NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.08
Volume:	261.72
LogP:	1.184
LogD:	1.036
LogS:	-1.411
# Rotatable Bonds:	3
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.541
Synthetic Accessibility Score:	2.377
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.052
MDCK Permeability:	4.519057711149799e-06
Pgp-inhibitor:	0.032
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.73
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	86.5385513305664%
Volume Distribution (VD):	0.638
Pgp-substrate:	7.7675909996032715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.405
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.277
CYP2C9-substrate:	0.499
CYP2D6-inhibitor:	0.243
CYP2D6-substrate:	0.555
CYP3A4-inhibitor:	0.09
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	17.246
Half-life (T1/2):	0.95

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.054
Drug-inuced Liver Injury (DILI):	0.759
AMES Toxicity:	0.735
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.045
Skin Sensitization:	0.959
Carcinogencity:	0.074
Eye Corrosion:	0.004
Eye Irritation:	0.954
Respiratory Toxicity:	0.051

Download Data

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

Natural Product: NPC471485

Natural Product ID:	NPC471485
*Common Name:**	4-(4,5-Dihydroxy-2-(Hydroxymethyl)Benzyl)Benzene-1,2-Diol
IUPAC Name:	4-[(3,4-dihydroxyphenyl)methyl]-5-(hydroxymethyl)benzene-1,2-diol
Synonyms:
Standard InCHIKey:	ICHHNWYBLKUNGP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H14O5/c15-7-10-6-14(19)13(18)5-9(10)3-8-1-2-11(16)12(17)4-8/h1-2,4-6,15-19H,3,7H2
SMILES:	OCc1cc(O)c(cc1Cc1ccc(c(c1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252872
PubChem CID:	44446406
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
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395508]
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18053715]
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	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
MIC	10

Activity Type	# Activity
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[512723]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[512723]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[512723]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[512723]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[512723]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[512723]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[512723]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[512723]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	100.0	ug.mL-1	PMID[512723]
NPT3173	Organism	Arthroderma benhamiae	Arthroderma benhamiae	MIC	>	100.0	ug.mL-1	PMID[512723]

☑ 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 NPC471485 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	392
0.1-0.2	1592
0.2-0.3	4636
0.3-0.4	13323
0.4-0.5	5670
0.5-0.6	7683
0.6-0.7	6709
0.7-0.8	2385
0.8-0.85	266
0.85-0.9	24
0.9-0.95	16
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC472071
0.9358	High Similarity	NPC120280
0.9167	High Similarity	NPC174096
0.9167	High Similarity	NPC226401
0.9167	High Similarity	NPC120982
0.9167	High Similarity	NPC79793
0.9167	High Similarity	NPC147634
0.9143	High Similarity	NPC12278
0.9143	High Similarity	NPC471511
0.9123	High Similarity	NPC470414
0.9083	High Similarity	NPC187583
0.9083	High Similarity	NPC257430
0.9083	High Similarity	NPC179002
0.9074	High Similarity	NPC55617
0.9074	High Similarity	NPC62258
0.9057	High Similarity	NPC239291
0.8981	High Similarity	NPC233835
0.8952	High Similarity	NPC110764
0.8929	High Similarity	NPC472893
0.8909	High Similarity	NPC268032
0.8899	High Similarity	NPC228343
0.8899	High Similarity	NPC254833
0.8857	High Similarity	NPC223393
0.8762	High Similarity	NPC131587
0.8729	High Similarity	NPC473451
0.8667	High Similarity	NPC109955
0.8636	High Similarity	NPC58427
0.8636	High Similarity	NPC105727
0.8636	High Similarity	NPC114392
0.8636	High Similarity	NPC34864
0.8621	High Similarity	NPC217174
0.8621	High Similarity	NPC176893
0.8611	High Similarity	NPC323810
0.8611	High Similarity	NPC120719
0.8559	High Similarity	NPC237667
0.8547	High Similarity	NPC475245
0.8545	High Similarity	NPC176527
0.8509	High Similarity	NPC12656
0.8509	High Similarity	NPC473137
0.85	High Similarity	NPC131747
0.85	High Similarity	NPC257682
0.85	High Similarity	NPC146355
0.8491	Intermediate Similarity	NPC32674
0.8487	Intermediate Similarity	NPC471794
0.8487	Intermediate Similarity	NPC85488
0.8476	Intermediate Similarity	NPC274678
0.8462	Intermediate Similarity	NPC470214
0.8462	Intermediate Similarity	NPC470215
0.8462	Intermediate Similarity	NPC109371
0.8455	Intermediate Similarity	NPC477814
0.8455	Intermediate Similarity	NPC474614
0.8448	Intermediate Similarity	NPC200988
0.8448	Intermediate Similarity	NPC278652
0.8448	Intermediate Similarity	NPC145023
0.8448	Intermediate Similarity	NPC175799
0.8448	Intermediate Similarity	NPC610
0.8443	Intermediate Similarity	NPC5428
0.8443	Intermediate Similarity	NPC118533
0.8443	Intermediate Similarity	NPC106511
0.8443	Intermediate Similarity	NPC165045
0.843	Intermediate Similarity	NPC148627
0.8421	Intermediate Similarity	NPC264558
0.8417	Intermediate Similarity	NPC53567
0.8417	Intermediate Similarity	NPC471693
0.8417	Intermediate Similarity	NPC280704
0.8407	Intermediate Similarity	NPC308689
0.8407	Intermediate Similarity	NPC297657
0.8403	Intermediate Similarity	NPC39029
0.84	Intermediate Similarity	NPC300678
0.839	Intermediate Similarity	NPC34634
0.839	Intermediate Similarity	NPC265454
0.8376	Intermediate Similarity	NPC86198
0.8376	Intermediate Similarity	NPC144343
0.8374	Intermediate Similarity	NPC307050
0.8374	Intermediate Similarity	NPC277458
0.8349	Intermediate Similarity	NPC196479
0.8349	Intermediate Similarity	NPC477802
0.8349	Intermediate Similarity	NPC477801
0.8333	Intermediate Similarity	NPC294741
0.8333	Intermediate Similarity	NPC471179
0.8319	Intermediate Similarity	NPC44732
0.8319	Intermediate Similarity	NPC207613
0.8306	Intermediate Similarity	NPC475875
0.8305	Intermediate Similarity	NPC320987
0.8305	Intermediate Similarity	NPC70084
0.8305	Intermediate Similarity	NPC181969
0.8304	Intermediate Similarity	NPC95344
0.8302	Intermediate Similarity	NPC107522
0.8293	Intermediate Similarity	NPC108659
0.8293	Intermediate Similarity	NPC79715
0.8293	Intermediate Similarity	NPC476536
0.8293	Intermediate Similarity	NPC231607
0.8293	Intermediate Similarity	NPC264900
0.8291	Intermediate Similarity	NPC293619
0.8291	Intermediate Similarity	NPC277588
0.8279	Intermediate Similarity	NPC33654
0.8273	Intermediate Similarity	NPC30506
0.8273	Intermediate Similarity	NPC254965
0.8273	Intermediate Similarity	NPC327811
0.8268	Intermediate Similarity	NPC311256
0.8264	Intermediate Similarity	NPC84086
0.8257	Intermediate Similarity	NPC40258
0.8257	Intermediate Similarity	NPC7686
0.8257	Intermediate Similarity	NPC91461
0.825	Intermediate Similarity	NPC184651
0.825	Intermediate Similarity	NPC113865
0.825	Intermediate Similarity	NPC262156
0.825	Intermediate Similarity	NPC470212
0.825	Intermediate Similarity	NPC343720
0.825	Intermediate Similarity	NPC472271
0.825	Intermediate Similarity	NPC476343
0.825	Intermediate Similarity	NPC324571
0.825	Intermediate Similarity	NPC54872
0.825	Intermediate Similarity	NPC266045
0.825	Intermediate Similarity	NPC147654
0.825	Intermediate Similarity	NPC312675
0.825	Intermediate Similarity	NPC473853
0.8241	Intermediate Similarity	NPC132078
0.8241	Intermediate Similarity	NPC216468
0.8241	Intermediate Similarity	NPC51333
0.8241	Intermediate Similarity	NPC78119
0.824	Intermediate Similarity	NPC187998
0.824	Intermediate Similarity	NPC153739
0.824	Intermediate Similarity	NPC64201
0.824	Intermediate Similarity	NPC145305
0.824	Intermediate Similarity	NPC77040
0.824	Intermediate Similarity	NPC257582
0.824	Intermediate Similarity	NPC92164
0.824	Intermediate Similarity	NPC242807
0.824	Intermediate Similarity	NPC42300
0.824	Intermediate Similarity	NPC241522
0.824	Intermediate Similarity	NPC174495
0.824	Intermediate Similarity	NPC143483
0.8235	Intermediate Similarity	NPC148615
0.8235	Intermediate Similarity	NPC95614
0.8235	Intermediate Similarity	NPC35071
0.8235	Intermediate Similarity	NPC117780
0.8235	Intermediate Similarity	NPC56214
0.8235	Intermediate Similarity	NPC165133
0.8235	Intermediate Similarity	NPC232316
0.8235	Intermediate Similarity	NPC242885
0.8235	Intermediate Similarity	NPC227217
0.8235	Intermediate Similarity	NPC177475
0.8235	Intermediate Similarity	NPC223451
0.823	Intermediate Similarity	NPC202647
0.823	Intermediate Similarity	NPC473524
0.8226	Intermediate Similarity	NPC245826
0.8226	Intermediate Similarity	NPC11258
0.8226	Intermediate Similarity	NPC128208
0.8226	Intermediate Similarity	NPC184733
0.8226	Intermediate Similarity	NPC474178
0.8226	Intermediate Similarity	NPC472968
0.8226	Intermediate Similarity	NPC21867
0.8226	Intermediate Similarity	NPC282703
0.8226	Intermediate Similarity	NPC252307
0.8226	Intermediate Similarity	NPC129570
0.8226	Intermediate Similarity	NPC45774
0.822	Intermediate Similarity	NPC255675
0.822	Intermediate Similarity	NPC470626
0.822	Intermediate Similarity	NPC63126
0.8211	Intermediate Similarity	NPC94179
0.8211	Intermediate Similarity	NPC178284
0.8211	Intermediate Similarity	NPC58607
0.8211	Intermediate Similarity	NPC191037
0.8205	Intermediate Similarity	NPC221049
0.8198	Intermediate Similarity	NPC471350
0.8197	Intermediate Similarity	NPC224342
0.819	Intermediate Similarity	NPC45040
0.8189	Intermediate Similarity	NPC163560
0.8189	Intermediate Similarity	NPC474453
0.8182	Intermediate Similarity	NPC233827
0.8182	Intermediate Similarity	NPC86900
0.8182	Intermediate Similarity	NPC321402
0.8175	Intermediate Similarity	NPC474017
0.8175	Intermediate Similarity	NPC277804
0.8167	Intermediate Similarity	NPC24125
0.8167	Intermediate Similarity	NPC98305
0.8167	Intermediate Similarity	NPC284078
0.8165	Intermediate Similarity	NPC213730
0.8165	Intermediate Similarity	NPC130103
0.816	Intermediate Similarity	NPC470747
0.816	Intermediate Similarity	NPC476968
0.816	Intermediate Similarity	NPC170844
0.816	Intermediate Similarity	NPC184092
0.8151	Intermediate Similarity	NPC141791
0.8151	Intermediate Similarity	NPC477803
0.8151	Intermediate Similarity	NPC263386
0.8151	Intermediate Similarity	NPC281298
0.8151	Intermediate Similarity	NPC151197
0.8151	Intermediate Similarity	NPC310338
0.8151	Intermediate Similarity	NPC191866
0.8148	Intermediate Similarity	NPC474073
0.8148	Intermediate Similarity	NPC156313
0.8145	Intermediate Similarity	NPC41706
0.8145	Intermediate Similarity	NPC118787
0.8145	Intermediate Similarity	NPC163332
0.8145	Intermediate Similarity	NPC111247
0.8145	Intermediate Similarity	NPC147821
0.8145	Intermediate Similarity	NPC292056
0.8145	Intermediate Similarity	NPC21563

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 NPC471485 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	908
0.2-0.3	1561
0.3-0.4	3012
0.4-0.5	1707
0.5-0.6	1100
0.6-0.7	419
0.7-0.8	78
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8899	High Similarity	NPD3021	Approved
0.8899	High Similarity	NPD3022	Approved
0.816	Intermediate Similarity	NPD3027	Phase 3
0.8083	Intermediate Similarity	NPD9381	Approved
0.8083	Intermediate Similarity	NPD9384	Approved
0.8073	Intermediate Similarity	NPD3020	Approved
0.8	Intermediate Similarity	NPD1242	Phase 1
0.8	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD3094	Phase 2
0.7969	Intermediate Similarity	NPD1613	Approved
0.7969	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD2860	Approved
0.7963	Intermediate Similarity	NPD2859	Approved
0.7951	Intermediate Similarity	NPD3092	Approved
0.7931	Intermediate Similarity	NPD228	Approved
0.787	Intermediate Similarity	NPD2934	Approved
0.787	Intermediate Similarity	NPD2933	Approved
0.7829	Intermediate Similarity	NPD3061	Approved
0.7829	Intermediate Similarity	NPD3059	Approved
0.7829	Intermediate Similarity	NPD3062	Approved
0.7823	Intermediate Similarity	NPD9622	Approved
0.7795	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD3091	Approved
0.7744	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD9379	Approved
0.7712	Intermediate Similarity	NPD9377	Approved
0.771	Intermediate Similarity	NPD5314	Approved
0.7706	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5283	Phase 1
0.7638	Intermediate Similarity	NPD9621	Approved
0.7638	Intermediate Similarity	NPD9619	Approved
0.7638	Intermediate Similarity	NPD9620	Approved
0.7586	Intermediate Similarity	NPD2342	Discontinued
0.7568	Intermediate Similarity	NPD288	Approved
0.7563	Intermediate Similarity	NPD7635	Approved
0.7557	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD3620	Phase 2
0.7538	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3095	Discontinued
0.7481	Intermediate Similarity	NPD7266	Discontinued
0.7477	Intermediate Similarity	NPD844	Approved
0.7456	Intermediate Similarity	NPD940	Approved
0.7456	Intermediate Similarity	NPD846	Approved
0.7444	Intermediate Similarity	NPD823	Approved
0.7444	Intermediate Similarity	NPD817	Approved
0.7424	Intermediate Similarity	NPD943	Approved
0.7422	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD601	Approved
0.7405	Intermediate Similarity	NPD597	Approved
0.7405	Intermediate Similarity	NPD598	Approved
0.7402	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD2286	Discontinued
0.7358	Intermediate Similarity	NPD111	Approved
0.7355	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD1130	Approved
0.7348	Intermediate Similarity	NPD1136	Approved
0.7348	Intermediate Similarity	NPD1132	Approved
0.7344	Intermediate Similarity	NPD5311	Approved
0.7344	Intermediate Similarity	NPD5310	Approved
0.7311	Intermediate Similarity	NPD4750	Phase 3
0.7311	Intermediate Similarity	NPD1792	Phase 2
0.7311	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2861	Phase 2
0.7293	Intermediate Similarity	NPD4060	Phase 1
0.7287	Intermediate Similarity	NPD3055	Approved
0.7287	Intermediate Similarity	NPD3053	Approved
0.728	Intermediate Similarity	NPD4093	Discontinued
0.7279	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1201	Approved
0.7244	Intermediate Similarity	NPD3705	Approved
0.7244	Intermediate Similarity	NPD1610	Phase 2
0.7234	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3019	Approved
0.7222	Intermediate Similarity	NPD2932	Approved
0.7222	Intermediate Similarity	NPD4059	Approved
0.7222	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD968	Approved
0.7188	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1809	Phase 2
0.7164	Intermediate Similarity	NPD1558	Phase 1
0.7154	Intermediate Similarity	NPD497	Approved
0.7154	Intermediate Similarity	NPD1470	Approved
0.7153	Intermediate Similarity	NPD9570	Approved
0.7143	Intermediate Similarity	NPD845	Approved
0.7143	Intermediate Similarity	NPD6190	Approved
0.7122	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD257	Approved
0.7099	Intermediate Similarity	NPD258	Approved
0.7097	Intermediate Similarity	NPD7157	Approved
0.7087	Intermediate Similarity	NPD1751	Approved
0.7083	Intermediate Similarity	NPD2684	Approved
0.7077	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2229	Approved
0.7073	Intermediate Similarity	NPD2234	Approved
0.7073	Intermediate Similarity	NPD498	Approved
0.7073	Intermediate Similarity	NPD2228	Approved
0.7073	Intermediate Similarity	NPD495	Approved
0.7073	Intermediate Similarity	NPD496	Approved
0.7071	Intermediate Similarity	NPD8166	Discontinued
0.7069	Intermediate Similarity	NPD3028	Approved
0.7063	Intermediate Similarity	NPD1548	Phase 1
0.7059	Intermediate Similarity	NPD1445	Approved
0.7059	Intermediate Similarity	NPD1444	Approved
0.7054	Intermediate Similarity	NPD9269	Phase 2
0.7045	Intermediate Similarity	NPD5736	Approved
0.7037	Intermediate Similarity	NPD825	Approved
0.7037	Intermediate Similarity	NPD826	Approved
0.7023	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD4103	Phase 2
0.7016	Intermediate Similarity	NPD9614	Approved
0.7016	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD9618	Approved
0.7008	Intermediate Similarity	NPD1357	Approved
0.7	Intermediate Similarity	NPD9094	Approved
0.7	Intermediate Similarity	NPD3060	Approved
0.7	Intermediate Similarity	NPD4659	Approved
0.6992	Remote Similarity	NPD4908	Phase 1
0.6992	Remote Similarity	NPD7843	Approved
0.6985	Remote Similarity	NPD5735	Approved
0.6985	Remote Similarity	NPD230	Phase 1
0.6977	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1283	Approved
0.6934	Remote Similarity	NPD2568	Approved
0.6923	Remote Similarity	NPD2561	Approved
0.6923	Remote Similarity	NPD2562	Approved
0.6923	Remote Similarity	NPD1840	Phase 2
0.6917	Remote Similarity	NPD9569	Approved
0.6912	Remote Similarity	NPD2238	Phase 2
0.6911	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5111	Phase 2
0.6889	Remote Similarity	NPD3764	Approved
0.6889	Remote Similarity	NPD5110	Phase 2
0.6889	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5109	Approved
0.6875	Remote Similarity	NPD3645	Discontinued
0.6875	Remote Similarity	NPD1651	Approved
0.687	Remote Similarity	NPD2982	Phase 2
0.687	Remote Similarity	NPD1669	Approved
0.687	Remote Similarity	NPD2983	Phase 2
0.6861	Remote Similarity	NPD555	Phase 2
0.6853	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3845	Phase 1
0.685	Remote Similarity	NPD856	Approved
0.685	Remote Similarity	NPD9615	Approved
0.685	Remote Similarity	NPD317	Approved
0.685	Remote Similarity	NPD9613	Approved
0.685	Remote Similarity	NPD9616	Approved
0.685	Remote Similarity	NPD16	Approved
0.685	Remote Similarity	NPD5536	Phase 2
0.685	Remote Similarity	NPD318	Approved
0.6842	Remote Similarity	NPD6584	Phase 3
0.6838	Remote Similarity	NPD259	Phase 1
0.6838	Remote Similarity	NPD6663	Approved
0.6838	Remote Similarity	NPD6405	Approved
0.6838	Remote Similarity	NPD6407	Approved
0.6825	Remote Similarity	NPD709	Approved
0.6825	Remote Similarity	NPD6671	Approved
0.6822	Remote Similarity	NPD5126	Approved
0.6822	Remote Similarity	NPD4626	Approved
0.6822	Remote Similarity	NPD5846	Approved
0.6822	Remote Similarity	NPD5125	Phase 3
0.6822	Remote Similarity	NPD6516	Phase 2
0.6815	Remote Similarity	NPD4625	Phase 3
0.6806	Remote Similarity	NPD2420	Approved
0.6806	Remote Similarity	NPD1511	Approved
0.6806	Remote Similarity	NPD2421	Approved
0.68	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD316	Approved
0.6794	Remote Similarity	NPD2232	Approved
0.6794	Remote Similarity	NPD2233	Approved
0.6794	Remote Similarity	NPD2981	Phase 2
0.6794	Remote Similarity	NPD2230	Approved
0.6791	Remote Similarity	NPD9494	Approved
0.6791	Remote Similarity	NPD3018	Phase 2
0.6783	Remote Similarity	NPD5241	Discontinued
0.6783	Remote Similarity	NPD2677	Approved
0.6779	Remote Similarity	NPD37	Approved
0.6779	Remote Similarity	NPD1934	Approved
0.6776	Remote Similarity	NPD6234	Discontinued
0.6772	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD3023	Approved
0.6769	Remote Similarity	NPD3026	Approved
0.6763	Remote Similarity	NPD4538	Approved
0.6763	Remote Similarity	NPD4536	Approved
0.6763	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD9294	Approved
0.6761	Remote Similarity	NPD6674	Discontinued
0.675	Remote Similarity	NPD9610	Approved
0.675	Remote Similarity	NPD9608	Approved
0.6744	Remote Similarity	NPD9268	Approved
0.6744	Remote Similarity	NPD3025	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