NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	206.09
Volume:	220.74
LogP:	1.475
LogD:	1.753
LogS:	-1.952
# Rotatable Bonds:	5
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.736
Synthetic Accessibility Score:	2.695
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.319
MDCK Permeability:	3.4184049582108855e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.978
Plasma Protein Binding (PPB):	51.39109420776367%
Volume Distribution (VD):	1.585
Pgp-substrate:	15.988130569458008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.588
CYP1A2-substrate:	0.73
CYP2C19-inhibitor:	0.635
CYP2C19-substrate:	0.744
CYP2C9-inhibitor:	0.102
CYP2C9-substrate:	0.515
CYP2D6-inhibitor:	0.088
CYP2D6-substrate:	0.751
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.611

ADMET: Excretion

Clearance (CL):	7.99
Half-life (T1/2):	0.665

ADMET: Toxicity

hERG Blockers:	0.129
Human Hepatotoxicity (H-HT):	0.425
Drug-inuced Liver Injury (DILI):	0.372
AMES Toxicity:	0.798
Rat Oral Acute Toxicity:	0.875
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.883
Carcinogencity:	0.458
Eye Corrosion:	0.01
Eye Irritation:	0.733
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC115379

Natural Product ID:	NPC115379
*Common Name:**	1-O-Methylterricolyne
IUPAC Name:	(2S)-1-[4-(methoxymethyl)phenoxy]but-3-yn-2-ol
Synonyms:	1-O-Methylterricolyne
Standard InCHIKey:	JCJDSZJTMTUHJC-NSHDSACASA-N
Standard InCHI:	InChI=1S/C12H14O3/c1-3-11(13)9-15-12-6-4-10(5-7-12)8-14-2/h1,4-7,11,13H,8-9H2,2H3/t11-/m0/s1
SMILES:	C#C[C@@H](COc1ccc(cc1)COC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078080
PubChem CID:	45102790
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002542] Benzylethers

*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
NPO1743	Neurospora terricola	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19795843]
NPO1743	Neurospora terricola	Species	Sordariaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	92600.0	nM	PMID[557063]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	115700.0	nM	PMID[557063]

☑ 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 NPC115379 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	328
0.1-0.2	1631
0.2-0.3	6215
0.3-0.4	13206
0.4-0.5	4321
0.5-0.6	8705
0.6-0.7	6710
0.7-0.8	1493
0.8-0.85	74
0.85-0.9	11
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9717	High Similarity	NPC301735
0.9455	High Similarity	NPC101503
0.8972	High Similarity	NPC251306
0.8962	High Similarity	NPC8302
0.8796	High Similarity	NPC194034
0.8774	High Similarity	NPC305205
0.8727	High Similarity	NPC46844
0.8692	High Similarity	NPC108875
0.8692	High Similarity	NPC38079
0.8679	High Similarity	NPC51633
0.8611	High Similarity	NPC470393
0.8598	High Similarity	NPC192596
0.8584	High Similarity	NPC235250
0.8491	Intermediate Similarity	NPC100870
0.8421	Intermediate Similarity	NPC161696
0.8403	Intermediate Similarity	NPC71090
0.8393	Intermediate Similarity	NPC88868
0.8393	Intermediate Similarity	NPC231251
0.8393	Intermediate Similarity	NPC25067
0.839	Intermediate Similarity	NPC469412
0.839	Intermediate Similarity	NPC269242
0.839	Intermediate Similarity	NPC198734
0.8378	Intermediate Similarity	NPC291837
0.8319	Intermediate Similarity	NPC55300
0.8305	Intermediate Similarity	NPC60589
0.8305	Intermediate Similarity	NPC469708
0.8291	Intermediate Similarity	NPC255675
0.8276	Intermediate Similarity	NPC221049
0.8273	Intermediate Similarity	NPC238115
0.8264	Intermediate Similarity	NPC109822
0.8264	Intermediate Similarity	NPC94276
0.8246	Intermediate Similarity	NPC165646
0.824	Intermediate Similarity	NPC104854
0.822	Intermediate Similarity	NPC135961
0.822	Intermediate Similarity	NPC181969
0.822	Intermediate Similarity	NPC320987
0.8197	Intermediate Similarity	NPC194519
0.8173	Intermediate Similarity	NPC318429
0.8167	Intermediate Similarity	NPC470804
0.8158	Intermediate Similarity	NPC266932
0.8151	Intermediate Similarity	NPC35071
0.8151	Intermediate Similarity	NPC177475
0.8151	Intermediate Similarity	NPC148615
0.8148	Intermediate Similarity	NPC471576
0.813	Intermediate Similarity	NPC58607
0.813	Intermediate Similarity	NPC178284
0.813	Intermediate Similarity	NPC191037
0.8125	Intermediate Similarity	NPC227894
0.8125	Intermediate Similarity	NPC258171
0.8115	Intermediate Similarity	NPC293701
0.8115	Intermediate Similarity	NPC48990
0.8115	Intermediate Similarity	NPC114901
0.8108	Intermediate Similarity	NPC473855
0.8099	Intermediate Similarity	NPC209567
0.8099	Intermediate Similarity	NPC476142
0.8095	Intermediate Similarity	NPC321956
0.8083	Intermediate Similarity	NPC475529
0.8083	Intermediate Similarity	NPC199023
0.8083	Intermediate Similarity	NPC473875
0.8077	Intermediate Similarity	NPC8002
0.8077	Intermediate Similarity	NPC259134
0.8077	Intermediate Similarity	NPC99886
0.8077	Intermediate Similarity	NPC177844
0.807	Intermediate Similarity	NPC106141
0.807	Intermediate Similarity	NPC137685
0.8067	Intermediate Similarity	NPC163036
0.8065	Intermediate Similarity	NPC319625
0.8065	Intermediate Similarity	NPC147821
0.8065	Intermediate Similarity	NPC41706
0.8065	Intermediate Similarity	NPC474119
0.8065	Intermediate Similarity	NPC183181
0.8065	Intermediate Similarity	NPC163332
0.8065	Intermediate Similarity	NPC111247
0.8065	Intermediate Similarity	NPC292056
0.8065	Intermediate Similarity	NPC118787
0.8051	Intermediate Similarity	NPC142042
0.8049	Intermediate Similarity	NPC207179
0.8049	Intermediate Similarity	NPC167571
0.8049	Intermediate Similarity	NPC278552
0.8018	Intermediate Similarity	NPC283546
0.8017	Intermediate Similarity	NPC226712
0.8	Intermediate Similarity	NPC71853
0.8	Intermediate Similarity	NPC139617
0.8	Intermediate Similarity	NPC78918
0.7982	Intermediate Similarity	NPC474272
0.7967	Intermediate Similarity	NPC287429
0.7966	Intermediate Similarity	NPC290470
0.7966	Intermediate Similarity	NPC154256
0.7946	Intermediate Similarity	NPC128730
0.7937	Intermediate Similarity	NPC5851
0.7937	Intermediate Similarity	NPC190629
0.7937	Intermediate Similarity	NPC270849
0.7937	Intermediate Similarity	NPC210623
0.7937	Intermediate Similarity	NPC166040
0.7937	Intermediate Similarity	NPC273295
0.7937	Intermediate Similarity	NPC26653
0.7937	Intermediate Similarity	NPC470258
0.7937	Intermediate Similarity	NPC285339
0.7937	Intermediate Similarity	NPC226788
0.7937	Intermediate Similarity	NPC222004
0.7937	Intermediate Similarity	NPC202582
0.7937	Intermediate Similarity	NPC3439
0.7937	Intermediate Similarity	NPC218856
0.7937	Intermediate Similarity	NPC86030
0.7934	Intermediate Similarity	NPC267064
0.792	Intermediate Similarity	NPC198798
0.7909	Intermediate Similarity	NPC107101
0.7899	Intermediate Similarity	NPC164386
0.789	Intermediate Similarity	NPC95755
0.7886	Intermediate Similarity	NPC471693
0.7876	Intermediate Similarity	NPC176971
0.7874	Intermediate Similarity	NPC472024
0.7874	Intermediate Similarity	NPC472338
0.7874	Intermediate Similarity	NPC474491
0.7874	Intermediate Similarity	NPC80600
0.787	Intermediate Similarity	NPC313650
0.7869	Intermediate Similarity	NPC290451
0.7869	Intermediate Similarity	NPC127389
0.7869	Intermediate Similarity	NPC476343
0.7857	Intermediate Similarity	NPC302378
0.7857	Intermediate Similarity	NPC222572
0.7857	Intermediate Similarity	NPC87224
0.7857	Intermediate Similarity	NPC292792
0.7857	Intermediate Similarity	NPC72529
0.7851	Intermediate Similarity	NPC93398
0.7851	Intermediate Similarity	NPC258979
0.7851	Intermediate Similarity	NPC229401
0.7851	Intermediate Similarity	NPC8283
0.7845	Intermediate Similarity	NPC257124
0.7845	Intermediate Similarity	NPC156840
0.7845	Intermediate Similarity	NPC8547
0.7845	Intermediate Similarity	NPC173746
0.7838	Intermediate Similarity	NPC310905
0.7838	Intermediate Similarity	NPC12714
0.7838	Intermediate Similarity	NPC307425
0.7833	Intermediate Similarity	NPC74821
0.7833	Intermediate Similarity	NPC63083
0.7826	Intermediate Similarity	NPC36108
0.7826	Intermediate Similarity	NPC7097
0.7826	Intermediate Similarity	NPC246358
0.7826	Intermediate Similarity	NPC233731
0.7823	Intermediate Similarity	NPC74478
0.7815	Intermediate Similarity	NPC175771
0.7815	Intermediate Similarity	NPC301651
0.7815	Intermediate Similarity	NPC473556
0.7812	Intermediate Similarity	NPC472597
0.7812	Intermediate Similarity	NPC30043
0.7812	Intermediate Similarity	NPC469625
0.7812	Intermediate Similarity	NPC29734
0.7812	Intermediate Similarity	NPC103799
0.7812	Intermediate Similarity	NPC469613
0.7807	Intermediate Similarity	NPC157473
0.7807	Intermediate Similarity	NPC151530
0.7805	Intermediate Similarity	NPC100099
0.7805	Intermediate Similarity	NPC150026
0.7805	Intermediate Similarity	NPC36016
0.7805	Intermediate Similarity	NPC261661
0.7795	Intermediate Similarity	NPC295970
0.7795	Intermediate Similarity	NPC248355
0.7778	Intermediate Similarity	NPC471581
0.7769	Intermediate Similarity	NPC172253
0.7769	Intermediate Similarity	NPC24474
0.7769	Intermediate Similarity	NPC311595
0.7769	Intermediate Similarity	NPC59561
0.7769	Intermediate Similarity	NPC295259
0.7769	Intermediate Similarity	NPC20674
0.7768	Intermediate Similarity	NPC179686
0.776	Intermediate Similarity	NPC320242
0.776	Intermediate Similarity	NPC148627
0.776	Intermediate Similarity	NPC470510
0.776	Intermediate Similarity	NPC81641
0.7752	Intermediate Similarity	NPC35932
0.7752	Intermediate Similarity	NPC16208
0.7752	Intermediate Similarity	NPC160991
0.7752	Intermediate Similarity	NPC7903
0.7752	Intermediate Similarity	NPC184447
0.775	Intermediate Similarity	NPC259638
0.7748	Intermediate Similarity	NPC13755
0.7742	Intermediate Similarity	NPC279379
0.7742	Intermediate Similarity	NPC165375
0.7742	Intermediate Similarity	NPC76465
0.7742	Intermediate Similarity	NPC220598
0.7742	Intermediate Similarity	NPC38761
0.7734	Intermediate Similarity	NPC113098
0.7734	Intermediate Similarity	NPC469614
0.7734	Intermediate Similarity	NPC469612
0.7727	Intermediate Similarity	NPC175298
0.7724	Intermediate Similarity	NPC97432
0.7724	Intermediate Similarity	NPC49341
0.7724	Intermediate Similarity	NPC190454
0.7719	Intermediate Similarity	NPC113457
0.7717	Intermediate Similarity	NPC245826
0.7717	Intermediate Similarity	NPC252307
0.7717	Intermediate Similarity	NPC474178
0.7717	Intermediate Similarity	NPC470084
0.7712	Intermediate Similarity	NPC303522
0.7712	Intermediate Similarity	NPC204120
0.7699	Intermediate Similarity	NPC12987
0.7699	Intermediate Similarity	NPC474603
0.7699	Intermediate Similarity	NPC2518

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 NPC115379 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	944
0.2-0.3	2053
0.3-0.4	2670
0.4-0.5	1574
0.5-0.6	995
0.6-0.7	522
0.7-0.8	81
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD2684	Approved
0.8796	High Similarity	NPD290	Approved
0.8571	High Similarity	NPD7843	Approved
0.8348	Intermediate Similarity	NPD7157	Approved
0.8173	Intermediate Similarity	NPD9365	Approved
0.8017	Intermediate Similarity	NPD1091	Approved
0.7937	Intermediate Similarity	NPD3180	Approved
0.7937	Intermediate Similarity	NPD3179	Approved
0.7931	Intermediate Similarity	NPD821	Approved
0.7876	Intermediate Similarity	NPD968	Approved
0.7851	Intermediate Similarity	NPD5846	Approved
0.7851	Intermediate Similarity	NPD6516	Phase 2
0.7845	Intermediate Similarity	NPD228	Approved
0.7838	Intermediate Similarity	NPD291	Approved
0.7833	Intermediate Similarity	NPD1548	Phase 1
0.7823	Intermediate Similarity	NPD8651	Approved
0.7807	Intermediate Similarity	NPD1358	Approved
0.776	Intermediate Similarity	NPD1820	Approved
0.776	Intermediate Similarity	NPD1819	Approved
0.776	Intermediate Similarity	NPD1817	Approved
0.776	Intermediate Similarity	NPD1818	Approved
0.7615	Intermediate Similarity	NPD1613	Approved
0.7615	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD1610	Phase 2
0.7565	Intermediate Similarity	NPD3134	Approved
0.7563	Intermediate Similarity	NPD1241	Discontinued
0.7519	Intermediate Similarity	NPD3164	Approved
0.7519	Intermediate Similarity	NPD3167	Approved
0.7519	Intermediate Similarity	NPD3027	Phase 3
0.7519	Intermediate Similarity	NPD3165	Approved
0.7519	Intermediate Similarity	NPD3166	Approved
0.748	Intermediate Similarity	NPD1794	Approved
0.748	Intermediate Similarity	NPD1357	Approved
0.746	Intermediate Similarity	NPD3685	Discontinued
0.7444	Intermediate Similarity	NPD4538	Approved
0.7444	Intermediate Similarity	NPD4536	Approved
0.7444	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD422	Phase 1
0.7419	Intermediate Similarity	NPD1778	Approved
0.7405	Intermediate Similarity	NPD1423	Approved
0.7391	Intermediate Similarity	NPD9501	Approved
0.7373	Intermediate Similarity	NPD556	Approved
0.7364	Intermediate Similarity	NPD2861	Phase 2
0.735	Intermediate Similarity	NPD9552	Approved
0.7333	Intermediate Similarity	NPD5535	Approved
0.7328	Intermediate Similarity	NPD6798	Discontinued
0.7308	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4908	Phase 1
0.7302	Intermediate Similarity	NPD3705	Approved
0.7299	Intermediate Similarity	NPD1652	Phase 2
0.7293	Intermediate Similarity	NPD4340	Discontinued
0.7293	Intermediate Similarity	NPD5735	Approved
0.7273	Intermediate Similarity	NPD5283	Phase 1
0.7273	Intermediate Similarity	NPD4062	Phase 3
0.7273	Intermediate Similarity	NPD6233	Phase 2
0.7259	Intermediate Similarity	NPD5588	Approved
0.7259	Intermediate Similarity	NPD5960	Phase 3
0.7258	Intermediate Similarity	NPD1182	Approved
0.7258	Intermediate Similarity	NPD1894	Discontinued
0.7246	Intermediate Similarity	NPD4628	Phase 3
0.7239	Intermediate Similarity	NPD6353	Approved
0.7236	Intermediate Similarity	NPD3596	Phase 2
0.7231	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5451	Approved
0.7218	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD1558	Phase 1
0.7209	Intermediate Similarity	NPD987	Approved
0.7197	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6582	Phase 2
0.7188	Intermediate Similarity	NPD6583	Phase 3
0.7179	Intermediate Similarity	NPD9697	Approved
0.7174	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD776	Approved
0.7164	Intermediate Similarity	NPD6355	Discontinued
0.7154	Intermediate Similarity	NPD3691	Phase 2
0.7154	Intermediate Similarity	NPD6671	Approved
0.7154	Intermediate Similarity	NPD3690	Phase 2
0.7143	Intermediate Similarity	NPD3162	Approved
0.7143	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3163	Approved
0.7143	Intermediate Similarity	NPD9296	Approved
0.7143	Intermediate Similarity	NPD5058	Phase 3
0.712	Intermediate Similarity	NPD9545	Approved
0.712	Intermediate Similarity	NPD6581	Approved
0.712	Intermediate Similarity	NPD6580	Approved
0.7111	Intermediate Similarity	NPD3054	Approved
0.7111	Intermediate Similarity	NPD3052	Approved
0.7109	Intermediate Similarity	NPD1608	Approved
0.7109	Intermediate Similarity	NPD2235	Phase 2
0.7109	Intermediate Similarity	NPD2231	Phase 2
0.7103	Intermediate Similarity	NPD111	Approved
0.709	Intermediate Similarity	NPD4060	Phase 1
0.709	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD3496	Discontinued
0.708	Intermediate Similarity	NPD2240	Approved
0.708	Intermediate Similarity	NPD2239	Approved
0.7071	Intermediate Similarity	NPD2677	Approved
0.7063	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5327	Phase 3
0.7054	Intermediate Similarity	NPD2982	Phase 2
0.7054	Intermediate Similarity	NPD2983	Phase 2
0.7029	Intermediate Similarity	NPD5763	Approved
0.7029	Intermediate Similarity	NPD6005	Phase 3
0.7029	Intermediate Similarity	NPD5762	Approved
0.7029	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6004	Phase 3
0.7029	Intermediate Similarity	NPD1375	Discontinued
0.7029	Intermediate Similarity	NPD6002	Phase 3
0.7023	Intermediate Similarity	NPD4624	Approved
0.7023	Intermediate Similarity	NPD5647	Approved
0.7023	Intermediate Similarity	NPD6584	Phase 3
0.7016	Intermediate Similarity	NPD2557	Approved
0.7008	Intermediate Similarity	NPD17	Approved
0.7007	Intermediate Similarity	NPD3152	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9295	Approved
0.6992	Remote Similarity	NPD592	Approved
0.6992	Remote Similarity	NPD594	Approved
0.6992	Remote Similarity	NPD7095	Approved
0.6991	Remote Similarity	NPD2933	Approved
0.6991	Remote Similarity	NPD2934	Approved
0.6985	Remote Similarity	NPD6653	Approved
0.6978	Remote Similarity	NPD2424	Discontinued
0.6977	Remote Similarity	NPD2981	Phase 2
0.6977	Remote Similarity	NPD1840	Phase 2
0.697	Remote Similarity	NPD3018	Phase 2
0.6963	Remote Similarity	NPD4140	Approved
0.6957	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1048	Approved
0.6934	Remote Similarity	NPD7097	Phase 1
0.693	Remote Similarity	NPD2859	Approved
0.693	Remote Similarity	NPD2860	Approved
0.6929	Remote Similarity	NPD4162	Approved
0.6929	Remote Similarity	NPD5691	Approved
0.6929	Remote Similarity	NPD5585	Approved
0.6929	Remote Similarity	NPD4237	Approved
0.6929	Remote Similarity	NPD4236	Phase 3
0.6923	Remote Similarity	NPD4749	Approved
0.6923	Remote Similarity	NPD940	Approved
0.6923	Remote Similarity	NPD2428	Approved
0.6923	Remote Similarity	NPD3536	Discontinued
0.6923	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2429	Approved
0.6923	Remote Similarity	NPD846	Approved
0.6917	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5124	Phase 1
0.6912	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5536	Phase 2
0.6899	Remote Similarity	NPD1535	Discovery
0.6894	Remote Similarity	NPD558	Phase 2
0.6884	Remote Similarity	NPD2154	Approved
0.6884	Remote Similarity	NPD7033	Discontinued
0.6884	Remote Similarity	NPD2156	Approved
0.6884	Remote Similarity	NPD2155	Approved
0.688	Remote Similarity	NPD191	Approved
0.6879	Remote Similarity	NPD4535	Phase 3
0.6875	Remote Similarity	NPD2667	Approved
0.6875	Remote Similarity	NPD2554	Approved
0.6875	Remote Similarity	NPD4626	Approved
0.6875	Remote Similarity	NPD2556	Approved
0.6875	Remote Similarity	NPD2668	Approved
0.6866	Remote Similarity	NPD6179	Discontinued
0.6866	Remote Similarity	NPD5163	Phase 2
0.6857	Remote Similarity	NPD4534	Discontinued
0.6853	Remote Similarity	NPD6799	Approved
0.6853	Remote Similarity	NPD1774	Approved
0.6846	Remote Similarity	NPD1481	Phase 2
0.6842	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4993	Discontinued
0.6842	Remote Similarity	NPD454	Approved
0.6842	Remote Similarity	NPD9494	Approved
0.6838	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD3620	Phase 2
0.6835	Remote Similarity	NPD2161	Phase 2
0.6822	Remote Similarity	NPD3847	Discontinued
0.6822	Remote Similarity	NPD3294	Phase 2
0.6818	Remote Similarity	NPD6362	Approved
0.6818	Remote Similarity	NPD3567	Approved
0.6818	Remote Similarity	NPD2082	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3568	Approved
0.6815	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3445	Approved
0.6797	Remote Similarity	NPD3049	Approved
0.6797	Remote Similarity	NPD6382	Discontinued
0.6797	Remote Similarity	NPD3444	Approved
0.6797	Remote Similarity	NPD1798	Approved
0.6797	Remote Similarity	NPD1797	Approved
0.6797	Remote Similarity	NPD3443	Approved
0.6794	Remote Similarity	NPD6542	Approved
0.6794	Remote Similarity	NPD6543	Approved
0.6794	Remote Similarity	NPD6540	Phase 3
0.6794	Remote Similarity	NPD6539	Approved
0.6791	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3686	Approved
0.6781	Remote Similarity	NPD3687	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