(+-)-2c,6c-bis-(1-oxy-2,3-dimethoxyphenyl)-3,7-dioxabicyclo-[3.3.0]-octane - Compound Card

(+-)-2c,6c-bis-(1-oxy-2,3-dimethoxyphenyl)-3,7-dioxabicyclo-[3.3.0]-octane

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(+-)-2c,6c-bis-(1-oxy-2,3-dimethoxyphenyl)-3,7-dioxabicyclo-[3.3.0]-octane

Structure
Zoomed Structure
  • Family: Plantae - Tamaricaceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Diaryloxy Furanofuran Lignan
Canonical Smiles COc1c(O[C@H]2OCC3C2CO[C@@H]3Oc2cccc(c2OC)OC)cccc1OC
InChI InChI=1S/C22H26O8/c1-23-15-7-5-9-17(19(15)25-3)29-21-13-11-28-22(14(13)12-27-21)30-18-10-6-8-16(24-2)20(18)26-4/h5-10,13-14,21-22H,11-12H2,1-4H3/t13?,14?,21-,22-/m1/s1
InChIKey NEWIMESFSVSIEO-HICDVDAHSA-N
Formula C22H26O8
HBA 8
HBD 0
MW 418.44
Rotatable Bonds 8
TPSA 73.84
LogP 3.12
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.45
Exact Mass 418.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tamarix aphylla Tamaricaceae Plantae 189786

Showing of synonyms

  • Souliman A, Barakat H, et al. (1991). Phenolics From The Bark Of Tamarix Aphylla. Phytochemistry, 1991, 30(11), 3763-3766. [View]
Pubchem: 101616808

No compound-protein relationship available.

Structure

SMILES: c1ccccc1OC(OC2)C(C23)COC3Oc4ccccc4

Level: 2

Mol. Weight: 418.44 g/mol

Structure

SMILES: C1OCC(C12)COC2Oc3ccccc3

Level: 1

Mol. Weight: 418.44 g/mol

Structure

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 418.44 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 418.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.570
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.280
Plasma Protein Binding
62.31
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.570
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.000
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.600
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
7.240
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-61.210
Rat (Acute)
3.020
Rat (Chronic Oral)
1.660
Fathead Minnow
5.130
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
414.060
Hydration Free Energy
-3.360
Log(D) at pH=7.4
2.650
Log(P)
2.84
Log S
-4.11
Log(Vapor Pressure)
-6.96
Melting Point
102.3
pKa Acid
9.25
pKa Basic
-2.75
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9445
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9228
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8632
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.8579
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.8474
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8380
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8330
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8253
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8244
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8152
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.8071
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7970
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.7961
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7959
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7941
Isoliquiritigenin 2'-O-methyltransferase P93324 CHOMT_MEDSA Medicago sativa 3 0.7923
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7889
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7888
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.7798
Pol protein Q000H7 Q000H7_9HIV1 Human immunodeficiency virus 1 3 0.7791
Cyclic GMP-AMP synthase Q8C6L5 CGAS_MOUSE Mus musculus 3 0.7786
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7774
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7774
Aminopeptidase N P04825 AMPN_ECOLI Escherichia coli 3 0.7720
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7719
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7716
Uridine phosphorylase P12758 UDP_ECOLI Escherichia coli 3 0.7700
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.7657
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7652
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7616
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7612
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7608
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7559
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7557
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7548
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7547
Tryptase alpha/beta-1 Q15661 TRYB1_HUMAN Homo sapiens 3 0.7512
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7511
Ditrans,polycis-undecaprenyl-diphosphate synthase ((2E,6E)-farnesyl-diphosphate specific) P60472 UPPS_ECOLI Escherichia coli 4 0.7510
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7504
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7499
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7491
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7490
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7489
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7464
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7461
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7456
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7455
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7434
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7423
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 3 0.7413
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7399
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7395
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7362
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7358
Thymidylate kinase Q8I4S1 Q8I4S1_PLAF7 Plasmodium falciparum 4 0.7350
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7348
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7339
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7336
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 4 0.7334
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7331
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7325
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7313
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7310
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7307
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7295
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7293
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7293
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7282
Decaprenylphosphoryl-beta-D-ribose oxidase I6X8C4 I6X8C4_MYCTU Mycobacterium tuberculosis 3 0.7278
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7278
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7275
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7268
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7257
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7257
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 2 0.7246
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7238
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7235
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7230
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7221
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7207
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7204
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7196
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7181
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7176
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7170
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7169
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7163
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7156
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7154
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7152
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 4 0.7151
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7150
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 2 0.7149
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7138
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7130
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7119
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7116
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7113
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 2 0.7113
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7110
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7108
DNA topoisomerase 1 P06612 TOP1_ECOLI Escherichia coli 3 0.7104
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7104
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 2 0.7102
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7101
Kelch-like ECH-associated protein 1 Q14145 KEAP1_HUMAN Homo sapiens 3 0.7098
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7098
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7093
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7080
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7077
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7069
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7062
Lethal factor P15917 LEF_BACAN Bacillus anthracis 2 0.7059
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7058
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7056
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7037
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7037
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7026
Unconventional myosin-Va Q02440 MYO5A_CHICK Gallus gallus 2 0.7025
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7021
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 2 0.7003

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