NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	134.07
Volume:	153.908
LogP:	2.475
LogD:	2.457
LogS:	-2.825
# Rotatable Bonds:	2
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.566
Synthetic Accessibility Score:	1.596
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:	-4.291
MDCK Permeability:	2.4928251150413416e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.979
Plasma Protein Binding (PPB):	84.3832778930664%
Volume Distribution (VD):	1.126
Pgp-substrate:	10.935189247131348%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.303
CYP2C19-inhibitor:	0.678
CYP2C19-substrate:	0.381
CYP2C9-inhibitor:	0.247
CYP2C9-substrate:	0.542
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.424
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.355

ADMET: Excretion

Clearance (CL):	5.227
Half-life (T1/2):	0.548

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.024
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.307
Carcinogencity:	0.218
Eye Corrosion:	0.963
Eye Irritation:	0.995
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC197581

Natural Product ID:	NPC197581
*Common Name:**	4-Ethylbenzaldehyde
IUPAC Name:	4-ethylbenzaldehyde
Synonyms:
Standard InCHIKey:	QNGNSVIICDLXHT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10O/c1-2-8-3-5-9(7-10)6-4-8/h3-7H,2H2,1H3
SMILES:	CCc1ccc(cc1)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1887227
PubChem CID:	20861
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000321] Benzoyl 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
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

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

Biological Activity

Activity Type	# Activity
Potency	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[493045]
NPT2	Others	Unspecified		Potency	n.a.	489.7	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 NPC197581 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	331
0.1-0.2	2480
0.2-0.3	7251
0.3-0.4	15804
0.4-0.5	12556
0.5-0.6	3566
0.6-0.7	548
0.7-0.8	102
0.8-0.85	29
0.85-0.9	20
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9747	High Similarity	NPC252067
0.974	High Similarity	NPC100039
0.939	High Similarity	NPC153308
0.925	High Similarity	NPC39600
0.9241	High Similarity	NPC145053
0.9167	High Similarity	NPC58872
0.9146	High Similarity	NPC164526
0.9103	High Similarity	NPC76455
0.9103	High Similarity	NPC137847
0.9091	High Similarity	NPC78500
0.9	High Similarity	NPC73978
0.8974	High Similarity	NPC329318
0.8875	High Similarity	NPC157055
0.8875	High Similarity	NPC190567
0.8861	High Similarity	NPC36342
0.8861	High Similarity	NPC285470
0.8861	High Similarity	NPC2785
0.8837	High Similarity	NPC103346
0.8831	High Similarity	NPC208075
0.875	High Similarity	NPC300205
0.8734	High Similarity	NPC298023
0.8734	High Similarity	NPC245966
0.8701	High Similarity	NPC271437
0.869	High Similarity	NPC160339
0.869	High Similarity	NPC307
0.8659	High Similarity	NPC230068
0.8642	High Similarity	NPC164086
0.8605	High Similarity	NPC325709
0.8588	High Similarity	NPC69057
0.8571	High Similarity	NPC326200
0.8537	High Similarity	NPC273033
0.8537	High Similarity	NPC12936
0.8415	Intermediate Similarity	NPC17408
0.8415	Intermediate Similarity	NPC285716
0.8415	Intermediate Similarity	NPC71664
0.8333	Intermediate Similarity	NPC273758
0.8333	Intermediate Similarity	NPC149263
0.8312	Intermediate Similarity	NPC16190
0.8312	Intermediate Similarity	NPC169222
0.8312	Intermediate Similarity	NPC235059
0.8295	Intermediate Similarity	NPC173413
0.8295	Intermediate Similarity	NPC277277
0.8276	Intermediate Similarity	NPC157778
0.8228	Intermediate Similarity	NPC285679
0.8202	Intermediate Similarity	NPC133461
0.8171	Intermediate Similarity	NPC103488
0.8161	Intermediate Similarity	NPC43945
0.8111	Intermediate Similarity	NPC155232
0.8111	Intermediate Similarity	NPC153885
0.8101	Intermediate Similarity	NPC74458
0.8085	Intermediate Similarity	NPC473325
0.8068	Intermediate Similarity	NPC267262
0.8022	Intermediate Similarity	NPC238219
0.8022	Intermediate Similarity	NPC289883
0.8	Intermediate Similarity	NPC284475
0.7976	Intermediate Similarity	NPC95868
0.7935	Intermediate Similarity	NPC260233
0.7912	Intermediate Similarity	NPC323420
0.7912	Intermediate Similarity	NPC188844
0.7912	Intermediate Similarity	NPC59677
0.7912	Intermediate Similarity	NPC1682
0.7907	Intermediate Similarity	NPC324624
0.7907	Intermediate Similarity	NPC215008
0.7889	Intermediate Similarity	NPC19256
0.7857	Intermediate Similarity	NPC139901
0.7857	Intermediate Similarity	NPC151405
0.7849	Intermediate Similarity	NPC219573
0.7849	Intermediate Similarity	NPC185208
0.7848	Intermediate Similarity	NPC98880
0.7812	Intermediate Similarity	NPC188895
0.7802	Intermediate Similarity	NPC125226
0.7778	Intermediate Similarity	NPC418308
0.7778	Intermediate Similarity	NPC113307
0.7766	Intermediate Similarity	NPC239185
0.775	Intermediate Similarity	NPC95289
0.7722	Intermediate Similarity	NPC311343
0.77	Intermediate Similarity	NPC470252
0.7684	Intermediate Similarity	NPC75724
0.7684	Intermediate Similarity	NPC49994
0.7684	Intermediate Similarity	NPC134882
0.7667	Intermediate Similarity	NPC473345
0.7619	Intermediate Similarity	NPC9796
0.7604	Intermediate Similarity	NPC217621
0.7579	Intermediate Similarity	NPC265220
0.7553	Intermediate Similarity	NPC472880
0.7528	Intermediate Similarity	NPC294134
0.7526	Intermediate Similarity	NPC70624
0.7526	Intermediate Similarity	NPC476993
0.7526	Intermediate Similarity	NPC109514
0.75	Intermediate Similarity	NPC303967
0.75	Intermediate Similarity	NPC288903
0.75	Intermediate Similarity	NPC110420
0.75	Intermediate Similarity	NPC67585
0.7449	Intermediate Similarity	NPC304873
0.7449	Intermediate Similarity	NPC25458
0.7447	Intermediate Similarity	NPC246757
0.7447	Intermediate Similarity	NPC291070
0.7442	Intermediate Similarity	NPC272260
0.7423	Intermediate Similarity	NPC203925
0.7403	Intermediate Similarity	NPC54368
0.7403	Intermediate Similarity	NPC248705
0.7396	Intermediate Similarity	NPC253423
0.7396	Intermediate Similarity	NPC276775
0.7396	Intermediate Similarity	NPC249912
0.7396	Intermediate Similarity	NPC92754
0.7374	Intermediate Similarity	NPC247976
0.7368	Intermediate Similarity	NPC130398
0.7356	Intermediate Similarity	NPC477703
0.7347	Intermediate Similarity	NPC472879
0.7326	Intermediate Similarity	NPC50192
0.732	Intermediate Similarity	NPC78701
0.732	Intermediate Similarity	NPC225060
0.732	Intermediate Similarity	NPC35448
0.7312	Intermediate Similarity	NPC86670
0.7312	Intermediate Similarity	NPC274455
0.7312	Intermediate Similarity	NPC70940
0.7253	Intermediate Similarity	NPC318107
0.7245	Intermediate Similarity	NPC146351
0.7241	Intermediate Similarity	NPC78517
0.7241	Intermediate Similarity	NPC167577
0.7234	Intermediate Similarity	NPC476484
0.7234	Intermediate Similarity	NPC110704
0.7228	Intermediate Similarity	NPC172483
0.7228	Intermediate Similarity	NPC105899
0.7228	Intermediate Similarity	NPC474910
0.7216	Intermediate Similarity	NPC240042
0.7215	Intermediate Similarity	NPC88566
0.7212	Intermediate Similarity	NPC265513
0.7209	Intermediate Similarity	NPC287790
0.7209	Intermediate Similarity	NPC179726
0.7209	Intermediate Similarity	NPC3672
0.7204	Intermediate Similarity	NPC298115
0.7204	Intermediate Similarity	NPC231591
0.72	Intermediate Similarity	NPC274443
0.72	Intermediate Similarity	NPC472691
0.72	Intermediate Similarity	NPC471829
0.72	Intermediate Similarity	NPC474866
0.72	Intermediate Similarity	NPC475939
0.7174	Intermediate Similarity	NPC322387
0.7172	Intermediate Similarity	NPC42211
0.7172	Intermediate Similarity	NPC112552
0.7159	Intermediate Similarity	NPC127343
0.7158	Intermediate Similarity	NPC77273
0.7157	Intermediate Similarity	NPC83409
0.7157	Intermediate Similarity	NPC185763
0.7157	Intermediate Similarity	NPC100767
0.7143	Intermediate Similarity	NPC8235
0.7143	Intermediate Similarity	NPC123476
0.7143	Intermediate Similarity	NPC229242
0.7129	Intermediate Similarity	NPC329282
0.7129	Intermediate Similarity	NPC249067
0.7126	Intermediate Similarity	NPC176228
0.7125	Intermediate Similarity	NPC198023
0.7113	Intermediate Similarity	NPC61944
0.7113	Intermediate Similarity	NPC12695
0.7111	Intermediate Similarity	NPC285773
0.7111	Intermediate Similarity	NPC44830
0.71	Intermediate Similarity	NPC244427
0.71	Intermediate Similarity	NPC222390
0.7097	Intermediate Similarity	NPC329064
0.7087	Intermediate Similarity	NPC249811
0.7087	Intermediate Similarity	NPC112903
0.7083	Intermediate Similarity	NPC261181
0.7079	Intermediate Similarity	NPC303245
0.7079	Intermediate Similarity	NPC89950
0.7075	Intermediate Similarity	NPC470253
0.7071	Intermediate Similarity	NPC118343
0.7048	Intermediate Similarity	NPC167504
0.7048	Intermediate Similarity	NPC137315
0.7037	Intermediate Similarity	NPC178527
0.703	Intermediate Similarity	NPC474365
0.703	Intermediate Similarity	NPC329556
0.703	Intermediate Similarity	NPC301943
0.7021	Intermediate Similarity	NPC9822
0.7019	Intermediate Similarity	NPC265407
0.7019	Intermediate Similarity	NPC83628
0.7019	Intermediate Similarity	NPC469636
0.7013	Intermediate Similarity	NPC120441
0.7013	Intermediate Similarity	NPC300345
0.7013	Intermediate Similarity	NPC65873
0.7013	Intermediate Similarity	NPC212114
0.7	Intermediate Similarity	NPC323103
0.699	Remote Similarity	NPC472700
0.699	Remote Similarity	NPC472699
0.699	Remote Similarity	NPC119271
0.6981	Remote Similarity	NPC280789
0.6977	Remote Similarity	NPC32203
0.6977	Remote Similarity	NPC206800
0.697	Remote Similarity	NPC145052
0.697	Remote Similarity	NPC329387
0.697	Remote Similarity	NPC317280
0.6966	Remote Similarity	NPC121800
0.6962	Remote Similarity	NPC135924
0.6962	Remote Similarity	NPC150196
0.6962	Remote Similarity	NPC210849
0.6961	Remote Similarity	NPC31786
0.6957	Remote Similarity	NPC95965
0.6951	Remote Similarity	NPC6107
0.6951	Remote Similarity	NPC267443
0.6947	Remote Similarity	NPC62765

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 NPC197581 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	1132
0.2-0.3	1851
0.3-0.4	3452
0.4-0.5	1738
0.5-0.6	550
0.6-0.7	81
0.7-0.8	29
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8537	High Similarity	NPD942	Approved
0.8161	Intermediate Similarity	NPD650	Approved
0.8	Intermediate Similarity	NPD7609	Phase 3
0.7976	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD7631	Approved
0.7766	Intermediate Similarity	NPD3495	Discontinued
0.7556	Intermediate Similarity	NPD1087	Approved
0.7527	Intermediate Similarity	NPD1508	Approved
0.7449	Intermediate Similarity	NPD2648	Phase 3
0.7449	Intermediate Similarity	NPD2193	Phase 2
0.7449	Intermediate Similarity	NPD2196	Discontinued
0.7391	Intermediate Similarity	NPD800	Approved
0.7326	Intermediate Similarity	NPD227	Approved
0.7326	Intermediate Similarity	NPD225	Approved
0.7312	Intermediate Similarity	NPD1086	Approved
0.7312	Intermediate Similarity	NPD1090	Approved
0.7312	Intermediate Similarity	NPD1089	Approved
0.7292	Intermediate Similarity	NPD1843	Approved
0.7292	Intermediate Similarity	NPD1989	Approved
0.7273	Intermediate Similarity	NPD1932	Approved
0.7253	Intermediate Similarity	NPD9259	Approved
0.7253	Intermediate Similarity	NPD9257	Approved
0.7245	Intermediate Similarity	NPD2066	Phase 3
0.7241	Intermediate Similarity	NPD9490	Approved
0.7228	Intermediate Similarity	NPD2192	Approved
0.7228	Intermediate Similarity	NPD1677	Discontinued
0.7228	Intermediate Similarity	NPD2197	Approved
0.7216	Intermediate Similarity	NPD1100	Approved
0.7216	Intermediate Similarity	NPD1099	Approved
0.7212	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD1088	Approved
0.7129	Intermediate Similarity	NPD1237	Approved
0.7128	Intermediate Similarity	NPD3672	Approved
0.7128	Intermediate Similarity	NPD3673	Approved
0.7111	Intermediate Similarity	NPD9491	Approved
0.7083	Intermediate Similarity	NPD1563	Approved
0.7083	Intermediate Similarity	NPD1202	Approved
0.7079	Intermediate Similarity	NPD226	Approved
0.7071	Intermediate Similarity	NPD1238	Approved
0.7053	Intermediate Similarity	NPD1239	Approved
0.703	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1930	Approved
0.703	Intermediate Similarity	NPD1929	Approved
0.7019	Intermediate Similarity	NPD2329	Discontinued
0.701	Intermediate Similarity	NPD1693	Approved
0.6977	Remote Similarity	NPD9716	Approved
0.6961	Remote Similarity	NPD164	Approved
0.6952	Remote Similarity	NPD1317	Discontinued
0.6947	Remote Similarity	NPD9258	Approved
0.6947	Remote Similarity	NPD9256	Approved
0.6931	Remote Similarity	NPD2171	Approved
0.6931	Remote Similarity	NPD813	Approved
0.6907	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD1564	Approved
0.6869	Remote Similarity	NPD1566	Phase 3
0.6869	Remote Similarity	NPD1565	Approved
0.6857	Remote Similarity	NPD2182	Approved
0.6842	Remote Similarity	NPD5347	Phase 2
0.6842	Remote Similarity	NPD5346	Phase 2
0.6809	Remote Similarity	NPD4793	Discontinued
0.6796	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9260	Approved
0.6667	Remote Similarity	NPD4094	Approved
0.6667	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5951	Approved
0.6596	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD675	Discontinued
0.6559	Remote Similarity	NPD3971	Phase 1
0.6535	Remote Similarity	NPD4655	Approved
0.6535	Remote Similarity	NPD4657	Approved
0.6522	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.65	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD466	Approved
0.6471	Remote Similarity	NPD9495	Approved
0.646	Remote Similarity	NPD7610	Discontinued
0.6458	Remote Similarity	NPD1282	Approved
0.6408	Remote Similarity	NPD742	Approved
0.6404	Remote Similarity	NPD7009	Phase 2
0.6381	Remote Similarity	NPD3357	Discontinued
0.6381	Remote Similarity	NPD6647	Phase 2
0.6364	Remote Similarity	NPD1007	Discontinued
0.6364	Remote Similarity	NPD9508	Approved
0.6348	Remote Similarity	NPD1245	Approved
0.6346	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD1246	Approved
0.6339	Remote Similarity	NPD851	Approved
0.6339	Remote Similarity	NPD853	Approved
0.6337	Remote Similarity	NPD6049	Phase 2
0.6337	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.633	Remote Similarity	NPD2067	Discontinued
0.633	Remote Similarity	NPD664	Approved
0.6325	Remote Similarity	NPD6287	Discontinued
0.6321	Remote Similarity	NPD5909	Discontinued
0.6311	Remote Similarity	NPD5926	Approved
0.631	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6858	Approved
0.6306	Remote Similarity	NPD7094	Approved
0.6293	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6027	Approved
0.6286	Remote Similarity	NPD4803	Discontinued
0.6286	Remote Similarity	NPD6024	Approved
0.6271	Remote Similarity	NPD3972	Approved
0.625	Remote Similarity	NPD7076	Approved
0.625	Remote Similarity	NPD294	Approved
0.625	Remote Similarity	NPD7077	Approved
0.625	Remote Similarity	NPD292	Approved
0.625	Remote Similarity	NPD7798	Approved
0.625	Remote Similarity	NPD1241	Discontinued
0.6238	Remote Similarity	NPD1066	Discontinued
0.6226	Remote Similarity	NPD9261	Approved
0.6207	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD1074	Approved
0.6195	Remote Similarity	NPD1075	Approved
0.6195	Remote Similarity	NPD1073	Approved
0.6182	Remote Similarity	NPD1752	Approved
0.6182	Remote Similarity	NPD4234	Approved
0.6182	Remote Similarity	NPD4233	Approved
0.6182	Remote Similarity	NPD1756	Approved
0.6162	Remote Similarity	NPD689	Discontinued
0.6161	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5277	Phase 2
0.6154	Remote Similarity	NPD5836	Discontinued
0.6154	Remote Similarity	NPD253	Approved
0.6121	Remote Similarity	NPD9545	Approved
0.6117	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1765	Approved
0.6111	Remote Similarity	NPD1766	Approved
0.6111	Remote Similarity	NPD1761	Approved
0.6111	Remote Similarity	NPD1763	Approved
0.6111	Remote Similarity	NPD1018	Approved
0.6111	Remote Similarity	NPD1767	Approved
0.6111	Remote Similarity	NPD5048	Discontinued
0.6095	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD9493	Approved
0.6087	Remote Similarity	NPD9294	Approved
0.6083	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD5157	Phase 1
0.6083	Remote Similarity	NPD5159	Phase 2
0.6078	Remote Similarity	NPD3718	Approved
0.6078	Remote Similarity	NPD3719	Approved
0.6061	Remote Similarity	NPD1101	Approved
0.6058	Remote Similarity	NPD9566	Approved
0.6055	Remote Similarity	NPD467	Phase 1
0.6053	Remote Similarity	NPD690	Clinical (unspecified phase)
0.605	Remote Similarity	NPD3624	Phase 2
0.605	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD7008	Discontinued
0.6036	Remote Similarity	NPD3581	Discontinued
0.6036	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD997	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD2056	Discontinued
0.6023	Remote Similarity	NPD1673	Approved
0.6019	Remote Similarity	NPD4814	Discontinued
0.6018	Remote Similarity	NPD2607	Approved
0.6017	Remote Similarity	NPD2345	Approved
0.6017	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9264	Approved
0.6	Remote Similarity	NPD9263	Approved
0.6	Remote Similarity	NPD3317	Approved
0.6	Remote Similarity	NPD1323	Discontinued
0.6	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9267	Approved
0.6	Remote Similarity	NPD1025	Discontinued
0.6	Remote Similarity	NPD1077	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD5653	Discontinued
0.5966	Remote Similarity	NPD4879	Approved
0.5965	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD1175	Approved
0.5965	Remote Similarity	NPD2652	Approved
0.5965	Remote Similarity	NPD2650	Approved
0.5952	Remote Similarity	NPD7713	Phase 3
0.5952	Remote Similarity	NPD7961	Discontinued
0.5946	Remote Similarity	NPD9266	Approved
0.5946	Remote Similarity	NPD74	Approved
0.5934	Remote Similarity	NPD80	Approved
0.5934	Remote Similarity	NPD9592	Approved
0.5934	Remote Similarity	NPD9590	Approved
0.5934	Remote Similarity	NPD9591	Approved
0.5934	Remote Similarity	NPD9593	Approved
0.5934	Remote Similarity	NPD9589	Approved
0.5934	Remote Similarity	NPD9594	Approved
0.5934	Remote Similarity	NPD9588	Approved
0.5932	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD2124	Approved
0.5926	Remote Similarity	NPD5765	Approved
0.5917	Remote Similarity	NPD518	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD2629	Approved
0.5913	Remote Similarity	NPD2508	Discontinued
0.5913	Remote Similarity	NPD4766	Approved
0.5909	Remote Similarity	NPD6685	Approved
0.5902	Remote Similarity	NPD2634	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD1876	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