NPASS Compound

Structure

CID320394 OpenBabel06191716152D 22 23 0 0 1 0 0 0 0 0999 V2000 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 2.5981 0.5000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 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 -1.7321 -1.0000 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 -0.8660 0.5000 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 0.8660 -1.5000 0.0000 C 0 0 3 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 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 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 12 2 0 0 0 0 7 12 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 13 1 0 0 0 0 10 15 2 0 0 0 0 12 17 1 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 14 18 2 0 0 0 0 15 18 1 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	301.13
Volume:	313.178
LogP:	2.353
LogD:	2.252
LogS:	-3.34
# Rotatable Bonds:	6
TPSA:	79.39
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.832
Synthetic Accessibility Score:	3.216
Fsp3:	0.294
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:	-4.766
MDCK Permeability:	1.5925868865451775e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.905
Plasma Protein Binding (PPB):	84.17163848876953%
Volume Distribution (VD):	0.764
Pgp-substrate:	13.482858657836914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.189
CYP2C19-substrate:	0.123
CYP2C9-inhibitor:	0.518
CYP2C9-substrate:	0.976
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.179
CYP3A4-inhibitor:	0.082
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	4.442
Half-life (T1/2):	0.624

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.377
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.195
Maximum Recommended Daily Dose:	0.326
Skin Sensitization:	0.122
Carcinogencity:	0.175
Eye Corrosion:	0.004
Eye Irritation:	0.065
Respiratory Toxicity:	0.789

Download Data

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

Natural Product: NPC320394

Natural Product ID:	NPC320394
*Common Name:**	[(4-Hydroxy-6-Oxo-1H-Pyridin-2-Yl)-Phenylmethyl] 3-Methylbutanoate
IUPAC Name:	[(4-hydroxy-6-oxo-1H-pyridin-2-yl)-phenylmethyl] 3-methylbutanoate
Synonyms:
Standard InCHIKey:	ATDHCZKCFPIQOT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H19NO4/c1-11(2)8-16(21)22-17(12-6-4-3-5-7-12)14-9-13(19)10-15(20)18-14/h3-7,9-11,17H,8H2,1-2H3,(H2,18,19,20)
SMILES:	CC(CC(=O)OC(c1cc(O)cc(n1)O)c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1770955
PubChem CID:	54687215
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0001097] Benzyloxycarbonyls

*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
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10724005]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10724008]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11099218]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332861]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387518]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16568716]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7649881]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8002401]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9711252]

☑ 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
IC50	3
Others	8

Activity Type	# Activity
Cell Line	6
Individual Protein	1
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5013	Individual Protein	Chymase	Homo sapiens	IC50	=	0.25	ug.mL-1	PMID[508189]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	8.22	%	PMID[508189]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	25.54	%	PMID[508189]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	37.22	%	PMID[508189]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	50.21	%	PMID[508189]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	74.02	%	PMID[508189]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	28000.0	nM	PMID[508189]
NPT2	Others	Unspecified		IC50	=	4.9	ug.mL-1	PMID[508189]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IZ	=	9.0	mm	PMID[508189]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	IZ	=	7.0	mm	PMID[508189]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	IZ	=	13.0	mm	PMID[508189]

☑ 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 NPC320394 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	253
0.1-0.2	1338
0.2-0.3	7103
0.3-0.4	10144
0.4-0.5	13308
0.5-0.6	8511
0.6-0.7	1848
0.7-0.8	183
0.8-0.85	7
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9056	High Similarity	NPC317572
0.8343	Intermediate Similarity	NPC283152
0.8268	Intermediate Similarity	NPC42591
0.8171	Intermediate Similarity	NPC471598
0.8098	Intermediate Similarity	NPC245657
0.8095	Intermediate Similarity	NPC153769
0.8037	Intermediate Similarity	NPC280853
0.8022	Intermediate Similarity	NPC194040
0.8011	Intermediate Similarity	NPC62069
0.7988	Intermediate Similarity	NPC285016
0.7978	Intermediate Similarity	NPC66083
0.7978	Intermediate Similarity	NPC194724
0.7978	Intermediate Similarity	NPC288943
0.7975	Intermediate Similarity	NPC471596
0.7866	Intermediate Similarity	NPC471594
0.7857	Intermediate Similarity	NPC161292
0.7766	Intermediate Similarity	NPC279401
0.7766	Intermediate Similarity	NPC230403
0.7766	Intermediate Similarity	NPC79293
0.7754	Intermediate Similarity	NPC469390
0.7749	Intermediate Similarity	NPC280714
0.7732	Intermediate Similarity	NPC137929
0.7732	Intermediate Similarity	NPC164374
0.772	Intermediate Similarity	NPC66815
0.7713	Intermediate Similarity	NPC141915
0.7713	Intermediate Similarity	NPC114335
0.7713	Intermediate Similarity	NPC280964
0.7701	Intermediate Similarity	NPC116573
0.763	Intermediate Similarity	NPC26872
0.7624	Intermediate Similarity	NPC314270
0.7574	Intermediate Similarity	NPC470404
0.7574	Intermediate Similarity	NPC470394
0.7574	Intermediate Similarity	NPC470403
0.7572	Intermediate Similarity	NPC284348
0.754	Intermediate Similarity	NPC61350
0.7528	Intermediate Similarity	NPC473057
0.7527	Intermediate Similarity	NPC303225
0.7515	Intermediate Similarity	NPC60553
0.7513	Intermediate Similarity	NPC472286
0.7513	Intermediate Similarity	NPC472287
0.7513	Intermediate Similarity	NPC144381
0.75	Intermediate Similarity	NPC26850
0.75	Intermediate Similarity	NPC257142
0.7485	Intermediate Similarity	NPC470395
0.7472	Intermediate Similarity	NPC177404
0.746	Intermediate Similarity	NPC183805
0.7459	Intermediate Similarity	NPC478032
0.743	Intermediate Similarity	NPC118511
0.7424	Intermediate Similarity	NPC304183
0.7415	Intermediate Similarity	NPC315804
0.7415	Intermediate Similarity	NPC313804
0.7403	Intermediate Similarity	NPC44161
0.7396	Intermediate Similarity	NPC289786
0.7377	Intermediate Similarity	NPC191310
0.7376	Intermediate Similarity	NPC203168
0.7374	Intermediate Similarity	NPC315214
0.7374	Intermediate Similarity	NPC47298
0.7363	Intermediate Similarity	NPC219664
0.7363	Intermediate Similarity	NPC126481
0.736	Intermediate Similarity	NPC84508
0.7351	Intermediate Similarity	NPC211997
0.7348	Intermediate Similarity	NPC108469
0.734	Intermediate Similarity	NPC207851
0.7333	Intermediate Similarity	NPC159319
0.7333	Intermediate Similarity	NPC263439
0.7333	Intermediate Similarity	NPC32028
0.7323	Intermediate Similarity	NPC469440
0.732	Intermediate Similarity	NPC473053
0.7312	Intermediate Similarity	NPC472168
0.731	Intermediate Similarity	NPC470586
0.7306	Intermediate Similarity	NPC45850
0.7297	Intermediate Similarity	NPC84347
0.7297	Intermediate Similarity	NPC134586
0.7282	Intermediate Similarity	NPC224928
0.7277	Intermediate Similarity	NPC110741
0.7268	Intermediate Similarity	NPC74969
0.7255	Intermediate Similarity	NPC151781
0.7255	Intermediate Similarity	NPC316181
0.7255	Intermediate Similarity	NPC74562
0.7245	Intermediate Similarity	NPC472284
0.7234	Intermediate Similarity	NPC470474
0.7215	Intermediate Similarity	NPC316224
0.7212	Intermediate Similarity	NPC128115
0.7204	Intermediate Similarity	NPC200888
0.7198	Intermediate Similarity	NPC174576
0.7189	Intermediate Similarity	NPC471294
0.7189	Intermediate Similarity	NPC259545
0.7178	Intermediate Similarity	NPC39679
0.7173	Intermediate Similarity	NPC314573
0.7171	Intermediate Similarity	NPC474594
0.7165	Intermediate Similarity	NPC56170
0.7164	Intermediate Similarity	NPC472111
0.7157	Intermediate Similarity	NPC306376
0.7156	Intermediate Similarity	NPC473449
0.7151	Intermediate Similarity	NPC312872
0.715	Intermediate Similarity	NPC312645
0.7143	Intermediate Similarity	NPC469589
0.7143	Intermediate Similarity	NPC477587
0.7143	Intermediate Similarity	NPC477589
0.7136	Intermediate Similarity	NPC118228
0.7129	Intermediate Similarity	NPC314297
0.7129	Intermediate Similarity	NPC469439
0.7129	Intermediate Similarity	NPC474595
0.7129	Intermediate Similarity	NPC315545
0.7129	Intermediate Similarity	NPC316403
0.7127	Intermediate Similarity	NPC322644
0.7122	Intermediate Similarity	NPC472098
0.7121	Intermediate Similarity	NPC128823
0.712	Intermediate Similarity	NPC470894
0.7111	Intermediate Similarity	NPC132680
0.7111	Intermediate Similarity	NPC269919
0.7109	Intermediate Similarity	NPC205372
0.7108	Intermediate Similarity	NPC269367
0.7107	Intermediate Similarity	NPC243834
0.7107	Intermediate Similarity	NPC70956
0.7104	Intermediate Similarity	NPC471178
0.7101	Intermediate Similarity	NPC3207
0.7101	Intermediate Similarity	NPC330009
0.7092	Intermediate Similarity	NPC276517
0.7089	Intermediate Similarity	NPC244536
0.7083	Intermediate Similarity	NPC204385
0.7079	Intermediate Similarity	NPC313796
0.7079	Intermediate Similarity	NPC313345
0.7079	Intermediate Similarity	NPC314855
0.7079	Intermediate Similarity	NPC315638
0.7079	Intermediate Similarity	NPC475841
0.7079	Intermediate Similarity	NPC474145
0.7078	Intermediate Similarity	NPC477586
0.7078	Intermediate Similarity	NPC477588
0.7078	Intermediate Similarity	NPC477585
0.7078	Intermediate Similarity	NPC477590
0.7075	Intermediate Similarity	NPC97746
0.707	Intermediate Similarity	NPC474701
0.7065	Intermediate Similarity	NPC476098
0.7053	Intermediate Similarity	NPC118776
0.7048	Intermediate Similarity	NPC54066
0.7047	Intermediate Similarity	NPC206186
0.7044	Intermediate Similarity	NPC53344
0.7044	Intermediate Similarity	NPC321428
0.7043	Intermediate Similarity	NPC158129
0.7042	Intermediate Similarity	NPC24370
0.7042	Intermediate Similarity	NPC319232
0.7041	Intermediate Similarity	NPC475190
0.7037	Intermediate Similarity	NPC232340
0.7035	Intermediate Similarity	NPC18487
0.7035	Intermediate Similarity	NPC123395
0.7033	Intermediate Similarity	NPC184408
0.7031	Intermediate Similarity	NPC241025
0.703	Intermediate Similarity	NPC47059
0.703	Intermediate Similarity	NPC118832
0.703	Intermediate Similarity	NPC165349
0.703	Intermediate Similarity	NPC264166
0.703	Intermediate Similarity	NPC329708
0.703	Intermediate Similarity	NPC274291
0.703	Intermediate Similarity	NPC314648
0.7028	Intermediate Similarity	NPC51388
0.7024	Intermediate Similarity	NPC314834
0.7023	Intermediate Similarity	NPC322135
0.7023	Intermediate Similarity	NPC95240
0.7019	Intermediate Similarity	NPC152768
0.7019	Intermediate Similarity	NPC148183
0.7019	Intermediate Similarity	NPC469928
0.701	Intermediate Similarity	NPC470931
0.7009	Intermediate Similarity	NPC304307
0.7009	Intermediate Similarity	NPC118559
0.7009	Intermediate Similarity	NPC186351
0.7009	Intermediate Similarity	NPC34580
0.7009	Intermediate Similarity	NPC124920
0.7005	Intermediate Similarity	NPC471080
0.7005	Intermediate Similarity	NPC89508
0.7005	Intermediate Similarity	NPC469592
0.7	Intermediate Similarity	NPC168486
0.7	Intermediate Similarity	NPC63562
0.7	Intermediate Similarity	NPC222592
0.6995	Remote Similarity	NPC476106
0.6995	Remote Similarity	NPC471177
0.6995	Remote Similarity	NPC59779
0.6995	Remote Similarity	NPC124542
0.699	Remote Similarity	NPC220337
0.699	Remote Similarity	NPC87413
0.6989	Remote Similarity	NPC473764
0.6989	Remote Similarity	NPC314940
0.6986	Remote Similarity	NPC476995
0.6982	Remote Similarity	NPC291609
0.6977	Remote Similarity	NPC100547
0.6974	Remote Similarity	NPC3715
0.6971	Remote Similarity	NPC16066
0.6967	Remote Similarity	NPC174760
0.6965	Remote Similarity	NPC155792
0.6963	Remote Similarity	NPC219963
0.6961	Remote Similarity	NPC193238
0.6959	Remote Similarity	NPC321592
0.6959	Remote Similarity	NPC54803
0.6957	Remote Similarity	NPC264176
0.6954	Remote Similarity	NPC192306
0.6952	Remote Similarity	NPC473822
0.6952	Remote Similarity	NPC469594
0.6952	Remote Similarity	NPC131885
0.6947	Remote Similarity	NPC72980
0.6944	Remote Similarity	NPC223409

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 NPC320394 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	553
0.2-0.3	778
0.3-0.4	1195
0.4-0.5	2571
0.5-0.6	3038
0.6-0.7	768
0.7-0.8	66
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
0.8011	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7968	Intermediate Similarity	NPD5512	Phase 3
0.7955	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6642	Approved
0.7933	Intermediate Similarity	NPD6641	Approved
0.7872	Intermediate Similarity	NPD6550	Discontinued
0.7653	Intermediate Similarity	NPD5429	Discontinued
0.7641	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5256	Discontinued
0.76	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD3525	Discontinued
0.7562	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD5003	Discontinued
0.7552	Intermediate Similarity	NPD1229	Phase 2
0.7552	Intermediate Similarity	NPD6988	Phase 1
0.7539	Intermediate Similarity	NPD6590	Discontinued
0.7538	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4204	Approved
0.7514	Intermediate Similarity	NPD4203	Approved
0.75	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD4889	Approved
0.7463	Intermediate Similarity	NPD7069	Discontinued
0.7446	Intermediate Similarity	NPD6159	Phase 2
0.7436	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2564	Approved
0.7421	Intermediate Similarity	NPD2565	Phase 2
0.7413	Intermediate Similarity	NPD5416	Discontinued
0.7396	Intermediate Similarity	NPD4526	Approved
0.7396	Intermediate Similarity	NPD4529	Approved
0.7396	Intermediate Similarity	NPD4528	Approved
0.7374	Intermediate Similarity	NPD1685	Approved
0.7374	Intermediate Similarity	NPD1684	Approved
0.7351	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6569	Phase 2
0.733	Intermediate Similarity	NPD5316	Approved
0.733	Intermediate Similarity	NPD8063	Discontinued
0.7322	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3925	Approved
0.7316	Intermediate Similarity	NPD2383	Phase 1
0.7312	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2581	Approved
0.7303	Intermediate Similarity	NPD2582	Approved
0.7282	Intermediate Similarity	NPD7395	Discontinued
0.7245	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD4897	Phase 2
0.7219	Intermediate Similarity	NPD3920	Phase 2
0.7214	Intermediate Similarity	NPD7222	Phase 2
0.7213	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2177	Approved
0.7208	Intermediate Similarity	NPD2175	Phase 3
0.7208	Intermediate Similarity	NPD2176	Approved
0.7184	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6298	Discontinued
0.7171	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4502	Phase 2
0.715	Intermediate Similarity	NPD7284	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD1213	Phase 3
0.7143	Intermediate Similarity	NPD3477	Phase 2
0.7143	Intermediate Similarity	NPD8356	Approved
0.7143	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD862	Approved
0.7143	Intermediate Similarity	NPD861	Approved
0.7143	Intermediate Similarity	NPD863	Approved
0.7136	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD9383	Approved
0.7111	Intermediate Similarity	NPD9382	Approved
0.7108	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD3395	Approved
0.7092	Intermediate Similarity	NPD3396	Approved
0.7092	Intermediate Similarity	NPD4418	Discontinued
0.7089	Intermediate Similarity	NPD4086	Phase 1
0.7081	Intermediate Similarity	NPD3875	Discontinued
0.7045	Intermediate Similarity	NPD7417	Discontinued
0.7044	Intermediate Similarity	NPD7452	Approved
0.7044	Intermediate Similarity	NPD6290	Phase 2
0.7044	Intermediate Similarity	NPD7453	Approved
0.7041	Intermediate Similarity	NPD6361	Phase 2
0.7039	Intermediate Similarity	NPD5866	Approved
0.703	Intermediate Similarity	NPD4033	Approved
0.703	Intermediate Similarity	NPD32	Approved
0.703	Intermediate Similarity	NPD4038	Approved
0.703	Intermediate Similarity	NPD4122	Approved
0.703	Intermediate Similarity	NPD4039	Approved
0.703	Intermediate Similarity	NPD4034	Approved
0.703	Intermediate Similarity	NPD4036	Approved
0.703	Intermediate Similarity	NPD4035	Approved
0.703	Intermediate Similarity	NPD4037	Approved
0.703	Intermediate Similarity	NPD31	Approved
0.7024	Intermediate Similarity	NPD5420	Discontinued
0.7014	Intermediate Similarity	NPD5507	Approved
0.7014	Intermediate Similarity	NPD5506	Approved
0.7009	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8430	Approved
0.7005	Intermediate Similarity	NPD6182	Approved
0.7005	Intermediate Similarity	NPD43	Approved
0.7005	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD2077	Approved
0.7005	Intermediate Similarity	NPD2076	Approved
0.7	Intermediate Similarity	NPD6974	Phase 3
0.7	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2920	Discontinued
0.6974	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD3386	Phase 2
0.6963	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5632	Approved
0.6943	Remote Similarity	NPD6227	Discontinued
0.6935	Remote Similarity	NPD2781	Approved
0.6931	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5596	Phase 2
0.6927	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4334	Discontinued
0.6919	Remote Similarity	NPD2780	Approved
0.6919	Remote Similarity	NPD926	Approved
0.6919	Remote Similarity	NPD925	Approved
0.6919	Remote Similarity	NPD2782	Approved
0.6912	Remote Similarity	NPD3003	Approved
0.6905	Remote Similarity	NPD5164	Discontinued
0.6905	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD3924	Approved
0.6904	Remote Similarity	NPD3923	Approved
0.6904	Remote Similarity	NPD3922	Approved
0.6904	Remote Similarity	NPD4372	Phase 1
0.6904	Remote Similarity	NPD3921	Approved
0.6904	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.69	Remote Similarity	NPD53	Approved
0.69	Remote Similarity	NPD7777	Approved
0.69	Remote Similarity	NPD7778	Approved
0.6898	Remote Similarity	NPD7474	Suspended
0.6897	Remote Similarity	NPD6991	Approved
0.6888	Remote Similarity	NPD3321	Discontinued
0.6885	Remote Similarity	NPD5255	Approved
0.6885	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5640	Discontinued
0.6875	Remote Similarity	NPD3037	Phase 1
0.6872	Remote Similarity	NPD1034	Phase 3
0.6872	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1768	Approved
0.6859	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.685	Remote Similarity	NPD2952	Discontinued
0.6848	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD2779	Approved
0.6845	Remote Similarity	NPD2916	Discontinued
0.6835	Remote Similarity	NPD6962	Phase 2
0.6834	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD4427	Phase 2
0.6829	Remote Similarity	NPD3842	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5936	Approved
0.6827	Remote Similarity	NPD5939	Approved
0.6825	Remote Similarity	NPD7418	Discontinued
0.6823	Remote Similarity	NPD6452	Discontinued
0.6822	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4375	Approved
0.682	Remote Similarity	NPD5014	Discontinued
0.6818	Remote Similarity	NPD4950	Approved
0.6816	Remote Similarity	NPD2727	Phase 2
0.6813	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6529	Discontinued
0.681	Remote Similarity	NPD5903	Approved
0.681	Remote Similarity	NPD5902	Approved
0.6808	Remote Similarity	NPD7180	Phase 3
0.6806	Remote Similarity	NPD7426	Phase 1
0.6806	Remote Similarity	NPD3263	Phase 3
0.6804	Remote Similarity	NPD7031	Phase 1
0.6796	Remote Similarity	NPD6158	Phase 2
0.6796	Remote Similarity	NPD2882	Phase 1
0.6796	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD9690	Approved
0.6786	Remote Similarity	NPD6716	Phase 1
0.6786	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD4551	Phase 2
0.6774	Remote Similarity	NPD3259	Approved
0.6774	Remote Similarity	NPD5088	Discontinued
0.6774	Remote Similarity	NPD6326	Phase 2
0.6772	Remote Similarity	NPD2123	Phase 3
0.6771	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1622	Discontinued
0.6763	Remote Similarity	NPD7672	Approved
0.6763	Remote Similarity	NPD7671	Approved
0.6762	Remote Similarity	NPD3243	Approved
0.6761	Remote Similarity	NPD3258	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