NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	134.07
Volume:	153.908
LogP:	1.454
LogD:	1.637
LogS:	-1.583
# Rotatable Bonds:	3
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.576
Synthetic Accessibility Score:	1.644
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.366
MDCK Permeability:	2.4419958208454773e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.092
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.972
Plasma Protein Binding (PPB):	36.304195404052734%
Volume Distribution (VD):	1.534
Pgp-substrate:	50.90926742553711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.651
CYP1A2-substrate:	0.569
CYP2C19-inhibitor:	0.274
CYP2C19-substrate:	0.338
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.211
CYP2D6-inhibitor:	0.223
CYP2D6-substrate:	0.535
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	7.618
Half-life (T1/2):	0.743

ADMET: Toxicity

hERG Blockers:	0.13
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.509
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.069
Skin Sensitization:	0.962
Carcinogencity:	0.3
Eye Corrosion:	0.983
Eye Irritation:	0.995
Respiratory Toxicity:	0.872

Download Data

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

Natural Product: NPC271437

Natural Product ID:	NPC271437
*Common Name:**	Dihydrocinnamaldehyde
IUPAC Name:	3-phenylpropanal
Synonyms:	3-Phenyl-Propionaldehyde
Standard InCHIKey:	YGCZTXZTJXYWCO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6,8H,4,7H2
SMILES:	c1ccc(cc1)CCC=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL440161
PubChem CID:	7707
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
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	twigs	n.a.	n.a.	PMID[19555125]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	twigs	n.a.	n.a.	PMID[22677314]
NPO3689	Cinnamomum verum	Species	Lauraceae	Eukaryota	Bark	n.a.	n.a.	PMID[33151073]
NPO3689	Cinnamomum verum	Species	Lauraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3689	Cinnamomum verum	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3689	Cinnamomum verum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO3689	Cinnamomum verum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15081	Aleuroglyphus ovatus	Species	Acaridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17642	Chondropetalum paniculatum	Species	Restionaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21797	Derris brevipes	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3689	Cinnamomum verum	Species	Lauraceae	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
NPO3689	NPC271437	Other	Bark	10	4	16	mg/100g	Database [DUKE]

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Kd	1
MIC	14
Potency	5

Activity Type	# Activity
Organism	14
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Kd	=	150000.0	nM	PMID[522525]
NPT2	Others	Unspecified		IC50	>	300000.0	nM	PMID[522525]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	7450000.0	nM	PMID[522526]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	=	7450000.0	nM	PMID[522526]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	3720000.0	nM	PMID[522526]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	=	3720000.0	nM	PMID[522526]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	7450000.0	nM	PMID[522526]
NPT1262	Organism	Aspergillus parasiticus	Aspergillus parasiticus	MIC	=	14900000.0	nM	PMID[522526]
NPT1263	Organism	Aspergillus sydowii	Aspergillus sydowii	MIC	=	3720000.0	nM	PMID[522526]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	3720000.0	nM	PMID[522526]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	7450000.0	nM	PMID[522526]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	14900000.0	nM	PMID[522526]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	7450000.0	nM	PMID[522526]
NPT1264	Organism	Burkholderia cepacia	Burkholderia cepacia	MIC	=	14900000.0	nM	PMID[522526]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	7450000.0	nM	PMID[522526]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	7450000.0	nM	PMID[522526]
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	218.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	19493.8	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 NPC271437 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	299
0.1-0.2	2629
0.2-0.3	9198
0.3-0.4	17426
0.4-0.5	10656
0.5-0.6	1908
0.6-0.7	416
0.7-0.8	131
0.8-0.85	15
0.85-0.9	13
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9853	High Similarity	NPC208075
0.9437	High Similarity	NPC298023
0.9306	High Similarity	NPC76455
0.9306	High Similarity	NPC137847
0.9167	High Similarity	NPC329318
0.9054	High Similarity	NPC157055
0.9	High Similarity	NPC74458
0.8873	High Similarity	NPC285679
0.8816	High Similarity	NPC230068
0.8767	High Similarity	NPC78500
0.8732	High Similarity	NPC326200
0.8714	High Similarity	NPC16190
0.8714	High Similarity	NPC235059
0.8714	High Similarity	NPC169222
0.8701	High Similarity	NPC39600
0.8701	High Similarity	NPC197581
0.8684	High Similarity	NPC100039
0.8684	High Similarity	NPC73978
0.8481	Intermediate Similarity	NPC252067
0.84	Intermediate Similarity	NPC245966
0.84	Intermediate Similarity	NPC9796
0.8289	Intermediate Similarity	NPC2785
0.8289	Intermediate Similarity	NPC285470
0.8289	Intermediate Similarity	NPC103488
0.8289	Intermediate Similarity	NPC36342
0.8182	Intermediate Similarity	NPC300205
0.8182	Intermediate Similarity	NPC151405
0.8182	Intermediate Similarity	NPC139901
0.8182	Intermediate Similarity	NPC272260
0.8171	Intermediate Similarity	NPC153308
0.8148	Intermediate Similarity	NPC164526
0.8077	Intermediate Similarity	NPC190567
0.8077	Intermediate Similarity	NPC477703
0.8077	Intermediate Similarity	NPC17408
0.8077	Intermediate Similarity	NPC95868
0.8077	Intermediate Similarity	NPC71664
0.8077	Intermediate Similarity	NPC285716
0.8077	Intermediate Similarity	NPC164086
0.8077	Intermediate Similarity	NPC127343
0.8072	Intermediate Similarity	NPC325709
0.8025	Intermediate Similarity	NPC294134
0.8	Intermediate Similarity	NPC288903
0.7976	Intermediate Similarity	NPC58872
0.7975	Intermediate Similarity	NPC273033
0.7975	Intermediate Similarity	NPC145053
0.7975	Intermediate Similarity	NPC12936
0.7945	Intermediate Similarity	NPC98880
0.791	Intermediate Similarity	NPC198841
0.7882	Intermediate Similarity	NPC125226
0.7882	Intermediate Similarity	NPC103346
0.7838	Intermediate Similarity	NPC95289
0.7808	Intermediate Similarity	NPC82770
0.7808	Intermediate Similarity	NPC239931
0.7808	Intermediate Similarity	NPC78954
0.7808	Intermediate Similarity	NPC311343
0.7794	Intermediate Similarity	NPC120441
0.7794	Intermediate Similarity	NPC65873
0.7794	Intermediate Similarity	NPC212114
0.7794	Intermediate Similarity	NPC300345
0.7778	Intermediate Similarity	NPC44830
0.7778	Intermediate Similarity	NPC273758
0.7778	Intermediate Similarity	NPC285773
0.7761	Intermediate Similarity	NPC149436
0.7733	Intermediate Similarity	NPC208302
0.7733	Intermediate Similarity	NPC155429
0.7654	Intermediate Similarity	NPC323103
0.7647	Intermediate Similarity	NPC269586
0.7647	Intermediate Similarity	NPC231591
0.7647	Intermediate Similarity	NPC9822
0.7625	Intermediate Similarity	NPC121800
0.759	Intermediate Similarity	NPC123476
0.759	Intermediate Similarity	NPC95965
0.7564	Intermediate Similarity	NPC175393
0.7561	Intermediate Similarity	NPC270507
0.7561	Intermediate Similarity	NPC215008
0.7561	Intermediate Similarity	NPC324624
0.7532	Intermediate Similarity	NPC108218
0.75	Intermediate Similarity	NPC277704
0.75	Intermediate Similarity	NPC160339
0.75	Intermediate Similarity	NPC307
0.75	Intermediate Similarity	NPC170484
0.7471	Intermediate Similarity	NPC187725
0.7471	Intermediate Similarity	NPC317645
0.7471	Intermediate Similarity	NPC141607
0.7468	Intermediate Similarity	NPC179726
0.7465	Intermediate Similarity	NPC210849
0.7465	Intermediate Similarity	NPC310758
0.7465	Intermediate Similarity	NPC238023
0.7465	Intermediate Similarity	NPC54368
0.7465	Intermediate Similarity	NPC150196
0.7465	Intermediate Similarity	NPC135924
0.7465	Intermediate Similarity	NPC248705
0.7465	Intermediate Similarity	NPC246588
0.7439	Intermediate Similarity	NPC103387
0.7429	Intermediate Similarity	NPC114327
0.7429	Intermediate Similarity	NPC8235
0.7429	Intermediate Similarity	NPC36357
0.7412	Intermediate Similarity	NPC43945
0.7412	Intermediate Similarity	NPC69057
0.7412	Intermediate Similarity	NPC322387
0.7386	Intermediate Similarity	NPC77273
0.7375	Intermediate Similarity	NPC176228
0.7361	Intermediate Similarity	NPC29680
0.7361	Intermediate Similarity	NPC71009
0.7361	Intermediate Similarity	NPC66517
0.7361	Intermediate Similarity	NPC22786
0.7356	Intermediate Similarity	NPC110420
0.7356	Intermediate Similarity	NPC67585
0.7356	Intermediate Similarity	NPC303967
0.7349	Intermediate Similarity	NPC149263
0.7326	Intermediate Similarity	NPC477693
0.7326	Intermediate Similarity	NPC477704
0.7326	Intermediate Similarity	NPC267262
0.7326	Intermediate Similarity	NPC329064
0.7326	Intermediate Similarity	NPC157778
0.7324	Intermediate Similarity	NPC169110
0.7324	Intermediate Similarity	NPC147062
0.7284	Intermediate Similarity	NPC167577
0.7284	Intermediate Similarity	NPC78517
0.7273	Intermediate Similarity	NPC476484
0.726	Intermediate Similarity	NPC113670
0.726	Intermediate Similarity	NPC88566
0.726	Intermediate Similarity	NPC21211
0.725	Intermediate Similarity	NPC3672
0.725	Intermediate Similarity	NPC287790
0.7241	Intermediate Similarity	NPC113307
0.7241	Intermediate Similarity	NPC298115
0.7241	Intermediate Similarity	NPC418308
0.7222	Intermediate Similarity	NPC206764
0.7215	Intermediate Similarity	NPC206800
0.7215	Intermediate Similarity	NPC32203
0.7204	Intermediate Similarity	NPC473325
0.7183	Intermediate Similarity	NPC64270
0.7162	Intermediate Similarity	NPC155172
0.7162	Intermediate Similarity	NPC32312
0.7162	Intermediate Similarity	NPC291066
0.7162	Intermediate Similarity	NPC198023
0.716	Intermediate Similarity	NPC224544
0.7159	Intermediate Similarity	NPC19256
0.7159	Intermediate Similarity	NPC173413
0.7159	Intermediate Similarity	NPC70940
0.7159	Intermediate Similarity	NPC277277
0.7159	Intermediate Similarity	NPC274455
0.7159	Intermediate Similarity	NPC84288
0.7159	Intermediate Similarity	NPC86670
0.7126	Intermediate Similarity	NPC473345
0.7123	Intermediate Similarity	NPC200745
0.7108	Intermediate Similarity	NPC303245
0.7108	Intermediate Similarity	NPC89950
0.7079	Intermediate Similarity	NPC133461
0.7079	Intermediate Similarity	NPC284475
0.7067	Intermediate Similarity	NPC178527
0.7065	Intermediate Similarity	NPC270654
0.7065	Intermediate Similarity	NPC289201
0.7027	Intermediate Similarity	NPC50266
0.7027	Intermediate Similarity	NPC45756
0.7011	Intermediate Similarity	NPC89377
0.7011	Intermediate Similarity	NPC194326
0.7	Intermediate Similarity	NPC189371
0.7	Intermediate Similarity	NPC59677
0.7	Intermediate Similarity	NPC323164
0.7	Intermediate Similarity	NPC1682
0.7	Intermediate Similarity	NPC153885
0.7	Intermediate Similarity	NPC188844
0.7	Intermediate Similarity	NPC155232
0.6989	Remote Similarity	NPC317280
0.6989	Remote Similarity	NPC175852
0.6989	Remote Similarity	NPC160548
0.6989	Remote Similarity	NPC210529
0.6989	Remote Similarity	NPC329387
0.6988	Remote Similarity	NPC164449
0.6988	Remote Similarity	NPC184030
0.6988	Remote Similarity	NPC309279
0.6986	Remote Similarity	NPC45255
0.6977	Remote Similarity	NPC475710
0.6974	Remote Similarity	NPC267443
0.6974	Remote Similarity	NPC6107
0.6957	Remote Similarity	NPC12695
0.6951	Remote Similarity	NPC50192
0.6947	Remote Similarity	NPC188895
0.6941	Remote Similarity	NPC127491
0.6941	Remote Similarity	NPC308619
0.6941	Remote Similarity	NPC324835
0.6941	Remote Similarity	NPC243289
0.6941	Remote Similarity	NPC208183
0.6923	Remote Similarity	NPC291070
0.6923	Remote Similarity	NPC71140
0.6923	Remote Similarity	NPC238219
0.6923	Remote Similarity	NPC34243
0.6923	Remote Similarity	NPC246757
0.6923	Remote Similarity	NPC289883
0.6905	Remote Similarity	NPC117180
0.6897	Remote Similarity	NPC318107
0.6889	Remote Similarity	NPC110704
0.6889	Remote Similarity	NPC86987
0.6882	Remote Similarity	NPC249912
0.6882	Remote Similarity	NPC226041
0.6882	Remote Similarity	NPC92754
0.6882	Remote Similarity	NPC103048
0.6882	Remote Similarity	NPC276775

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 NPC271437 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	1173
0.2-0.3	2122
0.3-0.4	3351
0.4-0.5	1567
0.5-0.6	560
0.6-0.7	80
0.7-0.8	23
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8289	Intermediate Similarity	NPD225	Approved
0.8289	Intermediate Similarity	NPD227	Approved
0.8077	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD942	Approved
0.7975	Intermediate Similarity	NPD226	Approved
0.7949	Intermediate Similarity	NPD9490	Approved
0.7778	Intermediate Similarity	NPD9491	Approved
0.7558	Intermediate Similarity	NPD3672	Approved
0.7558	Intermediate Similarity	NPD3673	Approved
0.7412	Intermediate Similarity	NPD4793	Discontinued
0.7412	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD650	Approved
0.7412	Intermediate Similarity	NPD1087	Approved
0.726	Intermediate Similarity	NPD675	Discontinued
0.7241	Intermediate Similarity	NPD5347	Phase 2
0.7241	Intermediate Similarity	NPD800	Approved
0.7241	Intermediate Similarity	NPD5346	Phase 2
0.7215	Intermediate Similarity	NPD9716	Approved
0.7162	Intermediate Similarity	NPD173	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD1090	Approved
0.7159	Intermediate Similarity	NPD1086	Approved
0.7159	Intermediate Similarity	NPD1089	Approved
0.7143	Intermediate Similarity	NPD1989	Approved
0.7079	Intermediate Similarity	NPD1239	Approved
0.7079	Intermediate Similarity	NPD7609	Phase 3
0.7013	Intermediate Similarity	NPD9497	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1088	Approved
0.7	Intermediate Similarity	NPD1508	Approved
0.7	Intermediate Similarity	NPD7631	Approved
0.6989	Remote Similarity	NPD9495	Approved
0.6923	Remote Similarity	NPD1563	Approved
0.6923	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7798	Approved
0.6897	Remote Similarity	NPD9259	Approved
0.6897	Remote Similarity	NPD9257	Approved
0.6848	Remote Similarity	NPD1693	Approved
0.6848	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4094	Approved
0.6829	Remote Similarity	NPD9294	Approved
0.6774	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1843	Approved
0.6744	Remote Similarity	NPD3971	Phase 1
0.6739	Remote Similarity	NPD1202	Approved
0.6739	Remote Similarity	NPD1066	Discontinued
0.6737	Remote Similarity	NPD1238	Approved
0.6702	Remote Similarity	NPD4655	Approved
0.6702	Remote Similarity	NPD1564	Approved
0.6702	Remote Similarity	NPD1565	Approved
0.6702	Remote Similarity	NPD1100	Approved
0.6702	Remote Similarity	NPD1099	Approved
0.6702	Remote Similarity	NPD9566	Approved
0.6702	Remote Similarity	NPD1566	Phase 3
0.6702	Remote Similarity	NPD4657	Approved
0.6702	Remote Similarity	NPD3495	Discontinued
0.6633	Remote Similarity	NPD1237	Approved
0.6632	Remote Similarity	NPD253	Approved
0.6632	Remote Similarity	NPD466	Approved
0.6629	Remote Similarity	NPD1282	Approved
0.6625	Remote Similarity	NPD292	Approved
0.6625	Remote Similarity	NPD294	Approved
0.6593	Remote Similarity	NPD9256	Approved
0.6593	Remote Similarity	NPD9258	Approved
0.6591	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2066	Phase 3
0.6562	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD742	Approved
0.6543	Remote Similarity	NPD9728	Phase 1
0.65	Remote Similarity	NPD467	Phase 1
0.6495	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD689	Discontinued
0.6465	Remote Similarity	NPD164	Approved
0.6463	Remote Similarity	NPD9593	Approved
0.6463	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD9589	Approved
0.6463	Remote Similarity	NPD9594	Approved
0.6463	Remote Similarity	NPD9588	Approved
0.6463	Remote Similarity	NPD80	Approved
0.6463	Remote Similarity	NPD9592	Approved
0.6463	Remote Similarity	NPD9591	Approved
0.6463	Remote Similarity	NPD9590	Approved
0.6429	Remote Similarity	NPD2648	Phase 3
0.6429	Remote Similarity	NPD2193	Phase 2
0.6429	Remote Similarity	NPD4803	Discontinued
0.6429	Remote Similarity	NPD6024	Approved
0.6429	Remote Similarity	NPD2196	Discontinued
0.6429	Remote Similarity	NPD2171	Approved
0.6429	Remote Similarity	NPD1932	Approved
0.6429	Remote Similarity	NPD6027	Approved
0.64	Remote Similarity	NPD5048	Discontinued
0.6375	Remote Similarity	NPD1673	Approved
0.6374	Remote Similarity	NPD531	Approved
0.6373	Remote Similarity	NPD2182	Approved
0.6364	Remote Similarity	NPD3357	Discontinued
0.6364	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6647	Phase 2
0.6364	Remote Similarity	NPD1930	Approved
0.6364	Remote Similarity	NPD5765	Approved
0.6364	Remote Similarity	NPD1929	Approved
0.6364	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD1007	Discontinued
0.6322	Remote Similarity	NPD9250	Approved
0.6316	Remote Similarity	NPD9260	Approved
0.6311	Remote Similarity	NPD4233	Approved
0.6311	Remote Similarity	NPD4234	Approved
0.6311	Remote Similarity	NPD1756	Approved
0.6311	Remote Similarity	NPD1752	Approved
0.6311	Remote Similarity	NPD2067	Discontinued
0.6311	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.63	Remote Similarity	NPD5909	Discontinued
0.63	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5926	Approved
0.6263	Remote Similarity	NPD813	Approved
0.625	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD1767	Approved
0.6238	Remote Similarity	NPD1677	Discontinued
0.6238	Remote Similarity	NPD1018	Approved
0.6238	Remote Similarity	NPD1765	Approved
0.6238	Remote Similarity	NPD2192	Approved
0.6238	Remote Similarity	NPD1761	Approved
0.6238	Remote Similarity	NPD1763	Approved
0.6238	Remote Similarity	NPD1766	Approved
0.6238	Remote Similarity	NPD2197	Approved
0.6235	Remote Similarity	NPD4147	Approved
0.6235	Remote Similarity	NPD4144	Approved
0.6176	Remote Similarity	NPD6685	Approved
0.6163	Remote Similarity	NPD295	Approved
0.6163	Remote Similarity	NPD293	Approved
0.6163	Remote Similarity	NPD9393	Approved
0.6163	Remote Similarity	NPD296	Approved
0.6163	Remote Similarity	NPD9564	Approved
0.6163	Remote Similarity	NPD9397	Approved
0.6163	Remote Similarity	NPD79	Approved
0.6163	Remote Similarity	NPD9563	Approved
0.6132	Remote Similarity	NPD7094	Approved
0.6132	Remote Similarity	NPD2607	Approved
0.6132	Remote Similarity	NPD6858	Approved
0.6092	Remote Similarity	NPD1052	Approved
0.6092	Remote Similarity	NPD589	Approved
0.6092	Remote Similarity	NPD1051	Approved
0.6092	Remote Similarity	NPD1053	Approved
0.6092	Remote Similarity	NPD1475	Approved
0.6092	Remote Similarity	NPD590	Approved
0.6087	Remote Similarity	NPD9538	Approved
0.6075	Remote Similarity	NPD2652	Approved
0.6075	Remote Similarity	NPD1241	Discontinued
0.6075	Remote Similarity	NPD2650	Approved
0.6058	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD2329	Discontinued
0.6047	Remote Similarity	NPD603	Approved
0.6042	Remote Similarity	NPD3718	Approved
0.6042	Remote Similarity	NPD3719	Approved
0.6038	Remote Similarity	NPD2124	Approved
0.6023	Remote Similarity	NPD1617	Discontinued
0.6023	Remote Similarity	NPD3904	Approved
0.6023	Remote Similarity	NPD3979	Approved
0.6023	Remote Similarity	NPD3981	Approved
0.6023	Remote Similarity	NPD5371	Approved
0.6023	Remote Similarity	NPD3903	Approved
0.6023	Remote Similarity	NPD260	Discontinued
0.6023	Remote Similarity	NPD5372	Approved
0.6022	Remote Similarity	NPD1101	Approved
0.6019	Remote Similarity	NPD4766	Approved
0.6019	Remote Similarity	NPD2629	Approved
0.6019	Remote Similarity	NPD1711	Phase 2
0.6	Remote Similarity	NPD5278	Discontinued
0.6	Remote Similarity	NPD1317	Discontinued
0.6	Remote Similarity	NPD664	Approved
0.6	Remote Similarity	NPD5630	Phase 1
0.6	Remote Similarity	NPD3581	Discontinued
0.5981	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4814	Discontinued
0.5979	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD6049	Phase 2
0.5979	Remote Similarity	NPD7343	Discovery
0.5979	Remote Similarity	NPD7344	Phase 1
0.5963	Remote Similarity	NPD3317	Approved
0.5957	Remote Similarity	NPD1628	Approved
0.5957	Remote Similarity	NPD1629	Approved
0.5955	Remote Similarity	NPD4026	Approved
0.5955	Remote Similarity	NPD3035	Approved
0.5955	Remote Similarity	NPD472	Approved
0.5955	Remote Similarity	NPD4027	Approved
0.5943	Remote Similarity	NPD188	Approved
0.5943	Remote Similarity	NPD3643	Approved
0.5943	Remote Similarity	NPD3642	Approved
0.5943	Remote Similarity	NPD189	Phase 3
0.5943	Remote Similarity	NPD3644	Approved
0.5941	Remote Similarity	NPD6588	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD1370	Approved
0.5926	Remote Similarity	NPD1374	Approved
0.5926	Remote Similarity	NPD1371	Approved
0.5926	Remote Similarity	NPD1373	Approved
0.5926	Remote Similarity	NPD6010	Discontinued
0.5922	Remote Similarity	NPD1040	Phase 2
0.5922	Remote Similarity	NPD999	Phase 2
0.5914	Remote Similarity	NPD187	Approved
0.5909	Remote Similarity	NPD507	Approved
0.5909	Remote Similarity	NPD4576	Approved
0.5909	Remote Similarity	NPD508	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