NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	214.08
Volume:	209.002
LogP:	-0.586
LogD:	0.128
LogS:	-0.376
# Rotatable Bonds:	4
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.556
Synthetic Accessibility Score:	2.913
Fsp3:	0.4
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:	-4.991
MDCK Permeability:	0.0002487168530933559
Pgp-inhibitor:	0.0
Pgp-substrate:	0.156
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.099
30% Bioavailability (F30%):	0.222

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.668
Plasma Protein Binding (PPB):	29.53685188293457%
Volume Distribution (VD):	1.113
Pgp-substrate:	62.54021453857422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.335
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.603
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.708
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.392
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.128

ADMET: Excretion

Clearance (CL):	10.689
Half-life (T1/2):	0.873

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.038
Drug-inuced Liver Injury (DILI):	0.059
AMES Toxicity:	0.101
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.161
Carcinogencity:	0.04
Eye Corrosion:	0.004
Eye Irritation:	0.399
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: NPC177475

Natural Product ID:	NPC177475
*Common Name:**	Threo-Guaiacylglycerol
IUPAC Name:	(1S,2S)-1-(4-hydroxy-3-methoxyphenyl)propane-1,2,3-triol
Synonyms:
Standard InCHIKey:	LSKFUSLVUZISST-WPRPVWTQSA-N
Standard InCHI:	InChI=1S/C10H14O5/c1-15-9-4-6(2-3-7(9)12)10(14)8(13)5-11/h2-4,8,10-14H,5H2,1H3/t8-,10-/m0/s1
SMILES:	COc1cc(ccc1O)[C@@H]([C@H](CO)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3608840
PubChem CID:	12310249
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
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	stem	n.a.	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	skin-removed stems	Pingle Town, Sichuang Province, China	2008-AUG	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22690646]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[26238320]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26767291]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	bark	n.a.	PMID[26767291]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	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
Others	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	Inhibition	=	48.4	%	PMID[474092]

☑ 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 NPC177475 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	340
0.1-0.2	1535
0.2-0.3	5086
0.3-0.4	12401
0.4-0.5	5399
0.5-0.6	5254
0.6-0.7	8264
0.7-0.8	3231
0.8-0.85	720
0.85-0.9	364
0.9-0.95	91
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC148615
1.0	High Similarity	NPC35071
0.9911	High Similarity	NPC181969
0.9911	High Similarity	NPC320987
0.9825	High Similarity	NPC470804
0.9821	High Similarity	NPC255675
0.9739	High Similarity	NPC209567
0.9735	High Similarity	NPC135961
0.9652	High Similarity	NPC476343
0.9643	High Similarity	NPC221049
0.9487	High Similarity	NPC220598
0.9487	High Similarity	NPC165375
0.9391	High Similarity	NPC24474
0.9391	High Similarity	NPC311595
0.9333	High Similarity	NPC163332
0.9333	High Similarity	NPC41706
0.9333	High Similarity	NPC319625
0.9333	High Similarity	NPC292056
0.9333	High Similarity	NPC147821
0.9333	High Similarity	NPC165045
0.9333	High Similarity	NPC118787
0.9333	High Similarity	NPC183181
0.9333	High Similarity	NPC118533
0.9333	High Similarity	NPC111247
0.9322	High Similarity	NPC471693
0.9316	High Similarity	NPC49341
0.931	High Similarity	NPC229401
0.9256	High Similarity	NPC252307
0.9256	High Similarity	NPC245826
0.9256	High Similarity	NPC474178
0.925	High Similarity	NPC178284
0.925	High Similarity	NPC58607
0.925	High Similarity	NPC191037
0.9224	High Similarity	NPC20674
0.9217	High Similarity	NPC164386
0.9196	High Similarity	NPC78918
0.9196	High Similarity	NPC257124
0.9196	High Similarity	NPC173746
0.9196	High Similarity	NPC139617
0.9196	High Similarity	NPC8547
0.9196	High Similarity	NPC156840
0.918	High Similarity	NPC86030
0.918	High Similarity	NPC170844
0.918	High Similarity	NPC476968
0.918	High Similarity	NPC5851
0.9174	High Similarity	NPC5428
0.9167	High Similarity	NPC148627
0.9167	High Similarity	NPC194519
0.9153	High Similarity	NPC312675
0.9153	High Similarity	NPC54872
0.9153	High Similarity	NPC184651
0.9153	High Similarity	NPC470212
0.9153	High Similarity	NPC473853
0.9153	High Similarity	NPC262156
0.9153	High Similarity	NPC113865
0.9153	High Similarity	NPC343720
0.9153	High Similarity	NPC324571
0.9106	High Similarity	NPC187998
0.9106	High Similarity	NPC77040
0.9106	High Similarity	NPC42300
0.9106	High Similarity	NPC153739
0.9106	High Similarity	NPC174495
0.9106	High Similarity	NPC92164
0.9106	High Similarity	NPC257582
0.9106	High Similarity	NPC145305
0.9106	High Similarity	NPC242807
0.9106	High Similarity	NPC64201
0.9106	High Similarity	NPC241522
0.9098	High Similarity	NPC470213
0.9098	High Similarity	NPC98631
0.9098	High Similarity	NPC186843
0.9098	High Similarity	NPC206615
0.9098	High Similarity	NPC72529
0.9083	High Similarity	NPC109822
0.9083	High Similarity	NPC293701
0.9083	High Similarity	NPC48990
0.9083	High Similarity	NPC94276
0.9083	High Similarity	NPC114901
0.9068	High Similarity	NPC207613
0.9052	High Similarity	NPC259638
0.9032	High Similarity	NPC65942
0.9032	High Similarity	NPC474017
0.9032	High Similarity	NPC470095
0.9032	High Similarity	NPC472597
0.9032	High Similarity	NPC248307
0.9032	High Similarity	NPC470096
0.9032	High Similarity	NPC277804
0.9024	High Similarity	NPC475875
0.9018	High Similarity	NPC36108
0.9018	High Similarity	NPC7097
0.9018	High Similarity	NPC246358
0.9018	High Similarity	NPC233731
0.9	High Similarity	NPC280704
0.8974	High Similarity	NPC63083
0.8966	High Similarity	NPC193067
0.896	High Similarity	NPC35932
0.896	High Similarity	NPC201587
0.896	High Similarity	NPC7903
0.896	High Similarity	NPC253105
0.896	High Similarity	NPC184447
0.896	High Similarity	NPC16208
0.896	High Similarity	NPC160991
0.8952	High Similarity	NPC472338
0.8952	High Similarity	NPC143483
0.8943	High Similarity	NPC45774
0.8943	High Similarity	NPC11258
0.8943	High Similarity	NPC21867
0.8943	High Similarity	NPC184733
0.8943	High Similarity	NPC128208
0.8943	High Similarity	NPC282703
0.8943	High Similarity	NPC470084
0.8943	High Similarity	NPC129570
0.8938	High Similarity	NPC137685
0.8926	High Similarity	NPC183446
0.8917	High Similarity	NPC85488
0.8917	High Similarity	NPC71090
0.8898	High Similarity	NPC477803
0.8889	High Similarity	NPC293619
0.888	High Similarity	NPC115207
0.888	High Similarity	NPC27843
0.888	High Similarity	NPC7171
0.888	High Similarity	NPC161557
0.888	High Similarity	NPC40432
0.888	High Similarity	NPC228346
0.888	High Similarity	NPC158079
0.8871	High Similarity	NPC3439
0.8871	High Similarity	NPC212015
0.8871	High Similarity	NPC226788
0.8871	High Similarity	NPC210623
0.8871	High Similarity	NPC285339
0.8871	High Similarity	NPC273295
0.8871	High Similarity	NPC218856
0.8871	High Similarity	NPC202582
0.8871	High Similarity	NPC222004
0.8871	High Similarity	NPC470258
0.8871	High Similarity	NPC190629
0.8871	High Similarity	NPC307110
0.886	High Similarity	NPC195873
0.8852	High Similarity	NPC203133
0.8852	High Similarity	NPC251855
0.8852	High Similarity	NPC17943
0.8852	High Similarity	NPC208950
0.8852	High Similarity	NPC57490
0.8852	High Similarity	NPC475169
0.8852	High Similarity	NPC233410
0.8852	High Similarity	NPC116907
0.8852	High Similarity	NPC221077
0.8852	High Similarity	NPC298757
0.8852	High Similarity	NPC117214
0.8852	High Similarity	NPC472093
0.8852	High Similarity	NPC193544
0.8843	High Similarity	NPC197757
0.8843	High Similarity	NPC228922
0.8839	High Similarity	NPC251306
0.8839	High Similarity	NPC227894
0.8833	High Similarity	NPC285289
0.8824	High Similarity	NPC61516
0.8824	High Similarity	NPC247364
0.8824	High Similarity	NPC10932
0.8824	High Similarity	NPC232084
0.8819	High Similarity	NPC287745
0.8819	High Similarity	NPC170694
0.8819	High Similarity	NPC35731
0.8819	High Similarity	NPC237594
0.8819	High Similarity	NPC310854
0.8819	High Similarity	NPC249791
0.8819	High Similarity	NPC135127
0.8819	High Similarity	NPC470881
0.8819	High Similarity	NPC119060
0.8819	High Similarity	NPC476387
0.8814	High Similarity	NPC474214
0.8814	High Similarity	NPC470626
0.881	High Similarity	NPC207400
0.881	High Similarity	NPC470752
0.881	High Similarity	NPC4940
0.881	High Similarity	NPC181049
0.88	High Similarity	NPC142985
0.88	High Similarity	NPC195292
0.879	High Similarity	NPC472968
0.878	High Similarity	NPC18924
0.878	High Similarity	NPC214406
0.878	High Similarity	NPC78974
0.878	High Similarity	NPC28730
0.878	High Similarity	NPC44748
0.878	High Similarity	NPC103823
0.878	High Similarity	NPC473960
0.878	High Similarity	NPC206882
0.878	High Similarity	NPC223136
0.877	High Similarity	NPC5796
0.877	High Similarity	NPC206487
0.876	High Similarity	NPC270326
0.876	High Similarity	NPC41562
0.876	High Similarity	NPC262253
0.876	High Similarity	NPC473411
0.876	High Similarity	NPC71579
0.875	High Similarity	NPC472337
0.875	High Similarity	NPC256262
0.874	High Similarity	NPC158331
0.874	High Similarity	NPC129889
0.874	High Similarity	NPC307006

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 NPC177475 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	867
0.2-0.3	2036
0.3-0.4	2748
0.4-0.5	1531
0.5-0.6	913
0.6-0.7	602
0.7-0.8	143
0.8-0.85	4
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9196	High Similarity	NPD228	Approved
0.918	High Similarity	NPD3027	Phase 3
0.8661	High Similarity	NPD1613	Approved
0.8661	High Similarity	NPD1612	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8279	Intermediate Similarity	NPD1357	Approved
0.8268	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8083	Intermediate Similarity	NPD5283	Phase 1
0.808	Intermediate Similarity	NPD3705	Approved
0.8034	Intermediate Similarity	NPD290	Approved
0.7966	Intermediate Similarity	NPD2684	Approved
0.7955	Intermediate Similarity	NPD1558	Phase 1
0.7955	Intermediate Similarity	NPD3620	Phase 2
0.7955	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7913	Intermediate Similarity	NPD291	Approved
0.7857	Intermediate Similarity	NPD9296	Approved
0.7851	Intermediate Similarity	NPD7843	Approved
0.7846	Intermediate Similarity	NPD9494	Approved
0.7812	Intermediate Similarity	NPD2983	Phase 2
0.7812	Intermediate Similarity	NPD2982	Phase 2
0.7805	Intermediate Similarity	NPD7157	Approved
0.7795	Intermediate Similarity	NPD1091	Approved
0.7778	Intermediate Similarity	NPD9381	Approved
0.7778	Intermediate Similarity	NPD9384	Approved
0.7754	Intermediate Similarity	NPD3060	Approved
0.775	Intermediate Similarity	NPD3022	Approved
0.775	Intermediate Similarity	NPD3021	Approved
0.7744	Intermediate Similarity	NPD2674	Phase 3
0.7737	Intermediate Similarity	NPD7266	Discontinued
0.7734	Intermediate Similarity	NPD2981	Phase 2
0.771	Intermediate Similarity	NPD3018	Phase 2
0.7692	Intermediate Similarity	NPD1653	Approved
0.7674	Intermediate Similarity	NPD9622	Approved
0.7626	Intermediate Similarity	NPD4236	Phase 3
0.7626	Intermediate Similarity	NPD4237	Approved
0.7619	Intermediate Similarity	NPD1548	Phase 1
0.7603	Intermediate Similarity	NPD1934	Approved
0.7576	Intermediate Similarity	NPD2861	Phase 2
0.7541	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD5536	Phase 2
0.7537	Intermediate Similarity	NPD3145	Approved
0.7537	Intermediate Similarity	NPD3144	Approved
0.7519	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD9621	Approved
0.75	Intermediate Similarity	NPD968	Approved
0.75	Intermediate Similarity	NPD9619	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD9620	Approved
0.7482	Intermediate Similarity	NPD1375	Discontinued
0.7481	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD3687	Approved
0.7448	Intermediate Similarity	NPD3686	Approved
0.7432	Intermediate Similarity	NPD2978	Approved
0.7432	Intermediate Similarity	NPD2977	Approved
0.7391	Intermediate Similarity	NPD4536	Approved
0.7391	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4538	Approved
0.7388	Intermediate Similarity	NPD4908	Phase 1
0.7381	Intermediate Similarity	NPD6671	Approved
0.7376	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD6674	Discontinued
0.7348	Intermediate Similarity	NPD8651	Approved
0.7319	Intermediate Similarity	NPD6653	Approved
0.7317	Intermediate Similarity	NPD556	Approved
0.7315	Intermediate Similarity	NPD2801	Approved
0.7315	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2238	Phase 2
0.7299	Intermediate Similarity	NPD4060	Phase 1
0.7295	Intermediate Similarity	NPD1358	Approved
0.7292	Intermediate Similarity	NPD1774	Approved
0.7292	Intermediate Similarity	NPD1511	Approved
0.728	Intermediate Similarity	NPD9379	Approved
0.728	Intermediate Similarity	NPD821	Approved
0.728	Intermediate Similarity	NPD9377	Approved
0.7279	Intermediate Similarity	NPD601	Approved
0.7279	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD597	Approved
0.7279	Intermediate Similarity	NPD598	Approved
0.7273	Intermediate Similarity	NPD6190	Approved
0.7273	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2219	Phase 1
0.7273	Intermediate Similarity	NPD2677	Approved
0.7254	Intermediate Similarity	NPD5177	Phase 3
0.7254	Intermediate Similarity	NPD4162	Approved
0.7252	Intermediate Similarity	NPD422	Phase 1
0.7248	Intermediate Similarity	NPD37	Approved
0.7241	Intermediate Similarity	NPD4123	Phase 3
0.7239	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6234	Discontinued
0.7234	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD1242	Phase 1
0.7226	Intermediate Similarity	NPD6166	Phase 2
0.7226	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1136	Approved
0.7226	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1130	Approved
0.7226	Intermediate Similarity	NPD1132	Approved
0.7219	Intermediate Similarity	NPD3882	Suspended
0.7214	Intermediate Similarity	NPD5588	Approved
0.7214	Intermediate Similarity	NPD5960	Phase 3
0.7206	Intermediate Similarity	NPD3180	Approved
0.7206	Intermediate Similarity	NPD3179	Approved
0.72	Intermediate Similarity	NPD5773	Approved
0.72	Intermediate Similarity	NPD5772	Approved
0.7197	Intermediate Similarity	NPD2235	Phase 2
0.7197	Intermediate Similarity	NPD2231	Phase 2
0.7192	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD52	Approved
0.7192	Intermediate Similarity	NPD1512	Approved
0.7192	Intermediate Similarity	NPD7526	Approved
0.7176	Intermediate Similarity	NPD3496	Discontinued
0.7174	Intermediate Similarity	NPD3061	Approved
0.7174	Intermediate Similarity	NPD3062	Approved
0.7174	Intermediate Similarity	NPD3059	Approved
0.7172	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD940	Approved
0.7167	Intermediate Similarity	NPD846	Approved
0.7164	Intermediate Similarity	NPD3094	Phase 2
0.7163	Intermediate Similarity	NPD2161	Phase 2
0.7153	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5241	Discontinued
0.7153	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4749	Approved
0.7133	Intermediate Similarity	NPD1652	Phase 2
0.7132	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD600	Approved
0.7132	Intermediate Similarity	NPD596	Approved
0.713	Intermediate Similarity	NPD9365	Approved
0.7122	Intermediate Similarity	NPD5735	Approved
0.7122	Intermediate Similarity	NPD447	Suspended
0.7114	Intermediate Similarity	NPD4678	Approved
0.7114	Intermediate Similarity	NPD4675	Approved
0.7113	Intermediate Similarity	NPD3540	Phase 1
0.7111	Intermediate Similarity	NPD558	Phase 2
0.7111	Intermediate Similarity	NPD6584	Phase 3
0.7105	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4966	Approved
0.7105	Intermediate Similarity	NPD4965	Approved
0.7105	Intermediate Similarity	NPD9295	Approved
0.7105	Intermediate Similarity	NPD4967	Phase 2
0.7103	Intermediate Similarity	NPD5058	Phase 3
0.7101	Intermediate Similarity	NPD6233	Phase 2
0.7101	Intermediate Similarity	NPD840	Approved
0.7101	Intermediate Similarity	NPD839	Approved
0.7099	Intermediate Similarity	NPD5846	Approved
0.7099	Intermediate Similarity	NPD4626	Approved
0.7099	Intermediate Similarity	NPD1778	Approved
0.7099	Intermediate Similarity	NPD6516	Phase 2
0.7094	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD2933	Approved
0.7094	Intermediate Similarity	NPD2934	Approved
0.7089	Intermediate Similarity	NPD7054	Approved
0.7086	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4628	Phase 3
0.7083	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4110	Phase 3
0.7083	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5314	Approved
0.7059	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4357	Discontinued
0.7054	Intermediate Similarity	NPD111	Approved
0.7047	Intermediate Similarity	NPD4005	Discontinued
0.7044	Intermediate Similarity	NPD7074	Phase 3
0.7044	Intermediate Similarity	NPD7472	Approved
0.7042	Intermediate Similarity	NPD9570	Approved
0.7042	Intermediate Similarity	NPD3539	Phase 1
0.704	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2563	Approved
0.7039	Intermediate Similarity	NPD2560	Approved
0.7037	Intermediate Similarity	NPD1817	Approved
0.7037	Intermediate Similarity	NPD1818	Approved
0.7037	Intermediate Similarity	NPD1820	Approved
0.7037	Intermediate Similarity	NPD1819	Approved
0.7034	Intermediate Similarity	NPD2860	Approved
0.7034	Intermediate Similarity	NPD844	Approved
0.7034	Intermediate Similarity	NPD2859	Approved
0.7029	Intermediate Similarity	NPD5111	Phase 2
0.7029	Intermediate Similarity	NPD5109	Approved
0.7029	Intermediate Similarity	NPD5110	Phase 2
0.7025	Intermediate Similarity	NPD7228	Approved
0.7025	Intermediate Similarity	NPD3818	Discontinued
0.7021	Intermediate Similarity	NPD6111	Discontinued
0.7015	Intermediate Similarity	NPD3685	Discontinued
0.7	Intermediate Similarity	NPD3020	Approved
0.7	Intermediate Similarity	NPD3657	Discovery
0.6993	Remote Similarity	NPD5763	Approved
0.6993	Remote Similarity	NPD5762	Approved
0.6992	Remote Similarity	NPD3092	Approved
0.6975	Remote Similarity	NPD288	Approved
0.6966	Remote Similarity	NPD6331	Phase 2
0.6963	Remote Similarity	NPD6696	Suspended
0.6963	Remote Similarity	NPD2922	Phase 1
0.6959	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7095	Approved
0.6957	Remote Similarity	NPD4625	Phase 3
0.695	Remote Similarity	NPD817	Approved
0.695	Remote Similarity	NPD823	Approved
0.6947	Remote Similarity	NPD1182	Approved
0.6947	Remote Similarity	NPD9545	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