NPASS Compound

Structure

CID1474 OpenBabel06191715322D 32 35 0 0 1 0 0 0 0 0999 V2000 2.7213 0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4371 0.8994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9487 -4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4128 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0528 -1.4806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2508 -4.3925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5468 -4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7391 -4.1077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9487 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8147 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0579 -1.6230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3767 -2.5937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9781 -0.2079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9487 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0604 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8147 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6808 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6183 -2.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1838 -3.4219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0827 -1.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6808 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1812 -3.3507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8147 -4.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5468 -1.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6157 -2.3800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2533 -4.3213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5468 -3.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7416 -4.1789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1691 -1.6092 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 13 1 0 0 0 0 2 23 1 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 14 2 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 17 2 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 19 2 0 0 0 0 13 20 1 0 0 0 0 13 23 1 6 0 0 0 16 21 2 0 0 0 0 16 25 1 0 0 0 0 17 21 1 0 0 0 0 17 26 1 0 0 0 0 18 22 2 0 0 0 0 18 27 1 0 0 0 0 19 22 1 0 0 0 0 19 28 1 0 0 0 0 20 14 1 1 0 0 0 20 31 1 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 23 24 1 6 0 0 0 23 32 1 0 0 0 0 24 15 1 6 0 0 0 24 31 1 0 0 0 0 24 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.19
Volume:	443.937
LogP:	3.489
LogD:	3.277
LogS:	-5.187
# Rotatable Bonds:	8
TPSA:	77.14
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.562
Synthetic Accessibility Score:	3.989
Fsp3:	0.5
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:	-4.708
MDCK Permeability:	3.8238045817706734e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.251

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.411
Plasma Protein Binding (PPB):	56.32960510253906%
Volume Distribution (VD):	0.637
Pgp-substrate:	28.9149227142334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.99
CYP2C19-inhibitor:	0.092
CYP2C19-substrate:	0.957
CYP2C9-inhibitor:	0.066
CYP2C9-substrate:	0.403
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.806
CYP3A4-substrate:	0.936

ADMET: Excretion

Clearance (CL):	10.697
Half-life (T1/2):	0.359

ADMET: Toxicity

hERG Blockers:	0.118
Human Hepatotoxicity (H-HT):	0.293
Drug-inuced Liver Injury (DILI):	0.661
AMES Toxicity:	0.138
Rat Oral Acute Toxicity:	0.193
Maximum Recommended Daily Dose:	0.251
Skin Sensitization:	0.762
Carcinogencity:	0.493
Eye Corrosion:	0.003
Eye Irritation:	0.075
Respiratory Toxicity:	0.597

Download Data

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

Natural Product: NPC1474

Natural Product ID:	NPC1474
*Common Name:**	4Alpha,5Alpha-Epoxybeilschmin B
IUPAC Name:	(1S,3S,4R,5S)-4,5-dimethyl-1,3-bis(3,4,5-trimethoxyphenyl)-2,6-dioxabicyclo[3.1.0]hexane
Synonyms:	4Alpha,5Alpha-Epoxybeilschmin B
Standard InCHIKey:	VPWGVHVPLFYMJZ-POAYHSMPSA-N
Standard InCHI:	InChI=1S/C24H30O8/c1-13-20(14-9-16(25-3)21(29-7)17(10-14)26-4)31-24(23(13,2)32-24)15-11-18(27-5)22(30-8)19(12-15)28-6/h9-13,20H,1-8H3/t13-,20+,23+,24+/m1/s1
SMILES:	COc1c(OC)cc(cc1OC)[C@H]1O[C@@]2([C@]([C@@H]1C)(O2)C)c1cc(OC)c(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204389
PubChem CID:	71459474
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]
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	=	40.0	ug.mL-1	PMID[457270]

☑ 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 NPC1474 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	505
0.1-0.2	1587
0.2-0.3	4443
0.3-0.4	11400
0.4-0.5	7509
0.5-0.6	6180
0.6-0.7	8550
0.7-0.8	2025
0.8-0.85	385
0.85-0.9	93
0.9-0.95	17
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC121651
0.9618	High Similarity	NPC113550
0.9457	High Similarity	NPC261812
0.9457	High Similarity	NPC72046
0.9457	High Similarity	NPC65183
0.9389	High Similarity	NPC25333
0.9389	High Similarity	NPC49235
0.9389	High Similarity	NPC148893
0.9385	High Similarity	NPC266848
0.9385	High Similarity	NPC136750
0.9313	High Similarity	NPC31530
0.9297	High Similarity	NPC281864
0.9297	High Similarity	NPC54321
0.9297	High Similarity	NPC328682
0.9291	High Similarity	NPC186845
0.9291	High Similarity	NPC50683
0.9291	High Similarity	NPC9891
0.9291	High Similarity	NPC112571
0.9291	High Similarity	NPC88297
0.9291	High Similarity	NPC285725
0.9242	High Similarity	NPC189474
0.9231	High Similarity	NPC192255
0.9219	High Similarity	NPC8050
0.9219	High Similarity	NPC473092
0.9219	High Similarity	NPC473093
0.9173	High Similarity	NPC143895
0.9173	High Similarity	NPC11453
0.9147	High Similarity	NPC222127
0.9147	High Similarity	NPC82862
0.9111	High Similarity	NPC46591
0.9104	High Similarity	NPC283949
0.9098	High Similarity	NPC236522
0.9098	High Similarity	NPC150534
0.9091	High Similarity	NPC196937
0.9044	High Similarity	NPC312199
0.9015	High Similarity	NPC7744
0.9008	High Similarity	NPC470624
0.9008	High Similarity	NPC237169
0.9	High Similarity	NPC158471
0.9	High Similarity	NPC57119
0.9	High Similarity	NPC165128
0.9	High Similarity	NPC226862
0.8978	High Similarity	NPC287124
0.8971	High Similarity	NPC177868
0.8971	High Similarity	NPC56091
0.8971	High Similarity	NPC226547
0.8971	High Similarity	NPC103448
0.8971	High Similarity	NPC216434
0.8963	High Similarity	NPC474039
0.8963	High Similarity	NPC185908
0.8939	High Similarity	NPC227160
0.8939	High Similarity	NPC82111
0.8913	High Similarity	NPC12728
0.8913	High Similarity	NPC218510
0.8913	High Similarity	NPC185071
0.8913	High Similarity	NPC76415
0.8898	High Similarity	NPC172676
0.8898	High Similarity	NPC57268
0.8898	High Similarity	NPC65933
0.8898	High Similarity	NPC216929
0.8898	High Similarity	NPC126935
0.8898	High Similarity	NPC312713
0.8881	High Similarity	NPC185680
0.8881	High Similarity	NPC145722
0.8881	High Similarity	NPC326095
0.8881	High Similarity	NPC244983
0.8881	High Similarity	NPC256776
0.8872	High Similarity	NPC175067
0.8872	High Similarity	NPC204215
0.8872	High Similarity	NPC475856
0.8864	High Similarity	NPC271208
0.8864	High Similarity	NPC233224
0.8849	High Similarity	NPC141569
0.8849	High Similarity	NPC187774
0.8849	High Similarity	NPC472713
0.8849	High Similarity	NPC166884
0.8849	High Similarity	NPC326144
0.8849	High Similarity	NPC477701
0.8849	High Similarity	NPC118385
0.8849	High Similarity	NPC473046
0.8849	High Similarity	NPC472712
0.8841	High Similarity	NPC472562
0.8841	High Similarity	NPC80326
0.8841	High Similarity	NPC174522
0.8841	High Similarity	NPC474295
0.8837	High Similarity	NPC121783
0.8837	High Similarity	NPC34902
0.8837	High Similarity	NPC18449
0.8824	High Similarity	NPC196420
0.8815	High Similarity	NPC24490
0.8815	High Similarity	NPC141765
0.8815	High Similarity	NPC34103
0.8815	High Similarity	NPC165155
0.8806	High Similarity	NPC158331
0.8786	High Similarity	NPC318286
0.8786	High Similarity	NPC477702
0.8786	High Similarity	NPC327651
0.8777	High Similarity	NPC298317
0.8777	High Similarity	NPC324962
0.8777	High Similarity	NPC255566
0.8768	High Similarity	NPC58137
0.8768	High Similarity	NPC300798
0.8759	High Similarity	NPC201404
0.8759	High Similarity	NPC290714
0.8759	High Similarity	NPC53722
0.875	High Similarity	NPC197166
0.875	High Similarity	NPC477886
0.875	High Similarity	NPC172818
0.875	High Similarity	NPC25695
0.875	High Similarity	NPC32189
0.8741	High Similarity	NPC474478
0.8741	High Similarity	NPC287745
0.8731	High Similarity	NPC129687
0.8731	High Similarity	NPC33611
0.8731	High Similarity	NPC171928
0.8731	High Similarity	NPC158526
0.8731	High Similarity	NPC100223
0.8731	High Similarity	NPC16830
0.8723	High Similarity	NPC321696
0.8723	High Similarity	NPC321958
0.8723	High Similarity	NPC212890
0.8722	High Similarity	NPC63574
0.8705	High Similarity	NPC41782
0.8705	High Similarity	NPC311057
0.8705	High Similarity	NPC229172
0.8705	High Similarity	NPC103637
0.8705	High Similarity	NPC151423
0.8705	High Similarity	NPC5262
0.8705	High Similarity	NPC230538
0.8705	High Similarity	NPC472714
0.8705	High Similarity	NPC40237
0.8705	High Similarity	NPC36531
0.8702	High Similarity	NPC206882
0.8682	High Similarity	NPC261661
0.8676	High Similarity	NPC72796
0.8676	High Similarity	NPC44245
0.8676	High Similarity	NPC126409
0.8676	High Similarity	NPC99572
0.8676	High Similarity	NPC474139
0.8667	High Similarity	NPC58585
0.8662	High Similarity	NPC39657
0.8661	High Similarity	NPC475961
0.8661	High Similarity	NPC254625
0.8657	High Similarity	NPC184928
0.8657	High Similarity	NPC469698
0.8657	High Similarity	NPC141493
0.8657	High Similarity	NPC473412
0.8652	High Similarity	NPC205316
0.8652	High Similarity	NPC475868
0.8652	High Similarity	NPC180953
0.8643	High Similarity	NPC474808
0.8643	High Similarity	NPC81638
0.8623	High Similarity	NPC30951
0.8623	High Similarity	NPC6369
0.8623	High Similarity	NPC9068
0.8613	High Similarity	NPC78047
0.8603	High Similarity	NPC47181
0.8603	High Similarity	NPC145769
0.8603	High Similarity	NPC90083
0.8603	High Similarity	NPC170779
0.8601	High Similarity	NPC248132
0.8601	High Similarity	NPC252281
0.8601	High Similarity	NPC477375
0.8601	High Similarity	NPC198129
0.8601	High Similarity	NPC325720
0.8601	High Similarity	NPC327352
0.8601	High Similarity	NPC316676
0.8601	High Similarity	NPC130449
0.8601	High Similarity	NPC270751
0.8594	High Similarity	NPC344161
0.8593	High Similarity	NPC147616
0.8593	High Similarity	NPC259742
0.8593	High Similarity	NPC219671
0.8593	High Similarity	NPC104077
0.8593	High Similarity	NPC471505
0.8582	High Similarity	NPC121661
0.8582	High Similarity	NPC239254
0.8582	High Similarity	NPC73467
0.8582	High Similarity	NPC79184
0.8582	High Similarity	NPC92693
0.8582	High Similarity	NPC218841
0.8582	High Similarity	NPC172171
0.8582	High Similarity	NPC475000
0.8582	High Similarity	NPC307042
0.8571	High Similarity	NPC210674
0.8571	High Similarity	NPC176586
0.8571	High Similarity	NPC31707
0.8571	High Similarity	NPC210354
0.8571	High Similarity	NPC470084
0.8561	High Similarity	NPC284464
0.8561	High Similarity	NPC473960
0.8552	High Similarity	NPC224472
0.8551	High Similarity	NPC261714
0.8551	High Similarity	NPC865
0.8551	High Similarity	NPC477938
0.8551	High Similarity	NPC101807
0.8542	High Similarity	NPC35877
0.8542	High Similarity	NPC85141
0.8542	High Similarity	NPC55715
0.8542	High Similarity	NPC51328

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 NPC1474 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	871
0.2-0.3	1968
0.3-0.4	2929
0.4-0.5	1580
0.5-0.6	990
0.6-0.7	385
0.7-0.8	37
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
0.8605	High Similarity	NPD3705	Approved
0.837	Intermediate Similarity	NPD3027	Phase 3
0.8189	Intermediate Similarity	NPD5283	Phase 1
0.8188	Intermediate Similarity	NPD37	Approved
0.8146	Intermediate Similarity	NPD4967	Phase 2
0.8146	Intermediate Similarity	NPD4965	Approved
0.8146	Intermediate Similarity	NPD4966	Approved
0.812	Intermediate Similarity	NPD2981	Phase 2
0.806	Intermediate Similarity	NPD2983	Phase 2
0.806	Intermediate Similarity	NPD2982	Phase 2
0.8039	Intermediate Similarity	NPD6234	Discontinued
0.7956	Intermediate Similarity	NPD3018	Phase 2
0.7852	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1613	Approved
0.7755	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD7199	Phase 2
0.7698	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7228	Approved
0.7643	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD1357	Approved
0.7518	Intermediate Similarity	NPD4908	Phase 1
0.75	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD6674	Discontinued
0.7483	Intermediate Similarity	NPD1375	Discontinued
0.7467	Intermediate Similarity	NPD7124	Phase 2
0.7421	Intermediate Similarity	NPD5494	Approved
0.7417	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD3539	Phase 1
0.7413	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD6111	Discontinued
0.7391	Intermediate Similarity	NPD1610	Phase 2
0.7365	Intermediate Similarity	NPD3540	Phase 1
0.7362	Intermediate Similarity	NPD3818	Discontinued
0.7351	Intermediate Similarity	NPD5058	Phase 3
0.7338	Intermediate Similarity	NPD1653	Approved
0.7324	Intermediate Similarity	NPD2861	Phase 2
0.732	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD4749	Approved
0.7279	Intermediate Similarity	NPD5536	Phase 2
0.7261	Intermediate Similarity	NPD3383	Approved
0.7261	Intermediate Similarity	NPD3382	Approved
0.7261	Intermediate Similarity	NPD3384	Approved
0.726	Intermediate Similarity	NPD3657	Discovery
0.7248	Intermediate Similarity	NPD7266	Discontinued
0.7208	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3620	Phase 2
0.7179	Intermediate Similarity	NPD4005	Discontinued
0.7172	Intermediate Similarity	NPD5110	Phase 2
0.7172	Intermediate Similarity	NPD5109	Approved
0.7172	Intermediate Similarity	NPD5111	Phase 2
0.7172	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3817	Phase 2
0.7169	Intermediate Similarity	NPD7074	Phase 3
0.7152	Intermediate Similarity	NPD4236	Phase 3
0.7152	Intermediate Similarity	NPD4237	Approved
0.7152	Intermediate Similarity	NPD1934	Approved
0.7143	Intermediate Similarity	NPD1091	Approved
0.7133	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD7157	Approved
0.7125	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4210	Discontinued
0.7108	Intermediate Similarity	NPD7054	Approved
0.7105	Intermediate Similarity	NPD7466	Approved
0.7105	Intermediate Similarity	NPD4110	Phase 3
0.7105	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4625	Phase 3
0.7101	Intermediate Similarity	NPD1548	Phase 1
0.709	Intermediate Similarity	NPD228	Approved
0.7083	Intermediate Similarity	NPD7685	Pre-registration
0.7067	Intermediate Similarity	NPD2438	Suspended
0.7066	Intermediate Similarity	NPD7472	Approved
0.7059	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5585	Approved
0.7042	Intermediate Similarity	NPD5327	Phase 3
0.7037	Intermediate Similarity	NPD7843	Approved
0.7034	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4675	Approved
0.7025	Intermediate Similarity	NPD4678	Approved
0.7019	Intermediate Similarity	NPD3882	Suspended
0.7012	Intermediate Similarity	NPD3787	Discontinued
0.7	Intermediate Similarity	NPD2978	Approved
0.7	Intermediate Similarity	NPD5126	Approved
0.7	Intermediate Similarity	NPD2977	Approved
0.7	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4108	Discontinued
0.7	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5125	Phase 3
0.6993	Remote Similarity	NPD6331	Phase 2
0.6992	Remote Similarity	NPD2684	Approved
0.697	Remote Similarity	NPD5242	Approved
0.697	Remote Similarity	NPD3926	Phase 2
0.6968	Remote Similarity	NPD4357	Discontinued
0.6962	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2238	Phase 2
0.6959	Remote Similarity	NPD4060	Phase 1
0.6957	Remote Similarity	NPD5353	Approved
0.6941	Remote Similarity	NPD7808	Phase 3
0.694	Remote Similarity	NPD3021	Approved
0.694	Remote Similarity	NPD3022	Approved
0.6933	Remote Similarity	NPD7097	Phase 1
0.6933	Remote Similarity	NPD6895	Approved
0.6933	Remote Similarity	NPD6896	Approved
0.6928	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6166	Phase 2
0.6928	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6797	Phase 2
0.6918	Remote Similarity	NPD7028	Phase 2
0.6913	Remote Similarity	NPD6355	Discontinued
0.6912	Remote Similarity	NPD5535	Approved
0.6909	Remote Similarity	NPD6232	Discontinued
0.6905	Remote Similarity	NPD5844	Phase 1
0.6894	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2801	Approved
0.6892	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5588	Approved
0.6886	Remote Similarity	NPD7473	Discontinued
0.6883	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3892	Phase 2
0.6882	Remote Similarity	NPD7251	Discontinued
0.6882	Remote Similarity	NPD6559	Discontinued
0.6879	Remote Similarity	NPD17	Approved
0.6872	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7095	Approved
0.6871	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4055	Discovery
0.6859	Remote Similarity	NPD5297	Approved
0.6846	Remote Similarity	NPD2979	Phase 3
0.6842	Remote Similarity	NPD2796	Approved
0.6842	Remote Similarity	NPD2161	Phase 2
0.6842	Remote Similarity	NPD7549	Discontinued
0.6842	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3454	Phase 3
0.6839	Remote Similarity	NPD2219	Phase 1
0.6829	Remote Similarity	NPD919	Approved
0.6821	Remote Similarity	NPD4536	Approved
0.6821	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4538	Approved
0.6818	Remote Similarity	NPD3060	Approved
0.6818	Remote Similarity	NPD5177	Phase 3
0.6815	Remote Similarity	NPD5451	Approved
0.6809	Remote Similarity	NPD5691	Approved
0.6806	Remote Similarity	NPD4359	Approved
0.6806	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5735	Approved
0.68	Remote Similarity	NPD5124	Phase 1
0.68	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5763	Approved
0.6797	Remote Similarity	NPD5762	Approved
0.6791	Remote Similarity	NPD1358	Approved
0.6779	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5960	Phase 3
0.6772	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6387	Discontinued
0.6759	Remote Similarity	NPD8651	Approved
0.6759	Remote Similarity	NPD2922	Phase 1
0.6747	Remote Similarity	NPD1247	Approved
0.6747	Remote Similarity	NPD8127	Discontinued
0.6746	Remote Similarity	NPD3751	Discontinued
0.6743	Remote Similarity	NPD6842	Approved
0.6743	Remote Similarity	NPD6841	Approved
0.6743	Remote Similarity	NPD6843	Phase 3
0.6738	Remote Similarity	NPD1182	Approved
0.6736	Remote Similarity	NPD1840	Phase 2
0.6736	Remote Similarity	NPD1608	Approved
0.6733	Remote Similarity	NPD1558	Phase 1
0.6733	Remote Similarity	NPD4140	Approved
0.6732	Remote Similarity	NPD6099	Approved
0.6732	Remote Similarity	NPD6100	Approved
0.6731	Remote Similarity	NPD6190	Approved
0.673	Remote Similarity	NPD5976	Discontinued
0.6728	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7680	Approved
0.6716	Remote Similarity	NPD3134	Approved
0.6711	Remote Similarity	NPD5718	Phase 2
0.671	Remote Similarity	NPD1652	Phase 2
0.671	Remote Similarity	NPD4162	Approved
0.6709	Remote Similarity	NPD4123	Phase 3
0.6708	Remote Similarity	NPD4380	Phase 2
0.6707	Remote Similarity	NPD7229	Phase 3
0.6691	Remote Similarity	NPD4750	Phase 3
0.669	Remote Similarity	NPD1651	Approved
0.669	Remote Similarity	NPD3685	Discontinued
0.6689	Remote Similarity	NPD230	Phase 1
0.6689	Remote Similarity	NPD1933	Approved
0.6687	Remote Similarity	NPD7819	Suspended
0.6687	Remote Similarity	NPD8455	Phase 2
0.6687	Remote Similarity	NPD1465	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