Crinamine - Compound Card

Crinamine

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Crinamine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CO[C@H]1C=C[C@]23[C@@H](C1)N(C[C@@H]2O)Cc1c3cc2OCOc2c1
InChI InChI=1S/C17H19NO4/c1-20-11-2-3-17-12-6-14-13(21-9-22-14)4-10(12)7-18(8-16(17)19)15(17)5-11/h2-4,6,11,15-16,19H,5,7-9H2,1H3/t11-,15+,16-,17-/m0/s1
InChIKey YGPRSGKVLATIHT-FKSAFCJBSA-N
Formula C17H19NO4
HBA 5
HBD 1
MW 301.34
Rotatable Bonds 1
TPSA 51.16
LogP 1.19
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 301.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Crinum augustum Amaryllidaceae Plantae 16055

Showing of synonyms

  • Ali AA, Kating H and Frahm AW. (1981). Four 6-hydroxylated alkaloids in the crinine series from Crinum augustum. Phytochemistry,1981,20(7),1731-1733. [View]
Pubchem: 73620
Kegg Ligand: C08525
Chebi: 3914
Metabolights: MTBLC3914
CPRiL: 101582
Structure

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

Level: 0

Mol. Weight: 301.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.590
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.580
Plasma Protein Binding
30.93
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
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-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
7.950
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.850
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.010
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.140
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
-4.000
Rat (Acute)
3.050
Rat (Chronic Oral)
1.540
Fathead Minnow
4.010
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
377.940
Hydration Free Energy
-8.470
Log(D) at pH=7.4
1.560
Log(P)
1.16
Log S
-1.53
Log(Vapor Pressure)
-7.96
Melting Point
174.18
pKa Acid
9.42
pKa Basic
6.83
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 0.9616
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9616
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8857
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8857
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8806
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8806
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8451
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8451
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.8266
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.8266
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8261
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8261
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8232
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8232
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8226
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8226
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8189
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8189
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8136
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8136
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8112
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8112
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8059
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8059
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7874
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7874
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7872
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7872
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7851
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7851
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7844
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7844
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7811
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7811
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7793
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7793
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7735
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7735
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7682
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7682
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7629
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7629
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7619
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7619
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7583
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7583
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7487
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7487
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7480
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7480
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7414
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7414
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7379
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7379
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7332
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7332
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7293
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7293
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7268
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7268
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7247
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7247
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7244
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7244
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7126
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7126
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7094
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7094
Benzoylformate decarboxylase P20906 MDLC_PSEPU Pseudomonas putida 3 0.7057
Benzoylformate decarboxylase P20906 MDLC_PSEPU Pseudomonas putida 3 0.7057
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7032
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7032
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7029
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7029
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7013
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7013

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