NPASS Compound

Structure

NPC275538 OpenBabel07101718192D 34 35 0 0 1 0 0 0 0 0999 V2000 11.2583 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 4.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 4.5000 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 10.3923 4.0000 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 6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 4.5000 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 12.9904 5.5000 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 9.5263 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6603 4.0000 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 9.5263 5.5000 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 13.8564 6.0000 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 7.7942 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 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 8.6603 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 4.5000 0.0000 O 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 1 5 1 0 0 0 0 1 13 2 0 0 0 0 2 6 2 0 0 0 0 2 13 1 0 0 0 0 3 7 1 0 0 0 0 3 14 2 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 15 2 0 0 0 0 6 15 1 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 11 33 1 0 0 0 0 12 20 1 0 0 0 0 12 34 1 0 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 17 21 1 0 0 0 0 17 23 2 0 0 0 0 18 22 1 0 0 0 0 18 24 2 0 0 0 0 19 20 1 0 0 0 0 19 27 1 6 0 0 0 20 28 1 6 0 0 0 21 29 2 0 0 0 0 21 33 1 0 0 0 0 22 30 2 0 0 0 0 22 34 1 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.14
Volume:	455.486
LogP:	1.256
LogD:	0.265
LogS:	-2.536
# Rotatable Bonds:	13
TPSA:	198.7
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.114
Synthetic Accessibility Score:	3.743
Fsp3:	0.273
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.017
MDCK Permeability:	1.4164764252200257e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.872
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	95.57677459716797%
Volume Distribution (VD):	0.284
Pgp-substrate:	2.889178991317749%

ADMET: Metabolism

CYP1A2-inhibitor:	0.398
CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	0.636
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.927
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.391
CYP3A4-substrate:	0.153

ADMET: Excretion

Clearance (CL):	1.86
Half-life (T1/2):	0.903

ADMET: Toxicity

hERG Blockers:	0.335
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.613
AMES Toxicity:	0.296
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.347
Carcinogencity:	0.363
Eye Corrosion:	0.003
Eye Irritation:	0.221
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: NPC275538

Natural Product ID:	NPC275538
*Common Name:**	Aspergillusol A
IUPAC Name:	[(2S,3R)-2,3-dihydroxy-4-[(2Z)-2-hydroxyimino-3-(4-hydroxyphenyl)propanoyl]oxybutyl] (2Z)-2-hydroxyimino-3-(4-hydroxyphenyl)propanoate
Synonyms:
Standard InCHIKey:	BXRQJOBHKCDAJW-KMMADPOHSA-N
Standard InCHI:	InChI=1S/C22H24N2O10/c25-15-5-1-13(2-6-15)9-17(23-31)21(29)33-11-19(27)20(28)12-34-22(30)18(24-32)10-14-3-7-16(26)8-4-14/h1-8,19-20,25-28,31-32H,9-12H2/b23-17-,24-18-/t19-,20+
SMILES:	c1cc(ccc1C/C(=N/O)/C(=O)OC[C@@H]([C@@H](COC(=O)/C(=NO)/Cc1ccc(cc1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1088570
PubChem CID:	44605528
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

*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
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075772]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16155971]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19824618]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21667999]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[324959]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	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	7
MIC	1

Activity Type	# Activity
Cell Line	3
Individual Protein	1
NON-MOLECULAR	1
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	>	100000.0	nM	PMID[550364]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	105000.0	nM	PMID[550364]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	74000.0	nM	PMID[550364]
NPT793	Cell Line	MOLT-3	Homo sapiens	IC50	=	19000.0	nM	PMID[550364]
NPT2	Others	Unspecified		IC50	=	465000.0	nM	PMID[550364]
NPT2	Others	Unspecified		IC50	=	1060000.0	nM	PMID[550364]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	50000.0	nM	PMID[550364]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	>	100.0	ug.mL-1	PMID[550365]

☑ 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 NPC275538 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	186
0.1-0.2	741
0.2-0.3	3228
0.3-0.4	9822
0.4-0.5	9870
0.5-0.6	11107
0.6-0.7	7259
0.7-0.8	477
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8537	High Similarity	NPC309808
0.8116	Intermediate Similarity	NPC6570
0.8088	Intermediate Similarity	NPC45191
0.803	Intermediate Similarity	NPC469927
0.8	Intermediate Similarity	NPC63345
0.7941	Intermediate Similarity	NPC158673
0.792	Intermediate Similarity	NPC326187
0.7899	Intermediate Similarity	NPC108553
0.7874	Intermediate Similarity	NPC48525
0.784	Intermediate Similarity	NPC31274
0.7836	Intermediate Similarity	NPC236981
0.7826	Intermediate Similarity	NPC469705
0.7826	Intermediate Similarity	NPC470122
0.7826	Intermediate Similarity	NPC17968
0.782	Intermediate Similarity	NPC472271
0.781	Intermediate Similarity	NPC325651
0.7801	Intermediate Similarity	NPC123988
0.78	Intermediate Similarity	NPC56635
0.7795	Intermediate Similarity	NPC177576
0.7786	Intermediate Similarity	NPC311091
0.7786	Intermediate Similarity	NPC471033
0.777	Intermediate Similarity	NPC476407
0.7769	Intermediate Similarity	NPC128249
0.7746	Intermediate Similarity	NPC471345
0.7727	Intermediate Similarity	NPC470214
0.7727	Intermediate Similarity	NPC470215
0.7727	Intermediate Similarity	NPC109371
0.7727	Intermediate Similarity	NPC70084
0.7721	Intermediate Similarity	NPC123704
0.7717	Intermediate Similarity	NPC321252
0.7717	Intermediate Similarity	NPC252544
0.7714	Intermediate Similarity	NPC471066
0.7714	Intermediate Similarity	NPC471095
0.7704	Intermediate Similarity	NPC14141
0.7692	Intermediate Similarity	NPC84789
0.7692	Intermediate Similarity	NPC302583
0.7692	Intermediate Similarity	NPC100558
0.7692	Intermediate Similarity	NPC310252
0.766	Intermediate Similarity	NPC164172
0.7652	Intermediate Similarity	NPC104514
0.7652	Intermediate Similarity	NPC86198
0.7647	Intermediate Similarity	NPC85565
0.7643	Intermediate Similarity	NPC244866
0.7639	Intermediate Similarity	NPC91953
0.7626	Intermediate Similarity	NPC469549
0.7615	Intermediate Similarity	NPC285350
0.7609	Intermediate Similarity	NPC288416
0.7606	Intermediate Similarity	NPC106406
0.7606	Intermediate Similarity	NPC68517
0.7589	Intermediate Similarity	NPC18074
0.7589	Intermediate Similarity	NPC5419
0.7589	Intermediate Similarity	NPC61
0.7589	Intermediate Similarity	NPC25581
0.7582	Intermediate Similarity	NPC471203
0.7578	Intermediate Similarity	NPC183700
0.7576	Intermediate Similarity	NPC200988
0.7576	Intermediate Similarity	NPC175799
0.7576	Intermediate Similarity	NPC325295
0.7576	Intermediate Similarity	NPC610
0.7576	Intermediate Similarity	NPC145023
0.7576	Intermediate Similarity	NPC76308
0.7569	Intermediate Similarity	NPC67349
0.7569	Intermediate Similarity	NPC279676
0.7569	Intermediate Similarity	NPC197921
0.7557	Intermediate Similarity	NPC23402
0.7556	Intermediate Similarity	NPC474862
0.7552	Intermediate Similarity	NPC182217
0.7552	Intermediate Similarity	NPC233350
0.7552	Intermediate Similarity	NPC180171
0.7552	Intermediate Similarity	NPC113295
0.7552	Intermediate Similarity	NPC103398
0.7552	Intermediate Similarity	NPC158325
0.7552	Intermediate Similarity	NPC70680
0.754	Intermediate Similarity	NPC70843
0.754	Intermediate Similarity	NPC188677
0.7537	Intermediate Similarity	NPC265454
0.7537	Intermediate Similarity	NPC34634
0.7535	Intermediate Similarity	NPC168799
0.7535	Intermediate Similarity	NPC155209
0.752	Intermediate Similarity	NPC261573
0.752	Intermediate Similarity	NPC120693
0.752	Intermediate Similarity	NPC8931
0.7518	Intermediate Similarity	NPC288945
0.7518	Intermediate Similarity	NPC231767
0.7518	Intermediate Similarity	NPC198388
0.7517	Intermediate Similarity	NPC283560
0.7517	Intermediate Similarity	NPC24295
0.7517	Intermediate Similarity	NPC469360
0.75	Intermediate Similarity	NPC91461
0.75	Intermediate Similarity	NPC7686
0.75	Intermediate Similarity	NPC301651
0.75	Intermediate Similarity	NPC241354
0.75	Intermediate Similarity	NPC40258
0.75	Intermediate Similarity	NPC473556
0.7483	Intermediate Similarity	NPC148080
0.7483	Intermediate Similarity	NPC469623
0.7483	Intermediate Similarity	NPC6913
0.7482	Intermediate Similarity	NPC296712
0.7481	Intermediate Similarity	NPC201402
0.7481	Intermediate Similarity	NPC98305
0.7481	Intermediate Similarity	NPC469703
0.7481	Intermediate Similarity	NPC160854
0.7481	Intermediate Similarity	NPC469704
0.748	Intermediate Similarity	NPC245561
0.7466	Intermediate Similarity	NPC156709
0.7466	Intermediate Similarity	NPC179505
0.7463	Intermediate Similarity	NPC182240
0.7463	Intermediate Similarity	NPC319950
0.7451	Intermediate Similarity	NPC212699
0.7451	Intermediate Similarity	NPC207675
0.745	Intermediate Similarity	NPC132771
0.7448	Intermediate Similarity	NPC469696
0.7447	Intermediate Similarity	NPC326966
0.7438	Intermediate Similarity	NPC26108
0.7432	Intermediate Similarity	NPC478250
0.7429	Intermediate Similarity	NPC217431
0.7426	Intermediate Similarity	NPC27581
0.7426	Intermediate Similarity	NPC469686
0.7424	Intermediate Similarity	NPC51345
0.7422	Intermediate Similarity	NPC317305
0.7419	Intermediate Similarity	NPC213730
0.7419	Intermediate Similarity	NPC52472
0.7415	Intermediate Similarity	NPC100675
0.7413	Intermediate Similarity	NPC471749
0.7407	Intermediate Similarity	NPC473136
0.7405	Intermediate Similarity	NPC148969
0.7402	Intermediate Similarity	NPC92623
0.7402	Intermediate Similarity	NPC29989
0.7402	Intermediate Similarity	NPC69332
0.7402	Intermediate Similarity	NPC135464
0.7402	Intermediate Similarity	NPC95178
0.7397	Intermediate Similarity	NPC142703
0.7397	Intermediate Similarity	NPC37250
0.7397	Intermediate Similarity	NPC219428
0.7397	Intermediate Similarity	NPC152942
0.7397	Intermediate Similarity	NPC302857
0.7397	Intermediate Similarity	NPC278068
0.7394	Intermediate Similarity	NPC478255
0.7394	Intermediate Similarity	NPC318799
0.7394	Intermediate Similarity	NPC46137
0.7394	Intermediate Similarity	NPC235294
0.7388	Intermediate Similarity	NPC63126
0.7376	Intermediate Similarity	NPC214246
0.7372	Intermediate Similarity	NPC471067
0.7372	Intermediate Similarity	NPC86900
0.7372	Intermediate Similarity	NPC52097
0.7368	Intermediate Similarity	NPC148055
0.7365	Intermediate Similarity	NPC224389
0.7365	Intermediate Similarity	NPC206095
0.7365	Intermediate Similarity	NPC471027
0.7365	Intermediate Similarity	NPC477335
0.7365	Intermediate Similarity	NPC297517
0.7365	Intermediate Similarity	NPC35702
0.7365	Intermediate Similarity	NPC13818
0.7364	Intermediate Similarity	NPC88141
0.7361	Intermediate Similarity	NPC169398
0.7353	Intermediate Similarity	NPC476872
0.7353	Intermediate Similarity	NPC470848
0.7353	Intermediate Similarity	NPC470849
0.7348	Intermediate Similarity	NPC157338
0.7348	Intermediate Similarity	NPC221870
0.7347	Intermediate Similarity	NPC274891
0.7347	Intermediate Similarity	NPC205751
0.7347	Intermediate Similarity	NPC295492
0.7347	Intermediate Similarity	NPC476819
0.7347	Intermediate Similarity	NPC303683
0.7347	Intermediate Similarity	NPC26241
0.7347	Intermediate Similarity	NPC474875
0.7347	Intermediate Similarity	NPC476820
0.7344	Intermediate Similarity	NPC260952
0.7339	Intermediate Similarity	NPC132078
0.7339	Intermediate Similarity	NPC216468
0.7339	Intermediate Similarity	NPC78119
0.7339	Intermediate Similarity	NPC51333
0.7338	Intermediate Similarity	NPC280767
0.7338	Intermediate Similarity	NPC127975
0.7338	Intermediate Similarity	NPC83218
0.7338	Intermediate Similarity	NPC126991
0.7333	Intermediate Similarity	NPC263386
0.7333	Intermediate Similarity	NPC141791
0.7329	Intermediate Similarity	NPC308976
0.7325	Intermediate Similarity	NPC63931
0.7324	Intermediate Similarity	NPC329344
0.7324	Intermediate Similarity	NPC217052
0.7324	Intermediate Similarity	NPC237506
0.7324	Intermediate Similarity	NPC32626
0.7323	Intermediate Similarity	NPC154899
0.7323	Intermediate Similarity	NPC233396
0.7323	Intermediate Similarity	NPC13495
0.7319	Intermediate Similarity	NPC232454
0.7319	Intermediate Similarity	NPC470907
0.7319	Intermediate Similarity	NPC178449
0.7315	Intermediate Similarity	NPC319628
0.7315	Intermediate Similarity	NPC277315
0.7315	Intermediate Similarity	NPC37331
0.7315	Intermediate Similarity	NPC303090
0.7315	Intermediate Similarity	NPC284948
0.7315	Intermediate Similarity	NPC472016
0.7315	Intermediate Similarity	NPC43158
0.7315	Intermediate Similarity	NPC220664

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 NPC275538 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	128
0.1-0.2	508
0.2-0.3	1162
0.3-0.4	2380
0.4-0.5	2585
0.5-0.6	1794
0.6-0.7	567
0.7-0.8	26
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
0.7626	Intermediate Similarity	NPD3136	Phase 2
0.7603	Intermediate Similarity	NPD3400	Discontinued
0.7518	Intermediate Similarity	NPD6233	Phase 2
0.7397	Intermediate Similarity	NPD7978	Discontinued
0.7388	Intermediate Similarity	NPD1759	Phase 1
0.7353	Intermediate Similarity	NPD3421	Phase 3
0.7347	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6798	Discontinued
0.7315	Intermediate Similarity	NPD6190	Approved
0.7313	Intermediate Similarity	NPD1758	Phase 1
0.7273	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4062	Phase 3
0.7226	Intermediate Similarity	NPD3847	Discontinued
0.7222	Intermediate Similarity	NPD825	Approved
0.7222	Intermediate Similarity	NPD826	Approved
0.7174	Intermediate Similarity	NPD1535	Discovery
0.7172	Intermediate Similarity	NPD6355	Discontinued
0.7164	Intermediate Similarity	NPD255	Approved
0.7164	Intermediate Similarity	NPD256	Approved
0.7133	Intermediate Similarity	NPD4738	Phase 2
0.7132	Intermediate Similarity	NPD1894	Discontinued
0.7122	Intermediate Similarity	NPD1481	Phase 2
0.7111	Intermediate Similarity	NPD9568	Approved
0.7097	Intermediate Similarity	NPD3455	Phase 2
0.7095	Intermediate Similarity	NPD2438	Suspended
0.7095	Intermediate Similarity	NPD2239	Approved
0.7095	Intermediate Similarity	NPD9570	Approved
0.7095	Intermediate Similarity	NPD2240	Approved
0.709	Intermediate Similarity	NPD2629	Approved
0.7068	Intermediate Similarity	NPD821	Approved
0.7067	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD555	Phase 2
0.7047	Intermediate Similarity	NPD7266	Discontinued
0.7027	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4628	Phase 3
0.7016	Intermediate Similarity	NPD2934	Approved
0.7016	Intermediate Similarity	NPD2933	Approved
0.7006	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD9495	Approved
0.698	Remote Similarity	NPD7450	Phase 2
0.6978	Remote Similarity	NPD4136	Approved
0.6978	Remote Similarity	NPD4135	Approved
0.6978	Remote Similarity	NPD4106	Approved
0.6966	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD8019	Approved
0.696	Remote Similarity	NPD2859	Approved
0.696	Remote Similarity	NPD2860	Approved
0.6948	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2614	Approved
0.6935	Remote Similarity	NPD1066	Discontinued
0.6933	Remote Similarity	NPD7608	Discontinued
0.6923	Remote Similarity	NPD258	Approved
0.6923	Remote Similarity	NPD257	Approved
0.6918	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD520	Approved
0.6918	Remote Similarity	NPD6663	Approved
0.6918	Remote Similarity	NPD7972	Discontinued
0.6918	Remote Similarity	NPD259	Phase 1
0.6908	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4110	Phase 3
0.6906	Remote Similarity	NPD5305	Approved
0.6906	Remote Similarity	NPD5306	Approved
0.6884	Remote Similarity	NPD9545	Approved
0.6875	Remote Similarity	NPD5736	Approved
0.6875	Remote Similarity	NPD9569	Approved
0.687	Remote Similarity	NPD467	Phase 1
0.6867	Remote Similarity	NPD1537	Approved
0.6867	Remote Similarity	NPD1519	Approved
0.6867	Remote Similarity	NPD1538	Phase 1
0.6855	Remote Similarity	NPD7495	Discontinued
0.6853	Remote Similarity	NPD2626	Approved
0.6853	Remote Similarity	NPD2159	Approved
0.6853	Remote Similarity	NPD2160	Approved
0.6853	Remote Similarity	NPD2625	Approved
0.6853	Remote Similarity	NPD2627	Approved
0.6853	Remote Similarity	NPD2628	Approved
0.6839	Remote Similarity	NPD3536	Discontinued
0.6835	Remote Similarity	NPD4102	Approved
0.6835	Remote Similarity	NPD4105	Approved
0.6831	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4807	Approved
0.6809	Remote Similarity	NPD4806	Approved
0.6806	Remote Similarity	NPD5647	Approved
0.6797	Remote Similarity	NPD3020	Approved
0.6795	Remote Similarity	NPD6390	Discontinued
0.6792	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6653	Approved
0.6776	Remote Similarity	NPD5958	Discontinued
0.6776	Remote Similarity	NPD4534	Discontinued
0.6774	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5204	Approved
0.6757	Remote Similarity	NPD2979	Phase 3
0.6757	Remote Similarity	NPD4060	Phase 1
0.6755	Remote Similarity	NPD4476	Approved
0.6755	Remote Similarity	NPD2935	Discontinued
0.6755	Remote Similarity	NPD5712	Approved
0.6755	Remote Similarity	NPD1523	Approved
0.6755	Remote Similarity	NPD6032	Approved
0.6755	Remote Similarity	NPD4477	Approved
0.6755	Remote Similarity	NPD1522	Approved
0.6752	Remote Similarity	NPD7523	Phase 3
0.675	Remote Similarity	NPD4433	Discontinued
0.6746	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2797	Approved
0.6735	Remote Similarity	NPD3764	Approved
0.6735	Remote Similarity	NPD1048	Approved
0.6733	Remote Similarity	NPD7097	Phase 1
0.6733	Remote Similarity	NPD1536	Approved
0.6731	Remote Similarity	NPD3985	Discontinued
0.673	Remote Similarity	NPD6502	Phase 2
0.673	Remote Similarity	NPD4380	Phase 2
0.6716	Remote Similarity	NPD3021	Approved
0.6716	Remote Similarity	NPD3022	Approved
0.6712	Remote Similarity	NPD4617	Approved
0.6712	Remote Similarity	NPD4620	Approved
0.6712	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5203	Approved
0.6712	Remote Similarity	NPD5201	Approved
0.6711	Remote Similarity	NPD274	Approved
0.6711	Remote Similarity	NPD275	Approved
0.6708	Remote Similarity	NPD8455	Phase 2
0.6706	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7843	Approved
0.669	Remote Similarity	NPD7451	Discontinued
0.669	Remote Similarity	NPD6287	Discontinued
0.6689	Remote Similarity	NPD1423	Approved
0.6689	Remote Similarity	NPD7033	Discontinued
0.6688	Remote Similarity	NPD8166	Discontinued
0.6687	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6677	Suspended
0.6667	Remote Similarity	NPD5048	Discontinued
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD196	Phase 1
0.6667	Remote Similarity	NPD3027	Phase 3
0.6667	Remote Similarity	NPD2424	Discontinued
0.6667	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5163	Phase 2
0.6667	Remote Similarity	NPD7798	Approved
0.6667	Remote Similarity	NPD9536	Phase 1
0.6667	Remote Similarity	NPD9537	Phase 1
0.6646	Remote Similarity	NPD7131	Phase 3
0.6646	Remote Similarity	NPD5403	Approved
0.6645	Remote Similarity	NPD4172	Approved
0.6645	Remote Similarity	NPD4173	Approved
0.6644	Remote Similarity	NPD6310	Approved
0.6644	Remote Similarity	NPD6346	Approved
0.6644	Remote Similarity	NPD6311	Approved
0.6644	Remote Similarity	NPD6309	Approved
0.6643	Remote Similarity	NPD2561	Approved
0.6643	Remote Similarity	NPD2562	Approved
0.6642	Remote Similarity	NPD2684	Approved
0.6626	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3555	Approved
0.6623	Remote Similarity	NPD1520	Approved
0.6623	Remote Similarity	NPD3554	Approved
0.6623	Remote Similarity	NPD3553	Approved
0.6623	Remote Similarity	NPD1521	Approved
0.6623	Remote Similarity	NPD3552	Approved
0.6622	Remote Similarity	NPD4619	Approved
0.6622	Remote Similarity	NPD4621	Approved
0.6622	Remote Similarity	NPD3268	Approved
0.6621	Remote Similarity	NPD1203	Approved
0.6621	Remote Similarity	NPD1164	Approved
0.6619	Remote Similarity	NPD9493	Approved
0.6611	Remote Similarity	NPD7565	Approved
0.6604	Remote Similarity	NPD4003	Phase 3
0.66	Remote Similarity	NPD230	Phase 1
0.6599	Remote Similarity	NPD6832	Phase 2
0.6597	Remote Similarity	NPD4659	Approved
0.6597	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5981	Approved
0.6593	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.659	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7075	Discontinued
0.6584	Remote Similarity	NPD3274	Phase 2
0.6577	Remote Similarity	NPD6405	Approved
0.6577	Remote Similarity	NPD6407	Approved
0.6575	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5535	Approved
0.6567	Remote Similarity	NPD1358	Approved
0.6561	Remote Similarity	NPD6799	Approved
0.6556	Remote Similarity	NPD5314	Approved
0.6552	Remote Similarity	NPD1283	Approved
0.6549	Remote Similarity	NPD2932	Approved
0.6549	Remote Similarity	NPD3019	Approved
0.6547	Remote Similarity	NPD7157	Approved
0.6545	Remote Similarity	NPD6234	Discontinued
0.6543	Remote Similarity	NPD37	Approved
0.6543	Remote Similarity	NPD6801	Discontinued
0.6533	Remote Similarity	NPD5121	Approved
0.6533	Remote Similarity	NPD3059	Approved
0.6533	Remote Similarity	NPD3061	Approved
0.6533	Remote Similarity	NPD3062	Approved
0.6533	Remote Similarity	NPD5120	Approved

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