NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	264.072
LogP:	2.017
LogD:	1.341
LogS:	-3.496
# Rotatable Bonds:	1
TPSA:	51.21
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.667
Synthetic Accessibility Score:	3.616
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.732
MDCK Permeability:	2.6334586436860263e-05
Pgp-inhibitor:	0.889
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	83.58747863769531%
Volume Distribution (VD):	1.082
Pgp-substrate:	9.595209121704102%

ADMET: Metabolism

CYP1A2-inhibitor:	0.913
CYP1A2-substrate:	0.908
CYP2C19-inhibitor:	0.861
CYP2C19-substrate:	0.877
CYP2C9-inhibitor:	0.312
CYP2C9-substrate:	0.643
CYP2D6-inhibitor:	0.691
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.16
CYP3A4-substrate:	0.5

ADMET: Excretion

Clearance (CL):	7.336
Half-life (T1/2):	0.814

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.751
Drug-inuced Liver Injury (DILI):	0.165
AMES Toxicity:	0.504
Rat Oral Acute Toxicity:	0.585
Maximum Recommended Daily Dose:	0.818
Skin Sensitization:	0.854
Carcinogencity:	0.937
Eye Corrosion:	0.548
Eye Irritation:	0.47
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: NPC32285

Natural Product ID:	NPC32285
*Common Name:**	Enokipodin B
IUPAC Name:	2-methyl-5-[(1S)-1,2,2-trimethyl-3-oxocyclopentyl]cyclohexa-2,5-diene-1,4-dione
Synonyms:
Standard InCHIKey:	FZLVOEBHJNRBTE-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-9-7-12(17)10(8-11(9)16)15(4)6-5-13(18)14(15,2)3/h7-8H,5-6H2,1-4H3/t15-/m1/s1
SMILES:	O=C1C=C(C)C(=O)C=C1[C@@]1(C)CCC(=O)C1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506541
PubChem CID:	11288067
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
NPO3973	Flammulina velutipes	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473426]
NPO3973	Flammulina velutipes	Species	Physalacriaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3973	Flammulina velutipes	Species	Physalacriaceae	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
Others	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	0.0	mm	PMID[536047]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	0.0	mm	PMID[536047]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	14.0	mm	PMID[536047]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	17.0	mm	PMID[536047]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	21.0	mm	PMID[536047]

☑ 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 NPC32285 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	156
0.1-0.2	2554
0.2-0.3	15047
0.3-0.4	13528
0.4-0.5	7148
0.5-0.6	3317
0.6-0.7	778
0.7-0.8	140
0.8-0.85	18
0.85-0.9	7
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9355	High Similarity	NPC475523
0.918	High Similarity	NPC212210
0.9016	High Similarity	NPC165695
0.8871	High Similarity	NPC473902
0.8852	High Similarity	NPC475795
0.8852	High Similarity	NPC97322
0.8833	High Similarity	NPC259261
0.8689	High Similarity	NPC25853
0.8667	High Similarity	NPC94991
0.8667	High Similarity	NPC266295
0.8548	High Similarity	NPC213152
0.8485	Intermediate Similarity	NPC162867
0.8485	Intermediate Similarity	NPC61702
0.8438	Intermediate Similarity	NPC470329
0.8413	Intermediate Similarity	NPC288253
0.8361	Intermediate Similarity	NPC30215
0.8358	Intermediate Similarity	NPC265782
0.8358	Intermediate Similarity	NPC251929
0.8358	Intermediate Similarity	NPC2634
0.8235	Intermediate Similarity	NPC54123
0.8209	Intermediate Similarity	NPC139397
0.8197	Intermediate Similarity	NPC193695
0.8197	Intermediate Similarity	NPC267626
0.8197	Intermediate Similarity	NPC55004
0.8197	Intermediate Similarity	NPC230823
0.8197	Intermediate Similarity	NPC49575
0.8154	Intermediate Similarity	NPC251118
0.8136	Intermediate Similarity	NPC296311
0.8116	Intermediate Similarity	NPC303613
0.8116	Intermediate Similarity	NPC474228
0.8095	Intermediate Similarity	NPC127582
0.8088	Intermediate Similarity	NPC307176
0.8088	Intermediate Similarity	NPC260040
0.8065	Intermediate Similarity	NPC311852
0.8	Intermediate Similarity	NPC309852
0.7971	Intermediate Similarity	NPC181204
0.7971	Intermediate Similarity	NPC474562
0.7971	Intermediate Similarity	NPC5701
0.7945	Intermediate Similarity	NPC90965
0.7941	Intermediate Similarity	NPC256846
0.7937	Intermediate Similarity	NPC96551
0.7937	Intermediate Similarity	NPC285594
0.7931	Intermediate Similarity	NPC228776
0.7903	Intermediate Similarity	NPC115385
0.7857	Intermediate Similarity	NPC470045
0.7857	Intermediate Similarity	NPC470044
0.7857	Intermediate Similarity	NPC251705
0.7846	Intermediate Similarity	NPC167256
0.7833	Intermediate Similarity	NPC268564
0.7833	Intermediate Similarity	NPC474141
0.7826	Intermediate Similarity	NPC282593
0.7826	Intermediate Similarity	NPC246722
0.7826	Intermediate Similarity	NPC35734
0.7826	Intermediate Similarity	NPC151045
0.7826	Intermediate Similarity	NPC159577
0.7797	Intermediate Similarity	NPC64866
0.7794	Intermediate Similarity	NPC260474
0.7794	Intermediate Similarity	NPC155198
0.7794	Intermediate Similarity	NPC87141
0.7794	Intermediate Similarity	NPC188292
0.7778	Intermediate Similarity	NPC27610
0.7778	Intermediate Similarity	NPC69408
0.7778	Intermediate Similarity	NPC56905
0.7746	Intermediate Similarity	NPC474796
0.7746	Intermediate Similarity	NPC474797
0.7746	Intermediate Similarity	NPC329866
0.7746	Intermediate Similarity	NPC255021
0.7742	Intermediate Similarity	NPC20603
0.7727	Intermediate Similarity	NPC285371
0.7727	Intermediate Similarity	NPC6697
0.7727	Intermediate Similarity	NPC475124
0.7714	Intermediate Similarity	NPC304983
0.7714	Intermediate Similarity	NPC115023
0.7714	Intermediate Similarity	NPC305501
0.7714	Intermediate Similarity	NPC234707
0.7714	Intermediate Similarity	NPC223187
0.7656	Intermediate Similarity	NPC276764
0.7656	Intermediate Similarity	NPC143834
0.7656	Intermediate Similarity	NPC472304
0.7639	Intermediate Similarity	NPC293803
0.7627	Intermediate Similarity	NPC116906
0.7627	Intermediate Similarity	NPC32351
0.7619	Intermediate Similarity	NPC192427
0.7581	Intermediate Similarity	NPC275472
0.7576	Intermediate Similarity	NPC472306
0.7541	Intermediate Similarity	NPC37644
0.7541	Intermediate Similarity	NPC23117
0.7536	Intermediate Similarity	NPC20610
0.7536	Intermediate Similarity	NPC310992
0.7536	Intermediate Similarity	NPC469688
0.7534	Intermediate Similarity	NPC469796
0.7534	Intermediate Similarity	NPC469793
0.7532	Intermediate Similarity	NPC62214
0.75	Intermediate Similarity	NPC323005
0.75	Intermediate Similarity	NPC170799
0.75	Intermediate Similarity	NPC308108
0.7467	Intermediate Similarity	NPC170793
0.7463	Intermediate Similarity	NPC150162
0.7463	Intermediate Similarity	NPC4638
0.7458	Intermediate Similarity	NPC145311
0.7436	Intermediate Similarity	NPC7927
0.7436	Intermediate Similarity	NPC230527
0.7429	Intermediate Similarity	NPC182815
0.7424	Intermediate Similarity	NPC60565
0.7419	Intermediate Similarity	NPC63396
0.7419	Intermediate Similarity	NPC202850
0.7397	Intermediate Similarity	NPC251435
0.7397	Intermediate Similarity	NPC473171
0.7397	Intermediate Similarity	NPC255650
0.7391	Intermediate Similarity	NPC290350
0.7391	Intermediate Similarity	NPC4370
0.7377	Intermediate Similarity	NPC471751
0.7368	Intermediate Similarity	NPC45495
0.7368	Intermediate Similarity	NPC164218
0.7368	Intermediate Similarity	NPC474509
0.7342	Intermediate Similarity	NPC8571
0.7333	Intermediate Similarity	NPC163984
0.7333	Intermediate Similarity	NPC176819
0.7333	Intermediate Similarity	NPC58970
0.7333	Intermediate Similarity	NPC228911
0.7333	Intermediate Similarity	NPC115515
0.7333	Intermediate Similarity	NPC118788
0.7313	Intermediate Similarity	NPC202118
0.7313	Intermediate Similarity	NPC197238
0.7308	Intermediate Similarity	NPC41539
0.7273	Intermediate Similarity	NPC270042
0.726	Intermediate Similarity	NPC167049
0.726	Intermediate Similarity	NPC469691
0.7258	Intermediate Similarity	NPC45283
0.7258	Intermediate Similarity	NPC69898
0.7258	Intermediate Similarity	NPC14002
0.7258	Intermediate Similarity	NPC295777
0.7246	Intermediate Similarity	NPC176171
0.7246	Intermediate Similarity	NPC92327
0.7237	Intermediate Similarity	NPC7232
0.7222	Intermediate Similarity	NPC190035
0.7222	Intermediate Similarity	NPC144627
0.7222	Intermediate Similarity	NPC21944
0.7222	Intermediate Similarity	NPC470078
0.7213	Intermediate Similarity	NPC236623
0.7213	Intermediate Similarity	NPC27438
0.7206	Intermediate Similarity	NPC469662
0.7188	Intermediate Similarity	NPC473733
0.7183	Intermediate Similarity	NPC469677
0.7179	Intermediate Similarity	NPC129080
0.7179	Intermediate Similarity	NPC472239
0.7179	Intermediate Similarity	NPC142253
0.7179	Intermediate Similarity	NPC477271
0.7179	Intermediate Similarity	NPC477269
0.7179	Intermediate Similarity	NPC477270
0.7179	Intermediate Similarity	NPC3511
0.7164	Intermediate Similarity	NPC260573
0.7162	Intermediate Similarity	NPC216791
0.7162	Intermediate Similarity	NPC77501
0.7162	Intermediate Similarity	NPC476346
0.7143	Intermediate Similarity	NPC250539
0.7143	Intermediate Similarity	NPC176107
0.7143	Intermediate Similarity	NPC5626
0.7125	Intermediate Similarity	NPC142649
0.7125	Intermediate Similarity	NPC472940
0.7125	Intermediate Similarity	NPC472931
0.7125	Intermediate Similarity	NPC11711
0.7123	Intermediate Similarity	NPC474488
0.7123	Intermediate Similarity	NPC56747
0.7123	Intermediate Similarity	NPC180015
0.7123	Intermediate Similarity	NPC130016
0.7123	Intermediate Similarity	NPC109576
0.7105	Intermediate Similarity	NPC474056
0.7105	Intermediate Similarity	NPC469996
0.7101	Intermediate Similarity	NPC183422
0.7089	Intermediate Similarity	NPC65350
0.7083	Intermediate Similarity	NPC214770
0.7083	Intermediate Similarity	NPC40574
0.7083	Intermediate Similarity	NPC477856
0.7069	Intermediate Similarity	NPC25771
0.7067	Intermediate Similarity	NPC27205
0.7067	Intermediate Similarity	NPC470525
0.7067	Intermediate Similarity	NPC1254
0.7067	Intermediate Similarity	NPC469646
0.7067	Intermediate Similarity	NPC215481
0.7051	Intermediate Similarity	NPC477372
0.7051	Intermediate Similarity	NPC136150
0.7042	Intermediate Similarity	NPC469679
0.7031	Intermediate Similarity	NPC200258
0.7027	Intermediate Similarity	NPC20025
0.7	Intermediate Similarity	NPC87552
0.7	Intermediate Similarity	NPC320801
0.7	Intermediate Similarity	NPC154728
0.7	Intermediate Similarity	NPC238197
0.7	Intermediate Similarity	NPC304665
0.7	Intermediate Similarity	NPC91962
0.7	Intermediate Similarity	NPC126899
0.6986	Remote Similarity	NPC133253
0.6986	Remote Similarity	NPC225467
0.6974	Remote Similarity	NPC97377
0.697	Remote Similarity	NPC60772
0.6962	Remote Similarity	NPC320514
0.6962	Remote Similarity	NPC469805
0.6962	Remote Similarity	NPC472867
0.6962	Remote Similarity	NPC469806

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 NPC32285 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	2845
0.2-0.3	4428
0.3-0.4	1181
0.4-0.5	298
0.5-0.6	170
0.6-0.7	61
0.7-0.8	9
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
0.8358	Intermediate Similarity	NPD4691	Approved
0.8209	Intermediate Similarity	NPD4137	Phase 3
0.8088	Intermediate Similarity	NPD4747	Approved
0.8	Intermediate Similarity	NPD4058	Approved
0.7971	Intermediate Similarity	NPD5276	Approved
0.7746	Intermediate Similarity	NPD4687	Approved
0.7746	Intermediate Similarity	NPD5733	Approved
0.7536	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD287	Approved
0.7089	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7331	Phase 2
0.6962	Remote Similarity	NPD4223	Phase 3
0.6962	Remote Similarity	NPD4221	Approved
0.6829	Remote Similarity	NPD5690	Phase 2
0.679	Remote Similarity	NPD3133	Approved
0.679	Remote Similarity	NPD4197	Approved
0.679	Remote Similarity	NPD3665	Phase 1
0.679	Remote Similarity	NPD3666	Approved
0.6709	Remote Similarity	NPD4695	Discontinued
0.6707	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6627	Remote Similarity	NPD7521	Approved
0.6627	Remote Similarity	NPD5205	Approved
0.6627	Remote Similarity	NPD4689	Approved
0.6627	Remote Similarity	NPD3618	Phase 1
0.6627	Remote Similarity	NPD7334	Approved
0.6627	Remote Similarity	NPD6409	Approved
0.6627	Remote Similarity	NPD6684	Approved
0.6627	Remote Similarity	NPD4693	Phase 3
0.6627	Remote Similarity	NPD4690	Approved
0.6627	Remote Similarity	NPD7146	Approved
0.6627	Remote Similarity	NPD5279	Phase 3
0.6627	Remote Similarity	NPD5280	Approved
0.6627	Remote Similarity	NPD4688	Approved
0.6627	Remote Similarity	NPD4138	Approved
0.6627	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5330	Approved
0.6627	Remote Similarity	NPD4694	Approved
0.6591	Remote Similarity	NPD4629	Approved
0.6591	Remote Similarity	NPD5210	Approved
0.6543	Remote Similarity	NPD3667	Approved
0.6471	Remote Similarity	NPD4518	Approved
0.6471	Remote Similarity	NPD5208	Approved
0.6471	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6672	Approved
0.6471	Remote Similarity	NPD5737	Approved
0.6471	Remote Similarity	NPD6903	Approved
0.6437	Remote Similarity	NPD6079	Approved
0.642	Remote Similarity	NPD8028	Phase 2
0.6395	Remote Similarity	NPD5328	Approved
0.6395	Remote Similarity	NPD6904	Approved
0.6395	Remote Similarity	NPD6673	Approved
0.6395	Remote Similarity	NPD4753	Phase 2
0.6395	Remote Similarity	NPD6080	Approved
0.6389	Remote Similarity	NPD7341	Phase 2
0.6386	Remote Similarity	NPD4786	Approved
0.6386	Remote Similarity	NPD3668	Phase 3
0.6375	Remote Similarity	NPD4195	Approved
0.6338	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4096	Approved
0.6322	Remote Similarity	NPD5207	Approved
0.6322	Remote Similarity	NPD5692	Phase 3
0.631	Remote Similarity	NPD1694	Approved
0.6301	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5693	Phase 1
0.625	Remote Similarity	NPD5281	Approved
0.625	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5694	Approved
0.625	Remote Similarity	NPD6050	Approved
0.625	Remote Similarity	NPD5284	Approved
0.6235	Remote Similarity	NPD6098	Approved
0.6235	Remote Similarity	NPD4623	Approved
0.6235	Remote Similarity	NPD4519	Discontinued
0.6197	Remote Similarity	NPD4194	Approved
0.6197	Remote Similarity	NPD4192	Approved
0.6197	Remote Similarity	NPD4191	Approved
0.6197	Remote Similarity	NPD4193	Approved
0.6196	Remote Similarity	NPD5696	Approved
0.618	Remote Similarity	NPD4202	Approved
0.617	Remote Similarity	NPD5091	Approved
0.6163	Remote Similarity	NPD3573	Approved
0.6154	Remote Similarity	NPD5222	Approved
0.6154	Remote Similarity	NPD5221	Approved
0.6154	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6001	Approved
0.6098	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5173	Approved
0.6044	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD5695	Phase 3
0.6032	Remote Similarity	NPD345	Approved
0.6032	Remote Similarity	NPD344	Approved
0.6032	Remote Similarity	NPD343	Approved
0.6024	Remote Similarity	NPD4692	Approved
0.6024	Remote Similarity	NPD4139	Approved
0.6	Remote Similarity	NPD5133	Approved
0.5978	Remote Similarity	NPD4697	Phase 3
0.5957	Remote Similarity	NPD5285	Approved
0.5957	Remote Similarity	NPD5286	Approved
0.5957	Remote Similarity	NPD4696	Approved
0.5955	Remote Similarity	NPD5785	Approved
0.593	Remote Similarity	NPD1696	Phase 3
0.593	Remote Similarity	NPD5363	Approved
0.5918	Remote Similarity	NPD6614	Approved
0.5914	Remote Similarity	NPD4755	Approved
0.5914	Remote Similarity	NPD6084	Phase 2
0.5914	Remote Similarity	NPD6083	Phase 2
0.5895	Remote Similarity	NPD5223	Approved
0.5882	Remote Similarity	NPD4788	Approved
0.5875	Remote Similarity	NPD8039	Approved
0.587	Remote Similarity	NPD5654	Approved
0.5833	Remote Similarity	NPD5226	Approved
0.5833	Remote Similarity	NPD5211	Phase 2
0.5833	Remote Similarity	NPD5225	Approved
0.5833	Remote Similarity	NPD5224	Approved
0.5833	Remote Similarity	NPD4633	Approved
0.5824	Remote Similarity	NPD6399	Phase 3
0.5806	Remote Similarity	NPD7614	Phase 1
0.5806	Remote Similarity	NPD7732	Phase 3
0.5789	Remote Similarity	NPD4700	Approved
0.5773	Remote Similarity	NPD5174	Approved
0.5773	Remote Similarity	NPD5175	Approved
0.5765	Remote Similarity	NPD5209	Approved
0.5745	Remote Similarity	NPD5959	Approved
0.5714	Remote Similarity	NPD5141	Approved
0.5714	Remote Similarity	NPD5368	Approved
0.5714	Remote Similarity	NPD7515	Phase 2
0.5667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5783	Phase 3
0.5652	Remote Similarity	NPD9298	Approved
0.5647	Remote Similarity	NPD5369	Approved
0.5625	Remote Similarity	NPD6404	Discontinued
0.5612	Remote Similarity	NPD6052	Approved
0.5612	Remote Similarity	NPD4754	Approved
0.56	Remote Similarity	NPD5697	Approved
0.56	Remote Similarity	NPD5325	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