ANPDB

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Flexinine

Family: Plantae - Amaryllidaceae
Kingdom: Plantae
Class: Alkaloid

Canonical Smiles	O[C@@H]1C[C@H]2N3CC[C@]2([C@@H]2[C@H]1O2)c1c(C3)cc2c(c1)OCO2
InChI	InChI=1S/C16H17NO4/c18-10-5-13-16(15-14(10)21-15)1-2-17(13)6-8-3-11-12(4-9(8)16)20-7-19-11/h3-4,10,13-15,18H,1-2,5-7H2/t10-,13-,14+,15+,16+/m1/s1
InChIKey	WWSZBGJLESQTHB-DMHMKPBJSA-N
Formula	C₁₆H₁₇NO₄
HBA	5
HBD	1
MW	287.32
Rotatable Bonds	0
TPSA	54.46
LogP	0.77
Number Rings	6
Number Aromatic Rings	1
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.62
Exact Mass	287.12
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Crinum americanum	Amaryllidaceae	Plantae	164437

Showing of synonyms

Ali AA, El Sayed HM, et al. (1986). Oxocrinine and other alkaloids from Crinum americanum. Phytochemistry,1986,25(10),2399-2401. [View]

Pubchem: 398936

Cas: 509-88-6

Zinc: ZINC000006018156

Nmrshiftdb2: 60071231

Chembl: CHEMBL1997786

No compound-protein relationship available.

SMILES: C123C4C(O4)CCC1N(CC2)Cc5c3cc6c(c5)OCO6

Level: 0

Mol. Weight: 287.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.17
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.63
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.17

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.25
Plasma Protein Binding: 17.51
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 18.52
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.46
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.09
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.17
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: 0.57
Rat (Acute): 2.1
Rat (Chronic Oral): 1.24
Fathead Minnow: 3.76
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: 417.29
Hydration Free Energy: -7.82
Log(D) at pH=7.4: 0.95
Log(P): 0.56
Log S: -1.71
Log(Vapor Pressure): -8.35
Melting Point: 176.82
pKa Acid: 6.77
pKa Basic: 6.85

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	0.9617
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9617
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8300
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8300
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8258
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8258
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7717
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7717
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7687
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7687
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7292
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7292
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7267
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7267
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7251
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7251
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7250
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7250
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7230
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7230
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7206
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7206
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7164
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7164
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7062
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7062
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	3	0.7053
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	3	0.7053
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7038
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7038
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7018
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7018

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