NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	434.23
Volume:	440.42
LogP:	1.897
LogD:	1.842
LogS:	-3.449
# Rotatable Bonds:	4
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.506
Synthetic Accessibility Score:	6.143
Fsp3:	0.792
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.866
MDCK Permeability:	8.314407023135573e-05
Pgp-inhibitor:	0.967
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.938

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.406
Plasma Protein Binding (PPB):	34.165863037109375%
Volume Distribution (VD):	0.702
Pgp-substrate:	56.835060119628906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.173
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.16
CYP3A4-substrate:	0.231

ADMET: Excretion

Clearance (CL):	3.322
Half-life (T1/2):	0.26

ADMET: Toxicity

hERG Blockers:	0.664
Human Hepatotoxicity (H-HT):	0.09
Drug-inuced Liver Injury (DILI):	0.227
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.852
Carcinogencity:	0.326
Eye Corrosion:	0.169
Eye Irritation:	0.077
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC46844

Natural Product ID:	NPC46844
*Common Name:**	(R,E)-1-[4-(3-Hydroxyprop-1-Enyl)Phenoxy]-3-Methylbutane-2,3-Diol
IUPAC Name:	(2R)-1-[4-[(E)-3-hydroxyprop-1-enyl]phenoxy]-3-methylbutane-2,3-diol
Synonyms:
Standard InCHIKey:	HKPJLHUCTVFEFJ-ITDFMYJTSA-N
Standard InCHI:	InChI=1S/C14H20O4/c1-14(2,17)13(16)10-18-12-7-5-11(6-8-12)4-3-9-15/h3-8,13,15-17H,9-10H2,1-2H3/b4-3+/t13-/m1/s1
SMILES:	OC/C=C/c1ccc(cc1)OC[C@H](C(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400539
PubChem CID:	23642603
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002754] Cinnamyl alcohols

*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
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	fruit	Lanyu Island, Taitung County, Taiwan	n.a.	PMID[10395498]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17822293]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	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
NPT2740	Cell Line	Neutrophils		IC50	=	32550.0	nM	PMID[524555]

☑ 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 NPC46844 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	255
0.1-0.2	1317
0.2-0.3	5327
0.3-0.4	12578
0.4-0.5	5437
0.5-0.6	7459
0.6-0.7	7932
0.7-0.8	2199
0.8-0.85	168
0.85-0.9	18
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9216	High Similarity	NPC51633
0.9143	High Similarity	NPC194034
0.9126	High Similarity	NPC192596
0.9038	High Similarity	NPC38079
0.9038	High Similarity	NPC108875
0.8952	High Similarity	NPC470393
0.885	High Similarity	NPC163036
0.8818	High Similarity	NPC301735
0.8807	High Similarity	NPC55300
0.8785	High Similarity	NPC251306
0.8774	High Similarity	NPC8302
0.8727	High Similarity	NPC115379
0.8727	High Similarity	NPC165646
0.8696	High Similarity	NPC269242
0.8654	High Similarity	NPC100870
0.8624	High Similarity	NPC474272
0.8609	High Similarity	NPC469708
0.8609	High Similarity	NPC60589
0.8585	High Similarity	NPC305205
0.8559	High Similarity	NPC48990
0.8559	High Similarity	NPC114901
0.8559	High Similarity	NPC293701
0.8534	High Similarity	NPC198734
0.8534	High Similarity	NPC469412
0.8522	High Similarity	NPC311595
0.8522	High Similarity	NPC24474
0.8522	High Similarity	NPC135961
0.8476	Intermediate Similarity	NPC471576
0.8468	Intermediate Similarity	NPC78918
0.8468	Intermediate Similarity	NPC139617
0.8462	Intermediate Similarity	NPC470804
0.844	Intermediate Similarity	NPC258171
0.844	Intermediate Similarity	NPC227894
0.8435	Intermediate Similarity	NPC101503
0.8435	Intermediate Similarity	NPC329980
0.8421	Intermediate Similarity	NPC154256
0.8421	Intermediate Similarity	NPC290470
0.8407	Intermediate Similarity	NPC235250
0.8407	Intermediate Similarity	NPC161696
0.8403	Intermediate Similarity	NPC109822
0.8403	Intermediate Similarity	NPC94276
0.8403	Intermediate Similarity	NPC287429
0.839	Intermediate Similarity	NPC71090
0.8378	Intermediate Similarity	NPC137685
0.8376	Intermediate Similarity	NPC199023
0.8348	Intermediate Similarity	NPC164386
0.8347	Intermediate Similarity	NPC118787
0.8347	Intermediate Similarity	NPC183181
0.8347	Intermediate Similarity	NPC147821
0.8347	Intermediate Similarity	NPC111247
0.8347	Intermediate Similarity	NPC163332
0.8347	Intermediate Similarity	NPC292056
0.8347	Intermediate Similarity	NPC319625
0.8347	Intermediate Similarity	NPC41706
0.8333	Intermediate Similarity	NPC283546
0.8333	Intermediate Similarity	NPC194519
0.8333	Intermediate Similarity	NPC318429
0.8305	Intermediate Similarity	NPC184651
0.8305	Intermediate Similarity	NPC324571
0.8305	Intermediate Similarity	NPC343720
0.8305	Intermediate Similarity	NPC113865
0.8305	Intermediate Similarity	NPC262156
0.8305	Intermediate Similarity	NPC473853
0.8305	Intermediate Similarity	NPC470212
0.8305	Intermediate Similarity	NPC312675
0.8305	Intermediate Similarity	NPC226712
0.8305	Intermediate Similarity	NPC476343
0.8305	Intermediate Similarity	NPC127389
0.8305	Intermediate Similarity	NPC290451
0.8305	Intermediate Similarity	NPC54872
0.8291	Intermediate Similarity	NPC177475
0.8291	Intermediate Similarity	NPC148615
0.8291	Intermediate Similarity	NPC35071
0.8288	Intermediate Similarity	NPC7097
0.8288	Intermediate Similarity	NPC246358
0.8288	Intermediate Similarity	NPC36108
0.8288	Intermediate Similarity	NPC233731
0.8279	Intermediate Similarity	NPC222572
0.8279	Intermediate Similarity	NPC87224
0.8276	Intermediate Similarity	NPC283616
0.8276	Intermediate Similarity	NPC255675
0.8276	Intermediate Similarity	NPC474214
0.8264	Intermediate Similarity	NPC58607
0.8264	Intermediate Similarity	NPC178284
0.8264	Intermediate Similarity	NPC191037
0.8257	Intermediate Similarity	NPC473855
0.8235	Intermediate Similarity	NPC259134
0.8235	Intermediate Similarity	NPC8002
0.8235	Intermediate Similarity	NPC99886
0.8235	Intermediate Similarity	NPC177844
0.8235	Intermediate Similarity	NPC476142
0.8235	Intermediate Similarity	NPC209567
0.822	Intermediate Similarity	NPC473875
0.822	Intermediate Similarity	NPC207613
0.8211	Intermediate Similarity	NPC226788
0.8211	Intermediate Similarity	NPC210623
0.8211	Intermediate Similarity	NPC86030
0.8211	Intermediate Similarity	NPC248355
0.8211	Intermediate Similarity	NPC222004
0.8211	Intermediate Similarity	NPC166040
0.8211	Intermediate Similarity	NPC285339
0.8211	Intermediate Similarity	NPC273295
0.8211	Intermediate Similarity	NPC5851
0.8211	Intermediate Similarity	NPC190629
0.8211	Intermediate Similarity	NPC218856
0.8211	Intermediate Similarity	NPC202582
0.8211	Intermediate Similarity	NPC470258
0.8211	Intermediate Similarity	NPC3439
0.8205	Intermediate Similarity	NPC37858
0.8205	Intermediate Similarity	NPC320987
0.8205	Intermediate Similarity	NPC474320
0.8205	Intermediate Similarity	NPC181969
0.8197	Intermediate Similarity	NPC198798
0.8197	Intermediate Similarity	NPC473993
0.8197	Intermediate Similarity	NPC474119
0.8182	Intermediate Similarity	NPC470510
0.8182	Intermediate Similarity	NPC135464
0.8182	Intermediate Similarity	NPC167571
0.8182	Intermediate Similarity	NPC207179
0.8182	Intermediate Similarity	NPC113457
0.8182	Intermediate Similarity	NPC176971
0.8182	Intermediate Similarity	NPC92623
0.8182	Intermediate Similarity	NPC278552
0.8167	Intermediate Similarity	NPC474130
0.8165	Intermediate Similarity	NPC474603
0.8165	Intermediate Similarity	NPC12987
0.8155	Intermediate Similarity	NPC71853
0.8148	Intermediate Similarity	NPC101025
0.8148	Intermediate Similarity	NPC471578
0.8145	Intermediate Similarity	NPC472338
0.8145	Intermediate Similarity	NPC474491
0.8142	Intermediate Similarity	NPC257124
0.8142	Intermediate Similarity	NPC156840
0.8142	Intermediate Similarity	NPC266932
0.8142	Intermediate Similarity	NPC8547
0.8142	Intermediate Similarity	NPC173746
0.8136	Intermediate Similarity	NPC229401
0.813	Intermediate Similarity	NPC302378
0.813	Intermediate Similarity	NPC72529
0.8108	Intermediate Similarity	NPC151530
0.8108	Intermediate Similarity	NPC157473
0.8103	Intermediate Similarity	NPC301651
0.8103	Intermediate Similarity	NPC175771
0.8103	Intermediate Similarity	NPC473556
0.8103	Intermediate Similarity	NPC221049
0.8099	Intermediate Similarity	NPC74478
0.8095	Intermediate Similarity	NPC471581
0.8095	Intermediate Similarity	NPC25821
0.8091	Intermediate Similarity	NPC128730
0.8091	Intermediate Similarity	NPC233396
0.8091	Intermediate Similarity	NPC154899
0.8087	Intermediate Similarity	NPC313193
0.8083	Intermediate Similarity	NPC204535
0.8083	Intermediate Similarity	NPC46586
0.808	Intermediate Similarity	NPC469613
0.808	Intermediate Similarity	NPC29734
0.808	Intermediate Similarity	NPC103799
0.808	Intermediate Similarity	NPC30043
0.808	Intermediate Similarity	NPC472597
0.808	Intermediate Similarity	NPC469625
0.8077	Intermediate Similarity	NPC321956
0.8067	Intermediate Similarity	NPC475529
0.8067	Intermediate Similarity	NPC204466
0.8065	Intermediate Similarity	NPC26653
0.8065	Intermediate Similarity	NPC270849
0.8065	Intermediate Similarity	NPC295970
0.8056	Intermediate Similarity	NPC107101
0.8053	Intermediate Similarity	NPC231251
0.8053	Intermediate Similarity	NPC88868
0.8053	Intermediate Similarity	NPC25067
0.8049	Intermediate Similarity	NPC469386
0.8036	Intermediate Similarity	NPC201959
0.8036	Intermediate Similarity	NPC75440
0.8036	Intermediate Similarity	NPC241549
0.8036	Intermediate Similarity	NPC291837
0.8034	Intermediate Similarity	NPC86947
0.8034	Intermediate Similarity	NPC293619
0.8033	Intermediate Similarity	NPC12308
0.8017	Intermediate Similarity	NPC471693
0.8017	Intermediate Similarity	NPC220598
0.8017	Intermediate Similarity	NPC280704
0.8017	Intermediate Similarity	NPC38761
0.8017	Intermediate Similarity	NPC165375
0.8017	Intermediate Similarity	NPC301321
0.8017	Intermediate Similarity	NPC76465
0.8017	Intermediate Similarity	NPC474160
0.8016	Intermediate Similarity	NPC160991
0.8016	Intermediate Similarity	NPC7903
0.8016	Intermediate Similarity	NPC16208
0.8016	Intermediate Similarity	NPC184447
0.8016	Intermediate Similarity	NPC35932
0.8	Intermediate Similarity	NPC472024
0.8	Intermediate Similarity	NPC49341
0.8	Intermediate Similarity	NPC113098
0.8	Intermediate Similarity	NPC469612
0.8	Intermediate Similarity	NPC2518
0.8	Intermediate Similarity	NPC80600
0.8	Intermediate Similarity	NPC325292
0.8	Intermediate Similarity	NPC469614
0.8	Intermediate Similarity	NPC70752

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 NPC46844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	834
0.2-0.3	1904
0.3-0.4	2643
0.4-0.5	1715
0.5-0.6	1072
0.6-0.7	618
0.7-0.8	128
0.8-0.85	7
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9143	High Similarity	NPD290	Approved
0.9057	High Similarity	NPD2684	Approved
0.8899	High Similarity	NPD7843	Approved
0.8661	High Similarity	NPD7157	Approved
0.8491	Intermediate Similarity	NPD291	Approved
0.8333	Intermediate Similarity	NPD9365	Approved
0.8305	Intermediate Similarity	NPD1091	Approved
0.8273	Intermediate Similarity	NPD1358	Approved
0.823	Intermediate Similarity	NPD821	Approved
0.8182	Intermediate Similarity	NPD968	Approved
0.8142	Intermediate Similarity	NPD228	Approved
0.8051	Intermediate Similarity	NPD1357	Approved
0.7983	Intermediate Similarity	NPD6516	Phase 2
0.7983	Intermediate Similarity	NPD5846	Approved
0.7886	Intermediate Similarity	NPD1817	Approved
0.7886	Intermediate Similarity	NPD1819	Approved
0.7886	Intermediate Similarity	NPD1820	Approved
0.7886	Intermediate Similarity	NPD1818	Approved
0.7869	Intermediate Similarity	NPD3685	Discontinued
0.7857	Intermediate Similarity	NPD3134	Approved
0.7815	Intermediate Similarity	NPD1548	Phase 1
0.7807	Intermediate Similarity	NPD556	Approved
0.7795	Intermediate Similarity	NPD6233	Phase 2
0.7788	Intermediate Similarity	NPD9552	Approved
0.7778	Intermediate Similarity	NPD3180	Approved
0.7778	Intermediate Similarity	NPD3179	Approved
0.7778	Intermediate Similarity	NPD3027	Phase 3
0.7734	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD1613	Approved
0.7717	Intermediate Similarity	NPD6798	Discontinued
0.7712	Intermediate Similarity	NPD6671	Approved
0.7692	Intermediate Similarity	NPD4538	Approved
0.7692	Intermediate Similarity	NPD4536	Approved
0.7692	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD5647	Approved
0.7661	Intermediate Similarity	NPD8651	Approved
0.7656	Intermediate Similarity	NPD4062	Phase 3
0.7656	Intermediate Similarity	NPD1423	Approved
0.7638	Intermediate Similarity	NPD3167	Approved
0.7638	Intermediate Similarity	NPD3164	Approved
0.7638	Intermediate Similarity	NPD3166	Approved
0.7638	Intermediate Similarity	NPD3165	Approved
0.7615	Intermediate Similarity	NPD6653	Approved
0.7607	Intermediate Similarity	NPD5535	Approved
0.76	Intermediate Similarity	NPD1794	Approved
0.7597	Intermediate Similarity	NPD4060	Phase 1
0.7594	Intermediate Similarity	NPD2424	Discontinued
0.7593	Intermediate Similarity	NPD9296	Approved
0.7581	Intermediate Similarity	NPD6582	Phase 2
0.7581	Intermediate Similarity	NPD6583	Phase 3
0.7581	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1048	Approved
0.7573	Intermediate Similarity	NPD111	Approved
0.7561	Intermediate Similarity	NPD1610	Phase 2
0.7559	Intermediate Similarity	NPD4908	Phase 1
0.7542	Intermediate Similarity	NPD5283	Phase 1
0.7542	Intermediate Similarity	NPD1241	Discontinued
0.754	Intermediate Similarity	NPD3690	Phase 2
0.754	Intermediate Similarity	NPD3691	Phase 2
0.7538	Intermediate Similarity	NPD6355	Discontinued
0.7522	Intermediate Similarity	NPD9501	Approved
0.75	Intermediate Similarity	NPD2235	Phase 2
0.75	Intermediate Similarity	NPD5588	Approved
0.75	Intermediate Similarity	NPD5960	Phase 3
0.75	Intermediate Similarity	NPD2231	Phase 2
0.75	Intermediate Similarity	NPD7095	Approved
0.748	Intermediate Similarity	NPD3496	Discontinued
0.7462	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD987	Approved
0.7453	Intermediate Similarity	NPD9295	Approved
0.7442	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD2934	Approved
0.7431	Intermediate Similarity	NPD2933	Approved
0.7424	Intermediate Similarity	NPD7097	Phase 1
0.7422	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD422	Phase 1
0.7407	Intermediate Similarity	NPD1652	Phase 2
0.7405	Intermediate Similarity	NPD5735	Approved
0.7402	Intermediate Similarity	NPD558	Phase 2
0.7402	Intermediate Similarity	NPD6584	Phase 3
0.7398	Intermediate Similarity	NPD1778	Approved
0.7385	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD1894	Discontinued
0.7372	Intermediate Similarity	NPD5058	Phase 3
0.7364	Intermediate Similarity	NPD2860	Approved
0.7364	Intermediate Similarity	NPD2859	Approved
0.7355	Intermediate Similarity	NPD3596	Phase 2
0.7353	Intermediate Similarity	NPD4535	Phase 3
0.7353	Intermediate Similarity	NPD4628	Phase 3
0.735	Intermediate Similarity	NPD5451	Approved
0.7344	Intermediate Similarity	NPD2861	Phase 2
0.7344	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD6362	Approved
0.7313	Intermediate Similarity	NPD2240	Approved
0.7313	Intermediate Similarity	NPD2239	Approved
0.7308	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD5536	Phase 2
0.728	Intermediate Similarity	NPD1535	Discovery
0.728	Intermediate Similarity	NPD776	Approved
0.7279	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4340	Discontinued
0.7273	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD191	Approved
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD2667	Approved
0.7258	Intermediate Similarity	NPD2668	Approved
0.7252	Intermediate Similarity	NPD3163	Approved
0.7252	Intermediate Similarity	NPD3162	Approved
0.7239	Intermediate Similarity	NPD7033	Discontinued
0.7239	Intermediate Similarity	NPD3152	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6580	Approved
0.7236	Intermediate Similarity	NPD1182	Approved
0.7236	Intermediate Similarity	NPD6581	Approved
0.7222	Intermediate Similarity	NPD1481	Phase 2
0.7222	Intermediate Similarity	NPD9717	Approved
0.7218	Intermediate Similarity	NPD3052	Approved
0.7218	Intermediate Similarity	NPD3054	Approved
0.7209	Intermediate Similarity	NPD9494	Approved
0.7209	Intermediate Similarity	NPD4993	Discontinued
0.72	Intermediate Similarity	NPD3847	Discontinued
0.7197	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4140	Approved
0.7197	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3620	Phase 2
0.7193	Intermediate Similarity	NPD940	Approved
0.7193	Intermediate Similarity	NPD846	Approved
0.7188	Intermediate Similarity	NPD3827	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD3020	Approved
0.7165	Intermediate Similarity	NPD4749	Approved
0.7165	Intermediate Similarity	NPD5327	Phase 3
0.7165	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2983	Phase 2
0.7165	Intermediate Similarity	NPD2982	Phase 2
0.7155	Intermediate Similarity	NPD9697	Approved
0.7153	Intermediate Similarity	NPD4162	Approved
0.7143	Intermediate Similarity	NPD3536	Discontinued
0.7143	Intermediate Similarity	NPD3705	Approved
0.7132	Intermediate Similarity	NPD5763	Approved
0.7132	Intermediate Similarity	NPD5762	Approved
0.7131	Intermediate Similarity	NPD2557	Approved
0.7122	Intermediate Similarity	NPD5756	Phase 2
0.7122	Intermediate Similarity	NPD5295	Discontinued
0.712	Intermediate Similarity	NPD4626	Approved
0.7107	Intermediate Similarity	NPD594	Approved
0.7107	Intermediate Similarity	NPD592	Approved
0.7099	Intermediate Similarity	NPD5163	Phase 2
0.709	Intermediate Similarity	NPD6353	Approved
0.7087	Intermediate Similarity	NPD2981	Phase 2
0.708	Intermediate Similarity	NPD4534	Discontinued
0.7068	Intermediate Similarity	NPD2238	Phase 2
0.7068	Intermediate Similarity	NPD1558	Phase 1
0.7059	Intermediate Similarity	NPD5712	Approved
0.7059	Intermediate Similarity	NPD3021	Approved
0.7059	Intermediate Similarity	NPD2161	Phase 2
0.7059	Intermediate Similarity	NPD3022	Approved
0.7054	Intermediate Similarity	NPD2797	Approved
0.705	Intermediate Similarity	NPD2677	Approved
0.7045	Intermediate Similarity	NPD3144	Approved
0.7045	Intermediate Similarity	NPD3145	Approved
0.704	Intermediate Similarity	NPD1798	Approved
0.704	Intermediate Similarity	NPD5691	Approved
0.704	Intermediate Similarity	NPD1797	Approved
0.704	Intermediate Similarity	NPD5585	Approved
0.7031	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD2428	Approved
0.7031	Intermediate Similarity	NPD2429	Approved
0.7025	Intermediate Similarity	NPD1138	Approved
0.7023	Intermediate Similarity	NPD600	Approved
0.7023	Intermediate Similarity	NPD596	Approved
0.7023	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3985	Discontinued
0.7007	Intermediate Similarity	NPD1375	Discontinued
0.6993	Remote Similarity	NPD1653	Approved
0.6992	Remote Similarity	NPD839	Approved
0.6992	Remote Similarity	NPD840	Approved
0.6992	Remote Similarity	NPD5745	Approved
0.6992	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD2674	Phase 3
0.6985	Remote Similarity	NPD2156	Approved
0.6985	Remote Similarity	NPD2154	Approved
0.6985	Remote Similarity	NPD2155	Approved
0.6984	Remote Similarity	NPD2554	Approved
0.6984	Remote Similarity	NPD2556	Approved
0.6978	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4110	Phase 3
0.6977	Remote Similarity	NPD3225	Approved
0.6972	Remote Similarity	NPD7526	Approved
0.6972	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD52	Approved
0.697	Remote Similarity	NPD4625	Phase 3
0.697	Remote Similarity	NPD6179	Discontinued
0.696	Remote Similarity	NPD9545	Approved
0.6957	Remote Similarity	NPD1242	Phase 1
0.6957	Remote Similarity	NPD5958	Discontinued
0.6953	Remote Similarity	NPD2230	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