NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	134.07
Volume:	153.908
LogP:	2.726
LogD:	2.831
LogS:	-1.926
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.625
Synthetic Accessibility Score:	1.906
Fsp3:	0.111
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:	-4.516
MDCK Permeability:	2.3592792786075734e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.308
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.27
Plasma Protein Binding (PPB):	91.62480926513672%
Volume Distribution (VD):	2.825
Pgp-substrate:	8.872937202453613%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.723
CYP2C19-inhibitor:	0.393
CYP2C19-substrate:	0.489
CYP2C9-inhibitor:	0.108
CYP2C9-substrate:	0.936
CYP2D6-inhibitor:	0.113
CYP2D6-substrate:	0.905
CYP3A4-inhibitor:	0.137
CYP3A4-substrate:	0.358

ADMET: Excretion

Clearance (CL):	15.127
Half-life (T1/2):	0.89

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.1
Maximum Recommended Daily Dose:	0.071
Skin Sensitization:	0.946
Carcinogencity:	0.58
Eye Corrosion:	0.917
Eye Irritation:	0.993
Respiratory Toxicity:	0.524

Download Data

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

Natural Product: NPC248817

Natural Product ID:	NPC248817
*Common Name:**	4-Propenyl-Phenol
IUPAC Name:	4-[(E)-prop-1-enyl]phenol
Synonyms:	4-Propenyl-Phenol
Standard InCHIKey:	UMFCIIBZHQXRCJ-NSCUHMNNSA-N
Standard InCHI:	InChI=1S/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2-7,10H,1H3/b3-2+
SMILES:	C/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL163297
PubChem CID:	5474441
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000037] Styrenes

*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
NPO16682	Cirsium chinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16682	Cirsium chinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7250	Ventilago vitiensis	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10786	Trichocereus werdermannianus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5531	Protoceratium reticulatum	Species	Gonyaulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16682	Cirsium chinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10079	Chloropyron maritimum	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12940	Briareum stechei	Species	Briareidae	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
Ki	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2805	Individual Protein	Dopamine beta-hydroxylase	Bos taurus	Ki	>	20000000.0	nM	PMID[494197]
NPT2805	Individual Protein	Dopamine beta-hydroxylase	Bos taurus	Partition ratio	=	680.0	n.a.	PMID[494197]

☑ 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 NPC248817 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	266
0.1-0.2	3262
0.2-0.3	9100
0.3-0.4	10366
0.4-0.5	7380
0.5-0.6	8505
0.6-0.7	2875
0.7-0.8	715
0.8-0.85	129
0.85-0.9	62
0.9-0.95	23
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC197783
0.9875	High Similarity	NPC124436
0.9875	High Similarity	NPC265146
0.9756	High Similarity	NPC23167
0.9756	High Similarity	NPC184169
0.9753	High Similarity	NPC175313
0.9639	High Similarity	NPC25493
0.9639	High Similarity	NPC113460
0.9524	High Similarity	NPC123273
0.9524	High Similarity	NPC258219
0.9524	High Similarity	NPC98772
0.9524	High Similarity	NPC242240
0.9524	High Similarity	NPC318325
0.9524	High Similarity	NPC280347
0.9524	High Similarity	NPC177420
0.9412	High Similarity	NPC55561
0.9405	High Similarity	NPC104216
0.9302	High Similarity	NPC304541
0.9302	High Similarity	NPC204210
0.9302	High Similarity	NPC270547
0.9302	High Similarity	NPC155908
0.9286	High Similarity	NPC307235
0.9286	High Similarity	NPC407
0.9277	High Similarity	NPC286904
0.9277	High Similarity	NPC150837
0.9195	High Similarity	NPC138117
0.9195	High Similarity	NPC325292
0.9195	High Similarity	NPC181709
0.9186	High Similarity	NPC300017
0.9176	High Similarity	NPC27974
0.9167	High Similarity	NPC155393
0.9091	High Similarity	NPC27323
0.9091	High Similarity	NPC316301
0.908	High Similarity	NPC45040
0.907	High Similarity	NPC70436
0.8989	High Similarity	NPC313650
0.8989	High Similarity	NPC26244
0.8989	High Similarity	NPC8392
0.8966	High Similarity	NPC300478
0.8953	High Similarity	NPC19680
0.8889	High Similarity	NPC473388
0.8876	High Similarity	NPC128062
0.8876	High Similarity	NPC32977
0.8876	High Similarity	NPC81010
0.8876	High Similarity	NPC151715
0.8864	High Similarity	NPC306074
0.8864	High Similarity	NPC231150
0.8791	High Similarity	NPC225464
0.8791	High Similarity	NPC260000
0.8791	High Similarity	NPC77492
0.8778	High Similarity	NPC286006
0.8778	High Similarity	NPC107522
0.8778	High Similarity	NPC274678
0.8764	High Similarity	NPC147284
0.8764	High Similarity	NPC94139
0.8764	High Similarity	NPC3358
0.8764	High Similarity	NPC55903
0.8764	High Similarity	NPC306884
0.8764	High Similarity	NPC162314
0.8764	High Similarity	NPC210497
0.875	High Similarity	NPC192
0.875	High Similarity	NPC151764
0.8696	High Similarity	NPC122005
0.8696	High Similarity	NPC171843
0.8696	High Similarity	NPC80027
0.8696	High Similarity	NPC252821
0.8696	High Similarity	NPC280869
0.8696	High Similarity	NPC92730
0.8696	High Similarity	NPC128723
0.8681	High Similarity	NPC202986
0.8681	High Similarity	NPC292730
0.8681	High Similarity	NPC132271
0.8681	High Similarity	NPC216520
0.8681	High Similarity	NPC82664
0.8667	High Similarity	NPC152415
0.8667	High Similarity	NPC245187
0.8602	High Similarity	NPC289381
0.8602	High Similarity	NPC225506
0.8602	High Similarity	NPC253746
0.8602	High Similarity	NPC155847
0.8587	High Similarity	NPC107619
0.8587	High Similarity	NPC201967
0.8587	High Similarity	NPC109955
0.8587	High Similarity	NPC32674
0.8571	High Similarity	NPC144682
0.8556	High Similarity	NPC271440
0.8556	High Similarity	NPC29373
0.8539	High Similarity	NPC47950
0.8539	High Similarity	NPC312304
0.8511	High Similarity	NPC101025
0.8511	High Similarity	NPC472585
0.8511	High Similarity	NPC471578
0.85	High Similarity	NPC100980
0.8495	Intermediate Similarity	NPC125732
0.8495	Intermediate Similarity	NPC78119
0.8495	Intermediate Similarity	NPC130193
0.8495	Intermediate Similarity	NPC216468
0.8495	Intermediate Similarity	NPC275104
0.8495	Intermediate Similarity	NPC51333
0.8495	Intermediate Similarity	NPC131587
0.8495	Intermediate Similarity	NPC245561
0.8495	Intermediate Similarity	NPC132078
0.8478	Intermediate Similarity	NPC312132
0.8478	Intermediate Similarity	NPC259512
0.8462	Intermediate Similarity	NPC289769
0.8462	Intermediate Similarity	NPC76938
0.8427	Intermediate Similarity	NPC99886
0.8427	Intermediate Similarity	NPC8002
0.8427	Intermediate Similarity	NPC259134
0.8427	Intermediate Similarity	NPC177844
0.8421	Intermediate Similarity	NPC196479
0.8421	Intermediate Similarity	NPC62351
0.8421	Intermediate Similarity	NPC178902
0.8421	Intermediate Similarity	NPC304638
0.8404	Intermediate Similarity	NPC52472
0.8404	Intermediate Similarity	NPC275053
0.8404	Intermediate Similarity	NPC248573
0.8404	Intermediate Similarity	NPC213730
0.8404	Intermediate Similarity	NPC161571
0.8404	Intermediate Similarity	NPC223393
0.8404	Intermediate Similarity	NPC211885
0.8387	Intermediate Similarity	NPC152097
0.8387	Intermediate Similarity	NPC79241
0.8387	Intermediate Similarity	NPC6597
0.8387	Intermediate Similarity	NPC474073
0.8387	Intermediate Similarity	NPC475078
0.837	Intermediate Similarity	NPC246679
0.837	Intermediate Similarity	NPC222146
0.837	Intermediate Similarity	NPC32714
0.837	Intermediate Similarity	NPC257182
0.8352	Intermediate Similarity	NPC295295
0.8333	Intermediate Similarity	NPC474603
0.8333	Intermediate Similarity	NPC79672
0.8333	Intermediate Similarity	NPC52087
0.8333	Intermediate Similarity	NPC71853
0.8333	Intermediate Similarity	NPC12987
0.8333	Intermediate Similarity	NPC120719
0.8316	Intermediate Similarity	NPC110764
0.8316	Intermediate Similarity	NPC40258
0.8316	Intermediate Similarity	NPC7686
0.8316	Intermediate Similarity	NPC91461
0.8298	Intermediate Similarity	NPC299762
0.8298	Intermediate Similarity	NPC100870
0.8298	Intermediate Similarity	NPC33675
0.8298	Intermediate Similarity	NPC260775
0.828	Intermediate Similarity	NPC283711
0.8247	Intermediate Similarity	NPC138942
0.8247	Intermediate Similarity	NPC303141
0.8247	Intermediate Similarity	NPC154899
0.8247	Intermediate Similarity	NPC127676
0.8247	Intermediate Similarity	NPC233396
0.8242	Intermediate Similarity	NPC321956
0.8235	Intermediate Similarity	NPC133050
0.8229	Intermediate Similarity	NPC470202
0.8229	Intermediate Similarity	NPC168829
0.8229	Intermediate Similarity	NPC68269
0.8229	Intermediate Similarity	NPC135784
0.8229	Intermediate Similarity	NPC305205
0.8211	Intermediate Similarity	NPC166761
0.8211	Intermediate Similarity	NPC72729
0.8211	Intermediate Similarity	NPC174911
0.8211	Intermediate Similarity	NPC248396
0.8211	Intermediate Similarity	NPC70677
0.8211	Intermediate Similarity	NPC130756
0.8211	Intermediate Similarity	NPC12931
0.8211	Intermediate Similarity	NPC129373
0.8211	Intermediate Similarity	NPC29601
0.8211	Intermediate Similarity	NPC48730
0.8191	Intermediate Similarity	NPC156313
0.8191	Intermediate Similarity	NPC140619
0.8191	Intermediate Similarity	NPC291789
0.8163	Intermediate Similarity	NPC135464
0.8163	Intermediate Similarity	NPC6984
0.8163	Intermediate Similarity	NPC92623
0.8163	Intermediate Similarity	NPC477814
0.8163	Intermediate Similarity	NPC231705
0.8163	Intermediate Similarity	NPC113457
0.8163	Intermediate Similarity	NPC271274
0.8144	Intermediate Similarity	NPC471511
0.8144	Intermediate Similarity	NPC254965
0.8144	Intermediate Similarity	NPC8931
0.8144	Intermediate Similarity	NPC30506
0.8144	Intermediate Similarity	NPC261573
0.8144	Intermediate Similarity	NPC327811
0.8144	Intermediate Similarity	NPC119860
0.8144	Intermediate Similarity	NPC288411
0.8144	Intermediate Similarity	NPC12278
0.8144	Intermediate Similarity	NPC120693
0.814	Intermediate Similarity	NPC103326
0.814	Intermediate Similarity	NPC329319
0.814	Intermediate Similarity	NPC99394
0.814	Intermediate Similarity	NPC87299
0.8125	Intermediate Similarity	NPC51633
0.8125	Intermediate Similarity	NPC80800
0.8125	Intermediate Similarity	NPC252105
0.8125	Intermediate Similarity	NPC94343
0.8095	Intermediate Similarity	NPC65517
0.8081	Intermediate Similarity	NPC226699
0.8081	Intermediate Similarity	NPC142297
0.8081	Intermediate Similarity	NPC228737

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 NPC248817 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	1143
0.2-0.3	1585
0.3-0.4	2893
0.4-0.5	1851
0.5-0.6	946
0.6-0.7	333
0.7-0.8	53
0.8-0.85	9
0.85-0.9	5
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9875	High Similarity	NPD111	Approved
0.9091	High Similarity	NPD1432	Clinical (unspecified phase)
0.9091	High Similarity	NPD2933	Approved
0.9091	High Similarity	NPD2934	Approved
0.8989	High Similarity	NPD2859	Approved
0.8989	High Similarity	NPD2860	Approved
0.8696	High Similarity	NPD3020	Approved
0.8571	High Similarity	NPD1809	Phase 2
0.8571	High Similarity	NPD844	Approved
0.8556	High Similarity	NPD845	Approved
0.8511	High Similarity	NPD940	Approved
0.8511	High Similarity	NPD846	Approved
0.85	High Similarity	NPD9087	Approved
0.8478	Intermediate Similarity	NPD288	Approved
0.8404	Intermediate Similarity	NPD1242	Phase 1
0.8333	Intermediate Similarity	NPD9608	Approved
0.8333	Intermediate Similarity	NPD9610	Approved
0.8211	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD9088	Approved
0.7976	Intermediate Similarity	NPD9294	Approved
0.7921	Intermediate Similarity	NPD3021	Approved
0.7921	Intermediate Similarity	NPD3022	Approved
0.7857	Intermediate Similarity	NPD9500	Approved
0.7835	Intermediate Similarity	NPD3028	Approved
0.7812	Intermediate Similarity	NPD9273	Approved
0.78	Intermediate Similarity	NPD1445	Approved
0.78	Intermediate Similarity	NPD1444	Approved
0.7767	Intermediate Similarity	NPD228	Approved
0.7745	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD9089	Approved
0.7624	Intermediate Similarity	NPD968	Approved
0.7619	Intermediate Similarity	NPD2228	Approved
0.7619	Intermediate Similarity	NPD2229	Approved
0.7619	Intermediate Similarity	NPD2234	Approved
0.7614	Intermediate Similarity	NPD9093	Approved
0.7573	Intermediate Similarity	NPD1792	Phase 2
0.7549	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD9295	Approved
0.7524	Intermediate Similarity	NPD9379	Approved
0.7524	Intermediate Similarity	NPD9377	Approved
0.7477	Intermediate Similarity	NPD255	Approved
0.7477	Intermediate Similarity	NPD256	Approved
0.7476	Intermediate Similarity	NPD2684	Approved
0.7473	Intermediate Similarity	NPD9073	Approved
0.7429	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD4750	Phase 3
0.7379	Intermediate Similarity	NPD290	Approved
0.7379	Intermediate Similarity	NPD2342	Discontinued
0.7358	Intermediate Similarity	NPD821	Approved
0.7339	Intermediate Similarity	NPD317	Approved
0.7339	Intermediate Similarity	NPD16	Approved
0.7339	Intermediate Similarity	NPD856	Approved
0.7339	Intermediate Similarity	NPD318	Approved
0.7333	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD3134	Approved
0.7273	Intermediate Similarity	NPD5304	Approved
0.7273	Intermediate Similarity	NPD9545	Approved
0.7273	Intermediate Similarity	NPD3091	Approved
0.7273	Intermediate Similarity	NPD5303	Approved
0.7248	Intermediate Similarity	NPD9568	Approved
0.7234	Intermediate Similarity	NPD9094	Approved
0.7222	Intermediate Similarity	NPD9614	Approved
0.7222	Intermediate Similarity	NPD1793	Approved
0.7222	Intermediate Similarity	NPD9618	Approved
0.7222	Intermediate Similarity	NPD1791	Approved
0.7222	Intermediate Similarity	NPD475	Phase 2
0.7212	Intermediate Similarity	NPD1358	Approved
0.7207	Intermediate Similarity	NPD4093	Discontinued
0.7196	Intermediate Similarity	NPD7843	Approved
0.7196	Intermediate Similarity	NPD7635	Approved
0.7156	Intermediate Similarity	NPD6671	Approved
0.7143	Intermediate Similarity	NPD4059	Approved
0.7143	Intermediate Similarity	NPD2932	Approved
0.7143	Intermediate Similarity	NPD74	Approved
0.7143	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9266	Approved
0.7143	Intermediate Similarity	NPD9296	Approved
0.7143	Intermediate Similarity	NPD4589	Approved
0.7143	Intermediate Similarity	NPD1751	Approved
0.7143	Intermediate Similarity	NPD3019	Approved
0.7117	Intermediate Similarity	NPD1548	Phase 1
0.7091	Intermediate Similarity	NPD9493	Approved
0.7087	Intermediate Similarity	NPD9244	Approved
0.708	Intermediate Similarity	NPD3421	Phase 3
0.7075	Intermediate Similarity	NPD5451	Approved
0.7064	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1357	Approved
0.7048	Intermediate Similarity	NPD9263	Approved
0.7048	Intermediate Similarity	NPD9267	Approved
0.7048	Intermediate Similarity	NPD9264	Approved
0.7027	Intermediate Similarity	NPD9615	Approved
0.7027	Intermediate Similarity	NPD9613	Approved
0.7027	Intermediate Similarity	NPD9616	Approved
0.7018	Intermediate Similarity	NPD3092	Approved
0.7018	Intermediate Similarity	NPD422	Phase 1
0.7	Intermediate Similarity	NPD7157	Approved
0.6991	Remote Similarity	NPD2286	Discontinued
0.6991	Remote Similarity	NPD9384	Approved
0.6991	Remote Similarity	NPD9381	Approved
0.6964	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD316	Approved
0.6957	Remote Similarity	NPD2561	Approved
0.6957	Remote Similarity	NPD2562	Approved
0.6939	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD9612	Approved
0.6931	Remote Similarity	NPD9611	Approved
0.6931	Remote Similarity	NPD9609	Approved
0.6903	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6583	Phase 3
0.6897	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4659	Approved
0.6897	Remote Similarity	NPD9622	Approved
0.6897	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6582	Phase 2
0.6881	Remote Similarity	NPD5535	Approved
0.687	Remote Similarity	NPD1610	Phase 2
0.687	Remote Similarity	NPD1535	Discovery
0.6848	Remote Similarity	NPD9250	Approved
0.6842	Remote Similarity	NPD3095	Discontinued
0.6842	Remote Similarity	NPD4626	Approved
0.6842	Remote Similarity	NPD2668	Approved
0.6842	Remote Similarity	NPD2667	Approved
0.6838	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD9365	Approved
0.6818	Remote Similarity	NPD1241	Discontinued
0.6818	Remote Similarity	NPD5283	Phase 1
0.6814	Remote Similarity	NPD1759	Phase 1
0.681	Remote Similarity	NPD1481	Phase 2
0.681	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD1616	Discontinued
0.6786	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3847	Discontinued
0.6783	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3143	Discontinued
0.678	Remote Similarity	NPD1133	Approved
0.678	Remote Similarity	NPD1134	Approved
0.678	Remote Similarity	NPD3053	Approved
0.678	Remote Similarity	NPD4103	Phase 2
0.678	Remote Similarity	NPD3055	Approved
0.678	Remote Similarity	NPD3094	Phase 2
0.678	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.678	Remote Similarity	NPD1131	Approved
0.678	Remote Similarity	NPD1129	Approved
0.678	Remote Similarity	NPD1135	Approved
0.6765	Remote Similarity	NPD9495	Approved
0.6742	Remote Similarity	NPD9716	Approved
0.6735	Remote Similarity	NPD9256	Approved
0.6735	Remote Similarity	NPD9258	Approved
0.6731	Remote Similarity	NPD854	Approved
0.6731	Remote Similarity	NPD855	Approved
0.6731	Remote Similarity	NPD4818	Approved
0.6731	Remote Similarity	NPD4817	Approved
0.6726	Remote Similarity	NPD1758	Phase 1
0.6724	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD2194	Approved
0.6723	Remote Similarity	NPD257	Approved
0.6723	Remote Similarity	NPD9621	Approved
0.6723	Remote Similarity	NPD6584	Phase 3
0.6723	Remote Similarity	NPD258	Approved
0.6723	Remote Similarity	NPD2195	Approved
0.6723	Remote Similarity	NPD9619	Approved
0.6723	Remote Similarity	NPD7451	Discontinued
0.6723	Remote Similarity	NPD9620	Approved
0.6702	Remote Similarity	NPD9491	Approved
0.6698	Remote Similarity	NPD9697	Approved
0.6696	Remote Similarity	NPD709	Approved
0.6695	Remote Similarity	NPD5311	Approved
0.6695	Remote Similarity	NPD5310	Approved
0.6667	Remote Similarity	NPD9261	Approved
0.6667	Remote Similarity	NPD3636	Approved
0.6667	Remote Similarity	NPD3635	Approved
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD1894	Discontinued
0.6667	Remote Similarity	NPD7330	Discontinued
0.6667	Remote Similarity	NPD9494	Approved
0.6667	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3070	Discontinued
0.6667	Remote Similarity	NPD3637	Approved
0.6639	Remote Similarity	NPD1164	Approved
0.6638	Remote Similarity	NPD1983	Approved
0.6638	Remote Similarity	NPD1981	Approved
0.6638	Remote Similarity	NPD1980	Approved
0.6637	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD3596	Phase 2
0.6612	Remote Similarity	NPD4908	Phase 1
0.6612	Remote Similarity	NPD2605	Approved
0.6612	Remote Similarity	NPD2606	Approved
0.661	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.661	Remote Similarity	NPD1755	Approved
0.661	Remote Similarity	NPD3685	Discontinued
0.6607	Remote Similarity	NPD497	Approved
0.6607	Remote Similarity	NPD9281	Approved
0.6604	Remote Similarity	NPD310	Approved
0.6604	Remote Similarity	NPD309	Approved
0.6604	Remote Similarity	NPD314	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