(3R,4R,3'R,4'R)-6,6'-dimethoxy-3,4,3',4'-tetrahydro-2H,2'H-[3,3']bichromenyl-4,4'-diol - Compound Card

(3R,4R,3'R,4'R)-6,6'-dimethoxy-3,4,3',4'-tetrahydro-2H,2'H-[3,3']bichromenyl-4,4'-diol

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(3R,4R,3'R,4'R)-6,6'-dimethoxy-3,4,3',4'-tetrahydro-2H,2'H-[3,3']bichromenyl-4,4'-diol

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Ellagic Acid Derivative
Canonical Smiles COc1ccc2c(c1)[C@H](O)[C@@H](CO2)[C@@H]1COc2c([C@@H]1O)cc(cc2)OC
InChI InChI=1S/C20H22O6/c1-23-11-3-5-17-13(7-11)19(21)15(9-25-17)16-10-26-18-6-4-12(24-2)8-14(18)20(16)22/h3-8,15-16,19-22H,9-10H2,1-2H3/t15-,16-,19-,20-/m0/s1
InChIKey ANVSINVPZBSBDR-FVCZOJIISA-N
Formula C20H22O6
HBA 6
HBD 2
MW 358.39
Rotatable Bonds 3
TPSA 77.38
LogP 2.49
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.4
Exact Mass 358.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Turraeanthus mannii Meliaceae Plantae 1317901

Showing of synonyms

  • Sielinou V, Vardamides J, et al. (2012). Phenolic derivatives and an antifungal and cytototoxic labdane diterpenoid from the root bark of Turraeanthus mannii. Phytochemistry Letters, 2012, 5(3), 409-413. [View]
Pubchem: 101717550

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OCC(C2)C(C3)COc(c34)cccc4

Level: 1

Mol. Weight: 358.39 g/mol

Structure

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 358.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.57
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.550
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.13

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.110
Plasma Protein Binding
71.15
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.650
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.580
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.440
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.020
Micronucleos
Toxic
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
Toxic
T. Pyriformis
-5.160
Rat (Acute)
2.230
Rat (Chronic Oral)
2.400
Fathead Minnow
4.090
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
433.340
Hydration Free Energy
-7.640
Log(D) at pH=7.4
2.660
Log(P)
2.27
Log S
-2.9
Log(Vapor Pressure)
-8.33
Melting Point
180.72
pKa Acid
9.97
pKa Basic
1.29
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.9275
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9258
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9031
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9026
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.9018
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8990
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8919
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8863
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8840
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8788
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8788
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8749
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8696
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8693
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8679
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8619
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.8556
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8536
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8499
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.8491
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8468
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8455
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8424
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8391
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8318
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8307
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8260
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8244
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8188
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8186
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8168
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8132
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8105
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8081
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8079
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8075
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 4 0.8040
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.8024
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8023
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7968
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7964
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7958
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7946
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7937
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7922
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7917
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7910
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7895
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7878
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7872
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7868
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7779
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7755
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7727
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7726
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7651
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7645
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7637
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7586
Inorganic pyrophosphatase Q3JUV5 Q3JUV5_BURP1 Burkholderia pseudomallei 3 0.7584
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7581
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7579
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7551
Decaprenylphosphoryl-beta-D-ribose oxidase I6X8C4 I6X8C4_MYCTU Mycobacterium tuberculosis 3 0.7537
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7519
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7516
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.7496
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7491
Beta-lactamase Q79MP6 Q79MP6_PSEAI Pseudomonas aeruginosa 2 0.7490
Large structural protein Q91L20 Q91L20_9MONO Human metapneumovirus 3 0.7470
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7470
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 3 0.7469
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7455
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7446
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7444
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7439
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7431
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 3 0.7428
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7410
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7410
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7366
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7354
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7342
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 3 0.7337
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7333
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 2 0.7329
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7324
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7323
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7311
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7309
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7296
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7295
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7292
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 2 0.7279
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7271
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7264
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7250
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7248
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7248
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7247
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7243
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7242
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 4 0.7235
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7227
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7211
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7210
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7205
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7202
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7201
Geranyl diphosphate 2-C-methyltransferase D3KYU3 GPPMT_STRLS Streptomyces lasalocidi 3 0.7199
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7197
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7193
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7187
Serine hydroxymethyltransferase Q7SIB6 Q7SIB6_GEOSE Geobacillus stearothermophilus 3 0.7181
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7171
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7166
Cytosolic IMP-GMP specific 5'-nucleotidase Q5ZZB6 Q5ZZB6_LEGPH Legionella pneumophila subsp. pneumophila 3 0.7163
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7157
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7156
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7152
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7147
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7141
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7140
GTPase IMAP family member 2 Q9UG22 GIMA2_HUMAN Homo sapiens 3 0.7137
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 2 0.7137
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7132
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 2 0.7121
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 3 0.7116
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 2 0.7113
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 2 0.7112
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7112
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7103
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7097
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7096
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7087
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7086
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7083
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7080
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7072
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7063
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7057
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7054
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7051
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7042
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7037
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7031
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7024
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7021
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7020
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7015
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7007
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7006
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7005
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7002

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