NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	372.27
Volume:	419.736
LogP:	6.199
LogD:	5.018
LogS:	-5.114
# Rotatable Bonds:	5
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.452
Synthetic Accessibility Score:	4.745
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.714
MDCK Permeability:	1.5159139366005547e-05
Pgp-inhibitor:	0.661
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.185
Plasma Protein Binding (PPB):	94.33253479003906%
Volume Distribution (VD):	2.434
Pgp-substrate:	5.291028022766113%

ADMET: Metabolism

CYP1A2-inhibitor:	0.128
CYP1A2-substrate:	0.702
CYP2C19-inhibitor:	0.876
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.859
CYP2C9-substrate:	0.271
CYP2D6-inhibitor:	0.551
CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.903
CYP3A4-substrate:	0.851

ADMET: Excretion

Clearance (CL):	12.362
Half-life (T1/2):	0.043

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.907
Drug-inuced Liver Injury (DILI):	0.292
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.152
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.194
Carcinogencity:	0.942
Eye Corrosion:	0.008
Eye Irritation:	0.042
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC478246

Natural Product ID:	NPC478246
*Common Name:**	Frutescone R
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YLLJLJGJAVHFKG-YADARESESA-N
Standard InCHI:	InChI=1S/C24H36O3/c1-15(2)10-9-11-18-12-13-19(16(3)4)24(14-18)20(25)17(5)21(27-8)23(6,7)22(24)26/h10,12,16,19H,9,11,13-14H2,1-8H3/t19-,24+/m0/s1
SMILES:	COC1=C(C)C(=O)[C@]2(CC(CCC=C(C)C)=CC[C@H]2C(C)C)C(=O)C1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(98)00534-2]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932146]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	aerial parts	Nanning, Guangxi Province, China	2014-OCT	PMID[28753309]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11277	Baeckea frutescens	Species	Myrtaceae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC478246 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	207
0.1-0.2	1550
0.2-0.3	7135
0.3-0.4	15804
0.4-0.5	10238
0.5-0.6	5579
0.6-0.7	1927
0.7-0.8	247
0.8-0.85	5
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC478247
0.8659	High Similarity	NPC38885
0.8608	High Similarity	NPC472684
0.8608	High Similarity	NPC44963
0.8375	Intermediate Similarity	NPC474085
0.8375	Intermediate Similarity	NPC189237
0.8228	Intermediate Similarity	NPC469996
0.814	Intermediate Similarity	NPC213636
0.814	Intermediate Similarity	NPC280592
0.814	Intermediate Similarity	NPC253177
0.8125	Intermediate Similarity	NPC28319
0.8101	Intermediate Similarity	NPC472300
0.8095	Intermediate Similarity	NPC477478
0.8095	Intermediate Similarity	NPC470345
0.8095	Intermediate Similarity	NPC477479
0.8046	Intermediate Similarity	NPC296114
0.8046	Intermediate Similarity	NPC471329
0.7976	Intermediate Similarity	NPC133652
0.7976	Intermediate Similarity	NPC263997
0.7976	Intermediate Similarity	NPC132228
0.7976	Intermediate Similarity	NPC8518
0.7949	Intermediate Similarity	NPC306928
0.7927	Intermediate Similarity	NPC478262
0.7927	Intermediate Similarity	NPC116797
0.7907	Intermediate Similarity	NPC143025
0.7907	Intermediate Similarity	NPC478261
0.7907	Intermediate Similarity	NPC478259
0.7907	Intermediate Similarity	NPC478260
0.7889	Intermediate Similarity	NPC21681
0.7889	Intermediate Similarity	NPC472734
0.7889	Intermediate Similarity	NPC472675
0.7889	Intermediate Similarity	NPC472733
0.7882	Intermediate Similarity	NPC470346
0.7838	Intermediate Similarity	NPC251118
0.7805	Intermediate Similarity	NPC2482
0.7805	Intermediate Similarity	NPC108955
0.7802	Intermediate Similarity	NPC472731
0.7802	Intermediate Similarity	NPC472732
0.7802	Intermediate Similarity	NPC27105
0.7778	Intermediate Similarity	NPC275494
0.7778	Intermediate Similarity	NPC74410
0.7778	Intermediate Similarity	NPC471409
0.7778	Intermediate Similarity	NPC189485
0.7765	Intermediate Similarity	NPC241512
0.7765	Intermediate Similarity	NPC6185
0.775	Intermediate Similarity	NPC899
0.775	Intermediate Similarity	NPC470525
0.7738	Intermediate Similarity	NPC53733
0.7717	Intermediate Similarity	NPC472730
0.7717	Intermediate Similarity	NPC99657
0.7717	Intermediate Similarity	NPC203388
0.7717	Intermediate Similarity	NPC472687
0.7717	Intermediate Similarity	NPC177680
0.7717	Intermediate Similarity	NPC472729
0.7717	Intermediate Similarity	NPC471330
0.7717	Intermediate Similarity	NPC153776
0.7717	Intermediate Similarity	NPC471331
0.7711	Intermediate Similarity	NPC55869
0.7711	Intermediate Similarity	NPC149237
0.7683	Intermediate Similarity	NPC476177
0.7662	Intermediate Similarity	NPC256846
0.7654	Intermediate Similarity	NPC283087
0.7647	Intermediate Similarity	NPC473246
0.7634	Intermediate Similarity	NPC472728
0.7634	Intermediate Similarity	NPC472727
0.7619	Intermediate Similarity	NPC129080
0.7619	Intermediate Similarity	NPC321289
0.7619	Intermediate Similarity	NPC103486
0.7619	Intermediate Similarity	NPC477270
0.7619	Intermediate Similarity	NPC327969
0.7619	Intermediate Similarity	NPC477271
0.7619	Intermediate Similarity	NPC470813
0.7619	Intermediate Similarity	NPC477269
0.7614	Intermediate Similarity	NPC472676
0.7614	Intermediate Similarity	NPC472688
0.759	Intermediate Similarity	NPC267517
0.7582	Intermediate Similarity	NPC777
0.7561	Intermediate Similarity	NPC23778
0.7561	Intermediate Similarity	NPC30321
0.7561	Intermediate Similarity	NPC321514
0.7561	Intermediate Similarity	NPC4827
0.7561	Intermediate Similarity	NPC62336
0.7558	Intermediate Similarity	NPC478245
0.7558	Intermediate Similarity	NPC469948
0.7532	Intermediate Similarity	NPC260474
0.7532	Intermediate Similarity	NPC87141
0.7532	Intermediate Similarity	NPC188292
0.7531	Intermediate Similarity	NPC263582
0.7531	Intermediate Similarity	NPC180886
0.7531	Intermediate Similarity	NPC40353
0.7531	Intermediate Similarity	NPC92080
0.7528	Intermediate Similarity	NPC223093
0.75	Intermediate Similarity	NPC225515
0.75	Intermediate Similarity	NPC471898
0.75	Intermediate Similarity	NPC477372
0.75	Intermediate Similarity	NPC470524
0.75	Intermediate Similarity	NPC53454
0.75	Intermediate Similarity	NPC166797
0.75	Intermediate Similarity	NPC474353
0.75	Intermediate Similarity	NPC278459
0.75	Intermediate Similarity	NPC121984
0.75	Intermediate Similarity	NPC476988
0.7473	Intermediate Similarity	NPC114162
0.7473	Intermediate Similarity	NPC469819
0.7471	Intermediate Similarity	NPC229717
0.7471	Intermediate Similarity	NPC195640
0.7471	Intermediate Similarity	NPC220478
0.7471	Intermediate Similarity	NPC194417
0.7468	Intermediate Similarity	NPC474539
0.7442	Intermediate Similarity	NPC120158
0.7442	Intermediate Similarity	NPC476412
0.7442	Intermediate Similarity	NPC214043
0.7442	Intermediate Similarity	NPC85774
0.7442	Intermediate Similarity	NPC320801
0.7442	Intermediate Similarity	NPC475193
0.7439	Intermediate Similarity	NPC266193
0.7439	Intermediate Similarity	NPC197659
0.7439	Intermediate Similarity	NPC257666
0.7439	Intermediate Similarity	NPC165711
0.7436	Intermediate Similarity	NPC469914
0.7432	Intermediate Similarity	NPC60565
0.7416	Intermediate Similarity	NPC275740
0.7416	Intermediate Similarity	NPC280833
0.7416	Intermediate Similarity	NPC284561
0.7416	Intermediate Similarity	NPC469546
0.7416	Intermediate Similarity	NPC86319
0.7412	Intermediate Similarity	NPC163236
0.7412	Intermediate Similarity	NPC70479
0.7412	Intermediate Similarity	NPC240302
0.7412	Intermediate Similarity	NPC100297
0.7407	Intermediate Similarity	NPC114236
0.7407	Intermediate Similarity	NPC65650
0.7391	Intermediate Similarity	NPC31021
0.7386	Intermediate Similarity	NPC476079
0.7386	Intermediate Similarity	NPC471728
0.7386	Intermediate Similarity	NPC113370
0.7386	Intermediate Similarity	NPC470523
0.7386	Intermediate Similarity	NPC103743
0.7381	Intermediate Similarity	NPC26139
0.7381	Intermediate Similarity	NPC45495
0.7381	Intermediate Similarity	NPC279667
0.7381	Intermediate Similarity	NPC476809
0.7363	Intermediate Similarity	NPC474807
0.7363	Intermediate Similarity	NPC263780
0.7356	Intermediate Similarity	NPC2709
0.7356	Intermediate Similarity	NPC189311
0.7356	Intermediate Similarity	NPC474853
0.7356	Intermediate Similarity	NPC179006
0.7356	Intermediate Similarity	NPC470048
0.7356	Intermediate Similarity	NPC474537
0.7356	Intermediate Similarity	NPC474680
0.7356	Intermediate Similarity	NPC323765
0.7349	Intermediate Similarity	NPC178852
0.7349	Intermediate Similarity	NPC207772
0.734	Intermediate Similarity	NPC147954
0.7333	Intermediate Similarity	NPC113393
0.7333	Intermediate Similarity	NPC288253
0.7326	Intermediate Similarity	NPC193198
0.7326	Intermediate Similarity	NPC470047
0.7326	Intermediate Similarity	NPC64600
0.7326	Intermediate Similarity	NPC271784
0.7326	Intermediate Similarity	NPC49019
0.7326	Intermediate Similarity	NPC477373
0.7326	Intermediate Similarity	NPC470046
0.7317	Intermediate Similarity	NPC26504
0.7308	Intermediate Similarity	NPC155198
0.7308	Intermediate Similarity	NPC310992
0.7303	Intermediate Similarity	NPC471724
0.7303	Intermediate Similarity	NPC131470
0.7303	Intermediate Similarity	NPC472302
0.7303	Intermediate Similarity	NPC471722
0.7303	Intermediate Similarity	NPC307298
0.7303	Intermediate Similarity	NPC72397
0.7303	Intermediate Similarity	NPC318578
0.7303	Intermediate Similarity	NPC474854
0.7303	Intermediate Similarity	NPC143767
0.7297	Intermediate Similarity	NPC127582
0.7294	Intermediate Similarity	NPC282293
0.7294	Intermediate Similarity	NPC473217
0.7294	Intermediate Similarity	NPC475665
0.7294	Intermediate Similarity	NPC3915
0.7294	Intermediate Similarity	NPC14151
0.7294	Intermediate Similarity	NPC201912
0.7294	Intermediate Similarity	NPC99308
0.7294	Intermediate Similarity	NPC38350
0.7294	Intermediate Similarity	NPC474955
0.7294	Intermediate Similarity	NPC327002
0.7284	Intermediate Similarity	NPC167049
0.7284	Intermediate Similarity	NPC469691
0.7284	Intermediate Similarity	NPC301065
0.7273	Intermediate Similarity	NPC118648
0.7273	Intermediate Similarity	NPC470955
0.7273	Intermediate Similarity	NPC31564
0.7273	Intermediate Similarity	NPC474778
0.7273	Intermediate Similarity	NPC474732
0.7273	Intermediate Similarity	NPC222613
0.7273	Intermediate Similarity	NPC474733
0.7273	Intermediate Similarity	NPC327115
0.7273	Intermediate Similarity	NPC475022
0.7273	Intermediate Similarity	NPC72133

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 NPC478246 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	2164
0.2-0.3	4062
0.3-0.4	1956
0.4-0.5	466
0.5-0.6	213
0.6-0.7	83
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7471	Intermediate Similarity	NPD6684	Approved
0.7471	Intermediate Similarity	NPD7521	Approved
0.7471	Intermediate Similarity	NPD7334	Approved
0.7471	Intermediate Similarity	NPD5330	Approved
0.7471	Intermediate Similarity	NPD7146	Approved
0.7471	Intermediate Similarity	NPD6409	Approved
0.7381	Intermediate Similarity	NPD4695	Discontinued
0.7303	Intermediate Similarity	NPD6903	Approved
0.7303	Intermediate Similarity	NPD6672	Approved
0.7303	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5737	Approved
0.7284	Intermediate Similarity	NPD5733	Approved
0.7273	Intermediate Similarity	NPD7331	Phase 2
0.7241	Intermediate Similarity	NPD3666	Approved
0.7241	Intermediate Similarity	NPD3665	Phase 1
0.7241	Intermediate Similarity	NPD3133	Approved
0.7222	Intermediate Similarity	NPD5328	Approved
0.7215	Intermediate Similarity	NPD4137	Phase 3
0.7209	Intermediate Similarity	NPD4221	Approved
0.7209	Intermediate Similarity	NPD4223	Phase 3
0.7191	Intermediate Similarity	NPD3573	Approved
0.7159	Intermediate Similarity	NPD5329	Approved
0.7143	Intermediate Similarity	NPD3617	Approved
0.7143	Intermediate Similarity	NPD7341	Phase 2
0.7125	Intermediate Similarity	NPD4691	Approved
0.7125	Intermediate Similarity	NPD4747	Approved
0.7079	Intermediate Similarity	NPD5280	Approved
0.7079	Intermediate Similarity	NPD3618	Phase 1
0.7079	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5690	Phase 2
0.7079	Intermediate Similarity	NPD5279	Phase 3
0.7079	Intermediate Similarity	NPD4694	Approved
0.7073	Intermediate Similarity	NPD4687	Approved
0.7065	Intermediate Similarity	NPD6079	Approved
0.7065	Intermediate Similarity	NPD6050	Approved
0.7051	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4786	Approved
0.7045	Intermediate Similarity	NPD4197	Approved
0.7037	Intermediate Similarity	NPD5276	Approved
0.7033	Intermediate Similarity	NPD6904	Approved
0.7033	Intermediate Similarity	NPD6080	Approved
0.7033	Intermediate Similarity	NPD6673	Approved
0.7033	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3667	Approved
0.6957	Remote Similarity	NPD5207	Approved
0.6957	Remote Similarity	NPD5692	Phase 3
0.6947	Remote Similarity	NPD7732	Phase 3
0.6923	Remote Similarity	NPD5208	Approved
0.6915	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7900	Approved
0.6915	Remote Similarity	NPD7748	Approved
0.6889	Remote Similarity	NPD5205	Approved
0.6889	Remote Similarity	NPD4519	Discontinued
0.6889	Remote Similarity	NPD4688	Approved
0.6889	Remote Similarity	NPD4693	Phase 3
0.6889	Remote Similarity	NPD6098	Approved
0.6889	Remote Similarity	NPD4138	Approved
0.6889	Remote Similarity	NPD4689	Approved
0.6889	Remote Similarity	NPD4623	Approved
0.6889	Remote Similarity	NPD4690	Approved
0.6882	Remote Similarity	NPD7515	Phase 2
0.6882	Remote Similarity	NPD5694	Approved
0.6882	Remote Similarity	NPD6411	Approved
0.6867	Remote Similarity	NPD4058	Approved
0.6854	Remote Similarity	NPD3668	Phase 3
0.6848	Remote Similarity	NPD4753	Phase 2
0.6842	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5695	Phase 3
0.6818	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.68	Remote Similarity	NPD287	Approved
0.6778	Remote Similarity	NPD1694	Approved
0.6737	Remote Similarity	NPD5282	Discontinued
0.6702	Remote Similarity	NPD5284	Approved
0.6702	Remote Similarity	NPD5693	Phase 1
0.6702	Remote Similarity	NPD5281	Approved
0.6701	Remote Similarity	NPD7902	Approved
0.6701	Remote Similarity	NPD6083	Phase 2
0.6701	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4202	Approved
0.6632	Remote Similarity	NPD6399	Phase 3
0.6598	Remote Similarity	NPD5221	Approved
0.6598	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7614	Phase 1
0.6598	Remote Similarity	NPD5222	Approved
0.6598	Remote Similarity	NPD4697	Phase 3
0.6596	Remote Similarity	NPD4096	Approved
0.6562	Remote Similarity	NPD6001	Approved
0.6559	Remote Similarity	NPD4518	Approved
0.6556	Remote Similarity	NPD4788	Approved
0.6531	Remote Similarity	NPD5173	Approved
0.6531	Remote Similarity	NPD4755	Approved
0.6517	Remote Similarity	NPD4139	Approved
0.6517	Remote Similarity	NPD8028	Phase 2
0.6517	Remote Similarity	NPD4692	Approved
0.6495	Remote Similarity	NPD5654	Approved
0.6495	Remote Similarity	NPD5210	Approved
0.6495	Remote Similarity	NPD4629	Approved
0.6477	Remote Similarity	NPD4195	Approved
0.6465	Remote Similarity	NPD5696	Approved
0.6458	Remote Similarity	NPD5778	Approved
0.6458	Remote Similarity	NPD5779	Approved
0.6458	Remote Similarity	NPD5133	Approved
0.6444	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6402	Approved
0.6408	Remote Similarity	NPD7128	Approved
0.6408	Remote Similarity	NPD5739	Approved
0.6408	Remote Similarity	NPD6675	Approved
0.6404	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5285	Approved
0.64	Remote Similarity	NPD4700	Approved
0.64	Remote Similarity	NPD4696	Approved
0.64	Remote Similarity	NPD5286	Approved
0.6395	Remote Similarity	NPD8039	Approved
0.6374	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5959	Approved
0.6337	Remote Similarity	NPD5223	Approved
0.6286	Remote Similarity	NPD6881	Approved
0.6286	Remote Similarity	NPD7320	Approved
0.6286	Remote Similarity	NPD6899	Approved
0.6275	Remote Similarity	NPD5225	Approved
0.6275	Remote Similarity	NPD4633	Approved
0.6275	Remote Similarity	NPD5211	Phase 2
0.6275	Remote Similarity	NPD5224	Approved
0.6275	Remote Similarity	NPD5226	Approved
0.625	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6008	Approved
0.625	Remote Similarity	NPD5785	Approved
0.6226	Remote Similarity	NPD6372	Approved
0.6226	Remote Similarity	NPD6373	Approved
0.622	Remote Similarity	NPD3704	Approved
0.6214	Remote Similarity	NPD4754	Approved
0.6214	Remote Similarity	NPD6052	Approved
0.6214	Remote Similarity	NPD5175	Approved
0.6214	Remote Similarity	NPD5174	Approved
0.619	Remote Similarity	NPD6412	Phase 2
0.619	Remote Similarity	NPD5697	Approved
0.619	Remote Similarity	NPD5701	Approved
0.6168	Remote Similarity	NPD4634	Approved
0.6168	Remote Similarity	NPD7290	Approved
0.6168	Remote Similarity	NPD7102	Approved
0.6168	Remote Similarity	NPD6883	Approved
0.6162	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5369	Approved
0.6154	Remote Similarity	NPD5141	Approved
0.6132	Remote Similarity	NPD6011	Approved
0.6111	Remote Similarity	NPD8130	Phase 1
0.6111	Remote Similarity	NPD6649	Approved
0.6111	Remote Similarity	NPD6869	Approved
0.6111	Remote Similarity	NPD6617	Approved
0.6111	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6650	Approved
0.6111	Remote Similarity	NPD7645	Phase 2
0.6111	Remote Similarity	NPD6847	Approved
0.6095	Remote Similarity	NPD4767	Approved
0.6095	Remote Similarity	NPD4768	Approved
0.6087	Remote Similarity	NPD5209	Approved
0.6078	Remote Similarity	NPD6404	Discontinued
0.6075	Remote Similarity	NPD6013	Approved
0.6075	Remote Similarity	NPD6014	Approved
0.6075	Remote Similarity	NPD6012	Approved
0.6067	Remote Similarity	NPD4756	Discovery
0.6064	Remote Similarity	NPD5363	Approved
0.6064	Remote Similarity	NPD1696	Phase 3
0.6055	Remote Similarity	NPD8297	Approved
0.6055	Remote Similarity	NPD6882	Approved
0.6047	Remote Similarity	NPD4243	Approved
0.6038	Remote Similarity	NPD6614	Approved
0.6026	Remote Similarity	NPD8779	Phase 3
0.6023	Remote Similarity	NPD7339	Approved
0.6023	Remote Similarity	NPD6942	Approved
0.6022	Remote Similarity	NPD6110	Phase 1
0.6	Remote Similarity	NPD5786	Approved
0.6	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD7115	Discovery
0.5981	Remote Similarity	NPD4729	Approved
0.5981	Remote Similarity	NPD5168	Approved
0.5981	Remote Similarity	NPD5128	Approved
0.5981	Remote Similarity	NPD4730	Approved
0.598	Remote Similarity	NPD7638	Approved
0.5965	Remote Similarity	NPD6054	Approved
0.5965	Remote Similarity	NPD6059	Approved
0.5962	Remote Similarity	NPD5091	Approved
0.5955	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD7639	Approved
0.5922	Remote Similarity	NPD7640	Approved
0.5914	Remote Similarity	NPD4270	Approved
0.5914	Remote Similarity	NPD6435	Approved
0.5914	Remote Similarity	NPD4269	Approved
0.5909	Remote Similarity	NPD6053	Discontinued
0.5909	Remote Similarity	NPD4784	Approved
0.5909	Remote Similarity	NPD4785	Approved
0.5895	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6868	Approved
0.5872	Remote Similarity	NPD5250	Approved
0.5872	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD5135	Approved
0.5872	Remote Similarity	NPD5169	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