O-acetylcrinine - Compound Card

O-acetylcrinine

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O-acetylcrinine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CC(=O)OC1C=C[C@@]23[C@@H](C1)N(CC2)Cc1c3cc2OCOc2c1
InChI InChI=1S/C18H19NO4/c1-11(20)23-13-2-3-18-4-5-19(17(18)7-13)9-12-6-15-16(8-14(12)18)22-10-21-15/h2-3,6,8,13,17H,4-5,7,9-10H2,1H3/t13?,17-,18-/m1/s1
InChIKey YEIGSYFTXGPBIB-NGKGQXKNSA-N
Formula C18H19NO4
HBA 5
HBD 0
MW 313.35
Rotatable Bonds 1
TPSA 48.0
LogP 2.13
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 313.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Crinum americanum Amaryllidaceae Plantae 164437

Showing of synonyms

  • Ali AA, El Sayed HM, et al. (1986). Oxocrinine and other alkaloids from Crinum americanum. Phytochemistry,1986,25(10),2399-2401. [View]
Pubchem: 185262
Nmrshiftdb2: 60071271

No compound-protein relationship available.

Structure

SMILES: O1COc(c2)c1cc3c2CN(CC4)C(C345)CCC=C5

Level: 0

Mol. Weight: 313.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.65
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.73
Plasma Protein Binding
40.83
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
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.29
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.81
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.21
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
9.22
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
-0.57
Rat (Acute)
2.62
Rat (Chronic Oral)
1.43
Fathead Minnow
4.0
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
383.61
Hydration Free Energy
-6.71
Log(D) at pH=7.4
2.18
Log(P)
2.09
Log S
-2.37
Log(Vapor Pressure)
-7.1
Melting Point
142.84
pKa Acid
9.03
pKa Basic
7.58
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9407
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9407
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9367
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9367
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9336
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9336
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9221
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9221
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9121
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9121
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9112
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9112
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8809
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8809
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8809
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8809
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8750
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8750
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8741
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8741
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.8672
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.8672
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8596
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8596
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8590
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8590
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8580
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8580
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8542
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8542
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8516
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8516
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8510
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8510
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8484
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8484
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8473
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8473
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8467
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8467
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8441
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8441
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8421
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8421
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8405
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8405
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8330
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8330
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8295
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8295
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8238
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8238
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8091
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8091
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8086
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8086
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.8063
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.8063
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8061
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8061
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8014
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8014
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7974
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7974
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7923
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7923
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7894
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7894
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7892
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7892
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7877
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7877
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7868
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7868
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7851
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7851
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7801
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7801
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7796
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7796
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7731
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7731
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7653
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7653
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7587
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7587
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7557
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7557
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.7477
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.7477
Acetylserotonin O-methyltransferase P46597 ASMT_HUMAN Homo sapiens 4 0.7462
Acetylserotonin O-methyltransferase P46597 ASMT_HUMAN Homo sapiens 4 0.7462
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7446
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7446
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7396
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7396
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7393
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7393
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7370
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7370
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7357
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7357
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7354
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7354
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7344
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7344
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7340
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7340
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7331
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7331
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7300
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7300
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7285
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7285
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7282
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7282
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7262
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7262
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7251
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7251
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 4 0.7234
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 4 0.7234
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7212
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7212
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7204
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7204
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic P49235 HGGL1_MAIZE Zea mays 2 0.7201
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic P49235 HGGL1_MAIZE Zea mays 2 0.7201
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7187
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7187
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 2 0.7180
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 2 0.7180
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7167
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7167
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7164
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7164
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7129
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7129
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7105
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7105
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7100
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7100
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7089
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7089
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7076
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7076
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7074
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7074
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7073
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7073
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7063
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7063
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7060
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7060
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7054
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7054
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7029
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7029
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7027
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7027
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7006
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7006

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