NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.03
Volume:	215.968
LogP:	3.198
LogD:	2.314
LogS:	-3.791
# Rotatable Bonds:	0
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.38
Synthetic Accessibility Score:	3.457
Fsp3:	0.25
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:	-4.396
MDCK Permeability:	3.063887561438605e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.324
Plasma Protein Binding (PPB):	93.28789520263672%
Volume Distribution (VD):	4.086
Pgp-substrate:	2.0628387928009033%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.308
CYP2C19-inhibitor:	0.968
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.876
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.089
CYP2D6-substrate:	0.51
CYP3A4-inhibitor:	0.459
CYP3A4-substrate:	0.164

ADMET: Excretion

Clearance (CL):	11.893
Half-life (T1/2):	0.682

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.829
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.961
Rat Oral Acute Toxicity:	0.954
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.939
Carcinogencity:	0.599
Eye Corrosion:	0.974
Eye Irritation:	0.991
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC100353

Natural Product ID:	NPC100353
*Common Name:**	(3S)-3-(3-Chloroprop-1-Ynyl)-3,4-Dihydroisochromen-1-One
IUPAC Name:	(3S)-3-(3-chloroprop-1-ynyl)-3,4-dihydroisochromen-1-one
Synonyms:
Standard InCHIKey:	HIULLKVUQCDVBL-SNVBAGLBSA-N
Standard InCHI:	InChI=1S/C12H9ClO2/c13-7-3-5-10-8-9-4-1-2-6-11(9)12(14)15-10/h1-2,4,6,10H,7-8H2/t10-/m1/s1
SMILES:	c1ccc2c(c1)C[C@@H](C#CCCl)OC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3086898
PubChem CID:	72945293
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO32834	gymnopus sp.	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24175638]

☑ 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	1
MIC	2

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	IC50	=	14000.0	nM	PMID[515720]
NPT3481	Organism	Mucor hiemalis	Mucor hiemalis	MIC	=	33.3	ug.mL-1	PMID[515720]
NPT2631	Organism	Chromobacterium violaceum	Chromobacterium violaceum	MIC	=	33.3	ug.mL-1	PMID[515720]

☑ 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 NPC100353 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	290
0.1-0.2	1586
0.2-0.3	4114
0.3-0.4	10860
0.4-0.5	11118
0.5-0.6	11386
0.6-0.7	3064
0.7-0.8	236
0.8-0.85	39
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC243355
0.8684	High Similarity	NPC474685
0.8661	High Similarity	NPC210089
0.8649	High Similarity	NPC99846
0.8649	High Similarity	NPC269023
0.8522	High Similarity	NPC210092
0.8496	Intermediate Similarity	NPC167504
0.8496	Intermediate Similarity	NPC474157
0.8482	Intermediate Similarity	NPC265407
0.8482	Intermediate Similarity	NPC83628
0.8455	Intermediate Similarity	NPC114594
0.8421	Intermediate Similarity	NPC79496
0.8378	Intermediate Similarity	NPC209632
0.8364	Intermediate Similarity	NPC89886
0.8364	Intermediate Similarity	NPC60679
0.8349	Intermediate Similarity	NPC42211
0.8348	Intermediate Similarity	NPC272524
0.8304	Intermediate Similarity	NPC119271
0.8276	Intermediate Similarity	NPC308744
0.8257	Intermediate Similarity	NPC118343
0.8241	Intermediate Similarity	NPC276775
0.8241	Intermediate Similarity	NPC249912
0.8241	Intermediate Similarity	NPC92754
0.823	Intermediate Similarity	NPC56493
0.8205	Intermediate Similarity	NPC306740
0.8174	Intermediate Similarity	NPC476003
0.8165	Intermediate Similarity	NPC225060
0.8165	Intermediate Similarity	NPC35448
0.8165	Intermediate Similarity	NPC78701
0.8158	Intermediate Similarity	NPC17417
0.8158	Intermediate Similarity	NPC10251
0.8142	Intermediate Similarity	NPC30594
0.8142	Intermediate Similarity	NPC37622
0.8136	Intermediate Similarity	NPC149691
0.8125	Intermediate Similarity	NPC31786
0.812	Intermediate Similarity	NPC477411
0.812	Intermediate Similarity	NPC307651
0.8108	Intermediate Similarity	NPC45613
0.8091	Intermediate Similarity	NPC146351
0.8087	Intermediate Similarity	NPC93084
0.8087	Intermediate Similarity	NPC214067
0.8087	Intermediate Similarity	NPC251854
0.8087	Intermediate Similarity	NPC196246
0.8087	Intermediate Similarity	NPC174099
0.8056	Intermediate Similarity	NPC130398
0.8049	Intermediate Similarity	NPC223351
0.8036	Intermediate Similarity	NPC474365
0.8036	Intermediate Similarity	NPC301943
0.8034	Intermediate Similarity	NPC128368
0.8018	Intermediate Similarity	NPC70624
0.8017	Intermediate Similarity	NPC305912
0.8017	Intermediate Similarity	NPC260818
0.8017	Intermediate Similarity	NPC1082
0.8	Intermediate Similarity	NPC469636
0.7983	Intermediate Similarity	NPC226093
0.7949	Intermediate Similarity	NPC82899
0.7949	Intermediate Similarity	NPC270699
0.7949	Intermediate Similarity	NPC321852
0.7949	Intermediate Similarity	NPC158282
0.7928	Intermediate Similarity	NPC325497
0.7895	Intermediate Similarity	NPC269457
0.7845	Intermediate Similarity	NPC474364
0.7845	Intermediate Similarity	NPC85493
0.784	Intermediate Similarity	NPC228739
0.7815	Intermediate Similarity	NPC153053
0.7815	Intermediate Similarity	NPC196075
0.7797	Intermediate Similarity	NPC212415
0.7788	Intermediate Similarity	NPC188895
0.7768	Intermediate Similarity	NPC203925
0.7759	Intermediate Similarity	NPC470391
0.7731	Intermediate Similarity	NPC474176
0.7705	Intermediate Similarity	NPC228318
0.7686	Intermediate Similarity	NPC135730
0.7679	Intermediate Similarity	NPC229242
0.7667	Intermediate Similarity	NPC237366
0.7661	Intermediate Similarity	NPC473243
0.7647	Intermediate Similarity	NPC474314
0.7638	Intermediate Similarity	NPC246166
0.7632	Intermediate Similarity	NPC284477
0.7603	Intermediate Similarity	NPC474095
0.76	Intermediate Similarity	NPC50872
0.7593	Intermediate Similarity	NPC173443
0.7589	Intermediate Similarity	NPC270654
0.7583	Intermediate Similarity	NPC13784
0.7583	Intermediate Similarity	NPC161611
0.7565	Intermediate Similarity	NPC255676
0.7521	Intermediate Similarity	NPC474363
0.75	Intermediate Similarity	NPC107846
0.75	Intermediate Similarity	NPC304760
0.75	Intermediate Similarity	NPC295664
0.7481	Intermediate Similarity	NPC82712
0.7481	Intermediate Similarity	NPC473247
0.748	Intermediate Similarity	NPC475692
0.748	Intermediate Similarity	NPC474283
0.7477	Intermediate Similarity	NPC318107
0.7477	Intermediate Similarity	NPC261181
0.7459	Intermediate Similarity	NPC228936
0.7458	Intermediate Similarity	NPC211439
0.7456	Intermediate Similarity	NPC98911
0.7456	Intermediate Similarity	NPC472318
0.7455	Intermediate Similarity	NPC119631
0.744	Intermediate Similarity	NPC204784
0.7434	Intermediate Similarity	NPC325499
0.7424	Intermediate Similarity	NPC473271
0.7422	Intermediate Similarity	NPC475691
0.7419	Intermediate Similarity	NPC469574
0.7407	Intermediate Similarity	NPC89377
0.7395	Intermediate Similarity	NPC40178
0.7391	Intermediate Similarity	NPC282895
0.7387	Intermediate Similarity	NPC77273
0.7377	Intermediate Similarity	NPC172525
0.7368	Intermediate Similarity	NPC470831
0.7368	Intermediate Similarity	NPC214702
0.736	Intermediate Similarity	NPC94298
0.736	Intermediate Similarity	NPC27633
0.7333	Intermediate Similarity	NPC311339
0.7323	Intermediate Similarity	NPC144547
0.7317	Intermediate Similarity	NPC470764
0.7317	Intermediate Similarity	NPC474408
0.7311	Intermediate Similarity	NPC47536
0.7311	Intermediate Similarity	NPC475465
0.7311	Intermediate Similarity	NPC472314
0.7311	Intermediate Similarity	NPC20485
0.7308	Intermediate Similarity	NPC476599
0.7308	Intermediate Similarity	NPC275576
0.728	Intermediate Similarity	NPC45104
0.7273	Intermediate Similarity	NPC291799
0.7273	Intermediate Similarity	NPC220893
0.7266	Intermediate Similarity	NPC26285
0.7265	Intermediate Similarity	NPC234305
0.7258	Intermediate Similarity	NPC220540
0.7252	Intermediate Similarity	NPC470753
0.7252	Intermediate Similarity	NPC473220
0.7252	Intermediate Similarity	NPC169913
0.725	Intermediate Similarity	NPC318327
0.7244	Intermediate Similarity	NPC289432
0.7244	Intermediate Similarity	NPC988
0.7241	Intermediate Similarity	NPC112552
0.7241	Intermediate Similarity	NPC473325
0.7222	Intermediate Similarity	NPC294134
0.7222	Intermediate Similarity	NPC58616
0.7213	Intermediate Similarity	NPC23332
0.7209	Intermediate Similarity	NPC46634
0.7209	Intermediate Similarity	NPC472703
0.7207	Intermediate Similarity	NPC240108
0.7207	Intermediate Similarity	NPC213156
0.7207	Intermediate Similarity	NPC62765
0.7203	Intermediate Similarity	NPC85977
0.7203	Intermediate Similarity	NPC249067
0.72	Intermediate Similarity	NPC131192
0.72	Intermediate Similarity	NPC190298
0.72	Intermediate Similarity	NPC470860
0.7197	Intermediate Similarity	NPC181715
0.7185	Intermediate Similarity	NPC472656
0.7179	Intermediate Similarity	NPC304873
0.7179	Intermediate Similarity	NPC25458
0.7176	Intermediate Similarity	NPC470765
0.7176	Intermediate Similarity	NPC49938
0.7155	Intermediate Similarity	NPC217621
0.7154	Intermediate Similarity	NPC472704
0.7153	Intermediate Similarity	NPC27407
0.7153	Intermediate Similarity	NPC142027
0.7153	Intermediate Similarity	NPC470844
0.7143	Intermediate Similarity	NPC217423
0.7143	Intermediate Similarity	NPC105899
0.7132	Intermediate Similarity	NPC43627
0.7132	Intermediate Similarity	NPC126516
0.7132	Intermediate Similarity	NPC66158
0.7132	Intermediate Similarity	NPC329913
0.7131	Intermediate Similarity	NPC183648
0.713	Intermediate Similarity	NPC253423
0.7121	Intermediate Similarity	NPC110211
0.7121	Intermediate Similarity	NPC472706
0.7121	Intermediate Similarity	NPC204579
0.7119	Intermediate Similarity	NPC160382
0.7117	Intermediate Similarity	NPC9822
0.7111	Intermediate Similarity	NPC104854
0.7109	Intermediate Similarity	NPC238861
0.7109	Intermediate Similarity	NPC233282
0.7109	Intermediate Similarity	NPC77000
0.7109	Intermediate Similarity	NPC232958
0.7101	Intermediate Similarity	NPC291454
0.7099	Intermediate Similarity	NPC184219
0.7097	Intermediate Similarity	NPC196673
0.7097	Intermediate Similarity	NPC87069
0.709	Intermediate Similarity	NPC272946
0.709	Intermediate Similarity	NPC42234
0.709	Intermediate Similarity	NPC27712
0.709	Intermediate Similarity	NPC147561
0.7087	Intermediate Similarity	NPC94637
0.7083	Intermediate Similarity	NPC474376
0.7083	Intermediate Similarity	NPC472315
0.7083	Intermediate Similarity	NPC472316
0.7083	Intermediate Similarity	NPC475203
0.708	Intermediate Similarity	NPC477893
0.708	Intermediate Similarity	NPC474097
0.708	Intermediate Similarity	NPC477896
0.7077	Intermediate Similarity	NPC291189
0.7077	Intermediate Similarity	NPC69403
0.7077	Intermediate Similarity	NPC217756

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 NPC100353 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	1007
0.2-0.3	1382
0.3-0.4	3007
0.4-0.5	2257
0.5-0.6	992
0.6-0.7	239
0.7-0.8	14
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.8257	Intermediate Similarity	NPD1238	Approved
0.8158	Intermediate Similarity	NPD2182	Approved
0.8125	Intermediate Similarity	NPD164	Approved
0.7797	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD9257	Approved
0.7477	Intermediate Similarity	NPD1202	Approved
0.7477	Intermediate Similarity	NPD9259	Approved
0.736	Intermediate Similarity	NPD9545	Approved
0.7207	Intermediate Similarity	NPD9258	Approved
0.7207	Intermediate Similarity	NPD9256	Approved
0.7203	Intermediate Similarity	NPD1237	Approved
0.7109	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7008	Discontinued
0.7069	Intermediate Similarity	NPD9495	Approved
0.704	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6287	Discontinued
0.7	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2199	Approved
0.697	Remote Similarity	NPD2198	Approved
0.6967	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.696	Remote Similarity	NPD1241	Discontinued
0.6957	Remote Similarity	NPD9260	Approved
0.6929	Remote Similarity	NPD9493	Approved
0.6911	Remote Similarity	NPD2067	Discontinued
0.6905	Remote Similarity	NPD5951	Approved
0.6897	Remote Similarity	NPD1989	Approved
0.6835	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1929	Approved
0.6833	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1930	Approved
0.6822	Remote Similarity	NPD9490	Approved
0.6818	Remote Similarity	NPD3972	Approved
0.6806	Remote Similarity	NPD3887	Approved
0.6788	Remote Similarity	NPD3764	Approved
0.6786	Remote Similarity	NPD1282	Approved
0.6777	Remote Similarity	NPD5909	Discontinued
0.6765	Remote Similarity	NPD6832	Phase 2
0.6748	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD9491	Approved
0.6723	Remote Similarity	NPD2066	Phase 3
0.6718	Remote Similarity	NPD17	Approved
0.6716	Remote Similarity	NPD1876	Approved
0.6716	Remote Similarity	NPD5667	Approved
0.6694	Remote Similarity	NPD6647	Phase 2
0.6694	Remote Similarity	NPD9261	Approved
0.6692	Remote Similarity	NPD4878	Approved
0.6667	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2569	Approved
0.6667	Remote Similarity	NPD2567	Approved
0.6644	Remote Similarity	NPD7236	Approved
0.6643	Remote Similarity	NPD7611	Approved
0.6643	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2353	Approved
0.6643	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD2629	Approved
0.6637	Remote Similarity	NPD650	Approved
0.6637	Remote Similarity	NPD1087	Approved
0.6621	Remote Similarity	NPD4628	Phase 3
0.6619	Remote Similarity	NPD7713	Phase 3
0.6618	Remote Similarity	NPD1019	Discontinued
0.6617	Remote Similarity	NPD1281	Approved
0.6612	Remote Similarity	NPD1932	Approved
0.6609	Remote Similarity	NPD3673	Approved
0.6609	Remote Similarity	NPD3672	Approved
0.6594	Remote Similarity	NPD6039	Approved
0.6591	Remote Similarity	NPD5306	Approved
0.6591	Remote Similarity	NPD5305	Approved
0.6574	Remote Similarity	NPD227	Approved
0.6574	Remote Similarity	NPD225	Approved
0.6571	Remote Similarity	NPD3142	Approved
0.6571	Remote Similarity	NPD3140	Approved
0.6567	Remote Similarity	NPD6637	Approved
0.6567	Remote Similarity	NPD9717	Approved
0.6567	Remote Similarity	NPD1608	Approved
0.6565	Remote Similarity	NPD1894	Discontinued
0.6562	Remote Similarity	NPD6010	Discontinued
0.6552	Remote Similarity	NPD1239	Approved
0.6544	Remote Similarity	NPD552	Approved
0.6544	Remote Similarity	NPD1203	Approved
0.6544	Remote Similarity	NPD9567	Approved
0.6544	Remote Similarity	NPD553	Approved
0.6538	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD3134	Approved
0.6528	Remote Similarity	NPD2346	Discontinued
0.6515	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD3748	Approved
0.6489	Remote Similarity	NPD2347	Approved
0.6483	Remote Similarity	NPD970	Clinical (unspecified phase)
0.648	Remote Similarity	NPD1358	Approved
0.648	Remote Similarity	NPD9267	Approved
0.648	Remote Similarity	NPD9264	Approved
0.648	Remote Similarity	NPD9263	Approved
0.6479	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1283	Approved
0.6466	Remote Similarity	NPD1089	Approved
0.6466	Remote Similarity	NPD1086	Approved
0.6466	Remote Similarity	NPD1090	Approved
0.6463	Remote Similarity	NPD2354	Approved
0.6457	Remote Similarity	NPD2201	Approved
0.6457	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD3373	Approved
0.6452	Remote Similarity	NPD9697	Approved
0.6449	Remote Similarity	NPD454	Approved
0.6446	Remote Similarity	NPD7798	Approved
0.6441	Remote Similarity	NPD1563	Approved
0.6441	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2313	Discontinued
0.6429	Remote Similarity	NPD9266	Approved
0.6429	Remote Similarity	NPD74	Approved
0.6424	Remote Similarity	NPD7239	Suspended
0.6423	Remote Similarity	NPD3267	Approved
0.6423	Remote Similarity	NPD3266	Approved
0.6418	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD1889	Phase 1
0.6414	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD405	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7609	Phase 3
0.6408	Remote Similarity	NPD230	Phase 1
0.6408	Remote Similarity	NPD1933	Approved
0.6408	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD9508	Approved
0.6406	Remote Similarity	NPD969	Suspended
0.64	Remote Similarity	NPD6273	Approved
0.6397	Remote Similarity	NPD4359	Approved
0.6396	Remote Similarity	NPD942	Approved
0.6396	Remote Similarity	NPD226	Approved
0.6391	Remote Similarity	NPD5691	Approved
0.6387	Remote Similarity	NPD1693	Approved
0.6382	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD800	Approved
0.6378	Remote Similarity	NPD5240	Approved
0.6378	Remote Similarity	NPD5237	Approved
0.6378	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5239	Approved
0.6378	Remote Similarity	NPD5235	Approved
0.6378	Remote Similarity	NPD1756	Approved
0.6378	Remote Similarity	NPD1752	Approved
0.6378	Remote Similarity	NPD5236	Approved
0.6377	Remote Similarity	NPD2798	Approved
0.6371	Remote Similarity	NPD3047	Approved
0.6371	Remote Similarity	NPD3048	Approved
0.6371	Remote Similarity	NPD3046	Approved
0.637	Remote Similarity	NPD1549	Phase 2
0.6364	Remote Similarity	NPD5926	Approved
0.6357	Remote Similarity	NPD7094	Approved
0.6357	Remote Similarity	NPD6858	Approved
0.6357	Remote Similarity	NPD5277	Phase 2
0.6356	Remote Similarity	NPD1088	Approved
0.6356	Remote Similarity	NPD1508	Approved
0.6356	Remote Similarity	NPD7631	Approved
0.6345	Remote Similarity	NPD2796	Approved
0.6338	Remote Similarity	NPD4307	Phase 2
0.6338	Remote Similarity	NPD2979	Phase 3
0.6336	Remote Similarity	NPD4198	Discontinued
0.6323	Remote Similarity	NPD7819	Suspended
0.632	Remote Similarity	NPD5048	Discontinued
0.6316	Remote Similarity	NPD957	Approved
0.6304	Remote Similarity	NPD2797	Approved
0.6301	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD1471	Phase 3
0.6301	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD2329	Discontinued
0.6296	Remote Similarity	NPD4136	Approved
0.6296	Remote Similarity	NPD4135	Approved
0.6296	Remote Similarity	NPD4879	Approved
0.6296	Remote Similarity	NPD4106	Approved
0.6288	Remote Similarity	NPD4574	Approved
0.6288	Remote Similarity	NPD4576	Approved
0.6284	Remote Similarity	NPD3750	Approved
0.6284	Remote Similarity	NPD7003	Approved
0.6281	Remote Similarity	NPD1564	Approved
0.6281	Remote Similarity	NPD1565	Approved
0.6281	Remote Similarity	NPD1566	Phase 3
0.6277	Remote Similarity	NPD5157	Phase 1
0.6277	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5159	Phase 2
0.6277	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD2799	Discontinued
0.6269	Remote Similarity	NPD5585	Approved
0.6269	Remote Similarity	NPD1651	Approved
0.6268	Remote Similarity	NPD520	Approved
0.6267	Remote Similarity	NPD1340	Discontinued
0.6267	Remote Similarity	NPD6799	Approved
0.6259	Remote Similarity	NPD2897	Discontinued
0.625	Remote Similarity	NPD4806	Approved
0.625	Remote Similarity	NPD4807	Approved
0.6233	Remote Similarity	NPD2438	Suspended
0.6233	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD1551	Phase 2
0.6232	Remote Similarity	NPD1888	Phase 1
0.6224	Remote Similarity	NPD1240	Approved
0.6224	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD9494	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