NPASS Compound

Structure

NPC471264 OpenBabel07101719252D 46 48 0 0 1 0 0 0 0 0999 V2000 0.4536 6.7002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4794 8.0958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1162 -2.0822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8456 -1.9868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4383 0.5068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4125 -0.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5698 -0.8218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8258 1.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9598 2.4775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8258 0.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3852 5.1823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0938 1.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9598 0.4775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3907 4.1823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6140 4.4276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1140 3.5615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4325 5.4860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1751 6.5096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2278 0.4775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3694 7.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9534 -1.5353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5225 0.1051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0938 0.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3617 0.9775 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4414 3.8680 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0651 5.5157 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1401 5.0843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8983 -0.5368 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7168 0.6973 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7260 0.2056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7399 2.9136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1683 1.5896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0274 5.2436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9044 -0.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3057 2.5801 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7124 1.9140 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8741 -0.3181 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8492 4.6738 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3835 5.9362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3828 -0.5485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7304 3.0510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1227 1.2910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4542 6.1480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6323 -1.3890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0666 5.4606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 22 1 0 0 0 0 7 38 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 11 14 1 0 0 0 0 11 17 1 0 0 0 0 12 23 2 0 0 0 0 13 23 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 35 1 0 0 0 0 17 39 1 0 0 0 0 18 20 1 0 0 0 0 19 23 1 0 0 0 0 24 19 1 1 0 0 0 24 30 1 0 0 0 0 24 36 1 0 0 0 0 25 14 1 1 0 0 0 25 31 1 0 0 0 0 25 39 1 0 0 0 0 26 18 1 1 0 0 0 26 33 1 0 0 0 0 26 46 1 0 0 0 0 27 40 2 0 0 0 0 27 46 1 0 0 0 0 28 21 1 1 0 0 0 28 34 1 0 0 0 0 28 37 1 0 0 0 0 29 22 1 1 0 0 0 29 32 1 0 0 0 0 29 38 1 0 0 0 0 30 37 2 3 0 0 0 30 41 1 0 0 0 0 31 36 2 3 0 0 0 31 42 1 0 0 0 0 32 35 2 3 0 0 0 32 43 1 0 0 0 0 33 39 1 0 0 0 0 33 44 2 0 0 0 0 34 38 1 0 0 0 0 34 45 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	641.38
Volume:	663.738
LogP:	3.245
LogD:	2.884
LogS:	-4.172
# Rotatable Bonds:	6
TPSA:	154.22
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.401
Synthetic Accessibility Score:	4.869
Fsp3:	0.647
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:	-5.322
MDCK Permeability:	5.5543434427818283e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.927
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.096
30% Bioavailability (F30%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	82.38451385498047%
Volume Distribution (VD):	0.506
Pgp-substrate:	6.7673563957214355%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.03
CYP2C19-inhibitor:	0.167
CYP2C19-substrate:	0.14
CYP2C9-inhibitor:	0.291
CYP2C9-substrate:	0.339
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.915
CYP3A4-substrate:	0.502

ADMET: Excretion

Clearance (CL):	7.65
Half-life (T1/2):	0.811

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.937
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.855
Maximum Recommended Daily Dose:	0.752
Skin Sensitization:	0.05
Carcinogencity:	0.067
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC471264

Natural Product ID:	NPC471264
*Common Name:**	Desmethylisaridin E
IUPAC Name:	(3S,10S,13S,16S,19S)-16-benzyl-11-methyl-3-(2-methylpropyl)-10,13-di(propan-2-yl)-4-oxa-1,8,11,14,17-pentazabicyclo[17.3.0]docosane-2,5,9,12,15,18-hexone
Synonyms:
Standard InCHIKey:	RCPWUQRPXYBTHY-PWOFSUAHSA-N
Standard InCHI:	InChI=1S/C34H51N5O7/c1-20(2)18-26-33(44)39-17-11-14-25(39)31(42)36-24(19-23-12-9-8-10-13-23)30(41)37-28(21(3)4)34(45)38(7)29(22(5)6)32(43)35-16-15-27(40)46-26/h8-10,12-13,20-22,24-26,28-29H,11,14-19H2,1-7H3,(H,35,43)(H,36,42)(H,37,41)/t24-,25-,26-,28-,29-/m0/s1
SMILES:	CC(C)CC1C(=O)N2CCCC2C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)NCCC(=O)O1)C(C)C)C)C(C)C)CC3=CC=CC=C3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2407689
PubChem CID:	71745526
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21438588]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23822585]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26295595]
NPO20842	Beauveria felina	Species	Cordycipitaceae	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

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10000.0	nM	PMID[536857]

☑ 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 NPC471264 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	124
0.1-0.2	597
0.2-0.3	3077
0.3-0.4	19969
0.4-0.5	15069
0.5-0.6	2853
0.6-0.7	588
0.7-0.8	291
0.8-0.85	73
0.85-0.9	44
0.9-0.95	4
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471265
0.9615	High Similarity	NPC92784
0.9615	High Similarity	NPC470884
0.9615	High Similarity	NPC476133
0.9615	High Similarity	NPC98424
0.9615	High Similarity	NPC178662
0.9549	High Similarity	NPC209509
0.947	High Similarity	NPC269398
0.947	High Similarity	NPC263493
0.9259	High Similarity	NPC5620
0.8993	High Similarity	NPC129666
0.8971	High Similarity	NPC139326
0.8921	High Similarity	NPC240848
0.8905	High Similarity	NPC476978
0.8865	High Similarity	NPC162104
0.8815	High Similarity	NPC68865
0.8806	High Similarity	NPC248283
0.8786	High Similarity	NPC471820
0.8786	High Similarity	NPC471821
0.876	High Similarity	NPC6975
0.876	High Similarity	NPC46427
0.8714	High Similarity	NPC225648
0.8714	High Similarity	NPC329761
0.8705	High Similarity	NPC313867
0.8705	High Similarity	NPC316008
0.8696	High Similarity	NPC161069
0.869	High Similarity	NPC197743
0.869	High Similarity	NPC297145
0.8686	High Similarity	NPC239762
0.8686	High Similarity	NPC163392
0.8682	High Similarity	NPC252878
0.8652	High Similarity	NPC105717
0.8643	High Similarity	NPC314358
0.8633	High Similarity	NPC314388
0.8633	High Similarity	NPC315283
0.8605	High Similarity	NPC202521
0.8593	High Similarity	NPC287401
0.8582	High Similarity	NPC145113
0.8551	High Similarity	NPC268841
0.8551	High Similarity	NPC307357
0.8551	High Similarity	NPC46098
0.8527	High Similarity	NPC200964
0.8527	High Similarity	NPC476990
0.8511	High Similarity	NPC262077
0.85	High Similarity	NPC52748
0.8489	Intermediate Similarity	NPC168113
0.8462	Intermediate Similarity	NPC2501
0.8451	Intermediate Similarity	NPC138775
0.8444	Intermediate Similarity	NPC130309
0.844	Intermediate Similarity	NPC315266
0.844	Intermediate Similarity	NPC322878
0.8429	Intermediate Similarity	NPC197682
0.8429	Intermediate Similarity	NPC176226
0.8414	Intermediate Similarity	NPC286551
0.8406	Intermediate Similarity	NPC127741
0.8403	Intermediate Similarity	NPC475168
0.8403	Intermediate Similarity	NPC7817
0.8357	Intermediate Similarity	NPC469426
0.8357	Intermediate Similarity	NPC469427
0.8288	Intermediate Similarity	NPC122590
0.8286	Intermediate Similarity	NPC476259
0.8248	Intermediate Similarity	NPC246079
0.8231	Intermediate Similarity	NPC470546
0.8231	Intermediate Similarity	NPC470902
0.8222	Intermediate Similarity	NPC319766
0.8175	Intermediate Similarity	NPC255447
0.8154	Intermediate Similarity	NPC169328
0.8154	Intermediate Similarity	NPC470545
0.8102	Intermediate Similarity	NPC300315
0.8092	Intermediate Similarity	NPC310467
0.8092	Intermediate Similarity	NPC237420
0.8077	Intermediate Similarity	NPC470544
0.806	Intermediate Similarity	NPC474082
0.806	Intermediate Similarity	NPC175726
0.8041	Intermediate Similarity	NPC473341
0.8029	Intermediate Similarity	NPC473322
0.7971	Intermediate Similarity	NPC200589
0.7959	Intermediate Similarity	NPC283783
0.7956	Intermediate Similarity	NPC71933
0.7956	Intermediate Similarity	NPC105114
0.7956	Intermediate Similarity	NPC89923
0.7956	Intermediate Similarity	NPC239990
0.7956	Intermediate Similarity	NPC152850
0.7945	Intermediate Similarity	NPC135121
0.7931	Intermediate Similarity	NPC201244
0.7931	Intermediate Similarity	NPC477217
0.7911	Intermediate Similarity	NPC317725
0.7911	Intermediate Similarity	NPC326407
0.7911	Intermediate Similarity	NPC318930
0.7911	Intermediate Similarity	NPC317362
0.7883	Intermediate Similarity	NPC136453
0.7834	Intermediate Similarity	NPC475204
0.7834	Intermediate Similarity	NPC475123
0.7821	Intermediate Similarity	NPC473502
0.781	Intermediate Similarity	NPC101719
0.7803	Intermediate Similarity	NPC14672
0.7803	Intermediate Similarity	NPC285926
0.7803	Intermediate Similarity	NPC239357
0.7803	Intermediate Similarity	NPC315276
0.7793	Intermediate Similarity	NPC77905
0.7786	Intermediate Similarity	NPC157311
0.7778	Intermediate Similarity	NPC1390
0.7778	Intermediate Similarity	NPC62104
0.777	Intermediate Similarity	NPC111428
0.7755	Intermediate Similarity	NPC81026
0.7746	Intermediate Similarity	NPC141050
0.7737	Intermediate Similarity	NPC222466
0.773	Intermediate Similarity	NPC44805
0.773	Intermediate Similarity	NPC8761
0.7727	Intermediate Similarity	NPC471527
0.7704	Intermediate Similarity	NPC45777
0.7704	Intermediate Similarity	NPC477061
0.7692	Intermediate Similarity	NPC472923
0.7688	Intermediate Similarity	NPC471165
0.7688	Intermediate Similarity	NPC477462
0.7687	Intermediate Similarity	NPC266741
0.7652	Intermediate Similarity	NPC33742
0.7647	Intermediate Similarity	NPC71684
0.7628	Intermediate Similarity	NPC471051
0.7628	Intermediate Similarity	NPC471052
0.7628	Intermediate Similarity	NPC471053
0.7625	Intermediate Similarity	NPC137627
0.7613	Intermediate Similarity	NPC469901
0.761	Intermediate Similarity	NPC40234
0.7609	Intermediate Similarity	NPC22746
0.7586	Intermediate Similarity	NPC89489
0.7586	Intermediate Similarity	NPC132636
0.7584	Intermediate Similarity	NPC16188
0.758	Intermediate Similarity	NPC5719
0.758	Intermediate Similarity	NPC210377
0.758	Intermediate Similarity	NPC217804
0.758	Intermediate Similarity	NPC22883
0.7578	Intermediate Similarity	NPC26108
0.7576	Intermediate Similarity	NPC35850
0.7576	Intermediate Similarity	NPC276949
0.7574	Intermediate Similarity	NPC190663
0.7566	Intermediate Similarity	NPC262166
0.7554	Intermediate Similarity	NPC47667
0.755	Intermediate Similarity	NPC473491
0.7548	Intermediate Similarity	NPC469898
0.7547	Intermediate Similarity	NPC473000
0.7546	Intermediate Similarity	NPC475421
0.7532	Intermediate Similarity	NPC254700
0.7532	Intermediate Similarity	NPC15068
0.7516	Intermediate Similarity	NPC39431
0.75	Intermediate Similarity	NPC273814
0.75	Intermediate Similarity	NPC196091
0.75	Intermediate Similarity	NPC300443
0.7484	Intermediate Similarity	NPC324850
0.7484	Intermediate Similarity	NPC294516
0.7484	Intermediate Similarity	NPC63040
0.7484	Intermediate Similarity	NPC107938
0.7483	Intermediate Similarity	NPC476989
0.7469	Intermediate Similarity	NPC476227
0.7468	Intermediate Similarity	NPC469903
0.7467	Intermediate Similarity	NPC311658
0.7464	Intermediate Similarity	NPC160493
0.7453	Intermediate Similarity	NPC89831
0.7451	Intermediate Similarity	NPC56685
0.7445	Intermediate Similarity	NPC478014
0.7445	Intermediate Similarity	NPC478016
0.7445	Intermediate Similarity	NPC478015
0.7426	Intermediate Similarity	NPC314992
0.7421	Intermediate Similarity	NPC61004
0.741	Intermediate Similarity	NPC470112
0.741	Intermediate Similarity	NPC470903
0.741	Intermediate Similarity	NPC167763
0.7397	Intermediate Similarity	NPC43755
0.7394	Intermediate Similarity	NPC469666
0.7391	Intermediate Similarity	NPC46009
0.7368	Intermediate Similarity	NPC474584
0.7355	Intermediate Similarity	NPC476268
0.7355	Intermediate Similarity	NPC244509
0.7346	Intermediate Similarity	NPC230611
0.7342	Intermediate Similarity	NPC73655
0.7338	Intermediate Similarity	NPC202198
0.7338	Intermediate Similarity	NPC261934
0.7338	Intermediate Similarity	NPC5194
0.7333	Intermediate Similarity	NPC197470
0.7333	Intermediate Similarity	NPC471680
0.7329	Intermediate Similarity	NPC186617
0.7325	Intermediate Similarity	NPC24617
0.7321	Intermediate Similarity	NPC299806
0.7319	Intermediate Similarity	NPC80150
0.7317	Intermediate Similarity	NPC469900
0.7317	Intermediate Similarity	NPC50016
0.7315	Intermediate Similarity	NPC468984
0.7301	Intermediate Similarity	NPC306804
0.7301	Intermediate Similarity	NPC273755
0.7287	Intermediate Similarity	NPC88267
0.7287	Intermediate Similarity	NPC224610
0.7287	Intermediate Similarity	NPC113326
0.7287	Intermediate Similarity	NPC194390
0.7284	Intermediate Similarity	NPC471568
0.7284	Intermediate Similarity	NPC473693
0.7279	Intermediate Similarity	NPC2265
0.7278	Intermediate Similarity	NPC114806
0.7278	Intermediate Similarity	NPC469902
0.7256	Intermediate Similarity	NPC155506
0.7256	Intermediate Similarity	NPC473354

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 NPC471264 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	98
0.1-0.2	279
0.2-0.3	640
0.3-0.4	2137
0.4-0.5	3868
0.5-0.6	1665
0.6-0.7	351
0.7-0.8	107
0.8-0.85	1
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8815	High Similarity	NPD8172	Phase 2
0.8815	High Similarity	NPD8173	Phase 2
0.8741	High Similarity	NPD7113	Clinical (unspecified phase)
0.8615	High Similarity	NPD2584	Suspended
0.8148	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD8416	Discontinued
0.8029	Intermediate Similarity	NPD4175	Approved
0.8029	Intermediate Similarity	NPD4177	Approved
0.7971	Intermediate Similarity	NPD4125	Approved
0.7945	Intermediate Similarity	NPD8323	Discontinued
0.7917	Intermediate Similarity	NPD8076	Discontinued
0.7887	Intermediate Similarity	NPD5725	Approved
0.7887	Intermediate Similarity	NPD6073	Approved
0.7852	Intermediate Similarity	NPD7613	Discontinued
0.7826	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD8643	Discontinued
0.7778	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD4153	Approved
0.7746	Intermediate Similarity	NPD8265	Approved
0.7708	Intermediate Similarity	NPD6852	Discontinued
0.7708	Intermediate Similarity	NPD6901	Phase 3
0.7687	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD3073	Approved
0.7664	Intermediate Similarity	NPD3071	Approved
0.7664	Intermediate Similarity	NPD3072	Approved
0.7591	Intermediate Similarity	NPD4762	Approved
0.7591	Intermediate Similarity	NPD4761	Approved
0.7552	Intermediate Similarity	NPD5747	Discontinued
0.7535	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD4794	Discontinued
0.7532	Intermediate Similarity	NPD8417	Discontinued
0.7517	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD8315	Phase 1
0.75	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD4676	Approved
0.7465	Intermediate Similarity	NPD5263	Approved
0.7447	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2022	Approved
0.7426	Intermediate Similarity	NPD2217	Approved
0.7426	Intermediate Similarity	NPD2218	Phase 2
0.7415	Intermediate Similarity	NPD3480	Approved
0.7413	Intermediate Similarity	NPD2045	Approved
0.7413	Intermediate Similarity	NPD2044	Approved
0.7413	Intermediate Similarity	NPD2046	Approved
0.7413	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD2043	Approved
0.7413	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD21	Approved
0.7413	Intermediate Similarity	NPD2051	Approved
0.7413	Intermediate Similarity	NPD2048	Approved
0.7413	Intermediate Similarity	NPD2047	Approved
0.7407	Intermediate Similarity	NPD8126	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD8124	Phase 3
0.7403	Intermediate Similarity	NPD4648	Approved
0.7403	Intermediate Similarity	NPD4646	Approved
0.7403	Intermediate Similarity	NPD4647	Approved
0.7394	Intermediate Similarity	NPD3040	Approved
0.7389	Intermediate Similarity	NPD4557	Approved
0.7383	Intermediate Similarity	NPD6681	Discovery
0.7379	Intermediate Similarity	NPD6623	Phase 3
0.7372	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1330	Phase 2
0.7361	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5264	Approved
0.7333	Intermediate Similarity	NPD1348	Approved
0.7333	Intermediate Similarity	NPD5265	Approved
0.7324	Intermediate Similarity	NPD3588	Discontinued
0.7315	Intermediate Similarity	NPD2087	Approved
0.7315	Intermediate Similarity	NPD2088	Approved
0.7308	Intermediate Similarity	NPD7267	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3125	Approved
0.7301	Intermediate Similarity	NPD7965	Phase 2
0.7301	Intermediate Similarity	NPD7964	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3626	Phase 3
0.7273	Intermediate Similarity	NPD5230	Approved
0.7273	Intermediate Similarity	NPD5229	Approved
0.7267	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5323	Approved
0.726	Intermediate Similarity	NPD5296	Approved
0.7255	Intermediate Similarity	NPD6088	Approved
0.7248	Intermediate Similarity	NPD7511	Approved
0.7248	Intermediate Similarity	NPD7512	Approved
0.7246	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2078	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD8303	Discontinued
0.7203	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD8351	Phase 2
0.7183	Intermediate Similarity	NPD5367	Discontinued
0.7172	Intermediate Similarity	NPD4738	Phase 2
0.7153	Intermediate Similarity	NPD5759	Approved
0.7152	Intermediate Similarity	NPD2436	Approved
0.7152	Intermediate Similarity	NPD2437	Approved
0.7143	Intermediate Similarity	NPD3987	Approved
0.7143	Intermediate Similarity	NPD3988	Approved
0.7143	Intermediate Similarity	NPD5613	Approved
0.7143	Intermediate Similarity	NPD5614	Approved
0.7123	Intermediate Similarity	NPD4619	Approved
0.7123	Intermediate Similarity	NPD5299	Approved
0.7123	Intermediate Similarity	NPD4621	Approved
0.7114	Intermediate Similarity	NPD6294	Approved
0.7114	Intermediate Similarity	NPD6295	Approved
0.7113	Intermediate Similarity	NPD4677	Discontinued
0.7103	Intermediate Similarity	NPD2613	Approved
0.7092	Intermediate Similarity	NPD4215	Approved
0.7092	Intermediate Similarity	NPD2608	Approved
0.7092	Intermediate Similarity	NPD2610	Approved
0.7092	Intermediate Similarity	NPD3132	Approved
0.7092	Intermediate Similarity	NPD2612	Approved
0.7092	Intermediate Similarity	NPD2611	Approved
0.7092	Intermediate Similarity	NPD4216	Approved
0.7092	Intermediate Similarity	NPD4218	Approved
0.7092	Intermediate Similarity	NPD4217	Approved
0.7092	Intermediate Similarity	NPD3131	Approved
0.7092	Intermediate Similarity	NPD2609	Approved
0.7078	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2572	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2571	Approved
0.7075	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3089	Approved
0.7075	Intermediate Similarity	NPD4746	Phase 3
0.7075	Intermediate Similarity	NPD2574	Discontinued
0.7075	Intermediate Similarity	NPD3615	Approved
0.7075	Intermediate Similarity	NPD3616	Approved
0.7075	Intermediate Similarity	NPD3090	Approved
0.7075	Intermediate Similarity	NPD2570	Approved
0.7075	Intermediate Similarity	NPD3087	Approved
0.7075	Intermediate Similarity	NPD3614	Approved
0.7075	Intermediate Similarity	NPD2573	Approved
0.7075	Intermediate Similarity	NPD2566	Approved
0.7075	Intermediate Similarity	NPD3088	Approved
0.7075	Intermediate Similarity	NPD4745	Approved
0.707	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6792	Phase 3
0.7059	Intermediate Similarity	NPD6676	Phase 2
0.7047	Intermediate Similarity	NPD7510	Approved
0.7044	Intermediate Similarity	NPD7749	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6119	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3661	Approved
0.7034	Intermediate Similarity	NPD3662	Phase 3
0.7034	Intermediate Similarity	NPD3664	Approved
0.7034	Intermediate Similarity	NPD3663	Approved
0.7014	Intermediate Similarity	NPD2160	Approved
0.7014	Intermediate Similarity	NPD2626	Approved
0.7014	Intermediate Similarity	NPD2627	Approved
0.7014	Intermediate Similarity	NPD2159	Approved
0.7014	Intermediate Similarity	NPD2625	Approved
0.7014	Intermediate Similarity	NPD2628	Approved
0.7006	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4126	Approved
0.698	Remote Similarity	NPD4684	Phase 3
0.698	Remote Similarity	NPD4686	Approved
0.698	Remote Similarity	NPD4685	Phase 3
0.6974	Remote Similarity	NPD4152	Approved
0.6972	Remote Similarity	NPD5338	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD3644	Approved
0.6963	Remote Similarity	NPD3642	Approved
0.6963	Remote Similarity	NPD3643	Approved
0.6957	Remote Similarity	NPD7599	Phase 2
0.695	Remote Similarity	NPD7342	Discontinued
0.6948	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5204	Approved
0.6914	Remote Similarity	NPD7600	Phase 2
0.6909	Remote Similarity	NPD7485	Phase 3
0.6909	Remote Similarity	NPD7484	Phase 3
0.6879	Remote Similarity	NPD5981	Approved
0.6867	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7720	Phase 2
0.6857	Remote Similarity	NPD2117	Pre-registration
0.6857	Remote Similarity	NPD2115	Approved
0.6857	Remote Similarity	NPD2116	Approved
0.6849	Remote Similarity	NPD4151	Approved
0.6846	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1967	Approved
0.6839	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1968	Approved
0.6835	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6325	Discontinued
0.6812	Remote Similarity	NPD3598	Phase 3
0.681	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.681	Remote Similarity	NPD2097	Approved
0.6809	Remote Similarity	NPD6345	Approved
0.6809	Remote Similarity	NPD2994	Approved
0.6809	Remote Similarity	NPD6343	Approved
0.6807	Remote Similarity	NPD6303	Approved
0.6807	Remote Similarity	NPD6304	Approved
0.6797	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7131	Phase 3
0.6791	Remote Similarity	NPD7130	Phase 3
0.6786	Remote Similarity	NPD3123	Discovery
0.6779	Remote Similarity	NPD5581	Approved
0.6776	Remote Similarity	NPD4214	Discontinued
0.677	Remote Similarity	NPD2891	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