NPASS Compound

Structure

NPC52801 OpenBabel07101718182D 46 56 0 0 1 0 0 0 0 0999 V2000 7.7710 -0.4503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7528 -3.3072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4503 -2.9766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8358 -1.4482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8756 -5.6297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1874 -5.2324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8456 -5.6324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5638 -5.2324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8448 -5.6722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1874 -4.4377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3805 -4.7471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5472 -2.2278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0460 -4.5344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1435 -3.0463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3790 -1.6727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1646 -2.8423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1002 -4.0572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2370 -3.5562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0348 -5.4030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1074 -1.5604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3728 -3.1257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6907 -3.9221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0040 -2.0033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3854 -4.8743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6120 -3.2257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0688 -3.0012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0575 -5.6148 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.9654 -3.4440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5638 -4.4377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3789 -4.8268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8756 -4.0404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3404 -3.1134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9146 -3.9017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3401 -4.4508 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.9138 -3.9416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1186 -4.4144 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5086 -3.6685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9603 -3.9609 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.0952 -3.7137 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.2520 -4.0404 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3645 -4.6581 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.2756 -2.1155 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.8756 -3.2457 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.6680 -3.7103 0.0000 N 0 3 3 0 0 0 0 0 0 0 0 0 1.4495 -3.0164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5070 -3.8019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 44 1 0 0 0 0 3 45 1 0 0 0 0 4 23 1 0 0 0 0 5 6 2 0 0 0 0 5 8 1 0 0 0 0 6 10 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 29 2 0 0 0 0 9 30 1 0 0 0 0 10 31 2 0 0 0 0 11 33 2 0 0 0 0 12 15 1 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 24 2 0 0 0 0 14 16 1 0 0 0 0 14 40 1 0 0 0 0 15 42 1 0 0 0 0 16 44 1 0 0 0 0 17 46 1 0 0 0 0 18 26 2 0 0 0 0 18 32 1 0 0 0 0 19 27 1 0 0 0 0 19 34 1 0 0 0 0 20 23 2 0 0 0 0 20 42 1 0 0 0 0 21 28 2 0 0 0 0 21 43 1 0 0 0 0 22 24 1 0 0 0 0 22 44 1 0 0 0 0 23 26 1 0 0 0 0 24 27 1 0 0 0 0 25 35 2 0 0 0 0 25 37 1 0 0 0 0 26 28 1 0 0 0 0 27 36 1 0 0 0 0 28 38 1 0 0 0 0 29 31 1 0 0 0 0 29 40 1 0 0 0 0 30 35 1 0 0 0 0 30 41 2 0 0 0 0 31 43 1 0 0 0 0 32 37 2 0 0 0 0 32 42 1 0 0 0 0 33 35 1 0 0 0 0 33 45 1 0 0 0 0 34 40 1 0 0 0 0 34 44 1 0 0 0 0 36 38 1 0 0 0 0 36 39 1 0 0 0 0 37 41 1 0 0 0 0 38 46 1 0 0 0 0 39 40 1 0 0 0 0 39 43 1 0 0 0 0 M CHG 1 44 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	609.32
Volume:	637.523
LogP:	4.756
LogD:	4.027
LogS:	-3.742
# Rotatable Bonds:	3
TPSA:	37.3
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	11
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.369
Synthetic Accessibility Score:	6.987
Fsp3:	0.425
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.522
MDCK Permeability:	1.3433733329293318e-05
Pgp-inhibitor:	0.158
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.963
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	79.09571838378906%
Volume Distribution (VD):	1.751
Pgp-substrate:	10.076910972595215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.292
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.911
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.093
CYP2D6-inhibitor:	0.97
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.733
CYP3A4-substrate:	0.933

ADMET: Excretion

Clearance (CL):	1.904
Half-life (T1/2):	0.884

ADMET: Toxicity

hERG Blockers:	0.975
Human Hepatotoxicity (H-HT):	0.929
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.981
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.781
Carcinogencity:	0.67
Eye Corrosion:	0.003
Eye Irritation:	0.004
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: NPC52801

Natural Product ID:	NPC52801
*Common Name:**	Guiaflavine
IUPAC Name:	(4aR,5aS,8aS,13aS,15aR,15bR)-15-(3-ethyl-8-methoxy-7,12-dihydro-6H-indolo[2,3-a]quinolizin-5-ium-2-yl)-6-methyl-2,4a,5,5a,7,8,13a,15a,15b,16-decahydro4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline-6-ium;dichloride
Synonyms:	Guiaflavine
Standard InCHIKey:	ZOQZMDXDYBAHPK-CZJFRNDDSA-M
Standard InCHI:	InChI=1S/C40H41N4O2.2ClH/c1-4-23-20-42-15-12-25-35-30(9-7-11-33(35)45-3)41-37(25)32(42)18-26(23)28-21-43-31-10-6-5-8-29(31)40-14-16-44(2)22-24-13-17-46-38(28)36(39(40)43)27(24)19-34(40)44;;/h5-11,13,18,20-21,27,34,36,38-39H,4,12,14-17,19,22H2,1-3H3;2*1H/q+1;;/p-1/t27-,34-,36-,38-,39-,40+,44?;;/m0../s1
SMILES:	CCc1cn2CCC3=c4c(=NC3=c2cc1C1=CN2c3ccccc3[C@]35[C@@H]2[C@@H]2[C@H]1OCC=C1[C@@H]2C[C@@H]5[N+](C1)(CC3)C)cccc4OC.Cl.[Cl-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL555473
PubChem CID:	11802688
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002749] Strychnos alkaloids

*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
NPO541	Strychnos guianensis	Species	Loganiaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[10395514]
NPO541	Strychnos guianensis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO541	Strychnos guianensis	Species	Loganiaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	LD100	=	100.0	mg kg-1	PMID[542486]

☑ 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 NPC52801 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	558
0.1-0.2	1929
0.2-0.3	8961
0.3-0.4	12078
0.4-0.5	14034
0.5-0.6	4122
0.6-0.7	971
0.7-0.8	43
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7711	Intermediate Similarity	NPC138830
0.7711	Intermediate Similarity	NPC67904
0.7464	Intermediate Similarity	NPC126066
0.7409	Intermediate Similarity	NPC320147
0.7339	Intermediate Similarity	NPC115588
0.7306	Intermediate Similarity	NPC473743
0.7268	Intermediate Similarity	NPC469740
0.723	Intermediate Similarity	NPC159815
0.722	Intermediate Similarity	NPC162440
0.7198	Intermediate Similarity	NPC127178
0.7198	Intermediate Similarity	NPC329747
0.7196	Intermediate Similarity	NPC478074
0.7158	Intermediate Similarity	NPC116519
0.7137	Intermediate Similarity	NPC151171
0.7135	Intermediate Similarity	NPC475420
0.7128	Intermediate Similarity	NPC473880
0.7092	Intermediate Similarity	NPC475097
0.7079	Intermediate Similarity	NPC21425
0.7064	Intermediate Similarity	NPC329982
0.7059	Intermediate Similarity	NPC22476
0.7056	Intermediate Similarity	NPC475422
0.705	Intermediate Similarity	NPC98197
0.7048	Intermediate Similarity	NPC473005
0.7047	Intermediate Similarity	NPC70172
0.7043	Intermediate Similarity	NPC473540
0.7042	Intermediate Similarity	NPC475910
0.7041	Intermediate Similarity	NPC139085
0.7041	Intermediate Similarity	NPC214626
0.7041	Intermediate Similarity	NPC251212
0.7037	Intermediate Similarity	NPC473006
0.7033	Intermediate Similarity	NPC329793
0.7028	Intermediate Similarity	NPC472111
0.7027	Intermediate Similarity	NPC469735
0.7009	Intermediate Similarity	NPC469589
0.7	Intermediate Similarity	NPC318525
0.7	Intermediate Similarity	NPC477066
0.7	Intermediate Similarity	NPC477157
0.7	Intermediate Similarity	NPC477533
0.7	Intermediate Similarity	NPC10653
0.7	Intermediate Similarity	NPC477156
0.6978	Remote Similarity	NPC223242
0.6976	Remote Similarity	NPC470483
0.697	Remote Similarity	NPC478081
0.6963	Remote Similarity	NPC87755
0.6952	Remote Similarity	NPC11017
0.6935	Remote Similarity	NPC285941
0.6923	Remote Similarity	NPC17437
0.6916	Remote Similarity	NPC139373
0.6912	Remote Similarity	NPC285841
0.6909	Remote Similarity	NPC96321
0.6909	Remote Similarity	NPC473041
0.6908	Remote Similarity	NPC470485
0.6902	Remote Similarity	NPC477155
0.6901	Remote Similarity	NPC329833
0.6901	Remote Similarity	NPC470484
0.6901	Remote Similarity	NPC14339
0.6898	Remote Similarity	NPC471304
0.6897	Remote Similarity	NPC476095
0.6897	Remote Similarity	NPC477067
0.6897	Remote Similarity	NPC478082
0.6891	Remote Similarity	NPC478080
0.6885	Remote Similarity	NPC243162
0.6884	Remote Similarity	NPC470931
0.6881	Remote Similarity	NPC475602
0.6878	Remote Similarity	NPC288110
0.6878	Remote Similarity	NPC217294
0.686	Remote Similarity	NPC473004
0.686	Remote Similarity	NPC204970
0.6857	Remote Similarity	NPC100863
0.6856	Remote Similarity	NPC216816
0.6856	Remote Similarity	NPC315498
0.6856	Remote Similarity	NPC230942
0.6845	Remote Similarity	NPC473569
0.6838	Remote Similarity	NPC81939
0.6835	Remote Similarity	NPC264176
0.6835	Remote Similarity	NPC127996
0.6835	Remote Similarity	NPC472098
0.6827	Remote Similarity	NPC473178
0.6827	Remote Similarity	NPC302001
0.6822	Remote Similarity	NPC285558
0.6822	Remote Similarity	NPC87714
0.6818	Remote Similarity	NPC85482
0.6814	Remote Similarity	NPC249405
0.6809	Remote Similarity	NPC475666
0.6808	Remote Similarity	NPC295898
0.6804	Remote Similarity	NPC471080
0.6804	Remote Similarity	NPC469592
0.6797	Remote Similarity	NPC131977
0.6794	Remote Similarity	NPC243626
0.6789	Remote Similarity	NPC206592
0.6784	Remote Similarity	NPC471294
0.6782	Remote Similarity	NPC287588
0.6767	Remote Similarity	NPC301501
0.6766	Remote Similarity	NPC260075
0.6765	Remote Similarity	NPC179704
0.6763	Remote Similarity	NPC105055
0.6763	Remote Similarity	NPC22689
0.6758	Remote Similarity	NPC251160
0.6758	Remote Similarity	NPC94157
0.6755	Remote Similarity	NPC264589
0.6749	Remote Similarity	NPC190461
0.6746	Remote Similarity	NPC203972
0.6741	Remote Similarity	NPC477532
0.674	Remote Similarity	NPC470126
0.6738	Remote Similarity	NPC469450
0.6732	Remote Similarity	NPC473007
0.673	Remote Similarity	NPC161804
0.6726	Remote Similarity	NPC222046
0.6725	Remote Similarity	NPC475253
0.672	Remote Similarity	NPC470925
0.6717	Remote Similarity	NPC33507
0.6715	Remote Similarity	NPC477186
0.6714	Remote Similarity	NPC230313
0.6713	Remote Similarity	NPC246140
0.6713	Remote Similarity	NPC195787
0.6712	Remote Similarity	NPC208284
0.6711	Remote Similarity	NPC162748
0.6701	Remote Similarity	NPC24954
0.6699	Remote Similarity	NPC33902
0.6699	Remote Similarity	NPC276674
0.6697	Remote Similarity	NPC476116
0.6696	Remote Similarity	NPC475720
0.6696	Remote Similarity	NPC474192
0.6695	Remote Similarity	NPC131486
0.6683	Remote Similarity	NPC312531
0.6683	Remote Similarity	NPC174629
0.6683	Remote Similarity	NPC474059
0.6683	Remote Similarity	NPC84478
0.6682	Remote Similarity	NPC10732
0.6682	Remote Similarity	NPC267423
0.6682	Remote Similarity	NPC469594
0.6681	Remote Similarity	NPC469722
0.6681	Remote Similarity	NPC469451
0.6681	Remote Similarity	NPC469452
0.6667	Remote Similarity	NPC234772
0.6667	Remote Similarity	NPC473458
0.6667	Remote Similarity	NPC475147
0.6667	Remote Similarity	NPC473177
0.6667	Remote Similarity	NPC476651
0.6652	Remote Similarity	NPC477531
0.6651	Remote Similarity	NPC28510
0.6651	Remote Similarity	NPC203628
0.6651	Remote Similarity	NPC272706
0.6651	Remote Similarity	NPC474077
0.6638	Remote Similarity	NPC314954
0.6634	Remote Similarity	NPC176127
0.6634	Remote Similarity	NPC56618
0.6634	Remote Similarity	NPC473432
0.6633	Remote Similarity	NPC225319
0.6627	Remote Similarity	NPC237901
0.6627	Remote Similarity	NPC195788
0.6625	Remote Similarity	NPC133609
0.6624	Remote Similarity	NPC329932
0.6622	Remote Similarity	NPC132642
0.6621	Remote Similarity	NPC475133
0.6621	Remote Similarity	NPC168250
0.662	Remote Similarity	NPC72211
0.662	Remote Similarity	NPC475774
0.6617	Remote Similarity	NPC66573
0.6615	Remote Similarity	NPC26850
0.6609	Remote Similarity	NPC209174
0.6606	Remote Similarity	NPC473180
0.6605	Remote Similarity	NPC295676
0.6604	Remote Similarity	NPC162653
0.6603	Remote Similarity	NPC473008
0.6603	Remote Similarity	NPC5630
0.6603	Remote Similarity	NPC474904
0.6599	Remote Similarity	NPC282339
0.6599	Remote Similarity	NPC99632
0.6598	Remote Similarity	NPC189079
0.6597	Remote Similarity	NPC469734
0.6595	Remote Similarity	NPC473105
0.6592	Remote Similarity	NPC183407
0.6592	Remote Similarity	NPC170114
0.6591	Remote Similarity	NPC290689
0.6591	Remote Similarity	NPC199667
0.6587	Remote Similarity	NPC249996
0.6584	Remote Similarity	NPC478083
0.6579	Remote Similarity	NPC472100
0.6578	Remote Similarity	NPC108826
0.657	Remote Similarity	NPC476202
0.6568	Remote Similarity	NPC81175
0.6567	Remote Similarity	NPC160113
0.6567	Remote Similarity	NPC476220
0.6565	Remote Similarity	NPC252251
0.6565	Remote Similarity	NPC253580
0.6565	Remote Similarity	NPC311906
0.6564	Remote Similarity	NPC315257
0.6564	Remote Similarity	NPC280272
0.6562	Remote Similarity	NPC305984
0.656	Remote Similarity	NPC477161
0.6555	Remote Similarity	NPC320088
0.6553	Remote Similarity	NPC19679
0.6549	Remote Similarity	NPC472099
0.6549	Remote Similarity	NPC128115
0.6548	Remote Similarity	NPC477158
0.6547	Remote Similarity	NPC470549
0.6547	Remote Similarity	NPC189661
0.6546	Remote Similarity	NPC26872
0.6546	Remote Similarity	NPC476568

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 NPC52801 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	587
0.2-0.3	790
0.3-0.4	1432
0.4-0.5	3262
0.5-0.6	2368
0.6-0.7	417
0.7-0.8	3
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
0.7358	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD5680	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5078	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6357	Discontinued
0.7062	Intermediate Similarity	NPD3984	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3983	Phase 3
0.7041	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5600	Discontinued
0.7016	Intermediate Similarity	NPD6060	Clinical (unspecified phase)
0.699	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4796	Discontinued
0.6957	Remote Similarity	NPD8016	Phase 3
0.6957	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD8403	Phase 1
0.6923	Remote Similarity	NPD8358	Approved
0.6916	Remote Similarity	NPD7222	Phase 2
0.6905	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7479	Phase 2
0.6875	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5530	Phase 1
0.6856	Remote Similarity	NPD19	Approved
0.6856	Remote Similarity	NPD1743	Approved
0.6856	Remote Similarity	NPD1742	Approved
0.6816	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7034	Discontinued
0.6798	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7877	Suspended
0.6759	Remote Similarity	NPD7453	Approved
0.6759	Remote Similarity	NPD7452	Approved
0.6754	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6738	Phase 2
0.6753	Remote Similarity	NPD6737	Phase 2
0.6746	Remote Similarity	NPD7262	Phase 1
0.6746	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD8363	Approved
0.6721	Remote Similarity	NPD8364	Approved
0.6683	Remote Similarity	NPD6281	Approved
0.6683	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5670	Approved
0.6667	Remote Similarity	NPD6526	Approved
0.6667	Remote Similarity	NPD4203	Approved
0.6667	Remote Similarity	NPD4204	Approved
0.6667	Remote Similarity	NPD4951	Discontinued
0.6667	Remote Similarity	NPD6037	Discontinued
0.6667	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD7671	Approved
0.6651	Remote Similarity	NPD7672	Approved
0.6634	Remote Similarity	NPD4354	Approved
0.6627	Remote Similarity	NPD8467	Approved
0.6627	Remote Similarity	NPD8427	Approved
0.6627	Remote Similarity	NPD8429	Approved
0.6627	Remote Similarity	NPD8466	Approved
0.6627	Remote Similarity	NPD8465	Approved
0.6627	Remote Similarity	NPD8428	Approved
0.6625	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7674	Phase 3
0.6623	Remote Similarity	NPD7675	Phase 3
0.6622	Remote Similarity	NPD7678	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6340	Approved
0.6618	Remote Similarity	NPD6339	Approved
0.6617	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7820	Phase 3
0.6606	Remote Similarity	NPD7225	Discontinued
0.6605	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5617	Suspended
0.6585	Remote Similarity	NPD3037	Phase 1
0.6584	Remote Similarity	NPD5938	Phase 3
0.6578	Remote Similarity	NPD7194	Discontinued
0.6575	Remote Similarity	NPD5658	Approved
0.6573	Remote Similarity	NPD6527	Approved
0.6564	Remote Similarity	NPD7221	Approved
0.6564	Remote Similarity	NPD7219	Approved
0.6564	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.656	Remote Similarity	NPD3003	Approved
0.656	Remote Similarity	NPD6150	Discontinued
0.6558	Remote Similarity	NPD6810	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD4418	Discontinued
0.6557	Remote Similarity	NPD7686	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7796	Approved
0.6552	Remote Similarity	NPD7797	Approved
0.6552	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6063	Approved
0.6547	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.654	Remote Similarity	NPD5587	Approved
0.654	Remote Similarity	NPD6569	Phase 2
0.6538	Remote Similarity	NPD5256	Discontinued
0.6526	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD3477	Phase 2
0.6526	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6523	Remote Similarity	NPD8426	Approved
0.6523	Remote Similarity	NPD8425	Approved
0.6523	Remote Similarity	NPD8459	Approved
0.6523	Remote Similarity	NPD8460	Approved
0.6522	Remote Similarity	NPD3109	Approved
0.6522	Remote Similarity	NPD3110	Approved
0.652	Remote Similarity	NPD3503	Approved
0.652	Remote Similarity	NPD3504	Approved
0.6514	Remote Similarity	NPD31	Approved
0.6514	Remote Similarity	NPD4036	Approved
0.6514	Remote Similarity	NPD4039	Approved
0.6514	Remote Similarity	NPD4033	Approved
0.6514	Remote Similarity	NPD4035	Approved
0.6514	Remote Similarity	NPD4037	Approved
0.6514	Remote Similarity	NPD4122	Approved
0.6514	Remote Similarity	NPD32	Approved
0.6514	Remote Similarity	NPD4038	Approved
0.6514	Remote Similarity	NPD4034	Approved
0.6512	Remote Similarity	NPD6874	Approved
0.6509	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD1034	Phase 3
0.6505	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD3763	Approved
0.6502	Remote Similarity	NPD7032	Approved
0.6498	Remote Similarity	NPD6208	Discontinued
0.6495	Remote Similarity	NPD5515	Phase 2
0.6495	Remote Similarity	NPD8401	Approved
0.6495	Remote Similarity	NPD8402	Approved
0.6495	Remote Similarity	NPD8400	Approved
0.649	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.649	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.649	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD3920	Phase 2
0.6486	Remote Similarity	NPD6220	Phase 3
0.6484	Remote Similarity	NPD6245	Phase 2
0.6479	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD6251	Discontinued
0.6476	Remote Similarity	NPD7291	Discontinued
0.6468	Remote Similarity	NPD6991	Approved
0.6468	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD6379	Discontinued
0.6462	Remote Similarity	NPD3924	Approved
0.6462	Remote Similarity	NPD3923	Approved
0.6462	Remote Similarity	NPD3921	Approved
0.6462	Remote Similarity	NPD5811	Approved
0.6462	Remote Similarity	NPD3922	Approved
0.6456	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6238	Discontinued
0.645	Remote Similarity	NPD6978	Phase 2
0.645	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6550	Discontinued
0.6445	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4795	Phase 2
0.6429	Remote Similarity	NPD5944	Phase 1
0.6429	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2383	Phase 1
0.6429	Remote Similarity	NPD5945	Phase 1
0.6425	Remote Similarity	NPD7020	Approved
0.6425	Remote Similarity	NPD7019	Approved
0.6425	Remote Similarity	NPD5845	Phase 2
0.6422	Remote Similarity	NPD3515	Approved
0.6422	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD3516	Approved
0.6419	Remote Similarity	NPD8311	Discontinued
0.6419	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD4889	Approved
0.6404	Remote Similarity	NPD4083	Discontinued
0.6402	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6590	Discontinued
0.64	Remote Similarity	NPD5903	Approved
0.64	Remote Similarity	NPD5902	Approved
0.64	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD3349	Phase 2
0.6396	Remote Similarity	NPD2789	Approved
0.6396	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.639	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.639	Remote Similarity	NPD8359	Phase 2
0.6387	Remote Similarity	NPD5754	Discontinued
0.6387	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD6457	Approved
0.6384	Remote Similarity	NPD3816	Phase 1
0.6384	Remote Similarity	NPD3815	Phase 1
0.6383	Remote Similarity	NPD7558	Phase 2
0.6383	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD5599	Discontinued
0.6381	Remote Similarity	NPD5565	Discontinued
0.6376	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD8149	Discontinued
0.6368	Remote Similarity	NPD2843	Phase 2

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