6beta-hydroxybuphaninisine - Compound Card

6beta-hydroxybuphaninisine

Select a section from the left sidebar

6beta-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-RDXUJYIISA-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: 162937368

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
-2.93

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.520
Plasma Protein Binding
26.38
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
11.160
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.300
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.320
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
-2.120
Rat (Acute)
2.580
Rat (Chronic Oral)
1.680
Fathead Minnow
3.930
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
377.040
Hydration Free Energy
-8.620
Log(D) at pH=7.4
1.470
Log(P)
1.34
Log S
-2.02
Log(Vapor Pressure)
-7.14
Melting Point
152.61
pKa Acid
9.55
pKa Basic
6.63
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 0.9449
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9449
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.9358
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.9358
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9078
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9078
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8825
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8825
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8681
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8681
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8499
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8499
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8364
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8364
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8329
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8329
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8205
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8205
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8185
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8185
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8022
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8022
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7978
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7978
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7964
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7964
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7953
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7953
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 3 0.7928
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 3 0.7928
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7853
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7853
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7830
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7830
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7778
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7778
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7743
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7743
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7719
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7719
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7645
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7645
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7626
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7626
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.7604
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.7604
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7561
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7561
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7559
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7559
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7534
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7534
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7529
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7529
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7451
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7451
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7434
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7434
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7417
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7417
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7344
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7344
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7288
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7288
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7269
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7269
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7264
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7264
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7252
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7252
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7225
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7225
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7136
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7136
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7097
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7097
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7071
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7071
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7031
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7031
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7027
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7027

Download SDF