NPASS Compound

Structure

NPC92803 OpenBabel07101718292D 23 26 0 0 1 0 0 0 0 0999 V2000 -0.5593 2.5984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1422 -2.0896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1672 -2.3121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4369 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4871 -1.5791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 1.6235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7568 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1906 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 1.4010 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1906 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 2 5 1 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 10 2 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 8 13 2 0 0 0 0 9 1 1 1 0 0 0 9 15 1 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 19 1 0 0 0 0 15 19 2 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	307.1
Volume:	303.995
LogP:	1.568
LogD:	1.267
LogS:	-4.459
# Rotatable Bonds:	0
TPSA:	84.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.664
Synthetic Accessibility Score:	2.983
Fsp3:	0.118
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:	-4.916
MDCK Permeability:	1.0089176612382289e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.779
Plasma Protein Binding (PPB):	87.18648529052734%
Volume Distribution (VD):	0.775
Pgp-substrate:	8.363256454467773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.173
CYP1A2-substrate:	0.401
CYP2C19-inhibitor:	0.113
CYP2C19-substrate:	0.557
CYP2C9-inhibitor:	0.49
CYP2C9-substrate:	0.718
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.29
CYP3A4-inhibitor:	0.414
CYP3A4-substrate:	0.821

ADMET: Excretion

Clearance (CL):	1.552
Half-life (T1/2):	0.652

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.546
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.374
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.262
Skin Sensitization:	0.107
Carcinogencity:	0.876
Eye Corrosion:	0.003
Eye Irritation:	0.054
Respiratory Toxicity:	0.116

Download Data

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

Natural Product: NPC92803

Natural Product ID:	NPC92803
*Common Name:**	Circumdatin G
IUPAC Name:	(7S)-9-hydroxy-7-methyl-6,7-dihydroquinazolino[3,2-a][1,4]benzodiazepine-5,13-dione
Synonyms:
Standard InCHIKey:	VNCYXASDDCJEJE-VIFPVBQESA-N
Standard InCHI:	InChI=1S/C17H13N3O3/c1-9-15-19-14-11(6-4-8-13(14)21)17(23)20(15)12-7-3-2-5-10(12)16(22)18-9/h2-9,21H,1H3,(H,18,22)/t9-/m0/s1
SMILES:	OC1=N[C@@H](C)c2n(c3c1cccc3)c(=O)c1c(n2)c(O)ccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375799
PubChem CID:	10804637
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001132] Pyrimidodiazepines

*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
NPO32643	aspergillus westerdijkiae dffscs013	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23701598]

☑ 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
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[485961]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000.0	nM	PMID[485961]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[485961]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[485961]

☑ 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 NPC92803 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	602
0.1-0.2	5682
0.2-0.3	11714
0.3-0.4	13558
0.4-0.5	7373
0.5-0.6	2752
0.6-0.7	877
0.7-0.8	116
0.8-0.85	13
0.85-0.9	3
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC18890
0.8876	High Similarity	NPC471130
0.8757	High Similarity	NPC88970
0.8138	Intermediate Similarity	NPC198401
0.7861	Intermediate Similarity	NPC150308
0.7771	Intermediate Similarity	NPC471132
0.7663	Intermediate Similarity	NPC475594
0.7644	Intermediate Similarity	NPC471196
0.7644	Intermediate Similarity	NPC471195
0.7622	Intermediate Similarity	NPC475607
0.759	Intermediate Similarity	NPC316282
0.7581	Intermediate Similarity	NPC474081
0.7553	Intermediate Similarity	NPC270301
0.75	Intermediate Similarity	NPC144691
0.7447	Intermediate Similarity	NPC474041
0.7447	Intermediate Similarity	NPC475761
0.7389	Intermediate Similarity	NPC84317
0.7371	Intermediate Similarity	NPC257851
0.7363	Intermediate Similarity	NPC295548
0.736	Intermediate Similarity	NPC472539
0.736	Intermediate Similarity	NPC470787
0.736	Intermediate Similarity	NPC472540
0.7358	Intermediate Similarity	NPC473815
0.734	Intermediate Similarity	NPC16249
0.734	Intermediate Similarity	NPC471155
0.7323	Intermediate Similarity	NPC472542
0.7323	Intermediate Similarity	NPC472541
0.7316	Intermediate Similarity	NPC475685
0.7308	Intermediate Similarity	NPC154478
0.7304	Intermediate Similarity	NPC270241
0.7291	Intermediate Similarity	NPC225400
0.7268	Intermediate Similarity	NPC93653
0.7268	Intermediate Similarity	NPC27904
0.7255	Intermediate Similarity	NPC470786
0.7255	Intermediate Similarity	NPC472538
0.7251	Intermediate Similarity	NPC300299
0.7228	Intermediate Similarity	NPC289776
0.7228	Intermediate Similarity	NPC191863
0.7228	Intermediate Similarity	NPC133470
0.7183	Intermediate Similarity	NPC220851
0.7157	Intermediate Similarity	NPC163829
0.715	Intermediate Similarity	NPC314659
0.7122	Intermediate Similarity	NPC158551
0.7098	Intermediate Similarity	NPC197335
0.7097	Intermediate Similarity	NPC189116
0.7083	Intermediate Similarity	NPC474815
0.7051	Intermediate Similarity	NPC157931
0.7029	Intermediate Similarity	NPC83214
0.7017	Intermediate Similarity	NPC241392
0.7005	Intermediate Similarity	NPC204867
0.7	Intermediate Similarity	NPC315829
0.6989	Remote Similarity	NPC207554
0.6979	Remote Similarity	NPC471743
0.6971	Remote Similarity	NPC43218
0.6954	Remote Similarity	NPC87391
0.6949	Remote Similarity	NPC2823
0.6944	Remote Similarity	NPC324445
0.6935	Remote Similarity	NPC144381
0.6916	Remote Similarity	NPC248601
0.6911	Remote Similarity	NPC355
0.6897	Remote Similarity	NPC184437
0.6892	Remote Similarity	NPC172222
0.6891	Remote Similarity	NPC8467
0.6872	Remote Similarity	NPC39822
0.6864	Remote Similarity	NPC471762
0.6847	Remote Similarity	NPC170333
0.6832	Remote Similarity	NPC230403
0.6823	Remote Similarity	NPC112336
0.6823	Remote Similarity	NPC474814
0.6814	Remote Similarity	NPC90229
0.6813	Remote Similarity	NPC254798
0.6791	Remote Similarity	NPC244425
0.6791	Remote Similarity	NPC15384
0.6782	Remote Similarity	NPC207428
0.678	Remote Similarity	NPC122553
0.6776	Remote Similarity	NPC237649
0.6776	Remote Similarity	NPC300596
0.6772	Remote Similarity	NPC199737
0.6753	Remote Similarity	NPC470548
0.6748	Remote Similarity	NPC106118
0.6732	Remote Similarity	NPC471199
0.672	Remote Similarity	NPC295021
0.6719	Remote Similarity	NPC33507
0.6714	Remote Similarity	NPC471191
0.6713	Remote Similarity	NPC471197
0.6712	Remote Similarity	NPC66777
0.6702	Remote Similarity	NPC299582
0.6701	Remote Similarity	NPC166169
0.6684	Remote Similarity	NPC475983
0.6684	Remote Similarity	NPC476231
0.6683	Remote Similarity	NPC203635
0.6682	Remote Similarity	NPC471198
0.6681	Remote Similarity	NPC477549
0.6667	Remote Similarity	NPC309845
0.6667	Remote Similarity	NPC133156
0.6667	Remote Similarity	NPC317727
0.6667	Remote Similarity	NPC301163
0.6667	Remote Similarity	NPC182131
0.6652	Remote Similarity	NPC477112
0.6651	Remote Similarity	NPC250448
0.6651	Remote Similarity	NPC285192
0.6649	Remote Similarity	NPC113056
0.6649	Remote Similarity	NPC138293
0.6633	Remote Similarity	NPC243058
0.6617	Remote Similarity	NPC262725
0.6616	Remote Similarity	NPC85613
0.6616	Remote Similarity	NPC5167
0.6616	Remote Similarity	NPC298320
0.6604	Remote Similarity	NPC270918
0.6604	Remote Similarity	NPC53344
0.6603	Remote Similarity	NPC471944
0.66	Remote Similarity	NPC471742
0.6599	Remote Similarity	NPC219848
0.6598	Remote Similarity	NPC471778
0.659	Remote Similarity	NPC62995
0.659	Remote Similarity	NPC322064
0.6578	Remote Similarity	NPC117032
0.6576	Remote Similarity	NPC146370
0.6574	Remote Similarity	NPC74562
0.6574	Remote Similarity	NPC316181
0.6574	Remote Similarity	NPC151781
0.6567	Remote Similarity	NPC161801
0.6566	Remote Similarity	NPC256268
0.6561	Remote Similarity	NPC478141
0.656	Remote Similarity	NPC313327
0.6553	Remote Similarity	NPC276517
0.6552	Remote Similarity	NPC230805
0.6535	Remote Similarity	NPC90415
0.6528	Remote Similarity	NPC153980
0.6528	Remote Similarity	NPC6865
0.6526	Remote Similarity	NPC283117
0.6526	Remote Similarity	NPC212123
0.652	Remote Similarity	NPC5630
0.6519	Remote Similarity	NPC204156
0.6519	Remote Similarity	NPC47986
0.6517	Remote Similarity	NPC253476
0.6517	Remote Similarity	NPC302235
0.6515	Remote Similarity	NPC9475
0.651	Remote Similarity	NPC257763
0.6497	Remote Similarity	NPC303225
0.6495	Remote Similarity	NPC330683
0.6495	Remote Similarity	NPC329567
0.6493	Remote Similarity	NPC211813
0.649	Remote Similarity	NPC470021
0.6484	Remote Similarity	NPC471574
0.6484	Remote Similarity	NPC43477
0.6481	Remote Similarity	NPC72956
0.6481	Remote Similarity	NPC294375
0.6477	Remote Similarity	NPC226662
0.6476	Remote Similarity	NPC477516
0.6471	Remote Similarity	NPC303374
0.6457	Remote Similarity	NPC476950
0.6455	Remote Similarity	NPC182853
0.6452	Remote Similarity	NPC305542
0.6452	Remote Similarity	NPC471194
0.6452	Remote Similarity	NPC471193
0.6449	Remote Similarity	NPC478075
0.6438	Remote Similarity	NPC469928
0.6432	Remote Similarity	NPC14849
0.6429	Remote Similarity	NPC280714
0.6425	Remote Similarity	NPC470485
0.6422	Remote Similarity	NPC206186
0.6418	Remote Similarity	NPC472163
0.6418	Remote Similarity	NPC28368
0.6409	Remote Similarity	NPC469727
0.6409	Remote Similarity	NPC293151
0.6398	Remote Similarity	NPC9373
0.6398	Remote Similarity	NPC259678
0.6395	Remote Similarity	NPC257490
0.6393	Remote Similarity	NPC316202
0.6393	Remote Similarity	NPC118228
0.6386	Remote Similarity	NPC470317
0.6381	Remote Similarity	NPC132874
0.6381	Remote Similarity	NPC138615
0.6381	Remote Similarity	NPC218733
0.6381	Remote Similarity	NPC265642
0.6379	Remote Similarity	NPC41501
0.6378	Remote Similarity	NPC136002
0.6378	Remote Similarity	NPC323798
0.6374	Remote Similarity	NPC471316
0.6373	Remote Similarity	NPC194040
0.6372	Remote Similarity	NPC243850
0.6368	Remote Similarity	NPC283810
0.6364	Remote Similarity	NPC314702
0.6364	Remote Similarity	NPC471192
0.6359	Remote Similarity	NPC290755
0.6359	Remote Similarity	NPC471771
0.6359	Remote Similarity	NPC304074
0.6355	Remote Similarity	NPC21429
0.635	Remote Similarity	NPC315631
0.6347	Remote Similarity	NPC30749
0.6339	Remote Similarity	NPC472243
0.6335	Remote Similarity	NPC27041
0.6332	Remote Similarity	NPC328611
0.633	Remote Similarity	NPC218303
0.633	Remote Similarity	NPC242000
0.6329	Remote Similarity	NPC470483
0.6329	Remote Similarity	NPC1820
0.6329	Remote Similarity	NPC203628
0.6327	Remote Similarity	NPC127362

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 NPC92803 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	683
0.2-0.3	857
0.3-0.4	1682
0.4-0.5	2683
0.5-0.6	2086
0.6-0.7	799
0.7-0.8	46
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
0.7914	Intermediate Similarity	NPD4515	Suspended
0.7849	Intermediate Similarity	NPD5923	Phase 1
0.7487	Intermediate Similarity	NPD7071	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD7225	Discontinued
0.738	Intermediate Similarity	NPD7449	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1919	Approved
0.7278	Intermediate Similarity	NPD1920	Approved
0.7245	Intermediate Similarity	NPD5042	Phase 1
0.7236	Intermediate Similarity	NPD5515	Phase 2
0.7225	Intermediate Similarity	NPD5445	Approved
0.7143	Intermediate Similarity	NPD5078	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3802	Phase 3
0.709	Intermediate Similarity	NPD1165	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD2791	Discontinued
0.7039	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5937	Approved
0.6905	Remote Similarity	NPD5860	Discontinued
0.6902	Remote Similarity	NPD3229	Phase 2
0.6889	Remote Similarity	NPD6017	Discontinued
0.6882	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4430	Phase 2
0.6845	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4539	Phase 1
0.6814	Remote Similarity	NPD4423	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2821	Approved
0.68	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5856	Discontinued
0.6776	Remote Similarity	NPD4942	Approved
0.6757	Remote Similarity	NPD6199	Discontinued
0.6748	Remote Similarity	NPD6874	Approved
0.6734	Remote Similarity	NPD6557	Phase 2
0.6731	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.673	Remote Similarity	NPD4082	Approved
0.6718	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD8025	Phase 2
0.6698	Remote Similarity	NPD5593	Approved
0.6698	Remote Similarity	NPD5594	Approved
0.6685	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5608	Approved
0.6667	Remote Similarity	NPD5882	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5609	Approved
0.665	Remote Similarity	NPD5591	Approved
0.665	Remote Similarity	NPD6162	Approved
0.665	Remote Similarity	NPD6161	Approved
0.6649	Remote Similarity	NPD2469	Approved
0.6649	Remote Similarity	NPD2468	Approved
0.6623	Remote Similarity	NPD3962	Phase 2
0.6623	Remote Similarity	NPD3959	Phase 2
0.6617	Remote Similarity	NPD3316	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD3277	Phase 3
0.6603	Remote Similarity	NPD3416	Discontinued
0.6601	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5183	Approved
0.6598	Remote Similarity	NPD5186	Approved
0.6597	Remote Similarity	NPD4871	Phase 2
0.6592	Remote Similarity	NPD4845	Discontinued
0.6582	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD3248	Phase 1
0.6566	Remote Similarity	NPD3239	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD8311	Discontinued
0.6561	Remote Similarity	NPD2672	Discontinued
0.656	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5546	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD1544	Phase 1
0.6548	Remote Similarity	NPD4020	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD7603	Discontinued
0.6544	Remote Similarity	NPD4897	Phase 2
0.6538	Remote Similarity	NPD5197	Approved
0.6538	Remote Similarity	NPD5196	Approved
0.6538	Remote Similarity	NPD5194	Approved
0.6535	Remote Similarity	NPD5469	Phase 3
0.653	Remote Similarity	NPD7292	Approved
0.6528	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7043	Discontinued
0.6524	Remote Similarity	NPD5552	Discontinued
0.6519	Remote Similarity	NPD3391	Approved
0.6514	Remote Similarity	NPD8149	Discontinued
0.6505	Remote Similarity	NPD4888	Discontinued
0.6503	Remote Similarity	NPD6301	Phase 2
0.6503	Remote Similarity	NPD1625	Approved
0.6495	Remote Similarity	NPD3472	Approved
0.6495	Remote Similarity	NPD4022	Approved
0.6495	Remote Similarity	NPD6376	Discontinued
0.6495	Remote Similarity	NPD2906	Approved
0.6495	Remote Similarity	NPD2907	Approved
0.6492	Remote Similarity	NPD6738	Phase 2
0.6492	Remote Similarity	NPD6737	Phase 2
0.6488	Remote Similarity	NPD5871	Discontinued
0.648	Remote Similarity	NPD3776	Discontinued
0.6471	Remote Similarity	NPD5748	Phase 2
0.6471	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2792	Approved
0.6468	Remote Similarity	NPD7559	Phase 2
0.6465	Remote Similarity	NPD2361	Approved
0.6462	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6379	Discontinued
0.6461	Remote Similarity	NPD2949	Approved
0.6461	Remote Similarity	NPD2950	Approved
0.6458	Remote Similarity	NPD5599	Discontinued
0.6456	Remote Similarity	NPD7569	Approved
0.6456	Remote Similarity	NPD7570	Approved
0.6455	Remote Similarity	NPD4429	Discontinued
0.6449	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD1189	Approved
0.6447	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7443	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD7817	Phase 1
0.6443	Remote Similarity	NPD1168	Approved
0.6439	Remote Similarity	NPD7617	Discontinued
0.6436	Remote Similarity	NPD7546	Discontinued
0.6435	Remote Similarity	NPD8157	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD3372	Discontinued
0.6432	Remote Similarity	NPD3793	Phase 3
0.6432	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD6159	Phase 2
0.6432	Remote Similarity	NPD4092	Approved
0.6425	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD3631	Phase 3
0.6421	Remote Similarity	NPD3684	Discontinued
0.642	Remote Similarity	NPD4894	Discontinued
0.6419	Remote Similarity	NPD7300	Phase 3
0.6419	Remote Similarity	NPD7302	Phase 3
0.6419	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD2359	Approved
0.6411	Remote Similarity	NPD5195	Discontinued
0.6411	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5823	Approved
0.6408	Remote Similarity	NPD6022	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD7660	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD4493	Discontinued
0.6406	Remote Similarity	NPD5416	Discontinued
0.6404	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2827	Approved
0.64	Remote Similarity	NPD2825	Approved
0.64	Remote Similarity	NPD2826	Approved
0.6398	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD1524	Phase 1
0.639	Remote Similarity	NPD1898	Discontinued
0.6387	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD951	Approved
0.6385	Remote Similarity	NPD5513	Phase 2
0.6382	Remote Similarity	NPD4091	Approved
0.6382	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5071	Phase 2
0.6376	Remote Similarity	NPD4492	Approved
0.6376	Remote Similarity	NPD4494	Approved
0.6372	Remote Similarity	NPD4596	Phase 1
0.6369	Remote Similarity	NPD1541	Approved
0.6368	Remote Similarity	NPD5506	Approved
0.6368	Remote Similarity	NPD5507	Approved
0.6368	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD3363	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD3439	Approved
0.6355	Remote Similarity	NPD4412	Phase 2
0.6355	Remote Similarity	NPD4465	Phase 2
0.6355	Remote Similarity	NPD4467	Phase 2
0.6355	Remote Similarity	NPD1294	Discontinued
0.6351	Remote Similarity	NPD5999	Phase 2
0.6351	Remote Similarity	NPD6757	Phase 3
0.635	Remote Similarity	NPD3755	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD2951	Discontinued
0.6347	Remote Similarity	NPD3243	Approved
0.6343	Remote Similarity	NPD7232	Discontinued
0.6343	Remote Similarity	NPD2916	Discontinued
0.6341	Remote Similarity	NPD4948	Discontinued
0.6338	Remote Similarity	NPD7316	Discontinued
0.6337	Remote Similarity	NPD5637	Discontinued
0.6335	Remote Similarity	NPD7072	Phase 2
0.6332	Remote Similarity	NPD3522	Approved
0.6332	Remote Similarity	NPD7324	Discontinued
0.6332	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4432	Discontinued
0.633	Remote Similarity	NPD979	Approved
0.6327	Remote Similarity	NPD3263	Phase 3
0.6326	Remote Similarity	NPD6807	Phase 3
0.6324	Remote Similarity	NPD2762	Phase 2
0.6323	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4393	Approved
0.6321	Remote Similarity	NPD33	Approved
0.6319	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD7428	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD3999	Approved
0.6318	Remote Similarity	NPD3998	Approved
0.6318	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD3997	Approved
0.6316	Remote Similarity	NPD6707	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4400	Approved
0.6316	Remote Similarity	NPD5022	Discontinued

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