NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	776.3
Volume:	772.438
LogP:	4.19
LogD:	2.425
LogS:	-4.727
# Rotatable Bonds:	15
TPSA:	187.26
# H-Bond Aceptor:	14
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.214
Synthetic Accessibility Score:	5.28
Fsp3:	0.524
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.366
MDCK Permeability:	0.00011021509999409318
Pgp-inhibitor:	1.0
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.353
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.193
Plasma Protein Binding (PPB):	73.45134735107422%
Volume Distribution (VD):	2.078
Pgp-substrate:	9.432897567749023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.016
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.473
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.311
CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.437
CYP3A4-substrate:	0.535

ADMET: Excretion

Clearance (CL):	3.663
Half-life (T1/2):	0.145

ADMET: Toxicity

hERG Blockers:	0.228
Human Hepatotoxicity (H-HT):	0.967
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.07
Rat Oral Acute Toxicity:	0.387
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.12
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC209567

Natural Product ID:	NPC209567
*Common Name:**	Epoxyconiferyl Alcohol
IUPAC Name:	4-[3-(hydroxymethyl)oxiran-2-yl]-2-methoxyphenol
Synonyms:	Epoxyconiferyl Alcohol
Standard InCHIKey:	DZDKPIKBVMNBEA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H12O4/c1-13-8-4-6(2-3-7(8)12)10-9(5-11)14-10/h2-4,9-12H,5H2,1H3
SMILES:	OCC1OC1c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1933705
PubChem CID:	57403796
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
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	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	>	50000.0	nM	PMID[540519]

☑ 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 NPC209567 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	378
0.1-0.2	1580
0.2-0.3	5406
0.3-0.4	12345
0.4-0.5	5257
0.5-0.6	6003
0.6-0.7	8159
0.7-0.8	2831
0.8-0.85	526
0.85-0.9	183
0.9-0.95	27
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9741	High Similarity	NPC470804
0.9739	High Similarity	NPC177475
0.9739	High Similarity	NPC35071
0.9739	High Similarity	NPC148615
0.9652	High Similarity	NPC320987
0.9652	High Similarity	NPC181969
0.9565	High Similarity	NPC255675
0.9483	High Similarity	NPC135961
0.9407	High Similarity	NPC476343
0.9391	High Similarity	NPC221049
0.9262	High Similarity	NPC147821
0.9262	High Similarity	NPC163332
0.9262	High Similarity	NPC183181
0.9262	High Similarity	NPC111247
0.9262	High Similarity	NPC292056
0.9262	High Similarity	NPC319625
0.9262	High Similarity	NPC41706
0.9262	High Similarity	NPC118787
0.925	High Similarity	NPC220598
0.925	High Similarity	NPC165375
0.9187	High Similarity	NPC252307
0.9187	High Similarity	NPC245826
0.9187	High Similarity	NPC474178
0.918	High Similarity	NPC191037
0.918	High Similarity	NPC178284
0.918	High Similarity	NPC58607
0.9153	High Similarity	NPC311595
0.9153	High Similarity	NPC24474
0.9113	High Similarity	NPC5851
0.9113	High Similarity	NPC86030
0.9106	High Similarity	NPC118533
0.9106	High Similarity	NPC165045
0.9098	High Similarity	NPC194519
0.9091	High Similarity	NPC471693
0.9083	High Similarity	NPC49341
0.9076	High Similarity	NPC229401
0.904	High Similarity	NPC42300
0.904	High Similarity	NPC145305
0.904	High Similarity	NPC77040
0.904	High Similarity	NPC174495
0.904	High Similarity	NPC92164
0.904	High Similarity	NPC64201
0.904	High Similarity	NPC241522
0.904	High Similarity	NPC257582
0.904	High Similarity	NPC187998
0.904	High Similarity	NPC153739
0.904	High Similarity	NPC242807
0.9032	High Similarity	NPC72529
0.9016	High Similarity	NPC94276
0.9016	High Similarity	NPC293701
0.9016	High Similarity	NPC114901
0.9016	High Similarity	NPC109822
0.9016	High Similarity	NPC48990
0.8992	High Similarity	NPC20674
0.8983	High Similarity	NPC164386
0.8968	High Similarity	NPC248307
0.8968	High Similarity	NPC277804
0.8968	High Similarity	NPC470096
0.8968	High Similarity	NPC472597
0.8968	High Similarity	NPC470095
0.8968	High Similarity	NPC65942
0.896	High Similarity	NPC475875
0.896	High Similarity	NPC476968
0.896	High Similarity	NPC170844
0.8957	High Similarity	NPC156840
0.8957	High Similarity	NPC139617
0.8957	High Similarity	NPC257124
0.8957	High Similarity	NPC8547
0.8957	High Similarity	NPC78918
0.8957	High Similarity	NPC173746
0.8952	High Similarity	NPC5428
0.8943	High Similarity	NPC148627
0.8926	High Similarity	NPC113865
0.8926	High Similarity	NPC324571
0.8926	High Similarity	NPC470212
0.8926	High Similarity	NPC343720
0.8926	High Similarity	NPC312675
0.8926	High Similarity	NPC262156
0.8926	High Similarity	NPC54872
0.8926	High Similarity	NPC184651
0.8926	High Similarity	NPC473853
0.8898	High Similarity	NPC7903
0.8898	High Similarity	NPC253105
0.8898	High Similarity	NPC184447
0.8898	High Similarity	NPC16208
0.8898	High Similarity	NPC35932
0.8898	High Similarity	NPC201587
0.8898	High Similarity	NPC160991
0.8889	High Similarity	NPC472338
0.888	High Similarity	NPC21867
0.888	High Similarity	NPC186843
0.888	High Similarity	NPC184733
0.888	High Similarity	NPC206615
0.888	High Similarity	NPC45774
0.888	High Similarity	NPC282703
0.888	High Similarity	NPC470084
0.888	High Similarity	NPC98631
0.888	High Similarity	NPC128208
0.888	High Similarity	NPC470213
0.888	High Similarity	NPC129570
0.888	High Similarity	NPC11258
0.8852	High Similarity	NPC71090
0.8843	High Similarity	NPC207613
0.8824	High Similarity	NPC259638
0.8819	High Similarity	NPC474017
0.8819	High Similarity	NPC161557
0.8819	High Similarity	NPC27843
0.8819	High Similarity	NPC228346
0.8819	High Similarity	NPC40432
0.8819	High Similarity	NPC158079
0.8819	High Similarity	NPC115207
0.8819	High Similarity	NPC7171
0.881	High Similarity	NPC226788
0.881	High Similarity	NPC190629
0.881	High Similarity	NPC202582
0.881	High Similarity	NPC222004
0.881	High Similarity	NPC3439
0.881	High Similarity	NPC218856
0.881	High Similarity	NPC307110
0.881	High Similarity	NPC210623
0.881	High Similarity	NPC285339
0.881	High Similarity	NPC273295
0.881	High Similarity	NPC470258
0.8783	High Similarity	NPC36108
0.8783	High Similarity	NPC233731
0.8783	High Similarity	NPC7097
0.8783	High Similarity	NPC246358
0.878	High Similarity	NPC280704
0.876	High Similarity	NPC476387
0.876	High Similarity	NPC35731
0.876	High Similarity	NPC170694
0.876	High Similarity	NPC119060
0.876	High Similarity	NPC287745
0.876	High Similarity	NPC310854
0.876	High Similarity	NPC237594
0.876	High Similarity	NPC135127
0.876	High Similarity	NPC470881
0.876	High Similarity	NPC249791
0.875	High Similarity	NPC207400
0.875	High Similarity	NPC181049
0.875	High Similarity	NPC4940
0.875	High Similarity	NPC470752
0.875	High Similarity	NPC63083
0.874	High Similarity	NPC143483
0.8739	High Similarity	NPC193067
0.872	High Similarity	NPC206882
0.871	High Similarity	NPC183446
0.8707	High Similarity	NPC137685
0.8699	High Similarity	NPC85488
0.8692	High Similarity	NPC472337
0.8682	High Similarity	NPC158331
0.8682	High Similarity	NPC6836
0.8682	High Similarity	NPC475840
0.8678	High Similarity	NPC477803
0.8672	High Similarity	NPC309787
0.8672	High Similarity	NPC30043
0.8672	High Similarity	NPC469480
0.8672	High Similarity	NPC469625
0.8672	High Similarity	NPC469613
0.8667	High Similarity	NPC293619
0.8661	High Similarity	NPC26653
0.8661	High Similarity	NPC166040
0.8661	High Similarity	NPC212015
0.8661	High Similarity	NPC270849
0.8651	High Similarity	NPC210355
0.8651	High Similarity	NPC474119
0.864	High Similarity	NPC57490
0.864	High Similarity	NPC117214
0.864	High Similarity	NPC208950
0.864	High Similarity	NPC298757
0.864	High Similarity	NPC221077
0.864	High Similarity	NPC116907
0.864	High Similarity	NPC251855
0.864	High Similarity	NPC17943
0.864	High Similarity	NPC203133
0.864	High Similarity	NPC475169
0.864	High Similarity	NPC233410
0.864	High Similarity	NPC472093
0.864	High Similarity	NPC193544
0.8632	High Similarity	NPC195873
0.8629	High Similarity	NPC197757
0.8629	High Similarity	NPC228922
0.8626	High Similarity	NPC177160
0.8626	High Similarity	NPC52277
0.8626	High Similarity	NPC10737
0.8626	High Similarity	NPC263367
0.8626	High Similarity	NPC306441
0.8626	High Similarity	NPC477939
0.8626	High Similarity	NPC472336
0.8626	High Similarity	NPC54743
0.8626	High Similarity	NPC29799
0.8626	High Similarity	NPC209985
0.8626	High Similarity	NPC199459
0.8626	High Similarity	NPC472334
0.8626	High Similarity	NPC156502
0.8626	High Similarity	NPC177035
0.8626	High Similarity	NPC16435
0.8618	High Similarity	NPC285289
0.8618	High Similarity	NPC290451
0.8618	High Similarity	NPC127389

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 NPC209567 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	876
0.2-0.3	2139
0.3-0.4	2754
0.4-0.5	1500
0.5-0.6	933
0.6-0.7	538
0.7-0.8	84
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.896	High Similarity	NPD3027	Phase 3
0.8957	High Similarity	NPD228	Approved
0.8605	High Similarity	NPD1612	Clinical (unspecified phase)
0.8605	High Similarity	NPD1613	Approved
0.8295	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.808	Intermediate Similarity	NPD1357	Approved
0.8031	Intermediate Similarity	NPD3705	Approved
0.7983	Intermediate Similarity	NPD290	Approved
0.7917	Intermediate Similarity	NPD2684	Approved
0.791	Intermediate Similarity	NPD1558	Phase 1
0.7907	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD5283	Phase 1
0.7863	Intermediate Similarity	NPD291	Approved
0.7805	Intermediate Similarity	NPD7843	Approved
0.7778	Intermediate Similarity	NPD3620	Phase 2
0.7778	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD7157	Approved
0.7752	Intermediate Similarity	NPD1091	Approved
0.7698	Intermediate Similarity	NPD7266	Discontinued
0.7669	Intermediate Similarity	NPD9494	Approved
0.7655	Intermediate Similarity	NPD1653	Approved
0.7652	Intermediate Similarity	NPD9296	Approved
0.7634	Intermediate Similarity	NPD2982	Phase 2
0.7634	Intermediate Similarity	NPD2983	Phase 2
0.7597	Intermediate Similarity	NPD9384	Approved
0.7597	Intermediate Similarity	NPD9381	Approved
0.7589	Intermediate Similarity	NPD3060	Approved
0.7589	Intermediate Similarity	NPD4236	Phase 3
0.7589	Intermediate Similarity	NPD4237	Approved
0.7578	Intermediate Similarity	NPD1548	Phase 1
0.7574	Intermediate Similarity	NPD2674	Phase 3
0.7568	Intermediate Similarity	NPD1934	Approved
0.7561	Intermediate Similarity	NPD3022	Approved
0.7561	Intermediate Similarity	NPD3021	Approved
0.7557	Intermediate Similarity	NPD2981	Phase 2
0.7537	Intermediate Similarity	NPD3018	Phase 2
0.7537	Intermediate Similarity	NPD2861	Phase 2
0.75	Intermediate Similarity	NPD9622	Approved
0.7481	Intermediate Similarity	NPD1610	Phase 2
0.7464	Intermediate Similarity	NPD230	Phase 1
0.7459	Intermediate Similarity	NPD968	Approved
0.7447	Intermediate Similarity	NPD1375	Discontinued
0.7445	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD3687	Approved
0.7415	Intermediate Similarity	NPD3686	Approved
0.7372	Intermediate Similarity	NPD3144	Approved
0.7372	Intermediate Similarity	NPD3145	Approved
0.7364	Intermediate Similarity	NPD5536	Phase 2
0.736	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD4538	Approved
0.7357	Intermediate Similarity	NPD4536	Approved
0.7357	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4908	Phase 1
0.7344	Intermediate Similarity	NPD6671	Approved
0.7343	Intermediate Similarity	NPD6674	Discontinued
0.7343	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9621	Approved
0.7333	Intermediate Similarity	NPD9620	Approved
0.7333	Intermediate Similarity	NPD9619	Approved
0.7313	Intermediate Similarity	NPD8651	Approved
0.7305	Intermediate Similarity	NPD5960	Phase 3
0.7286	Intermediate Similarity	NPD6653	Approved
0.7285	Intermediate Similarity	NPD2978	Approved
0.7285	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2977	Approved
0.7285	Intermediate Similarity	NPD2801	Approved
0.728	Intermediate Similarity	NPD556	Approved
0.7266	Intermediate Similarity	NPD4060	Phase 1
0.726	Intermediate Similarity	NPD1774	Approved
0.726	Intermediate Similarity	NPD1511	Approved
0.7258	Intermediate Similarity	NPD1358	Approved
0.7246	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD821	Approved
0.7241	Intermediate Similarity	NPD2677	Approved
0.7241	Intermediate Similarity	NPD6190	Approved
0.7222	Intermediate Similarity	NPD4162	Approved
0.7218	Intermediate Similarity	NPD422	Phase 1
0.7211	Intermediate Similarity	NPD4123	Phase 3
0.7208	Intermediate Similarity	NPD6234	Discontinued
0.7203	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6166	Phase 2
0.719	Intermediate Similarity	NPD3882	Suspended
0.7183	Intermediate Similarity	NPD5588	Approved
0.7174	Intermediate Similarity	NPD3180	Approved
0.7174	Intermediate Similarity	NPD3179	Approved
0.7171	Intermediate Similarity	NPD5772	Approved
0.7171	Intermediate Similarity	NPD5773	Approved
0.7164	Intermediate Similarity	NPD2231	Phase 2
0.7164	Intermediate Similarity	NPD2235	Phase 2
0.7162	Intermediate Similarity	NPD1512	Approved
0.7162	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD52	Approved
0.7162	Intermediate Similarity	NPD7526	Approved
0.7143	Intermediate Similarity	NPD2238	Phase 2
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3496	Discontinued
0.7133	Intermediate Similarity	NPD2161	Phase 2
0.7123	Intermediate Similarity	NPD2219	Phase 1
0.7123	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD598	Approved
0.7122	Intermediate Similarity	NPD601	Approved
0.7122	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD597	Approved
0.7111	Intermediate Similarity	NPD4749	Approved
0.7111	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD9379	Approved
0.7109	Intermediate Similarity	NPD9377	Approved
0.7105	Intermediate Similarity	NPD37	Approved
0.7103	Intermediate Similarity	NPD1652	Phase 2
0.7103	Intermediate Similarity	NPD5177	Phase 3
0.7101	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD9365	Approved
0.7092	Intermediate Similarity	NPD5735	Approved
0.7092	Intermediate Similarity	NPD447	Suspended
0.7086	Intermediate Similarity	NPD4678	Approved
0.7086	Intermediate Similarity	NPD4675	Approved
0.708	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD558	Phase 2
0.708	Intermediate Similarity	NPD6584	Phase 3
0.7078	Intermediate Similarity	NPD4966	Approved
0.7078	Intermediate Similarity	NPD4965	Approved
0.7078	Intermediate Similarity	NPD4967	Phase 2
0.7078	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5058	Phase 3
0.7071	Intermediate Similarity	NPD1130	Approved
0.7071	Intermediate Similarity	NPD6233	Phase 2
0.7071	Intermediate Similarity	NPD1136	Approved
0.7071	Intermediate Similarity	NPD1132	Approved
0.7068	Intermediate Similarity	NPD1778	Approved
0.7068	Intermediate Similarity	NPD5846	Approved
0.7068	Intermediate Similarity	NPD6516	Phase 2
0.7063	Intermediate Similarity	NPD7054	Approved
0.7055	Intermediate Similarity	NPD4110	Phase 3
0.7055	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4628	Phase 3
0.7049	Intermediate Similarity	NPD1242	Phase 1
0.7037	Intermediate Similarity	NPD7685	Pre-registration
0.7021	Intermediate Similarity	NPD3061	Approved
0.7021	Intermediate Similarity	NPD3062	Approved
0.7021	Intermediate Similarity	NPD3059	Approved
0.7019	Intermediate Similarity	NPD7074	Phase 3
0.7019	Intermediate Similarity	NPD7472	Approved
0.7013	Intermediate Similarity	NPD2563	Approved
0.7013	Intermediate Similarity	NPD2560	Approved
0.7007	Intermediate Similarity	NPD5241	Discontinued
0.7007	Intermediate Similarity	NPD1818	Approved
0.7007	Intermediate Similarity	NPD1820	Approved
0.7007	Intermediate Similarity	NPD3094	Phase 2
0.7007	Intermediate Similarity	NPD1819	Approved
0.7007	Intermediate Similarity	NPD1817	Approved
0.7	Intermediate Similarity	NPD3818	Discontinued
0.7	Intermediate Similarity	NPD7228	Approved
0.6992	Remote Similarity	NPD940	Approved
0.6992	Remote Similarity	NPD846	Approved
0.6985	Remote Similarity	NPD3685	Discontinued
0.6978	Remote Similarity	NPD600	Approved
0.6978	Remote Similarity	NPD596	Approved
0.6966	Remote Similarity	NPD3540	Phase 1
0.6966	Remote Similarity	NPD5762	Approved
0.6966	Remote Similarity	NPD5763	Approved
0.695	Remote Similarity	NPD840	Approved
0.695	Remote Similarity	NPD839	Approved
0.6948	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.694	Remote Similarity	NPD4626	Approved
0.6939	Remote Similarity	NPD6331	Phase 2
0.6934	Remote Similarity	NPD6696	Suspended
0.6933	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4625	Phase 3
0.6929	Remote Similarity	NPD3164	Approved
0.6929	Remote Similarity	NPD7095	Approved
0.6929	Remote Similarity	NPD3165	Approved
0.6929	Remote Similarity	NPD3167	Approved
0.6929	Remote Similarity	NPD3166	Approved
0.6923	Remote Similarity	NPD5314	Approved
0.6923	Remote Similarity	NPD9295	Approved
0.6923	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7153	Discontinued
0.6918	Remote Similarity	NPD2424	Discontinued
0.6917	Remote Similarity	NPD1182	Approved
0.6917	Remote Similarity	NPD9545	Approved
0.6917	Remote Similarity	NPD2934	Approved
0.6917	Remote Similarity	NPD2933	Approved
0.6917	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4357	Discontinued
0.6912	Remote Similarity	NPD1608	Approved
0.6911	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4005	Discontinued
0.6905	Remote Similarity	NPD3134	Approved
0.6903	Remote Similarity	NPD3817	Phase 2
0.6903	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD9570	Approved
0.6897	Remote Similarity	NPD3539	Phase 1
0.6887	Remote Similarity	NPD2122	Discontinued
0.6884	Remote Similarity	NPD987	Approved
0.6879	Remote Similarity	NPD5111	Phase 2
0.6879	Remote Similarity	NPD5110	Phase 2
0.6879	Remote Similarity	NPD6859	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