NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	178.1
Volume:	197.29
LogP:	2.734
LogD:	2.591
LogS:	-2.878
# Rotatable Bonds:	5
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.66
Synthetic Accessibility Score:	1.563
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.311
MDCK Permeability:	3.7202724342932925e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.875

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.627
Plasma Protein Binding (PPB):	86.5134506225586%
Volume Distribution (VD):	0.887
Pgp-substrate:	12.94743537902832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.27
CYP2C19-inhibitor:	0.953
CYP2C19-substrate:	0.156
CYP2C9-inhibitor:	0.508
CYP2C9-substrate:	0.18
CYP2D6-inhibitor:	0.178
CYP2D6-substrate:	0.179
CYP3A4-inhibitor:	0.101
CYP3A4-substrate:	0.371

ADMET: Excretion

Clearance (CL):	13.082
Half-life (T1/2):	0.839

ADMET: Toxicity

hERG Blockers:	0.099
Human Hepatotoxicity (H-HT):	0.051
Drug-inuced Liver Injury (DILI):	0.123
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.908
Carcinogencity:	0.393
Eye Corrosion:	0.467
Eye Irritation:	0.968
Respiratory Toxicity:	0.045

Download Data

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

Natural Product: NPC121800

Natural Product ID:	NPC121800
*Common Name:**	Phenethyl Propionate
IUPAC Name:	2-phenylethyl propanoate
Synonyms:
Standard InCHIKey:	HVGZQCSMLUDISR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H14O2/c1-2-11(12)13-9-8-10-6-4-3-5-7-10/h3-7H,2,8-9H2,1H3
SMILES:	CCC(=O)OCCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1867360
PubChem CID:	31225
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives

*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
NPO19592	Michelia alba	Species	Magnoliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[20584613]
NPO19592	Michelia alba	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19592	Michelia alba	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19592	Michelia alba	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19592	Michelia alba	Species	Magnoliaceae	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
LD50	1
Others	1
Potency	21

Activity Type	# Activity
Individual Protein	7
Organism	1
Others	15

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	52643.5	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	46491.2	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	52643.5	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	52643.5	nM	PubChem BioAssay data set
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	1584.9	nM	PMID[521541]
NPT2	Others	Unspecified		Potency	n.a.	59067	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	46918.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	23300.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	41816.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	58528.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	18508.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	41435.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	52643.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	73683.6	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	52643.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	186.8	nM	PubChem BioAssay data set
NPT734	Organism	Musca domestica	Musca domestica	LD50	=	66.6	ug	PMID[521542]
NPT735	Individual Protein	GABA receptor subunit	Musca domestica	Activity	=	95.0	%	PMID[521542]

☑ 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 NPC121800 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	178
0.1-0.2	1078
0.2-0.3	3816
0.3-0.4	14029
0.4-0.5	15809
0.5-0.6	6272
0.6-0.7	1236
0.7-0.8	244
0.8-0.85	17
0.85-0.9	12
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9865	High Similarity	NPC170484
0.9737	High Similarity	NPC103387
0.9737	High Similarity	NPC323103
0.961	High Similarity	NPC270507
0.9367	High Similarity	NPC294134
0.9114	High Similarity	NPC288903
0.8902	High Similarity	NPC89377
0.8889	High Similarity	NPC58616
0.8795	High Similarity	NPC304760
0.869	High Similarity	NPC220893
0.869	High Similarity	NPC9822
0.869	High Similarity	NPC173443
0.8659	High Similarity	NPC475710
0.8588	High Similarity	NPC185501
0.8462	Intermediate Similarity	NPC175393
0.8415	Intermediate Similarity	NPC285773
0.8372	Intermediate Similarity	NPC240108
0.8372	Intermediate Similarity	NPC213156
0.8272	Intermediate Similarity	NPC127343
0.8235	Intermediate Similarity	NPC96625
0.8235	Intermediate Similarity	NPC322387
0.8205	Intermediate Similarity	NPC108218
0.8182	Intermediate Similarity	NPC155429
0.8148	Intermediate Similarity	NPC78517
0.8148	Intermediate Similarity	NPC167577
0.814	Intermediate Similarity	NPC329064
0.809	Intermediate Similarity	NPC23453
0.8068	Intermediate Similarity	NPC119631
0.8068	Intermediate Similarity	NPC317645
0.8025	Intermediate Similarity	NPC224544
0.8025	Intermediate Similarity	NPC176228
0.8022	Intermediate Similarity	NPC249912
0.8022	Intermediate Similarity	NPC92754
0.8022	Intermediate Similarity	NPC325499
0.8022	Intermediate Similarity	NPC270654
0.8022	Intermediate Similarity	NPC276775
0.7976	Intermediate Similarity	NPC44830
0.7955	Intermediate Similarity	NPC274455
0.7955	Intermediate Similarity	NPC84288
0.7955	Intermediate Similarity	NPC86670
0.7955	Intermediate Similarity	NPC70940
0.7952	Intermediate Similarity	NPC89950
0.7952	Intermediate Similarity	NPC303245
0.7949	Intermediate Similarity	NPC208302
0.7935	Intermediate Similarity	NPC78701
0.7935	Intermediate Similarity	NPC35448
0.7935	Intermediate Similarity	NPC225060
0.7901	Intermediate Similarity	NPC287790
0.7901	Intermediate Similarity	NPC3672
0.7875	Intermediate Similarity	NPC189371
0.7857	Intermediate Similarity	NPC106313
0.7849	Intermediate Similarity	NPC146351
0.7831	Intermediate Similarity	NPC309279
0.7816	Intermediate Similarity	NPC286608
0.7816	Intermediate Similarity	NPC169050
0.7802	Intermediate Similarity	NPC130398
0.7791	Intermediate Similarity	NPC95965
0.7789	Intermediate Similarity	NPC160382
0.7766	Intermediate Similarity	NPC473325
0.7766	Intermediate Similarity	NPC70624
0.7766	Intermediate Similarity	NPC42211
0.7765	Intermediate Similarity	NPC308619
0.7765	Intermediate Similarity	NPC324835
0.7765	Intermediate Similarity	NPC127491
0.7738	Intermediate Similarity	NPC165212
0.7722	Intermediate Similarity	NPC326200
0.766	Intermediate Similarity	NPC472318
0.766	Intermediate Similarity	NPC118343
0.766	Intermediate Similarity	NPC98911
0.7647	Intermediate Similarity	NPC99240
0.7647	Intermediate Similarity	NPC87299
0.7647	Intermediate Similarity	NPC99394
0.7647	Intermediate Similarity	NPC103326
0.7647	Intermediate Similarity	NPC329319
0.764	Intermediate Similarity	NPC231591
0.7625	Intermediate Similarity	NPC271437
0.7619	Intermediate Similarity	NPC328178
0.7604	Intermediate Similarity	NPC301943
0.7604	Intermediate Similarity	NPC474365
0.7604	Intermediate Similarity	NPC234305
0.7586	Intermediate Similarity	NPC53299
0.7579	Intermediate Similarity	NPC469481
0.7558	Intermediate Similarity	NPC172984
0.7558	Intermediate Similarity	NPC208183
0.7558	Intermediate Similarity	NPC243289
0.7556	Intermediate Similarity	NPC258627
0.7553	Intermediate Similarity	NPC160548
0.7553	Intermediate Similarity	NPC210529
0.7553	Intermediate Similarity	NPC175852
0.7551	Intermediate Similarity	NPC119271
0.7531	Intermediate Similarity	NPC208075
0.7529	Intermediate Similarity	NPC117180
0.7526	Intermediate Similarity	NPC85977
0.75	Intermediate Similarity	NPC188895
0.75	Intermediate Similarity	NPC318107
0.75	Intermediate Similarity	NPC74458
0.7475	Intermediate Similarity	NPC56493
0.7474	Intermediate Similarity	NPC203925
0.7474	Intermediate Similarity	NPC325497
0.7474	Intermediate Similarity	NPC171843
0.7474	Intermediate Similarity	NPC7435
0.7473	Intermediate Similarity	NPC110704
0.7473	Intermediate Similarity	NPC476484
0.7471	Intermediate Similarity	NPC304538
0.7471	Intermediate Similarity	NPC267704
0.747	Intermediate Similarity	NPC298023
0.747	Intermediate Similarity	NPC66655
0.7468	Intermediate Similarity	NPC235059
0.7468	Intermediate Similarity	NPC98880
0.7468	Intermediate Similarity	NPC16190
0.7468	Intermediate Similarity	NPC169222
0.7449	Intermediate Similarity	NPC472919
0.7449	Intermediate Similarity	NPC473855
0.7449	Intermediate Similarity	NPC238115
0.7447	Intermediate Similarity	NPC226041
0.7439	Intermediate Similarity	NPC206800
0.7439	Intermediate Similarity	NPC32203
0.7423	Intermediate Similarity	NPC91820
0.7423	Intermediate Similarity	NPC89886
0.7423	Intermediate Similarity	NPC82426
0.7419	Intermediate Similarity	NPC5472
0.7419	Intermediate Similarity	NPC172925
0.7407	Intermediate Similarity	NPC285679
0.74	Intermediate Similarity	NPC83628
0.74	Intermediate Similarity	NPC17417
0.74	Intermediate Similarity	NPC31274
0.74	Intermediate Similarity	NPC265407
0.74	Intermediate Similarity	NPC10251
0.74	Intermediate Similarity	NPC469636
0.7391	Intermediate Similarity	NPC77273
0.7381	Intermediate Similarity	NPC137847
0.7381	Intermediate Similarity	NPC50192
0.7381	Intermediate Similarity	NPC76455
0.7375	Intermediate Similarity	NPC95289
0.7374	Intermediate Similarity	NPC472315
0.7374	Intermediate Similarity	NPC475203
0.7374	Intermediate Similarity	NPC477251
0.7374	Intermediate Similarity	NPC474376
0.7374	Intermediate Similarity	NPC136962
0.7374	Intermediate Similarity	NPC472316
0.7368	Intermediate Similarity	NPC229242
0.7368	Intermediate Similarity	NPC271475
0.7347	Intermediate Similarity	NPC31786
0.7347	Intermediate Similarity	NPC171831
0.7347	Intermediate Similarity	NPC242913
0.7347	Intermediate Similarity	NPC19136
0.7347	Intermediate Similarity	NPC280616
0.7342	Intermediate Similarity	NPC311343
0.7333	Intermediate Similarity	NPC325441
0.7327	Intermediate Similarity	NPC251854
0.7327	Intermediate Similarity	NPC196246
0.7327	Intermediate Similarity	NPC174099
0.7327	Intermediate Similarity	NPC214067
0.7327	Intermediate Similarity	NPC158854
0.7327	Intermediate Similarity	NPC93084
0.7326	Intermediate Similarity	NPC133050
0.7326	Intermediate Similarity	NPC71795
0.7312	Intermediate Similarity	NPC261181
0.7303	Intermediate Similarity	NPC93843
0.7297	Intermediate Similarity	NPC212114
0.7297	Intermediate Similarity	NPC120441
0.7297	Intermediate Similarity	NPC300345
0.7297	Intermediate Similarity	NPC65873
0.7292	Intermediate Similarity	NPC217621
0.7292	Intermediate Similarity	NPC221825
0.7283	Intermediate Similarity	NPC86987
0.7273	Intermediate Similarity	NPC209632
0.7273	Intermediate Similarity	NPC269457
0.7273	Intermediate Similarity	NPC44546
0.7273	Intermediate Similarity	NPC95429
0.7263	Intermediate Similarity	NPC253423
0.7262	Intermediate Similarity	NPC329318
0.7255	Intermediate Similarity	NPC474157
0.7255	Intermediate Similarity	NPC260818
0.7255	Intermediate Similarity	NPC305912
0.7255	Intermediate Similarity	NPC210089
0.7255	Intermediate Similarity	NPC1082
0.7253	Intermediate Similarity	NPC1793
0.7245	Intermediate Similarity	NPC304638
0.7245	Intermediate Similarity	NPC60679
0.7245	Intermediate Similarity	NPC179686
0.7241	Intermediate Similarity	NPC73637
0.7241	Intermediate Similarity	NPC121478
0.7228	Intermediate Similarity	NPC469511
0.7228	Intermediate Similarity	NPC281604
0.7228	Intermediate Similarity	NPC474364
0.7209	Intermediate Similarity	NPC192623
0.7209	Intermediate Similarity	NPC164449
0.7209	Intermediate Similarity	NPC184030
0.7209	Intermediate Similarity	NPC157055
0.7204	Intermediate Similarity	NPC323164
0.72	Intermediate Similarity	NPC30594
0.72	Intermediate Similarity	NPC142326
0.72	Intermediate Similarity	NPC94751
0.72	Intermediate Similarity	NPC37622
0.72	Intermediate Similarity	NPC1065
0.72	Intermediate Similarity	NPC329705
0.72	Intermediate Similarity	NPC474111
0.72	Intermediate Similarity	NPC37115
0.7184	Intermediate Similarity	NPC321852

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 NPC121800 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	859
0.2-0.3	1429
0.3-0.4	3342
0.4-0.5	2023
0.5-0.6	1043
0.6-0.7	238
0.7-0.8	48
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8608	High Similarity	NPD9490	Approved
0.8481	Intermediate Similarity	NPD227	Approved
0.8481	Intermediate Similarity	NPD225	Approved
0.8415	Intermediate Similarity	NPD9491	Approved
0.8372	Intermediate Similarity	NPD3672	Approved
0.8372	Intermediate Similarity	NPD3673	Approved
0.8315	Intermediate Similarity	NPD1989	Approved
0.8235	Intermediate Similarity	NPD1087	Approved
0.8171	Intermediate Similarity	NPD226	Approved
0.8046	Intermediate Similarity	NPD800	Approved
0.7955	Intermediate Similarity	NPD1090	Approved
0.7955	Intermediate Similarity	NPD1086	Approved
0.7955	Intermediate Similarity	NPD1089	Approved
0.7816	Intermediate Similarity	NPD1282	Approved
0.7778	Intermediate Similarity	NPD1088	Approved
0.7692	Intermediate Similarity	NPD1563	Approved
0.7692	Intermediate Similarity	NPD1066	Discontinued
0.7667	Intermediate Similarity	NPD1239	Approved
0.766	Intermediate Similarity	NPD1238	Approved
0.764	Intermediate Similarity	NPD5346	Phase 2
0.764	Intermediate Similarity	NPD5347	Phase 2
0.7614	Intermediate Similarity	NPD4793	Discontinued
0.7609	Intermediate Similarity	NPD1693	Approved
0.7553	Intermediate Similarity	NPD9495	Approved
0.7553	Intermediate Similarity	NPD5926	Approved
0.7528	Intermediate Similarity	NPD531	Approved
0.75	Intermediate Similarity	NPD9257	Approved
0.75	Intermediate Similarity	NPD9259	Approved
0.7474	Intermediate Similarity	NPD7798	Approved
0.747	Intermediate Similarity	NPD9294	Approved
0.7447	Intermediate Similarity	NPD1564	Approved
0.7447	Intermediate Similarity	NPD1566	Phase 3
0.7447	Intermediate Similarity	NPD1565	Approved
0.7439	Intermediate Similarity	NPD9716	Approved
0.7423	Intermediate Similarity	NPD6647	Phase 2
0.7419	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2182	Approved
0.7374	Intermediate Similarity	NPD5704	Approved
0.7374	Intermediate Similarity	NPD5705	Approved
0.7374	Intermediate Similarity	NPD5706	Approved
0.7347	Intermediate Similarity	NPD164	Approved
0.7327	Intermediate Similarity	NPD1752	Approved
0.7327	Intermediate Similarity	NPD2067	Discontinued
0.7327	Intermediate Similarity	NPD1756	Approved
0.7327	Intermediate Similarity	NPD4233	Approved
0.7327	Intermediate Similarity	NPD4234	Approved
0.7312	Intermediate Similarity	NPD1202	Approved
0.7312	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2066	Phase 3
0.7255	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD689	Discontinued
0.72	Intermediate Similarity	NPD6685	Approved
0.7174	Intermediate Similarity	NPD9258	Approved
0.7174	Intermediate Similarity	NPD9256	Approved
0.7159	Intermediate Similarity	NPD3971	Phase 1
0.7157	Intermediate Similarity	NPD3646	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD9250	Approved
0.7115	Intermediate Similarity	NPD2607	Approved
0.7071	Intermediate Similarity	NPD1929	Approved
0.7071	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1930	Approved
0.7071	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2652	Approved
0.7048	Intermediate Similarity	NPD2650	Approved
0.703	Intermediate Similarity	NPD3134	Approved
0.7	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5909	Discontinued
0.699	Remote Similarity	NPD5239	Approved
0.699	Remote Similarity	NPD5240	Approved
0.699	Remote Similarity	NPD5236	Approved
0.699	Remote Similarity	NPD5237	Approved
0.699	Remote Similarity	NPD5235	Approved
0.6981	Remote Similarity	NPD4766	Approved
0.6981	Remote Similarity	NPD2629	Approved
0.6979	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD1358	Approved
0.6957	Remote Similarity	NPD1101	Approved
0.6931	Remote Similarity	NPD5048	Discontinued
0.6923	Remote Similarity	NPD2201	Approved
0.6916	Remote Similarity	NPD4198	Discontinued
0.6907	Remote Similarity	NPD9566	Approved
0.69	Remote Similarity	NPD5765	Approved
0.6875	Remote Similarity	NPD9260	Approved
0.6852	Remote Similarity	NPD4576	Approved
0.6852	Remote Similarity	NPD4574	Approved
0.6848	Remote Similarity	NPD9538	Approved
0.6837	Remote Similarity	NPD253	Approved
0.6792	Remote Similarity	NPD6858	Approved
0.6792	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7094	Approved
0.6789	Remote Similarity	NPD2347	Approved
0.6771	Remote Similarity	NPD719	Approved
0.6771	Remote Similarity	NPD720	Approved
0.6768	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD9712	Approved
0.6768	Remote Similarity	NPD1067	Discontinued
0.6765	Remote Similarity	NPD1040	Phase 2
0.6737	Remote Similarity	NPD530	Approved
0.6731	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD1373	Approved
0.6729	Remote Similarity	NPD1371	Approved
0.6729	Remote Similarity	NPD1374	Approved
0.6729	Remote Similarity	NPD1370	Approved
0.67	Remote Similarity	NPD2558	Approved
0.67	Remote Similarity	NPD2553	Approved
0.67	Remote Similarity	NPD2550	Approved
0.67	Remote Similarity	NPD2555	Approved
0.67	Remote Similarity	NPD2549	Approved
0.67	Remote Similarity	NPD2552	Approved
0.6699	Remote Similarity	NPD467	Phase 1
0.6698	Remote Similarity	NPD969	Suspended
0.6698	Remote Similarity	NPD6912	Phase 3
0.6697	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD752	Approved
0.6667	Remote Similarity	NPD9711	Approved
0.6667	Remote Similarity	NPD9710	Approved
0.6667	Remote Similarity	NPD1237	Approved
0.6667	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5535	Approved
0.6634	Remote Similarity	NPD4188	Approved
0.6634	Remote Similarity	NPD1932	Approved
0.6634	Remote Similarity	NPD4189	Approved
0.6629	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD675	Discontinued
0.6607	Remote Similarity	NPD5306	Approved
0.6607	Remote Similarity	NPD5305	Approved
0.6602	Remote Similarity	NPD9697	Approved
0.6598	Remote Similarity	NPD3719	Approved
0.6598	Remote Similarity	NPD1409	Phase 3
0.6598	Remote Similarity	NPD3718	Approved
0.6577	Remote Similarity	NPD4479	Discontinued
0.6577	Remote Similarity	NPD9545	Approved
0.6577	Remote Similarity	NPD1894	Discontinued
0.6574	Remote Similarity	NPD6010	Discontinued
0.6574	Remote Similarity	NPD1241	Discontinued
0.6556	Remote Similarity	NPD942	Approved
0.6549	Remote Similarity	NPD4106	Approved
0.6549	Remote Similarity	NPD4135	Approved
0.6549	Remote Similarity	NPD4136	Approved
0.6545	Remote Similarity	NPD5291	Approved
0.6545	Remote Similarity	NPD5292	Approved
0.6543	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD2933	Approved
0.6531	Remote Similarity	NPD7343	Discovery
0.6531	Remote Similarity	NPD7344	Phase 1
0.6531	Remote Similarity	NPD4814	Discontinued
0.6531	Remote Similarity	NPD2934	Approved
0.6526	Remote Similarity	NPD9249	Phase 1
0.6518	Remote Similarity	NPD5691	Approved
0.6518	Remote Similarity	NPD5585	Approved
0.6505	Remote Similarity	NPD3048	Approved
0.6505	Remote Similarity	NPD3046	Approved
0.6505	Remote Similarity	NPD3047	Approved
0.65	Remote Similarity	NPD9612	Approved
0.65	Remote Similarity	NPD9609	Approved
0.65	Remote Similarity	NPD9611	Approved
0.6491	Remote Similarity	NPD2612	Approved
0.6491	Remote Similarity	NPD3131	Approved
0.6491	Remote Similarity	NPD4807	Approved
0.6491	Remote Similarity	NPD2608	Approved
0.6491	Remote Similarity	NPD7437	Approved
0.6491	Remote Similarity	NPD4216	Approved
0.6491	Remote Similarity	NPD4215	Approved
0.6491	Remote Similarity	NPD4218	Approved
0.6491	Remote Similarity	NPD3132	Approved
0.6491	Remote Similarity	NPD2610	Approved
0.6491	Remote Similarity	NPD4217	Approved
0.6491	Remote Similarity	NPD7436	Approved
0.6491	Remote Similarity	NPD2609	Approved
0.6491	Remote Similarity	NPD4806	Approved
0.6491	Remote Similarity	NPD2611	Approved
0.6489	Remote Similarity	NPD650	Approved
0.6486	Remote Similarity	NPD6065	Approved
0.6481	Remote Similarity	NPD181	Approved
0.6465	Remote Similarity	NPD2860	Approved
0.6465	Remote Similarity	NPD2859	Approved
0.646	Remote Similarity	NPD1778	Approved
0.6452	Remote Similarity	NPD111	Approved
0.6429	Remote Similarity	NPD2617	Discontinued
0.6429	Remote Similarity	NPD845	Approved
0.6422	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD2329	Discontinued
0.6415	Remote Similarity	NPD2684	Approved
0.6408	Remote Similarity	NPD9261	Approved
0.6404	Remote Similarity	NPD3496	Discontinued
0.64	Remote Similarity	NPD1875	Phase 1
0.6396	Remote Similarity	NPD9493	Approved
0.6389	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD2551	Approved
0.6381	Remote Similarity	NPD3526	Approved
0.6381	Remote Similarity	NPD811	Approved
0.6381	Remote Similarity	NPD3524	Approved
0.6381	Remote Similarity	NPD812	Approved
0.6381	Remote Similarity	NPD2559	Approved
0.6381	Remote Similarity	NPD810	Approved
0.6373	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4105	Approved
0.6372	Remote Similarity	NPD4102	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