NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.1
Volume:	226.298
LogP:	-0.861
LogD:	0.069
LogS:	-0.73
# Rotatable Bonds:	5
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.571
Synthetic Accessibility Score:	2.849
Fsp3:	0.455
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:	-5.001
MDCK Permeability:	0.003570504719391465
Pgp-inhibitor:	0.0
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.779
20% Bioavailability (F20%):	0.476
30% Bioavailability (F30%):	0.469

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.718
Plasma Protein Binding (PPB):	13.025976181030273%
Volume Distribution (VD):	0.919
Pgp-substrate:	70.01915740966797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.221
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.565
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.239
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.351
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.186

ADMET: Excretion

Clearance (CL):	9.221
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.411
Carcinogencity:	0.034
Eye Corrosion:	0.004
Eye Irritation:	0.778
Respiratory Toxicity:	0.018

Download Data

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

Natural Product: NPC476343

Natural Product ID:	NPC476343
*Common Name:**	Guaicylglycerol
IUPAC Name:	1-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)propane-1,3-diol
Synonyms:	Guaicylglycerol
Standard InCHIKey:	SKRUGJGVXQATKU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H16O5/c1-16-10-4-7(2-3-9(10)14)11(15)8(5-12)6-13/h2-4,8,11-15H,5-6H2,1H3
SMILES:	OCC(C(c1ccc(c(c1)OC)O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL573104
PubChem CID:	45482328
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
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	stem bark	Kunming, Yunnan Province, China	n.a.	PMID[18986199]
NPO12339	Daphne feddei	Species	Thymelaeaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	300000.0	nM	PMID[564338]

☑ 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 NPC476343 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	342
0.1-0.2	1401
0.2-0.3	4661
0.3-0.4	12016
0.4-0.5	6141
0.5-0.6	5270
0.6-0.7	8514
0.7-0.8	3200
0.8-0.85	701
0.85-0.9	353
0.9-0.95	85
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9655	High Similarity	NPC470804
0.9652	High Similarity	NPC148615
0.9652	High Similarity	NPC177475
0.9652	High Similarity	NPC35071
0.9565	High Similarity	NPC181969
0.9565	High Similarity	NPC24474
0.9565	High Similarity	NPC311595
0.9565	High Similarity	NPC135961
0.9565	High Similarity	NPC320987
0.95	High Similarity	NPC118533
0.95	High Similarity	NPC165045
0.9478	High Similarity	NPC255675
0.9407	High Similarity	NPC209567
0.9391	High Similarity	NPC164386
0.9344	High Similarity	NPC475875
0.9339	High Similarity	NPC5428
0.9333	High Similarity	NPC148627
0.9328	High Similarity	NPC280704
0.9328	High Similarity	NPC220598
0.9328	High Similarity	NPC471693
0.9328	High Similarity	NPC165375
0.9322	High Similarity	NPC343720
0.9322	High Similarity	NPC54872
0.9322	High Similarity	NPC113865
0.9322	High Similarity	NPC312675
0.9322	High Similarity	NPC184651
0.9322	High Similarity	NPC470212
0.9322	High Similarity	NPC473853
0.9322	High Similarity	NPC324571
0.9322	High Similarity	NPC262156
0.9304	High Similarity	NPC221049
0.9268	High Similarity	NPC145305
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	NPC92164
0.9268	High Similarity	NPC242807
0.9268	High Similarity	NPC174495
0.9268	High Similarity	NPC153739
0.9268	High Similarity	NPC187998
0.9262	High Similarity	NPC245826
0.9262	High Similarity	NPC474178
0.9262	High Similarity	NPC252307
0.9244	High Similarity	NPC85488
0.9237	High Similarity	NPC207613
0.9194	High Similarity	NPC277804
0.9194	High Similarity	NPC474017
0.9187	High Similarity	NPC170844
0.9187	High Similarity	NPC476968
0.918	High Similarity	NPC147821
0.918	High Similarity	NPC118787
0.918	High Similarity	NPC292056
0.918	High Similarity	NPC41706
0.918	High Similarity	NPC183181
0.918	High Similarity	NPC111247
0.918	High Similarity	NPC163332
0.918	High Similarity	NPC319625
0.916	High Similarity	NPC49341
0.9113	High Similarity	NPC195292
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
0.9098	High Similarity	NPC191037
0.9098	High Similarity	NPC58607
0.9098	High Similarity	NPC178284
0.9091	High Similarity	NPC114901
0.9091	High Similarity	NPC293701
0.9091	High Similarity	NPC48990
0.906	High Similarity	NPC293619
0.904	High Similarity	NPC40432
0.904	High Similarity	NPC27843
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
0.9035	High Similarity	NPC257124
0.9035	High Similarity	NPC173746
0.9035	High Similarity	NPC78918
0.9035	High Similarity	NPC8547
0.9035	High Similarity	NPC156840
0.9035	High Similarity	NPC139617
0.9032	High Similarity	NPC212015
0.9032	High Similarity	NPC5851
0.9032	High Similarity	NPC86030
0.9016	High Similarity	NPC194519
0.9008	High Similarity	NPC228922
0.9008	High Similarity	NPC197757
0.8992	High Similarity	NPC227217
0.8992	High Similarity	NPC242885
0.8992	High Similarity	NPC56214
0.8992	High Similarity	NPC95614
0.8992	High Similarity	NPC117780
0.8992	High Similarity	NPC229401
0.8992	High Similarity	NPC232316
0.8992	High Similarity	NPC165133
0.8983	High Similarity	NPC470626
0.8983	High Similarity	NPC474214
0.8976	High Similarity	NPC287745
0.8968	High Similarity	NPC106739
0.8968	High Similarity	NPC181049
0.8968	High Similarity	NPC201587
0.8968	High Similarity	NPC253105
0.8968	High Similarity	NPC207400
0.896	High Similarity	NPC142985
0.896	High Similarity	NPC143483
0.8952	High Similarity	NPC72529
0.8947	High Similarity	NPC137685
0.8943	High Similarity	NPC206882
0.8934	High Similarity	NPC94276
0.8934	High Similarity	NPC109822
0.8926	High Similarity	NPC41562
0.8908	High Similarity	NPC281298
0.8908	High Similarity	NPC20674
0.8908	High Similarity	NPC310338
0.8908	High Similarity	NPC474320
0.8906	High Similarity	NPC101624
0.8906	High Similarity	NPC184938
0.8906	High Similarity	NPC470990
0.8898	High Similarity	NPC158331
0.8889	High Similarity	NPC470095
0.8889	High Similarity	NPC470096
0.8889	High Similarity	NPC65942
0.8889	High Similarity	NPC248307
0.8889	High Similarity	NPC472597
0.8889	High Similarity	NPC469480
0.888	High Similarity	NPC158477
0.8871	High Similarity	NPC127587
0.8862	High Similarity	NPC475169
0.8862	High Similarity	NPC57490
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	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	NPC193544
0.886	High Similarity	NPC233731
0.886	High Similarity	NPC36108
0.886	High Similarity	NPC246358
0.886	High Similarity	NPC7097
0.8852	High Similarity	NPC317769
0.8852	High Similarity	NPC31344
0.8843	High Similarity	NPC290451
0.8843	High Similarity	NPC160380
0.8843	High Similarity	NPC38996
0.8843	High Similarity	NPC127389
0.8837	High Similarity	NPC263367
0.8837	High Similarity	NPC209985
0.8837	High Similarity	NPC10737
0.8837	High Similarity	NPC477939
0.8837	High Similarity	NPC54743
0.8837	High Similarity	NPC29799
0.8837	High Similarity	NPC177160
0.8837	High Similarity	NPC156502
0.8828	High Similarity	NPC244983
0.8828	High Similarity	NPC478085
0.8828	High Similarity	NPC67247
0.8828	High Similarity	NPC326095
0.8828	High Similarity	NPC311256
0.8824	High Similarity	NPC63083
0.8824	High Similarity	NPC474040
0.8819	High Similarity	NPC35932
0.8819	High Similarity	NPC175067
0.8819	High Similarity	NPC7903
0.8819	High Similarity	NPC471505
0.8819	High Similarity	NPC204215
0.8819	High Similarity	NPC160991
0.8819	High Similarity	NPC184447
0.8819	High Similarity	NPC16208
0.8819	High Similarity	NPC470752
0.8819	High Similarity	NPC4940
0.881	High Similarity	NPC472338
0.88	High Similarity	NPC277458
0.88	High Similarity	NPC307050
0.88	High Similarity	NPC472968
0.879	High Similarity	NPC76451
0.878	High Similarity	NPC183446
0.877	High Similarity	NPC71090
0.876	High Similarity	NPC126409
0.876	High Similarity	NPC256262
0.876	High Similarity	NPC99572
0.875	High Similarity	NPC477803
0.875	High Similarity	NPC475840
0.874	High Similarity	NPC309787

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 NPC476343 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	841
0.2-0.3	1978
0.3-0.4	2718
0.4-0.5	1596
0.5-0.6	939
0.6-0.7	616
0.7-0.8	146
0.8-0.85	9
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
0.8527	High Similarity	NPD1613	Approved
0.8527	High Similarity	NPD1612	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD5283	Phase 1
0.8293	Intermediate Similarity	NPD1357	Approved
0.8244	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8244	Intermediate Similarity	NPD3620	Phase 2
0.8217	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD2684	Approved
0.811	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD3021	Approved
0.8067	Intermediate Similarity	NPD3022	Approved
0.8017	Intermediate Similarity	NPD7843	Approved
0.7967	Intermediate Similarity	NPD7157	Approved
0.7953	Intermediate Similarity	NPD3705	Approved
0.7899	Intermediate Similarity	NPD290	Approved
0.7778	Intermediate Similarity	NPD291	Approved
0.777	Intermediate Similarity	NPD3060	Approved
0.7761	Intermediate Similarity	NPD2674	Phase 3
0.7727	Intermediate Similarity	NPD2861	Phase 2
0.7727	Intermediate Similarity	NPD9494	Approved
0.7719	Intermediate Similarity	NPD9296	Approved
0.7704	Intermediate Similarity	NPD1558	Phase 1
0.7692	Intermediate Similarity	NPD2983	Phase 2
0.7692	Intermediate Similarity	NPD2982	Phase 2
0.7687	Intermediate Similarity	NPD3145	Approved
0.7687	Intermediate Similarity	NPD3144	Approved
0.7674	Intermediate Similarity	NPD1091	Approved
0.7656	Intermediate Similarity	NPD9384	Approved
0.7656	Intermediate Similarity	NPD9381	Approved
0.7626	Intermediate Similarity	NPD7266	Discontinued
0.7615	Intermediate Similarity	NPD2981	Phase 2
0.7594	Intermediate Similarity	NPD3018	Phase 2
0.7586	Intermediate Similarity	NPD1653	Approved
0.7574	Intermediate Similarity	NPD2238	Phase 2
0.7574	Intermediate Similarity	NPD4060	Phase 1
0.7559	Intermediate Similarity	NPD5536	Phase 2
0.7557	Intermediate Similarity	NPD9622	Approved
0.7557	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
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
0.7518	Intermediate Similarity	NPD4237	Approved
0.7518	Intermediate Similarity	NPD5177	Phase 3
0.7518	Intermediate Similarity	NPD6674	Discontinued
0.7518	Intermediate Similarity	NPD4236	Phase 3
0.75	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1934	Approved
0.75	Intermediate Similarity	NPD1375	Discontinued
0.7464	Intermediate Similarity	NPD6653	Approved
0.745	Intermediate Similarity	NPD2978	Approved
0.745	Intermediate Similarity	NPD2977	Approved
0.7448	Intermediate Similarity	NPD7526	Approved
0.7448	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD52	Approved
0.7444	Intermediate Similarity	NPD3094	Phase 2
0.7429	Intermediate Similarity	NPD2161	Phase 2
0.7426	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5735	Approved
0.7388	Intermediate Similarity	NPD9621	Approved
0.7388	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD9620	Approved
0.7388	Intermediate Similarity	NPD9619	Approved
0.7383	Intermediate Similarity	NPD37	Approved
0.7377	Intermediate Similarity	NPD968	Approved
0.7368	Intermediate Similarity	NPD6234	Discontinued
0.7368	Intermediate Similarity	NPD8651	Approved
0.7364	Intermediate Similarity	NPD1548	Phase 1
0.7357	Intermediate Similarity	NPD5588	Approved
0.7357	Intermediate Similarity	NPD5960	Phase 3
0.7348	Intermediate Similarity	NPD2231	Phase 2
0.7348	Intermediate Similarity	NPD2235	Phase 2
0.7347	Intermediate Similarity	NPD3686	Approved
0.7347	Intermediate Similarity	NPD3687	Approved
0.7343	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4110	Phase 3
0.7333	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD940	Approved
0.7333	Intermediate Similarity	NPD846	Approved
0.7317	Intermediate Similarity	NPD1358	Approved
0.7311	Intermediate Similarity	NPD3020	Approved
0.7302	Intermediate Similarity	NPD821	Approved
0.7299	Intermediate Similarity	NPD597	Approved
0.7299	Intermediate Similarity	NPD5110	Phase 2
0.7299	Intermediate Similarity	NPD5111	Phase 2
0.7299	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD598	Approved
0.7299	Intermediate Similarity	NPD601	Approved
0.7299	Intermediate Similarity	NPD5109	Approved
0.7293	Intermediate Similarity	NPD4749	Approved
0.7293	Intermediate Similarity	NPD3685	Discontinued
0.7273	Intermediate Similarity	NPD3092	Approved
0.7273	Intermediate Similarity	NPD4162	Approved
0.7266	Intermediate Similarity	NPD230	Phase 1
0.7266	Intermediate Similarity	NPD3657	Discovery
0.7265	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6584	Phase 3
0.7254	Intermediate Similarity	NPD5763	Approved
0.7254	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD5762	Approved
0.7252	Intermediate Similarity	NPD6516	Phase 2
0.7252	Intermediate Similarity	NPD5846	Approved
0.7252	Intermediate Similarity	NPD4626	Approved
0.7246	Intermediate Similarity	NPD1136	Approved
0.7246	Intermediate Similarity	NPD1130	Approved
0.7246	Intermediate Similarity	NPD1132	Approved
0.7244	Intermediate Similarity	NPD6166	Phase 2
0.7244	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4965	Approved
0.7237	Intermediate Similarity	NPD4967	Phase 2
0.7237	Intermediate Similarity	NPD4966	Approved
0.7222	Intermediate Similarity	NPD6331	Phase 2
0.7219	Intermediate Similarity	NPD2801	Approved
0.7218	Intermediate Similarity	NPD2230	Approved
0.7218	Intermediate Similarity	NPD2232	Approved
0.7218	Intermediate Similarity	NPD2233	Approved
0.7203	Intermediate Similarity	NPD2859	Approved
0.7203	Intermediate Similarity	NPD2860	Approved
0.7203	Intermediate Similarity	NPD844	Approved
0.72	Intermediate Similarity	NPD556	Approved
0.7197	Intermediate Similarity	NPD3496	Discontinued
0.7194	Intermediate Similarity	NPD3062	Approved
0.7194	Intermediate Similarity	NPD3061	Approved
0.7194	Intermediate Similarity	NPD3059	Approved
0.7192	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1774	Approved
0.719	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD2677	Approved
0.7172	Intermediate Similarity	NPD2219	Phase 1
0.7172	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6190	Approved
0.7172	Intermediate Similarity	NPD5241	Discontinued
0.7165	Intermediate Similarity	NPD9377	Approved
0.7165	Intermediate Similarity	NPD9379	Approved
0.7163	Intermediate Similarity	NPD6111	Discontinued
0.7153	Intermediate Similarity	NPD596	Approved
0.7153	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD600	Approved
0.7152	Intermediate Similarity	NPD7228	Approved
0.7143	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD288	Approved
0.7143	Intermediate Similarity	NPD4123	Phase 3
0.7132	Intermediate Similarity	NPD558	Phase 2
0.7124	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3882	Suspended
0.7123	Intermediate Similarity	NPD5058	Phase 3
0.7122	Intermediate Similarity	NPD839	Approved
0.7122	Intermediate Similarity	NPD840	Approved
0.7122	Intermediate Similarity	NPD6233	Phase 2
0.7121	Intermediate Similarity	NPD2668	Approved
0.7121	Intermediate Similarity	NPD2667	Approved
0.7119	Intermediate Similarity	NPD2933	Approved
0.7119	Intermediate Similarity	NPD2934	Approved
0.7107	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1242	Phase 1
0.7105	Intermediate Similarity	NPD5772	Approved
0.7105	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5773	Approved
0.7103	Intermediate Similarity	NPD4628	Phase 3
0.7101	Intermediate Similarity	NPD3179	Approved
0.7101	Intermediate Similarity	NPD7095	Approved
0.7101	Intermediate Similarity	NPD3180	Approved
0.7099	Intermediate Similarity	NPD3091	Approved
0.7097	Intermediate Similarity	NPD3134	Approved
0.7092	Intermediate Similarity	NPD823	Approved
0.7092	Intermediate Similarity	NPD5314	Approved
0.7092	Intermediate Similarity	NPD817	Approved
0.7083	Intermediate Similarity	NPD2424	Discontinued
0.7075	Intermediate Similarity	NPD1511	Approved
0.7071	Intermediate Similarity	NPD4140	Approved
0.7067	Intermediate Similarity	NPD4005	Discontinued
0.7063	Intermediate Similarity	NPD4750	Phase 3
0.7063	Intermediate Similarity	NPD7074	Phase 3
0.7063	Intermediate Similarity	NPD5451	Approved
0.7059	Intermediate Similarity	NPD1818	Approved
0.7059	Intermediate Similarity	NPD1820	Approved
0.7059	Intermediate Similarity	NPD1819	Approved
0.7059	Intermediate Similarity	NPD2563	Approved
0.7059	Intermediate Similarity	NPD1817	Approved
0.7059	Intermediate Similarity	NPD2560	Approved
0.705	Intermediate Similarity	NPD6798	Discontinued
0.7045	Intermediate Similarity	NPD5691	Approved
0.7044	Intermediate Similarity	NPD3818	Discontinued
0.7042	Intermediate Similarity	NPD6896	Approved
0.7042	Intermediate Similarity	NPD6895	Approved
0.7037	Intermediate Similarity	NPD5327	Phase 3
0.7037	Intermediate Similarity	NPD6583	Phase 3
0.7037	Intermediate Similarity	NPD6582	Phase 2
0.7037	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1652	Phase 2
0.7027	Intermediate Similarity	NPD4160	Clinical (unspecified phase)

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