NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.12
Volume:	274.872
LogP:	2.185
LogD:	2.824
LogS:	-3.203
# Rotatable Bonds:	2
TPSA:	66.98
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.882
Synthetic Accessibility Score:	3.832
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.712
MDCK Permeability:	1.9529768906068057e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.88
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.436
30% Bioavailability (F30%):	0.453

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.697
Plasma Protein Binding (PPB):	92.28050231933594%
Volume Distribution (VD):	0.715
Pgp-substrate:	6.569943428039551%

ADMET: Metabolism

CYP1A2-inhibitor:	0.776
CYP1A2-substrate:	0.885
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.766
CYP2C9-inhibitor:	0.499
CYP2C9-substrate:	0.738
CYP2D6-inhibitor:	0.203
CYP2D6-substrate:	0.766
CYP3A4-inhibitor:	0.194
CYP3A4-substrate:	0.761

ADMET: Excretion

Clearance (CL):	9.484
Half-life (T1/2):	0.704

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.233
Drug-inuced Liver Injury (DILI):	0.684
AMES Toxicity:	0.183
Rat Oral Acute Toxicity:	0.215
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.413
Carcinogencity:	0.83
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.888

Download Data

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

Natural Product: NPC158551

Natural Product ID:	NPC158551
*Common Name:**	Limazepine C
IUPAC Name:	(6aS)-8-ethyl-4-hydroxy-3-methoxy-6a,7-dihydropyrrolo[2,1-c][1,4]benzodiazepin-11-one
Synonyms:	Limazepine C
Standard InCHIKey:	FLGURYUVNVBBFP-JTQLQIEISA-N
Standard InCHI:	InChI=1S/C15H16N2O3/c1-3-9-6-10-7-16-13-11(15(19)17(10)8-9)4-5-12(20-2)14(13)18/h4-5,7-8,10,18H,3,6H2,1-2H3/t10-/m0/s1
SMILES:	CCC1=CN2[C@@H](C1)C=Nc1c(ccc(c1O)OC)C2=O
Synthetic Gene Cluster:	BGC0001652;
ChEMBL Identifier:	CHEMBL555727
PubChem CID:	42639506
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000295] Benzodiazepines [CHEMONTID:0004097] 1,4-benzodiazepines

*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
NPO32521	micrococcus sp.	Species	Micrococcaceae	Bacteria	n.a.	Indonesian	n.a.	PMID[19388705]

☑ 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
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	18.0	mm	PMID[540292]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	10.0	mm	PMID[540292]

☑ 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 NPC158551 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	354
0.1-0.2	3135
0.2-0.3	12915
0.3-0.4	3958
0.4-0.5	13274
0.5-0.6	8043
0.6-0.7	988
0.7-0.8	26
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9728	High Similarity	NPC163829
0.8476	Intermediate Similarity	NPC172222
0.8441	Intermediate Similarity	NPC270301
0.8068	Intermediate Similarity	NPC313327
0.7788	Intermediate Similarity	NPC470481
0.7788	Intermediate Similarity	NPC470482
0.772	Intermediate Similarity	NPC98416
0.768	Intermediate Similarity	NPC28368
0.7464	Intermediate Similarity	NPC16249
0.7437	Intermediate Similarity	NPC87391
0.7383	Intermediate Similarity	NPC2905
0.7361	Intermediate Similarity	NPC182853
0.7339	Intermediate Similarity	NPC76478
0.733	Intermediate Similarity	NPC135006
0.7323	Intermediate Similarity	NPC197335
0.7286	Intermediate Similarity	NPC314659
0.7282	Intermediate Similarity	NPC161804
0.726	Intermediate Similarity	NPC7560
0.7256	Intermediate Similarity	NPC114468
0.7222	Intermediate Similarity	NPC148391
0.7202	Intermediate Similarity	NPC134702
0.7189	Intermediate Similarity	NPC471531
0.7182	Intermediate Similarity	NPC118189
0.7163	Intermediate Similarity	NPC295479
0.7163	Intermediate Similarity	NPC220241
0.7158	Intermediate Similarity	NPC470708
0.7156	Intermediate Similarity	NPC473460
0.7128	Intermediate Similarity	NPC469540
0.7128	Intermediate Similarity	NPC469539
0.7123	Intermediate Similarity	NPC473422
0.7122	Intermediate Similarity	NPC92803
0.7115	Intermediate Similarity	NPC316282
0.7103	Intermediate Similarity	NPC100573
0.7103	Intermediate Similarity	NPC207873
0.7098	Intermediate Similarity	NPC470480
0.7078	Intermediate Similarity	NPC126556
0.7056	Intermediate Similarity	NPC212123
0.7054	Intermediate Similarity	NPC285254
0.7024	Intermediate Similarity	NPC18890
0.7019	Intermediate Similarity	NPC198401
0.701	Intermediate Similarity	NPC262725
0.7005	Intermediate Similarity	NPC204970
0.7	Intermediate Similarity	NPC71124
0.6996	Remote Similarity	NPC250960
0.6996	Remote Similarity	NPC71539
0.6991	Remote Similarity	NPC471561
0.699	Remote Similarity	NPC174629
0.6971	Remote Similarity	NPC254957
0.6963	Remote Similarity	NPC14339
0.6963	Remote Similarity	NPC268077
0.6963	Remote Similarity	NPC119669
0.6947	Remote Similarity	NPC13249
0.694	Remote Similarity	NPC41501
0.6939	Remote Similarity	NPC299582
0.6935	Remote Similarity	NPC138438
0.6935	Remote Similarity	NPC908
0.6931	Remote Similarity	NPC39822
0.6931	Remote Similarity	NPC5167
0.6927	Remote Similarity	NPC471532
0.6903	Remote Similarity	NPC266994
0.6895	Remote Similarity	NPC119722
0.6887	Remote Similarity	NPC5374
0.6881	Remote Similarity	NPC287152
0.6864	Remote Similarity	NPC268223
0.6858	Remote Similarity	NPC122886
0.6844	Remote Similarity	NPC148124
0.6842	Remote Similarity	NPC74216
0.6842	Remote Similarity	NPC246381
0.684	Remote Similarity	NPC17677
0.6837	Remote Similarity	NPC207971
0.6832	Remote Similarity	NPC9475
0.6818	Remote Similarity	NPC305542
0.6816	Remote Similarity	NPC195120
0.6816	Remote Similarity	NPC87560
0.6806	Remote Similarity	NPC153644
0.6804	Remote Similarity	NPC269449
0.68	Remote Similarity	NPC99724
0.6796	Remote Similarity	NPC138083
0.6792	Remote Similarity	NPC24228
0.6789	Remote Similarity	NPC90185
0.6787	Remote Similarity	NPC30749
0.6781	Remote Similarity	NPC314702
0.6766	Remote Similarity	NPC73280
0.6765	Remote Similarity	NPC85613
0.6765	Remote Similarity	NPC32064
0.6759	Remote Similarity	NPC41216
0.6748	Remote Similarity	NPC132385
0.6742	Remote Similarity	NPC10732
0.6741	Remote Similarity	NPC173080
0.6736	Remote Similarity	NPC270515
0.6727	Remote Similarity	NPC474366
0.6725	Remote Similarity	NPC248903
0.6714	Remote Similarity	NPC28510
0.67	Remote Similarity	NPC35345
0.6683	Remote Similarity	NPC276120
0.6682	Remote Similarity	NPC206109
0.6682	Remote Similarity	NPC114039
0.6681	Remote Similarity	NPC26928
0.6681	Remote Similarity	NPC157983
0.6681	Remote Similarity	NPC118154
0.6667	Remote Similarity	NPC116178
0.6667	Remote Similarity	NPC471489
0.6667	Remote Similarity	NPC291173
0.6667	Remote Similarity	NPC174122
0.6667	Remote Similarity	NPC64140
0.6667	Remote Similarity	NPC170333
0.6667	Remote Similarity	NPC470821
0.6652	Remote Similarity	NPC128476
0.6638	Remote Similarity	NPC19175
0.6637	Remote Similarity	NPC217903
0.6636	Remote Similarity	NPC272706
0.6635	Remote Similarity	NPC1820
0.6634	Remote Similarity	NPC20395
0.662	Remote Similarity	NPC127178
0.6619	Remote Similarity	NPC162694
0.6619	Remote Similarity	NPC234069
0.6618	Remote Similarity	NPC8467
0.6605	Remote Similarity	NPC112937
0.6602	Remote Similarity	NPC222524
0.66	Remote Similarity	NPC153631
0.6597	Remote Similarity	NPC477395
0.6596	Remote Similarity	NPC231572
0.6591	Remote Similarity	NPC198160
0.6578	Remote Similarity	NPC122553
0.6576	Remote Similarity	NPC308885
0.6576	Remote Similarity	NPC255550
0.6575	Remote Similarity	NPC210256
0.6575	Remote Similarity	NPC475147
0.6573	Remote Similarity	NPC203972
0.6569	Remote Similarity	NPC160100
0.6569	Remote Similarity	NPC164608
0.6566	Remote Similarity	NPC301163
0.6562	Remote Similarity	NPC321166
0.6555	Remote Similarity	NPC473007
0.6547	Remote Similarity	NPC218303
0.6541	Remote Similarity	NPC93882
0.6541	Remote Similarity	NPC130595
0.654	Remote Similarity	NPC477186
0.6535	Remote Similarity	NPC10653
0.6535	Remote Similarity	NPC318525
0.6533	Remote Similarity	NPC93653
0.6533	Remote Similarity	NPC298449
0.6533	Remote Similarity	NPC176113
0.6531	Remote Similarity	NPC185172
0.6528	Remote Similarity	NPC100863
0.6524	Remote Similarity	NPC116007
0.6518	Remote Similarity	NPC159815
0.6516	Remote Similarity	NPC308943
0.6509	Remote Similarity	NPC29531
0.6505	Remote Similarity	NPC285078
0.6505	Remote Similarity	NPC6854
0.6505	Remote Similarity	NPC313737
0.6502	Remote Similarity	NPC134637
0.65	Remote Similarity	NPC257763
0.6497	Remote Similarity	NPC133011
0.6497	Remote Similarity	NPC82285
0.6495	Remote Similarity	NPC94499
0.6484	Remote Similarity	NPC474077
0.6483	Remote Similarity	NPC253675
0.6471	Remote Similarity	NPC218530
0.6463	Remote Similarity	NPC303374
0.6462	Remote Similarity	NPC124626
0.6462	Remote Similarity	NPC169387
0.6462	Remote Similarity	NPC241392
0.6462	Remote Similarity	NPC477259
0.646	Remote Similarity	NPC146976
0.6457	Remote Similarity	NPC475133
0.6456	Remote Similarity	NPC67978
0.6456	Remote Similarity	NPC303581
0.645	Remote Similarity	NPC235628
0.6449	Remote Similarity	NPC473004
0.6447	Remote Similarity	NPC82056
0.6445	Remote Similarity	NPC150308
0.6444	Remote Similarity	NPC316981
0.6443	Remote Similarity	NPC315829
0.6442	Remote Similarity	NPC283810
0.6441	Remote Similarity	NPC478075
0.6435	Remote Similarity	NPC329830
0.6432	Remote Similarity	NPC473008
0.6432	Remote Similarity	NPC470001
0.6432	Remote Similarity	NPC470002
0.6429	Remote Similarity	NPC470088
0.6425	Remote Similarity	NPC256935
0.6422	Remote Similarity	NPC207239
0.6419	Remote Similarity	NPC470485
0.6417	Remote Similarity	NPC266425
0.6416	Remote Similarity	NPC236668
0.6413	Remote Similarity	NPC329567
0.6413	Remote Similarity	NPC205926
0.6413	Remote Similarity	NPC330683
0.6411	Remote Similarity	NPC73555
0.641	Remote Similarity	NPC321505
0.641	Remote Similarity	NPC179825
0.641	Remote Similarity	NPC191376
0.6409	Remote Similarity	NPC15987
0.6404	Remote Similarity	NPC476569
0.6402	Remote Similarity	NPC43218
0.6396	Remote Similarity	NPC478189
0.6396	Remote Similarity	NPC477161
0.6394	Remote Similarity	NPC308267

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 NPC158551 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	669
0.2-0.3	1169
0.3-0.4	1646
0.4-0.5	3143
0.5-0.6	2043
0.6-0.7	264
0.7-0.8	11
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8058	Intermediate Similarity	NPD7559	Phase 2
0.7802	Intermediate Similarity	NPD824	Approved
0.7327	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2899	Discontinued
0.7216	Intermediate Similarity	NPD2821	Approved
0.7189	Intermediate Similarity	NPD5025	Approved
0.7083	Intermediate Similarity	NPD683	Approved
0.7039	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD6795	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.692	Remote Similarity	NPD4049	Phase 2
0.6919	Remote Similarity	NPD5071	Phase 2
0.6895	Remote Similarity	NPD7225	Discontinued
0.6888	Remote Similarity	NPD8091	Phase 3
0.6881	Remote Similarity	NPD5645	Phase 3
0.6869	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1670	Discontinued
0.6812	Remote Similarity	NPD4515	Suspended
0.681	Remote Similarity	NPD3631	Phase 3
0.6806	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3802	Phase 3
0.6753	Remote Similarity	NPD2592	Discontinued
0.675	Remote Similarity	NPD5183	Approved
0.675	Remote Similarity	NPD5186	Approved
0.675	Remote Similarity	NPD1293	Approved
0.6731	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.67	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7291	Discontinued
0.6698	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD743	Approved
0.6667	Remote Similarity	NPD7263	Phase 2
0.6651	Remote Similarity	NPD4539	Phase 1
0.6638	Remote Similarity	NPD3442	Approved
0.6638	Remote Similarity	NPD3441	Approved
0.6621	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.662	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3592	Approved
0.6606	Remote Similarity	NPD3591	Approved
0.6581	Remote Similarity	NPD6625	Approved
0.6578	Remote Similarity	NPD8149	Discontinued
0.6576	Remote Similarity	NPD3145	Approved
0.6576	Remote Similarity	NPD3144	Approved
0.6569	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD2674	Phase 3
0.6526	Remote Similarity	NPD3633	Approved
0.6526	Remote Similarity	NPD3634	Approved
0.652	Remote Similarity	NPD1220	Phase 1
0.6513	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD2843	Phase 2
0.6509	Remote Similarity	NPD2845	Phase 2
0.6507	Remote Similarity	NPD7280	Phase 3
0.6507	Remote Similarity	NPD7281	Phase 3
0.6505	Remote Similarity	NPD1221	Approved
0.6502	Remote Similarity	NPD5914	Approved
0.6502	Remote Similarity	NPD5860	Discontinued
0.65	Remote Similarity	NPD4465	Phase 2
0.65	Remote Similarity	NPD4467	Phase 2
0.65	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.649	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.649	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4082	Approved
0.6484	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD4493	Discontinued
0.6473	Remote Similarity	NPD4206	Approved
0.6471	Remote Similarity	NPD4083	Discontinued
0.6453	Remote Similarity	NPD2680	Approved
0.6453	Remote Similarity	NPD6199	Discontinued
0.6453	Remote Similarity	NPD2681	Approved
0.645	Remote Similarity	NPD5978	Approved
0.645	Remote Similarity	NPD5977	Approved
0.6445	Remote Similarity	NPD3153	Approved
0.6445	Remote Similarity	NPD3154	Approved
0.6442	Remote Similarity	NPD6297	Approved
0.6441	Remote Similarity	NPD4596	Phase 1
0.6429	Remote Similarity	NPD3893	Discontinued
0.6425	Remote Similarity	NPD3793	Phase 3
0.6414	Remote Similarity	NPD5617	Suspended
0.6413	Remote Similarity	NPD2907	Approved
0.6413	Remote Similarity	NPD3472	Approved
0.6413	Remote Similarity	NPD4022	Approved
0.6413	Remote Similarity	NPD2906	Approved
0.6408	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD6618	Phase 2
0.6396	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD2325	Approved
0.6385	Remote Similarity	NPD3349	Phase 2
0.6382	Remote Similarity	NPD6385	Approved
0.6382	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD7110	Phase 1
0.6382	Remote Similarity	NPD6386	Approved
0.6377	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD2247	Approved
0.6373	Remote Similarity	NPD2249	Approved
0.6372	Remote Similarity	NPD5937	Approved
0.6372	Remote Similarity	NPD4492	Approved
0.6372	Remote Similarity	NPD4494	Approved
0.6372	Remote Similarity	NPD3888	Discontinued
0.6371	Remote Similarity	NPD4373	Phase 2
0.6359	Remote Similarity	NPD2898	Approved
0.6356	Remote Similarity	NPD3372	Discontinued
0.6351	Remote Similarity	NPD7546	Discontinued
0.6351	Remote Similarity	NPD3298	Approved
0.6347	Remote Similarity	NPD6874	Approved
0.6347	Remote Similarity	NPD7810	Phase 3
0.6347	Remote Similarity	NPD7811	Phase 3
0.6346	Remote Similarity	NPD5312	Approved
0.6346	Remote Similarity	NPD5313	Approved
0.6345	Remote Similarity	NPD3639	Approved
0.6345	Remote Similarity	NPD3640	Phase 3
0.6345	Remote Similarity	NPD3641	Approved
0.6344	Remote Similarity	NPD4455	Discontinued
0.6343	Remote Similarity	NPD4466	Phase 1
0.6332	Remote Similarity	NPD3684	Discontinued
0.6332	Remote Similarity	NPD6875	Approved
0.6332	Remote Similarity	NPD6876	Approved
0.6332	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5515	Phase 2
0.6325	Remote Similarity	NPD5640	Discontinued
0.6324	Remote Similarity	NPD9494	Approved
0.6322	Remote Similarity	NPD6716	Phase 1
0.6321	Remote Similarity	NPD6851	Approved
0.6321	Remote Similarity	NPD6853	Approved
0.632	Remote Similarity	NPD3437	Discontinued
0.6313	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD4157	Discontinued
0.6308	Remote Similarity	NPD1898	Discontinued
0.6308	Remote Similarity	NPD2792	Approved
0.6305	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD1309	Phase 2
0.6305	Remote Similarity	NPD1307	Phase 2
0.63	Remote Similarity	NPD2672	Discontinued
0.6294	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD5561	Approved
0.6288	Remote Similarity	NPD5562	Approved
0.628	Remote Similarity	NPD6894	Phase 1
0.6279	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5519	Discontinued
0.6277	Remote Similarity	NPD5496	Approved
0.6276	Remote Similarity	NPD4357	Discontinued
0.6274	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6274	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD3965	Phase 1
0.6267	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD6997	Phase 2
0.6263	Remote Similarity	NPD711	Discontinued
0.6262	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD7316	Discontinued
0.6261	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD4605	Approved
0.6256	Remote Similarity	NPD1945	Phase 1
0.6256	Remote Similarity	NPD4604	Approved
0.6255	Remote Similarity	NPD7186	Phase 3
0.625	Remote Similarity	NPD5641	Discontinued
0.625	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD5022	Discontinued
0.6245	Remote Similarity	NPD4952	Phase 3
0.6244	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.624	Remote Similarity	NPD7560	Approved
0.624	Remote Similarity	NPD7886	Phase 2
0.624	Remote Similarity	NPD7885	Phase 2
0.624	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD3912	Discontinued
0.6239	Remote Similarity	NPD7278	Phase 2
0.6239	Remote Similarity	NPD7279	Phase 2
0.6224	Remote Similarity	NPD7048	Phase 3
0.6222	Remote Similarity	NPD6296	Discontinued
0.6218	Remote Similarity	NPD1505	Phase 2
0.6218	Remote Similarity	NPD6962	Phase 2
0.6217	Remote Similarity	NPD6744	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6790	Phase 1
0.621	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5967	Approved
0.6207	Remote Similarity	NPD6063	Approved
0.6203	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD7013	Phase 3
0.6194	Remote Similarity	NPD7012	Phase 3
0.6192	Remote Similarity	NPD7031	Phase 1
0.6189	Remote Similarity	NPD1483	Discontinued
0.6184	Remote Similarity	NPD4166	Phase 2
0.6183	Remote Similarity	NPD3006	Discontinued
0.6182	Remote Similarity	NPD5564	Approved
0.618	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD5871	Discontinued
0.6171	Remote Similarity	NPD5457	Discontinued
0.6171	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7922	Phase 1
0.6167	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD4429	Discontinued
0.6161	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7597	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