Oxocrinine - Compound Card

Oxocrinine

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Oxocrinine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles O=C1C=C[C@@]23[C@@H](C1)N(CC2)Cc1c3cc2OCOc2c1
InChI InChI=1S/C16H15NO3/c18-11-1-2-16-3-4-17(15(16)6-11)8-10-5-13-14(7-12(10)16)20-9-19-13/h1-2,5,7,15H,3-4,6,8-9H2/t15-,16-/m1/s1
InChIKey LUMDZQACZMCPFS-HZPDHXFCSA-N
Formula C16H15NO3
HBA 4
HBD 0
MW 269.3
Rotatable Bonds 0
TPSA 38.77
LogP 1.77
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 269.11
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: 11391548
Nmrshiftdb2: 60077304

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 269.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.560
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.620
Plasma Protein Binding
47.41
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
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.620
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.450
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.080
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.520
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
2.520
Rat (Acute)
2.440
Rat (Chronic Oral)
1.270
Fathead Minnow
3.890
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
389.690
Hydration Free Energy
-8.600
Log(D) at pH=7.4
1.860
Log(P)
0.93
Log S
-2.29
Log(Vapor Pressure)
-7.88
Melting Point
206.28
pKa Acid
10.03
pKa Basic
6.92
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 0.9322
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9322
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8617
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8617
Nitric oxide synthase, inducible P35228 NOS2_HUMAN Homo sapiens 3 0.8297
Nitric oxide synthase, inducible P35228 NOS2_HUMAN Homo sapiens 3 0.8297
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8294
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8294
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8081
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8081
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7809
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7809
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7696
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7696
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7613
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7613
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7595
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7595
Thymidylate synthase Q4JQW2 TYSY_VZVO Varicella-zoster virus 3 0.7586
Thymidylate synthase Q4JQW2 TYSY_VZVO Varicella-zoster virus 3 0.7586
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7562
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7562
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7541
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7541
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7508
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7508
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7379
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7379
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7351
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7351
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7325
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7325
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7214
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7214
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7212
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7212
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7206
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7206
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7118
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7118
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7110
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7110
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7107
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7107
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7092
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7092
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7055
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7055
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7053
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7053
Orotidine 5'-phosphate decarboxylase O58462 PYRF_PYRHO Pyrococcus horikoshii 3 0.7030
Orotidine 5'-phosphate decarboxylase O58462 PYRF_PYRHO Pyrococcus horikoshii 3 0.7030
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7025
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7025
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7011
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7011

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