NPASS Compound

Structure

CID316984 OpenBabel06191716132D 26 28 0 0 1 0 0 0 0 0999 V2000 -0.4108 -1.4086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1040 0.5777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7621 1.5148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0520 0.2889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2591 1.8629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2670 -1.1646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1428 1.3527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1303 -0.6652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7584 1.7368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3654 -0.6420 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8282 -0.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3958 1.3635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3833 -0.6544 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3896 0.3547 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0027 -1.0152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3778 1.3760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0046 0.7386 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1365 0.3439 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -2.6043 -1.2444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7139 -2.0672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3888 2.1522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0509 0.4628 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0198 1.7414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7414 -1.0198 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7762 -0.7666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 17 1 0 0 0 0 5 7 1 0 0 0 0 5 12 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 12 1 0 0 0 0 9 24 1 0 0 0 0 10 15 1 0 0 0 0 10 18 1 6 0 0 0 11 20 2 0 0 0 0 11 26 1 0 0 0 0 12 14 1 0 0 0 0 13 6 1 1 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 19 1 1 0 0 0 15 21 2 0 0 0 0 15 25 1 0 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 16 24 1 0 0 0 0 17 18 1 6 0 0 0 17 23 1 0 0 0 0 18 4 1 1 0 0 0 18 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	367.16
Volume:	356.197
LogP:	0.824
LogD:	1.091
LogS:	-2.326
# Rotatable Bonds:	2
TPSA:	102.37
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.398
Synthetic Accessibility Score:	5.163
Fsp3:	0.722
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:	-5.212
MDCK Permeability:	7.326954073505476e-05
Pgp-inhibitor:	0.211
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.839
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.404
Plasma Protein Binding (PPB):	27.450780868530273%
Volume Distribution (VD):	1.101
Pgp-substrate:	73.19798278808594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.075
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.45
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.19
CYP3A4-inhibitor:	0.157
CYP3A4-substrate:	0.396

ADMET: Excretion

Clearance (CL):	4.077
Half-life (T1/2):	0.527

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.783
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.323
Skin Sensitization:	0.189
Carcinogencity:	0.941
Eye Corrosion:	0.026
Eye Irritation:	0.022
Respiratory Toxicity:	0.762

Download Data

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

Natural Product: NPC316984

Natural Product ID:	NPC316984
*Common Name:**	ZVBPCOQJPAOXMI-AGMGMWSQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZVBPCOQJPAOXMI-AGMGMWSQSA-N
Standard InCHI:	InChI=1S/C18H25NO7/c1-10-15(21)25-13-6-8-19-7-5-12(14(13)19)9-24-16(22)17(3,23)18(10,4)26-11(2)20/h5,10,13-14,23H,6-9H2,1-4H3/t10-,13+,14+,17-,18-/m0/s1
SMILES:	CC(=O)O[C@@]1(C)[C@@H](C)C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]1(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1987428
PubChem CID:	259727
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids 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
NPO27009	Crotalaria retusa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27009	Crotalaria retusa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27009	Crotalaria retusa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27009	Crotalaria retusa	Species	Fabaceae	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	50

Activity Type	# Activity
Cell Line	50

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	41020.41	nM	PMID[536076]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[536076]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536076]

☑ 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 NPC316984 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	105
0.1-0.2	708
0.2-0.3	5214
0.3-0.4	20607
0.4-0.5	11539
0.5-0.6	4075
0.6-0.7	423
0.7-0.8	9
0.8-0.85	1
0.85-0.9	7
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC30911
0.9223	High Similarity	NPC64168
0.9126	High Similarity	NPC279833
0.9126	High Similarity	NPC80439
0.9126	High Similarity	NPC173690
0.9126	High Similarity	NPC6271
0.9091	High Similarity	NPC201889
0.9091	High Similarity	NPC106791
0.8899	High Similarity	NPC130124
0.8899	High Similarity	NPC193471
0.885	High Similarity	NPC23963
0.8584	High Similarity	NPC284656
0.8545	High Similarity	NPC168758
0.8545	High Similarity	NPC181510
0.8545	High Similarity	NPC47857
0.8103	Intermediate Similarity	NPC235625
0.7672	Intermediate Similarity	NPC275100
0.7652	Intermediate Similarity	NPC195435
0.7652	Intermediate Similarity	NPC196073
0.7521	Intermediate Similarity	NPC474497
0.7355	Intermediate Similarity	NPC156336
0.7355	Intermediate Similarity	NPC200412
0.7355	Intermediate Similarity	NPC120599
0.7094	Intermediate Similarity	NPC271562
0.7025	Intermediate Similarity	NPC469597
0.696	Remote Similarity	NPC230849
0.6953	Remote Similarity	NPC474371
0.686	Remote Similarity	NPC474431
0.686	Remote Similarity	NPC474411
0.681	Remote Similarity	NPC188785
0.6789	Remote Similarity	NPC52533
0.6769	Remote Similarity	NPC314282
0.6767	Remote Similarity	NPC133089
0.6752	Remote Similarity	NPC473289
0.6752	Remote Similarity	NPC474244
0.675	Remote Similarity	NPC474099
0.6718	Remote Similarity	NPC471086
0.6696	Remote Similarity	NPC52820
0.6695	Remote Similarity	NPC199831
0.6695	Remote Similarity	NPC474828
0.6695	Remote Similarity	NPC68001
0.6695	Remote Similarity	NPC474827
0.6693	Remote Similarity	NPC11379
0.6667	Remote Similarity	NPC150041
0.6667	Remote Similarity	NPC318445
0.6667	Remote Similarity	NPC316133
0.664	Remote Similarity	NPC30196
0.6638	Remote Similarity	NPC471144
0.6617	Remote Similarity	NPC215507
0.6617	Remote Similarity	NPC477988
0.6615	Remote Similarity	NPC314451
0.6615	Remote Similarity	NPC471087
0.6615	Remote Similarity	NPC477985
0.6615	Remote Similarity	NPC314512
0.6615	Remote Similarity	NPC313333
0.6615	Remote Similarity	NPC326386
0.6615	Remote Similarity	NPC313342
0.6593	Remote Similarity	NPC120420
0.6587	Remote Similarity	NPC6531
0.6587	Remote Similarity	NPC65045
0.6581	Remote Similarity	NPC475949
0.6567	Remote Similarity	NPC120335
0.6567	Remote Similarity	NPC316401
0.6565	Remote Similarity	NPC477987
0.6565	Remote Similarity	NPC329401
0.6555	Remote Similarity	NPC475945
0.6555	Remote Similarity	NPC475871
0.6552	Remote Similarity	NPC476344
0.6545	Remote Similarity	NPC478112
0.6544	Remote Similarity	NPC471256
0.6544	Remote Similarity	NPC99864
0.6535	Remote Similarity	NPC174463
0.6532	Remote Similarity	NPC261750
0.6532	Remote Similarity	NPC1111
0.6525	Remote Similarity	NPC474742
0.6509	Remote Similarity	NPC99651
0.6504	Remote Similarity	NPC469603
0.65	Remote Similarity	NPC469604
0.65	Remote Similarity	NPC474741
0.6493	Remote Similarity	NPC307165
0.6484	Remote Similarity	NPC471261
0.6471	Remote Similarity	NPC149371
0.6471	Remote Similarity	NPC474747
0.6466	Remote Similarity	NPC477793
0.6466	Remote Similarity	NPC329919
0.646	Remote Similarity	NPC316228
0.6446	Remote Similarity	NPC93179
0.6429	Remote Similarity	NPC472536
0.6429	Remote Similarity	NPC103391
0.6423	Remote Similarity	NPC38154
0.6417	Remote Similarity	NPC4620
0.6417	Remote Similarity	NPC475873
0.6412	Remote Similarity	NPC293550
0.6412	Remote Similarity	NPC477989
0.6412	Remote Similarity	NPC111162
0.6412	Remote Similarity	NPC323168
0.6412	Remote Similarity	NPC477990
0.6412	Remote Similarity	NPC471255
0.6404	Remote Similarity	NPC9447
0.64	Remote Similarity	NPC60432
0.64	Remote Similarity	NPC43648
0.6396	Remote Similarity	NPC469860
0.6396	Remote Similarity	NPC469861
0.6396	Remote Similarity	NPC130436
0.6396	Remote Similarity	NPC278283
0.6393	Remote Similarity	NPC26617
0.6391	Remote Similarity	NPC204556
0.6387	Remote Similarity	NPC46998
0.6387	Remote Similarity	NPC47880
0.6387	Remote Similarity	NPC133907
0.6387	Remote Similarity	NPC185141
0.6387	Remote Similarity	NPC164598
0.6387	Remote Similarity	NPC128733
0.6387	Remote Similarity	NPC474339
0.6387	Remote Similarity	NPC110443
0.6385	Remote Similarity	NPC470000
0.6379	Remote Similarity	NPC475659
0.6364	Remote Similarity	NPC212363
0.6364	Remote Similarity	NPC472756
0.6364	Remote Similarity	NPC475676
0.6364	Remote Similarity	NPC220964
0.6364	Remote Similarity	NPC44514
0.6348	Remote Similarity	NPC476300
0.6348	Remote Similarity	NPC81419
0.6348	Remote Similarity	NPC179746
0.6348	Remote Similarity	NPC475912
0.6343	Remote Similarity	NPC173173
0.6341	Remote Similarity	NPC70235
0.6333	Remote Similarity	NPC471148
0.6325	Remote Similarity	NPC477921
0.6325	Remote Similarity	NPC473859
0.632	Remote Similarity	NPC58281
0.6316	Remote Similarity	NPC473619
0.6316	Remote Similarity	NPC474232
0.6316	Remote Similarity	NPC51004
0.6316	Remote Similarity	NPC471263
0.6311	Remote Similarity	NPC9303
0.6311	Remote Similarity	NPC16313
0.6296	Remote Similarity	NPC316205
0.6296	Remote Similarity	NPC315387
0.6288	Remote Similarity	NPC314629
0.6283	Remote Similarity	NPC287089
0.6283	Remote Similarity	NPC476803
0.627	Remote Similarity	NPC276995
0.627	Remote Similarity	NPC76660
0.6269	Remote Similarity	NPC476951
0.6261	Remote Similarity	NPC30515
0.6261	Remote Similarity	NPC473321
0.6261	Remote Similarity	NPC72183
0.6261	Remote Similarity	NPC118844
0.6261	Remote Similarity	NPC299808
0.6261	Remote Similarity	NPC110875
0.6261	Remote Similarity	NPC184463
0.6261	Remote Similarity	NPC208886
0.6261	Remote Similarity	NPC12172
0.626	Remote Similarity	NPC477513
0.626	Remote Similarity	NPC194620
0.626	Remote Similarity	NPC474421
0.626	Remote Similarity	NPC72813
0.626	Remote Similarity	NPC326994
0.626	Remote Similarity	NPC324327
0.625	Remote Similarity	NPC472753
0.625	Remote Similarity	NPC469910
0.625	Remote Similarity	NPC476270
0.6241	Remote Similarity	NPC469999
0.6239	Remote Similarity	NPC471142
0.6239	Remote Similarity	NPC14961
0.6239	Remote Similarity	NPC477922
0.6239	Remote Similarity	NPC36954
0.6239	Remote Similarity	NPC475900
0.6239	Remote Similarity	NPC270013
0.6231	Remote Similarity	NPC138534
0.6231	Remote Similarity	NPC477986
0.623	Remote Similarity	NPC203659
0.623	Remote Similarity	NPC100487
0.623	Remote Similarity	NPC205176
0.6228	Remote Similarity	NPC473564
0.6228	Remote Similarity	NPC307411
0.6218	Remote Similarity	NPC473326
0.6216	Remote Similarity	NPC32676
0.6212	Remote Similarity	NPC471262
0.621	Remote Similarity	NPC474664
0.621	Remote Similarity	NPC117604
0.621	Remote Similarity	NPC169888
0.621	Remote Similarity	NPC327286
0.621	Remote Similarity	NPC233379
0.621	Remote Similarity	NPC14862
0.621	Remote Similarity	NPC55972
0.6207	Remote Similarity	NPC475302
0.6207	Remote Similarity	NPC469645
0.6207	Remote Similarity	NPC212486
0.6207	Remote Similarity	NPC165383
0.6207	Remote Similarity	NPC469692
0.6202	Remote Similarity	NPC469997
0.6198	Remote Similarity	NPC183571
0.6198	Remote Similarity	NPC472754
0.6195	Remote Similarity	NPC266957
0.6194	Remote Similarity	NPC309525
0.6186	Remote Similarity	NPC476009
0.6186	Remote Similarity	NPC17585

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 NPC316984 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	88
0.1-0.2	605
0.2-0.3	3349
0.3-0.4	3686
0.4-0.5	1155
0.5-0.6	242
0.6-0.7	24
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD2204	Approved
0.6822	Remote Similarity	NPD8451	Approved
0.6769	Remote Similarity	NPD8448	Approved
0.6667	Remote Similarity	NPD7642	Approved
0.6641	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD8390	Approved
0.6617	Remote Similarity	NPD8392	Approved
0.6617	Remote Similarity	NPD8391	Approved
0.6615	Remote Similarity	NPD8299	Approved
0.6615	Remote Similarity	NPD8340	Approved
0.6615	Remote Similarity	NPD8342	Approved
0.6615	Remote Similarity	NPD8341	Approved
0.6587	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD8415	Approved
0.6462	Remote Similarity	NPD8080	Discontinued
0.6439	Remote Similarity	NPD8273	Phase 1
0.6393	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD2575	Approved
0.6279	Remote Similarity	NPD7641	Discontinued
0.6159	Remote Similarity	NPD6845	Suspended
0.6154	Remote Similarity	NPD8384	Approved
0.6136	Remote Similarity	NPD8444	Approved
0.6111	Remote Similarity	NPD6421	Discontinued
0.6087	Remote Similarity	NPD3661	Approved
0.6087	Remote Similarity	NPD3663	Approved
0.6087	Remote Similarity	NPD3662	Phase 3
0.6087	Remote Similarity	NPD3664	Approved
0.6043	Remote Similarity	NPD2613	Approved
0.6028	Remote Similarity	NPD3614	Approved
0.6028	Remote Similarity	NPD3089	Approved
0.6028	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD2574	Discontinued
0.6028	Remote Similarity	NPD3087	Approved
0.6028	Remote Similarity	NPD2571	Approved
0.6028	Remote Similarity	NPD3616	Approved
0.6028	Remote Similarity	NPD3090	Approved
0.6028	Remote Similarity	NPD2570	Approved
0.6028	Remote Similarity	NPD2566	Approved
0.6028	Remote Similarity	NPD4745	Approved
0.6028	Remote Similarity	NPD4746	Phase 3
0.6028	Remote Similarity	NPD2573	Approved
0.6028	Remote Similarity	NPD3615	Approved
0.6028	Remote Similarity	NPD3088	Approved
0.5971	Remote Similarity	NPD7260	Phase 2
0.5969	Remote Similarity	NPD1376	Discontinued
0.5948	Remote Similarity	NPD8414	Discontinued
0.5944	Remote Similarity	NPD4686	Approved
0.5944	Remote Similarity	NPD4684	Phase 3
0.5944	Remote Similarity	NPD4685	Phase 3
0.5926	Remote Similarity	NPD7829	Approved
0.5926	Remote Similarity	NPD7830	Approved
0.5917	Remote Similarity	NPD4228	Discovery
0.5896	Remote Similarity	NPD6921	Approved
0.587	Remote Similarity	NPD8337	Approved
0.587	Remote Similarity	NPD8336	Approved
0.5857	Remote Similarity	NPD5204	Approved
0.5847	Remote Similarity	NPD7983	Approved
0.5845	Remote Similarity	NPD4621	Approved
0.5845	Remote Similarity	NPD4619	Approved
0.5798	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD8074	Phase 3
0.5794	Remote Similarity	NPD4211	Phase 1
0.5789	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD1773	Discontinued
0.5785	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD46	Approved
0.5763	Remote Similarity	NPD6698	Approved
0.576	Remote Similarity	NPD8275	Approved
0.576	Remote Similarity	NPD8276	Approved
0.5752	Remote Similarity	NPD883	Phase 2
0.5752	Remote Similarity	NPD882	Phase 2
0.5736	Remote Similarity	NPD6371	Approved
0.5714	Remote Similarity	NPD2628	Approved
0.5714	Remote Similarity	NPD2626	Approved
0.5714	Remote Similarity	NPD2625	Approved
0.5714	Remote Similarity	NPD2627	Approved
0.5714	Remote Similarity	NPD2160	Approved
0.5714	Remote Similarity	NPD2159	Approved
0.5704	Remote Similarity	NPD8338	Approved
0.5702	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD1719	Phase 1
0.5691	Remote Similarity	NPD4225	Approved
0.569	Remote Similarity	NPD4249	Approved
0.5688	Remote Similarity	NPD376	Approved
0.5688	Remote Similarity	NPD11	Approved
0.568	Remote Similarity	NPD8084	Approved
0.568	Remote Similarity	NPD8138	Approved
0.568	Remote Similarity	NPD8083	Approved
0.568	Remote Similarity	NPD8086	Approved
0.568	Remote Similarity	NPD8139	Approved
0.568	Remote Similarity	NPD8082	Approved
0.568	Remote Similarity	NPD8085	Approved
0.5669	Remote Similarity	NPD8393	Approved
0.5659	Remote Similarity	NPD6413	Approved
0.5655	Remote Similarity	NPD6309	Approved
0.5655	Remote Similarity	NPD6310	Approved
0.5655	Remote Similarity	NPD6311	Approved
0.5652	Remote Similarity	NPD2612	Approved
0.5652	Remote Similarity	NPD2609	Approved
0.5652	Remote Similarity	NPD2610	Approved
0.5652	Remote Similarity	NPD4218	Approved
0.5652	Remote Similarity	NPD2608	Approved
0.5652	Remote Similarity	NPD2611	Approved
0.5652	Remote Similarity	NPD4215	Approved
0.5652	Remote Similarity	NPD4217	Approved
0.5652	Remote Similarity	NPD3131	Approved
0.5652	Remote Similarity	NPD3132	Approved
0.5652	Remote Similarity	NPD4216	Approved
0.5641	Remote Similarity	NPD4251	Approved
0.5641	Remote Similarity	NPD4250	Approved
0.563	Remote Similarity	NPD3159	Discontinued
0.563	Remote Similarity	NPD2495	Phase 3
0.5625	Remote Similarity	NPD8140	Approved
0.562	Remote Similarity	NPD5282	Discontinued
0.5615	Remote Similarity	NPD6420	Discontinued
0.5603	Remote Similarity	NPD1733	Clinical (unspecified phase)

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