NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	180.08
Volume:	188.785
LogP:	2.169
LogD:	2.916
LogS:	-2.093
# Rotatable Bonds:	3
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.772
Synthetic Accessibility Score:	2.001
Fsp3:	0.3
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:	-4.665
MDCK Permeability:	3.656812623376027e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.504
Plasma Protein Binding (PPB):	89.08702850341797%
Volume Distribution (VD):	0.33
Pgp-substrate:	5.24458122253418%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.884
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.796
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.326
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.121

ADMET: Excretion

Clearance (CL):	2.017
Half-life (T1/2):	0.789

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.304
Drug-inuced Liver Injury (DILI):	0.939
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.245
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.218
Carcinogencity:	0.153
Eye Corrosion:	0.352
Eye Irritation:	0.89
Respiratory Toxicity:	0.103

Download Data

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

Natural Product: NPC109241

Natural Product ID:	NPC109241
*Common Name:**	2-(4-Methoxyphenyl)Propanoic Acid
IUPAC Name:	2-(4-methoxyphenyl)propanoic acid
Synonyms:
Standard InCHIKey:	KBDLTYNZHQRMQC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H12O3/c1-7(10(11)12)8-3-5-9(13-2)6-4-8/h3-7H,1-2H3,(H,11,12)
SMILES:	CC(c1ccc(cc1)OC)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL370087
PubChem CID:	257576
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
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15739361]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	seed	n.a.	PMID[23845552]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	seeds	n.a.	n.a.	PMID[23999046]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	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
Others	1

Activity Type	# Activity
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3781	Protein Family	Interleukin-8 receptors, CXCR1/CXCR2	Homo sapiens	Inhibition	=	34.0	%	PMID[558699]

☑ 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 NPC109241 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	230
0.1-0.2	1287
0.2-0.3	3363
0.3-0.4	9118
0.4-0.5	9797
0.5-0.6	5336
0.6-0.7	10729
0.7-0.8	2721
0.8-0.85	103
0.85-0.9	10
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9619	High Similarity	NPC234639
0.9333	High Similarity	NPC1065
0.8974	High Similarity	NPC111088
0.8962	High Similarity	NPC38209
0.8929	High Similarity	NPC322358
0.8868	High Similarity	NPC298224
0.886	High Similarity	NPC205502
0.8727	High Similarity	NPC259554
0.8621	High Similarity	NPC61779
0.8609	High Similarity	NPC240664
0.8596	High Similarity	NPC51345
0.8559	High Similarity	NPC194416
0.8559	High Similarity	NPC177291
0.8534	High Similarity	NPC293424
0.8505	High Similarity	NPC52472
0.8496	Intermediate Similarity	NPC17693
0.8468	Intermediate Similarity	NPC125153
0.844	Intermediate Similarity	NPC2518
0.8435	Intermediate Similarity	NPC220540
0.8411	Intermediate Similarity	NPC100870
0.8411	Intermediate Similarity	NPC245561
0.8407	Intermediate Similarity	NPC23332
0.8364	Intermediate Similarity	NPC238115
0.8364	Intermediate Similarity	NPC473855
0.8362	Intermediate Similarity	NPC19290
0.8361	Intermediate Similarity	NPC474476
0.8333	Intermediate Similarity	NPC69403
0.8333	Intermediate Similarity	NPC199462
0.8333	Intermediate Similarity	NPC291189
0.8319	Intermediate Similarity	NPC183648
0.8305	Intermediate Similarity	NPC299406
0.8304	Intermediate Similarity	NPC201959
0.8304	Intermediate Similarity	NPC31274
0.8293	Intermediate Similarity	NPC281020
0.8279	Intermediate Similarity	NPC280767
0.8264	Intermediate Similarity	NPC473942
0.8257	Intermediate Similarity	NPC300166
0.8257	Intermediate Similarity	NPC307425
0.825	Intermediate Similarity	NPC201777
0.8241	Intermediate Similarity	NPC280869
0.824	Intermediate Similarity	NPC475102
0.8211	Intermediate Similarity	NPC475236
0.8205	Intermediate Similarity	NPC470860
0.8205	Intermediate Similarity	NPC131192
0.8198	Intermediate Similarity	NPC227255
0.8198	Intermediate Similarity	NPC13495
0.8198	Intermediate Similarity	NPC288760
0.8197	Intermediate Similarity	NPC221798
0.819	Intermediate Similarity	NPC235250
0.819	Intermediate Similarity	NPC81808
0.819	Intermediate Similarity	NPC321956
0.8182	Intermediate Similarity	NPC116562
0.8182	Intermediate Similarity	NPC179686
0.8165	Intermediate Similarity	NPC107101
0.8158	Intermediate Similarity	NPC473809
0.8151	Intermediate Similarity	NPC264976
0.8148	Intermediate Similarity	NPC260000
0.8145	Intermediate Similarity	NPC121104
0.8145	Intermediate Similarity	NPC223807
0.8142	Intermediate Similarity	NPC75440
0.8136	Intermediate Similarity	NPC469954
0.813	Intermediate Similarity	NPC173608
0.8125	Intermediate Similarity	NPC113457
0.8125	Intermediate Similarity	NPC4982
0.8125	Intermediate Similarity	NPC300776
0.8125	Intermediate Similarity	NPC68779
0.8125	Intermediate Similarity	NPC5310
0.8125	Intermediate Similarity	NPC213122
0.8125	Intermediate Similarity	NPC326447
0.8125	Intermediate Similarity	NPC176814
0.812	Intermediate Similarity	NPC296526
0.812	Intermediate Similarity	NPC188907
0.8115	Intermediate Similarity	NPC163083
0.8115	Intermediate Similarity	NPC244876
0.8108	Intermediate Similarity	NPC283546
0.8108	Intermediate Similarity	NPC108875
0.8108	Intermediate Similarity	NPC109637
0.8108	Intermediate Similarity	NPC38079
0.8103	Intermediate Similarity	NPC148969
0.8095	Intermediate Similarity	NPC109778
0.8095	Intermediate Similarity	NPC71853
0.8087	Intermediate Similarity	NPC233238
0.8087	Intermediate Similarity	NPC57879
0.8083	Intermediate Similarity	NPC474874
0.808	Intermediate Similarity	NPC2596
0.8073	Intermediate Similarity	NPC171843
0.8067	Intermediate Similarity	NPC328694
0.8067	Intermediate Similarity	NPC94298
0.8067	Intermediate Similarity	NPC27633
0.8062	Intermediate Similarity	NPC113295
0.8062	Intermediate Similarity	NPC470990
0.8053	Intermediate Similarity	NPC228737
0.8051	Intermediate Similarity	NPC325646
0.8051	Intermediate Similarity	NPC128249
0.8051	Intermediate Similarity	NPC28951
0.8049	Intermediate Similarity	NPC470163
0.8049	Intermediate Similarity	NPC89630
0.8049	Intermediate Similarity	NPC470162
0.8036	Intermediate Similarity	NPC128730
0.8036	Intermediate Similarity	NPC470393
0.8033	Intermediate Similarity	NPC67300
0.8033	Intermediate Similarity	NPC114298
0.8018	Intermediate Similarity	NPC305205
0.8018	Intermediate Similarity	NPC13426
0.8017	Intermediate Similarity	NPC280760
0.8017	Intermediate Similarity	NPC48525
0.8016	Intermediate Similarity	NPC473019
0.8	Intermediate Similarity	NPC99886
0.8	Intermediate Similarity	NPC253746
0.8	Intermediate Similarity	NPC231251
0.8	Intermediate Similarity	NPC177844
0.8	Intermediate Similarity	NPC259134
0.8	Intermediate Similarity	NPC25067
0.8	Intermediate Similarity	NPC8002
0.8	Intermediate Similarity	NPC472593
0.8	Intermediate Similarity	NPC88868
0.7984	Intermediate Similarity	NPC53305
0.7984	Intermediate Similarity	NPC49938
0.7984	Intermediate Similarity	NPC137416
0.7984	Intermediate Similarity	NPC257589
0.7983	Intermediate Similarity	NPC45104
0.7983	Intermediate Similarity	NPC217423
0.7982	Intermediate Similarity	NPC291837
0.7982	Intermediate Similarity	NPC175298
0.7969	Intermediate Similarity	NPC470160
0.7967	Intermediate Similarity	NPC164778
0.7967	Intermediate Similarity	NPC242372
0.7967	Intermediate Similarity	NPC474691
0.7967	Intermediate Similarity	NPC4181
0.7967	Intermediate Similarity	NPC257976
0.7965	Intermediate Similarity	NPC176971
0.7965	Intermediate Similarity	NPC317592
0.7953	Intermediate Similarity	NPC470725
0.7953	Intermediate Similarity	NPC285776
0.7953	Intermediate Similarity	NPC245395
0.7949	Intermediate Similarity	NPC190212
0.7949	Intermediate Similarity	NPC303522
0.7949	Intermediate Similarity	NPC35344
0.7949	Intermediate Similarity	NPC141003
0.7946	Intermediate Similarity	NPC474603
0.7946	Intermediate Similarity	NPC12987
0.7937	Intermediate Similarity	NPC2401
0.7934	Intermediate Similarity	NPC478121
0.7931	Intermediate Similarity	NPC54626
0.792	Intermediate Similarity	NPC127937
0.792	Intermediate Similarity	NPC92207
0.7917	Intermediate Similarity	NPC471033
0.7917	Intermediate Similarity	NPC171023
0.7917	Intermediate Similarity	NPC311091
0.7913	Intermediate Similarity	NPC326187
0.7913	Intermediate Similarity	NPC474272
0.7913	Intermediate Similarity	NPC471954
0.7913	Intermediate Similarity	NPC75272
0.7907	Intermediate Similarity	NPC307006
0.7907	Intermediate Similarity	NPC129889
0.7903	Intermediate Similarity	NPC312404
0.7903	Intermediate Similarity	NPC6888
0.7903	Intermediate Similarity	NPC184219
0.7903	Intermediate Similarity	NPC145134
0.7903	Intermediate Similarity	NPC75432
0.7903	Intermediate Similarity	NPC273686
0.7899	Intermediate Similarity	NPC471924
0.7899	Intermediate Similarity	NPC128825
0.7899	Intermediate Similarity	NPC471925
0.7899	Intermediate Similarity	NPC471928
0.7895	Intermediate Similarity	NPC251306
0.7895	Intermediate Similarity	NPC157473
0.7895	Intermediate Similarity	NPC151530
0.7891	Intermediate Similarity	NPC196979
0.7891	Intermediate Similarity	NPC470977
0.7891	Intermediate Similarity	NPC258073
0.7891	Intermediate Similarity	NPC470976
0.7886	Intermediate Similarity	NPC46634
0.7886	Intermediate Similarity	NPC311219
0.7886	Intermediate Similarity	NPC121168
0.7881	Intermediate Similarity	NPC252004
0.7881	Intermediate Similarity	NPC294941
0.7881	Intermediate Similarity	NPC114144
0.7876	Intermediate Similarity	NPC473393
0.7876	Intermediate Similarity	NPC127676
0.7874	Intermediate Similarity	NPC66246
0.7874	Intermediate Similarity	NPC939
0.7874	Intermediate Similarity	NPC241354
0.7874	Intermediate Similarity	NPC170546
0.7869	Intermediate Similarity	NPC225245
0.7863	Intermediate Similarity	NPC90431
0.7863	Intermediate Similarity	NPC26615
0.7857	Intermediate Similarity	NPC12870
0.7857	Intermediate Similarity	NPC71525
0.7857	Intermediate Similarity	NPC12022
0.7857	Intermediate Similarity	NPC24327
0.7857	Intermediate Similarity	NPC16651
0.7857	Intermediate Similarity	NPC20404
0.7857	Intermediate Similarity	NPC20287
0.7857	Intermediate Similarity	NPC293641
0.7857	Intermediate Similarity	NPC32163
0.7857	Intermediate Similarity	NPC304638
0.7857	Intermediate Similarity	NPC293387
0.7851	Intermediate Similarity	NPC42657
0.7851	Intermediate Similarity	NPC234956

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 NPC109241 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	924
0.2-0.3	1301
0.3-0.4	2390
0.4-0.5	2073
0.5-0.6	1315
0.6-0.7	707
0.7-0.8	198
0.8-0.85	12
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8974	High Similarity	NPD1283	Approved
0.8718	High Similarity	NPD1281	Approved
0.8644	High Similarity	NPD1608	Approved
0.839	Intermediate Similarity	NPD17	Approved
0.8376	Intermediate Similarity	NPD1894	Discontinued
0.8319	Intermediate Similarity	NPD3847	Discontinued
0.8261	Intermediate Similarity	NPD1241	Discontinued
0.8189	Intermediate Similarity	NPD6355	Discontinued
0.8182	Intermediate Similarity	NPD1481	Phase 2
0.8151	Intermediate Similarity	NPD1651	Approved
0.813	Intermediate Similarity	NPD2797	Approved
0.8125	Intermediate Similarity	NPD3134	Approved
0.8099	Intermediate Similarity	NPD1535	Discovery
0.8083	Intermediate Similarity	NPD4626	Approved
0.8067	Intermediate Similarity	NPD9545	Approved
0.8049	Intermediate Similarity	NPD1876	Approved
0.8049	Intermediate Similarity	NPD196	Phase 1
0.8	Intermediate Similarity	NPD454	Approved
0.8	Intermediate Similarity	NPD2799	Discontinued
0.7984	Intermediate Similarity	NPD987	Approved
0.7969	Intermediate Similarity	NPD2979	Phase 3
0.7953	Intermediate Similarity	NPD6798	Discontinued
0.7939	Intermediate Similarity	NPD4476	Approved
0.7939	Intermediate Similarity	NPD4477	Approved
0.7937	Intermediate Similarity	NPD2614	Approved
0.7934	Intermediate Similarity	NPD1778	Approved
0.792	Intermediate Similarity	NPD2798	Approved
0.7899	Intermediate Similarity	NPD9493	Approved
0.7895	Intermediate Similarity	NPD1358	Approved
0.7886	Intermediate Similarity	NPD3972	Approved
0.7886	Intermediate Similarity	NPD9717	Approved
0.7863	Intermediate Similarity	NPD5535	Approved
0.7851	Intermediate Similarity	NPD5585	Approved
0.7851	Intermediate Similarity	NPD5691	Approved
0.7836	Intermediate Similarity	NPD7003	Approved
0.7826	Intermediate Similarity	NPD2684	Approved
0.7812	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD3268	Approved
0.7803	Intermediate Similarity	NPD2935	Discontinued
0.7778	Intermediate Similarity	NPD228	Approved
0.7752	Intermediate Similarity	NPD6233	Phase 2
0.7752	Intermediate Similarity	NPD8032	Phase 2
0.7752	Intermediate Similarity	NPD4062	Phase 3
0.7734	Intermediate Similarity	NPD7095	Approved
0.7704	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD4110	Phase 3
0.7704	Intermediate Similarity	NPD4628	Phase 3
0.7698	Intermediate Similarity	NPD3267	Approved
0.7698	Intermediate Similarity	NPD3266	Approved
0.7687	Intermediate Similarity	NPD5958	Discontinued
0.7687	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD4534	Discontinued
0.7669	Intermediate Similarity	NPD2531	Phase 2
0.7669	Intermediate Similarity	NPD2438	Suspended
0.7667	Intermediate Similarity	NPD256	Approved
0.7667	Intermediate Similarity	NPD255	Approved
0.7667	Intermediate Similarity	NPD7157	Approved
0.7647	Intermediate Similarity	NPD5283	Phase 1
0.7642	Intermediate Similarity	NPD2668	Approved
0.7642	Intermediate Similarity	NPD2667	Approved
0.7638	Intermediate Similarity	NPD5647	Approved
0.7612	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD3020	Approved
0.7586	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD9494	Approved
0.7563	Intermediate Similarity	NPD821	Approved
0.7563	Intermediate Similarity	NPD7843	Approved
0.7559	Intermediate Similarity	NPD1203	Approved
0.7559	Intermediate Similarity	NPD6362	Approved
0.7557	Intermediate Similarity	NPD4060	Phase 1
0.7557	Intermediate Similarity	NPD4140	Approved
0.7557	Intermediate Similarity	NPD1240	Approved
0.7554	Intermediate Similarity	NPD6273	Approved
0.7545	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD4359	Approved
0.7538	Intermediate Similarity	NPD3764	Approved
0.7538	Intermediate Similarity	NPD2313	Discontinued
0.752	Intermediate Similarity	NPD422	Phase 1
0.75	Intermediate Similarity	NPD1090	Approved
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4622	Approved
0.75	Intermediate Similarity	NPD4618	Approved
0.75	Intermediate Similarity	NPD1089	Approved
0.75	Intermediate Similarity	NPD1086	Approved
0.7481	Intermediate Similarity	NPD6002	Phase 3
0.7481	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD6005	Phase 3
0.7481	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD6004	Phase 3
0.7463	Intermediate Similarity	NPD4308	Phase 3
0.7458	Intermediate Similarity	NPD5451	Approved
0.7445	Intermediate Similarity	NPD3750	Approved
0.7444	Intermediate Similarity	NPD1607	Approved
0.7444	Intermediate Similarity	NPD6653	Approved
0.744	Intermediate Similarity	NPD3496	Discontinued
0.7438	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD290	Approved
0.7417	Intermediate Similarity	NPD1138	Approved
0.7414	Intermediate Similarity	NPD9697	Approved
0.741	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD800	Approved
0.7405	Intermediate Similarity	NPD411	Approved
0.7402	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7458	Discontinued
0.7388	Intermediate Similarity	NPD5688	Approved
0.7388	Intermediate Similarity	NPD5689	Approved
0.7388	Intermediate Similarity	NPD7097	Phase 1
0.7387	Intermediate Similarity	NPD1693	Approved
0.7385	Intermediate Similarity	NPD6832	Phase 2
0.7381	Intermediate Similarity	NPD1610	Phase 2
0.7381	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD7427	Discontinued
0.7368	Intermediate Similarity	NPD447	Suspended
0.7364	Intermediate Similarity	NPD1088	Approved
0.7364	Intermediate Similarity	NPD1019	Discontinued
0.736	Intermediate Similarity	NPD2932	Approved
0.736	Intermediate Similarity	NPD3019	Approved
0.7353	Intermediate Similarity	NPD2346	Discontinued
0.7353	Intermediate Similarity	NPD2344	Approved
0.735	Intermediate Similarity	NPD968	Approved
0.7348	Intermediate Similarity	NPD6663	Approved
0.7345	Intermediate Similarity	NPD9495	Approved
0.7333	Intermediate Similarity	NPD1139	Approved
0.7333	Intermediate Similarity	NPD1137	Approved
0.7333	Intermediate Similarity	NPD1510	Phase 2
0.7333	Intermediate Similarity	NPD9491	Approved
0.7333	Intermediate Similarity	NPD3748	Approved
0.7328	Intermediate Similarity	NPD5163	Phase 2
0.7328	Intermediate Similarity	NPD5909	Discontinued
0.7328	Intermediate Similarity	NPD164	Approved
0.7324	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2859	Approved
0.7321	Intermediate Similarity	NPD2860	Approved
0.7317	Intermediate Similarity	NPD9568	Approved
0.7313	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5736	Approved
0.7299	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4307	Phase 2
0.7288	Intermediate Similarity	NPD9267	Approved
0.7288	Intermediate Similarity	NPD9263	Approved
0.7288	Intermediate Similarity	NPD9264	Approved
0.7287	Intermediate Similarity	NPD1164	Approved
0.7279	Intermediate Similarity	NPD2239	Approved
0.7279	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2240	Approved
0.7273	Intermediate Similarity	NPD1296	Phase 2
0.7266	Intermediate Similarity	NPD3685	Discontinued
0.7266	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD2354	Approved
0.7259	Intermediate Similarity	NPD1536	Approved
0.7258	Intermediate Similarity	NPD5536	Phase 2
0.7257	Intermediate Similarity	NPD288	Approved
0.725	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1611	Approved
0.7239	Intermediate Similarity	NPD1184	Approved
0.7236	Intermediate Similarity	NPD709	Approved
0.7236	Intermediate Similarity	NPD6671	Approved
0.7234	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD2934	Approved
0.7232	Intermediate Similarity	NPD2933	Approved
0.7231	Intermediate Similarity	NPD4624	Approved
0.7227	Intermediate Similarity	NPD9266	Approved
0.7227	Intermediate Similarity	NPD74	Approved
0.7226	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1087	Approved
0.7218	Intermediate Similarity	NPD4870	Approved
0.7209	Intermediate Similarity	NPD3225	Approved
0.7206	Intermediate Similarity	NPD7033	Discontinued
0.7196	Intermediate Similarity	NPD111	Approved
0.7194	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2230	Approved
0.7188	Intermediate Similarity	NPD2232	Approved
0.7188	Intermediate Similarity	NPD2233	Approved
0.7174	Intermediate Similarity	NPD2897	Discontinued
0.7174	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD2203	Discontinued
0.7154	Intermediate Similarity	NPD2629	Approved
0.7153	Intermediate Similarity	NPD1537	Approved
0.7153	Intermediate Similarity	NPD1551	Phase 2
0.7153	Intermediate Similarity	NPD1538	Phase 1
0.7153	Intermediate Similarity	NPD1519	Approved
0.7143	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD1357	Approved
0.7143	Intermediate Similarity	NPD845	Approved
0.7143	Intermediate Similarity	NPD226	Approved
0.7132	Intermediate Similarity	NPD1521	Approved
0.7132	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1520	Approved
0.7132	Intermediate Similarity	NPD1669	Approved
0.713	Intermediate Similarity	NPD2066	Phase 3
0.713	Intermediate Similarity	NPD1238	Approved
0.7121	Intermediate Similarity	NPD4908	Phase 1
0.7117	Intermediate Similarity	NPD1239	Approved
0.7111	Intermediate Similarity	NPD230	Phase 1
0.7111	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1564	Approved
0.7105	Intermediate Similarity	NPD1566	Phase 3
0.7105	Intermediate Similarity	NPD1565	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