NPASS Compound

Structure

CID284656 OpenBabel06191716092D 25 27 0 0 1 0 0 0 0 0999 V2000 2.4704 3.6469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4994 1.5328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7898 -0.1327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3564 3.7437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2370 0.0105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2452 3.1138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1428 0.5335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1300 2.6019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2070 2.2656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7405 0.0946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3812 1.5397 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7155 2.8274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3522 0.5224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3394 2.5908 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3458 1.5564 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0191 3.0964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6996 0.2604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1981 0.8161 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1364 1.5675 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.1608 4.2056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3291 -0.6638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3156 0.8542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1117 1.5735 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7224 3.0110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 11 1 0 0 0 0 4 12 2 0 0 0 0 5 7 1 0 0 0 0 5 13 2 0 0 0 0 6 8 1 0 0 0 0 7 19 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 10 24 1 0 0 0 0 11 18 1 1 0 0 0 12 16 1 0 0 0 0 14 6 1 1 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 13 1 1 0 0 0 15 19 1 0 0 0 0 16 20 2 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 3 1 6 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	351.17
Volume:	347.407
LogP:	0.848
LogD:	0.701
LogS:	-0.94
# Rotatable Bonds:	0
TPSA:	95.89
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.232
Synthetic Accessibility Score:	5.694
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.307
MDCK Permeability:	6.772291817469522e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.896
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.26
Plasma Protein Binding (PPB):	30.286144256591797%
Volume Distribution (VD):	1.05
Pgp-substrate:	60.30366516113281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.143
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.296
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.271

ADMET: Excretion

Clearance (CL):	5.646
Half-life (T1/2):	0.957

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.23
Drug-inuced Liver Injury (DILI):	0.27
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.74
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.244
Carcinogencity:	0.941
Eye Corrosion:	0.004
Eye Irritation:	0.089
Respiratory Toxicity:	0.323

Download Data

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

Natural Product: NPC284656

Natural Product ID:	NPC284656
*Common Name:**	Senecionine N-Oxide
IUPAC Name:	n.a.
Synonyms:	Senecionine N-Oxide
Standard InCHIKey:	PLGBHVNNYDZWGZ-GPUZEBNTSA-N
Standard InCHI:	InChI=1S/C18H25NO6/c1-4-12-9-11(2)18(3,22)17(21)24-10-13-5-7-19(23)8-6-14(15(13)19)25-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4-/t11-,14-,15-,18-,19?/m1/s1
SMILES:	C/C=C1/C[C@@H](C)[C@](C)(C(=O)OCC2=CCN3(=O)CC[C@H]([C@@H]23)OC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471683
PubChem CID:	5380876
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives

*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
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19694	Senecio scandens	Species	Asteraceae	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	56
IC50	1
Others	3

Activity Type	# Activity
Cell Line	57
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2319	Cell Line	A204	Homo sapiens	IC50	=	150.0	ug.mL-1	PMID[497489]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	94623.72	nM	PMID[497490]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	48.19	nM	PMID[497490]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[497490]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	MIC50	=	2900.0	ug.mL-1	PMID[497491]
NPT2531	Organism	Heterodera schachtii	Heterodera schachtii	MIC50	=	3400.0	ug.mL-1	PMID[497491]
NPT2531	Organism	Heterodera schachtii	Heterodera schachtii	MIC50	=	7200.0	ug.mL-1	PMID[497491]

☑ 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 NPC284656 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	115
0.1-0.2	767
0.2-0.3	4816
0.3-0.4	19998
0.4-0.5	11944
0.5-0.6	4407
0.6-0.7	626
0.7-0.8	7
0.8-0.85	6
0.85-0.9	3
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC193471
0.963	High Similarity	NPC130124
0.9286	High Similarity	NPC106791
0.9286	High Similarity	NPC201889
0.9266	High Similarity	NPC47857
0.9266	High Similarity	NPC168758
0.9266	High Similarity	NPC181510
0.8621	High Similarity	NPC235625
0.8584	High Similarity	NPC30911
0.8584	High Similarity	NPC316984
0.8559	High Similarity	NPC23963
0.8214	Intermediate Similarity	NPC64168
0.8125	Intermediate Similarity	NPC6271
0.8125	Intermediate Similarity	NPC279833
0.8125	Intermediate Similarity	NPC173690
0.8125	Intermediate Similarity	NPC80439
0.8017	Intermediate Similarity	NPC196073
0.8017	Intermediate Similarity	NPC195435
0.7881	Intermediate Similarity	NPC474497
0.7881	Intermediate Similarity	NPC275100
0.7561	Intermediate Similarity	NPC156336
0.7561	Intermediate Similarity	NPC200412
0.7561	Intermediate Similarity	NPC120599
0.7165	Intermediate Similarity	NPC230849
0.6977	Remote Similarity	NPC470000
0.6967	Remote Similarity	NPC474099
0.6917	Remote Similarity	NPC474827
0.6917	Remote Similarity	NPC199831
0.6917	Remote Similarity	NPC474828
0.6917	Remote Similarity	NPC68001
0.6838	Remote Similarity	NPC133089
0.6825	Remote Similarity	NPC469597
0.6815	Remote Similarity	NPC477988
0.6797	Remote Similarity	NPC469997
0.678	Remote Similarity	NPC476344
0.6767	Remote Similarity	NPC329401
0.6767	Remote Similarity	NPC477987
0.6752	Remote Similarity	NPC150041
0.6748	Remote Similarity	NPC271562
0.6724	Remote Similarity	NPC81419
0.6724	Remote Similarity	NPC179746
0.6723	Remote Similarity	NPC471144
0.672	Remote Similarity	NPC469603
0.6719	Remote Similarity	NPC30196
0.6696	Remote Similarity	NPC51004
0.6694	Remote Similarity	NPC474244
0.6694	Remote Similarity	NPC473289
0.6692	Remote Similarity	NPC471087
0.6692	Remote Similarity	NPC477985
0.6692	Remote Similarity	NPC326386
0.6667	Remote Similarity	NPC65045
0.6667	Remote Similarity	NPC6531
0.6667	Remote Similarity	NPC474431
0.6667	Remote Similarity	NPC474411
0.6642	Remote Similarity	NPC316401
0.6641	Remote Similarity	NPC11379
0.6639	Remote Similarity	NPC475945
0.6639	Remote Similarity	NPC475871
0.6639	Remote Similarity	NPC52820
0.6638	Remote Similarity	NPC12172
0.6638	Remote Similarity	NPC30515
0.6638	Remote Similarity	NPC208886
0.6637	Remote Similarity	NPC469860
0.6637	Remote Similarity	NPC130436
0.6637	Remote Similarity	NPC469861
0.6617	Remote Similarity	NPC323168
0.6617	Remote Similarity	NPC293550
0.6617	Remote Similarity	NPC318445
0.6617	Remote Similarity	NPC316133
0.6617	Remote Similarity	NPC111162
0.6617	Remote Similarity	NPC477989
0.6617	Remote Similarity	NPC477990
0.6615	Remote Similarity	NPC174463
0.6614	Remote Similarity	NPC1111
0.6614	Remote Similarity	NPC60432
0.6614	Remote Similarity	NPC261750
0.6612	Remote Similarity	NPC474742
0.6609	Remote Similarity	NPC307411
0.6585	Remote Similarity	NPC474741
0.6583	Remote Similarity	NPC473326
0.6581	Remote Similarity	NPC476300
0.6581	Remote Similarity	NPC475912
0.6569	Remote Similarity	NPC307165
0.6557	Remote Similarity	NPC474747
0.6557	Remote Similarity	NPC149371
0.6552	Remote Similarity	NPC474761
0.6552	Remote Similarity	NPC476004
0.6552	Remote Similarity	NPC473619
0.6544	Remote Similarity	NPC471086
0.6535	Remote Similarity	NPC58281
0.6525	Remote Similarity	NPC474035
0.6525	Remote Similarity	NPC81386
0.6522	Remote Similarity	NPC202672
0.6519	Remote Similarity	NPC474371
0.6508	Remote Similarity	NPC38154
0.6496	Remote Similarity	NPC184463
0.6496	Remote Similarity	NPC473321
0.6484	Remote Similarity	NPC43648
0.6475	Remote Similarity	NPC47880
0.6475	Remote Similarity	NPC476270
0.6471	Remote Similarity	NPC270013
0.6471	Remote Similarity	NPC36954
0.6471	Remote Similarity	NPC476951
0.6471	Remote Similarity	NPC204556
0.6471	Remote Similarity	NPC314282
0.6471	Remote Similarity	NPC14961
0.6466	Remote Similarity	NPC295312
0.6452	Remote Similarity	NPC469604
0.6449	Remote Similarity	NPC215507
0.6441	Remote Similarity	NPC212486
0.6439	Remote Similarity	NPC138534
0.6439	Remote Similarity	NPC477986
0.6435	Remote Similarity	NPC160138
0.6429	Remote Similarity	NPC120420
0.6423	Remote Similarity	NPC173173
0.6404	Remote Similarity	NPC21469
0.6403	Remote Similarity	NPC120335
0.64	Remote Similarity	NPC93179
0.64	Remote Similarity	NPC243998
0.64	Remote Similarity	NPC223450
0.6393	Remote Similarity	NPC475949
0.6387	Remote Similarity	NPC473330
0.6387	Remote Similarity	NPC473316
0.6385	Remote Similarity	NPC472536
0.6385	Remote Similarity	NPC103391
0.6383	Remote Similarity	NPC471256
0.6383	Remote Similarity	NPC99864
0.6371	Remote Similarity	NPC475873
0.6371	Remote Similarity	NPC472755
0.6364	Remote Similarity	NPC9714
0.6349	Remote Similarity	NPC26617
0.6349	Remote Similarity	NPC477513
0.6348	Remote Similarity	NPC112685
0.6348	Remote Similarity	NPC284902
0.6341	Remote Similarity	NPC185141
0.6341	Remote Similarity	NPC15993
0.6341	Remote Similarity	NPC164598
0.6341	Remote Similarity	NPC110443
0.6341	Remote Similarity	NPC472753
0.6341	Remote Similarity	NPC46998
0.6341	Remote Similarity	NPC128733
0.6341	Remote Similarity	NPC133907
0.6341	Remote Similarity	NPC474339
0.6338	Remote Similarity	NPC243902
0.6333	Remote Similarity	NPC471142
0.6328	Remote Similarity	NPC122926
0.6328	Remote Similarity	NPC113012
0.6328	Remote Similarity	NPC5103
0.6325	Remote Similarity	NPC477011
0.6324	Remote Similarity	NPC313342
0.6324	Remote Similarity	NPC314451
0.6324	Remote Similarity	NPC314512
0.6324	Remote Similarity	NPC469999
0.6324	Remote Similarity	NPC313333
0.632	Remote Similarity	NPC44514
0.632	Remote Similarity	NPC203659
0.632	Remote Similarity	NPC100487
0.6316	Remote Similarity	NPC471261
0.6311	Remote Similarity	NPC187268
0.6303	Remote Similarity	NPC162205
0.6303	Remote Similarity	NPC288240
0.6303	Remote Similarity	NPC295204
0.6303	Remote Similarity	NPC273579
0.6303	Remote Similarity	NPC135776
0.6299	Remote Similarity	NPC70235
0.6293	Remote Similarity	NPC475703
0.6293	Remote Similarity	NPC186148
0.6293	Remote Similarity	NPC231889
0.629	Remote Similarity	NPC86077
0.629	Remote Similarity	NPC320019
0.629	Remote Similarity	NPC324017
0.629	Remote Similarity	NPC472754
0.6286	Remote Similarity	NPC189393
0.6286	Remote Similarity	NPC90814
0.6281	Remote Similarity	NPC476315
0.6281	Remote Similarity	NPC17585
0.6281	Remote Similarity	NPC477921
0.6279	Remote Similarity	NPC179798
0.6279	Remote Similarity	NPC304180
0.6271	Remote Similarity	NPC473448
0.6261	Remote Similarity	NPC477018
0.6261	Remote Similarity	NPC215364
0.6261	Remote Similarity	NPC100921
0.626	Remote Similarity	NPC26597
0.626	Remote Similarity	NPC288876
0.6259	Remote Similarity	NPC470539
0.6259	Remote Similarity	NPC315387
0.6259	Remote Similarity	NPC316205
0.625	Remote Similarity	NPC314050
0.625	Remote Similarity	NPC477131
0.625	Remote Similarity	NPC315809
0.625	Remote Similarity	NPC314629
0.624	Remote Similarity	NPC110989
0.624	Remote Similarity	NPC472750
0.624	Remote Similarity	NPC472747
0.6239	Remote Similarity	NPC153805
0.6239	Remote Similarity	NPC473715
0.6239	Remote Similarity	NPC58219
0.6239	Remote Similarity	NPC177629
0.6239	Remote Similarity	NPC89001

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 NPC284656 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	91
0.1-0.2	650
0.2-0.3	3199
0.3-0.4	3829
0.4-0.5	1135
0.5-0.6	225
0.6-0.7	20
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8584	High Similarity	NPD2204	Approved
0.6617	Remote Similarity	NPD7642	Approved
0.6541	Remote Similarity	NPD8080	Discontinued
0.6519	Remote Similarity	NPD8451	Approved
0.6489	Remote Similarity	NPD7641	Discontinued
0.6475	Remote Similarity	NPD6845	Suspended
0.6471	Remote Similarity	NPD8448	Approved
0.6466	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD8415	Approved
0.6349	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD8390	Approved
0.6331	Remote Similarity	NPD8391	Approved
0.6331	Remote Similarity	NPD8392	Approved
0.6324	Remote Similarity	NPD8341	Approved
0.6324	Remote Similarity	NPD8299	Approved
0.6324	Remote Similarity	NPD8342	Approved
0.6324	Remote Similarity	NPD8340	Approved
0.6286	Remote Similarity	NPD7260	Phase 2
0.6159	Remote Similarity	NPD8273	Phase 1
0.6026	Remote Similarity	NPD2575	Approved
0.6014	Remote Similarity	NPD7829	Approved
0.6014	Remote Similarity	NPD8384	Approved
0.6014	Remote Similarity	NPD7830	Approved
0.5954	Remote Similarity	NPD6421	Discontinued
0.5944	Remote Similarity	NPD3664	Approved
0.5944	Remote Similarity	NPD3663	Approved
0.5944	Remote Similarity	NPD3662	Phase 3
0.5944	Remote Similarity	NPD3661	Approved
0.594	Remote Similarity	NPD1376	Discontinued
0.5868	Remote Similarity	NPD6698	Approved
0.5868	Remote Similarity	NPD46	Approved
0.5845	Remote Similarity	NPD8336	Approved
0.5845	Remote Similarity	NPD8337	Approved
0.5823	Remote Similarity	NPD8414	Discontinued
0.5769	Remote Similarity	NPD4211	Phase 1
0.5755	Remote Similarity	NPD8444	Approved
0.5755	Remote Similarity	NPD6909	Approved
0.5755	Remote Similarity	NPD6908	Approved
0.5738	Remote Similarity	NPD7838	Discovery
0.5724	Remote Similarity	NPD5204	Approved
0.5714	Remote Similarity	NPD6371	Approved
0.5714	Remote Similarity	NPD4621	Approved
0.5714	Remote Similarity	NPD4619	Approved
0.5714	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5685	Remote Similarity	NPD2613	Approved
0.5685	Remote Similarity	NPD8338	Approved
0.5682	Remote Similarity	NPD6686	Approved
0.568	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD3615	Approved
0.5676	Remote Similarity	NPD3087	Approved
0.5676	Remote Similarity	NPD2573	Approved
0.5676	Remote Similarity	NPD3088	Approved
0.5676	Remote Similarity	NPD2571	Approved
0.5676	Remote Similarity	NPD2574	Discontinued
0.5676	Remote Similarity	NPD2570	Approved
0.5676	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD3614	Approved
0.5676	Remote Similarity	NPD4746	Phase 3
0.5676	Remote Similarity	NPD3089	Approved
0.5676	Remote Similarity	NPD2566	Approved
0.5676	Remote Similarity	NPD3616	Approved
0.5676	Remote Similarity	NPD4745	Approved
0.5676	Remote Similarity	NPD3090	Approved
0.5669	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD8074	Phase 3
0.5664	Remote Similarity	NPD1452	Discontinued
0.5645	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5643	Remote Similarity	NPD6921	Approved
0.5635	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.56	Remote Similarity	NPD4684	Phase 3
0.56	Remote Similarity	NPD4685	Phase 3
0.56	Remote Similarity	NPD6334	Approved
0.56	Remote Similarity	NPD4686	Approved
0.56	Remote Similarity	NPD6333	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