Ancistrobrevine D - Compound Card

Ancistrobrevine D

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Ancistrobrevine D

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc2C[C@H](C)N([C@@H](c2c(c1c1c(C)cc(c2c1cccc2OC)OC)O)C)C
InChI InChI=1S/C26H31NO4/c1-14-11-20(30-6)24-18(9-8-10-19(24)29-5)22(14)25-21(31-7)13-17-12-15(2)27(4)16(3)23(17)26(25)28/h8-11,13,15-16,28H,12H2,1-7H3/t15-,16+/m0/s1
InChIKey PGHJSNHPVCVQPJ-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 abbreviatus Ancistrocladaceae Plantae 122295

Showing of synonyms

  • François G, Bringmann G, et al. (1995). Activities of extracts and naphthylisoquinoline alkaloids from Triphyophyllum peltatum, Ancistrocladus abbreviatus and Ancistrocladus barteri against Plasmodium berghei (Anka strain) in vitro. Journal of Ethnopharmacology, 1995, 46(2), 115-120. [View]
Pubchem: 101664024
Nmrshiftdb2: 70016115

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)
-5.0
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.810
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.19

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.160
Plasma Protein Binding
76.63
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
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
9.070
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.260
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.270
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.990
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
-53.350
Rat (Acute)
2.660
Rat (Chronic Oral)
1.990
Fathead Minnow
5.230
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
456.860
Hydration Free Energy
-4.700
Log(D) at pH=7.4
4.220
Log(P)
4.37
Log S
-4.49
Log(Vapor Pressure)
-9.25
Melting Point
136.26
pKa Acid
9.65
pKa Basic
9.42
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 0.9581
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.9222
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9170
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9079
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8942
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8708
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8630
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.8623
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8563
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8532
Biphenyl-2,3-diol 1,2-dioxygenase P47228 BPHC_PARXL Paraburkholderia xenovorans 4 0.8402
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8311
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8264
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8198
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8182
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8108
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8088
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8024
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8001
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7952
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 4 0.7935
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7934
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7833
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7713
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7693
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7692
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7691
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7634
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7629
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7600
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7582
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7492
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7471
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7448
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7436
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7428
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7417
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7410
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7364
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7350
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7320
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7318
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 3 0.7261
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7255
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7226
Cytosol aminopeptidase P00727 AMPL_BOVIN Bos taurus 2 0.7217
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7196
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7184
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7137
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7130
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7108
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7107
Mitomycin-binding protein O05205 O05205_STRLA Streptomyces lavendulae 2 0.7091
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7090
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7077
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7050
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7042
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.7009

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