Methylancistrobertsonine D - Compound Card

Methylancistrobertsonine D

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Methylancistrobertsonine D

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1c2[C@H](C)N[C@@H](Cc2cc(c1c1c(C)cc(c2c1cccc2OC)OC)O)C
InChI InChI=1S/C25H29NO4/c1-13-10-20(29-5)23-17(8-7-9-19(23)28-4)21(13)24-18(27)12-16-11-14(2)26-15(3)22(16)25(24)30-6/h7-10,12,14-15,26-27H,11H2,1-6H3/t14-,15+/m1/s1
InChIKey RPYYNECGOSGRFR-CABCVRRESA-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 robertsoniorum Ancistrocladaceae Plantae 714105

Showing of synonyms

  • Bringmann G, Teltschika F, et al. (1999). Ancistrobertsonines B, C, and D as well as 1,2-didehydroancistrobertsonine D from Ancistrocladus robertsoniorum. Phytochemistry,1999,52(2),321-332. [View] [PubMed]
Pubchem: 162846777

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

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.99
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
-1.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.29
Plasma Protein Binding
78.1
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
8.77
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.93
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.15
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.64
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
Safe
T. Pyriformis
-34.04
Rat (Acute)
2.58
Rat (Chronic Oral)
2.0
Fathead Minnow
5.38
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
467.79
Hydration Free Energy
-5.9
Log(D) at pH=7.4
4.04
Log(P)
4.31
Log S
-4.71
Log(Vapor Pressure)
-8.75
Melting Point
157.04
pKa Acid
10.11
pKa Basic
9.53
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 0.9553
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9553
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9148
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9148
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.8754
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.8754
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8593
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8593
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 4 0.8432
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 4 0.8432
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8372
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8372
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8368
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8368
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8341
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8341
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8328
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8328
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8234
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8234
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8001
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8001
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7992
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7992
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7971
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7971
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7948
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7948
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7939
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7939
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7936
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7936
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7884
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7884
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7746
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7746
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7714
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7714
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7684
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7684
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7619
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7619
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7583
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7583
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7568
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7568
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7562
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7562
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7546
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7546
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 3 0.7517
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 3 0.7517
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7486
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7486
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7472
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7472
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7390
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7390
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7342
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7342
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7312
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7312
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7281
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7281
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7248
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7248
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7244
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7244
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7165
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7165
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 3 0.7141
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 3 0.7141
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7136
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7136
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7133
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7133
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7053
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7053
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7049
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7049
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7031
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7031
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7005
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7005

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