NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.1
Volume:	226.298
LogP:	-0.333
LogD:	-0.319
LogS:	-0.439
# Rotatable Bonds:	5
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	2.716
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.041
MDCK Permeability:	8.919397077988833e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.12
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.394
Plasma Protein Binding (PPB):	32.81036376953125%
Volume Distribution (VD):	1.591
Pgp-substrate:	54.39906311035156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.584
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.848
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.578
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.619
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	5.907
Half-life (T1/2):	0.806

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.078
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.067
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.473
Respiratory Toxicity:	0.017

Download Data

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

Natural Product: NPC135961

Natural Product ID:	NPC135961
*Common Name:**	(1'r,2'r)-4-O-Methylguaiacyl Glycerol
IUPAC Name:	(1R,2R)-1-(3,4-dimethoxyphenyl)propane-1,2,3-triol
Synonyms:
Standard InCHIKey:	NHELEQGRSPWRNT-LDYMZIIASA-N
Standard InCHI:	InChI=1S/C11H16O5/c1-15-9-4-3-7(5-10(9)16-2)11(14)8(13)6-12/h3-5,8,11-14H,6H2,1-2H3/t8-,11-/m1/s1
SMILES:	OC[C@H]([C@@H](c1ccc(c(c1)OC)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011543
PubChem CID:	11042473
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004113] Methoxybenzenes [CHEMONTID:0004111] Dimethoxybenzenes

*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
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	roots	n.a.	n.a.	PMID[22381047]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	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
EC50	4

Activity Type	# Activity
Individual Protein	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	EC50	=	22600.0	nM	PMID[565698]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	EC50	=	19300.0	nM	PMID[565698]
NPT2	Others	Unspecified		EC50	=	20300.0	nM	PMID[565698]
NPT866	Individual Protein	Peroxisome proliferator-activated receptor alpha	Homo sapiens	EC50	=	15700.0	nM	PMID[565698]

☑ 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 NPC135961 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	315
0.1-0.2	1490
0.2-0.3	4867
0.3-0.4	12090
0.4-0.5	5867
0.5-0.6	5455
0.6-0.7	8469
0.7-0.8	3118
0.8-0.85	673
0.85-0.9	278
0.9-0.95	66
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9737	High Similarity	NPC470804
0.9735	High Similarity	NPC177475
0.9735	High Similarity	NPC35071
0.9735	High Similarity	NPC148615
0.9646	High Similarity	NPC320987
0.9646	High Similarity	NPC181969
0.9565	High Similarity	NPC476343
0.9558	High Similarity	NPC255675
0.9483	High Similarity	NPC209567
0.9402	High Similarity	NPC220598
0.9402	High Similarity	NPC165375
0.9381	High Similarity	NPC221049
0.9322	High Similarity	NPC94276
0.9322	High Similarity	NPC109822
0.9304	High Similarity	NPC311595
0.9304	High Similarity	NPC24474
0.925	High Similarity	NPC319625
0.925	High Similarity	NPC118787
0.925	High Similarity	NPC292056
0.925	High Similarity	NPC118533
0.925	High Similarity	NPC111247
0.925	High Similarity	NPC41706
0.925	High Similarity	NPC183181
0.925	High Similarity	NPC163332
0.925	High Similarity	NPC147821
0.925	High Similarity	NPC165045
0.9237	High Similarity	NPC471693
0.9231	High Similarity	NPC49341
0.9217	High Similarity	NPC63083
0.9189	High Similarity	NPC137685
0.9174	High Similarity	NPC252307
0.9174	High Similarity	NPC245826
0.9174	High Similarity	NPC474178
0.9174	High Similarity	NPC470084
0.9167	High Similarity	NPC58607
0.9167	High Similarity	NPC178284
0.9167	High Similarity	NPC191037
0.916	High Similarity	NPC293701
0.916	High Similarity	NPC48990
0.916	High Similarity	NPC114901
0.9153	High Similarity	NPC71090
0.913	High Similarity	NPC164386
0.9098	High Similarity	NPC226788
0.9098	High Similarity	NPC3439
0.9098	High Similarity	NPC210623
0.9098	High Similarity	NPC5851
0.9098	High Similarity	NPC273295
0.9098	High Similarity	NPC170844
0.9098	High Similarity	NPC86030
0.9098	High Similarity	NPC218856
0.9098	High Similarity	NPC202582
0.9098	High Similarity	NPC476968
0.9098	High Similarity	NPC190629
0.9098	High Similarity	NPC222004
0.9098	High Similarity	NPC470258
0.9098	High Similarity	NPC285339
0.9091	High Similarity	NPC5428
0.9083	High Similarity	NPC194519
0.9083	High Similarity	NPC148627
0.9068	High Similarity	NPC470212
0.9068	High Similarity	NPC113865
0.9068	High Similarity	NPC473853
0.9068	High Similarity	NPC312675
0.9068	High Similarity	NPC184651
0.9068	High Similarity	NPC324571
0.9068	High Similarity	NPC54872
0.9068	High Similarity	NPC343720
0.9068	High Similarity	NPC262156
0.906	High Similarity	NPC229401
0.9052	High Similarity	NPC474214
0.9024	High Similarity	NPC77040
0.9024	High Similarity	NPC242807
0.9024	High Similarity	NPC153739
0.9024	High Similarity	NPC145305
0.9024	High Similarity	NPC42300
0.9024	High Similarity	NPC241522
0.9024	High Similarity	NPC257582
0.9024	High Similarity	NPC92164
0.9024	High Similarity	NPC187998
0.9024	High Similarity	NPC174495
0.9024	High Similarity	NPC64201
0.9016	High Similarity	NPC98631
0.9016	High Similarity	NPC470213
0.9016	High Similarity	NPC72529
0.9016	High Similarity	NPC186843
0.9016	High Similarity	NPC206615
0.9008	High Similarity	NPC206882
0.8992	High Similarity	NPC270326
0.8983	High Similarity	NPC207613
0.8974	High Similarity	NPC474320
0.8974	High Similarity	NPC20674
0.8952	High Similarity	NPC65942
0.8952	High Similarity	NPC470096
0.8952	High Similarity	NPC469613
0.8952	High Similarity	NPC472597
0.8952	High Similarity	NPC277804
0.8952	High Similarity	NPC474017
0.8952	High Similarity	NPC469625
0.8952	High Similarity	NPC30043
0.8952	High Similarity	NPC470095
0.8952	High Similarity	NPC248307
0.8943	High Similarity	NPC26653
0.8943	High Similarity	NPC475875
0.8943	High Similarity	NPC270849
0.8943	High Similarity	NPC166040
0.8938	High Similarity	NPC156840
0.8938	High Similarity	NPC139617
0.8938	High Similarity	NPC257124
0.8938	High Similarity	NPC78918
0.8938	High Similarity	NPC8547
0.8938	High Similarity	NPC173746
0.8934	High Similarity	NPC242032
0.8934	High Similarity	NPC474119
0.8919	High Similarity	NPC227894
0.8919	High Similarity	NPC251306
0.8917	High Similarity	NPC280704
0.888	High Similarity	NPC16208
0.888	High Similarity	NPC253105
0.888	High Similarity	NPC201587
0.888	High Similarity	NPC160991
0.888	High Similarity	NPC35932
0.888	High Similarity	NPC7903
0.888	High Similarity	NPC184447
0.8871	High Similarity	NPC472024
0.8871	High Similarity	NPC80600
0.8871	High Similarity	NPC469614
0.8871	High Similarity	NPC472338
0.8871	High Similarity	NPC143483
0.8871	High Similarity	NPC469612
0.8862	High Similarity	NPC129570
0.8862	High Similarity	NPC128208
0.8862	High Similarity	NPC21867
0.8862	High Similarity	NPC184733
0.8862	High Similarity	NPC282703
0.8862	High Similarity	NPC45774
0.8862	High Similarity	NPC11258
0.8852	High Similarity	NPC473960
0.8843	High Similarity	NPC183446
0.8833	High Similarity	NPC85488
0.8824	High Similarity	NPC199023
0.8814	High Similarity	NPC477803
0.8803	High Similarity	NPC293619
0.8803	High Similarity	NPC259638
0.88	High Similarity	NPC7171
0.88	High Similarity	NPC40432
0.88	High Similarity	NPC115207
0.88	High Similarity	NPC158079
0.88	High Similarity	NPC228346
0.88	High Similarity	NPC161557
0.88	High Similarity	NPC27843
0.879	High Similarity	NPC212015
0.879	High Similarity	NPC469963
0.879	High Similarity	NPC248355
0.879	High Similarity	NPC307110
0.879	High Similarity	NPC469951
0.8783	High Similarity	NPC204120
0.8772	High Similarity	NPC55300
0.877	High Similarity	NPC233410
0.877	High Similarity	NPC203133
0.877	High Similarity	NPC472093
0.877	High Similarity	NPC193544
0.877	High Similarity	NPC117214
0.877	High Similarity	NPC298757
0.877	High Similarity	NPC208950
0.877	High Similarity	NPC116907
0.877	High Similarity	NPC221077
0.877	High Similarity	NPC57490
0.877	High Similarity	NPC251855
0.877	High Similarity	NPC17943
0.877	High Similarity	NPC475169
0.8761	High Similarity	NPC7097
0.8761	High Similarity	NPC233731
0.8761	High Similarity	NPC246358
0.8761	High Similarity	NPC36108
0.876	High Similarity	NPC282496
0.876	High Similarity	NPC197757
0.876	High Similarity	NPC233526
0.876	High Similarity	NPC228922
0.875	High Similarity	NPC285289
0.874	High Similarity	NPC310854
0.874	High Similarity	NPC35731
0.874	High Similarity	NPC170694
0.874	High Similarity	NPC119060
0.874	High Similarity	NPC287745
0.874	High Similarity	NPC237594
0.874	High Similarity	NPC135127
0.874	High Similarity	NPC470881
0.874	High Similarity	NPC476387
0.874	High Similarity	NPC249791
0.873	High Similarity	NPC470752
0.873	High Similarity	NPC18842
0.873	High Similarity	NPC181049
0.873	High Similarity	NPC4940
0.873	High Similarity	NPC207400
0.8729	High Similarity	NPC470626
0.8729	High Similarity	NPC474040
0.872	High Similarity	NPC195292
0.872	High Similarity	NPC142985
0.8718	High Similarity	NPC193067
0.871	High Similarity	NPC302378

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 NPC135961 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	864
0.2-0.3	2006
0.3-0.4	2700
0.4-0.5	1582
0.5-0.6	950
0.6-0.7	606
0.7-0.8	142
0.8-0.85	10
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9098	High Similarity	NPD3027	Phase 3
0.8938	High Similarity	NPD228	Approved
0.85	High Similarity	NPD1357	Approved
0.8438	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD1613	Approved
0.8305	Intermediate Similarity	NPD5283	Phase 1
0.8293	Intermediate Similarity	NPD3705	Approved
0.819	Intermediate Similarity	NPD2684	Approved
0.8125	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD290	Approved
0.8067	Intermediate Similarity	NPD7843	Approved
0.8047	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD7157	Approved
0.8016	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8016	Intermediate Similarity	NPD2982	Phase 2
0.8016	Intermediate Similarity	NPD2983	Phase 2
0.8	Intermediate Similarity	NPD1091	Approved
0.7982	Intermediate Similarity	NPD291	Approved
0.7937	Intermediate Similarity	NPD2981	Phase 2
0.7907	Intermediate Similarity	NPD3018	Phase 2
0.7879	Intermediate Similarity	NPD3620	Phase 2
0.7879	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD3060	Approved
0.781	Intermediate Similarity	NPD4237	Approved
0.781	Intermediate Similarity	NPD4236	Phase 3
0.7744	Intermediate Similarity	NPD1558	Phase 1
0.7742	Intermediate Similarity	NPD5536	Phase 2
0.7669	Intermediate Similarity	NPD2674	Phase 3
0.7669	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3022	Approved
0.7667	Intermediate Similarity	NPD3021	Approved
0.7664	Intermediate Similarity	NPD1375	Discontinued
0.7664	Intermediate Similarity	NPD7266	Discontinued
0.7634	Intermediate Similarity	NPD9494	Approved
0.7634	Intermediate Similarity	NPD2861	Phase 2
0.7622	Intermediate Similarity	NPD3687	Approved
0.7622	Intermediate Similarity	NPD1653	Approved
0.7622	Intermediate Similarity	NPD3686	Approved
0.7611	Intermediate Similarity	NPD9296	Approved
0.7574	Intermediate Similarity	NPD4538	Approved
0.7574	Intermediate Similarity	NPD4536	Approved
0.7574	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD9381	Approved
0.7559	Intermediate Similarity	NPD9384	Approved
0.7554	Intermediate Similarity	NPD6674	Discontinued
0.7554	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD1548	Phase 1
0.7538	Intermediate Similarity	NPD8651	Approved
0.75	Intermediate Similarity	NPD6653	Approved
0.75	Intermediate Similarity	NPD1358	Approved
0.7481	Intermediate Similarity	NPD2238	Phase 2
0.748	Intermediate Similarity	NPD821	Approved
0.7465	Intermediate Similarity	NPD1774	Approved
0.7463	Intermediate Similarity	NPD3145	Approved
0.7463	Intermediate Similarity	NPD3144	Approved
0.7462	Intermediate Similarity	NPD9622	Approved
0.7447	Intermediate Similarity	NPD2219	Phase 1
0.7447	Intermediate Similarity	NPD2677	Approved
0.7444	Intermediate Similarity	NPD4908	Phase 1
0.7442	Intermediate Similarity	NPD1610	Phase 2
0.744	Intermediate Similarity	NPD6671	Approved
0.7429	Intermediate Similarity	NPD4162	Approved
0.7429	Intermediate Similarity	NPD5177	Phase 3
0.7424	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD968	Approved
0.7415	Intermediate Similarity	NPD1934	Approved
0.7415	Intermediate Similarity	NPD37	Approved
0.7413	Intermediate Similarity	NPD4123	Phase 3
0.7391	Intermediate Similarity	NPD5588	Approved
0.7391	Intermediate Similarity	NPD5960	Phase 3
0.7388	Intermediate Similarity	NPD3180	Approved
0.7388	Intermediate Similarity	NPD3179	Approved
0.7385	Intermediate Similarity	NPD2235	Phase 2
0.7385	Intermediate Similarity	NPD2231	Phase 2
0.7377	Intermediate Similarity	NPD556	Approved
0.7365	Intermediate Similarity	NPD2978	Approved
0.7365	Intermediate Similarity	NPD5773	Approved
0.7365	Intermediate Similarity	NPD5772	Approved
0.7365	Intermediate Similarity	NPD2977	Approved
0.7364	Intermediate Similarity	NPD3496	Discontinued
0.7361	Intermediate Similarity	NPD7526	Approved
0.7361	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD52	Approved
0.7353	Intermediate Similarity	NPD4060	Phase 1
0.7343	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2161	Phase 2
0.7333	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD5241	Discontinued
0.7317	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD596	Approved
0.7313	Intermediate Similarity	NPD600	Approved
0.7305	Intermediate Similarity	NPD1652	Phase 2
0.7299	Intermediate Similarity	NPD5735	Approved
0.7299	Intermediate Similarity	NPD230	Phase 1
0.7293	Intermediate Similarity	NPD9621	Approved
0.7293	Intermediate Similarity	NPD558	Phase 2
0.7293	Intermediate Similarity	NPD9620	Approved
0.7293	Intermediate Similarity	NPD9619	Approved
0.7287	Intermediate Similarity	NPD1778	Approved
0.7287	Intermediate Similarity	NPD4626	Approved
0.7287	Intermediate Similarity	NPD5846	Approved
0.7287	Intermediate Similarity	NPD6516	Phase 2
0.7286	Intermediate Similarity	NPD3540	Phase 1
0.7279	Intermediate Similarity	NPD840	Approved
0.7279	Intermediate Similarity	NPD4678	Approved
0.7279	Intermediate Similarity	NPD839	Approved
0.7279	Intermediate Similarity	NPD4675	Approved
0.7279	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD5058	Phase 3
0.7267	Intermediate Similarity	NPD4965	Approved
0.7267	Intermediate Similarity	NPD4967	Phase 2
0.7267	Intermediate Similarity	NPD4966	Approved
0.7254	Intermediate Similarity	NPD4110	Phase 3
0.7254	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4628	Phase 3
0.7248	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2801	Approved
0.7248	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD846	Approved
0.7227	Intermediate Similarity	NPD940	Approved
0.7222	Intermediate Similarity	NPD4357	Discontinued
0.7219	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD1818	Approved
0.7218	Intermediate Similarity	NPD3094	Phase 2
0.7218	Intermediate Similarity	NPD1817	Approved
0.7218	Intermediate Similarity	NPD1819	Approved
0.7218	Intermediate Similarity	NPD1820	Approved
0.7214	Intermediate Similarity	NPD3539	Phase 1
0.7211	Intermediate Similarity	NPD4005	Discontinued
0.7206	Intermediate Similarity	NPD598	Approved
0.7206	Intermediate Similarity	NPD5109	Approved
0.7206	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD597	Approved
0.7206	Intermediate Similarity	NPD5111	Phase 2
0.7206	Intermediate Similarity	NPD601	Approved
0.7206	Intermediate Similarity	NPD5110	Phase 2
0.7203	Intermediate Similarity	NPD6190	Approved
0.72	Intermediate Similarity	NPD2560	Approved
0.72	Intermediate Similarity	NPD2563	Approved
0.7197	Intermediate Similarity	NPD4749	Approved
0.7197	Intermediate Similarity	NPD3685	Discontinued
0.7194	Intermediate Similarity	NPD6111	Discontinued
0.7193	Intermediate Similarity	NPD9365	Approved
0.7176	Intermediate Similarity	NPD422	Phase 1
0.7174	Intermediate Similarity	NPD447	Suspended
0.7174	Intermediate Similarity	NPD3657	Discovery
0.7171	Intermediate Similarity	NPD6234	Discontinued
0.7164	Intermediate Similarity	NPD6584	Phase 3
0.7163	Intermediate Similarity	NPD5763	Approved
0.7163	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5762	Approved
0.7161	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6166	Phase 2
0.7155	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD2934	Approved
0.7155	Intermediate Similarity	NPD2933	Approved
0.7153	Intermediate Similarity	NPD1132	Approved
0.7153	Intermediate Similarity	NPD1130	Approved
0.7153	Intermediate Similarity	NPD1136	Approved
0.7152	Intermediate Similarity	NPD3882	Suspended
0.7143	Intermediate Similarity	NPD1242	Phase 1
0.7143	Intermediate Similarity	NPD2922	Phase 1
0.7133	Intermediate Similarity	NPD6331	Phase 2
0.7132	Intermediate Similarity	NPD7095	Approved
0.7131	Intermediate Similarity	NPD3134	Approved
0.7123	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD2233	Approved
0.7121	Intermediate Similarity	NPD2232	Approved
0.7121	Intermediate Similarity	NPD2230	Approved
0.7113	Intermediate Similarity	NPD7153	Discontinued
0.7113	Intermediate Similarity	NPD2424	Discontinued
0.7103	Intermediate Similarity	NPD1511	Approved
0.7101	Intermediate Similarity	NPD3059	Approved
0.7101	Intermediate Similarity	NPD3061	Approved
0.7101	Intermediate Similarity	NPD3062	Approved
0.7097	Intermediate Similarity	NPD5451	Approved
0.7094	Intermediate Similarity	NPD2859	Approved
0.7094	Intermediate Similarity	NPD2860	Approved
0.7094	Intermediate Similarity	NPD844	Approved
0.7086	Intermediate Similarity	NPD3817	Phase 2
0.7086	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5718	Phase 2
0.708	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6798	Discontinued
0.7077	Intermediate Similarity	NPD5691	Approved
0.7075	Intermediate Similarity	NPD2122	Discontinued
0.7068	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD9379	Approved
0.7063	Intermediate Similarity	NPD9377	Approved
0.7059	Intermediate Similarity	NPD3020	Approved
0.705	Intermediate Similarity	NPD4340	Discontinued
0.705	Intermediate Similarity	NPD6355	Discontinued
0.7045	Intermediate Similarity	NPD3092	Approved
0.7039	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3690	Phase 2
0.7037	Intermediate Similarity	NPD3691	Phase 2

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