NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.16
Volume:	304.584
LogP:	4.991
LogD:	4.352
LogS:	-4.178
# Rotatable Bonds:	7
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.747
Synthetic Accessibility Score:	2.18
Fsp3:	0.353
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.829
MDCK Permeability:	2.446332473482471e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.06
Plasma Protein Binding (PPB):	99.59697723388672%
Volume Distribution (VD):	0.279
Pgp-substrate:	1.8891971111297607%

ADMET: Metabolism

CYP1A2-inhibitor:	0.285
CYP1A2-substrate:	0.143
CYP2C19-inhibitor:	0.14
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.551
CYP2C9-substrate:	0.422
CYP2D6-inhibitor:	0.077
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.044
CYP3A4-substrate:	0.111

ADMET: Excretion

Clearance (CL):	3.983
Half-life (T1/2):	0.724

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.907
Drug-inuced Liver Injury (DILI):	0.749
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.598
Carcinogencity:	0.04
Eye Corrosion:	0.004
Eye Irritation:	0.867
Respiratory Toxicity:	0.04

Download Data

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

Natural Product: NPC221798

Natural Product ID:	NPC221798
*Common Name:**	Geranyloxy-P-Benzoic Acid
IUPAC Name:	4-[(2E)-3,7-dimethylocta-2,6-dienoxy]benzoic acid
Synonyms:	Geranyloxy-P-Benzoic Acid
Standard InCHIKey:	RMDHZUUXNBGDEM-SDNWHVSQSA-N
Standard InCHI:	InChI=1S/C17H22O3/c1-13(2)5-4-6-14(3)11-12-20-16-9-7-15(8-10-16)17(18)19/h5,7-11H,4,6,12H2,1-3H3,(H,18,19)/p-1/b14-11+
SMILES:	CC(=CCC/C(=C/COc1ccc(cc1)C(=O)[O-])/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2022664
PubChem CID:	12361500
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO20738	Piper crassinervium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22472691]
NPO20738	Piper crassinervium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20738	Piper crassinervium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20738	Piper crassinervium	Species	Piperaceae	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
IC50	1
Others	10

Activity Type	# Activity
Cell Line	1
Individual Protein	7
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	0.902	n.a.	PMID[477622]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	0.899	n.a.	PMID[477622]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	0.993	n.a.	PMID[477622]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.054	n.a.	PMID[477622]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.348	n.a.	PMID[477622]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.854	n.a.	PMID[477622]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	2.82	n.a.	PMID[477622]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	200000.0	nM	PMID[477623]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	10.0	%	PMID[477624]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	33.0	%	PMID[477624]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	3.0	%	PMID[477624]

☑ 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 NPC221798 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	263
0.1-0.2	1422
0.2-0.3	4127
0.3-0.4	9421
0.4-0.5	8691
0.5-0.6	4037
0.6-0.7	8740
0.7-0.8	5499
0.8-0.85	454
0.85-0.9	29
0.9-0.95	9
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9829	High Similarity	NPC291189
0.9829	High Similarity	NPC69403
0.9504	High Similarity	NPC475236
0.9487	High Similarity	NPC61779
0.935	High Similarity	NPC2596
0.9237	High Similarity	NPC27633
0.9237	High Similarity	NPC94298
0.9145	High Similarity	NPC220540
0.9068	High Similarity	NPC131192
0.9048	High Similarity	NPC327457
0.9048	High Similarity	NPC86774
0.904	High Similarity	NPC2401
0.8976	High Similarity	NPC104854
0.896	High Similarity	NPC121104
0.8952	High Similarity	NPC49938
0.8898	High Similarity	NPC109778
0.888	High Similarity	NPC110211
0.888	High Similarity	NPC204579
0.8871	High Similarity	NPC184219
0.8837	High Similarity	NPC66158
0.881	High Similarity	NPC37512
0.88	High Similarity	NPC165556
0.875	High Similarity	NPC470860
0.8739	High Similarity	NPC252004
0.8731	High Similarity	NPC184053
0.871	High Similarity	NPC67300
0.8672	High Similarity	NPC194979
0.8607	High Similarity	NPC293424
0.8605	High Similarity	NPC307732
0.8605	High Similarity	NPC285776
0.8605	High Similarity	NPC42292
0.8603	High Similarity	NPC473090
0.8583	High Similarity	NPC474476
0.8582	High Similarity	NPC473988
0.8571	High Similarity	NPC240593
0.855	High Similarity	NPC203817
0.8537	High Similarity	NPC264976
0.8527	High Similarity	NPC238309
0.8525	High Similarity	NPC240664
0.8519	High Similarity	NPC80098
0.8519	High Similarity	NPC326065
0.8512	High Similarity	NPC322358
0.8507	High Similarity	NPC188879
0.8487	Intermediate Similarity	NPC23332
0.8487	Intermediate Similarity	NPC57879
0.8475	Intermediate Similarity	NPC234639
0.8473	Intermediate Similarity	NPC302844
0.8462	Intermediate Similarity	NPC183348
0.8462	Intermediate Similarity	NPC157473
0.8462	Intermediate Similarity	NPC151530
0.8462	Intermediate Similarity	NPC282230
0.8456	Intermediate Similarity	NPC307990
0.8456	Intermediate Similarity	NPC16455
0.845	Intermediate Similarity	NPC473744
0.845	Intermediate Similarity	NPC293453
0.8444	Intermediate Similarity	NPC124269
0.8433	Intermediate Similarity	NPC187826
0.843	Intermediate Similarity	NPC235250
0.8421	Intermediate Similarity	NPC144027
0.8421	Intermediate Similarity	NPC236974
0.8413	Intermediate Similarity	NPC311219
0.8409	Intermediate Similarity	NPC283823
0.8409	Intermediate Similarity	NPC159418
0.8403	Intermediate Similarity	NPC183648
0.8397	Intermediate Similarity	NPC15083
0.8397	Intermediate Similarity	NPC470976
0.8397	Intermediate Similarity	NPC470977
0.8397	Intermediate Similarity	NPC196979
0.8385	Intermediate Similarity	NPC170546
0.8385	Intermediate Similarity	NPC66246
0.8385	Intermediate Similarity	NPC226855
0.8385	Intermediate Similarity	NPC939
0.8385	Intermediate Similarity	NPC78662
0.8385	Intermediate Similarity	NPC8005
0.8382	Intermediate Similarity	NPC230902
0.8382	Intermediate Similarity	NPC51181
0.8376	Intermediate Similarity	NPC176971
0.8376	Intermediate Similarity	NPC184658
0.8374	Intermediate Similarity	NPC469954
0.8361	Intermediate Similarity	NPC51345
0.8358	Intermediate Similarity	NPC294470
0.8357	Intermediate Similarity	NPC66991
0.8357	Intermediate Similarity	NPC472969
0.8346	Intermediate Similarity	NPC311339
0.8345	Intermediate Similarity	NPC291153
0.8333	Intermediate Similarity	NPC309717
0.8333	Intermediate Similarity	NPC111888
0.8333	Intermediate Similarity	NPC128348
0.8333	Intermediate Similarity	NPC112192
0.8333	Intermediate Similarity	NPC164236
0.8333	Intermediate Similarity	NPC66384
0.8333	Intermediate Similarity	NPC469615
0.8333	Intermediate Similarity	NPC189106
0.8321	Intermediate Similarity	NPC247779
0.832	Intermediate Similarity	NPC474874
0.8309	Intermediate Similarity	NPC99333
0.8309	Intermediate Similarity	NPC280284
0.8309	Intermediate Similarity	NPC475045
0.8309	Intermediate Similarity	NPC188947
0.8308	Intermediate Similarity	NPC186098
0.8308	Intermediate Similarity	NPC80694
0.8306	Intermediate Similarity	NPC161943
0.8306	Intermediate Similarity	NPC21831
0.8306	Intermediate Similarity	NPC273282
0.8306	Intermediate Similarity	NPC187547
0.8306	Intermediate Similarity	NPC474890
0.8305	Intermediate Similarity	NPC29883
0.8298	Intermediate Similarity	NPC98809
0.8298	Intermediate Similarity	NPC476394
0.8296	Intermediate Similarity	NPC156910
0.8296	Intermediate Similarity	NPC470398
0.8296	Intermediate Similarity	NPC470397
0.8296	Intermediate Similarity	NPC121243
0.8296	Intermediate Similarity	NPC240147
0.8295	Intermediate Similarity	NPC154275
0.8295	Intermediate Similarity	NPC95309
0.8293	Intermediate Similarity	NPC19290
0.8291	Intermediate Similarity	NPC128730
0.8291	Intermediate Similarity	NPC238115
0.8286	Intermediate Similarity	NPC286038
0.8284	Intermediate Similarity	NPC212729
0.8284	Intermediate Similarity	NPC61499
0.8281	Intermediate Similarity	NPC145134
0.8281	Intermediate Similarity	NPC89630
0.8281	Intermediate Similarity	NPC6888
0.8273	Intermediate Similarity	NPC469683
0.8271	Intermediate Similarity	NPC114116
0.8271	Intermediate Similarity	NPC10971
0.8261	Intermediate Similarity	NPC474385
0.8258	Intermediate Similarity	NPC473777
0.8258	Intermediate Similarity	NPC125153
0.8248	Intermediate Similarity	NPC23257
0.8248	Intermediate Similarity	NPC79908
0.8244	Intermediate Similarity	NPC474289
0.824	Intermediate Similarity	NPC90522
0.824	Intermediate Similarity	NPC328459
0.8239	Intermediate Similarity	NPC473091
0.8239	Intermediate Similarity	NPC182350
0.8235	Intermediate Similarity	NPC475005
0.8235	Intermediate Similarity	NPC207516
0.8235	Intermediate Similarity	NPC253616
0.8235	Intermediate Similarity	NPC275055
0.8235	Intermediate Similarity	NPC291837
0.8235	Intermediate Similarity	NPC62735
0.8235	Intermediate Similarity	NPC290291
0.8235	Intermediate Similarity	NPC266597
0.8235	Intermediate Similarity	NPC474943
0.8235	Intermediate Similarity	NPC250266
0.8231	Intermediate Similarity	NPC258567
0.8231	Intermediate Similarity	NPC121740
0.8231	Intermediate Similarity	NPC22783
0.8231	Intermediate Similarity	NPC224774
0.8231	Intermediate Similarity	NPC158654
0.8226	Intermediate Similarity	NPC45104
0.8226	Intermediate Similarity	NPC217423
0.8222	Intermediate Similarity	NPC64230
0.8222	Intermediate Similarity	NPC223616
0.8222	Intermediate Similarity	NPC163029
0.8222	Intermediate Similarity	NPC71638
0.822	Intermediate Similarity	NPC326447
0.822	Intermediate Similarity	NPC1065
0.8217	Intermediate Similarity	NPC2771
0.8217	Intermediate Similarity	NPC470858
0.8217	Intermediate Similarity	NPC4164
0.8217	Intermediate Similarity	NPC473626
0.8214	Intermediate Similarity	NPC469953
0.8214	Intermediate Similarity	NPC472034
0.8209	Intermediate Similarity	NPC263670
0.8209	Intermediate Similarity	NPC155098
0.8209	Intermediate Similarity	NPC472365
0.8209	Intermediate Similarity	NPC242294
0.8209	Intermediate Similarity	NPC312318
0.8209	Intermediate Similarity	NPC56031
0.8209	Intermediate Similarity	NPC188646
0.8209	Intermediate Similarity	NPC192304
0.8209	Intermediate Similarity	NPC139813
0.8209	Intermediate Similarity	NPC337373
0.8209	Intermediate Similarity	NPC175098
0.8209	Intermediate Similarity	NPC27643
0.8209	Intermediate Similarity	NPC223457
0.8205	Intermediate Similarity	NPC2518
0.8203	Intermediate Similarity	NPC11799
0.8203	Intermediate Similarity	NPC141252
0.8201	Intermediate Similarity	NPC471028
0.8197	Intermediate Similarity	NPC109241
0.8195	Intermediate Similarity	NPC31872
0.8195	Intermediate Similarity	NPC473584
0.8195	Intermediate Similarity	NPC308037
0.8195	Intermediate Similarity	NPC475589
0.8195	Intermediate Similarity	NPC64359
0.8188	Intermediate Similarity	NPC110228
0.8188	Intermediate Similarity	NPC76445
0.8188	Intermediate Similarity	NPC471587
0.8188	Intermediate Similarity	NPC188243
0.8188	Intermediate Similarity	NPC1704
0.8188	Intermediate Similarity	NPC284550
0.8188	Intermediate Similarity	NPC6407
0.8188	Intermediate Similarity	NPC475730
0.8188	Intermediate Similarity	NPC67650
0.8188	Intermediate Similarity	NPC129853

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 NPC221798 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	914
0.2-0.3	1554
0.3-0.4	2510
0.4-0.5	1895
0.5-0.6	1274
0.6-0.7	552
0.7-0.8	197
0.8-0.85	15
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9237	High Similarity	NPD9545	Approved
0.8797	High Similarity	NPD7421	Clinical (unspecified phase)
0.8731	High Similarity	NPD4628	Phase 3
0.8462	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8413	Intermediate Similarity	NPD9717	Approved
0.8347	Intermediate Similarity	NPD1241	Discontinued
0.8305	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD6799	Approved
0.8268	Intermediate Similarity	NPD1608	Approved
0.822	Intermediate Similarity	NPD3134	Approved
0.8175	Intermediate Similarity	NPD1778	Approved
0.816	Intermediate Similarity	NPD1894	Discontinued
0.8125	Intermediate Similarity	NPD7411	Suspended
0.8077	Intermediate Similarity	NPD1203	Approved
0.806	Intermediate Similarity	NPD1240	Approved
0.8043	Intermediate Similarity	NPD1549	Phase 2
0.8031	Intermediate Similarity	NPD17	Approved
0.803	Intermediate Similarity	NPD6832	Phase 2
0.8029	Intermediate Similarity	NPD1551	Phase 2
0.8029	Intermediate Similarity	NPD2796	Approved
0.8	Intermediate Similarity	NPD9493	Approved
0.8	Intermediate Similarity	NPD1358	Approved
0.8	Intermediate Similarity	NPD230	Phase 1
0.7984	Intermediate Similarity	NPD3972	Approved
0.7971	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD2799	Discontinued
0.7955	Intermediate Similarity	NPD9494	Approved
0.7941	Intermediate Similarity	NPD1607	Approved
0.7939	Intermediate Similarity	NPD2797	Approved
0.7931	Intermediate Similarity	NPD6599	Discontinued
0.7929	Intermediate Similarity	NPD3750	Approved
0.7926	Intermediate Similarity	NPD3140	Approved
0.7926	Intermediate Similarity	NPD3142	Approved
0.7914	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD422	Phase 1
0.7902	Intermediate Similarity	NPD2186	Approved
0.7891	Intermediate Similarity	NPD7819	Suspended
0.7891	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1019	Discontinued
0.7863	Intermediate Similarity	NPD3225	Approved
0.7852	Intermediate Similarity	NPD7075	Discontinued
0.7846	Intermediate Similarity	NPD1481	Phase 2
0.7832	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7033	Discontinued
0.7826	Intermediate Similarity	NPD1510	Phase 2
0.7823	Intermediate Similarity	NPD6801	Discontinued
0.7817	Intermediate Similarity	NPD7440	Discontinued
0.7778	Intermediate Similarity	NPD411	Approved
0.7778	Intermediate Similarity	NPD3268	Approved
0.7778	Intermediate Similarity	NPD3764	Approved
0.7778	Intermediate Similarity	NPD6798	Discontinued
0.777	Intermediate Similarity	NPD2935	Discontinued
0.7769	Intermediate Similarity	NPD1535	Discovery
0.7762	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD2354	Approved
0.7746	Intermediate Similarity	NPD3887	Approved
0.7737	Intermediate Similarity	NPD447	Suspended
0.7721	Intermediate Similarity	NPD4062	Phase 3
0.7721	Intermediate Similarity	NPD6233	Phase 2
0.7714	Intermediate Similarity	NPD2344	Approved
0.7708	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD3748	Approved
0.7698	Intermediate Similarity	NPD4308	Phase 3
0.7692	Intermediate Similarity	NPD3496	Discontinued
0.7687	Intermediate Similarity	NPD454	Approved
0.7676	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7768	Phase 2
0.7655	Intermediate Similarity	NPD6273	Approved
0.7647	Intermediate Similarity	NPD2313	Discontinued
0.7642	Intermediate Similarity	NPD2684	Approved
0.7634	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6355	Discontinued
0.7606	Intermediate Similarity	NPD1243	Approved
0.7603	Intermediate Similarity	NPD5403	Approved
0.76	Intermediate Similarity	NPD3817	Phase 2
0.7589	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD2353	Approved
0.7589	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD2533	Approved
0.7586	Intermediate Similarity	NPD2532	Approved
0.7586	Intermediate Similarity	NPD2534	Approved
0.7569	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD3847	Discontinued
0.7552	Intermediate Similarity	NPD7003	Approved
0.755	Intermediate Similarity	NPD3882	Suspended
0.7548	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD9697	Approved
0.754	Intermediate Similarity	NPD5535	Approved
0.7538	Intermediate Similarity	NPD5585	Approved
0.7533	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4477	Approved
0.7518	Intermediate Similarity	NPD4476	Approved
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2614	Approved
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD7458	Discontinued
0.7483	Intermediate Similarity	NPD920	Approved
0.7483	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD1933	Approved
0.7482	Intermediate Similarity	NPD4340	Discontinued
0.7481	Intermediate Similarity	NPD2798	Approved
0.7481	Intermediate Similarity	NPD5647	Approved
0.7481	Intermediate Similarity	NPD4626	Approved
0.7467	Intermediate Similarity	NPD1934	Approved
0.7466	Intermediate Similarity	NPD5401	Approved
0.7466	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD6002	Phase 3
0.7465	Intermediate Similarity	NPD6004	Phase 3
0.7465	Intermediate Similarity	NPD6005	Phase 3
0.7465	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD1283	Approved
0.7463	Intermediate Similarity	NPD1876	Approved
0.745	Intermediate Similarity	NPD4380	Phase 2
0.7431	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD9267	Approved
0.7419	Intermediate Similarity	NPD9263	Approved
0.7419	Intermediate Similarity	NPD9264	Approved
0.7417	Intermediate Similarity	NPD1238	Approved
0.7417	Intermediate Similarity	NPD2801	Approved
0.741	Intermediate Similarity	NPD4307	Phase 2
0.7407	Intermediate Similarity	NPD3266	Approved
0.7407	Intermediate Similarity	NPD3267	Approved
0.7405	Intermediate Similarity	NPD5844	Phase 1
0.7405	Intermediate Similarity	NPD5691	Approved
0.7402	Intermediate Similarity	NPD7843	Approved
0.7402	Intermediate Similarity	NPD821	Approved
0.74	Intermediate Similarity	NPD6385	Approved
0.74	Intermediate Similarity	NPD6386	Approved
0.7397	Intermediate Similarity	NPD1511	Approved
0.7391	Intermediate Similarity	NPD1296	Phase 2
0.7386	Intermediate Similarity	NPD3749	Approved
0.7381	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD74	Approved
0.736	Intermediate Similarity	NPD9266	Approved
0.736	Intermediate Similarity	NPD2182	Approved
0.7357	Intermediate Similarity	NPD5124	Phase 1
0.7357	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7577	Discontinued
0.7347	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3146	Approved
0.7343	Intermediate Similarity	NPD2346	Discontinued
0.7339	Intermediate Similarity	NPD968	Approved
0.7328	Intermediate Similarity	NPD1548	Phase 1
0.7319	Intermediate Similarity	NPD5163	Phase 2
0.7312	Intermediate Similarity	NPD5953	Discontinued
0.7297	Intermediate Similarity	NPD1512	Approved
0.7297	Intermediate Similarity	NPD5049	Phase 3
0.7296	Intermediate Similarity	NPD7286	Phase 2
0.7292	Intermediate Similarity	NPD4534	Discontinued
0.7285	Intermediate Similarity	NPD958	Approved
0.728	Intermediate Similarity	NPD290	Approved
0.7279	Intermediate Similarity	NPD6362	Approved
0.7273	Intermediate Similarity	NPD2240	Approved
0.7273	Intermediate Similarity	NPD9268	Approved
0.7273	Intermediate Similarity	NPD2239	Approved
0.7273	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6190	Approved
0.7259	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4359	Approved
0.7255	Intermediate Similarity	NPD5402	Approved
0.7248	Intermediate Similarity	NPD1670	Discontinued
0.7244	Intermediate Similarity	NPD2247	Approved
0.7244	Intermediate Similarity	NPD2249	Approved
0.7241	Intermediate Similarity	NPD2800	Approved
0.7239	Intermediate Similarity	NPD1281	Approved
0.7233	Intermediate Similarity	NPD7177	Discontinued
0.7231	Intermediate Similarity	NPD7157	Approved
0.7206	Intermediate Similarity	NPD196	Phase 1
0.72	Intermediate Similarity	NPD957	Approved
0.7194	Intermediate Similarity	NPD7095	Approved
0.7192	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4110	Phase 3
0.7185	Intermediate Similarity	NPD9269	Phase 2
0.7183	Intermediate Similarity	NPD6651	Approved
0.7183	Intermediate Similarity	NPD6653	Approved
0.7181	Intermediate Similarity	NPD9509	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD9258	Approved
0.7179	Intermediate Similarity	NPD9256	Approved
0.7172	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5958	Discontinued
0.7171	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4060	Phase 1
0.7163	Intermediate Similarity	NPD2979	Phase 3
0.7161	Intermediate Similarity	NPD6971	Discontinued
0.7153	Intermediate Similarity	NPD6100	Approved
0.7153	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD5353	Approved
0.7133	Intermediate Similarity	NPD7097	Phase 1
0.7133	Intermediate Similarity	NPD5586	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