NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	206.13
Volume:	231.882
LogP:	3.394
LogD:	3.364
LogS:	-3.483
# Rotatable Bonds:	6
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.692
Synthetic Accessibility Score:	2.125
Fsp3:	0.462
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:	-4.333
MDCK Permeability:	3.068850128329359e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.444
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.962
Plasma Protein Binding (PPB):	72.5550765991211%
Volume Distribution (VD):	1.588
Pgp-substrate:	23.12639617919922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.498
CYP2C19-inhibitor:	0.957
CYP2C19-substrate:	0.298
CYP2C9-inhibitor:	0.694
CYP2C9-substrate:	0.319
CYP2D6-inhibitor:	0.135
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.233
CYP3A4-substrate:	0.493

ADMET: Excretion

Clearance (CL):	11.592
Half-life (T1/2):	0.555

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.061
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.831
Carcinogencity:	0.235
Eye Corrosion:	0.204
Eye Irritation:	0.974
Respiratory Toxicity:	0.276

Download Data

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

Natural Product: NPC270507

Natural Product ID:	NPC270507
*Common Name:**	2-Phenylethyl 2-Methylbutanoate
IUPAC Name:	2-phenylethyl 2-methylbutanoate
Synonyms:
Standard InCHIKey:	KVKKTLBBYFABAZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H18O2/c1-3-11(2)13(14)15-10-9-12-7-5-4-6-8-12/h4-8,11H,3,9-10H2,1-2H3
SMILES:	CCC(C)C(=O)OCCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3183389
PubChem CID:	520148
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

*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
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jep.2005.01.054]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17996677]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31181920]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31418264]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28276	Artemisia argyi	Species	Asteraceae	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
Potency	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Potency	n.a.	38570.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43646.5	nM	PubChem BioAssay data set

☑ 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 NPC270507 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	181
0.1-0.2	1002
0.2-0.3	3403
0.3-0.4	12856
0.4-0.5	16706
0.5-0.6	7012
0.6-0.7	1261
0.7-0.8	241
0.8-0.85	21
0.85-0.9	7
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.987	High Similarity	NPC103387
0.987	High Similarity	NPC323103
0.961	High Similarity	NPC121800
0.9481	High Similarity	NPC170484
0.9259	High Similarity	NPC294134
0.9048	High Similarity	NPC220893
0.9012	High Similarity	NPC288903
0.8824	High Similarity	NPC9822
0.881	High Similarity	NPC89377
0.8571	High Similarity	NPC475710
0.8571	High Similarity	NPC58616
0.8488	Intermediate Similarity	NPC304760
0.8391	Intermediate Similarity	NPC173443
0.8372	Intermediate Similarity	NPC322387
0.8333	Intermediate Similarity	NPC285773
0.8295	Intermediate Similarity	NPC185501
0.8295	Intermediate Similarity	NPC213156
0.8295	Intermediate Similarity	NPC240108
0.8295	Intermediate Similarity	NPC84288
0.8295	Intermediate Similarity	NPC70940
0.8295	Intermediate Similarity	NPC274455
0.8295	Intermediate Similarity	NPC86670
0.8193	Intermediate Similarity	NPC127343
0.8172	Intermediate Similarity	NPC146351
0.8148	Intermediate Similarity	NPC175393
0.8118	Intermediate Similarity	NPC44830
0.8095	Intermediate Similarity	NPC303245
0.8068	Intermediate Similarity	NPC329064
0.8065	Intermediate Similarity	NPC35448
0.8065	Intermediate Similarity	NPC225060
0.8065	Intermediate Similarity	NPC78701
0.8022	Intermediate Similarity	NPC23453
0.8	Intermediate Similarity	NPC317645
0.7957	Intermediate Similarity	NPC276775
0.7957	Intermediate Similarity	NPC270654
0.7957	Intermediate Similarity	NPC249912
0.7957	Intermediate Similarity	NPC92754
0.7955	Intermediate Similarity	NPC96625
0.7952	Intermediate Similarity	NPC224544
0.7901	Intermediate Similarity	NPC108218
0.7895	Intermediate Similarity	NPC473325
0.7875	Intermediate Similarity	NPC155429
0.7857	Intermediate Similarity	NPC78517
0.7857	Intermediate Similarity	NPC167577
0.7802	Intermediate Similarity	NPC119631
0.7789	Intermediate Similarity	NPC7435
0.7778	Intermediate Similarity	NPC231591
0.7766	Intermediate Similarity	NPC325499
0.7766	Intermediate Similarity	NPC226041
0.7742	Intermediate Similarity	NPC130398
0.7738	Intermediate Similarity	NPC176228
0.7732	Intermediate Similarity	NPC474365
0.7732	Intermediate Similarity	NPC160382
0.7732	Intermediate Similarity	NPC301943
0.7727	Intermediate Similarity	NPC95965
0.7708	Intermediate Similarity	NPC42211
0.7708	Intermediate Similarity	NPC70624
0.7674	Intermediate Similarity	NPC89950
0.7654	Intermediate Similarity	NPC208302
0.7653	Intermediate Similarity	NPC19136
0.7624	Intermediate Similarity	NPC214067
0.7624	Intermediate Similarity	NPC196246
0.7619	Intermediate Similarity	NPC298023
0.7619	Intermediate Similarity	NPC287790
0.7619	Intermediate Similarity	NPC3672
0.7604	Intermediate Similarity	NPC221825
0.7604	Intermediate Similarity	NPC325497
0.7604	Intermediate Similarity	NPC118343
0.76	Intermediate Similarity	NPC56493
0.759	Intermediate Similarity	NPC189371
0.7586	Intermediate Similarity	NPC106313
0.7561	Intermediate Similarity	NPC271437
0.7558	Intermediate Similarity	NPC309279
0.7558	Intermediate Similarity	NPC157055
0.7556	Intermediate Similarity	NPC169050
0.7556	Intermediate Similarity	NPC286608
0.7549	Intermediate Similarity	NPC1082
0.7549	Intermediate Similarity	NPC305912
0.7529	Intermediate Similarity	NPC76455
0.7529	Intermediate Similarity	NPC137847
0.7528	Intermediate Similarity	NPC53299
0.7527	Intermediate Similarity	NPC77273
0.7526	Intermediate Similarity	NPC469481
0.7525	Intermediate Similarity	NPC469636
0.7525	Intermediate Similarity	NPC10251
0.7525	Intermediate Similarity	NPC17417
0.7525	Intermediate Similarity	NPC31274
0.7525	Intermediate Similarity	NPC469511
0.75	Intermediate Similarity	NPC119271
0.75	Intermediate Similarity	NPC243289
0.75	Intermediate Similarity	NPC142326
0.75	Intermediate Similarity	NPC208183
0.75	Intermediate Similarity	NPC94751
0.75	Intermediate Similarity	NPC175852
0.75	Intermediate Similarity	NPC477251
0.75	Intermediate Similarity	NPC271475
0.75	Intermediate Similarity	NPC160548
0.75	Intermediate Similarity	NPC474111
0.75	Intermediate Similarity	NPC308619
0.75	Intermediate Similarity	NPC329705
0.75	Intermediate Similarity	NPC210529
0.75	Intermediate Similarity	NPC324835
0.75	Intermediate Similarity	NPC127491
0.7476	Intermediate Similarity	NPC82899
0.7476	Intermediate Similarity	NPC270699
0.7474	Intermediate Similarity	NPC261947
0.7471	Intermediate Similarity	NPC165212
0.747	Intermediate Similarity	NPC208075
0.7451	Intermediate Similarity	NPC93084
0.7451	Intermediate Similarity	NPC158854
0.7451	Intermediate Similarity	NPC174099
0.7451	Intermediate Similarity	NPC251854
0.7449	Intermediate Similarity	NPC188895
0.7449	Intermediate Similarity	NPC474112
0.7444	Intermediate Similarity	NPC318107
0.7439	Intermediate Similarity	NPC74458
0.7439	Intermediate Similarity	NPC326200
0.7426	Intermediate Similarity	NPC21929
0.7423	Intermediate Similarity	NPC476042
0.7423	Intermediate Similarity	NPC472318
0.7423	Intermediate Similarity	NPC98911
0.7423	Intermediate Similarity	NPC203925
0.7419	Intermediate Similarity	NPC86987
0.7419	Intermediate Similarity	NPC476484
0.7419	Intermediate Similarity	NPC110704
0.7416	Intermediate Similarity	NPC304538
0.7416	Intermediate Similarity	NPC267704
0.7412	Intermediate Similarity	NPC329318
0.7404	Intermediate Similarity	NPC128368
0.74	Intermediate Similarity	NPC269457
0.74	Intermediate Similarity	NPC473855
0.7396	Intermediate Similarity	NPC477767
0.7386	Intermediate Similarity	NPC99240
0.7386	Intermediate Similarity	NPC103326
0.7386	Intermediate Similarity	NPC329319
0.7386	Intermediate Similarity	NPC87299
0.7386	Intermediate Similarity	NPC99394
0.7386	Intermediate Similarity	NPC230068
0.7379	Intermediate Similarity	NPC474157
0.7374	Intermediate Similarity	NPC234305
0.7374	Intermediate Similarity	NPC89886
0.7368	Intermediate Similarity	NPC172925
0.7356	Intermediate Similarity	NPC328178
0.7353	Intermediate Similarity	NPC83628
0.7353	Intermediate Similarity	NPC265407
0.7349	Intermediate Similarity	NPC285679
0.7333	Intermediate Similarity	NPC190212
0.7333	Intermediate Similarity	NPC153053
0.7327	Intermediate Similarity	NPC136962
0.7327	Intermediate Similarity	NPC474376
0.7327	Intermediate Similarity	NPC475203
0.7327	Intermediate Similarity	NPC472315
0.7327	Intermediate Similarity	NPC472316
0.7326	Intermediate Similarity	NPC103488
0.732	Intermediate Similarity	NPC145052
0.732	Intermediate Similarity	NPC229242
0.732	Intermediate Similarity	NPC179411
0.7317	Intermediate Similarity	NPC95289
0.7312	Intermediate Similarity	NPC258627
0.7308	Intermediate Similarity	NPC321852
0.7303	Intermediate Similarity	NPC477770
0.7303	Intermediate Similarity	NPC172984
0.73	Intermediate Similarity	NPC85977
0.73	Intermediate Similarity	NPC31786
0.7273	Intermediate Similarity	NPC304873
0.7273	Intermediate Similarity	NPC117180
0.7264	Intermediate Similarity	NPC210092
0.7263	Intermediate Similarity	NPC261181
0.7253	Intermediate Similarity	NPC93843
0.7245	Intermediate Similarity	NPC171843
0.7245	Intermediate Similarity	NPC217621
0.7238	Intermediate Similarity	NPC26615
0.7234	Intermediate Similarity	NPC187725
0.7234	Intermediate Similarity	NPC141607
0.7228	Intermediate Similarity	NPC472919
0.7228	Intermediate Similarity	NPC321670
0.7228	Intermediate Similarity	NPC238115
0.7228	Intermediate Similarity	NPC209632
0.7222	Intermediate Similarity	NPC44546
0.7222	Intermediate Similarity	NPC95429
0.7216	Intermediate Similarity	NPC289201
0.7216	Intermediate Similarity	NPC253423
0.7216	Intermediate Similarity	NPC103048
0.7212	Intermediate Similarity	NPC476003
0.7212	Intermediate Similarity	NPC260818
0.7212	Intermediate Similarity	NPC210089
0.7209	Intermediate Similarity	NPC66655
0.7204	Intermediate Similarity	NPC1793
0.72	Intermediate Similarity	NPC329556
0.72	Intermediate Similarity	NPC91820
0.72	Intermediate Similarity	NPC60679
0.72	Intermediate Similarity	NPC82426
0.7195	Intermediate Similarity	NPC98880
0.7195	Intermediate Similarity	NPC16190
0.7195	Intermediate Similarity	NPC235059
0.7195	Intermediate Similarity	NPC169222
0.7191	Intermediate Similarity	NPC73637
0.7191	Intermediate Similarity	NPC121478
0.7188	Intermediate Similarity	NPC5472
0.7184	Intermediate Similarity	NPC40178

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 NPC270507 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	828
0.2-0.3	1398
0.3-0.4	3311
0.4-0.5	2099
0.5-0.6	1041
0.6-0.7	247
0.7-0.8	50
0.8-0.85	10
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8721	High Similarity	NPD3672	Approved
0.8721	High Similarity	NPD3673	Approved
0.8588	High Similarity	NPD1087	Approved
0.8519	High Similarity	NPD9490	Approved
0.8444	Intermediate Similarity	NPD1989	Approved
0.8395	Intermediate Similarity	NPD227	Approved
0.8395	Intermediate Similarity	NPD225	Approved
0.8391	Intermediate Similarity	NPD800	Approved
0.8333	Intermediate Similarity	NPD9491	Approved
0.8295	Intermediate Similarity	NPD1086	Approved
0.8295	Intermediate Similarity	NPD1090	Approved
0.8295	Intermediate Similarity	NPD1089	Approved
0.8111	Intermediate Similarity	NPD1088	Approved
0.8095	Intermediate Similarity	NPD226	Approved
0.7978	Intermediate Similarity	NPD5347	Phase 2
0.7978	Intermediate Similarity	NPD5346	Phase 2
0.7935	Intermediate Similarity	NPD1693	Approved
0.7826	Intermediate Similarity	NPD1563	Approved
0.7826	Intermediate Similarity	NPD1066	Discontinued
0.7753	Intermediate Similarity	NPD4793	Discontinued
0.7732	Intermediate Similarity	NPD6647	Phase 2
0.7684	Intermediate Similarity	NPD5926	Approved
0.7634	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD1239	Approved
0.7604	Intermediate Similarity	NPD2066	Phase 3
0.7604	Intermediate Similarity	NPD7798	Approved
0.7604	Intermediate Similarity	NPD1238	Approved
0.7579	Intermediate Similarity	NPD1565	Approved
0.7579	Intermediate Similarity	NPD1564	Approved
0.7579	Intermediate Similarity	NPD1566	Phase 3
0.7556	Intermediate Similarity	NPD1282	Approved
0.7525	Intermediate Similarity	NPD2182	Approved
0.75	Intermediate Similarity	NPD9495	Approved
0.75	Intermediate Similarity	NPD6685	Approved
0.7473	Intermediate Similarity	NPD531	Approved
0.7451	Intermediate Similarity	NPD4234	Approved
0.7451	Intermediate Similarity	NPD4233	Approved
0.7451	Intermediate Similarity	NPD1752	Approved
0.7451	Intermediate Similarity	NPD1756	Approved
0.7451	Intermediate Similarity	NPD2067	Discontinued
0.7444	Intermediate Similarity	NPD9257	Approved
0.7444	Intermediate Similarity	NPD9259	Approved
0.7379	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2650	Approved
0.7333	Intermediate Similarity	NPD2652	Approved
0.7327	Intermediate Similarity	NPD5705	Approved
0.7327	Intermediate Similarity	NPD5704	Approved
0.7327	Intermediate Similarity	NPD5706	Approved
0.73	Intermediate Similarity	NPD164	Approved
0.73	Intermediate Similarity	NPD5909	Discontinued
0.7282	Intermediate Similarity	NPD3646	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD2629	Approved
0.7264	Intermediate Similarity	NPD4766	Approved
0.7263	Intermediate Similarity	NPD1202	Approved
0.7238	Intermediate Similarity	NPD2607	Approved
0.7209	Intermediate Similarity	NPD9294	Approved
0.72	Intermediate Similarity	NPD1929	Approved
0.72	Intermediate Similarity	NPD5765	Approved
0.72	Intermediate Similarity	NPD1930	Approved
0.72	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD9716	Approved
0.7157	Intermediate Similarity	NPD3134	Approved
0.713	Intermediate Similarity	NPD4574	Approved
0.713	Intermediate Similarity	NPD4576	Approved
0.7128	Intermediate Similarity	NPD9256	Approved
0.7128	Intermediate Similarity	NPD9258	Approved
0.7115	Intermediate Similarity	NPD5237	Approved
0.7115	Intermediate Similarity	NPD5236	Approved
0.7115	Intermediate Similarity	NPD5239	Approved
0.7115	Intermediate Similarity	NPD5235	Approved
0.7115	Intermediate Similarity	NPD5240	Approved
0.7113	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3971	Phase 1
0.7097	Intermediate Similarity	NPD1101	Approved
0.7075	Intermediate Similarity	NPD6858	Approved
0.7075	Intermediate Similarity	NPD7094	Approved
0.7059	Intermediate Similarity	NPD5048	Discontinued
0.7048	Intermediate Similarity	NPD2201	Approved
0.7021	Intermediate Similarity	NPD689	Discontinued
0.7009	Intermediate Similarity	NPD1373	Approved
0.7009	Intermediate Similarity	NPD1370	Approved
0.7009	Intermediate Similarity	NPD1371	Approved
0.7009	Intermediate Similarity	NPD1374	Approved
0.6981	Remote Similarity	NPD6912	Phase 3
0.697	Remote Similarity	NPD253	Approved
0.6957	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1358	Approved
0.6916	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.69	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.69	Remote Similarity	NPD1067	Discontinued
0.6889	Remote Similarity	NPD9250	Approved
0.6881	Remote Similarity	NPD4198	Discontinued
0.6875	Remote Similarity	NPD5306	Approved
0.6875	Remote Similarity	NPD5305	Approved
0.6869	Remote Similarity	NPD9566	Approved
0.6857	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4479	Discontinued
0.6837	Remote Similarity	NPD9260	Approved
0.6786	Remote Similarity	NPD5585	Approved
0.6757	Remote Similarity	NPD2347	Approved
0.6757	Remote Similarity	NPD6065	Approved
0.6754	Remote Similarity	NPD3131	Approved
0.6754	Remote Similarity	NPD4807	Approved
0.6754	Remote Similarity	NPD4215	Approved
0.6754	Remote Similarity	NPD4218	Approved
0.6754	Remote Similarity	NPD3132	Approved
0.6754	Remote Similarity	NPD2608	Approved
0.6754	Remote Similarity	NPD4217	Approved
0.6754	Remote Similarity	NPD2611	Approved
0.6754	Remote Similarity	NPD4806	Approved
0.6754	Remote Similarity	NPD4216	Approved
0.6754	Remote Similarity	NPD2610	Approved
0.6754	Remote Similarity	NPD2612	Approved
0.6754	Remote Similarity	NPD2609	Approved
0.6735	Remote Similarity	NPD1409	Phase 3
0.6731	Remote Similarity	NPD1040	Phase 2
0.6701	Remote Similarity	NPD530	Approved
0.6697	Remote Similarity	NPD6010	Discontinued
0.6667	Remote Similarity	NPD2558	Approved
0.6667	Remote Similarity	NPD2549	Approved
0.6667	Remote Similarity	NPD4106	Approved
0.6667	Remote Similarity	NPD467	Phase 1
0.6667	Remote Similarity	NPD2555	Approved
0.6667	Remote Similarity	NPD2553	Approved
0.6667	Remote Similarity	NPD4136	Approved
0.6667	Remote Similarity	NPD2552	Approved
0.6667	Remote Similarity	NPD4814	Discontinued
0.6667	Remote Similarity	NPD4135	Approved
0.6667	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2550	Approved
0.6637	Remote Similarity	NPD5981	Approved
0.6637	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1317	Discontinued
0.6636	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD1237	Approved
0.6632	Remote Similarity	NPD9538	Approved
0.6609	Remote Similarity	NPD5618	Discontinued
0.6609	Remote Similarity	NPD7437	Approved
0.6609	Remote Similarity	NPD7436	Approved
0.6606	Remote Similarity	NPD5535	Approved
0.6602	Remote Similarity	NPD4189	Approved
0.6602	Remote Similarity	NPD4188	Approved
0.6602	Remote Similarity	NPD1932	Approved
0.6593	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD1778	Approved
0.6574	Remote Similarity	NPD3643	Approved
0.6574	Remote Similarity	NPD3642	Approved
0.6574	Remote Similarity	NPD3644	Approved
0.6569	Remote Similarity	NPD9712	Approved
0.6566	Remote Similarity	NPD719	Approved
0.6566	Remote Similarity	NPD845	Approved
0.6566	Remote Similarity	NPD720	Approved
0.6566	Remote Similarity	NPD3719	Approved
0.6566	Remote Similarity	NPD3718	Approved
0.6549	Remote Similarity	NPD1894	Discontinued
0.6549	Remote Similarity	NPD2617	Discontinued
0.6549	Remote Similarity	NPD9545	Approved
0.6545	Remote Similarity	NPD1241	Discontinued
0.6545	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD2329	Discontinued
0.6522	Remote Similarity	NPD942	Approved
0.6518	Remote Similarity	NPD5291	Approved
0.6518	Remote Similarity	NPD5292	Approved
0.6518	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD969	Suspended
0.65	Remote Similarity	NPD6049	Phase 2
0.65	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7343	Discovery
0.65	Remote Similarity	NPD7344	Phase 1
0.65	Remote Similarity	NPD2934	Approved
0.65	Remote Similarity	NPD2933	Approved
0.6496	Remote Similarity	NPD4359	Approved
0.6491	Remote Similarity	NPD5691	Approved
0.6491	Remote Similarity	NPD4102	Approved
0.6491	Remote Similarity	NPD4105	Approved
0.6486	Remote Similarity	NPD5951	Approved
0.6486	Remote Similarity	NPD1246	Approved
0.6481	Remote Similarity	NPD5278	Discontinued
0.6476	Remote Similarity	NPD3048	Approved
0.6476	Remote Similarity	NPD3047	Approved
0.6476	Remote Similarity	NPD3046	Approved
0.6471	Remote Similarity	NPD9711	Approved
0.6471	Remote Similarity	NPD9710	Approved
0.6466	Remote Similarity	NPD6287	Discontinued
0.6466	Remote Similarity	NPD3603	Phase 3
0.6466	Remote Similarity	NPD4480	Approved
0.6465	Remote Similarity	NPD752	Approved
0.6465	Remote Similarity	NPD7631	Approved
0.646	Remote Similarity	NPD2117	Pre-registration
0.646	Remote Similarity	NPD2116	Approved
0.646	Remote Similarity	NPD2115	Approved
0.6458	Remote Similarity	NPD650	Approved
0.6455	Remote Similarity	NPD181	Approved
0.6455	Remote Similarity	NPD5277	Phase 2
0.6441	Remote Similarity	NPD5667	Approved
0.6436	Remote Similarity	NPD2859	Approved
0.6436	Remote Similarity	NPD2860	Approved
0.6435	Remote Similarity	NPD17	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