Vittatine - Compound Card

Vittatine

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Vittatine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Amaryllidaceae Alkaloid
Canonical Smiles O[C@@H]1C=C[C@]23[C@H](C1)N(CC2)Cc1c3cc2OCOc2c1
InChI InChI=1S/C16H17NO3/c18-11-1-2-16-3-4-17(15(16)6-11)8-10-5-13-14(7-12(10)16)20-9-19-13/h1-2,5,7,11,15,18H,3-4,6,8-9H2/t11-,15+,16+/m1/s1
InChIKey RPAORVSEYNOMBR-RLCCDNCMSA-N
Formula C16H17NO3
HBA 4
HBD 1
MW 271.32
Rotatable Bonds 0
TPSA 41.93
LogP 1.56
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 271.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Narcissus species Amaryllidaceae Plantae 54843

Showing of synonyms

  • Shawky E, Abou-Donia AH, et al. (2015). HPTLC and GC/MS study of Amaryllidaceae alkaloids of two Narcissus species. Chemistry and Biodiversity,2015,12(8),1184-1199. [View] [PubMed]
Pubchem: 443693
Kegg Ligand: C12193
Nmrshiftdb2: 60027245

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 271.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.8
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.4
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.59
Plasma Protein Binding
41.91
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
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
12.91
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.66
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.4
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.03
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
1.16
Rat (Acute)
2.64
Rat (Chronic Oral)
1.32
Fathead Minnow
3.87
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
388.27
Hydration Free Energy
-9.05
Log(D) at pH=7.4
1.72
Log(P)
1.03
Log S
-1.65
Log(Vapor Pressure)
-7.99
Melting Point
206.15
pKa Acid
10.29
pKa Basic
8.06
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 0.9666
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9666
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9008
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9008
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8908
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8908
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.8609
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.8609
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8565
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8565
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8514
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8514
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.8467
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.8467
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8446
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8446
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8306
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8306
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8218
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8218
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8162
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8162
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8158
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8158
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8136
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8136
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.8077
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.8077
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8075
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8075
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8067
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8067
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8066
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8066
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8033
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8033
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7992
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7992
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7986
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7986
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7958
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7958
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7949
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7949
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7817
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7817
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7747
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7747
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7739
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7739
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7715
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7715
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7642
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7642
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7634
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7634
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7595
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7595
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7592
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7592
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7585
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7585
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7559
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7559
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7510
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7510
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7415
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7415
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7407
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7407
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7403
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7403
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7395
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7395
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7393
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7393
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7376
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7376
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7330
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7330
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7311
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7311
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7299
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7299
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7297
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7297
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7273
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7273
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7271
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7271
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 2 0.7265
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 2 0.7265
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7262
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7262
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7244
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7244
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7167
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7167
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7141
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7141
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7118
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7118
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7117
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7117
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7111
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7111
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7105
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7105
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7099
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7099
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7066
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7066
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7065
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7065
Bifunctional metallophosphatase/5'-nucleotidase Q2G1L5 Q2G1L5_STAA8 Staphylococcus aureus 4 0.7059
Bifunctional metallophosphatase/5'-nucleotidase Q2G1L5 Q2G1L5_STAA8 Staphylococcus aureus 4 0.7059
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7054
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7054
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7041
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7041
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7036
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7036
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7032
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7032
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7015
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7015
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7010
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7010
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7004
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7004

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