Nobilisitine A - Compound Card

Nobilisitine A

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Nobilisitine A

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Masanane-Type Lactone Alkaloid
Canonical Smiles CN1CC[C@@H]2[C@H]1C1[C@H]([C@@H](C2)O)OC(=O)c2c1cc1OCOc1c2
InChI InChI=1S/C17H19NO5/c1-18-3-2-8-4-11(19)16-14(15(8)18)9-5-12-13(22-7-21-12)6-10(9)17(20)23-16/h5-6,8,11,14-16,19H,2-4,7H2,1H3/t8-,11+,14?,15-,16-/m0/s1
InChIKey ATGABXDKTMWXAQ-YNVFHBRFSA-N
Formula C17H19NO5
HBA 6
HBD 1
MW 317.34
Rotatable Bonds 0
TPSA 68.23
LogP 1.12
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 317.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Clivia nobilis Amaryllidaceae Plantae 112537
2 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]
  • Schwartz BD, White LV, et al. (2011). Structure of the Lycorinine Alkaloid Nobilisitine A. The Journal of Organic Chemistry,2011,76(20),8560-8563. [View] [PubMed]
Pubchem: 162891017
Nmrshiftdb2: 70114480

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 317.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.67
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.32

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.45
Plasma Protein Binding
34.94
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
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.97
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.4
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.6
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.81
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
0.44
Rat (Acute)
2.67
Rat (Chronic Oral)
1.61
Fathead Minnow
3.92
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
388.49
Hydration Free Energy
-7.84
Log(D) at pH=7.4
1.63
Log(P)
1.21
Log S
-3.11
Log(Vapor Pressure)
-8.77
Melting Point
186.13
pKa Acid
7.29
pKa Basic
7.47
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9739
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9739
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9110
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9110
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.9105
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.9105
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8752
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8752
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8659
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8659
Mitomycin biosynthesis 6-O-methyltransferase Q9X5T6 MMCR_STRLA Streptomyces lavendulae 3 0.8435
Mitomycin biosynthesis 6-O-methyltransferase Q9X5T6 MMCR_STRLA Streptomyces lavendulae 3 0.8435
Acidic mammalian chitinase Q9BZP6 CHIA_HUMAN Homo sapiens 3 0.8293
Acidic mammalian chitinase Q9BZP6 CHIA_HUMAN Homo sapiens 3 0.8293
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8253
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8253
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7820
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7820
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7735
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7735
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7724
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7724
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7694
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7694
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7568
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7568
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7511
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7511
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7467
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7467
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7434
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7434
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 3 0.7415
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 3 0.7415
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7382
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7382
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7344
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7344
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7342
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7342
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7305
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7305
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7296
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7296
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7264
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7264
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7256
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7256
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7242
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7242
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7201
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7201
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7191
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7191
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7182
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7182
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7168
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7168
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 4 0.7124
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 4 0.7124
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7064
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7064
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7048
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7048

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