NPASS Compound

Structure

NPC213529 OpenBabel07101719512D 48 53 0 0 1 0 0 0 0 0999 V2000 -7.0360 -5.6797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8657 -0.3380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3065 0.4686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9370 -2.7941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6626 -1.2569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5414 -1.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2177 -1.1615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7237 1.4951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7423 1.4951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0288 -0.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8355 -3.0634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8815 -2.2030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6305 -3.0634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7000 -0.4812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8446 -4.7171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7423 -3.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6305 1.1195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8355 1.1195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1231 -0.4197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1415 -2.3694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7237 -3.4390 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0020 -1.3234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3245 0.4255 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3245 -2.3694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6110 0.1470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8549 0.1470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1619 -1.9562 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7256 -1.5373 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7659 -1.4627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9685 -1.3971 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1415 0.4255 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8066 -0.5592 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8875 -0.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3883 -0.2804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3254 -2.9147 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -6.2808 -0.7372 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -5.9152 -4.4016 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8561 -1.8160 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.5825 -4.0700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3261 -0.3970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1405 0.9708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1405 -2.9147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2429 -2.9343 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5322 -2.0964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7000 -1.4627 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7659 -0.4812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5817 0.2787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 33 1 0 0 0 0 3 33 1 0 0 0 0 4 38 1 0 0 0 0 5 38 1 0 0 0 0 6 7 1 0 0 0 0 6 10 2 0 0 0 0 7 19 2 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 34 1 0 0 0 0 11 16 2 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 22 2 0 0 0 0 13 21 1 0 0 0 0 13 24 1 0 0 0 0 14 23 1 0 0 0 0 14 45 1 0 0 0 0 15 37 2 3 0 0 0 15 39 1 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 17 26 2 0 0 0 0 18 25 2 0 0 0 0 18 31 1 0 0 0 0 19 25 1 0 0 0 0 19 34 1 0 0 0 0 20 29 2 0 0 0 0 20 35 1 0 0 0 0 21 37 1 1 0 0 0 22 29 1 0 0 0 0 22 40 1 0 0 0 0 23 41 1 6 0 0 0 24 42 2 0 0 0 0 24 45 1 0 0 0 0 25 26 1 0 0 0 0 26 36 1 0 0 0 0 27 28 1 0 0 0 0 27 30 1 0 0 0 0 27 43 1 1 0 0 0 28 32 1 0 0 0 0 28 44 1 1 0 0 0 29 46 1 0 0 0 0 30 33 1 0 0 0 0 30 38 1 1 0 0 0 31 34 1 6 0 0 0 31 46 1 0 0 0 0 32 47 1 0 0 0 0 32 48 1 6 0 0 0 33 47 1 0 0 0 0 34 48 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	704.19
Volume:	659.235
LogP:	1.198
LogD:	0.64
LogS:	-3.457
# Rotatable Bonds:	5
TPSA:	167.25
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	9
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.296
Synthetic Accessibility Score:	7.225
Fsp3:	0.471
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.107
MDCK Permeability:	1.2820400115742814e-05
Pgp-inhibitor:	0.962
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.111
Plasma Protein Binding (PPB):	88.2417984008789%
Volume Distribution (VD):	1.389
Pgp-substrate:	5.194206237792969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.092
CYP2C19-substrate:	0.167
CYP2C9-inhibitor:	0.442
CYP2C9-substrate:	0.16
CYP2D6-inhibitor:	0.161
CYP2D6-substrate:	0.218
CYP3A4-inhibitor:	0.539
CYP3A4-substrate:	0.895

ADMET: Excretion

Clearance (CL):	1.867
Half-life (T1/2):	0.334

ADMET: Toxicity

hERG Blockers:	0.477
Human Hepatotoxicity (H-HT):	0.427
Drug-inuced Liver Injury (DILI):	0.474
AMES Toxicity:	0.305
Rat Oral Acute Toxicity:	0.665
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.191
Carcinogencity:	0.381
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC213529

Natural Product ID:	NPC213529
*Common Name:**	Fijiolide A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UOSXSYLUJCWXEX-POTPYSIGSA-N
Standard InCHI:	InChI=1S/C34H38Cl2N2O10/c1-15(39)37-21-13-24(42)45-14-23(41)17-8-9-18-25(26(17)36)19-7-6-10-34(19,31(18)46-29-20(35)11-16(21)12-22(29)40)48-32-28(44)27(43)30(38(4)5)33(2,3)47-32/h6-12,21,23,27-28,30-32,40-41,43-44H,13-14H2,1-5H3,(H,37,39)/t21-,23-,27-,28+,30-,31+,32-,34+/m0/s1
SMILES:	CC(=N[C@H]1CC(=O)OC[C@@H](c2ccc3c(C4=CC=C[C@@]4([C@@H]3Oc3c(cc1cc3O)Cl)O[C@H]1[C@@H]([C@@H]([C@@H](C(C)(C)O1)N(C)C)O)O)c2Cl)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1164839
PubChem CID:	46850183
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0003305] Aminosaccharides [CHEMONTID:0000282] Aminoglycosides

*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
NPO33173	nocardiopsis	Genus	0cardiopsaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20481500]

☑ 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
Others	3

Activity Type	# Activity
Individual Protein	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT365	Individual Protein	NAD(P)H dehydrogenase [quinone] 1	Mus musculus	Ratio	=	3.5	n.a.	PMID[459041]
NPT365	Individual Protein	NAD(P)H dehydrogenase [quinone] 1	Mus musculus	CD	=	1.8	uM	PMID[459041]
NPT2	Others	Unspecified		IC50	=	570.0	nM	PMID[459041]
NPT2	Others	Unspecified		Inhibition	=	70.3	%	PMID[459041]

☑ 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 NPC213529 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	348
0.1-0.2	1656
0.2-0.3	5532
0.3-0.4	12235
0.4-0.5	9092
0.5-0.6	12294
0.6-0.7	1522
0.7-0.8	16
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9624	High Similarity	NPC3921
0.7917	Intermediate Similarity	NPC319774
0.7908	Intermediate Similarity	NPC314743
0.76	Intermediate Similarity	NPC313627
0.7169	Intermediate Similarity	NPC230098
0.7143	Intermediate Similarity	NPC50548
0.7098	Intermediate Similarity	NPC144314
0.7054	Intermediate Similarity	NPC149962
0.7035	Intermediate Similarity	NPC123859
0.7005	Intermediate Similarity	NPC45112
0.7005	Intermediate Similarity	NPC263507
0.7005	Intermediate Similarity	NPC134413
0.7005	Intermediate Similarity	NPC271958
0.7004	Intermediate Similarity	NPC242728
0.6941	Remote Similarity	NPC86678
0.6941	Remote Similarity	NPC474745
0.6923	Remote Similarity	NPC475981
0.6923	Remote Similarity	NPC474746
0.6895	Remote Similarity	NPC474325
0.6878	Remote Similarity	NPC229234
0.686	Remote Similarity	NPC475624
0.6856	Remote Similarity	NPC323858
0.6849	Remote Similarity	NPC474470
0.6849	Remote Similarity	NPC237044
0.6837	Remote Similarity	NPC269383
0.6837	Remote Similarity	NPC151030
0.6824	Remote Similarity	NPC258128
0.682	Remote Similarity	NPC474953
0.682	Remote Similarity	NPC227778
0.6818	Remote Similarity	NPC475349
0.6818	Remote Similarity	NPC475565
0.6818	Remote Similarity	NPC475442
0.6818	Remote Similarity	NPC475292
0.6812	Remote Similarity	NPC267414
0.6804	Remote Similarity	NPC49353
0.6804	Remote Similarity	NPC304675
0.6774	Remote Similarity	NPC49315
0.6771	Remote Similarity	NPC156576
0.677	Remote Similarity	NPC319549
0.6769	Remote Similarity	NPC14622
0.6769	Remote Similarity	NPC124302
0.6769	Remote Similarity	NPC215098
0.6769	Remote Similarity	NPC73020
0.6769	Remote Similarity	NPC46744
0.6769	Remote Similarity	NPC70290
0.6758	Remote Similarity	NPC2314
0.6754	Remote Similarity	NPC33256
0.6748	Remote Similarity	NPC316461
0.6742	Remote Similarity	NPC329480
0.674	Remote Similarity	NPC94499
0.6738	Remote Similarity	NPC169605
0.6728	Remote Similarity	NPC252960
0.6726	Remote Similarity	NPC248642
0.6726	Remote Similarity	NPC474650
0.6726	Remote Similarity	NPC474498
0.6724	Remote Similarity	NPC202771
0.6724	Remote Similarity	NPC119818
0.6724	Remote Similarity	NPC328700
0.6724	Remote Similarity	NPC2173
0.6723	Remote Similarity	NPC315253
0.6723	Remote Similarity	NPC326027
0.6712	Remote Similarity	NPC477640
0.6712	Remote Similarity	NPC470739
0.6712	Remote Similarity	NPC208818
0.6712	Remote Similarity	NPC225597
0.6712	Remote Similarity	NPC32154
0.671	Remote Similarity	NPC314100
0.671	Remote Similarity	NPC72788
0.671	Remote Similarity	NPC120671
0.671	Remote Similarity	NPC226652
0.6709	Remote Similarity	NPC475768
0.6709	Remote Similarity	NPC326333
0.6708	Remote Similarity	NPC180210
0.6708	Remote Similarity	NPC478046
0.6708	Remote Similarity	NPC314914
0.6708	Remote Similarity	NPC478047
0.6708	Remote Similarity	NPC328856
0.6708	Remote Similarity	NPC321226
0.6698	Remote Similarity	NPC61604
0.6698	Remote Similarity	NPC245615
0.6698	Remote Similarity	NPC299706
0.6698	Remote Similarity	NPC115466
0.6695	Remote Similarity	NPC235698
0.6694	Remote Similarity	NPC274268
0.6694	Remote Similarity	NPC170101
0.6682	Remote Similarity	NPC474607
0.6682	Remote Similarity	NPC21956
0.6682	Remote Similarity	NPC163635
0.668	Remote Similarity	NPC316368
0.668	Remote Similarity	NPC284236
0.6667	Remote Similarity	NPC474708
0.6667	Remote Similarity	NPC474475
0.6667	Remote Similarity	NPC24260
0.6667	Remote Similarity	NPC320223
0.6667	Remote Similarity	NPC478048
0.6667	Remote Similarity	NPC114364
0.6654	Remote Similarity	NPC131258
0.6652	Remote Similarity	NPC234318
0.6651	Remote Similarity	NPC25889
0.6639	Remote Similarity	NPC148124
0.6639	Remote Similarity	NPC470846
0.6638	Remote Similarity	NPC475654
0.6638	Remote Similarity	NPC314946
0.6637	Remote Similarity	NPC474661
0.6637	Remote Similarity	NPC475794
0.6637	Remote Similarity	NPC126284
0.6637	Remote Similarity	NPC475919
0.6636	Remote Similarity	NPC477115
0.6623	Remote Similarity	NPC475754
0.6622	Remote Similarity	NPC241704
0.6622	Remote Similarity	NPC88739
0.6622	Remote Similarity	NPC276120
0.6622	Remote Similarity	NPC184485
0.6621	Remote Similarity	NPC158148
0.6621	Remote Similarity	NPC290759
0.6621	Remote Similarity	NPC58766
0.6621	Remote Similarity	NPC475686
0.6621	Remote Similarity	NPC266176
0.6621	Remote Similarity	NPC82533
0.6621	Remote Similarity	NPC475845
0.662	Remote Similarity	NPC179914
0.6609	Remote Similarity	NPC473371
0.6609	Remote Similarity	NPC64576
0.6609	Remote Similarity	NPC201055
0.6609	Remote Similarity	NPC254045
0.6609	Remote Similarity	NPC151470
0.6608	Remote Similarity	NPC174122
0.6608	Remote Similarity	NPC64140
0.6608	Remote Similarity	NPC29531
0.6608	Remote Similarity	NPC237579
0.6606	Remote Similarity	NPC198741
0.6605	Remote Similarity	NPC478055
0.6599	Remote Similarity	NPC248903
0.6598	Remote Similarity	NPC99724
0.6593	Remote Similarity	NPC34780
0.6592	Remote Similarity	NPC118633
0.6592	Remote Similarity	NPC294790
0.6592	Remote Similarity	NPC148693
0.6592	Remote Similarity	NPC329816
0.659	Remote Similarity	NPC218614
0.6586	Remote Similarity	NPC167027
0.6579	Remote Similarity	NPC470642
0.6578	Remote Similarity	NPC116284
0.6577	Remote Similarity	NPC128560
0.6577	Remote Similarity	NPC199465
0.6577	Remote Similarity	NPC187678
0.6577	Remote Similarity	NPC229166
0.6575	Remote Similarity	NPC190332
0.6575	Remote Similarity	NPC57812
0.6575	Remote Similarity	NPC100566
0.6575	Remote Similarity	NPC210140
0.6575	Remote Similarity	NPC150879
0.6575	Remote Similarity	NPC181653
0.6575	Remote Similarity	NPC474324
0.6574	Remote Similarity	NPC4304
0.6568	Remote Similarity	NPC80472
0.6564	Remote Similarity	NPC214116
0.6564	Remote Similarity	NPC162694
0.6564	Remote Similarity	NPC234069
0.6562	Remote Similarity	NPC193377
0.6562	Remote Similarity	NPC99179
0.6561	Remote Similarity	NPC286809
0.6559	Remote Similarity	NPC26928
0.6558	Remote Similarity	NPC38699
0.6557	Remote Similarity	NPC158635
0.6557	Remote Similarity	NPC229882
0.6555	Remote Similarity	NPC293347
0.6555	Remote Similarity	NPC476496
0.655	Remote Similarity	NPC226708
0.6547	Remote Similarity	NPC32064
0.6545	Remote Similarity	NPC252156
0.6545	Remote Similarity	NPC85735
0.654	Remote Similarity	NPC11708
0.6535	Remote Similarity	NPC22115
0.6535	Remote Similarity	NPC141440
0.6535	Remote Similarity	NPC275680
0.6531	Remote Similarity	NPC44040
0.6528	Remote Similarity	NPC228357
0.6524	Remote Similarity	NPC277857
0.6524	Remote Similarity	NPC115144
0.652	Remote Similarity	NPC83933
0.6516	Remote Similarity	NPC475621
0.6516	Remote Similarity	NPC476751
0.6513	Remote Similarity	NPC94687
0.6513	Remote Similarity	NPC106840
0.6513	Remote Similarity	NPC476495
0.6511	Remote Similarity	NPC286135
0.6508	Remote Similarity	NPC328287
0.6507	Remote Similarity	NPC82763
0.6507	Remote Similarity	NPC206900
0.6504	Remote Similarity	NPC35266
0.6504	Remote Similarity	NPC315542
0.6504	Remote Similarity	NPC138083
0.6502	Remote Similarity	NPC179240
0.65	Remote Similarity	NPC14294
0.65	Remote Similarity	NPC109990
0.65	Remote Similarity	NPC116759
0.6496	Remote Similarity	NPC313274
0.6494	Remote Similarity	NPC471563
0.6491	Remote Similarity	NPC471395

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 NPC213529 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	672
0.2-0.3	1256
0.3-0.4	2646
0.4-0.5	2743
0.5-0.6	1365
0.6-0.7	253
0.7-0.8	2
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
0.7261	Intermediate Similarity	NPD7827	Phase 1
0.7035	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7959	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7999	Approved
0.6972	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7930	Approved
0.6816	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6312	Discontinued
0.677	Remote Similarity	NPD7296	Approved
0.6769	Remote Similarity	NPD4420	Approved
0.6724	Remote Similarity	NPD5005	Approved
0.6724	Remote Similarity	NPD5006	Approved
0.6711	Remote Similarity	NPD7906	Approved
0.6654	Remote Similarity	NPD8153	Approved
0.6654	Remote Similarity	NPD8152	Approved
0.6637	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3819	Phase 2
0.6609	Remote Similarity	NPD3450	Approved
0.6609	Remote Similarity	NPD3452	Approved
0.6609	Remote Similarity	NPD2494	Approved
0.6609	Remote Similarity	NPD2493	Approved
0.6602	Remote Similarity	NPD8398	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7783	Phase 2
0.6569	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD7281	Phase 3
0.6533	Remote Similarity	NPD7280	Phase 3
0.6532	Remote Similarity	NPD5096	Phase 3
0.6532	Remote Similarity	NPD5095	Phase 3
0.6532	Remote Similarity	NPD3933	Discontinued
0.6531	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD4582	Approved
0.6525	Remote Similarity	NPD4583	Approved
0.6524	Remote Similarity	NPD7565	Approved
0.6518	Remote Similarity	NPD7685	Pre-registration
0.6513	Remote Similarity	NPD7701	Phase 2
0.6512	Remote Similarity	NPD5773	Approved
0.6512	Remote Similarity	NPD5772	Approved
0.6504	Remote Similarity	NPD6851	Approved
0.6504	Remote Similarity	NPD6853	Approved
0.6504	Remote Similarity	NPD6997	Phase 2
0.6498	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7228	Approved
0.6483	Remote Similarity	NPD4002	Approved
0.6483	Remote Similarity	NPD4004	Approved
0.6466	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD4361	Phase 2
0.6461	Remote Similarity	NPD7047	Phase 3
0.6458	Remote Similarity	NPD7874	Approved
0.6458	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD4873	Discontinued
0.6456	Remote Similarity	NPD8319	Approved
0.6456	Remote Similarity	NPD8320	Phase 1
0.6447	Remote Similarity	NPD4663	Approved
0.6444	Remote Similarity	NPD7585	Approved
0.6438	Remote Similarity	NPD2975	Approved
0.6438	Remote Similarity	NPD2973	Approved
0.6438	Remote Similarity	NPD2974	Approved
0.6435	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD8404	Phase 2
0.6432	Remote Similarity	NPD7309	Approved
0.6432	Remote Similarity	NPD7801	Approved
0.6432	Remote Similarity	NPD8053	Approved
0.6432	Remote Similarity	NPD8054	Approved
0.6422	Remote Similarity	NPD7831	Phase 2
0.6422	Remote Similarity	NPD4360	Phase 2
0.6422	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4363	Phase 3
0.6422	Remote Similarity	NPD7833	Phase 2
0.6414	Remote Similarity	NPD7497	Discontinued
0.6404	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7583	Approved
0.64	Remote Similarity	NPD8059	Phase 3
0.64	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6234	Discontinued
0.6388	Remote Similarity	NPD4578	Approved
0.6388	Remote Similarity	NPD7313	Approved
0.6388	Remote Similarity	NPD4577	Approved
0.6388	Remote Similarity	NPD7312	Approved
0.6388	Remote Similarity	NPD7310	Approved
0.6388	Remote Similarity	NPD7311	Approved
0.638	Remote Similarity	NPD7315	Approved
0.6372	Remote Similarity	NPD3303	Discontinued
0.6372	Remote Similarity	NPD7038	Approved
0.6372	Remote Similarity	NPD7039	Approved
0.6371	Remote Similarity	NPD6823	Phase 2
0.6368	Remote Similarity	NPD4123	Phase 3
0.6364	Remote Similarity	NPD4666	Phase 3
0.6364	Remote Similarity	NPD3365	Discontinued
0.6364	Remote Similarity	NPD2488	Approved
0.6364	Remote Similarity	NPD2490	Approved
0.6359	Remote Similarity	NPD2977	Approved
0.6359	Remote Similarity	NPD2978	Approved
0.6356	Remote Similarity	NPD3885	Approved
0.6356	Remote Similarity	NPD4580	Approved
0.6349	Remote Similarity	NPD8151	Discontinued
0.6348	Remote Similarity	NPD6842	Approved
0.6348	Remote Similarity	NPD6843	Phase 3
0.6348	Remote Similarity	NPD6841	Approved
0.6345	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6625	Approved
0.6339	Remote Similarity	NPD6620	Discovery
0.6335	Remote Similarity	NPD7199	Phase 2
0.6335	Remote Similarity	NPD6107	Approved
0.6327	Remote Similarity	NPD6297	Approved
0.6326	Remote Similarity	NPD4017	Approved
0.6325	Remote Similarity	NPD5582	Discontinued
0.6323	Remote Similarity	NPD27	Approved
0.6323	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD2489	Approved
0.6318	Remote Similarity	NPD5709	Phase 3
0.6314	Remote Similarity	NPD5544	Approved
0.6311	Remote Similarity	NPD5313	Approved
0.6311	Remote Similarity	NPD5312	Approved
0.6303	Remote Similarity	NPD4387	Approved
0.6303	Remote Similarity	NPD4386	Approved
0.6303	Remote Similarity	NPD4971	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD4965	Approved
0.6301	Remote Similarity	NPD4966	Approved
0.6301	Remote Similarity	NPD4967	Phase 2
0.6296	Remote Similarity	NPD4675	Approved
0.6296	Remote Similarity	NPD4678	Approved
0.6293	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD4914	Approved
0.6284	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5557	Phase 1
0.6278	Remote Similarity	NPD2970	Approved
0.6278	Remote Similarity	NPD2969	Approved
0.6275	Remote Similarity	NPD6723	Discontinued
0.6274	Remote Similarity	NPD5058	Phase 3
0.6267	Remote Similarity	NPD3909	Discontinued
0.6267	Remote Similarity	NPD6072	Discontinued
0.6265	Remote Similarity	NPD7805	Phase 3
0.6265	Remote Similarity	NPD7907	Approved
0.6262	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7007	Discovery
0.625	Remote Similarity	NPD2898	Approved
0.625	Remote Similarity	NPD4481	Phase 3
0.625	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD6315	Phase 2
0.6239	Remote Similarity	NPD37	Approved
0.6239	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD3051	Approved
0.6233	Remote Similarity	NPD6071	Discontinued
0.6218	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD6258	Discontinued
0.6208	Remote Similarity	NPD7697	Approved
0.6208	Remote Similarity	NPD7696	Phase 3
0.6208	Remote Similarity	NPD7698	Approved
0.6207	Remote Similarity	NPD7291	Discontinued
0.6205	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD5242	Approved
0.6201	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7584	Approved
0.6193	Remote Similarity	NPD4772	Phase 2
0.6193	Remote Similarity	NPD4773	Phase 2
0.6185	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD7871	Phase 2
0.6183	Remote Similarity	NPD7870	Phase 2
0.6167	Remote Similarity	NPD8156	Discontinued
0.6167	Remote Similarity	NPD42	Phase 2
0.6167	Remote Similarity	NPD6042	Phase 2
0.6157	Remote Similarity	NPD7240	Approved
0.6157	Remote Similarity	NPD8161	Suspended
0.6157	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6151	Remote Similarity	NPD6779	Approved
0.6151	Remote Similarity	NPD6778	Approved
0.6151	Remote Similarity	NPD6776	Approved
0.6151	Remote Similarity	NPD6782	Approved
0.6151	Remote Similarity	NPD6780	Approved
0.6151	Remote Similarity	NPD6777	Approved
0.6151	Remote Similarity	NPD6781	Approved
0.615	Remote Similarity	NPD5880	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD7942	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7048	Phase 3
0.6134	Remote Similarity	NPD4974	Approved
0.6134	Remote Similarity	NPD4975	Approved
0.6129	Remote Similarity	NPD3687	Approved
0.6129	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3686	Approved
0.6129	Remote Similarity	NPD4210	Discontinued
0.6123	Remote Similarity	NPD8251	Approved
0.6123	Remote Similarity	NPD8252	Approved
0.6123	Remote Similarity	NPD8099	Discontinued
0.6121	Remote Similarity	NPD6815	Approved
0.6119	Remote Similarity	NPD6385	Approved
0.6119	Remote Similarity	NPD8492	Approved
0.6119	Remote Similarity	NPD3274	Phase 2
0.6119	Remote Similarity	NPD6386	Approved
0.6116	Remote Similarity	NPD4040	Phase 1
0.6116	Remote Similarity	NPD8127	Discontinued
0.6114	Remote Similarity	NPD1375	Discontinued
0.6114	Remote Similarity	NPD3823	Discontinued

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