NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	219.04
Volume:	212.967
LogP:	3.3
LogD:	2.958
LogS:	-3.263
# Rotatable Bonds:	2
TPSA:	50.19
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.79
Synthetic Accessibility Score:	2.621
Fsp3:	0.091
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.544
MDCK Permeability:	2.461557960486971e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.21
30% Bioavailability (F30%):	0.211

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.588
Plasma Protein Binding (PPB):	95.3506851196289%
Volume Distribution (VD):	0.564
Pgp-substrate:	4.758148670196533%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.253
CYP2C19-inhibitor:	0.776
CYP2C19-substrate:	0.092
CYP2C9-inhibitor:	0.629
CYP2C9-substrate:	0.826
CYP2D6-inhibitor:	0.322
CYP2D6-substrate:	0.391
CYP3A4-inhibitor:	0.214
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	4.329
Half-life (T1/2):	0.333

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.046
Drug-inuced Liver Injury (DILI):	0.392
AMES Toxicity:	0.381
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.208
Carcinogencity:	0.466
Eye Corrosion:	0.641
Eye Irritation:	0.986
Respiratory Toxicity:	0.862

Download Data

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

Natural Product: NPC238242

Natural Product ID:	NPC238242
*Common Name:**	Pulicatin D
IUPAC Name:	n.a.
Synonyms:	Pulicatin D
Standard InCHIKey:	MJVDHWKRLKYQTC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H9NO2S/c1-7-9(6-13)12-11(15-7)8-4-2-3-5-10(8)14/h2-6,14H,1H3
SMILES:	O=Cc1nc(sc1C)c1ccccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651096
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000436] Azoles [CHEMONTID:0000095] Thiazoles [CHEMONTID:0002637] 2,4,5-trisubstituted thiazoles

*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
NPO30976	Streptomyces sp. cp32	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21028889]

☑ 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
Ki	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT291	Individual Protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	Ki	=	1541.0	nM	PMID[506333]

☑ 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 NPC238242 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	310
0.1-0.2	3568
0.2-0.3	13768
0.3-0.4	6648
0.4-0.5	15136
0.5-0.6	3007
0.6-0.7	253
0.7-0.8	5
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8523	High Similarity	NPC249662
0.7368	Intermediate Similarity	NPC241025
0.7277	Intermediate Similarity	NPC295158
0.7254	Intermediate Similarity	NPC188104
0.7136	Intermediate Similarity	NPC472284
0.6979	Remote Similarity	NPC222592
0.6979	Remote Similarity	NPC168486
0.6976	Remote Similarity	NPC472287
0.6976	Remote Similarity	NPC472286
0.6927	Remote Similarity	NPC161292
0.6908	Remote Similarity	NPC210828
0.6908	Remote Similarity	NPC86834
0.689	Remote Similarity	NPC23294
0.6869	Remote Similarity	NPC144381
0.685	Remote Similarity	NPC230403
0.6842	Remote Similarity	NPC303951
0.6816	Remote Similarity	NPC471598
0.6806	Remote Similarity	NPC474409
0.6794	Remote Similarity	NPC14877
0.6794	Remote Similarity	NPC475350
0.6794	Remote Similarity	NPC145178
0.678	Remote Similarity	NPC280853
0.6776	Remote Similarity	NPC153769
0.6742	Remote Similarity	NPC245657
0.6742	Remote Similarity	NPC285016
0.6733	Remote Similarity	NPC93390
0.673	Remote Similarity	NPC9894
0.6723	Remote Similarity	NPC471596
0.6723	Remote Similarity	NPC41982
0.6717	Remote Similarity	NPC194040
0.6704	Remote Similarity	NPC60553
0.6698	Remote Similarity	NPC247803
0.6698	Remote Similarity	NPC251036
0.6684	Remote Similarity	NPC303225
0.6683	Remote Similarity	NPC473821
0.6683	Remote Similarity	NPC206186
0.6667	Remote Similarity	NPC78767
0.6667	Remote Similarity	NPC473814
0.665	Remote Similarity	NPC212535
0.6649	Remote Similarity	NPC322644
0.6636	Remote Similarity	NPC150239
0.6635	Remote Similarity	NPC134848
0.6619	Remote Similarity	NPC183777
0.6619	Remote Similarity	NPC321428
0.6619	Remote Similarity	NPC283117
0.6616	Remote Similarity	NPC320394
0.6595	Remote Similarity	NPC284348
0.6588	Remote Similarity	NPC39679
0.6585	Remote Similarity	NPC74153
0.6583	Remote Similarity	NPC94943
0.6582	Remote Similarity	NPC72980
0.6575	Remote Similarity	NPC478141
0.6559	Remote Similarity	NPC26872
0.6555	Remote Similarity	NPC75498
0.6553	Remote Similarity	NPC306376
0.6542	Remote Similarity	NPC12344
0.654	Remote Similarity	NPC270918
0.654	Remote Similarity	NPC53344
0.6533	Remote Similarity	NPC190007
0.6531	Remote Similarity	NPC283152
0.6528	Remote Similarity	NPC3207
0.6526	Remote Similarity	NPC177404
0.6522	Remote Similarity	NPC257142
0.6509	Remote Similarity	NPC171787
0.6495	Remote Similarity	NPC294375
0.6484	Remote Similarity	NPC470404
0.6484	Remote Similarity	NPC470394
0.6484	Remote Similarity	NPC470403
0.6479	Remote Similarity	NPC325297
0.6476	Remote Similarity	NPC138562
0.6465	Remote Similarity	NPC308137
0.6465	Remote Similarity	NPC325705
0.6465	Remote Similarity	NPC52831
0.6465	Remote Similarity	NPC310211
0.6462	Remote Similarity	NPC247980
0.6462	Remote Similarity	NPC249583
0.6455	Remote Similarity	NPC26850
0.645	Remote Similarity	NPC62069
0.645	Remote Similarity	NPC207851
0.6447	Remote Similarity	NPC477589
0.6447	Remote Similarity	NPC477587
0.6444	Remote Similarity	NPC471594
0.6442	Remote Similarity	NPC280714
0.6425	Remote Similarity	NPC70956
0.6425	Remote Similarity	NPC243834
0.6425	Remote Similarity	NPC41717
0.6422	Remote Similarity	NPC293151
0.6419	Remote Similarity	NPC146418
0.6419	Remote Similarity	NPC87413
0.6415	Remote Similarity	NPC175602
0.6414	Remote Similarity	NPC88363
0.6413	Remote Similarity	NPC153467
0.6413	Remote Similarity	NPC470395
0.6408	Remote Similarity	NPC276517
0.6402	Remote Similarity	NPC61038
0.6398	Remote Similarity	NPC200836
0.6398	Remote Similarity	NPC317572
0.6396	Remote Similarity	NPC288943
0.6392	Remote Similarity	NPC44161
0.6391	Remote Similarity	NPC477585
0.6391	Remote Similarity	NPC477590
0.6391	Remote Similarity	NPC477586
0.6391	Remote Similarity	NPC477588
0.6383	Remote Similarity	NPC161108
0.6373	Remote Similarity	NPC122427
0.6373	Remote Similarity	NPC471178
0.6373	Remote Similarity	NPC329961
0.6368	Remote Similarity	NPC179287
0.6368	Remote Similarity	NPC116573
0.6364	Remote Similarity	NPC96890
0.636	Remote Similarity	NPC475635
0.6355	Remote Similarity	NPC46580
0.6354	Remote Similarity	NPC124542
0.6354	Remote Similarity	NPC471177
0.6354	Remote Similarity	NPC59779
0.6346	Remote Similarity	NPC153042
0.6346	Remote Similarity	NPC90229
0.6344	Remote Similarity	NPC477516
0.6343	Remote Similarity	NPC220337
0.6338	Remote Similarity	NPC45190
0.6337	Remote Similarity	NPC314002
0.6337	Remote Similarity	NPC42591
0.6335	Remote Similarity	NPC174760
0.6324	Remote Similarity	NPC128751
0.6324	Remote Similarity	NPC246700
0.6323	Remote Similarity	NPC314633
0.6322	Remote Similarity	NPC273714
0.6321	Remote Similarity	NPC165599
0.6321	Remote Similarity	NPC476098
0.6319	Remote Similarity	NPC85443
0.6318	Remote Similarity	NPC46561
0.6318	Remote Similarity	NPC159125
0.6313	Remote Similarity	NPC219087
0.6313	Remote Similarity	NPC110182
0.631	Remote Similarity	NPC13432
0.6301	Remote Similarity	NPC322064
0.63	Remote Similarity	NPC478032
0.6296	Remote Similarity	NPC269367
0.6295	Remote Similarity	NPC97746
0.6293	Remote Similarity	NPC469497
0.6293	Remote Similarity	NPC106833
0.6291	Remote Similarity	NPC472259
0.629	Remote Similarity	NPC269270
0.6287	Remote Similarity	NPC204717
0.6286	Remote Similarity	NPC151779
0.6284	Remote Similarity	NPC151781
0.6284	Remote Similarity	NPC74562
0.6284	Remote Similarity	NPC316181
0.6284	Remote Similarity	NPC207866
0.6281	Remote Similarity	NPC184964
0.6277	Remote Similarity	NPC264400
0.6275	Remote Similarity	NPC66083
0.6275	Remote Similarity	NPC36498
0.6274	Remote Similarity	NPC295898
0.6273	Remote Similarity	NPC27041
0.6268	Remote Similarity	NPC156704
0.6262	Remote Similarity	NPC469390
0.6261	Remote Similarity	NPC128115
0.6261	Remote Similarity	NPC473187
0.6261	Remote Similarity	NPC14686
0.6256	Remote Similarity	NPC49051
0.6256	Remote Similarity	NPC315491
0.6256	Remote Similarity	NPC237740
0.6256	Remote Similarity	NPC118228
0.6256	Remote Similarity	NPC45459
0.625	Remote Similarity	NPC42979
0.625	Remote Similarity	NPC67659
0.625	Remote Similarity	NPC205372
0.625	Remote Similarity	NPC84508
0.6244	Remote Similarity	NPC174576
0.6244	Remote Similarity	NPC53144
0.6238	Remote Similarity	NPC220765
0.6237	Remote Similarity	NPC473057
0.6235	Remote Similarity	NPC315411
0.6234	Remote Similarity	NPC6786
0.6233	Remote Similarity	NPC198503
0.6233	Remote Similarity	NPC4687
0.6232	Remote Similarity	NPC114335
0.6232	Remote Similarity	NPC280964
0.6232	Remote Similarity	NPC141915
0.6232	Remote Similarity	NPC165538
0.6232	Remote Similarity	NPC56170
0.6231	Remote Similarity	NPC224764
0.6225	Remote Similarity	NPC61350
0.6225	Remote Similarity	NPC171171
0.6224	Remote Similarity	NPC278874
0.6224	Remote Similarity	NPC24990
0.622	Remote Similarity	NPC242209
0.6219	Remote Similarity	NPC271792
0.6216	Remote Similarity	NPC48317
0.6216	Remote Similarity	NPC74360
0.6212	Remote Similarity	NPC471294
0.6201	Remote Similarity	NPC475196
0.6197	Remote Similarity	NPC475112
0.6197	Remote Similarity	NPC291535
0.6197	Remote Similarity	NPC475085
0.6193	Remote Similarity	NPC126481
0.6193	Remote Similarity	NPC473764
0.6193	Remote Similarity	NPC314940
0.6193	Remote Similarity	NPC187501

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 NPC238242 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	764
0.2-0.3	833
0.3-0.4	1347
0.4-0.5	4203
0.5-0.6	1632
0.6-0.7	105
0.7-0.8	11
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
0.799	Intermediate Similarity	NPD1976	Approved
0.7474	Intermediate Similarity	NPD3127	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1218	Approved
0.7436	Intermediate Similarity	NPD1219	Approved
0.7382	Intermediate Similarity	NPD2749	Discontinued
0.7317	Intermediate Similarity	NPD4331	Approved
0.7268	Intermediate Similarity	NPD5452	Phase 2
0.7265	Intermediate Similarity	NPD6475	Phase 2
0.7212	Intermediate Similarity	NPD5453	Phase 2
0.7204	Intermediate Similarity	NPD647	Approved
0.7129	Intermediate Similarity	NPD6324	Phase 1
0.7098	Intermediate Similarity	NPD3328	Phase 2
0.7005	Intermediate Similarity	NPD954	Phase 1
0.6995	Remote Similarity	NPD1897	Discontinued
0.6959	Remote Similarity	NPD2306	Approved
0.6903	Remote Similarity	NPD5817	Discontinued
0.684	Remote Similarity	NPD5191	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3074	Discontinued
0.6739	Remote Similarity	NPD5189	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5828	Phase 2
0.6681	Remote Similarity	NPD5857	Phase 3
0.6667	Remote Similarity	NPD5634	Approved
0.6667	Remote Similarity	NPD1631	Approved
0.6652	Remote Similarity	NPD7214	Phase 3
0.6633	Remote Similarity	NPD9542	Approved
0.6612	Remote Similarity	NPD1005	Phase 2
0.6612	Remote Similarity	NPD1004	Phase 2
0.6605	Remote Similarity	NPD7496	Phase 2
0.6595	Remote Similarity	NPD7215	Phase 2
0.658	Remote Similarity	NPD6205	Discontinued
0.6574	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3395	Approved
0.6569	Remote Similarity	NPD3396	Approved
0.6552	Remote Similarity	NPD981	Phase 2
0.6524	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD1630	Approved
0.6502	Remote Similarity	NPD4949	Discontinued
0.6465	Remote Similarity	NPD9510	Approved
0.6455	Remote Similarity	NPD4439	Discontinued
0.6447	Remote Similarity	NPD3488	Phase 1
0.6443	Remote Similarity	NPD1573	Approved
0.6443	Remote Similarity	NPD1575	Approved
0.6441	Remote Similarity	NPD6246	Approved
0.644	Remote Similarity	NPD9487	Approved
0.6432	Remote Similarity	NPD6376	Discontinued
0.6429	Remote Similarity	NPD158	Discontinued
0.6398	Remote Similarity	NPD4044	Discontinued
0.6393	Remote Similarity	NPD3525	Discontinued
0.6393	Remote Similarity	NPD3759	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5866	Approved
0.6372	Remote Similarity	NPD5420	Discontinued
0.6364	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4884	Discovery
0.6355	Remote Similarity	NPD2383	Phase 1
0.6351	Remote Similarity	NPD2779	Approved
0.6349	Remote Similarity	NPD1597	Phase 1
0.6346	Remote Similarity	NPD6988	Phase 1
0.6345	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD8284	Discontinued
0.6337	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD1587	Approved
0.633	Remote Similarity	NPD1638	Discovery
0.6318	Remote Similarity	NPD1745	Approved
0.6316	Remote Similarity	NPD1788	Approved
0.6316	Remote Similarity	NPD1789	Approved
0.6301	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.63	Remote Similarity	NPD1643	Phase 3
0.6296	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6974	Phase 3
0.629	Remote Similarity	NPD4312	Approved
0.6286	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD2916	Discontinued
0.6276	Remote Similarity	NPD4438	Approved
0.6276	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD9363	Approved
0.6275	Remote Similarity	NPD9364	Phase 2
0.6267	Remote Similarity	NPD3223	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD3250	Phase 1
0.6261	Remote Similarity	NPD7180	Phase 3
0.6256	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD4897	Phase 2
0.6256	Remote Similarity	NPD484	Approved
0.625	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1592	Phase 3
0.625	Remote Similarity	NPD6134	Phase 2
0.6244	Remote Similarity	NPD2792	Approved
0.6244	Remote Similarity	NPD6349	Phase 1
0.6239	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD444	Approved
0.6233	Remote Similarity	NPD5506	Approved
0.6233	Remote Similarity	NPD5507	Approved
0.623	Remote Similarity	NPD7416	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD1505	Phase 2
0.6225	Remote Similarity	NPD3315	Phase 3
0.6221	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD3327	Approved
0.6214	Remote Similarity	NPD6348	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD2778	Approved
0.6209	Remote Similarity	NPD1768	Approved
0.6207	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD3351	Approved
0.6202	Remote Similarity	NPD2717	Phase 2
0.62	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6159	Phase 2
0.6198	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4948	Discontinued
0.6193	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD3487	Phase 1
0.6186	Remote Similarity	NPD1684	Approved
0.6186	Remote Similarity	NPD1685	Approved
0.6181	Remote Similarity	NPD1586	Approved
0.6175	Remote Similarity	NPD8108	Approved
0.6174	Remote Similarity	NPD4850	Phase 1
0.6174	Remote Similarity	NPD4460	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD2021	Discontinued
0.6171	Remote Similarity	NPD5632	Approved
0.6169	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5144	Discontinued
0.6166	Remote Similarity	NPD704	Clinical (unspecified phase)
0.616	Remote Similarity	NPD6276	Discontinued
0.6158	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD3350	Approved
0.6157	Remote Similarity	NPD5050	Approved
0.6154	Remote Similarity	NPD5101	Discontinued
0.6154	Remote Similarity	NPD1545	Discontinued
0.615	Remote Similarity	NPD7719	Discontinued
0.6147	Remote Similarity	NPD3392	Approved
0.6143	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD5512	Phase 3
0.614	Remote Similarity	NPD5628	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD3945	Discontinued
0.6135	Remote Similarity	NPD5316	Approved
0.6133	Remote Similarity	NPD3611	Phase 3
0.6126	Remote Similarity	NPD8107	Approved
0.6126	Remote Similarity	NPD5059	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD1957	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD802	Phase 2
0.6124	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6123	Remote Similarity	NPD7540	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD925	Approved
0.6122	Remote Similarity	NPD926	Approved
0.6121	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD6641	Approved
0.6119	Remote Similarity	NPD5416	Discontinued
0.6119	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD6642	Approved
0.6114	Remote Similarity	NPD9383	Approved
0.6114	Remote Similarity	NPD9382	Approved
0.6109	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6109	Remote Similarity	NPD7873	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD3178	Discontinued
0.6108	Remote Similarity	NPD9362	Approved
0.6108	Remote Similarity	NPD4203	Approved
0.6108	Remote Similarity	NPD4204	Approved
0.6103	Remote Similarity	NPD5228	Phase 3
0.6099	Remote Similarity	NPD2011	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD3354	Phase 2
0.6096	Remote Similarity	NPD649	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD7691	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD946	Discontinued
0.6093	Remote Similarity	NPD5513	Phase 2
0.6091	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD7816	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD3910	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5020	Approved
0.6073	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD2882	Phase 1
0.6071	Remote Similarity	NPD863	Approved
0.6071	Remote Similarity	NPD861	Approved
0.6071	Remote Similarity	NPD862	Approved
0.607	Remote Similarity	NPD3325	Approved
0.6068	Remote Similarity	NPD2414	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6825	Phase 1
0.6061	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD2781	Approved
0.6058	Remote Similarity	NPD1213	Phase 3
0.6054	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6052	Remote Similarity	NPD6755	Phase 2
0.6051	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.605	Remote Similarity	NPD1925	Approved
0.6047	Remote Similarity	NPD6975	Discontinued
0.6045	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD6155	Phase 1
0.6041	Remote Similarity	NPD2782	Approved
0.6041	Remote Similarity	NPD2780	Approved
0.6037	Remote Similarity	NPD3003	Approved
0.6034	Remote Similarity	NPD4373	Phase 2

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