NPASS Compound

Structure

CID128210 OpenBabel06191715482D 39 42 0 0 1 0 0 0 0 0999 V2000 0.1860 5.4718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5547 6.4662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2693 2.6128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0471 -1.3086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3575 5.2412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1288 -2.0307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9878 1.5851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7663 3.1012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8373 3.4030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3575 2.3110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3575 1.3343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9767 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1574 5.5739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3404 2.3110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8373 -0.7345 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3575 4.2645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1574 -1.9287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9084 3.1012 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4884 2.7994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3404 1.3343 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3343 1.3343 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7663 0.5441 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9084 0.5441 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7315 4.7837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7663 -1.0364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3343 2.3110 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4884 0.8459 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8373 0.2422 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2693 1.0324 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -1.2034 3.7761 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5833 -2.7189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7029 4.8858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0681 -1.9653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8373 1.2190 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 0.4884 3.7761 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7601 -1.0364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3343 3.8914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3404 -0.2461 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 2 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 12 27 1 0 0 0 0 12 35 1 0 0 0 0 13 24 1 0 0 0 0 14 20 1 0 0 0 0 15 25 1 0 0 0 0 15 28 1 6 0 0 0 16 30 2 0 0 0 0 16 36 1 0 0 0 0 17 31 2 0 0 0 0 17 37 1 0 0 0 0 18 26 1 1 0 0 0 18 38 1 0 0 0 0 19 26 1 6 0 0 0 19 36 1 0 0 0 0 20 22 1 0 0 0 0 20 29 1 6 0 0 0 21 23 1 0 0 0 0 21 26 1 1 0 0 0 21 27 1 0 0 0 0 22 28 1 6 0 0 0 22 39 1 0 0 0 0 23 28 1 1 0 0 0 23 37 1 0 0 0 0 24 32 2 0 0 0 0 24 38 1 0 0 0 0 25 33 2 0 0 0 0 25 39 1 0 0 0 0 26 7 1 1 0 0 0 27 11 1 6 0 0 0 27 35 1 0 0 0 0 28 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.22
Volume:	548.549
LogP:	3.365
LogD:	1.674
LogS:	-4.363
# Rotatable Bonds:	7
TPSA:	137.96
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.176
Synthetic Accessibility Score:	6.138
Fsp3:	0.786
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.103
MDCK Permeability:	9.760475222719833e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.253
Plasma Protein Binding (PPB):	63.7562370300293%
Volume Distribution (VD):	1.402
Pgp-substrate:	48.18738555908203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.052
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.189
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.379
CYP3A4-substrate:	0.218

ADMET: Excretion

Clearance (CL):	3.24
Half-life (T1/2):	0.034

ADMET: Toxicity

hERG Blockers:	0.35
Human Hepatotoxicity (H-HT):	0.956
Drug-inuced Liver Injury (DILI):	0.846
AMES Toxicity:	0.222
Rat Oral Acute Toxicity:	0.489
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.417
Carcinogencity:	0.066
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC128210

Natural Product ID:	NPC128210
*Common Name:**	Juncenolide A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QOXJMKFHEPATMO-MGBCRWKJSA-N
Standard InCHI:	InChI=1S/C28H39ClO10/c1-13(2)24(32)38-18-9-8-14(3)20(29)22-28(34,15(4)25(33)39-22)23(37-17(6)31)21-26(18,7)19(36-16(5)30)10-11-27(21)12-35-27/h13,15,18-23,34H,3,8-12H2,1-2,4-7H3/t15-,18-,19-,20-,21+,22-,23-,26-,27+,28-/m0/s1
SMILES:	CC(C)C(=O)O[C@H]1CCC(=C)[C@@H]([C@H]2[C@@]([C@@H](C)C(=O)O2)([C@H]([C@@H]2[C@]1(C)[C@H](CC[C@]12CO1)OC(=O)C)OC(=O)C)O)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517799
PubChem CID:	44584125
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
NPO25525	Junceella juncea	Species	Ellisellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11809065]
NPO25525	Junceella juncea	Species	Ellisellidae	Eukaryota	n.a.	Taiwanese gorgonian	n.a.	PMID[12608873]
NPO25525	Junceella juncea	Species	Ellisellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22071302]
NPO25525	Junceella juncea	Species	Ellisellidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25525	Junceella juncea	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
IC50	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.4	ug.mL-1	PMID[571499]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5.9	ug.mL-1	PMID[571499]

☑ 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 NPC128210 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	252
0.1-0.2	2089
0.2-0.3	6757
0.3-0.4	14601
0.4-0.5	8194
0.5-0.6	7919
0.6-0.7	2765
0.7-0.8	95
0.8-0.85	11
0.85-0.9	4
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9802	High Similarity	NPC11491
0.9802	High Similarity	NPC156248
0.9802	High Similarity	NPC140409
0.9706	High Similarity	NPC170294
0.9519	High Similarity	NPC89018
0.9429	High Similarity	NPC226608
0.9429	High Similarity	NPC88867
0.934	High Similarity	NPC470466
0.901	High Similarity	NPC98225
0.8774	High Similarity	NPC475191
0.8673	High Similarity	NPC282003
0.8673	High Similarity	NPC188222
0.8673	High Similarity	NPC310035
0.8611	High Similarity	NPC470467
0.8596	High Similarity	NPC303006
0.8532	High Similarity	NPC470468
0.8482	Intermediate Similarity	NPC476714
0.8333	Intermediate Similarity	NPC94377
0.8099	Intermediate Similarity	NPC470185
0.7925	Intermediate Similarity	NPC152480
0.7895	Intermediate Similarity	NPC73314
0.7876	Intermediate Similarity	NPC473877
0.7843	Intermediate Similarity	NPC253618
0.7843	Intermediate Similarity	NPC77001
0.7826	Intermediate Similarity	NPC474333
0.7826	Intermediate Similarity	NPC329869
0.7768	Intermediate Similarity	NPC42662
0.7759	Intermediate Similarity	NPC296822
0.7727	Intermediate Similarity	NPC283850
0.7706	Intermediate Similarity	NPC183571
0.7685	Intermediate Similarity	NPC477656
0.7652	Intermediate Similarity	NPC477126
0.7636	Intermediate Similarity	NPC474165
0.7636	Intermediate Similarity	NPC61442
0.7636	Intermediate Similarity	NPC99510
0.7636	Intermediate Similarity	NPC69171
0.7627	Intermediate Similarity	NPC470186
0.7611	Intermediate Similarity	NPC475922
0.7589	Intermediate Similarity	NPC475510
0.7589	Intermediate Similarity	NPC475587
0.7544	Intermediate Similarity	NPC115257
0.7544	Intermediate Similarity	NPC473594
0.7544	Intermediate Similarity	NPC474586
0.7544	Intermediate Similarity	NPC473975
0.7544	Intermediate Similarity	NPC473843
0.7544	Intermediate Similarity	NPC161816
0.7523	Intermediate Similarity	NPC477655
0.7522	Intermediate Similarity	NPC473939
0.7522	Intermediate Similarity	NPC473595
0.75	Intermediate Similarity	NPC474101
0.75	Intermediate Similarity	NPC474395
0.7478	Intermediate Similarity	NPC194619
0.7478	Intermediate Similarity	NPC157476
0.7477	Intermediate Similarity	NPC72842
0.7458	Intermediate Similarity	NPC476713
0.7458	Intermediate Similarity	NPC476712
0.7455	Intermediate Similarity	NPC308824
0.7434	Intermediate Similarity	NPC216636
0.7429	Intermediate Similarity	NPC471378
0.7429	Intermediate Similarity	NPC312471
0.7417	Intermediate Similarity	NPC475003
0.7407	Intermediate Similarity	NPC473964
0.7407	Intermediate Similarity	NPC256227
0.7398	Intermediate Similarity	NPC470973
0.7391	Intermediate Similarity	NPC281624
0.7387	Intermediate Similarity	NPC474709
0.7373	Intermediate Similarity	NPC476710
0.7373	Intermediate Similarity	NPC476711
0.7368	Intermediate Similarity	NPC37628
0.7368	Intermediate Similarity	NPC153587
0.7368	Intermediate Similarity	NPC273155
0.7358	Intermediate Similarity	NPC122057
0.7345	Intermediate Similarity	NPC16313
0.7345	Intermediate Similarity	NPC9303
0.7345	Intermediate Similarity	NPC472655
0.7345	Intermediate Similarity	NPC470587
0.7339	Intermediate Similarity	NPC136781
0.7339	Intermediate Similarity	NPC473963
0.7339	Intermediate Similarity	NPC253586
0.7339	Intermediate Similarity	NPC111348
0.7321	Intermediate Similarity	NPC474166
0.7321	Intermediate Similarity	NPC19239
0.7321	Intermediate Similarity	NPC156681
0.7304	Intermediate Similarity	NPC204652
0.7304	Intermediate Similarity	NPC154906
0.7304	Intermediate Similarity	NPC16657
0.7304	Intermediate Similarity	NPC218853
0.7297	Intermediate Similarity	NPC475958
0.729	Intermediate Similarity	NPC147272
0.7282	Intermediate Similarity	NPC93616
0.7281	Intermediate Similarity	NPC166993
0.7281	Intermediate Similarity	NPC72813
0.7281	Intermediate Similarity	NPC284732
0.7281	Intermediate Similarity	NPC78966
0.7281	Intermediate Similarity	NPC474421
0.7281	Intermediate Similarity	NPC293512
0.7281	Intermediate Similarity	NPC326994
0.7281	Intermediate Similarity	NPC194620
0.7281	Intermediate Similarity	NPC319438
0.7281	Intermediate Similarity	NPC324327
0.7264	Intermediate Similarity	NPC153853
0.7255	Intermediate Similarity	NPC239308
0.7248	Intermediate Similarity	NPC93245
0.7238	Intermediate Similarity	NPC92370
0.7238	Intermediate Similarity	NPC471221
0.7217	Intermediate Similarity	NPC112895
0.7217	Intermediate Similarity	NPC55972
0.7217	Intermediate Similarity	NPC169888
0.7217	Intermediate Similarity	NPC218123
0.7217	Intermediate Similarity	NPC231278
0.7217	Intermediate Similarity	NPC474664
0.7217	Intermediate Similarity	NPC14862
0.7217	Intermediate Similarity	NPC233379
0.7217	Intermediate Similarity	NPC327286
0.7213	Intermediate Similarity	NPC477046
0.7213	Intermediate Similarity	NPC102822
0.7212	Intermediate Similarity	NPC246347
0.7212	Intermediate Similarity	NPC279260
0.7207	Intermediate Similarity	NPC108371
0.7203	Intermediate Similarity	NPC471252
0.72	Intermediate Similarity	NPC478207
0.7196	Intermediate Similarity	NPC312805
0.7196	Intermediate Similarity	NPC91251
0.7196	Intermediate Similarity	NPC165180
0.7193	Intermediate Similarity	NPC475802
0.7193	Intermediate Similarity	NPC200957
0.7193	Intermediate Similarity	NPC138908
0.7184	Intermediate Similarity	NPC97505
0.7182	Intermediate Similarity	NPC111187
0.7182	Intermediate Similarity	NPC190080
0.7182	Intermediate Similarity	NPC474921
0.7179	Intermediate Similarity	NPC272242
0.717	Intermediate Similarity	NPC469866
0.717	Intermediate Similarity	NPC161560
0.717	Intermediate Similarity	NPC471342
0.717	Intermediate Similarity	NPC291875
0.717	Intermediate Similarity	NPC194642
0.7168	Intermediate Similarity	NPC122811
0.7168	Intermediate Similarity	NPC87927
0.7168	Intermediate Similarity	NPC4620
0.7168	Intermediate Similarity	NPC225238
0.7168	Intermediate Similarity	NPC277074
0.7168	Intermediate Similarity	NPC209298
0.7167	Intermediate Similarity	NPC474654
0.7167	Intermediate Similarity	NPC176513
0.7167	Intermediate Similarity	NPC287343
0.7167	Intermediate Similarity	NPC97908
0.7167	Intermediate Similarity	NPC470775
0.7167	Intermediate Similarity	NPC122033
0.7167	Intermediate Similarity	NPC470854
0.7156	Intermediate Similarity	NPC157686
0.7156	Intermediate Similarity	NPC259042
0.7155	Intermediate Similarity	NPC15218
0.7155	Intermediate Similarity	NPC322912
0.7155	Intermediate Similarity	NPC131903
0.7155	Intermediate Similarity	NPC274827
0.7143	Intermediate Similarity	NPC471377
0.7131	Intermediate Similarity	NPC329008
0.7131	Intermediate Similarity	NPC317635
0.7119	Intermediate Similarity	NPC473397
0.7119	Intermediate Similarity	NPC317687
0.7119	Intermediate Similarity	NPC269530
0.7119	Intermediate Similarity	NPC474927
0.7117	Intermediate Similarity	NPC78427
0.7117	Intermediate Similarity	NPC16911
0.7115	Intermediate Similarity	NPC196911
0.7115	Intermediate Similarity	NPC471379
0.7105	Intermediate Similarity	NPC475036
0.7105	Intermediate Similarity	NPC301787
0.7105	Intermediate Similarity	NPC475676
0.7105	Intermediate Similarity	NPC146731
0.7105	Intermediate Similarity	NPC220964
0.7103	Intermediate Similarity	NPC65359
0.7094	Intermediate Similarity	NPC100908
0.7094	Intermediate Similarity	NPC474786
0.7094	Intermediate Similarity	NPC474567
0.7094	Intermediate Similarity	NPC137104
0.7094	Intermediate Similarity	NPC320383
0.7094	Intermediate Similarity	NPC475463
0.7094	Intermediate Similarity	NPC250956
0.7091	Intermediate Similarity	NPC470883
0.7091	Intermediate Similarity	NPC39859
0.7091	Intermediate Similarity	NPC76862
0.7091	Intermediate Similarity	NPC284518
0.7091	Intermediate Similarity	NPC158416
0.7083	Intermediate Similarity	NPC270478
0.708	Intermediate Similarity	NPC275990
0.708	Intermediate Similarity	NPC164551
0.708	Intermediate Similarity	NPC283567
0.7075	Intermediate Similarity	NPC470260
0.7075	Intermediate Similarity	NPC48824
0.7075	Intermediate Similarity	NPC229407
0.7075	Intermediate Similarity	NPC250687
0.7075	Intermediate Similarity	NPC75443
0.7075	Intermediate Similarity	NPC254572
0.7069	Intermediate Similarity	NPC469916
0.7069	Intermediate Similarity	NPC258323
0.7069	Intermediate Similarity	NPC472439
0.7069	Intermediate Similarity	NPC151393
0.7064	Intermediate Similarity	NPC225474

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 NPC128210 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	2593
0.2-0.3	3968
0.3-0.4	1639
0.4-0.5	436
0.5-0.6	262
0.6-0.7	31
0.7-0.8	0
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
0.6923	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4225	Approved
0.6615	Remote Similarity	NPD6033	Approved
0.6613	Remote Similarity	NPD7115	Discovery
0.6577	Remote Similarity	NPD8034	Phase 2
0.6577	Remote Similarity	NPD8035	Phase 2
0.6555	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1700	Approved
0.6535	Remote Similarity	NPD5983	Phase 2
0.6504	Remote Similarity	NPD8133	Approved
0.6504	Remote Similarity	NPD4632	Approved
0.6496	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD46	Approved
0.6486	Remote Similarity	NPD6698	Approved
0.648	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6008	Approved
0.6462	Remote Similarity	NPD6336	Discontinued
0.6457	Remote Similarity	NPD6319	Approved
0.6446	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5344	Discontinued
0.6406	Remote Similarity	NPD6921	Approved
0.6393	Remote Similarity	NPD6371	Approved
0.6378	Remote Similarity	NPD7100	Approved
0.6372	Remote Similarity	NPD6399	Phase 3
0.6364	Remote Similarity	NPD6686	Approved
0.6316	Remote Similarity	NPD5282	Discontinued
0.6308	Remote Similarity	NPD8328	Phase 3
0.6299	Remote Similarity	NPD6335	Approved
0.6283	Remote Similarity	NPD7983	Approved
0.626	Remote Similarity	NPD7492	Approved
0.625	Remote Similarity	NPD7101	Approved
0.622	Remote Similarity	NPD6009	Approved
0.6212	Remote Similarity	NPD6616	Approved
0.6202	Remote Similarity	NPD6054	Approved
0.6202	Remote Similarity	NPD6059	Approved
0.6194	Remote Similarity	NPD7319	Approved
0.6186	Remote Similarity	NPD6648	Approved
0.6182	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6373	Approved
0.6179	Remote Similarity	NPD6372	Approved
0.6172	Remote Similarity	NPD6313	Approved
0.6172	Remote Similarity	NPD6314	Approved
0.6165	Remote Similarity	NPD7078	Approved
0.6165	Remote Similarity	NPD8293	Discontinued
0.616	Remote Similarity	NPD8297	Approved
0.6154	Remote Similarity	NPD8517	Approved
0.6154	Remote Similarity	NPD8516	Approved
0.6154	Remote Similarity	NPD7902	Approved
0.6154	Remote Similarity	NPD8515	Approved
0.6154	Remote Similarity	NPD8513	Phase 3
0.6148	Remote Similarity	NPD5956	Approved
0.614	Remote Similarity	NPD6411	Approved
0.6119	Remote Similarity	NPD7736	Approved
0.6107	Remote Similarity	NPD6370	Approved
0.6102	Remote Similarity	NPD7638	Approved
0.609	Remote Similarity	NPD7507	Approved
0.6087	Remote Similarity	NPD5778	Approved
0.6087	Remote Similarity	NPD5779	Approved
0.608	Remote Similarity	NPD6650	Approved
0.608	Remote Similarity	NPD6649	Approved
0.6066	Remote Similarity	NPD7128	Approved
0.6066	Remote Similarity	NPD5739	Approved
0.6066	Remote Similarity	NPD6675	Approved
0.6066	Remote Similarity	NPD6402	Approved
0.605	Remote Similarity	NPD7639	Approved
0.605	Remote Similarity	NPD7640	Approved
0.6036	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD7748	Approved
0.6031	Remote Similarity	NPD6016	Approved
0.6031	Remote Similarity	NPD6015	Approved
0.6016	Remote Similarity	NPD6868	Approved
0.6016	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD4522	Approved
0.5985	Remote Similarity	NPD5988	Approved
0.5968	Remote Similarity	NPD6899	Approved
0.5968	Remote Similarity	NPD6881	Approved
0.5968	Remote Similarity	NPD7320	Approved
0.5965	Remote Similarity	NPD6101	Approved
0.5965	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD5215	Approved
0.594	Remote Similarity	NPD7604	Phase 2
0.5926	Remote Similarity	NPD8074	Phase 3
0.5923	Remote Similarity	NPD7328	Approved
0.5923	Remote Similarity	NPD7327	Approved
0.5913	Remote Similarity	NPD3168	Discontinued
0.5913	Remote Similarity	NPD7838	Discovery
0.5906	Remote Similarity	NPD6882	Approved
0.5897	Remote Similarity	NPD7900	Approved
0.5897	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD5701	Approved
0.5887	Remote Similarity	NPD5697	Approved
0.5878	Remote Similarity	NPD7516	Approved
0.5873	Remote Similarity	NPD4634	Approved
0.5873	Remote Similarity	NPD6883	Approved
0.5873	Remote Similarity	NPD7290	Approved
0.5873	Remote Similarity	NPD5169	Approved
0.5873	Remote Similarity	NPD7102	Approved
0.5862	Remote Similarity	NPD7637	Suspended
0.5862	Remote Similarity	NPD7515	Phase 2
0.5847	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6115	Approved
0.5833	Remote Similarity	NPD6118	Approved
0.5833	Remote Similarity	NPD6697	Approved
0.5833	Remote Similarity	NPD6114	Approved
0.5827	Remote Similarity	NPD5127	Approved
0.5827	Remote Similarity	NPD8130	Phase 1
0.5827	Remote Similarity	NPD5216	Approved
0.5827	Remote Similarity	NPD6617	Approved
0.5827	Remote Similarity	NPD6847	Approved
0.5827	Remote Similarity	NPD5217	Approved
0.5827	Remote Similarity	NPD6869	Approved
0.5826	Remote Similarity	NPD1695	Approved
0.5818	Remote Similarity	NPD5369	Approved
0.5814	Remote Similarity	NPD5167	Approved
0.5794	Remote Similarity	NPD6013	Approved
0.5794	Remote Similarity	NPD6014	Approved
0.5794	Remote Similarity	NPD6012	Approved
0.5789	Remote Similarity	NPD8033	Approved
0.575	Remote Similarity	NPD6083	Phase 2
0.575	Remote Similarity	NPD6084	Phase 2
0.5741	Remote Similarity	NPD6116	Phase 1
0.5714	Remote Similarity	NPD5128	Approved
0.5714	Remote Similarity	NPD6011	Approved
0.5714	Remote Similarity	NPD5695	Phase 3
0.5714	Remote Similarity	NPD8377	Approved
0.5714	Remote Similarity	NPD8294	Approved
0.5703	Remote Similarity	NPD1719	Phase 1
0.5703	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD5696	Approved
0.5702	Remote Similarity	NPD3618	Phase 1
0.5691	Remote Similarity	NPD7632	Discontinued
0.5672	Remote Similarity	NPD8378	Approved
0.5672	Remote Similarity	NPD8380	Approved
0.5672	Remote Similarity	NPD8296	Approved
0.5672	Remote Similarity	NPD8379	Approved
0.5672	Remote Similarity	NPD8335	Approved
0.5667	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD4786	Approved
0.5652	Remote Similarity	NPD7524	Approved
0.5648	Remote Similarity	NPD6117	Approved
0.5635	Remote Similarity	NPD6614	Approved
0.5625	Remote Similarity	NPD3667	Approved
0.562	Remote Similarity	NPD4755	Approved
0.5619	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.56	Remote Similarity	NPD8170	Clinical (unspecified phase)

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