NPASS Compound

Structure

NPC471782 OpenBabel07101719192D 51 58 0 0 1 0 0 0 0 0999 V2000 0.7652 3.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2143 2.2558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9851 -0.4492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9869 -1.3848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8148 -0.8559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7061 1.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8341 2.0172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5419 0.4383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8287 1.4862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4130 0.8914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9341 -3.8521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0204 -0.4198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4988 -1.2779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8287 -1.4862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6868 -1.0078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7309 1.9392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0380 -0.4051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8728 1.4608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9535 -1.2719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2781 -0.2132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1119 -0.4406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6772 2.6688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4811 -1.2926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0147 -0.9823 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8438 0.3965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4488 -0.1510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5190 -0.4686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6642 0.2602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7015 -0.0255 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5743 1.4353 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7198 1.2189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9996 1.6347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0473 0.9984 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4805 2.1033 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4341 0.8313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4636 1.5909 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4103 2.4208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9297 0.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9596 -2.1507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9428 -0.4033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8781 1.0357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5596 0.4530 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8581 0.4784 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 1.4952 1.1209 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4323 1.9138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6246 2.5601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6999 3.3596 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9419 -2.1654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4557 -2.9941 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3259 0.3349 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 40 1 0 0 0 0 5 40 1 0 0 0 0 6 41 1 0 0 0 0 7 41 1 0 0 0 0 9 43 1 0 0 0 0 11 50 1 0 0 0 0 12 13 1 0 0 0 0 12 17 2 0 0 0 0 13 23 2 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 29 1 0 0 0 0 16 18 1 0 0 0 0 16 30 1 0 0 0 0 17 42 1 0 0 0 0 18 43 1 0 0 0 0 19 24 1 0 0 0 0 19 27 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 28 2 0 0 0 0 21 40 1 0 0 0 0 23 39 1 0 0 0 0 24 44 1 6 0 0 0 25 28 1 0 0 0 0 25 31 1 0 0 0 0 26 27 1 0 0 0 0 26 35 2 0 0 0 0 27 38 2 0 0 0 0 29 42 1 1 0 0 0 29 43 1 0 0 0 0 30 42 1 1 0 0 0 30 46 1 0 0 0 0 31 32 2 0 0 0 0 31 36 1 0 0 0 0 32 35 1 0 0 0 0 32 37 1 0 0 0 0 33 28 1 6 0 0 0 33 36 1 0 0 0 0 33 41 1 0 0 0 0 34 22 1 1 0 0 0 34 37 1 0 0 0 0 34 45 1 0 0 0 0 35 45 1 0 0 0 0 36 47 1 1 0 0 0 37 48 2 0 0 0 0 38 44 1 0 0 0 0 38 45 1 0 0 0 0 39 49 2 0 0 0 0 39 50 1 0 0 0 0 40 51 1 0 0 0 0 41 51 1 0 0 0 0 42 8 1 1 0 0 0 43 44 1 6 0 0 0 44 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	693.4
Volume:	738.502
LogP:	7.872
LogD:	5.19
LogS:	-2.798
# Rotatable Bonds:	5
TPSA:	100.63
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.144
Synthetic Accessibility Score:	5.842
Fsp3:	0.568
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:	-5.486
MDCK Permeability:	2.0302408302086405e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.947
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.079
30% Bioavailability (F30%):	0.191

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.608
Plasma Protein Binding (PPB):	95.09972381591797%
Volume Distribution (VD):	1.422
Pgp-substrate:	8.70063591003418%

ADMET: Metabolism

CYP1A2-inhibitor:	0.129
CYP1A2-substrate:	0.85
CYP2C19-inhibitor:	0.471
CYP2C19-substrate:	0.662
CYP2C9-inhibitor:	0.854
CYP2C9-substrate:	0.653
CYP2D6-inhibitor:	0.783
CYP2D6-substrate:	0.123
CYP3A4-inhibitor:	0.871
CYP3A4-substrate:	0.913

ADMET: Excretion

Clearance (CL):	6.472
Half-life (T1/2):	0.034

ADMET: Toxicity

hERG Blockers:	0.524
Human Hepatotoxicity (H-HT):	0.49
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.339
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.123
Carcinogencity:	0.954
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.899

Download Data

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

Natural Product: NPC471782

Natural Product ID:	NPC471782
*Common Name:**	GXQVUYCPGXDGED-MVCWHVMQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GXQVUYCPGXDGED-MVCWHVMQSA-N
Standard InCHI:	InChI=1S/C44H55NO6/c1-22(2)34-37(48)32-31-25(28-21-40(4,5)51-41(6,7)33(28)36(31)47)20-26-27-19-24-14-15-29-42(8,17-12-13-23(3)39(49)50-11)30(46)16-18-43(29,9)44(24,10)38(27)45(34)35(26)32/h12-13,17,20-21,24,29-30,33-34,36,46-47H,1,14-16,18-19H2,2-11H3/b17-12+,23-13+/t24-,29-,30-,33+,34-,36+,42-,43-,44+/m0/s1
SMILES:	CC(=C)C1C(=O)C2=C3N1C4=C(C3=CC5=C2C(C6C5=CC(OC6(C)C)(C)C)O)CC7C4(C8(CCC(C(C8CC7)(C)C=CC=C(C)C(=O)OC)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL321523
PubChem CID:	44331493
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
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12270179]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542359]
NPO32628	nodulisporium	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387649]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17363259]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25978520]

☑ 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	2

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		LD90	=	10.0	p.p.m.	PMID[559022]
NPT2	Others	Unspecified		IC50	=	0.43	nM	PMID[559023]
NPT2523	Organism	Ctenocephalides felis	Ctenocephalides felis	LD90	=	14.4	uM	PMID[559023]

☑ 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 NPC471782 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	364
0.1-0.2	1543
0.2-0.3	4016
0.3-0.4	14747
0.4-0.5	16165
0.5-0.6	4067
0.6-0.7	1583
0.7-0.8	194
0.8-0.85	7
0.85-0.9	2
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471583
0.9953	High Similarity	NPC278540
0.9722	High Similarity	NPC311451
0.934	High Similarity	NPC245756
0.9336	High Similarity	NPC469312
0.9336	High Similarity	NPC41318
0.933	High Similarity	NPC131273
0.933	High Similarity	NPC473441
0.9074	High Similarity	NPC183426
0.8879	High Similarity	NPC473565
0.8479	Intermediate Similarity	NPC473650
0.8479	Intermediate Similarity	NPC160527
0.8409	Intermediate Similarity	NPC242446
0.8409	Intermediate Similarity	NPC475476
0.8238	Intermediate Similarity	NPC473806
0.8238	Intermediate Similarity	NPC471634
0.8028	Intermediate Similarity	NPC187456
0.8009	Intermediate Similarity	NPC250129
0.7964	Intermediate Similarity	NPC475165
0.7919	Intermediate Similarity	NPC284102
0.7902	Intermediate Similarity	NPC97388
0.789	Intermediate Similarity	NPC470843
0.789	Intermediate Similarity	NPC94541
0.7857	Intermediate Similarity	NPC473547
0.7792	Intermediate Similarity	NPC475424
0.7792	Intermediate Similarity	NPC79107
0.7634	Intermediate Similarity	NPC470280
0.7557	Intermediate Similarity	NPC475151
0.7511	Intermediate Similarity	NPC282033
0.7466	Intermediate Similarity	NPC473747
0.7425	Intermediate Similarity	NPC61813
0.7353	Intermediate Similarity	NPC470486
0.7353	Intermediate Similarity	NPC471190
0.7353	Intermediate Similarity	NPC475644
0.7353	Intermediate Similarity	NPC471977
0.7311	Intermediate Similarity	NPC477787
0.7311	Intermediate Similarity	NPC122968
0.7311	Intermediate Similarity	NPC328186
0.7311	Intermediate Similarity	NPC87152
0.7311	Intermediate Similarity	NPC228377
0.7311	Intermediate Similarity	NPC476110
0.7311	Intermediate Similarity	NPC475600
0.7311	Intermediate Similarity	NPC475631
0.7303	Intermediate Similarity	NPC237702
0.7296	Intermediate Similarity	NPC96131
0.7292	Intermediate Similarity	NPC473689
0.7292	Intermediate Similarity	NPC292416
0.7269	Intermediate Similarity	NPC473506
0.7261	Intermediate Similarity	NPC319880
0.7261	Intermediate Similarity	NPC244839
0.7261	Intermediate Similarity	NPC30456
0.7261	Intermediate Similarity	NPC320324
0.7238	Intermediate Similarity	NPC14116
0.7238	Intermediate Similarity	NPC285411
0.7227	Intermediate Similarity	NPC475498
0.7227	Intermediate Similarity	NPC475137
0.7227	Intermediate Similarity	NPC473850
0.7227	Intermediate Similarity	NPC235885
0.7224	Intermediate Similarity	NPC253482
0.722	Intermediate Similarity	NPC475303
0.722	Intermediate Similarity	NPC316841
0.722	Intermediate Similarity	NPC475596
0.7215	Intermediate Similarity	NPC477788
0.721	Intermediate Similarity	NPC471284
0.7208	Intermediate Similarity	NPC311196
0.7208	Intermediate Similarity	NPC475362
0.7208	Intermediate Similarity	NPC134384
0.7202	Intermediate Similarity	NPC475406
0.7202	Intermediate Similarity	NPC170751
0.7185	Intermediate Similarity	NPC76565
0.7185	Intermediate Similarity	NPC57797
0.7185	Intermediate Similarity	NPC250807
0.7172	Intermediate Similarity	NPC327904
0.7172	Intermediate Similarity	NPC38959
0.7168	Intermediate Similarity	NPC470279
0.7167	Intermediate Similarity	NPC146824
0.7161	Intermediate Similarity	NPC301368
0.7161	Intermediate Similarity	NPC84815
0.716	Intermediate Similarity	NPC70155
0.7149	Intermediate Similarity	NPC206967
0.7143	Intermediate Similarity	NPC106593
0.7137	Intermediate Similarity	NPC475648
0.7131	Intermediate Similarity	NPC263937
0.7131	Intermediate Similarity	NPC94428
0.7131	Intermediate Similarity	NPC327769
0.7126	Intermediate Similarity	NPC478083
0.7124	Intermediate Similarity	NPC235900
0.712	Intermediate Similarity	NPC107836
0.7119	Intermediate Similarity	NPC475316
0.7119	Intermediate Similarity	NPC473486
0.7119	Intermediate Similarity	NPC294579
0.7119	Intermediate Similarity	NPC144779
0.7113	Intermediate Similarity	NPC471980
0.7106	Intermediate Similarity	NPC477907
0.7106	Intermediate Similarity	NPC42678
0.7106	Intermediate Similarity	NPC477909
0.7095	Intermediate Similarity	NPC211920
0.7089	Intermediate Similarity	NPC216428
0.7083	Intermediate Similarity	NPC477902
0.7078	Intermediate Similarity	NPC473781
0.7078	Intermediate Similarity	NPC150698
0.7078	Intermediate Similarity	NPC35390
0.7078	Intermediate Similarity	NPC470631
0.7078	Intermediate Similarity	NPC96801
0.7076	Intermediate Similarity	NPC6981
0.7071	Intermediate Similarity	NPC127720
0.7071	Intermediate Similarity	NPC127026
0.7064	Intermediate Similarity	NPC4421
0.7061	Intermediate Similarity	NPC475426
0.7061	Intermediate Similarity	NPC35208
0.7059	Intermediate Similarity	NPC140311
0.7049	Intermediate Similarity	NPC213143
0.7047	Intermediate Similarity	NPC329982
0.7046	Intermediate Similarity	NPC62367
0.7042	Intermediate Similarity	NPC473667
0.7039	Intermediate Similarity	NPC234999
0.7031	Intermediate Similarity	NPC123019
0.7029	Intermediate Similarity	NPC2395
0.7025	Intermediate Similarity	NPC124029
0.7022	Intermediate Similarity	NPC181502
0.7022	Intermediate Similarity	NPC85066
0.702	Intermediate Similarity	NPC238278
0.7012	Intermediate Similarity	NPC328154
0.7004	Intermediate Similarity	NPC475408
0.7004	Intermediate Similarity	NPC102008
0.7004	Intermediate Similarity	NPC471014
0.7004	Intermediate Similarity	NPC471016
0.6983	Remote Similarity	NPC314297
0.6983	Remote Similarity	NPC315545
0.6979	Remote Similarity	NPC475778
0.6979	Remote Similarity	NPC476467
0.6977	Remote Similarity	NPC126492
0.6975	Remote Similarity	NPC75600
0.6975	Remote Similarity	NPC158020
0.6975	Remote Similarity	NPC473089
0.6975	Remote Similarity	NPC212768
0.6975	Remote Similarity	NPC473115
0.6975	Remote Similarity	NPC6576
0.697	Remote Similarity	NPC314648
0.6966	Remote Similarity	NPC314834
0.6962	Remote Similarity	NPC204491
0.6962	Remote Similarity	NPC470306
0.6962	Remote Similarity	NPC203614
0.6958	Remote Similarity	NPC477903
0.6958	Remote Similarity	NPC477912
0.6949	Remote Similarity	NPC317752
0.6944	Remote Similarity	NPC469734
0.694	Remote Similarity	NPC313796
0.694	Remote Similarity	NPC18661
0.694	Remote Similarity	NPC315638
0.694	Remote Similarity	NPC313345
0.694	Remote Similarity	NPC314855
0.6914	Remote Similarity	NPC148860
0.6907	Remote Similarity	NPC318299
0.6907	Remote Similarity	NPC323551
0.6907	Remote Similarity	NPC280473
0.6905	Remote Similarity	NPC476090
0.69	Remote Similarity	NPC32200
0.6897	Remote Similarity	NPC289086
0.6887	Remote Similarity	NPC478080
0.6885	Remote Similarity	NPC475601
0.6885	Remote Similarity	NPC57690
0.6885	Remote Similarity	NPC470873
0.6883	Remote Similarity	NPC137589
0.6881	Remote Similarity	NPC84347
0.688	Remote Similarity	NPC63041
0.6878	Remote Similarity	NPC51008
0.6878	Remote Similarity	NPC41724
0.6875	Remote Similarity	NPC34271
0.6875	Remote Similarity	NPC223590
0.6872	Remote Similarity	NPC233727
0.687	Remote Similarity	NPC477906
0.6862	Remote Similarity	NPC206343
0.6862	Remote Similarity	NPC246658
0.6862	Remote Similarity	NPC473837
0.6862	Remote Similarity	NPC477908
0.6858	Remote Similarity	NPC1203
0.6851	Remote Similarity	NPC472550
0.6851	Remote Similarity	NPC48042
0.6851	Remote Similarity	NPC304179
0.6849	Remote Similarity	NPC264674
0.6848	Remote Similarity	NPC244543
0.6846	Remote Similarity	NPC470874
0.6846	Remote Similarity	NPC477901
0.6842	Remote Similarity	NPC469748
0.6835	Remote Similarity	NPC472553
0.6831	Remote Similarity	NPC147446
0.6818	Remote Similarity	NPC280799
0.6805	Remote Similarity	NPC472555
0.6803	Remote Similarity	NPC477899
0.6803	Remote Similarity	NPC477900
0.6803	Remote Similarity	NPC141428
0.6802	Remote Similarity	NPC474701
0.6797	Remote Similarity	NPC475489
0.6795	Remote Similarity	NPC13603
0.679	Remote Similarity	NPC235364
0.6787	Remote Similarity	NPC475619
0.6787	Remote Similarity	NPC198339
0.6786	Remote Similarity	NPC37473
0.6784	Remote Similarity	NPC67551

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 NPC471782 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	596
0.2-0.3	663
0.3-0.4	1937
0.4-0.5	3306
0.5-0.6	1929
0.6-0.7	469
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
0.7811	Intermediate Similarity	NPD7688	Phase 1
0.7739	Intermediate Similarity	NPD6995	Phase 1
0.7269	Intermediate Similarity	NPD6987	Phase 1
0.7247	Intermediate Similarity	NPD7921	Approved
0.7215	Intermediate Similarity	NPD4948	Discontinued
0.7172	Intermediate Similarity	NPD5891	Approved
0.7119	Intermediate Similarity	NPD7878	Phase 2
0.7097	Intermediate Similarity	NPD7770	Phase 3
0.7031	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8016	Phase 3
0.7016	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD53	Approved
0.7004	Intermediate Similarity	NPD7778	Approved
0.7004	Intermediate Similarity	NPD7777	Approved
0.6988	Remote Similarity	NPD7417	Discontinued
0.6974	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6455	Phase 3
0.6942	Remote Similarity	NPD3925	Approved
0.693	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7769	Phase 3
0.692	Remote Similarity	NPD8363	Approved
0.692	Remote Similarity	NPD8364	Approved
0.6917	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6733	Discontinued
0.6891	Remote Similarity	NPD3389	Approved
0.6891	Remote Similarity	NPD3394	Approved
0.6891	Remote Similarity	NPD3393	Approved
0.688	Remote Similarity	NPD2509	Approved
0.688	Remote Similarity	NPD2510	Approved
0.6872	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7767	Approved
0.6857	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2920	Discontinued
0.6832	Remote Similarity	NPD6456	Discontinued
0.6824	Remote Similarity	NPD5901	Discontinued
0.6824	Remote Similarity	NPD3947	Discontinued
0.682	Remote Similarity	NPD8160	Phase 2
0.6811	Remote Similarity	NPD5488	Discontinued
0.6793	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7707	Approved
0.677	Remote Similarity	NPD2565	Phase 2
0.677	Remote Similarity	NPD2564	Approved
0.6766	Remote Similarity	NPD8429	Approved
0.6766	Remote Similarity	NPD8465	Approved
0.6766	Remote Similarity	NPD8428	Approved
0.6766	Remote Similarity	NPD8466	Approved
0.6766	Remote Similarity	NPD8427	Approved
0.6766	Remote Similarity	NPD8467	Approved
0.6763	Remote Similarity	NPD7395	Discontinued
0.6752	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD3259	Approved
0.6748	Remote Similarity	NPD7994	Phase 2
0.6748	Remote Similarity	NPD6978	Phase 2
0.6747	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD8468	Phase 2
0.6724	Remote Similarity	NPD4600	Approved
0.6724	Remote Similarity	NPD4601	Approved
0.6723	Remote Similarity	NPD7010	Phase 3
0.6723	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD6716	Phase 1
0.6681	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.668	Remote Similarity	NPD4373	Phase 2
0.668	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8426	Approved
0.6667	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3794	Approved
0.6667	Remote Similarity	NPD6962	Phase 2
0.6667	Remote Similarity	NPD3795	Approved
0.6667	Remote Similarity	NPD8460	Approved
0.6667	Remote Similarity	NPD8425	Approved
0.6667	Remote Similarity	NPD8459	Approved
0.6667	Remote Similarity	NPD5003	Discontinued
0.6654	Remote Similarity	NPD8358	Approved
0.6653	Remote Similarity	NPD6142	Phase 3
0.6653	Remote Similarity	NPD7470	Discontinued
0.6653	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD7001	Phase 3
0.6638	Remote Similarity	NPD8146	Phase 2
0.6627	Remote Similarity	NPD4952	Phase 3
0.6623	Remote Similarity	NPD6281	Approved
0.6621	Remote Similarity	NPD1573	Approved
0.6621	Remote Similarity	NPD1575	Approved
0.6611	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6770	Approved
0.6594	Remote Similarity	NPD2336	Approved
0.6594	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6790	Phase 1
0.6583	Remote Similarity	NPD5475	Discontinued
0.6579	Remote Similarity	NPD7233	Approved
0.6579	Remote Similarity	NPD7234	Approved
0.6578	Remote Similarity	NPD7776	Approved
0.6568	Remote Similarity	NPD6176	Phase 1
0.6567	Remote Similarity	NPD7925	Phase 2
0.6567	Remote Similarity	NPD7924	Phase 2
0.6562	Remote Similarity	NPD5897	Approved
0.6562	Remote Similarity	NPD5898	Approved
0.6562	Remote Similarity	NPD5899	Approved
0.6562	Remote Similarity	NPD5821	Approved
0.6561	Remote Similarity	NPD7853	Phase 2
0.6556	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7454	Approved
0.6556	Remote Similarity	NPD8097	Phase 3
0.6556	Remote Similarity	NPD8096	Phase 3
0.6556	Remote Similarity	NPD7455	Approved
0.6555	Remote Similarity	NPD5429	Discontinued
0.6545	Remote Similarity	NPD5506	Approved
0.6545	Remote Similarity	NPD5507	Approved
0.6542	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6999	Discontinued
0.6533	Remote Similarity	NPD7181	Phase 3
0.6528	Remote Similarity	NPD7708	Approved
0.6527	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD8463	Approved
0.6524	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6523	Remote Similarity	NPD7576	Discontinued
0.6514	Remote Similarity	NPD1631	Approved
0.6509	Remote Similarity	NPD7944	Discontinued
0.6508	Remote Similarity	NPD3746	Discontinued
0.6502	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7941	Phase 3
0.6498	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6452	Discontinued
0.6488	Remote Similarity	NPD7069	Discontinued
0.6481	Remote Similarity	NPD2307	Discontinued
0.6471	Remote Similarity	NPD7474	Suspended
0.6466	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7665	Phase 2
0.6458	Remote Similarity	NPD7666	Phase 3
0.6458	Remote Similarity	NPD2916	Discontinued
0.6458	Remote Similarity	NPD6376	Discontinued
0.6457	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4602	Approved
0.6437	Remote Similarity	NPD7398	Approved
0.6437	Remote Similarity	NPD7397	Approved
0.6435	Remote Similarity	NPD4334	Discontinued
0.6434	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7962	Phase 2
0.6432	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6431	Remote Similarity	NPD7803	Approved
0.6431	Remote Similarity	NPD3006	Discontinued
0.6429	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7824	Approved
0.6426	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.642	Remote Similarity	NPD5866	Approved
0.6419	Remote Similarity	NPD5809	Phase 3
0.6417	Remote Similarity	NPD7953	Approved
0.6417	Remote Similarity	NPD7790	Approved
0.6417	Remote Similarity	NPD7951	Approved
0.6417	Remote Similarity	NPD7950	Approved
0.6417	Remote Similarity	NPD7952	Approved
0.6417	Remote Similarity	NPD7791	Approved
0.6417	Remote Similarity	NPD7789	Approved
0.6416	Remote Similarity	NPD1643	Phase 3
0.6413	Remote Similarity	NPD7418	Discontinued
0.6409	Remote Similarity	NPD4946	Phase 2
0.6408	Remote Similarity	NPD8489	Phase 1
0.6407	Remote Similarity	NPD4499	Approved
0.64	Remote Similarity	NPD6642	Approved
0.64	Remote Similarity	NPD6641	Approved
0.6397	Remote Similarity	NPD3258	Approved
0.6393	Remote Similarity	NPD8094	Discontinued
0.6393	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD7772	Phase 3
0.6391	Remote Similarity	NPD5050	Approved
0.6391	Remote Similarity	NPD8091	Phase 3
0.639	Remote Similarity	NPD8423	Phase 2
0.639	Remote Similarity	NPD8399	Phase 1
0.6382	Remote Similarity	NPD5164	Discontinued
0.6381	Remote Similarity	NPD4938	Phase 2
0.6376	Remote Similarity	NPD1630	Approved
0.6375	Remote Similarity	NPD8289	Discontinued
0.6375	Remote Similarity	NPD7957	Phase 1
0.6375	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD8102	Discontinued
0.6368	Remote Similarity	NPD4418	Discontinued
0.6367	Remote Similarity	NPD7955	Approved
0.6367	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6367	Remote Similarity	NPD7956	Approved
0.6367	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6367	Remote Similarity	NPD4897	Phase 2
0.6364	Remote Similarity	NPD5835	Phase 3
0.6364	Remote Similarity	NPD4506	Discontinued
0.6364	Remote Similarity	NPD5834	Phase 3
0.6357	Remote Similarity	NPD4561	Discontinued
0.6356	Remote Similarity	NPD5471	Phase 3

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