NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.1
Volume:	260.447
LogP:	0.077
LogD:	-0.134
LogS:	-3.476
# Rotatable Bonds:	1
TPSA:	91.15
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.691
Synthetic Accessibility Score:	4.699
Fsp3:	0.429
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:	-5.324
MDCK Permeability:	3.2115192425408168e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.919
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.054

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.877
Plasma Protein Binding (PPB):	54.45880126953125%
Volume Distribution (VD):	0.795
Pgp-substrate:	58.2362060546875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.41
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.8
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.416
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.331
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.305

ADMET: Excretion

Clearance (CL):	4.841
Half-life (T1/2):	0.572

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.727
Drug-inuced Liver Injury (DILI):	0.271
AMES Toxicity:	0.481
Rat Oral Acute Toxicity:	0.755
Maximum Recommended Daily Dose:	0.595
Skin Sensitization:	0.289
Carcinogencity:	0.855
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC316161

Natural Product ID:	NPC316161
*Common Name:**	Vnezueline B
IUPAC Name:	n.a.
Synonyms:	Vnezueline B
Standard InCHIKey:	YDXKTQRGXVQESR-XPLICSAQSA-N
Standard InCHI:	InChI=1S/C14H14N2O4/c17-6-7-1-3-10-9(5-7)15-13-14(20-10)8(12(19)16-13)2-4-11(14)18/h1,3,5,8,11,17-18H,2,4,6H2,(H,15,16,19)/t8-,11-,14-/m1/s1
SMILES:	OCc1ccc2c(c1)N=C1[C@]3(O2)[C@H](O)CC[C@@H]3C(=N1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2311991
PubChem CID:	71517220
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001396] Benzoxazines

*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	=	6570.0	nM	PMID[485007]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7520.0	nM	PMID[485007]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	5740.0	nM	PMID[485007]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	6780.0	nM	PMID[485007]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	9670.0	nM	PMID[485007]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[485007]

☑ 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 NPC316161 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	378
0.1-0.2	1673
0.2-0.3	8186
0.3-0.4	9890
0.4-0.5	13234
0.5-0.6	8750
0.6-0.7	571
0.7-0.8	14
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8059	Intermediate Similarity	NPC57105
0.7895	Intermediate Similarity	NPC231862
0.7719	Intermediate Similarity	NPC10875
0.7719	Intermediate Similarity	NPC10730
0.747	Intermediate Similarity	NPC314113
0.7416	Intermediate Similarity	NPC314861
0.7407	Intermediate Similarity	NPC313466
0.7296	Intermediate Similarity	NPC315632
0.7273	Intermediate Similarity	NPC70549
0.7273	Intermediate Similarity	NPC313886
0.7268	Intermediate Similarity	NPC168153
0.7251	Intermediate Similarity	NPC473769
0.7216	Intermediate Similarity	NPC112766
0.7191	Intermediate Similarity	NPC306366
0.7167	Intermediate Similarity	NPC204179
0.7135	Intermediate Similarity	NPC315631
0.7134	Intermediate Similarity	NPC473987
0.7107	Intermediate Similarity	NPC214368
0.7045	Intermediate Similarity	NPC219383
0.7	Intermediate Similarity	NPC235628
0.699	Remote Similarity	NPC478049
0.6949	Remote Similarity	NPC184161
0.694	Remote Similarity	NPC127362
0.6904	Remote Similarity	NPC314948
0.6889	Remote Similarity	NPC87363
0.6848	Remote Similarity	NPC19555
0.6791	Remote Similarity	NPC225381
0.6786	Remote Similarity	NPC294244
0.6782	Remote Similarity	NPC159101
0.674	Remote Similarity	NPC51543
0.672	Remote Similarity	NPC470936
0.6718	Remote Similarity	NPC471395
0.6684	Remote Similarity	NPC257354
0.6667	Remote Similarity	NPC260118
0.6667	Remote Similarity	NPC291359
0.6649	Remote Similarity	NPC28425
0.6647	Remote Similarity	NPC471953
0.6633	Remote Similarity	NPC217294
0.6632	Remote Similarity	NPC215747
0.6632	Remote Similarity	NPC192939
0.6615	Remote Similarity	NPC265383
0.661	Remote Similarity	NPC473874
0.6609	Remote Similarity	NPC36434
0.6608	Remote Similarity	NPC297584
0.6607	Remote Similarity	NPC197680
0.6607	Remote Similarity	NPC259098
0.66	Remote Similarity	NPC108847
0.6598	Remote Similarity	NPC119579
0.6582	Remote Similarity	NPC219170
0.6582	Remote Similarity	NPC180253
0.6573	Remote Similarity	NPC313414
0.6571	Remote Similarity	NPC83289
0.6571	Remote Similarity	NPC212850
0.6571	Remote Similarity	NPC298821
0.6571	Remote Similarity	NPC189724
0.6569	Remote Similarity	NPC311357
0.6564	Remote Similarity	NPC276060
0.6554	Remote Similarity	NPC63628
0.6554	Remote Similarity	NPC178466
0.6548	Remote Similarity	NPC22928
0.6546	Remote Similarity	NPC311936
0.6536	Remote Similarity	NPC245974
0.6534	Remote Similarity	NPC123761
0.6534	Remote Similarity	NPC195814
0.6515	Remote Similarity	NPC112676
0.6515	Remote Similarity	NPC296742
0.6505	Remote Similarity	NPC69360
0.65	Remote Similarity	NPC279401
0.65	Remote Similarity	NPC79293
0.65	Remote Similarity	NPC115144
0.65	Remote Similarity	NPC277857
0.6497	Remote Similarity	NPC69213
0.6474	Remote Similarity	NPC310894
0.6465	Remote Similarity	NPC224293
0.6458	Remote Similarity	NPC8467
0.6455	Remote Similarity	NPC54125
0.6455	Remote Similarity	NPC89199
0.6453	Remote Similarity	NPC274732
0.6453	Remote Similarity	NPC208022
0.6445	Remote Similarity	NPC203168
0.6429	Remote Similarity	NPC14390
0.6429	Remote Similarity	NPC95733
0.6429	Remote Similarity	NPC62101
0.6429	Remote Similarity	NPC469829
0.6425	Remote Similarity	NPC247298
0.6425	Remote Similarity	NPC97004
0.6425	Remote Similarity	NPC161155
0.6425	Remote Similarity	NPC136951
0.6425	Remote Similarity	NPC184607
0.6421	Remote Similarity	NPC477888
0.6417	Remote Similarity	NPC67080
0.6404	Remote Similarity	NPC272706
0.64	Remote Similarity	NPC126637
0.64	Remote Similarity	NPC166667
0.6391	Remote Similarity	NPC29477
0.6389	Remote Similarity	NPC97282
0.6387	Remote Similarity	NPC83241
0.6387	Remote Similarity	NPC304846
0.6386	Remote Similarity	NPC29472
0.638	Remote Similarity	NPC258992
0.6378	Remote Similarity	NPC315257
0.6378	Remote Similarity	NPC98197
0.6374	Remote Similarity	NPC470935
0.6374	Remote Similarity	NPC471032
0.6373	Remote Similarity	NPC477115
0.6373	Remote Similarity	NPC211713
0.6373	Remote Similarity	NPC88378
0.6369	Remote Similarity	NPC260601
0.6369	Remote Similarity	NPC470937
0.6369	Remote Similarity	NPC211218
0.6364	Remote Similarity	NPC19023
0.6364	Remote Similarity	NPC156348
0.6364	Remote Similarity	NPC262725
0.6351	Remote Similarity	NPC219664
0.6346	Remote Similarity	NPC14339
0.634	Remote Similarity	NPC228040
0.6335	Remote Similarity	NPC198741
0.6328	Remote Similarity	NPC299583
0.6324	Remote Similarity	NPC275027
0.6321	Remote Similarity	NPC95412
0.6308	Remote Similarity	NPC472331
0.6308	Remote Similarity	NPC126515
0.6308	Remote Similarity	NPC274002
0.6296	Remote Similarity	NPC264782
0.6287	Remote Similarity	NPC269242
0.6271	Remote Similarity	NPC204848
0.6271	Remote Similarity	NPC312770
0.6271	Remote Similarity	NPC160607
0.6271	Remote Similarity	NPC41473
0.6271	Remote Similarity	NPC14600
0.6269	Remote Similarity	NPC182257
0.6267	Remote Similarity	NPC108826
0.6264	Remote Similarity	NPC247018
0.6264	Remote Similarity	NPC307123
0.6264	Remote Similarity	NPC97870
0.6263	Remote Similarity	NPC71205
0.6263	Remote Similarity	NPC315934
0.6263	Remote Similarity	NPC477392
0.6257	Remote Similarity	NPC476462
0.6256	Remote Similarity	NPC289743
0.6256	Remote Similarity	NPC250960
0.6256	Remote Similarity	NPC110374
0.6256	Remote Similarity	NPC71539
0.625	Remote Similarity	NPC90984
0.625	Remote Similarity	NPC139699
0.625	Remote Similarity	NPC114659
0.625	Remote Similarity	NPC474077
0.6243	Remote Similarity	NPC92191
0.6243	Remote Similarity	NPC116104
0.6243	Remote Similarity	NPC72291
0.6243	Remote Similarity	NPC263397
0.6243	Remote Similarity	NPC237872
0.6243	Remote Similarity	NPC302286
0.6243	Remote Similarity	NPC59028
0.6243	Remote Similarity	NPC88754
0.6237	Remote Similarity	NPC474953
0.6235	Remote Similarity	NPC325013
0.6231	Remote Similarity	NPC133591
0.6231	Remote Similarity	NPC474650
0.6229	Remote Similarity	NPC105541
0.6226	Remote Similarity	NPC168250
0.6221	Remote Similarity	NPC101372
0.6212	Remote Similarity	NPC469831
0.6211	Remote Similarity	NPC46844
0.6207	Remote Similarity	NPC255550
0.6207	Remote Similarity	NPC308885
0.6203	Remote Similarity	NPC56635
0.62	Remote Similarity	NPC38823
0.62	Remote Similarity	NPC207033
0.62	Remote Similarity	NPC291759
0.6196	Remote Similarity	NPC1986
0.6196	Remote Similarity	NPC301735
0.6196	Remote Similarity	NPC474544
0.6196	Remote Similarity	NPC20360
0.6196	Remote Similarity	NPC476744
0.6193	Remote Similarity	NPC218530
0.6193	Remote Similarity	NPC153923
0.6193	Remote Similarity	NPC37957
0.6193	Remote Similarity	NPC115343
0.6193	Remote Similarity	NPC1291
0.619	Remote Similarity	NPC469412
0.619	Remote Similarity	NPC198734
0.6185	Remote Similarity	NPC226662
0.6181	Remote Similarity	NPC315913
0.6181	Remote Similarity	NPC474607
0.6178	Remote Similarity	NPC179250
0.6178	Remote Similarity	NPC50380
0.6175	Remote Similarity	NPC132771
0.6171	Remote Similarity	NPC130595
0.6171	Remote Similarity	NPC266994
0.6171	Remote Similarity	NPC93882
0.6169	Remote Similarity	NPC469830
0.6158	Remote Similarity	NPC264956
0.6158	Remote Similarity	NPC64205
0.6158	Remote Similarity	NPC28510
0.6158	Remote Similarity	NPC22014
0.6157	Remote Similarity	NPC316297
0.6157	Remote Similarity	NPC314817
0.6157	Remote Similarity	NPC66191
0.615	Remote Similarity	NPC477391

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 NPC316161 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	617
0.2-0.3	925
0.3-0.4	2296
0.4-0.5	3072
0.5-0.6	1819
0.6-0.7	190
0.7-0.8	11
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
0.7824	Intermediate Similarity	NPD3778	Approved
0.7414	Intermediate Similarity	NPD980	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD681	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4604	Approved
0.7165	Intermediate Similarity	NPD4605	Approved
0.7143	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD3236	Phase 3
0.7119	Intermediate Similarity	NPD3237	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD2752	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD950	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2216	Approved
0.7011	Intermediate Similarity	NPD2215	Approved
0.701	Intermediate Similarity	NPD7125	Discontinued
0.7	Intermediate Similarity	NPD3560	Approved
0.7	Intermediate Similarity	NPD3559	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3557	Approved
0.7	Intermediate Similarity	NPD3558	Approved
0.7	Intermediate Similarity	NPD3556	Approved
0.6982	Remote Similarity	NPD696	Discontinued
0.6964	Remote Similarity	NPD654	Phase 3
0.6949	Remote Similarity	NPD4003	Phase 3
0.6722	Remote Similarity	NPD5811	Approved
0.6718	Remote Similarity	NPD1898	Discontinued
0.6684	Remote Similarity	NPD2845	Phase 2
0.6684	Remote Similarity	NPD2843	Phase 2
0.6649	Remote Similarity	NPD3453	Discontinued
0.6647	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6184	Discontinued
0.6609	Remote Similarity	NPD2161	Phase 2
0.6593	Remote Similarity	NPD3296	Phase 1
0.6592	Remote Similarity	NPD4123	Phase 3
0.6583	Remote Similarity	NPD5150	Phase 2
0.6582	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6034	Phase 2
0.6562	Remote Similarity	NPD5557	Phase 1
0.6545	Remote Similarity	NPD3909	Discontinued
0.6543	Remote Similarity	NPD254	Approved
0.6533	Remote Similarity	NPD3633	Approved
0.6533	Remote Similarity	NPD3634	Approved
0.6526	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD1422	Approved
0.6503	Remote Similarity	NPD4675	Approved
0.6503	Remote Similarity	NPD5617	Suspended
0.6503	Remote Similarity	NPD4678	Approved
0.6495	Remote Similarity	NPD6104	Discontinued
0.6489	Remote Similarity	NPD2341	Discontinued
0.6486	Remote Similarity	NPD5773	Approved
0.6486	Remote Similarity	NPD5772	Approved
0.6477	Remote Similarity	NPD1375	Discontinued
0.6474	Remote Similarity	NPD4083	Discontinued
0.6467	Remote Similarity	NPD6072	Discontinued
0.6457	Remote Similarity	NPD204	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6063	Approved
0.6447	Remote Similarity	NPD3153	Approved
0.6447	Remote Similarity	NPD3154	Approved
0.6429	Remote Similarity	NPD5645	Phase 3
0.6406	Remote Similarity	NPD5938	Phase 3
0.6396	Remote Similarity	NPD6045	Phase 3
0.6384	Remote Similarity	NPD521	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD3490	Discontinued
0.6377	Remote Similarity	NPD3802	Phase 3
0.6374	Remote Similarity	NPD7526	Approved
0.6374	Remote Similarity	NPD52	Approved
0.6374	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6331	Phase 2
0.6368	Remote Similarity	NPD2247	Approved
0.6368	Remote Similarity	NPD2249	Approved
0.6359	Remote Similarity	NPD7007	Discovery
0.6348	Remote Similarity	NPD7153	Discontinued
0.6324	Remote Similarity	NPD3538	Suspended
0.6316	Remote Similarity	NPD4993	Discontinued
0.631	Remote Similarity	NPD6283	Phase 2
0.6305	Remote Similarity	NPD7256	Discontinued
0.63	Remote Similarity	NPD3398	Discontinued
0.6296	Remote Similarity	NPD8070	Approved
0.6294	Remote Similarity	NPD3567	Approved
0.6294	Remote Similarity	NPD3568	Approved
0.629	Remote Similarity	NPD4255	Phase 1
0.6286	Remote Similarity	NPD6296	Discontinued
0.6276	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5582	Discontinued
0.6272	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD4258	Approved
0.6269	Remote Similarity	NPD4259	Approved
0.6264	Remote Similarity	NPD1423	Approved
0.6263	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD1861	Discovery
0.625	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4951	Discontinued
0.6237	Remote Similarity	NPD3679	Phase 2
0.6237	Remote Similarity	NPD1557	Discontinued
0.6236	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6419	Discontinued
0.623	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.623	Remote Similarity	NPD1850	Phase 3
0.6229	Remote Similarity	NPD756	Suspended
0.6219	Remote Similarity	NPD5800	Discontinued
0.6216	Remote Similarity	NPD5267	Discontinued
0.6211	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3144	Approved
0.6207	Remote Similarity	NPD3145	Approved
0.6202	Remote Similarity	NPD7476	Discontinued
0.6201	Remote Similarity	NPD3656	Approved
0.6201	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.62	Remote Similarity	NPD3316	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD7546	Discontinued
0.6176	Remote Similarity	NPD4129	Approved
0.6173	Remote Similarity	NPD3965	Phase 1
0.6171	Remote Similarity	NPD2674	Phase 3
0.6171	Remote Similarity	NPD7477	Discontinued
0.617	Remote Similarity	NPD1769	Discontinued
0.6167	Remote Similarity	NPD4597	Approved
0.6167	Remote Similarity	NPD4598	Approved
0.6162	Remote Similarity	NPD3037	Phase 1
0.6158	Remote Similarity	NPD7773	Phase 2
0.6158	Remote Similarity	NPD2157	Approved
0.6154	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD3179	Approved
0.6149	Remote Similarity	NPD3180	Approved
0.6139	Remote Similarity	NPD4157	Discontinued
0.6133	Remote Similarity	NPD4236	Phase 3
0.6133	Remote Similarity	NPD4237	Approved
0.6132	Remote Similarity	NPD7263	Phase 2
0.6131	Remote Similarity	NPD7883	Discontinued
0.6127	Remote Similarity	NPD4324	Phase 2
0.6127	Remote Similarity	NPD4325	Phase 2
0.6122	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD2366	Approved
0.6117	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD2821	Approved
0.6111	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5553	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD4502	Phase 2
0.6093	Remote Similarity	NPD4206	Approved
0.6087	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7491	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD3685	Discontinued
0.608	Remote Similarity	NPD839	Approved
0.608	Remote Similarity	NPD840	Approved
0.6077	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD2122	Discontinued
0.6075	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5605	Phase 2
0.6071	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD2525	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6590	Discontinued
0.6067	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD3052	Approved
0.6067	Remote Similarity	NPD3054	Approved
0.6066	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6669	Phase 2
0.6066	Remote Similarity	NPD3804	Discontinued
0.6063	Remote Similarity	NPD6298	Discontinued
0.6062	Remote Similarity	NPD4944	Phase 2
0.6062	Remote Similarity	NPD4943	Phase 2
0.6062	Remote Similarity	NPD8067	Phase 3
0.6061	Remote Similarity	NPD2827	Approved
0.6061	Remote Similarity	NPD2825	Approved
0.6061	Remote Similarity	NPD795	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD2826	Approved
0.6059	Remote Similarity	NPD1091	Approved
0.6059	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD3985	Discontinued
0.6053	Remote Similarity	NPD7972	Discontinued
0.6051	Remote Similarity	NPD2388	Discontinued
0.605	Remote Similarity	NPD2802	Phase 3
0.6049	Remote Similarity	NPD4740	Approved
0.6048	Remote Similarity	NPD6604	Discontinued
0.6045	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD1393	Approved
0.6044	Remote Similarity	NPD2458	Approved
0.6044	Remote Similarity	NPD2459	Approved
0.6044	Remote Similarity	NPD2460	Phase 3
0.6043	Remote Similarity	NPD1678	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD2883	Discontinued
0.6042	Remote Similarity	NPD5604	Discontinued
0.604	Remote Similarity	NPD6340	Approved
0.604	Remote Similarity	NPD6339	Approved
0.6039	Remote Similarity	NPD6550	Discontinued
0.6039	Remote Similarity	NPD5512	Phase 3
0.6037	Remote Similarity	NPD821	Approved
0.6031	Remote Similarity	NPD6379	Discontinued
0.6029	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD7630	Phase 3
0.6029	Remote Similarity	NPD7628	Phase 3
0.6028	Remote Similarity	NPD5845	Phase 2
0.6027	Remote Similarity	NPD3949	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