Cis-1,2-dihydroancistrocladisine - Compound Card

Cis-1,2-dihydroancistrocladisine

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Cis-1,2-dihydroancistrocladisine

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)OC)C
InChI InChI=1S/C26H31NO4/c1-14-11-20(29-5)24-18(9-8-10-19(24)28-4)22(14)25-21(30-6)13-17-12-15(2)27-16(3)23(17)26(25)31-7/h8-11,13,15-16,27H,12H2,1-7H3/t15-,16+/m1/s1
InChIKey BLPXNSSTDKKRFC-CVEARBPZSA-N
Formula C26H31NO4
HBA 5
HBD 1
MW 421.54
Rotatable Bonds 5
TPSA 48.95
LogP 5.44
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 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]

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)
-5.18
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
Substrate
Skin Permeability
-2.36

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.260
Plasma Protein Binding
74.34
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
8.320
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.940
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.030
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
10.100
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
-57.560
Rat (Acute)
2.950
Rat (Chronic Oral)
1.990
Fathead Minnow
5.810
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
469.050
Hydration Free Energy
-4.480
Log(D) at pH=7.4
3.850
Log(P)
4.76
Log S
-4.39
Log(Vapor Pressure)
-8.47
Melting Point
142.13
pKa Acid
12.22
pKa Basic
10.32
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 0.9674
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9674
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9252
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9252
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8964
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8964
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8879
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8879
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8874
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8874
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.8830
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.8830
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8728
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8728
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8678
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8678
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8587
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8587
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8582
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8582
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8481
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8481
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8395
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8395
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8362
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8362
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8215
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8215
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8193
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8193
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8156
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8156
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8143
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8143
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8138
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8138
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8134
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8134
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8123
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8123
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8069
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8069
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8047
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8047
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8027
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8027
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8011
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8011
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7997
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7997
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7975
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7975
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7906
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7906
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.7861
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.7861
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7837
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7837
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7741
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7741
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7734
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7734
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7700
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7700
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7668
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7668
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7621
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7621
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7613
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7613
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7560
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7560
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7556
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7556
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7554
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7554
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7532
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7532
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7521
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7521
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7459
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7459
Cytochrome P450 130 P9WPN5 CP130_MYCTU Mycobacterium tuberculosis 3 0.7451
Cytochrome P450 130 P9WPN5 CP130_MYCTU Mycobacterium tuberculosis 3 0.7451
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7406
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7406
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7393
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7393
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7363
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7363
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7358
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7358
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7352
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7352
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7314
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7314
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7301
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7301
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7259
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7259
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7233
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7233
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7181
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7181
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7178
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7178
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 3 0.7151
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 3 0.7151
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7150
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7150
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7129
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7129
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7083
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7083
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7057
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7057
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7038
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7038
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7030
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7030
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7029
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7029
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7020
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7020
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7010
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7010
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7005
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7005
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7002
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7002

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