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Crinine

Family: Plantae - Amaryllidaceae
Kingdom: Plantae
Class: 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+/m0/s1
InChIKey	RPAORVSEYNOMBR-IUIKQTSFSA-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	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: 398937

Zinc: ZINC000004102368

Kegg Ligand: C12162

Chebi: 31437

Nmrshiftdb2: 60025507

Metabolights: MTBLC31437

Chembl: CHEMBL1221864

CPRiL: 196464

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

Level: 0

Mol. Weight: 271.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.85
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: -2.95

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.59
Plasma Protein Binding: 38.92
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: 13.07
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.47
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.41
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.02
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: 1.03
Rat (Acute): 2.68
Rat (Chronic Oral): 1.33
Fathead Minnow: 3.89
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: 389.73
Hydration Free Energy: -9.05
Log(D) at pH=7.4: 1.7
Log(P): 0.88
Log S: -1.64
Log(Vapor Pressure): -7.94
Melting Point: 190.99
pKa Acid: 10.08
pKa Basic: 8.05

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	0.9635
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9635
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9338
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9338
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9207
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9207
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9196
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9196
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.9062
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.9062
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8965
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8965
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8925
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8925
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8809
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8809
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8718
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8718
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8717
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8717
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8592
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8592
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8572
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8572
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.8553
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.8553
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8503
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8503
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8460
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8460
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8458
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8458
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8388
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8388
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8349
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8349
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8284
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8284
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8279
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8279
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8266
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8266
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8219
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8219
HLA class I histocompatibility antigen, B alpha chain	P01889	HLAB_HUMAN	Homo sapiens	3	0.7987
HLA class I histocompatibility antigen, B alpha chain	P01889	HLAB_HUMAN	Homo sapiens	3	0.7987
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7835
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7835
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7804
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7804
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7750
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7750
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7694
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7694
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7645
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7645
Odorant binding protein ASP1	Q8WRW5	Q8WRW5_APIME	Apis mellifera	3	0.7637
Odorant binding protein ASP1	Q8WRW5	Q8WRW5_APIME	Apis mellifera	3	0.7637
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	3	0.7550
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	3	0.7550
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7535
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7535
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7512
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7512
Acetylserotonin O-methyltransferase	P46597	ASMT_HUMAN	Homo sapiens	4	0.7510
Acetylserotonin O-methyltransferase	P46597	ASMT_HUMAN	Homo sapiens	4	0.7510
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7438
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7438
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7321
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7321
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7262
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7262
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7252
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7252
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7244
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7244
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7227
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7227
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7209
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7209
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7183
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7183
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7160
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7160
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7150
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7150
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7144
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7144
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7142
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7142
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7142
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7142
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7106
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7106
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	2	0.7089
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	2	0.7089
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7044
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7044
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7043
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7043
Phytohormone-binding protein	G7J032	PHBP_MEDTR	Medicago truncatula	4	0.7043
Phytohormone-binding protein	G7J032	PHBP_MEDTR	Medicago truncatula	4	0.7043
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7041
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7041
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7031
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7031
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7029
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7029
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7010
Glucocorticoid receptor	P04150	GCR_HUMAN	Homo sapiens	3	0.7010
Glucocorticoid receptor	P04150	GCR_HUMAN	Homo sapiens	3	0.7010
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7010
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7003
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7003

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