NPASS Natural Product

Natural Product: NPC204251

Natural Product ID:	NPC204251
Common Name:	Ajoene
IUPAC Name:	(E)-1-(prop-2-enyldisulfanyl)-3-prop-2-enylsulfinylprop-1-ene
Synonyms:	Ajoene; E-Ajoene
Molecular Formula:	C9H14OS3
Standard InCHIKey:	IXELFRRANAOWSF-FNORWQNLSA-N
Standard InCHI:	InChI=1S/C9H14OS3/c1-3-6-11-12-7-5-9-13(10)8-4-2/h3-5,7H,1-2,6,8-9H2/b7-5+
Canonical SMILES:	C=CCSS/C=C/CS(=O)CC=C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota				TCM_Taiwan*
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota				TM-MC*

Biological Activity

Activity Type	# Activity
GI50	60
IC50	3
Others	2

Activity Type	# Activity
Cell Line	60
Individual Protein	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1557	Individual Protein	Glutathione reductase	Homo sapiens	Inhibition	=	50	%	9986706
NPT991	Individual Protein	Trypanothione reductase	Trypanosoma cruzi	Inhibition	=	50	%	9986706
NPT2	Others	Unspecified		IC50	=	17600	nM	18774712
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	3400	nM	16038536
NPT2	Others	Unspecified		IC50	=	39000	nM	22381354
NPT367	Cell Line	MDA-N	Homo sapiens	GI50		18836.49	nM	PubChem BioAssay data set
NPT368	Cell Line	SN12C	Homo sapiens	GI50		26001.6	nM	PubChem BioAssay data set
NPT369	Cell Line	ACHN	Homo sapiens	GI50		51050.5	nM	PubChem BioAssay data set
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50		46558.61	nM	PubChem BioAssay data set
NPT371	Cell Line	UO-31	Homo sapiens	GI50		37757.22	nM	PubChem BioAssay data set
NPT372	Cell Line	HOP-92	Homo sapiens	GI50		48305.88	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	GI50		5046.61	nM	PubChem BioAssay data set
NPT90	Cell Line	DU-145	Homo sapiens	GI50		68233.87	nM	PubChem BioAssay data set
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50		36559.48	nM	PubChem BioAssay data set
NPT374	Cell Line	SF-539	Homo sapiens	GI50		25003.45	nM	PubChem BioAssay data set
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50		49203.95	nM	PubChem BioAssay data set
NPT111	Cell Line	K562	Homo sapiens	GI50		5834.45	nM	PubChem BioAssay data set
NPT376	Cell Line	A498	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50		37068.07	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		3953.67	nM	PubChem BioAssay data set
NPT379	Cell Line	HOP-62	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50		26242.19	nM	PubChem BioAssay data set
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50		18492.69	nM	PubChem BioAssay data set
NPT380	Cell Line	U-251	Homo sapiens	GI50		59979.11	nM	PubChem BioAssay data set
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50		36643.76	nM	PubChem BioAssay data set
NPT383	Cell Line	SNB-19	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50		25234.81	nM	PubChem BioAssay data set
NPT385	Cell Line	SR	Homo sapiens	GI50		12416.52	nM	PubChem BioAssay data set
NPT384	Cell Line	TK-10	Homo sapiens	GI50		85703.78	nM	PubChem BioAssay data set
NPT323	Cell Line	SW-620	Homo sapiens	GI50		7798.3	nM	PubChem BioAssay data set
NPT386	Cell Line	KM12	Homo sapiens	GI50		57809.6	nM	PubChem BioAssay data set
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50		16749.43	nM	PubChem BioAssay data set
NPT387	Cell Line	M14	Homo sapiens	GI50		20892.96	nM	PubChem BioAssay data set
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50		10351.42	nM	PubChem BioAssay data set
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50		54827.7	nM	PubChem BioAssay data set
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50		14588.14	nM	PubChem BioAssay data set
NPT457	Cell Line	BT-549	Homo sapiens	GI50		25644.84	nM	PubChem BioAssay data set
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50		52239.62	nM	PubChem BioAssay data set
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50		63095.73	nM	PubChem BioAssay data set
NPT81	Cell Line	A549	Homo sapiens	GI50		60953.69	nM	PubChem BioAssay data set
NPT392	Cell Line	SNB-75	Homo sapiens	GI50		69984.2	nM	PubChem BioAssay data set
NPT148	Cell Line	HCT-15	Homo sapiens	GI50		35481.34	nM	PubChem BioAssay data set
NPT393	Cell Line	HCT-116	Homo sapiens	GI50		13122	nM	PubChem BioAssay data set
NPT395	Cell Line	SF-268	Homo sapiens	GI50		25003.45	nM	PubChem BioAssay data set
NPT394	Cell Line	EKVX	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT83	Cell Line	MCF7	Homo sapiens	GI50		44157.04	nM	PubChem BioAssay data set
NPT306	Cell Line	PC-3	Homo sapiens	GI50		39084.09	nM	PubChem BioAssay data set
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50		63973.48	nM	PubChem BioAssay data set
NPT396	Cell Line	T47D	Homo sapiens	GI50		56104.8	nM	PubChem BioAssay data set
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50		35809.64	nM	PubChem BioAssay data set
NPT398	Cell Line	UACC-62	Homo sapiens	GI50		36307.81	nM	PubChem BioAssay data set
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50		26915.35	nM	PubChem BioAssay data set
NPT399	Cell Line	SF-295	Homo sapiens	GI50		58748.94	nM	PubChem BioAssay data set
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50		18155.16	nM	PubChem BioAssay data set
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50		43351.09	nM	PubChem BioAssay data set
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50		26424.09	nM	PubChem BioAssay data set
NPT401	Cell Line	786-0	Homo sapiens	GI50		18281	nM	PubChem BioAssay data set
NPT403	Cell Line	UACC-257	Homo sapiens	GI50		50933.09	nM	PubChem BioAssay data set
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50		3435.58	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	GI50		29922.65	nM	PubChem BioAssay data set
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50		41304.75	nM	PubChem BioAssay data set
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50		20701.41	nM	PubChem BioAssay data set
NPT406	Cell Line	RXF 393	Homo sapiens	GI50		24945.95	nM	PubChem BioAssay data set
NPT407	Cell Line	COLO 205	Homo sapiens	GI50		24660.39	nM	PubChem BioAssay data set

Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC204251 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	7943
0.1-0.2	21048
0.2-0.3	1662
0.3-0.4	188
0.4-0.5	29
0.5-0.6	7
0.6-0.7	6
0.7-0.8	3
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC168614
0.8571	High Similarity	NPC2088
0.8276	Intermediate Similarity	NPC46648
0.7857	Intermediate Similarity	NPC156018
0.7143	Intermediate Similarity	NPC184203
0.7143	Intermediate Similarity	NPC220140
0.6897	Remote Similarity	NPC142438
0.6486	Remote Similarity	NPC277288
0.6333	Remote Similarity	NPC476550
0.6207	Remote Similarity	NPC326758
0.6207	Remote Similarity	NPC476548
0.6	Remote Similarity	NPC205586
0.5862	Remote Similarity	NPC476549

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC204251 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	3181
0.1-0.2	5523
0.2-0.3	411
0.3-0.4	36
0.4-0.5	5
0.5-0.6	5
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Structure

External Identifiers

PubChem CID	5386591
ChEMBL	CHEMBL122890
ZINC

Physicochemical Properties

Molecular Weight:	234.02
ALogP:	2.0566
MLogP:	2.01
XLogP:	1.416
# Rotatable Bonds:	8
Polar Surface Area:	86.88
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	0
# Heavy Atoms:	13

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs