NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	164.12
Volume:	191.137
LogP:	3.842
LogD:	3.715
LogS:	-2.963
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.678
Synthetic Accessibility Score:	1.444
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.412
MDCK Permeability:	1.8363909475738183e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.928
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.745
Plasma Protein Binding (PPB):	94.29759979248047%
Volume Distribution (VD):	1.939
Pgp-substrate:	4.865183353424072%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.727
CYP2C19-inhibitor:	0.936
CYP2C19-substrate:	0.294
CYP2C9-inhibitor:	0.684
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.795
CYP2D6-substrate:	0.701
CYP3A4-inhibitor:	0.14
CYP3A4-substrate:	0.289

ADMET: Excretion

Clearance (CL):	12.013
Half-life (T1/2):	0.766

ADMET: Toxicity

hERG Blockers:	0.073
Human Hepatotoxicity (H-HT):	0.029
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.243
Maximum Recommended Daily Dose:	0.044
Skin Sensitization:	0.91
Carcinogencity:	0.131
Eye Corrosion:	0.97
Eye Irritation:	0.992
Respiratory Toxicity:	0.312

Download Data

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

Natural Product: NPC242240

Natural Product ID:	NPC242240
*Common Name:**	4-Pentylphenol
IUPAC Name:	4-pentylphenol
Synonyms:	4-N-Amylphenol; 4-Pentyl-Phenol; 4-Pentylphenol
Standard InCHIKey:	ZNPSUQQXTRRSBM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H16O/c1-2-3-4-5-10-6-8-11(12)9-7-10/h6-9,12H,2-5H2,1H3
SMILES:	CCCCCc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL153388
PubChem CID:	26975
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004646] 1-hydroxy-2-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
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374978]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679317]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17997069]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	7
Potency	5

Activity Type	# Activity
Cell Line	2
Individual Protein	5
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1817	Individual Protein	Aryl sulfotransferase	Rattus norvegicus	Km	=	9000.0	nM	PMID[471342]
NPT1817	Individual Protein	Aryl sulfotransferase	Rattus norvegicus	Vmax	=	208.0	nM min-1	PMID[471342]
NPT1817	Individual Protein	Aryl sulfotransferase	Rattus norvegicus	Ratio	=	784.0	n.a.	PMID[471342]
NPT137	Cell Line	L1210	Mus musculus	log(1/ID50)	=	4.47	n.a.	PMID[471343]
NPT137	Cell Line	L1210	Mus musculus	Activity	<	15.0	%	PMID[471343]
NPT27	Others	Unspecified		log Ks	=	4.19	n.a.	PMID[471344]
NPT901	Individual Protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	Activity	=	0.0	pm/min/mg	PMID[471345]
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	6859	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43277.1	nM	PubChem BioAssay data set

☑ 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 NPC242240 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	240
0.1-0.2	2200
0.2-0.3	6801
0.3-0.4	12353
0.4-0.5	6663
0.5-0.6	9158
0.6-0.7	3997
0.7-0.8	932
0.8-0.85	224
0.85-0.9	76
0.9-0.95	36
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC318325
1.0	High Similarity	NPC123273
0.9881	High Similarity	NPC25493
0.9881	High Similarity	NPC113460
0.9765	High Similarity	NPC280347
0.9765	High Similarity	NPC177420
0.9765	High Similarity	NPC258219
0.9762	High Similarity	NPC23167
0.9651	High Similarity	NPC55561
0.9643	High Similarity	NPC197783
0.9545	High Similarity	NPC316301
0.9545	High Similarity	NPC27323
0.954	High Similarity	NPC304541
0.9529	High Similarity	NPC184169
0.9524	High Similarity	NPC248817
0.9524	High Similarity	NPC175313
0.9438	High Similarity	NPC26244
0.9405	High Similarity	NPC265146
0.9405	High Similarity	NPC124436
0.9333	High Similarity	NPC473388
0.9326	High Similarity	NPC151715
0.9318	High Similarity	NPC45040
0.9318	High Similarity	NPC155908
0.9318	High Similarity	NPC204210
0.931	High Similarity	NPC98772
0.9302	High Similarity	NPC407
0.9302	High Similarity	NPC307235
0.9231	High Similarity	NPC77492
0.9231	High Similarity	NPC225464
0.9222	High Similarity	NPC8392
0.9213	High Similarity	NPC3358
0.9213	High Similarity	NPC210497
0.9213	High Similarity	NPC138117
0.9213	High Similarity	NPC325292
0.9213	High Similarity	NPC306884
0.9213	High Similarity	NPC162314
0.9213	High Similarity	NPC147284
0.9213	High Similarity	NPC94139
0.9205	High Similarity	NPC300017
0.9205	High Similarity	NPC192
0.9195	High Similarity	NPC27974
0.9186	High Similarity	NPC155393
0.913	High Similarity	NPC122005
0.913	High Similarity	NPC252821
0.913	High Similarity	NPC92730
0.913	High Similarity	NPC128723
0.9111	High Similarity	NPC152415
0.9111	High Similarity	NPC128062
0.9101	High Similarity	NPC306074
0.9101	High Similarity	NPC270547
0.9091	High Similarity	NPC70436
0.907	High Similarity	NPC286904
0.9032	High Similarity	NPC225506
0.9011	High Similarity	NPC313650
0.9011	High Similarity	NPC274678
0.9011	High Similarity	NPC144682
0.9	High Similarity	NPC55903
0.8977	High Similarity	NPC104216
0.8925	High Similarity	NPC51333
0.8925	High Similarity	NPC78119
0.8925	High Similarity	NPC216468
0.8925	High Similarity	NPC132078
0.8913	High Similarity	NPC132271
0.8913	High Similarity	NPC82664
0.8913	High Similarity	NPC292730
0.8913	High Similarity	NPC216520
0.8901	High Similarity	NPC289769
0.8901	High Similarity	NPC76938
0.8851	High Similarity	NPC150837
0.883	High Similarity	NPC213730
0.883	High Similarity	NPC211885
0.8817	High Similarity	NPC6597
0.8817	High Similarity	NPC260000
0.8817	High Similarity	NPC474073
0.8817	High Similarity	NPC79241
0.8804	High Similarity	NPC222146
0.8804	High Similarity	NPC32714
0.8791	High Similarity	NPC271440
0.8791	High Similarity	NPC181709
0.8778	High Similarity	NPC300478
0.8764	High Similarity	NPC19680
0.8737	High Similarity	NPC40258
0.8737	High Similarity	NPC7686
0.8737	High Similarity	NPC91461
0.8723	High Similarity	NPC80027
0.8723	High Similarity	NPC299762
0.8723	High Similarity	NPC33675
0.8723	High Similarity	NPC280869
0.871	High Similarity	NPC312132
0.871	High Similarity	NPC259512
0.871	High Similarity	NPC202986
0.8696	High Similarity	NPC245187
0.8681	High Similarity	NPC231150
0.866	High Similarity	NPC154899
0.866	High Similarity	NPC138942
0.866	High Similarity	NPC233396
0.866	High Similarity	NPC303141
0.8646	High Similarity	NPC196479
0.8646	High Similarity	NPC168829
0.8632	High Similarity	NPC248396
0.8632	High Similarity	NPC48730
0.8632	High Similarity	NPC129373
0.8632	High Similarity	NPC72729
0.8617	High Similarity	NPC32674
0.8617	High Similarity	NPC107619
0.8617	High Similarity	NPC152097
0.8617	High Similarity	NPC109955
0.8571	High Similarity	NPC271274
0.8571	High Similarity	NPC113457
0.8571	High Similarity	NPC135464
0.8571	High Similarity	NPC477814
0.8571	High Similarity	NPC92623
0.8557	High Similarity	NPC120719
0.8557	High Similarity	NPC8931
0.8557	High Similarity	NPC119860
0.8557	High Similarity	NPC120693
0.8557	High Similarity	NPC261573
0.8557	High Similarity	NPC288411
0.8542	High Similarity	NPC471578
0.8542	High Similarity	NPC101025
0.8542	High Similarity	NPC252105
0.8542	High Similarity	NPC472585
0.8526	High Similarity	NPC245561
0.8526	High Similarity	NPC260775
0.8495	Intermediate Similarity	NPC81010
0.8495	Intermediate Similarity	NPC32977
0.8488	Intermediate Similarity	NPC133050
0.8485	Intermediate Similarity	NPC228737
0.8469	Intermediate Similarity	NPC474839
0.8469	Intermediate Similarity	NPC243677
0.8454	Intermediate Similarity	NPC235762
0.8454	Intermediate Similarity	NPC313030
0.8454	Intermediate Similarity	NPC471228
0.8454	Intermediate Similarity	NPC106396
0.8454	Intermediate Similarity	NPC71002
0.8454	Intermediate Similarity	NPC62351
0.8454	Intermediate Similarity	NPC108497
0.8454	Intermediate Similarity	NPC242342
0.8454	Intermediate Similarity	NPC222522
0.8454	Intermediate Similarity	NPC94351
0.8454	Intermediate Similarity	NPC302219
0.8454	Intermediate Similarity	NPC85479
0.8454	Intermediate Similarity	NPC146798
0.8454	Intermediate Similarity	NPC470202
0.8454	Intermediate Similarity	NPC53051
0.8454	Intermediate Similarity	NPC168303
0.8454	Intermediate Similarity	NPC249828
0.8454	Intermediate Similarity	NPC135784
0.8454	Intermediate Similarity	NPC24404
0.8438	Intermediate Similarity	NPC289381
0.8438	Intermediate Similarity	NPC10588
0.8438	Intermediate Similarity	NPC130756
0.8438	Intermediate Similarity	NPC174911
0.8438	Intermediate Similarity	NPC294741
0.8438	Intermediate Similarity	NPC12931
0.8438	Intermediate Similarity	NPC52472
0.8438	Intermediate Similarity	NPC166761
0.8438	Intermediate Similarity	NPC155847
0.8438	Intermediate Similarity	NPC70677
0.8421	Intermediate Similarity	NPC201967
0.8421	Intermediate Similarity	NPC475078
0.8409	Intermediate Similarity	NPC304538
0.8404	Intermediate Similarity	NPC286006
0.8404	Intermediate Similarity	NPC107522
0.84	Intermediate Similarity	NPC75440
0.84	Intermediate Similarity	NPC61885
0.84	Intermediate Similarity	NPC317305
0.84	Intermediate Similarity	NPC63698
0.84	Intermediate Similarity	NPC11554
0.8387	Intermediate Similarity	NPC29373
0.8384	Intermediate Similarity	NPC188677
0.8384	Intermediate Similarity	NPC21594
0.837	Intermediate Similarity	NPC151764
0.837	Intermediate Similarity	NPC47950
0.837	Intermediate Similarity	NPC312304
0.8367	Intermediate Similarity	NPC254965
0.8367	Intermediate Similarity	NPC471511
0.8367	Intermediate Similarity	NPC327811
0.8367	Intermediate Similarity	NPC30506
0.8367	Intermediate Similarity	NPC475225
0.8351	Intermediate Similarity	NPC110764
0.8351	Intermediate Similarity	NPC72947
0.8351	Intermediate Similarity	NPC137415
0.8351	Intermediate Similarity	NPC166313
0.8351	Intermediate Similarity	NPC147310
0.8351	Intermediate Similarity	NPC284011
0.8351	Intermediate Similarity	NPC294186
0.8351	Intermediate Similarity	NPC24407
0.8351	Intermediate Similarity	NPC11280
0.8351	Intermediate Similarity	NPC477685
0.8351	Intermediate Similarity	NPC51015
0.8351	Intermediate Similarity	NPC192032
0.8333	Intermediate Similarity	NPC130193
0.8333	Intermediate Similarity	NPC100870
0.8333	Intermediate Similarity	NPC171843
0.8333	Intermediate Similarity	NPC125732
0.8317	Intermediate Similarity	NPC75272
0.8317	Intermediate Similarity	NPC471954
0.8317	Intermediate Similarity	NPC254833
0.8317	Intermediate Similarity	NPC95172

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 NPC242240 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	1118
0.2-0.3	1291
0.3-0.4	2896
0.4-0.5	1933
0.5-0.6	1092
0.6-0.7	440
0.7-0.8	80
0.8-0.85	9
0.85-0.9	5
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9545	High Similarity	NPD1432	Clinical (unspecified phase)
0.9438	High Similarity	NPD2860	Approved
0.9438	High Similarity	NPD2859	Approved
0.9405	High Similarity	NPD111	Approved
0.9326	High Similarity	NPD2933	Approved
0.9326	High Similarity	NPD2934	Approved
0.913	High Similarity	NPD3020	Approved
0.9011	High Similarity	NPD844	Approved
0.9011	High Similarity	NPD1809	Phase 2
0.9	High Similarity	NPD845	Approved
0.8936	High Similarity	NPD940	Approved
0.8936	High Similarity	NPD846	Approved
0.871	High Similarity	NPD288	Approved
0.8438	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD9608	Approved
0.8367	Intermediate Similarity	NPD9610	Approved
0.8317	Intermediate Similarity	NPD3022	Approved
0.8317	Intermediate Similarity	NPD3021	Approved
0.82	Intermediate Similarity	NPD1445	Approved
0.82	Intermediate Similarity	NPD1444	Approved
0.8095	Intermediate Similarity	NPD9087	Approved
0.8061	Intermediate Similarity	NPD1242	Phase 1
0.8061	Intermediate Similarity	NPD3028	Approved
0.8	Intermediate Similarity	NPD2228	Approved
0.8	Intermediate Similarity	NPD2234	Approved
0.8	Intermediate Similarity	NPD2229	Approved
0.7961	Intermediate Similarity	NPD1792	Phase 2
0.7864	Intermediate Similarity	NPD2684	Approved
0.7816	Intermediate Similarity	NPD9294	Approved
0.781	Intermediate Similarity	NPD228	Approved
0.781	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD4750	Phase 3
0.7727	Intermediate Similarity	NPD9088	Approved
0.7723	Intermediate Similarity	NPD9500	Approved
0.7685	Intermediate Similarity	NPD255	Approved
0.7685	Intermediate Similarity	NPD256	Approved
0.7677	Intermediate Similarity	NPD9273	Approved
0.7664	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5303	Approved
0.7636	Intermediate Similarity	NPD5304	Approved
0.7636	Intermediate Similarity	NPD3091	Approved
0.7596	Intermediate Similarity	NPD2342	Discontinued
0.7593	Intermediate Similarity	NPD1793	Approved
0.7593	Intermediate Similarity	NPD1791	Approved
0.757	Intermediate Similarity	NPD821	Approved
0.757	Intermediate Similarity	NPD9379	Approved
0.757	Intermediate Similarity	NPD7843	Approved
0.757	Intermediate Similarity	NPD9377	Approved
0.757	Intermediate Similarity	NPD7635	Approved
0.7568	Intermediate Similarity	NPD4093	Discontinued
0.7545	Intermediate Similarity	NPD16	Approved
0.7545	Intermediate Similarity	NPD856	Approved
0.7523	Intermediate Similarity	NPD6671	Approved
0.75	Intermediate Similarity	NPD1751	Approved
0.75	Intermediate Similarity	NPD4589	Approved
0.75	Intermediate Similarity	NPD3019	Approved
0.75	Intermediate Similarity	NPD4059	Approved
0.75	Intermediate Similarity	NPD968	Approved
0.75	Intermediate Similarity	NPD2932	Approved
0.75	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5451	Approved
0.7431	Intermediate Similarity	NPD475	Phase 2
0.7429	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD9089	Approved
0.7387	Intermediate Similarity	NPD317	Approved
0.7387	Intermediate Similarity	NPD318	Approved
0.7368	Intermediate Similarity	NPD3092	Approved
0.7364	Intermediate Similarity	NPD7157	Approved
0.7297	Intermediate Similarity	NPD9568	Approved
0.7283	Intermediate Similarity	NPD9093	Approved
0.7273	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9614	Approved
0.7273	Intermediate Similarity	NPD9618	Approved
0.7264	Intermediate Similarity	NPD290	Approved
0.7257	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5535	Approved
0.7241	Intermediate Similarity	NPD6582	Phase 2
0.7241	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4659	Approved
0.7241	Intermediate Similarity	NPD6583	Phase 3
0.7222	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD9295	Approved
0.7193	Intermediate Similarity	NPD4626	Approved
0.7193	Intermediate Similarity	NPD3095	Discontinued
0.7193	Intermediate Similarity	NPD2668	Approved
0.7193	Intermediate Similarity	NPD2286	Discontinued
0.7193	Intermediate Similarity	NPD2667	Approved
0.7182	Intermediate Similarity	NPD5283	Phase 1
0.717	Intermediate Similarity	NPD3134	Approved
0.7168	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1548	Phase 1
0.7168	Intermediate Similarity	NPD9545	Approved
0.7158	Intermediate Similarity	NPD9073	Approved
0.7155	Intermediate Similarity	NPD2562	Approved
0.7155	Intermediate Similarity	NPD2561	Approved
0.713	Intermediate Similarity	NPD3421	Phase 3
0.713	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD3143	Discontinued
0.713	Intermediate Similarity	NPD3847	Discontinued
0.7119	Intermediate Similarity	NPD1134	Approved
0.7119	Intermediate Similarity	NPD1133	Approved
0.7119	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1129	Approved
0.7119	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1131	Approved
0.7119	Intermediate Similarity	NPD1135	Approved
0.7119	Intermediate Similarity	NPD3094	Phase 2
0.7119	Intermediate Similarity	NPD4103	Phase 2
0.7115	Intermediate Similarity	NPD4818	Approved
0.7115	Intermediate Similarity	NPD4817	Approved
0.7103	Intermediate Similarity	NPD1358	Approved
0.708	Intermediate Similarity	NPD9613	Approved
0.708	Intermediate Similarity	NPD9616	Approved
0.708	Intermediate Similarity	NPD9615	Approved
0.7069	Intermediate Similarity	NPD1610	Phase 2
0.7069	Intermediate Similarity	NPD422	Phase 1
0.7069	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2195	Approved
0.7059	Intermediate Similarity	NPD2194	Approved
0.7059	Intermediate Similarity	NPD6584	Phase 3
0.7048	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD9381	Approved
0.7043	Intermediate Similarity	NPD9384	Approved
0.7037	Intermediate Similarity	NPD9266	Approved
0.7037	Intermediate Similarity	NPD74	Approved
0.7019	Intermediate Similarity	NPD1616	Discontinued
0.7018	Intermediate Similarity	NPD7330	Discontinued
0.7018	Intermediate Similarity	NPD316	Approved
0.7018	Intermediate Similarity	NPD1759	Phase 1
0.7009	Intermediate Similarity	NPD3070	Discontinued
0.7	Intermediate Similarity	NPD5736	Approved
0.7	Intermediate Similarity	NPD159	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3637	Approved
0.7	Intermediate Similarity	NPD3635	Approved
0.7	Intermediate Similarity	NPD3636	Approved
0.6991	Remote Similarity	NPD3596	Phase 2
0.6991	Remote Similarity	NPD9493	Approved
0.6991	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.699	Remote Similarity	NPD9611	Approved
0.699	Remote Similarity	NPD9609	Approved
0.699	Remote Similarity	NPD9612	Approved
0.6975	Remote Similarity	NPD3053	Approved
0.6975	Remote Similarity	NPD3055	Approved
0.6957	Remote Similarity	NPD1357	Approved
0.6952	Remote Similarity	NPD855	Approved
0.6952	Remote Similarity	NPD854	Approved
0.6949	Remote Similarity	NPD1755	Approved
0.6949	Remote Similarity	NPD3685	Discontinued
0.6949	Remote Similarity	NPD9622	Approved
0.6944	Remote Similarity	NPD9267	Approved
0.6944	Remote Similarity	NPD9264	Approved
0.6944	Remote Similarity	NPD9263	Approved
0.6942	Remote Similarity	NPD2606	Approved
0.6942	Remote Similarity	NPD4908	Phase 1
0.6942	Remote Similarity	NPD2605	Approved
0.6939	Remote Similarity	NPD1101	Approved
0.6939	Remote Similarity	NPD9094	Approved
0.6937	Remote Similarity	NPD1138	Approved
0.693	Remote Similarity	NPD1758	Phase 1
0.6923	Remote Similarity	NPD1535	Discovery
0.6917	Remote Similarity	NPD7451	Discontinued
0.6917	Remote Similarity	NPD257	Approved
0.6917	Remote Similarity	NPD258	Approved
0.6897	Remote Similarity	NPD6516	Phase 2
0.6897	Remote Similarity	NPD5846	Approved
0.6891	Remote Similarity	NPD5311	Approved
0.6891	Remote Similarity	NPD5310	Approved
0.6891	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4229	Approved
0.6887	Remote Similarity	NPD4656	Approved
0.6887	Remote Similarity	NPD3680	Approved
0.6887	Remote Similarity	NPD4231	Approved
0.6887	Remote Similarity	NPD4658	Approved
0.6887	Remote Similarity	NPD3682	Approved
0.6887	Remote Similarity	NPD3683	Approved
0.6887	Remote Similarity	NPD3681	Approved
0.6885	Remote Similarity	NPD5156	Approved
0.6885	Remote Similarity	NPD3027	Phase 3
0.6885	Remote Similarity	NPD5155	Approved
0.6875	Remote Similarity	NPD1241	Discontinued
0.687	Remote Similarity	NPD6580	Approved
0.687	Remote Similarity	NPD6581	Approved
0.6869	Remote Similarity	NPD800	Approved
0.6864	Remote Similarity	NPD2232	Approved
0.6864	Remote Similarity	NPD2230	Approved
0.6864	Remote Similarity	NPD1481	Phase 2
0.6864	Remote Similarity	NPD2233	Approved
0.6863	Remote Similarity	NPD9296	Approved
0.686	Remote Similarity	NPD2861	Phase 2
0.6847	Remote Similarity	NPD1139	Approved
0.6847	Remote Similarity	NPD1137	Approved
0.6842	Remote Similarity	NPD7636	Approved
0.6842	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD3023	Approved
0.6838	Remote Similarity	NPD3026	Approved
0.6833	Remote Similarity	NPD1164	Approved
0.6829	Remote Similarity	NPD4907	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