NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	122.07
Volume:	139.249
LogP:	2.399
LogD:	2.399
LogS:	-1.526
# 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:	1.514
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:	-4.363
MDCK Permeability:	2.7186591978534125e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.122
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.358
30% Bioavailability (F30%):	0.268

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.737
Plasma Protein Binding (PPB):	84.98218536376953%
Volume Distribution (VD):	0.944
Pgp-substrate:	11.587724685668945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.862
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.583
CYP2C19-substrate:	0.727
CYP2C9-inhibitor:	0.135
CYP2C9-substrate:	0.826
CYP2D6-inhibitor:	0.589
CYP2D6-substrate:	0.908
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.382

ADMET: Excretion

Clearance (CL):	15.381
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.035
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.087
Rat Oral Acute Toxicity:	0.243
Maximum Recommended Daily Dose:	0.424
Skin Sensitization:	0.636
Carcinogencity:	0.602
Eye Corrosion:	0.983
Eye Irritation:	0.995
Respiratory Toxicity:	0.627

Download Data

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

Natural Product: NPC204210

Natural Product ID:	NPC204210
*Common Name:**	2,4-Dimethylphenol
IUPAC Name:	2,4-dimethylphenol
Synonyms:	2,4-Dimethyl-Phenol; 2,4-Dimethylphenol
Standard InCHIKey:	KUFFULVDNCHOFZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H10O/c1-6-3-4-8(9)7(2)5-6/h3-5,9H,1-2H3
SMILES:	Cc1ccc(c(c1)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL29878
PubChem CID:	7771
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004208] Xylenes [CHEMONTID:0004212] Xylenols

*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
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(00)97029-8]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18603435]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[20469887]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
AC50	1
EC50	1
LD50	1
Others	9
Potency	26

Activity Type	# Activity
Cell Line	3
Individual Protein	16
Organism	2
Others	17

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	log(1/ID50)	=	3.04	n.a.	PMID[551290]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	25118.9	nM	PMID[551292]
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	1000.0	nM	PMID[551292]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	39810.7	nM	PMID[551292]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	63095.7	nM	PMID[551292]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	50.1	nM	PMID[551292]
NPT546	Individual Protein	Retinoid X receptor alpha	Homo sapiens	Potency	n.a.	1000000.0	nM	PMID[551294]
NPT249	Individual Protein	Glucocorticoid receptor	Homo sapiens	Potency	n.a.	398107.2	nM	PMID[551294]
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	n.a.	158.5	nM	PMID[551294]
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	251188.6	nM	PMID[551294]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[551295]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	12197.2	nM	PMID[551295]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	398107.2	nM	PMID[551294]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	53080.4	nM	PMID[551292]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	145.8	nM	PMID[551293]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	7943.3	nM	PMID[551293]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	501187.2	nM	PMID[551294]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	26917.7	nM	PubChem BioAssay data set
NPT32	Organism	Mus musculus	Mus musculus	HD50	=	30.0	mg kg-1	PMID[551287]
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	100.0	mg.kg-1	PMID[551287]
NPT27	Others	Unspecified		EC50	=	45498806015.0	nM	PMID[551288]
NPT35	Others	n.a.		Log PNalk	=	0.34	n.a.	PMID[551289]
NPT27	Others	Unspecified		Papp	=	24.34	10^-6 cm/s	PMID[551291]
NPT27	Others	Unspecified		Papp	=	262.87	10^-6 cm/s	PMID[551291]
NPT27	Others	Unspecified		LogP app	=	-3.58	n.a.	PMID[551291]
NPT35	Others	n.a.		LogP	=	2.3	n.a.	PMID[551291]
NPT27	Others	Unspecified		LogP app	=	4.61	n.a.	PMID[551291]
NPT27	Others	Unspecified		R%	=	20.0	%	PMID[551291]
NPT2	Others	Unspecified		Potency	=	29092.9	nM	PMID[551293]
NPT2	Others	Unspecified		AC50	>	420000.0	nM	PMID[551293]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	Potency	n.a.	1412537.5	nM	PMID[551294]
NPT2	Others	Unspecified		Potency	n.a.	12589.3	nM	PMID[551293]
NPT610	Others	Molecular identity unknown		Potency	n.a.	891250.9	nM	PMID[551294]
NPT610	Others	Molecular identity unknown		Potency	n.a.	1412537.5	nM	PMID[551294]
NPT2	Others	Unspecified		Potency	n.a.	21575.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24208.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54195.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	60261.3	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 NPC204210 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	330
0.1-0.2	2612
0.2-0.3	8142
0.3-0.4	11446
0.4-0.5	6204
0.5-0.6	9120
0.6-0.7	3766
0.7-0.8	832
0.8-0.85	143
0.85-0.9	71
0.9-0.95	28
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC70436
0.9663	High Similarity	NPC8392
0.9451	High Similarity	NPC77492
0.9348	High Similarity	NPC252821
0.9348	High Similarity	NPC128723
0.9348	High Similarity	NPC122005
0.9318	High Similarity	NPC123273
0.9318	High Similarity	NPC258219
0.9318	High Similarity	NPC242240
0.9318	High Similarity	NPC318325
0.931	High Similarity	NPC23167
0.931	High Similarity	NPC407
0.931	High Similarity	NPC307235
0.9302	High Similarity	NPC248817
0.9302	High Similarity	NPC286904
0.9247	High Similarity	NPC225506
0.9231	High Similarity	NPC144682
0.9205	High Similarity	NPC113460
0.9205	High Similarity	NPC25493
0.9195	High Similarity	NPC155393
0.9195	High Similarity	NPC197783
0.9186	High Similarity	NPC124436
0.9186	High Similarity	NPC265146
0.9121	High Similarity	NPC128062
0.9121	High Similarity	NPC289769
0.9111	High Similarity	NPC304541
0.9111	High Similarity	NPC306074
0.9101	High Similarity	NPC177420
0.9101	High Similarity	NPC280347
0.9091	High Similarity	NPC184169
0.908	High Similarity	NPC175313
0.9	High Similarity	NPC55561
0.8989	High Similarity	NPC19680
0.8913	High Similarity	NPC152415
0.8913	High Similarity	NPC316301
0.8913	High Similarity	NPC27323
0.8901	High Similarity	NPC155908
0.8901	High Similarity	NPC45040
0.8901	High Similarity	NPC231150
0.8889	High Similarity	NPC98772
0.8866	High Similarity	NPC138942
0.8866	High Similarity	NPC303141
0.8854	High Similarity	NPC168829
0.8854	High Similarity	NPC470202
0.8817	High Similarity	NPC26244
0.8804	High Similarity	NPC271440
0.8804	High Similarity	NPC138117
0.8804	High Similarity	NPC325292
0.8791	High Similarity	NPC300017
0.8778	High Similarity	NPC27974
0.8778	High Similarity	NPC104216
0.8776	High Similarity	NPC271274
0.8763	High Similarity	NPC288411
0.8737	High Similarity	NPC80027
0.8723	High Similarity	NPC259512
0.8723	High Similarity	NPC473388
0.8723	High Similarity	NPC312132
0.871	High Similarity	NPC245187
0.871	High Similarity	NPC151715
0.8696	High Similarity	NPC270547
0.8687	High Similarity	NPC228737
0.8673	High Similarity	NPC243677
0.866	High Similarity	NPC108497
0.8652	High Similarity	NPC150837
0.8646	High Similarity	NPC211885
0.8632	High Similarity	NPC79241
0.8632	High Similarity	NPC6597
0.8632	High Similarity	NPC225464
0.8617	High Similarity	NPC274678
0.8617	High Similarity	NPC313650
0.8617	High Similarity	NPC222146
0.8602	High Similarity	NPC162314
0.8602	High Similarity	NPC55903
0.8602	High Similarity	NPC306884
0.8602	High Similarity	NPC147284
0.8602	High Similarity	NPC181709
0.8602	High Similarity	NPC210497
0.8602	High Similarity	NPC3358
0.8602	High Similarity	NPC29373
0.8602	High Similarity	NPC94139
0.86	High Similarity	NPC61885
0.86	High Similarity	NPC63698
0.8587	High Similarity	NPC47950
0.8587	High Similarity	NPC300478
0.8587	High Similarity	NPC192
0.8586	High Similarity	NPC21594
0.8586	High Similarity	NPC54765
0.8557	High Similarity	NPC51015
0.8542	High Similarity	NPC92730
0.8542	High Similarity	NPC33675
0.8542	High Similarity	NPC299762
0.8515	High Similarity	NPC471954
0.8515	High Similarity	NPC75272
0.8515	High Similarity	NPC58865
0.85	High Similarity	NPC151477
0.8485	Intermediate Similarity	NPC219286
0.8485	Intermediate Similarity	NPC99557
0.8469	Intermediate Similarity	NPC269212
0.8454	Intermediate Similarity	NPC129373
0.8454	Intermediate Similarity	NPC174911
0.8454	Intermediate Similarity	NPC248396
0.8454	Intermediate Similarity	NPC72729
0.8454	Intermediate Similarity	NPC48730
0.8438	Intermediate Similarity	NPC260000
0.8438	Intermediate Similarity	NPC475078
0.8438	Intermediate Similarity	NPC152097
0.8431	Intermediate Similarity	NPC13482
0.8431	Intermediate Similarity	NPC296683
0.8421	Intermediate Similarity	NPC246679
0.8416	Intermediate Similarity	NPC262365
0.8416	Intermediate Similarity	NPC95344
0.8416	Intermediate Similarity	NPC470039
0.8384	Intermediate Similarity	NPC272029
0.8384	Intermediate Similarity	NPC238696
0.8384	Intermediate Similarity	NPC119860
0.8367	Intermediate Similarity	NPC252105
0.8351	Intermediate Similarity	NPC51333
0.8351	Intermediate Similarity	NPC260775
0.8351	Intermediate Similarity	NPC216468
0.8351	Intermediate Similarity	NPC78119
0.8351	Intermediate Similarity	NPC132078
0.8351	Intermediate Similarity	NPC280869
0.835	Intermediate Similarity	NPC225679
0.835	Intermediate Similarity	NPC165770
0.835	Intermediate Similarity	NPC476632
0.835	Intermediate Similarity	NPC95716
0.835	Intermediate Similarity	NPC4493
0.8333	Intermediate Similarity	NPC202986
0.8333	Intermediate Similarity	NPC292730
0.8333	Intermediate Similarity	NPC82664
0.8333	Intermediate Similarity	NPC216520
0.8333	Intermediate Similarity	NPC314187
0.8333	Intermediate Similarity	NPC283711
0.8333	Intermediate Similarity	NPC132271
0.8316	Intermediate Similarity	NPC76938
0.8316	Intermediate Similarity	NPC81010
0.8316	Intermediate Similarity	NPC32977
0.83	Intermediate Similarity	NPC117115
0.83	Intermediate Similarity	NPC474839
0.8283	Intermediate Similarity	NPC235762
0.8283	Intermediate Similarity	NPC471228
0.8269	Intermediate Similarity	NPC228425
0.8269	Intermediate Similarity	NPC43525
0.8269	Intermediate Similarity	NPC46940
0.8269	Intermediate Similarity	NPC250323
0.8265	Intermediate Similarity	NPC130756
0.8265	Intermediate Similarity	NPC12931
0.8265	Intermediate Similarity	NPC213730
0.8265	Intermediate Similarity	NPC70677
0.8252	Intermediate Similarity	NPC224870
0.8252	Intermediate Similarity	NPC44732
0.8252	Intermediate Similarity	NPC141782
0.8247	Intermediate Similarity	NPC156313
0.8247	Intermediate Similarity	NPC109955
0.8247	Intermediate Similarity	NPC107619
0.8247	Intermediate Similarity	NPC474073
0.8247	Intermediate Similarity	NPC32674
0.8229	Intermediate Similarity	NPC286006
0.8229	Intermediate Similarity	NPC32714
0.8229	Intermediate Similarity	NPC107522
0.8218	Intermediate Similarity	NPC469913
0.8218	Intermediate Similarity	NPC248904
0.82	Intermediate Similarity	NPC120719
0.82	Intermediate Similarity	NPC475225
0.82	Intermediate Similarity	NPC475580
0.8191	Intermediate Similarity	NPC151764
0.8191	Intermediate Similarity	NPC312304
0.819	Intermediate Similarity	NPC141003
0.819	Intermediate Similarity	NPC715
0.819	Intermediate Similarity	NPC35344
0.819	Intermediate Similarity	NPC242136
0.819	Intermediate Similarity	NPC117846
0.8182	Intermediate Similarity	NPC101025
0.8182	Intermediate Similarity	NPC472585
0.8182	Intermediate Similarity	NPC7686
0.8182	Intermediate Similarity	NPC91461
0.8182	Intermediate Similarity	NPC40258
0.8182	Intermediate Similarity	NPC477685
0.8182	Intermediate Similarity	NPC12221
0.8182	Intermediate Similarity	NPC471578
0.8182	Intermediate Similarity	NPC80800
0.8173	Intermediate Similarity	NPC151537
0.8173	Intermediate Similarity	NPC260323
0.8173	Intermediate Similarity	NPC176279
0.8173	Intermediate Similarity	NPC308689
0.8163	Intermediate Similarity	NPC171843
0.8163	Intermediate Similarity	NPC245561
0.8119	Intermediate Similarity	NPC154899
0.8119	Intermediate Similarity	NPC292452
0.8119	Intermediate Similarity	NPC233396
0.8119	Intermediate Similarity	NPC47284
0.8113	Intermediate Similarity	NPC12656
0.8113	Intermediate Similarity	NPC195922
0.8113	Intermediate Similarity	NPC107240
0.81	Intermediate Similarity	NPC196479
0.81	Intermediate Similarity	NPC135784
0.81	Intermediate Similarity	NPC62351
0.8095	Intermediate Similarity	NPC286222
0.8095	Intermediate Similarity	NPC228988
0.809	Intermediate Similarity	NPC133050

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 NPC204210 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	1115
0.2-0.3	1540
0.3-0.4	2905
0.4-0.5	1815
0.5-0.6	987
0.6-0.7	339
0.7-0.8	68
0.8-0.85	1
0.85-0.9	10
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD1809	Phase 2
0.9222	High Similarity	NPD845	Approved
0.9186	High Similarity	NPD111	Approved
0.8913	High Similarity	NPD1432	Clinical (unspecified phase)
0.8817	High Similarity	NPD2859	Approved
0.8817	High Similarity	NPD2860	Approved
0.8817	High Similarity	NPD844	Approved
0.875	High Similarity	NPD940	Approved
0.875	High Similarity	NPD846	Approved
0.8723	High Similarity	NPD288	Approved
0.871	High Similarity	NPD2933	Approved
0.871	High Similarity	NPD2934	Approved
0.8542	High Similarity	NPD3020	Approved
0.8454	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.802	Intermediate Similarity	NPD9608	Approved
0.802	Intermediate Similarity	NPD9610	Approved
0.8	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD2342	Discontinued
0.7921	Intermediate Similarity	NPD9500	Approved
0.7907	Intermediate Similarity	NPD9087	Approved
0.79	Intermediate Similarity	NPD1242	Phase 1
0.7879	Intermediate Similarity	NPD9273	Approved
0.785	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5303	Approved
0.7818	Intermediate Similarity	NPD5304	Approved
0.781	Intermediate Similarity	NPD3021	Approved
0.781	Intermediate Similarity	NPD3022	Approved
0.7757	Intermediate Similarity	NPD7635	Approved
0.7692	Intermediate Similarity	NPD1445	Approved
0.7692	Intermediate Similarity	NPD1444	Approved
0.7679	Intermediate Similarity	NPD4589	Approved
0.7642	Intermediate Similarity	NPD4750	Phase 3
0.764	Intermediate Similarity	NPD9294	Approved
0.7556	Intermediate Similarity	NPD9088	Approved
0.7549	Intermediate Similarity	NPD3028	Approved
0.7523	Intermediate Similarity	NPD2228	Approved
0.7523	Intermediate Similarity	NPD2234	Approved
0.7523	Intermediate Similarity	NPD2229	Approved
0.75	Intermediate Similarity	NPD228	Approved
0.7477	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1792	Phase 2
0.7453	Intermediate Similarity	NPD290	Approved
0.7434	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6671	Approved
0.7387	Intermediate Similarity	NPD255	Approved
0.7387	Intermediate Similarity	NPD256	Approved
0.7383	Intermediate Similarity	NPD2684	Approved
0.7368	Intermediate Similarity	NPD4626	Approved
0.7358	Intermediate Similarity	NPD968	Approved
0.7345	Intermediate Similarity	NPD3091	Approved
0.7304	Intermediate Similarity	NPD3143	Discontinued
0.7304	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD1134	Approved
0.7288	Intermediate Similarity	NPD1129	Approved
0.7288	Intermediate Similarity	NPD1131	Approved
0.7288	Intermediate Similarity	NPD1133	Approved
0.7288	Intermediate Similarity	NPD1135	Approved
0.7281	Intermediate Similarity	NPD4093	Discontinued
0.7273	Intermediate Similarity	NPD9379	Approved
0.7273	Intermediate Similarity	NPD9377	Approved
0.7234	Intermediate Similarity	NPD9089	Approved
0.7222	Intermediate Similarity	NPD9266	Approved
0.7222	Intermediate Similarity	NPD74	Approved
0.7217	Intermediate Similarity	NPD2286	Discontinued
0.7217	Intermediate Similarity	NPD1751	Approved
0.7217	Intermediate Similarity	NPD2932	Approved
0.7217	Intermediate Similarity	NPD4059	Approved
0.7217	Intermediate Similarity	NPD3019	Approved
0.72	Intermediate Similarity	NPD159	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7330	Discontinued
0.7193	Intermediate Similarity	NPD1548	Phase 1
0.7179	Intermediate Similarity	NPD3070	Discontinued
0.7168	Intermediate Similarity	NPD9493	Approved
0.7168	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD497	Approved
0.7143	Intermediate Similarity	NPD1791	Approved
0.7143	Intermediate Similarity	NPD1793	Approved
0.7143	Intermediate Similarity	NPD1164	Approved
0.7143	Intermediate Similarity	NPD475	Phase 2
0.713	Intermediate Similarity	NPD9267	Approved
0.713	Intermediate Similarity	NPD9264	Approved
0.713	Intermediate Similarity	NPD9263	Approved
0.7128	Intermediate Similarity	NPD9093	Approved
0.7117	Intermediate Similarity	NPD7843	Approved
0.7117	Intermediate Similarity	NPD821	Approved
0.7117	Intermediate Similarity	NPD1138	Approved
0.7105	Intermediate Similarity	NPD317	Approved
0.7105	Intermediate Similarity	NPD16	Approved
0.7105	Intermediate Similarity	NPD856	Approved
0.7105	Intermediate Similarity	NPD318	Approved
0.7094	Intermediate Similarity	NPD422	Phase 1
0.7094	Intermediate Similarity	NPD3092	Approved
0.7094	Intermediate Similarity	NPD1610	Phase 2
0.7091	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD9295	Approved
0.7069	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD496	Approved
0.7054	Intermediate Similarity	NPD495	Approved
0.7054	Intermediate Similarity	NPD498	Approved
0.7043	Intermediate Similarity	NPD9545	Approved
0.7043	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1137	Approved
0.7027	Intermediate Similarity	NPD1139	Approved
0.7018	Intermediate Similarity	NPD9568	Approved
0.7018	Intermediate Similarity	NPD7636	Approved
0.701	Intermediate Similarity	NPD9073	Approved
0.7	Intermediate Similarity	NPD5451	Approved
0.6992	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD9618	Approved
0.6991	Remote Similarity	NPD9614	Approved
0.6983	Remote Similarity	NPD5691	Approved
0.6949	Remote Similarity	NPD1201	Approved
0.6942	Remote Similarity	NPD3690	Phase 2
0.6942	Remote Similarity	NPD3691	Phase 2
0.693	Remote Similarity	NPD7157	Approved
0.6923	Remote Similarity	NPD3095	Discontinued
0.6916	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD594	Approved
0.6903	Remote Similarity	NPD592	Approved
0.6897	Remote Similarity	NPD1759	Phase 1
0.6885	Remote Similarity	NPD4212	Discontinued
0.6885	Remote Similarity	NPD4208	Discontinued
0.6881	Remote Similarity	NPD3134	Approved
0.688	Remote Similarity	NPD4060	Phase 1
0.688	Remote Similarity	NPD1555	Discontinued
0.687	Remote Similarity	NPD405	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3094	Phase 2
0.6833	Remote Similarity	NPD6582	Phase 2
0.6833	Remote Similarity	NPD6583	Phase 3
0.6833	Remote Similarity	NPD4659	Approved
0.6829	Remote Similarity	NPD4207	Discontinued
0.6829	Remote Similarity	NPD4908	Phase 1
0.6818	Remote Similarity	NPD1358	Approved
0.6814	Remote Similarity	NPD5535	Approved
0.681	Remote Similarity	NPD1758	Phase 1
0.681	Remote Similarity	NPD9613	Approved
0.681	Remote Similarity	NPD9616	Approved
0.681	Remote Similarity	NPD9615	Approved
0.6803	Remote Similarity	NPD2195	Approved
0.6803	Remote Similarity	NPD2194	Approved
0.68	Remote Similarity	NPD6407	Approved
0.68	Remote Similarity	NPD6405	Approved
0.68	Remote Similarity	NPD9094	Approved
0.6789	Remote Similarity	NPD9697	Approved
0.6783	Remote Similarity	NPD6387	Discontinued
0.6783	Remote Similarity	NPD709	Approved
0.678	Remote Similarity	NPD2667	Approved
0.678	Remote Similarity	NPD9381	Approved
0.678	Remote Similarity	NPD2668	Approved
0.678	Remote Similarity	NPD9384	Approved
0.6777	Remote Similarity	NPD1283	Approved
0.6777	Remote Similarity	NPD6696	Suspended
0.6774	Remote Similarity	NPD4625	Phase 3
0.6759	Remote Similarity	NPD9261	Approved
0.6754	Remote Similarity	NPD5283	Phase 1
0.6754	Remote Similarity	NPD1398	Phase 1
0.6752	Remote Similarity	NPD316	Approved
0.675	Remote Similarity	NPD2562	Approved
0.675	Remote Similarity	NPD2561	Approved
0.6748	Remote Similarity	NPD5736	Approved
0.6748	Remote Similarity	NPD2861	Phase 2
0.6748	Remote Similarity	NPD3637	Approved
0.6748	Remote Similarity	NPD3635	Approved
0.6748	Remote Similarity	NPD3636	Approved
0.6731	Remote Similarity	NPD9296	Approved
0.6729	Remote Similarity	NPD1616	Discontinued
0.6723	Remote Similarity	NPD3421	Phase 3
0.6723	Remote Similarity	NPD1980	Approved
0.6723	Remote Similarity	NPD1981	Approved
0.6723	Remote Similarity	NPD1983	Approved
0.6723	Remote Similarity	NPD3847	Discontinued
0.6721	Remote Similarity	NPD4103	Phase 2
0.6721	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD1470	Approved
0.6721	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD3554	Approved
0.6719	Remote Similarity	NPD3552	Approved
0.6719	Remote Similarity	NPD3555	Approved
0.6719	Remote Similarity	NPD3553	Approved
0.6698	Remote Similarity	NPD9609	Approved
0.6698	Remote Similarity	NPD9612	Approved
0.6698	Remote Similarity	NPD9611	Approved
0.6697	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD9244	Approved
0.6696	Remote Similarity	NPD9281	Approved
0.6695	Remote Similarity	NPD1357	Approved
0.6695	Remote Similarity	NPD1651	Approved
0.6694	Remote Similarity	NPD9622	Approved
0.6694	Remote Similarity	NPD1669	Approved
0.6694	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD2605	Approved
0.6694	Remote Similarity	NPD2606	Approved
0.6694	Remote Similarity	NPD4749	Approved
0.6667	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4817	Approved
0.6667	Remote Similarity	NPD5351	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