NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	269.02
Volume:	242.903
LogP:	1.608
LogD:	1.676
LogS:	-3.301
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.785
Synthetic Accessibility Score:	2.558
Fsp3:	0.273
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:	-4.689
MDCK Permeability:	2.32114180107601e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.941
Plasma Protein Binding (PPB):	75.2244644165039%
Volume Distribution (VD):	0.849
Pgp-substrate:	9.371171951293945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.934
CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.94
CYP2C19-substrate:	0.905
CYP2C9-inhibitor:	0.574
CYP2C9-substrate:	0.862
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.556
CYP3A4-inhibitor:	0.643
CYP3A4-substrate:	0.823

ADMET: Excretion

Clearance (CL):	5.477
Half-life (T1/2):	0.343

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.255
Drug-inuced Liver Injury (DILI):	0.811
AMES Toxicity:	0.722
Rat Oral Acute Toxicity:	0.38
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.091
Carcinogencity:	0.865
Eye Corrosion:	0.011
Eye Irritation:	0.45
Respiratory Toxicity:	0.073

Download Data

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

Natural Product: NPC206941

Natural Product ID:	NPC206941
*Common Name:**	Bretschneiderazine B
IUPAC Name:	7,8-dimethoxy-3-methyl-2-sulfanylidene-1,3-benzothiazin-4-one
Synonyms:
Standard InCHIKey:	GQSCDKJMVQBKSC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H11NO3S2/c1-12-10(13)6-4-5-7(14-2)8(15-3)9(6)17-11(12)16/h4-5H,1-3H3
SMILES:	Cn1c(=O)c2ccc(c(c2sc1=S)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1223571
PubChem CID:	46938553
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000309] Benzothiazines

*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
NPO1813	Bretschneidera sinensis	Species	Akaniaceae	Eukaryota	stems	Jiujiang, Jiangxi Province, China	2008-AUG	PMID[20722446]
NPO1813	Bretschneidera sinensis	Species	Akaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1813	Bretschneidera sinensis	Species	Akaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1813	Bretschneidera sinensis	Species	Akaniaceae	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
IC50	4
Others	4

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT937	Cell Line	NCI-H446	Homo sapiens	IC50	=	60.21	ug.mL-1	PMID[511522]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[511522]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[511522]
NPT937	Cell Line	NCI-H446	Homo sapiens	GI	=	41.33	%	PMID[511522]
NPT116	Cell Line	HL-60	Homo sapiens	GI	=	8.04	%	PMID[511522]
NPT393	Cell Line	HCT-116	Homo sapiens	GI	=	0.0	%	PMID[511522]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100.0	ug.mL-1	PMID[511522]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	0.0	%	PMID[511522]

☑ 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 NPC206941 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	631
0.1-0.2	5663
0.2-0.3	12068
0.3-0.4	5122
0.4-0.5	16044
0.5-0.6	2907
0.6-0.7	250
0.7-0.8	10
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9141	High Similarity	NPC20395
0.8098	Intermediate Similarity	NPC119669
0.7765	Intermediate Similarity	NPC135006
0.7679	Intermediate Similarity	NPC470708
0.7337	Intermediate Similarity	NPC470088
0.7314	Intermediate Similarity	NPC153631
0.7239	Intermediate Similarity	NPC416184
0.7202	Intermediate Similarity	NPC469978
0.716	Intermediate Similarity	NPC266425
0.7126	Intermediate Similarity	NPC908
0.7126	Intermediate Similarity	NPC138438
0.7104	Intermediate Similarity	NPC222524
0.7033	Intermediate Similarity	NPC303581
0.7033	Intermediate Similarity	NPC67978
0.7017	Intermediate Similarity	NPC86469
0.6975	Remote Similarity	NPC160193
0.6963	Remote Similarity	NPC254957
0.6957	Remote Similarity	NPC172403
0.6957	Remote Similarity	NPC308267
0.6943	Remote Similarity	NPC225245
0.6943	Remote Similarity	NPC295317
0.6915	Remote Similarity	NPC116007
0.6909	Remote Similarity	NPC167096
0.6901	Remote Similarity	NPC110337
0.6886	Remote Similarity	NPC225745
0.6886	Remote Similarity	NPC470707
0.6867	Remote Similarity	NPC73883
0.6867	Remote Similarity	NPC255817
0.6867	Remote Similarity	NPC251454
0.6867	Remote Similarity	NPC196609
0.6867	Remote Similarity	NPC277042
0.6867	Remote Similarity	NPC136330
0.6867	Remote Similarity	NPC205178
0.6867	Remote Similarity	NPC180647
0.6867	Remote Similarity	NPC230698
0.6845	Remote Similarity	NPC231572
0.6842	Remote Similarity	NPC477259
0.6842	Remote Similarity	NPC169387
0.6839	Remote Similarity	NPC469539
0.6839	Remote Similarity	NPC469540
0.6833	Remote Similarity	NPC94292
0.6826	Remote Similarity	NPC99078
0.6825	Remote Similarity	NPC83511
0.6821	Remote Similarity	NPC71124
0.6813	Remote Similarity	NPC474691
0.6806	Remote Similarity	NPC208890
0.6802	Remote Similarity	NPC69623
0.6802	Remote Similarity	NPC226601
0.6796	Remote Similarity	NPC476569
0.6791	Remote Similarity	NPC121400
0.6786	Remote Similarity	NPC252107
0.6786	Remote Similarity	NPC220923
0.6782	Remote Similarity	NPC296858
0.677	Remote Similarity	NPC30216
0.6761	Remote Similarity	NPC476579
0.6755	Remote Similarity	NPC27887
0.6754	Remote Similarity	NPC471650
0.6747	Remote Similarity	NPC160692
0.6739	Remote Similarity	NPC130921
0.6728	Remote Similarity	NPC473626
0.6726	Remote Similarity	NPC7018
0.6726	Remote Similarity	NPC131204
0.6726	Remote Similarity	NPC301050
0.6723	Remote Similarity	NPC28414
0.6723	Remote Similarity	NPC298924
0.6706	Remote Similarity	NPC314682
0.6705	Remote Similarity	NPC189908
0.6704	Remote Similarity	NPC57512
0.6701	Remote Similarity	NPC5374
0.6687	Remote Similarity	NPC154275
0.6686	Remote Similarity	NPC153644
0.6685	Remote Similarity	NPC26353
0.6667	Remote Similarity	NPC35345
0.6667	Remote Similarity	NPC328750
0.6667	Remote Similarity	NPC213206
0.6667	Remote Similarity	NPC474915
0.6667	Remote Similarity	NPC227683
0.6667	Remote Similarity	NPC188163
0.665	Remote Similarity	NPC207971
0.6649	Remote Similarity	NPC5167
0.6646	Remote Similarity	NPC203719
0.6646	Remote Similarity	NPC286683
0.6646	Remote Similarity	NPC16651
0.6646	Remote Similarity	NPC32163
0.6646	Remote Similarity	NPC117237
0.6633	Remote Similarity	NPC477258
0.6629	Remote Similarity	NPC476580
0.6629	Remote Similarity	NPC58661
0.6628	Remote Similarity	NPC475698
0.6617	Remote Similarity	NPC268077
0.6611	Remote Similarity	NPC131440
0.6608	Remote Similarity	NPC59661
0.6599	Remote Similarity	NPC24228
0.6595	Remote Similarity	NPC284842
0.6592	Remote Similarity	NPC191200
0.6592	Remote Similarity	NPC291583
0.659	Remote Similarity	NPC474553
0.6588	Remote Similarity	NPC194359
0.6588	Remote Similarity	NPC253429
0.6588	Remote Similarity	NPC28641
0.6587	Remote Similarity	NPC217574
0.6578	Remote Similarity	NPC177023
0.6576	Remote Similarity	NPC231198
0.6562	Remote Similarity	NPC149571
0.6561	Remote Similarity	NPC35680
0.6556	Remote Similarity	NPC169742
0.6552	Remote Similarity	NPC308943
0.6548	Remote Similarity	NPC153453
0.6538	Remote Similarity	NPC106786
0.6538	Remote Similarity	NPC118804
0.6529	Remote Similarity	NPC469808
0.6527	Remote Similarity	NPC298268
0.6527	Remote Similarity	NPC66905
0.6527	Remote Similarity	NPC285776
0.6524	Remote Similarity	NPC120066
0.6517	Remote Similarity	NPC223125
0.6517	Remote Similarity	NPC478189
0.6514	Remote Similarity	NPC185838
0.6514	Remote Similarity	NPC130926
0.6509	Remote Similarity	NPC94280
0.6509	Remote Similarity	NPC328419
0.6509	Remote Similarity	NPC159150
0.6509	Remote Similarity	NPC103947
0.6509	Remote Similarity	NPC193673
0.6509	Remote Similarity	NPC45783
0.6506	Remote Similarity	NPC304747
0.6494	Remote Similarity	NPC476567
0.6494	Remote Similarity	NPC136860
0.6494	Remote Similarity	NPC128019
0.6494	Remote Similarity	NPC261940
0.6491	Remote Similarity	NPC113236
0.6491	Remote Similarity	NPC471316
0.6491	Remote Similarity	NPC214036
0.6486	Remote Similarity	NPC306669
0.648	Remote Similarity	NPC226708
0.6477	Remote Similarity	NPC474649
0.6477	Remote Similarity	NPC474652
0.6471	Remote Similarity	NPC96406
0.6455	Remote Similarity	NPC329992
0.645	Remote Similarity	NPC207239
0.645	Remote Similarity	NPC50763
0.645	Remote Similarity	NPC111888
0.6448	Remote Similarity	NPC257143
0.6444	Remote Similarity	NPC223124
0.6442	Remote Similarity	NPC298486
0.6441	Remote Similarity	NPC191376
0.6441	Remote Similarity	NPC16107
0.6441	Remote Similarity	NPC210437
0.6441	Remote Similarity	NPC106295
0.6441	Remote Similarity	NPC476151
0.6441	Remote Similarity	NPC321505
0.6441	Remote Similarity	NPC476144
0.6441	Remote Similarity	NPC179825
0.6441	Remote Similarity	NPC51957
0.6433	Remote Similarity	NPC137172
0.6433	Remote Similarity	NPC88065
0.6433	Remote Similarity	NPC89504
0.6433	Remote Similarity	NPC307682
0.6433	Remote Similarity	NPC95485
0.6433	Remote Similarity	NPC145446
0.6432	Remote Similarity	NPC59567
0.6429	Remote Similarity	NPC299010
0.6425	Remote Similarity	NPC102760
0.6412	Remote Similarity	NPC283823
0.6412	Remote Similarity	NPC159418
0.6406	Remote Similarity	NPC99723
0.6404	Remote Similarity	NPC7467
0.6404	Remote Similarity	NPC428
0.6404	Remote Similarity	NPC246587
0.6404	Remote Similarity	NPC147390
0.6404	Remote Similarity	NPC135538
0.6404	Remote Similarity	NPC24233
0.6404	Remote Similarity	NPC475959
0.6404	Remote Similarity	NPC476571
0.6395	Remote Similarity	NPC95366
0.6395	Remote Similarity	NPC248505
0.6391	Remote Similarity	NPC318862
0.6387	Remote Similarity	NPC85613
0.6374	Remote Similarity	NPC144662
0.6373	Remote Similarity	NPC163829
0.6369	Remote Similarity	NPC103379
0.6369	Remote Similarity	NPC472885
0.6369	Remote Similarity	NPC477565
0.6364	Remote Similarity	NPC294249
0.6359	Remote Similarity	NPC207873
0.6359	Remote Similarity	NPC100573
0.6358	Remote Similarity	NPC160747
0.6346	Remote Similarity	NPC183648
0.6341	Remote Similarity	NPC158551
0.6337	Remote Similarity	NPC139519
0.6333	Remote Similarity	NPC274026
0.6333	Remote Similarity	NPC55470
0.6332	Remote Similarity	NPC469816
0.6332	Remote Similarity	NPC469815
0.6327	Remote Similarity	NPC162694
0.6322	Remote Similarity	NPC470962
0.6318	Remote Similarity	NPC215098
0.6318	Remote Similarity	NPC46744
0.6318	Remote Similarity	NPC73020
0.6318	Remote Similarity	NPC70290

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 NPC206941 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	816
0.2-0.3	984
0.3-0.4	2161
0.4-0.5	3467
0.5-0.6	1242
0.6-0.7	99
0.7-0.8	1
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
0.8049	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD824	Approved
0.7346	Intermediate Similarity	NPD743	Approved
0.7341	Intermediate Similarity	NPD5978	Approved
0.7341	Intermediate Similarity	NPD5977	Approved
0.6971	Remote Similarity	NPD7110	Phase 1
0.6971	Remote Similarity	NPD6386	Approved
0.6971	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6385	Approved
0.6952	Remote Similarity	NPD6618	Phase 2
0.695	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5564	Approved
0.6936	Remote Similarity	NPD1670	Discontinued
0.6936	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD3641	Approved
0.6936	Remote Similarity	NPD3640	Phase 3
0.6936	Remote Similarity	NPD3639	Approved
0.6895	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD1307	Phase 2
0.6872	Remote Similarity	NPD1309	Phase 2
0.6868	Remote Similarity	NPD5242	Approved
0.6867	Remote Similarity	NPD2492	Phase 1
0.6848	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5071	Phase 2
0.6758	Remote Similarity	NPD7802	Discontinued
0.6754	Remote Similarity	NPD7291	Discontinued
0.6747	Remote Similarity	NPD3142	Approved
0.6747	Remote Similarity	NPD3140	Approved
0.6723	Remote Similarity	NPD6876	Approved
0.6723	Remote Similarity	NPD6875	Approved
0.6684	Remote Similarity	NPD2325	Approved
0.6667	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5708	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD9494	Approved
0.6629	Remote Similarity	NPD2592	Discontinued
0.6611	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6873	Phase 2
0.6575	Remote Similarity	NPD5353	Approved
0.6573	Remote Similarity	NPD746	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6990	Approved
0.6562	Remote Similarity	NPD6989	Approved
0.6561	Remote Similarity	NPD6297	Approved
0.6543	Remote Similarity	NPD5312	Approved
0.6543	Remote Similarity	NPD5313	Approved
0.6541	Remote Similarity	NPD5183	Approved
0.6541	Remote Similarity	NPD5186	Approved
0.6528	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD5718	Phase 2
0.6502	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5262	Discontinued
0.6477	Remote Similarity	NPD5297	Approved
0.6465	Remote Similarity	NPD6834	Approved
0.6452	Remote Similarity	NPD4166	Phase 2
0.6441	Remote Similarity	NPD4584	Approved
0.6441	Remote Similarity	NPD1424	Approved
0.6425	Remote Similarity	NPD6851	Approved
0.6425	Remote Similarity	NPD6853	Approved
0.6418	Remote Similarity	NPD5457	Discontinued
0.6414	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD6826	Discontinued
0.6382	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5025	Approved
0.6348	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD3146	Approved
0.634	Remote Similarity	NPD6734	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD6493	Phase 3
0.6322	Remote Similarity	NPD5085	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD4420	Approved
0.6318	Remote Similarity	NPD7942	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD6890	Discontinued
0.6298	Remote Similarity	NPD4017	Approved
0.6296	Remote Similarity	NPD2898	Approved
0.6289	Remote Similarity	NPD7280	Phase 3
0.6289	Remote Similarity	NPD7281	Phase 3
0.6286	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD4503	Phase 2
0.628	Remote Similarity	NPD5950	Discontinued
0.628	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD6030	Approved
0.6278	Remote Similarity	NPD6031	Approved
0.6273	Remote Similarity	NPD5536	Phase 2
0.6257	Remote Similarity	NPD3861	Approved
0.6257	Remote Similarity	NPD3862	Approved
0.625	Remote Similarity	NPD487	Discontinued
0.6236	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD3144	Approved
0.6235	Remote Similarity	NPD3145	Approved
0.6224	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD6107	Approved
0.6223	Remote Similarity	NPD2821	Approved
0.6207	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD1420	Approved
0.6205	Remote Similarity	NPD1421	Approved
0.6205	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD4357	Discontinued
0.62	Remote Similarity	NPD6181	Discontinued
0.6199	Remote Similarity	NPD2674	Phase 3
0.6195	Remote Similarity	NPD5006	Approved
0.6195	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5005	Approved
0.6195	Remote Similarity	NPD7316	Discontinued
0.6193	Remote Similarity	NPD7223	Discontinued
0.6193	Remote Similarity	NPD7224	Discontinued
0.6186	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD2653	Approved
0.6178	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD730	Discontinued
0.6176	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD6258	Discontinued
0.617	Remote Similarity	NPD5677	Discontinued
0.6166	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7225	Discontinued
0.6149	Remote Similarity	NPD6896	Approved
0.6149	Remote Similarity	NPD6895	Approved
0.6141	Remote Similarity	NPD4773	Phase 2
0.6141	Remote Similarity	NPD4772	Phase 2
0.6136	Remote Similarity	NPD3656	Approved
0.6131	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5967	Approved
0.6126	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD1194	Discontinued
0.6121	Remote Similarity	NPD5980	Discovery
0.612	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD7298	Approved
0.6108	Remote Similarity	NPD7577	Discontinued
0.6108	Remote Similarity	NPD5720	Discontinued
0.6105	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD7038	Approved
0.6103	Remote Similarity	NPD7039	Approved
0.6103	Remote Similarity	NPD7559	Phase 2
0.6099	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD6788	Approved
0.6089	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD3885	Approved
0.6077	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD8149	Discontinued
0.6071	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD1757	Discontinued
0.605	Remote Similarity	NPD5910	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD2236	Approved
0.6042	Remote Similarity	NPD6894	Phase 1
0.6041	Remote Similarity	NPD2971	Approved
0.6041	Remote Similarity	NPD2968	Approved
0.6033	Remote Similarity	NPD6813	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD6844	Discontinued
0.6022	Remote Similarity	NPD3124	Discontinued
0.602	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4107	Approved
0.6012	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD1914	Approved
0.601	Remote Similarity	NPD3366	Approved
0.6	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD2899	Discontinued
0.5989	Remote Similarity	NPD4739	Approved
0.5989	Remote Similarity	NPD6322	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD2654	Approved
0.5971	Remote Similarity	NPD7810	Phase 3
0.5971	Remote Similarity	NPD7811	Phase 3
0.5963	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD3057	Approved
0.5961	Remote Similarity	NPD4466	Phase 1
0.5957	Remote Similarity	NPD2563	Approved
0.5957	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD2560	Approved
0.5952	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD3972	Approved
0.5947	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD6862	Phase 2
0.5946	Remote Similarity	NPD2512	Phase 3
0.5946	Remote Similarity	NPD3455	Phase 2
0.5943	Remote Similarity	NPD447	Suspended
0.5938	Remote Similarity	NPD6071	Discontinued
0.5938	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD7317	Phase 3
0.5931	Remote Similarity	NPD2746	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD2745	Approved
0.593	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.593	Remote Similarity	NPD4483	Discontinued
0.5928	Remote Similarity	NPD3446	Phase 1
0.5928	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD1671	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data