NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	150.1
Volume:	173.841
LogP:	3.235
LogD:	3.294
LogS:	-2.586
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.603
Synthetic Accessibility Score:	1.838
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:	-4.453
MDCK Permeability:	2.3660630176891573e-05
Pgp-inhibitor:	0.035
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.253
30% Bioavailability (F30%):	0.459

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.583
Plasma Protein Binding (PPB):	93.75297546386719%
Volume Distribution (VD):	3.725
Pgp-substrate:	9.052578926086426%

ADMET: Metabolism

CYP1A2-inhibitor:	0.919
CYP1A2-substrate:	0.898
CYP2C19-inhibitor:	0.588
CYP2C19-substrate:	0.725
CYP2C9-inhibitor:	0.363
CYP2C9-substrate:	0.862
CYP2D6-inhibitor:	0.694
CYP2D6-substrate:	0.787
CYP3A4-inhibitor:	0.092
CYP3A4-substrate:	0.413

ADMET: Excretion

Clearance (CL):	9.28
Half-life (T1/2):	0.764

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.027
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.636
Maximum Recommended Daily Dose:	0.065
Skin Sensitization:	0.784
Carcinogencity:	0.084
Eye Corrosion:	0.99
Eye Irritation:	0.992
Respiratory Toxicity:	0.536

Download Data

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

Natural Product: NPC306074

Natural Product ID:	NPC306074
*Common Name:**	2-Tert-Butylphenol
IUPAC Name:	2-tert-butylphenol
Synonyms:	2-Tert-Butylphenol
Standard InCHIKey:	WJQOZHYUIDYNHM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H14O/c1-10(2,3)8-6-4-5-7-9(8)11/h4-7,11H,1-3H3
SMILES:	CC(C)(C)c1ccccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL108851
PubChem CID:	6923
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
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/hlca.19270100148]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Petals	n.a.	n.a.	PMID[15043425]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24338885]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Silk Stigma Style	n.a.	n.a.	Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9445	Crocus sativus	Species	Iridaceae	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
Others	8
Potency	29

Activity Type	# Activity
Cell Line	3
Individual Protein	8
Organism	4
Others	23

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	log(1/ID50)	=	2.42	n.a.	PMID[519194]
NPT137	Cell Line	L1210	Mus musculus	log(1/ID50)	=	4.0	n.a.	PMID[519194]
NPT137	Cell Line	L1210	Mus musculus	Activity	<	15.0	%	PMID[519194]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	8912.5	nM	PMID[519195]
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	39810.7	nM	PMID[519195]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[519196]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[519195]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[519196]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IC50	=	34500.0	nM	PMID[519192]
NPT35	Others	n.a.		LogP	=	3.31	n.a.	PMID[519192]
NPT35	Others	n.a.		pKa	=	11.3	n.a.	PMID[519192]
NPT35	Others	n.a.		LogD	=	3.31	n.a.	PMID[519192]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	Log 1/I50	=	4.46	1/M	PMID[519192]
NPT35	Others	n.a.		Log PNalk	=	2.31	n.a.	PMID[519193]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	31622.8	nM	PMID[519195]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	14715.7	nM	PMID[519196]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2332.3	nM	PMID[519196]
NPT2	Others	Unspecified		Potency	n.a.	24832.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27611.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	62377.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1380.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	2213.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	55092.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30637.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1949.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	69357.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	55593.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	49547.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	55593.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	88.1	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 NPC306074 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	262
0.1-0.2	1969
0.2-0.3	5353
0.3-0.4	13294
0.4-0.5	7368
0.5-0.6	9760
0.6-0.7	3645
0.7-0.8	771
0.8-0.85	173
0.85-0.9	70
0.9-0.95	29
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC152415
0.9551	High Similarity	NPC289769
0.9535	High Similarity	NPC307235
0.9535	High Similarity	NPC407
0.9438	High Similarity	NPC55903
0.9419	High Similarity	NPC155393
0.9348	High Similarity	NPC299762
0.9348	High Similarity	NPC252821
0.9348	High Similarity	NPC33675
0.9348	High Similarity	NPC122005
0.9333	High Similarity	NPC27323
0.9333	High Similarity	NPC316301
0.9326	High Similarity	NPC155908
0.9302	High Similarity	NPC286904
0.9247	High Similarity	NPC225506
0.9231	High Similarity	NPC144682
0.9231	High Similarity	NPC8392
0.9222	High Similarity	NPC271440
0.9149	High Similarity	NPC252105
0.913	High Similarity	NPC312132
0.913	High Similarity	NPC259512
0.9121	High Similarity	NPC245187
0.9111	High Similarity	NPC304541
0.9111	High Similarity	NPC204210
0.9101	High Similarity	NPC258219
0.9101	High Similarity	NPC242240
0.9101	High Similarity	NPC123273
0.9101	High Similarity	NPC318325
0.9091	High Similarity	NPC23167
0.9032	High Similarity	NPC77492
0.9032	High Similarity	NPC6597
0.9032	High Similarity	NPC79241
0.9032	High Similarity	NPC225464
0.9022	High Similarity	NPC222146
0.8989	High Similarity	NPC27974
0.8989	High Similarity	NPC25493
0.8989	High Similarity	NPC113460
0.8977	High Similarity	NPC197783
0.8936	High Similarity	NPC92730
0.8913	High Similarity	NPC128062
0.8901	High Similarity	NPC231150
0.8889	High Similarity	NPC98772
0.8889	High Similarity	NPC177420
0.8889	High Similarity	NPC70436
0.8889	High Similarity	NPC280347
0.8876	High Similarity	NPC184169
0.8866	High Similarity	NPC47284
0.8864	High Similarity	NPC175313
0.8864	High Similarity	NPC248817
0.8854	High Similarity	NPC269212
0.8842	High Similarity	NPC72729
0.8804	High Similarity	NPC210497
0.8804	High Similarity	NPC306884
0.8804	High Similarity	NPC3358
0.8804	High Similarity	NPC94139
0.8804	High Similarity	NPC147284
0.8804	High Similarity	NPC162314
0.8791	High Similarity	NPC55561
0.8791	High Similarity	NPC192
0.8776	High Similarity	NPC310456
0.8776	High Similarity	NPC53740
0.875	High Similarity	NPC265146
0.875	High Similarity	NPC124436
0.8737	High Similarity	NPC128723
0.8696	High Similarity	NPC270547
0.8696	High Similarity	NPC45040
0.8687	High Similarity	NPC320439
0.8652	High Similarity	NPC150837
0.8646	High Similarity	NPC129373
0.8646	High Similarity	NPC174911
0.8646	High Similarity	NPC248396
0.8646	High Similarity	NPC48730
0.8646	High Similarity	NPC211885
0.8632	High Similarity	NPC152097
0.8632	High Similarity	NPC156313
0.8617	High Similarity	NPC26244
0.8602	High Similarity	NPC138117
0.8602	High Similarity	NPC325292
0.8602	High Similarity	NPC29373
0.86	High Similarity	NPC306295
0.86	High Similarity	NPC64586
0.8587	High Similarity	NPC47950
0.8587	High Similarity	NPC300017
0.8586	High Similarity	NPC155072
0.8571	High Similarity	NPC475225
0.8571	High Similarity	NPC120719
0.8571	High Similarity	NPC475580
0.8571	High Similarity	NPC19680
0.8557	High Similarity	NPC51015
0.8557	High Similarity	NPC12221
0.8542	High Similarity	NPC260775
0.8542	High Similarity	NPC80027
0.8526	High Similarity	NPC473388
0.8511	High Similarity	NPC76938
0.8511	High Similarity	NPC151715
0.8506	High Similarity	NPC133050
0.8485	Intermediate Similarity	NPC219286
0.8485	Intermediate Similarity	NPC99557
0.8485	Intermediate Similarity	NPC138942
0.8469	Intermediate Similarity	NPC471228
0.8469	Intermediate Similarity	NPC235762
0.8469	Intermediate Similarity	NPC168829
0.8469	Intermediate Similarity	NPC108497
0.8454	Intermediate Similarity	NPC130756
0.8454	Intermediate Similarity	NPC12931
0.8454	Intermediate Similarity	NPC70677
0.8438	Intermediate Similarity	NPC474073
0.8438	Intermediate Similarity	NPC475078
0.8431	Intermediate Similarity	NPC13482
0.8421	Intermediate Similarity	NPC274678
0.8421	Intermediate Similarity	NPC313650
0.8421	Intermediate Similarity	NPC246679
0.8421	Intermediate Similarity	NPC32714
0.8416	Intermediate Similarity	NPC470039
0.84	Intermediate Similarity	NPC477814
0.84	Intermediate Similarity	NPC271274
0.8384	Intermediate Similarity	NPC272029
0.8384	Intermediate Similarity	NPC288411
0.8384	Intermediate Similarity	NPC238696
0.837	Intermediate Similarity	NPC104216
0.8367	Intermediate Similarity	NPC477685
0.835	Intermediate Similarity	NPC275627
0.835	Intermediate Similarity	NPC266937
0.835	Intermediate Similarity	NPC77772
0.835	Intermediate Similarity	NPC470770
0.8333	Intermediate Similarity	NPC202986
0.8333	Intermediate Similarity	NPC82664
0.8333	Intermediate Similarity	NPC216520
0.8333	Intermediate Similarity	NPC283711
0.8333	Intermediate Similarity	NPC132271
0.8333	Intermediate Similarity	NPC292730
0.8317	Intermediate Similarity	NPC228737
0.8317	Intermediate Similarity	NPC66834
0.83	Intermediate Similarity	NPC303141
0.83	Intermediate Similarity	NPC117115
0.83	Intermediate Similarity	NPC471350
0.8283	Intermediate Similarity	NPC470202
0.8283	Intermediate Similarity	NPC168393
0.8283	Intermediate Similarity	NPC233827
0.8269	Intermediate Similarity	NPC228425
0.8269	Intermediate Similarity	NPC177962
0.8269	Intermediate Similarity	NPC250323
0.8269	Intermediate Similarity	NPC62867
0.8265	Intermediate Similarity	NPC130103
0.8252	Intermediate Similarity	NPC141782
0.8247	Intermediate Similarity	NPC260000
0.8247	Intermediate Similarity	NPC32674
0.8222	Intermediate Similarity	NPC168855
0.8218	Intermediate Similarity	NPC248904
0.8218	Intermediate Similarity	NPC54765
0.8218	Intermediate Similarity	NPC21594
0.8211	Intermediate Similarity	NPC181709
0.82	Intermediate Similarity	NPC119860
0.82	Intermediate Similarity	NPC227458
0.82	Intermediate Similarity	NPC218879
0.82	Intermediate Similarity	NPC102216
0.82	Intermediate Similarity	NPC244513
0.8191	Intermediate Similarity	NPC300478
0.8191	Intermediate Similarity	NPC312304
0.8182	Intermediate Similarity	NPC101025
0.8182	Intermediate Similarity	NPC472585
0.8182	Intermediate Similarity	NPC471578
0.8182	Intermediate Similarity	NPC80800
0.8173	Intermediate Similarity	NPC260323
0.8173	Intermediate Similarity	NPC176279
0.8163	Intermediate Similarity	NPC216468
0.8163	Intermediate Similarity	NPC280869
0.8163	Intermediate Similarity	NPC51333
0.8163	Intermediate Similarity	NPC78119
0.8163	Intermediate Similarity	NPC132078
0.8155	Intermediate Similarity	NPC58865
0.8137	Intermediate Similarity	NPC158253
0.8137	Intermediate Similarity	NPC232523
0.8137	Intermediate Similarity	NPC151477
0.8137	Intermediate Similarity	NPC204901
0.8132	Intermediate Similarity	NPC474354
0.8119	Intermediate Similarity	NPC243677
0.8119	Intermediate Similarity	NPC474839
0.8119	Intermediate Similarity	NPC37802
0.8113	Intermediate Similarity	NPC195922
0.81	Intermediate Similarity	NPC24404
0.81	Intermediate Similarity	NPC302219
0.81	Intermediate Similarity	NPC222522
0.81	Intermediate Similarity	NPC94351
0.81	Intermediate Similarity	NPC13426
0.81	Intermediate Similarity	NPC71002
0.81	Intermediate Similarity	NPC168303
0.81	Intermediate Similarity	NPC313030
0.81	Intermediate Similarity	NPC53051
0.81	Intermediate Similarity	NPC242342
0.81	Intermediate Similarity	NPC85479
0.81	Intermediate Similarity	NPC62351
0.81	Intermediate Similarity	NPC106396
0.81	Intermediate Similarity	NPC146798
0.81	Intermediate Similarity	NPC249828
0.8095	Intermediate Similarity	NPC98372
0.8081	Intermediate Similarity	NPC213730
0.8081	Intermediate Similarity	NPC166761
0.8081	Intermediate Similarity	NPC10588
0.8081	Intermediate Similarity	NPC294741

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 NPC306074 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	1096
0.2-0.3	1279
0.3-0.4	2961
0.4-0.5	1900
0.5-0.6	1140
0.6-0.7	396
0.7-0.8	61
0.8-0.85	3
0.85-0.9	6
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9333	High Similarity	NPD1432	Clinical (unspecified phase)
0.9247	High Similarity	NPD289	Clinical (unspecified phase)
0.9231	High Similarity	NPD1809	Phase 2
0.9222	High Similarity	NPD845	Approved
0.913	High Similarity	NPD288	Approved
0.9022	High Similarity	NPD844	Approved
0.875	High Similarity	NPD111	Approved
0.8617	High Similarity	NPD2860	Approved
0.8617	High Similarity	NPD2859	Approved
0.8557	High Similarity	NPD940	Approved
0.8557	High Similarity	NPD846	Approved
0.8542	High Similarity	NPD3020	Approved
0.8511	High Similarity	NPD2933	Approved
0.8511	High Similarity	NPD2934	Approved
0.8039	Intermediate Similarity	NPD1445	Approved
0.8039	Intermediate Similarity	NPD1444	Approved
0.8	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7981	Intermediate Similarity	NPD4750	Phase 3
0.7961	Intermediate Similarity	NPD2342	Discontinued
0.7907	Intermediate Similarity	NPD9087	Approved
0.7879	Intermediate Similarity	NPD9273	Approved
0.785	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD9608	Approved
0.7843	Intermediate Similarity	NPD9610	Approved
0.781	Intermediate Similarity	NPD3021	Approved
0.781	Intermediate Similarity	NPD3022	Approved
0.781	Intermediate Similarity	NPD1792	Phase 2
0.7778	Intermediate Similarity	NPD1793	Approved
0.7778	Intermediate Similarity	NPD1791	Approved
0.7757	Intermediate Similarity	NPD7635	Approved
0.7679	Intermediate Similarity	NPD4589	Approved
0.764	Intermediate Similarity	NPD9294	Approved
0.7615	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD9500	Approved
0.7556	Intermediate Similarity	NPD9088	Approved
0.7549	Intermediate Similarity	NPD1242	Phase 1
0.7545	Intermediate Similarity	NPD6671	Approved
0.7523	Intermediate Similarity	NPD2229	Approved
0.7523	Intermediate Similarity	NPD2234	Approved
0.7523	Intermediate Similarity	NPD2228	Approved
0.75	Intermediate Similarity	NPD5304	Approved
0.75	Intermediate Similarity	NPD7330	Discontinued
0.75	Intermediate Similarity	NPD5303	Approved
0.75	Intermediate Similarity	NPD3091	Approved
0.7453	Intermediate Similarity	NPD290	Approved
0.7434	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD3028	Approved
0.7368	Intermediate Similarity	NPD2932	Approved
0.7368	Intermediate Similarity	NPD4059	Approved
0.7368	Intermediate Similarity	NPD3019	Approved
0.7368	Intermediate Similarity	NPD1751	Approved
0.7358	Intermediate Similarity	NPD968	Approved
0.7345	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD228	Approved
0.7321	Intermediate Similarity	NPD7636	Approved
0.7315	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD3143	Discontinued
0.7304	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3092	Approved
0.7241	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD9089	Approved
0.7232	Intermediate Similarity	NPD7157	Approved
0.7232	Intermediate Similarity	NPD255	Approved
0.7232	Intermediate Similarity	NPD256	Approved
0.7222	Intermediate Similarity	NPD74	Approved
0.7222	Intermediate Similarity	NPD2684	Approved
0.7222	Intermediate Similarity	NPD9266	Approved
0.7179	Intermediate Similarity	NPD3070	Discontinued
0.7168	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD9493	Approved
0.7168	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9618	Approved
0.7143	Intermediate Similarity	NPD497	Approved
0.7143	Intermediate Similarity	NPD9614	Approved
0.7143	Intermediate Similarity	NPD475	Phase 2
0.713	Intermediate Similarity	NPD9267	Approved
0.713	Intermediate Similarity	NPD4093	Discontinued
0.713	Intermediate Similarity	NPD9264	Approved
0.713	Intermediate Similarity	NPD9263	Approved
0.7128	Intermediate Similarity	NPD9093	Approved
0.7119	Intermediate Similarity	NPD1755	Approved
0.7119	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD9379	Approved
0.7117	Intermediate Similarity	NPD9377	Approved
0.7117	Intermediate Similarity	NPD1138	Approved
0.7094	Intermediate Similarity	NPD1201	Approved
0.7094	Intermediate Similarity	NPD1610	Phase 2
0.708	Intermediate Similarity	NPD709	Approved
0.7071	Intermediate Similarity	NPD9295	Approved
0.7069	Intermediate Similarity	NPD3095	Discontinued
0.7069	Intermediate Similarity	NPD4626	Approved
0.7059	Intermediate Similarity	NPD6696	Suspended
0.7054	Intermediate Similarity	NPD496	Approved
0.7054	Intermediate Similarity	NPD495	Approved
0.7054	Intermediate Similarity	NPD498	Approved
0.7048	Intermediate Similarity	NPD1616	Discontinued
0.7043	Intermediate Similarity	NPD1548	Phase 1
0.7043	Intermediate Similarity	NPD1759	Phase 1
0.7027	Intermediate Similarity	NPD1137	Approved
0.7027	Intermediate Similarity	NPD1139	Approved
0.701	Intermediate Similarity	NPD9073	Approved
0.7	Intermediate Similarity	NPD3094	Phase 2
0.6981	Remote Similarity	NPD4818	Approved
0.6981	Remote Similarity	NPD4817	Approved
0.6975	Remote Similarity	NPD4749	Approved
0.6972	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7843	Approved
0.6964	Remote Similarity	NPD821	Approved
0.6957	Remote Similarity	NPD1758	Phase 1
0.6957	Remote Similarity	NPD856	Approved
0.6957	Remote Similarity	NPD9616	Approved
0.6957	Remote Similarity	NPD318	Approved
0.6957	Remote Similarity	NPD9613	Approved
0.6957	Remote Similarity	NPD16	Approved
0.6957	Remote Similarity	NPD317	Approved
0.6957	Remote Similarity	NPD9615	Approved
0.6949	Remote Similarity	NPD422	Phase 1
0.6942	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD2194	Approved
0.6942	Remote Similarity	NPD2195	Approved
0.6923	Remote Similarity	NPD2286	Discontinued
0.6923	Remote Similarity	NPD1778	Approved
0.6923	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD316	Approved
0.6891	Remote Similarity	NPD2232	Approved
0.6891	Remote Similarity	NPD2233	Approved
0.6891	Remote Similarity	NPD2230	Approved
0.6885	Remote Similarity	NPD3636	Approved
0.6885	Remote Similarity	NPD5736	Approved
0.6885	Remote Similarity	NPD3637	Approved
0.6885	Remote Similarity	NPD3635	Approved
0.6885	Remote Similarity	NPD4212	Discontinued
0.6885	Remote Similarity	NPD4208	Discontinued
0.687	Remote Similarity	NPD9568	Approved
0.6864	Remote Similarity	NPD3496	Discontinued
0.6863	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD752	Approved
0.6863	Remote Similarity	NPD1088	Approved
0.686	Remote Similarity	NPD1470	Approved
0.686	Remote Similarity	NPD1133	Approved
0.686	Remote Similarity	NPD1164	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
0.686	Remote Similarity	NPD2797	Approved
0.6857	Remote Similarity	NPD9611	Approved
0.6857	Remote Similarity	NPD9612	Approved
0.6857	Remote Similarity	NPD9609	Approved
0.6855	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5451	Approved
0.6829	Remote Similarity	NPD4908	Phase 1
0.6829	Remote Similarity	NPD4207	Discontinued
0.6829	Remote Similarity	NPD2605	Approved
0.6829	Remote Similarity	NPD2606	Approved
0.68	Remote Similarity	NPD1101	Approved
0.68	Remote Similarity	NPD9094	Approved
0.6796	Remote Similarity	NPD719	Approved
0.6796	Remote Similarity	NPD720	Approved
0.6789	Remote Similarity	NPD9697	Approved
0.6786	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6387	Discontinued
0.6783	Remote Similarity	NPD2557	Approved
0.678	Remote Similarity	NPD2667	Approved
0.678	Remote Similarity	NPD2668	Approved
0.6774	Remote Similarity	NPD5155	Approved
0.6774	Remote Similarity	NPD4625	Phase 3
0.6774	Remote Similarity	NPD5156	Approved
0.6759	Remote Similarity	NPD3682	Approved
0.6759	Remote Similarity	NPD4658	Approved
0.6759	Remote Similarity	NPD4229	Approved
0.6759	Remote Similarity	NPD3680	Approved
0.6759	Remote Similarity	NPD9261	Approved
0.6759	Remote Similarity	NPD4231	Approved
0.6759	Remote Similarity	NPD3683	Approved
0.6759	Remote Similarity	NPD3681	Approved
0.6759	Remote Similarity	NPD4656	Approved
0.6754	Remote Similarity	NPD5283	Phase 1
0.6754	Remote Similarity	NPD1398	Phase 1
0.6752	Remote Similarity	NPD9545	Approved
0.6748	Remote Similarity	NPD2861	Phase 2
0.6731	Remote Similarity	NPD9296	Approved
0.6723	Remote Similarity	NPD3023	Approved
0.6723	Remote Similarity	NPD3026	Approved
0.6723	Remote Similarity	NPD1980	Approved
0.6723	Remote Similarity	NPD1981	Approved
0.6723	Remote Similarity	NPD1983	Approved
0.6721	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD4103	Phase 2
0.672	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD9495	Approved
0.6697	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD9244	Approved
0.6696	Remote Similarity	NPD593	Approved
0.6696	Remote Similarity	NPD9281	Approved
0.6696	Remote Similarity	NPD595	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