NPASS Compound

Structure

NPC250228 OpenBabel07101719242D 26 30 0 0 1 0 0 0 0 0999 V2000 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 -0.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0733 -0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0514 -1.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 -1.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6665 0.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 6 1 0 0 0 0 4 12 1 0 0 0 0 5 7 2 0 0 0 0 5 11 1 0 0 0 0 7 24 1 0 0 0 0 8 15 1 0 0 0 0 8 19 1 0 0 0 0 9 11 2 0 0 0 0 9 24 1 0 0 0 0 10 20 1 0 0 0 0 10 25 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 1 0 0 0 13 17 1 0 0 0 0 13 20 1 6 0 0 0 14 16 1 0 0 0 0 14 21 1 1 0 0 0 15 11 1 6 0 0 0 15 26 1 0 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 17 22 2 0 0 0 0 17 25 1 0 0 0 0 18 23 2 0 0 0 0 18 26 1 0 0 0 0 19 1 1 6 0 0 0 20 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.14
Volume:	351.253
LogP:	2.39
LogD:	1.723
LogS:	-4.183
# Rotatable Bonds:	1
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.777
Synthetic Accessibility Score:	5.302
Fsp3:	0.6
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:	-5.083
MDCK Permeability:	1.0778668183775153e-05
Pgp-inhibitor:	0.211
Pgp-substrate:	0.191
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.774

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.14
Plasma Protein Binding (PPB):	92.05750274658203%
Volume Distribution (VD):	1.424
Pgp-substrate:	11.177854537963867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.666
CYP2C19-inhibitor:	0.7
CYP2C19-substrate:	0.552
CYP2C9-inhibitor:	0.464
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.36

ADMET: Excretion

Clearance (CL):	8.227
Half-life (T1/2):	0.409

ADMET: Toxicity

hERG Blockers:	0.274
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.167
AMES Toxicity:	0.184
Rat Oral Acute Toxicity:	0.832
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.097
Carcinogencity:	0.6
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC250228

Natural Product ID:	NPC250228
*Common Name:**	MYHFDQGUNLKIHV-ODESWZHGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MYHFDQGUNLKIHV-ODESWZHGSA-N
Standard InCHI:	InChI=1S/C20H22O6/c1-19-8-15(11-5-7-24-9-11)26-18(23)12(19)4-6-20-10-25-17(22)13(20)2-3-14(21)16(19)20/h2-3,5,7,9,12-16,21H,4,6,8,10H2,1H3/t12-,13+,14-,15-,16-,19+,20-/m1/s1
SMILES:	C[C@]12C[C@H](c3ccoc3)OC(=O)[C@H]1CC[C@@]13COC(=O)[C@@H]1C=C[C@H]([C@H]23)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431792
PubChem CID:	73350928
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO33426	salvia shannoni	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24099364]

☑ 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
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2645	Organism	Giardia intestinalis	Giardia intestinalis	IC50	=	71.7	ug.mL-1	PMID[519465]
NPT3535	Organism	Entamoeba histolytica HM-1:IMSS	Entamoeba histolytica HM-1:IMSS	IC50	=	57.4	ug.mL-1	PMID[519465]

☑ 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 NPC250228 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	311
0.1-0.2	1146
0.2-0.3	2707
0.3-0.4	4994
0.4-0.5	9913
0.5-0.6	11490
0.6-0.7	9645
0.7-0.8	1973
0.8-0.85	322
0.85-0.9	150
0.9-0.95	42
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9507	High Similarity	NPC346
0.9452	High Similarity	NPC57998
0.9424	High Similarity	NPC90953
0.9375	High Similarity	NPC476942
0.9375	High Similarity	NPC476941
0.9366	High Similarity	NPC476944
0.931	High Similarity	NPC195325
0.9306	High Similarity	NPC476938
0.9306	High Similarity	NPC476937
0.9281	High Similarity	NPC310830
0.9262	High Similarity	NPC261597
0.9257	High Similarity	NPC44675
0.9257	High Similarity	NPC214541
0.9252	High Similarity	NPC469503
0.9189	High Similarity	NPC178932
0.9161	High Similarity	NPC470741
0.9161	High Similarity	NPC223415
0.9143	High Similarity	NPC186626
0.9133	High Similarity	NPC36655
0.9128	High Similarity	NPC469336
0.9128	High Similarity	NPC35000
0.9122	High Similarity	NPC476939
0.9122	High Similarity	NPC44577
0.9122	High Similarity	NPC476940
0.9122	High Similarity	NPC75906
0.9078	High Similarity	NPC220094
0.9078	High Similarity	NPC476943
0.9073	High Similarity	NPC475967
0.906	High Similarity	NPC282445
0.906	High Similarity	NPC30222
0.9048	High Similarity	NPC472654
0.9028	High Similarity	NPC267632
0.9013	High Similarity	NPC477402
0.9007	High Similarity	NPC187149
0.9007	High Similarity	NPC472777
0.9007	High Similarity	NPC299038
0.9007	High Similarity	NPC472776
0.9007	High Similarity	NPC472778
0.9	High Similarity	NPC92941
0.9	High Similarity	NPC264943
0.8966	High Similarity	NPC137295
0.8966	High Similarity	NPC251865
0.8947	High Similarity	NPC477403
0.8947	High Similarity	NPC262872
0.8912	High Similarity	NPC221809
0.8912	High Similarity	NPC470941
0.8896	High Similarity	NPC198047
0.8889	High Similarity	NPC205765
0.8882	High Similarity	NPC45101
0.8882	High Similarity	NPC472772
0.8882	High Similarity	NPC249021
0.8873	High Similarity	NPC470742
0.8859	High Similarity	NPC469335
0.8859	High Similarity	NPC159927
0.8846	High Similarity	NPC100333
0.8839	High Similarity	NPC123088
0.8836	High Similarity	NPC142113
0.8831	High Similarity	NPC200782
0.8831	High Similarity	NPC69028
0.8831	High Similarity	NPC211777
0.8831	High Similarity	NPC5079
0.8816	High Similarity	NPC469485
0.8784	High Similarity	NPC471174
0.8784	High Similarity	NPC10088
0.8776	High Similarity	NPC41182
0.8774	High Similarity	NPC234660
0.8774	High Similarity	NPC51568
0.8774	High Similarity	NPC663
0.8774	High Similarity	NPC224394
0.8774	High Similarity	NPC165218
0.8774	High Similarity	NPC419
0.8766	High Similarity	NPC335761
0.8759	High Similarity	NPC20500
0.8758	High Similarity	NPC173544
0.875	High Similarity	NPC281258
0.8733	High Similarity	NPC477404
0.8733	High Similarity	NPC196864
0.8733	High Similarity	NPC476936
0.8733	High Similarity	NPC476122
0.8732	High Similarity	NPC158525
0.8726	High Similarity	NPC472651
0.8726	High Similarity	NPC476861
0.8726	High Similarity	NPC476850
0.8725	High Similarity	NPC7388
0.8718	High Similarity	NPC470940
0.8718	High Similarity	NPC470182
0.8718	High Similarity	NPC276551
0.871	High Similarity	NPC149896
0.871	High Similarity	NPC207978
0.871	High Similarity	NPC193798
0.871	High Similarity	NPC472771
0.871	High Similarity	NPC82851
0.8701	High Similarity	NPC474611
0.8701	High Similarity	NPC475226
0.8701	High Similarity	NPC307383
0.8699	High Similarity	NPC121158
0.8699	High Similarity	NPC473152
0.8679	High Similarity	NPC160818
0.8679	High Similarity	NPC169299
0.8675	High Similarity	NPC18135
0.8671	High Similarity	NPC146872
0.8671	High Similarity	NPC472652
0.8671	High Similarity	NPC271235
0.8662	High Similarity	NPC214600
0.8662	High Similarity	NPC471998
0.8662	High Similarity	NPC478178
0.8662	High Similarity	NPC470875
0.8658	High Similarity	NPC216755
0.8654	High Similarity	NPC292389
0.8654	High Similarity	NPC302369
0.8654	High Similarity	NPC134254
0.8654	High Similarity	NPC477405
0.8654	High Similarity	NPC472773
0.8654	High Similarity	NPC469338
0.8654	High Similarity	NPC39986
0.8645	High Similarity	NPC472653
0.8645	High Similarity	NPC25255
0.8643	High Similarity	NPC21460
0.8636	High Similarity	NPC304692
0.8636	High Similarity	NPC470118
0.8633	High Similarity	NPC207294
0.8633	High Similarity	NPC112706
0.8627	High Similarity	NPC469850
0.8627	High Similarity	NPC92979
0.8627	High Similarity	NPC141538
0.8627	High Similarity	NPC155939
0.8627	High Similarity	NPC296807
0.8618	High Similarity	NPC33938
0.8618	High Similarity	NPC476201
0.8618	High Similarity	NPC268905
0.8616	High Similarity	NPC82602
0.8609	High Similarity	NPC470997
0.8599	High Similarity	NPC261184
0.8599	High Similarity	NPC476858
0.8599	High Similarity	NPC146991
0.8599	High Similarity	NPC469849
0.8599	High Similarity	NPC476856
0.8599	High Similarity	NPC271657
0.8599	High Similarity	NPC476857
0.8591	High Similarity	NPC262198
0.8591	High Similarity	NPC276676
0.859	High Similarity	NPC329938
0.859	High Similarity	NPC470792
0.859	High Similarity	NPC263432
0.859	High Similarity	NPC472767
0.859	High Similarity	NPC117986
0.859	High Similarity	NPC18347
0.8582	High Similarity	NPC89133
0.8581	High Similarity	NPC86935
0.8571	High Similarity	NPC20578
0.8571	High Similarity	NPC62103
0.8571	High Similarity	NPC209364
0.8571	High Similarity	NPC60973
0.8571	High Similarity	NPC104736
0.8562	High Similarity	NPC67003
0.8562	High Similarity	NPC114880
0.8561	High Similarity	NPC95567
0.8561	High Similarity	NPC319140
0.8553	High Similarity	NPC471397
0.8544	High Similarity	NPC93172
0.8544	High Similarity	NPC97574
0.8544	High Similarity	NPC23387
0.8544	High Similarity	NPC472141
0.8543	High Similarity	NPC211625
0.8543	High Similarity	NPC125182
0.8543	High Similarity	NPC69647
0.8543	High Similarity	NPC329180
0.8542	High Similarity	NPC46896
0.8535	High Similarity	NPC472139
0.8533	High Similarity	NPC255414
0.8526	High Similarity	NPC305016
0.8516	High Similarity	NPC286722
0.8516	High Similarity	NPC472283
0.8516	High Similarity	NPC197137
0.8514	High Similarity	NPC243577
0.8514	High Similarity	NPC476946
0.8506	High Similarity	NPC476262
0.8497	Intermediate Similarity	NPC147168
0.8497	Intermediate Similarity	NPC246164
0.8491	Intermediate Similarity	NPC173516
0.8491	Intermediate Similarity	NPC478179
0.8491	Intermediate Similarity	NPC472774
0.8491	Intermediate Similarity	NPC472282
0.8491	Intermediate Similarity	NPC476853
0.8491	Intermediate Similarity	NPC472775
0.8489	Intermediate Similarity	NPC23086
0.8487	Intermediate Similarity	NPC156189
0.8487	Intermediate Similarity	NPC46551
0.8481	Intermediate Similarity	NPC476860
0.8481	Intermediate Similarity	NPC472664
0.8471	Intermediate Similarity	NPC96443
0.8471	Intermediate Similarity	NPC290400
0.8462	Intermediate Similarity	NPC475295
0.8462	Intermediate Similarity	NPC473473
0.8456	Intermediate Similarity	NPC84479
0.8452	Intermediate Similarity	NPC107646
0.8452	Intermediate Similarity	NPC263265
0.8452	Intermediate Similarity	NPC126723
0.8451	Intermediate Similarity	NPC61788
0.8451	Intermediate Similarity	NPC298190

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 NPC250228 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	825
0.2-0.3	1921
0.3-0.4	2616
0.4-0.5	2143
0.5-0.6	1050
0.6-0.7	298
0.7-0.8	36
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD5761	Phase 2
0.875	High Similarity	NPD5760	Phase 2
0.7941	Intermediate Similarity	NPD8434	Phase 2
0.784	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4628	Phase 3
0.7544	Intermediate Similarity	NPD6765	Approved
0.7544	Intermediate Similarity	NPD6764	Approved
0.7532	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD920	Approved
0.7419	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7819	Suspended
0.7371	Intermediate Similarity	NPD6785	Approved
0.7371	Intermediate Similarity	NPD6784	Approved
0.7349	Intermediate Similarity	NPD3749	Approved
0.7341	Intermediate Similarity	NPD6559	Discontinued
0.7312	Intermediate Similarity	NPD2534	Approved
0.7312	Intermediate Similarity	NPD2533	Approved
0.7312	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2532	Approved
0.7273	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6273	Approved
0.7256	Intermediate Similarity	NPD7411	Suspended
0.7246	Intermediate Similarity	NPD7075	Discontinued
0.7244	Intermediate Similarity	NPD1551	Phase 2
0.7239	Intermediate Similarity	NPD3226	Approved
0.7239	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2800	Approved
0.7197	Intermediate Similarity	NPD6004	Phase 3
0.7197	Intermediate Similarity	NPD2346	Discontinued
0.7197	Intermediate Similarity	NPD6002	Phase 3
0.7197	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6005	Phase 3
0.7197	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6599	Discontinued
0.7188	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7033	Discontinued
0.7168	Intermediate Similarity	NPD5844	Phase 1
0.7152	Intermediate Similarity	NPD1549	Phase 2
0.7126	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6801	Discontinued
0.7099	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4380	Phase 2
0.7089	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2799	Discontinued
0.7066	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3750	Approved
0.7059	Intermediate Similarity	NPD5494	Approved
0.7044	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2796	Approved
0.7013	Intermediate Similarity	NPD2313	Discontinued
0.7	Intermediate Similarity	NPD1243	Approved
0.6994	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4965	Approved
0.6982	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7768	Phase 2
0.6982	Remote Similarity	NPD4967	Phase 2
0.6982	Remote Similarity	NPD4966	Approved
0.6981	Remote Similarity	NPD2344	Approved
0.6974	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD8312	Approved
0.6966	Remote Similarity	NPD8313	Approved
0.6957	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD9717	Approved
0.6933	Remote Similarity	NPD6799	Approved
0.6933	Remote Similarity	NPD1608	Approved
0.6923	Remote Similarity	NPD5402	Approved
0.6919	Remote Similarity	NPD6959	Discontinued
0.6918	Remote Similarity	NPD6100	Approved
0.6918	Remote Similarity	NPD6099	Approved
0.6918	Remote Similarity	NPD2935	Discontinued
0.6914	Remote Similarity	NPD3818	Discontinued
0.6909	Remote Similarity	NPD5403	Approved
0.6908	Remote Similarity	NPD2797	Approved
0.6905	Remote Similarity	NPD1934	Approved
0.6903	Remote Similarity	NPD3764	Approved
0.6903	Remote Similarity	NPD3268	Approved
0.6901	Remote Similarity	NPD919	Approved
0.6888	Remote Similarity	NPD8404	Phase 2
0.6883	Remote Similarity	NPD6832	Phase 2
0.6879	Remote Similarity	NPD5710	Approved
0.6879	Remote Similarity	NPD6232	Discontinued
0.6879	Remote Similarity	NPD5711	Approved
0.6875	Remote Similarity	NPD1471	Phase 3
0.6857	Remote Similarity	NPD7473	Discontinued
0.6855	Remote Similarity	NPD4308	Phase 3
0.6855	Remote Similarity	NPD3748	Approved
0.6855	Remote Similarity	NPD1510	Phase 2
0.6852	Remote Similarity	NPD7003	Approved
0.6826	Remote Similarity	NPD7458	Discontinued
0.6821	Remote Similarity	NPD8127	Discontinued
0.6818	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.681	Remote Similarity	NPD2309	Approved
0.6805	Remote Similarity	NPD37	Approved
0.6802	Remote Similarity	NPD6234	Discontinued
0.6797	Remote Similarity	NPD1203	Approved
0.6796	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5401	Approved
0.6784	Remote Similarity	NPD3882	Suspended
0.678	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD447	Suspended
0.6768	Remote Similarity	NPD7236	Approved
0.6758	Remote Similarity	NPD8150	Discontinued
0.6753	Remote Similarity	NPD5647	Approved
0.6733	Remote Similarity	NPD17	Approved
0.6731	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.673	Remote Similarity	NPD1607	Approved
0.6727	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD3817	Phase 2
0.6724	Remote Similarity	NPD1247	Approved
0.6723	Remote Similarity	NPD7228	Approved
0.6711	Remote Similarity	NPD9545	Approved
0.6709	Remote Similarity	NPD1240	Approved
0.6709	Remote Similarity	NPD4140	Approved
0.6705	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6166	Phase 2
0.6705	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD411	Approved
0.6686	Remote Similarity	NPD7229	Phase 3
0.6667	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5124	Phase 1
0.6648	Remote Similarity	NPD7074	Phase 3
0.6647	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2798	Approved
0.6645	Remote Similarity	NPD1019	Discontinued
0.6645	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7177	Discontinued
0.6629	Remote Similarity	NPD7799	Discontinued
0.6629	Remote Similarity	NPD3751	Discontinued
0.6629	Remote Similarity	NPD7199	Phase 2
0.6627	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD6651	Approved
0.6623	Remote Similarity	NPD1778	Approved
0.6623	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD5953	Discontinued
0.6611	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4307	Phase 2
0.6601	Remote Similarity	NPD3972	Approved
0.6592	Remote Similarity	NPD7054	Approved
0.6592	Remote Similarity	NPD7286	Phase 2
0.6591	Remote Similarity	NPD6808	Phase 2
0.6581	Remote Similarity	NPD3266	Approved
0.6581	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD3267	Approved
0.6575	Remote Similarity	NPD7685	Pre-registration
0.657	Remote Similarity	NPD1465	Phase 2
0.6568	Remote Similarity	NPD7239	Suspended
0.6562	Remote Similarity	NPD6355	Discontinued
0.6562	Remote Similarity	NPD1933	Approved
0.6562	Remote Similarity	NPD230	Phase 1
0.6556	Remote Similarity	NPD7472	Approved
0.6545	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4110	Phase 3
0.6541	Remote Similarity	NPD8032	Phase 2
0.6527	Remote Similarity	NPD1511	Approved
0.6522	Remote Similarity	NPD6653	Approved
0.652	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD6797	Phase 2
0.6516	Remote Similarity	NPD3225	Approved
0.6509	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4287	Approved
0.6505	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD4665	Approved
0.6485	Remote Similarity	NPD4111	Phase 1
0.6484	Remote Similarity	NPD7240	Approved
0.6484	Remote Similarity	NPD7251	Discontinued
0.6477	Remote Similarity	NPD3057	Approved
0.6474	Remote Similarity	NPD8455	Phase 2
0.6474	Remote Similarity	NPD6362	Approved
0.6467	Remote Similarity	NPD9493	Approved
0.6463	Remote Similarity	NPD5763	Approved
0.6463	Remote Similarity	NPD5762	Approved
0.6461	Remote Similarity	NPD3926	Phase 2
0.6461	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4107	Approved
0.645	Remote Similarity	NPD1512	Approved
0.6448	Remote Similarity	NPD7808	Phase 3
0.6447	Remote Similarity	NPD5585	Approved
0.6446	Remote Similarity	NPD8166	Discontinued
0.6443	Remote Similarity	NPD7435	Discontinued
0.6438	Remote Similarity	NPD6663	Approved
0.6438	Remote Similarity	NPD6233	Phase 2
0.6437	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4288	Approved
0.6433	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4575	Clinical (unspecified phase)

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