NPASS Compound

Structure

NPC244866 OpenBabel07101718182D 45 47 0 0 1 0 0 0 0 0999 V2000 -4.3301 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -7.5000 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 -1.7321 -7.0000 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 -7.7942 0.5000 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 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 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 0.0000 -4.0000 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 -1.7321 -0.0000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 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 -1.7321 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 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 -0.8660 -4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 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 0.0000 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 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 -6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 4 7 1 0 0 0 0 5 10 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 26 2 0 0 0 0 9 26 1 0 0 0 0 10 32 1 0 0 0 0 11 17 1 0 0 0 0 11 24 2 0 0 0 0 12 18 2 0 0 0 0 12 24 1 0 0 0 0 13 19 1 0 0 0 0 13 25 2 0 0 0 0 14 20 2 0 0 0 0 14 25 1 0 0 0 0 15 21 1 0 0 0 0 15 24 1 0 0 0 0 16 22 1 0 0 0 0 16 25 1 0 0 0 0 17 27 2 0 0 0 0 18 27 1 0 0 0 0 19 28 2 0 0 0 0 20 28 1 0 0 0 0 23 26 1 0 0 0 0 27 39 1 0 0 0 0 28 40 1 0 0 0 0 29 21 1 1 0 0 0 29 33 1 0 0 0 0 29 36 1 0 0 0 0 30 22 1 6 0 0 0 30 34 1 0 0 0 0 30 37 1 0 0 0 0 31 23 1 1 0 0 0 31 35 1 0 0 0 0 31 38 1 0 0 0 0 32 36 2 3 0 0 0 32 41 1 0 0 0 0 33 37 2 3 0 0 0 33 42 1 0 0 0 0 34 38 2 3 0 0 0 34 43 1 0 0 0 0 35 44 2 0 0 0 0 35 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	617.31
Volume:	648.494
LogP:	3.976
LogD:	3.748
LogS:	-3.85
# Rotatable Bonds:	21
TPSA:	165.06
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.117
Synthetic Accessibility Score:	3.384
Fsp3:	0.371
Lipinski Rule-of-5:	Rejected
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:	-5.697
MDCK Permeability:	1.2315206731727812e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.974
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	98.42443084716797%
Volume Distribution (VD):	0.477
Pgp-substrate:	0.6478725671768188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.037
CYP2C19-inhibitor:	0.367
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.909
CYP2C9-substrate:	0.978
CYP2D6-inhibitor:	0.17
CYP2D6-substrate:	0.382
CYP3A4-inhibitor:	0.858
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	2.207
Half-life (T1/2):	0.924

ADMET: Toxicity

hERG Blockers:	0.187
Human Hepatotoxicity (H-HT):	0.696
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.973
Maximum Recommended Daily Dose:	0.097
Skin Sensitization:	0.145
Carcinogencity:	0.048
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.011

Download Data

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

Natural Product: NPC244866

Natural Product ID:	NPC244866
*Common Name:**	Spiroidesin
IUPAC Name:	(2R)-2-[[(2S)-2-[[(2R)-2-(hexanoylamino)-4-(4-hydroxyphenyl)butanoyl]amino]-4-(4-hydroxyphenyl)butanoyl]amino]-3-phenylpropanoic acid
Synonyms:	Spiroidesin
Standard InCHIKey:	XFLVJFHNXBWJDL-MJSOWUPRSA-N
Standard InCHI:	InChI=1S/C35H43N3O7/c1-2-3-5-10-32(41)36-29(21-15-24-11-17-27(39)18-12-24)33(42)37-30(22-16-25-13-19-28(40)20-14-25)34(43)38-31(35(44)45)23-26-8-6-4-7-9-26/h4,6-9,11-14,17-20,29-31,39-40H,2-3,5,10,15-16,21-23H2,1H3,(H,36,41)(H,37,42)(H,38,43)(H,44,45)/t29-,30+,31-/m1/s1
SMILES:	CCCCCC(=N[C@H](CCc1ccc(cc1)O)C(=N[C@@H](CCc1ccc(cc1)O)C(=N[C@H](Cc1ccccc1)C(=O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453142
PubChem CID:	637849
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:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO32720	anabaena spiroides	Species	0stocaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12088439]

☑ 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	2

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6489	Organism	Microcystis aeruginosa NIES-88	Microcystis aeruginosa NIES-88	IC50	=	1600.0	nM	PMID[543441]
NPT2	Others	Unspecified		IC50	=	10000.0	nM	PMID[543441]

☑ 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 NPC244866 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	150
0.1-0.2	895
0.2-0.3	3601
0.3-0.4	12402
0.4-0.5	7206
0.5-0.6	14593
0.6-0.7	3403
0.7-0.8	388
0.8-0.85	44
0.85-0.9	10
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9141	High Similarity	NPC325651
0.9	High Similarity	NPC326966
0.8952	High Similarity	NPC319950
0.8769	High Similarity	NPC296712
0.874	High Similarity	NPC27581
0.8712	High Similarity	NPC45191
0.8702	High Similarity	NPC478147
0.8594	High Similarity	NPC142577
0.8593	High Similarity	NPC6913
0.8492	Intermediate Similarity	NPC311737
0.8492	Intermediate Similarity	NPC38458
0.8483	Intermediate Similarity	NPC56635
0.845	Intermediate Similarity	NPC474862
0.8413	Intermediate Similarity	NPC82963
0.8409	Intermediate Similarity	NPC476353
0.8397	Intermediate Similarity	NPC4974
0.8392	Intermediate Similarity	NPC233702
0.8333	Intermediate Similarity	NPC317254
0.8321	Intermediate Similarity	NPC6570
0.8267	Intermediate Similarity	NPC471771
0.8267	Intermediate Similarity	NPC290755
0.8267	Intermediate Similarity	NPC304074
0.8239	Intermediate Similarity	NPC16188
0.8214	Intermediate Similarity	NPC91953
0.82	Intermediate Similarity	NPC223207
0.8145	Intermediate Similarity	NPC258056
0.8143	Intermediate Similarity	NPC197921
0.8134	Intermediate Similarity	NPC199738
0.8134	Intermediate Similarity	NPC210950
0.8125	Intermediate Similarity	NPC188867
0.8125	Intermediate Similarity	NPC106551
0.8125	Intermediate Similarity	NPC281686
0.811	Intermediate Similarity	NPC118202
0.8102	Intermediate Similarity	NPC470392
0.8085	Intermediate Similarity	NPC469360
0.8077	Intermediate Similarity	NPC283760
0.8029	Intermediate Similarity	NPC257390
0.8	Intermediate Similarity	NPC475544
0.8	Intermediate Similarity	NPC469243
0.8	Intermediate Similarity	NPC132771
0.7959	Intermediate Similarity	NPC202198
0.7939	Intermediate Similarity	NPC239697
0.7937	Intermediate Similarity	NPC474149
0.792	Intermediate Similarity	NPC96224
0.792	Intermediate Similarity	NPC24101
0.7903	Intermediate Similarity	NPC231705
0.7898	Intermediate Similarity	NPC196243
0.7891	Intermediate Similarity	NPC309808
0.7887	Intermediate Similarity	NPC476989
0.7842	Intermediate Similarity	NPC328070
0.784	Intermediate Similarity	NPC142297
0.7834	Intermediate Similarity	NPC155506
0.7834	Intermediate Similarity	NPC159767
0.782	Intermediate Similarity	NPC56634
0.7817	Intermediate Similarity	NPC322526
0.7817	Intermediate Similarity	NPC48202
0.7817	Intermediate Similarity	NPC471201
0.7803	Intermediate Similarity	NPC268572
0.7793	Intermediate Similarity	NPC81026
0.7778	Intermediate Similarity	NPC153690
0.7748	Intermediate Similarity	NPC212699
0.7748	Intermediate Similarity	NPC207675
0.7746	Intermediate Similarity	NPC313694
0.7746	Intermediate Similarity	NPC473055
0.7746	Intermediate Similarity	NPC242159
0.7746	Intermediate Similarity	NPC473052
0.7742	Intermediate Similarity	NPC328649
0.7742	Intermediate Similarity	NPC141957
0.7733	Intermediate Similarity	NPC473580
0.7727	Intermediate Similarity	NPC63931
0.7727	Intermediate Similarity	NPC142638
0.7727	Intermediate Similarity	NPC317784
0.7724	Intermediate Similarity	NPC266741
0.7721	Intermediate Similarity	NPC47667
0.7707	Intermediate Similarity	NPC89831
0.7707	Intermediate Similarity	NPC230611
0.7687	Intermediate Similarity	NPC326079
0.7681	Intermediate Similarity	NPC161593
0.7681	Intermediate Similarity	NPC145888
0.7681	Intermediate Similarity	NPC16031
0.7662	Intermediate Similarity	NPC289776
0.7662	Intermediate Similarity	NPC191863
0.7662	Intermediate Similarity	NPC133470
0.7661	Intermediate Similarity	NPC178902
0.7658	Intermediate Similarity	NPC137627
0.7658	Intermediate Similarity	NPC306804
0.7656	Intermediate Similarity	NPC319579
0.7643	Intermediate Similarity	NPC198254
0.7643	Intermediate Similarity	NPC246913
0.7643	Intermediate Similarity	NPC275538
0.7643	Intermediate Similarity	NPC276506
0.7643	Intermediate Similarity	NPC274198
0.7628	Intermediate Similarity	NPC107938
0.7628	Intermediate Similarity	NPC294516
0.7612	Intermediate Similarity	NPC190663
0.761	Intermediate Similarity	NPC476227
0.761	Intermediate Similarity	NPC279871
0.761	Intermediate Similarity	NPC473402
0.7607	Intermediate Similarity	NPC294951
0.7597	Intermediate Similarity	NPC163674
0.7597	Intermediate Similarity	NPC241794
0.7594	Intermediate Similarity	NPC122009
0.7589	Intermediate Similarity	NPC88667
0.7584	Intermediate Similarity	NPC473491
0.7571	Intermediate Similarity	NPC120251
0.7564	Intermediate Similarity	NPC61004
0.755	Intermediate Similarity	NPC39431
0.7538	Intermediate Similarity	NPC474584
0.7535	Intermediate Similarity	NPC267237
0.7532	Intermediate Similarity	NPC40234
0.7519	Intermediate Similarity	NPC283468
0.7519	Intermediate Similarity	NPC169328
0.75	Intermediate Similarity	NPC26108
0.75	Intermediate Similarity	NPC160493
0.75	Intermediate Similarity	NPC136797
0.75	Intermediate Similarity	NPC31274
0.75	Intermediate Similarity	NPC473354
0.75	Intermediate Similarity	NPC158277
0.7483	Intermediate Similarity	NPC473360
0.7483	Intermediate Similarity	NPC106183
0.7482	Intermediate Similarity	NPC321561
0.748	Intermediate Similarity	NPC70843
0.748	Intermediate Similarity	NPC188677
0.7469	Intermediate Similarity	NPC194671
0.7469	Intermediate Similarity	NPC269750
0.7469	Intermediate Similarity	NPC45037
0.7468	Intermediate Similarity	NPC287757
0.7468	Intermediate Similarity	NPC319320
0.7463	Intermediate Similarity	NPC310467
0.7462	Intermediate Similarity	NPC227553
0.746	Intermediate Similarity	NPC8931
0.746	Intermediate Similarity	NPC261573
0.746	Intermediate Similarity	NPC120693
0.7445	Intermediate Similarity	NPC35996
0.7439	Intermediate Similarity	NPC471526
0.7438	Intermediate Similarity	NPC273755
0.7438	Intermediate Similarity	NPC248670
0.7425	Intermediate Similarity	NPC234069
0.7423	Intermediate Similarity	NPC32064
0.7419	Intermediate Similarity	NPC245561
0.7419	Intermediate Similarity	NPC12730
0.7407	Intermediate Similarity	NPC42657
0.7407	Intermediate Similarity	NPC43275
0.74	Intermediate Similarity	NPC245974
0.7397	Intermediate Similarity	NPC259800
0.7397	Intermediate Similarity	NPC318984
0.7397	Intermediate Similarity	NPC318028
0.7397	Intermediate Similarity	NPC328137
0.7397	Intermediate Similarity	NPC282087
0.7397	Intermediate Similarity	NPC317741
0.7397	Intermediate Similarity	NPC241086
0.7391	Intermediate Similarity	NPC164608
0.7383	Intermediate Similarity	NPC247298
0.7381	Intermediate Similarity	NPC174122
0.7381	Intermediate Similarity	NPC163961
0.7381	Intermediate Similarity	NPC473305
0.7381	Intermediate Similarity	NPC64140
0.7368	Intermediate Similarity	NPC5194
0.7368	Intermediate Similarity	NPC56685
0.7368	Intermediate Similarity	NPC261934
0.7368	Intermediate Similarity	NPC262166
0.736	Intermediate Similarity	NPC52472
0.7347	Intermediate Similarity	NPC168861
0.7346	Intermediate Similarity	NPC50016
0.7344	Intermediate Similarity	NPC95178
0.7344	Intermediate Similarity	NPC69332
0.7344	Intermediate Similarity	NPC29989
0.7333	Intermediate Similarity	NPC5462
0.7333	Intermediate Similarity	NPC9373
0.7329	Intermediate Similarity	NPC214988
0.7324	Intermediate Similarity	NPC474091
0.7317	Intermediate Similarity	NPC153554
0.731	Intermediate Similarity	NPC64205
0.7308	Intermediate Similarity	NPC88141
0.7299	Intermediate Similarity	NPC284078
0.7296	Intermediate Similarity	NPC209463
0.7293	Intermediate Similarity	NPC142599
0.7286	Intermediate Similarity	NPC137416
0.7284	Intermediate Similarity	NPC227778
0.7284	Intermediate Similarity	NPC471165
0.7279	Intermediate Similarity	NPC326860
0.7279	Intermediate Similarity	NPC197239
0.7273	Intermediate Similarity	NPC476268
0.7273	Intermediate Similarity	NPC48909
0.7273	Intermediate Similarity	NPC114102
0.7273	Intermediate Similarity	NPC476321
0.7266	Intermediate Similarity	NPC307020
0.7266	Intermediate Similarity	NPC13495
0.7262	Intermediate Similarity	NPC94862
0.7259	Intermediate Similarity	NPC471926
0.7254	Intermediate Similarity	NPC271808
0.7252	Intermediate Similarity	NPC21162
0.7248	Intermediate Similarity	NPC222039
0.7248	Intermediate Similarity	NPC100478
0.7246	Intermediate Similarity	NPC138083
0.7244	Intermediate Similarity	NPC244336
0.7244	Intermediate Similarity	NPC164859
0.7237	Intermediate Similarity	NPC324081
0.7234	Intermediate Similarity	NPC305717
0.723	Intermediate Similarity	NPC33011

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 NPC244866 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	122
0.1-0.2	488
0.2-0.3	800
0.3-0.4	1744
0.4-0.5	2684
0.5-0.6	2380
0.6-0.7	838
0.7-0.8	80
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8815	High Similarity	NPD7450	Phase 2
0.8496	Intermediate Similarity	NPD3136	Phase 2
0.8467	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD8019	Approved
0.8409	Intermediate Similarity	NPD7451	Discontinued
0.837	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD9568	Approved
0.8125	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD7978	Discontinued
0.8043	Intermediate Similarity	NPD6346	Approved
0.8042	Intermediate Similarity	NPD3400	Discontinued
0.8	Intermediate Similarity	NPD1759	Phase 1
0.7933	Intermediate Similarity	NPD7495	Discontinued
0.7923	Intermediate Similarity	NPD1758	Phase 1
0.7907	Intermediate Similarity	NPD255	Approved
0.7907	Intermediate Similarity	NPD256	Approved
0.7838	Intermediate Similarity	NPD7523	Phase 3
0.7704	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD9569	Approved
0.7656	Intermediate Similarity	NPD3642	Approved
0.7656	Intermediate Similarity	NPD3644	Approved
0.7656	Intermediate Similarity	NPD3643	Approved
0.7651	Intermediate Similarity	NPD6390	Discontinued
0.7589	Intermediate Similarity	NPD259	Phase 1
0.7518	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7131	Phase 3
0.7483	Intermediate Similarity	NPD555	Phase 2
0.7482	Intermediate Similarity	NPD257	Approved
0.7482	Intermediate Similarity	NPD258	Approved
0.7451	Intermediate Similarity	NPD6502	Phase 2
0.745	Intermediate Similarity	NPD7554	Discontinued
0.7447	Intermediate Similarity	NPD9537	Phase 1
0.7447	Intermediate Similarity	NPD9536	Phase 1
0.7445	Intermediate Similarity	NPD6624	Discontinued
0.7432	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7608	Discontinued
0.7405	Intermediate Similarity	NPD6746	Phase 2
0.7397	Intermediate Similarity	NPD1519	Approved
0.7397	Intermediate Similarity	NPD1537	Approved
0.7397	Intermediate Similarity	NPD1538	Phase 1
0.7348	Intermediate Similarity	NPD2228	Approved
0.7348	Intermediate Similarity	NPD2234	Approved
0.7348	Intermediate Similarity	NPD2229	Approved
0.7347	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD196	Phase 1
0.7308	Intermediate Similarity	NPD7972	Discontinued
0.7303	Intermediate Similarity	NPD7303	Discontinued
0.7299	Intermediate Similarity	NPD3421	Phase 3
0.7292	Intermediate Similarity	NPD826	Approved
0.7292	Intermediate Similarity	NPD825	Approved
0.729	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1522	Approved
0.7279	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4093	Discontinued
0.7279	Intermediate Similarity	NPD1523	Approved
0.7273	Intermediate Similarity	NPD3455	Phase 2
0.7266	Intermediate Similarity	NPD4659	Approved
0.726	Intermediate Similarity	NPD1536	Approved
0.7254	Intermediate Similarity	NPD2614	Approved
0.7241	Intermediate Similarity	NPD275	Approved
0.7241	Intermediate Similarity	NPD274	Approved
0.7237	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD8303	Discontinued
0.7222	Intermediate Similarity	NPD7477	Discontinued
0.7194	Intermediate Similarity	NPD2562	Approved
0.7194	Intermediate Similarity	NPD2561	Approved
0.7188	Intermediate Similarity	NPD9610	Approved
0.7188	Intermediate Similarity	NPD9608	Approved
0.7183	Intermediate Similarity	NPD7828	Discontinued
0.7163	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4103	Phase 2
0.7162	Intermediate Similarity	NPD9570	Approved
0.7152	Intermediate Similarity	NPD7695	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1520	Approved
0.7143	Intermediate Similarity	NPD1521	Approved
0.7133	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1040	Phase 2
0.7117	Intermediate Similarity	NPD5822	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1348	Approved
0.7108	Intermediate Similarity	NPD5445	Approved
0.7105	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7714	Approved
0.7103	Intermediate Similarity	NPD7715	Approved
0.7097	Intermediate Similarity	NPD2933	Approved
0.7097	Intermediate Similarity	NPD2934	Approved
0.7083	Intermediate Similarity	NPD9718	Approved
0.708	Intermediate Similarity	NPD2218	Phase 2
0.708	Intermediate Similarity	NPD5303	Approved
0.708	Intermediate Similarity	NPD5304	Approved
0.708	Intermediate Similarity	NPD2217	Approved
0.7071	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD3847	Discontinued
0.7047	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3053	Approved
0.7042	Intermediate Similarity	NPD3055	Approved
0.704	Intermediate Similarity	NPD2859	Approved
0.704	Intermediate Similarity	NPD2860	Approved
0.7039	Intermediate Similarity	NPD7740	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5981	Approved
0.7027	Intermediate Similarity	NPD3553	Approved
0.7027	Intermediate Similarity	NPD3552	Approved
0.7027	Intermediate Similarity	NPD3555	Approved
0.7027	Intermediate Similarity	NPD3554	Approved
0.7025	Intermediate Similarity	NPD5356	Approved
0.7025	Intermediate Similarity	NPD5355	Approved
0.7021	Intermediate Similarity	NPD1755	Approved
0.7008	Intermediate Similarity	NPD3020	Approved
0.7006	Intermediate Similarity	NPD7959	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5745	Approved
0.6978	Remote Similarity	NPD3019	Approved
0.6978	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7861	Discontinued
0.6972	Remote Similarity	NPD5311	Approved
0.6972	Remote Similarity	NPD5310	Approved
0.6968	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4738	Phase 2
0.6966	Remote Similarity	NPD5155	Approved
0.6966	Remote Similarity	NPD5156	Approved
0.6964	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2098	Approved
0.6954	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3764	Approved
0.6917	Remote Similarity	NPD1792	Phase 2
0.6908	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6583	Phase 3
0.6901	Remote Similarity	NPD6582	Phase 2
0.6901	Remote Similarity	NPD1669	Approved
0.6897	Remote Similarity	NPD2605	Approved
0.6897	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2606	Approved
0.689	Remote Similarity	NPD6747	Phase 1
0.6887	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD317	Approved
0.6884	Remote Similarity	NPD318	Approved
0.6875	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6584	Phase 3
0.6871	Remote Similarity	NPD6663	Approved
0.6867	Remote Similarity	NPD6865	Phase 2
0.6867	Remote Similarity	NPD6864	Phase 2
0.6857	Remote Similarity	NPD2932	Approved
0.6855	Remote Similarity	NPD7438	Suspended
0.6855	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3098	Discontinued
0.6853	Remote Similarity	NPD3125	Approved
0.6849	Remote Similarity	NPD5746	Approved
0.6846	Remote Similarity	NPD2568	Approved
0.6846	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5557	Phase 1
0.6835	Remote Similarity	NPD4479	Discontinued
0.6835	Remote Similarity	NPD5811	Approved
0.6832	Remote Similarity	NPD2097	Approved
0.6832	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2888	Approved
0.6829	Remote Similarity	NPD2890	Approved
0.6829	Remote Similarity	NPD2889	Approved
0.6829	Remote Similarity	NPD2017	Approved
0.6828	Remote Similarity	NPD3637	Approved
0.6828	Remote Similarity	NPD3636	Approved
0.6828	Remote Similarity	NPD5736	Approved
0.6828	Remote Similarity	NPD3635	Approved
0.6826	Remote Similarity	NPD3909	Discontinued
0.6821	Remote Similarity	NPD4476	Approved
0.6821	Remote Similarity	NPD4477	Approved
0.6818	Remote Similarity	NPD1444	Approved
0.6818	Remote Similarity	NPD8323	Discontinued
0.6818	Remote Similarity	NPD1445	Approved
0.6815	Remote Similarity	NPD7427	Discontinued
0.6813	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD3123	Discovery
0.6803	Remote Similarity	NPD6798	Discontinued
0.6803	Remote Similarity	NPD8011	Discontinued
0.6802	Remote Similarity	NPD6967	Phase 2
0.68	Remote Similarity	NPD6852	Discontinued
0.6795	Remote Similarity	NPD3536	Discontinued
0.6795	Remote Similarity	NPD4739	Approved
0.6791	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7773	Phase 2
0.6788	Remote Similarity	NPD9618	Approved
0.6788	Remote Similarity	NPD7315	Approved
0.6788	Remote Similarity	NPD4652	Approved
0.6788	Remote Similarity	NPD9614	Approved
0.6786	Remote Similarity	NPD4102	Approved
0.6786	Remote Similarity	NPD3965	Phase 1
0.6786	Remote Similarity	NPD4105	Approved
0.6781	Remote Similarity	NPD3594	Approved
0.6781	Remote Similarity	NPD3595	Approved
0.6774	Remote Similarity	NPD6667	Approved
0.6774	Remote Similarity	NPD6666	Approved
0.677	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD856	Approved
0.6763	Remote Similarity	NPD16	Approved
0.6761	Remote Similarity	NPD1535	Discovery

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