NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	154.06
Volume:	156.829
LogP:	0.518
LogD:	1.056
LogS:	-0.423
# Rotatable Bonds:	2
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.63
Synthetic Accessibility Score:	2.039
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.493
MDCK Permeability:	1.2756358955812175e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.085
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.193
30% Bioavailability (F30%):	0.893

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	32.943511962890625%
Volume Distribution (VD):	1.063
Pgp-substrate:	57.916378021240234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.199
CYP1A2-substrate:	0.725
CYP2C19-inhibitor:	0.072
CYP2C19-substrate:	0.1
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.573
CYP2D6-inhibitor:	0.163
CYP2D6-substrate:	0.807
CYP3A4-inhibitor:	0.07
CYP3A4-substrate:	0.247

ADMET: Excretion

Clearance (CL):	12.669
Half-life (T1/2):	0.916

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.056
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.737
Rat Oral Acute Toxicity:	0.684
Maximum Recommended Daily Dose:	0.048
Skin Sensitization:	0.935
Carcinogencity:	0.671
Eye Corrosion:	0.686
Eye Irritation:	0.979
Respiratory Toxicity:	0.101

Download Data

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

Natural Product: NPC130817

Natural Product ID:	NPC130817
*Common Name:**	2-(Methoxymethyl)Benzene-1,4-Diol
IUPAC Name:	2-(methoxymethyl)benzene-1,4-diol
Synonyms:
Standard InCHIKey:	JTWJYCAMRHQJDE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H10O3/c1-11-5-6-4-7(9)2-3-8(6)10/h2-4,9-10H,5H2,1H3
SMILES:	COCc1cc(O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256084
PubChem CID:	21320451
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002542] Benzylethers

*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
NPO28718	Penicillium terrestre	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18163588]
NPO28718	Penicillium terrestre	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100000.0	nM	PMID[567247]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	58900.0	nM	PMID[567247]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	86200.0	nM	PMID[567247]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[567247]
NPT35	Others	n.a.		IC50	=	9800.0	nM	PMID[567247]

☑ 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 NPC130817 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	296
0.1-0.2	1851
0.2-0.3	6103
0.3-0.4	13297
0.4-0.5	4544
0.5-0.6	8865
0.6-0.7	5931
0.7-0.8	1630
0.8-0.85	137
0.85-0.9	36
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9406	High Similarity	NPC241549
0.9406	High Similarity	NPC169450
0.9278	High Similarity	NPC88420
0.9118	High Similarity	NPC233320
0.9062	High Similarity	NPC29373
0.8972	High Similarity	NPC232165
0.89	High Similarity	NPC130103
0.8889	High Similarity	NPC475078
0.8889	High Similarity	NPC152097
0.8868	High Similarity	NPC228452
0.88	High Similarity	NPC260775
0.8796	High Similarity	NPC301321
0.8774	High Similarity	NPC275627
0.8713	High Similarity	NPC48730
0.8713	High Similarity	NPC70677
0.8713	High Similarity	NPC248396
0.8713	High Similarity	NPC174911
0.8713	High Similarity	NPC130756
0.8713	High Similarity	NPC129373
0.8713	High Similarity	NPC12931
0.8704	High Similarity	NPC470837
0.866	High Similarity	NPC47950
0.866	High Similarity	NPC312304
0.8649	High Similarity	NPC121866
0.8627	High Similarity	NPC80800
0.8571	High Similarity	NPC66834
0.8571	High Similarity	NPC474352
0.8571	High Similarity	NPC231150
0.8559	High Similarity	NPC283616
0.8558	High Similarity	NPC471350
0.8545	High Similarity	NPC154256
0.8545	High Similarity	NPC290470
0.8544	High Similarity	NPC108497
0.8544	High Similarity	NPC471228
0.8544	High Similarity	NPC235762
0.8519	High Similarity	NPC474920
0.8519	High Similarity	NPC302371
0.8519	High Similarity	NPC98372
0.8515	High Similarity	NPC474073
0.8476	Intermediate Similarity	NPC67250
0.8462	Intermediate Similarity	NPC475225
0.8462	Intermediate Similarity	NPC475580
0.8454	Intermediate Similarity	NPC27974
0.8447	Intermediate Similarity	NPC12221
0.8447	Intermediate Similarity	NPC477685
0.8411	Intermediate Similarity	NPC98392
0.8411	Intermediate Similarity	NPC473524
0.8407	Intermediate Similarity	NPC67791
0.84	Intermediate Similarity	NPC245187
0.8381	Intermediate Similarity	NPC47284
0.8365	Intermediate Similarity	NPC233827
0.8365	Intermediate Similarity	NPC269212
0.8351	Intermediate Similarity	NPC407
0.8351	Intermediate Similarity	NPC307235
0.8349	Intermediate Similarity	NPC26615
0.8348	Intermediate Similarity	NPC477151
0.8348	Intermediate Similarity	NPC132518
0.8333	Intermediate Similarity	NPC277798
0.8333	Intermediate Similarity	NPC471535
0.8333	Intermediate Similarity	NPC100108
0.8333	Intermediate Similarity	NPC286904
0.8333	Intermediate Similarity	NPC150837
0.8319	Intermediate Similarity	NPC38181
0.8319	Intermediate Similarity	NPC20230
0.8302	Intermediate Similarity	NPC164576
0.8302	Intermediate Similarity	NPC155072
0.8302	Intermediate Similarity	NPC53740
0.8288	Intermediate Similarity	NPC808
0.8288	Intermediate Similarity	NPC473718
0.8286	Intermediate Similarity	NPC272029
0.8286	Intermediate Similarity	NPC93831
0.8286	Intermediate Similarity	NPC12987
0.8286	Intermediate Similarity	NPC474603
0.8273	Intermediate Similarity	NPC190212
0.8269	Intermediate Similarity	NPC94343
0.8261	Intermediate Similarity	NPC285289
0.8257	Intermediate Similarity	NPC54373
0.8257	Intermediate Similarity	NPC195873
0.8247	Intermediate Similarity	NPC155393
0.8246	Intermediate Similarity	NPC328485
0.8235	Intermediate Similarity	NPC312132
0.8235	Intermediate Similarity	NPC259512
0.8224	Intermediate Similarity	NPC320439
0.8214	Intermediate Similarity	NPC203113
0.8214	Intermediate Similarity	NPC150624
0.8198	Intermediate Similarity	NPC41851
0.819	Intermediate Similarity	NPC474864
0.819	Intermediate Similarity	NPC168393
0.8174	Intermediate Similarity	NPC473875
0.8174	Intermediate Similarity	NPC96423
0.8174	Intermediate Similarity	NPC475529
0.8173	Intermediate Similarity	NPC72729
0.8173	Intermediate Similarity	NPC166761
0.8165	Intermediate Similarity	NPC168657
0.8165	Intermediate Similarity	NPC94045
0.8158	Intermediate Similarity	NPC32152
0.8155	Intermediate Similarity	NPC6597
0.8155	Intermediate Similarity	NPC79241
0.8148	Intermediate Similarity	NPC75440
0.8142	Intermediate Similarity	NPC33270
0.8142	Intermediate Similarity	NPC244816
0.8142	Intermediate Similarity	NPC69261
0.8142	Intermediate Similarity	NPC50521
0.8142	Intermediate Similarity	NPC221549
0.8142	Intermediate Similarity	NPC320864
0.8136	Intermediate Similarity	NPC33654
0.8131	Intermediate Similarity	NPC54765
0.8131	Intermediate Similarity	NPC30416
0.8131	Intermediate Similarity	NPC469913
0.812	Intermediate Similarity	NPC477152
0.8119	Intermediate Similarity	NPC306884
0.8119	Intermediate Similarity	NPC210497
0.8119	Intermediate Similarity	NPC162314
0.8119	Intermediate Similarity	NPC295295
0.8119	Intermediate Similarity	NPC138117
0.8119	Intermediate Similarity	NPC94139
0.8119	Intermediate Similarity	NPC3358
0.8119	Intermediate Similarity	NPC147284
0.8119	Intermediate Similarity	NPC55903
0.8119	Intermediate Similarity	NPC325292
0.8113	Intermediate Similarity	NPC227458
0.8113	Intermediate Similarity	NPC244513
0.8113	Intermediate Similarity	NPC102216
0.8113	Intermediate Similarity	NPC218879
0.8103	Intermediate Similarity	NPC476165
0.81	Intermediate Similarity	NPC192
0.81	Intermediate Similarity	NPC300017
0.8091	Intermediate Similarity	NPC296920
0.8091	Intermediate Similarity	NPC90520
0.8087	Intermediate Similarity	NPC474131
0.8087	Intermediate Similarity	NPC232295
0.8081	Intermediate Similarity	NPC104216
0.8081	Intermediate Similarity	NPC19680
0.8077	Intermediate Similarity	NPC299762
0.8077	Intermediate Similarity	NPC80027
0.8077	Intermediate Similarity	NPC33675
0.8077	Intermediate Similarity	NPC100870
0.8077	Intermediate Similarity	NPC171843
0.8077	Intermediate Similarity	NPC128723
0.8073	Intermediate Similarity	NPC316052
0.807	Intermediate Similarity	NPC329980
0.807	Intermediate Similarity	NPC190514
0.807	Intermediate Similarity	NPC63010
0.8058	Intermediate Similarity	NPC283711
0.8056	Intermediate Similarity	NPC204901
0.8056	Intermediate Similarity	NPC305603
0.8056	Intermediate Similarity	NPC232523
0.8056	Intermediate Similarity	NPC194034
0.8056	Intermediate Similarity	NPC158253
0.8056	Intermediate Similarity	NPC61033
0.8053	Intermediate Similarity	NPC69539
0.8051	Intermediate Similarity	NPC33402
0.8051	Intermediate Similarity	NPC183446
0.8039	Intermediate Similarity	NPC152415
0.8037	Intermediate Similarity	NPC154899
0.8037	Intermediate Similarity	NPC292452
0.8037	Intermediate Similarity	NPC233396
0.8037	Intermediate Similarity	NPC37802
0.8036	Intermediate Similarity	NPC276737
0.8036	Intermediate Similarity	NPC22610
0.8036	Intermediate Similarity	NPC197513
0.8034	Intermediate Similarity	NPC77789
0.8034	Intermediate Similarity	NPC135414
0.8034	Intermediate Similarity	NPC18128
0.8034	Intermediate Similarity	NPC325301
0.8034	Intermediate Similarity	NPC270326
0.8034	Intermediate Similarity	NPC246967
0.802	Intermediate Similarity	NPC306074
0.802	Intermediate Similarity	NPC204210
0.8019	Intermediate Similarity	NPC71002
0.8019	Intermediate Similarity	NPC242342
0.8019	Intermediate Similarity	NPC53051
0.8019	Intermediate Similarity	NPC302219
0.8019	Intermediate Similarity	NPC106396
0.8019	Intermediate Similarity	NPC24404
0.8019	Intermediate Similarity	NPC94351
0.8019	Intermediate Similarity	NPC168303
0.8019	Intermediate Similarity	NPC146798
0.8019	Intermediate Similarity	NPC222522
0.8019	Intermediate Similarity	NPC249828
0.8019	Intermediate Similarity	NPC85479
0.8019	Intermediate Similarity	NPC305205
0.8019	Intermediate Similarity	NPC313030
0.8018	Intermediate Similarity	NPC280606
0.8017	Intermediate Similarity	NPC129176
0.8	Intermediate Similarity	NPC10588
0.8	Intermediate Similarity	NPC294741
0.8	Intermediate Similarity	NPC471449
0.8	Intermediate Similarity	NPC51341
0.8	Intermediate Similarity	NPC184302
0.7982	Intermediate Similarity	NPC174981
0.7982	Intermediate Similarity	NPC95344
0.7982	Intermediate Similarity	NPC238176
0.7982	Intermediate Similarity	NPC279887
0.7982	Intermediate Similarity	NPC68260
0.7982	Intermediate Similarity	NPC187993
0.7981	Intermediate Similarity	NPC156313
0.7981	Intermediate Similarity	NPC291789
0.798	Intermediate Similarity	NPC23167
0.7966	Intermediate Similarity	NPC248786

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 NPC130817 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	1064
0.2-0.3	1714
0.3-0.4	2811
0.4-0.5	1686
0.5-0.6	1074
0.6-0.7	439
0.7-0.8	66
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8713	High Similarity	NPD289	Clinical (unspecified phase)
0.8317	Intermediate Similarity	NPD844	Approved
0.8302	Intermediate Similarity	NPD968	Approved
0.8288	Intermediate Similarity	NPD6671	Approved
0.8235	Intermediate Similarity	NPD288	Approved
0.8056	Intermediate Similarity	NPD290	Approved
0.7928	Intermediate Similarity	NPD228	Approved
0.7925	Intermediate Similarity	NPD940	Approved
0.7925	Intermediate Similarity	NPD846	Approved
0.79	Intermediate Similarity	NPD9295	Approved
0.7863	Intermediate Similarity	NPD3496	Discontinued
0.7857	Intermediate Similarity	NPD111	Approved
0.783	Intermediate Similarity	NPD1242	Phase 1
0.7787	Intermediate Similarity	NPD596	Approved
0.7787	Intermediate Similarity	NPD600	Approved
0.7767	Intermediate Similarity	NPD845	Approved
0.7748	Intermediate Similarity	NPD4750	Phase 3
0.7739	Intermediate Similarity	NPD9493	Approved
0.7699	Intermediate Similarity	NPD7635	Approved
0.7692	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2933	Approved
0.7692	Intermediate Similarity	NPD2934	Approved
0.7642	Intermediate Similarity	NPD9273	Approved
0.7619	Intermediate Similarity	NPD2859	Approved
0.7619	Intermediate Similarity	NPD2860	Approved
0.7607	Intermediate Similarity	NPD1548	Phase 1
0.76	Intermediate Similarity	NPD840	Approved
0.76	Intermediate Similarity	NPD839	Approved
0.757	Intermediate Similarity	NPD3020	Approved
0.7561	Intermediate Similarity	NPD2861	Phase 2
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD9088	Approved
0.7479	Intermediate Similarity	NPD1778	Approved
0.7453	Intermediate Similarity	NPD1809	Phase 2
0.7414	Intermediate Similarity	NPD9618	Approved
0.7414	Intermediate Similarity	NPD9614	Approved
0.7377	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD4749	Approved
0.7355	Intermediate Similarity	NPD1091	Approved
0.735	Intermediate Similarity	NPD709	Approved
0.7345	Intermediate Similarity	NPD2684	Approved
0.7339	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4626	Approved
0.7328	Intermediate Similarity	NPD1398	Phase 1
0.7321	Intermediate Similarity	NPD1444	Approved
0.7321	Intermediate Similarity	NPD1445	Approved
0.7317	Intermediate Similarity	NPD6696	Suspended
0.7302	Intermediate Similarity	NPD3027	Phase 3
0.7295	Intermediate Similarity	NPD2230	Approved
0.7295	Intermediate Similarity	NPD2233	Approved
0.7295	Intermediate Similarity	NPD2232	Approved
0.7281	Intermediate Similarity	NPD3022	Approved
0.7281	Intermediate Similarity	NPD3021	Approved
0.7266	Intermediate Similarity	NPD1613	Approved
0.7266	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD2342	Discontinued
0.7252	Intermediate Similarity	NPD2935	Discontinued
0.725	Intermediate Similarity	NPD1357	Approved
0.7244	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD821	Approved
0.7227	Intermediate Similarity	NPD9613	Approved
0.7227	Intermediate Similarity	NPD9615	Approved
0.7227	Intermediate Similarity	NPD9616	Approved
0.7222	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4908	Phase 1
0.7216	Intermediate Similarity	NPD9294	Approved
0.7213	Intermediate Similarity	NPD422	Phase 1
0.7207	Intermediate Similarity	NPD9500	Approved
0.7167	Intermediate Similarity	NPD316	Approved
0.7167	Intermediate Similarity	NPD9545	Approved
0.7165	Intermediate Similarity	NPD4625	Phase 3
0.7154	Intermediate Similarity	NPD2231	Phase 2
0.7154	Intermediate Similarity	NPD2235	Phase 2
0.7143	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7340	Approved
0.713	Intermediate Similarity	NPD1792	Phase 2
0.7119	Intermediate Similarity	NPD497	Approved
0.7109	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5691	Approved
0.7094	Intermediate Similarity	NPD7843	Approved
0.7083	Intermediate Similarity	NPD9087	Approved
0.7073	Intermediate Similarity	NPD1611	Approved
0.7063	Intermediate Similarity	NPD6584	Phase 3
0.7059	Intermediate Similarity	NPD7157	Approved
0.7043	Intermediate Similarity	NPD74	Approved
0.7043	Intermediate Similarity	NPD9266	Approved
0.7037	Intermediate Similarity	NPD9296	Approved
0.7034	Intermediate Similarity	NPD5283	Phase 1
0.7034	Intermediate Similarity	NPD495	Approved
0.7034	Intermediate Similarity	NPD496	Approved
0.7034	Intermediate Similarity	NPD498	Approved
0.703	Intermediate Similarity	NPD9089	Approved
0.7025	Intermediate Similarity	NPD3091	Approved
0.7025	Intermediate Similarity	NPD1182	Approved
0.7018	Intermediate Similarity	NPD3134	Approved
0.7016	Intermediate Similarity	NPD9717	Approved
0.7009	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD1712	Approved
0.7	Intermediate Similarity	NPD2238	Phase 2
0.7	Intermediate Similarity	NPD4060	Phase 1
0.6991	Remote Similarity	NPD9610	Approved
0.6991	Remote Similarity	NPD9608	Approved
0.6983	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5585	Approved
0.696	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1358	Approved
0.6957	Remote Similarity	NPD9264	Approved
0.6957	Remote Similarity	NPD9263	Approved
0.6957	Remote Similarity	NPD9267	Approved
0.6949	Remote Similarity	NPD9379	Approved
0.6949	Remote Similarity	NPD9377	Approved
0.6949	Remote Similarity	NPD1138	Approved
0.6947	Remote Similarity	NPD447	Suspended
0.6947	Remote Similarity	NPD230	Phase 1
0.6935	Remote Similarity	NPD1535	Discovery
0.6931	Remote Similarity	NPD9093	Approved
0.693	Remote Similarity	NPD9697	Approved
0.6929	Remote Similarity	NPD3691	Phase 2
0.6929	Remote Similarity	NPD558	Phase 2
0.6929	Remote Similarity	NPD3690	Phase 2
0.6923	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD9365	Approved
0.6911	Remote Similarity	NPD9384	Approved
0.6911	Remote Similarity	NPD9381	Approved
0.6894	Remote Similarity	NPD4097	Suspended
0.6891	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.688	Remote Similarity	NPD1481	Phase 2
0.6875	Remote Similarity	NPD9494	Approved
0.6875	Remote Similarity	NPD2237	Approved
0.6875	Remote Similarity	NPD3018	Phase 2
0.6864	Remote Similarity	NPD1139	Approved
0.6864	Remote Similarity	NPD1137	Approved
0.686	Remote Similarity	NPD405	Clinical (unspecified phase)
0.685	Remote Similarity	NPD1203	Approved
0.685	Remote Similarity	NPD2797	Approved
0.685	Remote Similarity	NPD3094	Phase 2
0.6846	Remote Similarity	NPD1048	Approved
0.6846	Remote Similarity	NPD411	Approved
0.6838	Remote Similarity	NPD5177	Phase 3
0.6838	Remote Similarity	NPD5451	Approved
0.6833	Remote Similarity	NPD1791	Approved
0.6833	Remote Similarity	NPD1793	Approved
0.6825	Remote Similarity	NPD6582	Phase 2
0.6825	Remote Similarity	NPD6583	Phase 3
0.6825	Remote Similarity	NPD9622	Approved
0.6814	Remote Similarity	NPD291	Approved
0.68	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3092	Approved
0.6797	Remote Similarity	NPD602	Approved
0.6797	Remote Similarity	NPD859	Approved
0.6797	Remote Similarity	NPD599	Approved
0.6797	Remote Similarity	NPD858	Approved
0.6791	Remote Similarity	NPD1753	Discontinued
0.6777	Remote Similarity	NPD2557	Approved
0.6774	Remote Similarity	NPD2667	Approved
0.6774	Remote Similarity	NPD2668	Approved
0.6772	Remote Similarity	NPD3225	Approved
0.6772	Remote Similarity	NPD1283	Approved
0.6767	Remote Similarity	NPD6653	Approved
0.675	Remote Similarity	NPD2228	Approved
0.675	Remote Similarity	NPD2234	Approved
0.675	Remote Similarity	NPD592	Approved
0.675	Remote Similarity	NPD1241	Discontinued
0.675	Remote Similarity	NPD2229	Approved
0.675	Remote Similarity	NPD594	Approved
0.6748	Remote Similarity	NPD1759	Phase 1
0.6746	Remote Similarity	NPD1608	Approved
0.6746	Remote Similarity	NPD1840	Phase 2
0.6742	Remote Similarity	NPD1240	Approved
0.6726	Remote Similarity	NPD3028	Approved
0.6719	Remote Similarity	NPD1133	Approved
0.6719	Remote Similarity	NPD1129	Approved
0.6719	Remote Similarity	NPD1135	Approved
0.6719	Remote Similarity	NPD1134	Approved
0.6719	Remote Similarity	NPD1131	Approved
0.6718	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD2504	Approved
0.6714	Remote Similarity	NPD2505	Approved
0.6694	Remote Similarity	NPD3445	Approved
0.6694	Remote Similarity	NPD595	Approved
0.6694	Remote Similarity	NPD6382	Discontinued
0.6694	Remote Similarity	NPD593	Approved
0.6694	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD3444	Approved
0.6694	Remote Similarity	NPD3443	Approved
0.6694	Remote Similarity	NPD1651	Approved
0.6693	Remote Similarity	NPD2982	Phase 2
0.6693	Remote Similarity	NPD1669	Approved
0.6693	Remote Similarity	NPD4359	Approved
0.6693	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD2983	Phase 2
0.6692	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1653	Approved
0.6667	Remote Similarity	NPD4624	Approved
0.6667	Remote Similarity	NPD9621	Approved
0.6667	Remote Similarity	NPD9620	Approved
0.6667	Remote Similarity	NPD1758	Phase 1

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