Molecule

Narciclasine

AlkaPlorer ID: AK002404

Synonym: None

IUPAC Name: (2S,3R,4S,4aR)-2,3,4,7-tetrahydroxy-3,4,4a,5-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one

Structure

SMILES: OC1=N[C@@H]2C(=C[C@H](O)[C@@H](O)[C@H]2O)C2=CC3=C(OCO3)C(O)=C12

InChI: InChI=1S/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h1-2,6,9-10,12,16-19H,3H2,(H,15,20)/t6-,9+,10+,12-/m0/s1

InChIKey: LZAZURSABQIKGB-AEKGRLRDSA-N

Reference

Effects of atmospheric CO<sub>2</sub> enrichment on the growth and development of <i>Hymenocallis littoralis</i> (Amaryllidaceae) and the concentrations of several antineoplastic and antiviral constituents of its bulbs

PubChem CID: 72376

CAS: 29477-83-6

LOTUS: LTS0202973

SuperNatural Ⅲ: SN0219281-09

NPASS: NPC182257

data_source: manually

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Narcissus pseudonarcissus	Narcissus	Amaryllidaceae	Asparagales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Discodermia polydiscus	Discodermia	Theonellidae	Tetractinellida	Demospongiae	Porifera	Metazoa	Eukaryota
Crinum asiaticum	Crinum	Amaryllidaceae	Asparagales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Croton kongensis	Croton	Euphorbiaceae	Malpighiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Fuligo cinerea	Fuligo	Physaraceae	Physariida	Eumycetozoa	Evosea	None	Eukaryota
Helichrysum kraussii	Helichrysum	Asteraceae	Asterales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Corynanthe paniculata	Corynanthe	Rubiaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
None	None	Amaryllidaceae	Asparagales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Scilla scilloides	Scilla	Hyacinthaceae	Asparagales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Brachystola magna	Brachystola	Romaleidae	Orthoptera	Insecta	Arthropoda	Metazoa	Eukaryota
Tulipa turkestanica	Tulipa	Liliaceae	Liliales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Aplidium glabrum	Aplidium	Polyclinidae	Aplousobranchia	Ascidiacea	Chordata	Metazoa	Eukaryota
None	Narcissus	Amaryllidaceae	Asparagales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
None	Narcissus	Amaryllidaceae	Asparagales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 307.25800000000004

TPSA？: 131.97000000000003

MolLogP？: -0.7126000000000003

Number of H-Donors: 5

Number of H-Acceptors: 7

RingCount: 4

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	62.0	%	10.1016/j.bmcl.2017.09.052
dengue virus type 4	dengue virus type 4	IC50	0.015	ug.mL-1	10.1021/np50089a003
Escherichia coli	Escherichia coli	GI	50.0	%	10.1016/j.bmcl.2017.09.052
Escherichia coli	Escherichia coli	IZ	13.0	mm	10.1016/j.bmcl.2017.09.052
Homo sapiens	A498	GI50	44.98	nM	None
Homo sapiens	A549	Activity	nan	None	10.1021/jm8013585
Homo sapiens	A549	GI50	44.98	nM	None
Homo sapiens	A549	IC50	29.0	nM	10.1021/jm8013585
Homo sapiens	A549	IC50	30.0	nM	10.1021/jm8013585
Homo sapiens	A549	IC50	50.0	nM	10.1021/np900731p
Homo sapiens	BXPC-3	ED50	0.0035	ug ml-1	10.1021/np068046e
Homo sapiens	BXPC-3	ED50	0.024	ug ml-1	10.1021/np0402367
Homo sapiens	BXPC-3	GI	0.026	ug ml-1	10.1021/np058068l
Homo sapiens	BXPC-3	GI50	0.0035	ug.mL-1	10.1021/np030299+
Homo sapiens	BXPC-3	IC50	28.0	nM	10.1021/jm8013585
Homo sapiens	BXPC-3	IC50	30.0	nM	10.1021/jm8013585
Homo sapiens	BXPC-3	IC50	50.0	nM	10.1016/j.bmcl.2011.06.068
Homo sapiens	BXPC-3	Inhibition	0.026	ug ml-1	10.1016/j.bmcl.2004.03.032
Homo sapiens	C32	IC50	25.0	nM	10.1021/jm8013585
Homo sapiens	CAKI-1	GI50	44.98	nM	None
Homo sapiens	CCRF-CEM	GI50	44.98	nM	None
Homo sapiens	COLO 205	GI50	44.98	nM	None
Homo sapiens	Cytochrome P450 3A4	Ki	630.0	nM	10.1016/j.bmcl.2009.04.086
Homo sapiens	Cytochrome P450 3A4	Ki	630.0	nM	10.1021/np100657w
Homo sapiens	Cytochrome P450 3A4	Ki	630.96	nM	10.1016/j.bmcl.2009.04.086
Homo sapiens	Daoy	IC50	22.0	nM	10.1021/jm8013585
Homo sapiens	DLD-1	GI50	44.98	nM	None
Homo sapiens	DMS-114	GI50	44.98	nM	None
Homo sapiens	DMS-273	GI50	44.98	nM	None
Homo sapiens	DU-145	ED50	0.012	ug ml-1	10.1021/np0402367
Homo sapiens	DU-145	GI50	0.0032	ug.mL-1	10.1021/np030299+
Homo sapiens	DU-145	GI50	0.0032	ug.mL-1	10.1021/np068046e
Homo sapiens	DU-145	GI50	0.011	ug.mL-1	10.1021/np058068l
Homo sapiens	DU-145	IC50	30.0	nM	10.1016/j.bmcl.2014.07.034
Homo sapiens	DU-145	IC50	50.0	nM	10.1016/j.bmcl.2011.06.068
Homo sapiens	DU-145	Inhibition	0.011	ug ml-1	10.1016/j.bmcl.2004.03.032
Homo sapiens	EKVX	GI50	44.98	nM	None
Homo sapiens	FaDu	IC50	8.0	nM	10.1021/jm8013585
Homo sapiens	G-361	IC50	99.0	nM	10.1021/jm8013585
Homo sapiens	GBM	Activity	nan	None	10.1021/jm8013585
Homo sapiens	HCC 2998	GI50	44.98	nM	None
Homo sapiens	HCT-116	GI50	44.98	nM	None
Homo sapiens	HCT-15	GI50	44.98	nM	None
Homo sapiens	HCT-15	IC50	32.0	nM	10.1021/jm8013585
Homo sapiens	HL-60	GI50	64.57	nM	None
Homo sapiens	HOP-18	GI50	53.46	nM	None
Homo sapiens	HOP-62	GI50	44.98	nM	None
Homo sapiens	HOP-92	GI50	44.98	nM	None
Homo sapiens	Hs 683	IC50	40.0	nM	10.1021/jm8013585
Homo sapiens	Hs 683	IC50	50.0	nM	10.1021/np900731p
Homo sapiens	HT-144	IC50	38.0	nM	10.1021/jm8013585
Homo sapiens	HT-29	GI50	44.98	nM	None
Homo sapiens	HUVEC	FC	0.31	None	10.1021/acs.jnatprod.8b00973
Homo sapiens	HUVEC	FC	0.8	None	10.1021/acs.jnatprod.8b00973
Homo sapiens	HUVEC	IC50	87.0	nM	10.1021/jm8013585
Homo sapiens	HUVEC	IC50	94.0	nM	10.1021/jm8013585
Homo sapiens	HUVEC	IC50	97.0	nM	10.1021/jm8013585
Homo sapiens	HUVEC	Inhibition	nan	%	10.1021/acs.jnatprod.8b00973
Homo sapiens	IGROV-1	GI50	44.98	nM	None
Homo sapiens	K562	GI50	44.98	nM	None
Homo sapiens	KM12	GI50	44.98	nM	None
Homo sapiens	KM-20L2	ED50	0.023	ug ml-1	10.1021/np0402367
Homo sapiens	KM-20L2	GI50	0.0032	ug.mL-1	10.1021/np030299+
Homo sapiens	KM-20L2	GI50	0.0032	ug.mL-1	10.1021/np068046e
Homo sapiens	KM-20L2	GI50	0.21	ug.mL-1	10.1021/np058068l
Homo sapiens	KM-20L2	GI50	44.98	nM	None
Homo sapiens	KM-20L2	Inhibition	0.021	ug ml-1	10.1016/j.bmcl.2004.03.032
Homo sapiens	Liver microsomes	Stability	nan	%	10.1021/jm8013585
Homo sapiens	LoVo	IC50	90.0	nM	10.1021/jm8013585
Homo sapiens	LoVo	IC50	94.0	nM	10.1021/jm8013585
Homo sapiens	LOX IMVI	GI50	44.98	nM	None
Homo sapiens	M19-MEL	GI50	44.98	nM	None
Homo sapiens	Malme-3M	GI50	44.98	nM	None
Homo sapiens	MCF7	ED50	0.0032	ug ml-1	10.1021/np068046e
Homo sapiens	MCF7	ED50	0.014	ug ml-1	10.1021/np0402367
Homo sapiens	MCF7	GI50	0.0032	ug.mL-1	10.1021/np030299+
Homo sapiens	MCF7	GI50	0.019	ug.mL-1	10.1021/np058068l
Homo sapiens	MCF7	GI50	44.98	nM	None
Homo sapiens	MCF7	IC50	10.0	nM	10.1016/j.bmcl.2012.08.005
Homo sapiens	MCF7	IC50	40.0	nM	10.1016/j.bmcl.2011.06.068
Homo sapiens	MCF7	IC50	45.0	nM	10.1021/jm8013585
Homo sapiens	MCF7	IC50	50.0	nM	10.1021/jm8013585
Homo sapiens	MCF7	Inhibition	0.019	ug ml-1	10.1016/j.bmcl.2004.03.032
Homo sapiens	MDA-MB-231	IC50	5.0	nM	10.1021/jm8013585
Homo sapiens	MOLT-4	GI50	44.98	nM	None
Homo sapiens	NCI/ADR-RES	GI50	44.98	nM	None
Homo sapiens	NCI-H226	GI50	44.98	nM	None
Homo sapiens	NCI-H23	GI50	44.98	nM	None
Homo sapiens	NCI-H322M	GI50	44.98	nM	None
Homo sapiens	NCI-H460	ED50	0.014	ug ml-1	10.1021/np0402367
Homo sapiens	NCI-H460	GI50	0.0084	ug.mL-1	10.1021/np030299+
Homo sapiens	NCI-H460	GI50	0.0084	ug.mL-1	10.1021/np068046e
Homo sapiens	NCI-H460	GI50	0.032	ug.mL-1	10.1021/np058068l
Homo sapiens	NCI-H460	GI50	44.98	nM	None
Homo sapiens	NCI-H460	IC50	40.0	nM	10.1016/j.bmcl.2011.06.068
Homo sapiens	NCI-H460	IC50	50.0	nM	10.1016/j.bmcl.2014.07.034
Homo sapiens	NCI-H460	Inhibition	0.032	ug ml-1	10.1016/j.bmcl.2004.03.032
Homo sapiens	NCI-H522	GI50	44.98	nM	None
Homo sapiens	OVCAR-3	GI50	44.98	nM	None
Homo sapiens	OVCAR-4	GI50	142.23	nM	None
Homo sapiens	OVCAR-5	GI50	63.24	nM	None
Homo sapiens	OVCAR-8	GI50	44.98	nM	None
Homo sapiens	Panel NCI-60 (60 carcinoma cell lines)	GI50	45.0	nM	10.1021/jm049838d
Homo sapiens	PC-3	Activity	85.0	%	10.1021/np400107t
Homo sapiens	PC-3	Activity	nan	None	10.1021/jm8013585
Homo sapiens	PC-3	IC50	28.0	nM	10.1021/jm8013585
Homo sapiens	PC-3	IC50	30.0	nM	10.1021/jm8013585
Homo sapiens	RPMI-8226	GI50	44.98	nM	None
Homo sapiens	RXF 393	GI50	44.98	nM	None
Homo sapiens	SF-268	ED50	0.018	ug ml-1	10.1021/np0402367
Homo sapiens	SF-268	GI50	0.0031	ug.mL-1	10.1021/np030299+
Homo sapiens	SF-268	GI50	0.0031	ug.mL-1	10.1021/np068046e
Homo sapiens	SF-268	GI50	44.98	nM	None
Homo sapiens	SF-268	Inhibition	0.021	ug ml-1	10.1016/j.bmcl.2004.03.032
Homo sapiens	SF-295	GI50	63.39	nM	None
Homo sapiens	SF-539	GI50	44.98	nM	None
Homo sapiens	SK-MEL-2	GI50	44.98	nM	None
Homo sapiens	SK-MEL-28	GI50	44.98	nM	None
Homo sapiens	SK-MEL-28	IC50	37.0	nM	10.1021/jm8013585
Homo sapiens	SK-MEL-28	IC50	50.0	nM	10.1021/np900731p
Homo sapiens	SK-MEL-5	GI50	44.98	nM	None
Homo sapiens	SK-OV-3	GI50	44.98	nM	None
Homo sapiens	SN12C	GI50	44.98	nM	None
Homo sapiens	SN12K1	GI50	44.98	nM	None
Homo sapiens	SNB-19	GI50	44.98	nM	None
Homo sapiens	SNB-75	GI50	44.98	nM	None
Homo sapiens	SNB-78	GI50	44.98	nM	None
Homo sapiens	SW-620	GI50	44.98	nM	None
Homo sapiens	T98G	IC50	48.0	nM	10.1021/jm8013585
Homo sapiens	U-251	GI50	44.98	nM	None
Homo sapiens	UACC-257	GI50	44.98	nM	None
Homo sapiens	UACC-62	GI50	44.98	nM	None
Homo sapiens	UO-31	GI50	44.98	nM	None
Homo sapiens	XF498	GI50	44.98	nM	None
Human alphaherpesvirus 1	Human alphaherpesvirus 1	Activity	nan	None	10.1021/acsmedchemlett.5b00318
Human alphaherpesvirus 1	Human alphaherpesvirus 1	FC	10.6	None	10.1021/acsmedchemlett.5b00318
Human alphaherpesvirus 1	Human alphaherpesvirus 1	FC	69.0	None	10.1021/acsmedchemlett.5b00318
Japanese encephalitis virus	Japanese encephalitis virus	IC50	0.008	ug.mL-1	10.1021/np50089a003
Mus musculus	B16-F10	IC50	35.0	nM	10.1021/jm8013585
Mus musculus	B16-F10	IC50	50.0	nM	10.1021/np900731p
Mus musculus	Mus musculus	Activity	23.6	%	10.1016/j.ejmech.2022.114405
Mus musculus	Mus musculus	AUC	835.48	ng.hr.mL-1	10.1021/jm8013585
Mus musculus	Mus musculus	AUC	1352.2	ng.hr.mL-1	10.1021/jm8013585
Mus musculus	Mus musculus	Cp	300.0	ng/ml	10.1021/jm8013585
Mus musculus	Mus musculus	F	32.0	%	10.1021/jm8013585
Mus musculus	Mus musculus	T1/2	0.9667	hr	10.1021/jm8013585
Mus musculus	Mus musculus	T1/2	1.1	hr	10.1021/jm8013585
Mus musculus	P388	ED50	0.0012	ug ml-1	10.1021/np068046e
Mus musculus	P388	ED50	0.002	ug ml-1	10.1021/np058068l
Mus musculus	P388	ED50	0.013	ug ml-1	10.1021/np030299+
Mus musculus	P388	ED50	0.018	ug ml-1	10.1021/np0402367
Mus musculus	P388	ED50	0.018	ug ml-1	10.1021/np200862y
Mus musculus	P388	GI50	44.98	nM	None
Mus musculus	P388	Inhibition	0.0012	ug ml-1	10.1016/j.bmcl.2004.03.032
Mus musculus	P388/ADR	GI50	44.98	nM	None
Punta Toro virus	Punta Toro virus	IC50	0.0074	ug.mL-1	10.1021/np50089a003
Rattus norvegicus	9L	IC50	32.0	nM	10.1021/jm8013585
Rattus norvegicus	C6	IC50	28.0	nM	10.1021/jm8013585
Rattus norvegicus	Liver microsomes	Stability	nan	%	10.1021/jm8013585
Rattus norvegicus	Rattus norvegicus	Activity	11.0	%	10.1021/jm8013585
Rattus norvegicus	Rattus norvegicus	Activity	nan	None	10.1021/jm8013585
Rhodococcus fascians	Rhodococcus fascians	IZ	0.0	mm	10.1021/np50040a008
Rift Valley fever virus	Rift Valley fever virus	IC50	nan	None	10.1021/np50089a003
Sandfly fever Sicilian virus	Sandfly fever Sicilian virus	IC50	nan	None	10.1021/np50089a003
Staphylococcus aureus	Staphylococcus aureus	IZ	11.0	mm	10.1016/j.bmcl.2017.09.052
Yellow fever virus	Yellow fever virus	IC50	0.006	ug.mL-1	10.1021/np50089a003
None	ADMET	Activity	nan	None	10.1021/jm8013585
None	ADMET	IC50	317.0	nM	10.1021/jm8013585
None	ADMET	IC50	10000.0	nM	10.1021/jm8013585
None	ADMET	Stability	nan	%	10.1021/jm8013585
None	ADMET	TI	3.9	None	10.1021/np50089a003
None	ADMET	TI	4.0	None	10.1021/np50089a003
None	ADMET	TI	4.08	None	10.1021/np50089a003
None	ADMET	TI	6.1	None	10.1021/np50089a003
None	NON-PROTEIN TARGET	Activity	nan	None	10.1021/jm8013585
None	NON-PROTEIN TARGET	GI50	0.021	ug.mL-1	10.1021/np058068l
None	NON-PROTEIN TARGET	GI50	29.0	nM	10.1016/j.bmc.2016.04.036
None	NON-PROTEIN TARGET	GI50	40.0	nM	10.1016/j.bmc.2016.04.036
None	NON-PROTEIN TARGET	IC50	6.0	nM	10.1021/jm8013585
None	NON-PROTEIN TARGET	IC50	14.0	nM	10.1021/jm8013585
None	NON-PROTEIN TARGET	IC50	29.0	nM	10.1021/jm8013585
None	NON-PROTEIN TARGET	IC50	30.0	nM	10.1021/jm8013585
None	NON-PROTEIN TARGET	IC50	50.0	nM	10.1016/j.bmcl.2014.07.034
None	NON-PROTEIN TARGET	IC50	50.0	nM	10.1021/np900731p
None	NON-PROTEIN TARGET	IC50	98.0	nM	10.1021/jm8013585
None	No relevant target	Stability	100.0	%	10.1021/jm8013585
None	Unchecked	Activity	nan	None	10.1021/acs.jnatprod.8b00973
None	Unchecked	Activity	nan	None	10.1021/jm8013585
None	Unchecked	IC50	50000.0	nM	10.1016/j.ejmech.2020.112754