Ancistrobertsonine D - Compound Card

Ancistrobertsonine D

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Ancistrobertsonine D

Structure
Zoomed Structure
  • Family: Dioncophyllaceae, Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline 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+/m0/s1
InChIKey RPYYNECGOSGRFR-LSDHHAIUSA-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
2 Ancistrocladus ileboensis Dioncophyllaceae Plantae 1367080

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]
  • 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: 10476498
Nmrshiftdb2: 70059357

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 259.35 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 133.19 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 128.17 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.01
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
-1.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.29
Plasma Protein Binding
78.08
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
8.78
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.94
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
-34.19
Rat (Acute)
2.58
Rat (Chronic Oral)
2.01
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
467.8
Hydration Free Energy
-5.9
Log(D) at pH=7.4
4.16
Log(P)
4.26
Log S
-4.7
Log(Vapor Pressure)
-8.77
Melting Point
156.79
pKa Acid
10.12
pKa Basic
9.54
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 0.9439
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9439
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8921
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8921
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8912
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8912
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8864
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8864
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8729
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8729
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8710
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8710
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8322
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8322
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8283
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8283
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8234
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8234
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8219
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8219
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8175
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8175
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8161
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8161
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7959
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7959
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7955
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7955
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7876
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7876
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7834
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7834
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7808
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7808
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7799
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7799
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7791
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7791
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7761
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7761
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7726
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7726
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7724
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7724
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7651
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7651
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7616
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7616
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7601
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7601
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7529
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7529
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7528
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7528
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7471
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7471
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7439
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7439
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7424
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7424
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 4 0.7420
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 4 0.7420
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7406
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7406
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7340
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7340
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7313
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7313
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7254
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7254
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7248
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7248
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7233
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7233
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7178
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7178
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7128
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7128
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7128
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7128
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7095
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7095
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7011
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7011

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