NPASS Compound

Structure

CID77294 OpenBabel06191715412D 26 27 0 0 1 0 0 0 0 0999 V2000 6.0622 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -5.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 18 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 7 18 1 0 0 0 0 8 11 1 0 0 0 0 8 19 2 0 0 0 0 9 12 2 0 0 0 0 9 19 1 0 0 0 0 10 13 2 0 0 0 0 10 19 1 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 24 1 0 0 0 0 16 26 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 18 25 1 0 0 0 0 20 23 1 0 0 0 0 21 24 1 0 0 0 0 22 25 2 3 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	371.21
Volume:	401.701
LogP:	4.964
LogD:	4.298
LogS:	-4.692
# Rotatable Bonds:	9
TPSA:	31.39
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.641
Synthetic Accessibility Score:	3.484
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.653
MDCK Permeability:	9.870235771813896e-06
Pgp-inhibitor:	0.558
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.97
Plasma Protein Binding (PPB):	89.6778335571289%
Volume Distribution (VD):	2.734
Pgp-substrate:	12.673134803771973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.696
CYP1A2-substrate:	0.957
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.29
CYP2D6-inhibitor:	0.942
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.395

ADMET: Excretion

Clearance (CL):	6.23
Half-life (T1/2):	0.067

ADMET: Toxicity

hERG Blockers:	0.99
Human Hepatotoxicity (H-HT):	0.529
Drug-inuced Liver Injury (DILI):	0.251
AMES Toxicity:	0.141
Rat Oral Acute Toxicity:	0.936
Maximum Recommended Daily Dose:	0.403
Skin Sensitization:	0.845
Carcinogencity:	0.033
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC77294

Natural Product ID:	NPC77294
*Common Name:**	4-N-[2-[(E)-2-(4-Chlorophenyl)Ethenyl]Pyridin-4-Yl]-1-N,1-N-Diethylpentane-1,4-Diamine
IUPAC Name:	4-N-[2-[(E)-2-(4-chlorophenyl)ethenyl]pyridin-4-yl]-1-N,1-N-diethylpentane-1,4-diamine
Synonyms:
Standard InCHIKey:	FIDFDSHBKIWNIN-JLHYYAGUSA-N
Standard InCHI:	InChI=1S/C22H30ClN3/c1-4-26(5-2)16-6-7-18(3)25-22-14-15-24-21(17-22)13-10-19-8-11-20(23)12-9-19/h8-15,17-18H,4-7,16H2,1-3H3,(H,24,25)/b13-10+
SMILES:	CCN(CC)CCCC(C)N=c1cc[nH]c(/C=C/c2ccc(cc2)Cl)c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2001157
PubChem CID:	5351244
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000037] Styrenes

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1021/np100392m]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[20879743]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21807513]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23738470]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[23738470]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23755850]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[25275213]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26509914]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868158]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24560	Ricinus communis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
GI50	57

Activity Type	# Activity
Cell Line	57

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	2065.38	nM	PMID[525414]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	1828.1	nM	PMID[525414]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	10115.79	nM	PMID[525414]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	3318.94	nM	PMID[525414]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	1524.05	nM	PMID[525414]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	1256.03	nM	PMID[525414]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	2074.91	nM	PMID[525414]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	1674.94	nM	PMID[525414]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	9078.21	nM	PMID[525414]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	3228.49	nM	PMID[525414]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	1207.81	nM	PMID[525414]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	135.21	nM	PMID[525414]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	1629.3	nM	PMID[525414]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	1224.62	nM	PMID[525414]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	1840.77	nM	PMID[525414]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	3118.89	nM	PMID[525414]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	1659.59	nM	PMID[525414]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	3427.68	nM	PMID[525414]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	2612.16	nM	PMID[525414]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	496.59	nM	PMID[525414]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	3396.25	nM	PMID[525414]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	2382.32	nM	PMID[525414]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	2301.44	nM	PMID[525414]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	1541.7	nM	PMID[525414]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	2018.37	nM	PMID[525414]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	1625.55	nM	PMID[525414]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	1106.62	nM	PMID[525414]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	2312.06	nM	PMID[525414]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	1717.91	nM	PMID[525414]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	3507.52	nM	PMID[525414]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	1256.03	nM	PMID[525414]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	2187.76	nM	PMID[525414]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	2108.63	nM	PMID[525414]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	1909.85	nM	PMID[525414]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	1770.11	nM	PMID[525414]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	1945.36	nM	PMID[525414]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	1819.7	nM	PMID[525414]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	1717.91	nM	PMID[525414]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	3061.96	nM	PMID[525414]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	2552.7	nM	PMID[525414]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	4197.59	nM	PMID[525414]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	1559.55	nM	PMID[525414]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	3614.1	nM	PMID[525414]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	1931.97	nM	PMID[525414]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	1940.89	nM	PMID[525414]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	2691.53	nM	PMID[525414]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	2285.6	nM	PMID[525414]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	1559.55	nM	PMID[525414]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	3019.95	nM	PMID[525414]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	2172.7	nM	PMID[525414]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	2264.64	nM	PMID[525414]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	2018.37	nM	PMID[525414]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	1412.54	nM	PMID[525414]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	1199.5	nM	PMID[525414]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	3491.4	nM	PMID[525414]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	1702.16	nM	PMID[525414]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	1352.07	nM	PMID[525414]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC77294 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	1688
0.1-0.2	14568
0.2-0.3	17445
0.3-0.4	3980
0.4-0.5	2446
0.5-0.6	1591
0.6-0.7	737
0.7-0.8	229
0.8-0.85	9
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7193	Intermediate Similarity	NPC275467
0.681	Remote Similarity	NPC471310
0.68	Remote Similarity	NPC320656
0.6727	Remote Similarity	NPC476160
0.6718	Remote Similarity	NPC469949
0.6712	Remote Similarity	NPC476464
0.6667	Remote Similarity	NPC139658
0.6639	Remote Similarity	NPC473498
0.6636	Remote Similarity	NPC169016
0.6619	Remote Similarity	NPC32002
0.6619	Remote Similarity	NPC315348
0.6587	Remote Similarity	NPC313449
0.6555	Remote Similarity	NPC474559
0.6549	Remote Similarity	NPC469330
0.6538	Remote Similarity	NPC12857
0.6522	Remote Similarity	NPC472258
0.6509	Remote Similarity	NPC231986
0.6491	Remote Similarity	NPC329430
0.648	Remote Similarity	NPC113099
0.6471	Remote Similarity	NPC122327
0.6471	Remote Similarity	NPC113000
0.6471	Remote Similarity	NPC112609
0.6442	Remote Similarity	NPC98269
0.6442	Remote Similarity	NPC325662
0.6404	Remote Similarity	NPC7067
0.64	Remote Similarity	NPC187036
0.64	Remote Similarity	NPC296163
0.6389	Remote Similarity	NPC119677
0.6371	Remote Similarity	NPC275410
0.6364	Remote Similarity	NPC258046
0.6346	Remote Similarity	NPC271642
0.6341	Remote Similarity	NPC470127
0.633	Remote Similarity	NPC133162
0.6328	Remote Similarity	NPC192209
0.6308	Remote Similarity	NPC317564
0.6304	Remote Similarity	NPC313352
0.6303	Remote Similarity	NPC291610
0.6293	Remote Similarity	NPC471319
0.6293	Remote Similarity	NPC471320
0.6286	Remote Similarity	NPC290638
0.627	Remote Similarity	NPC314141
0.626	Remote Similarity	NPC164802
0.625	Remote Similarity	NPC98976
0.625	Remote Similarity	NPC12429
0.6228	Remote Similarity	NPC470926
0.622	Remote Similarity	NPC471318
0.6214	Remote Similarity	NPC325599
0.6207	Remote Similarity	NPC303045
0.6207	Remote Similarity	NPC161972
0.6207	Remote Similarity	NPC108339
0.6176	Remote Similarity	NPC229235
0.6161	Remote Similarity	NPC473031
0.6154	Remote Similarity	NPC264580
0.6154	Remote Similarity	NPC220698
0.6124	Remote Similarity	NPC125416
0.6106	Remote Similarity	NPC262393
0.6102	Remote Similarity	NPC311242
0.6095	Remote Similarity	NPC276699
0.6091	Remote Similarity	NPC104070
0.6087	Remote Similarity	NPC226438
0.6071	Remote Similarity	NPC203076
0.6069	Remote Similarity	NPC476454
0.6047	Remote Similarity	NPC288232
0.6029	Remote Similarity	NPC476249
0.6019	Remote Similarity	NPC219246
0.6015	Remote Similarity	NPC71684
0.6	Remote Similarity	NPC302790
0.6	Remote Similarity	NPC14326
0.5985	Remote Similarity	NPC478079
0.5983	Remote Similarity	NPC322040
0.5969	Remote Similarity	NPC33742
0.5968	Remote Similarity	NPC45033
0.5929	Remote Similarity	NPC476689
0.5929	Remote Similarity	NPC476685
0.5929	Remote Similarity	NPC476687
0.5913	Remote Similarity	NPC470877
0.5905	Remote Similarity	NPC244738
0.5896	Remote Similarity	NPC475915
0.5882	Remote Similarity	NPC25565
0.5878	Remote Similarity	NPC119569
0.5877	Remote Similarity	NPC305602
0.5877	Remote Similarity	NPC17497
0.5862	Remote Similarity	NPC159178
0.5862	Remote Similarity	NPC471307
0.5862	Remote Similarity	NPC121872
0.5862	Remote Similarity	NPC78154
0.5862	Remote Similarity	NPC78041
0.5862	Remote Similarity	NPC74936
0.5862	Remote Similarity	NPC141139
0.5862	Remote Similarity	NPC209764
0.5849	Remote Similarity	NPC299134
0.5841	Remote Similarity	NPC3210
0.584	Remote Similarity	NPC471447
0.584	Remote Similarity	NPC327481
0.5833	Remote Similarity	NPC475439
0.5833	Remote Similarity	NPC473501
0.582	Remote Similarity	NPC474582
0.5818	Remote Similarity	NPC475573
0.5818	Remote Similarity	NPC475289
0.5816	Remote Similarity	NPC22079
0.5811	Remote Similarity	NPC473804
0.5797	Remote Similarity	NPC166424
0.5797	Remote Similarity	NPC245244
0.5797	Remote Similarity	NPC146373
0.5793	Remote Similarity	NPC125746
0.5786	Remote Similarity	NPC9856
0.5781	Remote Similarity	NPC319579
0.5781	Remote Similarity	NPC313981
0.5772	Remote Similarity	NPC239854
0.576	Remote Similarity	NPC143516
0.576	Remote Similarity	NPC474695
0.5758	Remote Similarity	NPC313673
0.5758	Remote Similarity	NPC314919
0.5755	Remote Similarity	NPC476950
0.5743	Remote Similarity	NPC63157
0.5743	Remote Similarity	NPC473868
0.5739	Remote Similarity	NPC262295
0.5739	Remote Similarity	NPC471638
0.5739	Remote Similarity	NPC60408
0.5726	Remote Similarity	NPC172128
0.5726	Remote Similarity	NPC191444
0.5725	Remote Similarity	NPC27740
0.5724	Remote Similarity	NPC325252
0.5714	Remote Similarity	NPC474804
0.5714	Remote Similarity	NPC130898
0.5714	Remote Similarity	NPC73767
0.5714	Remote Similarity	NPC471309
0.5714	Remote Similarity	NPC474973
0.5714	Remote Similarity	NPC116961
0.5692	Remote Similarity	NPC474584
0.569	Remote Similarity	NPC111233
0.569	Remote Similarity	NPC30445
0.5685	Remote Similarity	NPC471312
0.5683	Remote Similarity	NPC252794
0.5678	Remote Similarity	NPC245259
0.5676	Remote Similarity	NPC59084
0.5676	Remote Similarity	NPC469768
0.5676	Remote Similarity	NPC2949
0.5676	Remote Similarity	NPC469784
0.5676	Remote Similarity	NPC469767
0.5676	Remote Similarity	NPC469783
0.5676	Remote Similarity	NPC469780
0.5676	Remote Similarity	NPC469761
0.5676	Remote Similarity	NPC469779
0.5669	Remote Similarity	NPC318065
0.5669	Remote Similarity	NPC206819
0.5667	Remote Similarity	NPC256452
0.5664	Remote Similarity	NPC134825
0.5664	Remote Similarity	NPC474088
0.5655	Remote Similarity	NPC198988
0.5649	Remote Similarity	NPC276949
0.5649	Remote Similarity	NPC35850
0.5643	Remote Similarity	NPC145754
0.5641	Remote Similarity	NPC173991
0.5641	Remote Similarity	NPC176858
0.5639	Remote Similarity	NPC285926
0.5639	Remote Similarity	NPC315276
0.5639	Remote Similarity	NPC470544
0.5639	Remote Similarity	NPC14672
0.5639	Remote Similarity	NPC239357
0.5638	Remote Similarity	NPC469766
0.5635	Remote Similarity	NPC473418
0.563	Remote Similarity	NPC473661
0.5616	Remote Similarity	NPC218268
0.5615	Remote Similarity	NPC475013
0.5612	Remote Similarity	NPC474479
0.5608	Remote Similarity	NPC88097
0.5608	Remote Similarity	NPC110126
0.5603	Remote Similarity	NPC53492
0.56	Remote Similarity	NPC474430
0.56	Remote Similarity	NPC164859
0.56	Remote Similarity	NPC136002
0.56	Remote Similarity	NPC20144

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC77294 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	1015
0.2-0.3	993
0.3-0.4	1945
0.4-0.5	2213
0.5-0.6	1831
0.6-0.7	624
0.7-0.8	133
0.8-0.85	10
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7685	Intermediate Similarity	NPD728	Approved
0.7345	Intermediate Similarity	NPD2939	Approved
0.7345	Intermediate Similarity	NPD2937	Phase 1
0.7258	Intermediate Similarity	NPD4323	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4801	Phase 1
0.7248	Intermediate Similarity	NPD2655	Approved
0.7248	Intermediate Similarity	NPD2656	Approved
0.7167	Intermediate Similarity	NPD440	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2371	Approved
0.7143	Intermediate Similarity	NPD524	Approved
0.7143	Intermediate Similarity	NPD523	Approved
0.7034	Intermediate Similarity	NPD6235	Approved
0.7034	Intermediate Similarity	NPD6236	Approved
0.7019	Intermediate Similarity	NPD263	Approved
0.7019	Intermediate Similarity	NPD262	Approved
0.7018	Intermediate Similarity	NPD5753	Discontinued
0.6952	Remote Similarity	NPD785	Approved
0.6942	Remote Similarity	NPD2665	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1903	Approved
0.6916	Remote Similarity	NPD4146	Approved
0.6916	Remote Similarity	NPD4145	Approved
0.6891	Remote Similarity	NPD7120	Approved
0.6864	Remote Similarity	NPD1401	Approved
0.6863	Remote Similarity	NPD296	Approved
0.6863	Remote Similarity	NPD295	Approved
0.6863	Remote Similarity	NPD293	Approved
0.6857	Remote Similarity	NPD831	Approved
0.6857	Remote Similarity	NPD830	Approved
0.6855	Remote Similarity	NPD2109	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2108	Phase 2
0.6818	Remote Similarity	NPD4543	Discontinued
0.6803	Remote Similarity	NPD7060	Approved
0.6803	Remote Similarity	NPD7059	Approved
0.68	Remote Similarity	NPD2395	Approved
0.68	Remote Similarity	NPD2396	Approved
0.6783	Remote Similarity	NPD2657	Approved
0.675	Remote Similarity	NPD1107	Approved
0.675	Remote Similarity	NPD1108	Approved
0.6746	Remote Similarity	NPD3498	Approved
0.6746	Remote Similarity	NPD3499	Approved
0.6744	Remote Similarity	NPD2940	Approved
0.6744	Remote Similarity	NPD2938	Approved
0.6727	Remote Similarity	NPD5915	Approved
0.6721	Remote Similarity	NPD7121	Approved
0.6718	Remote Similarity	NPD6713	Approved
0.6718	Remote Similarity	NPD6712	Approved
0.6712	Remote Similarity	NPD3113	Approved
0.6712	Remote Similarity	NPD3115	Approved
0.6712	Remote Similarity	NPD3114	Approved
0.6712	Remote Similarity	NPD3112	Approved
0.6694	Remote Similarity	NPD652	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD986	Discontinued
0.6692	Remote Similarity	NPD1937	Approved
0.6667	Remote Similarity	NPD1635	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2165	Phase 1
0.6639	Remote Similarity	NPD4778	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD448	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD449	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3651	Discontinued
0.6637	Remote Similarity	NPD5554	Approved
0.6636	Remote Similarity	NPD5178	Approved
0.6636	Remote Similarity	NPD2539	Approved
0.6636	Remote Similarity	NPD2538	Approved
0.6635	Remote Similarity	NPD590	Approved
0.6635	Remote Similarity	NPD589	Approved
0.6619	Remote Similarity	NPD2074	Approved
0.6619	Remote Similarity	NPD2072	Approved
0.6619	Remote Similarity	NPD2075	Approved
0.6619	Remote Similarity	NPD2073	Approved
0.6612	Remote Similarity	NPD4063	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD782	Approved
0.6606	Remote Similarity	NPD783	Approved
0.6606	Remote Similarity	NPD781	Approved
0.6606	Remote Similarity	NPD780	Approved
0.6604	Remote Similarity	NPD4170	Approved
0.6604	Remote Similarity	NPD4169	Approved
0.6604	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4144	Approved
0.6602	Remote Similarity	NPD4147	Approved
0.6589	Remote Similarity	NPD2131	Approved
0.6587	Remote Similarity	NPD5130	Phase 3
0.6587	Remote Similarity	NPD410	Suspended
0.6587	Remote Similarity	NPD7481	Approved
0.6587	Remote Similarity	NPD7480	Approved
0.6583	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD233	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7160	Approved
0.6515	Remote Similarity	NPD1321	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD472	Approved
0.6509	Remote Similarity	NPD3035	Approved
0.6508	Remote Similarity	NPD2464	Approved
0.6508	Remote Similarity	NPD2463	Approved
0.6508	Remote Similarity	NPD2467	Approved
0.65	Remote Similarity	NPD9699	Approved
0.648	Remote Similarity	NPD1074	Approved
0.648	Remote Similarity	NPD1075	Approved
0.648	Remote Similarity	NPD1073	Approved
0.6476	Remote Similarity	NPD1051	Approved
0.6476	Remote Similarity	NPD1052	Approved
0.6476	Remote Similarity	NPD1053	Approved
0.6471	Remote Similarity	NPD9590	Approved
0.6471	Remote Similarity	NPD9592	Approved
0.6471	Remote Similarity	NPD9588	Approved
0.6471	Remote Similarity	NPD80	Approved
0.6471	Remote Similarity	NPD9591	Approved
0.6471	Remote Similarity	NPD9589	Approved
0.6471	Remote Similarity	NPD9594	Approved
0.6471	Remote Similarity	NPD9593	Approved
0.6463	Remote Similarity	NPD3339	Approved
0.6462	Remote Similarity	NPD1703	Clinical (unspecified phase)
0.646	Remote Similarity	NPD1814	Approved
0.646	Remote Similarity	NPD1812	Approved
0.6455	Remote Similarity	NPD2002	Discontinued
0.6455	Remote Similarity	NPD3428	Approved
0.6455	Remote Similarity	NPD3426	Approved
0.6449	Remote Similarity	NPD2867	Approved
0.6449	Remote Similarity	NPD2399	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6299	Approved
0.6446	Remote Similarity	NPD6300	Approved
0.6442	Remote Similarity	NPD603	Approved
0.6439	Remote Similarity	NPD2031	Discontinued
0.6435	Remote Similarity	NPD2005	Discontinued
0.6435	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD7220	Approved
0.6422	Remote Similarity	NPD5916	Discontinued
0.6415	Remote Similarity	NPD5372	Approved
0.6415	Remote Similarity	NPD5371	Approved
0.6412	Remote Similarity	NPD5335	Discontinued
0.6404	Remote Similarity	NPD199	Approved
0.6404	Remote Similarity	NPD197	Approved
0.6396	Remote Similarity	NPD3345	Approved
0.6387	Remote Similarity	NPD1415	Approved
0.6383	Remote Similarity	NPD1904	Approved
0.6383	Remote Similarity	NPD1902	Approved
0.6379	Remote Similarity	NPD1076	Approved
0.6379	Remote Similarity	NPD528	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD3000	Approved
0.6372	Remote Similarity	NPD2997	Approved
0.6372	Remote Similarity	NPD2998	Approved
0.6371	Remote Similarity	NPD2999	Approved
0.6371	Remote Similarity	NPD1935	Phase 3
0.6371	Remote Similarity	NPD9698	Approved
0.6371	Remote Similarity	NPD3001	Approved
0.637	Remote Similarity	NPD3852	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2866	Approved
0.6364	Remote Similarity	NPD993	Approved
0.6364	Remote Similarity	NPD990	Approved
0.6355	Remote Similarity	NPD4026	Approved
0.6355	Remote Similarity	NPD4027	Approved
0.635	Remote Similarity	NPD936	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD1020	Approved
0.6349	Remote Similarity	NPD7062	Discontinued
0.6349	Remote Similarity	NPD1022	Approved
0.6349	Remote Similarity	NPD1021	Approved
0.6349	Remote Similarity	NPD1023	Approved
0.6349	Remote Similarity	NPD5631	Phase 3
0.6339	Remote Similarity	NPD297	Approved
0.6339	Remote Similarity	NPD9	Approved
0.6331	Remote Similarity	NPD1998	Approved
0.633	Remote Similarity	NPD3427	Approved
0.633	Remote Similarity	NPD3429	Approved
0.632	Remote Similarity	NPD561	Approved
0.632	Remote Similarity	NPD560	Approved
0.6312	Remote Similarity	NPD1864	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD1320	Phase 1
0.6308	Remote Similarity	NPD5407	Approved
0.6308	Remote Similarity	NPD4630	Approved
0.6308	Remote Similarity	NPD4631	Approved
0.6304	Remote Similarity	NPD1106	Discontinued
0.6303	Remote Similarity	NPD5716	Approved
0.6294	Remote Similarity	NPD5009	Approved
0.6294	Remote Similarity	NPD5010	Approved
0.629	Remote Similarity	NPD2384	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD3346	Approved
0.6283	Remote Similarity	NPD3344	Approved
0.6282	Remote Similarity	NPD3117	Approved
0.6282	Remote Similarity	NPD3116	Approved
0.6281	Remote Similarity	NPD563	Approved
0.6281	Remote Similarity	NPD564	Approved
0.6279	Remote Similarity	NPD152	Suspended
0.6273	Remote Similarity	NPD2208	Approved
0.6273	Remote Similarity	NPD2205	Approved
0.6271	Remote Similarity	NPD1946	Clinical (unspecified phase)
0.627	Remote Similarity	NPD1656	Phase 2
0.6268	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD473	Clinical (unspecified phase)
0.626	Remote Similarity	NPD477	Phase 1
0.626	Remote Similarity	NPD2679	Approved
0.626	Remote Similarity	NPD2678	Approved
0.6259	Remote Similarity	NPD6086	Phase 2
0.6259	Remote Similarity	NPD3851	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD305	Approved
0.6216	Remote Similarity	NPD4636	Approved
0.6216	Remote Similarity	NPD304	Approved
0.6214	Remote Similarity	NPD1883	Approved
0.6214	Remote Similarity	NPD1515	Discontinued
0.6202	Remote Similarity	NPD828	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data