NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	148.05
Volume:	160.062
LogP:	2.014
LogD:	1.593
LogS:	-1.792
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.511
Synthetic Accessibility Score:	2.305
Fsp3:	0.0
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:	-4.515
MDCK Permeability:	1.9197350411559455e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.811
Plasma Protein Binding (PPB):	87.81016540527344%
Volume Distribution (VD):	0.888
Pgp-substrate:	10.921653747558594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.777
CYP1A2-substrate:	0.345
CYP2C19-inhibitor:	0.237
CYP2C19-substrate:	0.251
CYP2C9-inhibitor:	0.135
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.097
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.207

ADMET: Excretion

Clearance (CL):	7.743
Half-life (T1/2):	0.862

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.238
Drug-inuced Liver Injury (DILI):	0.178
AMES Toxicity:	0.729
Rat Oral Acute Toxicity:	0.974
Maximum Recommended Daily Dose:	0.175
Skin Sensitization:	0.946
Carcinogencity:	0.606
Eye Corrosion:	0.842
Eye Irritation:	0.993
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC283711

Natural Product ID:	NPC283711
*Common Name:**	2-Hydroxycinnamaldehyde
IUPAC Name:	(E)-3-(2-hydroxyphenyl)prop-2-enal
Synonyms:	2-Hydroxycinnamaldehyde
Standard InCHIKey:	BSDNZCQPDVTDET-HWKANZROSA-N
Standard InCHI:	InChI=1S/C9H8O2/c10-7-3-5-8-4-1-2-6-9(8)11/h1-7,11H/b5-3+
SMILES:	c1ccc(c(c1)/C=C/C=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL52569
PubChem CID:	5318169
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000029] Cinnamaldehydes

*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]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[21875098]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	twigs	n.a.	n.a.	PMID[22677314]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24868863]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25089845]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28682072]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[29883114]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8255	Cinnamomum aromaticum	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]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9546	Cinamomum cassia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8255	Cinnamomum aromaticum	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

☑ 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
GI50	1
IC50	7
Others	5

Activity Type	# Activity
Cell Line	7
Individual Protein	3
Protein Complex	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	470000.0	nM	PMID[543636]
NPT323	Cell Line	SW-620	Homo sapiens	FC	=	1.5	n.a.	PMID[543637]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	=	15000.0	nM	PMID[543637]
NPT393	Cell Line	HCT-116	Homo sapiens	TGI	=	69.0	%	PMID[543639]
NPT393	Cell Line	HCT-116	Homo sapiens	TGI	=	52.0	%	PMID[543639]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	6170.0	nM	PMID[543639]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	6620.0	nM	PMID[543639]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	8140.0	nM	PMID[543639]
NPT1560	Protein Complex	Cyclin-dependent kinase 4/cyclin D1	Homo sapiens	Inhibition	=	50.0	%	PMID[543635]
NPT1560	Protein Complex	Cyclin-dependent kinase 4/cyclin D1	Homo sapiens	IC50	=	35000.0	nM	PMID[543635]
NPT1570	Protein Complex	Cyclin-dependent kinase 1/cyclin B	Homo sapiens	IC50	=	130000.0	nM	PMID[543635]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	Inhibition	=	94.2	%	PMID[543638]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	IC50	=	14.6	ug.mL-1	PMID[543638]

☑ 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 NPC283711 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	243
0.1-0.2	2323
0.2-0.3	6029
0.3-0.4	12832
0.4-0.5	6025
0.5-0.6	10176
0.6-0.7	4161
0.7-0.8	804
0.8-0.85	82
0.85-0.9	19
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9457	High Similarity	NPC286006
0.9247	High Similarity	NPC246679
0.8911	High Similarity	NPC98392
0.883	High Similarity	NPC181709
0.8824	High Similarity	NPC471535
0.8817	High Similarity	NPC47950
0.8791	High Similarity	NPC155393
0.8737	High Similarity	NPC81010
0.8737	High Similarity	NPC32977
0.8713	High Similarity	NPC303264
0.8696	High Similarity	NPC407
0.8696	High Similarity	NPC307235
0.8687	High Similarity	NPC470202
0.8681	High Similarity	NPC286904
0.8654	High Similarity	NPC228988
0.8646	High Similarity	NPC257182
0.8617	High Similarity	NPC300017
0.8614	High Similarity	NPC19149
0.8602	High Similarity	NPC104216
0.86	High Similarity	NPC93831
0.8586	High Similarity	NPC84325
0.8515	High Similarity	NPC303141
0.85	High Similarity	NPC304638
0.8485	Intermediate Similarity	NPC253746
0.8469	Intermediate Similarity	NPC201967
0.8438	Intermediate Similarity	NPC325292
0.8438	Intermediate Similarity	NPC138117
0.8421	Intermediate Similarity	NPC300478
0.8421	Intermediate Similarity	NPC312304
0.84	Intermediate Similarity	NPC94343
0.8384	Intermediate Similarity	NPC130193
0.8384	Intermediate Similarity	NPC128723
0.837	Intermediate Similarity	NPC265146
0.8365	Intermediate Similarity	NPC75272
0.8365	Intermediate Similarity	NPC471954
0.8351	Intermediate Similarity	NPC128062
0.835	Intermediate Similarity	NPC141523
0.8333	Intermediate Similarity	NPC231150
0.8333	Intermediate Similarity	NPC306074
0.8333	Intermediate Similarity	NPC219913
0.8333	Intermediate Similarity	NPC243677
0.8333	Intermediate Similarity	NPC204210
0.8333	Intermediate Similarity	NPC227255
0.8333	Intermediate Similarity	NPC163734
0.8317	Intermediate Similarity	NPC135784
0.83	Intermediate Similarity	NPC130103
0.83	Intermediate Similarity	NPC174911
0.8298	Intermediate Similarity	NPC23167
0.8283	Intermediate Similarity	NPC88420
0.828	Intermediate Similarity	NPC248817
0.828	Intermediate Similarity	NPC175313
0.8269	Intermediate Similarity	NPC206341
0.8269	Intermediate Similarity	NPC224584
0.8265	Intermediate Similarity	NPC313650
0.8247	Intermediate Similarity	NPC29373
0.8247	Intermediate Similarity	NPC271440
0.8211	Intermediate Similarity	NPC27974
0.8211	Intermediate Similarity	NPC113460
0.8211	Intermediate Similarity	NPC25493
0.82	Intermediate Similarity	NPC171843
0.8191	Intermediate Similarity	NPC197783
0.8182	Intermediate Similarity	NPC184527
0.8182	Intermediate Similarity	NPC212743
0.8173	Intermediate Similarity	NPC260952
0.8172	Intermediate Similarity	NPC124436
0.8163	Intermediate Similarity	NPC152415
0.8163	Intermediate Similarity	NPC245187
0.8148	Intermediate Similarity	NPC163154
0.8148	Intermediate Similarity	NPC41851
0.8148	Intermediate Similarity	NPC197513
0.8144	Intermediate Similarity	NPC45040
0.8137	Intermediate Similarity	NPC68269
0.8137	Intermediate Similarity	NPC13426
0.8137	Intermediate Similarity	NPC235762
0.8137	Intermediate Similarity	NPC471228
0.8125	Intermediate Similarity	NPC280347
0.8125	Intermediate Similarity	NPC242240
0.8125	Intermediate Similarity	NPC318325
0.8125	Intermediate Similarity	NPC123273
0.8125	Intermediate Similarity	NPC70436
0.8125	Intermediate Similarity	NPC258219
0.8125	Intermediate Similarity	NPC177420
0.8119	Intermediate Similarity	NPC13755
0.8113	Intermediate Similarity	NPC183700
0.8105	Intermediate Similarity	NPC184169
0.81	Intermediate Similarity	NPC152097
0.81	Intermediate Similarity	NPC475078
0.81	Intermediate Similarity	NPC474073
0.81	Intermediate Similarity	NPC260000
0.81	Intermediate Similarity	NPC140619
0.8095	Intermediate Similarity	NPC470039
0.8085	Intermediate Similarity	NPC150837
0.8081	Intermediate Similarity	NPC8392
0.8077	Intermediate Similarity	NPC69332
0.8077	Intermediate Similarity	NPC95178
0.8077	Intermediate Similarity	NPC29989
0.8058	Intermediate Similarity	NPC79672
0.8058	Intermediate Similarity	NPC475225
0.8058	Intermediate Similarity	NPC130817
0.8041	Intermediate Similarity	NPC55561
0.8041	Intermediate Similarity	NPC192
0.8039	Intermediate Similarity	NPC472585
0.8037	Intermediate Similarity	NPC212718
0.8037	Intermediate Similarity	NPC114682
0.8037	Intermediate Similarity	NPC228609
0.802	Intermediate Similarity	NPC280869
0.802	Intermediate Similarity	NPC78119
0.802	Intermediate Similarity	NPC216468
0.802	Intermediate Similarity	NPC132078
0.802	Intermediate Similarity	NPC260775
0.802	Intermediate Similarity	NPC80027
0.802	Intermediate Similarity	NPC245561
0.802	Intermediate Similarity	NPC51333
0.8	Intermediate Similarity	NPC312132
0.8	Intermediate Similarity	NPC259512
0.8	Intermediate Similarity	NPC34715
0.8	Intermediate Similarity	NPC226699
0.7981	Intermediate Similarity	NPC471350
0.7981	Intermediate Similarity	NPC127676
0.798	Intermediate Similarity	NPC151715
0.798	Intermediate Similarity	NPC289769
0.7965	Intermediate Similarity	NPC131868
0.7965	Intermediate Similarity	NPC216216
0.7959	Intermediate Similarity	NPC270547
0.7959	Intermediate Similarity	NPC304541
0.7941	Intermediate Similarity	NPC129373
0.7941	Intermediate Similarity	NPC48730
0.7941	Intermediate Similarity	NPC294741
0.7941	Intermediate Similarity	NPC248396
0.7941	Intermediate Similarity	NPC72729
0.7941	Intermediate Similarity	NPC52472
0.7941	Intermediate Similarity	NPC130756
0.7941	Intermediate Similarity	NPC70677
0.7941	Intermediate Similarity	NPC213730
0.7941	Intermediate Similarity	NPC12931
0.7938	Intermediate Similarity	NPC98772
0.7928	Intermediate Similarity	NPC174087
0.7928	Intermediate Similarity	NPC28169
0.7925	Intermediate Similarity	NPC279887
0.7925	Intermediate Similarity	NPC100551
0.7925	Intermediate Similarity	NPC68260
0.7921	Intermediate Similarity	NPC79241
0.7921	Intermediate Similarity	NPC6597
0.7921	Intermediate Similarity	NPC77492
0.7921	Intermediate Similarity	NPC156313
0.7905	Intermediate Similarity	NPC294902
0.7905	Intermediate Similarity	NPC1786
0.7905	Intermediate Similarity	NPC70843
0.7905	Intermediate Similarity	NPC6984
0.7905	Intermediate Similarity	NPC1075
0.79	Intermediate Similarity	NPC274678
0.79	Intermediate Similarity	NPC26244
0.7895	Intermediate Similarity	NPC476165
0.7895	Intermediate Similarity	NPC251259
0.7895	Intermediate Similarity	NPC295034
0.789	Intermediate Similarity	NPC28784
0.789	Intermediate Similarity	NPC296144
0.789	Intermediate Similarity	NPC242136
0.789	Intermediate Similarity	NPC11824
0.7885	Intermediate Similarity	NPC52087
0.7885	Intermediate Similarity	NPC2518
0.7879	Intermediate Similarity	NPC94139
0.7879	Intermediate Similarity	NPC147284
0.7879	Intermediate Similarity	NPC55903
0.7879	Intermediate Similarity	NPC210497
0.7879	Intermediate Similarity	NPC3358
0.7879	Intermediate Similarity	NPC306884
0.7879	Intermediate Similarity	NPC162314
0.787	Intermediate Similarity	NPC470355
0.787	Intermediate Similarity	NPC139946
0.7864	Intermediate Similarity	NPC91461
0.7864	Intermediate Similarity	NPC12221
0.7864	Intermediate Similarity	NPC7686
0.7864	Intermediate Similarity	NPC80800
0.7864	Intermediate Similarity	NPC40258
0.7864	Intermediate Similarity	NPC110764
0.7857	Intermediate Similarity	NPC283844
0.7857	Intermediate Similarity	NPC94637
0.7857	Intermediate Similarity	NPC41567
0.785	Intermediate Similarity	NPC282855
0.785	Intermediate Similarity	NPC26013
0.785	Intermediate Similarity	NPC95172
0.785	Intermediate Similarity	NPC88141
0.7843	Intermediate Similarity	NPC33675
0.7843	Intermediate Similarity	NPC252821
0.7843	Intermediate Similarity	NPC299762
0.7843	Intermediate Similarity	NPC131587
0.7843	Intermediate Similarity	NPC122005
0.7838	Intermediate Similarity	NPC128825
0.7835	Intermediate Similarity	NPC19680
0.783	Intermediate Similarity	NPC228737
0.783	Intermediate Similarity	NPC474352
0.783	Intermediate Similarity	NPC66834
0.7822	Intermediate Similarity	NPC473388
0.7818	Intermediate Similarity	NPC474114
0.7818	Intermediate Similarity	NPC474050
0.7818	Intermediate Similarity	NPC114144
0.7818	Intermediate Similarity	NPC473931
0.7818	Intermediate Similarity	NPC285350
0.781	Intermediate Similarity	NPC288760

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 NPC283711 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	1132
0.2-0.3	1429
0.3-0.4	2990
0.4-0.5	1930
0.5-0.6	1062
0.6-0.7	323
0.7-0.8	52
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
0.8172	Intermediate Similarity	NPD111	Approved
0.8081	Intermediate Similarity	NPD844	Approved
0.8061	Intermediate Similarity	NPD845	Approved
0.8	Intermediate Similarity	NPD288	Approved
0.798	Intermediate Similarity	NPD2933	Approved
0.798	Intermediate Similarity	NPD2934	Approved
0.7941	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD74	Approved
0.7925	Intermediate Similarity	NPD9266	Approved
0.79	Intermediate Similarity	NPD2859	Approved
0.79	Intermediate Similarity	NPD2860	Approved
0.7864	Intermediate Similarity	NPD846	Approved
0.7864	Intermediate Similarity	NPD940	Approved
0.7838	Intermediate Similarity	NPD9493	Approved
0.783	Intermediate Similarity	NPD9263	Approved
0.783	Intermediate Similarity	NPD9264	Approved
0.783	Intermediate Similarity	NPD9267	Approved
0.78	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD9273	Approved
0.7723	Intermediate Similarity	NPD1809	Phase 2
0.7692	Intermediate Similarity	NPD9294	Approved
0.767	Intermediate Similarity	NPD3020	Approved
0.7664	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD968	Approved
0.7556	Intermediate Similarity	NPD9087	Approved
0.7544	Intermediate Similarity	NPD9545	Approved
0.7522	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD290	Approved
0.7477	Intermediate Similarity	NPD9697	Approved
0.7453	Intermediate Similarity	NPD9261	Approved
0.7429	Intermediate Similarity	NPD1242	Phase 1
0.7419	Intermediate Similarity	NPD9088	Approved
0.7407	Intermediate Similarity	NPD3134	Approved
0.7364	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD9281	Approved
0.7339	Intermediate Similarity	NPD1358	Approved
0.7232	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD9256	Approved
0.7228	Intermediate Similarity	NPD9258	Approved
0.7222	Intermediate Similarity	NPD1237	Approved
0.7222	Intermediate Similarity	NPD9608	Approved
0.7222	Intermediate Similarity	NPD9610	Approved
0.7207	Intermediate Similarity	NPD4750	Phase 3
0.7203	Intermediate Similarity	NPD3496	Discontinued
0.7182	Intermediate Similarity	NPD2342	Discontinued
0.7179	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD1201	Approved
0.7119	Intermediate Similarity	NPD4626	Approved
0.7113	Intermediate Similarity	NPD9089	Approved
0.7105	Intermediate Similarity	NPD1241	Discontinued
0.7105	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD9716	Approved
0.7094	Intermediate Similarity	NPD1548	Phase 1
0.7094	Intermediate Similarity	NPD1759	Phase 1
0.7091	Intermediate Similarity	NPD1444	Approved
0.7091	Intermediate Similarity	NPD1445	Approved
0.7083	Intermediate Similarity	NPD9717	Approved
0.708	Intermediate Similarity	NPD228	Approved
0.7075	Intermediate Similarity	NPD9495	Approved
0.7073	Intermediate Similarity	NPD9494	Approved
0.7054	Intermediate Similarity	NPD3021	Approved
0.7054	Intermediate Similarity	NPD3022	Approved
0.7049	Intermediate Similarity	NPD1203	Approved
0.7049	Intermediate Similarity	NPD1470	Approved
0.7049	Intermediate Similarity	NPD1164	Approved
0.7043	Intermediate Similarity	NPD9614	Approved
0.7043	Intermediate Similarity	NPD9618	Approved
0.7043	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7635	Approved
0.701	Intermediate Similarity	NPD9093	Approved
0.7009	Intermediate Similarity	NPD1758	Phase 1
0.6984	Remote Similarity	NPD520	Approved
0.6983	Remote Similarity	NPD256	Approved
0.6983	Remote Similarity	NPD6671	Approved
0.6983	Remote Similarity	NPD255	Approved
0.6975	Remote Similarity	NPD1778	Approved
0.6972	Remote Similarity	NPD9500	Approved
0.6964	Remote Similarity	NPD2684	Approved
0.6961	Remote Similarity	NPD9295	Approved
0.6944	Remote Similarity	NPD3028	Approved
0.6935	Remote Similarity	NPD4208	Discontinued
0.6923	Remote Similarity	NPD1551	Phase 2
0.6923	Remote Similarity	NPD9568	Approved
0.6903	Remote Similarity	NPD1792	Phase 2
0.6891	Remote Similarity	NPD5691	Approved
0.6885	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.687	Remote Similarity	NPD9377	Approved
0.687	Remote Similarity	NPD9379	Approved
0.687	Remote Similarity	NPD821	Approved
0.6864	Remote Similarity	NPD317	Approved
0.6864	Remote Similarity	NPD856	Approved
0.6864	Remote Similarity	NPD9616	Approved
0.6864	Remote Similarity	NPD9613	Approved
0.6864	Remote Similarity	NPD9615	Approved
0.6864	Remote Similarity	NPD16	Approved
0.6864	Remote Similarity	NPD318	Approved
0.686	Remote Similarity	NPD1610	Phase 2
0.686	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD9250	Approved
0.6832	Remote Similarity	NPD9259	Approved
0.6832	Remote Similarity	NPD9257	Approved
0.6829	Remote Similarity	NPD3225	Approved
0.681	Remote Similarity	NPD2234	Approved
0.681	Remote Similarity	NPD2228	Approved
0.681	Remote Similarity	NPD2229	Approved
0.6807	Remote Similarity	NPD3091	Approved
0.6807	Remote Similarity	NPD316	Approved
0.6797	Remote Similarity	NPD1240	Approved
0.6774	Remote Similarity	NPD2797	Approved
0.6746	Remote Similarity	NPD4207	Discontinued
0.6733	Remote Similarity	NPD9073	Approved
0.6724	Remote Similarity	NPD7843	Approved
0.6721	Remote Similarity	NPD1091	Approved
0.6718	Remote Similarity	NPD1510	Phase 2
0.67	Remote Similarity	NPD9491	Approved
0.6699	Remote Similarity	NPD9094	Approved
0.6698	Remote Similarity	NPD1202	Approved
0.6697	Remote Similarity	NPD1238	Approved
0.6696	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD2932	Approved
0.6694	Remote Similarity	NPD9381	Approved
0.6694	Remote Similarity	NPD9384	Approved
0.6694	Remote Similarity	NPD3019	Approved
0.6694	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1607	Approved
0.6667	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9365	Approved
0.6667	Remote Similarity	NPD6647	Phase 2
0.6667	Remote Similarity	NPD943	Approved
0.6667	Remote Similarity	NPD1894	Discontinued
0.6667	Remote Similarity	NPD4212	Discontinued
0.6667	Remote Similarity	NPD5303	Approved
0.6667	Remote Similarity	NPD5304	Approved
0.664	Remote Similarity	NPD1131	Approved
0.664	Remote Similarity	NPD1135	Approved
0.664	Remote Similarity	NPD1133	Approved
0.664	Remote Similarity	NPD1129	Approved
0.664	Remote Similarity	NPD1134	Approved
0.6638	Remote Similarity	NPD969	Suspended
0.6636	Remote Similarity	NPD9296	Approved
0.6635	Remote Similarity	NPD689	Discontinued
0.6613	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.661	Remote Similarity	NPD1791	Approved
0.661	Remote Similarity	NPD1793	Approved
0.6606	Remote Similarity	NPD9612	Approved
0.6606	Remote Similarity	NPD9611	Approved
0.6606	Remote Similarity	NPD9609	Approved
0.6604	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD1282	Approved
0.6589	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD1019	Discontinued
0.6587	Remote Similarity	NPD2798	Approved
0.6585	Remote Similarity	NPD1535	Discovery
0.6585	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3092	Approved
0.6583	Remote Similarity	NPD5536	Phase 2
0.6581	Remote Similarity	NPD1138	Approved
0.6567	Remote Similarity	NPD1549	Phase 2
0.6557	Remote Similarity	NPD4589	Approved
0.6555	Remote Similarity	NPD709	Approved
0.6555	Remote Similarity	NPD7157	Approved
0.6545	Remote Similarity	NPD9712	Approved
0.6541	Remote Similarity	NPD2935	Discontinued
0.6538	Remote Similarity	NPD4060	Phase 1
0.6535	Remote Similarity	NPD5736	Approved
0.6535	Remote Similarity	NPD2861	Phase 2
0.6532	Remote Similarity	NPD2562	Approved
0.6532	Remote Similarity	NPD2561	Approved
0.6532	Remote Similarity	NPD9269	Phase 2
0.6532	Remote Similarity	NPD1481	Phase 2
0.6529	Remote Similarity	NPD7330	Discontinued
0.6522	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD411	Approved
0.6512	Remote Similarity	NPD3764	Approved
0.6512	Remote Similarity	NPD1048	Approved
0.6512	Remote Similarity	NPD3268	Approved
0.6504	Remote Similarity	NPD3847	Discontinued
0.6504	Remote Similarity	NPD1980	Approved
0.6504	Remote Similarity	NPD1981	Approved
0.6504	Remote Similarity	NPD3421	Phase 3
0.6504	Remote Similarity	NPD1983	Approved
0.65	Remote Similarity	NPD694	Clinical (unspecified phase)
0.65	Remote Similarity	NPD226	Approved
0.65	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD1139	Approved
0.6496	Remote Similarity	NPD1137	Approved
0.6493	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD230	Phase 1
0.6489	Remote Similarity	NPD447	Suspended
0.6484	Remote Similarity	NPD6832	Phase 2
0.6484	Remote Similarity	NPD4908	Phase 1
0.648	Remote Similarity	NPD4659	Approved
0.648	Remote Similarity	NPD1755	Approved
0.648	Remote Similarity	NPD6583	Phase 3
0.648	Remote Similarity	NPD9622	Approved
0.648	Remote Similarity	NPD6582	Phase 2

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