NPASS Compound

Structure

NPC245756 OpenBabel07101719522D 49 56 0 0 1 0 0 0 0 0999 V2000 0.7647 3.6449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2141 2.2543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9812 -0.4489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9830 -1.3839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8104 -0.8553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7017 1.5636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8303 2.0159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5396 0.4380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8282 1.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4127 0.8909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0177 -0.4195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4959 -1.2771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8282 -1.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6857 -1.0071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7297 1.9380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0360 -0.4048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8722 1.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9529 -1.2711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2760 -0.2130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4608 1.5899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1086 -0.4403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6767 2.6670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4776 -1.2917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0147 -0.9817 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8413 0.3962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7174 1.2181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4472 -0.1509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5180 -0.4683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6612 0.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0440 0.9978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7004 -0.0254 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5726 1.4344 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9976 1.6336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4796 2.1019 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4325 0.8308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4087 2.4192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9291 0.3173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9557 -2.1493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9389 -0.4030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8743 1.0351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5579 0.4527 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8575 0.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4943 1.1202 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4301 1.9125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6981 3.3574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9374 -2.1640 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4522 -2.9921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3218 0.3347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 2 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 39 1 0 0 0 0 5 39 1 0 0 0 0 6 40 1 0 0 0 0 7 40 1 0 0 0 0 9 42 1 0 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 12 23 2 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 31 1 0 0 0 0 15 17 1 0 0 0 0 15 32 1 0 0 0 0 16 41 1 0 0 0 0 17 42 1 0 0 0 0 18 24 1 0 0 0 0 18 28 1 0 0 0 0 19 25 1 0 0 0 0 19 27 2 0 0 0 0 20 26 1 0 0 0 0 20 30 2 0 0 0 0 21 29 2 0 0 0 0 21 39 1 0 0 0 0 23 38 1 0 0 0 0 24 43 1 6 0 0 0 25 26 2 0 0 0 0 25 29 1 0 0 0 0 26 33 1 0 0 0 0 27 28 1 0 0 0 0 27 35 1 0 0 0 0 28 37 2 0 0 0 0 29 30 1 0 0 0 0 30 40 1 0 0 0 0 31 41 1 1 0 0 0 31 42 1 0 0 0 0 32 41 1 1 0 0 0 32 45 1 0 0 0 0 33 35 2 0 0 0 0 33 36 1 0 0 0 0 34 22 1 1 0 0 0 34 36 1 0 0 0 0 34 44 1 0 0 0 0 35 44 1 0 0 0 0 36 46 2 0 0 0 0 37 43 1 0 0 0 0 37 44 1 0 0 0 0 38 47 2 0 0 0 0 38 48 1 0 0 0 0 39 49 1 0 0 0 0 40 49 1 0 0 0 0 41 8 1 1 0 0 0 42 43 1 6 0 0 0 43 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	663.39
Volume:	712.415
LogP:	8.566
LogD:	5.271
LogS:	-2.596
# Rotatable Bonds:	5
TPSA:	91.4
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.186
Synthetic Accessibility Score:	5.8
Fsp3:	0.558
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:	-4.939
MDCK Permeability:	2.0423027308424935e-05
Pgp-inhibitor:	0.545
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.172
20% Bioavailability (F20%):	0.096
30% Bioavailability (F30%):	0.052

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	96.04763793945312%
Volume Distribution (VD):	1.254
Pgp-substrate:	4.197204113006592%

ADMET: Metabolism

CYP1A2-inhibitor:	0.328
CYP1A2-substrate:	0.834
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.678
CYP2C9-inhibitor:	0.634
CYP2C9-substrate:	0.636
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.429
CYP3A4-substrate:	0.224

ADMET: Excretion

Clearance (CL):	3.014
Half-life (T1/2):	0.114

ADMET: Toxicity

hERG Blockers:	0.103
Human Hepatotoxicity (H-HT):	0.321
Drug-inuced Liver Injury (DILI):	0.401
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.166
Carcinogencity:	0.927
Eye Corrosion:	0.003
Eye Irritation:	0.01
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: NPC245756

Natural Product ID:	NPC245756
*Common Name:**	LDGYIEXFZWQVLQ-MINZZOGMSA-N
IUPAC Name:	n.a.
Synonyms:	Delta-23-Nodulisporic Acid A4
Standard InCHIKey:	LDGYIEXFZWQVLQ-MINZZOGMSA-N
Standard InCHI:	InChI=1S/C43H53NO5/c1-22(2)34-36(46)33-26-20-30-29(21-39(4,5)49-40(30,6)7)25(26)19-27-28-18-24-13-14-31-41(8,16-11-12-23(3)38(47)48)32(45)15-17-42(31,9)43(24,10)37(28)44(34)35(27)33/h12,19-21,24,31-32,34,45H,1,11,13-18H2,2-10H3,(H,47,48)/b23-12+/t24-,31-,32-,34-,41-,42-,43+/m0/s1
SMILES:	C/C(=CCC[C@]1(C)[C@@H](O)CC[C@]2([C@H]1CC[C@@H]1[C@]2(C)c2n3[C@@H](C(=C)C)C(=O)c4c3c(c2C1)cc1c4C=C2C1=CC(OC2(C)C)(C)C)C)/C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507924
PubChem CID:	11239267
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO32628	nodulisporium	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387649]

☑ 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	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2523	Organism	Ctenocephalides felis	Ctenocephalides felis	LD90	>	15.1	uM	PMID[554339]
NPT2	Others	Unspecified		IC50	=	23.0	nM	PMID[554339]

☑ 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 NPC245756 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	333
0.1-0.2	1438
0.2-0.3	3611
0.3-0.4	15420
0.4-0.5	16527
0.5-0.6	3864
0.6-0.7	1387
0.7-0.8	95
0.8-0.85	11
0.85-0.9	6
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9384	High Similarity	NPC278540
0.934	High Similarity	NPC471583
0.934	High Similarity	NPC471782
0.9167	High Similarity	NPC311451
0.8795	High Similarity	NPC473441
0.8795	High Similarity	NPC131273
0.8768	High Similarity	NPC41318
0.8768	High Similarity	NPC469312
0.8605	High Similarity	NPC183426
0.8585	High Similarity	NPC187456
0.8341	Intermediate Similarity	NPC473565
0.8294	Intermediate Similarity	NPC250129
0.8263	Intermediate Similarity	NPC97388
0.8246	Intermediate Similarity	NPC475165
0.8216	Intermediate Similarity	NPC473547
0.8199	Intermediate Similarity	NPC284102
0.8194	Intermediate Similarity	NPC242446
0.8194	Intermediate Similarity	NPC475476
0.8178	Intermediate Similarity	NPC473650
0.8178	Intermediate Similarity	NPC160527
0.799	Intermediate Similarity	NPC475151
0.7973	Intermediate Similarity	NPC79107
0.7973	Intermediate Similarity	NPC475424
0.7946	Intermediate Similarity	NPC473806
0.7946	Intermediate Similarity	NPC471634
0.7895	Intermediate Similarity	NPC473747
0.7675	Intermediate Similarity	NPC282033
0.7668	Intermediate Similarity	NPC61813
0.765	Intermediate Similarity	NPC470280
0.7476	Intermediate Similarity	NPC206967
0.7458	Intermediate Similarity	NPC470843
0.7458	Intermediate Similarity	NPC94541
0.7455	Intermediate Similarity	NPC96131
0.7339	Intermediate Similarity	NPC123019
0.7304	Intermediate Similarity	NPC126492
0.7289	Intermediate Similarity	NPC471284
0.7277	Intermediate Similarity	NPC235900
0.7256	Intermediate Similarity	NPC181502
0.7256	Intermediate Similarity	NPC85066
0.7229	Intermediate Similarity	NPC235885
0.7183	Intermediate Similarity	NPC34271
0.7162	Intermediate Similarity	NPC18661
0.7137	Intermediate Similarity	NPC471190
0.7137	Intermediate Similarity	NPC470486
0.7137	Intermediate Similarity	NPC475644
0.7137	Intermediate Similarity	NPC471977
0.7095	Intermediate Similarity	NPC198339
0.7094	Intermediate Similarity	NPC228377
0.7094	Intermediate Similarity	NPC475631
0.7094	Intermediate Similarity	NPC328186
0.7094	Intermediate Similarity	NPC476110
0.7094	Intermediate Similarity	NPC475600
0.7094	Intermediate Similarity	NPC122968
0.7094	Intermediate Similarity	NPC87152
0.7094	Intermediate Similarity	NPC477787
0.7091	Intermediate Similarity	NPC470279
0.7089	Intermediate Similarity	NPC70155
0.7078	Intermediate Similarity	NPC477044
0.7078	Intermediate Similarity	NPC477041
0.7051	Intermediate Similarity	NPC473506
0.7048	Intermediate Similarity	NPC6093
0.7046	Intermediate Similarity	NPC30456
0.704	Intermediate Similarity	NPC477043
0.7026	Intermediate Similarity	NPC2395
0.7017	Intermediate Similarity	NPC237702
0.7013	Intermediate Similarity	NPC84815
0.7013	Intermediate Similarity	NPC301368
0.7009	Intermediate Similarity	NPC475498
0.7009	Intermediate Similarity	NPC473850
0.7009	Intermediate Similarity	NPC475137
0.7004	Intermediate Similarity	NPC316841
0.7004	Intermediate Similarity	NPC292416
0.7004	Intermediate Similarity	NPC473689
0.7004	Intermediate Similarity	NPC475303
0.7004	Intermediate Similarity	NPC475596
0.6996	Remote Similarity	NPC477788
0.6987	Remote Similarity	NPC170751
0.6975	Remote Similarity	NPC319880
0.6975	Remote Similarity	NPC244839
0.6975	Remote Similarity	NPC320324
0.697	Remote Similarity	NPC144779
0.697	Remote Similarity	NPC294579
0.6968	Remote Similarity	NPC477045
0.6966	Remote Similarity	NPC471980
0.6966	Remote Similarity	NPC76565
0.6966	Remote Similarity	NPC57797
0.6966	Remote Similarity	NPC250807
0.6957	Remote Similarity	NPC203614
0.6957	Remote Similarity	NPC204491
0.6957	Remote Similarity	NPC477907
0.6957	Remote Similarity	NPC42678
0.6957	Remote Similarity	NPC477909
0.6943	Remote Similarity	NPC317752
0.694	Remote Similarity	NPC216428
0.693	Remote Similarity	NPC99428
0.6926	Remote Similarity	NPC6981
0.6923	Remote Similarity	NPC127720
0.6923	Remote Similarity	NPC127026
0.692	Remote Similarity	NPC475362
0.6917	Remote Similarity	NPC327769
0.6917	Remote Similarity	NPC475406
0.6916	Remote Similarity	NPC165201
0.6913	Remote Similarity	NPC4421
0.69	Remote Similarity	NPC318299
0.6898	Remote Similarity	NPC119700
0.6897	Remote Similarity	NPC62367
0.6894	Remote Similarity	NPC147446
0.6892	Remote Similarity	NPC32200
0.6888	Remote Similarity	NPC327904
0.6888	Remote Similarity	NPC38959
0.6878	Remote Similarity	NPC14116
0.6878	Remote Similarity	NPC285411
0.6878	Remote Similarity	NPC57690
0.6878	Remote Similarity	NPC211920
0.6878	Remote Similarity	NPC146824
0.6872	Remote Similarity	NPC253482
0.6872	Remote Similarity	NPC258062
0.6872	Remote Similarity	NPC127677
0.6864	Remote Similarity	NPC477902
0.6864	Remote Similarity	NPC328154
0.6862	Remote Similarity	NPC150698
0.6862	Remote Similarity	NPC96801
0.6857	Remote Similarity	NPC97525
0.6853	Remote Similarity	NPC475408
0.6853	Remote Similarity	NPC471016
0.6853	Remote Similarity	NPC478083
0.6853	Remote Similarity	NPC471014
0.6849	Remote Similarity	NPC134384
0.6849	Remote Similarity	NPC311196
0.6844	Remote Similarity	NPC98715
0.684	Remote Similarity	NPC329982
0.6833	Remote Similarity	NPC472116
0.6828	Remote Similarity	NPC46225
0.6828	Remote Similarity	NPC225821
0.6824	Remote Similarity	NPC473115
0.6824	Remote Similarity	NPC75600
0.6824	Remote Similarity	NPC158020
0.6824	Remote Similarity	NPC473089
0.6824	Remote Similarity	NPC212768
0.6824	Remote Similarity	NPC6576
0.6812	Remote Similarity	NPC234999
0.681	Remote Similarity	NPC470306
0.6809	Remote Similarity	NPC477912
0.6807	Remote Similarity	NPC124029
0.6802	Remote Similarity	NPC469734
0.68	Remote Similarity	NPC137589
0.6793	Remote Similarity	NPC141428
0.6789	Remote Similarity	NPC475648
0.6783	Remote Similarity	NPC204303
0.6777	Remote Similarity	NPC263937
0.6777	Remote Similarity	NPC475426
0.6777	Remote Similarity	NPC35208
0.6777	Remote Similarity	NPC94428
0.6774	Remote Similarity	NPC107836
0.6771	Remote Similarity	NPC102008
0.6765	Remote Similarity	NPC472762
0.6765	Remote Similarity	NPC148860
0.6761	Remote Similarity	NPC476090
0.6757	Remote Similarity	NPC472293
0.6757	Remote Similarity	NPC231342
0.6756	Remote Similarity	NPC300183
0.6753	Remote Similarity	NPC151976
0.6753	Remote Similarity	NPC475778
0.6753	Remote Similarity	NPC87856
0.6744	Remote Similarity	NPC302191
0.6741	Remote Similarity	NPC472297
0.6741	Remote Similarity	NPC472296
0.674	Remote Similarity	NPC289086
0.6738	Remote Similarity	NPC132211
0.6737	Remote Similarity	NPC477903
0.6725	Remote Similarity	NPC63041
0.6724	Remote Similarity	NPC267965
0.6722	Remote Similarity	NPC290529
0.6716	Remote Similarity	NPC200743
0.6712	Remote Similarity	NPC46413
0.6711	Remote Similarity	NPC249150
0.6711	Remote Similarity	NPC49196
0.6711	Remote Similarity	NPC79129
0.6711	Remote Similarity	NPC81654
0.6711	Remote Similarity	NPC195461
0.6711	Remote Similarity	NPC313985
0.6709	Remote Similarity	NPC477908
0.6709	Remote Similarity	NPC206343
0.6709	Remote Similarity	NPC246658
0.6706	Remote Similarity	NPC244543
0.6696	Remote Similarity	NPC48042
0.6696	Remote Similarity	NPC271862
0.6696	Remote Similarity	NPC304179
0.6696	Remote Similarity	NPC472550
0.6695	Remote Similarity	NPC267926
0.6695	Remote Similarity	NPC470874
0.6694	Remote Similarity	NPC213143
0.6682	Remote Similarity	NPC245916
0.6681	Remote Similarity	NPC476467
0.6681	Remote Similarity	NPC266192
0.6681	Remote Similarity	NPC472553
0.6681	Remote Similarity	NPC315545
0.6681	Remote Similarity	NPC314297
0.6667	Remote Similarity	NPC475601
0.6667	Remote Similarity	NPC314648

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 NPC245756 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	578
0.2-0.3	635
0.3-0.4	1960
0.4-0.5	3434
0.5-0.6	1862
0.6-0.7	452
0.7-0.8	14
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
0.7675	Intermediate Similarity	NPD7688	Phase 1
0.76	Intermediate Similarity	NPD6995	Phase 1
0.7195	Intermediate Similarity	NPD6987	Phase 1
0.7149	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD4948	Discontinued
0.7104	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7921	Approved
0.7021	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD5891	Approved
0.692	Remote Similarity	NPD7767	Approved
0.6897	Remote Similarity	NPD7878	Phase 2
0.6886	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6733	Discontinued
0.6883	Remote Similarity	NPD3394	Approved
0.6883	Remote Similarity	NPD3393	Approved
0.6883	Remote Similarity	NPD3389	Approved
0.6872	Remote Similarity	NPD2509	Approved
0.6872	Remote Similarity	NPD2510	Approved
0.6856	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.684	Remote Similarity	NPD7707	Approved
0.6826	Remote Similarity	NPD7455	Approved
0.6826	Remote Similarity	NPD7454	Approved
0.6824	Remote Similarity	NPD7395	Discontinued
0.6807	Remote Similarity	NPD7994	Phase 2
0.6804	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD8016	Phase 3
0.6803	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD3925	Approved
0.6789	Remote Similarity	NPD7233	Approved
0.6789	Remote Similarity	NPD7234	Approved
0.6784	Remote Similarity	NPD7010	Phase 3
0.6776	Remote Similarity	NPD5897	Approved
0.6776	Remote Similarity	NPD5899	Approved
0.6776	Remote Similarity	NPD5898	Approved
0.6771	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD53	Approved
0.6771	Remote Similarity	NPD7777	Approved
0.6771	Remote Similarity	NPD7778	Approved
0.677	Remote Similarity	NPD6176	Phase 1
0.6762	Remote Similarity	NPD1573	Approved
0.6762	Remote Similarity	NPD1575	Approved
0.675	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7770	Phase 3
0.6739	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1631	Approved
0.6712	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4601	Approved
0.6711	Remote Similarity	NPD4600	Approved
0.6707	Remote Similarity	NPD7417	Discontinued
0.6697	Remote Similarity	NPD5809	Phase 3
0.6696	Remote Similarity	NPD5835	Phase 3
0.6696	Remote Similarity	NPD5834	Phase 3
0.6682	Remote Similarity	NPD6281	Approved
0.6667	Remote Similarity	NPD8160	Phase 2
0.6667	Remote Similarity	NPD8468	Phase 2
0.6667	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5901	Discontinued
0.6667	Remote Similarity	NPD3947	Discontinued
0.6653	Remote Similarity	NPD6455	Phase 3
0.6652	Remote Similarity	NPD3795	Approved
0.6652	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD2336	Approved
0.6652	Remote Similarity	NPD3794	Approved
0.6639	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6142	Phase 3
0.6638	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5475	Discontinued
0.6636	Remote Similarity	NPD4334	Discontinued
0.6636	Remote Similarity	NPD5104	Approved
0.6624	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD8146	Phase 2
0.6609	Remote Similarity	NPD5429	Discontinued
0.6604	Remote Similarity	NPD7795	Phase 2
0.6598	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD3259	Approved
0.6594	Remote Similarity	NPD8114	Approved
0.6594	Remote Similarity	NPD8115	Approved
0.659	Remote Similarity	NPD8363	Approved
0.659	Remote Similarity	NPD8364	Approved
0.6587	Remote Similarity	NPD7769	Phase 3
0.6587	Remote Similarity	NPD1630	Approved
0.6578	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7470	Discontinued
0.6565	Remote Similarity	NPD7001	Phase 3
0.6564	Remote Similarity	NPD6479	Discontinued
0.6562	Remote Similarity	NPD7776	Approved
0.6562	Remote Similarity	NPD7944	Discontinued
0.6558	Remote Similarity	NPD5471	Phase 3
0.655	Remote Similarity	NPD2920	Discontinued
0.6547	Remote Similarity	NPD4315	Phase 2
0.6546	Remote Similarity	NPD5821	Approved
0.6545	Remote Similarity	NPD7853	Phase 2
0.654	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD5488	Discontinued
0.6533	Remote Similarity	NPD2307	Discontinued
0.6529	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6978	Phase 2
0.6527	Remote Similarity	NPD5506	Approved
0.6527	Remote Similarity	NPD5507	Approved
0.6525	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD6962	Phase 2
0.6512	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6376	Discontinued
0.6502	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6456	Discontinued
0.65	Remote Similarity	NPD5075	Discontinued
0.6495	Remote Similarity	NPD7687	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7962	Phase 2
0.6483	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7941	Phase 3
0.6481	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6716	Phase 1
0.6479	Remote Similarity	NPD4639	Approved
0.6479	Remote Similarity	NPD4638	Approved
0.6479	Remote Similarity	NPD4640	Approved
0.6478	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD7824	Approved
0.6468	Remote Similarity	NPD7069	Discontinued
0.6468	Remote Similarity	NPD5866	Approved
0.6463	Remote Similarity	NPD7953	Approved
0.6463	Remote Similarity	NPD7789	Approved
0.6463	Remote Similarity	NPD7951	Approved
0.6463	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD7791	Approved
0.6463	Remote Similarity	NPD7950	Approved
0.6463	Remote Similarity	NPD7790	Approved
0.6463	Remote Similarity	NPD7952	Approved
0.6462	Remote Similarity	NPD2915	Discontinued
0.6457	Remote Similarity	NPD2564	Approved
0.6457	Remote Similarity	NPD4499	Approved
0.6457	Remote Similarity	NPD2565	Phase 2
0.6455	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD6249	Phase 2
0.6447	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD6999	Discontinued
0.6447	Remote Similarity	NPD6248	Phase 2
0.6446	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6770	Approved
0.6443	Remote Similarity	NPD8358	Approved
0.6442	Remote Similarity	NPD8429	Approved
0.6442	Remote Similarity	NPD8466	Approved
0.6442	Remote Similarity	NPD8427	Approved
0.6442	Remote Similarity	NPD8428	Approved
0.6442	Remote Similarity	NPD8465	Approved
0.6442	Remote Similarity	NPD8467	Approved
0.644	Remote Similarity	NPD6790	Phase 1
0.6435	Remote Similarity	NPD7187	Phase 2
0.6434	Remote Similarity	NPD7781	Approved
0.6434	Remote Similarity	NPD7780	Approved
0.6432	Remote Similarity	NPD6206	Phase 1
0.6429	Remote Similarity	NPD8325	Phase 3
0.6429	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8326	Phase 3
0.6422	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7957	Phase 1
0.6422	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7397	Approved
0.6417	Remote Similarity	NPD7398	Approved
0.6416	Remote Similarity	NPD4602	Approved
0.6415	Remote Similarity	NPD6635	Approved
0.6414	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6261	Phase 3
0.6398	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD4373	Phase 2
0.6393	Remote Similarity	NPD7730	Approved
0.6393	Remote Similarity	NPD7731	Approved
0.6391	Remote Similarity	NPD7727	Phase 2
0.638	Remote Similarity	NPD7482	Phase 2
0.638	Remote Similarity	NPD7483	Phase 2
0.6375	Remote Similarity	NPD7576	Discontinued
0.6375	Remote Similarity	NPD7404	Approved
0.6371	Remote Similarity	NPD8094	Discontinued
0.6371	Remote Similarity	NPD7772	Phase 3
0.6368	Remote Similarity	NPD7665	Phase 2
0.6368	Remote Similarity	NPD7666	Phase 3
0.6364	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7925	Phase 2
0.6364	Remote Similarity	NPD7924	Phase 2
0.636	Remote Similarity	NPD4938	Phase 2
0.636	Remote Similarity	NPD5003	Discontinued
0.6356	Remote Similarity	NPD4918	Discontinued
0.6352	Remote Similarity	NPD8289	Discontinued
0.6352	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD4500	Approved
0.6348	Remote Similarity	NPD4501	Approved
0.6347	Remote Similarity	NPD8425	Approved
0.6347	Remote Similarity	NPD1587	Approved
0.6347	Remote Similarity	NPD8460	Approved
0.6347	Remote Similarity	NPD8426	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