Korupensamine D - Compound Card

Korupensamine D

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Korupensamine D

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(C)cc2c1c(O)ccc2c1c(O)cc(c2c1C[C@H](C)N([C@@H]2C)C)O
InChI InChI=1S/C24H27NO4/c1-12-8-16-15(6-7-18(26)24(16)21(9-12)29-5)23-17-10-13(2)25(4)14(3)22(17)19(27)11-20(23)28/h6-9,11,13-14,26-28H,10H2,1-5H3/t13-,14+/m0/s1
InChIKey GWJJRDKEDFSIDL-UONOGXRCSA-N
Formula C24H27NO4
HBA 5
HBD 3
MW 393.48
Rotatable Bonds 2
TPSA 73.16
LogP 4.88
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 393.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus korupensis Ancistrocladaceae Plantae 63089

Showing of synonyms

  • Hallock YF, Manfredi KP, et al. (1994). Korupensamines A-D, Novel Antimalarial Alkaloids from Ancistrocladus korupensis. J. Org. Chem. 1994, 59, 21, 6349–6355. [View]
Pubchem: 10069155
Nmrshiftdb2: 70077122

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2-c3cccc(c34)CNCC4

Level: 1

Mol. Weight: 393.48 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 393.48 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 393.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.2
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.020
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.920
Plasma Protein Binding
80.26
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.520
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.280
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.580
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
8.210
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-17.380
Rat (Acute)
2.330
Rat (Chronic Oral)
2.240
Fathead Minnow
4.730
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
481.780
Hydration Free Energy
-8.510
Log(D) at pH=7.4
3.780
Log(P)
4.25
Log S
-4.29
Log(Vapor Pressure)
-8.67
Melting Point
183.25
pKa Acid
8.55
pKa Basic
8.43
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 0.9433
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9433
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9212
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9212
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9174
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9174
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9152
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9152
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8992
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8992
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8967
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8967
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8962
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8962
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8647
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8647
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8646
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8646
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8543
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8543
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.8526
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.8526
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8470
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8470
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8138
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8138
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8104
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8104
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8040
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8040
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8023
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8023
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7974
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7974
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7973
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7973
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7857
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7857
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7828
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7828
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7826
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7826
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7806
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7806
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7733
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7733
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7679
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7679
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7574
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7574
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7534
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7534
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.7506
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.7506
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7443
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7443
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7413
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7413
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 4 0.7392
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 4 0.7392
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7350
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7350
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7328
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7328
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7319
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7319
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7307
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7307
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7226
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7226
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7223
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7223
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 4 0.7219
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 4 0.7219
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7177
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7177
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7177
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7177
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7175
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7175
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7165
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7165
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7157
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7157
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7154
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7154
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7126
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7126
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7121
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7121
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7111
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7111
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7080
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7080
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7073
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7073
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7062
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7062
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7058
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7058
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7050
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7050
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7004
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7004
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7002
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7002
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7000
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7000

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