NPASS Compound

Structure

CID121651 OpenBabel06191715472D 31 35 0 0 1 0 0 0 0 0999 V2000 -2.6492 0.7745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6856 -0.1809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5969 5.5183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0238 4.3340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3929 -0.0025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1523 6.2041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4710 3.7194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9056 2.7488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6608 0.9975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7948 2.4975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8633 4.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6883 1.0516 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9081 2.8200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7948 1.4975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0314 4.5476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4660 3.5770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5269 1.4975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6608 2.9975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3477 1.9918 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0289 4.4764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5269 2.4975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8994 0.4371 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0712 0.9975 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5944 5.4471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4634 3.5058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3929 0.9975 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5893 5.3046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8687 3.9756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2700 3.1666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3483 1.9583 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 1 12 1 0 0 0 0 2 22 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 13 1 0 0 0 0 8 16 2 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 18 2 0 0 0 0 11 28 1 0 0 0 0 11 29 1 0 0 0 0 12 19 1 0 0 0 0 12 22 1 6 0 0 0 15 20 2 0 0 0 0 15 24 1 0 0 0 0 16 20 1 0 0 0 0 16 25 1 0 0 0 0 17 21 2 0 0 0 0 17 26 1 0 0 0 0 18 21 1 0 0 0 0 18 28 1 0 0 0 0 19 13 1 1 0 0 0 19 30 1 0 0 0 0 20 27 1 0 0 0 0 21 29 1 0 0 0 0 22 23 1 6 0 0 0 22 31 1 0 0 0 0 23 14 1 6 0 0 0 23 30 1 0 0 0 0 23 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.16
Volume:	418.085
LogP:	3.682
LogD:	3.449
LogS:	-5.657
# Rotatable Bonds:	6
TPSA:	77.14
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.641
Synthetic Accessibility Score:	4.146
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.735
MDCK Permeability:	5.17140724696219e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.084

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.205
Plasma Protein Binding (PPB):	74.53964233398438%
Volume Distribution (VD):	0.822
Pgp-substrate:	16.259449005126953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.99
CYP2C19-inhibitor:	0.558
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.25
CYP2C9-substrate:	0.537
CYP2D6-inhibitor:	0.201
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.957
CYP3A4-substrate:	0.928

ADMET: Excretion

Clearance (CL):	12.752
Half-life (T1/2):	0.294

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.473
Drug-inuced Liver Injury (DILI):	0.686
AMES Toxicity:	0.306
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.616
Skin Sensitization:	0.777
Carcinogencity:	0.932
Eye Corrosion:	0.003
Eye Irritation:	0.157
Respiratory Toxicity:	0.854

Download Data

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

Natural Product: NPC121651

Natural Product ID:	NPC121651
*Common Name:**	4Alpha,5Alpha-Epoxybeilschmin A
IUPAC Name:	6-[(1S,3S,4R,5S)-4,5-dimethyl-3-(3,4,5-trimethoxyphenyl)-2,6-dioxabicyclo[3.1.0]hexan-1-yl]-4-methoxy-1,3-benzodioxole
Synonyms:	4Alpha,5Alpha-Epoxybeilschmin A
Standard InCHIKey:	BHMOQQOVENTEQO-UHLCPZAPSA-N
Standard InCHI:	InChI=1S/C23H26O8/c1-12-19(13-7-15(24-3)20(27-6)16(8-13)25-4)30-23(22(12,2)31-23)14-9-17(26-5)21-18(10-14)28-11-29-21/h7-10,12,19H,11H2,1-6H3/t12-,19+,22+,23+/m1/s1
SMILES:	COc1cc(cc(c1OC)OC)[C@H]1O[C@@]2([C@]([C@@H]1C)(O2)C)c1cc(OC)c2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204388
PubChem CID:	71454057
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001969] Dibenzylbutane lignans

*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]
NPO134	Cassia artemisioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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]
NPO772	Bosistoa floydii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27884	Sphacelaria arctica	Species	Sphacelariaceae	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]

☑ 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	=	30.0	ug.mL-1	PMID[546625]

☑ 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 NPC121651 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	522
0.1-0.2	1570
0.2-0.3	4372
0.3-0.4	11173
0.4-0.5	7780
0.5-0.6	6282
0.6-0.7	8406
0.7-0.8	2045
0.8-0.85	406
0.85-0.9	114
0.9-0.95	24
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9847	High Similarity	NPC113550
0.9767	High Similarity	NPC1474
0.969	High Similarity	NPC72046
0.969	High Similarity	NPC65183
0.969	High Similarity	NPC261812
0.9618	High Similarity	NPC25333
0.9618	High Similarity	NPC49235
0.9618	High Similarity	NPC148893
0.9615	High Similarity	NPC136750
0.9615	High Similarity	NPC266848
0.9542	High Similarity	NPC31530
0.947	High Similarity	NPC189474
0.9462	High Similarity	NPC192255
0.9398	High Similarity	NPC11453
0.938	High Similarity	NPC328682
0.938	High Similarity	NPC54321
0.938	High Similarity	NPC281864
0.9333	High Similarity	NPC46591
0.9328	High Similarity	NPC283949
0.9323	High Similarity	NPC150534
0.9302	High Similarity	NPC473092
0.9302	High Similarity	NPC473093
0.9302	High Similarity	NPC8050
0.9265	High Similarity	NPC312199
0.9242	High Similarity	NPC7744
0.9231	High Similarity	NPC222127
0.9231	High Similarity	NPC158471
0.9231	High Similarity	NPC226862
0.9231	High Similarity	NPC165128
0.9231	High Similarity	NPC82862
0.9231	High Similarity	NPC57119
0.9197	High Similarity	NPC287124
0.9191	High Similarity	NPC216434
0.9191	High Similarity	NPC177868
0.9191	High Similarity	NPC226547
0.9191	High Similarity	NPC103448
0.9191	High Similarity	NPC56091
0.9185	High Similarity	NPC185908
0.9167	High Similarity	NPC227160
0.9167	High Similarity	NPC82111
0.913	High Similarity	NPC185071
0.913	High Similarity	NPC12728
0.9111	High Similarity	NPC143895
0.9091	High Similarity	NPC233224
0.9091	High Similarity	NPC271208
0.9077	High Similarity	NPC186845
0.9077	High Similarity	NPC285725
0.9077	High Similarity	NPC112571
0.9077	High Similarity	NPC50683
0.9077	High Similarity	NPC9891
0.9077	High Similarity	NPC88297
0.9065	High Similarity	NPC166884
0.9065	High Similarity	NPC477701
0.9065	High Similarity	NPC141569
0.9058	High Similarity	NPC472562
0.9058	High Similarity	NPC80326
0.9058	High Similarity	NPC474295
0.9058	High Similarity	NPC174522
0.9037	High Similarity	NPC236522
0.903	High Similarity	NPC196937
0.9	High Similarity	NPC477702
0.8993	High Similarity	NPC298317
0.8993	High Similarity	NPC255566
0.8986	High Similarity	NPC58137
0.8986	High Similarity	NPC300798
0.8971	High Similarity	NPC32189
0.8955	High Similarity	NPC100223
0.8955	High Similarity	NPC171928
0.8955	High Similarity	NPC16830
0.8955	High Similarity	NPC33611
0.8955	High Similarity	NPC129687
0.8955	High Similarity	NPC158526
0.8936	High Similarity	NPC212890
0.8923	High Similarity	NPC18449
0.8923	High Similarity	NPC121783
0.8923	High Similarity	NPC34902
0.8921	High Similarity	NPC151423
0.8921	High Similarity	NPC40237
0.8921	High Similarity	NPC311057
0.8905	High Similarity	NPC474039
0.8897	High Similarity	NPC24490
0.8897	High Similarity	NPC141765
0.8897	High Similarity	NPC474139
0.8897	High Similarity	NPC34103
0.8897	High Similarity	NPC165155
0.8865	High Similarity	NPC180953
0.8865	High Similarity	NPC205316
0.8865	High Similarity	NPC475868
0.8857	High Similarity	NPC474808
0.8857	High Similarity	NPC218510
0.8857	High Similarity	NPC76415
0.8841	High Similarity	NPC9068
0.8824	High Similarity	NPC256776
0.8824	High Similarity	NPC170779
0.8824	High Similarity	NPC47181
0.8824	High Similarity	NPC145722
0.8824	High Similarity	NPC185680
0.8824	High Similarity	NPC90083
0.8815	High Similarity	NPC104077
0.8815	High Similarity	NPC219671
0.8815	High Similarity	NPC259742
0.8815	High Similarity	NPC147616
0.8811	High Similarity	NPC130449
0.8811	High Similarity	NPC248132
0.8806	High Similarity	NPC237169
0.8806	High Similarity	NPC470624
0.8794	High Similarity	NPC187774
0.8794	High Similarity	NPC472712
0.8794	High Similarity	NPC172171
0.8794	High Similarity	NPC92693
0.8794	High Similarity	NPC475000
0.8794	High Similarity	NPC326144
0.8794	High Similarity	NPC218841
0.8794	High Similarity	NPC118385
0.8794	High Similarity	NPC239254
0.8794	High Similarity	NPC472713
0.8794	High Similarity	NPC473046
0.8786	High Similarity	NPC210354
0.8786	High Similarity	NPC176586
0.8768	High Similarity	NPC101807
0.8768	High Similarity	NPC196420
0.8759	High Similarity	NPC174191
0.8759	High Similarity	NPC18576
0.8759	High Similarity	NPC126409
0.8759	High Similarity	NPC99572
0.8759	High Similarity	NPC135777
0.8759	High Similarity	NPC142547
0.875	High Similarity	NPC286235
0.875	High Similarity	NPC51328
0.875	High Similarity	NPC95392
0.875	High Similarity	NPC55715
0.875	High Similarity	NPC35877
0.875	High Similarity	NPC55158
0.875	High Similarity	NPC85141
0.8732	High Similarity	NPC327651
0.8732	High Similarity	NPC318286
0.8731	High Similarity	NPC476748
0.8723	High Similarity	NPC474288
0.8723	High Similarity	NPC324962
0.8722	High Similarity	NPC158737
0.8705	High Similarity	NPC290714
0.8705	High Similarity	NPC156376
0.8705	High Similarity	NPC193666
0.8705	High Similarity	NPC53722
0.8705	High Similarity	NPC88640
0.8705	High Similarity	NPC201404
0.8705	High Similarity	NPC123526
0.8696	High Similarity	NPC78047
0.8696	High Similarity	NPC25695
0.8696	High Similarity	NPC172818
0.8696	High Similarity	NPC197166
0.8692	High Similarity	NPC312713
0.8692	High Similarity	NPC216929
0.8692	High Similarity	NPC126935
0.8692	High Similarity	NPC57268
0.8692	High Similarity	NPC301641
0.8692	High Similarity	NPC172676
0.8692	High Similarity	NPC80241
0.8692	High Similarity	NPC65933
0.869	High Similarity	NPC473989
0.8686	High Similarity	NPC244983
0.8686	High Similarity	NPC326095
0.8681	High Similarity	NPC71726
0.8676	High Similarity	NPC475856
0.8676	High Similarity	NPC204215
0.8676	High Similarity	NPC175067
0.8671	High Similarity	NPC162193
0.8671	High Similarity	NPC154971
0.8671	High Similarity	NPC321696
0.8671	High Similarity	NPC321958
0.8671	High Similarity	NPC252286
0.8671	High Similarity	NPC193779
0.8667	High Similarity	NPC63574
0.8662	High Similarity	NPC50696
0.8662	High Similarity	NPC177644
0.8662	High Similarity	NPC191158
0.8662	High Similarity	NPC84181
0.8652	High Similarity	NPC230538
0.8652	High Similarity	NPC103637
0.8652	High Similarity	NPC246947
0.8652	High Similarity	NPC229172
0.8652	High Similarity	NPC36531
0.8652	High Similarity	NPC472714
0.8652	High Similarity	NPC5262
0.8633	High Similarity	NPC166184
0.8633	High Similarity	NPC469981
0.863	High Similarity	NPC210642
0.863	High Similarity	NPC303519
0.863	High Similarity	NPC13985
0.8621	High Similarity	NPC477698
0.8613	High Similarity	NPC158331
0.8613	High Similarity	NPC58585
0.8611	High Similarity	NPC116019
0.8611	High Similarity	NPC39657
0.8603	High Similarity	NPC473412
0.8603	High Similarity	NPC469698
0.8601	High Similarity	NPC42716
0.8601	High Similarity	NPC474749
0.8601	High Similarity	NPC11422
0.8601	High Similarity	NPC178014

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 NPC121651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	868
0.2-0.3	2010
0.3-0.4	2901
0.4-0.5	1587
0.5-0.6	968
0.6-0.7	380
0.7-0.8	36
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.855	High Similarity	NPD3705	Approved
0.8344	Intermediate Similarity	NPD4966	Approved
0.8344	Intermediate Similarity	NPD4965	Approved
0.8344	Intermediate Similarity	NPD4967	Phase 2
0.8235	Intermediate Similarity	NPD6234	Discontinued
0.8188	Intermediate Similarity	NPD3027	Phase 3
0.8146	Intermediate Similarity	NPD37	Approved
0.8	Intermediate Similarity	NPD5283	Phase 1
0.7941	Intermediate Similarity	NPD2981	Phase 2
0.7883	Intermediate Similarity	NPD2983	Phase 2
0.7883	Intermediate Similarity	NPD2982	Phase 2
0.7875	Intermediate Similarity	NPD7228	Approved
0.7815	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD3018	Phase 2
0.7785	Intermediate Similarity	NPD7199	Phase 2
0.7688	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7240	Approved
0.7639	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1613	Approved
0.76	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1357	Approved
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6674	Discontinued
0.7361	Intermediate Similarity	NPD4908	Phase 1
0.7358	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1375	Discontinued
0.7333	Intermediate Similarity	NPD3818	Discontinued
0.732	Intermediate Similarity	NPD7124	Phase 2
0.7308	Intermediate Similarity	NPD1653	Approved
0.7284	Intermediate Similarity	NPD5494	Approved
0.7267	Intermediate Similarity	NPD3539	Phase 1
0.726	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6111	Discontinued
0.7235	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1610	Phase 2
0.7233	Intermediate Similarity	NPD3382	Approved
0.7233	Intermediate Similarity	NPD3384	Approved
0.7233	Intermediate Similarity	NPD3383	Approved
0.7219	Intermediate Similarity	NPD7266	Discontinued
0.7219	Intermediate Similarity	NPD3540	Phase 1
0.7208	Intermediate Similarity	NPD5058	Phase 3
0.7179	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD2861	Phase 2
0.7143	Intermediate Similarity	NPD7074	Phase 3
0.7133	Intermediate Similarity	NPD4749	Approved
0.7122	Intermediate Similarity	NPD5536	Phase 2
0.7114	Intermediate Similarity	NPD3657	Discovery
0.7113	Intermediate Similarity	NPD1091	Approved
0.7097	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4210	Discontinued
0.7083	Intermediate Similarity	NPD7054	Approved
0.707	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7685	Pre-registration
0.7047	Intermediate Similarity	NPD3620	Phase 2
0.7047	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4005	Discontinued
0.7041	Intermediate Similarity	NPD7472	Approved
0.7039	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3817	Phase 2
0.7027	Intermediate Similarity	NPD5111	Phase 2
0.7027	Intermediate Similarity	NPD5110	Phase 2
0.7027	Intermediate Similarity	NPD5109	Approved
0.7027	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1934	Approved
0.7013	Intermediate Similarity	NPD4237	Approved
0.7013	Intermediate Similarity	NPD4236	Phase 3
0.7	Intermediate Similarity	NPD7028	Phase 2
0.6994	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7157	Approved
0.6975	Remote Similarity	NPD2977	Approved
0.6975	Remote Similarity	NPD2978	Approved
0.6974	Remote Similarity	NPD4108	Discontinued
0.6968	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7466	Approved
0.6968	Remote Similarity	NPD4110	Phase 3
0.6959	Remote Similarity	NPD4625	Phase 3
0.695	Remote Similarity	NPD1548	Phase 1
0.6934	Remote Similarity	NPD228	Approved
0.6928	Remote Similarity	NPD2438	Suspended
0.6919	Remote Similarity	NPD7808	Phase 3
0.6913	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6797	Phase 2
0.6901	Remote Similarity	NPD5585	Approved
0.6897	Remote Similarity	NPD5327	Phase 3
0.6894	Remote Similarity	NPD4678	Approved
0.6894	Remote Similarity	NPD4675	Approved
0.6892	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3882	Suspended
0.6886	Remote Similarity	NPD3787	Discontinued
0.6885	Remote Similarity	NPD7680	Approved
0.6884	Remote Similarity	NPD7843	Approved
0.6871	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6559	Discontinued
0.686	Remote Similarity	NPD7251	Discontinued
0.6859	Remote Similarity	NPD6331	Phase 2
0.6853	Remote Similarity	NPD5125	Phase 3
0.6853	Remote Similarity	NPD5126	Approved
0.6848	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3926	Phase 2
0.6845	Remote Similarity	NPD5242	Approved
0.6838	Remote Similarity	NPD2684	Approved
0.6835	Remote Similarity	NPD4357	Discontinued
0.6832	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5353	Approved
0.6821	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2238	Phase 2
0.6821	Remote Similarity	NPD4060	Phase 1
0.6818	Remote Similarity	NPD2161	Phase 2
0.6818	Remote Similarity	NPD3454	Phase 3
0.6818	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6166	Phase 2
0.6805	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6895	Approved
0.6797	Remote Similarity	NPD7097	Phase 1
0.6797	Remote Similarity	NPD6896	Approved
0.6795	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3021	Approved
0.6788	Remote Similarity	NPD3022	Approved
0.6786	Remote Similarity	NPD6232	Discontinued
0.6784	Remote Similarity	NPD5844	Phase 1
0.6781	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6355	Discontinued
0.6776	Remote Similarity	NPD5735	Approved
0.6768	Remote Similarity	NPD2801	Approved
0.6765	Remote Similarity	NPD7473	Discontinued
0.6763	Remote Similarity	NPD5535	Approved
0.6755	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5588	Approved
0.6752	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD3892	Phase 2
0.6747	Remote Similarity	NPD4055	Discovery
0.6739	Remote Similarity	NPD5006	Approved
0.6739	Remote Similarity	NPD5005	Approved
0.6736	Remote Similarity	NPD17	Approved
0.6733	Remote Similarity	NPD7095	Approved
0.673	Remote Similarity	NPD5297	Approved
0.6724	Remote Similarity	NPD7549	Discontinued
0.6723	Remote Similarity	NPD6842	Approved
0.6723	Remote Similarity	NPD6841	Approved
0.6723	Remote Similarity	NPD6843	Phase 3
0.6711	Remote Similarity	NPD2979	Phase 3
0.671	Remote Similarity	NPD2796	Approved
0.6709	Remote Similarity	NPD2219	Phase 1
0.6708	Remote Similarity	NPD5976	Discontinued
0.6707	Remote Similarity	NPD919	Approved
0.6704	Remote Similarity	NPD7296	Approved
0.6688	Remote Similarity	NPD4536	Approved
0.6688	Remote Similarity	NPD5177	Phase 3
0.6688	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD3060	Approved
0.6688	Remote Similarity	NPD4538	Approved
0.6667	Remote Similarity	NPD5691	Approved
0.6667	Remote Similarity	NPD8455	Phase 2
0.6667	Remote Similarity	NPD4359	Approved
0.6667	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5124	Phase 1
0.6667	Remote Similarity	NPD5763	Approved
0.6667	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5451	Approved
0.6667	Remote Similarity	NPD5762	Approved
0.6646	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD5960	Phase 3
0.6642	Remote Similarity	NPD1358	Approved
0.6628	Remote Similarity	NPD3751	Discontinued
0.6627	Remote Similarity	NPD1247	Approved
0.6627	Remote Similarity	NPD8127	Discontinued
0.6623	Remote Similarity	NPD6353	Approved
0.6623	Remote Similarity	NPD2492	Phase 1
0.6622	Remote Similarity	NPD8651	Approved
0.6622	Remote Similarity	NPD2922	Phase 1
0.662	Remote Similarity	NPD6387	Discontinued
0.6612	Remote Similarity	NPD4420	Approved
0.6606	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6190	Approved
0.6603	Remote Similarity	NPD6100	Approved
0.6603	Remote Similarity	NPD6099	Approved
0.6601	Remote Similarity	NPD1558	Phase 1
0.6601	Remote Similarity	NPD4140	Approved
0.6599	Remote Similarity	NPD1608	Approved
0.6599	Remote Similarity	NPD1840	Phase 2
0.6597	Remote Similarity	NPD1182	Approved
0.659	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7229	Phase 3
0.6585	Remote Similarity	NPD4380	Phase 2
0.6584	Remote Similarity	NPD4123	Phase 3
0.6582	Remote Similarity	NPD1652	Phase 2
0.6582	Remote Similarity	NPD4162	Approved
0.6579	Remote Similarity	NPD5718	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