NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	269.992
LogP:	3.801
LogD:	3.237
LogS:	-4.423
# Rotatable Bonds:	5
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.64
Synthetic Accessibility Score:	2.23
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.704
MDCK Permeability:	1.693746708042454e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.875

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109
Plasma Protein Binding (PPB):	92.74628448486328%
Volume Distribution (VD):	0.305
Pgp-substrate:	5.668510913848877%

ADMET: Metabolism

CYP1A2-inhibitor:	0.388
CYP1A2-substrate:	0.382
CYP2C19-inhibitor:	0.09
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.269
CYP2C9-substrate:	0.862
CYP2D6-inhibitor:	0.187
CYP2D6-substrate:	0.344
CYP3A4-inhibitor:	0.039
CYP3A4-substrate:	0.098

ADMET: Excretion

Clearance (CL):	7.485
Half-life (T1/2):	0.698

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.814
Drug-inuced Liver Injury (DILI):	0.922
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.92
Carcinogencity:	0.536
Eye Corrosion:	0.072
Eye Irritation:	0.878
Respiratory Toxicity:	0.082

Download Data

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

Natural Product: NPC199462

Natural Product ID:	NPC199462
*Common Name:**	3-(4-Methoxy-3-Prenylphenyl)Acrylic Acid
IUPAC Name:	(E)-3-[4-methoxy-3-(3-methylbut-2-enyl)phenyl]prop-2-enoic acid
Synonyms:
Standard InCHIKey:	XWVOBHSSIJXKCV-RMKNXTFCSA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-11(2)4-7-13-10-12(6-9-15(16)17)5-8-14(13)18-3/h4-6,8-10H,7H2,1-3H3,(H,16,17)/b9-6+
SMILES:	COc1ccc(cc1CC=C(C)C)/C=C/C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1818959
PubChem CID:	13654710
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0002504] Cinnamic acids

*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
NPO32851	brazilian green propolis	Species	n.a.	n.a.	n.a.	Brazilian green propolis	n.a.	PMID[21865046]

☑ 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
Others	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	95.7	%	PMID[459595]
NPT2	Others	Unspecified		Ratio	=	0.82	n.a.	PMID[459595]

☑ 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 NPC199462 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	221
0.1-0.2	1560
0.2-0.3	4256
0.3-0.4	11505
0.4-0.5	6865
0.5-0.6	6139
0.6-0.7	9777
0.7-0.8	2237
0.8-0.85	103
0.85-0.9	26
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9619	High Similarity	NPC473809
0.934	High Similarity	NPC75272
0.934	High Similarity	NPC471954
0.9327	High Similarity	NPC227255
0.9231	High Similarity	NPC2518
0.9189	High Similarity	NPC183154
0.9189	High Similarity	NPC263754
0.8962	High Similarity	NPC303141
0.8785	High Similarity	NPC243677
0.8785	High Similarity	NPC288760
0.8774	High Similarity	NPC470202
0.8774	High Similarity	NPC179686
0.8729	High Similarity	NPC89630
0.8707	High Similarity	NPC131868
0.8704	High Similarity	NPC176971
0.8704	High Similarity	NPC326447
0.8632	High Similarity	NPC251259
0.8624	High Similarity	NPC157473
0.8624	High Similarity	NPC151530
0.8611	High Similarity	NPC473855
0.8611	High Similarity	NPC128730
0.8585	High Similarity	NPC253746
0.8571	High Similarity	NPC175298
0.8559	High Similarity	NPC248429
0.8559	High Similarity	NPC96286
0.8545	High Similarity	NPC470039
0.8519	High Similarity	NPC109637
0.8512	High Similarity	NPC121104
0.8512	High Similarity	NPC243688
0.8512	High Similarity	NPC473993
0.8509	High Similarity	NPC296526
0.8505	High Similarity	NPC84325
0.85	High Similarity	NPC244495
0.85	High Similarity	NPC93219
0.8496	Intermediate Similarity	NPC90903
0.8496	Intermediate Similarity	NPC141003
0.8496	Intermediate Similarity	NPC35344
0.8487	Intermediate Similarity	NPC472518
0.8468	Intermediate Similarity	NPC234639
0.8443	Intermediate Similarity	NPC478215
0.8443	Intermediate Similarity	NPC185066
0.8426	Intermediate Similarity	NPC304638
0.8421	Intermediate Similarity	NPC294941
0.8417	Intermediate Similarity	NPC201667
0.8417	Intermediate Similarity	NPC73413
0.8411	Intermediate Similarity	NPC13755
0.8403	Intermediate Similarity	NPC67300
0.8364	Intermediate Similarity	NPC1065
0.8364	Intermediate Similarity	NPC113457
0.8333	Intermediate Similarity	NPC307425
0.8333	Intermediate Similarity	NPC109241
0.8333	Intermediate Similarity	NPC109675
0.8333	Intermediate Similarity	NPC273772
0.8319	Intermediate Similarity	NPC139946
0.8318	Intermediate Similarity	NPC100870
0.8276	Intermediate Similarity	NPC33717
0.8276	Intermediate Similarity	NPC19290
0.8273	Intermediate Similarity	NPC127676
0.8273	Intermediate Similarity	NPC139891
0.8273	Intermediate Similarity	NPC238115
0.8269	Intermediate Similarity	NPC321956
0.8264	Intermediate Similarity	NPC27671
0.8264	Intermediate Similarity	NPC184219
0.8261	Intermediate Similarity	NPC41851
0.8261	Intermediate Similarity	NPC235250
0.8261	Intermediate Similarity	NPC114144
0.8254	Intermediate Similarity	NPC31849
0.8241	Intermediate Similarity	NPC107101
0.823	Intermediate Similarity	NPC183700
0.823	Intermediate Similarity	NPC141068
0.8226	Intermediate Similarity	NPC473019
0.8226	Intermediate Similarity	NPC168710
0.822	Intermediate Similarity	NPC61779
0.822	Intermediate Similarity	NPC37858
0.822	Intermediate Similarity	NPC264976
0.822	Intermediate Similarity	NPC98748
0.8214	Intermediate Similarity	NPC206341
0.8214	Intermediate Similarity	NPC75440
0.8211	Intermediate Similarity	NPC293387
0.8208	Intermediate Similarity	NPC246679
0.8197	Intermediate Similarity	NPC471827
0.8197	Intermediate Similarity	NPC471828
0.8189	Intermediate Similarity	NPC204353
0.8189	Intermediate Similarity	NPC326600
0.8189	Intermediate Similarity	NPC50896
0.8182	Intermediate Similarity	NPC283546
0.8182	Intermediate Similarity	NPC108875
0.8182	Intermediate Similarity	NPC38079
0.8175	Intermediate Similarity	NPC194277
0.8173	Intermediate Similarity	NPC71853
0.8167	Intermediate Similarity	NPC52247
0.8167	Intermediate Similarity	NPC144418
0.8165	Intermediate Similarity	NPC51633
0.8165	Intermediate Similarity	NPC94343
0.816	Intermediate Similarity	NPC109778
0.816	Intermediate Similarity	NPC86774
0.816	Intermediate Similarity	NPC327457
0.816	Intermediate Similarity	NPC32463
0.8151	Intermediate Similarity	NPC31314
0.8151	Intermediate Similarity	NPC474874
0.8151	Intermediate Similarity	NPC193193
0.8148	Intermediate Similarity	NPC171843
0.8148	Intermediate Similarity	NPC128723
0.8145	Intermediate Similarity	NPC2401
0.8145	Intermediate Similarity	NPC219923
0.8145	Intermediate Similarity	NPC472519
0.8142	Intermediate Similarity	NPC149545
0.8136	Intermediate Similarity	NPC70744
0.8136	Intermediate Similarity	NPC124916
0.8136	Intermediate Similarity	NPC131118
0.8136	Intermediate Similarity	NPC96705
0.8136	Intermediate Similarity	NPC137537
0.8136	Intermediate Similarity	NPC164706
0.8136	Intermediate Similarity	NPC272471
0.8136	Intermediate Similarity	NPC265547
0.8136	Intermediate Similarity	NPC107588
0.813	Intermediate Similarity	NPC471826
0.813	Intermediate Similarity	NPC234109
0.813	Intermediate Similarity	NPC188327
0.8125	Intermediate Similarity	NPC260952
0.8125	Intermediate Similarity	NPC233320
0.8115	Intermediate Similarity	NPC60517
0.8115	Intermediate Similarity	NPC291899
0.8115	Intermediate Similarity	NPC146886
0.8115	Intermediate Similarity	NPC111347
0.8115	Intermediate Similarity	NPC20443
0.8113	Intermediate Similarity	NPC32977
0.8113	Intermediate Similarity	NPC81010
0.811	Intermediate Similarity	NPC163557
0.8108	Intermediate Similarity	NPC473393
0.8108	Intermediate Similarity	NPC470393
0.8103	Intermediate Similarity	NPC161696
0.8103	Intermediate Similarity	NPC87563
0.8099	Intermediate Similarity	NPC13007
0.8099	Intermediate Similarity	NPC257188
0.8091	Intermediate Similarity	NPC192596
0.8091	Intermediate Similarity	NPC298224
0.8091	Intermediate Similarity	NPC305205
0.8087	Intermediate Similarity	NPC98372
0.8087	Intermediate Similarity	NPC266116
0.8087	Intermediate Similarity	NPC280760
0.8083	Intermediate Similarity	NPC204466
0.8083	Intermediate Similarity	NPC235190
0.8083	Intermediate Similarity	NPC163200
0.8083	Intermediate Similarity	NPC180006
0.8083	Intermediate Similarity	NPC322569
0.808	Intermediate Similarity	NPC170546
0.808	Intermediate Similarity	NPC66246
0.8077	Intermediate Similarity	NPC99886
0.8077	Intermediate Similarity	NPC8002
0.8077	Intermediate Similarity	NPC259134
0.8077	Intermediate Similarity	NPC177844
0.807	Intermediate Similarity	NPC25067
0.807	Intermediate Similarity	NPC88868
0.807	Intermediate Similarity	NPC231251
0.8067	Intermediate Similarity	NPC281356
0.8067	Intermediate Similarity	NPC298796
0.8065	Intermediate Similarity	NPC121740
0.8065	Intermediate Similarity	NPC224774
0.8065	Intermediate Similarity	NPC142087
0.8065	Intermediate Similarity	NPC258567
0.8065	Intermediate Similarity	NPC95034
0.8065	Intermediate Similarity	NPC37512
0.8062	Intermediate Similarity	NPC26954
0.8062	Intermediate Similarity	NPC38099
0.8053	Intermediate Similarity	NPC201959
0.8053	Intermediate Similarity	NPC291837
0.8051	Intermediate Similarity	NPC240664
0.8051	Intermediate Similarity	NPC122117
0.8049	Intermediate Similarity	NPC232692
0.8049	Intermediate Similarity	NPC202594
0.8049	Intermediate Similarity	NPC165556
0.8047	Intermediate Similarity	NPC62366
0.8034	Intermediate Similarity	NPC220540
0.8034	Intermediate Similarity	NPC188907
0.8033	Intermediate Similarity	NPC173350
0.8033	Intermediate Similarity	NPC154176
0.8033	Intermediate Similarity	NPC290605
0.8018	Intermediate Similarity	NPC38209
0.8017	Intermediate Similarity	NPC70752
0.8017	Intermediate Similarity	NPC187868
0.8016	Intermediate Similarity	NPC183348
0.8016	Intermediate Similarity	NPC245395
0.8016	Intermediate Similarity	NPC282230
0.8016	Intermediate Similarity	NPC80170
0.8	Intermediate Similarity	NPC247553
0.8	Intermediate Similarity	NPC275627
0.8	Intermediate Similarity	NPC199204
0.8	Intermediate Similarity	NPC14177
0.8	Intermediate Similarity	NPC202474
0.8	Intermediate Similarity	NPC81261
0.8	Intermediate Similarity	NPC469453
0.8	Intermediate Similarity	NPC300166
0.8	Intermediate Similarity	NPC23332
0.8	Intermediate Similarity	NPC473744
0.7984	Intermediate Similarity	NPC120225
0.7984	Intermediate Similarity	NPC213552
0.7983	Intermediate Similarity	NPC273282
0.7983	Intermediate Similarity	NPC152306
0.7983	Intermediate Similarity	NPC293424

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 NPC199462 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	1070
0.2-0.3	1332
0.3-0.4	2580
0.4-0.5	1964
0.5-0.6	1190
0.6-0.7	661
0.7-0.8	132
0.8-0.85	2
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9115	High Similarity	NPD4626	Approved
0.8704	High Similarity	NPD3134	Approved
0.8696	High Similarity	NPD5691	Approved
0.8624	High Similarity	NPD1358	Approved
0.8273	Intermediate Similarity	NPD9697	Approved
0.8235	Intermediate Similarity	NPD3496	Discontinued
0.8167	Intermediate Similarity	NPD422	Phase 1
0.8087	Intermediate Similarity	NPD5535	Approved
0.8053	Intermediate Similarity	NPD2684	Approved
0.8	Intermediate Similarity	NPD2935	Discontinued
0.7934	Intermediate Similarity	NPD3847	Discontinued
0.7931	Intermediate Similarity	NPD1138	Approved
0.7903	Intermediate Similarity	NPD2797	Approved
0.7891	Intermediate Similarity	NPD4060	Phase 1
0.7863	Intermediate Similarity	NPD1241	Discontinued
0.7845	Intermediate Similarity	NPD1139	Approved
0.7845	Intermediate Similarity	NPD1137	Approved
0.7823	Intermediate Similarity	NPD1283	Approved
0.782	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD9493	Approved
0.7805	Intermediate Similarity	NPD9717	Approved
0.7786	Intermediate Similarity	NPD2799	Discontinued
0.7778	Intermediate Similarity	NPD7843	Approved
0.7761	Intermediate Similarity	NPD7003	Approved
0.7742	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1281	Approved
0.7706	Intermediate Similarity	NPD1809	Phase 2
0.7705	Intermediate Similarity	NPD1778	Approved
0.7692	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5124	Phase 1
0.7692	Intermediate Similarity	NPD228	Approved
0.7686	Intermediate Similarity	NPD9545	Approved
0.7685	Intermediate Similarity	NPD845	Approved
0.7672	Intermediate Similarity	NPD5451	Approved
0.7652	Intermediate Similarity	NPD290	Approved
0.7627	Intermediate Similarity	NPD821	Approved
0.7623	Intermediate Similarity	NPD1651	Approved
0.7597	Intermediate Similarity	NPD3268	Approved
0.7597	Intermediate Similarity	NPD6798	Discontinued
0.7583	Intermediate Similarity	NPD7157	Approved
0.7583	Intermediate Similarity	NPD6671	Approved
0.7581	Intermediate Similarity	NPD1611	Approved
0.7559	Intermediate Similarity	NPD2798	Approved
0.7545	Intermediate Similarity	NPD2860	Approved
0.7545	Intermediate Similarity	NPD2859	Approved
0.7541	Intermediate Similarity	NPD1894	Discontinued
0.7522	Intermediate Similarity	NPD846	Approved
0.7522	Intermediate Similarity	NPD940	Approved
0.752	Intermediate Similarity	NPD3972	Approved
0.7481	Intermediate Similarity	NPD1240	Approved
0.748	Intermediate Similarity	NPD1203	Approved
0.7463	Intermediate Similarity	NPD4476	Approved
0.7463	Intermediate Similarity	NPD4477	Approved
0.7462	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD2313	Discontinued
0.746	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD5536	Phase 2
0.7455	Intermediate Similarity	NPD2934	Approved
0.7455	Intermediate Similarity	NPD2933	Approved
0.7455	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6832	Phase 2
0.744	Intermediate Similarity	NPD1535	Discovery
0.7438	Intermediate Similarity	NPD6387	Discontinued
0.7424	Intermediate Similarity	NPD6355	Discontinued
0.7422	Intermediate Similarity	NPD3691	Phase 2
0.7422	Intermediate Similarity	NPD3690	Phase 2
0.7417	Intermediate Similarity	NPD5283	Phase 1
0.7414	Intermediate Similarity	NPD968	Approved
0.7402	Intermediate Similarity	NPD3225	Approved
0.7398	Intermediate Similarity	NPD1548	Phase 1
0.7387	Intermediate Similarity	NPD844	Approved
0.7381	Intermediate Similarity	NPD1481	Phase 2
0.7368	Intermediate Similarity	NPD1607	Approved
0.7348	Intermediate Similarity	NPD4140	Approved
0.7348	Intermediate Similarity	NPD2203	Discontinued
0.7345	Intermediate Similarity	NPD3020	Approved
0.7344	Intermediate Similarity	NPD987	Approved
0.7344	Intermediate Similarity	NPD3266	Approved
0.7344	Intermediate Similarity	NPD3267	Approved
0.7328	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD7458	Discontinued
0.7323	Intermediate Similarity	NPD1669	Approved
0.7313	Intermediate Similarity	NPD7097	Phase 1
0.7308	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD1610	Phase 2
0.7295	Intermediate Similarity	NPD709	Approved
0.7293	Intermediate Similarity	NPD4340	Discontinued
0.7287	Intermediate Similarity	NPD1019	Discontinued
0.728	Intermediate Similarity	NPD2667	Approved
0.728	Intermediate Similarity	NPD2668	Approved
0.7279	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD594	Approved
0.7273	Intermediate Similarity	NPD592	Approved
0.7266	Intermediate Similarity	NPD196	Phase 1
0.7266	Intermediate Similarity	NPD8651	Approved
0.7266	Intermediate Similarity	NPD6666	Approved
0.7266	Intermediate Similarity	NPD6667	Approved
0.7266	Intermediate Similarity	NPD1876	Approved
0.7264	Intermediate Similarity	NPD111	Approved
0.7259	Intermediate Similarity	NPD4308	Phase 3
0.7252	Intermediate Similarity	NPD7095	Approved
0.7252	Intermediate Similarity	NPD5163	Phase 2
0.7246	Intermediate Similarity	NPD4628	Phase 3
0.7244	Intermediate Similarity	NPD1608	Approved
0.7239	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2424	Discontinued
0.7222	Intermediate Similarity	NPD7411	Suspended
0.7218	Intermediate Similarity	NPD2979	Phase 3
0.7209	Intermediate Similarity	NPD1164	Approved
0.7203	Intermediate Similarity	NPD9264	Approved
0.7203	Intermediate Similarity	NPD9267	Approved
0.7203	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD9263	Approved
0.72	Intermediate Similarity	NPD1357	Approved
0.72	Intermediate Similarity	NPD5585	Approved
0.72	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD411	Approved
0.7197	Intermediate Similarity	NPD1048	Approved
0.7197	Intermediate Similarity	NPD1296	Phase 2
0.7188	Intermediate Similarity	NPD6583	Phase 3
0.7188	Intermediate Similarity	NPD3685	Discontinued
0.7188	Intermediate Similarity	NPD6582	Phase 2
0.7176	Intermediate Similarity	NPD4908	Phase 1
0.7174	Intermediate Similarity	NPD1652	Phase 2
0.7168	Intermediate Similarity	NPD288	Approved
0.7164	Intermediate Similarity	NPD447	Suspended
0.7156	Intermediate Similarity	NPD9295	Approved
0.7154	Intermediate Similarity	NPD2557	Approved
0.7153	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6005	Phase 3
0.7153	Intermediate Similarity	NPD2346	Discontinued
0.7153	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6002	Phase 3
0.7153	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD5745	Approved
0.7143	Intermediate Similarity	NPD4062	Phase 3
0.7143	Intermediate Similarity	NPD5846	Approved
0.7143	Intermediate Similarity	NPD9266	Approved
0.7143	Intermediate Similarity	NPD74	Approved
0.7143	Intermediate Similarity	NPD6516	Phase 2
0.7132	Intermediate Similarity	NPD7033	Discontinued
0.7132	Intermediate Similarity	NPD1510	Phase 2
0.713	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3750	Approved
0.7122	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5049	Phase 3
0.7111	Intermediate Similarity	NPD4097	Suspended
0.7109	Intermediate Similarity	NPD2232	Approved
0.7109	Intermediate Similarity	NPD2233	Approved
0.7109	Intermediate Similarity	NPD2230	Approved
0.7107	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2861	Phase 2
0.7099	Intermediate Similarity	NPD454	Approved
0.7099	Intermediate Similarity	NPD9494	Approved
0.7099	Intermediate Similarity	NPD2237	Approved
0.7097	Intermediate Similarity	NPD3596	Phase 2
0.7092	Intermediate Similarity	NPD6799	Approved
0.709	Intermediate Similarity	NPD4307	Phase 2
0.708	Intermediate Similarity	NPD2862	Discontinued
0.7073	Intermediate Similarity	NPD595	Approved
0.7073	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD593	Approved
0.7055	Intermediate Similarity	NPD6801	Discontinued
0.705	Intermediate Similarity	NPD1243	Approved
0.7045	Intermediate Similarity	NPD2614	Approved
0.7042	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7644	Approved
0.7031	Intermediate Similarity	NPD1091	Approved
0.7029	Intermediate Similarity	NPD2344	Approved
0.7029	Intermediate Similarity	NPD5763	Approved
0.7029	Intermediate Similarity	NPD5762	Approved
0.7027	Intermediate Similarity	NPD7768	Phase 2
0.7023	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6584	Phase 3
0.7023	Intermediate Similarity	NPD4624	Approved
0.7016	Intermediate Similarity	NPD255	Approved
0.7016	Intermediate Similarity	NPD256	Approved
0.7015	Intermediate Similarity	NPD8032	Phase 2
0.7009	Intermediate Similarity	NPD9261	Approved
0.7007	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3748	Approved
0.7007	Intermediate Similarity	NPD7819	Suspended
0.7	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6696	Suspended
0.6993	Remote Similarity	NPD6273	Approved
0.6992	Remote Similarity	NPD4625	Phase 3
0.6992	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5746	Approved
0.6992	Remote Similarity	NPD1398	Phase 1
0.6985	Remote Similarity	NPD2157	Approved
0.6984	Remote Similarity	NPD6580	Approved
0.6984	Remote Similarity	NPD6581	Approved
0.698	Remote Similarity	NPD7075	Discontinued
0.6978	Remote Similarity	NPD1549	Phase 2
0.6972	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5808	Clinical (unspecified phase)

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