NPASS Compound

Structure

NPC469831 OpenBabel07101718222D 42 45 0 0 1 0 0 0 0 0999 V2000 1.7321 -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 -12.9904 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -3.0000 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -2.5000 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 -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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -1.0000 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 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 5 1 0 0 0 0 2 6 2 0 0 0 0 2 7 1 0 0 0 0 3 8 2 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 10 25 2 0 0 0 0 11 25 1 0 0 0 0 12 26 2 0 0 0 0 13 26 1 0 0 0 0 14 27 2 0 0 0 0 15 27 1 0 0 0 0 16 18 1 0 0 0 0 16 28 2 0 0 0 0 17 19 2 0 0 0 0 17 28 1 0 0 0 0 18 29 2 0 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 21 31 1 0 0 0 0 22 25 1 0 0 0 0 22 40 1 0 0 0 0 23 26 1 0 0 0 0 23 41 1 0 0 0 0 24 27 1 0 0 0 0 24 42 1 0 0 0 0 28 35 1 0 0 0 0 29 40 1 0 0 0 0 30 20 1 6 0 0 0 30 32 1 0 0 0 0 30 34 1 0 0 0 0 31 36 2 3 0 0 0 31 37 1 0 0 0 0 32 38 2 0 0 0 0 32 41 1 0 0 0 0 33 34 2 3 0 0 0 33 39 1 0 0 0 0 33 42 1 0 0 0 0 35 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	567.24
Volume:	591.283
LogP:	4.667
LogD:	5.273
LogS:	-4.679
# Rotatable Bonds:	18
TPSA:	114.99
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.136
Synthetic Accessibility Score:	2.751
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.213
MDCK Permeability:	0.0001567520812386647
Pgp-inhibitor:	0.982
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.759
20% Bioavailability (F20%):	0.648
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	99.21957397460938%
Volume Distribution (VD):	0.293
Pgp-substrate:	3.0952889919281006%

ADMET: Metabolism

CYP1A2-inhibitor:	0.628
CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.921
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.965
CYP2C9-substrate:	0.367
CYP2D6-inhibitor:	0.736
CYP2D6-substrate:	0.206
CYP3A4-inhibitor:	0.954
CYP3A4-substrate:	0.564

ADMET: Excretion

Clearance (CL):	8.69
Half-life (T1/2):	0.43

ADMET: Toxicity

hERG Blockers:	0.099
Human Hepatotoxicity (H-HT):	0.29
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.925
Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.051
Skin Sensitization:	0.312
Carcinogencity:	0.637
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC469831

Natural Product ID:	NPC469831
*Common Name:**	N2-(Benzyloxycarbonyl)-L-Glutamic Acid1-(Benzyl Ester)5-[(4-Benzyloxy-Phenyl)-Hydrazide]
IUPAC Name:	benzyl (2S)-5-oxo-2-(phenylmethoxycarbonylamino)-5-[2-(4-phenylmethoxyphenyl)hydrazinyl]pentanoate
Synonyms:
Standard InCHIKey:	DWZCLQMRHOJBPC-PMERELPUSA-N
Standard InCHI:	InChI=1S/C33H33N3O6/c37-31(36-35-28-16-18-29(19-17-28)40-22-25-10-4-1-5-11-25)21-20-30(32(38)41-23-26-12-6-2-7-13-26)34-33(39)42-24-27-14-8-3-9-15-27/h1-19,30,35H,20-24H2,(H,34,39)(H,36,37)/t30-/m0/s1
SMILES:	OC(=NNc1ccc(cc1)OCc1ccccc1)CC[C@@H](C(=O)OCc1ccccc1)N=C(OCc1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1210430
PubChem CID:	49863077
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0004315] Glutamine and derivatives

*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
NPO14642	Lichina pygmaea	Species	Lichinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20570625]
NPO14642	Lichina pygmaea	Species	Lichinaceae	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	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1083	Cell Line	A-375	Homo sapiens	IC50	>	50000.0	nM	PMID[559332]
NPT1083	Cell Line	A-375	Homo sapiens	Inhibition	=	4.0	%	PMID[559332]
NPT1083	Cell Line	A-375	Homo sapiens	Inhibition	=	19.0	%	PMID[559332]
NPT319	Cell Line	B16	Mus musculus	IC50	=	5000.0	nM	PMID[559332]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	100.0	%	PMID[559332]
NPT319	Cell Line	B16	Mus musculus	IC50	=	600.0	nM	PMID[559332]

☑ 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 NPC469831 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	242
0.1-0.2	1673
0.2-0.3	9761
0.3-0.4	7823
0.4-0.5	11825
0.5-0.6	10864
0.6-0.7	491
0.7-0.8	15
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC469829
0.9524	High Similarity	NPC469830
0.7394	Intermediate Similarity	NPC91615
0.7293	Intermediate Similarity	NPC314861
0.7288	Intermediate Similarity	NPC56635
0.7222	Intermediate Similarity	NPC311357
0.7101	Intermediate Similarity	NPC122542
0.71	Intermediate Similarity	NPC473460
0.7083	Intermediate Similarity	NPC232872
0.7024	Intermediate Similarity	NPC470392
0.7018	Intermediate Similarity	NPC469828
0.6971	Remote Similarity	NPC247298
0.6931	Remote Similarity	NPC315631
0.6919	Remote Similarity	NPC108847
0.6919	Remote Similarity	NPC127362
0.6915	Remote Similarity	NPC214368
0.6897	Remote Similarity	NPC473422
0.6893	Remote Similarity	NPC132771
0.6893	Remote Similarity	NPC245974
0.6885	Remote Similarity	NPC231862
0.6884	Remote Similarity	NPC478049
0.6884	Remote Similarity	NPC314948
0.6848	Remote Similarity	NPC57105
0.6839	Remote Similarity	NPC314113
0.6793	Remote Similarity	NPC19023
0.6743	Remote Similarity	NPC212850
0.6743	Remote Similarity	NPC91953
0.6743	Remote Similarity	NPC83289
0.6743	Remote Similarity	NPC189724
0.6743	Remote Similarity	NPC469360
0.6726	Remote Similarity	NPC210950
0.6726	Remote Similarity	NPC199738
0.6725	Remote Similarity	NPC471953
0.6725	Remote Similarity	NPC244866
0.6718	Remote Similarity	NPC313886
0.6703	Remote Similarity	NPC306366
0.6686	Remote Similarity	NPC197921
0.6684	Remote Similarity	NPC204179
0.6683	Remote Similarity	NPC471561
0.6667	Remote Similarity	NPC191863
0.6667	Remote Similarity	NPC326966
0.6667	Remote Similarity	NPC289776
0.6667	Remote Similarity	NPC133470
0.6648	Remote Similarity	NPC17760
0.6647	Remote Similarity	NPC325651
0.663	Remote Similarity	NPC212699
0.663	Remote Similarity	NPC207675
0.6618	Remote Similarity	NPC242728
0.6615	Remote Similarity	NPC8467
0.6596	Remote Similarity	NPC254700
0.6585	Remote Similarity	NPC472330
0.6585	Remote Similarity	NPC472329
0.658	Remote Similarity	NPC474902
0.6579	Remote Similarity	NPC477888
0.6556	Remote Similarity	NPC259678
0.6548	Remote Similarity	NPC315542
0.6548	Remote Similarity	NPC477391
0.6541	Remote Similarity	NPC10875
0.6541	Remote Similarity	NPC187028
0.6541	Remote Similarity	NPC305700
0.6541	Remote Similarity	NPC197741
0.6541	Remote Similarity	NPC10730
0.6541	Remote Similarity	NPC140915
0.6541	Remote Similarity	NPC18249
0.6541	Remote Similarity	NPC10221
0.6509	Remote Similarity	NPC4974
0.6497	Remote Similarity	NPC318028
0.6497	Remote Similarity	NPC282087
0.6497	Remote Similarity	NPC317741
0.6497	Remote Similarity	NPC318984
0.6497	Remote Similarity	NPC259800
0.6497	Remote Similarity	NPC241086
0.6497	Remote Similarity	NPC328137
0.6495	Remote Similarity	NPC9475
0.6488	Remote Similarity	NPC471315
0.6488	Remote Similarity	NPC471314
0.6477	Remote Similarity	NPC473402
0.6473	Remote Similarity	NPC474077
0.6468	Remote Similarity	NPC473378
0.6468	Remote Similarity	NPC475411
0.6468	Remote Similarity	NPC473407
0.6465	Remote Similarity	NPC138083
0.6464	Remote Similarity	NPC473769
0.6464	Remote Similarity	NPC313414
0.6462	Remote Similarity	NPC194671
0.6462	Remote Similarity	NPC269750
0.6462	Remote Similarity	NPC45037
0.6462	Remote Similarity	NPC471532
0.6458	Remote Similarity	NPC83241
0.6458	Remote Similarity	NPC230611
0.6452	Remote Similarity	NPC112766
0.6452	Remote Similarity	NPC315257
0.6441	Remote Similarity	NPC471316
0.6437	Remote Similarity	NPC274732
0.6422	Remote Similarity	NPC149962
0.642	Remote Similarity	NPC6570
0.6418	Remote Similarity	NPC174122
0.6418	Remote Similarity	NPC474059
0.6418	Remote Similarity	NPC64140
0.6417	Remote Similarity	NPC319320
0.6417	Remote Similarity	NPC287757
0.6417	Remote Similarity	NPC70549
0.6413	Remote Similarity	NPC182119
0.6409	Remote Similarity	NPC136951
0.6409	Remote Similarity	NPC97004
0.6409	Remote Similarity	NPC161155
0.6407	Remote Similarity	NPC160120
0.6407	Remote Similarity	NPC17388
0.6407	Remote Similarity	NPC289330
0.6407	Remote Similarity	NPC471308
0.6407	Remote Similarity	NPC53596
0.6404	Remote Similarity	NPC203972
0.6404	Remote Similarity	NPC326860
0.6404	Remote Similarity	NPC197239
0.64	Remote Similarity	NPC105541
0.6392	Remote Similarity	NPC155506
0.6392	Remote Similarity	NPC95412
0.6392	Remote Similarity	NPC158277
0.6392	Remote Similarity	NPC164608
0.6392	Remote Similarity	NPC159767
0.639	Remote Similarity	NPC144314
0.6386	Remote Similarity	NPC28510
0.6385	Remote Similarity	NPC326333
0.638	Remote Similarity	NPC264782
0.6379	Remote Similarity	NPC313466
0.6374	Remote Similarity	NPC97282
0.6373	Remote Similarity	NPC310894
0.6368	Remote Similarity	NPC472923
0.6368	Remote Similarity	NPC234069
0.6359	Remote Similarity	NPC50548
0.6354	Remote Similarity	NPC178466
0.6354	Remote Similarity	NPC63628
0.6353	Remote Similarity	NPC211218
0.6343	Remote Similarity	NPC208022
0.634	Remote Similarity	NPC306804
0.634	Remote Similarity	NPC273755
0.6339	Remote Similarity	NPC254798
0.6337	Remote Similarity	NPC283207
0.6335	Remote Similarity	NPC50380
0.6335	Remote Similarity	NPC179250
0.6335	Remote Similarity	NPC70172
0.6332	Remote Similarity	NPC477392
0.6332	Remote Similarity	NPC315934
0.6332	Remote Similarity	NPC294951
0.6329	Remote Similarity	NPC123859
0.6326	Remote Similarity	NPC326027
0.6324	Remote Similarity	NPC314083
0.6324	Remote Similarity	NPC114659
0.6324	Remote Similarity	NPC139699
0.6322	Remote Similarity	NPC473987
0.6321	Remote Similarity	NPC269383
0.6321	Remote Similarity	NPC151030
0.6316	Remote Similarity	NPC95733
0.6316	Remote Similarity	NPC62101
0.6313	Remote Similarity	NPC288305
0.6313	Remote Similarity	NPC314025
0.631	Remote Similarity	NPC263835
0.6308	Remote Similarity	NPC279871
0.6307	Remote Similarity	NPC297584
0.6302	Remote Similarity	NPC107938
0.6302	Remote Similarity	NPC294516
0.6302	Remote Similarity	NPC473502
0.6301	Remote Similarity	NPC296712
0.6301	Remote Similarity	NPC274268
0.63	Remote Similarity	NPC235194
0.6296	Remote Similarity	NPC314817
0.6296	Remote Similarity	NPC316297
0.6296	Remote Similarity	NPC66191
0.6296	Remote Similarity	NPC103250
0.6294	Remote Similarity	NPC476278
0.6286	Remote Similarity	NPC45191
0.6284	Remote Similarity	NPC9373
0.6283	Remote Similarity	NPC292143
0.6283	Remote Similarity	NPC139506
0.6281	Remote Similarity	NPC314656
0.6281	Remote Similarity	NPC314213
0.6279	Remote Similarity	NPC29477
0.6267	Remote Similarity	NPC471531
0.6263	Remote Similarity	NPC32064
0.6257	Remote Similarity	NPC315632
0.6256	Remote Similarity	NPC248670
0.625	Remote Similarity	NPC315913
0.625	Remote Similarity	NPC313375
0.625	Remote Similarity	NPC256369
0.625	Remote Similarity	NPC314725
0.6244	Remote Similarity	NPC474919
0.6237	Remote Similarity	NPC471568
0.6237	Remote Similarity	NPC46009
0.6237	Remote Similarity	NPC196091
0.6237	Remote Similarity	NPC473693
0.6237	Remote Similarity	NPC90984
0.6235	Remote Similarity	NPC27581
0.6233	Remote Similarity	NPC26928
0.623	Remote Similarity	NPC199737
0.6225	Remote Similarity	NPC248822
0.6224	Remote Similarity	NPC471165
0.6219	Remote Similarity	NPC299806
0.6218	Remote Similarity	NPC328649
0.6216	Remote Similarity	NPC277857
0.6216	Remote Similarity	NPC324081

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 NPC469831 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	553
0.2-0.3	1149
0.3-0.4	1347
0.4-0.5	2798
0.5-0.6	2672
0.6-0.7	455
0.7-0.8	17
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
0.7622	Intermediate Similarity	NPD6045	Phase 3
0.7448	Intermediate Similarity	NPD8249	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3965	Phase 1
0.7204	Intermediate Similarity	NPD5334	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5811	Approved
0.7135	Intermediate Similarity	NPD3952	Approved
0.7135	Intermediate Similarity	NPD3953	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3951	Phase 3
0.7105	Intermediate Similarity	NPD7546	Discontinued
0.7095	Intermediate Similarity	NPD2366	Approved
0.7062	Intermediate Similarity	NPD5871	Discontinued
0.7047	Intermediate Similarity	NPD5558	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7083	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7477	Discontinued
0.7022	Intermediate Similarity	NPD4003	Phase 3
0.6989	Remote Similarity	NPD2114	Discontinued
0.6982	Remote Similarity	NPD1393	Approved
0.6973	Remote Similarity	NPD2247	Approved
0.6973	Remote Similarity	NPD2249	Approved
0.6968	Remote Similarity	NPD3909	Discontinued
0.695	Remote Similarity	NPD6519	Phase 2
0.6947	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3154	Approved
0.6943	Remote Similarity	NPD3153	Approved
0.6919	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.691	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD3778	Approved
0.6895	Remote Similarity	NPD5557	Phase 1
0.6882	Remote Similarity	NPD756	Suspended
0.6872	Remote Similarity	NPD3627	Approved
0.6869	Remote Similarity	NPD7256	Discontinued
0.686	Remote Similarity	NPD5416	Discontinued
0.6856	Remote Similarity	NPD6967	Phase 2
0.6851	Remote Similarity	NPD3296	Phase 1
0.6848	Remote Similarity	NPD7773	Phase 2
0.6845	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7608	Discontinued
0.6837	Remote Similarity	NPD2843	Phase 2
0.6837	Remote Similarity	NPD2845	Phase 2
0.6832	Remote Similarity	NPD7476	Discontinued
0.6823	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6874	Approved
0.6793	Remote Similarity	NPD3557	Approved
0.6793	Remote Similarity	NPD3560	Approved
0.6793	Remote Similarity	NPD3558	Approved
0.6793	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD3556	Approved
0.6786	Remote Similarity	NPD1898	Discontinued
0.6778	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6184	Discontinued
0.6762	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.672	Remote Similarity	NPD2216	Approved
0.672	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.672	Remote Similarity	NPD3453	Discontinued
0.672	Remote Similarity	NPD2215	Approved
0.6716	Remote Similarity	NPD6034	Phase 2
0.6702	Remote Similarity	NPD3511	Discontinued
0.6686	Remote Similarity	NPD1422	Approved
0.6667	Remote Similarity	NPD6502	Phase 2
0.6667	Remote Similarity	NPD2458	Approved
0.6667	Remote Similarity	NPD2460	Phase 3
0.6667	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2459	Approved
0.6649	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7972	Discontinued
0.663	Remote Similarity	NPD6390	Discontinued
0.6626	Remote Similarity	NPD254	Approved
0.6618	Remote Similarity	NPD6810	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD2681	Approved
0.6614	Remote Similarity	NPD7484	Phase 3
0.6614	Remote Similarity	NPD7485	Phase 3
0.6614	Remote Similarity	NPD2680	Approved
0.661	Remote Similarity	NPD7153	Discontinued
0.6601	Remote Similarity	NPD6877	Discontinued
0.6598	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7131	Phase 3
0.6587	Remote Similarity	NPD6296	Discontinued
0.6585	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3416	Discontinued
0.6584	Remote Similarity	NPD6550	Discontinued
0.6573	Remote Similarity	NPD8015	Phase 3
0.6571	Remote Similarity	NPD1536	Approved
0.657	Remote Similarity	NPD7891	Discontinued
0.6569	Remote Similarity	NPD7810	Phase 3
0.6569	Remote Similarity	NPD7811	Phase 3
0.6567	Remote Similarity	NPD5150	Phase 2
0.6564	Remote Similarity	NPD3037	Phase 1
0.6561	Remote Similarity	NPD6746	Phase 2
0.6557	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD9694	Discovery
0.6545	Remote Similarity	NPD4083	Discontinued
0.6543	Remote Similarity	NPD8031	Discontinued
0.6541	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD2802	Phase 3
0.6526	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD2821	Approved
0.6524	Remote Similarity	NPD7318	Phase 3
0.6524	Remote Similarity	NPD6063	Approved
0.6519	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7853	Phase 2
0.6512	Remote Similarity	NPD7395	Discontinued
0.6512	Remote Similarity	NPD3136	Phase 2
0.651	Remote Similarity	NPD2248	Approved
0.651	Remote Similarity	NPD2246	Approved
0.6505	Remote Similarity	NPD8019	Approved
0.6505	Remote Similarity	NPD6604	Discontinued
0.6502	Remote Similarity	NPD5512	Phase 3
0.65	Remote Similarity	NPD4258	Approved
0.65	Remote Similarity	NPD7994	Phase 2
0.65	Remote Similarity	NPD4259	Approved
0.6497	Remote Similarity	NPD1537	Approved
0.6497	Remote Similarity	NPD1538	Phase 1
0.6497	Remote Similarity	NPD1519	Approved
0.6497	Remote Similarity	NPD7877	Suspended
0.6495	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD2874	Phase 2
0.6484	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD1521	Approved
0.6477	Remote Similarity	NPD5605	Phase 2
0.6477	Remote Similarity	NPD1520	Approved
0.6461	Remote Similarity	NPD3656	Approved
0.6459	Remote Similarity	NPD6905	Phase 2
0.6455	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD2614	Approved
0.6452	Remote Similarity	NPD7438	Suspended
0.6452	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4255	Phase 1
0.6447	Remote Similarity	NPD7883	Discontinued
0.6442	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6865	Phase 2
0.6441	Remote Similarity	NPD6864	Phase 2
0.644	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5445	Approved
0.6429	Remote Similarity	NPD5429	Discontinued
0.6425	Remote Similarity	NPD4597	Approved
0.6425	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4598	Approved
0.6425	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD7861	Discontinued
0.6417	Remote Similarity	NPD5356	Approved
0.6417	Remote Similarity	NPD5355	Approved
0.6417	Remote Similarity	NPD7317	Phase 3
0.6416	Remote Similarity	NPD5163	Phase 2
0.6412	Remote Similarity	NPD196	Phase 1
0.6406	Remote Similarity	NPD5847	Phase 1
0.6404	Remote Similarity	NPD7450	Phase 2
0.6404	Remote Similarity	NPD1522	Approved
0.6404	Remote Similarity	NPD1523	Approved
0.6398	Remote Similarity	NPD4154	Approved
0.6396	Remote Similarity	NPD6104	Discontinued
0.6395	Remote Similarity	NPD4993	Discontinued
0.6394	Remote Similarity	NPD7316	Discontinued
0.6393	Remote Similarity	NPD4123	Phase 3
0.6393	Remote Similarity	NPD3536	Discontinued
0.6392	Remote Similarity	NPD4443	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.639	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.639	Remote Similarity	NPD5651	Approved
0.639	Remote Similarity	NPD6988	Phase 1
0.639	Remote Similarity	NPD5652	Approved
0.639	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.639	Remote Similarity	NPD5650	Approved
0.6387	Remote Similarity	NPD3251	Approved
0.6386	Remote Similarity	NPD1924	Approved
0.6382	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7554	Discontinued
0.6373	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD955	Approved
0.6364	Remote Similarity	NPD6669	Phase 2
0.6364	Remote Similarity	NPD7105	Phase 1
0.6364	Remote Similarity	NPD2672	Discontinued
0.6364	Remote Similarity	NPD6677	Suspended
0.6359	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD4740	Approved
0.6354	Remote Similarity	NPD6379	Discontinued
0.6354	Remote Similarity	NPD6457	Approved
0.6354	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7222	Phase 2
0.635	Remote Similarity	NPD6340	Approved
0.635	Remote Similarity	NPD6339	Approved
0.6349	Remote Similarity	NPD1012	Discontinued
0.6348	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD822	Approved
0.6345	Remote Similarity	NPD5553	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD6147	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