NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.06
Volume:	244.691
LogP:	2.631
LogD:	2.505
LogS:	-2.766
# Rotatable Bonds:	3
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.663
Synthetic Accessibility Score:	3.708
Fsp3:	0.308
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.523
MDCK Permeability:	2.8682959964498878e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.031

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.99
Plasma Protein Binding (PPB):	94.32792663574219%
Volume Distribution (VD):	1.248
Pgp-substrate:	5.860170364379883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.186
CYP1A2-substrate:	0.109
CYP2C19-inhibitor:	0.073
CYP2C19-substrate:	0.498
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.426
CYP2D6-inhibitor:	0.079
CYP2D6-substrate:	0.194
CYP3A4-inhibitor:	0.259
CYP3A4-substrate:	0.326

ADMET: Excretion

Clearance (CL):	9.563
Half-life (T1/2):	0.805

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.222
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.057
Rat Oral Acute Toxicity:	0.565
Maximum Recommended Daily Dose:	0.892
Skin Sensitization:	0.957
Carcinogencity:	0.37
Eye Corrosion:	0.954
Eye Irritation:	0.965
Respiratory Toxicity:	0.901

Download Data

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

Natural Product: NPC472314

Natural Product ID:	NPC472314
*Common Name:**	MSNHEIXAOKHXKK-UHTWSYAYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MSNHEIXAOKHXKK-UHTWSYAYSA-N
Standard InCHI:	InChI=1S/C13H13ClO3/c14-12(9-5-2-1-3-6-9)13(16)10-7-4-8-11(15)17-10/h1-6,8,10,12-13,16H,7H2/t10-,12+,13-/m0/s1
SMILES:	O=C1C=CC[C@H](O1)[C@@H]([C@@H](c1ccccc1)Cl)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3358615
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives [CHEMONTID:0001211] Dihydropyranones

*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
NPO33111	polyalthia parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25419616]

☑ 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	4

Activity Type	# Activity
Cell Line	3
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	>	10000.0	nM	PMID[515257]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[515257]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[515257]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	30000.0	nM	PMID[515257]

☑ 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 NPC472314 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	232
0.1-0.2	1052
0.2-0.3	3612
0.3-0.4	10732
0.4-0.5	14309
0.5-0.6	11208
0.6-0.7	1401
0.7-0.8	121
0.8-0.85	19
0.85-0.9	9
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475465
0.875	High Similarity	NPC280616
0.875	High Similarity	NPC242913
0.875	High Similarity	NPC171831
0.8585	High Similarity	NPC472316
0.8585	High Similarity	NPC475203
0.8585	High Similarity	NPC136962
0.8585	High Similarity	NPC37115
0.8585	High Similarity	NPC472315
0.8585	High Similarity	NPC474376
0.8505	High Similarity	NPC277788
0.84	Intermediate Similarity	NPC472319
0.8198	Intermediate Similarity	NPC234376
0.819	Intermediate Similarity	NPC98911
0.819	Intermediate Similarity	NPC472318
0.8131	Intermediate Similarity	NPC82426
0.8131	Intermediate Similarity	NPC91820
0.8125	Intermediate Similarity	NPC265002
0.8	Intermediate Similarity	NPC325499
0.7982	Intermediate Similarity	NPC472919
0.7963	Intermediate Similarity	NPC234305
0.789	Intermediate Similarity	NPC85977
0.7885	Intermediate Similarity	NPC23453
0.7876	Intermediate Similarity	NPC185840
0.7876	Intermediate Similarity	NPC158282
0.7778	Intermediate Similarity	NPC308619
0.7778	Intermediate Similarity	NPC324835
0.7778	Intermediate Similarity	NPC127491
0.7767	Intermediate Similarity	NPC213156
0.7767	Intermediate Similarity	NPC240108
0.7748	Intermediate Similarity	NPC477251
0.7647	Intermediate Similarity	NPC96625
0.7573	Intermediate Similarity	NPC304760
0.7565	Intermediate Similarity	NPC477250
0.7524	Intermediate Similarity	NPC119631
0.7522	Intermediate Similarity	NPC20485
0.75	Intermediate Similarity	NPC173443
0.7477	Intermediate Similarity	NPC160382
0.7476	Intermediate Similarity	NPC169050
0.7476	Intermediate Similarity	NPC286608
0.7456	Intermediate Similarity	NPC184633
0.7436	Intermediate Similarity	NPC474363
0.7436	Intermediate Similarity	NPC172525
0.7431	Intermediate Similarity	NPC154517
0.7414	Intermediate Similarity	NPC474314
0.74	Intermediate Similarity	NPC89950
0.7368	Intermediate Similarity	NPC156648
0.7364	Intermediate Similarity	NPC80115
0.7358	Intermediate Similarity	NPC317645
0.735	Intermediate Similarity	NPC272524
0.7339	Intermediate Similarity	NPC471466
0.7328	Intermediate Similarity	NPC43584
0.7328	Intermediate Similarity	NPC323007
0.7311	Intermediate Similarity	NPC100353
0.7304	Intermediate Similarity	NPC281604
0.7304	Intermediate Similarity	NPC182549
0.7304	Intermediate Similarity	NPC114741
0.729	Intermediate Similarity	NPC77273
0.7282	Intermediate Similarity	NPC58616
0.7273	Intermediate Similarity	NPC175852
0.7273	Intermediate Similarity	NPC160548
0.7273	Intermediate Similarity	NPC135951
0.7273	Intermediate Similarity	NPC210529
0.7273	Intermediate Similarity	NPC176228
0.7265	Intermediate Similarity	NPC470825
0.7264	Intermediate Similarity	NPC185501
0.7228	Intermediate Similarity	NPC71795
0.7227	Intermediate Similarity	NPC474685
0.72	Intermediate Similarity	NPC170484
0.72	Intermediate Similarity	NPC78517
0.72	Intermediate Similarity	NPC167577
0.7182	Intermediate Similarity	NPC289201
0.7182	Intermediate Similarity	NPC270654
0.7179	Intermediate Similarity	NPC243355
0.7179	Intermediate Similarity	NPC183700
0.7179	Intermediate Similarity	NPC476003
0.7177	Intermediate Similarity	NPC475328
0.7168	Intermediate Similarity	NPC304638
0.7167	Intermediate Similarity	NPC473507
0.7157	Intermediate Similarity	NPC99240
0.7155	Intermediate Similarity	NPC206341
0.7143	Intermediate Similarity	NPC474641
0.7143	Intermediate Similarity	NPC308744
0.7143	Intermediate Similarity	NPC42211
0.7143	Intermediate Similarity	NPC89377
0.7143	Intermediate Similarity	NPC87069
0.7129	Intermediate Similarity	NPC121800
0.7119	Intermediate Similarity	NPC139946
0.7115	Intermediate Similarity	NPC475710
0.7107	Intermediate Similarity	NPC470820
0.7097	Intermediate Similarity	NPC229600
0.7087	Intermediate Similarity	NPC243289
0.7087	Intermediate Similarity	NPC79608
0.7087	Intermediate Similarity	NPC476033
0.7087	Intermediate Similarity	NPC208183
0.7083	Intermediate Similarity	NPC217472
0.7083	Intermediate Similarity	NPC306740
0.708	Intermediate Similarity	NPC154905
0.708	Intermediate Similarity	NPC60373
0.7069	Intermediate Similarity	NPC260952
0.7059	Intermediate Similarity	NPC303245
0.7059	Intermediate Similarity	NPC117180
0.7054	Intermediate Similarity	NPC118343
0.7045	Intermediate Similarity	NPC2363
0.7043	Intermediate Similarity	NPC152384
0.7043	Intermediate Similarity	NPC127676
0.7043	Intermediate Similarity	NPC269457
0.7043	Intermediate Similarity	NPC37714
0.7034	Intermediate Similarity	NPC474157
0.7027	Intermediate Similarity	NPC92754
0.7027	Intermediate Similarity	NPC249912
0.7027	Intermediate Similarity	NPC276775
0.7019	Intermediate Similarity	NPC304538
0.7009	Intermediate Similarity	NPC220893
0.7009	Intermediate Similarity	NPC265407
0.7009	Intermediate Similarity	NPC474364
0.7009	Intermediate Similarity	NPC469636
0.7009	Intermediate Similarity	NPC40178
0.7009	Intermediate Similarity	NPC83628
0.7	Intermediate Similarity	NPC3672
0.7	Intermediate Similarity	NPC287790
0.6992	Remote Similarity	NPC309434
0.6991	Remote Similarity	NPC469481
0.6991	Remote Similarity	NPC253746
0.699	Remote Similarity	NPC99394
0.699	Remote Similarity	NPC329319
0.699	Remote Similarity	NPC323103
0.699	Remote Similarity	NPC103326
0.699	Remote Similarity	NPC87299
0.699	Remote Similarity	NPC103387
0.6984	Remote Similarity	NPC12016
0.6984	Remote Similarity	NPC474283
0.6984	Remote Similarity	NPC475692
0.6983	Remote Similarity	NPC51174
0.6977	Remote Similarity	NPC473993
0.6964	Remote Similarity	NPC329387
0.6964	Remote Similarity	NPC225060
0.6964	Remote Similarity	NPC262826
0.6964	Remote Similarity	NPC78701
0.6964	Remote Similarity	NPC317280
0.6964	Remote Similarity	NPC35448
0.696	Remote Similarity	NPC476872
0.696	Remote Similarity	NPC470849
0.696	Remote Similarity	NPC470848
0.6957	Remote Similarity	NPC249067
0.6957	Remote Similarity	NPC148060
0.6957	Remote Similarity	NPC114594
0.6957	Remote Similarity	NPC269644
0.6957	Remote Similarity	NPC19136
0.6952	Remote Similarity	NPC53299
0.6952	Remote Similarity	NPC99482
0.6949	Remote Similarity	NPC471954
0.6949	Remote Similarity	NPC75272
0.6947	Remote Similarity	NPC319995
0.6947	Remote Similarity	NPC17567
0.6947	Remote Similarity	NPC289415
0.6942	Remote Similarity	NPC41851
0.6935	Remote Similarity	NPC263386
0.6935	Remote Similarity	NPC141791
0.693	Remote Similarity	NPC94343
0.6929	Remote Similarity	NPC475691
0.6929	Remote Similarity	NPC472373
0.6923	Remote Similarity	NPC270507
0.6923	Remote Similarity	NPC47536
0.6917	Remote Similarity	NPC266116
0.6917	Remote Similarity	NPC128368
0.6917	Remote Similarity	NPC474176
0.6911	Remote Similarity	NPC65791
0.6911	Remote Similarity	NPC122117
0.6905	Remote Similarity	NPC11724
0.6903	Remote Similarity	NPC171843
0.6903	Remote Similarity	NPC146351
0.69	Remote Similarity	NPC175393
0.6897	Remote Similarity	NPC209632
0.6891	Remote Similarity	NPC477247
0.6891	Remote Similarity	NPC210089
0.6891	Remote Similarity	NPC133308
0.6891	Remote Similarity	NPC260818
0.6891	Remote Similarity	NPC63345
0.6885	Remote Similarity	NPC210531
0.6885	Remote Similarity	NPC233669
0.6885	Remote Similarity	NPC476476
0.6875	Remote Similarity	NPC471758
0.6875	Remote Similarity	NPC145287
0.687	Remote Similarity	NPC301943
0.687	Remote Similarity	NPC60679
0.687	Remote Similarity	NPC474365
0.6869	Remote Similarity	NPC108218
0.6864	Remote Similarity	NPC475282
0.686	Remote Similarity	NPC95381
0.6855	Remote Similarity	NPC275519
0.6855	Remote Similarity	NPC203124
0.685	Remote Similarity	NPC141970
0.685	Remote Similarity	NPC223351
0.685	Remote Similarity	NPC327070
0.685	Remote Similarity	NPC52097
0.685	Remote Similarity	NPC140561
0.6847	Remote Similarity	NPC5472
0.6847	Remote Similarity	NPC130398
0.6846	Remote Similarity	NPC288416

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 NPC472314 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	803
0.2-0.3	1502
0.3-0.4	3151
0.4-0.5	2317
0.5-0.6	1012
0.6-0.7	165
0.7-0.8	8
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
0.8	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD1282	Approved
0.7273	Intermediate Similarity	NPD9495	Approved
0.7265	Intermediate Similarity	NPD969	Suspended
0.7217	Intermediate Similarity	NPD9532	Phase 3
0.717	Intermediate Similarity	NPD689	Discontinued
0.7168	Intermediate Similarity	NPD6647	Phase 2
0.7094	Intermediate Similarity	NPD2067	Discontinued
0.7083	Intermediate Similarity	NPD2629	Approved
0.7054	Intermediate Similarity	NPD1238	Approved
0.7025	Intermediate Similarity	NPD4198	Discontinued
0.7016	Intermediate Similarity	NPD5846	Approved
0.7016	Intermediate Similarity	NPD6516	Phase 2
0.6957	Remote Similarity	NPD5909	Discontinued
0.6957	Remote Similarity	NPD1237	Approved
0.6942	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5926	Approved
0.68	Remote Similarity	NPD9716	Approved
0.678	Remote Similarity	NPD1358	Approved
0.6762	Remote Similarity	NPD9491	Approved
0.6754	Remote Similarity	NPD2066	Phase 3
0.6692	Remote Similarity	NPD987	Approved
0.6667	Remote Similarity	NPD9294	Approved
0.6639	Remote Similarity	NPD290	Approved
0.6636	Remote Similarity	NPD9256	Approved
0.6636	Remote Similarity	NPD9258	Approved
0.661	Remote Similarity	NPD5048	Discontinued
0.661	Remote Similarity	NPD9697	Approved
0.6609	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6010	Discontinued
0.6583	Remote Similarity	NPD2684	Approved
0.6583	Remote Similarity	NPD2182	Approved
0.6581	Remote Similarity	NPD1930	Approved
0.6581	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD1929	Approved
0.6581	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1239	Approved
0.6571	Remote Similarity	NPD226	Approved
0.6555	Remote Similarity	NPD3134	Approved
0.6545	Remote Similarity	NPD800	Approved
0.6525	Remote Similarity	NPD164	Approved
0.65	Remote Similarity	NPD5958	Discontinued
0.65	Remote Similarity	NPD4534	Discontinued
0.6493	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD1989	Approved
0.6486	Remote Similarity	NPD1089	Approved
0.6486	Remote Similarity	NPD1090	Approved
0.6486	Remote Similarity	NPD1086	Approved
0.6484	Remote Similarity	NPD5306	Approved
0.6484	Remote Similarity	NPD5305	Approved
0.6484	Remote Similarity	NPD5126	Approved
0.6484	Remote Similarity	NPD5125	Phase 3
0.6475	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD454	Approved
0.6466	Remote Similarity	NPD7798	Approved
0.646	Remote Similarity	NPD1202	Approved
0.6457	Remote Similarity	NPD9545	Approved
0.6449	Remote Similarity	NPD3971	Phase 1
0.6446	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD4106	Approved
0.6434	Remote Similarity	NPD4135	Approved
0.6434	Remote Similarity	NPD4136	Approved
0.6422	Remote Similarity	NPD9259	Approved
0.6422	Remote Similarity	NPD9257	Approved
0.6417	Remote Similarity	NPD6685	Approved
0.641	Remote Similarity	NPD1616	Discontinued
0.6404	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD1693	Approved
0.6393	Remote Similarity	NPD9713	Approved
0.6391	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD4807	Approved
0.6385	Remote Similarity	NPD4806	Approved
0.6381	Remote Similarity	NPD9490	Approved
0.6372	Remote Similarity	NPD9251	Approved
0.6372	Remote Similarity	NPD1088	Approved
0.6371	Remote Similarity	NPD7843	Approved
0.6364	Remote Similarity	NPD4793	Discontinued
0.6364	Remote Similarity	NPD2354	Approved
0.6356	Remote Similarity	NPD1932	Approved
0.6341	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD3673	Approved
0.6339	Remote Similarity	NPD3672	Approved
0.6331	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD1894	Discontinued
0.6324	Remote Similarity	NPD6798	Discontinued
0.6316	Remote Similarity	NPD2625	Approved
0.6316	Remote Similarity	NPD2628	Approved
0.6316	Remote Similarity	NPD2160	Approved
0.6316	Remote Similarity	NPD2626	Approved
0.6316	Remote Similarity	NPD2627	Approved
0.6316	Remote Similarity	NPD2159	Approved
0.6312	Remote Similarity	NPD7266	Discontinued
0.6306	Remote Similarity	NPD531	Approved
0.6303	Remote Similarity	NPD5765	Approved
0.6299	Remote Similarity	NPD9493	Approved
0.6294	Remote Similarity	NPD4628	Phase 3
0.6293	Remote Similarity	NPD1564	Approved
0.6293	Remote Similarity	NPD1566	Phase 3
0.6293	Remote Similarity	NPD1565	Approved
0.629	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD227	Approved
0.6286	Remote Similarity	NPD225	Approved
0.6281	Remote Similarity	NPD5705	Approved
0.6281	Remote Similarity	NPD5706	Approved
0.6281	Remote Similarity	NPD5704	Approved
0.6279	Remote Similarity	NPD4105	Approved
0.6279	Remote Similarity	NPD4102	Approved
0.6271	Remote Similarity	NPD2553	Approved
0.6271	Remote Similarity	NPD2558	Approved
0.6271	Remote Similarity	NPD2549	Approved
0.6271	Remote Similarity	NPD2552	Approved
0.6271	Remote Similarity	NPD2555	Approved
0.6271	Remote Similarity	NPD2550	Approved
0.626	Remote Similarity	NPD5239	Approved
0.626	Remote Similarity	NPD5451	Approved
0.626	Remote Similarity	NPD5240	Approved
0.626	Remote Similarity	NPD422	Phase 1
0.626	Remote Similarity	NPD5235	Approved
0.626	Remote Similarity	NPD5237	Approved
0.626	Remote Similarity	NPD5236	Approved
0.625	Remote Similarity	NPD5346	Phase 2
0.625	Remote Similarity	NPD9249	Phase 1
0.625	Remote Similarity	NPD7008	Discontinued
0.625	Remote Similarity	NPD3887	Approved
0.625	Remote Similarity	NPD5347	Phase 2
0.6233	Remote Similarity	NPD1578	Phase 2
0.623	Remote Similarity	NPD9552	Approved
0.6224	Remote Similarity	NPD1652	Phase 2
0.6222	Remote Similarity	NPD5204	Approved
0.622	Remote Similarity	NPD7157	Approved
0.6218	Remote Similarity	NPD4189	Approved
0.6218	Remote Similarity	NPD4188	Approved
0.6216	Remote Similarity	NPD1087	Approved
0.6214	Remote Similarity	NPD4536	Approved
0.6214	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4538	Approved
0.621	Remote Similarity	NPD2201	Approved
0.6194	Remote Similarity	NPD2797	Approved
0.619	Remote Similarity	NPD2988	Approved
0.619	Remote Similarity	NPD2991	Approved
0.619	Remote Similarity	NPD1241	Discontinued
0.6187	Remote Similarity	NPD4340	Discontinued
0.6187	Remote Similarity	NPD6355	Discontinued
0.6183	Remote Similarity	NPD3496	Discontinued
0.6176	Remote Similarity	NPD5201	Approved
0.6176	Remote Similarity	NPD5203	Approved
0.6176	Remote Similarity	NPD4620	Approved
0.6176	Remote Similarity	NPD4617	Approved
0.6174	Remote Similarity	NPD1066	Discontinued
0.617	Remote Similarity	NPD5588	Approved
0.617	Remote Similarity	NPD5960	Phase 3
0.6167	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD7876	Discontinued
0.616	Remote Similarity	NPD6912	Phase 3
0.6159	Remote Similarity	NPD6233	Phase 2
0.6159	Remote Similarity	NPD4062	Phase 3
0.6154	Remote Similarity	NPD5691	Approved
0.6148	Remote Similarity	NPD968	Approved
0.6143	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD5951	Approved
0.6138	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4480	Approved
0.6136	Remote Similarity	NPD6287	Discontinued
0.6136	Remote Similarity	NPD1091	Approved
0.6124	Remote Similarity	NPD2347	Approved
0.6119	Remote Similarity	NPD5667	Approved
0.6116	Remote Similarity	NPD9501	Approved
0.6116	Remote Similarity	NPD3047	Approved
0.6116	Remote Similarity	NPD3046	Approved
0.6116	Remote Similarity	NPD3048	Approved
0.6115	Remote Similarity	NPD4060	Phase 1
0.6111	Remote Similarity	NPD5535	Approved
0.6107	Remote Similarity	NPD5723	Approved
0.6107	Remote Similarity	NPD4626	Approved
0.6103	Remote Similarity	NPD3663	Approved
0.6103	Remote Similarity	NPD3661	Approved
0.6103	Remote Similarity	NPD3662	Phase 3
0.6103	Remote Similarity	NPD3664	Approved
0.6102	Remote Similarity	NPD9609	Approved
0.6102	Remote Similarity	NPD9611	Approved
0.6102	Remote Similarity	NPD9612	Approved
0.609	Remote Similarity	NPD4878	Approved
0.609	Remote Similarity	NPD6637	Approved
0.6087	Remote Similarity	NPD2313	Discontinued
0.6084	Remote Similarity	NPD5762	Approved
0.6084	Remote Similarity	NPD2353	Approved
0.6084	Remote Similarity	NPD5763	Approved
0.6084	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD4016	Approved
0.6077	Remote Similarity	NPD7741	Discontinued
0.6071	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD1184	Approved
0.6071	Remote Similarity	NPD5124	Phase 1
0.6068	Remote Similarity	NPD2859	Approved
0.6068	Remote Similarity	NPD2860	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