Molecule

(-)-antofine

AlkaPlorer ID: AK001340

Synonym: '(-)-13a-alpha-antofine', '2,3,6-trimethoxy-9,10,11,12,12a,13-hexahydro-9a-aza-cyclopentabtriphenylene', '(R)-(-)-antofine', '7-demethoxytylophorine', '(13aR)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro9,10-findolizine', '9,11,12,13,13a,14-hexahydro-2,3,6-trimethoxydibenzof,hpyrrolo1,2-bisoquinoline', '(R)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzof,hpyrrolo1,2-bisoquinoline', '(-)-Antofine', '(-)-antofine', '2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrodibenzof,hpyrrolo1,2-bisoquinoline', 'Antofine', '(R)-antofine', 'antofine'

IUPAC Name: (13aR)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine

Structure

SMILES: COC1=CC=C2C3=C(C[C@H]4CCCN4C3)C3=CC(OC)=C(OC)C=C3C2=C1

InChI: InChI=1S/C23H25NO3/c1-25-15-6-7-16-18(10-15)20-12-23(27-3)22(26-2)11-19(20)17-9-14-5-4-8-24(14)13-21(16)17/h6-7,10-12,14H,4-5,8-9,13H2,1-3H3/t14-/m1/s1

InChIKey: NCVWJDISIZHFQS-CQSZACIVSA-N

Reference

Alkaloids of Cryptocarya phyllostemon

PubChem CID: 639288

LOTUS: LTS0118391

SuperNatural Ⅲ: SN0242046-02

NPASS: NPC95075

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Nandina domestica	Nandina	Berberidaceae	Ranunculales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Bryonia cretica	Bryonia	Cucurbitaceae	Cucurbitales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Vincetoxicum pycnostelma	Vincetoxicum	Apocynaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
None	Cynanchum	Apocynaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Parmelia omphalodes	Parmelia	Parmeliaceae	Lecanorales	Lecanoromycetes	Ascomycota	Fungi	Eukaryota
Isertia hypoleuca	Isertia	Rubiaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Dimetia capitellata	Dimetia	Rubiaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 363.4570000000001

TPSA？: 30.930000000000003

MolLogP？: 4.539300000000004

Number of H-Donors: 0

Number of H-Acceptors: 4

RingCount: 5

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	A549	GI50	10.0	nM	10.1016/j.ejmech.2012.02.048
Homo sapiens	A549	GI50	22.0	nM	10.1021/jm200330s
Homo sapiens	A549	IC50	8.0	nM	10.1021/jm061366a
Homo sapiens	A549	IC50	8.52	nM	10.1021/acs.jmedchem.5b00764
Homo sapiens	A549	IC50	10.0	nM	10.1016/j.bmcl.2014.11.086
Homo sapiens	A549	IC50	10.4	nM	10.1016/j.bmcl.2006.09.080
Homo sapiens	A549	IC50	11.0	nM	10.1016/j.bmc.2012.11.039
Homo sapiens	A549	IC50	18.0	nM	10.1016/j.bmc.2012.11.039
Homo sapiens	A549	IC50	22.0	nM	10.1016/j.bmcl.2017.04.022
Homo sapiens	A549	IC50	22.0	nM	10.1021/jm3001218
Homo sapiens	A549	IC50	22.0	nM	10.1021/jm9009263
Homo sapiens	A549	IC50	20000.0	nM	10.1016/j.bmc.2022.116614
Homo sapiens	CAKI-1	IC50	6.23	nM	10.1021/acs.jmedchem.5b00764
Homo sapiens	CCRF-CEM	GI50	5.2	nM	10.1016/j.bmcl.2007.11.054
Homo sapiens	DU-145	GI50	25.0	nM	10.1021/jm200330s
Homo sapiens	DU-145	IC50	9.0	nM	10.1021/jm061366a
Homo sapiens	DU-145	IC50	25.0	nM	10.1016/j.bmcl.2017.04.022
Homo sapiens	DU-145	IC50	25.0	nM	10.1021/jm3001218
Homo sapiens	DU-145	IC50	25.0	nM	10.1021/jm9009263
Homo sapiens	HCT-116	IC50	6.03	nM	10.1021/acs.jmedchem.5b00764
Homo sapiens	HCT-116	IC50	8.0	nM	10.1016/j.bmc.2012.11.039
Homo sapiens	HCT-116	IC50	9.9	nM	10.1016/j.bmcl.2006.09.080
Homo sapiens	HCT-15	IC50	13.0	nM	10.1016/j.bmc.2012.11.039
Homo sapiens	HL-60	GI50	1.0	nM	10.1016/j.ejmech.2012.02.048
Homo sapiens	HT-1080	IC50	9.6	nM	10.1016/j.bmcl.2006.09.080
Homo sapiens	KB	GI50	36.0	nM	10.1021/jm200330s
Homo sapiens	KB	IC50	13.0	nM	10.1021/jm061366a
Homo sapiens	KB	IC50	36.0	nM	10.1021/jm3001218
Homo sapiens	KB	IC50	36.0	nM	10.1021/jm9009263
Homo sapiens	MDA-MB-231	IC50	6.04	nM	10.1021/acs.jmedchem.5b00764
Homo sapiens	MDA-MB-231	IC50	12.0	nM	10.1016/j.bmcl.2017.04.022
Homo sapiens	PANC-1	GI50	2.2	nM	10.1016/j.bmcl.2007.11.054
Homo sapiens	PC-3	IC50	12.34	nM	10.1021/acs.jmedchem.5b00764
Homo sapiens	P-glycoprotein 1	Activity	37.9	%	10.1016/j.bmc.2012.11.039
Homo sapiens	SK-HEP1	IC50	8.0	nM	10.1016/j.bmc.2012.11.039
Homo sapiens	SNU-638	IC50	10.0	nM	10.1016/j.bmc.2012.11.039
Homo sapiens	ZR-75-1	IC50	8.0	nM	10.1021/jm061366a
Tobacco mosaic virus	Tobacco mosaic virus	Activity	15.3	%	10.1021/jf303550a
Tobacco mosaic virus	Tobacco mosaic virus	Activity	19.4	%	10.1021/jf303550a
Tobacco mosaic virus	Tobacco mosaic virus	Activity	20.4	%	10.1021/jf303550a
Tobacco mosaic virus	Tobacco mosaic virus	Activity	42.7	%	10.1021/jf303550a
Tobacco mosaic virus	Tobacco mosaic virus	Activity	45.5	%	10.1021/jf303550a
Tobacco mosaic virus	Tobacco mosaic virus	Activity	46.0	%	10.1021/jf303550a
Tobacco mosaic virus	Tobacco mosaic virus	GI	63.0	%	10.1021/jf302746m
Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	14.0	%	10.1021/jf051050w
Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	27.4	%	10.1021/jf303550a
Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	29.2	%	10.1021/jf051050w
Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	29.4	%	10.1021/jf304905k
Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	30.4	%	10.1021/jf304905k
Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	32.3	%	10.1021/jf304905k
Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	33.4	%	10.1021/jf304905k
Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	52.8	%	10.1021/jf303550a
Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	55.7	%	10.1021/jf304905k
Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	58.0	%	10.1021/jf304905k
Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	62.5	%	10.1021/jf304905k
Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	63.0	%	10.1021/jf3013376
Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	65.0	%	10.1021/np0702077
Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	65.8	%	10.1021/jf304905k
None	Molecular identity unknown	Activity	nan	None	10.1021/jm200330s
None	NON-PROTEIN TARGET	GI50	4.9	nM	10.1016/j.bmcl.2007.11.054
None	NON-PROTEIN TARGET	IC50	6.32	nM	10.1021/acs.jmedchem.5b00764
None	NON-PROTEIN TARGET	IC50	9.0	nM	10.1021/jm061366a
None	NON-PROTEIN TARGET	IC50	10.38	nM	10.1021/acs.jmedchem.5b00764
None	NON-PROTEIN TARGET	IC50	14.0	nM	10.1021/np0106384
None	NON-PROTEIN TARGET	IC50	16.0	nM	10.1021/np0106384
None	NON-PROTEIN TARGET	IC50	25.0	nM	10.1021/jm3001218
None	NON-PROTEIN TARGET	IC50	25.0	nM	10.1021/jm9009263
None	No relevant target	Solubility	1.0	ug.mL-1	10.1016/j.bmc.2012.11.039
None	No relevant target	Solubility	1.0	ug.mL-1	10.1016/j.bmc.2022.116614
None	No relevant target	Solubility	47.0	ug.mL-1	10.1016/j.bmc.2012.11.039
None	Unchecked	Activity	4.9	None	10.1016/j.bmcl.2007.11.054
None	Unchecked	Activity	28.0	None	10.1016/j.bmcl.2007.11.054
None	Unchecked	Activity	34.0	None	10.1016/j.bmcl.2007.11.054
None	Unchecked	Activity	nan	None	10.1016/j.bmcl.2007.11.054
None	Unchecked	CI	0.45	None	10.1016/j.ejmech.2017.06.047
None	Unchecked	IC50	7.3	nM	10.1016/j.bmcl.2007.11.054
None	Unchecked	IC50	24.0	nM	10.1016/j.bmcl.2007.11.054
None	Unchecked	IC50	135.0	nM	10.1016/j.bmcl.2007.11.054
None	Unchecked	IC50	167.0	nM	10.1016/j.bmcl.2007.11.054
None	Unchecked	Ratio	1.5	None	10.1016/j.bmcl.2007.11.054