Nobilisitine B - Compound Card

Nobilisitine B

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Nobilisitine B

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Masanane-Type Lactone Alkaloid
Canonical Smiles CC(CC(=O)O[C@H]1C[C@H]2CCN([C@H]2C2[C@H]1OC(=O)c1c2cc2c(c1)OCO2)C)O
InChI InChI=1S/C21H25NO7/c1-10(23)5-17(24)28-16-6-11-3-4-22(2)19(11)18-12-7-14-15(27-9-26-14)8-13(12)21(25)29-20(16)18/h7-8,10-11,16,18-20,23H,3-6,9H2,1-2H3/t10?,11-,16+,18?,19-,20+/m1/s1
InChIKey QYVZOJWDWWFSQK-FSSNJVJCSA-N
Formula C21H25NO7
HBA 8
HBD 1
MW 403.43
Rotatable Bonds 3
TPSA 94.53
LogP 1.44
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.62
Exact Mass 403.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Clivia nobilis Amaryllidaceae Plantae 112537

Showing of synonyms

  • Evidente A, Abou-Donia AH, et al. (1999). Nobilisitine A and B, two masanane-type alkaloids from Clivia nobilis. Phytochemistry,1999,51(8),1151-1155. [View]
Pubchem: 3083698
Nmrshiftdb2: 60053934

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)cc3c(c2)C(=O)OC4C3C5C(CC4)CCN5

Level: 0

Mol. Weight: 403.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.77
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.54
Plasma Protein Binding
34.55
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-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
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.25
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.2
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.92
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
9.67
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
-33.13
Rat (Acute)
2.68
Rat (Chronic Oral)
1.54
Fathead Minnow
3.97
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
423.7
Hydration Free Energy
-4.48
Log(D) at pH=7.4
1.71
Log(P)
1.22
Log S
-2.66
Log(Vapor Pressure)
-9.13
Melting Point
145.8
pKa Acid
7.04
pKa Basic
6.7
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9741
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9741
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9341
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9341
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8800
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8800
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8279
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8279
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8235
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8235
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8159
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8159
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8092
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8092
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8085
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8085
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7970
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7970
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7879
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7879
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7846
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7846
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7845
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7845
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7772
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7772
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7739
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7739
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7710
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7710
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7655
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7655
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7529
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7529
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7437
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7437
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7416
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7416
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7395
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7395
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7364
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7364
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7361
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7361
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7355
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7355
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7321
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7321
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7312
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7312
Riboflavin synthase Q58584 RISC_METJA Methanocaldococcus jannaschii 4 0.7307
Riboflavin synthase Q58584 RISC_METJA Methanocaldococcus jannaschii 4 0.7307
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7267
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7267
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7259
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7259
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7246
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7246
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7244
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7244
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7226
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7226
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7219
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7219
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7190
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7190
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 2 0.7122
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 2 0.7122
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7120
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7120
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7115
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7115
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7105
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7105
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7088
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7088
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7083
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7083
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7076
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7076
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7074
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7074
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7062
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7062
Acidic mammalian chitinase Q9BZP6 CHIA_HUMAN Homo sapiens 3 0.7010
Acidic mammalian chitinase Q9BZP6 CHIA_HUMAN Homo sapiens 3 0.7010
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7003
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7003
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7000
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7000

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