NPASS Compound

Structure

NPC472788 OpenBabel07101719512D 21 22 0 0 0 0 0 0 0 0999 V2000 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 3.4641 -2.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 11 2 0 0 0 0 7 11 1 0 0 0 0 8 9 2 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 13 17 2 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 16 20 2 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	283.12
Volume:	301.751
LogP:	4.184
LogD:	2.844
LogS:	-4.167
# Rotatable Bonds:	3
TPSA:	86.71
# H-Bond Aceptor:	4
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.3
Synthetic Accessibility Score:	2.863
Fsp3:	0.059
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.931
MDCK Permeability:	2.0125744413235225e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.107
30% Bioavailability (F30%):	0.164

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	100.15498352050781%
Volume Distribution (VD):	0.4
Pgp-substrate:	0.7830247282981873%

ADMET: Metabolism

CYP1A2-inhibitor:	0.893
CYP1A2-substrate:	0.324
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.144
CYP2C9-inhibitor:	0.549
CYP2C9-substrate:	0.617
CYP2D6-inhibitor:	0.361
CYP2D6-substrate:	0.693
CYP3A4-inhibitor:	0.115
CYP3A4-substrate:	0.125

ADMET: Excretion

Clearance (CL):	7.409
Half-life (T1/2):	0.527

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.215
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.46
Rat Oral Acute Toxicity:	0.527
Maximum Recommended Daily Dose:	0.719
Skin Sensitization:	0.953
Carcinogencity:	0.625
Eye Corrosion:	0.003
Eye Irritation:	0.788
Respiratory Toxicity:	0.399

Download Data

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

Natural Product: NPC472788

Natural Product ID:	NPC472788
*Common Name:**	UIFOBERPRVNZPL-CMDGGOBGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UIFOBERPRVNZPL-CMDGGOBGSA-N
Standard InCHI:	InChI=1S/C17H17NO3/c1-10(2)13-16(20)14(18)12(15(19)17(13)21)9-8-11-6-4-3-5-7-11/h3-10,21H,18H2,1-2H3/b9-8+
SMILES:	NC1=C(/C=C/c2ccccc2)C(=O)C(=C(C1=O)C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3582233
PubChem CID:	n.a.
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
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22909174]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25988621]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	10.0	mm	PMID[517592]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IZ	=	6.0	mm	PMID[517592]

☑ 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 NPC472788 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	96
0.1-0.2	1201
0.2-0.3	5259
0.3-0.4	16096
0.4-0.5	16314
0.5-0.6	3314
0.6-0.7	402
0.7-0.8	14
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.75	Intermediate Similarity	NPC472164
0.7479	Intermediate Similarity	NPC119326
0.7374	Intermediate Similarity	NPC477704
0.7374	Intermediate Similarity	NPC477693
0.7353	Intermediate Similarity	NPC34243
0.7282	Intermediate Similarity	NPC473347
0.7273	Intermediate Similarity	NPC194326
0.7228	Intermediate Similarity	NPC67585
0.7228	Intermediate Similarity	NPC303967
0.7228	Intermediate Similarity	NPC110420
0.7143	Intermediate Similarity	NPC240042
0.7128	Intermediate Similarity	NPC179726
0.7075	Intermediate Similarity	NPC145052
0.7071	Intermediate Similarity	NPC123476
0.7059	Intermediate Similarity	NPC108026
0.7033	Intermediate Similarity	NPC95289
0.7019	Intermediate Similarity	NPC246757
0.7019	Intermediate Similarity	NPC291070
0.7009	Intermediate Similarity	NPC474308
0.699	Remote Similarity	NPC476484
0.6981	Remote Similarity	NPC103048
0.6972	Remote Similarity	NPC202613
0.693	Remote Similarity	NPC275410
0.6923	Remote Similarity	NPC98880
0.6916	Remote Similarity	NPC179411
0.6916	Remote Similarity	NPC476120
0.6887	Remote Similarity	NPC12695
0.6881	Remote Similarity	NPC222390
0.6881	Remote Similarity	NPC244427
0.6852	Remote Similarity	NPC54647
0.6829	Remote Similarity	NPC477249
0.6829	Remote Similarity	NPC477248
0.6829	Remote Similarity	NPC472165
0.6822	Remote Similarity	NPC293628
0.6822	Remote Similarity	NPC122493
0.6822	Remote Similarity	NPC10781
0.6822	Remote Similarity	NPC324569
0.6822	Remote Similarity	NPC156021
0.6822	Remote Similarity	NPC278228
0.6818	Remote Similarity	NPC274443
0.6813	Remote Similarity	NPC311343
0.6804	Remote Similarity	NPC151405
0.6804	Remote Similarity	NPC139901
0.6786	Remote Similarity	NPC327481
0.6786	Remote Similarity	NPC100767
0.6783	Remote Similarity	NPC292834
0.6774	Remote Similarity	NPC155429
0.6735	Remote Similarity	NPC285716
0.6735	Remote Similarity	NPC17408
0.6733	Remote Similarity	NPC95965
0.6696	Remote Similarity	NPC172483
0.6695	Remote Similarity	NPC235421
0.6667	Remote Similarity	NPC247976
0.6667	Remote Similarity	NPC289201
0.6667	Remote Similarity	NPC110704
0.6667	Remote Similarity	NPC471317
0.6639	Remote Similarity	NPC473050
0.6639	Remote Similarity	NPC473051
0.6634	Remote Similarity	NPC44546
0.6633	Remote Similarity	NPC272260
0.6633	Remote Similarity	NPC469894
0.6633	Remote Similarity	NPC300205
0.6607	Remote Similarity	NPC329282
0.6606	Remote Similarity	NPC135951
0.6606	Remote Similarity	NPC154517
0.6606	Remote Similarity	NPC317280
0.6606	Remote Similarity	NPC329387
0.6604	Remote Similarity	NPC1682
0.6604	Remote Similarity	NPC153885
0.6604	Remote Similarity	NPC188844
0.6602	Remote Similarity	NPC69057
0.6598	Remote Similarity	NPC9796
0.6596	Remote Similarity	NPC74458
0.6581	Remote Similarity	NPC143768
0.6581	Remote Similarity	NPC474584
0.6579	Remote Similarity	NPC172170
0.6569	Remote Similarity	NPC53299
0.6569	Remote Similarity	NPC2672
0.6566	Remote Similarity	NPC192623
0.6566	Remote Similarity	NPC477703
0.6566	Remote Similarity	NPC190567
0.6566	Remote Similarity	NPC164086
0.6552	Remote Similarity	NPC319579
0.6549	Remote Similarity	NPC67043
0.6549	Remote Similarity	NPC167336
0.6549	Remote Similarity	NPC134120
0.6545	Remote Similarity	NPC80115
0.6545	Remote Similarity	NPC12730
0.6542	Remote Similarity	NPC238219
0.6535	Remote Similarity	NPC477770
0.6535	Remote Similarity	NPC44830
0.6531	Remote Similarity	NPC2785
0.6531	Remote Similarity	NPC36342
0.6531	Remote Similarity	NPC285470
0.6531	Remote Similarity	NPC103488
0.6526	Remote Similarity	NPC285679
0.6522	Remote Similarity	NPC182549
0.6522	Remote Similarity	NPC114741
0.6522	Remote Similarity	NPC475282
0.6518	Remote Similarity	NPC329556
0.6518	Remote Similarity	NPC68269
0.6518	Remote Similarity	NPC164859
0.6509	Remote Similarity	NPC133461
0.6509	Remote Similarity	NPC141607
0.6509	Remote Similarity	NPC187725
0.6509	Remote Similarity	NPC284475
0.6496	Remote Similarity	NPC477250
0.6491	Remote Similarity	NPC191215
0.6491	Remote Similarity	NPC274089
0.6489	Remote Similarity	NPC470441
0.6486	Remote Similarity	NPC112552
0.6481	Remote Similarity	NPC161972
0.6481	Remote Similarity	NPC303045
0.6481	Remote Similarity	NPC260233
0.6481	Remote Similarity	NPC5472
0.6481	Remote Similarity	NPC58674
0.6471	Remote Similarity	NPC93181
0.6471	Remote Similarity	NPC267704
0.646	Remote Similarity	NPC275467
0.6455	Remote Similarity	NPC201967
0.6449	Remote Similarity	NPC155232
0.6446	Remote Similarity	NPC471553
0.6442	Remote Similarity	NPC43945
0.6442	Remote Similarity	NPC322387
0.6429	Remote Similarity	NPC472585
0.6429	Remote Similarity	NPC474479
0.6429	Remote Similarity	NPC329318
0.6429	Remote Similarity	NPC245966
0.6422	Remote Similarity	NPC25565
0.6422	Remote Similarity	NPC469893
0.6421	Remote Similarity	NPC326200
0.6415	Remote Similarity	NPC86670
0.6415	Remote Similarity	NPC70940
0.6415	Remote Similarity	NPC274455
0.6415	Remote Similarity	NPC172128
0.641	Remote Similarity	NPC323007
0.641	Remote Similarity	NPC21162
0.641	Remote Similarity	NPC222905
0.641	Remote Similarity	NPC477247
0.6404	Remote Similarity	NPC474307
0.64	Remote Similarity	NPC71664
0.64	Remote Similarity	NPC127343
0.64	Remote Similarity	NPC472415
0.64	Remote Similarity	NPC95868
0.6396	Remote Similarity	NPC130193
0.6396	Remote Similarity	NPC476042
0.6393	Remote Similarity	NPC314992
0.6393	Remote Similarity	NPC318173
0.6392	Remote Similarity	NPC206800
0.6392	Remote Similarity	NPC189371
0.6392	Remote Similarity	NPC32203
0.6389	Remote Similarity	NPC181709
0.6381	Remote Similarity	NPC157778
0.6381	Remote Similarity	NPC12429
0.6379	Remote Similarity	NPC469511
0.6373	Remote Similarity	NPC215008
0.6373	Remote Similarity	NPC273758
0.6373	Remote Similarity	NPC270507
0.6373	Remote Similarity	NPC285773
0.6364	Remote Similarity	NPC473501
0.6364	Remote Similarity	NPC469843
0.6364	Remote Similarity	NPC50192
0.6364	Remote Similarity	NPC469892
0.6364	Remote Similarity	NPC76455
0.6364	Remote Similarity	NPC251579
0.6364	Remote Similarity	NPC475439
0.6364	Remote Similarity	NPC133135
0.6364	Remote Similarity	NPC239185
0.6364	Remote Similarity	NPC477767
0.6364	Remote Similarity	NPC2265
0.6364	Remote Similarity	NPC325646
0.6364	Remote Similarity	NPC239357
0.6364	Remote Similarity	NPC28951
0.6364	Remote Similarity	NPC469891
0.6364	Remote Similarity	NPC469890
0.6364	Remote Similarity	NPC108532
0.6364	Remote Similarity	NPC137847
0.6356	Remote Similarity	NPC218855
0.6356	Remote Similarity	NPC186128
0.6355	Remote Similarity	NPC317645
0.6348	Remote Similarity	NPC51174
0.6348	Remote Similarity	NPC29989
0.6348	Remote Similarity	NPC95178
0.6348	Remote Similarity	NPC473498
0.6348	Remote Similarity	NPC477251
0.6348	Remote Similarity	NPC69332
0.6348	Remote Similarity	NPC70843
0.6339	Remote Similarity	NPC158623
0.6337	Remote Similarity	NPC12936
0.6337	Remote Similarity	NPC145053
0.6337	Remote Similarity	NPC273033
0.633	Remote Similarity	NPC206764
0.6321	Remote Similarity	NPC231591
0.6321	Remote Similarity	NPC470877
0.6316	Remote Similarity	NPC249067
0.6311	Remote Similarity	NPC80605
0.6311	Remote Similarity	NPC222968
0.6311	Remote Similarity	NPC323440
0.6306	Remote Similarity	NPC322598
0.6306	Remote Similarity	NPC290515

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 NPC472788 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	97
0.1-0.2	625
0.2-0.3	1025
0.3-0.4	3180
0.4-0.5	2853
0.5-0.6	1253
0.6-0.7	114
0.7-0.8	3
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
0.7184	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3420	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD2066	Phase 3
0.6822	Remote Similarity	NPD9566	Approved
0.6698	Remote Similarity	NPD3718	Approved
0.6698	Remote Similarity	NPD3719	Approved
0.6667	Remote Similarity	NPD1099	Approved
0.6667	Remote Similarity	NPD1100	Approved
0.6613	Remote Similarity	NPD2371	Approved
0.661	Remote Similarity	NPD2319	Discontinued
0.6606	Remote Similarity	NPD253	Approved
0.6604	Remote Similarity	NPD7631	Approved
0.6577	Remote Similarity	NPD2193	Phase 2
0.6577	Remote Similarity	NPD2171	Approved
0.6577	Remote Similarity	NPD2648	Phase 3
0.6552	Remote Similarity	NPD3642	Approved
0.6552	Remote Similarity	NPD3643	Approved
0.6552	Remote Similarity	NPD3644	Approved
0.6542	Remote Similarity	NPD1066	Discontinued
0.6535	Remote Similarity	NPD3971	Phase 1
0.6518	Remote Similarity	NPD1930	Approved
0.6518	Remote Similarity	NPD1929	Approved
0.6518	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4657	Approved
0.6514	Remote Similarity	NPD4655	Approved
0.6509	Remote Similarity	NPD7609	Phase 3
0.6481	Remote Similarity	NPD1693	Approved
0.6481	Remote Similarity	NPD4094	Approved
0.6476	Remote Similarity	NPD5346	Phase 2
0.6476	Remote Similarity	NPD800	Approved
0.6476	Remote Similarity	NPD5347	Phase 2
0.6449	Remote Similarity	NPD1814	Approved
0.6449	Remote Similarity	NPD1812	Approved
0.6442	Remote Similarity	NPD650	Approved
0.6429	Remote Similarity	NPD1574	Approved
0.6429	Remote Similarity	NPD2196	Discontinued
0.6423	Remote Similarity	NPD4733	Approved
0.6421	Remote Similarity	NPD292	Approved
0.6421	Remote Similarity	NPD294	Approved
0.6417	Remote Similarity	NPD256	Approved
0.6417	Remote Similarity	NPD255	Approved
0.6415	Remote Similarity	NPD1090	Approved
0.6415	Remote Similarity	NPD1089	Approved
0.6415	Remote Similarity	NPD1086	Approved
0.6404	Remote Similarity	NPD2197	Approved
0.6404	Remote Similarity	NPD2192	Approved
0.6404	Remote Similarity	NPD1040	Phase 2
0.6404	Remote Similarity	NPD999	Phase 2
0.64	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD2217	Approved
0.6393	Remote Similarity	NPD2218	Phase 2
0.6392	Remote Similarity	NPD9716	Approved
0.6381	Remote Similarity	NPD1101	Approved
0.6379	Remote Similarity	NPD476	Approved
0.6378	Remote Similarity	NPD1593	Approved
0.6373	Remote Similarity	NPD9491	Approved
0.6372	Remote Similarity	NPD3357	Discontinued
0.6372	Remote Similarity	NPD6647	Phase 2
0.6364	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3495	Discontinued
0.6355	Remote Similarity	NPD530	Approved
0.6337	Remote Similarity	NPD942	Approved
0.6337	Remote Similarity	NPD226	Approved
0.6325	Remote Similarity	NPD664	Approved
0.6316	Remote Similarity	NPD1237	Approved
0.6316	Remote Similarity	NPD5909	Discontinued
0.6316	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD9612	Approved
0.6306	Remote Similarity	NPD9611	Approved
0.6306	Remote Similarity	NPD9609	Approved
0.6306	Remote Similarity	NPD5926	Approved
0.6296	Remote Similarity	NPD1088	Approved
0.6296	Remote Similarity	NPD6690	Approved
0.6289	Remote Similarity	NPD9589	Approved
0.6289	Remote Similarity	NPD9592	Approved
0.6289	Remote Similarity	NPD80	Approved
0.6289	Remote Similarity	NPD9593	Approved
0.6289	Remote Similarity	NPD9590	Approved
0.6289	Remote Similarity	NPD9594	Approved
0.6289	Remote Similarity	NPD9591	Approved
0.6289	Remote Similarity	NPD9588	Approved
0.6286	Remote Similarity	NPD4793	Discontinued
0.6286	Remote Similarity	NPD1282	Approved
0.6286	Remote Similarity	NPD9538	Approved
0.6283	Remote Similarity	NPD4817	Approved
0.6283	Remote Similarity	NPD6027	Approved
0.6283	Remote Similarity	NPD4719	Phase 2
0.6283	Remote Similarity	NPD6024	Approved
0.6283	Remote Similarity	NPD4119	Approved
0.6283	Remote Similarity	NPD4818	Approved
0.6273	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD2583	Phase 2
0.6261	Remote Similarity	NPD5717	Approved
0.625	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.624	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.623	Remote Similarity	NPD9568	Approved
0.6222	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5157	Phase 1
0.622	Remote Similarity	NPD5159	Phase 2
0.622	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD9508	Approved
0.6214	Remote Similarity	NPD2001	Discontinued
0.6195	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4063	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD3035	Approved
0.6174	Remote Similarity	NPD9610	Approved
0.6174	Remote Similarity	NPD9608	Approved
0.6172	Remote Similarity	NPD2056	Discontinued
0.6167	Remote Similarity	NPD181	Approved
0.616	Remote Similarity	NPD1727	Approved
0.6148	Remote Similarity	NPD1348	Approved
0.6143	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6637	Approved
0.6142	Remote Similarity	NPD1077	Clinical (unspecified phase)
0.614	Remote Similarity	NPD1932	Approved
0.6139	Remote Similarity	NPD590	Approved
0.6139	Remote Similarity	NPD589	Approved
0.6134	Remote Similarity	NPD5927	Discontinued
0.6132	Remote Similarity	NPD4145	Approved
0.6132	Remote Similarity	NPD4146	Approved
0.6132	Remote Similarity	NPD1087	Approved
0.6129	Remote Similarity	NPD4479	Discontinued
0.6129	Remote Similarity	NPD6093	Discontinued
0.6129	Remote Similarity	NPD922	Approved
0.6126	Remote Similarity	NPD2895	Discontinued
0.6121	Remote Similarity	NPD1677	Discontinued
0.6121	Remote Similarity	NPD1018	Approved
0.6117	Remote Similarity	NPD4169	Approved
0.6117	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4170	Approved
0.6116	Remote Similarity	NPD1370	Approved
0.6116	Remote Similarity	NPD1373	Approved
0.6116	Remote Similarity	NPD1374	Approved
0.6116	Remote Similarity	NPD1371	Approved
0.6111	Remote Similarity	NPD4879	Approved
0.6111	Remote Similarity	NPD1517	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD2329	Discontinued
0.6102	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4147	Approved
0.61	Remote Similarity	NPD4144	Approved
0.6098	Remote Similarity	NPD5162	Approved
0.6094	Remote Similarity	NPD4677	Discontinued
0.6091	Remote Similarity	NPD1409	Phase 3
0.6091	Remote Similarity	NPD719	Approved
0.6091	Remote Similarity	NPD720	Approved
0.6091	Remote Similarity	NPD1080	Approved
0.6087	Remote Similarity	NPD4231	Approved
0.6087	Remote Similarity	NPD3680	Approved
0.6087	Remote Similarity	NPD3683	Approved
0.6087	Remote Similarity	NPD3682	Approved
0.6087	Remote Similarity	NPD3681	Approved
0.6087	Remote Similarity	NPD4229	Approved
0.608	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD1560	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD531	Approved
0.6071	Remote Similarity	NPD1565	Approved
0.6071	Remote Similarity	NPD1566	Phase 3
0.6071	Remote Similarity	NPD1564	Approved
0.6071	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD5705	Approved
0.6068	Remote Similarity	NPD5704	Approved
0.6068	Remote Similarity	NPD5706	Approved
0.6068	Remote Similarity	NPD7130	Phase 3
0.6066	Remote Similarity	NPD1075	Approved
0.6066	Remote Similarity	NPD1074	Approved
0.6066	Remote Similarity	NPD1073	Approved
0.6066	Remote Similarity	NPD747	Discontinued
0.6063	Remote Similarity	NPD3132	Approved
0.6063	Remote Similarity	NPD2612	Approved
0.6063	Remote Similarity	NPD2609	Approved
0.6063	Remote Similarity	NPD2611	Approved
0.6063	Remote Similarity	NPD2608	Approved
0.6063	Remote Similarity	NPD4216	Approved
0.6063	Remote Similarity	NPD4217	Approved
0.6063	Remote Similarity	NPD3131	Approved
0.6063	Remote Similarity	NPD4218	Approved
0.6063	Remote Similarity	NPD2610	Approved
0.6063	Remote Similarity	NPD4215	Approved
0.6061	Remote Similarity	NPD3136	Phase 2
0.6061	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD1239	Approved
0.6053	Remote Similarity	NPD5630	Phase 1
0.605	Remote Similarity	NPD5237	Approved
0.605	Remote Similarity	NPD5236	Approved
0.605	Remote Similarity	NPD5239	Approved
0.605	Remote Similarity	NPD5240	Approved
0.605	Remote Similarity	NPD5235	Approved
0.6043	Remote Similarity	NPD7082	Approved
0.604	Remote Similarity	NPD79	Approved
0.604	Remote Similarity	NPD227	Approved
0.604	Remote Similarity	NPD9563	Approved
0.604	Remote Similarity	NPD225	Approved
0.604	Remote Similarity	NPD293	Approved
0.604	Remote Similarity	NPD9564	Approved
0.604	Remote Similarity	NPD295	Approved
0.604	Remote Similarity	NPD296	Approved
0.6036	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD3772	Phase 3
0.6036	Remote Similarity	NPD6049	Phase 2

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