Trans-1,2-dihydroancistrocladisine - Compound Card

Trans-1,2-dihydroancistrocladisine

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Trans-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-HZPDHXFCSA-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)
-5.19
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
-2.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.260
Plasma Protein Binding
74.28
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
8.370
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.890
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
-57.740
Rat (Acute)
2.950
Rat (Chronic Oral)
1.990
Fathead Minnow
5.780
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
469.430
Hydration Free Energy
-4.480
Log(D) at pH=7.4
3.850
Log(P)
4.76
Log S
-4.4
Log(Vapor Pressure)
-8.48
Melting Point
141.9
pKa Acid
12.25
pKa Basic
10.27
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 0.9671
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9671
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9253
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9253
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.9055
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.9055
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9050
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9050
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8921
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8921
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8887
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8887
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.8863
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.8863
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8578
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8578
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8559
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.8559
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8535
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8535
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8475
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8475
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8299
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8299
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8249
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8249
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8243
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8243
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8200
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8200
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8173
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8173
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8162
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8162
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8078
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8078
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8077
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8077
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8057
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8057
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8018
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8018
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.8008
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.8008
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8006
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8006
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8001
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8001
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7983
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7983
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7926
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7926
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7882
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7882
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7880
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7880
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7868
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7868
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7865
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7865
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7850
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7850
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7833
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7833
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7810
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7810
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7778
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7778
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7745
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7745
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7714
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7714
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7695
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7695
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7695
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7695
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7688
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7688
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7681
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7681
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7662
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7662
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7656
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7656
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7653
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7653
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7627
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7627
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 4 0.7502
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 4 0.7502
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7496
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7496
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7496
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7496
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7464
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7464
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7401
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7401
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7394
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7394
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7376
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7376
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7333
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7333
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7327
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7327
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7319
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7319
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7318
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7318
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7305
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7305
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7292
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7292
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7290
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7290
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7288
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7288
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7285
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7285
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7219
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7219
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7207
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 3 0.7207
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7207
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 3 0.7207
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7144
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7144
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7109
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7109
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7102
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7102
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7085
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7085
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7080
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7080
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7071
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7071
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7060
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7060
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7054
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7054
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7047
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7047
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7016
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7016
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7004
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7004

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