3-O-methyl-9-O-demethyl-maritidine - Compound Card

3-O-methyl-9-O-demethyl-maritidine

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3-O-methyl-9-O-demethyl-maritidine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Amaryllidaceae Alkaloid
Canonical Smiles CO[C@@H]1C=C[C@]23C(C1)N(CC2)Cc1c3cc(O)c(c1)OC
InChI InChI=1S/C17H21NO3/c1-20-12-3-4-17-5-6-18(16(17)8-12)10-11-7-15(21-2)14(19)9-13(11)17/h3-4,7,9,12,16,19H,5-6,8,10H2,1-2H3/t12-,16?,17+/m1/s1
InChIKey KGYVGKGCRKPXPT-PWBPUHETSA-N
Formula C17H21NO3
HBA 4
HBD 1
MW 287.36
Rotatable Bonds 2
TPSA 41.93
LogP 2.2
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 287.15
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: 162871625
Nmrshiftdb2: 80005092

No compound-protein relationship available.

Structure

SMILES: C1=CCCC(C123)N(CC2)Cc4c3cccc4

Level: 0

Mol. Weight: 287.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.730
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.420
Plasma Protein Binding
29.43
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.410
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.740
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.130
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.910
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
-0.420
Rat (Acute)
2.950
Rat (Chronic Oral)
1.660
Fathead Minnow
4.030
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
347.610
Hydration Free Energy
-8.580
Log(D) at pH=7.4
1.760
Log(P)
1.48
Log S
-1.22
Log(Vapor Pressure)
-5.81
Melting Point
182.57
pKa Acid
9.91
pKa Basic
7.75
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.9070
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.9070
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8998
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8998
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8796
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8796
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8509
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8509
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8465
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8465
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8407
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8407
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8327
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8327
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8156
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8156
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8074
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8074
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7764
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7764
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7748
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7748
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7742
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7742
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7730
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7730
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7727
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7727
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7705
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7705
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7701
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7701
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7699
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7699
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7670
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7670
Phytohormone-binding protein G7J032 PHBP_MEDTR Medicago truncatula 4 0.7649
Phytohormone-binding protein G7J032 PHBP_MEDTR Medicago truncatula 4 0.7649
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7647
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7647
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7629
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7629
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7602
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7602
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7591
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7591
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7574
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7574
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7571
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7571
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7570
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7570
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7567
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7567
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7537
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7537
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7536
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7536
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7536
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7536
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7509
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7509
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7497
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7497
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7494
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7494
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7484
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7484
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7443
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7443
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7397
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7397
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7384
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7384
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7358
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7358
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7356
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7356
Kallikrein-4 Q9Y5K2 KLK4_HUMAN Homo sapiens 3 0.7269
Kallikrein-4 Q9Y5K2 KLK4_HUMAN Homo sapiens 3 0.7269
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7252
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7252
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7252
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7252
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7250
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7250
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7246
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7246
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7238
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7238
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7233
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7233
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7222
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7222
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7182
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7182
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7179
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7179
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7178
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7178
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7156
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7156
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7154
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7154
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7131
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7131
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7130
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7130
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7115
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7115
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7085
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7085
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7047
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7047
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7042
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7042
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7012
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7012

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