NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	152.08
Volume:	165.335
LogP:	2.09
LogD:	1.902
LogS:	-1.369
# Rotatable Bonds:	0
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.597
Synthetic Accessibility Score:	2.204
Fsp3:	0.333
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:	-4.6
MDCK Permeability:	1.754115328367334e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.113
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.967
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.467
Plasma Protein Binding (PPB):	93.28075408935547%
Volume Distribution (VD):	0.504
Pgp-substrate:	5.097983360290527%

ADMET: Metabolism

CYP1A2-inhibitor:	0.859
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.159
CYP2C19-substrate:	0.573
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	0.719
CYP2D6-inhibitor:	0.281
CYP2D6-substrate:	0.775
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.281

ADMET: Excretion

Clearance (CL):	16.081
Half-life (T1/2):	0.868

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.446
Maximum Recommended Daily Dose:	0.81
Skin Sensitization:	0.923
Carcinogencity:	0.266
Eye Corrosion:	0.936
Eye Irritation:	0.973
Respiratory Toxicity:	0.52

Download Data

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

Natural Product: NPC224870

Natural Product ID:	NPC224870
*Common Name:**	2,4,5-Trimethylbenzene-1,3-Diol
IUPAC Name:	2,4,5-trimethylbenzene-1,3-diol
Synonyms:
Standard InCHIKey:	KRIDOPOPBBSDNT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H12O2/c1-5-4-8(10)7(3)9(11)6(5)2/h4,10-11H,1-3H3
SMILES:	Cc1c(C)cc(c(c1O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448432
PubChem CID:	15556234
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO32513	Penicillium citrinum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18281952]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	3800.0	nM	PMID[455994]

☑ 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 NPC224870 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	420
0.1-0.2	2142
0.2-0.3	6072
0.3-0.4	13239
0.4-0.5	5035
0.5-0.6	7554
0.6-0.7	6171
0.7-0.8	1766
0.8-0.85	188
0.85-0.9	91
0.9-0.95	17
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC263753
0.9259	High Similarity	NPC107240
0.9223	High Similarity	NPC244513
0.9223	High Similarity	NPC227458
0.9223	High Similarity	NPC218879
0.9167	High Similarity	NPC117846
0.9135	High Similarity	NPC37802
0.9074	High Similarity	NPC473521
0.9048	High Similarity	NPC201662
0.9048	High Similarity	NPC99836
0.9048	High Similarity	NPC12640
0.8981	High Similarity	NPC225679
0.8981	High Similarity	NPC4493
0.8981	High Similarity	NPC151537
0.8981	High Similarity	NPC165770
0.8981	High Similarity	NPC476632
0.8972	High Similarity	NPC186385
0.8972	High Similarity	NPC202647
0.8972	High Similarity	NPC299568
0.8962	High Similarity	NPC158253
0.8962	High Similarity	NPC204901
0.8962	High Similarity	NPC232523
0.8919	High Similarity	NPC115808
0.8909	High Similarity	NPC249270
0.8899	High Similarity	NPC43525
0.8899	High Similarity	NPC166995
0.8879	High Similarity	NPC174981
0.8868	High Similarity	NPC21594
0.8857	High Similarity	NPC272029
0.8839	High Similarity	NPC470760
0.8835	High Similarity	NPC80027
0.8829	High Similarity	NPC84999
0.8829	High Similarity	NPC246760
0.8807	High Similarity	NPC224527
0.8796	High Similarity	NPC33728
0.8796	High Similarity	NPC19808
0.8785	High Similarity	NPC151477
0.8761	High Similarity	NPC206
0.8718	High Similarity	NPC224342
0.8704	High Similarity	NPC61885
0.8704	High Similarity	NPC63698
0.8692	High Similarity	NPC248904
0.8684	High Similarity	NPC191866
0.8679	High Similarity	NPC102216
0.8679	High Similarity	NPC30506
0.8667	High Similarity	NPC24407
0.8667	High Similarity	NPC147310
0.8667	High Similarity	NPC166313
0.8667	High Similarity	NPC11280
0.8667	High Similarity	NPC137415
0.8667	High Similarity	NPC192032
0.8667	High Similarity	NPC294186
0.8649	High Similarity	NPC23804
0.8649	High Similarity	NPC319803
0.8644	High Similarity	NPC105031
0.8644	High Similarity	NPC293801
0.8636	High Similarity	NPC469912
0.8624	High Similarity	NPC58865
0.8621	High Similarity	NPC237667
0.8621	High Similarity	NPC39029
0.8609	High Similarity	NPC3239
0.8609	High Similarity	NPC282255
0.8598	High Similarity	NPC292452
0.8598	High Similarity	NPC471350
0.8598	High Similarity	NPC117115
0.8585	High Similarity	NPC302219
0.8585	High Similarity	NPC106396
0.8585	High Similarity	NPC53051
0.8585	High Similarity	NPC24404
0.8585	High Similarity	NPC242342
0.8585	High Similarity	NPC146798
0.8585	High Similarity	NPC85479
0.8585	High Similarity	NPC222522
0.8585	High Similarity	NPC168303
0.8585	High Similarity	NPC249828
0.8585	High Similarity	NPC313030
0.8585	High Similarity	NPC71002
0.8585	High Similarity	NPC94351
0.8571	High Similarity	NPC10588
0.8571	High Similarity	NPC166761
0.8571	High Similarity	NPC211885
0.8559	High Similarity	NPC46940
0.8559	High Similarity	NPC302371
0.8534	High Similarity	NPC24125
0.8529	High Similarity	NPC295295
0.8509	High Similarity	NPC277588
0.8509	High Similarity	NPC304510
0.8509	High Similarity	NPC172219
0.8505	High Similarity	NPC238696
0.8505	High Similarity	NPC119860
0.85	High Similarity	NPC53781
0.8496	Intermediate Similarity	NPC472893
0.8491	Intermediate Similarity	NPC72947
0.8491	Intermediate Similarity	NPC284011
0.8491	Intermediate Similarity	NPC100340
0.8491	Intermediate Similarity	NPC143659
0.8475	Intermediate Similarity	NPC53567
0.8468	Intermediate Similarity	NPC260323
0.8468	Intermediate Similarity	NPC176279
0.8468	Intermediate Similarity	NPC95716
0.8462	Intermediate Similarity	NPC312132
0.8462	Intermediate Similarity	NPC259512
0.8455	Intermediate Similarity	NPC314187
0.8447	Intermediate Similarity	NPC245187
0.8435	Intermediate Similarity	NPC471671
0.8435	Intermediate Similarity	NPC154030
0.8435	Intermediate Similarity	NPC144343
0.843	Intermediate Similarity	NPC215300
0.843	Intermediate Similarity	NPC38017
0.8426	Intermediate Similarity	NPC474839
0.8411	Intermediate Similarity	NPC168393
0.8403	Intermediate Similarity	NPC138248
0.8403	Intermediate Similarity	NPC228503
0.8396	Intermediate Similarity	NPC72729
0.8396	Intermediate Similarity	NPC161571
0.8396	Intermediate Similarity	NPC275053
0.8396	Intermediate Similarity	NPC248573
0.8393	Intermediate Similarity	NPC471179
0.8393	Intermediate Similarity	NPC250323
0.839	Intermediate Similarity	NPC57199
0.8381	Intermediate Similarity	NPC77492
0.8381	Intermediate Similarity	NPC79241
0.8381	Intermediate Similarity	NPC6597
0.8378	Intermediate Similarity	NPC132720
0.8365	Intermediate Similarity	NPC8392
0.8364	Intermediate Similarity	NPC95344
0.8362	Intermediate Similarity	NPC469644
0.8362	Intermediate Similarity	NPC176893
0.8362	Intermediate Similarity	NPC151197
0.8362	Intermediate Similarity	NPC217174
0.8333	Intermediate Similarity	NPC474486
0.8333	Intermediate Similarity	NPC241891
0.8333	Intermediate Similarity	NPC192948
0.8333	Intermediate Similarity	NPC105718
0.8333	Intermediate Similarity	NPC278955
0.8333	Intermediate Similarity	NPC35797
0.8319	Intermediate Similarity	NPC715
0.8319	Intermediate Similarity	NPC261343
0.8302	Intermediate Similarity	NPC33675
0.8302	Intermediate Similarity	NPC299762
0.8302	Intermediate Similarity	NPC122005
0.8302	Intermediate Similarity	NPC252821
0.8293	Intermediate Similarity	NPC62219
0.8291	Intermediate Similarity	NPC69006
0.8291	Intermediate Similarity	NPC223451
0.8291	Intermediate Similarity	NPC472071
0.8276	Intermediate Similarity	NPC63010
0.8276	Intermediate Similarity	NPC48781
0.8276	Intermediate Similarity	NPC9592
0.8273	Intermediate Similarity	NPC66834
0.8273	Intermediate Similarity	NPC305603
0.8273	Intermediate Similarity	NPC61033
0.8264	Intermediate Similarity	NPC82299
0.8264	Intermediate Similarity	NPC170485
0.8261	Intermediate Similarity	NPC38893
0.8261	Intermediate Similarity	NPC477137
0.8261	Intermediate Similarity	NPC261973
0.8261	Intermediate Similarity	NPC471668
0.8261	Intermediate Similarity	NPC308311
0.8257	Intermediate Similarity	NPC246056
0.8257	Intermediate Similarity	NPC134829
0.8252	Intermediate Similarity	NPC231150
0.8252	Intermediate Similarity	NPC204210
0.8246	Intermediate Similarity	NPC195922
0.8241	Intermediate Similarity	NPC269212
0.8235	Intermediate Similarity	NPC70436
0.8226	Intermediate Similarity	NPC160623
0.8224	Intermediate Similarity	NPC225506
0.8224	Intermediate Similarity	NPC174911
0.822	Intermediate Similarity	NPC102639
0.8214	Intermediate Similarity	NPC13482
0.8214	Intermediate Similarity	NPC141782
0.8208	Intermediate Similarity	NPC291789
0.8198	Intermediate Similarity	NPC11554
0.8198	Intermediate Similarity	NPC306295
0.8197	Intermediate Similarity	NPC473221
0.819	Intermediate Similarity	NPC222146
0.819	Intermediate Similarity	NPC144682
0.819	Intermediate Similarity	NPC477136
0.8182	Intermediate Similarity	NPC469913
0.8182	Intermediate Similarity	NPC470700
0.8182	Intermediate Similarity	NPC302681
0.8182	Intermediate Similarity	NPC39664
0.8182	Intermediate Similarity	NPC67250
0.8182	Intermediate Similarity	NPC54765
0.8182	Intermediate Similarity	NPC39097
0.8182	Intermediate Similarity	NPC109691
0.8182	Intermediate Similarity	NPC118286
0.8165	Intermediate Similarity	NPC475580
0.8165	Intermediate Similarity	NPC475225
0.8158	Intermediate Similarity	NPC322239
0.8151	Intermediate Similarity	NPC476633
0.8148	Intermediate Similarity	NPC252105
0.8148	Intermediate Similarity	NPC477685
0.8142	Intermediate Similarity	NPC268032
0.8137	Intermediate Similarity	NPC19680
0.8131	Intermediate Similarity	NPC128723
0.813	Intermediate Similarity	NPC24869
0.812	Intermediate Similarity	NPC190514
0.812	Intermediate Similarity	NPC469609

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 NPC224870 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	410
0.1-0.2	1084
0.2-0.3	1800
0.3-0.4	2964
0.4-0.5	1571
0.5-0.6	952
0.6-0.7	305
0.7-0.8	55
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8972	High Similarity	NPD4750	Phase 3
0.8846	High Similarity	NPD846	Approved
0.8846	High Similarity	NPD940	Approved
0.8462	Intermediate Similarity	NPD288	Approved
0.8396	Intermediate Similarity	NPD1242	Phase 1
0.8365	Intermediate Similarity	NPD844	Approved
0.819	Intermediate Similarity	NPD1809	Phase 2
0.8108	Intermediate Similarity	NPD2342	Discontinued
0.807	Intermediate Similarity	NPD7635	Approved
0.8065	Intermediate Similarity	NPD4625	Phase 3
0.8056	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD845	Approved
0.7925	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD4749	Approved
0.7823	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD3020	Approved
0.7686	Intermediate Similarity	NPD4626	Approved
0.7685	Intermediate Similarity	NPD2860	Approved
0.7685	Intermediate Similarity	NPD2859	Approved
0.7593	Intermediate Similarity	NPD2933	Approved
0.7593	Intermediate Similarity	NPD2934	Approved
0.7578	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD111	Approved
0.7561	Intermediate Similarity	NPD1610	Phase 2
0.7541	Intermediate Similarity	NPD2286	Discontinued
0.7521	Intermediate Similarity	NPD3091	Approved
0.752	Intermediate Similarity	NPD6696	Suspended
0.75	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD3022	Approved
0.7479	Intermediate Similarity	NPD497	Approved
0.7445	Intermediate Similarity	NPD7390	Discontinued
0.7442	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1201	Approved
0.7419	Intermediate Similarity	NPD3092	Approved
0.7398	Intermediate Similarity	NPD2932	Approved
0.7398	Intermediate Similarity	NPD4059	Approved
0.7398	Intermediate Similarity	NPD3019	Approved
0.7395	Intermediate Similarity	NPD498	Approved
0.7395	Intermediate Similarity	NPD495	Approved
0.7395	Intermediate Similarity	NPD496	Approved
0.7377	Intermediate Similarity	NPD1548	Phase 1
0.7373	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD9093	Approved
0.7344	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD3094	Phase 2
0.7317	Intermediate Similarity	NPD5691	Approved
0.7287	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4908	Phase 1
0.7282	Intermediate Similarity	NPD9089	Approved
0.7281	Intermediate Similarity	NPD9500	Approved
0.728	Intermediate Similarity	NPD422	Phase 1
0.7258	Intermediate Similarity	NPD1751	Approved
0.725	Intermediate Similarity	NPD1398	Phase 1
0.725	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1445	Approved
0.7241	Intermediate Similarity	NPD1444	Approved
0.7218	Intermediate Similarity	NPD4097	Suspended
0.7213	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1792	Phase 2
0.7188	Intermediate Similarity	NPD1470	Approved
0.7185	Intermediate Similarity	NPD5408	Approved
0.7185	Intermediate Similarity	NPD5404	Approved
0.7185	Intermediate Similarity	NPD5406	Approved
0.7185	Intermediate Similarity	NPD6099	Approved
0.7185	Intermediate Similarity	NPD5405	Approved
0.7185	Intermediate Similarity	NPD6100	Approved
0.7177	Intermediate Similarity	NPD4093	Discontinued
0.712	Intermediate Similarity	NPD3095	Discontinued
0.7111	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD1283	Approved
0.7099	Intermediate Similarity	NPD3027	Phase 3
0.7083	Intermediate Similarity	NPD228	Approved
0.708	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD9273	Approved
0.7073	Intermediate Similarity	NPD7340	Approved
0.7068	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD943	Approved
0.7068	Intermediate Similarity	NPD1613	Approved
0.7054	Intermediate Similarity	NPD1134	Approved
0.7054	Intermediate Similarity	NPD1129	Approved
0.7054	Intermediate Similarity	NPD1135	Approved
0.7054	Intermediate Similarity	NPD1133	Approved
0.7054	Intermediate Similarity	NPD1131	Approved
0.7054	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD1651	Approved
0.7021	Intermediate Similarity	NPD2532	Approved
0.7021	Intermediate Similarity	NPD2533	Approved
0.7021	Intermediate Similarity	NPD2534	Approved
0.6992	Remote Similarity	NPD6671	Approved
0.6984	Remote Similarity	NPD4589	Approved
0.6978	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD2228	Approved
0.6967	Remote Similarity	NPD2229	Approved
0.6967	Remote Similarity	NPD2234	Approved
0.6963	Remote Similarity	NPD1607	Approved
0.696	Remote Similarity	NPD5303	Approved
0.696	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.696	Remote Similarity	NPD5304	Approved
0.6947	Remote Similarity	NPD5736	Approved
0.694	Remote Similarity	NPD1555	Discontinued
0.694	Remote Similarity	NPD4060	Phase 1
0.6935	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9610	Approved
0.6923	Remote Similarity	NPD1164	Approved
0.6923	Remote Similarity	NPD9608	Approved
0.6917	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD9379	Approved
0.6885	Remote Similarity	NPD9377	Approved
0.6881	Remote Similarity	NPD9094	Approved
0.6875	Remote Similarity	NPD1281	Approved
0.6875	Remote Similarity	NPD1611	Approved
0.687	Remote Similarity	NPD858	Approved
0.687	Remote Similarity	NPD602	Approved
0.687	Remote Similarity	NPD599	Approved
0.687	Remote Similarity	NPD859	Approved
0.687	Remote Similarity	NPD2194	Approved
0.687	Remote Similarity	NPD2195	Approved
0.686	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD709	Approved
0.6838	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD9269	Phase 2
0.6818	Remote Similarity	NPD2861	Phase 2
0.6818	Remote Similarity	NPD3635	Approved
0.6818	Remote Similarity	NPD3636	Approved
0.6818	Remote Similarity	NPD3637	Approved
0.6815	Remote Similarity	NPD1240	Approved
0.6797	Remote Similarity	NPD3143	Discontinued
0.6797	Remote Similarity	NPD3023	Approved
0.6797	Remote Similarity	NPD3026	Approved
0.6774	Remote Similarity	NPD1793	Approved
0.6774	Remote Similarity	NPD1791	Approved
0.6772	Remote Similarity	NPD9268	Approved
0.6772	Remote Similarity	NPD3025	Approved
0.6772	Remote Similarity	NPD3024	Approved
0.6769	Remote Similarity	NPD1669	Approved
0.6767	Remote Similarity	NPD2605	Approved
0.6767	Remote Similarity	NPD2606	Approved
0.6742	Remote Similarity	NPD4624	Approved
0.6741	Remote Similarity	NPD6407	Approved
0.6741	Remote Similarity	NPD6405	Approved
0.6741	Remote Similarity	NPD6663	Approved
0.6739	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD3750	Approved
0.6719	Remote Similarity	NPD9384	Approved
0.6719	Remote Similarity	NPD9381	Approved
0.6716	Remote Similarity	NPD5156	Approved
0.6716	Remote Similarity	NPD5155	Approved
0.6715	Remote Similarity	NPD2568	Approved
0.6694	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD7330	Discontinued
0.6692	Remote Similarity	NPD3070	Discontinued
0.6692	Remote Similarity	NPD3018	Phase 2
0.6691	Remote Similarity	NPD3620	Phase 2
0.6691	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2238	Phase 2
0.6667	Remote Similarity	NPD6232	Discontinued
0.6667	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3028	Approved
0.6667	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD4721	Approved
0.6643	Remote Similarity	NPD4725	Approved
0.6643	Remote Similarity	NPD4726	Approved
0.6642	Remote Similarity	NPD3595	Approved
0.6642	Remote Similarity	NPD3594	Approved
0.6642	Remote Similarity	NPD230	Phase 1
0.6641	Remote Similarity	NPD9622	Approved
0.664	Remote Similarity	NPD9618	Approved
0.664	Remote Similarity	NPD475	Phase 2
0.664	Remote Similarity	NPD9614	Approved
0.6619	Remote Similarity	NPD1510	Phase 2
0.6614	Remote Similarity	NPD317	Approved
0.6614	Remote Similarity	NPD856	Approved
0.6614	Remote Similarity	NPD318	Approved
0.6614	Remote Similarity	NPD16	Approved
0.6612	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD290	Approved
0.6601	Remote Similarity	NPD6959	Discontinued
0.6594	Remote Similarity	NPD2157	Approved
0.6589	Remote Similarity	NPD1778	Approved
0.6589	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD256	Approved
0.6587	Remote Similarity	NPD255	Approved
0.6577	Remote Similarity	NPD37	Approved
0.6571	Remote Similarity	NPD2935	Discontinued
0.6569	Remote Similarity	NPD468	Phase 1
0.6565	Remote Similarity	NPD2232	Approved
0.6565	Remote Similarity	NPD2233	Approved
0.6565	Remote Similarity	NPD2230	Approved
0.656	Remote Similarity	NPD5283	Phase 1
0.6557	Remote Similarity	NPD2684	Approved
0.6557	Remote Similarity	NPD74	Approved
0.6557	Remote Similarity	NPD9266	Approved
0.6552	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD2211	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