NPASS Compound

Structure

CID13190 OpenBabel06191715342D 40 46 0 0 1 0 0 0 0 0999 V2000 -1.1244 3.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0429 1.5432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4157 0.3558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9535 -1.1078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1084 -3.5804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2625 -3.0923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3945 2.6446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1076 -0.6512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2616 -0.1631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9013 1.7685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7994 -3.5799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6442 -2.1148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7259 -1.6282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1228 1.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3140 -1.2355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6176 2.6437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3664 0.7905 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9541 -3.0919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6445 -3.0914 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2622 -2.1158 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1078 -1.6272 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4163 -1.6277 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7108 -0.3437 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7256 -0.6522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7988 -1.6267 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5701 -0.1636 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1368 0.4458 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1661 0.3435 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7693 -0.5483 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4160 -0.6517 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9538 -2.1153 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3960 0.8916 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5172 -3.5948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6815 -0.2414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5336 1.3377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5921 1.1331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3433 -1.3378 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6160 0.8907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7986 -0.6506 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 16 2 0 0 0 0 2 17 1 0 0 0 0 5 6 1 0 0 0 0 5 18 2 0 0 0 0 7 10 1 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 30 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 19 1 0 0 0 0 12 25 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 38 1 0 0 0 0 15 23 1 0 0 0 0 15 37 1 0 0 0 0 17 26 1 0 0 0 0 17 32 1 1 0 0 0 18 31 1 0 0 0 0 19 33 1 6 0 0 0 20 6 1 1 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 31 1 6 0 0 0 22 30 1 6 0 0 0 23 27 1 0 0 0 0 23 34 1 1 0 0 0 24 13 1 6 0 0 0 24 26 1 0 0 0 0 24 40 1 0 0 0 0 25 31 1 6 0 0 0 25 39 1 0 0 0 0 26 30 1 6 0 0 0 27 28 1 0 0 0 0 27 35 1 1 0 0 0 28 29 1 0 0 0 0 28 36 1 6 0 0 0 29 37 1 0 0 0 0 29 39 1 1 0 0 0 30 3 1 6 0 0 0 31 4 1 6 0 0 0 32 10 1 6 0 0 0 32 38 1 0 0 0 0 32 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	560.33
Volume:	567.182
LogP:	2.788
LogD:	3.077
LogS:	-4.607
# Rotatable Bonds:	2
TPSA:	117.84
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.381
Synthetic Accessibility Score:	5.994
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.079
MDCK Permeability:	6.566928732354427e-06
Pgp-inhibitor:	0.431
Pgp-substrate:	0.148
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.731
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	56.49980926513672%
Volume Distribution (VD):	0.911
Pgp-substrate:	37.728172302246094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.864
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.417
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.182
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	2.872
Half-life (T1/2):	0.45

ADMET: Toxicity

hERG Blockers:	0.939
Human Hepatotoxicity (H-HT):	0.333
Drug-inuced Liver Injury (DILI):	0.292
AMES Toxicity:	0.558
Rat Oral Acute Toxicity:	0.33
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.883
Carcinogencity:	0.862
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC13190

Natural Product ID:	NPC13190
*Common Name:**	UWZBWGTWUAQHLK-FWDMDKSGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UWZBWGTWUAQHLK-FWDMDKSGSA-N
Standard InCHI:	InChI=1S/C32H48O8/c1-16-7-10-32(38-14-16)17(2)26-24(40-32)13-22-20-6-5-18-11-19(33)12-25(31(18,4)21(20)8-9-30(22,26)3)39-29-28(36)27(35)23(34)15-37-29/h5,17,19-29,33-36H,1,6-15H2,2-4H3/t17-,19+,20+,21-,22-,23-,24-,25+,26-,27-,28+,29-,30-,31-,32+/m0/s1
SMILES:	O[C@H]1C[C@@H](O[C@@H]2OC[C@@H]([C@@H]([C@H]2O)O)O)[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3C[C@H]3[C@@H]2[C@H](C)[C@]2(O3)CCC(=C)CO2)C)C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454690
PubChem CID:	15719625
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

*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
NPO8452	Dracaena angustifolia	Species	Asparagaceae	Eukaryota	roots and rhizomes	n.a.	n.a.	PMID[11575942]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[15283458]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[15577257]
NPO8452	Dracaena angustifolia	Species	Asparagaceae	Eukaryota	stems	Xishuangbanna, Yunnan, China	2005-JUL	PMID[20718450]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9051910]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8452	Dracaena angustifolia	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12181	Albizia julibrissin	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
IC50	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	40000.0	nM	PMID[490497]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	77200.0	nM	PMID[490497]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	47900.0	nM	PMID[490497]

☑ 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 NPC13190 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	298
0.1-0.2	1941
0.2-0.3	5913
0.3-0.4	13053
0.4-0.5	9493
0.5-0.6	5972
0.6-0.7	3643
0.7-0.8	1736
0.8-0.85	339
0.85-0.9	192
0.9-0.95	106
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9903	High Similarity	NPC112274
0.9808	High Similarity	NPC51154
0.9714	High Similarity	NPC11548
0.9706	High Similarity	NPC476538
0.9706	High Similarity	NPC476541
0.9706	High Similarity	NPC476539
0.9706	High Similarity	NPC476540
0.9623	High Similarity	NPC477030
0.9623	High Similarity	NPC477029
0.9612	High Similarity	NPC475670
0.9612	High Similarity	NPC70204
0.9612	High Similarity	NPC477026
0.9612	High Similarity	NPC477027
0.9612	High Similarity	NPC306131
0.9524	High Similarity	NPC42171
0.951	High Similarity	NPC473476
0.951	High Similarity	NPC181845
0.951	High Similarity	NPC473923
0.9444	High Similarity	NPC475403
0.9444	High Similarity	NPC160888
0.9439	High Similarity	NPC148965
0.9429	High Similarity	NPC475247
0.9429	High Similarity	NPC294129
0.9423	High Similarity	NPC157530
0.9423	High Similarity	NPC250089
0.9423	High Similarity	NPC14630
0.9417	High Similarity	NPC470432
0.9417	High Similarity	NPC14704
0.9417	High Similarity	NPC230507
0.9417	High Similarity	NPC305423
0.9417	High Similarity	NPC161676
0.9417	High Similarity	NPC226642
0.9417	High Similarity	NPC283829
0.9417	High Similarity	NPC113044
0.9358	High Similarity	NPC473633
0.9358	High Similarity	NPC476085
0.9358	High Similarity	NPC195560
0.9358	High Similarity	NPC229962
0.9333	High Similarity	NPC141433
0.9327	High Similarity	NPC98696
0.932	High Similarity	NPC242748
0.9273	High Similarity	NPC233391
0.9273	High Similarity	NPC50689
0.9273	High Similarity	NPC207243
0.9273	High Similarity	NPC198325
0.9245	High Similarity	NPC197231
0.9238	High Similarity	NPC475550
0.9238	High Similarity	NPC224098
0.9238	High Similarity	NPC84956
0.9238	High Similarity	NPC244086
0.9238	High Similarity	NPC470433
0.9238	High Similarity	NPC194207
0.9238	High Similarity	NPC477809
0.9238	High Similarity	NPC249265
0.9238	High Similarity	NPC73243
0.9238	High Similarity	NPC248746
0.9238	High Similarity	NPC102016
0.9238	High Similarity	NPC46190
0.9238	High Similarity	NPC232054
0.9238	High Similarity	NPC6806
0.9238	High Similarity	NPC150372
0.9238	High Similarity	NPC171073
0.9238	High Similarity	NPC95051
0.9238	High Similarity	NPC42482
0.9238	High Similarity	NPC309278
0.9238	High Similarity	NPC218571
0.9238	High Similarity	NPC40440
0.9238	High Similarity	NPC300557
0.9238	High Similarity	NPC475333
0.9238	High Similarity	NPC208383
0.9238	High Similarity	NPC22779
0.9231	High Similarity	NPC473469
0.9223	High Similarity	NPC93352
0.9159	High Similarity	NPC19888
0.9151	High Similarity	NPC103627
0.9151	High Similarity	NPC477811
0.9151	High Similarity	NPC170974
0.9151	High Similarity	NPC269297
0.9151	High Similarity	NPC23808
0.9151	High Similarity	NPC222202
0.9151	High Similarity	NPC247037
0.9151	High Similarity	NPC224314
0.9151	High Similarity	NPC87998
0.9151	High Similarity	NPC191439
0.9135	High Similarity	NPC474569
0.9118	High Similarity	NPC176406
0.9107	High Similarity	NPC43842
0.9083	High Similarity	NPC63609
0.9074	High Similarity	NPC469347
0.9074	High Similarity	NPC469348
0.9065	High Similarity	NPC476547
0.9065	High Similarity	NPC13193
0.9065	High Similarity	NPC124677
0.9065	High Similarity	NPC477032
0.9065	High Similarity	NPC477028
0.9057	High Similarity	NPC473318
0.9057	High Similarity	NPC476835
0.9057	High Similarity	NPC473328
0.9057	High Similarity	NPC28844
0.9057	High Similarity	NPC128133
0.9048	High Similarity	NPC94272
0.9048	High Similarity	NPC33053
0.9038	High Similarity	NPC470885
0.9038	High Similarity	NPC187400
0.9038	High Similarity	NPC221562
0.9029	High Similarity	NPC272015
0.9027	High Similarity	NPC106589
0.9027	High Similarity	NPC257207
0.9027	High Similarity	NPC295133
0.9027	High Similarity	NPC202261
0.9	High Similarity	NPC477807
0.9	High Similarity	NPC476690
0.9	High Similarity	NPC20979
0.9	High Similarity	NPC100048
0.8991	High Similarity	NPC477810
0.8981	High Similarity	NPC210569
0.8981	High Similarity	NPC254255
0.8981	High Similarity	NPC263359
0.8981	High Similarity	NPC32361
0.8981	High Similarity	NPC31896
0.8981	High Similarity	NPC231797
0.8981	High Similarity	NPC473567
0.8981	High Similarity	NPC216595
0.8981	High Similarity	NPC244431
0.8972	High Similarity	NPC65155
0.8962	High Similarity	NPC295980
0.8962	High Similarity	NPC476513
0.8962	High Similarity	NPC7213
0.8952	High Similarity	NPC309448
0.8952	High Similarity	NPC26798
0.8919	High Similarity	NPC10366
0.8899	High Similarity	NPC79900
0.8899	High Similarity	NPC144068
0.8899	High Similarity	NPC476693
0.8889	High Similarity	NPC114188
0.8889	High Similarity	NPC473021
0.8889	High Similarity	NPC208189
0.8889	High Similarity	NPC472987
0.8889	High Similarity	NPC65034
0.8868	High Similarity	NPC54619
0.8868	High Similarity	NPC190395
0.8857	High Similarity	NPC75608
0.8857	High Similarity	NPC475365
0.8846	High Similarity	NPC159036
0.8846	High Similarity	NPC312553
0.8846	High Similarity	NPC288694
0.8835	High Similarity	NPC282669
0.8824	High Similarity	NPC177818
0.8824	High Similarity	NPC473890
0.8824	High Similarity	NPC243728
0.8818	High Similarity	NPC167183
0.8818	High Similarity	NPC32707
0.8818	High Similarity	NPC477808
0.8807	High Similarity	NPC308140
0.8785	High Similarity	NPC125324
0.8785	High Similarity	NPC49032
0.8785	High Similarity	NPC220427
0.8785	High Similarity	NPC51172
0.8774	High Similarity	NPC474015
0.8762	High Similarity	NPC213190
0.8762	High Similarity	NPC473198
0.8762	High Similarity	NPC131479
0.8762	High Similarity	NPC475701
0.8762	High Similarity	NPC157659
0.8762	High Similarity	NPC245280
0.8762	High Similarity	NPC189852
0.8762	High Similarity	NPC286969
0.8762	High Similarity	NPC114874
0.8762	High Similarity	NPC472252
0.8762	High Similarity	NPC31907
0.8762	High Similarity	NPC155010
0.8762	High Similarity	NPC473020
0.8762	High Similarity	NPC16520
0.8762	High Similarity	NPC8039
0.8762	High Similarity	NPC211879
0.8762	High Similarity	NPC120123
0.8762	High Similarity	NPC16573
0.8761	High Similarity	NPC475629
0.8761	High Similarity	NPC475556
0.8761	High Similarity	NPC107607
0.875	High Similarity	NPC470434
0.875	High Similarity	NPC218093
0.875	High Similarity	NPC285231
0.875	High Similarity	NPC21568
0.875	High Similarity	NPC475357
0.8739	High Similarity	NPC207637
0.8739	High Similarity	NPC477031
0.8738	High Similarity	NPC158088
0.8727	High Similarity	NPC476546
0.8727	High Similarity	NPC307642
0.8716	High Similarity	NPC470748
0.8704	High Similarity	NPC151134
0.8704	High Similarity	NPC472901
0.8704	High Similarity	NPC302057
0.8692	High Similarity	NPC231340
0.8684	High Similarity	NPC475219
0.8684	High Similarity	NPC173555
0.8684	High Similarity	NPC314535
0.8684	High Similarity	NPC231518
0.8679	High Similarity	NPC110656

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 NPC13190 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	2082
0.2-0.3	4218
0.3-0.4	1760
0.4-0.5	460
0.5-0.6	265
0.6-0.7	98
0.7-0.8	17
0.8-0.85	5
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8684	High Similarity	NPD8379	Approved
0.8684	High Similarity	NPD8033	Approved
0.8684	High Similarity	NPD8296	Approved
0.8684	High Similarity	NPD8335	Approved
0.8684	High Similarity	NPD8378	Approved
0.8684	High Similarity	NPD8380	Approved
0.8596	High Similarity	NPD8377	Approved
0.8596	High Similarity	NPD8294	Approved
0.8421	Intermediate Similarity	NPD7327	Approved
0.8421	Intermediate Similarity	NPD7328	Approved
0.8348	Intermediate Similarity	NPD7516	Approved
0.8051	Intermediate Similarity	NPD7503	Approved
0.7905	Intermediate Similarity	NPD8171	Discontinued
0.7857	Intermediate Similarity	NPD6412	Phase 2
0.7787	Intermediate Similarity	NPD7507	Approved
0.7759	Intermediate Similarity	NPD8133	Approved
0.7742	Intermediate Similarity	NPD7319	Approved
0.7698	Intermediate Similarity	NPD8449	Approved
0.7638	Intermediate Similarity	NPD8450	Suspended
0.7328	Intermediate Similarity	NPD6686	Approved
0.7265	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6370	Approved
0.7244	Intermediate Similarity	NPD7736	Approved
0.7217	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD8293	Discontinued
0.7131	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7524	Approved
0.7097	Intermediate Similarity	NPD6054	Approved
0.7097	Intermediate Similarity	NPD6059	Approved
0.7063	Intermediate Similarity	NPD8328	Phase 3
0.704	Intermediate Similarity	NPD8515	Approved
0.704	Intermediate Similarity	NPD8517	Approved
0.704	Intermediate Similarity	NPD8513	Phase 3
0.704	Intermediate Similarity	NPD8516	Approved
0.6981	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7638	Approved
0.6929	Remote Similarity	NPD6067	Discontinued
0.6923	Remote Similarity	NPD6928	Phase 2
0.6905	Remote Similarity	NPD6015	Approved
0.6905	Remote Similarity	NPD6016	Approved
0.6887	Remote Similarity	NPD6695	Phase 3
0.6875	Remote Similarity	NPD7492	Approved
0.687	Remote Similarity	NPD7639	Approved
0.687	Remote Similarity	NPD7640	Approved
0.6863	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7625	Phase 1
0.685	Remote Similarity	NPD5988	Approved
0.6822	Remote Similarity	NPD6616	Approved
0.6789	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7750	Discontinued
0.6769	Remote Similarity	NPD7078	Approved
0.6765	Remote Similarity	NPD7339	Approved
0.6765	Remote Similarity	NPD6942	Approved
0.6762	Remote Similarity	NPD7525	Registered
0.6721	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4159	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD7645	Phase 2
0.6667	Remote Similarity	NPD6929	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6604	Remote Similarity	NPD6931	Approved
0.6604	Remote Similarity	NPD6930	Phase 2
0.6591	Remote Similarity	NPD6033	Approved
0.6587	Remote Similarity	NPD7115	Discovery
0.6587	Remote Similarity	NPD6009	Approved
0.6562	Remote Similarity	NPD6319	Approved
0.6518	Remote Similarity	NPD6051	Approved
0.6496	Remote Similarity	NPD4225	Approved
0.6491	Remote Similarity	NPD6399	Phase 3
0.648	Remote Similarity	NPD4632	Approved
0.6476	Remote Similarity	NPD5776	Phase 2
0.6476	Remote Similarity	NPD6925	Approved
0.6475	Remote Similarity	NPD7320	Approved
0.6446	Remote Similarity	NPD6008	Approved
0.6446	Remote Similarity	NPD6675	Approved
0.6446	Remote Similarity	NPD5739	Approved
0.6446	Remote Similarity	NPD6402	Approved
0.6446	Remote Similarity	NPD7128	Approved
0.6423	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6372	Approved
0.6423	Remote Similarity	NPD6373	Approved
0.6415	Remote Similarity	NPD7145	Approved
0.6404	Remote Similarity	NPD7087	Discontinued
0.64	Remote Similarity	NPD6053	Discontinued
0.6381	Remote Similarity	NPD6933	Approved
0.6364	Remote Similarity	NPD4786	Approved
0.6346	Remote Similarity	NPD4784	Approved
0.6346	Remote Similarity	NPD4785	Approved
0.6341	Remote Similarity	NPD6899	Approved
0.6341	Remote Similarity	NPD6881	Approved
0.6333	Remote Similarity	NPD7632	Discontinued
0.6321	Remote Similarity	NPD6932	Approved
0.632	Remote Similarity	NPD8130	Phase 1
0.632	Remote Similarity	NPD6649	Approved
0.632	Remote Similarity	NPD6650	Approved
0.6311	Remote Similarity	NPD4243	Approved
0.6306	Remote Similarity	NPD6893	Approved
0.6296	Remote Similarity	NPD7514	Phase 3
0.6271	Remote Similarity	NPD6084	Phase 2
0.6271	Remote Similarity	NPD6083	Phase 2
0.6271	Remote Similarity	NPD4755	Approved
0.6269	Remote Similarity	NPD8074	Phase 3
0.6261	Remote Similarity	NPD7637	Suspended
0.626	Remote Similarity	NPD5697	Approved
0.626	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD5344	Discontinued
0.625	Remote Similarity	NPD5956	Approved
0.624	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.624	Remote Similarity	NPD7102	Approved
0.624	Remote Similarity	NPD7290	Approved
0.624	Remote Similarity	NPD6883	Approved
0.624	Remote Similarity	NPD4634	Approved
0.6239	Remote Similarity	NPD7991	Discontinued
0.6239	Remote Similarity	NPD6902	Approved
0.6218	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.621	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4202	Approved
0.6204	Remote Similarity	NPD6683	Phase 2
0.6198	Remote Similarity	NPD5211	Phase 2
0.619	Remote Similarity	NPD6847	Approved
0.619	Remote Similarity	NPD6869	Approved
0.619	Remote Similarity	NPD6924	Approved
0.619	Remote Similarity	NPD6617	Approved
0.619	Remote Similarity	NPD6926	Approved
0.6182	Remote Similarity	NPD3667	Approved
0.6179	Remote Similarity	NPD6640	Phase 3
0.6167	Remote Similarity	NPD5286	Approved
0.6167	Remote Similarity	NPD4700	Approved
0.6167	Remote Similarity	NPD4696	Approved
0.6167	Remote Similarity	NPD5285	Approved
0.6165	Remote Similarity	NPD7604	Phase 2
0.616	Remote Similarity	NPD6014	Approved
0.616	Remote Similarity	NPD6013	Approved
0.616	Remote Similarity	NPD6012	Approved
0.6154	Remote Similarity	NPD7748	Approved
0.6147	Remote Similarity	NPD7332	Phase 2
0.6147	Remote Similarity	NPD4748	Discontinued
0.6136	Remote Similarity	NPD5983	Phase 2
0.6134	Remote Similarity	NPD7902	Approved
0.6129	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD8034	Phase 2
0.6121	Remote Similarity	NPD8035	Phase 2
0.6098	Remote Similarity	NPD5141	Approved
0.6091	Remote Similarity	NPD6898	Phase 1
0.609	Remote Similarity	NPD5125	Phase 3
0.609	Remote Similarity	NPD5126	Approved
0.6087	Remote Similarity	NPD5328	Approved
0.6087	Remote Similarity	NPD4753	Phase 2
0.608	Remote Similarity	NPD6011	Approved
0.6074	Remote Similarity	NPD6336	Discontinued
0.6071	Remote Similarity	NPD3133	Approved
0.6071	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD3665	Phase 1
0.6071	Remote Similarity	NPD3666	Approved
0.6066	Remote Similarity	NPD4633	Approved
0.6066	Remote Similarity	NPD5225	Approved
0.6066	Remote Similarity	NPD5224	Approved
0.6066	Remote Similarity	NPD5226	Approved
0.6063	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD4768	Approved
0.6048	Remote Similarity	NPD4767	Approved
0.6034	Remote Similarity	NPD7838	Discovery
0.6034	Remote Similarity	NPD3168	Discontinued
0.6034	Remote Similarity	NPD6698	Approved
0.6034	Remote Similarity	NPD46	Approved
0.6016	Remote Similarity	NPD5174	Approved
0.6016	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD6903	Approved
0.6	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7152	Approved
0.6	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7151	Approved
0.6	Remote Similarity	NPD7150	Approved
0.5988	Remote Similarity	NPD7799	Discontinued
0.5985	Remote Similarity	NPD8336	Approved
0.5985	Remote Similarity	NPD8337	Approved
0.5984	Remote Similarity	NPD5223	Approved
0.5983	Remote Similarity	NPD6079	Approved
0.5983	Remote Similarity	NPD7515	Phase 2
0.5981	Remote Similarity	NPD5275	Approved
0.5981	Remote Similarity	NPD4190	Phase 3
0.5966	Remote Similarity	NPD5695	Phase 3
0.5966	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6684	Approved
0.5965	Remote Similarity	NPD7334	Approved
0.5965	Remote Similarity	NPD7146	Approved
0.5965	Remote Similarity	NPD3618	Phase 1
0.5965	Remote Similarity	NPD7521	Approved
0.5965	Remote Similarity	NPD6409	Approved
0.5965	Remote Similarity	NPD5330	Approved
0.5962	Remote Similarity	NPD6923	Approved
0.5962	Remote Similarity	NPD6922	Approved
0.5952	Remote Similarity	NPD4730	Approved
0.5952	Remote Similarity	NPD4729	Approved
0.595	Remote Similarity	NPD5696	Approved
0.594	Remote Similarity	NPD7741	Discontinued
0.5913	Remote Similarity	NPD4251	Approved
0.5913	Remote Similarity	NPD4250	Approved
0.5909	Remote Similarity	NPD4195	Approved
0.5905	Remote Similarity	NPD7144	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