9-hydroxypinoresinol - Compound Card

9-hydroxypinoresinol

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9-hydroxypinoresinol

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Tetrahydrofuran Lignan
Canonical Smiles COc1ccc(cc1O)C1OCC2C1C(O)OC2c1ccc(c(c1)OC)O
InChI InChI=1S/C20H22O7/c1-24-15-6-4-10(7-14(15)22)19-17-12(9-26-19)18(27-20(17)23)11-3-5-13(21)16(8-11)25-2/h3-8,12,17-23H,9H2,1-2H3
InChIKey RBYCOHVPQBHIAA-UHFFFAOYSA-N
Formula C20H22O7
HBA 7
HBD 3
MW 374.39
Rotatable Bonds 4
TPSA 97.61
LogP 2.51
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.4
Exact Mass 374.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Premna odorata Lamiaceae Plantae 1037421

Showing of synonyms

  • Elmaidomy A.H, Mohammed R, et al. (2019). Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco. Metabolites, 2019, 9(10), 223. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4

Level: 2

Mol. Weight: 374.39 g/mol

Structure

SMILES: C1OCC(C12)COC2c3ccccc3

Level: 1

Mol. Weight: 374.39 g/mol

Structure

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 374.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 374.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.07
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.000
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.73

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.980
Plasma Protein Binding
4.36
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-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
13.290
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.300
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.790
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.550
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
Safe
T. Pyriformis
-6.720
Rat (Acute)
2.140
Rat (Chronic Oral)
2.690
Fathead Minnow
4.350
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
428.630
Hydration Free Energy
-7.280
Log(D) at pH=7.4
2.310
Log(P)
1.2
Log S
-3.82
Log(Vapor Pressure)
-7.76
Melting Point
178.53
pKa Acid
8.19
pKa Basic
3.13
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9100
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.9039
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9006
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8937
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8906
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8892
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8864
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8830
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8807
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8799
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8769
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8706
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8693
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8676
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.8667
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 3 0.8589
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8544
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8482
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8481
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8464
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8433
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8418
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8401
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8388
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8384
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8339
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8211
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8196
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8097
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8076
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8065
chitinase B0Y2Y2 B0Y2Y2_ASPFC Aspergillus fumigatus 4 0.7977
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.7973
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 3 0.7960
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7945
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7940
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7916
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7885
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7867
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7863
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7858
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7858
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7841
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7807
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7754
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7716
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7683
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7623
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7623
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7587
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7567
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7512
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7501
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7478
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7478
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7465
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7442
Acetolactate synthase catalytic subunit, mitochondrial P07342 ILVB_YEAST Saccharomyces cerevisiae 3 0.7432
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7420
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7414
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 3 0.7413
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7398
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7390
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 2 0.7382
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7368
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7361
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7360
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7357
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7347
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7342
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7341
Large structural protein Q91L20 Q91L20_9MONO Human metapneumovirus 3 0.7336
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7327
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7326
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7325
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7314
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7308
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7296
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7296
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7294
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7283
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7266
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7253
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7244
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7225
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7219
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7218
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7215
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7213
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7187
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7186
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7181
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7167
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7160
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7157
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7142
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 4 0.7141
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7139
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7134
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7131
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7116
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7111
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7109
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7109
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7107
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7107
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7106
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7101
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7099
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7087
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7086
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 4 0.7074
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7068
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7062
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7061
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7059
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7051
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7050
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7034
Transitional endoplasmic reticulum ATPase Q01853 TERA_MOUSE Mus musculus 3 0.7029
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7029
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7029
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7026
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7026
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7026
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 2 0.7025
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7022
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7018
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7011
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7002

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