NPASS Compound

Structure

CID9891 OpenBabel06191715332D 31 33 0 0 1 0 0 0 0 0999 V2000 1.5522 -2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5759 -2.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4662 1.3975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8283 -2.0476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2350 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0704 0.2749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2514 -1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7796 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 -0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0649 0.3795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2460 -1.3431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5116 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6527 -0.4296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4716 1.2930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8337 -2.1521 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 1.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6472 -0.3250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 29 1 0 0 0 0 8 30 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 15 1 0 0 0 0 10 18 2 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 20 2 0 0 0 0 13 1 1 1 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 2 1 6 0 0 0 14 22 1 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 18 23 1 0 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 19 27 1 0 0 0 0 20 24 1 0 0 0 0 20 28 1 0 0 0 0 21 15 1 6 0 0 0 21 31 1 0 0 0 0 22 16 1 6 0 0 0 22 31 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.21
Volume:	443.704
LogP:	3.876
LogD:	3.632
LogS:	-4.622
# Rotatable Bonds:	8
TPSA:	64.61
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.592
Synthetic Accessibility Score:	3.311
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.768
MDCK Permeability:	3.632793959695846e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.573

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	69.28538513183594%
Volume Distribution (VD):	0.831
Pgp-substrate:	21.939022064208984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.982
CYP2C19-inhibitor:	0.409
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.447
CYP2C9-substrate:	0.789
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	9.201
Half-life (T1/2):	0.308

ADMET: Toxicity

hERG Blockers:	0.258
Human Hepatotoxicity (H-HT):	0.075
Drug-inuced Liver Injury (DILI):	0.897
AMES Toxicity:	0.108
Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.887
Carcinogencity:	0.04
Eye Corrosion:	0.004
Eye Irritation:	0.051
Respiratory Toxicity:	0.177

Download Data

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

Natural Product: NPC9891

Natural Product ID:	NPC9891
*Common Name:**	Beilschmin B
IUPAC Name:	(2S,3S,4S,5R)-3,4-dimethyl-2,5-bis(3,4,5-trimethoxyphenyl)oxolane
Synonyms:	Beilschmin B
Standard InCHIKey:	ZPINJJOPURFFNV-GKHNXXNSSA-N
Standard InCHI:	InChI=1S/C24H32O7/c1-13-14(2)22(16-11-19(27-5)24(30-8)20(12-16)28-6)31-21(13)15-9-17(25-3)23(29-7)18(10-15)26-4/h9-14,21-22H,1-8H3/t13-,14-,21-,22+/m0/s1
SMILES:	COc1cc(cc(c1OC)OC)[C@@H]1O[C@@H]([C@H]([C@@H]1C)C)c1cc(OC)c(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204392
PubChem CID:	14352170
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003423] 7,7'-epoxylignans

*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
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	Palauan	n.a.	PMID[10479343]
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[11277756]
NPO25126	Sarcophyton latum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724849]
NPO25126	Sarcophyton latum	Species	Orchidaceae	Eukaryota	n.a.	Hainan soft coral	n.a.	PMID[16724849]
NPO8247	Austrobaileya scandens	Species	Austrobaileyaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27214307]
NPO2861	Pentaceraster regulus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[28981263]
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9722494]
NPO569	Micromelum integerrimum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5844	Schlumbergera truncata	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO569	Micromelum integerrimum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO569	Micromelum integerrimum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7401	Centaurea dealbata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO569	Micromelum integerrimum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8247	Austrobaileya scandens	Species	Austrobaileyaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3331	Hedysarum sachalinense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25126	Sarcophyton latum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5582	Inocybe aeruginascens	Species	Inocybaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6053	Veronica intercedens	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1462	Amomum sulcatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9215	Papaver glaucum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27884	Sphacelaria arctica	Species	Sphacelariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO772	Bosistoa floydii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4888	Salvia divaricata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2861	Pentaceraster regulus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO345	Quercus laurifolia	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5844	Schlumbergera truncata	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6791	Malva rotundifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6305	Euphorbia jaxartica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO134	Cassia artemisioides	Species	Fabaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	7.5	ug.mL-1	PMID[515819]

☑ 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 NPC9891 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	464
0.1-0.2	1422
0.2-0.3	3932
0.3-0.4	11688
0.4-0.5	7337
0.5-0.6	5039
0.6-0.7	9176
0.7-0.8	2521
0.8-0.85	795
0.85-0.9	258
0.9-0.95	54
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC88297
1.0	High Similarity	NPC186845
0.9833	High Similarity	NPC50683
0.9833	High Similarity	NPC285725
0.9833	High Similarity	NPC112571
0.9752	High Similarity	NPC473093
0.9752	High Similarity	NPC473092
0.9752	High Similarity	NPC8050
0.9675	High Similarity	NPC470624
0.9675	High Similarity	NPC237169
0.9672	High Similarity	NPC54321
0.9672	High Similarity	NPC328682
0.9672	High Similarity	NPC222127
0.9672	High Similarity	NPC82862
0.9672	High Similarity	NPC281864
0.9417	High Similarity	NPC57268
0.9417	High Similarity	NPC65933
0.9417	High Similarity	NPC172676
0.9417	High Similarity	NPC477886
0.9417	High Similarity	NPC126935
0.9417	High Similarity	NPC312713
0.9417	High Similarity	NPC216929
0.9365	High Similarity	NPC475856
0.9365	High Similarity	NPC72046
0.9365	High Similarity	NPC65183
0.9365	High Similarity	NPC204215
0.9365	High Similarity	NPC261812
0.9365	High Similarity	NPC175067
0.9344	High Similarity	NPC34902
0.9344	High Similarity	NPC18449
0.9344	High Similarity	NPC121783
0.9291	High Similarity	NPC158331
0.9291	High Similarity	NPC136750
0.9291	High Similarity	NPC266848
0.9291	High Similarity	NPC1474
0.9286	High Similarity	NPC184928
0.9286	High Similarity	NPC141493
0.9219	High Similarity	NPC474478
0.9219	High Similarity	NPC244983
0.9219	High Similarity	NPC31530
0.9219	High Similarity	NPC287745
0.9219	High Similarity	NPC326095
0.9194	High Similarity	NPC206882
0.918	High Similarity	NPC261661
0.9167	High Similarity	NPC254625
0.9167	High Similarity	NPC475961
0.9147	High Similarity	NPC236522
0.9147	High Similarity	NPC148893
0.9147	High Similarity	NPC24490
0.9147	High Similarity	NPC99572
0.9147	High Similarity	NPC126409
0.9147	High Similarity	NPC141765
0.9147	High Similarity	NPC165155
0.9147	High Similarity	NPC25333
0.9147	High Similarity	NPC49235
0.9147	High Similarity	NPC34103
0.9147	High Similarity	NPC189474
0.9134	High Similarity	NPC192255
0.912	High Similarity	NPC202904
0.912	High Similarity	NPC189248
0.9077	High Similarity	NPC143895
0.9077	High Similarity	NPC78047
0.9077	High Similarity	NPC121651
0.9048	High Similarity	NPC149008
0.9048	High Similarity	NPC283114
0.9048	High Similarity	NPC207702
0.9048	High Similarity	NPC31707
0.9048	High Similarity	NPC470084
0.9016	High Similarity	NPC472596
0.9008	High Similarity	NPC15805
0.9008	High Similarity	NPC477938
0.8992	High Similarity	NPC196937
0.8984	High Similarity	NPC474017
0.8968	High Similarity	NPC98745
0.8968	High Similarity	NPC242032
0.8939	High Similarity	NPC113550
0.8931	High Similarity	NPC11453
0.8923	High Similarity	NPC145769
0.8917	High Similarity	NPC81067
0.8917	High Similarity	NPC9341
0.8917	High Similarity	NPC123948
0.8915	High Similarity	NPC7744
0.8906	High Similarity	NPC153739
0.8906	High Similarity	NPC469612
0.8906	High Similarity	NPC92164
0.8906	High Similarity	NPC64201
0.8906	High Similarity	NPC307042
0.8906	High Similarity	NPC79184
0.8906	High Similarity	NPC187998
0.8906	High Similarity	NPC145305
0.8906	High Similarity	NPC241522
0.8906	High Similarity	NPC242807
0.8906	High Similarity	NPC77040
0.8906	High Similarity	NPC174495
0.8906	High Similarity	NPC469614
0.8906	High Similarity	NPC42300
0.8906	High Similarity	NPC257582
0.8898	High Similarity	NPC184733
0.8898	High Similarity	NPC21867
0.8898	High Similarity	NPC11258
0.8898	High Similarity	NPC57119
0.8898	High Similarity	NPC210674
0.8898	High Similarity	NPC282703
0.8898	High Similarity	NPC45774
0.8898	High Similarity	NPC128208
0.8898	High Similarity	NPC226862
0.8898	High Similarity	NPC129570
0.8898	High Similarity	NPC165128
0.8898	High Similarity	NPC158471
0.8889	High Similarity	NPC76451
0.8872	High Similarity	NPC254759
0.8872	High Similarity	NPC160283
0.8872	High Similarity	NPC103448
0.8872	High Similarity	NPC309124
0.8872	High Similarity	NPC46591
0.8872	High Similarity	NPC27495
0.8872	High Similarity	NPC184797
0.8872	High Similarity	NPC216434
0.8872	High Similarity	NPC177868
0.8864	High Similarity	NPC865
0.8864	High Similarity	NPC185908
0.8864	High Similarity	NPC283949
0.8864	High Similarity	NPC474039
0.8855	High Similarity	NPC44245
0.8855	High Similarity	NPC211386
0.8855	High Similarity	NPC150534
0.8855	High Similarity	NPC72796
0.8837	High Similarity	NPC469613
0.8837	High Similarity	NPC27843
0.8837	High Similarity	NPC161557
0.8837	High Similarity	NPC228346
0.8837	High Similarity	NPC115207
0.8837	High Similarity	NPC82111
0.8837	High Similarity	NPC158079
0.8837	High Similarity	NPC30043
0.8837	High Similarity	NPC277804
0.8837	High Similarity	NPC227160
0.8837	High Similarity	NPC470095
0.8837	High Similarity	NPC7171
0.8837	High Similarity	NPC309787
0.8837	High Similarity	NPC470096
0.8837	High Similarity	NPC40432
0.8837	High Similarity	NPC469625
0.8828	High Similarity	NPC170844
0.8828	High Similarity	NPC190629
0.8828	High Similarity	NPC222004
0.8828	High Similarity	NPC285339
0.8828	High Similarity	NPC475875
0.8828	High Similarity	NPC470258
0.8828	High Similarity	NPC3439
0.8828	High Similarity	NPC476968
0.8828	High Similarity	NPC210623
0.8828	High Similarity	NPC202582
0.8828	High Similarity	NPC226788
0.8828	High Similarity	NPC273295
0.8828	High Similarity	NPC218856
0.8819	High Similarity	NPC127587
0.8819	High Similarity	NPC474119
0.8806	High Similarity	NPC263261
0.8806	High Similarity	NPC311530
0.8806	High Similarity	NPC87725
0.8806	High Similarity	NPC247291
0.8806	High Similarity	NPC312199
0.88	High Similarity	NPC282496
0.88	High Similarity	NPC233526
0.8797	High Similarity	NPC292882
0.8797	High Similarity	NPC236306
0.8797	High Similarity	NPC232164
0.8797	High Similarity	NPC473739
0.8797	High Similarity	NPC471183
0.8779	High Similarity	NPC256776
0.8779	High Similarity	NPC145722
0.8779	High Similarity	NPC185680
0.8769	High Similarity	NPC181049
0.8769	High Similarity	NPC201587
0.8769	High Similarity	NPC253105
0.8769	High Similarity	NPC230219
0.8769	High Similarity	NPC207400
0.8769	High Similarity	NPC102256
0.8769	High Similarity	NPC470752
0.876	High Similarity	NPC271208
0.876	High Similarity	NPC224157
0.876	High Similarity	NPC233224
0.876	High Similarity	NPC476399
0.876	High Similarity	NPC192687
0.875	High Similarity	NPC470213
0.875	High Similarity	NPC472712
0.875	High Similarity	NPC470097
0.875	High Similarity	NPC472713
0.875	High Similarity	NPC114119
0.875	High Similarity	NPC118385
0.875	High Similarity	NPC98631
0.875	High Similarity	NPC187774
0.875	High Similarity	NPC471415
0.875	High Similarity	NPC206615
0.875	High Similarity	NPC186843
0.875	High Similarity	NPC326144
0.875	High Similarity	NPC63879
0.875	High Similarity	NPC473046
0.8741	High Similarity	NPC474295

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 NPC9891 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	861
0.2-0.3	1760
0.3-0.4	2796
0.4-0.5	1733
0.5-0.6	1001
0.6-0.7	534
0.7-0.8	91
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8828	High Similarity	NPD3027	Phase 3
0.8667	High Similarity	NPD5283	Phase 1
0.8492	Intermediate Similarity	NPD3705	Approved
0.8425	Intermediate Similarity	NPD2981	Phase 2
0.8359	Intermediate Similarity	NPD2982	Phase 2
0.8359	Intermediate Similarity	NPD2983	Phase 2
0.8244	Intermediate Similarity	NPD3018	Phase 2
0.8209	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD1613	Approved
0.8143	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD37	Approved
0.7958	Intermediate Similarity	NPD7124	Phase 2
0.7919	Intermediate Similarity	NPD4967	Phase 2
0.7919	Intermediate Similarity	NPD4966	Approved
0.7919	Intermediate Similarity	NPD4965	Approved
0.791	Intermediate Similarity	NPD4908	Phase 1
0.7899	Intermediate Similarity	NPD6111	Discontinued
0.7852	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD6234	Discontinued
0.7794	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD1610	Phase 2
0.7763	Intermediate Similarity	NPD5494	Approved
0.7704	Intermediate Similarity	NPD2861	Phase 2
0.7674	Intermediate Similarity	NPD5536	Phase 2
0.766	Intermediate Similarity	NPD3539	Phase 1
0.763	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD3657	Discovery
0.7619	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD3540	Phase 1
0.758	Intermediate Similarity	NPD7228	Approved
0.7554	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD3620	Phase 2
0.7537	Intermediate Similarity	NPD5327	Phase 3
0.7537	Intermediate Similarity	NPD4749	Approved
0.7536	Intermediate Similarity	NPD5109	Approved
0.7536	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD5111	Phase 2
0.7536	Intermediate Similarity	NPD5110	Phase 2
0.7519	Intermediate Similarity	NPD7157	Approved
0.7518	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4005	Discontinued
0.7516	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4237	Approved
0.75	Intermediate Similarity	NPD4236	Phase 3
0.75	Intermediate Similarity	NPD6674	Discontinued
0.7484	Intermediate Similarity	NPD7199	Phase 2
0.7483	Intermediate Similarity	NPD1934	Approved
0.7481	Intermediate Similarity	NPD1548	Phase 1
0.748	Intermediate Similarity	NPD228	Approved
0.7448	Intermediate Similarity	NPD7466	Approved
0.7432	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD1357	Approved
0.7422	Intermediate Similarity	NPD7843	Approved
0.741	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6895	Approved
0.7394	Intermediate Similarity	NPD6896	Approved
0.7391	Intermediate Similarity	NPD7240	Approved
0.7389	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2684	Approved
0.7361	Intermediate Similarity	NPD1375	Discontinued
0.7351	Intermediate Similarity	NPD4678	Approved
0.7351	Intermediate Similarity	NPD4675	Approved
0.7343	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3882	Suspended
0.7338	Intermediate Similarity	NPD4625	Phase 3
0.7329	Intermediate Similarity	NPD4110	Phase 3
0.7329	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6331	Phase 2
0.7329	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD3022	Approved
0.7323	Intermediate Similarity	NPD3021	Approved
0.732	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4357	Discontinued
0.7279	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3817	Phase 2
0.7273	Intermediate Similarity	NPD5353	Approved
0.726	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6355	Discontinued
0.7254	Intermediate Similarity	NPD5735	Approved
0.7226	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD8651	Approved
0.7222	Intermediate Similarity	NPD5588	Approved
0.7219	Intermediate Similarity	NPD4210	Discontinued
0.7211	Intermediate Similarity	NPD3892	Phase 2
0.7208	Intermediate Similarity	NPD2801	Approved
0.7188	Intermediate Similarity	NPD5451	Approved
0.7183	Intermediate Similarity	NPD2238	Phase 2
0.7183	Intermediate Similarity	NPD4060	Phase 1
0.7181	Intermediate Similarity	NPD5297	Approved
0.7172	Intermediate Similarity	NPD2438	Suspended
0.7172	Intermediate Similarity	NPD2796	Approved
0.7172	Intermediate Similarity	NPD2161	Phase 2
0.717	Intermediate Similarity	NPD5242	Approved
0.717	Intermediate Similarity	NPD3926	Phase 2
0.7164	Intermediate Similarity	NPD5585	Approved
0.7163	Intermediate Similarity	NPD5718	Phase 2
0.7162	Intermediate Similarity	NPD2219	Phase 1
0.7154	Intermediate Similarity	NPD5535	Approved
0.7153	Intermediate Similarity	NPD4536	Approved
0.7153	Intermediate Similarity	NPD4538	Approved
0.7153	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3384	Approved
0.7143	Intermediate Similarity	NPD3382	Approved
0.7143	Intermediate Similarity	NPD3383	Approved
0.7143	Intermediate Similarity	NPD5177	Phase 3
0.7143	Intermediate Similarity	NPD3818	Discontinued
0.7143	Intermediate Similarity	NPD3060	Approved
0.7125	Intermediate Similarity	NPD6166	Phase 2
0.7125	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7266	Discontinued
0.7123	Intermediate Similarity	NPD5763	Approved
0.7123	Intermediate Similarity	NPD5762	Approved
0.7114	Intermediate Similarity	NPD5058	Phase 3
0.7113	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD17	Approved
0.7105	Intermediate Similarity	NPD1653	Approved
0.7101	Intermediate Similarity	NPD2922	Phase 1
0.7099	Intermediate Similarity	NPD5844	Phase 1
0.7092	Intermediate Similarity	NPD7095	Approved
0.709	Intermediate Similarity	NPD1182	Approved
0.7086	Intermediate Similarity	NPD7526	Approved
0.7086	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD52	Approved
0.7081	Intermediate Similarity	NPD7473	Discontinued
0.708	Intermediate Similarity	NPD1840	Phase 2
0.707	Intermediate Similarity	NPD4055	Discovery
0.7063	Intermediate Similarity	NPD2979	Phase 3
0.7063	Intermediate Similarity	NPD1558	Phase 1
0.7055	Intermediate Similarity	NPD6100	Approved
0.7055	Intermediate Similarity	NPD6099	Approved
0.7055	Intermediate Similarity	NPD7074	Phase 3
0.7054	Intermediate Similarity	NPD4750	Phase 3
0.7048	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1247	Approved
0.7037	Intermediate Similarity	NPD1651	Approved
0.7037	Intermediate Similarity	NPD5691	Approved
0.7031	Intermediate Similarity	NPD1358	Approved
0.7027	Intermediate Similarity	NPD4162	Approved
0.7025	Intermediate Similarity	NPD919	Approved
0.702	Intermediate Similarity	NPD4123	Phase 3
0.7007	Intermediate Similarity	NPD1091	Approved
0.7	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6232	Discontinued
0.7	Intermediate Similarity	NPD7229	Phase 3
0.6994	Remote Similarity	NPD8156	Discontinued
0.6994	Remote Similarity	NPD7054	Approved
0.6992	Remote Similarity	NPD6671	Approved
0.6987	Remote Similarity	NPD5772	Approved
0.6987	Remote Similarity	NPD5773	Approved
0.6986	Remote Similarity	NPD5960	Phase 3
0.6985	Remote Similarity	NPD6516	Phase 2
0.6985	Remote Similarity	NPD5846	Approved
0.6978	Remote Similarity	NPD6696	Suspended
0.6978	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6386	Approved
0.6968	Remote Similarity	NPD5089	Approved
0.6968	Remote Similarity	NPD6385	Approved
0.6968	Remote Similarity	NPD5090	Approved
0.6966	Remote Similarity	NPD6653	Approved
0.6966	Remote Similarity	NPD6353	Approved
0.6963	Remote Similarity	NPD7534	Approved
0.6963	Remote Similarity	NPD7533	Approved
0.696	Remote Similarity	NPD1242	Phase 1
0.6959	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1608	Approved
0.6954	Remote Similarity	NPD1511	Approved
0.6953	Remote Similarity	NPD3134	Approved
0.6951	Remote Similarity	NPD7472	Approved
0.6944	Remote Similarity	NPD4140	Approved
0.6943	Remote Similarity	NPD2560	Approved
0.6943	Remote Similarity	NPD2563	Approved
0.694	Remote Similarity	NPD3596	Phase 2
0.6937	Remote Similarity	NPD8127	Discontinued
0.6933	Remote Similarity	NPD8252	Approved
0.6933	Remote Similarity	NPD8251	Approved
0.6933	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD8099	Discontinued
0.6933	Remote Similarity	NPD2677	Approved
0.6928	Remote Similarity	NPD7549	Discontinued
0.6928	Remote Similarity	NPD5976	Discontinued
0.6913	Remote Similarity	NPD1652	Phase 2
0.6912	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7447	Phase 1
0.6906	Remote Similarity	NPD4359	Approved
0.6905	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4380	Phase 2
0.6901	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6788	Approved
0.6899	Remote Similarity	NPD290	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