NPASS Compound

Structure

NPC469318 OpenBabel07101718272D 38 42 0 0 1 0 0 0 0 0999 V2000 -0.4532 2.8628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4254 4.2608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8952 -2.7994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8719 -2.7994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7485 0.2244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8031 -0.0213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3973 -0.8923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2294 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3835 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0869 2.6040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9289 -0.3018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1888 2.2201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6352 3.6867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 0.9767 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9470 2.1412 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5031 0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5377 -1.4651 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.2294 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9289 1.2786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.1215 1.1801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3835 -1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0630 0.9203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -0.4884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8459 -0.4884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7429 4.0839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 1.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0753 -1.9535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7588 1.6057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7373 2.7153 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4788 0.4446 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 29 1 0 0 0 0 8 31 1 0 0 0 0 10 13 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 30 1 0 0 0 0 13 31 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 0 0 0 0 16 32 1 0 0 0 0 17 1 1 1 0 0 0 17 25 1 0 0 0 0 18 33 2 0 0 0 0 18 37 1 0 0 0 0 19 25 2 0 0 0 0 19 32 1 0 0 0 0 20 26 1 0 0 0 0 20 34 1 6 0 0 0 21 27 1 0 0 0 0 21 37 1 1 0 0 0 22 16 1 6 0 0 0 22 25 1 0 0 0 0 22 38 1 0 0 0 0 23 28 1 0 0 0 0 23 30 1 0 0 0 0 24 28 1 0 0 0 0 24 35 2 0 0 0 0 26 30 1 0 0 0 0 26 31 1 0 0 0 0 27 29 1 1 0 0 0 27 38 1 0 0 0 0 29 36 1 0 0 0 0 30 7 1 6 0 0 0 31 32 1 6 0 0 0 32 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	520.462
LogP:	4.263
LogD:	3.683
LogS:	-4.675
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.455
Synthetic Accessibility Score:	5.176
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.149
MDCK Permeability:	1.3708759979635943e-05
Pgp-inhibitor:	0.944
Pgp-substrate:	0.122
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.867
30% Bioavailability (F30%):	0.323

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.834
Plasma Protein Binding (PPB):	90.59960174560547%
Volume Distribution (VD):	1.205
Pgp-substrate:	6.73345947265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.506
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.136
CYP2C9-substrate:	0.214
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.818
CYP3A4-substrate:	0.783

ADMET: Excretion

Clearance (CL):	10.758
Half-life (T1/2):	0.097

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.264
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.395
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.036
Carcinogencity:	0.425
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC469318

Natural Product ID:	NPC469318
*Common Name:**	QJQGTCCCAJRIPR-BTEWYCRNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QJQGTCCCAJRIPR-BTEWYCRNSA-N
Standard InCHI:	InChI=1S/C32H50O6/c1-17-14-21(37-18(2)33)27(29(5,6)36)38-22-16-32(9)19(25(17)22)15-20(34)26-30(7)12-11-24(35)28(3,4)23(30)10-13-31(26,32)8/h17,20-23,26-27,34,36H,10-16H2,1-9H3/t17-,20+,21+,22+,23?,26?,27-,30+,31+,32+/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@@H](C)C2=C3C[C@H](O)C4[C@]([C@]3(C[C@@H]2O[C@H]1C(O)(C)C)C)(C)CCC1[C@]4(C)CCC(=O)C1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL103081
PubChem CID:	44335301
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10560729]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17541191]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	Rhizome	n.a.	n.a.	PMID[26425784]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	tuber	n.a.	PMID[26666273]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	1
Others	5

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	-4.5	%	PMID[471366]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	7.5	%	PMID[471366]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	13.5	%	PMID[471366]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	42.9	%	PMID[471366]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	90.8	%	PMID[471366]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	36000.0	nM	PMID[471366]

☑ 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 NPC469318 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	259
0.1-0.2	1604
0.2-0.3	4519
0.3-0.4	8615
0.4-0.5	12914
0.5-0.6	6524
0.6-0.7	5990
0.7-0.8	2196
0.8-0.85	60
0.85-0.9	14
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473173
0.93	High Similarity	NPC324001
0.898	High Similarity	NPC37787
0.898	High Similarity	NPC30677
0.898	High Similarity	NPC469329
0.898	High Similarity	NPC180557
0.898	High Similarity	NPC473415
0.89	High Similarity	NPC471784
0.89	High Similarity	NPC303777
0.8824	High Similarity	NPC469316
0.8785	High Similarity	NPC470063
0.87	High Similarity	NPC471777
0.8673	High Similarity	NPC473166
0.8529	High Similarity	NPC470066
0.8529	High Similarity	NPC470067
0.8505	High Similarity	NPC173905
0.8505	High Similarity	NPC472216
0.8505	High Similarity	NPC5475
0.8505	High Similarity	NPC284828
0.8491	Intermediate Similarity	NPC9457
0.8491	Intermediate Similarity	NPC471783
0.8447	Intermediate Similarity	NPC473176
0.844	Intermediate Similarity	NPC234042
0.844	Intermediate Similarity	NPC152117
0.8426	Intermediate Similarity	NPC475563
0.8426	Intermediate Similarity	NPC475134
0.8426	Intermediate Similarity	NPC250956
0.84	Intermediate Similarity	NPC198074
0.84	Intermediate Similarity	NPC274046
0.8396	Intermediate Similarity	NPC470587
0.8396	Intermediate Similarity	NPC472655
0.8365	Intermediate Similarity	NPC469327
0.8349	Intermediate Similarity	NPC475668
0.8349	Intermediate Similarity	NPC475480
0.8349	Intermediate Similarity	NPC473921
0.8333	Intermediate Similarity	NPC475304
0.8317	Intermediate Similarity	NPC240617
0.8286	Intermediate Similarity	NPC165250
0.8265	Intermediate Similarity	NPC241875
0.8265	Intermediate Similarity	NPC469314
0.8265	Intermediate Similarity	NPC469317
0.8257	Intermediate Similarity	NPC472215
0.8257	Intermediate Similarity	NPC472214
0.8252	Intermediate Similarity	NPC254121
0.8241	Intermediate Similarity	NPC472218
0.8241	Intermediate Similarity	NPC472219
0.8241	Intermediate Similarity	NPC472217
0.8224	Intermediate Similarity	NPC475414
0.8224	Intermediate Similarity	NPC173172
0.8208	Intermediate Similarity	NPC222153
0.8173	Intermediate Similarity	NPC119036
0.8173	Intermediate Similarity	NPC470068
0.8165	Intermediate Similarity	NPC218853
0.8165	Intermediate Similarity	NPC475065
0.8158	Intermediate Similarity	NPC42673
0.8158	Intermediate Similarity	NPC230513
0.8158	Intermediate Similarity	NPC469380
0.8155	Intermediate Similarity	NPC471822
0.8148	Intermediate Similarity	NPC187435
0.8148	Intermediate Similarity	NPC67321
0.8148	Intermediate Similarity	NPC131665
0.8148	Intermediate Similarity	NPC475176
0.8148	Intermediate Similarity	NPC255387
0.8148	Intermediate Similarity	NPC473165
0.8131	Intermediate Similarity	NPC473577
0.8131	Intermediate Similarity	NPC473175
0.8131	Intermediate Similarity	NPC475585
0.8131	Intermediate Similarity	NPC474550
0.8113	Intermediate Similarity	NPC295791
0.8095	Intermediate Similarity	NPC167974
0.8091	Intermediate Similarity	NPC5284
0.8087	Intermediate Similarity	NPC268530
0.8087	Intermediate Similarity	NPC154491
0.8087	Intermediate Similarity	NPC251226
0.8077	Intermediate Similarity	NPC272451
0.8073	Intermediate Similarity	NPC473482
0.8073	Intermediate Similarity	NPC469916
0.8073	Intermediate Similarity	NPC306265
0.8073	Intermediate Similarity	NPC88701
0.8073	Intermediate Similarity	NPC472439
0.8073	Intermediate Similarity	NPC475418
0.8073	Intermediate Similarity	NPC318363
0.8058	Intermediate Similarity	NPC86893
0.8058	Intermediate Similarity	NPC279974
0.8058	Intermediate Similarity	NPC292178
0.8056	Intermediate Similarity	NPC475290
0.8037	Intermediate Similarity	NPC474124
0.8037	Intermediate Similarity	NPC36688
0.8037	Intermediate Similarity	NPC159533
0.802	Intermediate Similarity	NPC472307
0.8019	Intermediate Similarity	NPC475617
0.8019	Intermediate Similarity	NPC476897
0.8019	Intermediate Similarity	NPC470054
0.8017	Intermediate Similarity	NPC4021
0.8017	Intermediate Similarity	NPC159456
0.8	Intermediate Similarity	NPC473636
0.8	Intermediate Similarity	NPC77689
0.8	Intermediate Similarity	NPC477071
0.8	Intermediate Similarity	NPC475041
0.8	Intermediate Similarity	NPC473839
0.8	Intermediate Similarity	NPC273433
0.8	Intermediate Similarity	NPC211093
0.8	Intermediate Similarity	NPC299590
0.7982	Intermediate Similarity	NPC329048
0.7982	Intermediate Similarity	NPC112780
0.7982	Intermediate Similarity	NPC55296
0.7982	Intermediate Similarity	NPC330011
0.7981	Intermediate Similarity	NPC91439
0.7981	Intermediate Similarity	NPC129569
0.7966	Intermediate Similarity	NPC469790
0.7965	Intermediate Similarity	NPC472274
0.7965	Intermediate Similarity	NPC284915
0.7963	Intermediate Similarity	NPC473543
0.7946	Intermediate Similarity	NPC269530
0.7946	Intermediate Similarity	NPC280782
0.7944	Intermediate Similarity	NPC475344
0.7944	Intermediate Similarity	NPC470053
0.7944	Intermediate Similarity	NPC476471
0.7944	Intermediate Similarity	NPC155332
0.7944	Intermediate Similarity	NPC476081
0.7944	Intermediate Similarity	NPC32577
0.7944	Intermediate Similarity	NPC165578
0.7944	Intermediate Similarity	NPC114540
0.7928	Intermediate Similarity	NPC470065
0.7925	Intermediate Similarity	NPC274643
0.7925	Intermediate Similarity	NPC473510
0.7925	Intermediate Similarity	NPC251680
0.7921	Intermediate Similarity	NPC469319
0.7921	Intermediate Similarity	NPC229871
0.7913	Intermediate Similarity	NPC473617
0.7913	Intermediate Similarity	NPC124676
0.7913	Intermediate Similarity	NPC473828
0.7913	Intermediate Similarity	NPC146280
0.7909	Intermediate Similarity	NPC472825
0.7909	Intermediate Similarity	NPC258323
0.7909	Intermediate Similarity	NPC325054
0.7905	Intermediate Similarity	NPC224356
0.7905	Intermediate Similarity	NPC151681
0.7905	Intermediate Similarity	NPC121402
0.7905	Intermediate Similarity	NPC132753
0.7905	Intermediate Similarity	NPC175351
0.79	Intermediate Similarity	NPC469322
0.7899	Intermediate Similarity	NPC15095
0.7895	Intermediate Similarity	NPC196931
0.789	Intermediate Similarity	NPC231530
0.789	Intermediate Similarity	NPC278628
0.789	Intermediate Similarity	NPC127609
0.789	Intermediate Similarity	NPC60315
0.789	Intermediate Similarity	NPC477877
0.789	Intermediate Similarity	NPC111952
0.7881	Intermediate Similarity	NPC469382
0.7876	Intermediate Similarity	NPC311592
0.7876	Intermediate Similarity	NPC75167
0.7876	Intermediate Similarity	NPC255017
0.787	Intermediate Similarity	NPC474822
0.787	Intermediate Similarity	NPC99266
0.787	Intermediate Similarity	NPC473694
0.787	Intermediate Similarity	NPC471208
0.787	Intermediate Similarity	NPC475623
0.787	Intermediate Similarity	NPC218513
0.787	Intermediate Similarity	NPC55954
0.787	Intermediate Similarity	NPC120321
0.787	Intermediate Similarity	NPC478057
0.787	Intermediate Similarity	NPC473523
0.787	Intermediate Similarity	NPC112009
0.787	Intermediate Similarity	NPC475334
0.787	Intermediate Similarity	NPC180204
0.7864	Intermediate Similarity	NPC469315
0.7863	Intermediate Similarity	NPC67569
0.7857	Intermediate Similarity	NPC469656
0.7857	Intermediate Similarity	NPC324683
0.7857	Intermediate Similarity	NPC474846
0.7857	Intermediate Similarity	NPC469655
0.7857	Intermediate Similarity	NPC86370
0.7857	Intermediate Similarity	NPC470076
0.7851	Intermediate Similarity	NPC35109
0.785	Intermediate Similarity	NPC289670
0.785	Intermediate Similarity	NPC471412
0.785	Intermediate Similarity	NPC473174
0.7838	Intermediate Similarity	NPC31522
0.7838	Intermediate Similarity	NPC477069
0.7838	Intermediate Similarity	NPC477070
0.7838	Intermediate Similarity	NPC41405
0.7833	Intermediate Similarity	NPC298841
0.783	Intermediate Similarity	NPC218107
0.7826	Intermediate Similarity	NPC183580
0.7826	Intermediate Similarity	NPC284068
0.7826	Intermediate Similarity	NPC475809
0.7826	Intermediate Similarity	NPC473590
0.7826	Intermediate Similarity	NPC10721
0.7826	Intermediate Similarity	NPC312824
0.7826	Intermediate Similarity	NPC470493
0.7826	Intermediate Similarity	NPC134430
0.7818	Intermediate Similarity	NPC144459
0.7818	Intermediate Similarity	NPC301666
0.7818	Intermediate Similarity	NPC473586
0.7818	Intermediate Similarity	NPC473284
0.7818	Intermediate Similarity	NPC230541
0.7818	Intermediate Similarity	NPC143609
0.7815	Intermediate Similarity	NPC75856

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 NPC469318 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	237
0.1-0.2	1900
0.2-0.3	3691
0.3-0.4	2178
0.4-0.5	678
0.5-0.6	274
0.6-0.7	174
0.7-0.8	18
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
0.8	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7638	Approved
0.7925	Intermediate Similarity	NPD7640	Approved
0.7925	Intermediate Similarity	NPD7639	Approved
0.7778	Intermediate Similarity	NPD7632	Discontinued
0.7672	Intermediate Similarity	NPD7115	Discovery
0.7611	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD7507	Approved
0.7522	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6686	Approved
0.7434	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7319	Approved
0.7417	Intermediate Similarity	NPD8033	Approved
0.7414	Intermediate Similarity	NPD8133	Approved
0.7345	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD4225	Approved
0.7333	Intermediate Similarity	NPD8377	Approved
0.7333	Intermediate Similarity	NPD8294	Approved
0.7328	Intermediate Similarity	NPD8297	Approved
0.7311	Intermediate Similarity	NPD7327	Approved
0.7311	Intermediate Similarity	NPD7328	Approved
0.729	Intermediate Similarity	NPD7748	Approved
0.7273	Intermediate Similarity	NPD8378	Approved
0.7273	Intermediate Similarity	NPD8380	Approved
0.7273	Intermediate Similarity	NPD8335	Approved
0.7273	Intermediate Similarity	NPD8379	Approved
0.7273	Intermediate Similarity	NPD8296	Approved
0.7265	Intermediate Similarity	NPD4632	Approved
0.7257	Intermediate Similarity	NPD7128	Approved
0.7257	Intermediate Similarity	NPD6675	Approved
0.7257	Intermediate Similarity	NPD6402	Approved
0.7257	Intermediate Similarity	NPD5739	Approved
0.725	Intermediate Similarity	NPD7516	Approved
0.7227	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6399	Phase 3
0.7193	Intermediate Similarity	NPD6412	Phase 2
0.719	Intermediate Similarity	NPD6319	Approved
0.7179	Intermediate Similarity	NPD6053	Discontinued
0.7155	Intermediate Similarity	NPD6371	Approved
0.713	Intermediate Similarity	NPD7320	Approved
0.713	Intermediate Similarity	NPD6881	Approved
0.713	Intermediate Similarity	NPD6899	Approved
0.7103	Intermediate Similarity	NPD7515	Phase 2
0.7103	Intermediate Similarity	NPD8034	Phase 2
0.7103	Intermediate Similarity	NPD8035	Phase 2
0.7094	Intermediate Similarity	NPD8130	Phase 1
0.7091	Intermediate Similarity	NPD6084	Phase 2
0.7091	Intermediate Similarity	NPD7902	Approved
0.7091	Intermediate Similarity	NPD6083	Phase 2
0.7069	Intermediate Similarity	NPD6373	Approved
0.7069	Intermediate Similarity	NPD6372	Approved
0.7063	Intermediate Similarity	NPD7736	Approved
0.7043	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5701	Approved
0.7043	Intermediate Similarity	NPD5697	Approved
0.7019	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7102	Approved
0.7009	Intermediate Similarity	NPD6883	Approved
0.7009	Intermediate Similarity	NPD7290	Approved
0.7	Intermediate Similarity	NPD6114	Approved
0.7	Intermediate Similarity	NPD6118	Approved
0.7	Intermediate Similarity	NPD6697	Approved
0.7	Intermediate Similarity	NPD6115	Approved
0.6984	Remote Similarity	NPD8293	Discontinued
0.696	Remote Similarity	NPD7492	Approved
0.6957	Remote Similarity	NPD6008	Approved
0.6949	Remote Similarity	NPD6649	Approved
0.6949	Remote Similarity	NPD6847	Approved
0.6949	Remote Similarity	NPD6650	Approved
0.6949	Remote Similarity	NPD6617	Approved
0.6949	Remote Similarity	NPD6869	Approved
0.6942	Remote Similarity	NPD6009	Approved
0.6923	Remote Similarity	NPD6014	Approved
0.6923	Remote Similarity	NPD6012	Approved
0.6923	Remote Similarity	NPD6013	Approved
0.6923	Remote Similarity	NPD4786	Approved
0.6911	Remote Similarity	NPD6054	Approved
0.6911	Remote Similarity	NPD6059	Approved
0.6905	Remote Similarity	NPD6616	Approved
0.6893	Remote Similarity	NPD3667	Approved
0.6891	Remote Similarity	NPD6882	Approved
0.688	Remote Similarity	NPD8328	Phase 3
0.688	Remote Similarity	NPD7604	Phase 2
0.6855	Remote Similarity	NPD7503	Approved
0.6855	Remote Similarity	NPD5983	Phase 2
0.6852	Remote Similarity	NPD6698	Approved
0.6852	Remote Similarity	NPD46	Approved
0.685	Remote Similarity	NPD7078	Approved
0.6838	Remote Similarity	NPD6011	Approved
0.6822	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7900	Approved
0.6807	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6117	Approved
0.68	Remote Similarity	NPD6370	Approved
0.6792	Remote Similarity	NPD7334	Approved
0.6792	Remote Similarity	NPD7146	Approved
0.6792	Remote Similarity	NPD6684	Approved
0.6792	Remote Similarity	NPD5330	Approved
0.6792	Remote Similarity	NPD7521	Approved
0.6792	Remote Similarity	NPD3618	Phase 1
0.6792	Remote Similarity	NPD6409	Approved
0.6786	Remote Similarity	NPD4755	Approved
0.6772	Remote Similarity	NPD6336	Discontinued
0.6759	Remote Similarity	NPD5328	Approved
0.6757	Remote Similarity	NPD5695	Phase 3
0.6754	Remote Similarity	NPD4159	Approved
0.6754	Remote Similarity	NPD5344	Discontinued
0.6733	Remote Similarity	NPD6116	Phase 1
0.6727	Remote Similarity	NPD4202	Approved
0.6726	Remote Similarity	NPD5696	Approved
0.6723	Remote Similarity	NPD4634	Approved
0.672	Remote Similarity	NPD8517	Approved
0.672	Remote Similarity	NPD8516	Approved
0.672	Remote Similarity	NPD6015	Approved
0.672	Remote Similarity	NPD8513	Phase 3
0.672	Remote Similarity	NPD8515	Approved
0.672	Remote Similarity	NPD6016	Approved
0.672	Remote Similarity	NPD6921	Approved
0.6696	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6636	Remote Similarity	NPD7637	Suspended
0.6636	Remote Similarity	NPD5693	Phase 1
0.6636	Remote Similarity	NPD6079	Approved
0.6607	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4753	Phase 2
0.6606	Remote Similarity	NPD6051	Approved
0.6604	Remote Similarity	NPD3665	Phase 1
0.6604	Remote Similarity	NPD3133	Approved
0.6604	Remote Similarity	NPD3666	Approved
0.66	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6274	Approved
0.6581	Remote Similarity	NPD5141	Approved
0.6581	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5779	Approved
0.6577	Remote Similarity	NPD5778	Approved
0.6574	Remote Similarity	NPD7524	Approved
0.6571	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7100	Approved
0.656	Remote Similarity	NPD7101	Approved
0.6552	Remote Similarity	NPD4633	Approved
0.6552	Remote Similarity	NPD5224	Approved
0.6552	Remote Similarity	NPD5225	Approved
0.6552	Remote Similarity	NPD5226	Approved
0.6542	Remote Similarity	NPD1694	Approved
0.6538	Remote Similarity	NPD7525	Registered
0.6535	Remote Similarity	NPD3703	Phase 2
0.6514	Remote Similarity	NPD5737	Approved
0.6514	Remote Similarity	NPD6672	Approved
0.6509	Remote Similarity	NPD4788	Approved
0.6496	Remote Similarity	NPD5175	Approved
0.6496	Remote Similarity	NPD5174	Approved
0.6486	Remote Similarity	NPD7983	Approved
0.6486	Remote Similarity	NPD6411	Approved
0.6484	Remote Similarity	NPD6067	Discontinued
0.6481	Remote Similarity	NPD6098	Approved
0.6481	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6335	Approved
0.6466	Remote Similarity	NPD5223	Approved
0.6462	Remote Similarity	NPD8074	Phase 3
0.6457	Remote Similarity	NPD6908	Approved
0.6457	Remote Similarity	NPD6909	Approved
0.6455	Remote Similarity	NPD6904	Approved
0.6455	Remote Similarity	NPD6080	Approved
0.6455	Remote Similarity	NPD6673	Approved
0.6449	Remote Similarity	NPD3668	Phase 3
0.6412	Remote Similarity	NPD6033	Approved
0.6404	Remote Similarity	NPD5222	Approved
0.6404	Remote Similarity	NPD5221	Approved
0.6404	Remote Similarity	NPD4697	Phase 3
0.6404	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5777	Approved
0.64	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6317	Approved
0.6396	Remote Similarity	NPD7838	Discovery
0.6396	Remote Similarity	NPD5785	Approved
0.6387	Remote Similarity	NPD4767	Approved
0.6387	Remote Similarity	NPD4768	Approved
0.6379	Remote Similarity	NPD6648	Approved
0.6364	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD4754	Approved
0.6355	Remote Similarity	NPD7154	Phase 3
0.6355	Remote Similarity	NPD6695	Phase 3
0.6355	Remote Similarity	NPD5362	Discontinued
0.6349	Remote Similarity	NPD6314	Approved
0.6349	Remote Similarity	NPD6313	Approved
0.6348	Remote Similarity	NPD5173	Approved
0.632	Remote Similarity	NPD6868	Approved
0.6316	Remote Similarity	NPD4629	Approved
0.6316	Remote Similarity	NPD5210	Approved
0.6316	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7285	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