NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.15
Volume:	249.178
LogP:	3.638
LogD:	3.15
LogS:	-3.739
# Rotatable Bonds:	6
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.747
Synthetic Accessibility Score:	1.947
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.297
MDCK Permeability:	2.3451679226127453e-05
Pgp-inhibitor:	0.181
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.332
30% Bioavailability (F30%):	0.85

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.898
Plasma Protein Binding (PPB):	95.77481842041016%
Volume Distribution (VD):	3.533
Pgp-substrate:	3.7487964630126953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.282
CYP2C19-inhibitor:	0.846
CYP2C19-substrate:	0.205
CYP2C9-inhibitor:	0.557
CYP2C9-substrate:	0.752
CYP2D6-inhibitor:	0.215
CYP2D6-substrate:	0.615
CYP3A4-inhibitor:	0.076
CYP3A4-substrate:	0.46

ADMET: Excretion

Clearance (CL):	15.139
Half-life (T1/2):	0.374

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.845
Drug-inuced Liver Injury (DILI):	0.077
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.791
Carcinogencity:	0.442
Eye Corrosion:	0.008
Eye Irritation:	0.927
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC108875

Natural Product ID:	NPC108875
*Common Name:**	3-(4-Isopentenyloxyphenyl)-1-Propanol
IUPAC Name:	3-[4-(3-methylbut-2-enoxy)phenyl]propan-1-ol
Synonyms:
Standard InCHIKey:	JYSMWPSRMOZRPR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H20O2/c1-12(2)9-11-16-14-7-5-13(6-8-14)4-3-10-15/h5-9,15H,3-4,10-11H2,1-2H3
SMILES:	CC(=CCOc1ccc(CCCO)cc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2022669
PubChem CID:	3009279
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers

*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
NPO26601	Zanthoxylum wutaiense	Species	Rutaceae	Eukaryota	root wood	n.a.	n.a.	PMID[18564877]
NPO5258	Fagara zanthoxyloides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22472691]
NPO26601	Zanthoxylum wutaiense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22472691]
NPO5258	Fagara zanthoxyloides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26601	Zanthoxylum wutaiense	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
Others	9

Activity Type	# Activity
Individual Protein	7
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.091	n.a.	PMID[568429]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	0.69	n.a.	PMID[568429]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	0.798	n.a.	PMID[568429]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	0.939	n.a.	PMID[568429]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.293	n.a.	PMID[568429]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.398	n.a.	PMID[568429]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.531	n.a.	PMID[568429]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	28.0	%	PMID[568430]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	68.0	%	PMID[568430]

☑ 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 NPC108875 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	236
0.1-0.2	1420
0.2-0.3	5116
0.3-0.4	13296
0.4-0.5	4985
0.5-0.6	7977
0.6-0.7	7448
0.7-0.8	2002
0.8-0.85	173
0.85-0.9	31
0.9-0.95	8
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC38079
0.9897	High Similarity	NPC470393
0.9588	High Similarity	NPC51633
0.9583	High Similarity	NPC100870
0.949	High Similarity	NPC192596
0.93	High Similarity	NPC8302
0.9109	High Similarity	NPC473855
0.91	High Similarity	NPC305205
0.9038	High Similarity	NPC46844
0.899	High Similarity	NPC471576
0.8958	High Similarity	NPC321956
0.8942	High Similarity	NPC474272
0.8932	High Similarity	NPC251306
0.8932	High Similarity	NPC194034
0.8879	High Similarity	NPC235250
0.8857	High Similarity	NPC137685
0.8854	High Similarity	NPC71853
0.8835	High Similarity	NPC113457
0.8774	High Similarity	NPC55300
0.875	High Similarity	NPC99886
0.875	High Similarity	NPC177844
0.875	High Similarity	NPC8002
0.875	High Similarity	NPC259134
0.8704	High Similarity	NPC161696
0.87	High Similarity	NPC95755
0.8692	High Similarity	NPC115379
0.8692	High Similarity	NPC165646
0.8667	High Similarity	NPC75440
0.8654	High Similarity	NPC176971
0.8641	High Similarity	NPC283546
0.8627	High Similarity	NPC307425
0.8611	High Similarity	NPC301735
0.8586	High Similarity	NPC471581
0.8571	High Similarity	NPC157473
0.8571	High Similarity	NPC151530
0.8571	High Similarity	NPC258171
0.8558	High Similarity	NPC128730
0.8529	High Similarity	NPC107101
0.8505	High Similarity	NPC25067
0.8505	High Similarity	NPC88868
0.8505	High Similarity	NPC231251
0.8491	Intermediate Similarity	NPC201959
0.8491	Intermediate Similarity	NPC291837
0.8485	Intermediate Similarity	NPC325292
0.8485	Intermediate Similarity	NPC138117
0.8476	Intermediate Similarity	NPC92623
0.8476	Intermediate Similarity	NPC135464
0.8469	Intermediate Similarity	NPC300017
0.8462	Intermediate Similarity	NPC12987
0.8462	Intermediate Similarity	NPC474603
0.8447	Intermediate Similarity	NPC300166
0.8426	Intermediate Similarity	NPC266932
0.8411	Intermediate Similarity	NPC234639
0.8396	Intermediate Similarity	NPC233320
0.8396	Intermediate Similarity	NPC227894
0.8393	Intermediate Similarity	NPC283616
0.8381	Intermediate Similarity	NPC154899
0.8381	Intermediate Similarity	NPC238115
0.8381	Intermediate Similarity	NPC233396
0.8381	Intermediate Similarity	NPC473393
0.8365	Intermediate Similarity	NPC179686
0.8365	Intermediate Similarity	NPC298224
0.835	Intermediate Similarity	NPC13755
0.8348	Intermediate Similarity	NPC71090
0.8333	Intermediate Similarity	NPC175298
0.8333	Intermediate Similarity	NPC470161
0.8319	Intermediate Similarity	NPC163036
0.8318	Intermediate Similarity	NPC241549
0.8317	Intermediate Similarity	NPC313650
0.8304	Intermediate Similarity	NPC164386
0.8304	Intermediate Similarity	NPC142042
0.8302	Intermediate Similarity	NPC326447
0.8302	Intermediate Similarity	NPC326801
0.8288	Intermediate Similarity	NPC51345
0.8286	Intermediate Similarity	NPC38209
0.8286	Intermediate Similarity	NPC292792
0.8286	Intermediate Similarity	NPC2518
0.8283	Intermediate Similarity	NPC318429
0.8273	Intermediate Similarity	NPC141003
0.8273	Intermediate Similarity	NPC26524
0.8273	Intermediate Similarity	NPC35344
0.8265	Intermediate Similarity	NPC104216
0.8265	Intermediate Similarity	NPC113460
0.8265	Intermediate Similarity	NPC25493
0.8261	Intermediate Similarity	NPC290451
0.8261	Intermediate Similarity	NPC127389
0.8257	Intermediate Similarity	NPC257124
0.8257	Intermediate Similarity	NPC78918
0.8257	Intermediate Similarity	NPC173746
0.8257	Intermediate Similarity	NPC8547
0.8257	Intermediate Similarity	NPC156840
0.8257	Intermediate Similarity	NPC139617
0.8252	Intermediate Similarity	NPC128723
0.8252	Intermediate Similarity	NPC171843
0.8246	Intermediate Similarity	NPC469708
0.8246	Intermediate Similarity	NPC60589
0.8241	Intermediate Similarity	NPC259554
0.823	Intermediate Similarity	NPC474214
0.823	Intermediate Similarity	NPC474040
0.823	Intermediate Similarity	NPC101503
0.823	Intermediate Similarity	NPC74821
0.8214	Intermediate Similarity	NPC290470
0.8214	Intermediate Similarity	NPC154256
0.8214	Intermediate Similarity	NPC221049
0.8205	Intermediate Similarity	NPC114901
0.8205	Intermediate Similarity	NPC94276
0.8205	Intermediate Similarity	NPC109822
0.8205	Intermediate Similarity	NPC293701
0.8205	Intermediate Similarity	NPC48990
0.819	Intermediate Similarity	NPC150026
0.819	Intermediate Similarity	NPC100099
0.819	Intermediate Similarity	NPC36016
0.8182	Intermediate Similarity	NPC177420
0.8182	Intermediate Similarity	NPC199462
0.8182	Intermediate Similarity	NPC123273
0.8182	Intermediate Similarity	NPC318325
0.8182	Intermediate Similarity	NPC474920
0.8182	Intermediate Similarity	NPC280347
0.8182	Intermediate Similarity	NPC242240
0.8174	Intermediate Similarity	NPC269242
0.8174	Intermediate Similarity	NPC469412
0.8174	Intermediate Similarity	NPC198734
0.8165	Intermediate Similarity	NPC106141
0.8163	Intermediate Similarity	NPC23167
0.8158	Intermediate Similarity	NPC295259
0.8158	Intermediate Similarity	NPC135961
0.8158	Intermediate Similarity	NPC32152
0.8158	Intermediate Similarity	NPC311595
0.8158	Intermediate Similarity	NPC24474
0.8158	Intermediate Similarity	NPC474320
0.8148	Intermediate Similarity	NPC146530
0.8142	Intermediate Similarity	NPC86947
0.8136	Intermediate Similarity	NPC81641
0.8136	Intermediate Similarity	NPC194519
0.8131	Intermediate Similarity	NPC1065
0.8131	Intermediate Similarity	NPC473653
0.8125	Intermediate Similarity	NPC301321
0.8125	Intermediate Similarity	NPC185541
0.8125	Intermediate Similarity	NPC464
0.8125	Intermediate Similarity	NPC296526
0.812	Intermediate Similarity	NPC76465
0.812	Intermediate Similarity	NPC38761
0.8113	Intermediate Similarity	NPC109637
0.8113	Intermediate Similarity	NPC241224
0.8108	Intermediate Similarity	NPC90903
0.8108	Intermediate Similarity	NPC109241
0.8108	Intermediate Similarity	NPC303522
0.8103	Intermediate Similarity	NPC54972
0.8103	Intermediate Similarity	NPC470804
0.81	Intermediate Similarity	NPC55561
0.81	Intermediate Similarity	NPC300478
0.8095	Intermediate Similarity	NPC310905
0.8095	Intermediate Similarity	NPC12714
0.8095	Intermediate Similarity	NPC84325
0.8091	Intermediate Similarity	NPC275627
0.8091	Intermediate Similarity	NPC166837
0.8087	Intermediate Similarity	NPC232295
0.8087	Intermediate Similarity	NPC193193
0.8087	Intermediate Similarity	NPC8283
0.8087	Intermediate Similarity	NPC258979
0.8087	Intermediate Similarity	NPC474131
0.8087	Intermediate Similarity	NPC263835
0.8087	Intermediate Similarity	NPC93398
0.8077	Intermediate Similarity	NPC216468
0.8077	Intermediate Similarity	NPC78119
0.8077	Intermediate Similarity	NPC51333
0.8077	Intermediate Similarity	NPC132078
0.8073	Intermediate Similarity	NPC36108
0.8073	Intermediate Similarity	NPC246358
0.8073	Intermediate Similarity	NPC7097
0.8073	Intermediate Similarity	NPC233731
0.8073	Intermediate Similarity	NPC306045
0.8073	Intermediate Similarity	NPC265211
0.807	Intermediate Similarity	NPC255675
0.807	Intermediate Similarity	NPC63083
0.807	Intermediate Similarity	NPC329980
0.807	Intermediate Similarity	NPC293424
0.8067	Intermediate Similarity	NPC178284
0.8067	Intermediate Similarity	NPC474476
0.8067	Intermediate Similarity	NPC276212
0.8067	Intermediate Similarity	NPC191037
0.8067	Intermediate Similarity	NPC58607
0.8061	Intermediate Similarity	NPC197783
0.8053	Intermediate Similarity	NPC19290
0.8053	Intermediate Similarity	NPC54507
0.8053	Intermediate Similarity	NPC85292
0.8053	Intermediate Similarity	NPC141090
0.8053	Intermediate Similarity	NPC229147
0.8051	Intermediate Similarity	NPC246648
0.8051	Intermediate Similarity	NPC197351
0.8051	Intermediate Similarity	NPC86502
0.8051	Intermediate Similarity	NPC134195
0.8051	Intermediate Similarity	NPC106914
0.8037	Intermediate Similarity	NPC227255
0.8036	Intermediate Similarity	NPC470837
0.8034	Intermediate Similarity	NPC476142
0.8034	Intermediate Similarity	NPC188997
0.8019	Intermediate Similarity	NPC304638
0.8019	Intermediate Similarity	NPC24327
0.8019	Intermediate Similarity	NPC12870

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 NPC108875 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	1006
0.2-0.3	1534
0.3-0.4	2544
0.4-0.5	1876
0.5-0.6	1102
0.6-0.7	643
0.7-0.8	200
0.8-0.85	18
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9406	High Similarity	NPD2684	Approved
0.9048	High Similarity	NPD7843	Approved
0.9048	High Similarity	NPD821	Approved
0.8932	High Similarity	NPD290	Approved
0.8796	High Similarity	NPD7157	Approved
0.8654	High Similarity	NPD968	Approved
0.8302	Intermediate Similarity	NPD3134	Approved
0.8283	Intermediate Similarity	NPD9365	Approved
0.8276	Intermediate Similarity	NPD3685	Discontinued
0.8273	Intermediate Similarity	NPD1241	Discontinued
0.8257	Intermediate Similarity	NPD228	Approved
0.8246	Intermediate Similarity	NPD5846	Approved
0.8246	Intermediate Similarity	NPD6516	Phase 2
0.823	Intermediate Similarity	NPD1548	Phase 1
0.8224	Intermediate Similarity	NPD1358	Approved
0.8182	Intermediate Similarity	NPD5535	Approved
0.8125	Intermediate Similarity	NPD6671	Approved
0.812	Intermediate Similarity	NPD6583	Phase 3
0.812	Intermediate Similarity	NPD6582	Phase 2
0.8073	Intermediate Similarity	NPD5451	Approved
0.807	Intermediate Similarity	NPD1894	Discontinued
0.8067	Intermediate Similarity	NPD3690	Phase 2
0.8067	Intermediate Similarity	NPD3691	Phase 2
0.8053	Intermediate Similarity	NPD3596	Phase 2
0.8039	Intermediate Similarity	NPD2933	Approved
0.8039	Intermediate Similarity	NPD2934	Approved
0.7983	Intermediate Similarity	NPD1817	Approved
0.7983	Intermediate Similarity	NPD1820	Approved
0.7983	Intermediate Similarity	NPD1819	Approved
0.7983	Intermediate Similarity	NPD1818	Approved
0.7961	Intermediate Similarity	NPD2860	Approved
0.7961	Intermediate Similarity	NPD2859	Approved
0.7949	Intermediate Similarity	NPD1610	Phase 2
0.7931	Intermediate Similarity	NPD1778	Approved
0.7925	Intermediate Similarity	NPD291	Approved
0.7917	Intermediate Similarity	NPD6584	Phase 3
0.7913	Intermediate Similarity	NPD6580	Approved
0.7913	Intermediate Similarity	NPD6581	Approved
0.7881	Intermediate Similarity	NPD2235	Phase 2
0.7881	Intermediate Similarity	NPD2231	Phase 2
0.7864	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD3496	Discontinued
0.7857	Intermediate Similarity	NPD111	Approved
0.7845	Intermediate Similarity	NPD1357	Approved
0.7845	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD2557	Approved
0.7797	Intermediate Similarity	NPD1091	Approved
0.7797	Intermediate Similarity	NPD422	Phase 1
0.7788	Intermediate Similarity	NPD5283	Phase 1
0.7787	Intermediate Similarity	NPD4908	Phase 1
0.7778	Intermediate Similarity	NPD2668	Approved
0.7778	Intermediate Similarity	NPD2667	Approved
0.7759	Intermediate Similarity	NPD1182	Approved
0.775	Intermediate Similarity	NPD8651	Approved
0.7742	Intermediate Similarity	NPD1423	Approved
0.7736	Intermediate Similarity	NPD3020	Approved
0.7724	Intermediate Similarity	NPD5163	Phase 2
0.7724	Intermediate Similarity	NPD3167	Approved
0.7724	Intermediate Similarity	NPD3165	Approved
0.7724	Intermediate Similarity	NPD3166	Approved
0.7724	Intermediate Similarity	NPD3164	Approved
0.7723	Intermediate Similarity	NPD9295	Approved
0.7712	Intermediate Similarity	NPD3847	Discontinued
0.7706	Intermediate Similarity	NPD9697	Approved
0.7705	Intermediate Similarity	NPD2861	Phase 2
0.7692	Intermediate Similarity	NPD5691	Approved
0.7686	Intermediate Similarity	NPD1794	Approved
0.768	Intermediate Similarity	NPD4140	Approved
0.7667	Intermediate Similarity	NPD5327	Phase 3
0.7661	Intermediate Similarity	NPD6798	Discontinued
0.7661	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1535	Discovery
0.7632	Intermediate Similarity	NPD592	Approved
0.7632	Intermediate Similarity	NPD594	Approved
0.7627	Intermediate Similarity	NPD4626	Approved
0.7623	Intermediate Similarity	NPD558	Phase 2
0.7619	Intermediate Similarity	NPD5735	Approved
0.76	Intermediate Similarity	NPD6233	Phase 2
0.76	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4062	Phase 3
0.7593	Intermediate Similarity	NPD940	Approved
0.7593	Intermediate Similarity	NPD846	Approved
0.7583	Intermediate Similarity	NPD1481	Phase 2
0.7583	Intermediate Similarity	NPD1840	Phase 2
0.7581	Intermediate Similarity	NPD3180	Approved
0.7581	Intermediate Similarity	NPD3179	Approved
0.7581	Intermediate Similarity	NPD6179	Discontinued
0.7561	Intermediate Similarity	NPD1712	Approved
0.7561	Intermediate Similarity	NPD454	Approved
0.7559	Intermediate Similarity	NPD3054	Approved
0.7559	Intermediate Similarity	NPD3052	Approved
0.7544	Intermediate Similarity	NPD1138	Approved
0.7542	Intermediate Similarity	NPD5585	Approved
0.7542	Intermediate Similarity	NPD3443	Approved
0.7542	Intermediate Similarity	NPD3444	Approved
0.7542	Intermediate Similarity	NPD3049	Approved
0.7542	Intermediate Similarity	NPD3445	Approved
0.7541	Intermediate Similarity	NPD6362	Approved
0.7541	Intermediate Similarity	NPD987	Approved
0.754	Intermediate Similarity	NPD4060	Phase 1
0.754	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD6542	Approved
0.7521	Intermediate Similarity	NPD2429	Approved
0.7521	Intermediate Similarity	NPD6540	Phase 3
0.7521	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD6543	Approved
0.7521	Intermediate Similarity	NPD2428	Approved
0.7521	Intermediate Similarity	NPD6539	Approved
0.7521	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4536	Approved
0.75	Intermediate Similarity	NPD4538	Approved
0.75	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD6355	Discontinued
0.7479	Intermediate Similarity	NPD2556	Approved
0.7479	Intermediate Similarity	NPD2554	Approved
0.746	Intermediate Similarity	NPD5745	Approved
0.746	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6538	Approved
0.7459	Intermediate Similarity	NPD6541	Approved
0.7456	Intermediate Similarity	NPD1139	Approved
0.7456	Intermediate Similarity	NPD1137	Approved
0.7455	Intermediate Similarity	NPD9501	Approved
0.7453	Intermediate Similarity	NPD1809	Phase 2
0.7453	Intermediate Similarity	NPD844	Approved
0.744	Intermediate Similarity	NPD7095	Approved
0.744	Intermediate Similarity	NPD3027	Phase 3
0.7438	Intermediate Similarity	NPD1608	Approved
0.7429	Intermediate Similarity	NPD845	Approved
0.7422	Intermediate Similarity	NPD6353	Approved
0.7422	Intermediate Similarity	NPD2157	Approved
0.7419	Intermediate Similarity	NPD4993	Discontinued
0.7411	Intermediate Similarity	NPD9552	Approved
0.7402	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD1613	Approved
0.7398	Intermediate Similarity	NPD2797	Approved
0.7398	Intermediate Similarity	NPD1770	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD6382	Discontinued
0.7395	Intermediate Similarity	NPD1651	Approved
0.7381	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD1669	Approved
0.7377	Intermediate Similarity	NPD4749	Approved
0.7364	Intermediate Similarity	NPD7097	Phase 1
0.736	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD2614	Approved
0.7358	Intermediate Similarity	NPD9296	Approved
0.7355	Intermediate Similarity	NPD3705	Approved
0.735	Intermediate Similarity	NPD709	Approved
0.7339	Intermediate Similarity	NPD3028	Approved
0.7339	Intermediate Similarity	NPD4624	Approved
0.7339	Intermediate Similarity	NPD5647	Approved
0.7339	Intermediate Similarity	NPD7018	Phase 2
0.7323	Intermediate Similarity	NPD7265	Discontinued
0.7323	Intermediate Similarity	NPD3163	Approved
0.7323	Intermediate Similarity	NPD3162	Approved
0.7323	Intermediate Similarity	NPD7477	Discontinued
0.7317	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1283	Approved
0.7311	Intermediate Similarity	NPD2486	Discontinued
0.7311	Intermediate Similarity	NPD9545	Approved
0.7308	Intermediate Similarity	NPD5960	Phase 3
0.7308	Intermediate Similarity	NPD5588	Approved
0.7302	Intermediate Similarity	NPD5746	Approved
0.7295	Intermediate Similarity	NPD2230	Approved
0.7295	Intermediate Similarity	NPD2232	Approved
0.7295	Intermediate Similarity	NPD2233	Approved
0.7295	Intermediate Similarity	NPD9717	Approved
0.7287	Intermediate Similarity	NPD6653	Approved
0.7281	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD556	Approved
0.7273	Intermediate Similarity	NPD2424	Discontinued
0.7266	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD595	Approved
0.7265	Intermediate Similarity	NPD593	Approved
0.7258	Intermediate Similarity	NPD4098	Discontinued
0.7257	Intermediate Similarity	NPD5373	Approved
0.7257	Intermediate Similarity	NPD5374	Approved
0.7252	Intermediate Similarity	NPD2240	Approved
0.7252	Intermediate Similarity	NPD2161	Phase 2
0.7252	Intermediate Similarity	NPD4476	Approved
0.7252	Intermediate Similarity	NPD2239	Approved
0.7252	Intermediate Similarity	NPD4477	Approved
0.725	Intermediate Similarity	NPD2595	Approved
0.725	Intermediate Similarity	NPD2594	Approved
0.7244	Intermediate Similarity	NPD1048	Approved
0.7244	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD4129	Approved
0.7236	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD4359	Approved
0.7227	Intermediate Similarity	NPD5536	Phase 2
0.7222	Intermediate Similarity	NPD600	Approved
0.7222	Intermediate Similarity	NPD682	Discontinued
0.7222	Intermediate Similarity	NPD596	Approved
0.7222	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD288	Approved
0.7218	Intermediate Similarity	NPD1652	Phase 2
0.7218	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD9294	Approved
0.7213	Intermediate Similarity	NPD1547	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