NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.07
Volume:	239.249
LogP:	1.932
LogD:	1.955
LogS:	-3.03
# Rotatable Bonds:	6
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.63
Synthetic Accessibility Score:	2.94
Fsp3:	0.25
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:	-4.557
MDCK Permeability:	1.6622103430563584e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.251

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.989
Plasma Protein Binding (PPB):	59.6722412109375%
Volume Distribution (VD):	0.645
Pgp-substrate:	46.91313552856445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.841
CYP1A2-substrate:	0.17
CYP2C19-inhibitor:	0.821
CYP2C19-substrate:	0.149
CYP2C9-inhibitor:	0.684
CYP2C9-substrate:	0.55
CYP2D6-inhibitor:	0.806
CYP2D6-substrate:	0.285
CYP3A4-inhibitor:	0.36
CYP3A4-substrate:	0.378

ADMET: Excretion

Clearance (CL):	7.987
Half-life (T1/2):	0.758

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.055
Drug-inuced Liver Injury (DILI):	0.548
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.822
Skin Sensitization:	0.948
Carcinogencity:	0.099
Eye Corrosion:	0.078
Eye Irritation:	0.947
Respiratory Toxicity:	0.208

Download Data

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

Natural Product: NPC472919

Natural Product ID:	NPC472919
*Common Name:**	PWKCZCDJWGKWSE-AEZGRPFRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PWKCZCDJWGKWSE-AEZGRPFRSA-N
Standard InCHI:	InChI=1S/C12H14O3S/c1-16-8-7-12(14)15-9-11(13)10-5-3-2-4-6-10/h2-8,11,13H,9H2,1H3/b8-7+/t11-/m0/s1
SMILES:	CS/C=C/C(=O)OC[C@@H](c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594098
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives

*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
NPO33045	bellevalia eigii	Species	Hyacinthaceae	Eukaryota	Bulbs	Irbid, Jordan	n.a.	PMID[26147490]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	>	20000.0	nM	PMID[453382]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	20000.0	nM	PMID[453382]

☑ 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 NPC472919 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	174
0.1-0.2	916
0.2-0.3	3692
0.3-0.4	10499
0.4-0.5	12178
0.5-0.6	12276
0.6-0.7	2671
0.7-0.8	266
0.8-0.85	16
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC136962
0.8738	High Similarity	NPC242913
0.8738	High Similarity	NPC171831
0.8738	High Similarity	NPC280616
0.866	High Similarity	NPC185501
0.8641	High Similarity	NPC91820
0.8641	High Similarity	NPC82426
0.8571	High Similarity	NPC472315
0.8571	High Similarity	NPC472316
0.8571	High Similarity	NPC475203
0.8571	High Similarity	NPC474376
0.8571	High Similarity	NPC37115
0.8318	Intermediate Similarity	NPC277788
0.8286	Intermediate Similarity	NPC160382
0.8265	Intermediate Similarity	NPC304760
0.82	Intermediate Similarity	NPC472319
0.8182	Intermediate Similarity	NPC158282
0.8182	Intermediate Similarity	NPC234376
0.8108	Intermediate Similarity	NPC265002
0.8018	Intermediate Similarity	NPC185840
0.8	Intermediate Similarity	NPC98911
0.8	Intermediate Similarity	NPC173443
0.8	Intermediate Similarity	NPC472318
0.7982	Intermediate Similarity	NPC475465
0.7982	Intermediate Similarity	NPC472314
0.7959	Intermediate Similarity	NPC58616
0.7944	Intermediate Similarity	NPC234305
0.7905	Intermediate Similarity	NPC210529
0.7905	Intermediate Similarity	NPC160548
0.7905	Intermediate Similarity	NPC175852
0.7876	Intermediate Similarity	NPC474363
0.787	Intermediate Similarity	NPC85977
0.7857	Intermediate Similarity	NPC474314
0.7835	Intermediate Similarity	NPC103326
0.7835	Intermediate Similarity	NPC87299
0.7835	Intermediate Similarity	NPC99394
0.7835	Intermediate Similarity	NPC329319
0.78	Intermediate Similarity	NPC89377
0.7778	Intermediate Similarity	NPC304638
0.7768	Intermediate Similarity	NPC476003
0.7732	Intermediate Similarity	NPC117180
0.7677	Intermediate Similarity	NPC304538
0.767	Intermediate Similarity	NPC119631
0.7664	Intermediate Similarity	NPC171843
0.7647	Intermediate Similarity	NPC220893
0.7642	Intermediate Similarity	NPC325499
0.7632	Intermediate Similarity	NPC272524
0.7593	Intermediate Similarity	NPC469481
0.7593	Intermediate Similarity	NPC253746
0.7573	Intermediate Similarity	NPC213156
0.7573	Intermediate Similarity	NPC240108
0.7568	Intermediate Similarity	NPC477251
0.7565	Intermediate Similarity	NPC172525
0.7551	Intermediate Similarity	NPC89950
0.7544	Intermediate Similarity	NPC139946
0.7542	Intermediate Similarity	NPC309434
0.7526	Intermediate Similarity	NPC170484
0.7524	Intermediate Similarity	NPC23453
0.7523	Intermediate Similarity	NPC94343
0.7523	Intermediate Similarity	NPC60373
0.7523	Intermediate Similarity	NPC154905
0.75	Intermediate Similarity	NPC217472
0.75	Intermediate Similarity	NPC317645
0.7477	Intermediate Similarity	NPC249912
0.7477	Intermediate Similarity	NPC92754
0.7477	Intermediate Similarity	NPC276775
0.7459	Intermediate Similarity	NPC471466
0.7458	Intermediate Similarity	NPC65791
0.7456	Intermediate Similarity	NPC183700
0.7456	Intermediate Similarity	NPC323007
0.7456	Intermediate Similarity	NPC260818
0.7451	Intermediate Similarity	NPC96625
0.7449	Intermediate Similarity	NPC121800
0.7436	Intermediate Similarity	NPC233669
0.7434	Intermediate Similarity	NPC182549
0.7434	Intermediate Similarity	NPC114741
0.7434	Intermediate Similarity	NPC281604
0.7434	Intermediate Similarity	NPC474364
0.7434	Intermediate Similarity	NPC206341
0.7414	Intermediate Similarity	NPC95381
0.7414	Intermediate Similarity	NPC87069
0.7407	Intermediate Similarity	NPC78701
0.7407	Intermediate Similarity	NPC225060
0.7407	Intermediate Similarity	NPC35448
0.74	Intermediate Similarity	NPC127491
0.74	Intermediate Similarity	NPC172984
0.74	Intermediate Similarity	NPC308619
0.74	Intermediate Similarity	NPC324835
0.7395	Intermediate Similarity	NPC203124
0.7391	Intermediate Similarity	NPC477250
0.7391	Intermediate Similarity	NPC321852
0.7387	Intermediate Similarity	NPC148060
0.7373	Intermediate Similarity	NPC281277
0.7368	Intermediate Similarity	NPC75272
0.7368	Intermediate Similarity	NPC471954
0.7355	Intermediate Similarity	NPC470848
0.7355	Intermediate Similarity	NPC470849
0.735	Intermediate Similarity	NPC328593
0.735	Intermediate Similarity	NPC41851
0.735	Intermediate Similarity	NPC33749
0.735	Intermediate Similarity	NPC474685
0.735	Intermediate Similarity	NPC235250
0.735	Intermediate Similarity	NPC261453
0.7347	Intermediate Similarity	NPC78517
0.7347	Intermediate Similarity	NPC167577
0.7345	Intermediate Similarity	NPC156648
0.7345	Intermediate Similarity	NPC260952
0.7339	Intermediate Similarity	NPC146351
0.7328	Intermediate Similarity	NPC48525
0.7321	Intermediate Similarity	NPC152384
0.7321	Intermediate Similarity	NPC37714
0.7321	Intermediate Similarity	NPC127676
0.7321	Intermediate Similarity	NPC227255
0.732	Intermediate Similarity	NPC66655
0.7311	Intermediate Similarity	NPC122117
0.7308	Intermediate Similarity	NPC1793
0.7304	Intermediate Similarity	NPC63345
0.73	Intermediate Similarity	NPC323103
0.73	Intermediate Similarity	NPC103387
0.7297	Intermediate Similarity	NPC474365
0.7297	Intermediate Similarity	NPC301943
0.729	Intermediate Similarity	NPC130398
0.7288	Intermediate Similarity	NPC474967
0.7288	Intermediate Similarity	NPC210531
0.7282	Intermediate Similarity	NPC286608
0.7282	Intermediate Similarity	NPC169050
0.7281	Intermediate Similarity	NPC85493
0.7281	Intermediate Similarity	NPC184633
0.7281	Intermediate Similarity	NPC83628
0.7281	Intermediate Similarity	NPC469636
0.7281	Intermediate Similarity	NPC265407
0.7273	Intermediate Similarity	NPC70624
0.7273	Intermediate Similarity	NPC42211
0.7265	Intermediate Similarity	NPC153053
0.7265	Intermediate Similarity	NPC308744
0.7248	Intermediate Similarity	NPC229242
0.7248	Intermediate Similarity	NPC154517
0.7248	Intermediate Similarity	NPC135951
0.7245	Intermediate Similarity	NPC176228
0.7241	Intermediate Similarity	NPC226250
0.7241	Intermediate Similarity	NPC470825
0.7236	Intermediate Similarity	NPC327070
0.7232	Intermediate Similarity	NPC2518
0.7228	Intermediate Similarity	NPC270507
0.7222	Intermediate Similarity	NPC246679
0.7222	Intermediate Similarity	NPC473993
0.7217	Intermediate Similarity	NPC326187
0.7217	Intermediate Similarity	NPC174099
0.7216	Intermediate Similarity	NPC175393
0.7213	Intermediate Similarity	NPC476872
0.7213	Intermediate Similarity	NPC229600
0.7207	Intermediate Similarity	NPC25458
0.7203	Intermediate Similarity	NPC306740
0.7203	Intermediate Similarity	NPC469509
0.72	Intermediate Similarity	NPC133050
0.72	Intermediate Similarity	NPC303245
0.72	Intermediate Similarity	NPC79608
0.7196	Intermediate Similarity	NPC138117
0.7196	Intermediate Similarity	NPC325292
0.7193	Intermediate Similarity	NPC194034
0.7193	Intermediate Similarity	NPC251306
0.7193	Intermediate Similarity	NPC20485
0.719	Intermediate Similarity	NPC263386
0.719	Intermediate Similarity	NPC141791
0.7184	Intermediate Similarity	NPC93843
0.7182	Intermediate Similarity	NPC80115
0.7182	Intermediate Similarity	NPC217621
0.7182	Intermediate Similarity	NPC118343
0.7182	Intermediate Similarity	NPC325497
0.7179	Intermediate Similarity	NPC26615
0.7168	Intermediate Similarity	NPC269457
0.7168	Intermediate Similarity	NPC288760
0.7156	Intermediate Similarity	NPC253423
0.7156	Intermediate Similarity	NPC289201
0.7155	Intermediate Similarity	NPC133308
0.7155	Intermediate Similarity	NPC30563
0.7155	Intermediate Similarity	NPC474157
0.7155	Intermediate Similarity	NPC43584
0.7154	Intermediate Similarity	NPC475328
0.7154	Intermediate Similarity	NPC11724
0.7143	Intermediate Similarity	NPC3672
0.7143	Intermediate Similarity	NPC179686
0.7143	Intermediate Similarity	NPC61181
0.7143	Intermediate Similarity	NPC287790
0.7131	Intermediate Similarity	NPC202474
0.713	Intermediate Similarity	NPC469511
0.713	Intermediate Similarity	NPC81010
0.713	Intermediate Similarity	NPC32977
0.713	Intermediate Similarity	NPC31274
0.7129	Intermediate Similarity	NPC106313
0.712	Intermediate Similarity	NPC60517
0.712	Intermediate Similarity	NPC469568
0.712	Intermediate Similarity	NPC146886
0.712	Intermediate Similarity	NPC20443
0.712	Intermediate Similarity	NPC246166
0.7119	Intermediate Similarity	NPC190212
0.7119	Intermediate Similarity	NPC264558
0.7119	Intermediate Similarity	NPC474641
0.7119	Intermediate Similarity	NPC237366
0.7115	Intermediate Similarity	NPC211237

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 NPC472919 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	696
0.2-0.3	1550
0.3-0.4	3049
0.4-0.5	2204
0.5-0.6	1188
0.6-0.7	291
0.7-0.8	20
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
0.7905	Intermediate Similarity	NPD9495	Approved
0.7826	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD969	Suspended
0.75	Intermediate Similarity	NPD2629	Approved
0.7455	Intermediate Similarity	NPD6647	Phase 2
0.735	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD9294	Approved
0.7308	Intermediate Similarity	NPD689	Discontinued
0.7288	Intermediate Similarity	NPD4198	Discontinued
0.7282	Intermediate Similarity	NPD1282	Approved
0.728	Intermediate Similarity	NPD6085	Phase 2
0.728	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD1358	Approved
0.7193	Intermediate Similarity	NPD290	Approved
0.7182	Intermediate Similarity	NPD1238	Approved
0.7179	Intermediate Similarity	NPD5277	Phase 2
0.7155	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD4480	Approved
0.7097	Intermediate Similarity	NPD1877	Discontinued
0.708	Intermediate Similarity	NPD1237	Approved
0.7075	Intermediate Similarity	NPD9258	Approved
0.7075	Intermediate Similarity	NPD9256	Approved
0.7069	Intermediate Similarity	NPD2067	Discontinued
0.7043	Intermediate Similarity	NPD9532	Phase 3
0.704	Intermediate Similarity	NPD7876	Discontinued
0.7037	Intermediate Similarity	NPD1652	Phase 2
0.7023	Intermediate Similarity	NPD4340	Discontinued
0.7	Intermediate Similarity	NPD4248	Discontinued
0.6983	Remote Similarity	NPD2684	Approved
0.6983	Remote Similarity	NPD2182	Approved
0.6967	Remote Similarity	NPD9545	Approved
0.6957	Remote Similarity	NPD3134	Approved
0.6939	Remote Similarity	NPD9716	Approved
0.693	Remote Similarity	NPD164	Approved
0.6893	Remote Similarity	NPD9491	Approved
0.687	Remote Similarity	NPD4062	Phase 3
0.6855	Remote Similarity	NPD5305	Approved
0.6855	Remote Similarity	NPD5306	Approved
0.6842	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD9493	Approved
0.68	Remote Similarity	NPD4136	Approved
0.68	Remote Similarity	NPD4135	Approved
0.68	Remote Similarity	NPD4106	Approved
0.6797	Remote Similarity	NPD2628	Approved
0.6797	Remote Similarity	NPD2160	Approved
0.6797	Remote Similarity	NPD2626	Approved
0.6797	Remote Similarity	NPD2159	Approved
0.6797	Remote Similarity	NPD2625	Approved
0.6797	Remote Similarity	NPD2627	Approved
0.6786	Remote Similarity	NPD9611	Approved
0.6786	Remote Similarity	NPD9609	Approved
0.6786	Remote Similarity	NPD9612	Approved
0.6783	Remote Similarity	NPD5909	Discontinued
0.678	Remote Similarity	NPD9713	Approved
0.6774	Remote Similarity	NPD446	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7843	Approved
0.6748	Remote Similarity	NPD2347	Approved
0.6746	Remote Similarity	NPD4806	Approved
0.6746	Remote Similarity	NPD4807	Approved
0.6724	Remote Similarity	NPD5048	Discontinued
0.672	Remote Similarity	NPD5125	Phase 3
0.672	Remote Similarity	NPD5126	Approved
0.6718	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD226	Approved
0.6698	Remote Similarity	NPD9257	Approved
0.6698	Remote Similarity	NPD9259	Approved
0.6695	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9260	Approved
0.6667	Remote Similarity	NPD800	Approved
0.6667	Remote Similarity	NPD3496	Discontinued
0.6667	Remote Similarity	NPD228	Approved
0.6642	Remote Similarity	NPD7266	Discontinued
0.664	Remote Similarity	NPD4105	Approved
0.664	Remote Similarity	NPD4102	Approved
0.6639	Remote Similarity	NPD1317	Discontinued
0.6637	Remote Similarity	NPD5926	Approved
0.6618	Remote Similarity	NPD7305	Phase 1
0.6615	Remote Similarity	NPD5647	Approved
0.6609	Remote Similarity	NPD854	Approved
0.6609	Remote Similarity	NPD855	Approved
0.6606	Remote Similarity	NPD1089	Approved
0.6606	Remote Similarity	NPD1090	Approved
0.6606	Remote Similarity	NPD1086	Approved
0.6593	Remote Similarity	NPD6653	Approved
0.6585	Remote Similarity	NPD7157	Approved
0.6581	Remote Similarity	NPD9697	Approved
0.6579	Remote Similarity	NPD9712	Approved
0.6579	Remote Similarity	NPD2066	Phase 3
0.6577	Remote Similarity	NPD1202	Approved
0.6571	Remote Similarity	NPD3971	Phase 1
0.6565	Remote Similarity	NPD5204	Approved
0.6565	Remote Similarity	NPD3664	Approved
0.6565	Remote Similarity	NPD3662	Phase 3
0.6565	Remote Similarity	NPD3661	Approved
0.6565	Remote Similarity	NPD3663	Approved
0.656	Remote Similarity	NPD1894	Discontinued
0.6557	Remote Similarity	NPD6010	Discontinued
0.6552	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6798	Discontinued
0.6525	Remote Similarity	NPD6685	Approved
0.6525	Remote Similarity	NPD968	Approved
0.6522	Remote Similarity	NPD2553	Approved
0.6522	Remote Similarity	NPD2552	Approved
0.6522	Remote Similarity	NPD2555	Approved
0.6522	Remote Similarity	NPD2550	Approved
0.6522	Remote Similarity	NPD2558	Approved
0.6522	Remote Similarity	NPD2549	Approved
0.6519	Remote Similarity	NPD2202	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD2934	Approved
0.6518	Remote Similarity	NPD2933	Approved
0.6518	Remote Similarity	NPD1693	Approved
0.6515	Remote Similarity	NPD4620	Approved
0.6515	Remote Similarity	NPD5203	Approved
0.6515	Remote Similarity	NPD5201	Approved
0.6515	Remote Similarity	NPD4617	Approved
0.6505	Remote Similarity	NPD9490	Approved
0.65	Remote Similarity	NPD5235	Approved
0.65	Remote Similarity	NPD5237	Approved
0.65	Remote Similarity	NPD5240	Approved
0.65	Remote Similarity	NPD5239	Approved
0.65	Remote Similarity	NPD5236	Approved
0.65	Remote Similarity	NPD4628	Phase 3
0.6496	Remote Similarity	NPD311	Approved
0.6496	Remote Similarity	NPD10	Approved
0.6496	Remote Similarity	NPD309	Approved
0.6496	Remote Similarity	NPD310	Approved
0.6496	Remote Similarity	NPD315	Approved
0.6496	Remote Similarity	NPD314	Approved
0.6493	Remote Similarity	NPD6233	Phase 2
0.6491	Remote Similarity	NPD9711	Approved
0.6491	Remote Similarity	NPD9710	Approved
0.6489	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD1088	Approved
0.6484	Remote Similarity	NPD1091	Approved
0.6484	Remote Similarity	NPD422	Phase 1
0.6466	Remote Similarity	NPD4189	Approved
0.6466	Remote Similarity	NPD7008	Discontinued
0.6466	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD4188	Approved
0.646	Remote Similarity	NPD1989	Approved
0.646	Remote Similarity	NPD2859	Approved
0.646	Remote Similarity	NPD2860	Approved
0.6457	Remote Similarity	NPD4626	Approved
0.6457	Remote Similarity	NPD1778	Approved
0.6457	Remote Similarity	NPD5723	Approved
0.6455	Remote Similarity	NPD3672	Approved
0.6455	Remote Similarity	NPD3673	Approved
0.6449	Remote Similarity	NPD111	Approved
0.6449	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD2201	Approved
0.6444	Remote Similarity	NPD4060	Phase 1
0.6435	Remote Similarity	NPD7798	Approved
0.6435	Remote Similarity	NPD1067	Discontinued
0.6434	Remote Similarity	NPD9717	Approved
0.6429	Remote Similarity	NPD1066	Discontinued
0.6429	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD845	Approved
0.6429	Remote Similarity	NPD7741	Discontinued
0.6423	Remote Similarity	NPD1241	Discontinued
0.6418	Remote Similarity	NPD1048	Approved
0.6412	Remote Similarity	NPD987	Approved
0.641	Remote Similarity	NPD1930	Approved
0.641	Remote Similarity	NPD1929	Approved
0.641	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD227	Approved
0.6408	Remote Similarity	NPD225	Approved
0.6408	Remote Similarity	NPD7440	Discontinued
0.6403	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5291	Approved
0.64	Remote Similarity	NPD5292	Approved
0.6397	Remote Similarity	NPD6355	Discontinued
0.6396	Remote Similarity	NPD1239	Approved
0.6396	Remote Similarity	NPD9365	Approved
0.6391	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD9250	Approved
0.6378	Remote Similarity	NPD1357	Approved
0.6378	Remote Similarity	NPD5691	Approved
0.6378	Remote Similarity	NPD1245	Approved
0.6372	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5951	Approved
0.6371	Remote Similarity	NPD1246	Approved
0.637	Remote Similarity	NPD4404	Approved
0.6364	Remote Similarity	NPD5347	Phase 2
0.6364	Remote Similarity	NPD5346	Phase 2
0.6356	Remote Similarity	NPD3046	Approved
0.6356	Remote Similarity	NPD3047	Approved
0.6356	Remote Similarity	NPD3048	Approved
0.635	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD821	Approved
0.6341	Remote Similarity	NPD5535	Approved
0.6336	Remote Similarity	NPD1888	Phase 1
0.6336	Remote Similarity	NPD5667	Approved
0.6333	Remote Similarity	NPD9263	Approved
0.6333	Remote Similarity	NPD9267	Approved
0.6333	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD9264	Approved
0.633	Remote Similarity	NPD4793	Discontinued
0.633	Remote Similarity	NPD1087	Approved
0.6328	Remote Similarity	NPD1104	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