NPASS Compound

Structure

CID94377 OpenBabel06191715432D 36 39 0 0 1 0 0 0 0 0999 V2000 -5.2599 -2.6082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0435 1.3063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1554 -5.5640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3569 -5.2319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1250 2.0271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9843 -1.5823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7595 -3.0957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8322 -3.3970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3569 -2.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3569 -1.3319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3326 -1.3319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9750 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3326 -2.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8322 0.7332 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7284 -4.7752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3569 -4.2569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1554 1.9252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9050 -3.0957 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4875 -2.7944 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7595 -0.5431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3319 -1.3319 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9050 -0.5431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7595 1.0345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3319 -2.3069 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4875 -0.8444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8322 -0.2418 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6981 -4.8771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2012 -3.7694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5823 2.7140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0608 1.9618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8322 -1.2168 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 -1.3319 -3.8845 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4875 -3.7694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7588 1.0345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3326 0.2457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 11 13 2 0 0 0 0 11 20 1 0 0 0 0 12 25 1 0 0 0 0 12 32 1 0 0 0 0 14 23 1 0 0 0 0 14 26 1 6 0 0 0 15 27 2 0 0 0 0 15 33 1 0 0 0 0 16 28 2 0 0 0 0 16 34 1 0 0 0 0 17 29 2 0 0 0 0 17 35 1 0 0 0 0 18 24 1 1 0 0 0 18 33 1 0 0 0 0 19 24 1 6 0 0 0 19 34 1 0 0 0 0 20 26 1 6 0 0 0 20 36 1 0 0 0 0 21 22 1 0 0 0 0 21 24 1 1 0 0 0 21 25 1 0 0 0 0 22 26 1 1 0 0 0 22 35 1 0 0 0 0 23 30 2 0 0 0 0 23 36 1 0 0 0 0 24 6 1 1 0 0 0 25 10 1 1 0 0 0 25 32 1 0 0 0 0 26 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	508.23
Volume:	498.746
LogP:	2.035
LogD:	1.259
LogS:	-4.062
# Rotatable Bonds:	6
TPSA:	137.96
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.261
Synthetic Accessibility Score:	5.871
Fsp3:	0.769
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.026
MDCK Permeability:	0.00010757381824078038
Pgp-inhibitor:	0.997
Pgp-substrate:	0.08
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.053
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.506
Plasma Protein Binding (PPB):	54.43645095825195%
Volume Distribution (VD):	1.643
Pgp-substrate:	45.240379333496094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.436
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	2.743
Half-life (T1/2):	0.432

ADMET: Toxicity

hERG Blockers:	0.195
Human Hepatotoxicity (H-HT):	0.898
Drug-inuced Liver Injury (DILI):	0.815
AMES Toxicity:	0.148
Rat Oral Acute Toxicity:	0.768
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.552
Carcinogencity:	0.033
Eye Corrosion:	0.005
Eye Irritation:	0.014
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC94377

Natural Product ID:	NPC94377
*Common Name:**	Junceellolide K
IUPAC Name:	n.a.
Synonyms:	Junceellolide K
Standard InCHIKey:	BBSUFGRORDMNJA-WCPNWAJNSA-N
Standard InCHI:	InChI=1S/C26H36O10/c1-13-7-8-18(33-15(3)27)24(6)19(34-16(4)28)9-10-25(12-32-25)21(24)22(35-17(5)29)26(31)14(2)23(30)36-20(26)11-13/h11,14,18-22,31H,7-10,12H2,1-6H3/b13-11-/t14-,18-,19-,20-,21+,22-,24-,25-,26-/m0/s1
SMILES:	CC(=O)O[C@H]1CC/C(=C[C@H]2[C@@]([C@H]([C@@H]3[C@]1(C)[C@H](CC[C@]13OC1)OC(=O)C)OC(=O)C)(O)[C@@H](C)C(=O)O2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455351
PubChem CID:	11706144
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO3708	Junceella fragilis	Species	Ellisellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075754]
NPO3708	Junceella fragilis	Species	Ellisellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087588]
NPO3708	Junceella fragilis	Species	Ellisellidae	Eukaryota	n.a.	West Pacific Ocean	n.a.	PMID[11087588]
NPO3708	Junceella fragilis	Species	Ellisellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499329]
NPO3708	Junceella fragilis	Species	Ellisellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18774864]
NPO3708	Junceella fragilis	Species	Ellisellidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3708	Junceella fragilis	Species	Ellisellidae	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	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	13.89	%	PMID[514588]
NPT2	Others	Unspecified		Inhibition	=	15.04	%	PMID[514588]

☑ 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 NPC94377 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	211
0.1-0.2	1325
0.2-0.3	4201
0.3-0.4	7503
0.4-0.5	13917
0.5-0.6	6972
0.6-0.7	6531
0.7-0.8	1876
0.8-0.85	103
0.85-0.9	38
0.9-0.95	18
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9429	High Similarity	NPC73314
0.9423	High Similarity	NPC473877
0.934	High Similarity	NPC474333
0.932	High Similarity	NPC42662
0.93	High Similarity	NPC183571
0.9252	High Similarity	NPC296822
0.9208	High Similarity	NPC474165
0.9208	High Similarity	NPC69171
0.9135	High Similarity	NPC475922
0.9126	High Similarity	NPC475510
0.9126	High Similarity	NPC475587
0.9083	High Similarity	NPC470186
0.9048	High Similarity	NPC161816
0.9048	High Similarity	NPC473843
0.9048	High Similarity	NPC473975
0.9048	High Similarity	NPC115257
0.9048	High Similarity	NPC473594
0.9048	High Similarity	NPC474586
0.9038	High Similarity	NPC473939
0.9038	High Similarity	NPC473595
0.8962	High Similarity	NPC194619
0.8868	High Similarity	NPC281624
0.8846	High Similarity	NPC16313
0.8846	High Similarity	NPC9303
0.8839	High Similarity	NPC282003
0.8839	High Similarity	NPC310035
0.8839	High Similarity	NPC188222
0.8835	High Similarity	NPC474166
0.8835	High Similarity	NPC19239
0.8824	High Similarity	NPC98225
0.8762	High Similarity	NPC474421
0.8762	High Similarity	NPC326994
0.8762	High Similarity	NPC72813
0.8762	High Similarity	NPC194620
0.8762	High Similarity	NPC324327
0.8761	High Similarity	NPC303006
0.8738	High Similarity	NPC474709
0.8727	High Similarity	NPC476713
0.8727	High Similarity	NPC476712
0.8679	High Similarity	NPC169888
0.8679	High Similarity	NPC14862
0.8679	High Similarity	NPC327286
0.8679	High Similarity	NPC55972
0.8679	High Similarity	NPC233379
0.8679	High Similarity	NPC474664
0.8667	High Similarity	NPC475802
0.8661	High Similarity	NPC475003
0.8654	High Similarity	NPC4620
0.8636	High Similarity	NPC476711
0.8636	High Similarity	NPC476710
0.8624	High Similarity	NPC477126
0.8598	High Similarity	NPC15218
0.8571	High Similarity	NPC220964
0.8571	High Similarity	NPC475676
0.8455	Intermediate Similarity	NPC89018
0.8396	Intermediate Similarity	NPC146731
0.8378	Intermediate Similarity	NPC226608
0.8378	Intermediate Similarity	NPC88867
0.8365	Intermediate Similarity	NPC474718
0.8364	Intermediate Similarity	NPC269530
0.8364	Intermediate Similarity	NPC317687
0.8333	Intermediate Similarity	NPC128210
0.8304	Intermediate Similarity	NPC470466
0.8273	Intermediate Similarity	NPC317107
0.825	Intermediate Similarity	NPC470185
0.8241	Intermediate Similarity	NPC187435
0.8241	Intermediate Similarity	NPC67321
0.823	Intermediate Similarity	NPC469684
0.823	Intermediate Similarity	NPC58662
0.823	Intermediate Similarity	NPC53396
0.823	Intermediate Similarity	NPC98249
0.8224	Intermediate Similarity	NPC283850
0.8224	Intermediate Similarity	NPC296950
0.819	Intermediate Similarity	NPC23786
0.819	Intermediate Similarity	NPC470265
0.8182	Intermediate Similarity	NPC472215
0.8182	Intermediate Similarity	NPC11491
0.8182	Intermediate Similarity	NPC475134
0.8182	Intermediate Similarity	NPC475563
0.8182	Intermediate Similarity	NPC140409
0.8182	Intermediate Similarity	NPC472214
0.8182	Intermediate Similarity	NPC156248
0.8165	Intermediate Similarity	NPC469916
0.8165	Intermediate Similarity	NPC151393
0.8165	Intermediate Similarity	NPC472439
0.8158	Intermediate Similarity	NPC284707
0.8155	Intermediate Similarity	NPC475659
0.8148	Intermediate Similarity	NPC470979
0.8148	Intermediate Similarity	NPC470975
0.8148	Intermediate Similarity	NPC103088
0.8142	Intermediate Similarity	NPC270478
0.8131	Intermediate Similarity	NPC159533
0.8131	Intermediate Similarity	NPC99510
0.8131	Intermediate Similarity	NPC61442
0.8113	Intermediate Similarity	NPC164598
0.8113	Intermediate Similarity	NPC308824
0.8113	Intermediate Similarity	NPC474339
0.8108	Intermediate Similarity	NPC473921
0.8108	Intermediate Similarity	NPC474846
0.8108	Intermediate Similarity	NPC469655
0.8108	Intermediate Similarity	NPC475480
0.8108	Intermediate Similarity	NPC475668
0.8108	Intermediate Similarity	NPC469656
0.8108	Intermediate Similarity	NPC170294
0.8103	Intermediate Similarity	NPC67569
0.8095	Intermediate Similarity	NPC222303
0.8087	Intermediate Similarity	NPC472667
0.8077	Intermediate Similarity	NPC473859
0.8077	Intermediate Similarity	NPC279621
0.8077	Intermediate Similarity	NPC230800
0.8073	Intermediate Similarity	NPC112780
0.807	Intermediate Similarity	NPC473656
0.807	Intermediate Similarity	NPC475323
0.807	Intermediate Similarity	NPC176513
0.807	Intermediate Similarity	NPC478204
0.807	Intermediate Similarity	NPC473590
0.807	Intermediate Similarity	NPC470775
0.8058	Intermediate Similarity	NPC161998
0.8056	Intermediate Similarity	NPC258532
0.8037	Intermediate Similarity	NPC472552
0.8037	Intermediate Similarity	NPC478156
0.8037	Intermediate Similarity	NPC471148
0.8037	Intermediate Similarity	NPC476081
0.8019	Intermediate Similarity	NPC288876
0.8019	Intermediate Similarity	NPC272223
0.8018	Intermediate Similarity	NPC235014
0.8017	Intermediate Similarity	NPC143755
0.8	Intermediate Similarity	NPC134454
0.8	Intermediate Similarity	NPC474395
0.8	Intermediate Similarity	NPC108581
0.8	Intermediate Similarity	NPC181994
0.8	Intermediate Similarity	NPC478206
0.8	Intermediate Similarity	NPC17326
0.8	Intermediate Similarity	NPC124676
0.8	Intermediate Similarity	NPC146280
0.8	Intermediate Similarity	NPC73911
0.8	Intermediate Similarity	NPC478205
0.8	Intermediate Similarity	NPC322903
0.8	Intermediate Similarity	NPC475372
0.8	Intermediate Similarity	NPC236999
0.8	Intermediate Similarity	NPC306265
0.7983	Intermediate Similarity	NPC473635
0.7982	Intermediate Similarity	NPC234858
0.7982	Intermediate Similarity	NPC477509
0.7982	Intermediate Similarity	NPC470980
0.7982	Intermediate Similarity	NPC154363
0.7982	Intermediate Similarity	NPC471127
0.7982	Intermediate Similarity	NPC472655
0.7981	Intermediate Similarity	NPC471141
0.7966	Intermediate Similarity	NPC469789
0.7966	Intermediate Similarity	NPC473802
0.7966	Intermediate Similarity	NPC67251
0.7966	Intermediate Similarity	NPC129992
0.7966	Intermediate Similarity	NPC472399
0.7965	Intermediate Similarity	NPC75167
0.7965	Intermediate Similarity	NPC471204
0.7965	Intermediate Similarity	NPC264153
0.7965	Intermediate Similarity	NPC311592
0.7963	Intermediate Similarity	NPC474775
0.7963	Intermediate Similarity	NPC475321
0.7963	Intermediate Similarity	NPC156681
0.7963	Intermediate Similarity	NPC72842
0.7961	Intermediate Similarity	NPC476300
0.7944	Intermediate Similarity	NPC472554
0.7931	Intermediate Similarity	NPC312536
0.7928	Intermediate Similarity	NPC469370
0.7928	Intermediate Similarity	NPC273433
0.7928	Intermediate Similarity	NPC5475
0.7928	Intermediate Similarity	NPC284828
0.7928	Intermediate Similarity	NPC475191
0.7928	Intermediate Similarity	NPC173905
0.7928	Intermediate Similarity	NPC218853
0.7928	Intermediate Similarity	NPC472216
0.7925	Intermediate Similarity	NPC216478
0.7925	Intermediate Similarity	NPC124512
0.7925	Intermediate Similarity	NPC159763
0.7925	Intermediate Similarity	NPC278386
0.7917	Intermediate Similarity	NPC470780
0.7913	Intermediate Similarity	NPC10721
0.7913	Intermediate Similarity	NPC13713
0.7909	Intermediate Similarity	NPC143609
0.7909	Intermediate Similarity	NPC180744
0.7909	Intermediate Similarity	NPC477513
0.7909	Intermediate Similarity	NPC293512
0.7905	Intermediate Similarity	NPC21302
0.7905	Intermediate Similarity	NPC473964
0.7905	Intermediate Similarity	NPC11396
0.7905	Intermediate Similarity	NPC476315
0.7899	Intermediate Similarity	NPC473709
0.7899	Intermediate Similarity	NPC8369
0.7899	Intermediate Similarity	NPC473919
0.7895	Intermediate Similarity	NPC181145
0.7895	Intermediate Similarity	NPC472400
0.7895	Intermediate Similarity	NPC117712
0.789	Intermediate Similarity	NPC475585
0.789	Intermediate Similarity	NPC239162
0.789	Intermediate Similarity	NPC473577
0.789	Intermediate Similarity	NPC474550
0.7885	Intermediate Similarity	NPC474247
0.7881	Intermediate Similarity	NPC170538

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 NPC94377 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1705
0.2-0.3	3671
0.3-0.4	2329
0.4-0.5	780
0.5-0.6	325
0.6-0.7	151
0.7-0.8	13
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
0.7925	Intermediate Similarity	NPD4225	Approved
0.7857	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD6698	Approved
0.7767	Intermediate Similarity	NPD46	Approved
0.7759	Intermediate Similarity	NPD7115	Discovery
0.7615	Intermediate Similarity	NPD5344	Discontinued
0.7589	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD6371	Approved
0.7522	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD6686	Approved
0.7364	Intermediate Similarity	NPD6648	Approved
0.7282	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7638	Approved
0.7222	Intermediate Similarity	NPD7319	Approved
0.7213	Intermediate Similarity	NPD8513	Phase 3
0.7213	Intermediate Similarity	NPD8516	Approved
0.7213	Intermediate Similarity	NPD8517	Approved
0.7213	Intermediate Similarity	NPD8515	Approved
0.7207	Intermediate Similarity	NPD7640	Approved
0.7207	Intermediate Similarity	NPD7639	Approved
0.7196	Intermediate Similarity	NPD7983	Approved
0.712	Intermediate Similarity	NPD7507	Approved
0.7103	Intermediate Similarity	NPD7838	Discovery
0.7043	Intermediate Similarity	NPD6008	Approved
0.7034	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6319	Approved
0.6972	Remote Similarity	NPD5778	Approved
0.6972	Remote Similarity	NPD5779	Approved
0.6972	Remote Similarity	NPD6399	Phase 3
0.6967	Remote Similarity	NPD7328	Approved
0.6967	Remote Similarity	NPD7327	Approved
0.6935	Remote Similarity	NPD6921	Approved
0.6929	Remote Similarity	NPD8074	Phase 3
0.6917	Remote Similarity	NPD8133	Approved
0.6911	Remote Similarity	NPD7516	Approved
0.6909	Remote Similarity	NPD5282	Discontinued
0.6885	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1695	Approved
0.6847	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD8328	Phase 3
0.68	Remote Similarity	NPD8033	Approved
0.6772	Remote Similarity	NPD7492	Approved
0.6727	Remote Similarity	NPD7637	Suspended
0.6727	Remote Similarity	NPD6411	Approved
0.6726	Remote Similarity	NPD7902	Approved
0.6723	Remote Similarity	NPD6373	Approved
0.6723	Remote Similarity	NPD6372	Approved
0.672	Remote Similarity	NPD8294	Approved
0.672	Remote Similarity	NPD6054	Approved
0.672	Remote Similarity	NPD8377	Approved
0.672	Remote Similarity	NPD6059	Approved
0.6719	Remote Similarity	NPD6616	Approved
0.6694	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD8378	Approved
0.6639	Remote Similarity	NPD4632	Approved
0.6638	Remote Similarity	NPD7632	Discontinued
0.6636	Remote Similarity	NPD5785	Approved
0.6636	Remote Similarity	NPD1694	Approved
0.6615	Remote Similarity	NPD7736	Approved
0.6614	Remote Similarity	NPD6370	Approved
0.6612	Remote Similarity	NPD6649	Approved
0.6612	Remote Similarity	NPD6650	Approved
0.661	Remote Similarity	NPD6675	Approved
0.661	Remote Similarity	NPD5739	Approved
0.661	Remote Similarity	NPD6402	Approved
0.661	Remote Similarity	NPD7128	Approved
0.6607	Remote Similarity	NPD7748	Approved
0.6577	Remote Similarity	NPD8035	Phase 2
0.6577	Remote Similarity	NPD8034	Phase 2
0.6557	Remote Similarity	NPD6053	Discontinued
0.6555	Remote Similarity	NPD6412	Phase 2
0.6552	Remote Similarity	NPD1700	Approved
0.6545	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6101	Approved
0.6535	Remote Similarity	NPD6015	Approved
0.6535	Remote Similarity	NPD6016	Approved
0.6535	Remote Similarity	NPD7503	Approved
0.6522	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6899	Approved
0.65	Remote Similarity	NPD6881	Approved
0.65	Remote Similarity	NPD7320	Approved
0.6486	Remote Similarity	NPD3168	Discontinued
0.6484	Remote Similarity	NPD5988	Approved
0.6462	Remote Similarity	NPD8273	Phase 1
0.646	Remote Similarity	NPD7900	Approved
0.646	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD7604	Phase 2
0.6429	Remote Similarity	NPD7515	Phase 2
0.6423	Remote Similarity	NPD6882	Approved
0.6417	Remote Similarity	NPD5701	Approved
0.6417	Remote Similarity	NPD5697	Approved
0.6415	Remote Similarity	NPD5369	Approved
0.6404	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD4634	Approved
0.6393	Remote Similarity	NPD7102	Approved
0.6393	Remote Similarity	NPD7290	Approved
0.6393	Remote Similarity	NPD6883	Approved
0.6364	Remote Similarity	NPD4250	Approved
0.6364	Remote Similarity	NPD4251	Approved
0.6364	Remote Similarity	NPD7524	Approved
0.6355	Remote Similarity	NPD4269	Approved
0.6355	Remote Similarity	NPD4270	Approved
0.6349	Remote Similarity	NPD6009	Approved
0.6348	Remote Similarity	NPD7839	Suspended
0.6343	Remote Similarity	NPD7260	Phase 2
0.6341	Remote Similarity	NPD6847	Approved
0.6341	Remote Similarity	NPD8130	Phase 1
0.6341	Remote Similarity	NPD6617	Approved
0.6341	Remote Similarity	NPD6869	Approved
0.6311	Remote Similarity	NPD6012	Approved
0.6311	Remote Similarity	NPD6013	Approved
0.6311	Remote Similarity	NPD6014	Approved
0.6308	Remote Similarity	NPD7642	Approved
0.6296	Remote Similarity	NPD7154	Phase 3
0.6293	Remote Similarity	NPD6083	Phase 2
0.6293	Remote Similarity	NPD6084	Phase 2
0.6279	Remote Similarity	NPD5983	Phase 2
0.6273	Remote Similarity	NPD4249	Approved
0.6273	Remote Similarity	NPD5786	Approved
0.6273	Remote Similarity	NPD3618	Phase 1
0.6261	Remote Similarity	NPD5695	Phase 3
0.6241	Remote Similarity	NPD6033	Approved
0.6239	Remote Similarity	NPD5696	Approved
0.6239	Remote Similarity	NPD4786	Approved
0.6239	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6011	Approved
0.6218	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD8451	Approved
0.6212	Remote Similarity	NPD6336	Discontinued
0.621	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD3667	Approved
0.6183	Remote Similarity	NPD7830	Approved
0.6183	Remote Similarity	NPD7829	Approved
0.6182	Remote Similarity	NPD5363	Approved
0.6182	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6845	Suspended
0.6168	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4821	Approved
0.6168	Remote Similarity	NPD4822	Approved
0.6168	Remote Similarity	NPD4820	Approved
0.6168	Remote Similarity	NPD4819	Approved
0.6168	Remote Similarity	NPD4252	Approved
0.6165	Remote Similarity	NPD8448	Approved
0.6154	Remote Similarity	NPD8039	Approved
0.6154	Remote Similarity	NPD4755	Approved
0.6147	Remote Similarity	NPD6695	Phase 3
0.6147	Remote Similarity	NPD5362	Discontinued
0.6132	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5330	Approved
0.6126	Remote Similarity	NPD7146	Approved
0.6126	Remote Similarity	NPD7334	Approved
0.6126	Remote Similarity	NPD6409	Approved
0.6126	Remote Similarity	NPD6684	Approved
0.6126	Remote Similarity	NPD7521	Approved
0.6106	Remote Similarity	NPD6051	Approved
0.6106	Remote Similarity	NPD5328	Approved
0.6087	Remote Similarity	NPD4202	Approved
0.6083	Remote Similarity	NPD5211	Phase 2
0.6066	Remote Similarity	NPD5357	Phase 1
0.6061	Remote Similarity	NPD6067	Discontinued
0.6055	Remote Similarity	NPD6435	Approved
0.6055	Remote Similarity	NPD5209	Approved
0.605	Remote Similarity	NPD4700	Approved
0.605	Remote Similarity	NPD5286	Approved
0.605	Remote Similarity	NPD5285	Approved
0.605	Remote Similarity	NPD4696	Approved
0.6034	Remote Similarity	NPD6001	Approved
0.6031	Remote Similarity	NPD8444	Approved
0.6029	Remote Similarity	NPD8392	Approved
0.6029	Remote Similarity	NPD8391	Approved
0.6029	Remote Similarity	NPD8390	Approved
0.6019	Remote Similarity	NPD7525	Registered
0.6018	Remote Similarity	NPD6903	Approved
0.6018	Remote Similarity	NPD5737	Approved
0.6018	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6672	Approved
0.6016	Remote Similarity	NPD6274	Approved
0.6015	Remote Similarity	NPD8342	Approved
0.6015	Remote Similarity	NPD8341	Approved
0.6015	Remote Similarity	NPD8340	Approved
0.6015	Remote Similarity	NPD8299	Approved
0.6	Remote Similarity	NPD7100	Approved
0.6	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD5693	Phase 1
0.6	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD6421	Discontinued
0.6	Remote Similarity	NPD5281	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