NPASS Compound

Structure

CID127085 OpenBabel06191715482D 21 22 0 0 0 0 0 0 0 0999 V2000 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7788 -0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 1 0 0 0 0 4 8 2 0 0 0 0 5 9 2 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 17 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 12 1 0 0 0 0 11 14 2 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 20 1 0 0 0 0 15 17 1 0 0 0 0 15 18 2 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	289.13
Volume:	298.518
LogP:	2.093
LogD:	2.278
LogS:	-2.468
# Rotatable Bonds:	7
TPSA:	49.69
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.82
Synthetic Accessibility Score:	2.238
Fsp3:	0.312
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:	-4.553
MDCK Permeability:	3.479086808511056e-05
Pgp-inhibitor:	0.905
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.984
Plasma Protein Binding (PPB):	92.3875503540039%
Volume Distribution (VD):	0.628
Pgp-substrate:	5.243875980377197%

ADMET: Metabolism

CYP1A2-inhibitor:	0.955
CYP1A2-substrate:	0.885
CYP2C19-inhibitor:	0.9
CYP2C19-substrate:	0.836
CYP2C9-inhibitor:	0.376
CYP2C9-substrate:	0.691
CYP2D6-inhibitor:	0.635
CYP2D6-substrate:	0.641
CYP3A4-inhibitor:	0.623
CYP3A4-substrate:	0.788

ADMET: Excretion

Clearance (CL):	9.838
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.231
Drug-inuced Liver Injury (DILI):	0.442
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.652
Skin Sensitization:	0.863
Carcinogencity:	0.656
Eye Corrosion:	0.004
Eye Irritation:	0.045
Respiratory Toxicity:	0.009

Download Data

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

Natural Product: NPC127085

Natural Product ID:	NPC127085
*Common Name:**	3-(3,4,5-Trimethoxyphenyl)Propanoylpyrrole
IUPAC Name:	1-pyrrol-1-yl-3-(3,4,5-trimethoxyphenyl)propan-1-one
Synonyms:	3-(3,4,5-Trimethoxyphenyl)Propanoylpyrrole
Standard InCHIKey:	OEPMYHLWGJDONN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H19NO4/c1-19-13-10-12(11-14(20-2)16(13)21-3)6-7-15(18)17-8-4-5-9-17/h4-5,8-11H,6-7H2,1-3H3
SMILES:	COc1cc(CCC(=O)n2cccc2)cc(c1OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669583
PubChem CID:	50994067
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
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	whole plant	Luxi County, Yunnan Province, China	2008-OCT	PMID[21158422]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21158422]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	8

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[505797]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[505797]
NPT133	Cell Line	ZR-75-1	Homo sapiens	IC50	>	40000.0	nM	PMID[505797]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	40000.0	nM	PMID[505797]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	40000.0	nM	PMID[505797]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	40000.0	nM	PMID[505797]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	40000.0	nM	PMID[505797]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	40000.0	nM	PMID[505797]

☑ 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 NPC127085 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	415
0.1-0.2	2978
0.2-0.3	13037
0.3-0.4	3410
0.4-0.5	11564
0.5-0.6	9769
0.6-0.7	1375
0.7-0.8	146
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC210256
0.8408	Intermediate Similarity	NPC54066
0.7784	Intermediate Similarity	NPC195268
0.7784	Intermediate Similarity	NPC133140
0.7688	Intermediate Similarity	NPC477019
0.767	Intermediate Similarity	NPC236668
0.7638	Intermediate Similarity	NPC476578
0.7638	Intermediate Similarity	NPC4071
0.7638	Intermediate Similarity	NPC476582
0.7633	Intermediate Similarity	NPC146976
0.7632	Intermediate Similarity	NPC271792
0.7604	Intermediate Similarity	NPC90875
0.7593	Intermediate Similarity	NPC233334
0.7549	Intermediate Similarity	NPC313189
0.7537	Intermediate Similarity	NPC16452
0.7537	Intermediate Similarity	NPC476581
0.7537	Intermediate Similarity	NPC36229
0.7536	Intermediate Similarity	NPC174049
0.7524	Intermediate Similarity	NPC473822
0.7523	Intermediate Similarity	NPC253675
0.7513	Intermediate Similarity	NPC471448
0.7489	Intermediate Similarity	NPC124313
0.7477	Intermediate Similarity	NPC84164
0.7477	Intermediate Similarity	NPC207283
0.7465	Intermediate Similarity	NPC122463
0.7452	Intermediate Similarity	NPC53069
0.7452	Intermediate Similarity	NPC296482
0.7452	Intermediate Similarity	NPC202768
0.7432	Intermediate Similarity	NPC119134
0.7419	Intermediate Similarity	NPC24019
0.7397	Intermediate Similarity	NPC172222
0.7389	Intermediate Similarity	NPC31930
0.7379	Intermediate Similarity	NPC135549
0.7366	Intermediate Similarity	NPC15406
0.7363	Intermediate Similarity	NPC224928
0.7356	Intermediate Similarity	NPC290689
0.734	Intermediate Similarity	NPC234197
0.7333	Intermediate Similarity	NPC266931
0.733	Intermediate Similarity	NPC108342
0.733	Intermediate Similarity	NPC312872
0.7325	Intermediate Similarity	NPC183537
0.7324	Intermediate Similarity	NPC308906
0.7306	Intermediate Similarity	NPC201508
0.7297	Intermediate Similarity	NPC182907
0.7297	Intermediate Similarity	NPC189903
0.7286	Intermediate Similarity	NPC96405
0.7286	Intermediate Similarity	NPC202605
0.7286	Intermediate Similarity	NPC171409
0.7286	Intermediate Similarity	NPC112206
0.7265	Intermediate Similarity	NPC166722
0.7249	Intermediate Similarity	NPC77878
0.724	Intermediate Similarity	NPC96584
0.724	Intermediate Similarity	NPC255800
0.7222	Intermediate Similarity	NPC210434
0.7212	Intermediate Similarity	NPC193238
0.7205	Intermediate Similarity	NPC134637
0.7204	Intermediate Similarity	NPC251160
0.72	Intermediate Similarity	NPC92111
0.7177	Intermediate Similarity	NPC82548
0.7172	Intermediate Similarity	NPC204385
0.717	Intermediate Similarity	NPC271215
0.717	Intermediate Similarity	NPC149471
0.7162	Intermediate Similarity	NPC22481
0.715	Intermediate Similarity	NPC76748
0.7149	Intermediate Similarity	NPC476999
0.7143	Intermediate Similarity	NPC174758
0.7143	Intermediate Similarity	NPC206201
0.7129	Intermediate Similarity	NPC16249
0.7129	Intermediate Similarity	NPC307963
0.7124	Intermediate Similarity	NPC210296
0.7123	Intermediate Similarity	NPC316981
0.7112	Intermediate Similarity	NPC169742
0.7109	Intermediate Similarity	NPC470020
0.7104	Intermediate Similarity	NPC278525
0.71	Intermediate Similarity	NPC296527
0.7083	Intermediate Similarity	NPC168209
0.7074	Intermediate Similarity	NPC107123
0.7067	Intermediate Similarity	NPC475774
0.7059	Intermediate Similarity	NPC476997
0.7059	Intermediate Similarity	NPC246381
0.7059	Intermediate Similarity	NPC473053
0.7056	Intermediate Similarity	NPC470474
0.7048	Intermediate Similarity	NPC217554
0.7044	Intermediate Similarity	NPC289786
0.704	Intermediate Similarity	NPC471004
0.7037	Intermediate Similarity	NPC100079
0.7037	Intermediate Similarity	NPC23614
0.7031	Intermediate Similarity	NPC284141
0.7028	Intermediate Similarity	NPC188420
0.7027	Intermediate Similarity	NPC476998
0.7027	Intermediate Similarity	NPC469792
0.7027	Intermediate Similarity	NPC476996
0.7019	Intermediate Similarity	NPC295898
0.7	Intermediate Similarity	NPC472287
0.7	Intermediate Similarity	NPC472286
0.6996	Remote Similarity	NPC217176
0.6986	Remote Similarity	NPC243633
0.6986	Remote Similarity	NPC175150
0.6982	Remote Similarity	NPC476994
0.6979	Remote Similarity	NPC318068
0.6976	Remote Similarity	NPC251090
0.696	Remote Similarity	NPC11408
0.6952	Remote Similarity	NPC264166
0.6952	Remote Similarity	NPC118832
0.6952	Remote Similarity	NPC47059
0.6952	Remote Similarity	NPC274291
0.6952	Remote Similarity	NPC165349
0.6952	Remote Similarity	NPC329708
0.695	Remote Similarity	NPC295158
0.6944	Remote Similarity	NPC274982
0.6934	Remote Similarity	NPC287208
0.6927	Remote Similarity	NPC46451
0.692	Remote Similarity	NPC129897
0.6916	Remote Similarity	NPC476995
0.6912	Remote Similarity	NPC473513
0.6912	Remote Similarity	NPC305984
0.6912	Remote Similarity	NPC12100
0.6901	Remote Similarity	NPC174672
0.69	Remote Similarity	NPC99891
0.6898	Remote Similarity	NPC4421
0.6898	Remote Similarity	NPC235076
0.6891	Remote Similarity	NPC108469
0.6884	Remote Similarity	NPC472098
0.6884	Remote Similarity	NPC264176
0.6881	Remote Similarity	NPC303658
0.6857	Remote Similarity	NPC66815
0.6852	Remote Similarity	NPC162530
0.6849	Remote Similarity	NPC313804
0.6849	Remote Similarity	NPC136924
0.6849	Remote Similarity	NPC284685
0.6849	Remote Similarity	NPC315804
0.684	Remote Similarity	NPC188400
0.6837	Remote Similarity	NPC146418
0.6837	Remote Similarity	NPC242923
0.6829	Remote Similarity	NPC56170
0.6823	Remote Similarity	NPC177404
0.682	Remote Similarity	NPC264674
0.682	Remote Similarity	NPC191489
0.681	Remote Similarity	NPC148896
0.681	Remote Similarity	NPC180668
0.681	Remote Similarity	NPC471013
0.6804	Remote Similarity	NPC158020
0.6804	Remote Similarity	NPC204446
0.6804	Remote Similarity	NPC75600
0.6804	Remote Similarity	NPC173080
0.6804	Remote Similarity	NPC212768
0.6804	Remote Similarity	NPC6576
0.6804	Remote Similarity	NPC473089
0.6804	Remote Similarity	NPC473115
0.6794	Remote Similarity	NPC287437
0.6792	Remote Similarity	NPC257511
0.6792	Remote Similarity	NPC285558
0.6791	Remote Similarity	NPC471304
0.6789	Remote Similarity	NPC42678
0.6789	Remote Similarity	NPC477909
0.6789	Remote Similarity	NPC477907
0.6788	Remote Similarity	NPC473057
0.6787	Remote Similarity	NPC17305
0.6787	Remote Similarity	NPC60621
0.6783	Remote Similarity	NPC168922
0.6781	Remote Similarity	NPC475533
0.6773	Remote Similarity	NPC74360
0.6773	Remote Similarity	NPC84815
0.6773	Remote Similarity	NPC17565
0.6773	Remote Similarity	NPC301368
0.6771	Remote Similarity	NPC235628
0.6771	Remote Similarity	NPC473449
0.6767	Remote Similarity	NPC316224
0.6763	Remote Similarity	NPC146724
0.6762	Remote Similarity	NPC176538
0.6761	Remote Similarity	NPC472111
0.6758	Remote Similarity	NPC471016
0.6757	Remote Similarity	NPC46970
0.6752	Remote Similarity	NPC324619
0.6752	Remote Similarity	NPC1608
0.6752	Remote Similarity	NPC475315
0.6749	Remote Similarity	NPC61350
0.6746	Remote Similarity	NPC472284
0.6744	Remote Similarity	NPC472550
0.6744	Remote Similarity	NPC48042
0.6744	Remote Similarity	NPC304179
0.6741	Remote Similarity	NPC319232
0.6741	Remote Similarity	NPC24370
0.6737	Remote Similarity	NPC137353
0.6733	Remote Similarity	NPC62069
0.673	Remote Similarity	NPC232727
0.6729	Remote Similarity	NPC475835
0.6728	Remote Similarity	NPC26679
0.6727	Remote Similarity	NPC62367
0.6726	Remote Similarity	NPC122436
0.6725	Remote Similarity	NPC295228
0.6723	Remote Similarity	NPC270515
0.6715	Remote Similarity	NPC79293
0.6715	Remote Similarity	NPC279401
0.6715	Remote Similarity	NPC198673
0.6713	Remote Similarity	NPC219664
0.6712	Remote Similarity	NPC30570
0.6712	Remote Similarity	NPC470306
0.6712	Remote Similarity	NPC477912
0.6712	Remote Similarity	NPC288349

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 NPC127085 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	673
0.2-0.3	919
0.3-0.4	1212
0.4-0.5	2990
0.5-0.6	2505
0.6-0.7	551
0.7-0.8	42
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7989	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7968	Intermediate Similarity	NPD3386	Phase 2
0.7953	Intermediate Similarity	NPD7886	Phase 2
0.7953	Intermediate Similarity	NPD7885	Phase 2
0.7947	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD3921	Approved
0.7784	Intermediate Similarity	NPD3924	Approved
0.7784	Intermediate Similarity	NPD3922	Approved
0.7784	Intermediate Similarity	NPD3923	Approved
0.7703	Intermediate Similarity	NPD8350	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5601	Phase 2
0.7581	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD6361	Phase 2
0.7512	Intermediate Similarity	NPD6219	Discontinued
0.7487	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD3816	Phase 1
0.7452	Intermediate Similarity	NPD3815	Phase 1
0.7436	Intermediate Similarity	NPD4375	Approved
0.7385	Intermediate Similarity	NPD4889	Approved
0.7358	Intermediate Similarity	NPD6568	Discontinued
0.732	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5513	Phase 2
0.73	Intermediate Similarity	NPD4551	Phase 2
0.729	Intermediate Similarity	NPD8479	Phase 2
0.7286	Intermediate Similarity	NPD7069	Discontinued
0.7285	Intermediate Similarity	NPD6964	Approved
0.7285	Intermediate Similarity	NPD6963	Approved
0.725	Intermediate Similarity	NPD4372	Phase 1
0.7243	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3920	Phase 2
0.7209	Intermediate Similarity	NPD6856	Discontinued
0.7207	Intermediate Similarity	NPD7807	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5866	Approved
0.7202	Intermediate Similarity	NPD5640	Discontinued
0.7195	Intermediate Similarity	NPD4885	Approved
0.7178	Intermediate Similarity	NPD4418	Discontinued
0.7129	Intermediate Similarity	NPD1038	Approved
0.7116	Intermediate Similarity	NPD3354	Phase 2
0.7095	Intermediate Similarity	NPD7467	Discontinued
0.7094	Intermediate Similarity	NPD3395	Approved
0.7094	Intermediate Similarity	NPD3396	Approved
0.7092	Intermediate Similarity	NPD2600	Approved
0.7092	Intermediate Similarity	NPD2599	Approved
0.7092	Intermediate Similarity	NPD2601	Approved
0.708	Intermediate Similarity	NPD2929	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6242	Discontinued
0.7047	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6727	Phase 2
0.7019	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6517	Phase 3
0.7009	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2060	Approved
0.6995	Remote Similarity	NPD6569	Phase 2
0.6991	Remote Similarity	NPD4989	Phase 2
0.6991	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6790	Phase 1
0.6972	Remote Similarity	NPD3590	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5015	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7967	Discontinued
0.6952	Remote Similarity	NPD4038	Approved
0.6952	Remote Similarity	NPD4035	Approved
0.6952	Remote Similarity	NPD4037	Approved
0.6952	Remote Similarity	NPD4033	Approved
0.6952	Remote Similarity	NPD32	Approved
0.6952	Remote Similarity	NPD4039	Approved
0.6952	Remote Similarity	NPD31	Approved
0.6952	Remote Similarity	NPD4034	Approved
0.6952	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD4036	Approved
0.6952	Remote Similarity	NPD3397	Phase 2
0.6952	Remote Similarity	NPD4122	Approved
0.6943	Remote Similarity	NPD1483	Discontinued
0.6942	Remote Similarity	NPD4899	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7826	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD6366	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD5658	Approved
0.6931	Remote Similarity	NPD4021	Phase 2
0.6927	Remote Similarity	NPD3763	Approved
0.6923	Remote Similarity	NPD7859	Phase 2
0.691	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD4072	Approved
0.6904	Remote Similarity	NPD4071	Approved
0.6904	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5612	Discontinued
0.6859	Remote Similarity	NPD2511	Approved
0.6858	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7955	Approved
0.6849	Remote Similarity	NPD7956	Approved
0.6848	Remote Similarity	NPD2219	Phase 1
0.6847	Remote Similarity	NPD4132	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2780	Approved
0.6839	Remote Similarity	NPD2782	Approved
0.6835	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4333	Phase 1
0.6821	Remote Similarity	NPD5319	Approved
0.6821	Remote Similarity	NPD5320	Approved
0.682	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.682	Remote Similarity	NPD7708	Approved
0.682	Remote Similarity	NPD5149	Phase 2
0.6818	Remote Similarity	NPD1032	Phase 2
0.6816	Remote Similarity	NPD7426	Phase 1
0.6812	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5437	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD7263	Phase 2
0.6808	Remote Similarity	NPD2886	Approved
0.6808	Remote Similarity	NPD2885	Approved
0.6807	Remote Similarity	NPD8091	Phase 3
0.6804	Remote Similarity	NPD3313	Phase 2
0.6804	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.68	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3825	Phase 3
0.6794	Remote Similarity	NPD3541	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3947	Discontinued
0.6791	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD4923	Phase 1
0.6786	Remote Similarity	NPD4083	Discontinued
0.6784	Remote Similarity	NPD6494	Phase 2
0.678	Remote Similarity	NPD2334	Discontinued
0.6779	Remote Similarity	NPD2952	Discontinued
0.6777	Remote Similarity	NPD7123	Suspended
0.6774	Remote Similarity	NPD5297	Approved
0.6773	Remote Similarity	NPD6974	Phase 3
0.6769	Remote Similarity	NPD2781	Approved
0.6766	Remote Similarity	NPD7588	Discontinued
0.6759	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4131	Phase 3
0.6757	Remote Similarity	NPD8356	Approved
0.6753	Remote Similarity	NPD7417	Discontinued
0.6749	Remote Similarity	NPD2917	Approved
0.6749	Remote Similarity	NPD7757	Approved
0.6749	Remote Similarity	NPD7758	Approved
0.6743	Remote Similarity	NPD3257	Approved
0.6738	Remote Similarity	NPD7792	Phase 1
0.6731	Remote Similarity	NPD3477	Phase 2
0.6731	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7134	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4429	Discontinued
0.672	Remote Similarity	NPD9596	Approved
0.672	Remote Similarity	NPD9595	Approved
0.6714	Remote Similarity	NPD4548	Discontinued
0.6714	Remote Similarity	NPD5999	Phase 2
0.6714	Remote Similarity	NPD2831	Approved
0.6712	Remote Similarity	NPD6298	Discontinued
0.6712	Remote Similarity	NPD5147	Discontinued
0.6711	Remote Similarity	NPD4080	Discontinued
0.6711	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.671	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.671	Remote Similarity	NPD8016	Phase 3
0.6708	Remote Similarity	NPD7803	Approved
0.6703	Remote Similarity	NPD201	Phase 2
0.6703	Remote Similarity	NPD200	Phase 2
0.6701	Remote Similarity	NPD5088	Discontinued
0.6698	Remote Similarity	NPD2187	Approved
0.6698	Remote Similarity	NPD2189	Approved
0.6697	Remote Similarity	NPD3258	Approved
0.6696	Remote Similarity	NPD7719	Discontinued
0.6681	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD5559	Phase 2
0.6667	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2582	Approved
0.6667	Remote Similarity	NPD5293	Phase 2
0.6667	Remote Similarity	NPD2581	Approved
0.6653	Remote Similarity	NPD4558	Phase 2
0.6652	Remote Similarity	NPD4876	Phase 3
0.6652	Remote Similarity	NPD4875	Phase 3
0.6652	Remote Similarity	NPD3006	Discontinued
0.6651	Remote Similarity	NPD1392	Approved
0.6651	Remote Similarity	NPD7452	Approved
0.6651	Remote Similarity	NPD5512	Phase 3
0.6651	Remote Similarity	NPD7453	Approved
0.6651	Remote Similarity	NPD6550	Discontinued
0.6651	Remote Similarity	NPD7222	Phase 2
0.665	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4678	Approved
0.6649	Remote Similarity	NPD4675	Approved
0.6638	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4328	Approved
0.6637	Remote Similarity	NPD8430	Approved
0.6636	Remote Similarity	NPD4795	Phase 2
0.6636	Remote Similarity	NPD4048	Approved
0.6635	Remote Similarity	NPD4052	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD1034	Phase 3
0.6633	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.662	Remote Similarity	NPD3853	Clinical (unspecified phase)
0.662	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6276	Discontinued
0.6608	Remote Similarity	NPD5014	Discontinued
0.6606	Remote Similarity	NPD5067	Phase 2
0.6606	Remote Similarity	NPD5066	Phase 2
0.6604	Remote Similarity	NPD1739	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