NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.18
Volume:	307.134
LogP:	4.898
LogD:	3.957
LogS:	-4.982
# Rotatable Bonds:	5
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.888
Synthetic Accessibility Score:	2.376
Fsp3:	0.588
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.885
MDCK Permeability:	1.9862687622662634e-05
Pgp-inhibitor:	0.149
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.187
20% Bioavailability (F20%):	0.73
30% Bioavailability (F30%):	0.349

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.095
Plasma Protein Binding (PPB):	98.84312438964844%
Volume Distribution (VD):	0.231
Pgp-substrate:	2.686138391494751%

ADMET: Metabolism

CYP1A2-inhibitor:	0.179
CYP1A2-substrate:	0.804
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.373
CYP2C9-substrate:	0.971
CYP2D6-inhibitor:	0.445
CYP2D6-substrate:	0.52
CYP3A4-inhibitor:	0.065
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	1.513
Half-life (T1/2):	0.662

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.277
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.59
Skin Sensitization:	0.116
Carcinogencity:	0.035
Eye Corrosion:	0.038
Eye Irritation:	0.652
Respiratory Toxicity:	0.641

Download Data

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

Natural Product: NPC86987

Natural Product ID:	NPC86987
*Common Name:**	3-(3,5-Ditert-Butyl-4-Fluorophenyl)Propanoic Acid
IUPAC Name:	3-(3,5-ditert-butyl-4-fluorophenyl)propanoic acid
Synonyms:
Standard InCHIKey:	XAOZUAPXTWNERM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H25FO2/c1-16(2,3)12-9-11(7-8-14(19)20)10-13(15(12)18)17(4,5)6/h9-10H,7-8H2,1-6H3,(H,19,20)
SMILES:	OC(=O)CCc1cc(c(c(c1)C(C)(C)C)F)C(C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3104961
PubChem CID:	73891091
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
NPO32453	Streptomyces sp. TC1	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24387661]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3
Others	6

Activity Type	# Activity
NON-MOLECULAR	5
Others	1
Uncleic Acid	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1514	Uncleic Acid	DNA	Bos taurus	Kapp	=	1.6	10'5/M	PMID[448658]
NPT1514	Uncleic Acid	DNA	Bos taurus	Kq	=	1.71	10'4/M	PMID[448658]
NPT1514	Uncleic Acid	DNA	Bos taurus	Kb	=	3.13	10'4/M	PMID[448658]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8400.0	nM	PMID[448658]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	25800.0	nM	PMID[448658]
NPT1	Others	Radical scavenging activity		IC50	=	8400.0	nM	PMID[448658]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	6736.5	umol/g	PMID[448658]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	4.5	mg/g	PMID[448658]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	6031.1	mmol/g	PMID[448658]

☑ 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 NPC86987 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	959
0.2-0.3	3103
0.3-0.4	11219
0.4-0.5	19455
0.5-0.6	6573
0.6-0.7	1038
0.7-0.8	138
0.8-0.85	18
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8837	High Similarity	NPC44830
0.8556	High Similarity	NPC329064
0.8542	High Similarity	NPC128248
0.8542	High Similarity	NPC133809
0.8542	High Similarity	NPC136810
0.8542	High Similarity	NPC225079
0.8488	Intermediate Similarity	NPC127343
0.8444	Intermediate Similarity	NPC322387
0.837	Intermediate Similarity	NPC86670
0.837	Intermediate Similarity	NPC70940
0.837	Intermediate Similarity	NPC274455
0.8351	Intermediate Similarity	NPC264728
0.8229	Intermediate Similarity	NPC226041
0.8202	Intermediate Similarity	NPC285773
0.8144	Intermediate Similarity	NPC120393
0.8125	Intermediate Similarity	NPC469893
0.8119	Intermediate Similarity	NPC94751
0.8119	Intermediate Similarity	NPC142326
0.8061	Intermediate Similarity	NPC221825
0.8041	Intermediate Similarity	NPC469891
0.8041	Intermediate Similarity	NPC469890
0.8041	Intermediate Similarity	NPC469892
0.8022	Intermediate Similarity	NPC95965
0.8021	Intermediate Similarity	NPC172925
0.7941	Intermediate Similarity	NPC85560
0.7941	Intermediate Similarity	NPC244933
0.7912	Intermediate Similarity	NPC267704
0.7857	Intermediate Similarity	NPC477767
0.7822	Intermediate Similarity	NPC329556
0.781	Intermediate Similarity	NPC95126
0.781	Intermediate Similarity	NPC475002
0.7802	Intermediate Similarity	NPC288903
0.7789	Intermediate Similarity	NPC84288
0.7778	Intermediate Similarity	NPC271475
0.7745	Intermediate Similarity	NPC329282
0.77	Intermediate Similarity	NPC54647
0.767	Intermediate Similarity	NPC471186
0.7664	Intermediate Similarity	NPC93287
0.7634	Intermediate Similarity	NPC294134
0.7624	Intermediate Similarity	NPC94487
0.7596	Intermediate Similarity	NPC37914
0.7593	Intermediate Similarity	NPC471721
0.7579	Intermediate Similarity	NPC477693
0.7579	Intermediate Similarity	NPC477704
0.7576	Intermediate Similarity	NPC261947
0.7549	Intermediate Similarity	NPC475978
0.7549	Intermediate Similarity	NPC474820
0.7526	Intermediate Similarity	NPC187725
0.7526	Intermediate Similarity	NPC141607
0.7526	Intermediate Similarity	NPC317645
0.7524	Intermediate Similarity	NPC21929
0.7524	Intermediate Similarity	NPC249811
0.7523	Intermediate Similarity	NPC221275
0.75	Intermediate Similarity	NPC9822
0.75	Intermediate Similarity	NPC477476
0.75	Intermediate Similarity	NPC323103
0.75	Intermediate Similarity	NPC477475
0.7476	Intermediate Similarity	NPC247976
0.7455	Intermediate Similarity	NPC9274
0.7451	Intermediate Similarity	NPC469481
0.7449	Intermediate Similarity	NPC323164
0.7431	Intermediate Similarity	NPC294458
0.7426	Intermediate Similarity	NPC229242
0.7419	Intermediate Similarity	NPC270507
0.7404	Intermediate Similarity	NPC19136
0.7387	Intermediate Similarity	NPC212891
0.7379	Intermediate Similarity	NPC304873
0.7358	Intermediate Similarity	NPC112903
0.7356	Intermediate Similarity	NPC155429
0.7353	Intermediate Similarity	NPC217621
0.7353	Intermediate Similarity	NPC7435
0.7347	Intermediate Similarity	NPC110704
0.7321	Intermediate Similarity	NPC45794
0.732	Intermediate Similarity	NPC231591
0.732	Intermediate Similarity	NPC298115
0.7315	Intermediate Similarity	NPC265513
0.7312	Intermediate Similarity	NPC230068
0.7312	Intermediate Similarity	NPC103387
0.73	Intermediate Similarity	NPC206764
0.729	Intermediate Similarity	NPC475006
0.7283	Intermediate Similarity	NPC121800
0.7264	Intermediate Similarity	NPC100767
0.7263	Intermediate Similarity	NPC475710
0.7253	Intermediate Similarity	NPC103488
0.7248	Intermediate Similarity	NPC280789
0.7248	Intermediate Similarity	NPC471189
0.7248	Intermediate Similarity	NPC66208
0.7248	Intermediate Similarity	NPC471188
0.7234	Intermediate Similarity	NPC477770
0.7212	Intermediate Similarity	NPC25458
0.7193	Intermediate Similarity	NPC202015
0.7184	Intermediate Similarity	NPC228435
0.7184	Intermediate Similarity	NPC12730
0.7182	Intermediate Similarity	NPC470253
0.7174	Intermediate Similarity	NPC272260
0.7174	Intermediate Similarity	NPC170484
0.7172	Intermediate Similarity	NPC125226
0.7172	Intermediate Similarity	NPC220596
0.717	Intermediate Similarity	NPC321670
0.717	Intermediate Similarity	NPC105899
0.7159	Intermediate Similarity	NPC74458
0.7157	Intermediate Similarity	NPC253423
0.7157	Intermediate Similarity	NPC293628
0.7157	Intermediate Similarity	NPC10781
0.7157	Intermediate Similarity	NPC122493
0.7157	Intermediate Similarity	NPC251579
0.7157	Intermediate Similarity	NPC324569
0.7157	Intermediate Similarity	NPC133135
0.7143	Intermediate Similarity	NPC255676
0.7143	Intermediate Similarity	NPC298023
0.7143	Intermediate Similarity	NPC9796
0.713	Intermediate Similarity	NPC133389
0.713	Intermediate Similarity	NPC470039
0.713	Intermediate Similarity	NPC183339
0.713	Intermediate Similarity	NPC318327
0.713	Intermediate Similarity	NPC234337
0.7111	Intermediate Similarity	NPC189371
0.7103	Intermediate Similarity	NPC83409
0.7103	Intermediate Similarity	NPC185763
0.71	Intermediate Similarity	NPC323420
0.71	Intermediate Similarity	NPC59677
0.7097	Intermediate Similarity	NPC17408
0.7097	Intermediate Similarity	NPC157055
0.7097	Intermediate Similarity	NPC285716
0.7091	Intermediate Similarity	NPC218855
0.7087	Intermediate Similarity	NPC175852
0.7087	Intermediate Similarity	NPC210529
0.7087	Intermediate Similarity	NPC160548
0.7087	Intermediate Similarity	NPC317280
0.7087	Intermediate Similarity	NPC329387
0.7079	Intermediate Similarity	NPC285679
0.7075	Intermediate Similarity	NPC472222
0.7075	Intermediate Similarity	NPC472221
0.7071	Intermediate Similarity	NPC62765
0.7071	Intermediate Similarity	NPC26224
0.7069	Intermediate Similarity	NPC164852
0.7069	Intermediate Similarity	NPC241001
0.7065	Intermediate Similarity	NPC224544
0.7054	Intermediate Similarity	NPC186933
0.7054	Intermediate Similarity	NPC93181
0.7054	Intermediate Similarity	NPC215419
0.7054	Intermediate Similarity	NPC217111
0.7048	Intermediate Similarity	NPC474112
0.7048	Intermediate Similarity	NPC284477
0.7043	Intermediate Similarity	NPC42657
0.7043	Intermediate Similarity	NPC204784
0.7037	Intermediate Similarity	NPC228737
0.703	Intermediate Similarity	NPC34243
0.7027	Intermediate Similarity	NPC206414
0.7027	Intermediate Similarity	NPC471481
0.7027	Intermediate Similarity	NPC287055
0.7027	Intermediate Similarity	NPC242957
0.7027	Intermediate Similarity	NPC143768
0.7027	Intermediate Similarity	NPC306977
0.7019	Intermediate Similarity	NPC245561
0.701	Intermediate Similarity	NPC243166
0.7009	Intermediate Similarity	NPC249340
0.7009	Intermediate Similarity	NPC474307
0.7009	Intermediate Similarity	NPC269923
0.7009	Intermediate Similarity	NPC293831
0.7009	Intermediate Similarity	NPC369
0.7009	Intermediate Similarity	NPC167323
0.7009	Intermediate Similarity	NPC162935
0.7009	Intermediate Similarity	NPC172483
0.7	Intermediate Similarity	NPC475023
0.7	Intermediate Similarity	NPC475059
0.699	Remote Similarity	NPC239185
0.699	Remote Similarity	NPC289201
0.699	Remote Similarity	NPC265220
0.699	Remote Similarity	NPC240042
0.6983	Remote Similarity	NPC474223
0.6983	Remote Similarity	NPC475827
0.6981	Remote Similarity	NPC274443
0.6981	Remote Similarity	NPC160382
0.6972	Remote Similarity	NPC31274
0.6972	Remote Similarity	NPC469636
0.6966	Remote Similarity	NPC208302
0.6964	Remote Similarity	NPC130591
0.6964	Remote Similarity	NPC234637
0.6952	Remote Similarity	NPC52472
0.6952	Remote Similarity	NPC282895
0.6949	Remote Similarity	NPC121168
0.6947	Remote Similarity	NPC73637
0.6947	Remote Similarity	NPC121478
0.6944	Remote Similarity	NPC475905
0.6944	Remote Similarity	NPC25385
0.6944	Remote Similarity	NPC193640
0.6937	Remote Similarity	NPC292834
0.6931	Remote Similarity	NPC155232
0.6931	Remote Similarity	NPC475057
0.6931	Remote Similarity	NPC153885
0.693	Remote Similarity	NPC105141
0.693	Remote Similarity	NPC469843
0.693	Remote Similarity	NPC242764
0.693	Remote Similarity	NPC83718
0.6923	Remote Similarity	NPC179411
0.6923	Remote Similarity	NPC145052
0.6923	Remote Similarity	NPC134882
0.6923	Remote Similarity	NPC75724
0.6923	Remote Similarity	NPC322598

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 NPC86987 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	825
0.2-0.3	1613
0.3-0.4	3100
0.4-0.5	2274
0.5-0.6	909
0.6-0.7	204
0.7-0.8	36
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8587	High Similarity	NPD1088	Approved
0.8462	Intermediate Similarity	NPD5347	Phase 2
0.8462	Intermediate Similarity	NPD5346	Phase 2
0.8444	Intermediate Similarity	NPD4793	Discontinued
0.8391	Intermediate Similarity	NPD226	Approved
0.837	Intermediate Similarity	NPD1086	Approved
0.837	Intermediate Similarity	NPD1090	Approved
0.837	Intermediate Similarity	NPD1089	Approved
0.8298	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD800	Approved
0.8229	Intermediate Similarity	NPD1565	Approved
0.8229	Intermediate Similarity	NPD1566	Phase 3
0.8229	Intermediate Similarity	NPD1564	Approved
0.8202	Intermediate Similarity	NPD9491	Approved
0.8046	Intermediate Similarity	NPD225	Approved
0.8046	Intermediate Similarity	NPD227	Approved
0.8043	Intermediate Similarity	NPD1087	Approved
0.8021	Intermediate Similarity	NPD1693	Approved
0.8021	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD3672	Approved
0.7979	Intermediate Similarity	NPD3673	Approved
0.7917	Intermediate Similarity	NPD1563	Approved
0.7895	Intermediate Similarity	NPD1239	Approved
0.7879	Intermediate Similarity	NPD2066	Phase 3
0.7826	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD1930	Approved
0.7822	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD1929	Approved
0.7788	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD9490	Approved
0.7619	Intermediate Similarity	NPD2329	Discontinued
0.7593	Intermediate Similarity	NPD6010	Discontinued
0.7576	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1989	Approved
0.7525	Intermediate Similarity	NPD3097	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD5951	Approved
0.7426	Intermediate Similarity	NPD253	Approved
0.7404	Intermediate Similarity	NPD5909	Discontinued
0.7383	Intermediate Similarity	NPD5278	Discontinued
0.7379	Intermediate Similarity	NPD1932	Approved
0.7207	Intermediate Similarity	NPD2629	Approved
0.72	Intermediate Similarity	NPD1066	Discontinued
0.7157	Intermediate Similarity	NPD9566	Approved
0.7156	Intermediate Similarity	NPD3644	Approved
0.7156	Intermediate Similarity	NPD3642	Approved
0.7156	Intermediate Similarity	NPD3643	Approved
0.7143	Intermediate Similarity	NPD6647	Phase 2
0.7143	Intermediate Similarity	NPD5765	Approved
0.713	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD4199	Phase 3
0.7129	Intermediate Similarity	NPD6049	Phase 2
0.7129	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6685	Approved
0.7087	Intermediate Similarity	NPD9495	Approved
0.708	Intermediate Similarity	NPD3797	Approved
0.7071	Intermediate Similarity	NPD9258	Approved
0.7071	Intermediate Similarity	NPD9256	Approved
0.7064	Intermediate Similarity	NPD4234	Approved
0.7064	Intermediate Similarity	NPD4233	Approved
0.7053	Intermediate Similarity	NPD3971	Phase 1
0.7043	Intermediate Similarity	NPD1855	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6858	Approved
0.7027	Intermediate Similarity	NPD7094	Approved
0.7009	Intermediate Similarity	NPD5048	Discontinued
0.7009	Intermediate Similarity	NPD1018	Approved
0.7	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.699	Remote Similarity	NPD3495	Discontinued
0.6981	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD2650	Approved
0.6964	Remote Similarity	NPD2652	Approved
0.6957	Remote Similarity	NPD3798	Phase 3
0.6957	Remote Similarity	NPD7009	Phase 2
0.6917	Remote Similarity	NPD6565	Approved
0.6917	Remote Similarity	NPD6564	Approved
0.6917	Remote Similarity	NPD6563	Approved
0.6909	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1752	Approved
0.6909	Remote Similarity	NPD1756	Approved
0.6909	Remote Similarity	NPD1317	Discontinued
0.6903	Remote Similarity	NPD4766	Approved
0.6875	Remote Similarity	NPD2607	Approved
0.6857	Remote Similarity	NPD7798	Approved
0.6837	Remote Similarity	NPD9259	Approved
0.6837	Remote Similarity	NPD9257	Approved
0.6832	Remote Similarity	NPD7609	Phase 3
0.6829	Remote Similarity	NPD7008	Discontinued
0.6814	Remote Similarity	NPD3598	Phase 3
0.6796	Remote Similarity	NPD3772	Phase 3
0.6789	Remote Similarity	NPD467	Phase 1
0.6765	Remote Similarity	NPD7631	Approved
0.6754	Remote Similarity	NPD747	Discontinued
0.6752	Remote Similarity	NPD6993	Approved
0.6752	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6994	Approved
0.6739	Remote Similarity	NPD9716	Approved
0.6731	Remote Similarity	NPD1809	Phase 2
0.6724	Remote Similarity	NPD7610	Discontinued
0.67	Remote Similarity	NPD1101	Approved
0.6699	Remote Similarity	NPD719	Approved
0.6699	Remote Similarity	NPD1202	Approved
0.6699	Remote Similarity	NPD720	Approved
0.6698	Remote Similarity	NPD1067	Discontinued
0.6696	Remote Similarity	NPD188	Approved
0.6696	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD189	Phase 3
0.6695	Remote Similarity	NPD2345	Approved
0.6667	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2994	Approved
0.6667	Remote Similarity	NPD2182	Approved
0.6667	Remote Similarity	NPD476	Approved
0.6639	Remote Similarity	NPD3881	Discontinued
0.6638	Remote Similarity	NPD5162	Approved
0.6637	Remote Similarity	NPD6912	Phase 3
0.6635	Remote Similarity	NPD4094	Approved
0.661	Remote Similarity	NPD5981	Approved
0.661	Remote Similarity	NPD4105	Approved
0.661	Remote Similarity	NPD4102	Approved
0.6607	Remote Similarity	NPD2067	Discontinued
0.6606	Remote Similarity	NPD164	Approved
0.6602	Remote Similarity	NPD752	Approved
0.66	Remote Similarity	NPD650	Approved
0.6581	Remote Similarity	NPD6065	Approved
0.6579	Remote Similarity	NPD5277	Phase 2
0.6562	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.656	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD4382	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5306	Approved
0.6555	Remote Similarity	NPD5305	Approved
0.6555	Remote Similarity	NPD3019	Approved
0.6555	Remote Similarity	NPD2932	Approved
0.6552	Remote Similarity	NPD4198	Discontinued
0.6552	Remote Similarity	NPD3317	Approved
0.6538	Remote Similarity	NPD845	Approved
0.6529	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD2617	Discontinued
0.6522	Remote Similarity	NPD1682	Approved
0.6522	Remote Similarity	NPD1681	Approved
0.6522	Remote Similarity	NPD1680	Approved
0.6509	Remote Similarity	NPD4657	Approved
0.6509	Remote Similarity	NPD4655	Approved
0.6509	Remote Similarity	NPD1875	Phase 1
0.6504	Remote Similarity	NPD1164	Approved
0.65	Remote Similarity	NPD4136	Approved
0.65	Remote Similarity	NPD4135	Approved
0.65	Remote Similarity	NPD2946	Phase 2
0.65	Remote Similarity	NPD4106	Approved
0.6495	Remote Similarity	NPD942	Approved
0.6486	Remote Similarity	NPD5704	Approved
0.6486	Remote Similarity	NPD5706	Approved
0.6486	Remote Similarity	NPD5705	Approved
0.6476	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4814	Discontinued
0.6471	Remote Similarity	NPD3032	Approved
0.6471	Remote Similarity	NPD3031	Approved
0.6471	Remote Similarity	NPD3030	Approved
0.6466	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD1246	Approved
0.6455	Remote Similarity	NPD1237	Approved
0.6452	Remote Similarity	NPD6085	Phase 2
0.6452	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5926	Approved
0.6446	Remote Similarity	NPD2609	Approved
0.6446	Remote Similarity	NPD2612	Approved
0.6446	Remote Similarity	NPD3603	Phase 3
0.6446	Remote Similarity	NPD4806	Approved
0.6446	Remote Similarity	NPD4216	Approved
0.6446	Remote Similarity	NPD4807	Approved
0.6446	Remote Similarity	NPD2611	Approved
0.6446	Remote Similarity	NPD3132	Approved
0.6446	Remote Similarity	NPD2608	Approved
0.6446	Remote Similarity	NPD2610	Approved
0.6446	Remote Similarity	NPD4217	Approved
0.6446	Remote Similarity	NPD4218	Approved
0.6446	Remote Similarity	NPD3131	Approved
0.6446	Remote Similarity	NPD5618	Discontinued
0.6446	Remote Similarity	NPD4215	Approved
0.6436	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD181	Approved
0.6415	Remote Similarity	NPD1843	Approved
0.641	Remote Similarity	NPD255	Approved
0.641	Remote Similarity	NPD1348	Approved
0.641	Remote Similarity	NPD256	Approved
0.6404	Remote Similarity	NPD5927	Discontinued
0.6396	Remote Similarity	NPD1040	Phase 2
0.6389	Remote Similarity	NPD1238	Approved
0.6387	Remote Similarity	NPD4479	Discontinued
0.6381	Remote Similarity	NPD3718	Approved
0.6381	Remote Similarity	NPD1409	Phase 3
0.6381	Remote Similarity	NPD3719	Approved
0.6379	Remote Similarity	NPD1370	Approved
0.6379	Remote Similarity	NPD1371	Approved
0.6379	Remote Similarity	NPD1373	Approved
0.6379	Remote Similarity	NPD1374	Approved
0.6373	Remote Similarity	NPD531	Approved
0.6364	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD4576	Approved
0.6356	Remote Similarity	NPD4574	Approved
0.6346	Remote Similarity	NPD530	Approved
0.6341	Remote Similarity	NPD182	Clinical (unspecified phase)

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