NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.12
Volume:	274.872
LogP:	2.006
LogD:	1.951
LogS:	-2.724
# Rotatable Bonds:	1
TPSA:	62.13
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.798
Synthetic Accessibility Score:	3.788
Fsp3:	0.333
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:	-4.522
MDCK Permeability:	1.699965650914237e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.837
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.911
Plasma Protein Binding (PPB):	85.10845184326172%
Volume Distribution (VD):	1.274
Pgp-substrate:	15.551410675048828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.225
CYP1A2-substrate:	0.282
CYP2C19-inhibitor:	0.212
CYP2C19-substrate:	0.801
CYP2C9-inhibitor:	0.206
CYP2C9-substrate:	0.888
CYP2D6-inhibitor:	0.127
CYP2D6-substrate:	0.464
CYP3A4-inhibitor:	0.247
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	5.012
Half-life (T1/2):	0.635

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.648
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.549
Rat Oral Acute Toxicity:	0.139
Maximum Recommended Daily Dose:	0.074
Skin Sensitization:	0.097
Carcinogencity:	0.938
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.063

Download Data

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

Natural Product: NPC163829

Natural Product ID:	NPC163829
*Common Name:**	Limazepine E
IUPAC Name:	(6aS,8E)-8-ethylidene-4-hydroxy-3-methoxy-7,9-dihydro-6aH-pyrrolo[2,1-c][1,4]benzodiazepin-11-one
Synonyms:	Limazepine E
Standard InCHIKey:	FOMJEHKAWAOFOV-RZCNENHTSA-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/h3-5,7,10,18H,6,8H2,1-2H3/b9-3+/t10-/m0/s1
SMILES:	C/C=C/1C[C@H]2C=Nc3c(ccc(c3O)OC)C(=O)N2C1
Synthetic Gene Cluster:	BGC0001652;
ChEMBL Identifier:	CHEMBL550498
PubChem CID:	42639507
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	=	12.0	mm	PMID[502307]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	10.0	mm	PMID[502307]

☑ 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 NPC163829 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	347
0.1-0.2	2653
0.2-0.3	12205
0.3-0.4	4886
0.4-0.5	12995
0.5-0.6	8397
0.6-0.7	1174
0.7-0.8	36
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9728	High Similarity	NPC158551
0.8689	High Similarity	NPC270301
0.8606	High Similarity	NPC172222
0.8284	Intermediate Similarity	NPC313327
0.8	Intermediate Similarity	NPC470481
0.8	Intermediate Similarity	NPC470482
0.776	Intermediate Similarity	NPC98416
0.767	Intermediate Similarity	NPC16249
0.7538	Intermediate Similarity	NPC197335
0.7538	Intermediate Similarity	NPC28368
0.75	Intermediate Similarity	NPC314659
0.7488	Intermediate Similarity	NPC161804
0.7418	Intermediate Similarity	NPC2905
0.7395	Intermediate Similarity	NPC182853
0.7373	Intermediate Similarity	NPC76478
0.7368	Intermediate Similarity	NPC135006
0.7351	Intermediate Similarity	NPC469539
0.7351	Intermediate Similarity	NPC469540
0.7299	Intermediate Similarity	NPC100573
0.7299	Intermediate Similarity	NPC207873
0.7294	Intermediate Similarity	NPC7560
0.729	Intermediate Similarity	NPC114468
0.7287	Intermediate Similarity	NPC470708
0.7285	Intermediate Similarity	NPC470480
0.7269	Intermediate Similarity	NPC126556
0.7256	Intermediate Similarity	NPC148391
0.7235	Intermediate Similarity	NPC134702
0.7222	Intermediate Similarity	NPC471531
0.722	Intermediate Similarity	NPC198401
0.7215	Intermediate Similarity	NPC118189
0.7214	Intermediate Similarity	NPC87391
0.7196	Intermediate Similarity	NPC295479
0.7196	Intermediate Similarity	NPC220241
0.719	Intermediate Similarity	NPC473460
0.7157	Intermediate Similarity	NPC92803
0.7156	Intermediate Similarity	NPC473422
0.7115	Intermediate Similarity	NPC71124
0.7089	Intermediate Similarity	NPC212123
0.7087	Intermediate Similarity	NPC254957
0.7085	Intermediate Similarity	NPC285254
0.7083	Intermediate Similarity	NPC119722
0.7075	Intermediate Similarity	NPC268077
0.7059	Intermediate Similarity	NPC18890
0.705	Intermediate Similarity	NPC5167
0.7044	Intermediate Similarity	NPC262725
0.704	Intermediate Similarity	NPC122886
0.7039	Intermediate Similarity	NPC204970
0.7027	Intermediate Similarity	NPC250960
0.7027	Intermediate Similarity	NPC71539
0.7027	Intermediate Similarity	NPC148124
0.7024	Intermediate Similarity	NPC174629
0.7023	Intermediate Similarity	NPC471561
0.7	Intermediate Similarity	NPC5374
0.7	Intermediate Similarity	NPC287152
0.7	Intermediate Similarity	NPC119669
0.6995	Remote Similarity	NPC14339
0.6991	Remote Similarity	NPC269449
0.6982	Remote Similarity	NPC99724
0.6978	Remote Similarity	NPC13249
0.6977	Remote Similarity	NPC90185
0.6974	Remote Similarity	NPC299582
0.6973	Remote Similarity	NPC908
0.6973	Remote Similarity	NPC138438
0.6965	Remote Similarity	NPC39822
0.6959	Remote Similarity	NPC471532
0.6948	Remote Similarity	NPC207971
0.6933	Remote Similarity	NPC266994
0.6927	Remote Similarity	NPC10732
0.6923	Remote Similarity	NPC87560
0.6923	Remote Similarity	NPC195120
0.6905	Remote Similarity	NPC316282
0.6905	Remote Similarity	NPC24228
0.6904	Remote Similarity	NPC35345
0.6903	Remote Similarity	NPC248903
0.6897	Remote Similarity	NPC41501
0.6895	Remote Similarity	NPC268223
0.6881	Remote Similarity	NPC85613
0.6872	Remote Similarity	NPC17677
0.6872	Remote Similarity	NPC74216
0.6869	Remote Similarity	NPC41216
0.6866	Remote Similarity	NPC9475
0.6858	Remote Similarity	NPC26928
0.6849	Remote Similarity	NPC305542
0.6842	Remote Similarity	NPC153644
0.684	Remote Similarity	NPC291173
0.683	Remote Similarity	NPC128476
0.6829	Remote Similarity	NPC138083
0.6818	Remote Similarity	NPC30749
0.6814	Remote Similarity	NPC19175
0.6812	Remote Similarity	NPC162694
0.6808	Remote Similarity	NPC127178
0.68	Remote Similarity	NPC73280
0.6798	Remote Similarity	NPC246381
0.6798	Remote Similarity	NPC32064
0.6793	Remote Similarity	NPC122553
0.6786	Remote Similarity	NPC157983
0.6786	Remote Similarity	NPC118154
0.6773	Remote Similarity	NPC116178
0.6766	Remote Similarity	NPC477395
0.6759	Remote Similarity	NPC475147
0.6758	Remote Similarity	NPC474366
0.6748	Remote Similarity	NPC473007
0.6742	Remote Similarity	NPC217903
0.6731	Remote Similarity	NPC477186
0.6715	Remote Similarity	NPC276120
0.6714	Remote Similarity	NPC100863
0.6714	Remote Similarity	NPC112937
0.6714	Remote Similarity	NPC114039
0.6714	Remote Similarity	NPC206109
0.6711	Remote Similarity	NPC10653
0.6711	Remote Similarity	NPC318525
0.6707	Remote Similarity	NPC132385
0.6701	Remote Similarity	NPC257763
0.6699	Remote Similarity	NPC64140
0.6699	Remote Similarity	NPC174122
0.6698	Remote Similarity	NPC471489
0.6698	Remote Similarity	NPC170333
0.6697	Remote Similarity	NPC159815
0.6697	Remote Similarity	NPC198160
0.6696	Remote Similarity	NPC470821
0.6696	Remote Similarity	NPC173080
0.6695	Remote Similarity	NPC270515
0.6682	Remote Similarity	NPC94499
0.6682	Remote Similarity	NPC210256
0.6667	Remote Similarity	NPC272706
0.6667	Remote Similarity	NPC321166
0.6667	Remote Similarity	NPC160100
0.6667	Remote Similarity	NPC20395
0.6651	Remote Similarity	NPC234069
0.665	Remote Similarity	NPC8467
0.6636	Remote Similarity	NPC475133
0.6635	Remote Similarity	NPC116007
0.6635	Remote Similarity	NPC473004
0.6635	Remote Similarity	NPC150308
0.6634	Remote Similarity	NPC222524
0.6633	Remote Similarity	NPC153631
0.6631	Remote Similarity	NPC231572
0.6626	Remote Similarity	NPC303374
0.6621	Remote Similarity	NPC478075
0.6619	Remote Similarity	NPC473008
0.6612	Remote Similarity	NPC255550
0.6612	Remote Similarity	NPC308885
0.6601	Remote Similarity	NPC164608
0.6599	Remote Similarity	NPC301163
0.6596	Remote Similarity	NPC314702
0.6588	Remote Similarity	NPC1820
0.6588	Remote Similarity	NPC28510
0.6581	Remote Similarity	NPC253675
0.6577	Remote Similarity	NPC218303
0.6576	Remote Similarity	NPC93882
0.6576	Remote Similarity	NPC130595
0.6571	Remote Similarity	NPC477259
0.6571	Remote Similarity	NPC169387
0.657	Remote Similarity	NPC99723
0.6569	Remote Similarity	NPC67978
0.6569	Remote Similarity	NPC303581
0.6566	Remote Similarity	NPC93653
0.6562	Remote Similarity	NPC176113
0.6562	Remote Similarity	NPC298449
0.6558	Remote Similarity	NPC293624
0.6553	Remote Similarity	NPC283810
0.6547	Remote Similarity	NPC127996
0.6547	Remote Similarity	NPC316981
0.6546	Remote Similarity	NPC470088
0.6545	Remote Similarity	NPC125852
0.6545	Remote Similarity	NPC308943
0.6542	Remote Similarity	NPC33256
0.6541	Remote Similarity	NPC6854
0.6541	Remote Similarity	NPC313737
0.6541	Remote Similarity	NPC285078
0.654	Remote Similarity	NPC29531
0.6535	Remote Similarity	NPC329830
0.6528	Remote Similarity	NPC207239
0.6526	Remote Similarity	NPC470485
0.6522	Remote Similarity	NPC179287
0.652	Remote Similarity	NPC222046
0.6515	Remote Similarity	NPC37205
0.6515	Remote Similarity	NPC160931
0.6515	Remote Similarity	NPC147091
0.651	Remote Similarity	NPC469978
0.6509	Remote Similarity	NPC66777
0.6509	Remote Similarity	NPC194740
0.6505	Remote Similarity	NPC218530
0.6505	Remote Similarity	NPC308267
0.6504	Remote Similarity	NPC195636
0.6502	Remote Similarity	NPC473188
0.65	Remote Similarity	NPC195787
0.65	Remote Similarity	NPC477161
0.65	Remote Similarity	NPC246140
0.6495	Remote Similarity	NPC241392
0.6493	Remote Similarity	NPC124626
0.6489	Remote Similarity	NPC55470
0.6486	Remote Similarity	NPC477160
0.6481	Remote Similarity	NPC138615
0.6481	Remote Similarity	NPC265642
0.6481	Remote Similarity	NPC23080
0.6481	Remote Similarity	NPC193906
0.6481	Remote Similarity	NPC132874
0.6481	Remote Similarity	NPC218733
0.6479	Remote Similarity	NPC196231

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 NPC163829 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	618
0.2-0.3	1142
0.3-0.4	1634
0.4-0.5	3152
0.5-0.6	2092
0.6-0.7	298
0.7-0.8	12
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
0.8276	Intermediate Similarity	NPD7559	Phase 2
0.7845	Intermediate Similarity	NPD824	Approved
0.7383	Intermediate Similarity	NPD5025	Approved
0.7363	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD2899	Discontinued
0.7254	Intermediate Similarity	NPD2821	Approved
0.7241	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD683	Approved
0.7104	Intermediate Similarity	NPD4049	Phase 2
0.7074	Intermediate Similarity	NPD1670	Discontinued
0.707	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6795	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5071	Phase 2
0.6927	Remote Similarity	NPD7225	Discontinued
0.6901	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD743	Approved
0.6846	Remote Similarity	NPD8091	Phase 3
0.6845	Remote Similarity	NPD4515	Suspended
0.6842	Remote Similarity	NPD3631	Phase 3
0.6837	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD1293	Approved
0.6784	Remote Similarity	NPD5186	Approved
0.6784	Remote Similarity	NPD5183	Approved
0.6763	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3442	Approved
0.6739	Remote Similarity	NPD3441	Approved
0.6732	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7291	Discontinued
0.673	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD3591	Approved
0.6712	Remote Similarity	NPD3592	Approved
0.6711	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7281	Phase 3
0.6699	Remote Similarity	NPD7280	Phase 3
0.6697	Remote Similarity	NPD7263	Phase 2
0.6682	Remote Similarity	NPD5914	Approved
0.6682	Remote Similarity	NPD5645	Phase 3
0.6682	Remote Similarity	NPD4539	Phase 1
0.6681	Remote Similarity	NPD6625	Approved
0.6651	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.665	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD3802	Phase 3
0.6635	Remote Similarity	NPD3633	Approved
0.6635	Remote Similarity	NPD3634	Approved
0.6615	Remote Similarity	NPD2592	Discontinued
0.6612	Remote Similarity	NPD3145	Approved
0.6612	Remote Similarity	NPD3144	Approved
0.6607	Remote Similarity	NPD8149	Discontinued
0.6606	Remote Similarity	NPD4467	Phase 2
0.6606	Remote Similarity	NPD4465	Phase 2
0.6601	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4493	Discontinued
0.6576	Remote Similarity	NPD2674	Phase 3
0.6575	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6199	Discontinued
0.6552	Remote Similarity	NPD1220	Phase 1
0.6546	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4373	Phase 2
0.6537	Remote Similarity	NPD1221	Approved
0.6532	Remote Similarity	NPD3893	Discontinued
0.6522	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD5515	Phase 2
0.6502	Remote Similarity	NPD4083	Discontinued
0.6502	Remote Similarity	NPD4206	Approved
0.6493	Remote Similarity	NPD3349	Phase 2
0.6493	Remote Similarity	NPD2792	Approved
0.6485	Remote Similarity	NPD6716	Phase 1
0.6485	Remote Similarity	NPD2680	Approved
0.6485	Remote Similarity	NPD2681	Approved
0.6482	Remote Similarity	NPD5978	Approved
0.6482	Remote Similarity	NPD5977	Approved
0.6476	Remote Similarity	NPD3154	Approved
0.6476	Remote Similarity	NPD3153	Approved
0.6473	Remote Similarity	NPD4492	Approved
0.6473	Remote Similarity	NPD3888	Discontinued
0.6473	Remote Similarity	NPD6297	Approved
0.6473	Remote Similarity	NPD4494	Approved
0.6457	Remote Similarity	NPD5860	Discontinued
0.6456	Remote Similarity	NPD3793	Phase 3
0.6455	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD4466	Phase 1
0.6447	Remote Similarity	NPD5519	Discontinued
0.6444	Remote Similarity	NPD4455	Discontinued
0.6441	Remote Similarity	NPD4082	Approved
0.6439	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6997	Phase 2
0.6429	Remote Similarity	NPD6618	Phase 2
0.6414	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD7110	Phase 1
0.6414	Remote Similarity	NPD6385	Approved
0.6414	Remote Similarity	NPD6386	Approved
0.641	Remote Similarity	NPD4952	Phase 3
0.6407	Remote Similarity	NPD7278	Phase 2
0.6407	Remote Similarity	NPD7279	Phase 2
0.6404	Remote Similarity	NPD2247	Approved
0.6404	Remote Similarity	NPD2249	Approved
0.6402	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD4596	Phase 1
0.639	Remote Similarity	NPD2898	Approved
0.6385	Remote Similarity	NPD2845	Phase 2
0.6385	Remote Similarity	NPD2843	Phase 2
0.6383	Remote Similarity	NPD1505	Phase 2
0.6383	Remote Similarity	NPD6962	Phase 2
0.6381	Remote Similarity	NPD7546	Discontinued
0.638	Remote Similarity	NPD3298	Approved
0.6378	Remote Similarity	NPD3639	Approved
0.6378	Remote Similarity	NPD3640	Phase 3
0.6378	Remote Similarity	NPD3641	Approved
0.6377	Remote Similarity	NPD5312	Approved
0.6377	Remote Similarity	NPD5313	Approved
0.6376	Remote Similarity	NPD7810	Phase 3
0.6376	Remote Similarity	NPD6874	Approved
0.6376	Remote Similarity	NPD7811	Phase 3
0.6373	Remote Similarity	NPD4166	Phase 2
0.6368	Remote Similarity	NPD2906	Approved
0.6368	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD4022	Approved
0.6368	Remote Similarity	NPD3472	Approved
0.6368	Remote Similarity	NPD2907	Approved
0.6364	Remote Similarity	NPD3684	Discontinued
0.6364	Remote Similarity	NPD6875	Approved
0.6364	Remote Similarity	NPD6876	Approved
0.636	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.636	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD9494	Approved
0.6359	Remote Similarity	NPD5564	Approved
0.6356	Remote Similarity	NPD7031	Phase 1
0.6352	Remote Similarity	NPD7186	Phase 3
0.6351	Remote Similarity	NPD6851	Approved
0.6351	Remote Similarity	NPD6853	Approved
0.635	Remote Similarity	NPD5773	Approved
0.635	Remote Similarity	NPD5772	Approved
0.6348	Remote Similarity	NPD3437	Discontinued
0.6348	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD2325	Approved
0.6338	Remote Similarity	NPD1898	Discontinued
0.6337	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7560	Approved
0.6332	Remote Similarity	NPD2672	Discontinued
0.6329	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6326	Remote Similarity	NPD5937	Approved
0.6325	Remote Similarity	NPD3259	Approved
0.6316	Remote Similarity	NPD5561	Approved
0.6316	Remote Similarity	NPD5562	Approved
0.6311	Remote Similarity	NPD6894	Phase 1
0.6311	Remote Similarity	NPD3372	Discontinued
0.6308	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD6790	Phase 1
0.6303	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7565	Approved
0.6298	Remote Similarity	NPD3965	Phase 1
0.6296	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD711	Discontinued
0.6293	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7316	Discontinued
0.6284	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD4604	Approved
0.6284	Remote Similarity	NPD4605	Approved
0.6283	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD5640	Discontinued
0.6281	Remote Similarity	NPD5617	Suspended
0.6281	Remote Similarity	NPD6517	Phase 3
0.6279	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD5641	Discontinued
0.6277	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD3006	Discontinued
0.6275	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5457	Discontinued
0.6266	Remote Similarity	NPD3912	Discontinued
0.6266	Remote Similarity	NPD5566	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD1307	Phase 2
0.6256	Remote Similarity	NPD1309	Phase 2
0.625	Remote Similarity	NPD6296	Discontinued
0.625	Remote Similarity	NPD7048	Phase 3
0.6239	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5582	Discontinued
0.6238	Remote Similarity	NPD6063	Approved
0.6238	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD5496	Approved
0.6232	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4859	Phase 1
0.6211	Remote Similarity	NPD2492	Phase 1
0.6211	Remote Similarity	NPD1945	Phase 1
0.6207	Remote Similarity	NPD7180	Phase 3
0.6205	Remote Similarity	NPD3507	Phase 2
0.6204	Remote Similarity	NPD5871	Discontinued
0.6204	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD4981	Phase 2

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