NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	122.07
Volume:	139.249
LogP:	2.441
LogD:	2.465
LogS:	-1.435
# Rotatable Bonds:	0
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.558
Synthetic Accessibility Score:	1.662
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.329
MDCK Permeability:	3.1648687581764534e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.196
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.347
30% Bioavailability (F30%):	0.612

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.756
Plasma Protein Binding (PPB):	81.21269226074219%
Volume Distribution (VD):	1.295
Pgp-substrate:	15.076929092407227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.905
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.62
CYP2C19-substrate:	0.741
CYP2C9-inhibitor:	0.18
CYP2C9-substrate:	0.873
CYP2D6-inhibitor:	0.635
CYP2D6-substrate:	0.903
CYP3A4-inhibitor:	0.098
CYP3A4-substrate:	0.341

ADMET: Excretion

Clearance (CL):	14.637
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.031
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.486
Maximum Recommended Daily Dose:	0.338
Skin Sensitization:	0.716
Carcinogencity:	0.574
Eye Corrosion:	0.989
Eye Irritation:	0.996
Respiratory Toxicity:	0.21

Download Data

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

Natural Product: NPC245187

Natural Product ID:	NPC245187
*Common Name:**	2,3-Dimethylphenol
IUPAC Name:	2,3-dimethylphenol
Synonyms:
Standard InCHIKey:	QWBBPBRQALCEIZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H10O/c1-6-4-3-5-8(9)7(6)2/h3-5,9H,1-2H3
SMILES:	Cc1c(C)cccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1490403
PubChem CID:	10687
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001272] Cresols [CHEMONTID:0001274] Ortho cresols

*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
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473446]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17432574]
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]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22234	Ficus carica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22234	Ficus carica	Species	Moraceae	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]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22234	Ficus carica	Species	Moraceae	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
EC50	1
Others	1
Potency	11

Activity Type	# Activity
Individual Protein	6
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT524	Individual Protein	Serine-protein kinase ATM	Homo sapiens	Potency	=	6309.6	nM	PMID[470467]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	37578.0	nM	PMID[470466]
NPT446	Individual Protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[470467]
NPT346	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Homo sapiens	Activity	=	82.0	%	PMID[470468]
NPT346	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Homo sapiens	EC50	=	86000.0	nM	PMID[470468]
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	31622.8	nM	PMID[470466]
NPT2	Others	Unspecified		Potency	n.a.	29092.9	nM	PMID[470467]
NPT2	Others	Unspecified		Potency	n.a.	61200.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	35694.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21714.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	70617.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	25269.7	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 NPC245187 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	340
0.1-0.2	2260
0.2-0.3	7209
0.3-0.4	12153
0.4-0.5	6288
0.5-0.6	9482
0.6-0.7	3754
0.7-0.8	916
0.8-0.85	176
0.85-0.9	91
0.9-0.95	27
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9457	High Similarity	NPC156313
0.9432	High Similarity	NPC27974
0.9348	High Similarity	NPC259512
0.9348	High Similarity	NPC312132
0.9333	High Similarity	NPC231150
0.9318	High Similarity	NPC407
0.9318	High Similarity	NPC307235
0.9247	High Similarity	NPC79241
0.9247	High Similarity	NPC6597
0.9231	High Similarity	NPC55903
0.9205	High Similarity	NPC155393
0.9167	High Similarity	NPC475580
0.9149	High Similarity	NPC33675
0.9149	High Similarity	NPC299762
0.914	High Similarity	NPC202986
0.913	High Similarity	NPC152415
0.9121	High Similarity	NPC306074
0.9091	High Similarity	NPC150837
0.9091	High Similarity	NPC286904
0.9072	High Similarity	NPC471350
0.9062	High Similarity	NPC233827
0.9062	High Similarity	NPC168393
0.9053	High Similarity	NPC72729
0.9043	High Similarity	NPC32674
0.9043	High Similarity	NPC152097
0.9022	High Similarity	NPC29373
0.9022	High Similarity	NPC147284
0.9022	High Similarity	NPC210497
0.9022	High Similarity	NPC162314
0.9022	High Similarity	NPC3358
0.9022	High Similarity	NPC94139
0.9022	High Similarity	NPC306884
0.9011	High Similarity	NPC192
0.8969	High Similarity	NPC238696
0.8969	High Similarity	NPC272029
0.8958	High Similarity	NPC252105
0.8947	High Similarity	NPC260775
0.8913	High Similarity	NPC304541
0.8889	High Similarity	NPC23167
0.8878	High Similarity	NPC117115
0.8854	High Similarity	NPC248396
0.8854	High Similarity	NPC48730
0.8854	High Similarity	NPC211885
0.8854	High Similarity	NPC12931
0.8854	High Similarity	NPC130756
0.8854	High Similarity	NPC70677
0.8854	High Similarity	NPC174911
0.8854	High Similarity	NPC129373
0.8842	High Similarity	NPC77492
0.8842	High Similarity	NPC475078
0.883	High Similarity	NPC222146
0.883	High Similarity	NPC8392
0.8817	High Similarity	NPC271440
0.8791	High Similarity	NPC19680
0.8791	High Similarity	NPC113460
0.8791	High Similarity	NPC25493
0.8788	High Similarity	NPC21594
0.8788	High Similarity	NPC67250
0.8778	High Similarity	NPC197783
0.8776	High Similarity	NPC475225
0.8763	High Similarity	NPC12221
0.875	High Similarity	NPC252821
0.875	High Similarity	NPC122005
0.8723	High Similarity	NPC76938
0.8723	High Similarity	NPC27323
0.8723	High Similarity	NPC289769
0.8723	High Similarity	NPC316301
0.8713	High Similarity	NPC58865
0.871	High Similarity	NPC204210
0.871	High Similarity	NPC155908
0.87	High Similarity	NPC320439
0.87	High Similarity	NPC151477
0.8696	High Similarity	NPC258219
0.8696	High Similarity	NPC280347
0.8696	High Similarity	NPC123273
0.8696	High Similarity	NPC242240
0.8696	High Similarity	NPC318325
0.8696	High Similarity	NPC177420
0.8687	High Similarity	NPC47284
0.8673	High Similarity	NPC269212
0.8673	High Similarity	NPC108497
0.8673	High Similarity	NPC471228
0.8673	High Similarity	NPC235762
0.8667	High Similarity	NPC248817
0.8667	High Similarity	NPC175313
0.866	High Similarity	NPC225506
0.866	High Similarity	NPC130103
0.8646	High Similarity	NPC474073
0.8632	High Similarity	NPC274678
0.8632	High Similarity	NPC32714
0.8627	High Similarity	NPC13482
0.8614	High Similarity	NPC64586
0.8614	High Similarity	NPC233835
0.8602	High Similarity	NPC55561
0.8602	High Similarity	NPC312304
0.86	High Similarity	NPC310456
0.86	High Similarity	NPC53740
0.86	High Similarity	NPC155072
0.8586	High Similarity	NPC327811
0.8586	High Similarity	NPC254965
0.8571	High Similarity	NPC80800
0.8571	High Similarity	NPC477685
0.8556	High Similarity	NPC265146
0.8556	High Similarity	NPC124436
0.8544	High Similarity	NPC95716
0.8529	High Similarity	NPC314187
0.8529	High Similarity	NPC202647
0.8526	High Similarity	NPC128062
0.8515	High Similarity	NPC66834
0.8495	Intermediate Similarity	NPC70436
0.8478	Intermediate Similarity	NPC184169
0.8469	Intermediate Similarity	NPC166761
0.8462	Intermediate Similarity	NPC250323
0.8462	Intermediate Similarity	NPC46940
0.8462	Intermediate Similarity	NPC302371
0.8454	Intermediate Similarity	NPC225464
0.8454	Intermediate Similarity	NPC88420
0.8454	Intermediate Similarity	NPC109955
0.8447	Intermediate Similarity	NPC141782
0.8447	Intermediate Similarity	NPC224870
0.8447	Intermediate Similarity	NPC132720
0.8438	Intermediate Similarity	NPC144682
0.8431	Intermediate Similarity	NPC11554
0.8431	Intermediate Similarity	NPC306295
0.8421	Intermediate Similarity	NPC138117
0.8421	Intermediate Similarity	NPC325292
0.8416	Intermediate Similarity	NPC54765
0.8404	Intermediate Similarity	NPC47950
0.8404	Intermediate Similarity	NPC300017
0.84	Intermediate Similarity	NPC120719
0.84	Intermediate Similarity	NPC227458
0.84	Intermediate Similarity	NPC218879
0.84	Intermediate Similarity	NPC102216
0.84	Intermediate Similarity	NPC130817
0.84	Intermediate Similarity	NPC244513
0.8381	Intermediate Similarity	NPC715
0.8367	Intermediate Similarity	NPC128723
0.8367	Intermediate Similarity	NPC92730
0.8367	Intermediate Similarity	NPC80027
0.8365	Intermediate Similarity	NPC77772
0.8365	Intermediate Similarity	NPC151537
0.8365	Intermediate Similarity	NPC176279
0.8365	Intermediate Similarity	NPC260323
0.8365	Intermediate Similarity	NPC470770
0.8365	Intermediate Similarity	NPC469912
0.8365	Intermediate Similarity	NPC266937
0.8333	Intermediate Similarity	NPC233320
0.8333	Intermediate Similarity	NPC232523
0.8333	Intermediate Similarity	NPC204901
0.8333	Intermediate Similarity	NPC158253
0.8317	Intermediate Similarity	NPC37802
0.8317	Intermediate Similarity	NPC138942
0.8316	Intermediate Similarity	NPC45040
0.8302	Intermediate Similarity	NPC107240
0.8302	Intermediate Similarity	NPC195922
0.8302	Intermediate Similarity	NPC249270
0.83	Intermediate Similarity	NPC24404
0.83	Intermediate Similarity	NPC302219
0.83	Intermediate Similarity	NPC222522
0.83	Intermediate Similarity	NPC94351
0.83	Intermediate Similarity	NPC196479
0.83	Intermediate Similarity	NPC71002
0.83	Intermediate Similarity	NPC168303
0.83	Intermediate Similarity	NPC313030
0.83	Intermediate Similarity	NPC53051
0.83	Intermediate Similarity	NPC242342
0.83	Intermediate Similarity	NPC85479
0.83	Intermediate Similarity	NPC106396
0.83	Intermediate Similarity	NPC146798
0.83	Intermediate Similarity	NPC168829
0.83	Intermediate Similarity	NPC249828
0.8298	Intermediate Similarity	NPC98772
0.8286	Intermediate Similarity	NPC62867
0.8286	Intermediate Similarity	NPC473521
0.8286	Intermediate Similarity	NPC177962
0.8283	Intermediate Similarity	NPC10588
0.8283	Intermediate Similarity	NPC294741
0.8252	Intermediate Similarity	NPC174981
0.8252	Intermediate Similarity	NPC95344
0.8247	Intermediate Similarity	NPC313650
0.8247	Intermediate Similarity	NPC257182
0.8247	Intermediate Similarity	NPC26244
0.8247	Intermediate Similarity	NPC107522
0.8247	Intermediate Similarity	NPC246679
0.8235	Intermediate Similarity	NPC469913
0.8235	Intermediate Similarity	NPC99836
0.8235	Intermediate Similarity	NPC477814
0.8235	Intermediate Similarity	NPC271274
0.8235	Intermediate Similarity	NPC12640
0.8235	Intermediate Similarity	NPC201662
0.8229	Intermediate Similarity	NPC295295
0.8224	Intermediate Similarity	NPC474486
0.8218	Intermediate Similarity	NPC288411
0.8218	Intermediate Similarity	NPC323810
0.8218	Intermediate Similarity	NPC93831
0.8208	Intermediate Similarity	NPC263753
0.8208	Intermediate Similarity	NPC322239
0.82	Intermediate Similarity	NPC100340
0.82	Intermediate Similarity	NPC110764
0.82	Intermediate Similarity	NPC143659

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 NPC245187 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	1082
0.2-0.3	1451
0.3-0.4	2923
0.4-0.5	1815
0.5-0.6	1035
0.6-0.7	375
0.7-0.8	58
0.8-0.85	15
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9348	High Similarity	NPD288	Approved
0.9239	High Similarity	NPD844	Approved
0.9053	High Similarity	NPD289	Clinical (unspecified phase)
0.8817	High Similarity	NPD845	Approved
0.8723	High Similarity	NPD1432	Clinical (unspecified phase)
0.8556	High Similarity	NPD111	Approved
0.8515	High Similarity	NPD2342	Discontinued
0.8438	Intermediate Similarity	NPD1809	Phase 2
0.8367	Intermediate Similarity	NPD3020	Approved
0.8333	Intermediate Similarity	NPD2933	Approved
0.8333	Intermediate Similarity	NPD2934	Approved
0.8286	Intermediate Similarity	NPD7635	Approved
0.8247	Intermediate Similarity	NPD2859	Approved
0.8247	Intermediate Similarity	NPD2860	Approved
0.8235	Intermediate Similarity	NPD1445	Approved
0.8235	Intermediate Similarity	NPD1444	Approved
0.82	Intermediate Similarity	NPD940	Approved
0.82	Intermediate Similarity	NPD846	Approved
0.8173	Intermediate Similarity	NPD4750	Phase 3
0.8173	Intermediate Similarity	NPD1792	Phase 2
0.8	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3021	Approved
0.8	Intermediate Similarity	NPD3022	Approved
0.7921	Intermediate Similarity	NPD1242	Phase 1
0.7818	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD9500	Approved
0.7727	Intermediate Similarity	NPD709	Approved
0.7727	Intermediate Similarity	NPD9087	Approved
0.7727	Intermediate Similarity	NPD6671	Approved
0.7723	Intermediate Similarity	NPD9273	Approved
0.7692	Intermediate Similarity	NPD9608	Approved
0.7692	Intermediate Similarity	NPD9610	Approved
0.7685	Intermediate Similarity	NPD228	Approved
0.7679	Intermediate Similarity	NPD3091	Approved
0.7636	Intermediate Similarity	NPD1791	Approved
0.7636	Intermediate Similarity	NPD1793	Approved
0.7636	Intermediate Similarity	NPD497	Approved
0.7611	Intermediate Similarity	NPD4093	Discontinued
0.7586	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD1201	Approved
0.7545	Intermediate Similarity	NPD498	Approved
0.7545	Intermediate Similarity	NPD496	Approved
0.7545	Intermediate Similarity	NPD495	Approved
0.7544	Intermediate Similarity	NPD1751	Approved
0.7544	Intermediate Similarity	NPD4626	Approved
0.7544	Intermediate Similarity	NPD3019	Approved
0.7544	Intermediate Similarity	NPD4059	Approved
0.7544	Intermediate Similarity	NPD2932	Approved
0.7477	Intermediate Similarity	NPD9618	Approved
0.7477	Intermediate Similarity	NPD9614	Approved
0.7473	Intermediate Similarity	NPD9294	Approved
0.7455	Intermediate Similarity	NPD9379	Approved
0.7455	Intermediate Similarity	NPD9377	Approved
0.7414	Intermediate Similarity	NPD3092	Approved
0.7391	Intermediate Similarity	NPD9088	Approved
0.7391	Intermediate Similarity	NPD2286	Discontinued
0.7387	Intermediate Similarity	NPD2229	Approved
0.7387	Intermediate Similarity	NPD2234	Approved
0.7387	Intermediate Similarity	NPD2228	Approved
0.7364	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD290	Approved
0.7311	Intermediate Similarity	NPD1470	Approved
0.7281	Intermediate Similarity	NPD9615	Approved
0.7281	Intermediate Similarity	NPD9613	Approved
0.7281	Intermediate Similarity	NPD9616	Approved
0.7241	Intermediate Similarity	NPD3095	Discontinued
0.7241	Intermediate Similarity	NPD4589	Approved
0.7238	Intermediate Similarity	NPD3028	Approved
0.7232	Intermediate Similarity	NPD1398	Phase 1
0.7232	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD6696	Suspended
0.7222	Intermediate Similarity	NPD968	Approved
0.7217	Intermediate Similarity	NPD5304	Approved
0.7217	Intermediate Similarity	NPD5303	Approved
0.7217	Intermediate Similarity	NPD316	Approved
0.7213	Intermediate Similarity	NPD4625	Phase 3
0.7203	Intermediate Similarity	NPD2232	Approved
0.7203	Intermediate Similarity	NPD2233	Approved
0.7203	Intermediate Similarity	NPD2230	Approved
0.7182	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD3094	Phase 2
0.7167	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5691	Approved
0.7143	Intermediate Similarity	NPD4749	Approved
0.7119	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2194	Approved
0.7107	Intermediate Similarity	NPD2195	Approved
0.7103	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD74	Approved
0.7091	Intermediate Similarity	NPD9266	Approved
0.7083	Intermediate Similarity	NPD9089	Approved
0.7049	Intermediate Similarity	NPD3637	Approved
0.7049	Intermediate Similarity	NPD3636	Approved
0.7049	Intermediate Similarity	NPD3635	Approved
0.7049	Intermediate Similarity	NPD1712	Approved
0.7049	Intermediate Similarity	NPD5736	Approved
0.7043	Intermediate Similarity	NPD9493	Approved
0.7043	Intermediate Similarity	NPD7340	Approved
0.704	Intermediate Similarity	NPD4060	Phase 1
0.7037	Intermediate Similarity	NPD9244	Approved
0.7034	Intermediate Similarity	NPD1983	Approved
0.7034	Intermediate Similarity	NPD1980	Approved
0.7034	Intermediate Similarity	NPD1981	Approved
0.7034	Intermediate Similarity	NPD3496	Discontinued
0.7018	Intermediate Similarity	NPD475	Phase 2
0.7	Intermediate Similarity	NPD9267	Approved
0.7	Intermediate Similarity	NPD1755	Approved
0.7	Intermediate Similarity	NPD9263	Approved
0.7	Intermediate Similarity	NPD9264	Approved
0.6992	Remote Similarity	NPD2606	Approved
0.6992	Remote Similarity	NPD2605	Approved
0.6979	Remote Similarity	NPD9093	Approved
0.6975	Remote Similarity	NPD1611	Approved
0.6975	Remote Similarity	NPD1610	Phase 2
0.6967	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD255	Approved
0.6957	Remote Similarity	NPD256	Approved
0.6949	Remote Similarity	NPD1778	Approved
0.6949	Remote Similarity	NPD9381	Approved
0.6949	Remote Similarity	NPD9384	Approved
0.6942	Remote Similarity	NPD1283	Approved
0.6937	Remote Similarity	NPD2684	Approved
0.6935	Remote Similarity	NPD5155	Approved
0.6935	Remote Similarity	NPD5156	Approved
0.6931	Remote Similarity	NPD9295	Approved
0.693	Remote Similarity	NPD5283	Phase 1
0.6923	Remote Similarity	NPD7330	Discontinued
0.6923	Remote Similarity	NPD1759	Phase 1
0.6923	Remote Similarity	NPD1548	Phase 1
0.6916	Remote Similarity	NPD1616	Discontinued
0.6911	Remote Similarity	NPD2861	Phase 2
0.6891	Remote Similarity	NPD3026	Approved
0.6891	Remote Similarity	NPD3023	Approved
0.6869	Remote Similarity	NPD9073	Approved
0.6864	Remote Similarity	NPD1651	Approved
0.6864	Remote Similarity	NPD3024	Approved
0.6864	Remote Similarity	NPD3445	Approved
0.6864	Remote Similarity	NPD3443	Approved
0.6864	Remote Similarity	NPD3025	Approved
0.6864	Remote Similarity	NPD3444	Approved
0.6864	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.686	Remote Similarity	NPD9622	Approved
0.686	Remote Similarity	NPD1669	Approved
0.6855	Remote Similarity	NPD3594	Approved
0.6855	Remote Similarity	NPD3595	Approved
0.6847	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1138	Approved
0.6842	Remote Similarity	NPD821	Approved
0.6838	Remote Similarity	NPD1758	Phase 1
0.6838	Remote Similarity	NPD317	Approved
0.6838	Remote Similarity	NPD856	Approved
0.6838	Remote Similarity	NPD318	Approved
0.6838	Remote Similarity	NPD16	Approved
0.6833	Remote Similarity	NPD422	Phase 1
0.6829	Remote Similarity	NPD4624	Approved
0.6825	Remote Similarity	NPD6663	Approved
0.681	Remote Similarity	NPD7157	Approved
0.6803	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1024	Discontinued
0.6797	Remote Similarity	NPD4097	Suspended
0.6777	Remote Similarity	NPD1608	Approved
0.6754	Remote Similarity	NPD1139	Approved
0.6754	Remote Similarity	NPD1137	Approved
0.6752	Remote Similarity	NPD9568	Approved
0.6752	Remote Similarity	NPD7636	Approved
0.675	Remote Similarity	NPD3143	Discontinued
0.675	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD3055	Approved
0.6748	Remote Similarity	NPD3053	Approved
0.6748	Remote Similarity	NPD1164	Approved
0.6746	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD9609	Approved
0.6729	Remote Similarity	NPD9611	Approved
0.6729	Remote Similarity	NPD9612	Approved
0.6727	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD1357	Approved
0.672	Remote Similarity	NPD596	Approved
0.672	Remote Similarity	NPD4908	Phase 1
0.672	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.672	Remote Similarity	NPD600	Approved
0.6697	Remote Similarity	NPD4818	Approved
0.6697	Remote Similarity	NPD4817	Approved
0.6696	Remote Similarity	NPD7843	Approved
0.6694	Remote Similarity	NPD1281	Approved
0.6694	Remote Similarity	NPD9620	Approved
0.6694	Remote Similarity	NPD257	Approved
0.6694	Remote Similarity	NPD6584	Phase 3
0.6694	Remote Similarity	NPD9621	Approved
0.6694	Remote Similarity	NPD9619	Approved
0.6694	Remote Similarity	NPD258	Approved
0.6692	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1753	Discontinued
0.6692	Remote Similarity	NPD1509	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