NPASS Compound

Structure

NPC469830 OpenBabel07101718222D 42 45 0 0 1 0 0 0 0 0999 V2000 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -0.5000 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 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 0.8660 -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 8.6603 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 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 8.6603 -3.0000 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 1.7321 -0.0000 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 6.0622 -1.5000 0.0000 C 0 0 1 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 6.9282 -2.0000 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 6.0622 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 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 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 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 11 1 0 0 0 0 5 12 2 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 17 2 0 0 0 0 10 18 1 0 0 0 0 11 25 2 0 0 0 0 12 25 1 0 0 0 0 13 26 2 0 0 0 0 14 26 1 0 0 0 0 15 27 2 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 29 2 0 0 0 0 19 20 1 0 0 0 0 20 31 1 0 0 0 0 21 28 2 0 0 0 0 21 29 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 19 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:	4.673
LogD:	5.209
LogS:	-4.734
# 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:	2.787
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:	-5.207
MDCK Permeability:	0.000160012801643461
Pgp-inhibitor:	0.98
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.832
20% Bioavailability (F20%):	0.7
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	99.35037231445312%
Volume Distribution (VD):	0.305
Pgp-substrate:	3.208894968032837%

ADMET: Metabolism

CYP1A2-inhibitor:	0.808
CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	0.947
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.969
CYP2C9-substrate:	0.184
CYP2D6-inhibitor:	0.845
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.966
CYP3A4-substrate:	0.505

ADMET: Excretion

Clearance (CL):	8.792
Half-life (T1/2):	0.452

ADMET: Toxicity

hERG Blockers:	0.107
Human Hepatotoxicity (H-HT):	0.338
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.91
Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.072
Skin Sensitization:	0.317
Carcinogencity:	0.603
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC469830

Natural Product ID:	NPC469830
*Common Name:**	N2-(Benzyloxycarbonyl)-L-Glutamic Acid1-(Benzyl Ester)5-[(3-Benzyloxy-Phenyl)-Hydrazide]
IUPAC Name:	benzyl (2S)-5-oxo-2-(phenylmethoxycarbonylamino)-5-[2-(3-phenylmethoxyphenyl)hydrazinyl]pentanoate
Synonyms:
Standard InCHIKey:	UNBCLNDLTZGOIX-PMERELPUSA-N
Standard InCHI:	InChI=1S/C33H33N3O6/c37-31(36-35-28-17-10-18-29(21-28)40-22-25-11-4-1-5-12-25)20-19-30(32(38)41-23-26-13-6-2-7-14-26)34-33(39)42-24-27-15-8-3-9-16-27/h1-18,21,30,35H,19-20,22-24H2,(H,34,39)(H,36,37)/t30-/m0/s1
SMILES:	OC(=NNc1cccc(c1)OCc1ccccc1)CC[C@@H](C(=O)OCc1ccccc1)N=C(OCc1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1210429
PubChem CID:	49863076
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	=	28000.0	nM	PMID[519987]
NPT1083	Cell Line	A-375	Homo sapiens	Inhibition	=	80.0	%	PMID[519987]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	29000.0	nM	PMID[519987]
NPT1083	Cell Line	A-375	Homo sapiens	Inhibition	=	73.0	%	PMID[519987]
NPT319	Cell Line	B16	Mus musculus	IC50	=	8000.0	nM	PMID[519987]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	100.0	%	PMID[519987]
NPT319	Cell Line	B16	Mus musculus	IC50	=	14500.0	nM	PMID[519987]

☑ 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 NPC469830 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	254
0.1-0.2	1806
0.2-0.3	10822
0.3-0.4	6858
0.4-0.5	13439
0.5-0.6	8918
0.6-0.7	574
0.7-0.8	23
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC469831
0.9467	High Similarity	NPC469829
0.7456	Intermediate Similarity	NPC469828
0.73	Intermediate Similarity	NPC473460
0.7264	Intermediate Similarity	NPC473422
0.7164	Intermediate Similarity	NPC311357
0.7135	Intermediate Similarity	NPC314861
0.7127	Intermediate Similarity	NPC56635
0.7018	Intermediate Similarity	NPC91615
0.6946	Remote Similarity	NPC472329
0.6946	Remote Similarity	NPC472330
0.6939	Remote Similarity	NPC232872
0.6936	Remote Similarity	NPC122542
0.6875	Remote Similarity	NPC471561
0.6875	Remote Similarity	NPC9475
0.6863	Remote Similarity	NPC214368
0.6862	Remote Similarity	NPC127362
0.686	Remote Similarity	NPC470392
0.6833	Remote Similarity	NPC132771
0.6816	Remote Similarity	NPC247298
0.681	Remote Similarity	NPC471532
0.6788	Remote Similarity	NPC315631
0.6784	Remote Similarity	NPC474059
0.6782	Remote Similarity	NPC108847
0.675	Remote Similarity	NPC28510
0.674	Remote Similarity	NPC245974
0.6738	Remote Similarity	NPC231862
0.6702	Remote Similarity	NPC57105
0.6685	Remote Similarity	NPC314113
0.6667	Remote Similarity	NPC10730
0.6667	Remote Similarity	NPC10875
0.665	Remote Similarity	NPC242728
0.6636	Remote Similarity	NPC274268
0.6632	Remote Similarity	NPC254700
0.6615	Remote Similarity	NPC477888
0.6614	Remote Similarity	NPC191863
0.6614	Remote Similarity	NPC289776
0.6614	Remote Similarity	NPC133470
0.6605	Remote Similarity	NPC471531
0.6592	Remote Similarity	NPC91953
0.6592	Remote Similarity	NPC469360
0.6592	Remote Similarity	NPC212850
0.6592	Remote Similarity	NPC189724
0.6592	Remote Similarity	NPC83289
0.6585	Remote Similarity	NPC478049
0.6585	Remote Similarity	NPC314948
0.6583	Remote Similarity	NPC313886
0.6583	Remote Similarity	NPC315542
0.658	Remote Similarity	NPC310894
0.6578	Remote Similarity	NPC212699
0.6578	Remote Similarity	NPC207675
0.6571	Remote Similarity	NPC244866
0.6571	Remote Similarity	NPC471953
0.657	Remote Similarity	NPC210950
0.657	Remote Similarity	NPC199738
0.6564	Remote Similarity	NPC8467
0.6564	Remote Similarity	NPC168153
0.6546	Remote Similarity	NPC225381
0.6536	Remote Similarity	NPC197921
0.6514	Remote Similarity	NPC326966
0.6503	Remote Similarity	NPC259678
0.6503	Remote Similarity	NPC17760
0.65	Remote Similarity	NPC138083
0.6494	Remote Similarity	NPC325651
0.648	Remote Similarity	NPC473432
0.6474	Remote Similarity	NPC19023
0.6471	Remote Similarity	NPC204970
0.6456	Remote Similarity	NPC149962
0.6453	Remote Similarity	NPC174122
0.6453	Remote Similarity	NPC174629
0.6453	Remote Similarity	NPC283207
0.6453	Remote Similarity	NPC64140
0.6447	Remote Similarity	NPC474902
0.6445	Remote Similarity	NPC87714
0.6442	Remote Similarity	NPC123859
0.6439	Remote Similarity	NPC314083
0.6429	Remote Similarity	NPC473402
0.6429	Remote Similarity	NPC164608
0.6425	Remote Similarity	NPC144314
0.6422	Remote Similarity	NPC473378
0.6422	Remote Similarity	NPC473407
0.6418	Remote Similarity	NPC477391
0.6414	Remote Similarity	NPC194671
0.6414	Remote Similarity	NPC269750
0.6414	Remote Similarity	NPC45037
0.6413	Remote Similarity	NPC26928
0.641	Remote Similarity	NPC230611
0.6404	Remote Similarity	NPC234069
0.6402	Remote Similarity	NPC305700
0.6402	Remote Similarity	NPC315257
0.6402	Remote Similarity	NPC140915
0.6402	Remote Similarity	NPC18249
0.6402	Remote Similarity	NPC187028
0.6402	Remote Similarity	NPC197741
0.6402	Remote Similarity	NPC10221
0.6394	Remote Similarity	NPC50548
0.6387	Remote Similarity	NPC306366
0.6384	Remote Similarity	NPC248903
0.638	Remote Similarity	NPC99724
0.6378	Remote Similarity	NPC73280
0.6373	Remote Similarity	NPC204179
0.6364	Remote Similarity	NPC182119
0.6359	Remote Similarity	NPC136951
0.6359	Remote Similarity	NPC97004
0.6359	Remote Similarity	NPC161155
0.6358	Remote Similarity	NPC4974
0.6354	Remote Similarity	NPC328137
0.6354	Remote Similarity	NPC318028
0.6354	Remote Similarity	NPC72291
0.6354	Remote Similarity	NPC259800
0.6354	Remote Similarity	NPC318984
0.6354	Remote Similarity	NPC282087
0.6354	Remote Similarity	NPC241086
0.6354	Remote Similarity	NPC317741
0.6351	Remote Similarity	NPC474077
0.6351	Remote Similarity	NPC148124
0.6346	Remote Similarity	NPC472191
0.6345	Remote Similarity	NPC158277
0.6345	Remote Similarity	NPC155506
0.6345	Remote Similarity	NPC159767
0.6343	Remote Similarity	NPC326333
0.6341	Remote Similarity	NPC475411
0.6337	Remote Similarity	NPC471315
0.6337	Remote Similarity	NPC471314
0.6337	Remote Similarity	NPC473007
0.6336	Remote Similarity	NPC469722
0.6332	Remote Similarity	NPC472331
0.6332	Remote Similarity	NPC274002
0.6332	Remote Similarity	NPC126515
0.633	Remote Similarity	NPC184161
0.6327	Remote Similarity	NPC83241
0.6324	Remote Similarity	NPC97282
0.6324	Remote Similarity	NPC313414
0.6305	Remote Similarity	NPC276120
0.63	Remote Similarity	NPC32064
0.63	Remote Similarity	NPC70092
0.63	Remote Similarity	NPC227033
0.6298	Remote Similarity	NPC471316
0.6294	Remote Similarity	NPC306804
0.6294	Remote Similarity	NPC273755
0.6293	Remote Similarity	NPC473008
0.6292	Remote Similarity	NPC274732
0.629	Remote Similarity	NPC254798
0.6287	Remote Similarity	NPC294951
0.6284	Remote Similarity	NPC326027
0.6283	Remote Similarity	NPC287757
0.6283	Remote Similarity	NPC319320
0.628	Remote Similarity	NPC203972
0.6278	Remote Similarity	NPC6570
0.6276	Remote Similarity	NPC151030
0.6276	Remote Similarity	NPC269383
0.6266	Remote Similarity	NPC124300
0.6264	Remote Similarity	NPC197239
0.6264	Remote Similarity	NPC326860
0.6263	Remote Similarity	NPC476227
0.6263	Remote Similarity	NPC471165
0.6263	Remote Similarity	NPC279871
0.6263	Remote Similarity	NPC95412
0.6257	Remote Similarity	NPC160120
0.6257	Remote Similarity	NPC17388
0.6257	Remote Similarity	NPC53596
0.6257	Remote Similarity	NPC471308
0.6257	Remote Similarity	NPC289330
0.6257	Remote Similarity	NPC105541
0.6256	Remote Similarity	NPC316297
0.6256	Remote Similarity	NPC19555
0.6256	Remote Similarity	NPC328649
0.6256	Remote Similarity	NPC314817
0.6256	Remote Similarity	NPC66191
0.6256	Remote Similarity	NPC294516
0.6256	Remote Similarity	NPC473502
0.6256	Remote Similarity	NPC107938
0.6256	Remote Similarity	NPC235194
0.625	Remote Similarity	NPC477160
0.6244	Remote Similarity	NPC89831
0.6243	Remote Similarity	NPC219383
0.6239	Remote Similarity	NPC291609
0.6237	Remote Similarity	NPC472923
0.6236	Remote Similarity	NPC313466
0.6233	Remote Similarity	NPC477532
0.6231	Remote Similarity	NPC475215
0.6231	Remote Similarity	NPC108434
0.6231	Remote Similarity	NPC50016
0.6227	Remote Similarity	NPC152768
0.6227	Remote Similarity	NPC148183
0.6222	Remote Similarity	NPC21638
0.6219	Remote Similarity	NPC39822
0.6216	Remote Similarity	NPC63628
0.6216	Remote Similarity	NPC178466
0.6215	Remote Similarity	NPC14339
0.6214	Remote Similarity	NPC29531
0.6212	Remote Similarity	NPC248670
0.6207	Remote Similarity	NPC320394
0.6207	Remote Similarity	NPC211218
0.6207	Remote Similarity	NPC315934
0.6207	Remote Similarity	NPC477392
0.6205	Remote Similarity	NPC179250
0.6205	Remote Similarity	NPC50380
0.6205	Remote Similarity	NPC70172
0.6202	Remote Similarity	NPC471825

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 NPC469830 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	563
0.2-0.3	1144
0.3-0.4	1477
0.4-0.5	2769
0.5-0.6	2572
0.6-0.7	444
0.7-0.8	14
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
0.7842	Intermediate Similarity	NPD8249	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6045	Phase 3
0.7225	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3965	Phase 1
0.7112	Intermediate Similarity	NPD2216	Approved
0.7112	Intermediate Similarity	NPD2215	Approved
0.7074	Intermediate Similarity	NPD3952	Approved
0.7074	Intermediate Similarity	NPD3953	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD3951	Phase 3
0.7072	Intermediate Similarity	NPD3296	Phase 1
0.7047	Intermediate Similarity	NPD7546	Discontinued
0.7041	Intermediate Similarity	NPD2843	Phase 2
0.7041	Intermediate Similarity	NPD2845	Phase 2
0.7017	Intermediate Similarity	NPD5811	Approved
0.7	Intermediate Similarity	NPD3909	Discontinued
0.6944	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5557	Phase 1
0.6904	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6519	Phase 2
0.6895	Remote Similarity	NPD2248	Approved
0.6895	Remote Similarity	NPD2246	Approved
0.6875	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7877	Suspended
0.6868	Remote Similarity	NPD4003	Phase 3
0.686	Remote Similarity	NPD7477	Discontinued
0.6825	Remote Similarity	NPD2247	Approved
0.6825	Remote Similarity	NPD2249	Approved
0.6816	Remote Similarity	NPD7256	Discontinued
0.6812	Remote Similarity	NPD6905	Phase 2
0.6804	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6877	Discontinued
0.6791	Remote Similarity	NPD7773	Phase 2
0.6779	Remote Similarity	NPD6296	Discontinued
0.6769	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2366	Approved
0.6757	Remote Similarity	NPD3778	Approved
0.6755	Remote Similarity	NPD955	Approved
0.675	Remote Similarity	NPD5871	Discontinued
0.6749	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD5652	Approved
0.6749	Remote Similarity	NPD5651	Approved
0.6749	Remote Similarity	NPD5650	Approved
0.6731	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD6967	Phase 2
0.6717	Remote Similarity	NPD3154	Approved
0.6717	Remote Similarity	NPD3153	Approved
0.6702	Remote Similarity	NPD7608	Discontinued
0.6702	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5560	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3037	Phase 1
0.6683	Remote Similarity	NPD6874	Approved
0.6667	Remote Similarity	NPD4604	Approved
0.6667	Remote Similarity	NPD4605	Approved
0.6667	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD5416	Discontinued
0.665	Remote Similarity	NPD1898	Discontinued
0.665	Remote Similarity	NPD2339	Phase 3
0.6649	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD2680	Approved
0.6649	Remote Similarity	NPD3557	Approved
0.6649	Remote Similarity	NPD3556	Approved
0.6649	Remote Similarity	NPD3558	Approved
0.6649	Remote Similarity	NPD3560	Approved
0.6649	Remote Similarity	NPD3511	Discontinued
0.6649	Remote Similarity	NPD2681	Approved
0.6648	Remote Similarity	NPD2114	Discontinued
0.6631	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.663	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD1393	Approved
0.6618	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7476	Discontinued
0.6613	Remote Similarity	NPD6502	Phase 2
0.6611	Remote Similarity	NPD2458	Approved
0.6611	Remote Similarity	NPD2459	Approved
0.6611	Remote Similarity	NPD2460	Phase 3
0.6602	Remote Similarity	NPD7810	Phase 3
0.6602	Remote Similarity	NPD7811	Phase 3
0.66	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7479	Phase 2
0.6569	Remote Similarity	NPD4523	Approved
0.6567	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7485	Phase 3
0.6562	Remote Similarity	NPD7484	Phase 3
0.6556	Remote Similarity	NPD7153	Discontinued
0.6552	Remote Similarity	NPD4740	Approved
0.6545	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3627	Approved
0.6534	Remote Similarity	NPD756	Suspended
0.6524	Remote Similarity	NPD7891	Discontinued
0.6522	Remote Similarity	NPD2874	Phase 2
0.6522	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.652	Remote Similarity	NPD5150	Phase 2
0.652	Remote Similarity	NPD5984	Phase 2
0.6519	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD7972	Discontinued
0.6508	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6034	Phase 2
0.6495	Remote Similarity	NPD4083	Discontinued
0.6486	Remote Similarity	NPD6390	Discontinued
0.6482	Remote Similarity	NPD4012	Approved
0.6481	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.648	Remote Similarity	NPD4354	Approved
0.6479	Remote Similarity	NPD4710	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD2821	Approved
0.6476	Remote Similarity	NPD7853	Phase 2
0.6474	Remote Similarity	NPD6063	Approved
0.6474	Remote Similarity	NPD7318	Phase 3
0.6471	Remote Similarity	NPD5587	Approved
0.6468	Remote Similarity	NPD5632	Approved
0.6465	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5445	Approved
0.6465	Remote Similarity	NPD6184	Discontinued
0.6462	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD6550	Discontinued
0.6456	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD8019	Approved
0.6452	Remote Similarity	NPD7131	Phase 3
0.6445	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD1422	Approved
0.6439	Remote Similarity	NPD4539	Phase 1
0.6432	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6746	Phase 2
0.6425	Remote Similarity	NPD1536	Approved
0.6425	Remote Similarity	NPD2941	Discontinued
0.6422	Remote Similarity	NPD1924	Approved
0.6411	Remote Similarity	NPD6810	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD3656	Approved
0.6408	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD3453	Discontinued
0.6406	Remote Similarity	NPD5902	Approved
0.6406	Remote Similarity	NPD5903	Approved
0.6406	Remote Similarity	NPD8031	Discontinued
0.6402	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD6669	Phase 2
0.6398	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7395	Discontinued
0.639	Remote Similarity	NPD4302	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD204	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD7994	Phase 2
0.6378	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD5512	Phase 3
0.6376	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7861	Discontinued
0.6373	Remote Similarity	NPD3342	Phase 2
0.6373	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD6644	Discontinued
0.6368	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD7317	Phase 3
0.6364	Remote Similarity	NPD2151	Approved
0.6364	Remote Similarity	NPD5163	Phase 2
0.6364	Remote Similarity	NPD3136	Phase 2
0.6359	Remote Similarity	NPD5847	Phase 1
0.6359	Remote Similarity	NPD7125	Discontinued
0.6355	Remote Similarity	NPD3065	Discontinued
0.6354	Remote Similarity	NPD1519	Approved
0.6354	Remote Similarity	NPD1537	Approved
0.6354	Remote Similarity	NPD1538	Phase 1
0.6351	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7316	Discontinued
0.6349	Remote Similarity	NPD5617	Suspended
0.6345	Remote Similarity	NPD5605	Phase 2
0.6344	Remote Similarity	NPD4123	Phase 3
0.6338	Remote Similarity	NPD3003	Approved
0.6337	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6853	Approved
0.6337	Remote Similarity	NPD6851	Approved
0.6333	Remote Similarity	NPD1520	Approved
0.6333	Remote Similarity	NPD1521	Approved
0.6324	Remote Similarity	NPD7554	Discontinued
0.6324	Remote Similarity	NPD3349	Phase 2
0.6321	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD7753	Approved
0.6319	Remote Similarity	NPD7752	Approved
0.6318	Remote Similarity	NPD6985	Discontinued
0.6318	Remote Similarity	NPD7883	Discontinued
0.6318	Remote Similarity	NPD1381	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD6461	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6677	Suspended
0.6316	Remote Similarity	NPD7438	Suspended
0.6313	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD3963	Phase 1
0.6308	Remote Similarity	NPD5429	Discontinued
0.6307	Remote Similarity	NPD2614	Approved
0.6305	Remote Similarity	NPD6339	Approved
0.6305	Remote Similarity	NPD6340	Approved
0.6303	Remote Similarity	NPD3416	Discontinued
0.6303	Remote Similarity	NPD6604	Discontinued
0.6301	Remote Similarity	NPD8015	Phase 3
0.63	Remote Similarity	NPD5553	Clinical (unspecified phase)
0.63	Remote Similarity	NPD8067	Phase 3

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