NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	206.13
Volume:	231.882
LogP:	3.687
LogD:	3.318
LogS:	-3.701
# Rotatable Bonds:	4
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.822
Synthetic Accessibility Score:	2.192
Fsp3:	0.462
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.377
MDCK Permeability:	3.547169399098493e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.463
Plasma Protein Binding (PPB):	94.36505126953125%
Volume Distribution (VD):	0.238
Pgp-substrate:	3.6475677490234375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.079
CYP1A2-substrate:	0.317
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.91
CYP2C9-inhibitor:	0.416
CYP2C9-substrate:	0.982
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.195

ADMET: Excretion

Clearance (CL):	0.778
Half-life (T1/2):	0.687

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.431
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.538
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.17
Carcinogencity:	0.072
Eye Corrosion:	0.018
Eye Irritation:	0.586
Respiratory Toxicity:	0.066

Download Data

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

Natural Product: NPC86670

Natural Product ID:	NPC86670
*Common Name:**	(R)-Ibuprophen
IUPAC Name:	(2R)-2-[4-(2-methylpropyl)phenyl]propanoic acid
Synonyms:	Ibuprofen
Standard InCHIKey:	HEFNNWSXXWATRW-SNVBAGLBSA-N
Standard InCHI:	InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)/t10-/m1/s1
SMILES:	CC(C)Cc1ccc(cc1)[C@@H](C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL427526
PubChem CID:	114864
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002551] Phenylpropanoic acids

*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
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jep.2005.01.054]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17996677]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31181920]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31418264]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10492	Artemisia montana	Species	Asteraceae	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
IC50	5
Ki	1
Others	16

Activity Type	# Activity
Cell Line	3
Individual Protein	3
Organism	4
Others	3
Protein Family	3
SINGLE PROTEIN	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4009	Cell Line	L1.2	Mus musculus	Activity	>	95.0	%	PMID[501006]
NPT102	Individual Protein	Interleukin-8	Homo sapiens	IC50	=	50.0	nM	PMID[501006]
NPT1260	Individual Protein	Anandamide amidohydrolase	Rattus norvegicus	IC50	=	204173.79	nM	PMID[501008]
NPT984	Cell Line	Hepatocyte		Cmax	=	1.3	nM	PMID[501013]
NPT984	Cell Line	Hepatocyte		Cmax	=	2600.0	nM	PMID[501013]
NPT3781	Protein Family	Interleukin-8 receptors, CXCR1/CXCR2	Homo sapiens	Inhibition	=	30.0	%	PMID[501004]
NPT3782	Protein Family	Prostaglandin G/H synthase (cyclooxygenase)	Mus musculus	Inhibition	=	37.0	%	PMID[501004]
NPT3781	Protein Family	Interleukin-8 receptors, CXCR1/CXCR2	Homo sapiens	IC50	=	110.0	nM	PMID[501004]
NPT605	Organism	Homo sapiens	Homo sapiens	F	=	80.0	%	PMID[501005]
NPT27	Others	Unspecified		Activity	>	95.0	%	PMID[501006]
NPT2	Others	Unspecified		Ki	=	11.3	nM	PMID[501009]
NPT694	Individual Protein	UDP-glucuronosyltransferase 1-3	Homo sapiens	Activity	=	121.0	pm/min/mg	PMID[501010]
NPT35	Others	n.a.		pKa	n.a.	4.44	n.a.	PMID[501012]
NPT23188	SINGLE PROTEIN	Amiloride-sensitive cation channel 3	Rattus norvegicus	IC50	=	389045.14	nM	PMID[501014]
NPT23188	SINGLE PROTEIN	Amiloride-sensitive cation channel 3	Rattus norvegicus	Imax	=	86.0	%	PMID[501014]
NPT23191	SINGLE PROTEIN	Acid-sensing ion channel 2	Rattus norvegicus	Imax	=	47.0	%	PMID[501014]
NPT23190	SINGLE PROTEIN	Acid-sensing ion channel 1	Rattus norvegicus	Imax	=	96.0	%	PMID[501014]
NPT23190	SINGLE PROTEIN	Acid-sensing ion channel 1	Rattus norvegicus	IC50	=	288403.15	nM	PMID[501014]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	3.52	%	PMID[501015]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	28.94	%	PMID[501016]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.17	%	PMID[501017]

☑ 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 NPC86670 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	189
0.1-0.2	977
0.2-0.3	3043
0.3-0.4	10840
0.4-0.5	16873
0.5-0.6	8671
0.6-0.7	1727
0.7-0.8	326
0.8-0.85	37
0.85-0.9	6
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC274455
1.0	High Similarity	NPC70940
0.9643	High Similarity	NPC322387
0.9167	High Similarity	NPC285773
0.908	High Similarity	NPC329064
0.8941	High Similarity	NPC44830
0.881	High Similarity	NPC127343
0.8737	High Similarity	NPC304873
0.8721	High Similarity	NPC288903
0.8602	High Similarity	NPC261947
0.8526	High Similarity	NPC217621
0.8523	High Similarity	NPC95965
0.8523	High Similarity	NPC294134
0.8495	Intermediate Similarity	NPC172925
0.8438	Intermediate Similarity	NPC128248
0.8438	Intermediate Similarity	NPC136810
0.8438	Intermediate Similarity	NPC225079
0.8438	Intermediate Similarity	NPC133809
0.8384	Intermediate Similarity	NPC37914
0.8384	Intermediate Similarity	NPC94751
0.8384	Intermediate Similarity	NPC142326
0.837	Intermediate Similarity	NPC86987
0.8351	Intermediate Similarity	NPC25458
0.8316	Intermediate Similarity	NPC253423
0.83	Intermediate Similarity	NPC249811
0.8295	Intermediate Similarity	NPC270507
0.8283	Intermediate Similarity	NPC105899
0.8265	Intermediate Similarity	NPC329556
0.8247	Intermediate Similarity	NPC264728
0.8229	Intermediate Similarity	NPC229242
0.8202	Intermediate Similarity	NPC267704
0.8182	Intermediate Similarity	NPC323103
0.8182	Intermediate Similarity	NPC329282
0.8182	Intermediate Similarity	NPC103387
0.8172	Intermediate Similarity	NPC317645
0.8172	Intermediate Similarity	NPC110704
0.8155	Intermediate Similarity	NPC66208
0.8152	Intermediate Similarity	NPC9822
0.814	Intermediate Similarity	NPC103488
0.8125	Intermediate Similarity	NPC477767
0.8125	Intermediate Similarity	NPC226041
0.8065	Intermediate Similarity	NPC84288
0.8061	Intermediate Similarity	NPC473325
0.8058	Intermediate Similarity	NPC475002
0.8058	Intermediate Similarity	NPC95126
0.8041	Intermediate Similarity	NPC120393
0.8021	Intermediate Similarity	NPC469893
0.8021	Intermediate Similarity	NPC61944
0.8	Intermediate Similarity	NPC471721
0.7959	Intermediate Similarity	NPC221825
0.7955	Intermediate Similarity	NPC285716
0.7955	Intermediate Similarity	NPC121800
0.7955	Intermediate Similarity	NPC17408
0.7955	Intermediate Similarity	NPC157055
0.7938	Intermediate Similarity	NPC469891
0.7938	Intermediate Similarity	NPC469890
0.7938	Intermediate Similarity	NPC469892
0.7931	Intermediate Similarity	NPC224544
0.7925	Intermediate Similarity	NPC186933
0.7921	Intermediate Similarity	NPC471186
0.79	Intermediate Similarity	NPC255676
0.79	Intermediate Similarity	NPC247976
0.7879	Intermediate Similarity	NPC469481
0.7872	Intermediate Similarity	NPC62765
0.7864	Intermediate Similarity	NPC318327
0.7857	Intermediate Similarity	NPC271475
0.7857	Intermediate Similarity	NPC160548
0.7857	Intermediate Similarity	NPC175852
0.7857	Intermediate Similarity	NPC210529
0.7857	Intermediate Similarity	NPC155429
0.7843	Intermediate Similarity	NPC83409
0.7843	Intermediate Similarity	NPC244933
0.7843	Intermediate Similarity	NPC185763
0.7843	Intermediate Similarity	NPC85560
0.7841	Intermediate Similarity	NPC170484
0.7826	Intermediate Similarity	NPC474211
0.78	Intermediate Similarity	NPC475978
0.78	Intermediate Similarity	NPC284477
0.78	Intermediate Similarity	NPC474820
0.7791	Intermediate Similarity	NPC189371
0.7778	Intermediate Similarity	NPC7435
0.7778	Intermediate Similarity	NPC230068
0.7757	Intermediate Similarity	NPC221275
0.7745	Intermediate Similarity	NPC172483
0.7736	Intermediate Similarity	NPC93287
0.7723	Intermediate Similarity	NPC160382
0.7723	Intermediate Similarity	NPC274443
0.7717	Intermediate Similarity	NPC474354
0.7714	Intermediate Similarity	NPC474057
0.7708	Intermediate Similarity	NPC323164
0.77	Intermediate Similarity	NPC94487
0.77	Intermediate Similarity	NPC282895
0.77	Intermediate Similarity	NPC52472
0.767	Intermediate Similarity	NPC100767
0.766	Intermediate Similarity	NPC477704
0.766	Intermediate Similarity	NPC477693
0.7647	Intermediate Similarity	NPC19136
0.7647	Intermediate Similarity	NPC472221
0.7647	Intermediate Similarity	NPC472222
0.7642	Intermediate Similarity	NPC292834
0.7634	Intermediate Similarity	NPC93843
0.7634	Intermediate Similarity	NPC318107
0.7624	Intermediate Similarity	NPC222390
0.7624	Intermediate Similarity	NPC244427
0.7615	Intermediate Similarity	NPC212891
0.7614	Intermediate Similarity	NPC298023
0.7609	Intermediate Similarity	NPC168855
0.7604	Intermediate Similarity	NPC141607
0.7604	Intermediate Similarity	NPC187725
0.76	Intermediate Similarity	NPC245561
0.76	Intermediate Similarity	NPC203925
0.76	Intermediate Similarity	NPC476042
0.76	Intermediate Similarity	NPC146351
0.76	Intermediate Similarity	NPC228435
0.7596	Intermediate Similarity	NPC112903
0.7593	Intermediate Similarity	NPC476357
0.7579	Intermediate Similarity	NPC1793
0.7579	Intermediate Similarity	NPC220893
0.7573	Intermediate Similarity	NPC321670
0.7558	Intermediate Similarity	NPC285679
0.7551	Intermediate Similarity	NPC130398
0.7549	Intermediate Similarity	NPC13426
0.7545	Intermediate Similarity	NPC160199
0.7545	Intermediate Similarity	NPC45794
0.7527	Intermediate Similarity	NPC252067
0.7525	Intermediate Similarity	NPC70624
0.7524	Intermediate Similarity	NPC85493
0.75	Intermediate Similarity	NPC109241
0.75	Intermediate Similarity	NPC225060
0.75	Intermediate Similarity	NPC477770
0.75	Intermediate Similarity	NPC78701
0.75	Intermediate Similarity	NPC317280
0.75	Intermediate Similarity	NPC35448
0.75	Intermediate Similarity	NPC153053
0.75	Intermediate Similarity	NPC329387
0.7477	Intermediate Similarity	NPC471188
0.7477	Intermediate Similarity	NPC328694
0.7477	Intermediate Similarity	NPC321852
0.7477	Intermediate Similarity	NPC471189
0.7473	Intermediate Similarity	NPC133050
0.7473	Intermediate Similarity	NPC145053
0.7471	Intermediate Similarity	NPC108218
0.7451	Intermediate Similarity	NPC188895
0.7449	Intermediate Similarity	NPC261181
0.7449	Intermediate Similarity	NPC34243
0.7442	Intermediate Similarity	NPC74458
0.7431	Intermediate Similarity	NPC93181
0.7429	Intermediate Similarity	NPC21929
0.7429	Intermediate Similarity	NPC228737
0.7426	Intermediate Similarity	NPC280869
0.7426	Intermediate Similarity	NPC12730
0.7426	Intermediate Similarity	NPC325497
0.7423	Intermediate Similarity	NPC133461
0.7411	Intermediate Similarity	NPC472708
0.7407	Intermediate Similarity	NPC128368
0.7407	Intermediate Similarity	NPC143768
0.7404	Intermediate Similarity	NPC13495
0.74	Intermediate Similarity	NPC270654
0.74	Intermediate Similarity	NPC249912
0.74	Intermediate Similarity	NPC324569
0.74	Intermediate Similarity	NPC156021
0.74	Intermediate Similarity	NPC276775
0.74	Intermediate Similarity	NPC293628
0.74	Intermediate Similarity	NPC92754
0.74	Intermediate Similarity	NPC289201
0.74	Intermediate Similarity	NPC10781
0.74	Intermediate Similarity	NPC122493
0.7396	Intermediate Similarity	NPC231591
0.7383	Intermediate Similarity	NPC265513
0.7383	Intermediate Similarity	NPC260818
0.7374	Intermediate Similarity	NPC206764
0.7368	Intermediate Similarity	NPC69057
0.7368	Intermediate Similarity	NPC167323
0.7368	Intermediate Similarity	NPC269923
0.7368	Intermediate Similarity	NPC89377
0.7368	Intermediate Similarity	NPC25168
0.7364	Intermediate Similarity	NPC9274
0.7363	Intermediate Similarity	NPC477703
0.7363	Intermediate Similarity	NPC328178
0.7363	Intermediate Similarity	NPC190567
0.7358	Intermediate Similarity	NPC31274
0.7347	Intermediate Similarity	NPC314690
0.7347	Intermediate Similarity	NPC153885
0.7345	Intermediate Similarity	NPC183339
0.7345	Intermediate Similarity	NPC133389
0.7345	Intermediate Similarity	NPC234337
0.734	Intermediate Similarity	NPC475710
0.7339	Intermediate Similarity	NPC294458
0.7333	Intermediate Similarity	NPC50192
0.7333	Intermediate Similarity	NPC317592
0.7327	Intermediate Similarity	NPC260000
0.7327	Intermediate Similarity	NPC145052
0.732	Intermediate Similarity	NPC26224
0.732	Intermediate Similarity	NPC258627
0.7315	Intermediate Similarity	NPC82899
0.7315	Intermediate Similarity	NPC280789
0.7315	Intermediate Similarity	NPC270699
0.7312	Intermediate Similarity	NPC197581
0.7308	Intermediate Similarity	NPC31786
0.7297	Intermediate Similarity	NPC158157

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 NPC86670 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	842
0.2-0.3	1365
0.3-0.4	2960
0.4-0.5	2355
0.5-0.6	1034
0.6-0.7	320
0.7-0.8	57
0.8-0.85	13
0.85-0.9	8
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1086	Approved
1.0	High Similarity	NPD1090	Approved
1.0	High Similarity	NPD1089	Approved
0.9881	High Similarity	NPD800	Approved
0.9767	High Similarity	NPD1088	Approved
0.9643	High Similarity	NPD1087	Approved
0.9545	High Similarity	NPD1693	Approved
0.9205	High Similarity	NPD1239	Approved
0.9167	High Similarity	NPD9491	Approved
0.913	High Similarity	NPD2066	Phase 3
0.9121	High Similarity	NPD1566	Phase 3
0.9121	High Similarity	NPD1565	Approved
0.9121	High Similarity	NPD1564	Approved
0.8791	High Similarity	NPD1563	Approved
0.8764	High Similarity	NPD5347	Phase 2
0.8764	High Similarity	NPD5346	Phase 2
0.8706	High Similarity	NPD226	Approved
0.869	High Similarity	NPD9490	Approved
0.8602	High Similarity	NPD1989	Approved
0.8587	High Similarity	NPD5122	Clinical (unspecified phase)
0.8539	High Similarity	NPD4793	Discontinued
0.8495	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD227	Approved
0.8353	Intermediate Similarity	NPD225	Approved
0.8265	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.8265	Intermediate Similarity	NPD1929	Approved
0.8265	Intermediate Similarity	NPD1930	Approved
0.8261	Intermediate Similarity	NPD3672	Approved
0.8261	Intermediate Similarity	NPD3673	Approved
0.798	Intermediate Similarity	NPD1932	Approved
0.7872	Intermediate Similarity	NPD9258	Approved
0.7872	Intermediate Similarity	NPD9256	Approved
0.7864	Intermediate Similarity	NPD2329	Discontinued
0.7857	Intermediate Similarity	NPD9495	Approved
0.7857	Intermediate Similarity	NPD253	Approved
0.7849	Intermediate Similarity	NPD1101	Approved
0.783	Intermediate Similarity	NPD1280	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD1317	Discontinued
0.7757	Intermediate Similarity	NPD5951	Approved
0.7692	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD2652	Approved
0.7664	Intermediate Similarity	NPD2650	Approved
0.7653	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5909	Discontinued
0.7634	Intermediate Similarity	NPD9257	Approved
0.7634	Intermediate Similarity	NPD9259	Approved
0.76	Intermediate Similarity	NPD3097	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD3643	Approved
0.7547	Intermediate Similarity	NPD3644	Approved
0.7547	Intermediate Similarity	NPD3642	Approved
0.7449	Intermediate Similarity	NPD1409	Phase 3
0.7449	Intermediate Similarity	NPD1202	Approved
0.7449	Intermediate Similarity	NPD1066	Discontinued
0.7431	Intermediate Similarity	NPD2629	Approved
0.7411	Intermediate Similarity	NPD1245	Approved
0.7407	Intermediate Similarity	NPD1279	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD9566	Approved
0.7383	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6647	Phase 2
0.7379	Intermediate Similarity	NPD5765	Approved
0.7345	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6685	Approved
0.7308	Intermediate Similarity	NPD164	Approved
0.729	Intermediate Similarity	NPD1752	Approved
0.729	Intermediate Similarity	NPD4233	Approved
0.729	Intermediate Similarity	NPD4234	Approved
0.729	Intermediate Similarity	NPD1756	Approved
0.7273	Intermediate Similarity	NPD1246	Approved
0.7222	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD2182	Approved
0.7193	Intermediate Similarity	NPD5306	Approved
0.7193	Intermediate Similarity	NPD5305	Approved
0.7182	Intermediate Similarity	NPD1370	Approved
0.7182	Intermediate Similarity	NPD1371	Approved
0.7182	Intermediate Similarity	NPD1374	Approved
0.7182	Intermediate Similarity	NPD1373	Approved
0.7172	Intermediate Similarity	NPD7631	Approved
0.7158	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD9508	Approved
0.7143	Intermediate Similarity	NPD1237	Approved
0.713	Intermediate Similarity	NPD3646	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5278	Discontinued
0.7128	Intermediate Similarity	NPD3971	Phase 1
0.7117	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4766	Approved
0.7113	Intermediate Similarity	NPD531	Approved
0.7105	Intermediate Similarity	NPD5981	Approved
0.7105	Intermediate Similarity	NPD1855	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4105	Approved
0.7105	Intermediate Similarity	NPD4102	Approved
0.7091	Intermediate Similarity	NPD181	Approved
0.7091	Intermediate Similarity	NPD5277	Phase 2
0.7091	Intermediate Similarity	NPD2607	Approved
0.7087	Intermediate Similarity	NPD1238	Approved
0.7087	Intermediate Similarity	NPD1067	Discontinued
0.7075	Intermediate Similarity	NPD1018	Approved
0.7075	Intermediate Similarity	NPD5048	Discontinued
0.7071	Intermediate Similarity	NPD530	Approved
0.7071	Intermediate Similarity	NPD7609	Phase 3
0.7069	Intermediate Similarity	NPD4217	Approved
0.7069	Intermediate Similarity	NPD2611	Approved
0.7069	Intermediate Similarity	NPD4216	Approved
0.7069	Intermediate Similarity	NPD3131	Approved
0.7069	Intermediate Similarity	NPD4807	Approved
0.7069	Intermediate Similarity	NPD4215	Approved
0.7069	Intermediate Similarity	NPD4218	Approved
0.7069	Intermediate Similarity	NPD3132	Approved
0.7069	Intermediate Similarity	NPD2609	Approved
0.7069	Intermediate Similarity	NPD2612	Approved
0.7069	Intermediate Similarity	NPD4806	Approved
0.7069	Intermediate Similarity	NPD2608	Approved
0.7069	Intermediate Similarity	NPD2610	Approved
0.7064	Intermediate Similarity	NPD189	Phase 3
0.7064	Intermediate Similarity	NPD188	Approved
0.7059	Intermediate Similarity	NPD3495	Discontinued
0.7043	Intermediate Similarity	NPD2345	Approved
0.7034	Intermediate Similarity	NPD1283	Approved
0.703	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD9260	Approved
0.703	Intermediate Similarity	NPD4814	Discontinued
0.703	Intermediate Similarity	NPD6049	Phase 2
0.7027	Intermediate Similarity	NPD3598	Phase 3
0.701	Intermediate Similarity	NPD650	Approved
0.7009	Intermediate Similarity	NPD467	Phase 1
0.7	Intermediate Similarity	NPD9716	Approved
0.6991	Remote Similarity	NPD4574	Approved
0.6991	Remote Similarity	NPD4576	Approved
0.6989	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4135	Approved
0.6983	Remote Similarity	NPD4106	Approved
0.6983	Remote Similarity	NPD4136	Approved
0.6972	Remote Similarity	NPD2067	Discontinued
0.6957	Remote Similarity	NPD6994	Approved
0.6957	Remote Similarity	NPD6993	Approved
0.6949	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6858	Approved
0.6937	Remote Similarity	NPD7094	Approved
0.6931	Remote Similarity	NPD719	Approved
0.6931	Remote Similarity	NPD720	Approved
0.6931	Remote Similarity	NPD845	Approved
0.693	Remote Similarity	NPD7610	Discontinued
0.6923	Remote Similarity	NPD7798	Approved
0.6923	Remote Similarity	NPD5618	Discontinued
0.6916	Remote Similarity	NPD1040	Phase 2
0.6915	Remote Similarity	NPD942	Approved
0.6903	Remote Similarity	NPD255	Approved
0.6903	Remote Similarity	NPD256	Approved
0.6903	Remote Similarity	NPD4198	Discontinued
0.6897	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4199	Phase 3
0.6893	Remote Similarity	NPD288	Approved
0.6881	Remote Similarity	NPD476	Approved
0.687	Remote Similarity	NPD4479	Discontinued
0.687	Remote Similarity	NPD7009	Phase 2
0.6864	Remote Similarity	NPD1608	Approved
0.6848	Remote Similarity	NPD9294	Approved
0.6847	Remote Similarity	NPD6912	Phase 3
0.6842	Remote Similarity	NPD3797	Approved
0.6833	Remote Similarity	NPD6563	Approved
0.6833	Remote Similarity	NPD6564	Approved
0.6833	Remote Similarity	NPD6565	Approved
0.6832	Remote Similarity	NPD752	Approved
0.6796	Remote Similarity	NPD844	Approved
0.6789	Remote Similarity	NPD9267	Approved
0.6789	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD9264	Approved
0.6789	Remote Similarity	NPD9263	Approved
0.678	Remote Similarity	NPD1281	Approved
0.6774	Remote Similarity	NPD7715	Approved
0.6774	Remote Similarity	NPD7714	Approved
0.6765	Remote Similarity	NPD3718	Approved
0.6765	Remote Similarity	NPD3719	Approved
0.6762	Remote Similarity	NPD3020	Approved
0.6752	Remote Similarity	NPD3019	Approved
0.6752	Remote Similarity	NPD2932	Approved
0.6748	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7008	Discontinued
0.6729	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD74	Approved
0.6727	Remote Similarity	NPD9266	Approved
0.6726	Remote Similarity	NPD1681	Approved
0.6726	Remote Similarity	NPD6010	Discontinued
0.6726	Remote Similarity	NPD1682	Approved
0.6726	Remote Similarity	NPD1680	Approved
0.6724	Remote Similarity	NPD3798	Phase 3
0.6721	Remote Similarity	NPD3664	Approved
0.6721	Remote Similarity	NPD3662	Phase 3
0.6721	Remote Similarity	NPD3661	Approved
0.6721	Remote Similarity	NPD3663	Approved
0.6699	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5162	Approved
0.6696	Remote Similarity	NPD9493	Approved
0.6696	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4879	Approved
0.6694	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD5240	Approved
0.6667	Remote Similarity	NPD5239	Approved
0.6667	Remote Similarity	NPD9538	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