NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.09
Volume:	252.929
LogP:	2.799
LogD:	2.773
LogS:	-3.648
# Rotatable Bonds:	3
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.874
Synthetic Accessibility Score:	1.845
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:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.773
MDCK Permeability:	2.2674110368825495e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.132
Plasma Protein Binding (PPB):	97.18008422851562%
Volume Distribution (VD):	0.519
Pgp-substrate:	3.0107662677764893%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.943
CYP2C19-inhibitor:	0.706
CYP2C19-substrate:	0.285
CYP2C9-inhibitor:	0.517
CYP2C9-substrate:	0.837
CYP2D6-inhibitor:	0.676
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.573
CYP3A4-substrate:	0.377

ADMET: Excretion

Clearance (CL):	11.246
Half-life (T1/2):	0.9

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.075
Drug-inuced Liver Injury (DILI):	0.26
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.206
Maximum Recommended Daily Dose:	0.099
Skin Sensitization:	0.923
Carcinogencity:	0.233
Eye Corrosion:	0.115
Eye Irritation:	0.934
Respiratory Toxicity:	0.375

Download Data

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

Natural Product: NPC266555

Natural Product ID:	NPC266555
*Common Name:**	2'-Hydroxyaucuparin
IUPAC Name:	4-(2-hydroxyphenyl)-2,6-dimethoxyphenol
Synonyms:	2'-Hydroxyaucuparin
Standard InCHIKey:	CBRMMSPVRYLGMR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H14O4/c1-17-12-7-9(8-13(18-2)14(12)16)10-5-3-4-6-11(10)15/h3-8,15-16H,1-2H3
SMILES:	COc1cc(cc(c1O)OC)c1ccccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080486
PubChem CID:	46879744
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000041] Biphenyls and derivatives

*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
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19813743]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	trunk	Jeju island, Korea	2005-Dec	PMID[21420296]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21420296]
NPO4001	Berberis koreana	Species	Berberidaceae	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
Others	3

Activity Type	# Activity
Cell Line	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[533823]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[533823]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	10000.0	nM	PMID[533823]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	>	10000.0	nM	PMID[533823]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	118.53	%	PMID[533824]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	137.33	%	PMID[533824]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	38060.0	nM	PMID[533824]
NPT27	Others	Unspecified		Activity	=	117.68	%	PMID[533824]

☑ 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 NPC266555 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	478
0.1-0.2	1856
0.2-0.3	5601
0.3-0.4	13255
0.4-0.5	3889
0.5-0.6	4080
0.6-0.7	7143
0.7-0.8	4774
0.8-0.85	819
0.85-0.9	497
0.9-0.95	240
0.95-1	65

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC154866
0.9752	High Similarity	NPC223953
0.975	High Similarity	NPC5796
0.975	High Similarity	NPC206487
0.9672	High Similarity	NPC169474
0.9672	High Similarity	NPC159968
0.9672	High Similarity	NPC236791
0.9672	High Similarity	NPC246620
0.9672	High Similarity	NPC282000
0.9672	High Similarity	NPC124452
0.9672	High Similarity	NPC324112
0.9672	High Similarity	NPC293054
0.9672	High Similarity	NPC74817
0.9672	High Similarity	NPC82679
0.9667	High Similarity	NPC84086
0.9597	High Similarity	NPC126836
0.959	High Similarity	NPC18924
0.959	High Similarity	NPC28730
0.959	High Similarity	NPC78974
0.959	High Similarity	NPC214406
0.959	High Similarity	NPC44748
0.959	High Similarity	NPC103823
0.959	High Similarity	NPC223136
0.9524	High Similarity	NPC32778
0.9512	High Similarity	NPC127587
0.9508	High Similarity	NPC82483
0.9508	High Similarity	NPC116907
0.9508	High Similarity	NPC472093
0.9508	High Similarity	NPC57490
0.9508	High Similarity	NPC298757
0.9508	High Similarity	NPC203133
0.9508	High Similarity	NPC117214
0.9508	High Similarity	NPC193544
0.9508	High Similarity	NPC475169
0.9508	High Similarity	NPC265483
0.9508	High Similarity	NPC105925
0.9508	High Similarity	NPC60885
0.9508	High Similarity	NPC299584
0.9508	High Similarity	NPC221077
0.9508	High Similarity	NPC234400
0.9508	High Similarity	NPC233410
0.9508	High Similarity	NPC17943
0.9508	High Similarity	NPC251855
0.9508	High Similarity	NPC208950
0.9504	High Similarity	NPC197757
0.9504	High Similarity	NPC228922
0.9504	High Similarity	NPC121115
0.9449	High Similarity	NPC160697
0.9444	High Similarity	NPC6451
0.944	High Similarity	NPC51840
0.944	High Similarity	NPC299221
0.944	High Similarity	NPC234488
0.944	High Similarity	NPC311680
0.9435	High Similarity	NPC28765
0.9431	High Similarity	NPC76451
0.9421	High Similarity	NPC41562
0.9375	High Similarity	NPC158142
0.9375	High Similarity	NPC200557
0.9375	High Similarity	NPC108198
0.9375	High Similarity	NPC69029
0.9375	High Similarity	NPC10314
0.9375	High Similarity	NPC294884
0.9375	High Similarity	NPC256262
0.9365	High Similarity	NPC45715
0.9365	High Similarity	NPC232275
0.9365	High Similarity	NPC12275
0.9365	High Similarity	NPC474356
0.936	High Similarity	NPC10225
0.936	High Similarity	NPC58164
0.936	High Similarity	NPC212015
0.9355	High Similarity	NPC236760
0.9355	High Similarity	NPC252131
0.9344	High Similarity	NPC282496
0.9344	High Similarity	NPC233526
0.9344	High Similarity	NPC95168
0.9344	High Similarity	NPC136319
0.9333	High Similarity	NPC247364
0.9333	High Similarity	NPC61516
0.9333	High Similarity	NPC232084
0.9333	High Similarity	NPC10932
0.9302	High Similarity	NPC143139
0.9302	High Similarity	NPC202846
0.9297	High Similarity	NPC555
0.9297	High Similarity	NPC7515
0.9297	High Similarity	NPC289258
0.9297	High Similarity	NPC56764
0.9297	High Similarity	NPC276026
0.9297	High Similarity	NPC206737
0.9297	High Similarity	NPC469659
0.9297	High Similarity	NPC125649
0.9297	High Similarity	NPC188378
0.9291	High Similarity	NPC86655
0.9291	High Similarity	NPC202762
0.9286	High Similarity	NPC192687
0.9286	High Similarity	NPC224157
0.928	High Similarity	NPC186843
0.928	High Similarity	NPC206615
0.928	High Similarity	NPC266691
0.928	High Similarity	NPC470213
0.928	High Similarity	NPC98631
0.9262	High Similarity	NPC262253
0.9262	High Similarity	NPC71579
0.9262	High Similarity	NPC473411
0.925	High Similarity	NPC226629
0.925	High Similarity	NPC20674
0.9231	High Similarity	NPC25111
0.9231	High Similarity	NPC272157
0.9231	High Similarity	NPC200935
0.9231	High Similarity	NPC73535
0.9231	High Similarity	NPC266453
0.9231	High Similarity	NPC56329
0.9231	High Similarity	NPC201145
0.9231	High Similarity	NPC151656
0.9231	High Similarity	NPC90615
0.9231	High Similarity	NPC230919
0.9231	High Similarity	NPC6262
0.9231	High Similarity	NPC242715
0.9225	High Similarity	NPC240279
0.9225	High Similarity	NPC214853
0.9225	High Similarity	NPC55239
0.9225	High Similarity	NPC180602
0.9225	High Similarity	NPC241241
0.9225	High Similarity	NPC313081
0.9219	High Similarity	NPC475840
0.9213	High Similarity	NPC15543
0.9213	High Similarity	NPC474017
0.9206	High Similarity	NPC170844
0.9206	High Similarity	NPC476968
0.9206	High Similarity	NPC190144
0.92	High Similarity	NPC210355
0.92	High Similarity	NPC21563
0.918	High Similarity	NPC75713
0.916	High Similarity	NPC243996
0.916	High Similarity	NPC132804
0.916	High Similarity	NPC218131
0.916	High Similarity	NPC79622
0.916	High Similarity	NPC220344
0.916	High Similarity	NPC212942
0.916	High Similarity	NPC243759
0.916	High Similarity	NPC105847
0.916	High Similarity	NPC29868
0.916	High Similarity	NPC275061
0.9154	High Similarity	NPC300846
0.9154	High Similarity	NPC162659
0.9154	High Similarity	NPC270456
0.9154	High Similarity	NPC30632
0.9154	High Similarity	NPC476639
0.9154	High Similarity	NPC114155
0.9154	High Similarity	NPC248727
0.9154	High Similarity	NPC133025
0.9154	High Similarity	NPC265433
0.9147	High Similarity	NPC317380
0.9147	High Similarity	NPC209199
0.9141	High Similarity	NPC127624
0.9134	High Similarity	NPC91291
0.9127	High Similarity	NPC226331
0.9127	High Similarity	NPC46274
0.9113	High Similarity	NPC183446
0.9098	High Similarity	NPC166759
0.9091	High Similarity	NPC266650
0.9091	High Similarity	NPC12668
0.9091	High Similarity	NPC308768
0.9091	High Similarity	NPC15805
0.9091	High Similarity	NPC295719
0.9091	High Similarity	NPC34431
0.9091	High Similarity	NPC73505
0.9091	High Similarity	NPC165026
0.9084	High Similarity	NPC22902
0.9084	High Similarity	NPC301765
0.9084	High Similarity	NPC156948
0.9084	High Similarity	NPC46277
0.9084	High Similarity	NPC3072
0.9084	High Similarity	NPC86605
0.9083	High Similarity	NPC244816
0.9083	High Similarity	NPC50521
0.9083	High Similarity	NPC221549
0.9083	High Similarity	NPC195466
0.9083	High Similarity	NPC259638
0.9077	High Similarity	NPC261873
0.9077	High Similarity	NPC111655
0.9077	High Similarity	NPC112939
0.9077	High Similarity	NPC470356
0.9077	High Similarity	NPC474206
0.9077	High Similarity	NPC94750
0.9077	High Similarity	NPC112246
0.9077	High Similarity	NPC283009
0.9077	High Similarity	NPC121812
0.907	High Similarity	NPC471391
0.907	High Similarity	NPC471390
0.907	High Similarity	NPC229442
0.907	High Similarity	NPC158331
0.907	High Similarity	NPC168059
0.9055	High Similarity	NPC469951
0.9055	High Similarity	NPC45824
0.9055	High Similarity	NPC469963
0.9048	High Similarity	NPC242032
0.9048	High Similarity	NPC470699
0.9048	High Similarity	NPC250432
0.9048	High Similarity	NPC5447
0.9024	High Similarity	NPC145780

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 NPC266555 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	419
0.1-0.2	979
0.2-0.3	1806
0.3-0.4	2741
0.4-0.5	1574
0.5-0.6	883
0.6-0.7	611
0.7-0.8	120
0.8-0.85	11
0.85-0.9	3
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9206	High Similarity	NPD3027	Phase 3
0.9127	High Similarity	NPD1529	Clinical (unspecified phase)
0.9048	High Similarity	NPD1530	Clinical (unspecified phase)
0.8992	High Similarity	NPD1612	Clinical (unspecified phase)
0.8992	High Similarity	NPD1613	Approved
0.8583	High Similarity	NPD228	Approved
0.8462	Intermediate Similarity	NPD3018	Phase 2
0.8425	Intermediate Similarity	NPD1610	Phase 2
0.8295	Intermediate Similarity	NPD2982	Phase 2
0.8295	Intermediate Similarity	NPD2983	Phase 2
0.8293	Intermediate Similarity	NPD5283	Phase 1
0.8258	Intermediate Similarity	NPD4908	Phase 1
0.8254	Intermediate Similarity	NPD1548	Phase 1
0.8217	Intermediate Similarity	NPD2981	Phase 2
0.8134	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD4625	Phase 3
0.8027	Intermediate Similarity	NPD1934	Approved
0.8015	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD3022	Approved
0.7967	Intermediate Similarity	NPD3021	Approved
0.7883	Intermediate Similarity	NPD1558	Phase 1
0.7879	Intermediate Similarity	NPD4749	Approved
0.7852	Intermediate Similarity	NPD2801	Approved
0.7847	Intermediate Similarity	NPD1511	Approved
0.7801	Intermediate Similarity	NPD3540	Phase 1
0.775	Intermediate Similarity	NPD1242	Phase 1
0.7748	Intermediate Similarity	NPD3882	Suspended
0.7744	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1512	Approved
0.7733	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD3539	Phase 1
0.7727	Intermediate Similarity	NPD422	Phase 1
0.7704	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD846	Approved
0.7686	Intermediate Similarity	NPD940	Approved
0.7647	Intermediate Similarity	NPD2861	Phase 2
0.7647	Intermediate Similarity	NPD6234	Discontinued
0.7635	Intermediate Similarity	NPD1653	Approved
0.7626	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD4060	Phase 1
0.7626	Intermediate Similarity	NPD1240	Approved
0.7626	Intermediate Similarity	NPD3620	Phase 2
0.7616	Intermediate Similarity	NPD1465	Phase 2
0.7613	Intermediate Similarity	NPD6232	Discontinued
0.7609	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD37	Approved
0.754	Intermediate Similarity	NPD4750	Phase 3
0.7535	Intermediate Similarity	NPD1510	Phase 2
0.7534	Intermediate Similarity	NPD7124	Phase 2
0.7518	Intermediate Similarity	NPD1607	Approved
0.7516	Intermediate Similarity	NPD6166	Phase 2
0.7516	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD943	Approved
0.7483	Intermediate Similarity	NPD4357	Discontinued
0.7482	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD5536	Phase 2
0.7468	Intermediate Similarity	NPD7473	Discontinued
0.7468	Intermediate Similarity	NPD4055	Discovery
0.7467	Intermediate Similarity	NPD4005	Discontinued
0.7463	Intermediate Similarity	NPD3705	Approved
0.7436	Intermediate Similarity	NPD7199	Phase 2
0.7403	Intermediate Similarity	NPD4966	Approved
0.7403	Intermediate Similarity	NPD4965	Approved
0.7403	Intermediate Similarity	NPD4967	Phase 2
0.7381	Intermediate Similarity	NPD290	Approved
0.7379	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1357	Approved
0.7355	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6111	Discontinued
0.7342	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3817	Phase 2
0.7333	Intermediate Similarity	NPD9296	Approved
0.7333	Intermediate Similarity	NPD1091	Approved
0.7329	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7074	Phase 3
0.7329	Intermediate Similarity	NPD3060	Approved
0.7328	Intermediate Similarity	NPD7157	Approved
0.7328	Intermediate Similarity	NPD709	Approved
0.7328	Intermediate Similarity	NPD6671	Approved
0.7324	Intermediate Similarity	NPD230	Phase 1
0.7323	Intermediate Similarity	NPD2684	Approved
0.7312	Intermediate Similarity	NPD3818	Discontinued
0.7312	Intermediate Similarity	NPD7228	Approved
0.731	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2674	Phase 3
0.7303	Intermediate Similarity	NPD4678	Approved
0.7303	Intermediate Similarity	NPD4675	Approved
0.7299	Intermediate Similarity	NPD8651	Approved
0.7279	Intermediate Similarity	NPD3750	Approved
0.7267	Intermediate Similarity	NPD5844	Phase 1
0.7267	Intermediate Similarity	NPD7054	Approved
0.7266	Intermediate Similarity	NPD9494	Approved
0.726	Intermediate Similarity	NPD1549	Phase 2
0.7248	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6099	Approved
0.7241	Intermediate Similarity	NPD6100	Approved
0.7236	Intermediate Similarity	NPD3020	Approved
0.7234	Intermediate Similarity	NPD5109	Approved
0.7234	Intermediate Similarity	NPD5111	Phase 2
0.7234	Intermediate Similarity	NPD5110	Phase 2
0.7231	Intermediate Similarity	NPD7843	Approved
0.723	Intermediate Similarity	NPD2219	Phase 1
0.7222	Intermediate Similarity	NPD7472	Approved
0.7219	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD8054	Approved
0.7212	Intermediate Similarity	NPD8053	Approved
0.7211	Intermediate Similarity	NPD6674	Discontinued
0.7211	Intermediate Similarity	NPD5177	Phase 3
0.72	Intermediate Similarity	NPD7447	Phase 1
0.72	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7266	Discontinued
0.719	Intermediate Similarity	NPD4380	Phase 2
0.7185	Intermediate Similarity	NPD4626	Approved
0.7174	Intermediate Similarity	NPD1283	Approved
0.7174	Intermediate Similarity	NPD2922	Phase 1
0.7165	Intermediate Similarity	NPD968	Approved
0.7163	Intermediate Similarity	NPD7095	Approved
0.7162	Intermediate Similarity	NPD3892	Phase 2
0.7153	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD5089	Approved
0.7143	Intermediate Similarity	NPD5090	Approved
0.7133	Intermediate Similarity	NPD7213	Phase 3
0.7133	Intermediate Similarity	NPD7212	Phase 2
0.7133	Intermediate Similarity	NPD2238	Phase 2
0.7131	Intermediate Similarity	NPD2860	Approved
0.7131	Intermediate Similarity	NPD2859	Approved
0.7123	Intermediate Similarity	NPD2935	Discontinued
0.7113	Intermediate Similarity	NPD3145	Approved
0.7113	Intermediate Similarity	NPD3144	Approved
0.7111	Intermediate Similarity	NPD1651	Approved
0.7101	Intermediate Similarity	NPD1669	Approved
0.7095	Intermediate Similarity	NPD1652	Phase 2
0.7095	Intermediate Similarity	NPD4237	Approved
0.7095	Intermediate Similarity	NPD4236	Phase 3
0.7083	Intermediate Similarity	NPD6355	Discontinued
0.7075	Intermediate Similarity	NPD1375	Discontinued
0.7073	Intermediate Similarity	NPD288	Approved
0.7073	Intermediate Similarity	NPD6797	Phase 2
0.7071	Intermediate Similarity	NPD6584	Phase 3
0.7055	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2933	Approved
0.7049	Intermediate Similarity	NPD2934	Approved
0.7047	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5494	Approved
0.704	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4097	Suspended
0.703	Intermediate Similarity	NPD7251	Discontinued
0.7029	Intermediate Similarity	NPD2232	Approved
0.7029	Intermediate Similarity	NPD2233	Approved
0.7029	Intermediate Similarity	NPD2230	Approved
0.7025	Intermediate Similarity	NPD7075	Discontinued
0.702	Intermediate Similarity	NPD6799	Approved
0.7019	Intermediate Similarity	NPD3926	Phase 2
0.7013	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1551	Phase 2
0.7006	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2677	Approved
0.7	Intermediate Similarity	NPD5451	Approved
0.6993	Remote Similarity	NPD6798	Discontinued
0.6992	Remote Similarity	NPD844	Approved
0.6988	Remote Similarity	NPD7808	Phase 3
0.6988	Remote Similarity	NPD7549	Discontinued
0.6988	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4538	Approved
0.6986	Remote Similarity	NPD6896	Approved
0.6986	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4536	Approved
0.6986	Remote Similarity	NPD6895	Approved
0.6984	Remote Similarity	NPD291	Approved
0.6981	Remote Similarity	NPD919	Approved
0.6974	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1424	Approved
0.6974	Remote Similarity	NPD4123	Phase 3
0.6972	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6599	Discontinued
0.6966	Remote Similarity	NPD447	Suspended
0.6966	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5124	Phase 1
0.6962	Remote Similarity	NPD6788	Approved
0.6962	Remote Similarity	NPD7768	Phase 2
0.6959	Remote Similarity	NPD5763	Approved
0.6959	Remote Similarity	NPD5762	Approved
0.6957	Remote Similarity	NPD1611	Approved
0.6957	Remote Similarity	NPD1281	Approved
0.6947	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2977	Approved
0.6943	Remote Similarity	NPD7819	Suspended
0.6943	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2978	Approved
0.6939	Remote Similarity	NPD3748	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