NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.1
Volume:	279.016
LogP:	1.587
LogD:	2.083
LogS:	-1.102
# Rotatable Bonds:	4
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.643
Synthetic Accessibility Score:	2.492
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.895
MDCK Permeability:	6.256980213947827e-06
Pgp-inhibitor:	0.092
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.11
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	89.65028381347656%
Volume Distribution (VD):	0.822
Pgp-substrate:	7.202359199523926%

ADMET: Metabolism

CYP1A2-inhibitor:	0.236
CYP1A2-substrate:	0.832
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.377
CYP2C9-substrate:	0.564
CYP2D6-inhibitor:	0.494
CYP2D6-substrate:	0.771
CYP3A4-inhibitor:	0.164
CYP3A4-substrate:	0.246

ADMET: Excretion

Clearance (CL):	13.532
Half-life (T1/2):	0.94

ADMET: Toxicity

hERG Blockers:	0.124
Human Hepatotoxicity (H-HT):	0.089
Drug-inuced Liver Injury (DILI):	0.341
AMES Toxicity:	0.634
Rat Oral Acute Toxicity:	0.093
Maximum Recommended Daily Dose:	0.171
Skin Sensitization:	0.956
Carcinogencity:	0.18
Eye Corrosion:	0.005
Eye Irritation:	0.942
Respiratory Toxicity:	0.065

Download Data

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

Natural Product: NPC232165

Natural Product ID:	NPC232165
*Common Name:**	2-(2,5-Dihydroxybenzyl)-5-(Methoxymethyl)Benzene-1,4-Diol
IUPAC Name:	2-[(2,5-dihydroxyphenyl)methyl]-5-(methoxymethyl)benzene-1,4-diol
Synonyms:
Standard InCHIKey:	MFQGMLGUVGXVOO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O5/c1-20-8-11-7-14(18)10(6-15(11)19)4-9-5-12(16)2-3-13(9)17/h2-3,5-7,16-19H,4,8H2,1H3
SMILES:	COCc1cc(c(Cc2cc(ccc2O)O)cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL255495
PubChem CID:	24770576
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	6300.0	nM	PMID[521462]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	5800.0	nM	PMID[521462]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	33800.0	nM	PMID[521462]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	61900.0	nM	PMID[521462]
NPT35	Others	n.a.		IC50	=	6300.0	nM	PMID[521462]

☑ 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 NPC232165 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	1599
0.2-0.3	4474
0.3-0.4	13078
0.4-0.5	5493
0.5-0.6	6641
0.6-0.7	8445
0.7-0.8	2325
0.8-0.85	267
0.85-0.9	31
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.964	High Similarity	NPC121866
0.9167	High Similarity	NPC169450
0.8974	High Similarity	NPC77789
0.8974	High Similarity	NPC18128
0.8972	High Similarity	NPC130817
0.8929	High Similarity	NPC261343
0.887	High Similarity	NPC190514
0.8839	High Similarity	NPC228452
0.8818	High Similarity	NPC174981
0.8793	High Similarity	NPC184302
0.8772	High Similarity	NPC808
0.875	High Similarity	NPC33654
0.8739	High Similarity	NPC33728
0.8739	High Similarity	NPC19808
0.8696	High Similarity	NPC150624
0.8644	High Similarity	NPC277798
0.8644	High Similarity	NPC100108
0.8621	High Similarity	NPC320864
0.8621	High Similarity	NPC33270
0.8621	High Similarity	NPC69261
0.8609	High Similarity	NPC301321
0.8584	High Similarity	NPC54373
0.8584	High Similarity	NPC224527
0.8583	High Similarity	NPC261992
0.8571	High Similarity	NPC473524
0.8559	High Similarity	NPC233320
0.8559	High Similarity	NPC66834
0.8547	High Similarity	NPC9592
0.8547	High Similarity	NPC48781
0.8532	High Similarity	NPC235762
0.8532	High Similarity	NPC471228
0.8522	High Similarity	NPC22610
0.8522	High Similarity	NPC276737
0.8519	High Similarity	NPC130103
0.8519	High Similarity	NPC174911
0.8509	High Similarity	NPC302371
0.8509	High Similarity	NPC166995
0.85	High Similarity	NPC188997
0.8487	Intermediate Similarity	NPC129176
0.8482	Intermediate Similarity	NPC241549
0.8462	Intermediate Similarity	NPC15860
0.8462	Intermediate Similarity	NPC470759
0.8462	Intermediate Similarity	NPC50521
0.8462	Intermediate Similarity	NPC219070
0.8462	Intermediate Similarity	NPC221549
0.8462	Intermediate Similarity	NPC244816
0.8462	Intermediate Similarity	NPC127894
0.8455	Intermediate Similarity	NPC244513
0.8455	Intermediate Similarity	NPC475225
0.8455	Intermediate Similarity	NPC257947
0.8455	Intermediate Similarity	NPC227458
0.8455	Intermediate Similarity	NPC66331
0.8455	Intermediate Similarity	NPC218879
0.8455	Intermediate Similarity	NPC473221
0.8455	Intermediate Similarity	NPC102216
0.8448	Intermediate Similarity	NPC53906
0.844	Intermediate Similarity	NPC477685
0.844	Intermediate Similarity	NPC12221
0.8435	Intermediate Similarity	NPC23804
0.8435	Intermediate Similarity	NPC117846
0.8421	Intermediate Similarity	NPC275627
0.8417	Intermediate Similarity	NPC476633
0.8403	Intermediate Similarity	NPC328485
0.8393	Intermediate Similarity	NPC474352
0.8393	Intermediate Similarity	NPC232523
0.8393	Intermediate Similarity	NPC158253
0.8393	Intermediate Similarity	NPC204901
0.839	Intermediate Similarity	NPC283616
0.839	Intermediate Similarity	NPC63010
0.8387	Intermediate Similarity	NPC266691
0.8378	Intermediate Similarity	NPC37802
0.8378	Intermediate Similarity	NPC47284
0.8376	Intermediate Similarity	NPC141090
0.8376	Intermediate Similarity	NPC114064
0.8376	Intermediate Similarity	NPC203113
0.8374	Intermediate Similarity	NPC82299
0.8362	Intermediate Similarity	NPC470837
0.8349	Intermediate Similarity	NPC48730
0.8349	Intermediate Similarity	NPC129373
0.8349	Intermediate Similarity	NPC248396
0.8348	Intermediate Similarity	NPC26615
0.8348	Intermediate Similarity	NPC43525
0.8346	Intermediate Similarity	NPC269528
0.8333	Intermediate Similarity	NPC152097
0.8333	Intermediate Similarity	NPC472590
0.8333	Intermediate Similarity	NPC88420
0.8333	Intermediate Similarity	NPC96423
0.8319	Intermediate Similarity	NPC95344
0.8319	Intermediate Similarity	NPC75440
0.8319	Intermediate Similarity	NPC151197
0.8306	Intermediate Similarity	NPC236760
0.8305	Intermediate Similarity	NPC476266
0.8305	Intermediate Similarity	NPC474933
0.8305	Intermediate Similarity	NPC470760
0.8304	Intermediate Similarity	NPC67250
0.8304	Intermediate Similarity	NPC470700
0.8304	Intermediate Similarity	NPC109691
0.8304	Intermediate Similarity	NPC12640
0.8304	Intermediate Similarity	NPC302681
0.8304	Intermediate Similarity	NPC39664
0.8304	Intermediate Similarity	NPC201662
0.8304	Intermediate Similarity	NPC53740
0.8304	Intermediate Similarity	NPC39097
0.8304	Intermediate Similarity	NPC99836
0.8304	Intermediate Similarity	NPC118286
0.8295	Intermediate Similarity	NPC476698
0.8293	Intermediate Similarity	NPC131397
0.8293	Intermediate Similarity	NPC476254
0.8293	Intermediate Similarity	NPC105031
0.8291	Intermediate Similarity	NPC84999
0.8291	Intermediate Similarity	NPC246760
0.8291	Intermediate Similarity	NPC167934
0.8288	Intermediate Similarity	NPC323810
0.8288	Intermediate Similarity	NPC241891
0.8279	Intermediate Similarity	NPC121115
0.8279	Intermediate Similarity	NPC474160
0.8276	Intermediate Similarity	NPC190212
0.8276	Intermediate Similarity	NPC319803
0.8273	Intermediate Similarity	NPC143659
0.8273	Intermediate Similarity	NPC100340
0.8273	Intermediate Similarity	NPC80800
0.8268	Intermediate Similarity	NPC218884
0.8261	Intermediate Similarity	NPC225679
0.8261	Intermediate Similarity	NPC476632
0.8261	Intermediate Similarity	NPC165770
0.8261	Intermediate Similarity	NPC4493
0.8257	Intermediate Similarity	NPC260775
0.8254	Intermediate Similarity	NPC192687
0.8254	Intermediate Similarity	NPC51840
0.8254	Intermediate Similarity	NPC224157
0.8254	Intermediate Similarity	NPC311680
0.8254	Intermediate Similarity	NPC299221
0.8254	Intermediate Similarity	NPC234488
0.825	Intermediate Similarity	NPC223451
0.8246	Intermediate Similarity	NPC299568
0.8246	Intermediate Similarity	NPC186385
0.8235	Intermediate Similarity	NPC144343
0.823	Intermediate Similarity	NPC320439
0.823	Intermediate Similarity	NPC54844
0.822	Intermediate Similarity	NPC229147
0.822	Intermediate Similarity	NPC85292
0.822	Intermediate Similarity	NPC115808
0.822	Intermediate Similarity	NPC54507
0.8217	Intermediate Similarity	NPC261873
0.8217	Intermediate Similarity	NPC201357
0.8217	Intermediate Similarity	NPC283009
0.8217	Intermediate Similarity	NPC281521
0.8217	Intermediate Similarity	NPC255147
0.8217	Intermediate Similarity	NPC111655
0.8214	Intermediate Similarity	NPC246056
0.8214	Intermediate Similarity	NPC233396
0.8214	Intermediate Similarity	NPC134829
0.8214	Intermediate Similarity	NPC292452
0.8214	Intermediate Similarity	NPC471350
0.8214	Intermediate Similarity	NPC154899
0.8205	Intermediate Similarity	NPC41851
0.8205	Intermediate Similarity	NPC249270
0.8198	Intermediate Similarity	NPC108497
0.8198	Intermediate Similarity	NPC233827
0.8197	Intermediate Similarity	NPC325301
0.819	Intermediate Similarity	NPC42911
0.819	Intermediate Similarity	NPC290353
0.819	Intermediate Similarity	NPC98372
0.819	Intermediate Similarity	NPC153795
0.8189	Intermediate Similarity	NPC232275
0.8182	Intermediate Similarity	NPC130756
0.8182	Intermediate Similarity	NPC102639
0.8182	Intermediate Similarity	NPC72729
0.8182	Intermediate Similarity	NPC12931
0.8182	Intermediate Similarity	NPC218753
0.8182	Intermediate Similarity	NPC294741
0.8182	Intermediate Similarity	NPC473875
0.8182	Intermediate Similarity	NPC70677
0.8175	Intermediate Similarity	NPC58164
0.8175	Intermediate Similarity	NPC10225
0.8175	Intermediate Similarity	NPC190144
0.8174	Intermediate Similarity	NPC94045
0.8174	Intermediate Similarity	NPC132720
0.8174	Intermediate Similarity	NPC168657
0.8174	Intermediate Similarity	NPC475018
0.8167	Intermediate Similarity	NPC38181
0.8167	Intermediate Similarity	NPC20230
0.8167	Intermediate Similarity	NPC471449
0.8165	Intermediate Similarity	NPC474073
0.8165	Intermediate Similarity	NPC475078
0.8165	Intermediate Similarity	NPC79241
0.8165	Intermediate Similarity	NPC6597
0.8154	Intermediate Similarity	NPC300846
0.8154	Intermediate Similarity	NPC476639
0.8154	Intermediate Similarity	NPC114155
0.8151	Intermediate Similarity	NPC195466
0.8145	Intermediate Similarity	NPC278955
0.8145	Intermediate Similarity	NPC105718
0.8145	Intermediate Similarity	NPC105925
0.8145	Intermediate Similarity	NPC113495
0.8142	Intermediate Similarity	NPC135464
0.8142	Intermediate Similarity	NPC155072
0.8142	Intermediate Similarity	NPC92623
0.8142	Intermediate Similarity	NPC54765
0.8142	Intermediate Similarity	NPC30416

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 NPC232165 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	970
0.2-0.3	1513
0.3-0.4	2792
0.4-0.5	1815
0.5-0.6	1120
0.6-0.7	555
0.7-0.8	71
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8318	Intermediate Similarity	NPD844	Approved
0.8246	Intermediate Similarity	NPD4750	Phase 3
0.819	Intermediate Similarity	NPD7635	Approved
0.8182	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD6671	Approved
0.8073	Intermediate Similarity	NPD288	Approved
0.8016	Intermediate Similarity	NPD2861	Phase 2
0.7982	Intermediate Similarity	NPD968	Approved
0.7946	Intermediate Similarity	NPD846	Approved
0.7946	Intermediate Similarity	NPD940	Approved
0.7891	Intermediate Similarity	NPD4625	Phase 3
0.7891	Intermediate Similarity	NPD3027	Phase 3
0.7857	Intermediate Similarity	NPD1242	Phase 1
0.784	Intermediate Similarity	NPD4749	Approved
0.7823	Intermediate Similarity	NPD1610	Phase 2
0.7818	Intermediate Similarity	NPD2860	Approved
0.7818	Intermediate Similarity	NPD2859	Approved
0.7812	Intermediate Similarity	NPD4908	Phase 1
0.7795	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD1548	Phase 1
0.7768	Intermediate Similarity	NPD3020	Approved
0.7727	Intermediate Similarity	NPD2934	Approved
0.7727	Intermediate Similarity	NPD2933	Approved
0.771	Intermediate Similarity	NPD1613	Approved
0.771	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD6696	Suspended
0.7627	Intermediate Similarity	NPD3021	Approved
0.7627	Intermediate Similarity	NPD3022	Approved
0.7607	Intermediate Similarity	NPD2342	Discontinued
0.7603	Intermediate Similarity	NPD497	Approved
0.76	Intermediate Similarity	NPD3496	Discontinued
0.7597	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD2935	Discontinued
0.754	Intermediate Similarity	NPD1611	Approved
0.7521	Intermediate Similarity	NPD495	Approved
0.7521	Intermediate Similarity	NPD496	Approved
0.7521	Intermediate Similarity	NPD498	Approved
0.7521	Intermediate Similarity	NPD1398	Phase 1
0.7477	Intermediate Similarity	NPD845	Approved
0.7411	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD600	Approved
0.7405	Intermediate Similarity	NPD596	Approved
0.7402	Intermediate Similarity	NPD1091	Approved
0.7391	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1778	Approved
0.7381	Intermediate Similarity	NPD4626	Approved
0.7377	Intermediate Similarity	NPD5283	Phase 1
0.7368	Intermediate Similarity	NPD839	Approved
0.7368	Intermediate Similarity	NPD840	Approved
0.7355	Intermediate Similarity	NPD228	Approved
0.7344	Intermediate Similarity	NPD2232	Approved
0.7344	Intermediate Similarity	NPD2233	Approved
0.7344	Intermediate Similarity	NPD2230	Approved
0.7339	Intermediate Similarity	NPD7340	Approved
0.7313	Intermediate Similarity	NPD4060	Phase 1
0.7313	Intermediate Similarity	NPD2238	Phase 2
0.7311	Intermediate Similarity	NPD290	Approved
0.7308	Intermediate Similarity	NPD3094	Phase 2
0.7258	Intermediate Similarity	NPD709	Approved
0.7252	Intermediate Similarity	NPD6584	Phase 3
0.7222	Intermediate Similarity	NPD3091	Approved
0.7206	Intermediate Similarity	NPD1607	Approved
0.7206	Intermediate Similarity	NPD4097	Suspended
0.7197	Intermediate Similarity	NPD3018	Phase 2
0.7193	Intermediate Similarity	NPD1809	Phase 2
0.719	Intermediate Similarity	NPD1792	Phase 2
0.7174	Intermediate Similarity	NPD6099	Approved
0.7174	Intermediate Similarity	NPD6100	Approved
0.7165	Intermediate Similarity	NPD5691	Approved
0.7165	Intermediate Similarity	NPD1651	Approved
0.7164	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3092	Approved
0.7132	Intermediate Similarity	NPD422	Phase 1
0.7132	Intermediate Similarity	NPD1201	Approved
0.7122	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD9295	Approved
0.7111	Intermediate Similarity	NPD6405	Approved
0.7111	Intermediate Similarity	NPD6407	Approved
0.7109	Intermediate Similarity	NPD5126	Approved
0.7109	Intermediate Similarity	NPD5125	Phase 3
0.7107	Intermediate Similarity	NPD2684	Approved
0.7101	Intermediate Similarity	NPD1510	Phase 2
0.7099	Intermediate Similarity	NPD1283	Approved
0.7083	Intermediate Similarity	NPD1445	Approved
0.7083	Intermediate Similarity	NPD6090	Discontinued
0.7083	Intermediate Similarity	NPD1444	Approved
0.7077	Intermediate Similarity	NPD2235	Phase 2
0.7077	Intermediate Similarity	NPD2231	Phase 2
0.7077	Intermediate Similarity	NPD1608	Approved
0.7064	Intermediate Similarity	NPD111	Approved
0.7063	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD9493	Approved
0.7059	Intermediate Similarity	NPD1240	Approved
0.705	Intermediate Similarity	NPD1551	Phase 2
0.7049	Intermediate Similarity	NPD5451	Approved
0.7045	Intermediate Similarity	NPD1470	Approved
0.7045	Intermediate Similarity	NPD2797	Approved
0.704	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD2982	Phase 2
0.7023	Intermediate Similarity	NPD6582	Phase 2
0.7023	Intermediate Similarity	NPD2983	Phase 2
0.7023	Intermediate Similarity	NPD6583	Phase 3
0.7021	Intermediate Similarity	NPD5177	Phase 3
0.7016	Intermediate Similarity	NPD7843	Approved
0.7	Intermediate Similarity	NPD1535	Discovery
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD7266	Discontinued
0.7	Intermediate Similarity	NPD5763	Approved
0.6984	Remote Similarity	NPD2557	Approved
0.6984	Remote Similarity	NPD7157	Approved
0.6978	Remote Similarity	NPD7033	Discontinued
0.6977	Remote Similarity	NPD3095	Discontinued
0.6977	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3892	Phase 2
0.6972	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2568	Approved
0.6949	Remote Similarity	NPD3028	Approved
0.6947	Remote Similarity	NPD1481	Phase 2
0.6947	Remote Similarity	NPD2981	Phase 2
0.694	Remote Similarity	NPD2237	Approved
0.6935	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6032	Approved
0.6923	Remote Similarity	NPD3847	Discontinued
0.6923	Remote Similarity	NPD9273	Approved
0.6917	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD3268	Approved
0.6912	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4538	Approved
0.6906	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4536	Approved
0.6905	Remote Similarity	NPD9614	Approved
0.6905	Remote Similarity	NPD9618	Approved
0.6899	Remote Similarity	NPD3444	Approved
0.6899	Remote Similarity	NPD3445	Approved
0.6899	Remote Similarity	NPD5585	Approved
0.6899	Remote Similarity	NPD3443	Approved
0.6897	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7447	Phase 1
0.6894	Remote Similarity	NPD1669	Approved
0.688	Remote Similarity	NPD1138	Approved
0.688	Remote Similarity	NPD5535	Approved
0.688	Remote Similarity	NPD821	Approved
0.6879	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1281	Approved
0.687	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5929	Approved
0.6867	Remote Similarity	NPD2801	Approved
0.6867	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4624	Approved
0.6861	Remote Similarity	NPD6233	Phase 2
0.6857	Remote Similarity	NPD4308	Phase 3
0.6857	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6387	Discontinued
0.6846	Remote Similarity	NPD2286	Discontinued
0.6846	Remote Similarity	NPD2932	Approved
0.6846	Remote Similarity	NPD17	Approved
0.6846	Remote Similarity	NPD2668	Approved
0.6846	Remote Similarity	NPD3019	Approved
0.6846	Remote Similarity	NPD4059	Approved
0.6846	Remote Similarity	NPD2667	Approved
0.6842	Remote Similarity	NPD3225	Approved
0.6842	Remote Similarity	NPD8651	Approved
0.6833	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1549	Phase 2
0.6828	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7041	Phase 2
0.6828	Remote Similarity	NPD7213	Phase 3
0.6828	Remote Similarity	NPD7212	Phase 2
0.6825	Remote Similarity	NPD2234	Approved
0.6825	Remote Similarity	NPD2228	Approved
0.6825	Remote Similarity	NPD2229	Approved
0.6825	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7741	Discontinued
0.6822	Remote Similarity	NPD1182	Approved
0.6822	Remote Similarity	NPD9545	Approved
0.6822	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1712	Approved
0.6815	Remote Similarity	NPD5736	Approved
0.6812	Remote Similarity	NPD943	Approved
0.6812	Remote Similarity	NPD2979	Phase 3
0.6812	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD3620	Phase 2
0.6809	Remote Similarity	NPD5404	Approved
0.6809	Remote Similarity	NPD5406	Approved
0.6809	Remote Similarity	NPD5408	Approved
0.6809	Remote Similarity	NPD5405	Approved
0.68	Remote Similarity	NPD1137	Approved
0.68	Remote Similarity	NPD1934	Approved
0.68	Remote Similarity	NPD1139	Approved
0.6794	Remote Similarity	NPD1983	Approved
0.6794	Remote Similarity	NPD1981	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