NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.12
Volume:	274.872
LogP:	1.824
LogD:	1.474
LogS:	-2.619
# Rotatable Bonds:	2
TPSA:	58.64
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.892
Synthetic Accessibility Score:	3.501
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.495
MDCK Permeability:	3.643795207608491e-05
Pgp-inhibitor:	0.205
Pgp-substrate:	0.087
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.086
30% Bioavailability (F30%):	0.317

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988
Plasma Protein Binding (PPB):	69.27054595947266%
Volume Distribution (VD):	0.831
Pgp-substrate:	36.95912551879883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.144
CYP1A2-substrate:	0.14
CYP2C19-inhibitor:	0.318
CYP2C19-substrate:	0.729
CYP2C9-inhibitor:	0.321
CYP2C9-substrate:	0.427
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.76
CYP3A4-inhibitor:	0.161
CYP3A4-substrate:	0.403

ADMET: Excretion

Clearance (CL):	4.522
Half-life (T1/2):	0.799

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.729
Drug-inuced Liver Injury (DILI):	0.564
AMES Toxicity:	0.457
Rat Oral Acute Toxicity:	0.701
Maximum Recommended Daily Dose:	0.466
Skin Sensitization:	0.637
Carcinogencity:	0.828
Eye Corrosion:	0.004
Eye Irritation:	0.091
Respiratory Toxicity:	0.377

Download Data

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

Natural Product: NPC87391

Natural Product ID:	NPC87391
*Common Name:**	(6As)-8-Acetyl-4-Methoxy-5,6,6A,7-Tetrahydropyrrolo[2,1-C][1,4]Benzodiazepin-11-One
IUPAC Name:	(6aS)-8-acetyl-4-methoxy-5,6,6a,7-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one
Synonyms:
Standard InCHIKey:	LCCQQLMYXVRWOK-NSHDSACASA-N
Standard InCHI:	InChI=1S/C15H16N2O3/c1-9(18)10-6-11-7-16-14-12(15(19)17(11)8-10)4-3-5-13(14)20-2/h3-5,8,11,16H,6-7H2,1-2H3/t11-/m0/s1
SMILES:	COc1cccc2c1NC[C@H]1N(C2=O)C=C(C1)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3233163
PubChem CID:	90669958
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
NPO32984	streptomyces sp. 11a057	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24613164]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	72000.0	nM	PMID[479206]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[479206]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000.0	nM	PMID[479206]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	56100.0	nM	PMID[479206]

☑ 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 NPC87391 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	3808
0.2-0.3	12722
0.3-0.4	4019
0.4-0.5	16764
0.5-0.6	4445
0.6-0.7	559
0.7-0.8	21
0.8-0.85	2
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9521	High Similarity	NPC197335
0.9464	High Similarity	NPC314659
0.8212	Intermediate Similarity	NPC270301
0.8128	Intermediate Similarity	NPC316282
0.7989	Intermediate Similarity	NPC257763
0.7831	Intermediate Similarity	NPC198401
0.7771	Intermediate Similarity	NPC301163
0.7642	Intermediate Similarity	NPC314702
0.7622	Intermediate Similarity	NPC472163
0.7617	Intermediate Similarity	NPC112937
0.7528	Intermediate Similarity	NPC93653
0.7437	Intermediate Similarity	NPC158551
0.7313	Intermediate Similarity	NPC478075
0.7214	Intermediate Similarity	NPC163829
0.7204	Intermediate Similarity	NPC73280
0.7172	Intermediate Similarity	NPC100863
0.717	Intermediate Similarity	NPC122886
0.716	Intermediate Similarity	NPC162417
0.716	Intermediate Similarity	NPC316104
0.7158	Intermediate Similarity	NPC28368
0.7108	Intermediate Similarity	NPC330683
0.7108	Intermediate Similarity	NPC329567
0.7103	Intermediate Similarity	NPC257851
0.7077	Intermediate Similarity	NPC45389
0.7059	Intermediate Similarity	NPC471648
0.7016	Intermediate Similarity	NPC85613
0.7016	Intermediate Similarity	NPC283810
0.7016	Intermediate Similarity	NPC5167
0.701	Intermediate Similarity	NPC262725
0.6989	Remote Similarity	NPC471652
0.6983	Remote Similarity	NPC241392
0.6954	Remote Similarity	NPC92803
0.6935	Remote Similarity	NPC299582
0.6927	Remote Similarity	NPC477161
0.6919	Remote Similarity	NPC173295
0.6912	Remote Similarity	NPC41216
0.689	Remote Similarity	NPC470481
0.689	Remote Similarity	NPC470482
0.6885	Remote Similarity	NPC470708
0.686	Remote Similarity	NPC266425
0.6854	Remote Similarity	NPC288987
0.6853	Remote Similarity	NPC18890
0.685	Remote Similarity	NPC243626
0.685	Remote Similarity	NPC230313
0.6845	Remote Similarity	NPC246140
0.6845	Remote Similarity	NPC195787
0.6832	Remote Similarity	NPC71124
0.6818	Remote Similarity	NPC471164
0.68	Remote Similarity	NPC254957
0.6786	Remote Similarity	NPC473007
0.6771	Remote Similarity	NPC8467
0.6749	Remote Similarity	NPC218733
0.6749	Remote Similarity	NPC132874
0.6749	Remote Similarity	NPC265642
0.6749	Remote Similarity	NPC138615
0.6748	Remote Similarity	NPC207971
0.6718	Remote Similarity	NPC116096
0.6716	Remote Similarity	NPC5374
0.6715	Remote Similarity	NPC268077
0.6712	Remote Similarity	NPC478078
0.67	Remote Similarity	NPC22476
0.6667	Remote Similarity	NPC70092
0.6667	Remote Similarity	NPC323969
0.6651	Remote Similarity	NPC212123
0.665	Remote Similarity	NPC469732
0.665	Remote Similarity	NPC473008
0.6636	Remote Similarity	NPC157931
0.6633	Remote Similarity	NPC21425
0.6621	Remote Similarity	NPC115588
0.6619	Remote Similarity	NPC285192
0.6618	Remote Similarity	NPC41488
0.6617	Remote Similarity	NPC1820
0.6615	Remote Similarity	NPC287152
0.6613	Remote Similarity	NPC471649
0.6595	Remote Similarity	NPC119669
0.6592	Remote Similarity	NPC49547
0.6588	Remote Similarity	NPC477160
0.6584	Remote Similarity	NPC473004
0.6574	Remote Similarity	NPC77777
0.6567	Remote Similarity	NPC5630
0.6567	Remote Similarity	NPC174629
0.6562	Remote Similarity	NPC172222
0.6557	Remote Similarity	NPC474366
0.6555	Remote Similarity	NPC475147
0.6554	Remote Similarity	NPC43218
0.6542	Remote Similarity	NPC30749
0.6542	Remote Similarity	NPC268223
0.6538	Remote Similarity	NPC146370
0.6536	Remote Similarity	NPC43477
0.6528	Remote Similarity	NPC313327
0.6528	Remote Similarity	NPC126556
0.6522	Remote Similarity	NPC144691
0.6522	Remote Similarity	NPC138830
0.6518	Remote Similarity	NPC102593
0.6518	Remote Similarity	NPC196718
0.6517	Remote Similarity	NPC319645
0.651	Remote Similarity	NPC471651
0.6504	Remote Similarity	NPC154922
0.6498	Remote Similarity	NPC195120
0.6498	Remote Similarity	NPC87560
0.6497	Remote Similarity	NPC166169
0.6493	Remote Similarity	NPC16249
0.6493	Remote Similarity	NPC222561
0.6493	Remote Similarity	NPC308943
0.6489	Remote Similarity	NPC329631
0.6486	Remote Similarity	NPC314223
0.6482	Remote Similarity	NPC302235
0.6479	Remote Similarity	NPC471304
0.6477	Remote Similarity	NPC253476
0.6471	Remote Similarity	NPC203972
0.6468	Remote Similarity	NPC475609
0.6467	Remote Similarity	NPC324081
0.6467	Remote Similarity	NPC242000
0.6463	Remote Similarity	NPC148889
0.6459	Remote Similarity	NPC1464
0.6458	Remote Similarity	NPC214960
0.6458	Remote Similarity	NPC279527
0.6457	Remote Similarity	NPC194740
0.6453	Remote Similarity	NPC250476
0.6452	Remote Similarity	NPC471197
0.645	Remote Similarity	NPC322621
0.6449	Remote Similarity	NPC187501
0.6448	Remote Similarity	NPC471646
0.6448	Remote Similarity	NPC471647
0.6444	Remote Similarity	NPC139373
0.644	Remote Similarity	NPC189116
0.6435	Remote Similarity	NPC148391
0.6435	Remote Similarity	NPC2905
0.6432	Remote Similarity	NPC475133
0.6422	Remote Similarity	NPC248601
0.6422	Remote Similarity	NPC471198
0.6422	Remote Similarity	NPC204970
0.6419	Remote Similarity	NPC305542
0.6414	Remote Similarity	NPC98416
0.6413	Remote Similarity	NPC74575
0.6409	Remote Similarity	NPC76478
0.6398	Remote Similarity	NPC473422
0.639	Remote Similarity	NPC470485
0.6389	Remote Similarity	NPC114468
0.6389	Remote Similarity	NPC39500
0.6388	Remote Similarity	NPC39370
0.6385	Remote Similarity	NPC100573
0.6385	Remote Similarity	NPC207873
0.6384	Remote Similarity	NPC471762
0.6384	Remote Similarity	NPC311906
0.6379	Remote Similarity	NPC208522
0.6377	Remote Similarity	NPC470021
0.6374	Remote Similarity	NPC308197
0.6373	Remote Similarity	NPC182131
0.6372	Remote Similarity	NPC473186
0.6372	Remote Similarity	NPC218303
0.6364	Remote Similarity	NPC118154
0.6364	Remote Similarity	NPC157983
0.6364	Remote Similarity	NPC113455
0.6359	Remote Similarity	NPC66191
0.6359	Remote Similarity	NPC55470
0.6359	Remote Similarity	NPC316297
0.6359	Remote Similarity	NPC9373
0.6359	Remote Similarity	NPC176113
0.6359	Remote Similarity	NPC314817
0.6356	Remote Similarity	NPC223242
0.6354	Remote Similarity	NPC135006
0.6351	Remote Similarity	NPC473460
0.6347	Remote Similarity	NPC182853
0.6347	Remote Similarity	NPC134702
0.6347	Remote Similarity	NPC96321
0.6347	Remote Similarity	NPC131885
0.6343	Remote Similarity	NPC119722
0.6343	Remote Similarity	NPC10732
0.634	Remote Similarity	NPC33507
0.6337	Remote Similarity	NPC226794
0.6335	Remote Similarity	NPC7560
0.6335	Remote Similarity	NPC118189
0.6333	Remote Similarity	NPC471316
0.6324	Remote Similarity	NPC474059
0.6321	Remote Similarity	NPC87714
0.6321	Remote Similarity	NPC14339
0.6318	Remote Similarity	NPC222046
0.6314	Remote Similarity	NPC67401
0.6311	Remote Similarity	NPC66777
0.631	Remote Similarity	NPC469540
0.631	Remote Similarity	NPC469539
0.6308	Remote Similarity	NPC471778
0.6307	Remote Similarity	NPC231382
0.6304	Remote Similarity	NPC301501
0.6304	Remote Similarity	NPC151171
0.6303	Remote Similarity	NPC185172
0.6301	Remote Similarity	NPC195636
0.63	Remote Similarity	NPC288305
0.63	Remote Similarity	NPC121400
0.6298	Remote Similarity	NPC161804
0.6295	Remote Similarity	NPC470018
0.6293	Remote Similarity	NPC203628
0.6293	Remote Similarity	NPC470483
0.629	Remote Similarity	NPC225279
0.629	Remote Similarity	NPC472099
0.6289	Remote Similarity	NPC127362
0.6287	Remote Similarity	NPC299806
0.6286	Remote Similarity	NPC122235
0.6286	Remote Similarity	NPC67904

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 NPC87391 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	658
0.2-0.3	1123
0.3-0.4	1287
0.4-0.5	3158
0.5-0.6	2325
0.6-0.7	364
0.7-0.8	22
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
0.7701	Intermediate Similarity	NPD4515	Suspended
0.7692	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD4082	Approved
0.7538	Intermediate Similarity	NPD3472	Approved
0.7538	Intermediate Similarity	NPD4022	Approved
0.7526	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD4492	Approved
0.7475	Intermediate Similarity	NPD4494	Approved
0.7473	Intermediate Similarity	NPD5183	Approved
0.7473	Intermediate Similarity	NPD5186	Approved
0.7473	Intermediate Similarity	NPD6654	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD3372	Discontinued
0.7418	Intermediate Similarity	NPD2681	Approved
0.7418	Intermediate Similarity	NPD2680	Approved
0.7389	Intermediate Similarity	NPD3888	Discontinued
0.7374	Intermediate Similarity	NPD5294	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5071	Phase 2
0.7313	Intermediate Similarity	NPD4596	Phase 1
0.7308	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD4456	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD4465	Phase 2
0.73	Intermediate Similarity	NPD4467	Phase 2
0.7291	Intermediate Similarity	NPD3893	Discontinued
0.7286	Intermediate Similarity	NPD6795	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7071	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4455	Discontinued
0.7255	Intermediate Similarity	NPD4493	Discontinued
0.7246	Intermediate Similarity	NPD3940	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD5860	Discontinued
0.7196	Intermediate Similarity	NPD6293	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2249	Approved
0.7135	Intermediate Similarity	NPD2247	Approved
0.7127	Intermediate Similarity	NPD1769	Discontinued
0.7108	Intermediate Similarity	NPD2907	Approved
0.7108	Intermediate Similarity	NPD2906	Approved
0.7072	Intermediate Similarity	NPD4205	Phase 3
0.7065	Intermediate Similarity	NPD6238	Discontinued
0.7059	Intermediate Similarity	NPD5143	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4429	Discontinued
0.6981	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6321	Discontinued
0.6974	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD795	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7126	Discontinued
0.6923	Remote Similarity	NPD1945	Phase 1
0.6912	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6199	Discontinued
0.6872	Remote Similarity	NPD1802	Approved
0.6872	Remote Similarity	NPD1801	Approved
0.6865	Remote Similarity	NPD1012	Discontinued
0.6853	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD743	Approved
0.6834	Remote Similarity	NPD3479	Discontinued
0.6822	Remote Similarity	NPD3437	Discontinued
0.6811	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6618	Phase 2
0.6771	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD1670	Discontinued
0.6737	Remote Similarity	NPD5847	Phase 1
0.673	Remote Similarity	NPD7225	Discontinued
0.6728	Remote Similarity	NPD3912	Discontinued
0.6727	Remote Similarity	NPD5022	Discontinued
0.6719	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD4539	Phase 1
0.6703	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD1307	Phase 2
0.6702	Remote Similarity	NPD1309	Phase 2
0.67	Remote Similarity	NPD5515	Phase 2
0.6696	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD824	Approved
0.6683	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2248	Approved
0.6667	Remote Similarity	NPD2246	Approved
0.6667	Remote Similarity	NPD3802	Phase 3
0.6667	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3154	Approved
0.6667	Remote Similarity	NPD3153	Approved
0.6652	Remote Similarity	NPD3006	Discontinued
0.665	Remote Similarity	NPD3964	Approved
0.6636	Remote Similarity	NPD8149	Discontinued
0.6635	Remote Similarity	NPD6644	Discontinued
0.6632	Remote Similarity	NPD1559	Discontinued
0.6617	Remote Similarity	NPD5994	Discontinued
0.6617	Remote Similarity	NPD7668	Phase 2
0.6613	Remote Similarity	NPD2672	Discontinued
0.6612	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD4130	Phase 3
0.6602	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4020	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4981	Phase 2
0.6571	Remote Similarity	NPD7043	Discontinued
0.657	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3416	Discontinued
0.6567	Remote Similarity	NPD4258	Approved
0.6567	Remote Similarity	NPD4259	Approved
0.6567	Remote Similarity	NPD5114	Approved
0.6567	Remote Similarity	NPD5112	Approved
0.6567	Remote Similarity	NPD5113	Approved
0.6564	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD3684	Discontinued
0.6559	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5941	Approved
0.6557	Remote Similarity	NPD5942	Approved
0.6548	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD3945	Discontinued
0.6538	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5457	Discontinued
0.6522	Remote Similarity	NPD6519	Phase 2
0.652	Remote Similarity	NPD7669	Phase 3
0.6517	Remote Similarity	NPD1110	Approved
0.6517	Remote Similarity	NPD1109	Approved
0.6514	Remote Similarity	NPD2949	Approved
0.6514	Remote Similarity	NPD2950	Approved
0.6512	Remote Similarity	NPD5293	Phase 2
0.6512	Remote Similarity	NPD7559	Phase 2
0.6505	Remote Similarity	NPD5196	Approved
0.6505	Remote Similarity	NPD5197	Approved
0.6505	Remote Similarity	NPD5194	Approved
0.6502	Remote Similarity	NPD7570	Approved
0.6502	Remote Similarity	NPD7569	Approved
0.6497	Remote Similarity	NPD6297	Approved
0.6495	Remote Similarity	NPD5997	Discontinued
0.6493	Remote Similarity	NPD5514	Discontinued
0.6489	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5025	Approved
0.6476	Remote Similarity	NPD8157	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1059	Phase 2
0.6462	Remote Similarity	NPD7467	Discontinued
0.6462	Remote Similarity	NPD4859	Phase 1
0.6462	Remote Similarity	NPD2514	Approved
0.6462	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.646	Remote Similarity	NPD2951	Discontinued
0.6455	Remote Similarity	NPD8311	Discontinued
0.6453	Remote Similarity	NPD5042	Phase 1
0.645	Remote Similarity	NPD6853	Approved
0.645	Remote Similarity	NPD6851	Approved
0.6448	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7186	Phase 3
0.6438	Remote Similarity	NPD6242	Discontinued
0.6436	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD1420	Approved
0.6433	Remote Similarity	NPD1421	Approved
0.6432	Remote Similarity	NPD7853	Phase 2
0.6429	Remote Similarity	NPD1544	Phase 1
0.6429	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6457	Approved
0.642	Remote Similarity	NPD2245	Discovery
0.641	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD6768	Approved
0.6402	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD4503	Phase 2
0.6396	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD1880	Phase 3
0.6394	Remote Similarity	NPD6874	Approved
0.6393	Remote Similarity	NPD2899	Discontinued
0.6392	Remote Similarity	NPD4166	Phase 2
0.639	Remote Similarity	NPD3631	Phase 3
0.6386	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD5950	Discontinued
0.6383	Remote Similarity	NPD2592	Discontinued
0.6378	Remote Similarity	NPD7528	Approved
0.6377	Remote Similarity	NPD5195	Discontinued
0.6374	Remote Similarity	NPD5024	Approved
0.6368	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD4393	Approved
0.6368	Remote Similarity	NPD33	Approved
0.6364	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD2120	Phase 2
0.6359	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD4679	Discontinued
0.6356	Remote Similarity	NPD1659	Phase 1
0.6353	Remote Similarity	NPD1123	Approved
0.6353	Remote Similarity	NPD1124	Approved
0.6351	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.635	Remote Similarity	NPD1891	Discontinued
0.6344	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.634	Remote Similarity	NPD2821	Approved
0.634	Remote Similarity	NPD6379	Discontinued
0.6333	Remote Similarity	NPD3170	Approved
0.6332	Remote Similarity	NPD4368	Phase 2
0.633	Remote Similarity	NPD2649	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