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Cystophloroketal D

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-RDGRMOMZSA-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: 132556023

No compound-protein relationship available.

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

Level: 2

Mol. Weight: 564.72 g/mol

SMILES: C1CCCC1CC(=O)CC=CCc2ccccc2

Level: 1

Mol. Weight: 564.72 g/mol

SMILES: C1CCCC1C23CC(CO2)c4c(O3)cccc4

Level: 1

Mol. Weight: 564.72 g/mol

SMILES: c1cccc(c1C23)OC(C2)OC3

Level: 0

Mol. Weight: 564.72 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 564.72 g/mol

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: 99.9
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: 10.870
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.610
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: 7.160
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: -4380.900
Rat (Acute): 2.330
Rat (Chronic Oral): 1.990
Fathead Minnow: 16.770
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 465.010
Hydration Free Energy: -2.970
Log(D) at pH=7.4: 5.180
Log(P): 6.17
Log S: -6.94
Log(Vapor Pressure): -8.36
Melting Point: 190.57
pKa Acid: 8.49
pKa Basic: 4.97

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	0.9151
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9139
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8802
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8749
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8745
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	3	0.8681
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.8672
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.8670
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8570
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	3	0.8521
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8442
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.8178
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8052
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8024
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8000
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7920
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7919
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7909
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.7898
AGAP003309-PA	A0A1U7F4W2	A0A1U7F4W2_ANOGA	Anopheles gambiae	3	0.7840
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7833
Dipeptidyl peptidase 4	P14740	DPP4_RAT	Rattus norvegicus	3	0.7831
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7797
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7768
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.7759
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7752
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7745
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7714
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7704
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7699
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7678
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7605
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7591
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7558
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7527
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7513
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7504
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7465
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7458
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7457
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7456
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7456
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7449
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7447
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7433
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7428
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7417
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7416
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7396
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7393
Nitroreductase domain-containing protein	Q8DW21	Q8DW21_STRMU	Streptococcus mutans serotype c	3	0.7374
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7357
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7357
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7356
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7321
Troponin C, slow skeletal and cardiac muscles	P63316	TNNC1_HUMAN	Homo sapiens	2	0.7308
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7304
Cytochrome b-c1 complex subunit 1, mitochondrial	P31800	QCR1_BOVIN	Bos taurus	3	0.7290
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7286
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7279
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7275
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7271
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7235
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7233
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7233
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.7231
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7218
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7215
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7206
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7193
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7189
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7166
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7143
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7142
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7140
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7133
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7122
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7120
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7120
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7115
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7114
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7105
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7093
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	2	0.7087
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7087
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7081
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7060
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	2	0.7060
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7052
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7044
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7034
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7034
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	2	0.7033
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	2	0.7031
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7024
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7017
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7014
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7011
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	2	0.7009
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7006

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