6alpha-hydroxybuphaninisine - Compound Card

6alpha-hydroxybuphaninisine

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6alpha-hydroxybuphaninisine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CO[C@H]1C=C[C@@]23C(C1)N(CC2)[C@@H](c1c3cc2OCOc2c1)O
InChI InChI=1S/C17H19NO4/c1-20-10-2-3-17-4-5-18(15(17)6-10)16(19)11-7-13-14(8-12(11)17)22-9-21-13/h2-3,7-8,10,15-16,19H,4-6,9H2,1H3/t10-,15?,16+,17+/m0/s1
InChIKey VCFGXYUXSWZFDE-SJHRMCHKSA-N
Formula C17H19NO4
HBA 5
HBD 1
MW 301.34
Rotatable Bonds 1
TPSA 51.16
LogP 1.71
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: 162937367

No compound-protein relationship available.

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
-4.550
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.94

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.520
Plasma Protein Binding
25.92
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
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
11.180
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.220
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.330
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.400
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
-2.270
Rat (Acute)
2.570
Rat (Chronic Oral)
1.690
Fathead Minnow
3.940
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
377.240
Hydration Free Energy
-8.700
Log(D) at pH=7.4
1.510
Log(P)
1.41
Log S
-2.01
Log(Vapor Pressure)
-7.15
Melting Point
149.84
pKa Acid
9.48
pKa Basic
6.54
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 0.9392
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9392
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9341
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9341
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8433
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8433
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8431
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8431
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8425
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8425
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.8267
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.8267
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8222
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8222
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8152
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8152
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.8084
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.8084
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.8074
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.8074
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7926
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7926
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 3 0.7921
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 3 0.7921
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7889
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7889
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7829
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7829
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7707
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7707
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7646
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7646
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7502
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7502
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7459
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7459
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7413
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7413
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7325
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7325
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7285
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7285
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7277
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7277
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7268
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7268
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7249
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7249
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7212
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7212
Proline iminopeptidase O32449 PIP_SERMA Serratia marcescens 3 0.7203
Proline iminopeptidase O32449 PIP_SERMA Serratia marcescens 3 0.7203
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7173
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7173
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7125
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7125
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.7111
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.7111
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7094
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7094
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7083
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7083
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7066
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7066
Proline iminopeptidase O32449 PIP_SERMA Serratia marcescens 3 0.7035
Proline iminopeptidase O32449 PIP_SERMA Serratia marcescens 3 0.7035
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7009
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7009
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7008
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7008

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