NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	189.08
Volume:	197.094
LogP:	1.968
LogD:	2.125
LogS:	-2.406
# Rotatable Bonds:	3
TPSA:	53.09
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.777
Synthetic Accessibility Score:	1.718
Fsp3:	0.182
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:	-4.497
MDCK Permeability:	1.0948709132208023e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.709

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.403
Plasma Protein Binding (PPB):	88.77806854248047%
Volume Distribution (VD):	0.266
Pgp-substrate:	8.048563003540039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.229
CYP1A2-substrate:	0.333
CYP2C19-inhibitor:	0.082
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.088
CYP2D6-substrate:	0.747
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.071

ADMET: Excretion

Clearance (CL):	6.017
Half-life (T1/2):	0.901

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.252
Drug-inuced Liver Injury (DILI):	0.169
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.744
Maximum Recommended Daily Dose:	0.346
Skin Sensitization:	0.368
Carcinogencity:	0.19
Eye Corrosion:	0.027
Eye Irritation:	0.911
Respiratory Toxicity:	0.328

Download Data

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

Natural Product: NPC78020

Natural Product ID:	NPC78020
*Common Name:**	Indolylpropionic Acid
IUPAC Name:	3-(1H-indol-3-yl)propanoic acid
Synonyms:	3-Indolepropionicacid; Indole-3-Propionic Acid
Standard InCHIKey:	GOLXRNDWAUTYKT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14)
SMILES:	OC(=O)CCc1c[nH]c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL207225
PubChem CID:	3744
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001290] Indolyl carboxylic acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference

☑ 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	4
Ki	1
Others	17

Activity Type	# Activity
Cell Line	4
Individual Protein	1
Organism	9
Others	7
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3926	Cell Line	Mixed cortical cells	Rattus norvegicus	Inhibition	=	87.7	%	PMID[470202]
NPT3926	Cell Line	Mixed cortical cells	Rattus norvegicus	Inhibition	=	83.8	%	PMID[470202]
NPT3926	Cell Line	Mixed cortical cells	Rattus norvegicus	Inhibition	=	76.1	%	PMID[470202]
NPT3170	Individual Protein	Kynurenine--oxoglutarate transaminase I	Homo sapiens	IC50	=	140000.0	nM	PMID[470204]
NPT65	Cell Line	HepG2	Homo sapiens	CC50	>	1000000.0	nM	PMID[470207]
NPT35	Others	n.a.		Ki	=	22908676527.68	nM	PMID[470202]
NPT1	Others	Radical scavenging activity		Activity	=	95.7	nM	PMID[470202]
NPT1	Others	Radical scavenging activity		Activity	=	96.5	nM	PMID[470202]
NPT3927	Organism	Rotifers	Rotifera	Activity	=	67.9	%	PMID[470202]
NPT3927	Organism	Rotifers	Rotifera	Activity	=	53.8	%	PMID[470202]
NPT27	Others	Unspecified		LogP app	=	-5.68	n.a.	PMID[470203]
NPT35	Others	n.a.		LogP	=	1.75	n.a.	PMID[470203]
NPT2	Others	Unspecified		IC50	>	1000000.0	nM	PMID[470205]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-17.48	%	PMID[470206]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC50	=	68000.0	nM	PMID[470207]
NPT27	Others	Unspecified		F	=	30.0	%	PMID[470207]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	FC	=	7.0	n.a.	PMID[470207]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	10.15	%	PMID[470208]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.15	%	PMID[470209]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[470210]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[470210]

☑ 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 NPC78020 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	324
0.1-0.2	2733
0.2-0.3	14943
0.3-0.4	17249
0.4-0.5	3050
0.5-0.6	1970
0.6-0.7	1588
0.7-0.8	674
0.8-0.85	97
0.85-0.9	40
0.9-0.95	20
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9744	High Similarity	NPC110500
0.9744	High Similarity	NPC203468
0.9744	High Similarity	NPC149155
0.9682	High Similarity	NPC267885
0.956	High Similarity	NPC55772
0.956	High Similarity	NPC126709
0.956	High Similarity	NPC248041
0.956	High Similarity	NPC283219
0.9497	High Similarity	NPC111275
0.9255	High Similarity	NPC145885
0.9255	High Similarity	NPC84827
0.9255	High Similarity	NPC14113
0.9212	High Similarity	NPC235684
0.9212	High Similarity	NPC315555
0.9198	High Similarity	NPC213468
0.9102	High Similarity	NPC321708
0.8982	High Similarity	NPC62749
0.897	High Similarity	NPC71037
0.8924	High Similarity	NPC279918
0.8868	High Similarity	NPC282231
0.8788	High Similarity	NPC217372
0.8788	High Similarity	NPC15573
0.8788	High Similarity	NPC183662
0.8786	High Similarity	NPC179701
0.8742	High Similarity	NPC230869
0.8736	High Similarity	NPC272483
0.8736	High Similarity	NPC262898
0.8735	High Similarity	NPC219336
0.8726	High Similarity	NPC73952
0.8726	High Similarity	NPC469765
0.8726	High Similarity	NPC469763
0.8726	High Similarity	NPC25008
0.8726	High Similarity	NPC469760
0.8726	High Similarity	NPC259644
0.8726	High Similarity	NPC469786
0.8713	High Similarity	NPC83111
0.8704	High Similarity	NPC160105
0.8704	High Similarity	NPC474561
0.8704	High Similarity	NPC49954
0.8704	High Similarity	NPC54988
0.8679	High Similarity	NPC469762
0.8671	High Similarity	NPC70922
0.8671	High Similarity	NPC75540
0.8671	High Similarity	NPC212376
0.8671	High Similarity	NPC80597
0.8671	High Similarity	NPC211572
0.865	High Similarity	NPC63751
0.8616	High Similarity	NPC469785
0.8596	High Similarity	NPC278434
0.8588	High Similarity	NPC213308
0.8588	High Similarity	NPC45459
0.8588	High Similarity	NPC315491
0.8581	High Similarity	NPC314372
0.858	High Similarity	NPC469358
0.8571	High Similarity	NPC190296
0.8497	Intermediate Similarity	NPC154339
0.8494	Intermediate Similarity	NPC314603
0.8488	Intermediate Similarity	NPC17059
0.8466	Intermediate Similarity	NPC194640
0.8466	Intermediate Similarity	NPC311276
0.8462	Intermediate Similarity	NPC159856
0.8457	Intermediate Similarity	NPC131718
0.8457	Intermediate Similarity	NPC88315
0.8421	Intermediate Similarity	NPC228835
0.8418	Intermediate Similarity	NPC227582
0.8402	Intermediate Similarity	NPC11126
0.8398	Intermediate Similarity	NPC473376
0.8389	Intermediate Similarity	NPC476874
0.8354	Intermediate Similarity	NPC102423
0.8354	Intermediate Similarity	NPC40779
0.8353	Intermediate Similarity	NPC469896
0.8352	Intermediate Similarity	NPC267343
0.8343	Intermediate Similarity	NPC59269
0.8343	Intermediate Similarity	NPC248454
0.8333	Intermediate Similarity	NPC213629
0.8315	Intermediate Similarity	NPC156704
0.8313	Intermediate Similarity	NPC201700
0.8306	Intermediate Similarity	NPC88008
0.8305	Intermediate Similarity	NPC202812
0.8301	Intermediate Similarity	NPC96102
0.8301	Intermediate Similarity	NPC261195
0.8301	Intermediate Similarity	NPC29886
0.8278	Intermediate Similarity	NPC252338
0.8268	Intermediate Similarity	NPC67288
0.8268	Intermediate Similarity	NPC131887
0.825	Intermediate Similarity	NPC105818
0.825	Intermediate Similarity	NPC24678
0.8247	Intermediate Similarity	NPC105127
0.8247	Intermediate Similarity	NPC84911
0.8239	Intermediate Similarity	NPC138370
0.8239	Intermediate Similarity	NPC471957
0.8222	Intermediate Similarity	NPC293917
0.8218	Intermediate Similarity	NPC94752
0.8216	Intermediate Similarity	NPC478158
0.8198	Intermediate Similarity	NPC233936
0.8193	Intermediate Similarity	NPC42372
0.8187	Intermediate Similarity	NPC476073
0.8167	Intermediate Similarity	NPC171317
0.8158	Intermediate Similarity	NPC82295
0.8156	Intermediate Similarity	NPC11445
0.815	Intermediate Similarity	NPC163055
0.8141	Intermediate Similarity	NPC110126
0.8141	Intermediate Similarity	NPC73767
0.8128	Intermediate Similarity	NPC82370
0.8125	Intermediate Similarity	NPC175474
0.8103	Intermediate Similarity	NPC165495
0.8101	Intermediate Similarity	NPC195239
0.8101	Intermediate Similarity	NPC157828
0.8089	Intermediate Similarity	NPC469779
0.8089	Intermediate Similarity	NPC469767
0.8089	Intermediate Similarity	NPC469780
0.8089	Intermediate Similarity	NPC469783
0.8089	Intermediate Similarity	NPC469784
0.8089	Intermediate Similarity	NPC469761
0.8089	Intermediate Similarity	NPC469768
0.8089	Intermediate Similarity	NPC279081
0.8086	Intermediate Similarity	NPC216713
0.8085	Intermediate Similarity	NPC207020
0.8081	Intermediate Similarity	NPC248462
0.8059	Intermediate Similarity	NPC313791
0.8057	Intermediate Similarity	NPC314002
0.8057	Intermediate Similarity	NPC188387
0.8057	Intermediate Similarity	NPC280290
0.8057	Intermediate Similarity	NPC163421
0.8049	Intermediate Similarity	NPC285469
0.8046	Intermediate Similarity	NPC220765
0.8042	Intermediate Similarity	NPC54744
0.8042	Intermediate Similarity	NPC229348
0.8038	Intermediate Similarity	NPC469766
0.8023	Intermediate Similarity	NPC64436
0.8023	Intermediate Similarity	NPC151939
0.8022	Intermediate Similarity	NPC74413
0.8012	Intermediate Similarity	NPC293216
0.8	Intermediate Similarity	NPC313640
0.8	Intermediate Similarity	NPC478157
0.8	Intermediate Similarity	NPC204717
0.7989	Intermediate Similarity	NPC193761
0.7975	Intermediate Similarity	NPC230002
0.7966	Intermediate Similarity	NPC317030
0.7966	Intermediate Similarity	NPC46580
0.7952	Intermediate Similarity	NPC135141
0.7952	Intermediate Similarity	NPC92796
0.7931	Intermediate Similarity	NPC300688
0.7931	Intermediate Similarity	NPC91179
0.7927	Intermediate Similarity	NPC200214
0.7919	Intermediate Similarity	NPC184964
0.7919	Intermediate Similarity	NPC284775
0.7914	Intermediate Similarity	NPC54420
0.791	Intermediate Similarity	NPC474707
0.791	Intermediate Similarity	NPC171171
0.7907	Intermediate Similarity	NPC469938
0.7898	Intermediate Similarity	NPC477003
0.7895	Intermediate Similarity	NPC75634
0.7892	Intermediate Similarity	NPC260900
0.7877	Intermediate Similarity	NPC329858
0.7877	Intermediate Similarity	NPC314333
0.7876	Intermediate Similarity	NPC281049
0.7869	Intermediate Similarity	NPC473640
0.7869	Intermediate Similarity	NPC50503
0.7869	Intermediate Similarity	NPC52557
0.7865	Intermediate Similarity	NPC204565
0.7857	Intermediate Similarity	NPC16667
0.7853	Intermediate Similarity	NPC15102
0.784	Intermediate Similarity	NPC143872
0.784	Intermediate Similarity	NPC288838
0.7838	Intermediate Similarity	NPC475506
0.7838	Intermediate Similarity	NPC300183
0.7831	Intermediate Similarity	NPC162860
0.7826	Intermediate Similarity	NPC241024
0.7826	Intermediate Similarity	NPC100321
0.7821	Intermediate Similarity	NPC65215
0.7821	Intermediate Similarity	NPC102338
0.7821	Intermediate Similarity	NPC196251
0.7821	Intermediate Similarity	NPC111602
0.7821	Intermediate Similarity	NPC173028
0.7821	Intermediate Similarity	NPC63199
0.7819	Intermediate Similarity	NPC323927
0.7802	Intermediate Similarity	NPC276517
0.7802	Intermediate Similarity	NPC294693
0.7796	Intermediate Similarity	NPC155143
0.7791	Intermediate Similarity	NPC470498
0.7791	Intermediate Similarity	NPC469811
0.779	Intermediate Similarity	NPC55493
0.779	Intermediate Similarity	NPC477167
0.779	Intermediate Similarity	NPC47190
0.779	Intermediate Similarity	NPC473342
0.779	Intermediate Similarity	NPC99666
0.7784	Intermediate Similarity	NPC129721
0.7784	Intermediate Similarity	NPC470497
0.7784	Intermediate Similarity	NPC195461
0.7784	Intermediate Similarity	NPC81654
0.7784	Intermediate Similarity	NPC470677
0.7784	Intermediate Similarity	NPC249150
0.7784	Intermediate Similarity	NPC49196
0.7784	Intermediate Similarity	NPC313985
0.7784	Intermediate Similarity	NPC79129
0.7778	Intermediate Similarity	NPC95783
0.7778	Intermediate Similarity	NPC171787
0.7772	Intermediate Similarity	NPC306376
0.7772	Intermediate Similarity	NPC470499

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 NPC78020 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	566
0.2-0.3	941
0.3-0.4	1737
0.4-0.5	2535
0.5-0.6	2098
0.6-0.7	872
0.7-0.8	173
0.8-0.85	15
0.85-0.9	3
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9744	High Similarity	NPD482	Approved
0.9682	High Similarity	NPD749	Clinical (unspecified phase)
0.9383	High Similarity	NPD2095	Phase 2
0.9383	High Similarity	NPD2092	Phase 2
0.9383	High Similarity	NPD2094	Phase 2
0.9325	High Similarity	NPD2091	Phase 2
0.9325	High Similarity	NPD2096	Phase 2
0.9308	High Similarity	NPD750	Phase 2
0.903	High Similarity	NPD5728	Clinical (unspecified phase)
0.8598	High Similarity	NPD4184	Clinical (unspecified phase)
0.8588	High Similarity	NPD484	Approved
0.8398	Intermediate Similarity	NPD5901	Discontinued
0.8385	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8251	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD6595	Phase 3
0.8222	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD2844	Phase 3
0.8172	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.8172	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD786	Approved
0.8128	Intermediate Similarity	NPD7470	Discontinued
0.8128	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD5426	Phase 3
0.8087	Intermediate Similarity	NPD8073	Approved
0.8043	Intermediate Similarity	NPD8072	Approved
0.8038	Intermediate Similarity	NPD1722	Approved
0.8023	Intermediate Similarity	NPD2144	Approved
0.8012	Intermediate Similarity	NPD5065	Approved
0.7989	Intermediate Similarity	NPD3178	Discontinued
0.7966	Intermediate Similarity	NPD8431	Approved
0.7962	Intermediate Similarity	NPD2896	Discontinued
0.7957	Intermediate Similarity	NPD7957	Phase 1
0.7957	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7906	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6178	Phase 3
0.7886	Intermediate Similarity	NPD3038	Discontinued
0.7877	Intermediate Similarity	NPD4499	Approved
0.7857	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1534	Approved
0.7819	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7970	Approved
0.7802	Intermediate Similarity	NPD7618	Phase 3
0.7802	Intermediate Similarity	NPD7619	Phase 3
0.7801	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4600	Approved
0.7784	Intermediate Similarity	NPD4601	Approved
0.7778	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD3100	Discontinued
0.7744	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1326	Approved
0.7733	Intermediate Similarity	NPD1325	Approved
0.7713	Intermediate Similarity	NPD8272	Phase 2
0.7701	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2172	Phase 1
0.7684	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD4076	Approved
0.767	Intermediate Similarity	NPD4079	Approved
0.765	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD1038	Approved
0.7641	Intermediate Similarity	NPD5818	Discontinued
0.7632	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6664	Approved
0.7622	Intermediate Similarity	NPD7948	Phase 1
0.7614	Intermediate Similarity	NPD3506	Approved
0.7614	Intermediate Similarity	NPD3505	Approved
0.7611	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7944	Discontinued
0.7594	Intermediate Similarity	NPD2305	Discontinued
0.7594	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD2510	Approved
0.7592	Intermediate Similarity	NPD2509	Approved
0.759	Intermediate Similarity	NPD4462	Approved
0.759	Intermediate Similarity	NPD4463	Approved
0.7588	Intermediate Similarity	NPD1403	Approved
0.7588	Intermediate Similarity	NPD1404	Approved
0.7584	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4948	Discontinued
0.7557	Intermediate Similarity	NPD4075	Phase 2
0.7551	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD5003	Discontinued
0.7526	Intermediate Similarity	NPD6987	Phase 1
0.7514	Intermediate Similarity	NPD7865	Approved
0.7514	Intermediate Similarity	NPD5611	Phase 2
0.7513	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2837	Discontinued
0.7485	Intermediate Similarity	NPD1592	Phase 3
0.7459	Intermediate Similarity	NPD802	Phase 2
0.7458	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6999	Discontinued
0.7447	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD2336	Approved
0.7436	Intermediate Similarity	NPD8093	Discontinued
0.743	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD2642	Approved
0.7414	Intermediate Similarity	NPD2639	Approved
0.7411	Intermediate Similarity	NPD3389	Approved
0.7411	Intermediate Similarity	NPD3393	Approved
0.7411	Intermediate Similarity	NPD3394	Approved
0.7407	Intermediate Similarity	NPD4501	Approved
0.7407	Intermediate Similarity	NPD4500	Approved
0.7405	Intermediate Similarity	NPD6665	Discontinued
0.7405	Intermediate Similarity	NPD5505	Discontinued
0.7401	Intermediate Similarity	NPD4128	Approved
0.7399	Intermediate Similarity	NPD1631	Approved
0.7398	Intermediate Similarity	NPD8094	Discontinued
0.7394	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2564	Approved
0.7391	Intermediate Similarity	NPD2565	Phase 2
0.7386	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD3961	Discontinued
0.7374	Intermediate Similarity	NPD8386	Phase 2
0.7371	Intermediate Similarity	NPD2640	Approved
0.7371	Intermediate Similarity	NPD2641	Approved
0.7371	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4703	Approved
0.7365	Intermediate Similarity	NPD4702	Approved
0.7353	Intermediate Similarity	NPD2809	Approved
0.7341	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7234	Approved
0.7337	Intermediate Similarity	NPD7233	Approved
0.7333	Intermediate Similarity	NPD5897	Approved
0.7333	Intermediate Similarity	NPD5898	Approved
0.7333	Intermediate Similarity	NPD5899	Approved
0.733	Intermediate Similarity	NPD1573	Approved
0.733	Intermediate Similarity	NPD1575	Approved
0.7318	Intermediate Similarity	NPD4181	Approved
0.7316	Intermediate Similarity	NPD6479	Discontinued
0.7312	Intermediate Similarity	NPD3404	Approved
0.7303	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3323	Discontinued
0.7287	Intermediate Similarity	NPD2307	Discontinued
0.7283	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7866	Approved
0.7262	Intermediate Similarity	NPD1661	Suspended
0.7257	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7711	Discontinued
0.7241	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4602	Approved
0.7234	Intermediate Similarity	NPD4427	Phase 2
0.7225	Intermediate Similarity	NPD5043	Discontinued
0.7225	Intermediate Similarity	NPD1630	Approved
0.722	Intermediate Similarity	NPD6165	Phase 2
0.722	Intermediate Similarity	NPD6164	Phase 2
0.7216	Intermediate Similarity	NPD7001	Phase 3
0.7216	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD991	Phase 2
0.7212	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4397	Phase 1
0.7205	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6176	Phase 1
0.72	Intermediate Similarity	NPD5140	Approved
0.72	Intermediate Similarity	NPD5138	Approved
0.7184	Intermediate Similarity	NPD2511	Approved
0.7184	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6242	Discontinued
0.7175	Intermediate Similarity	NPD4640	Approved
0.7175	Intermediate Similarity	NPD4639	Approved
0.7175	Intermediate Similarity	NPD4638	Approved
0.7171	Intermediate Similarity	NPD7603	Discontinued
0.7168	Intermediate Similarity	NPD4326	Phase 2
0.7165	Intermediate Similarity	NPD3947	Discontinued
0.7164	Intermediate Similarity	NPD3354	Phase 2
0.7159	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD3320	Approved
0.7158	Intermediate Similarity	NPD3318	Approved
0.7158	Intermediate Similarity	NPD3319	Phase 1
0.7158	Intermediate Similarity	NPD5213	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1037	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7666	Phase 3
0.7143	Intermediate Similarity	NPD6452	Discontinued
0.7143	Intermediate Similarity	NPD7665	Phase 2
0.7136	Intermediate Similarity	NPD7730	Approved
0.7136	Intermediate Similarity	NPD7731	Approved
0.7135	Intermediate Similarity	NPD6217	Discontinued
0.7135	Intermediate Similarity	NPD510	Phase 1
0.7134	Intermediate Similarity	NPD200	Phase 2
0.7134	Intermediate Similarity	NPD201	Phase 2
0.7129	Intermediate Similarity	NPD7952	Approved
0.7129	Intermediate Similarity	NPD7789	Approved
0.7129	Intermediate Similarity	NPD7951	Approved
0.7129	Intermediate Similarity	NPD7790	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