Cis-isoshinanolone - Compound Card

Cis-isoshinanolone

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Cis-isoshinanolone

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Tetrahydronaphthalene
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles C[C@@H]1CC(=O)c2c([C@@H]1O)cccc2O
InChI InChI=1S/C11H12O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-4,6,11-12,14H,5H2,1H3/t6-,11-/m1/s1
InChIKey YUPNHTWYVBHLMG-KSBSHMNSSA-N
Formula C11H12O3
HBA 3
HBD 2
MW 192.21
Rotatable Bonds 0
TPSA 57.53
LogP 1.65
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 14
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 192.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus ealaensis Ancistrocladaceae Plantae 714098
2 Ancistrocladus likoko Ancistrocladaceae Plantae 714102
3 Ancistrocladus likoko Ancistrocladaceae Plantae 714102
4 Ancistrocladus abbreviatus Ancistrocladaceae Plantae 122295

Showing of synonyms

  • Tshitenge DT, Bruhn T, et al. (2019). An Unusually Broad Series of Seven Cyclombandakamines, Bridged Dimeric Naphthylisoquinoline Alkaloids from the Congolese Liana Ancistrocladus ealaensis.. Scientific reports,2019, 9(1), 9812. [View] [PubMed]
  • Fayez S, Feineis D, et al. (2018). Ancistrobrevines E-J and related naphthylisoquinoline alkaloids from the West African liana Ancistrocladus abbreviatus with inhibitory activities against Plasmodium falciparum and PANC-1 human pancreatic cancer cells. Fitoterapia, 2018, 131, 245-259. [View]
  • Bringmann G, Saeb W, et al. (2003). Ancistrolikokine D, a 5,8'-coupled naphthylisoquinoline alkaloid, and related natural products from Ancistrocladus likoko. Phytochemistry,2003, 62(4), 631-636. [View] [PubMed]
  • Fayez S, Feineis D, et al. (2017). Ancistrolikokines E-H and related 5,8'-coupled naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus likoko with antiausterity activities against PANC-1 human pancreatic cancer cells.. RSC Adv., 2017,7, 53740-53751. [View]
Pubchem: 443777
Kegg Ligand: C12343
Chebi: 31733
Nmrshiftdb2: 60027076
Bindingdb: 93041

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)CCCC2=O

Level: 0

Mol. Weight: 192.21 g/mol

Anti-leishmanial
Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.32
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.53
Plasma Protein Binding
57.39
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.86
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.41
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.71
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.34
Micronucleos
Toxic
NR-AhR
Safe
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
2.01
Rat (Acute)
2.41
Rat (Chronic Oral)
2.76
Fathead Minnow
3.93
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
307.39
Hydration Free Energy
-10.39
Log(D) at pH=7.4
1.2
Log(P)
1.6
Log S
-1.82
Log(Vapor Pressure)
-4.93
Melting Point
122.54
pKa Acid
7.27
pKa Basic
5.29
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9157
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9157
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.9075
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.9075
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.9048
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.9048
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9045
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9045
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.8969
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.8969
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8821
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8821
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8793
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8793
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8788
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8788
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8748
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8748
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8287
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8287
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8202
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8202
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8090
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8090
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8069
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8069
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7976
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7976
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7949
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7949
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7830
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7830
Lactose operon repressor P03023 LACI_ECOLI Escherichia coli 3 0.7811
Lactose operon repressor P03023 LACI_ECOLI Escherichia coli 3 0.7811
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7786
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7786
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7682
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7682
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.7678
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.7678
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7670
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7670
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7668
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7668
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7654
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7654
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7642
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7642
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.7556
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.7556
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7524
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7524
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7523
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7523
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7519
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7519
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7511
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7511
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7506
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7506
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7497
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7497
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7437
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7437
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7421
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7421
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7410
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7410
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7408
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7408
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7402
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7402
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7383
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7383
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7348
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7348
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7324
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7324
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7310
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7310
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7294
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7294
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7287
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7287
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7269
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7269
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7261
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7261
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7251
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7251
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7240
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7240
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7235
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7235
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7233
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7233
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7229
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7229
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7221
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7221
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7216
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7216
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7202
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7202
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7125
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7125
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7122
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7122
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7102
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7102
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7083
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7083
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7068
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B Q13370 PDE3B_HUMAN Homo sapiens 3 0.7068
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B Q13370 PDE3B_HUMAN Homo sapiens 3 0.7068
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7068
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7063
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7063
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7048
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7048
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7047
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7047
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7030
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7030
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7028
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7028
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7028
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7028
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7014
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7014
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7013
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7013

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