11-hydroxyvittatine - Compound Card

11-hydroxyvittatine

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11-hydroxyvittatine

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(CC2O)Cc1c3cc2OCOc2c1
InChI InChI=1S/C16H17NO4/c18-10-1-2-16-11-5-13-12(20-8-21-13)3-9(11)6-17(7-15(16)19)14(16)4-10/h1-3,5,10,14-15,18-19H,4,6-8H2/t10-,14+,15?,16+/m1/s1
InChIKey KWAOMPWGIIXDPH-UJONCCOVSA-N
Formula C16H17NO4
HBA 5
HBD 2
MW 287.31
Rotatable Bonds 0
TPSA 62.16
LogP 0.53
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 287.12
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: 443694
Kegg Ligand: C12194
Chebi: 31052
Nmrshiftdb2: 80005095
Metabolights: MTBLC31052
CPRiL: 215590
Structure

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

Level: 0

Mol. Weight: 287.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.37
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.91

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.59
Plasma Protein Binding
30.6
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.67
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.31
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.35
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.69
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
0.5
Rat (Acute)
2.65
Rat (Chronic Oral)
1.62
Fathead Minnow
3.92
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
403.2
Hydration Free Energy
-11.27
Log(D) at pH=7.4
1.01
Log(P)
0.43
Log S
-1.66
Log(Vapor Pressure)
-9.3
Melting Point
213.9
pKa Acid
8.79
pKa Basic
7.29
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8678
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8678
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.8594
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.8594
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8427
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8427
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.8267
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.8267
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8128
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8128
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8084
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8084
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8068
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8068
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.8040
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.8040
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7998
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7998
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7913
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7913
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7897
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7897
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7666
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7666
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7595
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7595
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7558
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7558
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7531
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7531
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7466
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7466
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7446
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7446
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7399
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7399
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7376
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7376
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7356
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7356
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7340
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7340
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7340
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7340
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7292
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7292
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7254
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7254
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 4 0.7197
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 4 0.7197
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7182
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7182
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7144
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7144
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7078
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7078
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7061
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7061
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7018
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7018

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