NPASS Compound

Structure

NPC41318 OpenBabel07101718322D 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 -2.4087 -2.4192 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 -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 -2.9976 -1.6336 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 -1.4796 -2.1019 0.0000 C 0 0 2 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 -3.7174 -1.2181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0440 -0.9978 0.0000 C 0 0 2 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 -4.4608 -1.5899 0.0000 C 0 0 2 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 -4.6216 -2.5584 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 2 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 27 1 0 0 0 0 19 25 2 0 0 0 0 19 26 1 0 0 0 0 20 28 1 0 0 0 0 20 30 1 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 29 1 0 0 0 0 25 33 1 0 0 0 0 26 27 1 0 0 0 0 26 35 2 0 0 0 0 27 37 2 0 0 0 0 28 33 2 0 0 0 0 28 35 1 0 0 0 0 30 22 1 1 0 0 0 30 44 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 36 1 0 0 0 0 34 29 1 6 0 0 0 34 36 1 0 0 0 0 34 40 1 0 0 0 0 35 44 1 0 0 0 0 36 46 1 1 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:	665.41
Volume:	715.052
LogP:	7.458
LogD:	4.612
LogS:	-2.393
# Rotatable Bonds:	4
TPSA:	91.92
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.173
Synthetic Accessibility Score:	5.827
Fsp3:	0.605
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:	-5.467
MDCK Permeability:	2.5066661692108028e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.978
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.374
30% Bioavailability (F30%):	0.705

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.952
Plasma Protein Binding (PPB):	95.46812438964844%
Volume Distribution (VD):	1.361
Pgp-substrate:	8.592663764953613%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.832
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.628
CYP2C9-inhibitor:	0.323
CYP2C9-substrate:	0.757
CYP2D6-inhibitor:	0.588
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.718
CYP3A4-substrate:	0.88

ADMET: Excretion

Clearance (CL):	4.244
Half-life (T1/2):	0.02

ADMET: Toxicity

hERG Blockers:	0.769
Human Hepatotoxicity (H-HT):	0.675
Drug-inuced Liver Injury (DILI):	0.297
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.958
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.101
Carcinogencity:	0.931
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC41318

Natural Product ID:	NPC41318
*Common Name:**	Nodulisporic Acids B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WCAKZBQMVHYHED-XWOVQGDBSA-N
Standard InCHI:	InChI=1S/C43H55NO5/c1-22(2)30-20-28-33-25(29-21-39(4,5)49-40(6,7)34(29)36(33)46)19-26-27-18-24-13-14-31-41(8,16-11-12-23(3)38(47)48)32(45)15-17-42(31,9)43(24,10)37(27)44(30)35(26)28/h11-12,16,19,21,24,30-32,34,36,45-46H,1,13-15,17-18,20H2,2-10H3,(H,47,48)/b16-11+,23-12+/t24-,30+,31-,32-,34+,36+,41-,42-,43+/m0/s1
SMILES:	C/C(=CC=C[C@]1(C)[C@@H](O)CC[C@]2([C@H]1CC[C@@H]1[C@]2(C)c2n3[C@H](Cc4c3c(c2C1)cc1c4[C@@H](O)[C@H]2C1=CC(OC2(C)C)(C)C)C(=C)C)C)/C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446129
PubChem CID:	44331215
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
NPT2	Others	Unspecified		IC50	=	17.4	nM	PMID[564477]
NPT2523	Organism	Ctenocephalides felis	Ctenocephalides felis	LD90	=	150.0	uM	PMID[564477]

☑ 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 NPC41318 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	343
0.1-0.2	1459
0.2-0.3	3872
0.3-0.4	15745
0.4-0.5	15479
0.5-0.6	4086
0.6-0.7	1579
0.7-0.8	108
0.8-0.85	10
0.85-0.9	8
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469312
0.9703	High Similarity	NPC183426
0.9336	High Similarity	NPC471583
0.9336	High Similarity	NPC471782
0.9289	High Similarity	NPC278540
0.9074	High Similarity	NPC311451
0.9064	High Similarity	NPC473650
0.9064	High Similarity	NPC160527
0.9019	High Similarity	NPC473565
0.8981	High Similarity	NPC242446
0.8981	High Similarity	NPC475476
0.8768	High Similarity	NPC245756
0.8705	High Similarity	NPC131273
0.8705	High Similarity	NPC473441
0.8578	High Similarity	NPC187456
0.8551	High Similarity	NPC250129
0.8502	High Similarity	NPC475165
0.8429	Intermediate Similarity	NPC97388
0.8381	Intermediate Similarity	NPC473547
0.8349	Intermediate Similarity	NPC471634
0.8349	Intermediate Similarity	NPC473806
0.8222	Intermediate Similarity	NPC470843
0.8222	Intermediate Similarity	NPC94541
0.8068	Intermediate Similarity	NPC475151
0.8019	Intermediate Similarity	NPC284102
0.7971	Intermediate Similarity	NPC473747
0.7883	Intermediate Similarity	NPC79107
0.7883	Intermediate Similarity	NPC475424
0.7822	Intermediate Similarity	NPC282033
0.7738	Intermediate Similarity	NPC61813
0.7633	Intermediate Similarity	NPC206967
0.7602	Intermediate Similarity	NPC96131
0.7463	Intermediate Similarity	NPC126492
0.7432	Intermediate Similarity	NPC471284
0.7421	Intermediate Similarity	NPC235900
0.7349	Intermediate Similarity	NPC32200
0.7339	Intermediate Similarity	NPC94428
0.7339	Intermediate Similarity	NPC263937
0.7333	Intermediate Similarity	NPC34271
0.7327	Intermediate Similarity	NPC123019
0.7318	Intermediate Similarity	NPC470280
0.7304	Intermediate Similarity	NPC470873
0.7269	Intermediate Similarity	NPC470874
0.7246	Intermediate Similarity	NPC198339
0.7217	Intermediate Similarity	NPC235885
0.7209	Intermediate Similarity	NPC231342
0.7198	Intermediate Similarity	NPC6093
0.7196	Intermediate Similarity	NPC473178
0.7163	Intermediate Similarity	NPC85066
0.7163	Intermediate Similarity	NPC181502
0.7155	Intermediate Similarity	NPC249342
0.7143	Intermediate Similarity	NPC102008
0.7123	Intermediate Similarity	NPC119700
0.7072	Intermediate Similarity	NPC18661
0.7069	Intermediate Similarity	NPC313884
0.7069	Intermediate Similarity	NPC98371
0.7062	Intermediate Similarity	NPC165201
0.7059	Intermediate Similarity	NPC477135
0.7051	Intermediate Similarity	NPC475644
0.7051	Intermediate Similarity	NPC471977
0.7051	Intermediate Similarity	NPC471190
0.7051	Intermediate Similarity	NPC470486
0.7048	Intermediate Similarity	NPC302191
0.7014	Intermediate Similarity	NPC19679
0.7014	Intermediate Similarity	NPC472444
0.7013	Intermediate Similarity	NPC2395
0.7009	Intermediate Similarity	NPC87152
0.7009	Intermediate Similarity	NPC228377
0.7009	Intermediate Similarity	NPC477787
0.7009	Intermediate Similarity	NPC475631
0.7009	Intermediate Similarity	NPC328186
0.7009	Intermediate Similarity	NPC475600
0.7009	Intermediate Similarity	NPC476110
0.7009	Intermediate Similarity	NPC122968
0.7005	Intermediate Similarity	NPC97525
0.7004	Intermediate Similarity	NPC237702
0.7	Intermediate Similarity	NPC470279
0.6996	Remote Similarity	NPC469734
0.6992	Remote Similarity	NPC292416
0.6992	Remote Similarity	NPC473689
0.6972	Remote Similarity	NPC205403
0.6967	Remote Similarity	NPC107836
0.6966	Remote Similarity	NPC473506
0.6964	Remote Similarity	NPC329982
0.6963	Remote Similarity	NPC473177
0.6962	Remote Similarity	NPC319880
0.6962	Remote Similarity	NPC244839
0.6962	Remote Similarity	NPC30456
0.6962	Remote Similarity	NPC320324
0.6957	Remote Similarity	NPC294579
0.6957	Remote Similarity	NPC144779
0.6952	Remote Similarity	NPC472443
0.6947	Remote Similarity	NPC475422
0.6947	Remote Similarity	NPC234999
0.6943	Remote Similarity	NPC203614
0.6943	Remote Similarity	NPC204491
0.6938	Remote Similarity	NPC56618
0.6935	Remote Similarity	NPC478080
0.693	Remote Similarity	NPC46413
0.6923	Remote Similarity	NPC475137
0.6923	Remote Similarity	NPC475498
0.6923	Remote Similarity	NPC473850
0.692	Remote Similarity	NPC475596
0.692	Remote Similarity	NPC316841
0.692	Remote Similarity	NPC475303
0.6913	Remote Similarity	NPC6981
0.691	Remote Similarity	NPC477788
0.6907	Remote Similarity	NPC475362
0.6904	Remote Similarity	NPC475406
0.6904	Remote Similarity	NPC170751
0.689	Remote Similarity	NPC472586
0.6886	Remote Similarity	NPC475778
0.688	Remote Similarity	NPC76565
0.688	Remote Similarity	NPC57797
0.688	Remote Similarity	NPC250807
0.6875	Remote Similarity	NPC38959
0.6875	Remote Similarity	NPC327904
0.6864	Remote Similarity	NPC57690
0.6864	Remote Similarity	NPC146824
0.6861	Remote Similarity	NPC137589
0.6861	Remote Similarity	NPC193761
0.6858	Remote Similarity	NPC87755
0.6853	Remote Similarity	NPC84815
0.6853	Remote Similarity	NPC301368
0.6847	Remote Similarity	NPC313985
0.6847	Remote Similarity	NPC249150
0.6847	Remote Similarity	NPC195461
0.6847	Remote Similarity	NPC79129
0.6847	Remote Similarity	NPC81654
0.6847	Remote Similarity	NPC49196
0.6833	Remote Similarity	NPC327769
0.6825	Remote Similarity	NPC211997
0.682	Remote Similarity	NPC473486
0.682	Remote Similarity	NPC475316
0.6809	Remote Similarity	NPC147446
0.6809	Remote Similarity	NPC471980
0.6803	Remote Similarity	NPC473540
0.6798	Remote Similarity	NPC126066
0.6797	Remote Similarity	NPC477909
0.6797	Remote Similarity	NPC42678
0.6797	Remote Similarity	NPC477907
0.6794	Remote Similarity	NPC158129
0.6793	Remote Similarity	NPC14116
0.6793	Remote Similarity	NPC470126
0.6793	Remote Similarity	NPC285411
0.6792	Remote Similarity	NPC70155
0.6792	Remote Similarity	NPC270009
0.6791	Remote Similarity	NPC476319
0.679	Remote Similarity	NPC253482
0.6787	Remote Similarity	NPC189079
0.6784	Remote Similarity	NPC470931
0.6783	Remote Similarity	NPC475602
0.6781	Remote Similarity	NPC216428
0.678	Remote Similarity	NPC141428
0.6778	Remote Similarity	NPC477531
0.6778	Remote Similarity	NPC35390
0.6778	Remote Similarity	NPC470631
0.6778	Remote Similarity	NPC473781
0.6777	Remote Similarity	NPC472122
0.6777	Remote Similarity	NPC24594
0.6777	Remote Similarity	NPC84347
0.6777	Remote Similarity	NPC134586
0.6773	Remote Similarity	NPC195314
0.677	Remote Similarity	NPC472111
0.6767	Remote Similarity	NPC471014
0.6767	Remote Similarity	NPC314552
0.6767	Remote Similarity	NPC475408
0.6766	Remote Similarity	NPC127026
0.6766	Remote Similarity	NPC127720
0.6766	Remote Similarity	NPC106593
0.6765	Remote Similarity	NPC252251
0.6765	Remote Similarity	NPC253580
0.6765	Remote Similarity	NPC33949
0.6765	Remote Similarity	NPC134384
0.6765	Remote Similarity	NPC311196
0.6763	Remote Similarity	NPC470508
0.6762	Remote Similarity	NPC34508
0.6759	Remote Similarity	NPC99428
0.6757	Remote Similarity	NPC50503
0.6754	Remote Similarity	NPC469589
0.6753	Remote Similarity	NPC4421
0.6752	Remote Similarity	NPC132642
0.6752	Remote Similarity	NPC140311
0.6752	Remote Similarity	NPC477533
0.6751	Remote Similarity	NPC202503
0.6748	Remote Similarity	NPC476090
0.6745	Remote Similarity	NPC326575
0.6743	Remote Similarity	NPC95783
0.6742	Remote Similarity	NPC245916
0.6739	Remote Similarity	NPC151976
0.6739	Remote Similarity	NPC87856
0.6738	Remote Similarity	NPC62367
0.6737	Remote Similarity	NPC473667
0.6736	Remote Similarity	NPC209174
0.6726	Remote Similarity	NPC289086
0.6724	Remote Similarity	NPC470306
0.6724	Remote Similarity	NPC132211
0.6724	Remote Similarity	NPC30570
0.6723	Remote Similarity	NPC280799
0.6723	Remote Similarity	NPC211920

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 NPC41318 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	579
0.2-0.3	631
0.3-0.4	1788
0.4-0.5	3424
0.5-0.6	2028
0.6-0.7	474
0.7-0.8	18
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
0.7668	Intermediate Similarity	NPD6995	Phase 1
0.7588	Intermediate Similarity	NPD7688	Phase 1
0.7378	Intermediate Similarity	NPD6455	Phase 3
0.7345	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7770	Phase 3
0.7198	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7921	Approved
0.7155	Intermediate Similarity	NPD6978	Phase 2
0.7155	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7777	Approved
0.7143	Intermediate Similarity	NPD7778	Approved
0.7143	Intermediate Similarity	NPD53	Approved
0.7119	Intermediate Similarity	NPD7769	Phase 3
0.7091	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD8016	Phase 3
0.7071	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6281	Approved
0.7032	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD5891	Approved
0.6996	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2920	Discontinued
0.6936	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7474	Suspended
0.6901	Remote Similarity	NPD7417	Discontinued
0.69	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD2564	Approved
0.6898	Remote Similarity	NPD2565	Phase 2
0.6884	Remote Similarity	NPD4948	Discontinued
0.6875	Remote Similarity	NPD6987	Phase 1
0.6869	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5506	Approved
0.6867	Remote Similarity	NPD5507	Approved
0.6857	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4600	Approved
0.6847	Remote Similarity	NPD4601	Approved
0.6842	Remote Similarity	NPD7418	Discontinued
0.6836	Remote Similarity	NPD8363	Approved
0.6836	Remote Similarity	NPD8364	Approved
0.6833	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7707	Approved
0.681	Remote Similarity	NPD7878	Phase 2
0.6798	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD5003	Discontinued
0.6783	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD4418	Discontinued
0.677	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD5164	Discontinued
0.6765	Remote Similarity	NPD7767	Approved
0.6761	Remote Similarity	NPD5899	Approved
0.6761	Remote Similarity	NPD5898	Approved
0.6761	Remote Similarity	NPD6452	Discontinued
0.6761	Remote Similarity	NPD5897	Approved
0.674	Remote Similarity	NPD7222	Phase 2
0.6726	Remote Similarity	NPD5901	Discontinued
0.6721	Remote Similarity	NPD5488	Discontinued
0.6712	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3763	Approved
0.6697	Remote Similarity	NPD4334	Discontinued
0.6696	Remote Similarity	NPD5936	Approved
0.6696	Remote Similarity	NPD5939	Approved
0.6696	Remote Similarity	NPD7470	Discontinued
0.6696	Remote Similarity	NPD7001	Phase 3
0.6681	Remote Similarity	NPD4897	Phase 2
0.6681	Remote Similarity	NPD5835	Phase 3
0.6681	Remote Similarity	NPD5834	Phase 3
0.668	Remote Similarity	NPD6456	Discontinued
0.6679	Remote Similarity	NPD8465	Approved
0.6679	Remote Similarity	NPD8429	Approved
0.6679	Remote Similarity	NPD8467	Approved
0.6679	Remote Similarity	NPD8428	Approved
0.6679	Remote Similarity	NPD8427	Approved
0.6679	Remote Similarity	NPD8466	Approved
0.6667	Remote Similarity	NPD7453	Approved
0.6667	Remote Similarity	NPD1326	Approved
0.6667	Remote Similarity	NPD7452	Approved
0.6667	Remote Similarity	NPD7395	Discontinued
0.6667	Remote Similarity	NPD1325	Approved
0.6652	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5913	Phase 3
0.6636	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD8358	Approved
0.6624	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD5530	Phase 1
0.6623	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7957	Phase 1
0.6621	Remote Similarity	NPD7234	Approved
0.6621	Remote Similarity	NPD7233	Approved
0.662	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.662	Remote Similarity	NPD5104	Approved
0.6619	Remote Similarity	NPD4639	Approved
0.6619	Remote Similarity	NPD4640	Approved
0.6619	Remote Similarity	NPD4638	Approved
0.6609	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6716	Phase 1
0.6598	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD7069	Discontinued
0.6594	Remote Similarity	NPD5429	Discontinued
0.6589	Remote Similarity	NPD6641	Approved
0.6589	Remote Similarity	NPD6642	Approved
0.6586	Remote Similarity	NPD8468	Phase 2
0.6583	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6733	Discontinued
0.6579	Remote Similarity	NPD8460	Approved
0.6579	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD8459	Approved
0.6579	Remote Similarity	NPD8426	Approved
0.6579	Remote Similarity	NPD8425	Approved
0.6578	Remote Similarity	NPD6999	Discontinued
0.6578	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3925	Approved
0.6565	Remote Similarity	NPD2509	Approved
0.6565	Remote Similarity	NPD2916	Discontinued
0.6565	Remote Similarity	NPD2510	Approved
0.6561	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7576	Discontinued
0.655	Remote Similarity	NPD7010	Phase 3
0.6548	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD7944	Discontinued
0.6547	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.654	Remote Similarity	NPD5021	Discontinued
0.6532	Remote Similarity	NPD4315	Phase 2
0.6529	Remote Similarity	NPD7567	Approved
0.6529	Remote Similarity	NPD7824	Approved
0.6511	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6248	Phase 2
0.6504	Remote Similarity	NPD6249	Phase 2
0.65	Remote Similarity	NPD2383	Phase 1
0.6496	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7666	Phase 3
0.6494	Remote Similarity	NPD7665	Phase 2
0.6491	Remote Similarity	NPD6975	Discontinued
0.6489	Remote Similarity	NPD6206	Phase 1
0.6488	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD6158	Phase 2
0.6488	Remote Similarity	NPD7555	Discontinued
0.6484	Remote Similarity	NPD5075	Discontinued
0.6481	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6635	Approved
0.6476	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD7797	Approved
0.6475	Remote Similarity	NPD7796	Approved
0.6468	Remote Similarity	NPD7962	Phase 2
0.6468	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5100	Phase 3
0.646	Remote Similarity	NPD7946	Pre-registration
0.646	Remote Similarity	NPD6261	Phase 3
0.6449	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7731	Approved
0.6446	Remote Similarity	NPD7730	Approved
0.6445	Remote Similarity	NPD2915	Discontinued
0.6444	Remote Similarity	NPD7935	Phase 2
0.6442	Remote Similarity	NPD7181	Phase 3
0.6441	Remote Similarity	NPD8160	Phase 2
0.6438	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD3947	Discontinued
0.6432	Remote Similarity	NPD7271	Approved
0.6426	Remote Similarity	NPD8094	Discontinued
0.6425	Remote Similarity	NPD8431	Approved
0.6422	Remote Similarity	NPD8399	Phase 1
0.6422	Remote Similarity	NPD8423	Phase 2
0.6422	Remote Similarity	NPD7672	Approved
0.6422	Remote Similarity	NPD7671	Approved
0.6416	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4501	Approved
0.6404	Remote Similarity	NPD4500	Approved
0.6402	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7678	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7856	Phase 2
0.64	Remote Similarity	NPD4602	Approved
0.64	Remote Similarity	NPD7857	Phase 3
0.6398	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7955	Approved
0.6395	Remote Similarity	NPD7956	Approved
0.6393	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD8093	Discontinued
0.6382	Remote Similarity	NPD7789	Approved
0.6382	Remote Similarity	NPD7951	Approved
0.6382	Remote Similarity	NPD7950	Approved
0.6382	Remote Similarity	NPD7791	Approved
0.6382	Remote Similarity	NPD7952	Approved
0.6382	Remote Similarity	NPD7790	Approved
0.6382	Remote Similarity	NPD7953	Approved
0.6382	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.638	Remote Similarity	NPD5444	Phase 1
0.6378	Remote Similarity	NPD8101	Phase 3
0.6376	Remote Similarity	NPD4511	Phase 1
0.6376	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD3394	Approved
0.6371	Remote Similarity	NPD3389	Approved
0.6371	Remote Similarity	NPD3393	Approved
0.6371	Remote Similarity	NPD7708	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