6-O-demethylancistrobrevine A - Compound Card

6-O-demethylancistrobrevine A

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6-O-demethylancistrobrevine A

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1c2c(C[C@@H](N([C@@H]2C)C)C)cc(c1c1ccc(c2c1cc(C)cc2OC)OC)O
InChI InChI=1S/C26H31NO4/c1-14-10-19-18(8-9-21(29-5)25(19)22(11-14)30-6)24-20(28)13-17-12-15(2)27(4)16(3)23(17)26(24)31-7/h8-11,13,15-16,28H,12H2,1-7H3/t15-,16+/m0/s1
InChIKey LJOLOTQJTYGVTJ-JKSUJKDBSA-N
Formula C26H31NO4
HBA 5
HBD 1
MW 421.54
Rotatable Bonds 4
TPSA 51.16
LogP 5.48
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 421.23
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus ealaensis Ancistrocladaceae Plantae 714098
2 Ancistrocladus congolensis Ancistrocladaceae Plantae 714097

Showing of synonyms

  • Tshitenge DT, Bruhn T, et al. (2019). Ealamines A-H, a Series of Naphthylisoquinolines with the Rare 7,8'-Coupling Site, from the Congolese Liana <i>Ancistrocladus ealaensis</i>, Targeting Pancreatic Cancer Cells.. Journal of natural products,2019, 82(11), 3150-3164. [View] [PubMed]
  • Bringmann G, Spuziak J, et al. (2008). Six naphthylisoquinoline alkaloids and a related benzopyranone from a Congolese Ancistrocladus species related to Ancistrocladus congolensis. Phytochemistry,2008, 69(4), 1065-1075. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 421.54 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 421.54 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 421.54 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.98
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.83
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.36

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.21
Plasma Protein Binding
74.51
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.22
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.75
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.37
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
10.08
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
-51.53
Rat (Acute)
2.67
Rat (Chronic Oral)
1.93
Fathead Minnow
5.37
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
470.64
Hydration Free Energy
-5.04
Log(D) at pH=7.4
4.24
Log(P)
4.89
Log S
-4.88
Log(Vapor Pressure)
-9.1
Melting Point
142.84
pKa Acid
10.0
pKa Basic
9.22
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 0.9499
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9499
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9114
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9114
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9035
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9035
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8671
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8671
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8515
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8515
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 4 0.8435
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 4 0.8435
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8430
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8430
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8430
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8430
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8412
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8412
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8267
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8267
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8215
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8215
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8197
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8197
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 4 0.8163
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 4 0.8163
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8126
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8126
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8083
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8083
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8030
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8030
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7957
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7957
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7938
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7938
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7899
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7899
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7862
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7862
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7846
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7846
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7843
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7843
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7830
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7830
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7795
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7795
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7764
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7764
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7747
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7747
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7728
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7728
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7716
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7716
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7702
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7702
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7700
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7700
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7646
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7646
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7612
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7612
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7576
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7576
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7569
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7569
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7565
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7565
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7564
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7564
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7549
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7549
Ketimine reductase mu-crystallin O54983 CRYM_MOUSE Mus musculus 3 0.7543
Ketimine reductase mu-crystallin O54983 CRYM_MOUSE Mus musculus 3 0.7543
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7542
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7542
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7514
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7514
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7507
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7507
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 4 0.7496
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 4 0.7496
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7484
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7484
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7475
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7475
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7439
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7439
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7407
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7407
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7358
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7358
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 3 0.7343
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 3 0.7343
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7312
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7312
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7311
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7311
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7305
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7305
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7279
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7279
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7249
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7249
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7234
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7234
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7203
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7203
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7186
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7186
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7181
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7181
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7153
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7153
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7149
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7149
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7140
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7140
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7130
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7130
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7128
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7128
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7125
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7125
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7124
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7124
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7121
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7121
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7118
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7118
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7118
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7118
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7110
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7110
Granule-bound starch synthase 1, chloroplastic/amyloplastic Q0DEV5 SSG1_ORYSJ Oryza sativa subsp. japonica 3 0.7086
Granule-bound starch synthase 1, chloroplastic/amyloplastic Q0DEV5 SSG1_ORYSJ Oryza sativa subsp. japonica 3 0.7086
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7086
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7086
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7059
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7059
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7058
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7058
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7046
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7046
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7045
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7045
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7043
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7043
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7040
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7040
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7039
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7039
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7038
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7038
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7023
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7023

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