
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7042
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7034
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7033
Naphthalene 1,2-dioxygenase system, large oxygenase component P0A110 NDOB_PSEPU Pseudomonas putida 2 0.7031
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7030
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7028
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7026
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7026
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7023
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7022
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7016
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7002

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