NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	152.05
Volume:	154.193
LogP:	0.65
LogD:	0.711
LogS:	-1.279
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.659
Synthetic Accessibility Score:	2.055
Fsp3:	0.125
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:	-5.419
MDCK Permeability:	0.0006637893966399133
Pgp-inhibitor:	0.0
Pgp-substrate:	0.166
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.508
Plasma Protein Binding (PPB):	46.28861999511719%
Volume Distribution (VD):	0.185
Pgp-substrate:	53.48195266723633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.069
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.231
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.591
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.223
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.062

ADMET: Excretion

Clearance (CL):	1.491
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.81
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.176
Carcinogencity:	0.011
Eye Corrosion:	0.025
Eye Irritation:	0.985
Respiratory Toxicity:	0.06

Download Data

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

Natural Product: NPC210529

Natural Product ID:	NPC210529
*Common Name:**	(2R)-2-Hydroxy-2-Phenylacetic Acid
IUPAC Name:	(2R)-2-hydroxy-2-phenylacetic acid
Synonyms:	Hydroxy-Phenyl-Acetic Acid Anion
Standard InCHIKey:	IWYDHOAUDWTVEP-SSDOTTSWSA-N
Standard InCHI:	InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m1/s1
SMILES:	O[C@H](c1ccccc1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL292411
PubChem CID:	11914
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted 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
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	Flowers	Tantempango, Hidalgo, Mexico	2019-May	DOI[10.1007/s11130-020-00822-2]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[12575075]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	stem	n.a.	PMID[12575075]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15577255]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16297615]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18543151]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24358188]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30188125]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778246]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14763	Aloe ferox	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14763	Aloe ferox	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14763	Aloe ferox	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14763	Aloe ferox	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2837	Aloe spicata	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2997	Aloe africana	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14763	Aloe ferox	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2997	Aloe africana	Species	Xanthorrhoeaceae	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
AC50	1
IC50	5
Ki	2
Others	5
Potency	2

Activity Type	# Activity
Individual Protein	7
ORGANISM	3
Others	4
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	5500000.0	nM	PMID[554199]
NPT4970	Individual Protein	Mandelate racemase	Pseudomonas putida	Ki	=	590000.0	nM	PMID[554200]
NPT4970	Individual Protein	Mandelate racemase	Pseudomonas putida	Ki	=	810000.0	nM	PMID[554201]
NPT2570	Individual Protein	Protein-tyrosine phosphatase LC-PTP	Homo sapiens	IC50	>	100000.0	nM	PMID[554202]
NPT1224	Individual Protein	Glyceraldehyde-3-phosphate dehydrogenase liver	Homo sapiens	IC50	>	100000.0	nM	PMID[554202]
NPT1498	Individual Protein	Dual specificity protein phosphatase 6	Rattus norvegicus	IC50	>	100000.0	nM	PMID[554202]
NPT2	Others	Unspecified		Ac50	n.a.	44.67	uM	PMID[554203]
NPT2	Others	Unspecified		AC50	n.a.	44668.4	nM	PMID[554203]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	48.36	%	PMID[554204]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	14.61	%	PMID[554205]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.41	%	PMID[554206]
NPT2	Others	Unspecified		Potency	n.a.	6681.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	33491.5	nM	PubChem BioAssay data set

☑ 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 NPC210529 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	246
0.1-0.2	945
0.2-0.3	3188
0.3-0.4	10370
0.4-0.5	12530
0.5-0.6	12180
0.6-0.7	2817
0.7-0.8	385
0.8-0.85	29
0.85-0.9	2
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC160548
1.0	High Similarity	NPC175852
0.9579	High Similarity	NPC160382
0.9341	High Similarity	NPC317645
0.8824	High Similarity	NPC326187
0.8515	High Similarity	NPC249067
0.8478	Intermediate Similarity	NPC95965
0.8476	Intermediate Similarity	NPC158282
0.8462	Intermediate Similarity	NPC285773
0.8396	Intermediate Similarity	NPC48525
0.8252	Intermediate Similarity	NPC13495
0.8242	Intermediate Similarity	NPC117180
0.8229	Intermediate Similarity	NPC62765
0.8218	Intermediate Similarity	NPC52472
0.82	Intermediate Similarity	NPC229242
0.8152	Intermediate Similarity	NPC103326
0.8152	Intermediate Similarity	NPC87299
0.8152	Intermediate Similarity	NPC329319
0.8152	Intermediate Similarity	NPC99394
0.8144	Intermediate Similarity	NPC110704
0.8137	Intermediate Similarity	NPC25458
0.8132	Intermediate Similarity	NPC127343
0.8131	Intermediate Similarity	NPC474314
0.8119	Intermediate Similarity	NPC245561
0.8119	Intermediate Similarity	NPC217621
0.8108	Intermediate Similarity	NPC104514
0.8108	Intermediate Similarity	NPC63126
0.8105	Intermediate Similarity	NPC322387
0.81	Intermediate Similarity	NPC253423
0.81	Intermediate Similarity	NPC289201
0.8085	Intermediate Similarity	NPC294134
0.8065	Intermediate Similarity	NPC288903
0.8058	Intermediate Similarity	NPC91820
0.8058	Intermediate Similarity	NPC13426
0.8058	Intermediate Similarity	NPC82426
0.8039	Intermediate Similarity	NPC469481
0.8037	Intermediate Similarity	NPC476003
0.8021	Intermediate Similarity	NPC329064
0.8	Intermediate Similarity	NPC210531
0.8	Intermediate Similarity	NPC61944
0.7982	Intermediate Similarity	NPC172525
0.7982	Intermediate Similarity	NPC474363
0.7981	Intermediate Similarity	NPC242913
0.7981	Intermediate Similarity	NPC280616
0.7981	Intermediate Similarity	NPC171831
0.7979	Intermediate Similarity	NPC304538
0.7961	Intermediate Similarity	NPC304873
0.7961	Intermediate Similarity	NPC284477
0.7925	Intermediate Similarity	NPC211439
0.7905	Intermediate Similarity	NPC472919
0.7905	Intermediate Similarity	NPC321670
0.79	Intermediate Similarity	NPC206764
0.789	Intermediate Similarity	NPC272524
0.7885	Intermediate Similarity	NPC255676
0.7876	Intermediate Similarity	NPC472708
0.7872	Intermediate Similarity	NPC44830
0.7864	Intermediate Similarity	NPC282895
0.7857	Intermediate Similarity	NPC70940
0.7857	Intermediate Similarity	NPC274455
0.7857	Intermediate Similarity	NPC86670
0.785	Intermediate Similarity	NPC31274
0.7845	Intermediate Similarity	NPC471466
0.7835	Intermediate Similarity	NPC304760
0.783	Intermediate Similarity	NPC136962
0.783	Intermediate Similarity	NPC37115
0.783	Intermediate Similarity	NPC317592
0.7818	Intermediate Similarity	NPC87069
0.7812	Intermediate Similarity	NPC318107
0.7802	Intermediate Similarity	NPC66655
0.7798	Intermediate Similarity	NPC212718
0.7768	Intermediate Similarity	NPC212891
0.7767	Intermediate Similarity	NPC228435
0.7767	Intermediate Similarity	NPC280869
0.7757	Intermediate Similarity	NPC156648
0.7755	Intermediate Similarity	NPC9822
0.7748	Intermediate Similarity	NPC221870
0.7745	Intermediate Similarity	NPC276775
0.7745	Intermediate Similarity	NPC92754
0.7745	Intermediate Similarity	NPC249912
0.7736	Intermediate Similarity	NPC105899
0.7732	Intermediate Similarity	NPC89377
0.7723	Intermediate Similarity	NPC130398
0.7712	Intermediate Similarity	NPC65310
0.7706	Intermediate Similarity	NPC222084
0.7706	Intermediate Similarity	NPC260818
0.7692	Intermediate Similarity	NPC42211
0.7685	Intermediate Similarity	NPC317305
0.7685	Intermediate Similarity	NPC281604
0.7685	Intermediate Similarity	NPC85493
0.7684	Intermediate Similarity	NPC172984
0.767	Intermediate Similarity	NPC78701
0.767	Intermediate Similarity	NPC329387
0.767	Intermediate Similarity	NPC260000
0.767	Intermediate Similarity	NPC35448
0.767	Intermediate Similarity	NPC317280
0.767	Intermediate Similarity	NPC225060
0.7664	Intermediate Similarity	NPC474376
0.7664	Intermediate Similarity	NPC472315
0.7664	Intermediate Similarity	NPC472316
0.7664	Intermediate Similarity	NPC475203
0.7658	Intermediate Similarity	NPC148969
0.7642	Intermediate Similarity	NPC19136
0.7636	Intermediate Similarity	NPC321852
0.7627	Intermediate Similarity	NPC57607
0.7624	Intermediate Similarity	NPC261181
0.7615	Intermediate Similarity	NPC234639
0.76	Intermediate Similarity	NPC187725
0.76	Intermediate Similarity	NPC141607
0.7596	Intermediate Similarity	NPC146351
0.7596	Intermediate Similarity	NPC118343
0.7593	Intermediate Similarity	NPC249811
0.7593	Intermediate Similarity	NPC277788
0.7589	Intermediate Similarity	NPC306740
0.7589	Intermediate Similarity	NPC474685
0.7579	Intermediate Similarity	NPC323103
0.7576	Intermediate Similarity	NPC1793
0.7576	Intermediate Similarity	NPC220893
0.7573	Intermediate Similarity	NPC270654
0.7553	Intermediate Similarity	NPC121800
0.7551	Intermediate Similarity	NPC211237
0.7549	Intermediate Similarity	NPC172925
0.7547	Intermediate Similarity	NPC301943
0.7547	Intermediate Similarity	NPC474365
0.7545	Intermediate Similarity	NPC252544
0.7545	Intermediate Similarity	NPC321252
0.7526	Intermediate Similarity	NPC58616
0.7524	Intermediate Similarity	NPC70624
0.7523	Intermediate Similarity	NPC469636
0.7523	Intermediate Similarity	NPC474364
0.7523	Intermediate Similarity	NPC83628
0.7523	Intermediate Similarity	NPC265407
0.7523	Intermediate Similarity	NPC318327
0.7522	Intermediate Similarity	NPC4665
0.75	Intermediate Similarity	NPC237366
0.75	Intermediate Similarity	NPC11824
0.75	Intermediate Similarity	NPC270507
0.75	Intermediate Similarity	NPC153053
0.7477	Intermediate Similarity	NPC234376
0.7477	Intermediate Similarity	NPC177576
0.7477	Intermediate Similarity	NPC114682
0.7477	Intermediate Similarity	NPC471188
0.7474	Intermediate Similarity	NPC133050
0.7473	Intermediate Similarity	NPC108218
0.7458	Intermediate Similarity	NPC469927
0.7456	Intermediate Similarity	NPC128249
0.7453	Intermediate Similarity	NPC188895
0.7451	Intermediate Similarity	NPC325292
0.7451	Intermediate Similarity	NPC34243
0.7451	Intermediate Similarity	NPC138117
0.7449	Intermediate Similarity	NPC93843
0.7447	Intermediate Similarity	NPC170484
0.7438	Intermediate Similarity	NPC472707
0.7434	Intermediate Similarity	NPC469509
0.7431	Intermediate Similarity	NPC20485
0.7429	Intermediate Similarity	NPC203925
0.7429	Intermediate Similarity	NPC325497
0.7426	Intermediate Similarity	NPC300017
0.7426	Intermediate Similarity	NPC472319
0.7411	Intermediate Similarity	NPC17693
0.7411	Intermediate Similarity	NPC265002
0.7411	Intermediate Similarity	NPC161611
0.7407	Intermediate Similarity	NPC269457
0.74	Intermediate Similarity	NPC173443
0.7396	Intermediate Similarity	NPC475199
0.7396	Intermediate Similarity	NPC283012
0.7396	Intermediate Similarity	NPC103387
0.7387	Intermediate Similarity	NPC474157
0.7387	Intermediate Similarity	NPC21162
0.7387	Intermediate Similarity	NPC95126
0.7387	Intermediate Similarity	NPC475002
0.7383	Intermediate Similarity	NPC60679
0.7383	Intermediate Similarity	NPC89886
0.7383	Intermediate Similarity	NPC291426
0.7377	Intermediate Similarity	NPC301857
0.7373	Intermediate Similarity	NPC322332
0.7364	Intermediate Similarity	NPC475282
0.735	Intermediate Similarity	NPC470585
0.735	Intermediate Similarity	NPC183339
0.735	Intermediate Similarity	NPC234337
0.735	Intermediate Similarity	NPC133389
0.7347	Intermediate Similarity	NPC99482
0.7345	Intermediate Similarity	NPC308744
0.7345	Intermediate Similarity	NPC109241
0.7345	Intermediate Similarity	NPC196673
0.7339	Intermediate Similarity	NPC119271
0.7339	Intermediate Similarity	NPC187913
0.7339	Intermediate Similarity	NPC184658
0.7339	Intermediate Similarity	NPC1065
0.7328	Intermediate Similarity	NPC311091
0.7328	Intermediate Similarity	NPC471033
0.7321	Intermediate Similarity	NPC185840
0.7321	Intermediate Similarity	NPC66208
0.7315	Intermediate Similarity	NPC31786
0.7315	Intermediate Similarity	NPC120693
0.7315	Intermediate Similarity	NPC261573
0.7315	Intermediate Similarity	NPC8931
0.7315	Intermediate Similarity	NPC114594
0.7315	Intermediate Similarity	NPC324786
0.7311	Intermediate Similarity	NPC223351
0.7308	Intermediate Similarity	NPC246679

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 NPC210529 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	761
0.2-0.3	1528
0.3-0.4	2937
0.4-0.5	2231
0.5-0.6	1099
0.6-0.7	298
0.7-0.8	79
0.8-0.85	5
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	NPD9495	Approved
0.8585	High Similarity	NPD2629	Approved
0.8515	High Similarity	NPD1237	Approved
0.8462	Intermediate Similarity	NPD9491	Approved
0.8229	Intermediate Similarity	NPD9256	Approved
0.8229	Intermediate Similarity	NPD9258	Approved
0.8043	Intermediate Similarity	NPD226	Approved
0.8022	Intermediate Similarity	NPD9490	Approved
0.7938	Intermediate Similarity	NPD800	Approved
0.7857	Intermediate Similarity	NPD1089	Approved
0.7857	Intermediate Similarity	NPD1090	Approved
0.7857	Intermediate Similarity	NPD1086	Approved
0.7812	Intermediate Similarity	NPD9257	Approved
0.7812	Intermediate Similarity	NPD9259	Approved
0.7807	Intermediate Similarity	NPD5306	Approved
0.7807	Intermediate Similarity	NPD5305	Approved
0.7802	Intermediate Similarity	NPD9294	Approved
0.7778	Intermediate Similarity	NPD1239	Approved
0.7748	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD4135	Approved
0.7739	Intermediate Similarity	NPD4106	Approved
0.7739	Intermediate Similarity	NPD4136	Approved
0.7723	Intermediate Similarity	NPD1693	Approved
0.7717	Intermediate Similarity	NPD227	Approved
0.7717	Intermediate Similarity	NPD225	Approved
0.7714	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2626	Approved
0.7712	Intermediate Similarity	NPD2625	Approved
0.7712	Intermediate Similarity	NPD2160	Approved
0.7712	Intermediate Similarity	NPD2628	Approved
0.7712	Intermediate Similarity	NPD2627	Approved
0.7712	Intermediate Similarity	NPD2159	Approved
0.77	Intermediate Similarity	NPD1088	Approved
0.7672	Intermediate Similarity	NPD4807	Approved
0.7672	Intermediate Similarity	NPD4806	Approved
0.7624	Intermediate Similarity	NPD1202	Approved
0.7596	Intermediate Similarity	NPD1238	Approved
0.7565	Intermediate Similarity	NPD4102	Approved
0.7565	Intermediate Similarity	NPD4105	Approved
0.7551	Intermediate Similarity	NPD4793	Discontinued
0.7551	Intermediate Similarity	NPD1087	Approved
0.7549	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6647	Phase 2
0.7523	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD2067	Discontinued
0.7438	Intermediate Similarity	NPD3664	Approved
0.7438	Intermediate Similarity	NPD5204	Approved
0.7438	Intermediate Similarity	NPD3661	Approved
0.7438	Intermediate Similarity	NPD3662	Phase 3
0.7438	Intermediate Similarity	NPD3663	Approved
0.7429	Intermediate Similarity	NPD2066	Phase 3
0.7407	Intermediate Similarity	NPD5048	Discontinued
0.7404	Intermediate Similarity	NPD1565	Approved
0.7404	Intermediate Similarity	NPD1564	Approved
0.7404	Intermediate Similarity	NPD1566	Phase 3
0.74	Intermediate Similarity	NPD5346	Phase 2
0.74	Intermediate Similarity	NPD5347	Phase 2
0.7387	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD4617	Approved
0.7377	Intermediate Similarity	NPD5203	Approved
0.7377	Intermediate Similarity	NPD4620	Approved
0.7377	Intermediate Similarity	NPD5201	Approved
0.7321	Intermediate Similarity	NPD969	Suspended
0.7315	Intermediate Similarity	NPD164	Approved
0.7308	Intermediate Similarity	NPD1989	Approved
0.7282	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9263	Approved
0.7273	Intermediate Similarity	NPD9267	Approved
0.7273	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9264	Approved
0.7236	Intermediate Similarity	NPD5202	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1930	Approved
0.7222	Intermediate Similarity	NPD1929	Approved
0.7217	Intermediate Similarity	NPD4198	Discontinued
0.7212	Intermediate Similarity	NPD9260	Approved
0.7207	Intermediate Similarity	NPD9266	Approved
0.7207	Intermediate Similarity	NPD2182	Approved
0.7207	Intermediate Similarity	NPD74	Approved
0.7179	Intermediate Similarity	NPD9545	Approved
0.7168	Intermediate Similarity	NPD9508	Approved
0.7157	Intermediate Similarity	NPD3672	Approved
0.7157	Intermediate Similarity	NPD3673	Approved
0.7155	Intermediate Similarity	NPD9493	Approved
0.7155	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5120	Approved
0.7143	Intermediate Similarity	NPD5121	Approved
0.7143	Intermediate Similarity	NPD6310	Approved
0.7143	Intermediate Similarity	NPD5119	Approved
0.7143	Intermediate Similarity	NPD6311	Approved
0.7143	Intermediate Similarity	NPD6309	Approved
0.713	Intermediate Similarity	NPD5951	Approved
0.712	Intermediate Similarity	NPD4621	Approved
0.712	Intermediate Similarity	NPD4619	Approved
0.7117	Intermediate Similarity	NPD9532	Phase 3
0.7115	Intermediate Similarity	NPD1563	Approved
0.7105	Intermediate Similarity	NPD5277	Phase 2
0.7103	Intermediate Similarity	NPD7798	Approved
0.7073	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD255	Approved
0.7069	Intermediate Similarity	NPD256	Approved
0.7064	Intermediate Similarity	NPD5765	Approved
0.7034	Intermediate Similarity	NPD1894	Discontinued
0.7027	Intermediate Similarity	NPD467	Phase 1
0.7021	Intermediate Similarity	NPD9716	Approved
0.7009	Intermediate Similarity	NPD9611	Approved
0.7009	Intermediate Similarity	NPD9609	Approved
0.7009	Intermediate Similarity	NPD9612	Approved
0.7009	Intermediate Similarity	NPD9568	Approved
0.7	Intermediate Similarity	NPD5909	Discontinued
0.6984	Remote Similarity	NPD6798	Discontinued
0.6981	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1932	Approved
0.6952	Remote Similarity	NPD1066	Discontinued
0.6949	Remote Similarity	NPD1758	Phase 1
0.6944	Remote Similarity	NPD9712	Approved
0.6935	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6085	Phase 2
0.693	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6233	Phase 2
0.6929	Remote Similarity	NPD4062	Phase 3
0.6916	Remote Similarity	NPD9566	Approved
0.6911	Remote Similarity	NPD5667	Approved
0.6909	Remote Similarity	NPD9261	Approved
0.6897	Remote Similarity	NPD2652	Approved
0.6897	Remote Similarity	NPD2650	Approved
0.6893	Remote Similarity	NPD689	Discontinued
0.6891	Remote Similarity	NPD1759	Phase 1
0.6875	Remote Similarity	NPD6685	Approved
0.6852	Remote Similarity	NPD9711	Approved
0.6852	Remote Similarity	NPD253	Approved
0.6852	Remote Similarity	NPD9710	Approved
0.6838	Remote Similarity	NPD9281	Approved
0.6833	Remote Similarity	NPD446	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5157	Phase 1
0.6829	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5159	Phase 2
0.6822	Remote Similarity	NPD6355	Discontinued
0.6818	Remote Similarity	NPD855	Approved
0.6818	Remote Similarity	NPD854	Approved
0.68	Remote Similarity	NPD5647	Approved
0.6797	Remote Similarity	NPD7715	Approved
0.6797	Remote Similarity	NPD7714	Approved
0.6791	Remote Similarity	NPD2575	Approved
0.6789	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7008	Discontinued
0.6772	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD9250	Approved
0.6757	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6010	Discontinued
0.6748	Remote Similarity	NPD1481	Phase 2
0.6742	Remote Similarity	NPD4173	Approved
0.6742	Remote Similarity	NPD4172	Approved
0.6742	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD2933	Approved
0.6729	Remote Similarity	NPD2934	Approved
0.6699	Remote Similarity	NPD1282	Approved
0.6696	Remote Similarity	NPD309	Approved
0.6696	Remote Similarity	NPD4233	Approved
0.6696	Remote Similarity	NPD10	Approved
0.6696	Remote Similarity	NPD4234	Approved
0.6696	Remote Similarity	NPD310	Approved
0.6696	Remote Similarity	NPD315	Approved
0.6696	Remote Similarity	NPD311	Approved
0.6696	Remote Similarity	NPD314	Approved
0.6667	Remote Similarity	NPD2612	Approved
0.6667	Remote Similarity	NPD2859	Approved
0.6667	Remote Similarity	NPD111	Approved
0.6667	Remote Similarity	NPD290	Approved
0.6667	Remote Similarity	NPD3132	Approved
0.6667	Remote Similarity	NPD2860	Approved
0.6667	Remote Similarity	NPD2610	Approved
0.6667	Remote Similarity	NPD2608	Approved
0.6667	Remote Similarity	NPD258	Approved
0.6667	Remote Similarity	NPD4217	Approved
0.6667	Remote Similarity	NPD4216	Approved
0.6667	Remote Similarity	NPD2609	Approved
0.6667	Remote Similarity	NPD3131	Approved
0.6667	Remote Similarity	NPD4218	Approved
0.6667	Remote Similarity	NPD4215	Approved
0.6667	Remote Similarity	NPD257	Approved
0.6667	Remote Similarity	NPD2611	Approved
0.6667	Remote Similarity	NPD1535	Discovery
0.6641	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.664	Remote Similarity	NPD1283	Approved
0.6639	Remote Similarity	NPD1104	Approved
0.6639	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD845	Approved
0.6634	Remote Similarity	NPD3971	Phase 1
0.6617	Remote Similarity	NPD9570	Approved
0.6615	Remote Similarity	NPD826	Approved
0.6615	Remote Similarity	NPD825	Approved
0.6614	Remote Similarity	NPD454	Approved
0.6614	Remote Similarity	NPD9569	Approved
0.6613	Remote Similarity	NPD9717	Approved
0.6613	Remote Similarity	NPD1608	Approved
0.661	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.661	Remote Similarity	NPD1241	Discontinued
0.6609	Remote Similarity	NPD2329	Discontinued

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