NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	180.12
Volume:	199.927
LogP:	2.589
LogD:	2.514
LogS:	-2.14
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.747
Synthetic Accessibility Score:	2.292
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.319
MDCK Permeability:	2.2553764210897498e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.127
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.209
Plasma Protein Binding (PPB):	56.83729934692383%
Volume Distribution (VD):	2.358
Pgp-substrate:	36.02931594848633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.682
CYP1A2-substrate:	0.889
CYP2C19-inhibitor:	0.379
CYP2C19-substrate:	0.466
CYP2C9-inhibitor:	0.229
CYP2C9-substrate:	0.907
CYP2D6-inhibitor:	0.355
CYP2D6-substrate:	0.736
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.319

ADMET: Excretion

Clearance (CL):	12.891
Half-life (T1/2):	0.762

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.028
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.24
Maximum Recommended Daily Dose:	0.339
Skin Sensitization:	0.891
Carcinogencity:	0.048
Eye Corrosion:	0.222
Eye Irritation:	0.973
Respiratory Toxicity:	0.111

Download Data

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

Natural Product: NPC474073

Natural Product ID:	NPC474073
*Common Name:**	3-(1-Hydroxypentyl)Phenol
IUPAC Name:	3-(1-hydroxypentyl)phenol
Synonyms:	3-(1'-Hydroxypentyl)Phenol
Standard InCHIKey:	RUMUPMSZUNLFBX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H16O2/c1-2-3-7-11(13)9-5-4-6-10(12)8-9/h4-6,8,11-13H,2-3,7H2,1H3
SMILES:	CCCCC(C1=CC(=CC=C1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459832
PubChem CID:	10035212
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004647] 1-hydroxy-4-unsubstituted benzenoids

*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
NPO5602	Bombardioidea anartia	Species	Lasiosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421752]

☑ 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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	12.0	mm	PMID[494284]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	19.0	mm	PMID[494284]

☑ 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 NPC474073 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	205
0.1-0.2	1325
0.2-0.3	4352
0.3-0.4	12936
0.4-0.5	7222
0.5-0.6	10178
0.6-0.7	4807
0.7-0.8	1328
0.8-0.85	197
0.85-0.9	120
0.9-0.95	26
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC235762
0.9375	High Similarity	NPC471228
0.9368	High Similarity	NPC294741
0.9368	High Similarity	NPC174911
0.9341	High Similarity	NPC312304
0.9278	High Similarity	NPC475225
0.914	High Similarity	NPC325292
0.914	High Similarity	NPC138117
0.914	High Similarity	NPC162314
0.914	High Similarity	NPC306884
0.914	High Similarity	NPC147284
0.914	High Similarity	NPC94139
0.914	High Similarity	NPC210497
0.914	High Similarity	NPC3358
0.913	High Similarity	NPC192
0.9121	High Similarity	NPC27974
0.9082	High Similarity	NPC323810
0.901	High Similarity	NPC473524
0.9	High Similarity	NPC66834
0.9	High Similarity	NPC61033
0.9	High Similarity	NPC305603
0.8969	High Similarity	NPC48730
0.8969	High Similarity	NPC248396
0.8969	High Similarity	NPC130103
0.8969	High Similarity	NPC129373
0.8958	High Similarity	NPC152097
0.8947	High Similarity	NPC313650
0.8936	High Similarity	NPC55903
0.8925	High Similarity	NPC300017
0.8866	High Similarity	NPC260775
0.8866	High Similarity	NPC216468
0.8866	High Similarity	NPC78119
0.8866	High Similarity	NPC132078
0.8866	High Similarity	NPC128723
0.8866	High Similarity	NPC51333
0.8842	High Similarity	NPC76938
0.8817	High Similarity	NPC318325
0.8817	High Similarity	NPC242240
0.8817	High Similarity	NPC123273
0.8812	High Similarity	NPC474352
0.88	High Similarity	NPC471350
0.8791	High Similarity	NPC150837
0.8788	High Similarity	NPC108497
0.8776	High Similarity	NPC213730
0.8776	High Similarity	NPC70677
0.8776	High Similarity	NPC72729
0.8776	High Similarity	NPC130756
0.8776	High Similarity	NPC12931
0.8763	High Similarity	NPC79241
0.8763	High Similarity	NPC6597
0.8763	High Similarity	NPC475078
0.8763	High Similarity	NPC88420
0.875	High Similarity	NPC32714
0.875	High Similarity	NPC274678
0.875	High Similarity	NPC222146
0.8737	High Similarity	NPC29373
0.871	High Similarity	NPC19680
0.871	High Similarity	NPC104216
0.871	High Similarity	NPC25493
0.871	High Similarity	NPC113460
0.8687	High Similarity	NPC7686
0.8687	High Similarity	NPC110764
0.8687	High Similarity	NPC471578
0.8687	High Similarity	NPC40258
0.8687	High Similarity	NPC101025
0.8687	High Similarity	NPC477685
0.8687	High Similarity	NPC91461
0.8673	High Similarity	NPC299762
0.8673	High Similarity	NPC33675
0.866	High Similarity	NPC312132
0.866	High Similarity	NPC259512
0.8646	High Similarity	NPC316301
0.8646	High Similarity	NPC27323
0.8646	High Similarity	NPC245187
0.8646	High Similarity	NPC152415
0.8641	High Similarity	NPC62258
0.8641	High Similarity	NPC55617
0.8632	High Similarity	NPC304541
0.8632	High Similarity	NPC231150
0.8617	High Similarity	NPC177420
0.8617	High Similarity	NPC258219
0.8617	High Similarity	NPC280347
0.8614	High Similarity	NPC233396
0.8614	High Similarity	NPC154899
0.8614	High Similarity	NPC47284
0.8602	High Similarity	NPC307235
0.8602	High Similarity	NPC23167
0.8602	High Similarity	NPC407
0.86	High Similarity	NPC302219
0.86	High Similarity	NPC94351
0.86	High Similarity	NPC71002
0.86	High Similarity	NPC269212
0.86	High Similarity	NPC168303
0.86	High Similarity	NPC24404
0.86	High Similarity	NPC313030
0.86	High Similarity	NPC53051
0.86	High Similarity	NPC242342
0.86	High Similarity	NPC222522
0.86	High Similarity	NPC85479
0.86	High Similarity	NPC106396
0.86	High Similarity	NPC146798
0.86	High Similarity	NPC249828
0.8586	High Similarity	NPC10588
0.8586	High Similarity	NPC166761
0.8571	High Similarity	NPC228452
0.8571	High Similarity	NPC302371
0.8571	High Similarity	NPC304538
0.8558	High Similarity	NPC174096
0.8558	High Similarity	NPC132720
0.8558	High Similarity	NPC120982
0.8558	High Similarity	NPC79793
0.8558	High Similarity	NPC226401
0.8558	High Similarity	NPC147634
0.8557	High Similarity	NPC26244
0.8544	High Similarity	NPC262365
0.8529	High Similarity	NPC135464
0.8529	High Similarity	NPC155072
0.8529	High Similarity	NPC92623
0.8529	High Similarity	NPC53740
0.8526	High Similarity	NPC55561
0.8526	High Similarity	NPC47950
0.8526	High Similarity	NPC300478
0.8515	High Similarity	NPC130817
0.8515	High Similarity	NPC475580
0.8515	High Similarity	NPC12278
0.85	High Similarity	NPC11280
0.85	High Similarity	NPC137415
0.85	High Similarity	NPC147310
0.85	High Similarity	NPC252105
0.85	High Similarity	NPC166313
0.85	High Similarity	NPC294186
0.85	High Similarity	NPC24407
0.85	High Similarity	NPC284011
0.85	High Similarity	NPC80800
0.85	High Similarity	NPC72947
0.85	High Similarity	NPC192032
0.85	High Similarity	NPC12221
0.8495	Intermediate Similarity	NPC155393
0.8495	Intermediate Similarity	NPC197783
0.8485	Intermediate Similarity	NPC92730
0.8485	Intermediate Similarity	NPC131587
0.8476	Intermediate Similarity	NPC187583
0.8476	Intermediate Similarity	NPC257430
0.8476	Intermediate Similarity	NPC179002
0.8469	Intermediate Similarity	NPC473388
0.8462	Intermediate Similarity	NPC98392
0.8454	Intermediate Similarity	NPC151715
0.8447	Intermediate Similarity	NPC320439
0.8447	Intermediate Similarity	NPC233320
0.8438	Intermediate Similarity	NPC306074
0.8438	Intermediate Similarity	NPC155908
0.8438	Intermediate Similarity	NPC45040
0.8416	Intermediate Similarity	NPC196479
0.8416	Intermediate Similarity	NPC62351
0.8411	Intermediate Similarity	NPC473931
0.8411	Intermediate Similarity	NPC474050
0.8411	Intermediate Similarity	NPC474114
0.8404	Intermediate Similarity	NPC184169
0.84	Intermediate Similarity	NPC211885
0.8396	Intermediate Similarity	NPC26615
0.8396	Intermediate Similarity	NPC473521
0.8396	Intermediate Similarity	NPC228425
0.8387	Intermediate Similarity	NPC248817
0.8387	Intermediate Similarity	NPC175313
0.8387	Intermediate Similarity	NPC286904
0.8384	Intermediate Similarity	NPC77492
0.8384	Intermediate Similarity	NPC109955
0.8384	Intermediate Similarity	NPC225464
0.8365	Intermediate Similarity	NPC317305
0.8365	Intermediate Similarity	NPC75440
0.8352	Intermediate Similarity	NPC87299
0.8352	Intermediate Similarity	NPC99394
0.8352	Intermediate Similarity	NPC103326
0.8352	Intermediate Similarity	NPC329319
0.835	Intermediate Similarity	NPC310456
0.835	Intermediate Similarity	NPC477814
0.835	Intermediate Similarity	NPC469913
0.8349	Intermediate Similarity	NPC320864
0.8333	Intermediate Similarity	NPC241891
0.8333	Intermediate Similarity	NPC244513
0.8333	Intermediate Similarity	NPC272029
0.8333	Intermediate Similarity	NPC474486
0.8333	Intermediate Similarity	NPC218879
0.8333	Intermediate Similarity	NPC227458
0.8333	Intermediate Similarity	NPC120719
0.8318	Intermediate Similarity	NPC28784
0.8318	Intermediate Similarity	NPC190212
0.8318	Intermediate Similarity	NPC261343
0.8318	Intermediate Similarity	NPC296144
0.8318	Intermediate Similarity	NPC319803
0.8317	Intermediate Similarity	NPC100340
0.8317	Intermediate Similarity	NPC143659
0.8316	Intermediate Similarity	NPC1793
0.8302	Intermediate Similarity	NPC308689
0.8302	Intermediate Similarity	NPC275627
0.8302	Intermediate Similarity	NPC54373
0.83	Intermediate Similarity	NPC252821
0.83	Intermediate Similarity	NPC122005
0.8283	Intermediate Similarity	NPC132271
0.8283	Intermediate Similarity	NPC82664

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 NPC474073 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	937
0.2-0.3	1459
0.3-0.4	2813
0.4-0.5	1974
0.5-0.6	1134
0.6-0.7	510
0.7-0.8	92
0.8-0.85	10
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8947	High Similarity	NPD844	Approved
0.8776	High Similarity	NPD289	Clinical (unspecified phase)
0.866	High Similarity	NPD288	Approved
0.8646	High Similarity	NPD1432	Clinical (unspecified phase)
0.8557	High Similarity	NPD2859	Approved
0.8557	High Similarity	NPD2860	Approved
0.8485	Intermediate Similarity	NPD3020	Approved
0.8454	Intermediate Similarity	NPD2933	Approved
0.8454	Intermediate Similarity	NPD2934	Approved
0.8351	Intermediate Similarity	NPD845	Approved
0.828	Intermediate Similarity	NPD111	Approved
0.8241	Intermediate Similarity	NPD9614	Approved
0.8241	Intermediate Similarity	NPD9618	Approved
0.8173	Intermediate Similarity	NPD1444	Approved
0.8173	Intermediate Similarity	NPD1445	Approved
0.8137	Intermediate Similarity	NPD846	Approved
0.8137	Intermediate Similarity	NPD940	Approved
0.8113	Intermediate Similarity	NPD3021	Approved
0.8113	Intermediate Similarity	NPD3022	Approved
0.8108	Intermediate Similarity	NPD3091	Approved
0.8018	Intermediate Similarity	NPD9613	Approved
0.8018	Intermediate Similarity	NPD9615	Approved
0.8018	Intermediate Similarity	NPD9616	Approved
0.8	Intermediate Similarity	NPD1809	Phase 2
0.7946	Intermediate Similarity	NPD316	Approved
0.7944	Intermediate Similarity	NPD1792	Phase 2
0.7944	Intermediate Similarity	NPD4750	Phase 3
0.789	Intermediate Similarity	NPD7635	Approved
0.7864	Intermediate Similarity	NPD1242	Phase 1
0.7838	Intermediate Similarity	NPD6671	Approved
0.7826	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3092	Approved
0.7802	Intermediate Similarity	NPD9294	Approved
0.7798	Intermediate Similarity	NPD228	Approved
0.7778	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD9500	Approved
0.7712	Intermediate Similarity	NPD3094	Phase 2
0.7685	Intermediate Similarity	NPD2684	Approved
0.7664	Intermediate Similarity	NPD968	Approved
0.7652	Intermediate Similarity	NPD9384	Approved
0.7652	Intermediate Similarity	NPD3095	Discontinued
0.7652	Intermediate Similarity	NPD9381	Approved
0.7593	Intermediate Similarity	NPD290	Approved
0.7593	Intermediate Similarity	NPD2342	Discontinued
0.7589	Intermediate Similarity	NPD1791	Approved
0.7589	Intermediate Similarity	NPD1793	Approved
0.7544	Intermediate Similarity	NPD856	Approved
0.7544	Intermediate Similarity	NPD16	Approved
0.7542	Intermediate Similarity	NPD9622	Approved
0.7527	Intermediate Similarity	NPD9088	Approved
0.75	Intermediate Similarity	NPD2229	Approved
0.75	Intermediate Similarity	NPD2228	Approved
0.75	Intermediate Similarity	NPD2234	Approved
0.75	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD9610	Approved
0.7477	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD9608	Approved
0.7473	Intermediate Similarity	NPD9087	Approved
0.7459	Intermediate Similarity	NPD3027	Phase 3
0.7458	Intermediate Similarity	NPD2231	Phase 2
0.7458	Intermediate Similarity	NPD2235	Phase 2
0.7414	Intermediate Similarity	NPD1357	Approved
0.7411	Intermediate Similarity	NPD9379	Approved
0.7411	Intermediate Similarity	NPD7843	Approved
0.7411	Intermediate Similarity	NPD9377	Approved
0.7391	Intermediate Similarity	NPD317	Approved
0.7391	Intermediate Similarity	NPD318	Approved
0.7383	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7157	Approved
0.7358	Intermediate Similarity	NPD3028	Approved
0.7355	Intermediate Similarity	NPD9619	Approved
0.7355	Intermediate Similarity	NPD858	Approved
0.7355	Intermediate Similarity	NPD9620	Approved
0.7355	Intermediate Similarity	NPD602	Approved
0.7355	Intermediate Similarity	NPD9621	Approved
0.7355	Intermediate Similarity	NPD599	Approved
0.7355	Intermediate Similarity	NPD859	Approved
0.735	Intermediate Similarity	NPD2932	Approved
0.735	Intermediate Similarity	NPD3019	Approved
0.735	Intermediate Similarity	NPD4059	Approved
0.7333	Intermediate Similarity	NPD9273	Approved
0.7311	Intermediate Similarity	NPD2233	Approved
0.7311	Intermediate Similarity	NPD2230	Approved
0.7311	Intermediate Similarity	NPD2232	Approved
0.7295	Intermediate Similarity	NPD5736	Approved
0.7295	Intermediate Similarity	NPD2861	Phase 2
0.7288	Intermediate Similarity	NPD3496	Discontinued
0.7265	Intermediate Similarity	NPD4093	Discontinued
0.7258	Intermediate Similarity	NPD597	Approved
0.7258	Intermediate Similarity	NPD598	Approved
0.7258	Intermediate Similarity	NPD601	Approved
0.7257	Intermediate Similarity	NPD821	Approved
0.725	Intermediate Similarity	NPD4659	Approved
0.725	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD600	Approved
0.7236	Intermediate Similarity	NPD596	Approved
0.7232	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD9295	Approved
0.7213	Intermediate Similarity	NPD6584	Phase 3
0.7203	Intermediate Similarity	NPD4626	Approved
0.7203	Intermediate Similarity	NPD1751	Approved
0.72	Intermediate Similarity	NPD1136	Approved
0.72	Intermediate Similarity	NPD1130	Approved
0.72	Intermediate Similarity	NPD1132	Approved
0.7193	Intermediate Similarity	NPD5283	Phase 1
0.7179	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD9612	Approved
0.717	Intermediate Similarity	NPD9611	Approved
0.717	Intermediate Similarity	NPD9495	Approved
0.717	Intermediate Similarity	NPD9609	Approved
0.7167	Intermediate Similarity	NPD2561	Approved
0.7167	Intermediate Similarity	NPD2562	Approved
0.7143	Intermediate Similarity	NPD2238	Phase 2
0.7131	Intermediate Similarity	NPD1131	Approved
0.7131	Intermediate Similarity	NPD1133	Approved
0.7131	Intermediate Similarity	NPD1134	Approved
0.7131	Intermediate Similarity	NPD1135	Approved
0.7131	Intermediate Similarity	NPD4103	Phase 2
0.7131	Intermediate Similarity	NPD1129	Approved
0.7131	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD854	Approved
0.713	Intermediate Similarity	NPD855	Approved
0.713	Intermediate Similarity	NPD497	Approved
0.7107	Intermediate Similarity	NPD1755	Approved
0.7073	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD558	Phase 2
0.7069	Intermediate Similarity	NPD255	Approved
0.7069	Intermediate Similarity	NPD256	Approved
0.7063	Intermediate Similarity	NPD6663	Approved
0.7063	Intermediate Similarity	NPD839	Approved
0.7063	Intermediate Similarity	NPD840	Approved
0.7059	Intermediate Similarity	NPD1778	Approved
0.7059	Intermediate Similarity	NPD2286	Discontinued
0.7043	Intermediate Similarity	NPD498	Approved
0.7043	Intermediate Similarity	NPD495	Approved
0.7043	Intermediate Similarity	NPD496	Approved
0.7041	Intermediate Similarity	NPD9089	Approved
0.7031	Intermediate Similarity	NPD817	Approved
0.7031	Intermediate Similarity	NPD2568	Approved
0.7031	Intermediate Similarity	NPD823	Approved
0.7009	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD3059	Approved
0.7008	Intermediate Similarity	NPD3620	Phase 2
0.7008	Intermediate Similarity	NPD3061	Approved
0.7008	Intermediate Similarity	NPD3062	Approved
0.7008	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD1613	Approved
0.7	Intermediate Similarity	NPD1237	Approved
0.6992	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5451	Approved
0.6984	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD475	Phase 2
0.6983	Remote Similarity	NPD2629	Approved
0.6975	Remote Similarity	NPD5691	Approved
0.6967	Remote Similarity	NPD6583	Phase 3
0.6967	Remote Similarity	NPD3685	Discontinued
0.6967	Remote Similarity	NPD6582	Phase 2
0.6967	Remote Similarity	NPD4749	Approved
0.6942	Remote Similarity	NPD1201	Approved
0.6942	Remote Similarity	NPD1091	Approved
0.6942	Remote Similarity	NPD1610	Phase 2
0.6939	Remote Similarity	NPD9093	Approved
0.6923	Remote Similarity	NPD7743	Approved
0.6923	Remote Similarity	NPD709	Approved
0.6923	Remote Similarity	NPD7742	Approved
0.6917	Remote Similarity	NPD4589	Approved
0.6917	Remote Similarity	NPD2667	Approved
0.6917	Remote Similarity	NPD2668	Approved
0.6911	Remote Similarity	NPD6696	Suspended
0.6899	Remote Similarity	NPD5314	Approved
0.6899	Remote Similarity	NPD6653	Approved
0.6897	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1398	Phase 1
0.6891	Remote Similarity	NPD5304	Approved
0.6891	Remote Similarity	NPD9545	Approved
0.6891	Remote Similarity	NPD1548	Phase 1
0.6891	Remote Similarity	NPD5303	Approved
0.688	Remote Similarity	NPD1712	Approved
0.6875	Remote Similarity	NPD825	Approved
0.6875	Remote Similarity	NPD4140	Approved
0.6875	Remote Similarity	NPD4060	Phase 1
0.6875	Remote Similarity	NPD3134	Approved
0.6875	Remote Similarity	NPD826	Approved
0.6864	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD9493	Approved
0.686	Remote Similarity	NPD3421	Phase 3
0.6855	Remote Similarity	NPD3055	Approved
0.6855	Remote Similarity	NPD3053	Approved
0.6847	Remote Similarity	NPD9244	Approved
0.6847	Remote Similarity	NPD314	Approved
0.6847	Remote Similarity	NPD311	Approved
0.6847	Remote Similarity	NPD315	Approved
0.6847	Remote Similarity	NPD309	Approved
0.6847	Remote Similarity	NPD310	Approved
0.6847	Remote Similarity	NPD10	Approved
0.6833	Remote Similarity	NPD1651	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