NPASS Compound

Structure

CID314948 OpenBabel06191716132D 25 27 0 0 0 0 0 0 0 0999 V2000 -2.5981 -3.5000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 0.8660 -1.5000 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 -0.8660 -1.5000 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 -0.8660 -0.5000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 14 1 0 0 0 0 4 10 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 5 13 2 0 0 0 0 6 15 2 0 0 0 0 6 16 1 0 0 0 0 7 10 1 0 0 0 0 7 20 1 0 0 0 0 8 17 1 0 0 0 0 8 21 1 0 0 0 0 9 18 2 3 0 0 0 9 22 1 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 24 1 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.1
Volume:	330.562
LogP:	0.926
LogD:	0.823
LogS:	-5.803
# Rotatable Bonds:	6
TPSA:	117.12
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.422
Synthetic Accessibility Score:	2.663
Fsp3:	0.176
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:	-5.011
MDCK Permeability:	3.85E-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	51.33%
Volume Distribution (VD):	0.548
Pgp-substrate:	53.48%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.101
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.091
CYP2C9-inhibitor:	0.227
CYP2C9-substrate:	0.353
CYP2D6-inhibitor:	0.108
CYP2D6-substrate:	0.29
CYP3A4-inhibitor:	0.495
CYP3A4-substrate:	0.452

ADMET: Excretion

Clearance (CL):	2.524
Half-life (T1/2):	0.873

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.073
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.222
Rat Oral Acute Toxicity:	0.247
Maximum Recommended Daily Dose:	0.82
Skin Sensitization:	0.938
Carcinogencity:	0.097
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.642

Download Data

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

Natural Product: NPC314948

Natural Product ID:	NPC314948
*Common Name:**	Vnezueline C
IUPAC Name:	[2-acetamido-8-(hydroxymethyl)-10H-phenoxazin-3-yl] 2-hydroxyacetate
Synonyms:	Vnezueline C
Standard InCHIKey:	OMNPWACYOUMUON-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H16N2O6/c1-9(22)18-12-5-13-15(6-16(12)25-17(23)8-21)24-14-3-2-10(7-20)4-11(14)19-13/h2-6,19-21H,7-8H2,1H3,(H,18,22)
SMILES:	OCC(=O)Oc1cc2Oc3ccc(cc3Nc2cc1N=C(O)C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2311992
PubChem CID:	71517221
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001396] Benzoxazines [CHEMONTID:0001855] Phenoxazines

*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
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11720530]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16724858]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	Guam Island, Pacific Ocean	n.a.	PMID[21774474]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22050382]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	Guam Island, Pacific Ocean	n.a.	PMID[23164710]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26203536]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	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	6

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[523202]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[523202]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[523202]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[523202]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50.0	ug.mL-1	PMID[523202]

☑ 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 NPC314948 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	296
0.1-0.2	2138
0.2-0.3	11615
0.3-0.4	5895
0.4-0.5	9639
0.5-0.6	12437
0.6-0.7	661
0.7-0.8	14
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9886	High Similarity	NPC478049
0.7514	Intermediate Similarity	NPC204179
0.7474	Intermediate Similarity	NPC220560
0.7421	Intermediate Similarity	NPC290069
0.7405	Intermediate Similarity	NPC57105
0.738	Intermediate Similarity	NPC314861
0.7351	Intermediate Similarity	NPC231862
0.7351	Intermediate Similarity	NPC306366
0.733	Intermediate Similarity	NPC314113
0.7323	Intermediate Similarity	NPC475411
0.7189	Intermediate Similarity	NPC112766
0.7151	Intermediate Similarity	NPC70549
0.7127	Intermediate Similarity	NPC473769
0.7087	Intermediate Similarity	NPC214368
0.7071	Intermediate Similarity	NPC313886
0.6939	Remote Similarity	NPC315631
0.6935	Remote Similarity	NPC469829
0.6923	Remote Similarity	NPC260601
0.6904	Remote Similarity	NPC316161
0.6884	Remote Similarity	NPC469831
0.6875	Remote Similarity	NPC313466
0.6833	Remote Similarity	NPC476475
0.6825	Remote Similarity	NPC10875
0.6825	Remote Similarity	NPC10730
0.6823	Remote Similarity	NPC139506
0.6823	Remote Similarity	NPC292143
0.6813	Remote Similarity	NPC476462
0.6806	Remote Similarity	NPC235628
0.6762	Remote Similarity	NPC470586
0.6761	Remote Similarity	NPC257266
0.675	Remote Similarity	NPC314025
0.6745	Remote Similarity	NPC470484
0.673	Remote Similarity	NPC311357
0.6729	Remote Similarity	NPC257728
0.6719	Remote Similarity	NPC19023
0.6716	Remote Similarity	NPC314213
0.6716	Remote Similarity	NPC314656
0.6698	Remote Similarity	NPC153365
0.6683	Remote Similarity	NPC108847
0.6683	Remote Similarity	NPC315913
0.6682	Remote Similarity	NPC203168
0.6667	Remote Similarity	NPC79293
0.6667	Remote Similarity	NPC279401
0.6652	Remote Similarity	NPC291609
0.6652	Remote Similarity	NPC314702
0.6651	Remote Similarity	NPC217903
0.6649	Remote Similarity	NPC315257
0.6634	Remote Similarity	NPC217294
0.6609	Remote Similarity	NPC124300
0.6606	Remote Similarity	NPC116178
0.6606	Remote Similarity	NPC182853
0.6601	Remote Similarity	NPC320394
0.6595	Remote Similarity	NPC168750
0.6592	Remote Similarity	NPC118189
0.659	Remote Similarity	NPC25961
0.659	Remote Similarity	NPC219664
0.6589	Remote Similarity	NPC164374
0.6589	Remote Similarity	NPC473422
0.6589	Remote Similarity	NPC137929
0.6587	Remote Similarity	NPC471825
0.6585	Remote Similarity	NPC469830
0.6584	Remote Similarity	NPC116096
0.6584	Remote Similarity	NPC472163
0.6582	Remote Similarity	NPC127362
0.658	Remote Similarity	NPC476995
0.6578	Remote Similarity	NPC313414
0.6573	Remote Similarity	NPC288759
0.657	Remote Similarity	NPC469390
0.656	Remote Similarity	NPC218303
0.6559	Remote Similarity	NPC63628
0.6559	Remote Similarity	NPC178466
0.655	Remote Similarity	NPC473432
0.655	Remote Similarity	NPC168153
0.6545	Remote Similarity	NPC176113
0.6537	Remote Similarity	NPC61350
0.6526	Remote Similarity	NPC111492
0.6525	Remote Similarity	NPC310618
0.6524	Remote Similarity	NPC97004
0.6524	Remote Similarity	NPC161155
0.6524	Remote Similarity	NPC136951
0.652	Remote Similarity	NPC473458
0.652	Remote Similarity	NPC62069
0.652	Remote Similarity	NPC471513
0.6518	Remote Similarity	NPC76478
0.6517	Remote Similarity	NPC283152
0.6515	Remote Similarity	NPC329717
0.6514	Remote Similarity	NPC474366
0.6512	Remote Similarity	NPC313112
0.6512	Remote Similarity	NPC301292
0.6509	Remote Similarity	NPC241263
0.6504	Remote Similarity	NPC19175
0.6502	Remote Similarity	NPC288110
0.65	Remote Similarity	NPC30749
0.65	Remote Similarity	NPC321166
0.6495	Remote Similarity	NPC66815
0.6489	Remote Similarity	NPC251071
0.6489	Remote Similarity	NPC148124
0.6489	Remote Similarity	NPC97282
0.6488	Remote Similarity	NPC477391
0.6481	Remote Similarity	NPC195787
0.6481	Remote Similarity	NPC246140
0.6477	Remote Similarity	NPC18249
0.6477	Remote Similarity	NPC187028
0.6477	Remote Similarity	NPC140915
0.6477	Remote Similarity	NPC305700
0.6477	Remote Similarity	NPC10221
0.6477	Remote Similarity	NPC197741
0.6476	Remote Similarity	NPC200888
0.6473	Remote Similarity	NPC476069
0.6468	Remote Similarity	NPC194724
0.6465	Remote Similarity	NPC469440
0.6463	Remote Similarity	NPC477397
0.6457	Remote Similarity	NPC134702
0.6456	Remote Similarity	NPC262725
0.6455	Remote Similarity	NPC245974
0.6455	Remote Similarity	NPC127996
0.6452	Remote Similarity	NPC198160
0.645	Remote Similarity	NPC225381
0.645	Remote Similarity	NPC73280
0.6444	Remote Similarity	NPC99724
0.6441	Remote Similarity	NPC288349
0.6441	Remote Similarity	NPC234772
0.6436	Remote Similarity	NPC474902
0.6435	Remote Similarity	NPC476999
0.6429	Remote Similarity	NPC78284
0.6425	Remote Similarity	NPC66083
0.6425	Remote Similarity	NPC268223
0.6421	Remote Similarity	NPC115144
0.6421	Remote Similarity	NPC277857
0.6419	Remote Similarity	NPC476997
0.6415	Remote Similarity	NPC472191
0.6415	Remote Similarity	NPC272706
0.6409	Remote Similarity	NPC295479
0.6409	Remote Similarity	NPC220241
0.6408	Remote Similarity	NPC42591
0.6398	Remote Similarity	NPC83289
0.6398	Remote Similarity	NPC469722
0.6398	Remote Similarity	NPC212850
0.6398	Remote Similarity	NPC189724
0.6395	Remote Similarity	NPC291173
0.6394	Remote Similarity	NPC295287
0.6393	Remote Similarity	NPC477160
0.6392	Remote Similarity	NPC56635
0.6391	Remote Similarity	NPC476996
0.6391	Remote Similarity	NPC476998
0.639	Remote Similarity	NPC98197
0.6389	Remote Similarity	NPC473460
0.6384	Remote Similarity	NPC195120
0.6384	Remote Similarity	NPC473822
0.6384	Remote Similarity	NPC469594
0.6384	Remote Similarity	NPC315632
0.6384	Remote Similarity	NPC87560
0.6381	Remote Similarity	NPC294244
0.638	Remote Similarity	NPC305542
0.6376	Remote Similarity	NPC212123
0.6376	Remote Similarity	NPC248903
0.6372	Remote Similarity	NPC128476
0.6372	Remote Similarity	NPC329830
0.6368	Remote Similarity	NPC132771
0.6368	Remote Similarity	NPC204908
0.6368	Remote Similarity	NPC83198
0.6364	Remote Similarity	NPC474059
0.6364	Remote Similarity	NPC204546
0.6359	Remote Similarity	NPC477392
0.6359	Remote Similarity	NPC315934
0.6356	Remote Similarity	NPC222046
0.6356	Remote Similarity	NPC475844
0.6354	Remote Similarity	NPC473987
0.6351	Remote Similarity	NPC474594
0.6351	Remote Similarity	NPC117717
0.6349	Remote Similarity	NPC247298
0.6348	Remote Similarity	NPC476994
0.6347	Remote Similarity	NPC308392
0.6346	Remote Similarity	NPC232872
0.6346	Remote Similarity	NPC219170
0.6346	Remote Similarity	NPC180253
0.6344	Remote Similarity	NPC124149
0.6343	Remote Similarity	NPC15987
0.6341	Remote Similarity	NPC215837
0.6339	Remote Similarity	NPC195636
0.6335	Remote Similarity	NPC92235
0.6333	Remote Similarity	NPC11296
0.6333	Remote Similarity	NPC274661
0.6333	Remote Similarity	NPC175890
0.6333	Remote Similarity	NPC48490
0.6333	Remote Similarity	NPC82457
0.6332	Remote Similarity	NPC26928
0.633	Remote Similarity	NPC471736
0.6329	Remote Similarity	NPC276060
0.6329	Remote Similarity	NPC477395
0.6323	Remote Similarity	NPC148391
0.6318	Remote Similarity	NPC310894
0.6318	Remote Similarity	NPC120239
0.6318	Remote Similarity	NPC83241
0.6316	Remote Similarity	NPC22928
0.6316	Remote Similarity	NPC110741
0.6316	Remote Similarity	NPC320088
0.6313	Remote Similarity	NPC223427
0.6311	Remote Similarity	NPC474507
0.6311	Remote Similarity	NPC77777

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 NPC314948 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	674
0.2-0.3	1067
0.3-0.4	1637
0.4-0.5	2817
0.5-0.6	2375
0.6-0.7	381
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
0.7846	Intermediate Similarity	NPD6034	Phase 2
0.7672	Intermediate Similarity	NPD6211	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD3558	Approved
0.7446	Intermediate Similarity	NPD3556	Approved
0.7446	Intermediate Similarity	NPD3557	Approved
0.7446	Intermediate Similarity	NPD3559	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD3560	Approved
0.7436	Intermediate Similarity	NPD4587	Phase 3
0.7415	Intermediate Similarity	NPD7263	Phase 2
0.74	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4586	Phase 3
0.7313	Intermediate Similarity	NPD4605	Approved
0.7313	Intermediate Similarity	NPD4604	Approved
0.7308	Intermediate Similarity	NPD4003	Phase 3
0.7263	Intermediate Similarity	NPD4083	Discontinued
0.7222	Intermediate Similarity	NPD1898	Discontinued
0.7216	Intermediate Similarity	NPD6184	Discontinued
0.7112	Intermediate Similarity	NPD6283	Phase 2
0.7074	Intermediate Similarity	NPD1012	Discontinued
0.7068	Intermediate Similarity	NPD6379	Discontinued
0.7065	Intermediate Similarity	NPD8330	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD3536	Discontinued
0.7041	Intermediate Similarity	NPD6496	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6060	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7880	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3778	Approved
0.7005	Intermediate Similarity	NPD6604	Discontinued
0.7	Intermediate Similarity	NPD6793	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3453	Discontinued
0.699	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD2247	Approved
0.6979	Remote Similarity	NPD2249	Approved
0.6931	Remote Similarity	NPD2845	Phase 2
0.6931	Remote Similarity	NPD2843	Phase 2
0.6927	Remote Similarity	NPD6550	Discontinued
0.6927	Remote Similarity	NPD5582	Discontinued
0.6927	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5938	Phase 3
0.6912	Remote Similarity	NPD5150	Phase 2
0.6908	Remote Similarity	NPD6874	Approved
0.6907	Remote Similarity	NPD2216	Approved
0.6907	Remote Similarity	NPD2215	Approved
0.6906	Remote Similarity	NPD4597	Approved
0.6906	Remote Similarity	NPD4598	Approved
0.6887	Remote Similarity	NPD2514	Approved
0.6881	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD1769	Discontinued
0.6869	Remote Similarity	NPD4502	Phase 2
0.6866	Remote Similarity	NPD3153	Approved
0.6866	Remote Similarity	NPD3154	Approved
0.6862	Remote Similarity	NPD3538	Suspended
0.685	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7476	Discontinued
0.6839	Remote Similarity	NPD4944	Phase 2
0.6839	Remote Similarity	NPD4943	Phase 2
0.6833	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4255	Phase 1
0.6825	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD795	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5811	Approved
0.6796	Remote Similarity	NPD7256	Discontinued
0.6796	Remote Similarity	NPD1422	Approved
0.6791	Remote Similarity	NPD5416	Discontinued
0.6768	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7583	Approved
0.6754	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5677	Discontinued
0.675	Remote Similarity	NPD6104	Discontinued
0.6748	Remote Similarity	NPD7125	Discontinued
0.6737	Remote Similarity	NPD2366	Approved
0.6733	Remote Similarity	NPD6045	Phase 3
0.6731	Remote Similarity	NPD2952	Discontinued
0.6729	Remote Similarity	NPD7585	Approved
0.6719	Remote Similarity	NPD6063	Approved
0.6714	Remote Similarity	NPD6519	Phase 2
0.6712	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4324	Phase 2
0.6699	Remote Similarity	NPD4325	Phase 2
0.6684	Remote Similarity	NPD4675	Approved
0.6684	Remote Similarity	NPD4678	Approved
0.6684	Remote Similarity	NPD3296	Phase 1
0.6683	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5512	Phase 3
0.6682	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7262	Phase 1
0.6667	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6298	Discontinued
0.6667	Remote Similarity	NPD3656	Approved
0.6667	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD2498	Approved
0.665	Remote Similarity	NPD5641	Discontinued
0.6649	Remote Similarity	NPD8031	Discontinued
0.6636	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4206	Approved
0.6633	Remote Similarity	NPD3511	Discontinued
0.6631	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD6877	Discontinued
0.6618	Remote Similarity	NPD6340	Approved
0.6618	Remote Similarity	NPD6339	Approved
0.6614	Remote Similarity	NPD3627	Approved
0.6611	Remote Similarity	NPD1393	Approved
0.6605	Remote Similarity	NPD2434	Approved
0.6603	Remote Similarity	NPD3964	Approved
0.6599	Remote Similarity	NPD5847	Phase 1
0.6595	Remote Similarity	NPD2460	Phase 3
0.6595	Remote Similarity	NPD2458	Approved
0.6595	Remote Similarity	NPD2459	Approved
0.6582	Remote Similarity	NPD4666	Phase 3
0.658	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3516	Approved
0.6573	Remote Similarity	NPD3515	Approved
0.6571	Remote Similarity	NPD6988	Phase 1
0.6562	Remote Similarity	NPD3236	Phase 3
0.6562	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6072	Discontinued
0.6562	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6220	Phase 3
0.6557	Remote Similarity	NPD822	Approved
0.6555	Remote Similarity	NPD6590	Discontinued
0.655	Remote Similarity	NPD4354	Approved
0.6538	Remote Similarity	NPD3054	Approved
0.6538	Remote Similarity	NPD3052	Approved
0.6538	Remote Similarity	NPD4740	Approved
0.6535	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6199	Discontinued
0.6533	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD3951	Phase 3
0.6533	Remote Similarity	NPD7548	Discontinued
0.6533	Remote Similarity	NPD3953	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD3952	Approved
0.6531	Remote Similarity	NPD5709	Phase 3
0.6528	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4259	Approved
0.6522	Remote Similarity	NPD4258	Approved
0.6515	Remote Similarity	NPD7608	Discontinued
0.6512	Remote Similarity	NPD6644	Discontinued
0.6505	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD2899	Discontinued
0.6493	Remote Similarity	NPD5872	Discontinued
0.6493	Remote Similarity	NPD5652	Approved
0.6493	Remote Similarity	NPD5651	Approved
0.6493	Remote Similarity	NPD5650	Approved
0.6493	Remote Similarity	NPD7491	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD1678	Clinical (unspecified phase)
0.649	Remote Similarity	NPD5871	Discontinued
0.6489	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD4889	Approved
0.6485	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD3842	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD6810	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4523	Approved
0.6474	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD4021	Phase 2
0.6471	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2241	Approved
0.6471	Remote Similarity	NPD7883	Discontinued
0.6471	Remote Similarity	NPD4679	Discontinued
0.6468	Remote Similarity	NPD5132	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6669	Phase 2
0.6463	Remote Similarity	NPD5022	Discontinued
0.6458	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6357	Discontinued
0.6456	Remote Similarity	NPD5256	Discontinued
0.6455	Remote Similarity	NPD7213	Phase 3
0.6455	Remote Similarity	NPD7212	Phase 2
0.6452	Remote Similarity	NPD7043	Discontinued
0.6452	Remote Similarity	NPD7222	Phase 2
0.6452	Remote Similarity	NPD5429	Discontinued
0.6452	Remote Similarity	NPD5719	Approved
0.6452	Remote Similarity	NPD6296	Discontinued
0.6452	Remote Similarity	NPD6290	Phase 2
0.6442	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4428	Discontinued
0.644	Remote Similarity	NPD6030	Approved
0.644	Remote Similarity	NPD6031	Approved
0.6436	Remote Similarity	NPD3965	Phase 1
0.6435	Remote Similarity	NPD7891	Discontinued
0.6435	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1191	Discontinued
0.6429	Remote Similarity	NPD756	Suspended
0.6425	Remote Similarity	NPD5944	Phase 1
0.6425	Remote Similarity	NPD5945	Phase 1
0.6422	Remote Similarity	NPD3386	Phase 2
0.6422	Remote Similarity	NPD5845	Phase 2
0.6421	Remote Similarity	NPD7447	Phase 1
0.6421	Remote Similarity	NPD4123	Phase 3
0.6419	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD7316	Discontinued
0.6415	Remote Similarity	NPD7238	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