NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	272.628
LogP:	4.669
LogD:	3.646
LogS:	-3.488
# Rotatable Bonds:	6
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.802
Synthetic Accessibility Score:	2.357
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.602
MDCK Permeability:	1.907450132421218e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117
Plasma Protein Binding (PPB):	95.41619110107422%
Volume Distribution (VD):	0.531
Pgp-substrate:	4.591291427612305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.389
CYP1A2-substrate:	0.143
CYP2C19-inhibitor:	0.091
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.612
CYP2C9-substrate:	0.273
CYP2D6-inhibitor:	0.3
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.074

ADMET: Excretion

Clearance (CL):	1.806
Half-life (T1/2):	0.837

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.648
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.248
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.439
Carcinogencity:	0.088
Eye Corrosion:	0.009
Eye Irritation:	0.384
Respiratory Toxicity:	0.708

Download Data

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

Natural Product: NPC160199

Natural Product ID:	NPC160199
*Common Name:**	ADTCKTBSGPXMDB-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ADTCKTBSGPXMDB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-10(2)5-4-6-11(3)13-8-7-12(15(17)18)9-14(13)16/h7-10,16H,3-6H2,1-2H3,(H,17,18)
SMILES:	CC(CCCC(=C)c1ccc(cc1O)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577366
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32607	penicillium aculeatum sd-321	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25763602]

☑ 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
LD50	1
MIC	13

Activity Type	# Activity
Organism	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	32.0	ug.mL-1	PMID[524512]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[524512]
NPT1843	Organism	Aeromonas hydrophila	Aeromonas hydrophila	MIC	>	32.0	ug.mL-1	PMID[524512]
NPT1844	Organism	Edwardsiella tarda	Edwardsiella tarda	MIC	>	32.0	ug.mL-1	PMID[524512]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	32.0	ug.mL-1	PMID[524512]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	32.0	ug.mL-1	PMID[524512]
NPT1845	Organism	Vibrio alginolyticus	Vibrio alginolyticus	MIC	>	32.0	ug.mL-1	PMID[524512]
NPT1311	Organism	Listonella anguillarum	Listonella anguillarum	MIC	>	32.0	ug.mL-1	PMID[524512]
NPT1726	Organism	Vibrio harveyi	Vibrio harveyi	MIC	=	4.0	ug.mL-1	PMID[524512]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	MIC	=	32.0	ug.mL-1	PMID[524512]
NPT1846	Organism	Alternaria brassicae	Alternaria brassicae	MIC	>	32.0	ug.mL-1	PMID[524512]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	MIC	>	32.0	ug.mL-1	PMID[524512]
NPT1847	Organism	Gaeumannomyces graminis	Gaeumannomyces graminis	MIC	=	0.5	ug.mL-1	PMID[524512]
NPT176	Organism	Artemia salina	Artemia salina	LD50	>	10.0	ug ml-1	PMID[524512]

☑ 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 NPC160199 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	253
0.1-0.2	1346
0.2-0.3	3448
0.3-0.4	9328
0.4-0.5	10209
0.5-0.6	6391
0.6-0.7	9513
0.7-0.8	1931
0.8-0.85	213
0.85-0.9	53
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9561	High Similarity	NPC25168
0.9474	High Similarity	NPC165197
0.9316	High Similarity	NPC117794
0.931	High Similarity	NPC297193
0.9237	High Similarity	NPC472592
0.9231	High Similarity	NPC275145
0.9115	High Similarity	NPC161304
0.9068	High Similarity	NPC477153
0.8991	High Similarity	NPC187913
0.8909	High Similarity	NPC34715
0.8879	High Similarity	NPC41567
0.886	High Similarity	NPC81808
0.8793	High Similarity	NPC269414
0.8783	High Similarity	NPC240163
0.8761	High Similarity	NPC228609
0.876	High Similarity	NPC287473
0.8716	High Similarity	NPC13426
0.8696	High Similarity	NPC41851
0.8667	High Similarity	NPC46634
0.8655	High Similarity	NPC301987
0.8655	High Similarity	NPC26433
0.8655	High Similarity	NPC35856
0.8655	High Similarity	NPC178395
0.8655	High Similarity	NPC159760
0.8655	High Similarity	NPC292665
0.8655	High Similarity	NPC115188
0.8655	High Similarity	NPC272454
0.8655	High Similarity	NPC179092
0.8655	High Similarity	NPC244994
0.8655	High Similarity	NPC222876
0.8651	High Similarity	NPC472591
0.8644	High Similarity	NPC233165
0.8644	High Similarity	NPC184579
0.8632	High Similarity	NPC125252
0.8609	High Similarity	NPC190212
0.8559	High Similarity	NPC474890
0.8559	High Similarity	NPC161943
0.8559	High Similarity	NPC273282
0.8547	High Similarity	NPC477453
0.8547	High Similarity	NPC312800
0.8534	High Similarity	NPC114918
0.8534	High Similarity	NPC197513
0.8522	High Similarity	NPC26615
0.8512	High Similarity	NPC307174
0.8512	High Similarity	NPC282577
0.8496	Intermediate Similarity	NPC224584
0.8475	Intermediate Similarity	NPC240664
0.8468	Intermediate Similarity	NPC209959
0.8455	Intermediate Similarity	NPC304873
0.8455	Intermediate Similarity	NPC25458
0.8448	Intermediate Similarity	NPC242136
0.8448	Intermediate Similarity	NPC211421
0.844	Intermediate Similarity	NPC217621
0.8421	Intermediate Similarity	NPC95172
0.8417	Intermediate Similarity	NPC285829
0.8417	Intermediate Similarity	NPC206778
0.8413	Intermediate Similarity	NPC31539
0.8407	Intermediate Similarity	NPC141523
0.839	Intermediate Similarity	NPC83718
0.8387	Intermediate Similarity	NPC49647
0.8387	Intermediate Similarity	NPC227741
0.8387	Intermediate Similarity	NPC295202
0.8387	Intermediate Similarity	NPC306765
0.8387	Intermediate Similarity	NPC136342
0.8374	Intermediate Similarity	NPC236189
0.8374	Intermediate Similarity	NPC234890
0.8374	Intermediate Similarity	NPC74507
0.8361	Intermediate Similarity	NPC244351
0.8347	Intermediate Similarity	NPC241001
0.8333	Intermediate Similarity	NPC472593
0.8333	Intermediate Similarity	NPC473767
0.8333	Intermediate Similarity	NPC100551
0.8319	Intermediate Similarity	NPC317592
0.8306	Intermediate Similarity	NPC123506
0.8306	Intermediate Similarity	NPC131799
0.8306	Intermediate Similarity	NPC167055
0.8306	Intermediate Similarity	NPC240744
0.8304	Intermediate Similarity	NPC93831
0.8291	Intermediate Similarity	NPC98543
0.8268	Intermediate Similarity	NPC108129
0.8264	Intermediate Similarity	NPC478121
0.8264	Intermediate Similarity	NPC72977
0.8264	Intermediate Similarity	NPC260837
0.8257	Intermediate Similarity	NPC253423
0.8254	Intermediate Similarity	NPC48248
0.8254	Intermediate Similarity	NPC96024
0.825	Intermediate Similarity	NPC328694
0.8246	Intermediate Similarity	NPC226699
0.824	Intermediate Similarity	NPC3224
0.8235	Intermediate Similarity	NPC128825
0.8235	Intermediate Similarity	NPC108288
0.8231	Intermediate Similarity	NPC176102
0.8231	Intermediate Similarity	NPC267539
0.8231	Intermediate Similarity	NPC161632
0.8231	Intermediate Similarity	NPC71108
0.8231	Intermediate Similarity	NPC204257
0.8231	Intermediate Similarity	NPC254832
0.8231	Intermediate Similarity	NPC29317
0.8231	Intermediate Similarity	NPC229638
0.823	Intermediate Similarity	NPC303141
0.823	Intermediate Similarity	NPC163734
0.8226	Intermediate Similarity	NPC199273
0.8226	Intermediate Similarity	NPC152525
0.8226	Intermediate Similarity	NPC310540
0.8226	Intermediate Similarity	NPC68756
0.8226	Intermediate Similarity	NPC142956
0.822	Intermediate Similarity	NPC186933
0.822	Intermediate Similarity	NPC163154
0.8214	Intermediate Similarity	NPC235762
0.8214	Intermediate Similarity	NPC471228
0.8211	Intermediate Similarity	NPC121168
0.8211	Intermediate Similarity	NPC68167
0.8211	Intermediate Similarity	NPC300274
0.8211	Intermediate Similarity	NPC283514
0.8211	Intermediate Similarity	NPC475192
0.8211	Intermediate Similarity	NPC67300
0.8205	Intermediate Similarity	NPC231717
0.8203	Intermediate Similarity	NPC7012
0.8198	Intermediate Similarity	NPC52472
0.8198	Intermediate Similarity	NPC72729
0.8197	Intermediate Similarity	NPC164852
0.8197	Intermediate Similarity	NPC190971
0.8189	Intermediate Similarity	NPC109123
0.8189	Intermediate Similarity	NPC117899
0.8182	Intermediate Similarity	NPC328459
0.8182	Intermediate Similarity	NPC79241
0.8182	Intermediate Similarity	NPC90522
0.8182	Intermediate Similarity	NPC6597
0.8175	Intermediate Similarity	NPC72667
0.8175	Intermediate Similarity	NPC78364
0.8175	Intermediate Similarity	NPC176130
0.8175	Intermediate Similarity	NPC69424
0.8175	Intermediate Similarity	NPC84672
0.8175	Intermediate Similarity	NPC71525
0.8174	Intermediate Similarity	NPC279887
0.8174	Intermediate Similarity	NPC68260
0.8168	Intermediate Similarity	NPC472308
0.8167	Intermediate Similarity	NPC150919
0.8165	Intermediate Similarity	NPC246679
0.8165	Intermediate Similarity	NPC257182
0.8158	Intermediate Similarity	NPC6984
0.8154	Intermediate Similarity	NPC288089
0.8151	Intermediate Similarity	NPC322197
0.8145	Intermediate Similarity	NPC273683
0.8145	Intermediate Similarity	NPC174991
0.8145	Intermediate Similarity	NPC375356
0.8142	Intermediate Similarity	NPC475225
0.813	Intermediate Similarity	NPC198336
0.813	Intermediate Similarity	NPC162935
0.813	Intermediate Similarity	NPC249340
0.8115	Intermediate Similarity	NPC7151
0.8115	Intermediate Similarity	NPC216297
0.8115	Intermediate Similarity	NPC473662
0.811	Intermediate Similarity	NPC229894
0.811	Intermediate Similarity	NPC3009
0.811	Intermediate Similarity	NPC282923
0.811	Intermediate Similarity	NPC193203
0.811	Intermediate Similarity	NPC473744
0.8108	Intermediate Similarity	NPC245561
0.8103	Intermediate Similarity	NPC26013
0.8103	Intermediate Similarity	NPC98392
0.8103	Intermediate Similarity	NPC282855
0.8099	Intermediate Similarity	NPC94637
0.8095	Intermediate Similarity	NPC254492
0.8095	Intermediate Similarity	NPC231774
0.8095	Intermediate Similarity	NPC96915
0.8095	Intermediate Similarity	NPC473751
0.8091	Intermediate Similarity	NPC312132
0.8091	Intermediate Similarity	NPC259512
0.8087	Intermediate Similarity	NPC249811
0.8087	Intermediate Similarity	NPC29883
0.8087	Intermediate Similarity	NPC228737
0.808	Intermediate Similarity	NPC173978
0.808	Intermediate Similarity	NPC265910
0.808	Intermediate Similarity	NPC184219
0.808	Intermediate Similarity	NPC91475
0.8077	Intermediate Similarity	NPC157478
0.8077	Intermediate Similarity	NPC289572
0.8077	Intermediate Similarity	NPC115458
0.8077	Intermediate Similarity	NPC295406
0.8077	Intermediate Similarity	NPC239855
0.8077	Intermediate Similarity	NPC200422
0.807	Intermediate Similarity	NPC243677
0.807	Intermediate Similarity	NPC105899
0.8065	Intermediate Similarity	NPC325301
0.8065	Intermediate Similarity	NPC327070
0.8065	Intermediate Similarity	NPC217756
0.8062	Intermediate Similarity	NPC18798
0.8062	Intermediate Similarity	NPC205992
0.8062	Intermediate Similarity	NPC471851
0.806	Intermediate Similarity	NPC147542
0.806	Intermediate Similarity	NPC241349
0.806	Intermediate Similarity	NPC225243
0.806	Intermediate Similarity	NPC37992
0.806	Intermediate Similarity	NPC42262
0.806	Intermediate Similarity	NPC220496
0.806	Intermediate Similarity	NPC32749
0.806	Intermediate Similarity	NPC327916
0.8053	Intermediate Similarity	NPC470202
0.8051	Intermediate Similarity	NPC17693

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 NPC160199 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	913
0.2-0.3	1352
0.3-0.4	2526
0.4-0.5	2276
0.5-0.6	1247
0.6-0.7	461
0.7-0.8	107
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD74	Approved
0.8333	Intermediate Similarity	NPD9266	Approved
0.8246	Intermediate Similarity	NPD9267	Approved
0.8246	Intermediate Similarity	NPD9263	Approved
0.8246	Intermediate Similarity	NPD9264	Approved
0.8235	Intermediate Similarity	NPD9493	Approved
0.8235	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD844	Approved
0.8091	Intermediate Similarity	NPD288	Approved
0.8087	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8016	Intermediate Similarity	NPD1470	Approved
0.7984	Intermediate Similarity	NPD1201	Approved
0.7895	Intermediate Similarity	NPD9261	Approved
0.7874	Intermediate Similarity	NPD1164	Approved
0.7836	Intermediate Similarity	NPD2935	Discontinued
0.7805	Intermediate Similarity	NPD9545	Approved
0.7769	Intermediate Similarity	NPD9281	Approved
0.7742	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD411	Approved
0.7706	Intermediate Similarity	NPD9258	Approved
0.7706	Intermediate Similarity	NPD9256	Approved
0.7704	Intermediate Similarity	NPD5404	Approved
0.7704	Intermediate Similarity	NPD5406	Approved
0.7704	Intermediate Similarity	NPD5405	Approved
0.7704	Intermediate Similarity	NPD5408	Approved
0.7669	Intermediate Similarity	NPD447	Suspended
0.7647	Intermediate Similarity	NPD2346	Discontinued
0.7638	Intermediate Similarity	NPD9269	Phase 2
0.7638	Intermediate Similarity	NPD9717	Approved
0.7632	Intermediate Similarity	NPD2066	Phase 3
0.7623	Intermediate Similarity	NPD5951	Approved
0.7615	Intermediate Similarity	NPD800	Approved
0.76	Intermediate Similarity	NPD9268	Approved
0.7563	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD1090	Approved
0.7545	Intermediate Similarity	NPD1086	Approved
0.7545	Intermediate Similarity	NPD1089	Approved
0.754	Intermediate Similarity	NPD3019	Approved
0.754	Intermediate Similarity	NPD2932	Approved
0.754	Intermediate Similarity	NPD4626	Approved
0.7538	Intermediate Similarity	NPD2798	Approved
0.7519	Intermediate Similarity	NPD1283	Approved
0.75	Intermediate Similarity	NPD4308	Phase 3
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD4750	Phase 3
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD845	Approved
0.7482	Intermediate Similarity	NPD7003	Approved
0.7463	Intermediate Similarity	NPD943	Approved
0.7462	Intermediate Similarity	NPD2797	Approved
0.7462	Intermediate Similarity	NPD1203	Approved
0.7459	Intermediate Similarity	NPD7635	Approved
0.7444	Intermediate Similarity	NPD3764	Approved
0.7444	Intermediate Similarity	NPD2313	Discontinued
0.7436	Intermediate Similarity	NPD1929	Approved
0.7436	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1930	Approved
0.7434	Intermediate Similarity	NPD1693	Approved
0.7419	Intermediate Similarity	NPD255	Approved
0.7419	Intermediate Similarity	NPD256	Approved
0.7411	Intermediate Similarity	NPD1088	Approved
0.7407	Intermediate Similarity	NPD230	Phase 1
0.7402	Intermediate Similarity	NPD1778	Approved
0.7381	Intermediate Similarity	NPD1759	Phase 1
0.7364	Intermediate Similarity	NPD1608	Approved
0.7357	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1317	Discontinued
0.735	Intermediate Similarity	NPD1932	Approved
0.7339	Intermediate Similarity	NPD9257	Approved
0.7339	Intermediate Similarity	NPD9259	Approved
0.7328	Intermediate Similarity	NPD3020	Approved
0.731	Intermediate Similarity	NPD3226	Approved
0.7302	Intermediate Similarity	NPD1758	Phase 1
0.7287	Intermediate Similarity	NPD1281	Approved
0.7281	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2329	Discontinued
0.7273	Intermediate Similarity	NPD1087	Approved
0.7266	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6663	Approved
0.7246	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD9508	Approved
0.7227	Intermediate Similarity	NPD1237	Approved
0.7227	Intermediate Similarity	NPD164	Approved
0.7226	Intermediate Similarity	NPD1607	Approved
0.7218	Intermediate Similarity	NPD9494	Approved
0.7218	Intermediate Similarity	NPD5736	Approved
0.7217	Intermediate Similarity	NPD2859	Approved
0.7217	Intermediate Similarity	NPD2860	Approved
0.7214	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3496	Discontinued
0.7206	Intermediate Similarity	NPD4307	Phase 2
0.7203	Intermediate Similarity	NPD940	Approved
0.7203	Intermediate Similarity	NPD846	Approved
0.7194	Intermediate Similarity	NPD1551	Phase 2
0.7193	Intermediate Similarity	NPD1202	Approved
0.7192	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5691	Approved
0.7185	Intermediate Similarity	NPD3268	Approved
0.7176	Intermediate Similarity	NPD1755	Approved
0.7154	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2533	Approved
0.7153	Intermediate Similarity	NPD2534	Approved
0.7153	Intermediate Similarity	NPD2532	Approved
0.7143	Intermediate Similarity	NPD258	Approved
0.7143	Intermediate Similarity	NPD257	Approved
0.7133	Intermediate Similarity	NPD3300	Phase 2
0.7132	Intermediate Similarity	NPD17	Approved
0.7132	Intermediate Similarity	NPD520	Approved
0.7131	Intermediate Similarity	NPD2182	Approved
0.713	Intermediate Similarity	NPD2934	Approved
0.713	Intermediate Similarity	NPD2933	Approved
0.7122	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD8166	Discontinued
0.7113	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4628	Phase 3
0.7107	Intermediate Similarity	NPD1445	Approved
0.7107	Intermediate Similarity	NPD1444	Approved
0.7099	Intermediate Similarity	NPD3972	Approved
0.7095	Intermediate Similarity	NPD2672	Discontinued
0.7094	Intermediate Similarity	NPD9495	Approved
0.7087	Intermediate Similarity	NPD9568	Approved
0.7083	Intermediate Similarity	NPD7390	Discontinued
0.708	Intermediate Similarity	NPD1240	Approved
0.7075	Intermediate Similarity	NPD7458	Discontinued
0.7073	Intermediate Similarity	NPD3022	Approved
0.7073	Intermediate Similarity	NPD3021	Approved
0.7069	Intermediate Similarity	NPD1809	Phase 2
0.7064	Intermediate Similarity	NPD9491	Approved
0.7063	Intermediate Similarity	NPD2629	Approved
0.7049	Intermediate Similarity	NPD2342	Discontinued
0.7043	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD5277	Phase 2
0.7037	Intermediate Similarity	NPD6832	Phase 2
0.7029	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2344	Approved
0.7018	Intermediate Similarity	NPD1239	Approved
0.7015	Intermediate Similarity	NPD1019	Discontinued
0.7014	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD1564	Approved
0.7009	Intermediate Similarity	NPD1565	Approved
0.7009	Intermediate Similarity	NPD1566	Phase 3
0.7008	Intermediate Similarity	NPD6671	Approved
0.7	Intermediate Similarity	NPD1362	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3750	Approved
0.6986	Remote Similarity	NPD6273	Approved
0.697	Remote Similarity	NPD1481	Phase 2
0.6957	Remote Similarity	NPD2979	Phase 3
0.6957	Remote Similarity	NPD826	Approved
0.6957	Remote Similarity	NPD825	Approved
0.6947	Remote Similarity	NPD3023	Approved
0.6947	Remote Similarity	NPD3026	Approved
0.6942	Remote Similarity	NPD5909	Discontinued
0.6937	Remote Similarity	NPD111	Approved
0.6935	Remote Similarity	NPD1792	Phase 2
0.6929	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3025	Approved
0.6923	Remote Similarity	NPD1651	Approved
0.6923	Remote Similarity	NPD3024	Approved
0.6917	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6232	Discontinued
0.6894	Remote Similarity	NPD1535	Discovery
0.6894	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD1238	Approved
0.6889	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD226	Approved
0.6879	Remote Similarity	NPD7473	Discontinued
0.6879	Remote Similarity	NPD1510	Phase 2
0.6866	Remote Similarity	NPD1876	Approved
0.6861	Remote Similarity	NPD7008	Discontinued
0.6861	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.685	Remote Similarity	NPD1241	Discontinued
0.6842	Remote Similarity	NPD4878	Approved
0.6842	Remote Similarity	NPD5347	Phase 2
0.6842	Remote Similarity	NPD5346	Phase 2
0.6838	Remote Similarity	NPD9569	Approved
0.6838	Remote Similarity	NPD9260	Approved
0.6831	Remote Similarity	NPD6099	Approved
0.6831	Remote Similarity	NPD6100	Approved
0.6829	Remote Similarity	NPD3134	Approved
0.6828	Remote Similarity	NPD2309	Approved
0.6825	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3266	Approved
0.6815	Remote Similarity	NPD3267	Approved
0.6803	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3684	Discontinued
0.6797	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5585	Approved
0.6786	Remote Similarity	NPD275	Approved
0.6786	Remote Similarity	NPD274	Approved
0.6786	Remote Similarity	NPD6355	Discontinued
0.6779	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD422	Phase 1
0.6767	Remote Similarity	NPD1611	Approved
0.6767	Remote Similarity	NPD6287	Discontinued
0.6763	Remote Similarity	NPD259	Phase 1
0.6752	Remote Similarity	NPD1563	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