NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.12
Volume:	243.594
LogP:	0.184
LogD:	0.919
LogS:	-1.087
# Rotatable Bonds:	6
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.688
Synthetic Accessibility Score:	3.114
Fsp3:	0.5
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:	-4.583
MDCK Permeability:	8.249526581494138e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.53
Plasma Protein Binding (PPB):	31.207290649414062%
Volume Distribution (VD):	2.197
Pgp-substrate:	59.228782653808594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.548
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.784
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.605
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.369
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.212

ADMET: Excretion

Clearance (CL):	10.708
Half-life (T1/2):	0.776

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.087
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.47
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.123
Carcinogencity:	0.049
Eye Corrosion:	0.003
Eye Irritation:	0.102
Respiratory Toxicity:	0.019

Download Data

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

Natural Product: NPC470804

Natural Product ID:	NPC470804
*Common Name:**	7-O-Ethylguaiacylglycerol
IUPAC Name:	3-ethoxy-3-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol
Synonyms:	7-O-Ethylguaiacylglycerol
Standard InCHIKey:	AAOACSSPCZAJCZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H18O5/c1-3-17-12(10(15)7-13)8-4-5-9(14)11(6-8)16-2/h4-6,10,12-15H,3,7H2,1-2H3
SMILES:	CCOC(c1ccc(c(c1)OC)O)C(CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL224843
PubChem CID:	44421292
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792422]
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17343407]
NPO14922	Tarenna attenuata	Species	Rubiaceae	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	1
Others	4

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	54.1	%	PMID[464742]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	54.9	%	PMID[464742]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	56.8	%	PMID[464742]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	57.3	%	PMID[464742]
NPT1	Others	Radical scavenging activity		IC50	=	132000.0	nM	PMID[464742]

☑ 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 NPC470804 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	343
0.1-0.2	1496
0.2-0.3	5008
0.3-0.4	11987
0.4-0.5	5841
0.5-0.6	5052
0.6-0.7	8386
0.7-0.8	3332
0.8-0.85	751
0.85-0.9	381
0.9-0.95	109
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9825	High Similarity	NPC148615
0.9825	High Similarity	NPC177475
0.9825	High Similarity	NPC35071
0.9741	High Similarity	NPC209567
0.9737	High Similarity	NPC181969
0.9737	High Similarity	NPC320987
0.9737	High Similarity	NPC135961
0.9655	High Similarity	NPC476343
0.9649	High Similarity	NPC255675
0.95	High Similarity	NPC319625
0.95	High Similarity	NPC118787
0.95	High Similarity	NPC163332
0.95	High Similarity	NPC41706
0.95	High Similarity	NPC183181
0.95	High Similarity	NPC147821
0.95	High Similarity	NPC111247
0.95	High Similarity	NPC292056
0.9492	High Similarity	NPC165375
0.9492	High Similarity	NPC220598
0.9474	High Similarity	NPC221049
0.9421	High Similarity	NPC474178
0.9421	High Similarity	NPC252307
0.9421	High Similarity	NPC245826
0.9417	High Similarity	NPC178284
0.9417	High Similarity	NPC191037
0.9417	High Similarity	NPC58607
0.9397	High Similarity	NPC24474
0.9397	High Similarity	NPC311595
0.9344	High Similarity	NPC5851
0.9344	High Similarity	NPC86030
0.9339	High Similarity	NPC165045
0.9339	High Similarity	NPC118533
0.9333	High Similarity	NPC194519
0.9328	High Similarity	NPC471693
0.9322	High Similarity	NPC49341
0.9268	High Similarity	NPC92164
0.9268	High Similarity	NPC145305
0.9268	High Similarity	NPC153739
0.9268	High Similarity	NPC241522
0.9268	High Similarity	NPC257582
0.9268	High Similarity	NPC64201
0.9268	High Similarity	NPC77040
0.9268	High Similarity	NPC42300
0.9268	High Similarity	NPC242807
0.9268	High Similarity	NPC174495
0.9268	High Similarity	NPC187998
0.9262	High Similarity	NPC72529
0.925	High Similarity	NPC48990
0.925	High Similarity	NPC109822
0.925	High Similarity	NPC114901
0.925	High Similarity	NPC293701
0.925	High Similarity	NPC94276
0.9224	High Similarity	NPC164386
0.9194	High Similarity	NPC277804
0.9194	High Similarity	NPC470096
0.9194	High Similarity	NPC65942
0.9194	High Similarity	NPC248307
0.9194	High Similarity	NPC472597
0.9194	High Similarity	NPC470095
0.9187	High Similarity	NPC170844
0.9187	High Similarity	NPC475875
0.9187	High Similarity	NPC476968
0.918	High Similarity	NPC5428
0.9174	High Similarity	NPC148627
0.916	High Similarity	NPC184651
0.916	High Similarity	NPC324571
0.916	High Similarity	NPC343720
0.916	High Similarity	NPC54872
0.916	High Similarity	NPC473853
0.916	High Similarity	NPC262156
0.916	High Similarity	NPC470212
0.916	High Similarity	NPC312675
0.916	High Similarity	NPC113865
0.9153	High Similarity	NPC229401
0.912	High Similarity	NPC16208
0.912	High Similarity	NPC7903
0.912	High Similarity	NPC160991
0.912	High Similarity	NPC253105
0.912	High Similarity	NPC201587
0.912	High Similarity	NPC184447
0.912	High Similarity	NPC35932
0.9113	High Similarity	NPC472338
0.9106	High Similarity	NPC21867
0.9106	High Similarity	NPC470084
0.9106	High Similarity	NPC45774
0.9106	High Similarity	NPC186843
0.9106	High Similarity	NPC11258
0.9106	High Similarity	NPC128208
0.9106	High Similarity	NPC470213
0.9106	High Similarity	NPC129570
0.9106	High Similarity	NPC206615
0.9106	High Similarity	NPC98631
0.9106	High Similarity	NPC282703
0.9106	High Similarity	NPC184733
0.9083	High Similarity	NPC71090
0.9076	High Similarity	NPC207613
0.9068	High Similarity	NPC20674
0.904	High Similarity	NPC40432
0.904	High Similarity	NPC7171
0.904	High Similarity	NPC228346
0.904	High Similarity	NPC158079
0.904	High Similarity	NPC161557
0.904	High Similarity	NPC115207
0.904	High Similarity	NPC474017
0.904	High Similarity	NPC27843
0.9035	High Similarity	NPC173746
0.9035	High Similarity	NPC257124
0.9035	High Similarity	NPC78918
0.9035	High Similarity	NPC8547
0.9035	High Similarity	NPC156840
0.9035	High Similarity	NPC139617
0.9032	High Similarity	NPC226788
0.9032	High Similarity	NPC470258
0.9032	High Similarity	NPC307110
0.9032	High Similarity	NPC218856
0.9032	High Similarity	NPC210623
0.9032	High Similarity	NPC273295
0.9032	High Similarity	NPC3439
0.9032	High Similarity	NPC222004
0.9032	High Similarity	NPC285339
0.9032	High Similarity	NPC202582
0.9032	High Similarity	NPC190629
0.9008	High Similarity	NPC280704
0.8983	High Similarity	NPC63083
0.8976	High Similarity	NPC470881
0.8976	High Similarity	NPC249791
0.8976	High Similarity	NPC35731
0.8976	High Similarity	NPC135127
0.8976	High Similarity	NPC237594
0.8976	High Similarity	NPC287745
0.8976	High Similarity	NPC476387
0.8976	High Similarity	NPC170694
0.8976	High Similarity	NPC310854
0.8976	High Similarity	NPC119060
0.8968	High Similarity	NPC470752
0.8968	High Similarity	NPC181049
0.8968	High Similarity	NPC4940
0.8968	High Similarity	NPC207400
0.896	High Similarity	NPC143483
0.8947	High Similarity	NPC137685
0.8943	High Similarity	NPC206882
0.8934	High Similarity	NPC183446
0.8926	High Similarity	NPC85488
0.8908	High Similarity	NPC477803
0.8906	High Similarity	NPC472337
0.8898	High Similarity	NPC475840
0.8898	High Similarity	NPC259638
0.8898	High Similarity	NPC158331
0.8898	High Similarity	NPC6836
0.8898	High Similarity	NPC293619
0.8889	High Similarity	NPC309787
0.8889	High Similarity	NPC30043
0.8889	High Similarity	NPC469625
0.8889	High Similarity	NPC469480
0.8889	High Similarity	NPC469613
0.888	High Similarity	NPC270849
0.888	High Similarity	NPC26653
0.888	High Similarity	NPC212015
0.888	High Similarity	NPC166040
0.8871	High Similarity	NPC474119
0.8871	High Similarity	NPC210355
0.8862	High Similarity	NPC475169
0.8862	High Similarity	NPC233410
0.8862	High Similarity	NPC221077
0.8862	High Similarity	NPC116907
0.8862	High Similarity	NPC472093
0.8862	High Similarity	NPC298757
0.8862	High Similarity	NPC193544
0.8862	High Similarity	NPC117214
0.8862	High Similarity	NPC203133
0.8862	High Similarity	NPC251855
0.8862	High Similarity	NPC17943
0.8862	High Similarity	NPC208950
0.8862	High Similarity	NPC57490
0.886	High Similarity	NPC36108
0.886	High Similarity	NPC246358
0.886	High Similarity	NPC233731
0.886	High Similarity	NPC7097
0.8852	High Similarity	NPC228922
0.8852	High Similarity	NPC197757
0.8843	High Similarity	NPC290451
0.8843	High Similarity	NPC127389
0.8837	High Similarity	NPC263367
0.8837	High Similarity	NPC199459
0.8837	High Similarity	NPC477939
0.8837	High Similarity	NPC16435
0.8837	High Similarity	NPC209985
0.8837	High Similarity	NPC10737
0.8837	High Similarity	NPC52277
0.8837	High Similarity	NPC54743
0.8837	High Similarity	NPC472334
0.8837	High Similarity	NPC29799
0.8837	High Similarity	NPC177035
0.8837	High Similarity	NPC306441
0.8837	High Similarity	NPC472336
0.8837	High Similarity	NPC177160
0.8837	High Similarity	NPC156502
0.8828	High Similarity	NPC244983
0.8828	High Similarity	NPC478085
0.8828	High Similarity	NPC107478

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 NPC470804 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	861
0.2-0.3	2071
0.3-0.4	2698
0.4-0.5	1551
0.5-0.6	896
0.6-0.7	617
0.7-0.8	141
0.8-0.85	7
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9187	High Similarity	NPD3027	Phase 3
0.9035	High Similarity	NPD228	Approved
0.8672	High Similarity	NPD1613	Approved
0.8672	High Similarity	NPD1612	Clinical (unspecified phase)
0.8359	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD1357	Approved
0.8281	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.824	Intermediate Similarity	NPD3705	Approved
0.8136	Intermediate Similarity	NPD2684	Approved
0.811	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD5283	Phase 1
0.8051	Intermediate Similarity	NPD290	Approved
0.8017	Intermediate Similarity	NPD7843	Approved
0.797	Intermediate Similarity	NPD3620	Phase 2
0.797	Intermediate Similarity	NPD1558	Phase 1
0.797	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD7157	Approved
0.7953	Intermediate Similarity	NPD1091	Approved
0.7931	Intermediate Similarity	NPD291	Approved
0.7883	Intermediate Similarity	NPD7266	Discontinued
0.7832	Intermediate Similarity	NPD1653	Approved
0.7829	Intermediate Similarity	NPD2982	Phase 2
0.7829	Intermediate Similarity	NPD2983	Phase 2
0.777	Intermediate Similarity	NPD4237	Approved
0.777	Intermediate Similarity	NPD3060	Approved
0.777	Intermediate Similarity	NPD4236	Phase 3
0.7769	Intermediate Similarity	NPD3021	Approved
0.7769	Intermediate Similarity	NPD3022	Approved
0.7761	Intermediate Similarity	NPD2674	Phase 3
0.7752	Intermediate Similarity	NPD2981	Phase 2
0.7727	Intermediate Similarity	NPD2861	Phase 2
0.7727	Intermediate Similarity	NPD3018	Phase 2
0.7727	Intermediate Similarity	NPD9494	Approved
0.7719	Intermediate Similarity	NPD9296	Approved
0.7656	Intermediate Similarity	NPD9384	Approved
0.7656	Intermediate Similarity	NPD9381	Approved
0.7638	Intermediate Similarity	NPD1548	Phase 1
0.763	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD1375	Discontinued
0.7619	Intermediate Similarity	NPD1934	Approved
0.7586	Intermediate Similarity	NPD3687	Approved
0.7586	Intermediate Similarity	NPD3686	Approved
0.7559	Intermediate Similarity	NPD5536	Phase 2
0.7557	Intermediate Similarity	NPD9622	Approved
0.7556	Intermediate Similarity	NPD3144	Approved
0.7556	Intermediate Similarity	NPD3145	Approved
0.754	Intermediate Similarity	NPD6671	Approved
0.7538	Intermediate Similarity	NPD1610	Phase 2
0.7537	Intermediate Similarity	NPD4908	Phase 1
0.7536	Intermediate Similarity	NPD4536	Approved
0.7536	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD4538	Approved
0.7521	Intermediate Similarity	NPD968	Approved
0.7518	Intermediate Similarity	NPD6674	Discontinued
0.7518	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD8651	Approved
0.7464	Intermediate Similarity	NPD6653	Approved
0.7459	Intermediate Similarity	NPD1358	Approved
0.745	Intermediate Similarity	NPD2978	Approved
0.745	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2977	Approved
0.745	Intermediate Similarity	NPD2801	Approved
0.7445	Intermediate Similarity	NPD4060	Phase 1
0.744	Intermediate Similarity	NPD821	Approved
0.7431	Intermediate Similarity	NPD1774	Approved
0.7426	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD2677	Approved
0.7413	Intermediate Similarity	NPD6190	Approved
0.7394	Intermediate Similarity	NPD4162	Approved
0.7388	Intermediate Similarity	NPD9619	Approved
0.7388	Intermediate Similarity	NPD9621	Approved
0.7388	Intermediate Similarity	NPD9620	Approved
0.7379	Intermediate Similarity	NPD4123	Phase 3
0.7376	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6234	Discontinued
0.7357	Intermediate Similarity	NPD5588	Approved
0.7357	Intermediate Similarity	NPD5960	Phase 3
0.7355	Intermediate Similarity	NPD6166	Phase 2
0.7355	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3180	Approved
0.7353	Intermediate Similarity	NPD3179	Approved
0.7351	Intermediate Similarity	NPD3882	Suspended
0.7348	Intermediate Similarity	NPD2231	Phase 2
0.7348	Intermediate Similarity	NPD2235	Phase 2
0.7339	Intermediate Similarity	NPD556	Approved
0.7333	Intermediate Similarity	NPD5773	Approved
0.7333	Intermediate Similarity	NPD5772	Approved
0.7329	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7526	Approved
0.7329	Intermediate Similarity	NPD52	Approved
0.7328	Intermediate Similarity	NPD3496	Discontinued
0.7319	Intermediate Similarity	NPD2238	Phase 2
0.731	Intermediate Similarity	NPD1511	Approved
0.731	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2161	Phase 2
0.7299	Intermediate Similarity	NPD597	Approved
0.7299	Intermediate Similarity	NPD598	Approved
0.7299	Intermediate Similarity	NPD601	Approved
0.7299	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4749	Approved
0.7293	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2219	Phase 1
0.7279	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1652	Phase 2
0.7273	Intermediate Similarity	NPD5177	Phase 3
0.7273	Intermediate Similarity	NPD422	Phase 1
0.7267	Intermediate Similarity	NPD37	Approved
0.7266	Intermediate Similarity	NPD5735	Approved
0.7259	Intermediate Similarity	NPD6584	Phase 3
0.7259	Intermediate Similarity	NPD558	Phase 2
0.7259	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD6516	Phase 2
0.7252	Intermediate Similarity	NPD5846	Approved
0.7252	Intermediate Similarity	NPD1778	Approved
0.7248	Intermediate Similarity	NPD4675	Approved
0.7248	Intermediate Similarity	NPD4678	Approved
0.7246	Intermediate Similarity	NPD1136	Approved
0.7246	Intermediate Similarity	NPD1132	Approved
0.7246	Intermediate Similarity	NPD1130	Approved
0.7246	Intermediate Similarity	NPD6233	Phase 2
0.7241	Intermediate Similarity	NPD5058	Phase 3
0.7237	Intermediate Similarity	NPD4965	Approved
0.7237	Intermediate Similarity	NPD4967	Phase 2
0.7237	Intermediate Similarity	NPD4966	Approved
0.7237	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4628	Phase 3
0.7222	Intermediate Similarity	NPD4110	Phase 3
0.7222	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7054	Approved
0.7211	Intermediate Similarity	NPD1512	Approved
0.7194	Intermediate Similarity	NPD3062	Approved
0.7194	Intermediate Similarity	NPD3061	Approved
0.7194	Intermediate Similarity	NPD3059	Approved
0.719	Intermediate Similarity	NPD846	Approved
0.719	Intermediate Similarity	NPD940	Approved
0.7185	Intermediate Similarity	NPD1817	Approved
0.7185	Intermediate Similarity	NPD1818	Approved
0.7185	Intermediate Similarity	NPD1820	Approved
0.7185	Intermediate Similarity	NPD1819	Approved
0.7185	Intermediate Similarity	NPD3094	Phase 2
0.7172	Intermediate Similarity	NPD5241	Discontinued
0.7171	Intermediate Similarity	NPD2560	Approved
0.7171	Intermediate Similarity	NPD2563	Approved
0.717	Intermediate Similarity	NPD7472	Approved
0.717	Intermediate Similarity	NPD7074	Phase 3
0.7165	Intermediate Similarity	NPD9377	Approved
0.7165	Intermediate Similarity	NPD9379	Approved
0.7164	Intermediate Similarity	NPD3685	Discontinued
0.7155	Intermediate Similarity	NPD9365	Approved
0.7153	Intermediate Similarity	NPD600	Approved
0.7153	Intermediate Similarity	NPD596	Approved
0.7152	Intermediate Similarity	NPD7228	Approved
0.7152	Intermediate Similarity	NPD3818	Discontinued
0.7143	Intermediate Similarity	NPD447	Suspended
0.7133	Intermediate Similarity	NPD5762	Approved
0.7133	Intermediate Similarity	NPD3540	Phase 1
0.7133	Intermediate Similarity	NPD5763	Approved
0.7122	Intermediate Similarity	NPD839	Approved
0.7122	Intermediate Similarity	NPD840	Approved
0.7121	Intermediate Similarity	NPD4626	Approved
0.7119	Intermediate Similarity	NPD2933	Approved
0.7119	Intermediate Similarity	NPD2934	Approved
0.7119	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6696	Suspended
0.7107	Intermediate Similarity	NPD1242	Phase 1
0.7105	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6331	Phase 2
0.7101	Intermediate Similarity	NPD4625	Phase 3
0.7101	Intermediate Similarity	NPD7095	Approved
0.7097	Intermediate Similarity	NPD3134	Approved
0.7095	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5314	Approved
0.7083	Intermediate Similarity	NPD7153	Discontinued
0.7083	Intermediate Similarity	NPD2424	Discontinued
0.7078	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4357	Discontinued
0.7067	Intermediate Similarity	NPD4005	Discontinued
0.7063	Intermediate Similarity	NPD3539	Phase 1
0.7059	Intermediate Similarity	NPD3817	Phase 2
0.7059	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2859	Approved
0.7059	Intermediate Similarity	NPD2860	Approved
0.7059	Intermediate Similarity	NPD844	Approved
0.705	Intermediate Similarity	NPD5109	Approved
0.705	Intermediate Similarity	NPD5110	Phase 2
0.705	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6798	Discontinued
0.705	Intermediate Similarity	NPD5111	Phase 2
0.7047	Intermediate Similarity	NPD2122	Discontinued
0.7045	Intermediate Similarity	NPD5691	Approved
0.7042	Intermediate Similarity	NPD6111	Discontinued
0.7037	Intermediate Similarity	NPD6583	Phase 3
0.7037	Intermediate Similarity	NPD6582	Phase 2
0.7027	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3020	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