NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	150.1
Volume:	173.841
LogP:	3.383
LogD:	3.398
LogS:	-2.634
# Rotatable Bonds:	3
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.702
Synthetic Accessibility Score:	1.422
Fsp3:	0.4
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:	-4.366
MDCK Permeability:	2.0188908820273355e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.874
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.568
Plasma Protein Binding (PPB):	92.29537963867188%
Volume Distribution (VD):	1.888
Pgp-substrate:	8.85508918762207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.807
CYP2C19-inhibitor:	0.926
CYP2C19-substrate:	0.38
CYP2C9-inhibitor:	0.658
CYP2C9-substrate:	0.924
CYP2D6-inhibitor:	0.766
CYP2D6-substrate:	0.752
CYP3A4-inhibitor:	0.097
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	13.238
Half-life (T1/2):	0.813

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.031
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.337
Maximum Recommended Daily Dose:	0.043
Skin Sensitization:	0.876
Carcinogencity:	0.166
Eye Corrosion:	0.968
Eye Irritation:	0.992
Respiratory Toxicity:	0.236

Download Data

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

Natural Product: NPC23167

Natural Product ID:	NPC23167
*Common Name:**	4-Butylphenol
IUPAC Name:	4-butylphenol
Synonyms:	4-Butyl-Phenol; 4-Butylphenol; 4-N-Butylphenol; 4-N-Ethylphenol
Standard InCHIKey:	CYYZDBDROVLTJU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H14O/c1-2-3-4-9-5-7-10(11)8-6-9/h5-8,11H,2-4H2,1H3
SMILES:	CCCCc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL152295
PubChem CID:	15420
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
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB10.140]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB2010.000-3252]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	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]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	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	4

Activity Type	# Activity
Cell Line	2
Individual Protein	5
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1817	Individual Protein	Aryl sulfotransferase	Rattus norvegicus	Km	=	5000.0	nM	PMID[479555]
NPT1817	Individual Protein	Aryl sulfotransferase	Rattus norvegicus	Vmax	=	296.0	nM min-1	PMID[479555]
NPT1817	Individual Protein	Aryl sulfotransferase	Rattus norvegicus	Ratio	=	2230.0	n.a.	PMID[479555]
NPT137	Cell Line	L1210	Mus musculus	log(1/ID50)	=	4.33	n.a.	PMID[479556]
NPT137	Cell Line	L1210	Mus musculus	Activity	<	15.0	%	PMID[479556]
NPT27	Others	Unspecified		log Ks	=	3.97	n.a.	PMID[479557]
NPT901	Individual Protein	UDP-glucuronosyltransferase 1-1	Homo sapiens	Activity	=	40.0	pm/min/mg	PMID[479558]
NPT2	Others	Unspecified		Potency	n.a.	48508.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68519.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30606.7	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	61576.9	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 NPC23167 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	234
0.1-0.2	2444
0.2-0.3	7197
0.3-0.4	12104
0.4-0.5	6742
0.5-0.6	9078
0.6-0.7	3690
0.7-0.8	881
0.8-0.85	205
0.85-0.9	71
0.9-0.95	36
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.988	High Similarity	NPC113460
0.988	High Similarity	NPC25493
0.9878	High Similarity	NPC197783
0.9762	High Similarity	NPC258219
0.9762	High Similarity	NPC242240
0.9762	High Similarity	NPC280347
0.9762	High Similarity	NPC318325
0.9762	High Similarity	NPC177420
0.9762	High Similarity	NPC123273
0.9756	High Similarity	NPC175313
0.9756	High Similarity	NPC248817
0.9647	High Similarity	NPC55561
0.9634	High Similarity	NPC265146
0.9634	High Similarity	NPC124436
0.9535	High Similarity	NPC304541
0.9524	High Similarity	NPC307235
0.9524	High Similarity	NPC407
0.9524	High Similarity	NPC184169
0.9425	High Similarity	NPC138117
0.9425	High Similarity	NPC325292
0.9419	High Similarity	NPC300017
0.9412	High Similarity	NPC27974
0.9405	High Similarity	NPC155393
0.9318	High Similarity	NPC316301
0.9318	High Similarity	NPC27323
0.931	High Similarity	NPC45040
0.931	High Similarity	NPC204210
0.931	High Similarity	NPC155908
0.9302	High Similarity	NPC98772
0.9286	High Similarity	NPC286904
0.9213	High Similarity	NPC26244
0.9213	High Similarity	NPC8392
0.9213	High Similarity	NPC313650
0.9186	High Similarity	NPC104216
0.9111	High Similarity	NPC473388
0.9101	High Similarity	NPC151715
0.9101	High Similarity	NPC128062
0.9091	High Similarity	NPC306074
0.9091	High Similarity	NPC270547
0.908	High Similarity	NPC70436
0.9059	High Similarity	NPC150837
0.9011	High Similarity	NPC77492
0.9011	High Similarity	NPC260000
0.9011	High Similarity	NPC225464
0.9	High Similarity	NPC274678
0.8989	High Similarity	NPC94139
0.8989	High Similarity	NPC147284
0.8989	High Similarity	NPC210497
0.8989	High Similarity	NPC306884
0.8989	High Similarity	NPC55903
0.8989	High Similarity	NPC3358
0.8989	High Similarity	NPC181709
0.8989	High Similarity	NPC162314
0.8977	High Similarity	NPC192
0.8977	High Similarity	NPC300478
0.8913	High Similarity	NPC280869
0.8913	High Similarity	NPC92730
0.8913	High Similarity	NPC80027
0.8913	High Similarity	NPC252821
0.8913	High Similarity	NPC122005
0.8913	High Similarity	NPC128723
0.8901	High Similarity	NPC202986
0.8889	High Similarity	NPC152415
0.8889	High Similarity	NPC245187
0.8876	High Similarity	NPC231150
0.8817	High Similarity	NPC225506
0.8804	High Similarity	NPC32674
0.8804	High Similarity	NPC109955
0.8804	High Similarity	NPC107619
0.8791	High Similarity	NPC144682
0.8778	High Similarity	NPC271440
0.875	High Similarity	NPC19680
0.871	High Similarity	NPC245561
0.871	High Similarity	NPC51333
0.871	High Similarity	NPC132078
0.871	High Similarity	NPC78119
0.871	High Similarity	NPC216468
0.8696	High Similarity	NPC292730
0.8696	High Similarity	NPC259512
0.8696	High Similarity	NPC132271
0.8696	High Similarity	NPC216520
0.8696	High Similarity	NPC82664
0.8696	High Similarity	NPC312132
0.8681	High Similarity	NPC81010
0.8681	High Similarity	NPC289769
0.8681	High Similarity	NPC76938
0.8681	High Similarity	NPC32977
0.8632	High Similarity	NPC196479
0.8617	High Similarity	NPC213730
0.8617	High Similarity	NPC155847
0.8617	High Similarity	NPC211885
0.8617	High Similarity	NPC52472
0.8617	High Similarity	NPC289381
0.8602	High Similarity	NPC79241
0.8602	High Similarity	NPC6597
0.8602	High Similarity	NPC152097
0.8602	High Similarity	NPC474073
0.8587	High Similarity	NPC107522
0.8587	High Similarity	NPC222146
0.8587	High Similarity	NPC286006
0.8587	High Similarity	NPC32714
0.8571	High Similarity	NPC29373
0.8556	High Similarity	NPC47950
0.8556	High Similarity	NPC151764
0.8556	High Similarity	NPC312304
0.8542	High Similarity	NPC120719
0.8526	High Similarity	NPC91461
0.8526	High Similarity	NPC40258
0.8526	High Similarity	NPC7686
0.8526	High Similarity	NPC110764
0.8511	High Similarity	NPC33675
0.8511	High Similarity	NPC100870
0.8511	High Similarity	NPC299762
0.8511	High Similarity	NPC171843
0.8511	High Similarity	NPC260775
0.8511	High Similarity	NPC125732
0.8471	Intermediate Similarity	NPC133050
0.8462	Intermediate Similarity	NPC321956
0.8454	Intermediate Similarity	NPC138942
0.8454	Intermediate Similarity	NPC303141
0.8454	Intermediate Similarity	NPC154899
0.8454	Intermediate Similarity	NPC233396
0.8438	Intermediate Similarity	NPC168829
0.8438	Intermediate Similarity	NPC135784
0.8438	Intermediate Similarity	NPC178902
0.8438	Intermediate Similarity	NPC470202
0.8421	Intermediate Similarity	NPC12931
0.8421	Intermediate Similarity	NPC72729
0.8421	Intermediate Similarity	NPC248396
0.8421	Intermediate Similarity	NPC48730
0.8421	Intermediate Similarity	NPC70677
0.8421	Intermediate Similarity	NPC166761
0.8421	Intermediate Similarity	NPC129373
0.8421	Intermediate Similarity	NPC174911
0.8421	Intermediate Similarity	NPC130756
0.8421	Intermediate Similarity	NPC253746
0.8404	Intermediate Similarity	NPC201967
0.8404	Intermediate Similarity	NPC156313
0.8404	Intermediate Similarity	NPC475078
0.8387	Intermediate Similarity	NPC246679
0.8372	Intermediate Similarity	NPC87299
0.8372	Intermediate Similarity	NPC99394
0.8372	Intermediate Similarity	NPC103326
0.8372	Intermediate Similarity	NPC329319
0.8367	Intermediate Similarity	NPC271274
0.8367	Intermediate Similarity	NPC477814
0.8367	Intermediate Similarity	NPC92623
0.8367	Intermediate Similarity	NPC135464
0.8367	Intermediate Similarity	NPC113457
0.8352	Intermediate Similarity	NPC71853
0.8351	Intermediate Similarity	NPC119860
0.8351	Intermediate Similarity	NPC120693
0.8351	Intermediate Similarity	NPC327811
0.8351	Intermediate Similarity	NPC261573
0.8351	Intermediate Similarity	NPC12278
0.8351	Intermediate Similarity	NPC471511
0.8351	Intermediate Similarity	NPC254965
0.8351	Intermediate Similarity	NPC8931
0.8351	Intermediate Similarity	NPC288411
0.8351	Intermediate Similarity	NPC30506
0.8333	Intermediate Similarity	NPC472585
0.8333	Intermediate Similarity	NPC471578
0.8333	Intermediate Similarity	NPC252105
0.8333	Intermediate Similarity	NPC101025
0.8316	Intermediate Similarity	NPC275104
0.8316	Intermediate Similarity	NPC131587
0.8316	Intermediate Similarity	NPC130193
0.8298	Intermediate Similarity	NPC283711
0.8293	Intermediate Similarity	NPC100980
0.8283	Intermediate Similarity	NPC226699
0.8283	Intermediate Similarity	NPC228737
0.8265	Intermediate Similarity	NPC474839
0.8265	Intermediate Similarity	NPC243677
0.8265	Intermediate Similarity	NPC13495
0.8265	Intermediate Similarity	NPC239291
0.8256	Intermediate Similarity	NPC117180
0.8247	Intermediate Similarity	NPC235762
0.8247	Intermediate Similarity	NPC302219
0.8247	Intermediate Similarity	NPC242342
0.8247	Intermediate Similarity	NPC94351
0.8247	Intermediate Similarity	NPC71002
0.8247	Intermediate Similarity	NPC304638
0.8247	Intermediate Similarity	NPC62351
0.8247	Intermediate Similarity	NPC313030
0.8247	Intermediate Similarity	NPC249828
0.8247	Intermediate Similarity	NPC146798
0.8247	Intermediate Similarity	NPC471228
0.8247	Intermediate Similarity	NPC108497
0.8247	Intermediate Similarity	NPC53051
0.8247	Intermediate Similarity	NPC85479
0.8247	Intermediate Similarity	NPC305205
0.8247	Intermediate Similarity	NPC168303
0.8247	Intermediate Similarity	NPC24404
0.8247	Intermediate Similarity	NPC106396
0.8247	Intermediate Similarity	NPC222522
0.8242	Intermediate Similarity	NPC177844
0.8242	Intermediate Similarity	NPC259134
0.8242	Intermediate Similarity	NPC8002
0.8242	Intermediate Similarity	NPC99886
0.8229	Intermediate Similarity	NPC248573

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 NPC23167 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	1129
0.2-0.3	1356
0.3-0.4	2885
0.4-0.5	1921
0.5-0.6	1056
0.6-0.7	441
0.7-0.8	69
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
0.9634	High Similarity	NPD111	Approved
0.9318	High Similarity	NPD2933	Approved
0.9318	High Similarity	NPD1432	Clinical (unspecified phase)
0.9318	High Similarity	NPD2934	Approved
0.9213	High Similarity	NPD2860	Approved
0.9213	High Similarity	NPD2859	Approved
0.8913	High Similarity	NPD3020	Approved
0.8791	High Similarity	NPD844	Approved
0.8791	High Similarity	NPD1809	Phase 2
0.8778	High Similarity	NPD845	Approved
0.8723	High Similarity	NPD940	Approved
0.8723	High Similarity	NPD846	Approved
0.8696	High Similarity	NPD288	Approved
0.8542	High Similarity	NPD9610	Approved
0.8542	High Similarity	NPD9608	Approved
0.8421	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD9087	Approved
0.8229	Intermediate Similarity	NPD1242	Phase 1
0.8119	Intermediate Similarity	NPD3021	Approved
0.8119	Intermediate Similarity	NPD3022	Approved
0.8041	Intermediate Similarity	NPD3028	Approved
0.8	Intermediate Similarity	NPD1445	Approved
0.8	Intermediate Similarity	NPD9294	Approved
0.8	Intermediate Similarity	NPD1444	Approved
0.7961	Intermediate Similarity	NPD228	Approved
0.7941	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD9088	Approved
0.7835	Intermediate Similarity	NPD9273	Approved
0.781	Intermediate Similarity	NPD2228	Approved
0.781	Intermediate Similarity	NPD2229	Approved
0.781	Intermediate Similarity	NPD2234	Approved
0.7767	Intermediate Similarity	NPD1792	Phase 2
0.7714	Intermediate Similarity	NPD9379	Approved
0.7714	Intermediate Similarity	NPD9377	Approved
0.77	Intermediate Similarity	NPD9500	Approved
0.767	Intermediate Similarity	NPD2684	Approved
0.7664	Intermediate Similarity	NPD256	Approved
0.7664	Intermediate Similarity	NPD255	Approved
0.7647	Intermediate Similarity	NPD968	Approved
0.7619	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD4750	Phase 3
0.7573	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD2342	Discontinued
0.7556	Intermediate Similarity	NPD9089	Approved
0.7547	Intermediate Similarity	NPD821	Approved
0.7523	Intermediate Similarity	NPD856	Approved
0.7523	Intermediate Similarity	NPD16	Approved
0.7523	Intermediate Similarity	NPD317	Approved
0.7523	Intermediate Similarity	NPD318	Approved
0.7477	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5303	Approved
0.7455	Intermediate Similarity	NPD5304	Approved
0.7455	Intermediate Similarity	NPD3091	Approved
0.7444	Intermediate Similarity	NPD9093	Approved
0.7431	Intermediate Similarity	NPD9568	Approved
0.7407	Intermediate Similarity	NPD1791	Approved
0.7407	Intermediate Similarity	NPD1793	Approved
0.7407	Intermediate Similarity	NPD9618	Approved
0.7407	Intermediate Similarity	NPD9614	Approved
0.7407	Intermediate Similarity	NPD475	Phase 2
0.7404	Intermediate Similarity	NPD290	Approved
0.7387	Intermediate Similarity	NPD4093	Discontinued
0.7383	Intermediate Similarity	NPD7635	Approved
0.7383	Intermediate Similarity	NPD7843	Approved
0.7368	Intermediate Similarity	NPD9295	Approved
0.7358	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6671	Approved
0.7321	Intermediate Similarity	NPD1751	Approved
0.7321	Intermediate Similarity	NPD4059	Approved
0.7321	Intermediate Similarity	NPD2932	Approved
0.7321	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3019	Approved
0.7321	Intermediate Similarity	NPD4589	Approved
0.7312	Intermediate Similarity	NPD9073	Approved
0.7297	Intermediate Similarity	NPD9545	Approved
0.7297	Intermediate Similarity	NPD1548	Phase 1
0.7264	Intermediate Similarity	NPD5451	Approved
0.7248	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD9616	Approved
0.7207	Intermediate Similarity	NPD9613	Approved
0.7207	Intermediate Similarity	NPD9615	Approved
0.7193	Intermediate Similarity	NPD422	Phase 1
0.7193	Intermediate Similarity	NPD3092	Approved
0.7182	Intermediate Similarity	NPD7157	Approved
0.717	Intermediate Similarity	NPD74	Approved
0.717	Intermediate Similarity	NPD9266	Approved
0.7168	Intermediate Similarity	NPD2286	Discontinued
0.7168	Intermediate Similarity	NPD9381	Approved
0.7168	Intermediate Similarity	NPD9384	Approved
0.7143	Intermediate Similarity	NPD3134	Approved
0.7143	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD316	Approved
0.713	Intermediate Similarity	NPD2562	Approved
0.713	Intermediate Similarity	NPD2561	Approved
0.7129	Intermediate Similarity	NPD9609	Approved
0.7129	Intermediate Similarity	NPD9611	Approved
0.7129	Intermediate Similarity	NPD9612	Approved
0.7117	Intermediate Similarity	NPD9493	Approved
0.7105	Intermediate Similarity	NPD3421	Phase 3
0.7083	Intermediate Similarity	NPD9094	Approved
0.708	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1358	Approved
0.7075	Intermediate Similarity	NPD9263	Approved
0.7075	Intermediate Similarity	NPD9267	Approved
0.7075	Intermediate Similarity	NPD9264	Approved
0.7069	Intermediate Similarity	NPD9622	Approved
0.7069	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6583	Phase 3
0.7069	Intermediate Similarity	NPD4659	Approved
0.7069	Intermediate Similarity	NPD6582	Phase 2
0.7064	Intermediate Similarity	NPD5535	Approved
0.7043	Intermediate Similarity	NPD1610	Phase 2
0.7043	Intermediate Similarity	NPD1535	Discovery
0.7018	Intermediate Similarity	NPD3095	Discontinued
0.7018	Intermediate Similarity	NPD4626	Approved
0.7018	Intermediate Similarity	NPD2667	Approved
0.7018	Intermediate Similarity	NPD2668	Approved
0.7009	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5283	Phase 1
0.7	Intermediate Similarity	NPD9296	Approved
0.7	Intermediate Similarity	NPD1241	Discontinued
0.6991	Remote Similarity	NPD1759	Phase 1
0.699	Remote Similarity	NPD1616	Discontinued
0.6983	Remote Similarity	NPD1481	Phase 2
0.697	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD9495	Approved
0.6957	Remote Similarity	NPD3143	Discontinued
0.6957	Remote Similarity	NPD3847	Discontinued
0.6957	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD9244	Approved
0.6949	Remote Similarity	NPD3094	Phase 2
0.6949	Remote Similarity	NPD3053	Approved
0.6949	Remote Similarity	NPD1134	Approved
0.6949	Remote Similarity	NPD4103	Phase 2
0.6949	Remote Similarity	NPD1131	Approved
0.6949	Remote Similarity	NPD1135	Approved
0.6949	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD1129	Approved
0.6949	Remote Similarity	NPD3055	Approved
0.6949	Remote Similarity	NPD1133	Approved
0.693	Remote Similarity	NPD1357	Approved
0.6923	Remote Similarity	NPD855	Approved
0.6923	Remote Similarity	NPD4817	Approved
0.6923	Remote Similarity	NPD854	Approved
0.6923	Remote Similarity	NPD4818	Approved
0.6915	Remote Similarity	NPD9491	Approved
0.6903	Remote Similarity	NPD1758	Phase 1
0.6897	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2194	Approved
0.6891	Remote Similarity	NPD9620	Approved
0.6891	Remote Similarity	NPD7451	Discontinued
0.6891	Remote Similarity	NPD258	Approved
0.6891	Remote Similarity	NPD2195	Approved
0.6891	Remote Similarity	NPD9619	Approved
0.6891	Remote Similarity	NPD9621	Approved
0.6891	Remote Similarity	NPD6584	Phase 3
0.6891	Remote Similarity	NPD257	Approved
0.6882	Remote Similarity	NPD9250	Approved
0.6875	Remote Similarity	NPD709	Approved
0.6864	Remote Similarity	NPD5311	Approved
0.6864	Remote Similarity	NPD5310	Approved
0.6857	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7330	Discontinued
0.6842	Remote Similarity	NPD1894	Discontinued
0.6838	Remote Similarity	NPD3070	Discontinued
0.6833	Remote Similarity	NPD5736	Approved
0.6833	Remote Similarity	NPD3636	Approved
0.6833	Remote Similarity	NPD3635	Approved
0.6833	Remote Similarity	NPD3637	Approved
0.6814	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD3596	Phase 2
0.6807	Remote Similarity	NPD1164	Approved
0.6792	Remote Similarity	NPD311	Approved
0.6792	Remote Similarity	NPD315	Approved
0.6792	Remote Similarity	NPD10	Approved
0.6792	Remote Similarity	NPD310	Approved
0.6792	Remote Similarity	NPD309	Approved
0.6792	Remote Similarity	NPD314	Approved
0.6786	Remote Similarity	NPD497	Approved
0.678	Remote Similarity	NPD1755	Approved
0.678	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3685	Discontinued
0.678	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD4908	Phase 1
0.6777	Remote Similarity	NPD2606	Approved
0.6777	Remote Similarity	NPD2605	Approved
0.6768	Remote Similarity	NPD9258	Approved
0.6768	Remote Similarity	NPD9256	Approved
0.6757	Remote Similarity	NPD1138	Approved
0.6752	Remote Similarity	NPD1201	Approved
0.6735	Remote Similarity	NPD1101	Approved
0.6729	Remote Similarity	NPD9697	Approved
0.6724	Remote Similarity	NPD6516	Phase 2
0.6724	Remote Similarity	NPD5846	Approved
0.6723	Remote Similarity	NPD1283	Approved
0.6721	Remote Similarity	NPD3136	Phase 2

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