NPASS Compound

Structure

NPC88970 OpenBabel07101719242D 21 24 0 0 0 0 0 0 0 0999 V2000 3.4641 -0.0000 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 3.4641 -1.0000 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 2.5981 0.5000 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 -1.5000 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 -0.7818 -1.6235 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 -1.7568 0.4010 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 -0.7818 0.6235 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 -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 1 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 10 2 0 0 0 0 6 11 2 0 0 0 0 7 12 2 0 0 0 0 8 13 2 0 0 0 0 9 14 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 15 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 17 2 0 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 16 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	277.09
Volume:	277.909
LogP:	0.876
LogD:	1.127
LogS:	-3.745
# Rotatable Bonds:	0
TPSA:	63.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.679
Synthetic Accessibility Score:	2.254
Fsp3:	0.062
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:	-4.794
MDCK Permeability:	2.3304652131628245e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.938
Plasma Protein Binding (PPB):	65.79586029052734%
Volume Distribution (VD):	0.852
Pgp-substrate:	12.097026824951172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.476
CYP1A2-substrate:	0.452
CYP2C19-inhibitor:	0.147
CYP2C19-substrate:	0.703
CYP2C9-inhibitor:	0.238
CYP2C9-substrate:	0.638
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.266
CYP3A4-inhibitor:	0.289
CYP3A4-substrate:	0.78

ADMET: Excretion

Clearance (CL):	2.722
Half-life (T1/2):	0.81

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.331
Drug-inuced Liver Injury (DILI):	0.873
AMES Toxicity:	0.471
Rat Oral Acute Toxicity:	0.205
Maximum Recommended Daily Dose:	0.046
Skin Sensitization:	0.094
Carcinogencity:	0.443
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.074

Download Data

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

Natural Product: NPC88970

Natural Product ID:	NPC88970
*Common Name:**	Sclerotigenin
IUPAC Name:	6,7-dihydroquinazolino[3,2-a][1,4]benzodiazepine-5,13-dione
Synonyms:	Sclerotigenin
Standard InCHIKey:	NGYKOTTXJAPLPC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H11N3O2/c20-15-11-6-2-4-8-13(11)19-14(9-17-15)18-12-7-3-1-5-10(12)16(19)21/h1-8H,9H2,(H,17,20)
SMILES:	c1ccc2c(c1)c(=O)n1-c3ccccc3C(=NCc1n2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490538
PubChem CID:	10802469
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
NPO1394	Penicillium sclerotigenum	Species	Aspergillaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[10217735]
NPO40987	Penicillium raistrickii IMB17-034	Strain	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31013089]
NPO1394	Penicillium sclerotigenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
EC50	1
IC50	3
MIC	4
Others	3

Activity Type	# Activity
Cell Line	3
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>=	100000.0	nM	PMID[570195]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>=	100000.0	nM	PMID[570195]
NPT81	Cell Line	A549	Homo sapiens	IC50	>=	100000.0	nM	PMID[570195]
NPT915	Organism	Helicoverpa zea	Helicoverpa zea	Activity	=	42.0	%	PMID[570194]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[570195]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	128.0	ug.mL-1	PMID[570195]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[570195]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	128.0	ug.mL-1	PMID[570195]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	EC50	=	5800.0	nM	PMID[570195]
NPT2	Others	Unspecified		CC50	>	200000.0	nM	PMID[570195]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	35.0	n.a.	PMID[570195]

☑ 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 NPC88970 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	525
0.1-0.2	5480
0.2-0.3	12269
0.3-0.4	16862
0.4-0.5	3661
0.5-0.6	2979
0.6-0.7	770
0.7-0.8	94
0.8-0.85	44
0.85-0.9	10
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC471130
0.8862	High Similarity	NPC18890
0.8757	High Similarity	NPC92803
0.8471	Intermediate Similarity	NPC471132
0.8313	Intermediate Similarity	NPC475594
0.8263	Intermediate Similarity	NPC475607
0.8214	Intermediate Similarity	NPC474081
0.8166	Intermediate Similarity	NPC474041
0.8166	Intermediate Similarity	NPC475761
0.8146	Intermediate Similarity	NPC300299
0.7955	Intermediate Similarity	NPC471196
0.7955	Intermediate Similarity	NPC471195
0.7914	Intermediate Similarity	NPC84317
0.7879	Intermediate Similarity	NPC27904
0.7871	Intermediate Similarity	NPC83214
0.7841	Intermediate Similarity	NPC473815
0.7821	Intermediate Similarity	NPC207554
0.7803	Intermediate Similarity	NPC475685
0.7784	Intermediate Similarity	NPC150308
0.7771	Intermediate Similarity	NPC2823
0.773	Intermediate Similarity	NPC295548
0.7712	Intermediate Similarity	NPC207428
0.7711	Intermediate Similarity	NPC154478
0.7701	Intermediate Similarity	NPC471155
0.7679	Intermediate Similarity	NPC189116
0.766	Intermediate Similarity	NPC270241
0.7647	Intermediate Similarity	NPC225400
0.764	Intermediate Similarity	NPC324445
0.7637	Intermediate Similarity	NPC472540
0.7637	Intermediate Similarity	NPC472539
0.7637	Intermediate Similarity	NPC470787
0.7606	Intermediate Similarity	NPC472538
0.7606	Intermediate Similarity	NPC470786
0.7596	Intermediate Similarity	NPC472542
0.7596	Intermediate Similarity	NPC472541
0.7582	Intermediate Similarity	NPC198401
0.75	Intermediate Similarity	NPC184437
0.747	Intermediate Similarity	NPC295021
0.7468	Intermediate Similarity	NPC122553
0.7439	Intermediate Similarity	NPC300596
0.7439	Intermediate Similarity	NPC237649
0.7429	Intermediate Similarity	NPC471743
0.7394	Intermediate Similarity	NPC144691
0.7378	Intermediate Similarity	NPC254798
0.7371	Intermediate Similarity	NPC470548
0.7356	Intermediate Similarity	NPC355
0.7355	Intermediate Similarity	NPC226662
0.734	Intermediate Similarity	NPC471944
0.7305	Intermediate Similarity	NPC117032
0.7288	Intermediate Similarity	NPC219848
0.7283	Intermediate Similarity	NPC182131
0.7278	Intermediate Similarity	NPC253476
0.7247	Intermediate Similarity	NPC256268
0.7222	Intermediate Similarity	NPC471574
0.7222	Intermediate Similarity	NPC243058
0.7222	Intermediate Similarity	NPC43477
0.7222	Intermediate Similarity	NPC248601
0.7219	Intermediate Similarity	NPC471199
0.7209	Intermediate Similarity	NPC476231
0.7188	Intermediate Similarity	NPC471191
0.7182	Intermediate Similarity	NPC203635
0.7182	Intermediate Similarity	NPC471742
0.7164	Intermediate Similarity	NPC220851
0.7143	Intermediate Similarity	NPC106118
0.7104	Intermediate Similarity	NPC90415
0.7091	Intermediate Similarity	NPC136002
0.7088	Intermediate Similarity	NPC21429
0.7059	Intermediate Similarity	NPC257490
0.7006	Intermediate Similarity	NPC259678
0.7	Intermediate Similarity	NPC244425
0.7	Intermediate Similarity	NPC15384
0.7	Intermediate Similarity	NPC474916
0.6974	Remote Similarity	NPC16249
0.6971	Remote Similarity	NPC113056
0.6971	Remote Similarity	NPC138293
0.6951	Remote Similarity	NPC472243
0.6937	Remote Similarity	NPC476687
0.6937	Remote Similarity	NPC476685
0.6937	Remote Similarity	NPC476689
0.6923	Remote Similarity	NPC88110
0.6919	Remote Similarity	NPC72956
0.6915	Remote Similarity	NPC471197
0.6914	Remote Similarity	NPC289776
0.6914	Remote Similarity	NPC133470
0.6914	Remote Similarity	NPC191863
0.6899	Remote Similarity	NPC476950
0.6888	Remote Similarity	NPC243850
0.6884	Remote Similarity	NPC471194
0.6884	Remote Similarity	NPC471193
0.6884	Remote Similarity	NPC153980
0.6884	Remote Similarity	NPC6865
0.6883	Remote Similarity	NPC130931
0.6881	Remote Similarity	NPC471198
0.6875	Remote Similarity	NPC314098
0.6875	Remote Similarity	NPC204867
0.6872	Remote Similarity	NPC318183
0.6853	Remote Similarity	NPC285192
0.6848	Remote Similarity	NPC470317
0.6848	Remote Similarity	NPC242933
0.6826	Remote Similarity	NPC308197
0.6818	Remote Similarity	NPC177684
0.6818	Remote Similarity	NPC291962
0.6813	Remote Similarity	NPC14849
0.681	Remote Similarity	NPC173295
0.6796	Remote Similarity	NPC328611
0.6788	Remote Similarity	NPC181527
0.6782	Remote Similarity	NPC471192
0.6776	Remote Similarity	NPC147298
0.6776	Remote Similarity	NPC182057
0.6776	Remote Similarity	NPC131450
0.6774	Remote Similarity	NPC112373
0.6774	Remote Similarity	NPC258531
0.6774	Remote Similarity	NPC161956
0.6772	Remote Similarity	NPC205946
0.677	Remote Similarity	NPC316746
0.677	Remote Similarity	NPC231382
0.6766	Remote Similarity	NPC472241
0.6761	Remote Similarity	NPC93653
0.6761	Remote Similarity	NPC322644
0.675	Remote Similarity	NPC150863
0.6748	Remote Similarity	NPC162417
0.6748	Remote Similarity	NPC316104
0.6746	Remote Similarity	NPC471762
0.673	Remote Similarity	NPC250476
0.672	Remote Similarity	NPC285923
0.6707	Remote Similarity	NPC471164
0.6703	Remote Similarity	NPC248862
0.6699	Remote Similarity	NPC157931
0.6688	Remote Similarity	NPC39818
0.6687	Remote Similarity	NPC315224
0.6667	Remote Similarity	NPC221873
0.6667	Remote Similarity	NPC66777
0.6648	Remote Similarity	NPC299582
0.6647	Remote Similarity	NPC472242
0.6632	Remote Similarity	NPC313293
0.6629	Remote Similarity	NPC199737
0.6628	Remote Similarity	NPC242000
0.6626	Remote Similarity	NPC40364
0.6619	Remote Similarity	NPC257851
0.6613	Remote Similarity	NPC270301
0.661	Remote Similarity	NPC471122
0.6607	Remote Similarity	NPC316202
0.6605	Remote Similarity	NPC472245
0.6605	Remote Similarity	NPC194562
0.6605	Remote Similarity	NPC280807
0.6605	Remote Similarity	NPC314431
0.6598	Remote Similarity	NPC316282
0.6561	Remote Similarity	NPC179605
0.6561	Remote Similarity	NPC279385
0.6558	Remote Similarity	NPC288232
0.6538	Remote Similarity	NPC471943
0.6537	Remote Similarity	NPC62995
0.6533	Remote Similarity	NPC314648
0.6529	Remote Similarity	NPC314287
0.6526	Remote Similarity	NPC278434
0.6524	Remote Similarity	NPC325479
0.6522	Remote Similarity	NPC469529
0.6519	Remote Similarity	NPC103292
0.6512	Remote Similarity	NPC478039
0.6508	Remote Similarity	NPC476341
0.6503	Remote Similarity	NPC292265
0.65	Remote Similarity	NPC226794
0.6495	Remote Similarity	NPC202812
0.6479	Remote Similarity	NPC116622
0.6478	Remote Similarity	NPC268534
0.6471	Remote Similarity	NPC298320
0.6467	Remote Similarity	NPC177261
0.6464	Remote Similarity	NPC471124
0.6461	Remote Similarity	NPC104345
0.6456	Remote Similarity	NPC322064
0.6455	Remote Similarity	NPC470003
0.645	Remote Similarity	NPC315051
0.6448	Remote Similarity	NPC472118
0.6444	Remote Similarity	NPC472117
0.6442	Remote Similarity	NPC122235
0.6442	Remote Similarity	NPC209389
0.6438	Remote Similarity	NPC328683
0.6438	Remote Similarity	NPC283130
0.6433	Remote Similarity	NPC220698
0.6432	Remote Similarity	NPC303225
0.6429	Remote Similarity	NPC296163
0.6421	Remote Similarity	NPC133003
0.6418	Remote Similarity	NPC315638
0.6418	Remote Similarity	NPC314855
0.6418	Remote Similarity	NPC313345
0.6418	Remote Similarity	NPC313796
0.6413	Remote Similarity	NPC112336
0.6413	Remote Similarity	NPC474814
0.641	Remote Similarity	NPC147957
0.64	Remote Similarity	NPC288445
0.6387	Remote Similarity	NPC135601
0.6387	Remote Similarity	NPC17273
0.6387	Remote Similarity	NPC141612
0.6386	Remote Similarity	NPC315545
0.6386	Remote Similarity	NPC314297
0.6383	Remote Similarity	NPC39822
0.6369	Remote Similarity	NPC325599
0.6364	Remote Similarity	NPC9475
0.6358	Remote Similarity	NPC37584
0.6354	Remote Similarity	NPC206186

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 NPC88970 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	712
0.2-0.3	793
0.3-0.4	1837
0.4-0.5	2333
0.5-0.6	2125
0.6-0.7	940
0.7-0.8	115
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8402	Intermediate Similarity	NPD5923	Phase 1
0.8188	Intermediate Similarity	NPD1919	Approved
0.8188	Intermediate Similarity	NPD1920	Approved
0.7976	Intermediate Similarity	NPD1165	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD5042	Phase 1
0.7677	Intermediate Similarity	NPD2791	Discontinued
0.7651	Intermediate Similarity	NPD7735	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD4939	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD4942	Approved
0.7542	Intermediate Similarity	NPD4515	Suspended
0.7453	Intermediate Similarity	NPD4430	Phase 2
0.7362	Intermediate Similarity	NPD6017	Discontinued
0.7308	Intermediate Similarity	NPD7855	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3248	Phase 1
0.7284	Intermediate Similarity	NPD1189	Approved
0.7273	Intermediate Similarity	NPD5856	Discontinued
0.7239	Intermediate Similarity	NPD1625	Approved
0.7238	Intermediate Similarity	NPD6557	Phase 2
0.7229	Intermediate Similarity	NPD4888	Discontinued
0.7215	Intermediate Similarity	NPD2950	Approved
0.7215	Intermediate Similarity	NPD2949	Approved
0.7212	Intermediate Similarity	NPD1524	Phase 1
0.7186	Intermediate Similarity	NPD5546	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7662	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3277	Phase 3
0.7134	Intermediate Similarity	NPD6301	Phase 2
0.7128	Intermediate Similarity	NPD5515	Phase 2
0.7111	Intermediate Similarity	NPD5445	Approved
0.7107	Intermediate Similarity	NPD1541	Approved
0.7101	Intermediate Similarity	NPD6707	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5748	Phase 2
0.7062	Intermediate Similarity	NPD3776	Discontinued
0.7056	Intermediate Similarity	NPD7225	Discontinued
0.7037	Intermediate Similarity	NPD4077	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3363	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7443	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7072	Phase 2
0.7017	Intermediate Similarity	NPD7014	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD3434	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3802	Phase 3
0.6994	Remote Similarity	NPD1626	Approved
0.6989	Remote Similarity	NPD3439	Approved
0.6977	Remote Similarity	NPD951	Approved
0.6977	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4948	Discontinued
0.6952	Remote Similarity	NPD6022	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1230	Approved
0.6928	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4432	Discontinued
0.6923	Remote Similarity	NPD979	Approved
0.6915	Remote Similarity	NPD7569	Approved
0.6915	Remote Similarity	NPD7570	Approved
0.6915	Remote Similarity	NPD6887	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4871	Phase 2
0.6909	Remote Similarity	NPD9477	Approved
0.6906	Remote Similarity	NPD3755	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7091	Discontinued
0.6875	Remote Similarity	NPD1619	Phase 3
0.6868	Remote Similarity	NPD7428	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2365	Approved
0.6839	Remote Similarity	NPD212	Discontinued
0.6835	Remote Similarity	NPD1593	Approved
0.6826	Remote Similarity	NPD2820	Phase 3
0.6825	Remote Similarity	NPD3406	Suspended
0.6825	Remote Similarity	NPD5937	Approved
0.6824	Remote Similarity	NPD4161	Discontinued
0.6821	Remote Similarity	NPD1514	Discontinued
0.6813	Remote Similarity	NPD4092	Approved
0.6811	Remote Similarity	NPD4412	Phase 2
0.6804	Remote Similarity	NPD7817	Phase 1
0.68	Remote Similarity	NPD33	Approved
0.68	Remote Similarity	NPD4393	Approved
0.6796	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD3522	Approved
0.6791	Remote Similarity	NPD4988	Discontinued
0.679	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1594	Phase 3
0.679	Remote Similarity	NPD1595	Approved
0.6789	Remote Similarity	NPD4539	Phase 1
0.6784	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3997	Approved
0.6776	Remote Similarity	NPD3998	Approved
0.6776	Remote Similarity	NPD3999	Approved
0.6774	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5086	Approved
0.6763	Remote Similarity	NPD3229	Phase 2
0.6761	Remote Similarity	NPD2506	Approved
0.6758	Remote Similarity	NPD4091	Approved
0.6758	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD3315	Phase 3
0.6736	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD1664	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD3792	Approved
0.6721	Remote Similarity	NPD3994	Approved
0.6721	Remote Similarity	NPD3991	Approved
0.6721	Remote Similarity	NPD3996	Approved
0.6721	Remote Similarity	NPD3993	Approved
0.6721	Remote Similarity	NPD3995	Approved
0.6721	Remote Similarity	NPD3992	Approved
0.672	Remote Similarity	NPD721	Approved
0.6705	Remote Similarity	NPD4485	Approved
0.6705	Remote Similarity	NPD2882	Phase 1
0.6703	Remote Similarity	NPD3990	Phase 3
0.6687	Remote Similarity	NPD12	Approved
0.6687	Remote Similarity	NPD699	Approved
0.6687	Remote Similarity	NPD697	Approved
0.6687	Remote Similarity	NPD1527	Phase 2
0.6687	Remote Similarity	NPD700	Approved
0.6687	Remote Similarity	NPD13	Approved
0.6686	Remote Similarity	NPD2836	Approved
0.6686	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3782	Discontinued
0.6685	Remote Similarity	NPD3239	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7232	Discontinued
0.6667	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4334	Discontinued
0.6667	Remote Similarity	NPD1001	Discontinued
0.6649	Remote Similarity	NPD4330	Approved
0.6649	Remote Similarity	NPD3989	Phase 3
0.6649	Remote Similarity	NPD4329	Approved
0.6649	Remote Similarity	NPD8146	Phase 2
0.6648	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1781	Discontinued
0.6635	Remote Similarity	NPD6752	Phase 1
0.6635	Remote Similarity	NPD6753	Phase 1
0.663	Remote Similarity	NPD2369	Discontinued
0.663	Remote Similarity	NPD7795	Phase 2
0.6629	Remote Similarity	NPD1210	Approved
0.6627	Remote Similarity	NPD5024	Approved
0.6618	Remote Similarity	NPD7439	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD1173	Approved
0.6615	Remote Similarity	NPD5882	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD6483	Approved
0.6614	Remote Similarity	NPD6484	Approved
0.6614	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.661	Remote Similarity	NPD2427	Approved
0.6609	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD3773	Approved
0.6599	Remote Similarity	NPD3774	Approved
0.6599	Remote Similarity	NPD3775	Approved
0.6598	Remote Similarity	NPD5591	Approved
0.6598	Remote Similarity	NPD4423	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2336	Approved
0.6595	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3805	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD2037	Approved
0.6568	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD6768	Approved
0.6564	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4376	Phase 3
0.6548	Remote Similarity	NPD5552	Discontinued
0.6541	Remote Similarity	NPD7065	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD1175	Approved
0.6534	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5423	Phase 2
0.6531	Remote Similarity	NPD8050	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD4214	Discontinued
0.6522	Remote Similarity	NPD4883	Approved
0.6522	Remote Similarity	NPD5153	Clinical (unspecified phase)
0.652	Remote Similarity	NPD7616	Discontinued
0.652	Remote Similarity	NPD3780	Phase 2
0.6517	Remote Similarity	NPD6486	Approved
0.6517	Remote Similarity	NPD7599	Phase 2
0.6517	Remote Similarity	NPD6487	Approved
0.6517	Remote Similarity	NPD4514	Approved
0.6515	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD7572	Phase 2
0.6512	Remote Similarity	NPD6142	Phase 3
0.6505	Remote Similarity	NPD6710	Phase 3
0.6505	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2432	Approved
0.6503	Remote Similarity	NPD3824	Phase 1
0.6503	Remote Similarity	NPD2431	Approved
0.6502	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3789	Approved
0.6497	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD2468	Approved
0.6497	Remote Similarity	NPD2351	Discontinued
0.6497	Remote Similarity	NPD2469	Approved
0.6497	Remote Similarity	NPD6395	Phase 2
0.6495	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD8025	Phase 2
0.6491	Remote Similarity	NPD2387	Approved
0.6491	Remote Similarity	NPD5918	Discontinued
0.6485	Remote Similarity	NPD5593	Approved
0.6485	Remote Similarity	NPD5594	Approved
0.6484	Remote Similarity	NPD2821	Approved
0.648	Remote Similarity	NPD7600	Phase 2
0.6477	Remote Similarity	NPD4315	Phase 2
0.6474	Remote Similarity	NPD4940	Approved
0.6471	Remote Similarity	NPD3227	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