(+)-dimethylsmoracin O - Compound Card

(+)-dimethylsmoracin O

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(+)-dimethylsmoracin O

Structure
Zoomed Structure
  • Family: Plantae - Moraceae
  • Kingdom: Plantae
  • Class: Lignan
Canonical Smiles COc1cc(OC)cc(c1)c1oc2c(c1)cc1c(c2)O[C@@H](C1)C(O)(C)C
InChI InChI=1S/C21H22O5/c1-21(2,22)20-9-13-5-12-8-17(25-18(12)11-19(13)26-20)14-6-15(23-3)10-16(7-14)24-4/h5-8,10-11,20,22H,9H2,1-4H3/t20-/m0/s1
InChIKey NQUPJFXAERIMOG-FQEVSTJZSA-N
Formula C21H22O5
HBA 5
HBD 1
MW 354.4
Rotatable Bonds 4
TPSA 61.06
LogP 4.19
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 354.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Morus mesozygia Moraceae Plantae 3054370

Showing of synonyms

  • Fozing CD, Ali Z, et al. (2012). Phosphodiesterase I-inhibiting Diels-Alder adducts from the leaves of Morus mesozygia.. Planta medica,2012, 78(2), 154-159. [View] [PubMed]
Pubchem: 162864247

No compound-protein relationship available.

Structure

SMILES: O1CCc(c2)c1cc(c23)oc(c3)-c4ccccc4

Level: 1

Mol. Weight: 354.4 g/mol

Structure

SMILES: c1coc(c12)cc3c(c2)CCO3

Level: 0

Mol. Weight: 354.4 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 354.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.500
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.66

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.420
Plasma Protein Binding
79.03
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
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.230
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.480
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.590
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.820
Micronucleos
Toxic
NR-AhR
Toxic
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
-3.090
Rat (Acute)
2.160
Rat (Chronic Oral)
1.930
Fathead Minnow
5.180
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
450.630
Hydration Free Energy
-7.660
Log(D) at pH=7.4
3.380
Log(P)
4.73
Log S
-4.86
Log(Vapor Pressure)
-7.9
Melting Point
161.71
pKa Acid
10.72
pKa Basic
6.37
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9538
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.9370
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9233
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9193
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9173
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9167
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9015
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 4 0.8928
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8926
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8922
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8891
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8778
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8712
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8697
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8617
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8599
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.8590
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.8546
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8469
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8397
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8375
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8349
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8214
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8080
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8072
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8023
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8000
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7998
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7949
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7928
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7918
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7909
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7883
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7843
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7843
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7775
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7736
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7734
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 4 0.7717
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7683
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7677
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7665
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7642
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 4 0.7573
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7537
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7508
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7493
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7491
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7486
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7468
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7438
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7423
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7421
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.7392
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7383
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7383
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7372
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7347
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7347
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7341
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7335
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7334
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7321
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7316
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7302
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7289
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7281
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7265
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7258
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7251
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7217
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7215
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7207
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7181
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7172
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7148
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7138
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7126
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7125
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7120
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7096
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7087
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7083
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 2 0.7080
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7068
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7058
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7051
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7050
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7040
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7034
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 3 0.7021
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7008

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