6-O-demethyl ancistrobrevine H - Compound Card

6-O-demethyl ancistrobrevine H

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6-O-demethyl ancistrobrevine H

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1c2[C@@H](C)N[C@@H](Cc2cc(c1c1ccc(c2c1cc(C)cc2OC)OC)O)C
InChI InChI=1S/C25H29NO4/c1-13-9-18-17(7-8-20(28-4)24(18)21(10-13)29-5)23-19(27)12-16-11-14(2)26-15(3)22(16)25(23)30-6/h7-10,12,14-15,26-27H,11H2,1-6H3/t14-,15-/m1/s1
InChIKey CGBBXIBLWODGSI-HUUCEWRRSA-N
Formula C25H29NO4
HBA 5
HBD 2
MW 407.51
Rotatable Bonds 4
TPSA 59.95
LogP 5.14
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 407.21
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus abbreviatus Ancistrocladaceae Plantae 122295

Showing of synonyms

  • Fayez S, Feineis D, et al. (2018). Ancistrobrevines E-J and related naphthylisoquinoline alkaloids from the West African liana Ancistrocladus abbreviatus with inhibitory activities against Plasmodium falciparum and PANC-1 human pancreatic cancer cells. Fitoterapia, 2018, 131, 245-259. [View]
Pubchem: 135015338

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 407.51 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 407.51 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 407.51 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-5.05
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.87
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.62

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.29
Plasma Protein Binding
76.72
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
8.6
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.96
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.2
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.75
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
-33.48
Rat (Acute)
2.55
Rat (Chronic Oral)
2.05
Fathead Minnow
5.32
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
468.96
Hydration Free Energy
-6.05
Log(D) at pH=7.4
4.22
Log(P)
4.56
Log S
-4.82
Log(Vapor Pressure)
-8.73
Melting Point
161.07
pKa Acid
10.27
pKa Basic
9.4
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 0.9492
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9197
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9015
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8542
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8528
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8519
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8484
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 4 0.8360
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8343
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8300
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8281
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8266
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8214
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8202
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8164
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8159
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8111
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7874
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7868
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7843
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7835
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7816
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7813
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7796
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7725
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7714
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7671
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7658
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7635
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7561
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7535
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7509
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7499
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7497
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7496
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7480
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7463
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7462
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7453
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7446
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7440
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7426
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7360
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7357
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7355
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7315
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 3 0.7270
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7243
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7233
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7231
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7222
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7215
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7208
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7196
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7183
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7159
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7140
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 4 0.7126
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7108
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7102
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7092
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7089
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7079
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7059
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7059
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7053
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7045
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7036
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7020
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7016
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7012

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