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Papyramine

Family: Plantae - Amaryllidaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Amaryllidaceae Alkaloid

Canonical Smiles	CO[C@@H]1C=C[C@]23C(C1)N(CC2)C(c1c3cc(OC)c(c1)OC)O
InChI	InChI=1S/C18H23NO4/c1-21-11-4-5-18-6-7-19(16(18)8-11)17(20)12-9-14(22-2)15(23-3)10-13(12)18/h4-5,9-11,16-17,20H,6-8H2,1-3H3/t11-,16?,17?,18+/m1/s1
InChIKey	JFWCEOZJEWNPOW-GQOQCBKBSA-N
Formula	C₁₈H₂₃NO₄
HBA	5
HBD	1
MW	317.39
Rotatable Bonds	3
TPSA	51.16
LogP	2.0
Number Rings	4
Number Aromatic Rings	1
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.56
Exact Mass	317.16
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: 443727

Cas: 81149-33-9

Kegg Ligand: C12238

Chebi: 31961

Nmrshiftdb2: 60114956

CPRiL: 425547

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

Level: 0

Mol. Weight: 317.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.65
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.630
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.31

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.580
Plasma Protein Binding: 21.23
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: Non-Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 3.770
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.370
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.340
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 8.330
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: -2.380
Rat (Acute): 2.970
Rat (Chronic Oral): 1.760
Fathead Minnow: 4.040
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: 355.100
Hydration Free Energy: -9.020
Log(D) at pH=7.4: 1.300
Log(P): 1.18
Log S: -0.96
Log(Vapor Pressure): -6.41
Melting Point: 168.05
pKa Acid: 10.52
pKa Basic: 6.71

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	0.9446
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9446
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8466
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8466
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.8064
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.8064
Mandelate racemase	P11444	MANR_PSEPU	Pseudomonas putida	3	0.7831
Mandelate racemase	P11444	MANR_PSEPU	Pseudomonas putida	3	0.7831
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7739
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7739
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7733
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7733
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7668
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7668
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7638
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7638
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7587
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7587
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	3	0.7550
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	3	0.7550
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7538
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7538
HLA class I histocompatibility antigen, B alpha chain	P01889	HLAB_HUMAN	Homo sapiens	3	0.7507
HLA class I histocompatibility antigen, B alpha chain	P01889	HLAB_HUMAN	Homo sapiens	3	0.7507
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7471
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7471
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7385
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7385
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7368
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7368
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7244
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7244
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7237
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7237
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7219
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7219
histone deacetylase	A5H660	A5H660_SCHMA	Schistosoma mansoni	3	0.7186
histone deacetylase	A5H660	A5H660_SCHMA	Schistosoma mansoni	3	0.7186
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	2	0.7173
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	2	0.7173
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7134
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7134
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7119
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7119
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	3	0.7117
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	3	0.7117
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7106
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7106
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7102
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7102
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7090
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7090
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7042
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7042
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7033
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7033
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7022
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7022
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7000
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7000

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