NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	190.1
Volume:	211.95
LogP:	2.789
LogD:	3.188
LogS:	-2.49
# Rotatable Bonds:	4
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.541
Synthetic Accessibility Score:	1.858
Fsp3:	0.25
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:	-4.282
MDCK Permeability:	2.8557860787259415e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.14

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.305
Plasma Protein Binding (PPB):	89.76773071289062%
Volume Distribution (VD):	1.637
Pgp-substrate:	9.45634937286377%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.857
CYP2C19-inhibitor:	0.968
CYP2C19-substrate:	0.325
CYP2C9-inhibitor:	0.824
CYP2C9-substrate:	0.177
CYP2D6-inhibitor:	0.827
CYP2D6-substrate:	0.161
CYP3A4-inhibitor:	0.173
CYP3A4-substrate:	0.424

ADMET: Excretion

Clearance (CL):	11.115
Half-life (T1/2):	0.817

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.037
Drug-inuced Liver Injury (DILI):	0.355
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.755
Carcinogencity:	0.172
Eye Corrosion:	0.743
Eye Irritation:	0.989
Respiratory Toxicity:	0.13

Download Data

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

Natural Product: NPC173443

Natural Product ID:	NPC173443
*Common Name:**	Benzyl (E)-2-Methylbut-2-Enoate
IUPAC Name:	benzyl (E)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	QRGSTISKDZCDHV-XCVCLJGOSA-N
Standard InCHI:	InChI=1S/C12H14O2/c1-3-10(2)12(13)14-9-11-7-5-4-6-8-11/h3-8H,9H2,1-2H3/b10-3+
SMILES:	C/C=C(C)/C(=O)OCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3186295
PubChem CID:	250096
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0001097] Benzyloxycarbonyls

*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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402962]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[26977531]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8904847]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10597	Fructus syzygii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10597	Fructus syzygii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30949	Eugenia caryopyhllata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	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	14

Activity Type	# Activity
Individual Protein	3
Others	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	54947.7	nM	PubChem BioAssay data set
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	61652.4	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	54947.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61652.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48972.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54947.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48557.7	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 NPC173443 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	198
0.1-0.2	1529
0.2-0.3	4266
0.3-0.4	11396
0.4-0.5	11687
0.5-0.6	10875
0.6-0.7	2281
0.7-0.8	359
0.8-0.85	68
0.85-0.9	24
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC89377
0.9518	High Similarity	NPC58616
0.931	High Similarity	NPC119631
0.9302	High Similarity	NPC220893
0.9222	High Similarity	NPC276775
0.9222	High Similarity	NPC249912
0.9222	High Similarity	NPC92754
0.9186	High Similarity	NPC304760
0.9121	High Similarity	NPC35448
0.9121	High Similarity	NPC225060
0.9121	High Similarity	NPC78701
0.9022	High Similarity	NPC146351
0.9	High Similarity	NPC130398
0.8925	High Similarity	NPC70624
0.8817	High Similarity	NPC118343
0.8795	High Similarity	NPC167577
0.8795	High Similarity	NPC78517
0.8764	High Similarity	NPC213156
0.8764	High Similarity	NPC240108
0.8737	High Similarity	NPC474365
0.8737	High Similarity	NPC301943
0.8723	High Similarity	NPC42211
0.869	High Similarity	NPC121800
0.8675	High Similarity	NPC176228
0.8632	High Similarity	NPC188895
0.8617	High Similarity	NPC325497
0.8617	High Similarity	NPC98911
0.8617	High Similarity	NPC472318
0.8617	High Similarity	NPC203925
0.8588	High Similarity	NPC303245
0.8588	High Similarity	NPC89950
0.8571	High Similarity	NPC170484
0.8556	High Similarity	NPC185501
0.8554	High Similarity	NPC3672
0.8554	High Similarity	NPC287790
0.8542	High Similarity	NPC234305
0.8488	Intermediate Similarity	NPC323103
0.8488	Intermediate Similarity	NPC103387
0.8488	Intermediate Similarity	NPC106313
0.8469	Intermediate Similarity	NPC119271
0.8454	Intermediate Similarity	NPC85977
0.8434	Intermediate Similarity	NPC175393
0.8427	Intermediate Similarity	NPC96625
0.8404	Intermediate Similarity	NPC325499
0.8391	Intermediate Similarity	NPC324835
0.8391	Intermediate Similarity	NPC308619
0.8391	Intermediate Similarity	NPC270507
0.8391	Intermediate Similarity	NPC127491
0.8387	Intermediate Similarity	NPC5472
0.8384	Intermediate Similarity	NPC56493
0.8372	Intermediate Similarity	NPC165212
0.8367	Intermediate Similarity	NPC269457
0.8351	Intermediate Similarity	NPC89886
0.8351	Intermediate Similarity	NPC179686
0.83	Intermediate Similarity	NPC17417
0.83	Intermediate Similarity	NPC469636
0.83	Intermediate Similarity	NPC10251
0.83	Intermediate Similarity	NPC265407
0.83	Intermediate Similarity	NPC474364
0.83	Intermediate Similarity	NPC83628
0.8283	Intermediate Similarity	NPC474376
0.8283	Intermediate Similarity	NPC472315
0.8283	Intermediate Similarity	NPC475203
0.8283	Intermediate Similarity	NPC472316
0.828	Intermediate Similarity	NPC23453
0.8265	Intermediate Similarity	NPC31786
0.8222	Intermediate Similarity	NPC286608
0.8222	Intermediate Similarity	NPC169050
0.8218	Intermediate Similarity	NPC251854
0.8218	Intermediate Similarity	NPC196246
0.8218	Intermediate Similarity	NPC174099
0.8218	Intermediate Similarity	NPC93084
0.8218	Intermediate Similarity	NPC214067
0.8211	Intermediate Similarity	NPC270654
0.8202	Intermediate Similarity	NPC294134
0.8182	Intermediate Similarity	NPC128730
0.8182	Intermediate Similarity	NPC208183
0.8182	Intermediate Similarity	NPC243289
0.8182	Intermediate Similarity	NPC209632
0.8163	Intermediate Similarity	NPC82426
0.8163	Intermediate Similarity	NPC304638
0.8163	Intermediate Similarity	NPC60679
0.8163	Intermediate Similarity	NPC91820
0.8137	Intermediate Similarity	NPC476003
0.8137	Intermediate Similarity	NPC1082
0.8137	Intermediate Similarity	NPC305912
0.8137	Intermediate Similarity	NPC260818
0.8137	Intermediate Similarity	NPC210089
0.8137	Intermediate Similarity	NPC474157
0.8111	Intermediate Similarity	NPC318107
0.81	Intermediate Similarity	NPC136962
0.81	Intermediate Similarity	NPC30594
0.81	Intermediate Similarity	NPC326447
0.81	Intermediate Similarity	NPC176971
0.81	Intermediate Similarity	NPC37622
0.8081	Intermediate Similarity	NPC114594
0.8081	Intermediate Similarity	NPC242913
0.8081	Intermediate Similarity	NPC280616
0.8081	Intermediate Similarity	NPC171831
0.8068	Intermediate Similarity	NPC99240
0.8061	Intermediate Similarity	NPC45613
0.8058	Intermediate Similarity	NPC321852
0.8058	Intermediate Similarity	NPC270699
0.8058	Intermediate Similarity	NPC82899
0.802	Intermediate Similarity	NPC151530
0.802	Intermediate Similarity	NPC277788
0.802	Intermediate Similarity	NPC157473
0.8	Intermediate Similarity	NPC472919
0.8	Intermediate Similarity	NPC238115
0.8	Intermediate Similarity	NPC53299
0.8	Intermediate Similarity	NPC227255
0.7981	Intermediate Similarity	NPC128368
0.7981	Intermediate Similarity	NPC161611
0.7981	Intermediate Similarity	NPC272524
0.7978	Intermediate Similarity	NPC288903
0.7961	Intermediate Similarity	NPC167504
0.7959	Intermediate Similarity	NPC253746
0.7955	Intermediate Similarity	NPC71795
0.7941	Intermediate Similarity	NPC206341
0.7941	Intermediate Similarity	NPC99846
0.7941	Intermediate Similarity	NPC85493
0.7941	Intermediate Similarity	NPC269023
0.7921	Intermediate Similarity	NPC37115
0.7905	Intermediate Similarity	NPC308744
0.7905	Intermediate Similarity	NPC307651
0.7905	Intermediate Similarity	NPC153053
0.7905	Intermediate Similarity	NPC474363
0.79	Intermediate Similarity	NPC2518
0.79	Intermediate Similarity	NPC109637
0.7895	Intermediate Similarity	NPC261181
0.7885	Intermediate Similarity	NPC79496
0.7885	Intermediate Similarity	NPC474314
0.7885	Intermediate Similarity	NPC158282
0.7879	Intermediate Similarity	NPC94343
0.7879	Intermediate Similarity	NPC84325
0.7864	Intermediate Similarity	NPC273837
0.7857	Intermediate Similarity	NPC171843
0.7835	Intermediate Similarity	NPC253423
0.783	Intermediate Similarity	NPC474685
0.783	Intermediate Similarity	NPC210092
0.7822	Intermediate Similarity	NPC473855
0.7822	Intermediate Similarity	NPC288760
0.781	Intermediate Similarity	NPC474176
0.7789	Intermediate Similarity	NPC77273
0.7778	Intermediate Similarity	NPC13755
0.7766	Intermediate Similarity	NPC62765
0.7757	Intermediate Similarity	NPC149691
0.7755	Intermediate Similarity	NPC175298
0.7755	Intermediate Similarity	NPC229242
0.7723	Intermediate Similarity	NPC283546
0.7714	Intermediate Similarity	NPC185840
0.7692	Intermediate Similarity	NPC149545
0.7684	Intermediate Similarity	NPC472319
0.7677	Intermediate Similarity	NPC217621
0.7674	Intermediate Similarity	NPC32203
0.7674	Intermediate Similarity	NPC206800
0.767	Intermediate Similarity	NPC260952
0.7664	Intermediate Similarity	NPC41851
0.7664	Intermediate Similarity	NPC306740
0.766	Intermediate Similarity	NPC9822
0.7647	Intermediate Similarity	NPC127676
0.7647	Intermediate Similarity	NPC139891
0.7642	Intermediate Similarity	NPC265002
0.7624	Intermediate Similarity	NPC160382
0.7619	Intermediate Similarity	NPC183700
0.7619	Intermediate Similarity	NPC473809
0.7615	Intermediate Similarity	NPC217423
0.7615	Intermediate Similarity	NPC45104
0.7614	Intermediate Similarity	NPC50192
0.7609	Intermediate Similarity	NPC475710
0.76	Intermediate Similarity	NPC107101
0.7596	Intermediate Similarity	NPC469511
0.7596	Intermediate Similarity	NPC291837
0.7593	Intermediate Similarity	NPC216387
0.7593	Intermediate Similarity	NPC100353
0.7573	Intermediate Similarity	NPC1065
0.7573	Intermediate Similarity	NPC477251
0.757	Intermediate Similarity	NPC237366
0.7551	Intermediate Similarity	NPC61944
0.7551	Intermediate Similarity	NPC246679
0.7547	Intermediate Similarity	NPC234376
0.7547	Intermediate Similarity	NPC139946
0.7545	Intermediate Similarity	NPC94298
0.7545	Intermediate Similarity	NPC94637
0.7545	Intermediate Similarity	NPC27633
0.7529	Intermediate Similarity	NPC326200
0.7525	Intermediate Similarity	NPC304873
0.7525	Intermediate Similarity	NPC25458
0.7525	Intermediate Similarity	NPC307425
0.7524	Intermediate Similarity	NPC471954
0.7524	Intermediate Similarity	NPC75272
0.75	Intermediate Similarity	NPC66655
0.75	Intermediate Similarity	NPC81808
0.75	Intermediate Similarity	NPC472314
0.75	Intermediate Similarity	NPC44546
0.75	Intermediate Similarity	NPC475465
0.75	Intermediate Similarity	NPC87563
0.7477	Intermediate Similarity	NPC98748
0.7477	Intermediate Similarity	NPC90522
0.7477	Intermediate Similarity	NPC328459

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 NPC173443 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	961
0.2-0.3	1268
0.3-0.4	3101
0.4-0.5	2165
0.5-0.6	1133
0.6-0.7	293
0.7-0.8	46
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8817	High Similarity	NPD1238	Approved
0.83	Intermediate Similarity	NPD2182	Approved
0.8265	Intermediate Similarity	NPD164	Approved
0.8222	Intermediate Similarity	NPD1282	Approved
0.8137	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD9257	Approved
0.8111	Intermediate Similarity	NPD9259	Approved
0.81	Intermediate Similarity	NPD3134	Approved
0.802	Intermediate Similarity	NPD1358	Approved
0.7895	Intermediate Similarity	NPD1202	Approved
0.7766	Intermediate Similarity	NPD9256	Approved
0.7766	Intermediate Similarity	NPD9258	Approved
0.7755	Intermediate Similarity	NPD5926	Approved
0.7674	Intermediate Similarity	NPD9716	Approved
0.766	Intermediate Similarity	NPD689	Discontinued
0.7647	Intermediate Similarity	NPD9697	Approved
0.7547	Intermediate Similarity	NPD969	Suspended
0.7545	Intermediate Similarity	NPD9545	Approved
0.7528	Intermediate Similarity	NPD9490	Approved
0.7524	Intermediate Similarity	NPD2067	Discontinued
0.75	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9294	Approved
0.7451	Intermediate Similarity	NPD6647	Phase 2
0.7449	Intermediate Similarity	NPD9260	Approved
0.7416	Intermediate Similarity	NPD225	Approved
0.7416	Intermediate Similarity	NPD227	Approved
0.7407	Intermediate Similarity	NPD1241	Discontinued
0.74	Intermediate Similarity	NPD9495	Approved
0.7396	Intermediate Similarity	NPD3672	Approved
0.7396	Intermediate Similarity	NPD3673	Approved
0.7391	Intermediate Similarity	NPD9491	Approved
0.7374	Intermediate Similarity	NPD1989	Approved
0.7364	Intermediate Similarity	NPD9493	Approved
0.7358	Intermediate Similarity	NPD5236	Approved
0.7358	Intermediate Similarity	NPD5239	Approved
0.7358	Intermediate Similarity	NPD5235	Approved
0.7358	Intermediate Similarity	NPD5237	Approved
0.7358	Intermediate Similarity	NPD5240	Approved
0.729	Intermediate Similarity	NPD2201	Approved
0.7273	Intermediate Similarity	NPD4198	Discontinued
0.7263	Intermediate Similarity	NPD1087	Approved
0.7222	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5909	Discontinued
0.7207	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD9250	Approved
0.7174	Intermediate Similarity	NPD226	Approved
0.7168	Intermediate Similarity	NPD5691	Approved
0.713	Intermediate Similarity	NPD6287	Discontinued
0.7113	Intermediate Similarity	NPD800	Approved
0.7103	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD2199	Approved
0.7094	Intermediate Similarity	NPD2198	Approved
0.7087	Intermediate Similarity	NPD2555	Approved
0.7087	Intermediate Similarity	NPD2550	Approved
0.7087	Intermediate Similarity	NPD2553	Approved
0.7087	Intermediate Similarity	NPD2549	Approved
0.7087	Intermediate Similarity	NPD2552	Approved
0.7087	Intermediate Similarity	NPD2558	Approved
0.7054	Intermediate Similarity	NPD5291	Approved
0.7054	Intermediate Similarity	NPD5292	Approved
0.7048	Intermediate Similarity	NPD1237	Approved
0.7043	Intermediate Similarity	NPD3496	Discontinued
0.7041	Intermediate Similarity	NPD1089	Approved
0.7041	Intermediate Similarity	NPD1086	Approved
0.7041	Intermediate Similarity	NPD1090	Approved
0.7034	Intermediate Similarity	NPD9567	Approved
0.7034	Intermediate Similarity	NPD552	Approved
0.7034	Intermediate Similarity	NPD553	Approved
0.7021	Intermediate Similarity	NPD3971	Phase 1
0.7019	Intermediate Similarity	NPD4188	Approved
0.7019	Intermediate Similarity	NPD4189	Approved
0.7018	Intermediate Similarity	NPD5585	Approved
0.7	Intermediate Similarity	NPD5535	Approved
0.6991	Remote Similarity	NPD2347	Approved
0.699	Remote Similarity	NPD2066	Phase 3
0.6983	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1019	Discontinued
0.6957	Remote Similarity	NPD1778	Approved
0.6952	Remote Similarity	NPD9261	Approved
0.693	Remote Similarity	NPD1894	Discontinued
0.6923	Remote Similarity	NPD9717	Approved
0.69	Remote Similarity	NPD1088	Approved
0.6887	Remote Similarity	NPD3048	Approved
0.6887	Remote Similarity	NPD3046	Approved
0.6887	Remote Similarity	NPD3047	Approved
0.6875	Remote Similarity	NPD2629	Approved
0.6875	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6832	Phase 2
0.6852	Remote Similarity	NPD290	Approved
0.6847	Remote Similarity	NPD5277	Phase 2
0.6832	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1563	Approved
0.6832	Remote Similarity	NPD1066	Discontinued
0.6827	Remote Similarity	NPD9712	Approved
0.6822	Remote Similarity	NPD794	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4626	Approved
0.6803	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1239	Approved
0.6792	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1930	Approved
0.6792	Remote Similarity	NPD1929	Approved
0.6789	Remote Similarity	NPD2684	Approved
0.6768	Remote Similarity	NPD5346	Phase 2
0.6768	Remote Similarity	NPD5347	Phase 2
0.6765	Remote Similarity	NPD1693	Approved
0.6759	Remote Similarity	NPD2559	Approved
0.6759	Remote Similarity	NPD3524	Approved
0.6759	Remote Similarity	NPD3526	Approved
0.6759	Remote Similarity	NPD968	Approved
0.6759	Remote Similarity	NPD812	Approved
0.6759	Remote Similarity	NPD810	Approved
0.6759	Remote Similarity	NPD811	Approved
0.6759	Remote Similarity	NPD2551	Approved
0.6757	Remote Similarity	NPD9508	Approved
0.6735	Remote Similarity	NPD4793	Discontinued
0.6731	Remote Similarity	NPD9710	Approved
0.6731	Remote Similarity	NPD9711	Approved
0.6726	Remote Similarity	NPD5951	Approved
0.6723	Remote Similarity	NPD4359	Approved
0.6697	Remote Similarity	NPD9263	Approved
0.6697	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD9264	Approved
0.6697	Remote Similarity	NPD9267	Approved
0.6696	Remote Similarity	NPD5536	Phase 2
0.6695	Remote Similarity	NPD4480	Approved
0.6695	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD422	Phase 1
0.6667	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD531	Approved
0.6667	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD7798	Approved
0.6667	Remote Similarity	NPD5667	Approved
0.664	Remote Similarity	NPD3373	Approved
0.6639	Remote Similarity	NPD1877	Discontinued
0.6636	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD74	Approved
0.6636	Remote Similarity	NPD9266	Approved
0.6635	Remote Similarity	NPD1565	Approved
0.6635	Remote Similarity	NPD1566	Phase 3
0.6635	Remote Similarity	NPD1564	Approved
0.6612	Remote Similarity	NPD3266	Approved
0.6612	Remote Similarity	NPD3267	Approved
0.6612	Remote Similarity	NPD2797	Approved
0.6612	Remote Similarity	NPD1203	Approved
0.661	Remote Similarity	NPD3847	Discontinued
0.6606	Remote Similarity	NPD5704	Approved
0.6606	Remote Similarity	NPD5705	Approved
0.6606	Remote Similarity	NPD5706	Approved
0.6602	Remote Similarity	NPD688	Clinical (unspecified phase)
0.66	Remote Similarity	NPD9249	Phase 1
0.6587	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD551	Approved
0.6577	Remote Similarity	NPD4234	Approved
0.6577	Remote Similarity	NPD1756	Approved
0.6577	Remote Similarity	NPD1752	Approved
0.6577	Remote Similarity	NPD550	Approved
0.6577	Remote Similarity	NPD4233	Approved
0.6555	Remote Similarity	NPD1281	Approved
0.6549	Remote Similarity	NPD821	Approved
0.6549	Remote Similarity	NPD7843	Approved
0.6531	Remote Similarity	NPD111	Approved
0.6529	Remote Similarity	NPD3225	Approved
0.6525	Remote Similarity	NPD5305	Approved
0.6525	Remote Similarity	NPD5306	Approved
0.6514	Remote Similarity	NPD5048	Discontinued
0.6504	Remote Similarity	NPD4006	Discontinued
0.65	Remote Similarity	NPD3972	Approved
0.65	Remote Similarity	NPD6637	Approved
0.65	Remote Similarity	NPD1608	Approved
0.6491	Remote Similarity	NPD6010	Discontinued
0.6484	Remote Similarity	NPD2569	Approved
0.6484	Remote Similarity	NPD2567	Approved
0.6484	Remote Similarity	NPD2670	Approved
0.6471	Remote Similarity	NPD4135	Approved
0.6471	Remote Similarity	NPD4106	Approved
0.6471	Remote Similarity	NPD4136	Approved
0.646	Remote Similarity	NPD4572	Approved
0.646	Remote Similarity	NPD4571	Approved
0.646	Remote Similarity	NPD1139	Approved
0.646	Remote Similarity	NPD1137	Approved
0.646	Remote Similarity	NPD4573	Approved
0.6457	Remote Similarity	NPD230	Phase 1
0.6457	Remote Similarity	NPD1933	Approved
0.6455	Remote Similarity	NPD6685	Approved
0.6452	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD2933	Approved
0.6442	Remote Similarity	NPD2934	Approved
0.6434	Remote Similarity	NPD3170	Approved
0.6434	Remote Similarity	NPD1109	Approved
0.6434	Remote Similarity	NPD1110	Approved
0.6429	Remote Similarity	NPD9713	Approved
0.6429	Remote Similarity	NPD5451	Approved
0.6429	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6085	Phase 2
0.6417	Remote Similarity	NPD4806	Approved
0.6417	Remote Similarity	NPD4807	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