5′-O-methyldioncophylline D - Compound Card

5′-O-methyldioncophylline D

Select a section from the left sidebar

5′-O-methyldioncophylline D

Structure
Zoomed Structure
  • Family: Plantae - Dioncophyllaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1ccc(c2c1c(OC)cc(c2)C)c1ccc2c(c1O)[C@@H](C)N[C@@H](C2)C
InChI InChI=1S/C24H27NO3/c1-13-10-19-17(8-9-20(27-4)23(19)21(11-13)28-5)18-7-6-16-12-14(2)25-15(3)22(16)24(18)26/h6-11,14-15,25-26H,12H2,1-5H3/t14-,15-/m1/s1
InChIKey JJFZCSYBMKNTJY-HUUCEWRRSA-N
Formula C24H27NO3
HBA 4
HBD 2
MW 377.48
Rotatable Bonds 3
TPSA 50.72
LogP 5.13
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 377.2
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus ileboensis Ancistrocladaceae Plantae 1367080
2 Ancistrocladus ileboensis Dioncophyllaceae Plantae 1367080

Showing of synonyms

  • Li J, Seupel R, et al. (2017). Dioncophyllines C2, D2, and F and related naphthylisoquinoline alkaloids from the Congolese Liana Ancistrocladus ileboensis with potent activities against Plasmodium falciparum and against multiple myeloma and leukemia cell lines. Journal of natural products,2017, 80(2), 443-458. [View] [PubMed]
Pubchem: 132542154

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2-c(c3)ccc(c34)CCNC4

Level: 1

Mol. Weight: 377.48 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 377.48 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 377.48 g/mol

Antimalarial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.2
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.820
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.1

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.230
Plasma Protein Binding
84.67
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.170
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.660
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.620
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.360
Micronucleos
Toxic
NR-AhR
Toxic
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
-12.870
Rat (Acute)
2.660
Rat (Chronic Oral)
2.040
Fathead Minnow
5.070
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
448.830
Hydration Free Energy
-7.240
Log(D) at pH=7.4
3.760
Log(P)
4.46
Log S
-4.13
Log(Vapor Pressure)
-8.72
Melting Point
163.28
pKa Acid
10.26
pKa Basic
9.64
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9221
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9085
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8935
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8932
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8866
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8726
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.8506
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8403
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8311
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8300
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.8288
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8236
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8205
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8196
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8168
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8088
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7972
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7847
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7844
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7841
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7840
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7830
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7819
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7818
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7775
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7728
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7716
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7627
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7627
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7618
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7614
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7579
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7571
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7509
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7488
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7480
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7462
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7434
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7411
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7377
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7376
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 3 0.7371
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7360
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7356
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7346
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7325
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.7287
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7261
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7232
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7191
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7174
Granule-bound starch synthase 1, chloroplastic/amyloplastic Q0DEV5 SSG1_ORYSJ Oryza sativa subsp. japonica 3 0.7127
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7126
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7120
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7110
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7093
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7091
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7070
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7065
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7048
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7027
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7026
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7010

Download SDF