NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	137.02
Volume:	135.579
LogP:	-0.606
LogD:	-1.425
LogS:	0.438
# Rotatable Bonds:	1
TPSA:	60.36
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.58
Synthetic Accessibility Score:	2.455
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.517
MDCK Permeability:	2.702739402593579e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.513
Plasma Protein Binding (PPB):	66.2210922241211%
Volume Distribution (VD):	0.294
Pgp-substrate:	21.87535858154297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.064
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.535
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.103

ADMET: Excretion

Clearance (CL):	5.5
Half-life (T1/2):	0.881

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.837
Drug-inuced Liver Injury (DILI):	0.191
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.667
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.308
Carcinogencity:	0.268
Eye Corrosion:	0.288
Eye Irritation:	0.992
Respiratory Toxicity:	0.171

Download Data

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

Natural Product: NPC184658

Natural Product ID:	NPC184658
*Common Name:**	Sodium;4-Hydroxybenzoate
IUPAC Name:	sodium;4-hydroxybenzoate
Synonyms:	Sodium 4-Hydroxybenzoate
Standard InCHIKey:	ZLVSYODPTJZFMK-UHFFFAOYSA-M
Standard InCHI:	InChI=1S/C7H6O3.Na/c8-6-3-1-5(2-4-6)7(9)10;/h1-4,8H,(H,9,10);/q;+1/p-1
SMILES:	c1cc(ccc1C(=O)O)[O-].[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1762656
PubChem CID:	16219477
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid 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
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[10423860]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15863936]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20581114]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21848266]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21848266]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25515814]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31211	Eurycoma sp	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	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
Ki	4
Others	2

Activity Type	# Activity
Individual Protein	2
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	=	7280.0	nM	PMID[453483]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	=	7610.0	nM	PMID[453483]
NPT2	Others	Unspecified		Ki	=	9.5	nM	PMID[453483]
NPT2	Others	Unspecified		Ki	=	110.0	nM	PMID[453483]
NPT2	Others	Unspecified		Ratio Ki	=	766.3	n.a.	PMID[453483]
NPT2	Others	Unspecified		Ratio Ki	=	66.2	n.a.	PMID[453483]

☑ 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 NPC184658 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	367
0.1-0.2	2223
0.2-0.3	5018
0.3-0.4	12154
0.4-0.5	6295
0.5-0.6	8847
0.6-0.7	6641
0.7-0.8	1042
0.8-0.85	84
0.85-0.9	23
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9899	High Similarity	NPC29883
0.9074	High Similarity	NPC131192
0.8942	High Similarity	NPC226699
0.8932	High Similarity	NPC219913
0.8909	High Similarity	NPC94298
0.8909	High Similarity	NPC273282
0.8909	High Similarity	NPC27633
0.8909	High Similarity	NPC474890
0.8909	High Similarity	NPC241089
0.8909	High Similarity	NPC161943
0.8846	High Similarity	NPC187913
0.8846	High Similarity	NPC6984
0.8829	High Similarity	NPC156654
0.8829	High Similarity	NPC61779
0.8774	High Similarity	NPC95172
0.8727	High Similarity	NPC83718
0.8725	High Similarity	NPC52472
0.8679	High Similarity	NPC100551
0.8679	High Similarity	NPC17525
0.8667	High Similarity	NPC317592
0.8627	High Similarity	NPC245561
0.8611	High Similarity	NPC212718
0.8611	High Similarity	NPC114682
0.8571	High Similarity	NPC62765
0.8522	High Similarity	NPC291189
0.8522	High Similarity	NPC69403
0.8522	High Similarity	NPC67300
0.8519	High Similarity	NPC116842
0.8468	Intermediate Similarity	NPC220540
0.8455	Intermediate Similarity	NPC11824
0.8455	Intermediate Similarity	NPC242136
0.8455	Intermediate Similarity	NPC98543
0.8455	Intermediate Similarity	NPC223004
0.8448	Intermediate Similarity	NPC174991
0.844	Intermediate Similarity	NPC268388
0.8416	Intermediate Similarity	NPC32977
0.8416	Intermediate Similarity	NPC81010
0.8407	Intermediate Similarity	NPC283844
0.8396	Intermediate Similarity	NPC13495
0.8376	Intermediate Similarity	NPC184219
0.8376	Intermediate Similarity	NPC221798
0.8364	Intermediate Similarity	NPC231717
0.8362	Intermediate Similarity	NPC225710
0.8333	Intermediate Similarity	NPC161617
0.8333	Intermediate Similarity	NPC158222
0.8305	Intermediate Similarity	NPC49938
0.8304	Intermediate Similarity	NPC322197
0.8304	Intermediate Similarity	NPC4665
0.8269	Intermediate Similarity	NPC280869
0.8269	Intermediate Similarity	NPC228435
0.8261	Intermediate Similarity	NPC159525
0.8241	Intermediate Similarity	NPC141523
0.8241	Intermediate Similarity	NPC303264
0.8241	Intermediate Similarity	NPC34715
0.8235	Intermediate Similarity	NPC475236
0.8235	Intermediate Similarity	NPC204579
0.8235	Intermediate Similarity	NPC110211
0.8235	Intermediate Similarity	NPC473751
0.8235	Intermediate Similarity	NPC95309
0.8224	Intermediate Similarity	NPC163734
0.8214	Intermediate Similarity	NPC81808
0.8208	Intermediate Similarity	NPC13426
0.8205	Intermediate Similarity	NPC68167
0.8205	Intermediate Similarity	NPC475192
0.8198	Intermediate Similarity	NPC17693
0.819	Intermediate Similarity	NPC297186
0.819	Intermediate Similarity	NPC248363
0.8173	Intermediate Similarity	NPC260000
0.8167	Intermediate Similarity	NPC158654
0.8165	Intermediate Similarity	NPC224584
0.8163	Intermediate Similarity	NPC318107
0.8158	Intermediate Similarity	NPC230349
0.8158	Intermediate Similarity	NPC150919
0.8155	Intermediate Similarity	NPC61944
0.8155	Intermediate Similarity	NPC246679
0.8148	Intermediate Similarity	NPC29989
0.8148	Intermediate Similarity	NPC69332
0.8148	Intermediate Similarity	NPC95178
0.8142	Intermediate Similarity	NPC278102
0.8142	Intermediate Similarity	NPC160179
0.8125	Intermediate Similarity	NPC211421
0.812	Intermediate Similarity	NPC267552
0.812	Intermediate Similarity	NPC115159
0.812	Intermediate Similarity	NPC45438
0.812	Intermediate Similarity	NPC224273
0.812	Intermediate Similarity	NPC156139
0.812	Intermediate Similarity	NPC73532
0.812	Intermediate Similarity	NPC143427
0.812	Intermediate Similarity	NPC19174
0.8113	Intermediate Similarity	NPC284477
0.8099	Intermediate Similarity	NPC473744
0.8099	Intermediate Similarity	NPC2401
0.8099	Intermediate Similarity	NPC193203
0.8099	Intermediate Similarity	NPC229894
0.8099	Intermediate Similarity	NPC2596
0.8087	Intermediate Similarity	NPC249435
0.8087	Intermediate Similarity	NPC40649
0.8087	Intermediate Similarity	NPC209486
0.8077	Intermediate Similarity	NPC253423
0.807	Intermediate Similarity	NPC312800
0.807	Intermediate Similarity	NPC128825
0.8051	Intermediate Similarity	NPC309765
0.8051	Intermediate Similarity	NPC133909
0.8051	Intermediate Similarity	NPC32032
0.8037	Intermediate Similarity	NPC470202
0.8033	Intermediate Similarity	NPC117899
0.8033	Intermediate Similarity	NPC94810
0.8033	Intermediate Similarity	NPC194979
0.8033	Intermediate Similarity	NPC226855
0.8019	Intermediate Similarity	NPC253746
0.8017	Intermediate Similarity	NPC214620
0.8017	Intermediate Similarity	NPC473767
0.8017	Intermediate Similarity	NPC121104
0.8	Intermediate Similarity	NPC201728
0.8	Intermediate Similarity	NPC240664
0.8	Intermediate Similarity	NPC160199
0.8	Intermediate Similarity	NPC31274
0.8	Intermediate Similarity	NPC229242
0.8	Intermediate Similarity	NPC140619
0.8	Intermediate Similarity	NPC262671
0.7982	Intermediate Similarity	NPC70843
0.7981	Intermediate Similarity	NPC257182
0.7967	Intermediate Similarity	NPC285776
0.7967	Intermediate Similarity	NPC42292
0.7967	Intermediate Similarity	NPC109778
0.7967	Intermediate Similarity	NPC307732
0.7966	Intermediate Similarity	NPC303737
0.7966	Intermediate Similarity	NPC242895
0.7961	Intermediate Similarity	NPC181709
0.7949	Intermediate Similarity	NPC294037
0.7946	Intermediate Similarity	NPC23332
0.7944	Intermediate Similarity	NPC25458
0.7931	Intermediate Similarity	NPC94637
0.7928	Intermediate Similarity	NPC234639
0.7928	Intermediate Similarity	NPC326187
0.7928	Intermediate Similarity	NPC88141
0.7925	Intermediate Similarity	NPC217621
0.7917	Intermediate Similarity	NPC13238
0.7913	Intermediate Similarity	NPC128249
0.7913	Intermediate Similarity	NPC470860
0.7903	Intermediate Similarity	NPC473777
0.7903	Intermediate Similarity	NPC18798
0.7903	Intermediate Similarity	NPC104854
0.7903	Intermediate Similarity	NPC198249
0.7899	Intermediate Similarity	NPC297193
0.7895	Intermediate Similarity	NPC276111
0.7895	Intermediate Similarity	NPC118288
0.789	Intermediate Similarity	NPC303141
0.7881	Intermediate Similarity	NPC146642
0.7881	Intermediate Similarity	NPC149246
0.7881	Intermediate Similarity	NPC216216
0.787	Intermediate Similarity	NPC304638
0.7863	Intermediate Similarity	NPC328459
0.7863	Intermediate Similarity	NPC90522
0.7857	Intermediate Similarity	NPC222084
0.7857	Intermediate Similarity	NPC183648
0.7857	Intermediate Similarity	NPC21162
0.785	Intermediate Similarity	NPC282895
0.7845	Intermediate Similarity	NPC125252
0.7845	Intermediate Similarity	NPC174087
0.784	Intermediate Similarity	NPC302844
0.784	Intermediate Similarity	NPC111888
0.7826	Intermediate Similarity	NPC322358
0.7823	Intermediate Similarity	NPC17840
0.7823	Intermediate Similarity	NPC86774
0.7823	Intermediate Similarity	NPC327457
0.7823	Intermediate Similarity	NPC247477
0.7815	Intermediate Similarity	NPC295034
0.7815	Intermediate Similarity	NPC120545
0.7815	Intermediate Similarity	NPC198336
0.7815	Intermediate Similarity	NPC215392
0.781	Intermediate Similarity	NPC286006
0.7805	Intermediate Similarity	NPC41263
0.7805	Intermediate Similarity	NPC95537
0.7805	Intermediate Similarity	NPC293453
0.7798	Intermediate Similarity	NPC261573
0.7798	Intermediate Similarity	NPC120693
0.7798	Intermediate Similarity	NPC8931
0.7797	Intermediate Similarity	NPC72977
0.7797	Intermediate Similarity	NPC233282
0.7797	Intermediate Similarity	NPC260837
0.7788	Intermediate Similarity	NPC57879
0.7787	Intermediate Similarity	NPC8745
0.7787	Intermediate Similarity	NPC62952
0.7778	Intermediate Similarity	NPC184527
0.7778	Intermediate Similarity	NPC304873
0.7778	Intermediate Similarity	NPC471033
0.7778	Intermediate Similarity	NPC283823
0.7778	Intermediate Similarity	NPC114116
0.7778	Intermediate Similarity	NPC66158
0.7778	Intermediate Similarity	NPC159418
0.7778	Intermediate Similarity	NPC472585
0.7778	Intermediate Similarity	NPC311091
0.7767	Intermediate Similarity	NPC300478
0.7767	Intermediate Similarity	NPC110704
0.776	Intermediate Similarity	NPC264145
0.775	Intermediate Similarity	NPC139171
0.775	Intermediate Similarity	NPC91478
0.775	Intermediate Similarity	NPC91105
0.775	Intermediate Similarity	NPC283514

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 NPC184658 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	349
0.1-0.2	978
0.2-0.3	1598
0.3-0.4	2889
0.4-0.5	1921
0.5-0.6	1031
0.6-0.7	319
0.7-0.8	49
0.8-0.85	10
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9899	High Similarity	NPD9265	Clinical (unspecified phase)
0.8909	High Similarity	NPD9545	Approved
0.8762	High Similarity	NPD9267	Approved
0.8762	High Similarity	NPD9264	Approved
0.8762	High Similarity	NPD9263	Approved
0.8679	High Similarity	NPD9266	Approved
0.8679	High Similarity	NPD74	Approved
0.8571	High Similarity	NPD9256	Approved
0.8571	High Similarity	NPD9258	Approved
0.8496	Intermediate Similarity	NPD9268	Approved
0.8381	Intermediate Similarity	NPD9261	Approved
0.8362	Intermediate Similarity	NPD9269	Phase 2
0.8214	Intermediate Similarity	NPD9281	Approved
0.8163	Intermediate Similarity	NPD9259	Approved
0.8163	Intermediate Similarity	NPD9257	Approved
0.807	Intermediate Similarity	NPD9493	Approved
0.7712	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD1164	Approved
0.768	Intermediate Similarity	NPD3764	Approved
0.7638	Intermediate Similarity	NPD230	Phase 1
0.7619	Intermediate Similarity	NPD1202	Approved
0.7607	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD9717	Approved
0.7547	Intermediate Similarity	NPD9260	Approved
0.7525	Intermediate Similarity	NPD111	Approved
0.7521	Intermediate Similarity	NPD255	Approved
0.7521	Intermediate Similarity	NPD256	Approved
0.7458	Intermediate Similarity	NPD9568	Approved
0.7422	Intermediate Similarity	NPD1240	Approved
0.7422	Intermediate Similarity	NPD943	Approved
0.7419	Intermediate Similarity	NPD1203	Approved
0.7377	Intermediate Similarity	NPD1201	Approved
0.7368	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD9495	Approved
0.7327	Intermediate Similarity	NPD9491	Approved
0.7321	Intermediate Similarity	NPD1237	Approved
0.7317	Intermediate Similarity	NPD1608	Approved
0.7313	Intermediate Similarity	NPD4628	Phase 3
0.7308	Intermediate Similarity	NPD1607	Approved
0.7302	Intermediate Similarity	NPD9494	Approved
0.728	Intermediate Similarity	NPD1470	Approved
0.7273	Intermediate Similarity	NPD1238	Approved
0.7222	Intermediate Similarity	NPD2933	Approved
0.7222	Intermediate Similarity	NPD2934	Approved
0.7203	Intermediate Similarity	NPD1241	Discontinued
0.7197	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1510	Phase 2
0.7179	Intermediate Similarity	NPD9508	Approved
0.7177	Intermediate Similarity	NPD1481	Phase 2
0.7177	Intermediate Similarity	NPD3972	Approved
0.7164	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD2859	Approved
0.7156	Intermediate Similarity	NPD2860	Approved
0.7143	Intermediate Similarity	NPD5406	Approved
0.7143	Intermediate Similarity	NPD5408	Approved
0.7143	Intermediate Similarity	NPD846	Approved
0.7143	Intermediate Similarity	NPD5405	Approved
0.7143	Intermediate Similarity	NPD5404	Approved
0.7143	Intermediate Similarity	NPD940	Approved
0.7132	Intermediate Similarity	NPD411	Approved
0.7119	Intermediate Similarity	NPD5277	Phase 2
0.7107	Intermediate Similarity	NPD1758	Phase 1
0.71	Intermediate Similarity	NPD9490	Approved
0.7097	Intermediate Similarity	NPD1535	Discovery
0.708	Intermediate Similarity	NPD1930	Approved
0.708	Intermediate Similarity	NPD1929	Approved
0.708	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD520	Approved
0.7073	Intermediate Similarity	NPD17	Approved
0.7068	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3750	Approved
0.7054	Intermediate Similarity	NPD1242	Phase 1
0.705	Intermediate Similarity	NPD9509	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD1759	Phase 1
0.7049	Intermediate Similarity	NPD1894	Discontinued
0.7043	Intermediate Similarity	NPD3134	Approved
0.7037	Intermediate Similarity	NPD1549	Phase 2
0.7018	Intermediate Similarity	NPD164	Approved
0.7015	Intermediate Similarity	NPD2935	Discontinued
0.7015	Intermediate Similarity	NPD1551	Phase 2
0.7	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5951	Approved
0.6983	Remote Similarity	NPD1358	Approved
0.697	Remote Similarity	NPD447	Suspended
0.6964	Remote Similarity	NPD3020	Approved
0.6964	Remote Similarity	NPD2066	Phase 3
0.6963	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD226	Approved
0.696	Remote Similarity	NPD422	Phase 1
0.6957	Remote Similarity	NPD9697	Approved
0.694	Remote Similarity	NPD2799	Discontinued
0.6929	Remote Similarity	NPD1283	Approved
0.6929	Remote Similarity	NPD3225	Approved
0.6916	Remote Similarity	NPD800	Approved
0.6906	Remote Similarity	NPD6799	Approved
0.6884	Remote Similarity	NPD2354	Approved
0.6884	Remote Similarity	NPD6190	Approved
0.6875	Remote Similarity	NPD2797	Approved
0.687	Remote Similarity	NPD2313	Discontinued
0.6866	Remote Similarity	NPD9279	Approved
0.686	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1089	Approved
0.6852	Remote Similarity	NPD1090	Approved
0.6852	Remote Similarity	NPD1086	Approved
0.6842	Remote Similarity	NPD1932	Approved
0.6838	Remote Similarity	NPD2344	Approved
0.6822	Remote Similarity	NPD258	Approved
0.6822	Remote Similarity	NPD1019	Discontinued
0.6822	Remote Similarity	NPD257	Approved
0.6822	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD2798	Approved
0.6815	Remote Similarity	NPD4308	Phase 3
0.6815	Remote Similarity	NPD3748	Approved
0.6812	Remote Similarity	NPD7003	Approved
0.6812	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7411	Suspended
0.68	Remote Similarity	NPD3019	Approved
0.68	Remote Similarity	NPD1778	Approved
0.68	Remote Similarity	NPD2932	Approved
0.6797	Remote Similarity	NPD196	Phase 1
0.6797	Remote Similarity	NPD1876	Approved
0.6789	Remote Similarity	NPD1239	Approved
0.6786	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.678	Remote Similarity	NPD2182	Approved
0.6769	Remote Similarity	NPD9569	Approved
0.6769	Remote Similarity	NPD454	Approved
0.6768	Remote Similarity	NPD9087	Approved
0.6757	Remote Similarity	NPD1693	Approved
0.675	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3847	Discontinued
0.6742	Remote Similarity	NPD3268	Approved
0.6739	Remote Similarity	NPD1243	Approved
0.6731	Remote Similarity	NPD9089	Approved
0.6727	Remote Similarity	NPD1088	Approved
0.6726	Remote Similarity	NPD9273	Approved
0.6723	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1755	Approved
0.6718	Remote Similarity	NPD6832	Phase 2
0.6715	Remote Similarity	NPD9276	Approved
0.6715	Remote Similarity	NPD9278	Suspended
0.6715	Remote Similarity	NPD9274	Approved
0.6715	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD9275	Approved
0.6715	Remote Similarity	NPD2353	Approved
0.6714	Remote Similarity	NPD7440	Discontinued
0.6714	Remote Similarity	NPD643	Clinical (unspecified phase)
0.67	Remote Similarity	NPD9716	Approved
0.6696	Remote Similarity	NPD1809	Phase 2
0.6696	Remote Similarity	NPD844	Approved
0.6693	Remote Similarity	NPD1281	Approved
0.6693	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD845	Approved
0.6667	Remote Similarity	NPD9088	Approved
0.6667	Remote Similarity	NPD227	Approved
0.6667	Remote Similarity	NPD1104	Approved
0.6667	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD225	Approved
0.6667	Remote Similarity	NPD4626	Approved
0.6667	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9272	Approved
0.6667	Remote Similarity	NPD1511	Approved
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD75	Approved
0.6667	Remote Similarity	NPD9277	Approved
0.6667	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2309	Approved
0.6643	Remote Similarity	NPD1670	Discontinued
0.6642	Remote Similarity	NPD3142	Approved
0.6642	Remote Similarity	NPD2796	Approved
0.6642	Remote Similarity	NPD3140	Approved
0.6637	Remote Similarity	NPD288	Approved
0.6635	Remote Similarity	NPD9093	Approved
0.6621	Remote Similarity	NPD6599	Discontinued
0.662	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.662	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.662	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD1195	Approved
0.6617	Remote Similarity	NPD1296	Phase 2
0.6609	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD7819	Suspended
0.6599	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2614	Approved
0.6581	Remote Similarity	NPD5909	Discontinued
0.6581	Remote Similarity	NPD9610	Approved
0.6581	Remote Similarity	NPD9608	Approved
0.6577	Remote Similarity	NPD7075	Discontinued
0.6577	Remote Similarity	NPD3749	Approved
0.6574	Remote Similarity	NPD1087	Approved
0.6574	Remote Similarity	NPD4793	Discontinued
0.6573	Remote Similarity	NPD2186	Approved
0.6573	Remote Similarity	NPD1512	Approved
0.6571	Remote Similarity	NPD1196	Approved
0.6569	Remote Similarity	NPD9294	Approved
0.6567	Remote Similarity	NPD259	Phase 1

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