NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.12
Volume:	258.253
LogP:	1.802
LogD:	2.471
LogS:	-2.507
# Rotatable Bonds:	7
TPSA:	53.99
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.725
Synthetic Accessibility Score:	1.798
Fsp3:	0.462
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.546
MDCK Permeability:	3.471985473879613e-05
Pgp-inhibitor:	0.725
Pgp-substrate:	0.071
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.277

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.979
Plasma Protein Binding (PPB):	63.047096252441406%
Volume Distribution (VD):	0.591
Pgp-substrate:	18.220561981201172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.869
CYP1A2-substrate:	0.927
CYP2C19-inhibitor:	0.538
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.846
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.537

ADMET: Excretion

Clearance (CL):	9.929
Half-life (T1/2):	0.872

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.183
Drug-inuced Liver Injury (DILI):	0.636
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.088
Skin Sensitization:	0.39
Carcinogencity:	0.041
Eye Corrosion:	0.021
Eye Irritation:	0.366
Respiratory Toxicity:	0.116

Download Data

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

Natural Product: NPC153547

Natural Product ID:	NPC153547
*Common Name:**	Methyl 3-(2,4,5-Trimethoxyphenyl)Propanoate
IUPAC Name:	methyl 3-(2,4,5-trimethoxyphenyl)propanoate
Synonyms:
Standard InCHIKey:	SULPGCHHOCMNSJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H18O5/c1-15-10-8-12(17-3)11(16-2)7-9(10)5-6-13(14)18-4/h7-8H,5-6H2,1-4H3
SMILES:	COC(=O)CCc1cc(OC)c(cc1OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506090
PubChem CID:	10377602
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO5373	Cordia alliodora	Species	Cordiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[10757739]
NPO5373	Cordia alliodora	Species	Cordiaceae	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
MIC	1
Others	3

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	Activity	=	5.0	ug	PMID[530157]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	MIC	=	15.0	ug.mL-1	PMID[530157]
NPT20	Organism	Candida albicans	Candida albicans	Activity	>	50.0	ug	PMID[530157]
NPT1381	Organism	Aedes aegypti	Aedes aegypti	Activity	=	12.5	ug ml-1	PMID[530157]

☑ 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 NPC153547 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	368
0.1-0.2	1799
0.2-0.3	5292
0.3-0.4	11899
0.4-0.5	5591
0.5-0.6	4688
0.6-0.7	7588
0.7-0.8	5199
0.8-0.85	239
0.85-0.9	29
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.952	High Similarity	NPC150809
0.92	High Similarity	NPC173608
0.8992	High Similarity	NPC299010
0.8943	High Similarity	NPC308217
0.8931	High Similarity	NPC288743
0.8797	High Similarity	NPC143649
0.878	High Similarity	NPC304208
0.878	High Similarity	NPC52464
0.876	High Similarity	NPC474670
0.8731	High Similarity	NPC471182
0.8722	High Similarity	NPC155098
0.8712	High Similarity	NPC319969
0.8682	High Similarity	NPC474632
0.8667	High Similarity	NPC157944
0.8667	High Similarity	NPC474274
0.8633	High Similarity	NPC27106
0.8615	High Similarity	NPC474821
0.8605	High Similarity	NPC64391
0.8593	High Similarity	NPC209229
0.8582	High Similarity	NPC474600
0.8571	High Similarity	NPC137669
0.8571	High Similarity	NPC222175
0.8561	High Similarity	NPC18211
0.8561	High Similarity	NPC476399
0.8561	High Similarity	NPC244799
0.8561	High Similarity	NPC240722
0.856	High Similarity	NPC474612
0.8551	High Similarity	NPC58229
0.854	High Similarity	NPC203351
0.8538	High Similarity	NPC154275
0.8529	High Similarity	NPC125417
0.8529	High Similarity	NPC95679
0.8529	High Similarity	NPC112068
0.8529	High Similarity	NPC110899
0.8529	High Similarity	NPC25305
0.8527	High Similarity	NPC191768
0.8527	High Similarity	NPC92869
0.8527	High Similarity	NPC283170
0.8519	High Similarity	NPC44245
0.8519	High Similarity	NPC211386
0.8519	High Similarity	NPC72796
0.8516	High Similarity	NPC264885
0.8516	High Similarity	NPC270326
0.8516	High Similarity	NPC211231
0.8507	High Similarity	NPC233018
0.8507	High Similarity	NPC241341
0.8507	High Similarity	NPC36437
0.8485	Intermediate Similarity	NPC123127
0.8485	Intermediate Similarity	NPC27239
0.8473	Intermediate Similarity	NPC281020
0.8467	Intermediate Similarity	NPC44573
0.8456	Intermediate Similarity	NPC286843
0.8455	Intermediate Similarity	NPC204120
0.844	Intermediate Similarity	NPC287275
0.844	Intermediate Similarity	NPC474446
0.8438	Intermediate Similarity	NPC285289
0.8429	Intermediate Similarity	NPC143092
0.8417	Intermediate Similarity	NPC472332
0.8417	Intermediate Similarity	NPC472335
0.8414	Intermediate Similarity	NPC474514
0.8414	Intermediate Similarity	NPC289968
0.8413	Intermediate Similarity	NPC205502
0.8409	Intermediate Similarity	NPC474651
0.8409	Intermediate Similarity	NPC474616
0.8409	Intermediate Similarity	NPC474636
0.8409	Intermediate Similarity	NPC304747
0.8409	Intermediate Similarity	NPC474623
0.8409	Intermediate Similarity	NPC210674
0.8403	Intermediate Similarity	NPC474975
0.8385	Intermediate Similarity	NPC183446
0.8382	Intermediate Similarity	NPC234865
0.8382	Intermediate Similarity	NPC73071
0.838	Intermediate Similarity	NPC302408
0.838	Intermediate Similarity	NPC14958
0.838	Intermediate Similarity	NPC216314
0.838	Intermediate Similarity	NPC106461
0.838	Intermediate Similarity	NPC195919
0.838	Intermediate Similarity	NPC283002
0.838	Intermediate Similarity	NPC215932
0.838	Intermediate Similarity	NPC40818
0.838	Intermediate Similarity	NPC165389
0.838	Intermediate Similarity	NPC120924
0.838	Intermediate Similarity	NPC110639
0.8372	Intermediate Similarity	NPC288238
0.8372	Intermediate Similarity	NPC194626
0.8369	Intermediate Similarity	NPC182842
0.8357	Intermediate Similarity	NPC29536
0.8356	Intermediate Similarity	NPC186507
0.8345	Intermediate Similarity	NPC474663
0.8345	Intermediate Similarity	NPC207418
0.8345	Intermediate Similarity	NPC470991
0.8333	Intermediate Similarity	NPC207516
0.8333	Intermediate Similarity	NPC270256
0.8333	Intermediate Similarity	NPC202904
0.8333	Intermediate Similarity	NPC189248
0.8333	Intermediate Similarity	NPC46947
0.8322	Intermediate Similarity	NPC119660
0.8322	Intermediate Similarity	NPC205522
0.8322	Intermediate Similarity	NPC85233
0.8322	Intermediate Similarity	NPC139839
0.8322	Intermediate Similarity	NPC93034
0.831	Intermediate Similarity	NPC87295
0.831	Intermediate Similarity	NPC213482
0.831	Intermediate Similarity	NPC165512
0.8309	Intermediate Similarity	NPC309953
0.8299	Intermediate Similarity	NPC276059
0.8299	Intermediate Similarity	NPC241774
0.8299	Intermediate Similarity	NPC122623
0.8299	Intermediate Similarity	NPC34725
0.8298	Intermediate Similarity	NPC70853
0.8298	Intermediate Similarity	NPC9966
0.8295	Intermediate Similarity	NPC310373
0.8293	Intermediate Similarity	NPC203924
0.8286	Intermediate Similarity	NPC46180
0.8284	Intermediate Similarity	NPC285776
0.8284	Intermediate Similarity	NPC79184
0.8284	Intermediate Similarity	NPC474617
0.8284	Intermediate Similarity	NPC307042
0.8284	Intermediate Similarity	NPC19242
0.8279	Intermediate Similarity	NPC165386
0.8276	Intermediate Similarity	NPC29056
0.8268	Intermediate Similarity	NPC63083
0.8264	Intermediate Similarity	NPC10304
0.8264	Intermediate Similarity	NPC63256
0.8264	Intermediate Similarity	NPC476058
0.8258	Intermediate Similarity	NPC127604
0.8252	Intermediate Similarity	NPC231013
0.8248	Intermediate Similarity	NPC311430
0.8248	Intermediate Similarity	NPC224941
0.8248	Intermediate Similarity	NPC208760
0.8243	Intermediate Similarity	NPC257277
0.8239	Intermediate Similarity	NPC232883
0.8239	Intermediate Similarity	NPC23955
0.8239	Intermediate Similarity	NPC113089
0.8235	Intermediate Similarity	NPC307006
0.8235	Intermediate Similarity	NPC129889
0.8235	Intermediate Similarity	NPC472522
0.8235	Intermediate Similarity	NPC474810
0.8231	Intermediate Similarity	NPC77430
0.8227	Intermediate Similarity	NPC185607
0.8227	Intermediate Similarity	NPC474288
0.8222	Intermediate Similarity	NPC147317
0.8219	Intermediate Similarity	NPC472535
0.8219	Intermediate Similarity	NPC474388
0.8219	Intermediate Similarity	NPC198615
0.8219	Intermediate Similarity	NPC473732
0.8219	Intermediate Similarity	NPC474170
0.8217	Intermediate Similarity	NPC267064
0.8214	Intermediate Similarity	NPC19158
0.8209	Intermediate Similarity	NPC58164
0.8209	Intermediate Similarity	NPC10225
0.8207	Intermediate Similarity	NPC238366
0.8207	Intermediate Similarity	NPC102003
0.8207	Intermediate Similarity	NPC92722
0.8207	Intermediate Similarity	NPC181250
0.8207	Intermediate Similarity	NPC69752
0.8207	Intermediate Similarity	NPC328119
0.8203	Intermediate Similarity	NPC475961
0.8203	Intermediate Similarity	NPC254625
0.8201	Intermediate Similarity	NPC43500
0.8201	Intermediate Similarity	NPC233780
0.8201	Intermediate Similarity	NPC164148
0.8201	Intermediate Similarity	NPC470962
0.8194	Intermediate Similarity	NPC61871
0.8194	Intermediate Similarity	NPC30647
0.8194	Intermediate Similarity	NPC55557
0.8188	Intermediate Similarity	NPC167517
0.8188	Intermediate Similarity	NPC160425
0.8182	Intermediate Similarity	NPC296575
0.8182	Intermediate Similarity	NPC136278
0.8182	Intermediate Similarity	NPC472917
0.8182	Intermediate Similarity	NPC27352
0.8176	Intermediate Similarity	NPC471800
0.8169	Intermediate Similarity	NPC476054
0.8169	Intermediate Similarity	NPC119663
0.8169	Intermediate Similarity	NPC27159
0.8163	Intermediate Similarity	NPC475116
0.8156	Intermediate Similarity	NPC210354
0.8156	Intermediate Similarity	NPC176586
0.8156	Intermediate Similarity	NPC110419
0.8156	Intermediate Similarity	NPC40237
0.8156	Intermediate Similarity	NPC151423
0.8154	Intermediate Similarity	NPC177291
0.8154	Intermediate Similarity	NPC194416
0.8151	Intermediate Similarity	NPC96501
0.8151	Intermediate Similarity	NPC259058
0.8151	Intermediate Similarity	NPC201547
0.8151	Intermediate Similarity	NPC177839
0.8151	Intermediate Similarity	NPC239363
0.8148	Intermediate Similarity	NPC192687
0.8148	Intermediate Similarity	NPC51840
0.8148	Intermediate Similarity	NPC234488
0.8148	Intermediate Similarity	NPC470624
0.8148	Intermediate Similarity	NPC311680
0.8148	Intermediate Similarity	NPC224157
0.8148	Intermediate Similarity	NPC299221
0.8148	Intermediate Similarity	NPC237169
0.8138	Intermediate Similarity	NPC15329
0.8138	Intermediate Similarity	NPC131451
0.8138	Intermediate Similarity	NPC287395

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 NPC153547 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	1001
0.2-0.3	2065
0.3-0.4	2702
0.4-0.5	1572
0.5-0.6	950
0.6-0.7	428
0.7-0.8	97
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8148	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD3817	Phase 2
0.7987	Intermediate Similarity	NPD2801	Approved
0.7971	Intermediate Similarity	NPD230	Phase 1
0.7887	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD37	Approved
0.7794	Intermediate Similarity	NPD3018	Phase 2
0.7763	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6232	Discontinued
0.7727	Intermediate Similarity	NPD5494	Approved
0.7722	Intermediate Similarity	NPD5844	Phase 1
0.7697	Intermediate Similarity	NPD5353	Approved
0.7687	Intermediate Similarity	NPD2981	Phase 2
0.7682	Intermediate Similarity	NPD1934	Approved
0.7681	Intermediate Similarity	NPD3027	Phase 3
0.7677	Intermediate Similarity	NPD7199	Phase 2
0.7662	Intermediate Similarity	NPD919	Approved
0.7647	Intermediate Similarity	NPD4965	Approved
0.7647	Intermediate Similarity	NPD4967	Phase 2
0.7647	Intermediate Similarity	NPD4966	Approved
0.7635	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD2983	Phase 2
0.763	Intermediate Similarity	NPD2982	Phase 2
0.7619	Intermediate Similarity	NPD1511	Approved
0.7619	Intermediate Similarity	NPD6799	Approved
0.7619	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD3705	Approved
0.7595	Intermediate Similarity	NPD7473	Discontinued
0.7594	Intermediate Similarity	NPD17	Approved
0.7589	Intermediate Similarity	NPD447	Suspended
0.758	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3146	Approved
0.7568	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1247	Approved
0.7548	Intermediate Similarity	NPD6234	Discontinued
0.7536	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1653	Approved
0.7532	Intermediate Similarity	NPD3882	Suspended
0.7519	Intermediate Similarity	NPD9268	Approved
0.7517	Intermediate Similarity	NPD1512	Approved
0.7516	Intermediate Similarity	NPD1465	Phase 2
0.7516	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1296	Phase 2
0.75	Intermediate Similarity	NPD5536	Phase 2
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7482	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5242	Approved
0.7463	Intermediate Similarity	NPD1778	Approved
0.7462	Intermediate Similarity	NPD5283	Phase 1
0.745	Intermediate Similarity	NPD2534	Approved
0.745	Intermediate Similarity	NPD2532	Approved
0.745	Intermediate Similarity	NPD2533	Approved
0.7426	Intermediate Similarity	NPD9269	Phase 2
0.7426	Intermediate Similarity	NPD1608	Approved
0.7423	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1240	Approved
0.7394	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1613	Approved
0.7386	Intermediate Similarity	NPD6385	Approved
0.7386	Intermediate Similarity	NPD6386	Approved
0.7379	Intermediate Similarity	NPD2796	Approved
0.7353	Intermediate Similarity	NPD422	Phase 1
0.7347	Intermediate Similarity	NPD1243	Approved
0.7324	Intermediate Similarity	NPD6233	Phase 2
0.732	Intermediate Similarity	NPD6599	Discontinued
0.7312	Intermediate Similarity	NPD6166	Phase 2
0.7312	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3748	Approved
0.731	Intermediate Similarity	NPD1510	Phase 2
0.7308	Intermediate Similarity	NPD228	Approved
0.7297	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1607	Approved
0.729	Intermediate Similarity	NPD7819	Suspended
0.729	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD9494	Approved
0.7284	Intermediate Similarity	NPD7054	Approved
0.7279	Intermediate Similarity	NPD3496	Discontinued
0.7266	Intermediate Similarity	NPD1358	Approved
0.726	Intermediate Similarity	NPD6100	Approved
0.726	Intermediate Similarity	NPD6099	Approved
0.726	Intermediate Similarity	NPD3539	Phase 1
0.725	Intermediate Similarity	NPD3926	Phase 2
0.7248	Intermediate Similarity	NPD6190	Approved
0.7244	Intermediate Similarity	NPD5402	Approved
0.7239	Intermediate Similarity	NPD7074	Phase 3
0.7239	Intermediate Similarity	NPD7472	Approved
0.7237	Intermediate Similarity	NPD920	Approved
0.7234	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2654	Approved
0.7226	Intermediate Similarity	NPD1281	Approved
0.7222	Intermediate Similarity	NPD7228	Approved
0.7222	Intermediate Similarity	NPD1933	Approved
0.7222	Intermediate Similarity	NPD3818	Discontinued
0.7219	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3540	Phase 1
0.7195	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4110	Phase 3
0.7152	Intermediate Similarity	NPD7075	Discontinued
0.7133	Intermediate Similarity	NPD6798	Discontinued
0.7133	Intermediate Similarity	NPD2219	Phase 1
0.7133	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1651	Approved
0.7132	Intermediate Similarity	NPD5691	Approved
0.7123	Intermediate Similarity	NPD6111	Discontinued
0.7122	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6801	Discontinued
0.7114	Intermediate Similarity	NPD1652	Phase 2
0.7108	Intermediate Similarity	NPD7808	Phase 3
0.7105	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6355	Discontinued
0.7101	Intermediate Similarity	NPD1535	Discovery
0.7097	Intermediate Similarity	NPD4380	Phase 2
0.7095	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6797	Phase 2
0.7086	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7229	Phase 3
0.708	Intermediate Similarity	NPD4626	Approved
0.7071	Intermediate Similarity	NPD1283	Approved
0.7067	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3750	Approved
0.7067	Intermediate Similarity	NPD4628	Phase 3
0.7059	Intermediate Similarity	NPD9545	Approved
0.7051	Intermediate Similarity	NPD7411	Suspended
0.705	Intermediate Similarity	NPD1481	Phase 2
0.7048	Intermediate Similarity	NPD7240	Approved
0.7048	Intermediate Similarity	NPD7251	Discontinued
0.7047	Intermediate Similarity	NPD1549	Phase 2
0.7039	Intermediate Similarity	NPD4357	Discontinued
0.7034	Intermediate Similarity	NPD943	Approved
0.7034	Intermediate Similarity	NPD2979	Phase 3
0.7027	Intermediate Similarity	NPD2438	Suspended
0.7027	Intermediate Similarity	NPD1551	Phase 2
0.7021	Intermediate Similarity	NPD3266	Approved
0.7021	Intermediate Similarity	NPD3267	Approved
0.702	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5585	Approved
0.7	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6832	Phase 2
0.6993	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1611	Approved
0.6975	Remote Similarity	NPD3787	Discontinued
0.6972	Remote Similarity	NPD1019	Discontinued
0.6959	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7033	Discontinued
0.6943	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5089	Approved
0.6943	Remote Similarity	NPD5090	Approved
0.694	Remote Similarity	NPD1241	Discontinued
0.6939	Remote Similarity	NPD2653	Approved
0.6937	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1548	Phase 1
0.6929	Remote Similarity	NPD9717	Approved
0.6923	Remote Similarity	NPD3134	Approved
0.6906	Remote Similarity	NPD3847	Discontinued
0.6903	Remote Similarity	NPD5403	Approved
0.6901	Remote Similarity	NPD2797	Approved
0.6897	Remote Similarity	NPD3268	Approved
0.6884	Remote Similarity	NPD1357	Approved
0.6883	Remote Similarity	NPD5401	Approved
0.6882	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4749	Approved
0.6875	Remote Similarity	NPD4908	Phase 1
0.6867	Remote Similarity	NPD6004	Phase 3
0.6867	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6005	Phase 3
0.6867	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6002	Phase 3
0.6866	Remote Similarity	NPD5535	Approved
0.6863	Remote Similarity	NPD7124	Phase 2
0.6863	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3686	Approved
0.6859	Remote Similarity	NPD3687	Approved
0.6857	Remote Similarity	NPD1610	Phase 2
0.6855	Remote Similarity	NPD4585	Approved
0.6853	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5677	Discontinued
0.6849	Remote Similarity	NPD4062	Phase 3
0.6839	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD3225	Approved
0.6828	Remote Similarity	NPD7095	Approved
0.6824	Remote Similarity	NPD6651	Approved
0.6824	Remote Similarity	NPD6653	Approved
0.6818	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5297	Approved
0.6812	Remote Similarity	NPD1894	Discontinued
0.681	Remote Similarity	NPD8127	Discontinued
0.6809	Remote Similarity	NPD3972	Approved
0.6806	Remote Similarity	NPD2237	Approved
0.6805	Remote Similarity	NPD7549	Discontinued
0.6803	Remote Similarity	NPD4060	Phase 1
0.6795	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD9493	Approved
0.6781	Remote Similarity	NPD411	Approved
0.6781	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2800	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