Cystophloroketal B - Compound Card

Cystophloroketal B

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Cystophloroketal B

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-/m1/s1
InChIKey VXQJPLFMJDLQGJ-HJQNCSGPSA-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: 132556021

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)
-5.15
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
0.59

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.240
Plasma Protein Binding
100.03
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.900
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.650
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
-4379.620
Rat (Acute)
2.330
Rat (Chronic Oral)
1.990
Fathead Minnow
17.410
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
466.060
Hydration Free Energy
-2.970
Log(D) at pH=7.4
5.150
Log(P)
6.16
Log S
-6.94
Log(Vapor Pressure)
-8.32
Melting Point
199.28
pKa Acid
8.48
pKa Basic
4.99
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 0.9796
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9131
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9106
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8922
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.8845
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8814
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8773
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8748
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8747
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.8688
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8668
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8651
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.8638
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8611
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8601
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8585
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8472
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8463
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8410
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8322
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8313
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8304
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8273
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8230
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8208
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8177
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8168
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8167
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8102
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8078
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8044
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8039
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.8011
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7890
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7884
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7877
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7872
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7821
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7796
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7779
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7727
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7693
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7689
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7660
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7636
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7618
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7606
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7585
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7549
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7539
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7533
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7523
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7505
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7497
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7487
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7477
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7475
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7473
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7469
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7464
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7460
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7457
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7433
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 2 0.7431
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 2 0.7426
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7413
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7412
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7403
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7403
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7399
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7381
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7377
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7374
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7374
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7360
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase Q9WY79 MURE_THEMA Thermotoga maritima 3 0.7357
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7357
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7345
Aromatic/aminoadipate aminotransferase 1 P53090 ARO8_YEAST Saccharomyces cerevisiae 3 0.7336
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7323
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7323
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7310
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7307
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7302
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7300
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7292
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7288
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7287
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7287
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7286
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7280
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7274
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.7267
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7266
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7253
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7242
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7236
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7235
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7230
Naphthalene 1,2-dioxygenase system, large oxygenase component P0A110 NDOB_PSEPU Pseudomonas putida 2 0.7227
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7220
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7218
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7217
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7214
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7207
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7204
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7204
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7204
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7198
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7196
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7191
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7188
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7181
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7179
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7176
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.7175
Dipeptidyl peptidase 4 P14740 DPP4_RAT Rattus norvegicus 3 0.7171
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7170
Glycolate oxidase P05414 GOX_SPIOL Spinacia oleracea 4 0.7163
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7149
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7140
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7133
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7130
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7124
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7112
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7110
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7095
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7095
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7085
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7084
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7079
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7077
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7076
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7075
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7073
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7061
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7060
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7051
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7046
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7044
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7041
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7036
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7035
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7033
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7031
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7028
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7019
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7015
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7014

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