6beta-hydroxycrinine - Compound Card

6beta-hydroxycrinine

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6beta-hydroxycrinine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles O[C@H]1C=C[C@@]23C(C1)N(CC2)[C@H](c1c3cc2OCOc2c1)O
InChI InChI=1S/C16H17NO4/c18-9-1-2-16-3-4-17(14(16)5-9)15(19)10-6-12-13(7-11(10)16)21-8-20-12/h1-2,6-7,9,14-15,18-19H,3-5,8H2/t9-,14?,15-,16+/m0/s1
InChIKey ILMBZGCGIXQNFZ-PGTGIHDKSA-N
Formula C16H17NO4
HBA 5
HBD 2
MW 287.31
Rotatable Bonds 0
TPSA 62.16
LogP 1.05
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 287.12
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: 162885745

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 287.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.91
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.34
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.15

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.48
Plasma Protein Binding
26.73
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.25
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.08
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.38
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.91
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
-0.79
Rat (Acute)
2.48
Rat (Chronic Oral)
1.69
Fathead Minnow
3.92
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
395.56
Hydration Free Energy
-10.74
Log(D) at pH=7.4
0.74
Log(P)
0.25
Log S
-1.87
Log(Vapor Pressure)
-8.57
Melting Point
197.42
pKa Acid
9.25
pKa Basic
6.13
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.9274
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.9274
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9217
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9217
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8924
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8924
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8899
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8899
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8612
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8612
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8423
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8423
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8394
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8394
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8297
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8297
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8123
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8123
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8092
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8092
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7933
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7933
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7926
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7926
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7836
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7836
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7814
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7814
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7789
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7789
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7781
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7781
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7780
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7780
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7735
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7735
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7723
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7723
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7667
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7667
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7630
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7630
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7543
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7543
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7521
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7521
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 3 0.7397
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 3 0.7397
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7361
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7361
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7353
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7353
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7340
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7340
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7330
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7330
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7265
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7265
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7241
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7241
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7217
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7217
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.7143
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.7143
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7138
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7138
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7078
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7078

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