NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	122.07
Volume:	139.249
LogP:	2.479
LogD:	2.613
LogS:	-1.492
# 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:	1.586
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:	-4.356
MDCK Permeability:	2.6891293600783683e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.12
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.321
30% Bioavailability (F30%):	0.356

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.744
Plasma Protein Binding (PPB):	84.00629425048828%
Volume Distribution (VD):	1.406
Pgp-substrate:	12.740068435668945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.902
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.643
CYP2C19-substrate:	0.69
CYP2C9-inhibitor:	0.199
CYP2C9-substrate:	0.851
CYP2D6-inhibitor:	0.651
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.096
CYP3A4-substrate:	0.396

ADMET: Excretion

Clearance (CL):	15.302
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.042
Drug-inuced Liver Injury (DILI):	0.057
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.284
Maximum Recommended Daily Dose:	0.375
Skin Sensitization:	0.534
Carcinogencity:	0.539
Eye Corrosion:	0.973
Eye Irritation:	0.994
Respiratory Toxicity:	0.436

Download Data

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

Natural Product: NPC231150

Natural Product ID:	NPC231150
*Common Name:**	2,5-Dimethylphenol
IUPAC Name:	2,5-dimethylphenol
Synonyms:	2,5-Dimethyl-Phenol; 2,5-Dimethylphenol
Standard InCHIKey:	NKTOLZVEWDHZMU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H10O/c1-6-3-4-7(2)8(9)5-6/h3-5,9H,1-2H3
SMILES:	Cc1ccc(c(c1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL192591
PubChem CID:	7267
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004208] Xylenes [CHEMONTID:0004212] Xylenols [CHEMONTID:0004215] p-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
NPO5949	Pericarpium arecae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO5949	Pericarpium arecae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1
Potency	4

Activity Type	# Activity
Individual Protein	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	14.1	nM	PMID[478647]
NPT35	Others	n.a.		Log PNalk	=	0.38	n.a.	PMID[478645]
NPT2	Others	Unspecified		Potency	n.a.	477.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21327.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1068.9	nM	PubChem BioAssay data set

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC231150 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	331
0.1-0.2	2645
0.2-0.3	8417
0.3-0.4	11331
0.4-0.5	6508
0.5-0.6	9211
0.6-0.7	3196
0.7-0.8	782
0.8-0.85	165
0.85-0.9	84
0.9-0.95	26
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9556	High Similarity	NPC259512
0.9556	High Similarity	NPC312132
0.9451	High Similarity	NPC79241
0.9451	High Similarity	NPC6597
0.9425	High Similarity	NPC27974
0.9348	High Similarity	NPC299762
0.9348	High Similarity	NPC33675
0.9333	High Similarity	NPC245187
0.931	High Similarity	NPC407
0.931	High Similarity	NPC307235
0.9302	High Similarity	NPC150837
0.9302	High Similarity	NPC286904
0.9247	High Similarity	NPC174911
0.9247	High Similarity	NPC72729
0.9222	High Similarity	NPC29373
0.9195	High Similarity	NPC155393
0.9149	High Similarity	NPC80800
0.9149	High Similarity	NPC252105
0.9053	High Similarity	NPC235762
0.9053	High Similarity	NPC471228
0.9032	High Similarity	NPC152097
0.9032	High Similarity	NPC475078
0.9011	High Similarity	NPC162314
0.9011	High Similarity	NPC147284
0.9011	High Similarity	NPC3358
0.9011	High Similarity	NPC94139
0.9011	High Similarity	NPC210497
0.9011	High Similarity	NPC306884
0.9011	High Similarity	NPC55903
0.9	High Similarity	NPC192
0.8989	High Similarity	NPC19680
0.8958	High Similarity	NPC475225
0.8947	High Similarity	NPC477685
0.8936	High Similarity	NPC260775
0.8913	High Similarity	NPC152415
0.8901	High Similarity	NPC306074
0.8901	High Similarity	NPC204210
0.8876	High Similarity	NPC23167
0.8866	High Similarity	NPC47284
0.8864	High Similarity	NPC248817
0.8842	High Similarity	NPC70677
0.8842	High Similarity	NPC12931
0.8842	High Similarity	NPC130756
0.8842	High Similarity	NPC129373
0.8842	High Similarity	NPC248396
0.8842	High Similarity	NPC48730
0.883	High Similarity	NPC156313
0.8791	High Similarity	NPC312304
0.8778	High Similarity	NPC25493
0.8778	High Similarity	NPC113460
0.8776	High Similarity	NPC310456
0.8776	High Similarity	NPC53740
0.8764	High Similarity	NPC197783
0.8763	High Similarity	NPC238696
0.8763	High Similarity	NPC218879
0.8763	High Similarity	NPC272029
0.8763	High Similarity	NPC244513
0.8763	High Similarity	NPC227458
0.875	High Similarity	NPC124436
0.875	High Similarity	NPC265146
0.871	High Similarity	NPC76938
0.8696	High Similarity	NPC304541
0.8687	High Similarity	NPC66834
0.8687	High Similarity	NPC474352
0.8687	High Similarity	NPC232523
0.8687	High Similarity	NPC158253
0.8687	High Similarity	NPC204901
0.8681	High Similarity	NPC242240
0.8681	High Similarity	NPC258219
0.8681	High Similarity	NPC318325
0.8681	High Similarity	NPC123273
0.8681	High Similarity	NPC70436
0.8681	High Similarity	NPC177420
0.8681	High Similarity	NPC280347
0.8673	High Similarity	NPC117115
0.8673	High Similarity	NPC37802
0.8667	High Similarity	NPC184169
0.866	High Similarity	NPC108497
0.8652	High Similarity	NPC175313
0.8646	High Similarity	NPC130103
0.8632	High Similarity	NPC77492
0.8632	High Similarity	NPC88420
0.8632	High Similarity	NPC474073
0.8617	High Similarity	NPC274678
0.8617	High Similarity	NPC8392
0.8617	High Similarity	NPC222146
0.8617	High Similarity	NPC32714
0.8602	High Similarity	NPC271440
0.86	High Similarity	NPC174981
0.86	High Similarity	NPC306295
0.86	High Similarity	NPC64586
0.8587	High Similarity	NPC47950
0.8587	High Similarity	NPC55561
0.8586	High Similarity	NPC21594
0.8586	High Similarity	NPC99836
0.8586	High Similarity	NPC12640
0.8586	High Similarity	NPC201662
0.8571	High Similarity	NPC130817
0.8571	High Similarity	NPC475580
0.8557	High Similarity	NPC12221
0.8542	High Similarity	NPC122005
0.8542	High Similarity	NPC252821
0.8526	High Similarity	NPC202986
0.8515	High Similarity	NPC33728
0.8515	High Similarity	NPC19808
0.8515	High Similarity	NPC58865
0.8511	High Similarity	NPC289769
0.8511	High Similarity	NPC27323
0.8511	High Similarity	NPC128062
0.8511	High Similarity	NPC316301
0.85	High Similarity	NPC151477
0.8495	Intermediate Similarity	NPC155908
0.8485	Intermediate Similarity	NPC471350
0.8478	Intermediate Similarity	NPC98772
0.8469	Intermediate Similarity	NPC269212
0.8469	Intermediate Similarity	NPC233827
0.8469	Intermediate Similarity	NPC168393
0.8454	Intermediate Similarity	NPC225506
0.8454	Intermediate Similarity	NPC166761
0.8438	Intermediate Similarity	NPC109955
0.8438	Intermediate Similarity	NPC32674
0.8421	Intermediate Similarity	NPC257182
0.8421	Intermediate Similarity	NPC246679
0.8421	Intermediate Similarity	NPC107522
0.8404	Intermediate Similarity	NPC138117
0.8404	Intermediate Similarity	NPC295295
0.8404	Intermediate Similarity	NPC325292
0.84	Intermediate Similarity	NPC155072
0.8387	Intermediate Similarity	NPC300017
0.8384	Intermediate Similarity	NPC102216
0.8384	Intermediate Similarity	NPC93831
0.837	Intermediate Similarity	NPC104216
0.8351	Intermediate Similarity	NPC80027
0.8351	Intermediate Similarity	NPC128723
0.835	Intermediate Similarity	NPC224527
0.8333	Intermediate Similarity	NPC299568
0.8333	Intermediate Similarity	NPC314187
0.8333	Intermediate Similarity	NPC186385
0.8333	Intermediate Similarity	NPC283711
0.8317	Intermediate Similarity	NPC320439
0.8317	Intermediate Similarity	NPC233320
0.83	Intermediate Similarity	NPC292452
0.8298	Intermediate Similarity	NPC270547
0.8298	Intermediate Similarity	NPC45040
0.8283	Intermediate Similarity	NPC196479
0.8283	Intermediate Similarity	NPC94351
0.8283	Intermediate Similarity	NPC242342
0.8283	Intermediate Similarity	NPC146798
0.8283	Intermediate Similarity	NPC71002
0.8283	Intermediate Similarity	NPC53051
0.8283	Intermediate Similarity	NPC313030
0.8283	Intermediate Similarity	NPC249828
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	NPC46940
0.8269	Intermediate Similarity	NPC26615
0.8269	Intermediate Similarity	NPC166995
0.8269	Intermediate Similarity	NPC228452
0.8269	Intermediate Similarity	NPC302371
0.8269	Intermediate Similarity	NPC250323
0.8265	Intermediate Similarity	NPC211885
0.8265	Intermediate Similarity	NPC294741
0.8265	Intermediate Similarity	NPC10588
0.8252	Intermediate Similarity	NPC224870
0.8252	Intermediate Similarity	NPC132720
0.8247	Intermediate Similarity	NPC225464
0.8247	Intermediate Similarity	NPC291789
0.8229	Intermediate Similarity	NPC144682
0.8229	Intermediate Similarity	NPC313650
0.8229	Intermediate Similarity	NPC26244
0.8222	Intermediate Similarity	NPC168855
0.8218	Intermediate Similarity	NPC54765
0.8218	Intermediate Similarity	NPC469913
0.8218	Intermediate Similarity	NPC67250
0.8211	Intermediate Similarity	NPC181709
0.82	Intermediate Similarity	NPC120719
0.8191	Intermediate Similarity	NPC300478
0.819	Intermediate Similarity	NPC715
0.819	Intermediate Similarity	NPC190212
0.819	Intermediate Similarity	NPC117846
0.8182	Intermediate Similarity	NPC24407
0.8182	Intermediate Similarity	NPC137415
0.8182	Intermediate Similarity	NPC100340
0.8182	Intermediate Similarity	NPC294186
0.8182	Intermediate Similarity	NPC166313
0.8182	Intermediate Similarity	NPC94343
0.8182	Intermediate Similarity	NPC72947
0.8182	Intermediate Similarity	NPC284011
0.8182	Intermediate Similarity	NPC192032
0.8182	Intermediate Similarity	NPC110764
0.8182	Intermediate Similarity	NPC143659
0.8182	Intermediate Similarity	NPC11280
0.8182	Intermediate Similarity	NPC147310
0.8173	Intermediate Similarity	NPC95716
0.8173	Intermediate Similarity	NPC77772
0.8173	Intermediate Similarity	NPC266937

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 NPC231150 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	1114
0.2-0.3	1631
0.3-0.4	2901
0.4-0.5	1781
0.5-0.6	954
0.6-0.7	328
0.7-0.8	56
0.8-0.85	12
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9663	High Similarity	NPD844	Approved
0.9556	High Similarity	NPD288	Approved
0.8842	High Similarity	NPD289	Clinical (unspecified phase)
0.875	High Similarity	NPD111	Approved
0.8602	High Similarity	NPD845	Approved
0.8511	High Similarity	NPD1432	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4750	Phase 3
0.8317	Intermediate Similarity	NPD2342	Discontinued
0.8316	Intermediate Similarity	NPD2933	Approved
0.8316	Intermediate Similarity	NPD2934	Approved
0.8229	Intermediate Similarity	NPD1809	Phase 2
0.8229	Intermediate Similarity	NPD2859	Approved
0.8229	Intermediate Similarity	NPD2860	Approved
0.8182	Intermediate Similarity	NPD846	Approved
0.8182	Intermediate Similarity	NPD940	Approved
0.8163	Intermediate Similarity	NPD3020	Approved
0.8095	Intermediate Similarity	NPD7635	Approved
0.8081	Intermediate Similarity	NPD1242	Phase 1
0.8039	Intermediate Similarity	NPD1445	Approved
0.8039	Intermediate Similarity	NPD1444	Approved
0.7921	Intermediate Similarity	NPD9500	Approved
0.7907	Intermediate Similarity	NPD9087	Approved
0.7879	Intermediate Similarity	NPD9273	Approved
0.781	Intermediate Similarity	NPD3021	Approved
0.781	Intermediate Similarity	NPD3022	Approved
0.781	Intermediate Similarity	NPD1792	Phase 2
0.7706	Intermediate Similarity	NPD6671	Approved
0.767	Intermediate Similarity	NPD9610	Approved
0.767	Intermediate Similarity	NPD9608	Approved
0.7664	Intermediate Similarity	NPD228	Approved
0.764	Intermediate Similarity	NPD9294	Approved
0.7556	Intermediate Similarity	NPD9088	Approved
0.75	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD1980	Approved
0.7456	Intermediate Similarity	NPD1983	Approved
0.7456	Intermediate Similarity	NPD1981	Approved
0.7455	Intermediate Similarity	NPD9614	Approved
0.7455	Intermediate Similarity	NPD497	Approved
0.7455	Intermediate Similarity	NPD1793	Approved
0.7455	Intermediate Similarity	NPD1791	Approved
0.7455	Intermediate Similarity	NPD9618	Approved
0.7453	Intermediate Similarity	NPD290	Approved
0.7431	Intermediate Similarity	NPD9377	Approved
0.7431	Intermediate Similarity	NPD9379	Approved
0.7368	Intermediate Similarity	NPD1778	Approved
0.7368	Intermediate Similarity	NPD4626	Approved
0.7364	Intermediate Similarity	NPD495	Approved
0.7364	Intermediate Similarity	NPD496	Approved
0.7364	Intermediate Similarity	NPD498	Approved
0.7358	Intermediate Similarity	NPD968	Approved
0.7345	Intermediate Similarity	NPD3091	Approved
0.7321	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD4749	Approved
0.7257	Intermediate Similarity	NPD9616	Approved
0.7257	Intermediate Similarity	NPD9613	Approved
0.7257	Intermediate Similarity	NPD9615	Approved
0.7248	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1201	Approved
0.7234	Intermediate Similarity	NPD9089	Approved
0.7232	Intermediate Similarity	NPD709	Approved
0.7222	Intermediate Similarity	NPD74	Approved
0.7222	Intermediate Similarity	NPD9266	Approved
0.7217	Intermediate Similarity	NPD2932	Approved
0.7217	Intermediate Similarity	NPD2286	Discontinued
0.7217	Intermediate Similarity	NPD1751	Approved
0.7217	Intermediate Similarity	NPD3019	Approved
0.7217	Intermediate Similarity	NPD4059	Approved
0.7212	Intermediate Similarity	NPD3028	Approved
0.7207	Intermediate Similarity	NPD2234	Approved
0.7207	Intermediate Similarity	NPD2229	Approved
0.7207	Intermediate Similarity	NPD2228	Approved
0.7193	Intermediate Similarity	NPD316	Approved
0.7182	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD9244	Approved
0.7168	Intermediate Similarity	NPD9493	Approved
0.7168	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD9267	Approved
0.713	Intermediate Similarity	NPD9263	Approved
0.713	Intermediate Similarity	NPD9264	Approved
0.713	Intermediate Similarity	NPD4093	Discontinued
0.7128	Intermediate Similarity	NPD9093	Approved
0.7119	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD3092	Approved
0.7071	Intermediate Similarity	NPD9295	Approved
0.7069	Intermediate Similarity	NPD4589	Approved
0.7059	Intermediate Similarity	NPD6696	Suspended
0.7054	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1398	Phase 1
0.7049	Intermediate Similarity	NPD4625	Phase 3
0.7048	Intermediate Similarity	NPD1616	Discontinued
0.7043	Intermediate Similarity	NPD5304	Approved
0.7043	Intermediate Similarity	NPD5303	Approved
0.701	Intermediate Similarity	NPD9073	Approved
0.7009	Intermediate Similarity	NPD3496	Discontinued
0.7	Intermediate Similarity	NPD1470	Approved
0.6983	Remote Similarity	NPD5691	Approved
0.6972	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.693	Remote Similarity	NPD256	Approved
0.693	Remote Similarity	NPD255	Approved
0.6923	Remote Similarity	NPD9384	Approved
0.6923	Remote Similarity	NPD9381	Approved
0.6923	Remote Similarity	NPD3095	Discontinued
0.6916	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD2684	Approved
0.6897	Remote Similarity	NPD1548	Phase 1
0.6897	Remote Similarity	NPD1759	Phase 1
0.6891	Remote Similarity	NPD2232	Approved
0.6891	Remote Similarity	NPD2233	Approved
0.6891	Remote Similarity	NPD2230	Approved
0.687	Remote Similarity	NPD7340	Approved
0.686	Remote Similarity	NPD3094	Phase 2
0.6855	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD475	Phase 2
0.6838	Remote Similarity	NPD1357	Approved
0.6833	Remote Similarity	NPD9622	Approved
0.6833	Remote Similarity	NPD1755	Approved
0.6814	Remote Similarity	NPD821	Approved
0.681	Remote Similarity	NPD856	Approved
0.681	Remote Similarity	NPD1758	Phase 1
0.681	Remote Similarity	NPD318	Approved
0.681	Remote Similarity	NPD16	Approved
0.681	Remote Similarity	NPD317	Approved
0.6807	Remote Similarity	NPD1610	Phase 2
0.6807	Remote Similarity	NPD1611	Approved
0.6807	Remote Similarity	NPD422	Phase 1
0.6803	Remote Similarity	NPD2195	Approved
0.6803	Remote Similarity	NPD2194	Approved
0.68	Remote Similarity	NPD9094	Approved
0.6789	Remote Similarity	NPD9697	Approved
0.6777	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD1283	Approved
0.6759	Remote Similarity	NPD9261	Approved
0.6754	Remote Similarity	NPD5283	Phase 1
0.6752	Remote Similarity	NPD7330	Discontinued
0.6752	Remote Similarity	NPD9545	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
0.6724	Remote Similarity	NPD9568	Approved
0.6721	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD3053	Approved
0.6721	Remote Similarity	NPD3055	Approved
0.672	Remote Similarity	NPD411	Approved
0.6699	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD9609	Approved
0.6698	Remote Similarity	NPD9612	Approved
0.6698	Remote Similarity	NPD9611	Approved
0.6696	Remote Similarity	NPD9281	Approved
0.6695	Remote Similarity	NPD1651	Approved
0.6695	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD2606	Approved
0.6694	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD600	Approved
0.6694	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD2605	Approved
0.6694	Remote Similarity	NPD596	Approved
0.6667	Remote Similarity	NPD9621	Approved
0.6667	Remote Similarity	NPD9619	Approved
0.6667	Remote Similarity	NPD9620	Approved
0.6667	Remote Similarity	NPD6584	Phase 3
0.6667	Remote Similarity	NPD258	Approved
0.6667	Remote Similarity	NPD1138	Approved
0.6667	Remote Similarity	NPD7843	Approved
0.6667	Remote Similarity	NPD257	Approved
0.6641	Remote Similarity	NPD4097	Suspended
0.664	Remote Similarity	NPD5156	Approved
0.664	Remote Similarity	NPD5155	Approved
0.6639	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5311	Approved
0.6639	Remote Similarity	NPD5310	Approved
0.6638	Remote Similarity	NPD7157	Approved
0.6634	Remote Similarity	NPD1101	Approved
0.6614	Remote Similarity	NPD4060	Phase 1
0.6613	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD1712	Approved
0.6612	Remote Similarity	NPD1608	Approved
0.6612	Remote Similarity	NPD9717	Approved
0.6612	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD2235	Phase 2
0.6612	Remote Similarity	NPD2231	Phase 2
0.6598	Remote Similarity	NPD9250	Approved
0.6585	Remote Similarity	NPD1129	Approved
0.6585	Remote Similarity	NPD1135	Approved
0.6585	Remote Similarity	NPD1131	Approved
0.6585	Remote Similarity	NPD1164	Approved
0.6585	Remote Similarity	NPD1134	Approved
0.6585	Remote Similarity	NPD1133	Approved
0.6583	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD3026	Approved
0.6583	Remote Similarity	NPD3023	Approved
0.6583	Remote Similarity	NPD3143	Discontinued

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