Trans-4',5-dihydroxy-3-methoxystilbene-5-O-[a-L-rhamnopyranosyl-(1→6)]-b-D-glucopyranoside - Compound Card

Trans-4',5-dihydroxy-3-methoxystilbene-5-O-[a-L-rhamnopyranosyl-(1→6)]-b-D-glucopyranoside

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Trans-4',5-dihydroxy-3-methoxystilbene-5-O-[a-L-rhamnopyranosyl-(1→6)]-b-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Burseraceae
  • Kingdom: Plantae
  • Class: Stilbene
Canonical Smiles COc1ccc(cc1)/C=C/c1cc(cc(c1)O)O[C@@H]1O[C@@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C27H34O12/c1-13-20(29)22(31)24(33)26(37-13)36-12-19-21(30)23(32)25(34)27(39-19)38-18-10-15(9-16(28)11-18)4-3-14-5-7-17(35-2)8-6-14/h3-11,13,19-34H,12H2,1-2H3/b4-3+/t13-,19-,20-,21-,22+,23+,24+,25-,26+,27+/m0/s1
InChIKey APSWPPWVYKLISI-OZRPVXBFSA-N
Formula C27H34O12
HBA 12
HBD 7
MW 550.56
Rotatable Bonds 8
TPSA 187.76
LogP -0.4
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.48
Exact Mass 550.21
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Boswellia dalzielii Burseraceae Plantae 2303552

Showing of synonyms

  • Tegasne C, Kapche GDWF, et al. (2021). Bioguided chemical study of Boswellia dalzielii Hutch. (Burseraceae) for antibacterial agents and a new glucopyranoxylmethoxybenzyle.. Natural product research,2021, 35(23), 5199-5208. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=Cc2cc(ccc2)OC(O3)CCCC3COC4CCCCO4

Level: 3

Mol. Weight: 550.56 g/mol

Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc3ccccc3

Level: 2

Mol. Weight: 550.56 g/mol

Structure

SMILES: c1ccccc1C=Cc2cc(ccc2)OC3CCCCO3

Level: 2

Mol. Weight: 550.56 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 550.56 g/mol

Structure

SMILES: c1ccccc1C=Cc2ccccc2

Level: 1

Mol. Weight: 550.56 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 550.56 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 550.56 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 550.56 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.55
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.170
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.32

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.960
Plasma Protein Binding
80.12
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
6.430
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.000
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.640
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.330
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
Safe
T. Pyriformis
-2095.980
Rat (Acute)
2.480
Rat (Chronic Oral)
4.120
Fathead Minnow
5.660
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
560.370
Hydration Free Energy
-2.930
Log(D) at pH=7.4
1.400
Log(P)
1.12
Log S
-3.8
Log(Vapor Pressure)
-12.81
Melting Point
180.38
pKa Acid
4.55
pKa Basic
4.37
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9479
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9239
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9084
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8839
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8775
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8674
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8514
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8481
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8319
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.8273
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8273
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8263
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8257
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8254
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8162
Cytokinin dehydrogenase 1 Q9T0N8 CKX1_MAIZE Zea mays 3 0.8138
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.8092
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8031
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.8027
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8001
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7990
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7932
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7891
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7839
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7802
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7792
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7753
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7739
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7730
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7696
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7669
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7665
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7654
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7645
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7644
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7620
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7618
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7614
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7595
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7584
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7565
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7562
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7555
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7522
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7522
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7518
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7516
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7512
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7489
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7476
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7455
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7449
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7442
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7439
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7433
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7427
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7425
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial Q6NVY1 HIBCH_HUMAN Homo sapiens 3 0.7423
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7416
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 2 0.7386
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7383
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7380
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7374
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7370
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7368
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7362
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7355
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7344
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7333
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7328
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7322
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 3 0.7318
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7309
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7307
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7306
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7306
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7301
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7293
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7286
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7269
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7267
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7264
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 2 0.7262
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7257
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7253
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7252
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7250
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7241
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7241
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7218
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7218
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7217
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7212
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7208
UDP-N-acetylglucosamine 1-carboxyvinyltransferase P33038 MURA_ENTCC Enterobacter cloacae subsp. cloacae 2 0.7205
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7202
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7202
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7195
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 2 0.7186
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7185
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7182
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7177
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7176
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 2 0.7174
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7173
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7163
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7163
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7150
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7148
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7145
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7131
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7126
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7124
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7123
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7110
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 2 0.7108
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 2 0.7095
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 2 0.7084
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase P47229 BPHD_PARXL Paraburkholderia xenovorans 2 0.7084
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 2 0.7082
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7080
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7079
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7078
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7078
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7074
72 kDa type IV collagenase P08253 MMP2_HUMAN Homo sapiens 3 0.7063
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7060
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 3 0.7056
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7052
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7051
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7049
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7046
Amine oxidase [flavin-containing] B P27338 AOFB_HUMAN Homo sapiens 2 0.7045
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7029
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7024
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7014
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7009
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7001

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