NPASS Compound

Structure

NPC475286 OpenBabel07101719252D 36 40 0 0 1 0 0 0 0 0999 V2000 4.2112 -2.6668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1092 -5.5507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6021 -8.2327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1931 -4.0681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7079 -6.3597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1409 -7.7327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8112 -5.2436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5893 -4.1211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1067 -3.6613 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7024 -6.4642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5531 -8.5417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9157 -4.2491 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.1247 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -4.8815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6021 -7.2327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6382 -4.4302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8292 -3.8424 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.9338 -2.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4706 -3.8870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7931 -6.6449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5893 -5.7392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4338 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2024 -7.3302 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 5.8622 -9.4928 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 7.8983 -6.6902 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.0215 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -5.3815 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.5531 -6.9237 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3841 -3.4803 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8976 -5.6504 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.1771 -4.9302 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.4338 -1.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.6382 -5.4302 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.7428 -2.2601 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6615 -3.2992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8795 -7.0516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 1 13 1 0 0 0 0 2 10 1 0 0 0 0 2 14 2 0 0 0 0 3 11 1 0 0 0 0 3 15 2 0 0 0 0 4 9 1 0 0 0 0 4 29 1 0 0 0 0 5 10 2 0 0 0 0 5 27 1 0 0 0 0 6 11 2 0 0 0 0 6 28 1 0 0 0 0 7 12 1 0 0 0 0 7 30 1 0 0 0 0 8 16 2 0 0 0 0 8 31 1 0 0 0 0 9 12 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 13 32 1 0 0 0 0 14 19 1 0 0 0 0 14 27 1 0 0 0 0 15 20 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 33 1 0 0 0 0 17 18 1 0 0 0 0 18 34 1 0 0 0 0 19 29 1 0 0 0 0 19 35 2 0 0 0 0 20 30 1 0 0 0 0 20 36 2 0 0 0 0 21 25 2 0 0 0 0 21 31 1 0 0 0 0 21 33 1 0 0 0 0 22 26 2 0 0 0 0 22 32 1 0 0 0 0 22 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	618.05
Volume:	486.037
LogP:	0.588
LogD:	1.479
LogS:	-3.627
# Rotatable Bonds:	9
TPSA:	200.64
# H-Bond Aceptor:	12
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.151
Synthetic Accessibility Score:	4.983
Fsp3:	0.273
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:	-5.817
MDCK Permeability:	4.176297352387337e-06
Pgp-inhibitor:	0.989
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.98
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.277

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.488
Plasma Protein Binding (PPB):	90.80856323242188%
Volume Distribution (VD):	0.6
Pgp-substrate:	24.035167694091797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.355
CYP2C19-inhibitor:	0.645
CYP2C19-substrate:	0.019
CYP2C9-inhibitor:	0.215
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.013
CYP3A4-inhibitor:	0.812
CYP3A4-substrate:	0.098

ADMET: Excretion

Clearance (CL):	2.646
Half-life (T1/2):	0.938

ADMET: Toxicity

hERG Blockers:	0.945
Human Hepatotoxicity (H-HT):	0.996
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.804
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.554
Carcinogencity:	0.174
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC475286

Natural Product ID:	NPC475286
*Common Name:**	Ageliferin
IUPAC Name:	n.a.
Synonyms:	Ageliferin
Standard InCHIKey:	DNQPQSFZLPZAIA-HHJICFAHSA-N
Standard InCHI:	InChI=1S/C22H24Br2N10O2.2C2HF3O2/c23-10-2-14(27-5-10)19(35)29-4-9-1-13-18(34-22(26)32-13)17(16-8-31-21(25)33-16)12(9)7-30-20(36)15-3-11(24)6-28-15;23-2(4,5)1(6)7/h2-3,5-6,8-9,12,17,27-28H,1,4,7H2,(H,29,35)(H,30,36)(H3,25,31,33)(H3,26,32,34);2(H,6,7)/t9-,12-,17-;;/m1../s1
SMILES:	OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.Brc1c[nH]c(c1)C(=O)NC[C@H]1Cc2[nH]c(=N)[nH]c2[C@H]([C@@H]1CNC(=O)c1[nH]cc(c1)Br)c1c[nH]c(=N)[nH]1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502866
PubChem CID:	44575311 11513454
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001093] Carboxylic acid derivatives [CHEMONTID:0000475] Carboxylic acid amides [CHEMONTID:0004817] 2-heteroaryl carboxamides

*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
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	at a depth of 14 m near the island of Ambon (Seram Seilale), Indonesia	1997-AUG	PMID[10514317]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14677933]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332839]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562840]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19209898]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[26083682]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584409]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	papua new guinean	n.a.	PMID[9784179]
NPO11199	Agelas nakamurai	Species	Agelasidae	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	1
MIC	3
Others	4

Activity Type	# Activity
Organism	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	4.17	ug.mL-1	PMID[509513]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	8.33	ug.mL-1	PMID[509513]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	33.3	ug.mL-1	PMID[509513]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[509513]
NPT2709	Organism	Bacillus subtilis subsp. subtilis str. 168	Bacillus subtilis subsp. subtilis str. 168	IZ	=	14.0	mm	PMID[509514]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	11.0	mm	PMID[509514]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	8.0	mm	PMID[509514]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	11.0	mm	PMID[509514]

☑ 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 NPC475286 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	721
0.1-0.2	12760
0.2-0.3	21391
0.3-0.4	3303
0.4-0.5	2675
0.5-0.6	1509
0.6-0.7	300
0.7-0.8	20
0.8-0.85	4
0.85-0.9	8
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC174281
0.9886	High Similarity	NPC136957
0.9886	High Similarity	NPC19696
0.9716	High Similarity	NPC48117
0.9716	High Similarity	NPC476526
0.9716	High Similarity	NPC329765
0.9492	High Similarity	NPC19342
0.9153	High Similarity	NPC111566
0.9153	High Similarity	NPC476527
0.9101	High Similarity	NPC310633
0.9016	High Similarity	NPC469717
0.8939	High Similarity	NPC63571
0.8743	High Similarity	NPC476524
0.8743	High Similarity	NPC476525
0.8531	High Similarity	NPC54214
0.8526	High Similarity	NPC9635
0.8249	Intermediate Similarity	NPC206148
0.8022	Intermediate Similarity	NPC469976
0.801	Intermediate Similarity	NPC469716
0.7845	Intermediate Similarity	NPC73687
0.7826	Intermediate Similarity	NPC476421
0.7826	Intermediate Similarity	NPC28096
0.7826	Intermediate Similarity	NPC227489
0.7796	Intermediate Similarity	NPC136441
0.7766	Intermediate Similarity	NPC40530
0.7766	Intermediate Similarity	NPC314281
0.773	Intermediate Similarity	NPC226835
0.7725	Intermediate Similarity	NPC472861
0.7725	Intermediate Similarity	NPC184932
0.7692	Intermediate Similarity	NPC188821
0.7692	Intermediate Similarity	NPC474180
0.765	Intermediate Similarity	NPC476418
0.7626	Intermediate Similarity	NPC474389
0.759	Intermediate Similarity	NPC210123
0.7536	Intermediate Similarity	NPC470703
0.75	Intermediate Similarity	NPC66642
0.7488	Intermediate Similarity	NPC473218
0.7488	Intermediate Similarity	NPC470702
0.7487	Intermediate Similarity	NPC16659
0.7474	Intermediate Similarity	NPC240088
0.7474	Intermediate Similarity	NPC473380
0.746	Intermediate Similarity	NPC37268
0.746	Intermediate Similarity	NPC97106
0.7435	Intermediate Similarity	NPC265710
0.7413	Intermediate Similarity	NPC477004
0.7409	Intermediate Similarity	NPC270834
0.7407	Intermediate Similarity	NPC271927
0.7371	Intermediate Similarity	NPC469814
0.7351	Intermediate Similarity	NPC473706
0.7316	Intermediate Similarity	NPC80528
0.7308	Intermediate Similarity	NPC472260
0.726	Intermediate Similarity	NPC470323
0.725	Intermediate Similarity	NPC476414
0.7234	Intermediate Similarity	NPC233380
0.7222	Intermediate Similarity	NPC260041
0.7206	Intermediate Similarity	NPC269203
0.7206	Intermediate Similarity	NPC13456
0.7206	Intermediate Similarity	NPC77241
0.7206	Intermediate Similarity	NPC166209
0.72	Intermediate Similarity	NPC476413
0.7196	Intermediate Similarity	NPC474696
0.7195	Intermediate Similarity	NPC474357
0.7194	Intermediate Similarity	NPC477003
0.7157	Intermediate Similarity	NPC268744
0.7157	Intermediate Similarity	NPC474318
0.7157	Intermediate Similarity	NPC475914
0.7157	Intermediate Similarity	NPC153123
0.7157	Intermediate Similarity	NPC201266
0.7157	Intermediate Similarity	NPC220797
0.715	Intermediate Similarity	NPC476460
0.7149	Intermediate Similarity	NPC935
0.7149	Intermediate Similarity	NPC267078
0.7143	Intermediate Similarity	NPC2414
0.7101	Intermediate Similarity	NPC317701
0.7083	Intermediate Similarity	NPC474195
0.707	Intermediate Similarity	NPC475736
0.7065	Intermediate Similarity	NPC471655
0.7048	Intermediate Similarity	NPC116555
0.7045	Intermediate Similarity	NPC150592
0.7035	Intermediate Similarity	NPC46022
0.7035	Intermediate Similarity	NPC112489
0.7032	Intermediate Similarity	NPC474196
0.7014	Intermediate Similarity	NPC156003
0.6986	Remote Similarity	NPC473376
0.6985	Remote Similarity	NPC308931
0.6985	Remote Similarity	NPC99939
0.6968	Remote Similarity	NPC27296
0.6954	Remote Similarity	NPC234403
0.6954	Remote Similarity	NPC477042
0.6952	Remote Similarity	NPC474236
0.6947	Remote Similarity	NPC253687
0.6944	Remote Similarity	NPC267811
0.6916	Remote Similarity	NPC477413
0.6911	Remote Similarity	NPC274981
0.691	Remote Similarity	NPC291517
0.6908	Remote Similarity	NPC237414
0.6893	Remote Similarity	NPC20021
0.6875	Remote Similarity	NPC474383
0.6869	Remote Similarity	NPC79777
0.686	Remote Similarity	NPC171317
0.6853	Remote Similarity	NPC284775
0.6842	Remote Similarity	NPC474492
0.6834	Remote Similarity	NPC307191
0.683	Remote Similarity	NPC69843
0.6829	Remote Similarity	NPC304203
0.6823	Remote Similarity	NPC306160
0.6816	Remote Similarity	NPC476423
0.6816	Remote Similarity	NPC23215
0.6806	Remote Similarity	NPC282247
0.6804	Remote Similarity	NPC168209
0.6796	Remote Similarity	NPC46811
0.6791	Remote Similarity	NPC320968
0.6787	Remote Similarity	NPC175150
0.6787	Remote Similarity	NPC243633
0.6786	Remote Similarity	NPC477611
0.6749	Remote Similarity	NPC17059
0.6748	Remote Similarity	NPC326422
0.6733	Remote Similarity	NPC133003
0.6728	Remote Similarity	NPC54744
0.6719	Remote Similarity	NPC470680
0.6719	Remote Similarity	NPC100104
0.6716	Remote Similarity	NPC213629
0.67	Remote Similarity	NPC182940
0.67	Remote Similarity	NPC94752
0.6684	Remote Similarity	NPC100726
0.6683	Remote Similarity	NPC110158
0.6683	Remote Similarity	NPC228835
0.6682	Remote Similarity	NPC471194
0.6682	Remote Similarity	NPC471193
0.6681	Remote Similarity	NPC201831
0.6681	Remote Similarity	NPC17487
0.6667	Remote Similarity	NPC221726
0.6667	Remote Similarity	NPC477414
0.6667	Remote Similarity	NPC225622
0.6652	Remote Similarity	NPC477108
0.6652	Remote Similarity	NPC477107
0.6652	Remote Similarity	NPC477109
0.6651	Remote Similarity	NPC167710
0.665	Remote Similarity	NPC262338
0.665	Remote Similarity	NPC11126
0.6649	Remote Similarity	NPC74357
0.6636	Remote Similarity	NPC72956
0.6634	Remote Similarity	NPC473666
0.6634	Remote Similarity	NPC473628
0.6634	Remote Similarity	NPC470205
0.6618	Remote Similarity	NPC304187
0.6618	Remote Similarity	NPC477167
0.6618	Remote Similarity	NPC477166
0.6618	Remote Similarity	NPC473342
0.6615	Remote Similarity	NPC280864
0.6615	Remote Similarity	NPC17751
0.6606	Remote Similarity	NPC469715
0.6606	Remote Similarity	NPC6865
0.6606	Remote Similarity	NPC153980
0.6602	Remote Similarity	NPC324091
0.6602	Remote Similarity	NPC475874
0.6601	Remote Similarity	NPC108011
0.6598	Remote Similarity	NPC470203
0.6597	Remote Similarity	NPC75135
0.6589	Remote Similarity	NPC88115
0.6584	Remote Similarity	NPC191415
0.6583	Remote Similarity	NPC469529
0.6583	Remote Similarity	NPC186068
0.6578	Remote Similarity	NPC467188
0.656	Remote Similarity	NPC54981
0.6552	Remote Similarity	NPC117027
0.6552	Remote Similarity	NPC102755
0.6546	Remote Similarity	NPC470204
0.6545	Remote Similarity	NPC251391
0.654	Remote Similarity	NPC131887
0.6537	Remote Similarity	NPC141612
0.6537	Remote Similarity	NPC135601
0.6537	Remote Similarity	NPC17273
0.6533	Remote Similarity	NPC476817
0.6533	Remote Similarity	NPC161861
0.6528	Remote Similarity	NPC54420
0.6526	Remote Similarity	NPC473878
0.652	Remote Similarity	NPC21429
0.6516	Remote Similarity	NPC470731
0.6516	Remote Similarity	NPC470732
0.6516	Remote Similarity	NPC471192
0.651	Remote Similarity	NPC477815
0.6508	Remote Similarity	NPC105811
0.6497	Remote Similarity	NPC49217
0.6495	Remote Similarity	NPC106757
0.6486	Remote Similarity	NPC477114
0.6485	Remote Similarity	NPC233050
0.6485	Remote Similarity	NPC276540
0.648	Remote Similarity	NPC247987
0.6473	Remote Similarity	NPC209917
0.6471	Remote Similarity	NPC50562
0.6468	Remote Similarity	NPC107077
0.6468	Remote Similarity	NPC162860
0.6468	Remote Similarity	NPC223791
0.6468	Remote Similarity	NPC474958
0.6467	Remote Similarity	NPC472288
0.6462	Remote Similarity	NPC473640
0.6462	Remote Similarity	NPC477044
0.6462	Remote Similarity	NPC477041
0.6449	Remote Similarity	NPC475506

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 NPC475286 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	897
0.2-0.3	1889
0.3-0.4	2335
0.4-0.5	2109
0.5-0.6	1340
0.6-0.7	261
0.7-0.8	12
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
0.7716	Intermediate Similarity	NPD7459	Phase 2
0.71	Intermediate Similarity	NPD5685	Approved
0.71	Intermediate Similarity	NPD5686	Approved
0.7095	Intermediate Similarity	NPD7704	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD2289	Phase 3
0.7094	Intermediate Similarity	NPD2290	Phase 3
0.7048	Intermediate Similarity	NPD2443	Approved
0.7048	Intermediate Similarity	NPD2442	Approved
0.7	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD2008	Discontinued
0.6919	Remote Similarity	NPD1506	Discontinued
0.6912	Remote Similarity	NPD460	Discontinued
0.6881	Remote Similarity	NPD5198	Approved
0.6881	Remote Similarity	NPD5199	Approved
0.6866	Remote Similarity	NPD5643	Phase 2
0.686	Remote Similarity	NPD1982	Phase 1
0.6854	Remote Similarity	NPD1600	Suspended
0.6854	Remote Similarity	NPD2408	Discontinued
0.6837	Remote Similarity	NPD2411	Approved
0.6827	Remote Similarity	NPD2405	Phase 3
0.6814	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2880	Discontinued
0.6712	Remote Similarity	NPD8256	Approved
0.6712	Remote Similarity	NPD8257	Approved
0.6712	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7970	Approved
0.6697	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5017	Discontinued
0.6667	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD5446	Phase 2
0.6635	Remote Similarity	NPD5855	Phase 3
0.6635	Remote Similarity	NPD5853	Phase 3
0.6618	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6470	Phase 3
0.659	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5854	Approved
0.6574	Remote Similarity	NPD6459	Phase 2
0.6571	Remote Similarity	NPD6664	Approved
0.6558	Remote Similarity	NPD3967	Approved
0.6538	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD3411	Phase 2
0.6528	Remote Similarity	NPD3410	Approved
0.6526	Remote Similarity	NPD3890	Phase 2
0.6526	Remote Similarity	NPD3891	Phase 2
0.6505	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD3178	Discontinued
0.6502	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6465	Phase 2
0.6493	Remote Similarity	NPD1952	Discontinued
0.6476	Remote Similarity	NPD7618	Phase 3
0.6476	Remote Similarity	NPD7619	Phase 3
0.6473	Remote Similarity	NPD6210	Phase 3
0.6471	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD3968	Approved
0.6468	Remote Similarity	NPD2367	Phase 2
0.6459	Remote Similarity	NPD4922	Phase 2
0.6449	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD6164	Phase 2
0.6447	Remote Similarity	NPD6165	Phase 2
0.6439	Remote Similarity	NPD1096	Discontinued
0.6439	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6268	Phase 1
0.6411	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6579	Phase 2
0.6386	Remote Similarity	NPD4075	Phase 2
0.6379	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD7026	Phase 2
0.6368	Remote Similarity	NPD3353	Approved
0.6368	Remote Similarity	NPD7027	Phase 3
0.6364	Remote Similarity	NPD8316	Phase 2
0.6364	Remote Similarity	NPD8317	Phase 2
0.6359	Remote Similarity	NPD7207	Approved
0.6359	Remote Similarity	NPD7208	Approved
0.6359	Remote Similarity	NPD4299	Phase 1
0.6359	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7209	Approved
0.6359	Remote Similarity	NPD5426	Phase 3
0.6346	Remote Similarity	NPD4988	Discontinued
0.6346	Remote Similarity	NPD3961	Discontinued
0.6343	Remote Similarity	NPD2881	Approved
0.6343	Remote Similarity	NPD2879	Approved
0.6341	Remote Similarity	NPD1895	Discontinued
0.6339	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4883	Approved
0.6335	Remote Similarity	NPD4863	Approved
0.6335	Remote Similarity	NPD3915	Approved
0.6333	Remote Similarity	NPD1658	Discontinued
0.6323	Remote Similarity	NPD4395	Phase 1
0.6318	Remote Similarity	NPD5510	Approved
0.6316	Remote Similarity	NPD7175	Phase 1
0.6316	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD3583	Phase 2
0.6306	Remote Similarity	NPD7656	Approved
0.6306	Remote Similarity	NPD3917	Approved
0.6306	Remote Similarity	NPD3918	Approved
0.6306	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7657	Approved
0.6301	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD1031	Discontinued
0.6296	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD3927	Phase 2
0.6291	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD8169	Discontinued
0.6284	Remote Similarity	NPD803	Phase 1
0.6281	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.628	Remote Similarity	NPD7564	Discontinued
0.6274	Remote Similarity	NPD3460	Discontinued
0.627	Remote Similarity	NPD272	Approved
0.6269	Remote Similarity	NPD971	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD6802	Phase 3
0.6263	Remote Similarity	NPD6771	Discontinued
0.6256	Remote Similarity	NPD5491	Phase 3
0.6256	Remote Similarity	NPD2061	Approved
0.6256	Remote Similarity	NPD5489	Phase 1
0.6255	Remote Similarity	NPD6986	Phase 1
0.625	Remote Similarity	NPD439	Approved
0.625	Remote Similarity	NPD438	Approved
0.6245	Remote Similarity	NPD6849	Phase 2
0.6245	Remote Similarity	NPD6752	Phase 1
0.6245	Remote Similarity	NPD6753	Phase 1
0.6245	Remote Similarity	NPD6850	Phase 2
0.6244	Remote Similarity	NPD2819	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4541	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD3318	Approved
0.6232	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD3319	Phase 1
0.6232	Remote Similarity	NPD3320	Approved
0.6227	Remote Similarity	NPD3905	Phase 3
0.6226	Remote Similarity	NPD5974	Approved
0.6226	Remote Similarity	NPD5973	Phase 2
0.6225	Remote Similarity	NPD6044	Discontinued
0.622	Remote Similarity	NPD6217	Discontinued
0.6217	Remote Similarity	NPD5987	Approved
0.6217	Remote Similarity	NPD5986	Approved
0.6216	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5508	Phase 1
0.6214	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7888	Approved
0.6207	Remote Similarity	NPD7887	Approved
0.6205	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD2363	Discontinued
0.6203	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD4558	Phase 2
0.6197	Remote Similarity	NPD5274	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4181	Approved
0.6195	Remote Similarity	NPD3041	Approved
0.619	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD2172	Phase 1
0.6184	Remote Similarity	NPD1707	Approved
0.6184	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD1996	Discontinued
0.6184	Remote Similarity	NPD1708	Approved
0.6179	Remote Similarity	NPD3517	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD482	Approved
0.6176	Remote Similarity	NPD4128	Approved
0.6169	Remote Similarity	NPD5611	Phase 2
0.6161	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD1250	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD1722	Approved
0.6157	Remote Similarity	NPD4364	Phase 1
0.6154	Remote Similarity	NPD7445	Phase 1
0.6154	Remote Similarity	NPD2092	Phase 2
0.6154	Remote Similarity	NPD2095	Phase 2
0.6154	Remote Similarity	NPD2094	Phase 2
0.615	Remote Similarity	NPD3431	Approved
0.615	Remote Similarity	NPD198	Clinical (unspecified phase)
0.615	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.615	Remote Similarity	NPD3430	Approved
0.6147	Remote Similarity	NPD7817	Phase 1
0.6146	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD2793	Discontinued
0.6142	Remote Similarity	NPD276	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6226	Phase 3
0.614	Remote Similarity	NPD4848	Phase 1
0.6139	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD786	Approved
0.6138	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD8272	Phase 2
0.6135	Remote Similarity	NPD6595	Phase 3
0.6135	Remote Similarity	NPD2481	Approved
0.6135	Remote Similarity	NPD2479	Phase 3
0.6133	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7000	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