NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	150.1
Volume:	173.841
LogP:	3.41
LogD:	3.272
LogS:	-2.531
# Rotatable Bonds:	2
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	2.082
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:	-4.361
MDCK Permeability:	1.8442773580318317e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.292
30% Bioavailability (F30%):	0.715

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.538
Plasma Protein Binding (PPB):	92.02079010009766%
Volume Distribution (VD):	2.47
Pgp-substrate:	9.465142250061035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.92
CYP2C19-inhibitor:	0.87
CYP2C19-substrate:	0.561
CYP2C9-inhibitor:	0.647
CYP2C9-substrate:	0.932
CYP2D6-inhibitor:	0.463
CYP2D6-substrate:	0.7
CYP3A4-inhibitor:	0.225
CYP3A4-substrate:	0.429

ADMET: Excretion

Clearance (CL):	14.046
Half-life (T1/2):	0.711

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.036
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.35
Maximum Recommended Daily Dose:	0.229
Skin Sensitization:	0.505
Carcinogencity:	0.234
Eye Corrosion:	0.949
Eye Irritation:	0.992
Respiratory Toxicity:	0.5

Download Data

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

Natural Product: NPC304541

Natural Product ID:	NPC304541
*Common Name:**	4-Butan-2-Ylphenol
IUPAC Name:	4-butan-2-ylphenol
Synonyms:	4-Sec-Butylphenol
Standard InCHIKey:	ZUTYZAFDFLLILI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H14O/c1-3-8(2)9-4-6-10(11)7-5-9/h4-8,11H,3H2,1-2H3
SMILES:	CCC(C)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL29398
PubChem CID:	7453
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002811] Phenylpropanes

*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]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	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]
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
IC50	1
LD50	1
Others	1
Potency	17

Activity Type	# Activity
Individual Protein	5
Organism	1
Others	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT299	Individual Protein	Androgen Receptor	Rattus norvegicus	IC50	=	85113.8	nM	PMID[558007]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	54482.7	nM	PMID[558009]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[558009]
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	55438.8	nM	PubChem BioAssay data set
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	40.0	mg.kg-1	PMID[558006]
NPT27	Others	Unspecified		log Ks	=	4.18	n.a.	PMID[558008]
NPT2	Others	Unspecified		Potency	n.a.	55438.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43641.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	77663.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27556.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24336.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	15496	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	13810.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43277.1	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	55438.8	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 NPC304541 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	260
0.1-0.2	1926
0.2-0.3	5115
0.3-0.4	13275
0.4-0.5	6914
0.5-0.6	9596
0.6-0.7	4274
0.7-0.8	1012
0.8-0.85	201
0.85-0.9	71
0.9-0.95	44
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC258219
0.9551	High Similarity	NPC27323
0.9551	High Similarity	NPC316301
0.9545	High Similarity	NPC155908
0.954	High Similarity	NPC318325
0.954	High Similarity	NPC123273
0.954	High Similarity	NPC242240
0.9535	High Similarity	NPC23167
0.9451	High Similarity	NPC77492
0.9444	High Similarity	NPC8392
0.9425	High Similarity	NPC25493
0.9425	High Similarity	NPC113460
0.9419	High Similarity	NPC197783
0.9318	High Similarity	NPC177420
0.9318	High Similarity	NPC280347
0.9302	High Similarity	NPC248817
0.9302	High Similarity	NPC175313
0.9239	High Similarity	NPC225464
0.9222	High Similarity	NPC55903
0.9213	High Similarity	NPC55561
0.9205	High Similarity	NPC27974
0.9186	High Similarity	NPC124436
0.9186	High Similarity	NPC265146
0.914	High Similarity	NPC122005
0.914	High Similarity	NPC252821
0.914	High Similarity	NPC92730
0.913	High Similarity	NPC82664
0.913	High Similarity	NPC312132
0.913	High Similarity	NPC259512
0.913	High Similarity	NPC292730
0.913	High Similarity	NPC216520
0.913	High Similarity	NPC132271
0.913	High Similarity	NPC473388
0.9121	High Similarity	NPC152415
0.9111	High Similarity	NPC45040
0.9111	High Similarity	NPC204210
0.9111	High Similarity	NPC306074
0.9091	High Similarity	NPC407
0.9091	High Similarity	NPC184169
0.9091	High Similarity	NPC307235
0.9043	High Similarity	NPC225506
0.9032	High Similarity	NPC79241
0.9032	High Similarity	NPC6597
0.9022	High Similarity	NPC26244
0.9022	High Similarity	NPC274678
0.9011	High Similarity	NPC162314
0.9011	High Similarity	NPC147284
0.9011	High Similarity	NPC94139
0.9011	High Similarity	NPC210497
0.9011	High Similarity	NPC306884
0.9011	High Similarity	NPC3358
0.9011	High Similarity	NPC138117
0.9011	High Similarity	NPC325292
0.9	High Similarity	NPC300017
0.9	High Similarity	NPC192
0.8977	High Similarity	NPC155393
0.8925	High Similarity	NPC202986
0.8913	High Similarity	NPC128062
0.8913	High Similarity	NPC151715
0.8913	High Similarity	NPC245187
0.8889	High Similarity	NPC98772
0.8889	High Similarity	NPC70436
0.8864	High Similarity	NPC286904
0.8864	High Similarity	NPC150837
0.8842	High Similarity	NPC72729
0.8842	High Similarity	NPC211885
0.883	High Similarity	NPC32674
0.8817	High Similarity	NPC313650
0.8817	High Similarity	NPC222146
0.8817	High Similarity	NPC144682
0.8804	High Similarity	NPC271440
0.8778	High Similarity	NPC19680
0.8778	High Similarity	NPC104216
0.8776	High Similarity	NPC271274
0.8763	High Similarity	NPC120719
0.8737	High Similarity	NPC128723
0.8737	High Similarity	NPC33675
0.8737	High Similarity	NPC299762
0.871	High Similarity	NPC76938
0.871	High Similarity	NPC289769
0.8696	High Similarity	NPC270547
0.8696	High Similarity	NPC231150
0.8673	High Similarity	NPC138942
0.8673	High Similarity	NPC239291
0.866	High Similarity	NPC168829
0.8632	High Similarity	NPC260000
0.8632	High Similarity	NPC474073
0.8632	High Similarity	NPC109955
0.8617	High Similarity	NPC32714
0.8602	High Similarity	NPC181709
0.86	High Similarity	NPC11554
0.8587	High Similarity	NPC300478
0.8586	High Similarity	NPC21594
0.8586	High Similarity	NPC477814
0.8586	High Similarity	NPC248904
0.8571	High Similarity	NPC475580
0.8571	High Similarity	NPC254965
0.8571	High Similarity	NPC327811
0.8571	High Similarity	NPC475225
0.8571	High Similarity	NPC288411
0.8557	High Similarity	NPC252105
0.8557	High Similarity	NPC12221
0.8542	High Similarity	NPC280869
0.8542	High Similarity	NPC216468
0.8542	High Similarity	NPC80027
0.8542	High Similarity	NPC132078
0.8542	High Similarity	NPC78119
0.8542	High Similarity	NPC51333
0.8515	High Similarity	NPC228343
0.8515	High Similarity	NPC254833
0.8515	High Similarity	NPC58865
0.8506	High Similarity	NPC133050
0.85	High Similarity	NPC228737
0.85	High Similarity	NPC151477
0.8469	Intermediate Similarity	NPC471228
0.8469	Intermediate Similarity	NPC235762
0.8469	Intermediate Similarity	NPC196479
0.8454	Intermediate Similarity	NPC48730
0.8454	Intermediate Similarity	NPC129373
0.8454	Intermediate Similarity	NPC174911
0.8454	Intermediate Similarity	NPC248396
0.8454	Intermediate Similarity	NPC213730
0.8438	Intermediate Similarity	NPC107619
0.8438	Intermediate Similarity	NPC156313
0.8438	Intermediate Similarity	NPC152097
0.8431	Intermediate Similarity	NPC13482
0.8431	Intermediate Similarity	NPC296683
0.8427	Intermediate Similarity	NPC168855
0.8421	Intermediate Similarity	NPC107522
0.8416	Intermediate Similarity	NPC201959
0.8404	Intermediate Similarity	NPC29373
0.84	Intermediate Similarity	NPC54765
0.8387	Intermediate Similarity	NPC312304
0.8384	Intermediate Similarity	NPC471511
0.8384	Intermediate Similarity	NPC30506
0.8384	Intermediate Similarity	NPC323810
0.8367	Intermediate Similarity	NPC7686
0.8367	Intermediate Similarity	NPC471578
0.8367	Intermediate Similarity	NPC101025
0.8367	Intermediate Similarity	NPC51015
0.8367	Intermediate Similarity	NPC91461
0.8367	Intermediate Similarity	NPC110764
0.8367	Intermediate Similarity	NPC40258
0.8351	Intermediate Similarity	NPC245561
0.8351	Intermediate Similarity	NPC260775
0.835	Intermediate Similarity	NPC322753
0.8333	Intermediate Similarity	NPC474354
0.8317	Intermediate Similarity	NPC66834
0.8317	Intermediate Similarity	NPC320439
0.8316	Intermediate Similarity	NPC81010
0.8316	Intermediate Similarity	NPC32977
0.83	Intermediate Similarity	NPC154899
0.83	Intermediate Similarity	NPC303141
0.83	Intermediate Similarity	NPC233396
0.83	Intermediate Similarity	NPC117115
0.83	Intermediate Similarity	NPC47284
0.8283	Intermediate Similarity	NPC94351
0.8283	Intermediate Similarity	NPC269212
0.8283	Intermediate Similarity	NPC242342
0.8283	Intermediate Similarity	NPC146798
0.8283	Intermediate Similarity	NPC135784
0.8283	Intermediate Similarity	NPC62351
0.8283	Intermediate Similarity	NPC71002
0.8283	Intermediate Similarity	NPC470202
0.8283	Intermediate Similarity	NPC313030
0.8283	Intermediate Similarity	NPC249828
0.8283	Intermediate Similarity	NPC53051
0.8283	Intermediate Similarity	NPC108497
0.8283	Intermediate Similarity	NPC24404
0.8283	Intermediate Similarity	NPC168303
0.8283	Intermediate Similarity	NPC85479
0.8283	Intermediate Similarity	NPC302219
0.8283	Intermediate Similarity	NPC106396
0.8283	Intermediate Similarity	NPC222522
0.8269	Intermediate Similarity	NPC228425
0.8269	Intermediate Similarity	NPC250323
0.8265	Intermediate Similarity	NPC130756
0.8265	Intermediate Similarity	NPC12931
0.8265	Intermediate Similarity	NPC294741
0.8265	Intermediate Similarity	NPC10588
0.8265	Intermediate Similarity	NPC166761
0.8265	Intermediate Similarity	NPC52472
0.8265	Intermediate Similarity	NPC70677
0.8265	Intermediate Similarity	NPC289381
0.8265	Intermediate Similarity	NPC155847
0.8252	Intermediate Similarity	NPC141782
0.8247	Intermediate Similarity	NPC475078
0.8242	Intermediate Similarity	NPC93843
0.8242	Intermediate Similarity	NPC474211
0.8235	Intermediate Similarity	NPC64586
0.8235	Intermediate Similarity	NPC262365
0.8235	Intermediate Similarity	NPC95344
0.8235	Intermediate Similarity	NPC75440
0.8229	Intermediate Similarity	NPC286006
0.8218	Intermediate Similarity	NPC113457
0.8218	Intermediate Similarity	NPC135464
0.8218	Intermediate Similarity	NPC92623
0.8218	Intermediate Similarity	NPC53740
0.8218	Intermediate Similarity	NPC310456
0.82	Intermediate Similarity	NPC119860

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 NPC304541 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	1057
0.2-0.3	1282
0.3-0.4	2899
0.4-0.5	1921
0.5-0.6	1124
0.6-0.7	466
0.7-0.8	80
0.8-0.85	6
0.85-0.9	6
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9551	High Similarity	NPD1432	Clinical (unspecified phase)
0.9348	High Similarity	NPD3020	Approved
0.9186	High Similarity	NPD111	Approved
0.913	High Similarity	NPD288	Approved
0.9022	High Similarity	NPD2860	Approved
0.9022	High Similarity	NPD2859	Approved
0.9011	High Similarity	NPD845	Approved
0.8913	High Similarity	NPD2933	Approved
0.8913	High Similarity	NPD2934	Approved
0.8817	High Similarity	NPD1809	Phase 2
0.8817	High Similarity	NPD844	Approved
0.8646	High Similarity	NPD289	Clinical (unspecified phase)
0.8557	High Similarity	NPD940	Approved
0.8557	High Similarity	NPD846	Approved
0.8515	High Similarity	NPD3022	Approved
0.8515	High Similarity	NPD3021	Approved
0.84	Intermediate Similarity	NPD1445	Approved
0.84	Intermediate Similarity	NPD1444	Approved
0.82	Intermediate Similarity	NPD9610	Approved
0.82	Intermediate Similarity	NPD9608	Approved
0.819	Intermediate Similarity	NPD2234	Approved
0.819	Intermediate Similarity	NPD2228	Approved
0.819	Intermediate Similarity	NPD2229	Approved
0.8155	Intermediate Similarity	NPD1792	Phase 2
0.8081	Intermediate Similarity	NPD1242	Phase 1
0.7981	Intermediate Similarity	NPD4750	Phase 3
0.7907	Intermediate Similarity	NPD9087	Approved
0.783	Intermediate Similarity	NPD228	Approved
0.7818	Intermediate Similarity	NPD3091	Approved
0.7788	Intermediate Similarity	NPD2342	Discontinued
0.7778	Intermediate Similarity	NPD475	Phase 2
0.7757	Intermediate Similarity	NPD7635	Approved
0.7748	Intermediate Similarity	NPD4093	Discontinued
0.7745	Intermediate Similarity	NPD9500	Approved
0.7723	Intermediate Similarity	NPD3028	Approved
0.7679	Intermediate Similarity	NPD4059	Approved
0.7679	Intermediate Similarity	NPD1751	Approved
0.7679	Intermediate Similarity	NPD2932	Approved
0.7679	Intermediate Similarity	NPD3019	Approved
0.7664	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD5303	Approved
0.7658	Intermediate Similarity	NPD5304	Approved
0.7642	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD9294	Approved
0.7615	Intermediate Similarity	NPD1793	Approved
0.7615	Intermediate Similarity	NPD1791	Approved
0.7593	Intermediate Similarity	NPD9377	Approved
0.7593	Intermediate Similarity	NPD9379	Approved
0.7556	Intermediate Similarity	NPD9088	Approved
0.7547	Intermediate Similarity	NPD2684	Approved
0.7545	Intermediate Similarity	NPD256	Approved
0.7545	Intermediate Similarity	NPD255	Approved
0.7544	Intermediate Similarity	NPD3092	Approved
0.7525	Intermediate Similarity	NPD9273	Approved
0.7523	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD4589	Approved
0.7455	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1610	Phase 2
0.7387	Intermediate Similarity	NPD6671	Approved
0.7387	Intermediate Similarity	NPD7157	Approved
0.7368	Intermediate Similarity	NPD2668	Approved
0.7368	Intermediate Similarity	NPD3095	Discontinued
0.7368	Intermediate Similarity	NPD2667	Approved
0.7368	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2286	Discontinued
0.7364	Intermediate Similarity	NPD5283	Phase 1
0.7358	Intermediate Similarity	NPD968	Approved
0.7297	Intermediate Similarity	NPD9614	Approved
0.7297	Intermediate Similarity	NPD9618	Approved
0.729	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD3094	Phase 2
0.7273	Intermediate Similarity	NPD7843	Approved
0.7273	Intermediate Similarity	NPD821	Approved
0.7257	Intermediate Similarity	NPD856	Approved
0.7257	Intermediate Similarity	NPD317	Approved
0.7257	Intermediate Similarity	NPD16	Approved
0.7257	Intermediate Similarity	NPD318	Approved
0.7248	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD9089	Approved
0.7227	Intermediate Similarity	NPD2194	Approved
0.7227	Intermediate Similarity	NPD2195	Approved
0.7217	Intermediate Similarity	NPD4626	Approved
0.7212	Intermediate Similarity	NPD1616	Discontinued
0.7193	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD9568	Approved
0.7168	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5736	Approved
0.7167	Intermediate Similarity	NPD3637	Approved
0.7167	Intermediate Similarity	NPD3635	Approved
0.7167	Intermediate Similarity	NPD3636	Approved
0.7156	Intermediate Similarity	NPD5451	Approved
0.7143	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4817	Approved
0.7143	Intermediate Similarity	NPD4818	Approved
0.713	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD290	Approved
0.713	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD9093	Approved
0.7119	Intermediate Similarity	NPD4659	Approved
0.7107	Intermediate Similarity	NPD4908	Phase 1
0.7107	Intermediate Similarity	NPD2605	Approved
0.7107	Intermediate Similarity	NPD2606	Approved
0.7105	Intermediate Similarity	NPD9616	Approved
0.7105	Intermediate Similarity	NPD9615	Approved
0.7105	Intermediate Similarity	NPD9613	Approved
0.7071	Intermediate Similarity	NPD9295	Approved
0.7069	Intermediate Similarity	NPD9384	Approved
0.7069	Intermediate Similarity	NPD9381	Approved
0.7059	Intermediate Similarity	NPD1283	Approved
0.7049	Intermediate Similarity	NPD5156	Approved
0.7049	Intermediate Similarity	NPD5155	Approved
0.7043	Intermediate Similarity	NPD9545	Approved
0.7043	Intermediate Similarity	NPD1548	Phase 1
0.7043	Intermediate Similarity	NPD316	Approved
0.7037	Intermediate Similarity	NPD3134	Approved
0.7034	Intermediate Similarity	NPD2230	Approved
0.7034	Intermediate Similarity	NPD2233	Approved
0.7034	Intermediate Similarity	NPD2232	Approved
0.7025	Intermediate Similarity	NPD2861	Phase 2
0.7018	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD9073	Approved
0.7009	Intermediate Similarity	NPD3026	Approved
0.7009	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD3143	Discontinued
0.7009	Intermediate Similarity	NPD3023	Approved
0.7	Intermediate Similarity	NPD987	Approved
0.7	Intermediate Similarity	NPD1164	Approved
0.7	Intermediate Similarity	NPD4103	Phase 2
0.7	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD497	Approved
0.6983	Remote Similarity	NPD3025	Approved
0.6983	Remote Similarity	NPD3024	Approved
0.6975	Remote Similarity	NPD9622	Approved
0.6975	Remote Similarity	NPD6582	Phase 2
0.6975	Remote Similarity	NPD1755	Approved
0.6975	Remote Similarity	NPD4749	Approved
0.6975	Remote Similarity	NPD6583	Phase 3
0.697	Remote Similarity	NPD1101	Approved
0.6967	Remote Similarity	NPD3594	Approved
0.6967	Remote Similarity	NPD3595	Approved
0.6964	Remote Similarity	NPD5535	Approved
0.6964	Remote Similarity	NPD1138	Approved
0.6949	Remote Similarity	NPD422	Phase 1
0.6949	Remote Similarity	NPD1201	Approved
0.6942	Remote Similarity	NPD257	Approved
0.6942	Remote Similarity	NPD258	Approved
0.6942	Remote Similarity	NPD4624	Approved
0.6942	Remote Similarity	NPD6584	Phase 3
0.6935	Remote Similarity	NPD6663	Approved
0.693	Remote Similarity	NPD709	Approved
0.6917	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD3680	Approved
0.6916	Remote Similarity	NPD3683	Approved
0.6916	Remote Similarity	NPD4231	Approved
0.6916	Remote Similarity	NPD3682	Approved
0.6916	Remote Similarity	NPD3681	Approved
0.6916	Remote Similarity	NPD4229	Approved
0.6909	Remote Similarity	NPD9266	Approved
0.6909	Remote Similarity	NPD74	Approved
0.6903	Remote Similarity	NPD498	Approved
0.6903	Remote Similarity	NPD495	Approved
0.6903	Remote Similarity	NPD496	Approved
0.6897	Remote Similarity	NPD7330	Discontinued
0.6891	Remote Similarity	NPD1608	Approved
0.6891	Remote Similarity	NPD2561	Approved
0.6891	Remote Similarity	NPD2562	Approved
0.6891	Remote Similarity	NPD3070	Discontinued
0.688	Remote Similarity	NPD4060	Phase 1
0.6875	Remote Similarity	NPD1139	Approved
0.6875	Remote Similarity	NPD1137	Approved
0.687	Remote Similarity	NPD9493	Approved
0.6864	Remote Similarity	NPD3847	Discontinued
0.6864	Remote Similarity	NPD3421	Phase 3
0.6863	Remote Similarity	NPD159	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1133	Approved
0.686	Remote Similarity	NPD3055	Approved
0.686	Remote Similarity	NPD3053	Approved
0.686	Remote Similarity	NPD1135	Approved
0.686	Remote Similarity	NPD1129	Approved
0.686	Remote Similarity	NPD1131	Approved
0.686	Remote Similarity	NPD1134	Approved
0.6857	Remote Similarity	NPD9612	Approved
0.6857	Remote Similarity	NPD9611	Approved
0.6857	Remote Similarity	NPD9609	Approved
0.6855	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD9244	Approved
0.6838	Remote Similarity	NPD1651	Approved
0.6838	Remote Similarity	NPD1357	Approved
0.6838	Remote Similarity	NPD5691	Approved
0.6833	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD3685	Discontinued
0.6833	Remote Similarity	NPD1669	Approved
0.6832	Remote Similarity	NPD1089	Approved
0.6832	Remote Similarity	NPD1090	Approved
0.6832	Remote Similarity	NPD1086	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