NPASS Compound

Structure

CID245059 OpenBabel06191716042D 42 46 0 0 1 0 0 0 0 0999 V2000 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 9 1 0 0 0 0 2 36 1 0 0 0 0 3 37 1 0 0 0 0 4 9 2 0 0 0 0 4 11 1 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 10 1 0 0 0 0 6 14 2 0 0 0 0 7 13 1 0 0 0 0 7 38 1 0 0 0 0 8 39 1 0 0 0 0 9 40 1 0 0 0 0 10 36 1 0 0 0 0 11 17 2 0 0 0 0 11 24 1 0 0 0 0 12 16 1 0 0 0 0 12 24 2 0 0 0 0 13 18 1 0 0 0 0 13 28 1 6 0 0 0 14 16 1 0 0 0 0 14 41 1 0 0 0 0 15 8 1 1 0 0 0 15 19 1 0 0 0 0 15 42 1 0 0 0 0 16 20 2 0 0 0 0 17 20 1 0 0 0 0 17 25 1 0 0 0 0 18 22 1 0 0 0 0 18 29 1 6 0 0 0 19 21 1 0 0 0 0 19 30 1 6 0 0 0 20 31 1 0 0 0 0 21 23 1 0 0 0 0 21 32 1 1 0 0 0 22 26 1 0 0 0 0 22 33 1 1 0 0 0 23 27 1 0 0 0 0 23 34 1 6 0 0 0 24 37 1 0 0 0 0 25 35 2 0 0 0 0 25 40 1 0 0 0 0 26 38 1 0 0 0 0 26 39 1 6 0 0 0 27 41 1 1 0 0 0 27 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	596.17
Volume:	546.164
LogP:	0.555
LogD:	0.051
LogS:	-4.155
# Rotatable Bonds:	7
TPSA:	227.2
# H-Bond Aceptor:	15
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.156
Synthetic Accessibility Score:	4.826
Fsp3:	0.519
Lipinski Rule-of-5:	Rejected
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:	-6.299
MDCK Permeability:	3.120482142549008e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.761
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.152
Plasma Protein Binding (PPB):	68.35914611816406%
Volume Distribution (VD):	0.629
Pgp-substrate:	22.722190856933594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.508
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.167
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.162
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	1.133
Half-life (T1/2):	0.418

ADMET: Toxicity

hERG Blockers:	0.469
Human Hepatotoxicity (H-HT):	0.231
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.538
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.312
Carcinogencity:	0.097
Eye Corrosion:	0.003
Eye Irritation:	0.041
Respiratory Toxicity:	0.021

Download Data

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

Natural Product: NPC245059

Natural Product ID:	NPC245059
*Common Name:**	Paepalantine-9-O-Alpha-L-Arabinopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name:	10-hydroxy-5,7-dimethoxy-3-methyl-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxybenzo[g]isochromen-1-one
Synonyms:
Standard InCHIKey:	QIZARGSUDZBXDB-JHVBERTJSA-N
Standard InCHI:	InChI=1S/C27H32O15/c1-9-4-11-17(25(35)40-9)20(31)16-12(24(11)37-3)5-10(36-2)6-14(16)41-27-23(34)21(32)19(30)15(42-27)8-39-26-22(33)18(29)13(28)7-38-26/h4-6,13,15,18-19,21-23,26-34H,7-8H2,1-3H3/t13-,15+,18-,19+,21-,22+,23+,26-,27+/m0/s1
SMILES:	Cc1cc2c(c(c3c(cc(cc3O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]4[C@@H]([C@H]([C@H](CO4)O)O)O)O3)O)O)O)OC)c2OC)O)c(=O)o1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503057
PubChem CID:	11082549
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones [CHEMONTID:0001646] Naphthopyranone glycosides

*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
NPO7519	Paepalanthus microphyllus	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374977]
NPO7519	Paepalanthus microphyllus	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5130	Platycapnos saxicola	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26869	Cephalanthus pilulifera	Species	Rubiaceae	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
EC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	TC50	=	160.0	ug ml-1	PMID[496312]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	18.0	ug.mL-1	PMID[496312]
NPT2	Others	Unspecified		Selectivity Index	=	8.9	n.a.	PMID[496312]

☑ 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 NPC245059 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	437
0.1-0.2	1910
0.2-0.3	3854
0.3-0.4	9078
0.4-0.5	8928
0.5-0.6	5366
0.6-0.7	5580
0.7-0.8	5737
0.8-0.85	1309
0.85-0.9	465
0.9-0.95	23
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC84494
0.994	High Similarity	NPC164047
0.994	High Similarity	NPC470452
0.994	High Similarity	NPC470453
0.994	High Similarity	NPC470448
0.9818	High Similarity	NPC470454
0.9818	High Similarity	NPC63105
0.9818	High Similarity	NPC199533
0.9639	High Similarity	NPC213052
0.9471	High Similarity	NPC475161
0.9471	High Similarity	NPC477860
0.9458	High Similarity	NPC259905
0.9419	High Similarity	NPC241847
0.9408	High Similarity	NPC46958
0.9401	High Similarity	NPC298778
0.9349	High Similarity	NPC68381
0.9337	High Similarity	NPC178851
0.9294	High Similarity	NPC475246
0.9281	High Similarity	NPC249977
0.9235	High Similarity	NPC3718
0.9235	High Similarity	NPC474345
0.9231	High Similarity	NPC271385
0.9231	High Similarity	NPC76128
0.9231	High Similarity	NPC111536
0.9231	High Similarity	NPC30432
0.9231	High Similarity	NPC5029
0.9217	High Similarity	NPC17432
0.9195	High Similarity	NPC475352
0.9195	High Similarity	NPC229817
0.9195	High Similarity	NPC475220
0.9195	High Similarity	NPC473686
0.9195	High Similarity	NPC221140
0.9195	High Similarity	NPC87583
0.9191	High Similarity	NPC293227
0.9191	High Similarity	NPC473631
0.9191	High Similarity	NPC475662
0.9191	High Similarity	NPC473717
0.9186	High Similarity	NPC153578
0.9186	High Similarity	NPC114257
0.9186	High Similarity	NPC299149
0.9186	High Similarity	NPC277710
0.9172	High Similarity	NPC210808
0.9172	High Similarity	NPC199079
0.9162	High Similarity	NPC99216
0.9162	High Similarity	NPC7752
0.9118	High Similarity	NPC288152
0.9118	High Similarity	NPC9002
0.9118	High Similarity	NPC257011
0.9118	High Similarity	NPC137871
0.9112	High Similarity	NPC473202
0.9107	High Similarity	NPC70441
0.9102	High Similarity	NPC257566
0.9102	High Similarity	NPC124155
0.9096	High Similarity	NPC321046
0.9096	High Similarity	NPC48474
0.907	High Similarity	NPC475233
0.907	High Similarity	NPC102053
0.9064	High Similarity	NPC472054
0.9059	High Similarity	NPC477571
0.9059	High Similarity	NPC477572
0.9059	High Similarity	NPC241874
0.9059	High Similarity	NPC477573
0.905	High Similarity	NPC470196
0.905	High Similarity	NPC282474
0.905	High Similarity	NPC470200
0.905	High Similarity	NPC470194
0.905	High Similarity	NPC470193
0.905	High Similarity	NPC470195
0.905	High Similarity	NPC316274
0.905	High Similarity	NPC470197
0.905	High Similarity	NPC470198
0.9042	High Similarity	NPC44947
0.9042	High Similarity	NPC216752
0.904	High Similarity	NPC314672
0.9036	High Similarity	NPC328093
0.9034	High Similarity	NPC105591
0.9006	High Similarity	NPC472386
0.9	High Similarity	NPC222455
0.9	High Similarity	NPC246274
0.8989	High Similarity	NPC264302
0.8982	High Similarity	NPC101636
0.8982	High Similarity	NPC47923
0.8966	High Similarity	NPC212290
0.8966	High Similarity	NPC58538
0.896	High Similarity	NPC312630
0.896	High Similarity	NPC324220
0.8953	High Similarity	NPC204693
0.8953	High Similarity	NPC25724
0.8953	High Similarity	NPC98776
0.8953	High Similarity	NPC203751
0.8953	High Similarity	NPC85368
0.8953	High Similarity	NPC208668
0.8947	High Similarity	NPC313304
0.8947	High Similarity	NPC150767
0.8947	High Similarity	NPC78734
0.8947	High Similarity	NPC76047
0.8944	High Similarity	NPC314687
0.8939	High Similarity	NPC314459
0.8939	High Similarity	NPC470199
0.8933	High Similarity	NPC31208
0.8933	High Similarity	NPC472724
0.8933	High Similarity	NPC472720
0.8933	High Similarity	NPC160543
0.8933	High Similarity	NPC472721
0.8933	High Similarity	NPC469652
0.8933	High Similarity	NPC93065
0.8929	High Similarity	NPC298171
0.8929	High Similarity	NPC190450
0.8922	High Similarity	NPC470358
0.892	High Similarity	NPC148710
0.892	High Similarity	NPC49690
0.8916	High Similarity	NPC257309
0.8908	High Similarity	NPC472387
0.8908	High Similarity	NPC477682
0.8908	High Similarity	NPC477683
0.8902	High Similarity	NPC146803
0.8902	High Similarity	NPC102028
0.8901	High Similarity	NPC131405
0.8901	High Similarity	NPC174140
0.8895	High Similarity	NPC301683
0.8895	High Similarity	NPC211594
0.8895	High Similarity	NPC315619
0.8895	High Similarity	NPC475155
0.8895	High Similarity	NPC254540
0.8895	High Similarity	NPC267254
0.8895	High Similarity	NPC172807
0.8895	High Similarity	NPC256760
0.8889	High Similarity	NPC5319
0.8889	High Similarity	NPC472381
0.8889	High Similarity	NPC472383
0.8882	High Similarity	NPC178173
0.8876	High Similarity	NPC240200
0.8876	High Similarity	NPC158214
0.8876	High Similarity	NPC223534
0.8876	High Similarity	NPC290289
0.887	High Similarity	NPC111490
0.887	High Similarity	NPC261623
0.8869	High Similarity	NPC303913
0.8864	High Similarity	NPC470445
0.8864	High Similarity	NPC313452
0.8864	High Similarity	NPC470447
0.8864	High Similarity	NPC470446
0.8864	High Similarity	NPC470449
0.8862	High Similarity	NPC138811
0.8862	High Similarity	NPC22062
0.8862	High Similarity	NPC473634
0.8855	High Similarity	NPC261866
0.8851	High Similarity	NPC472384
0.8851	High Similarity	NPC472382
0.8851	High Similarity	NPC289876
0.8851	High Similarity	NPC472380
0.8851	High Similarity	NPC255799
0.8844	High Similarity	NPC219600
0.8844	High Similarity	NPC166674
0.8844	High Similarity	NPC51774
0.8844	High Similarity	NPC263119
0.8844	High Similarity	NPC236191
0.8844	High Similarity	NPC34436
0.8844	High Similarity	NPC46640
0.8844	High Similarity	NPC239549
0.8837	High Similarity	NPC105511
0.8837	High Similarity	NPC293004
0.8837	High Similarity	NPC21190
0.8837	High Similarity	NPC44558
0.8837	High Similarity	NPC52353
0.8837	High Similarity	NPC22195
0.8837	High Similarity	NPC183357
0.8837	High Similarity	NPC224462
0.8837	High Similarity	NPC251144
0.8837	High Similarity	NPC241387
0.8837	High Similarity	NPC218488
0.883	High Similarity	NPC477502
0.883	High Similarity	NPC93099
0.883	High Similarity	NPC225419
0.883	High Similarity	NPC63470
0.883	High Similarity	NPC298847
0.8827	High Similarity	NPC187632
0.8824	High Similarity	NPC475979
0.8824	High Similarity	NPC178281
0.8824	High Similarity	NPC294722
0.882	High Similarity	NPC469649
0.882	High Similarity	NPC260521
0.8817	High Similarity	NPC473961
0.8817	High Similarity	NPC259834
0.8817	High Similarity	NPC131745
0.8814	High Similarity	NPC75574
0.8814	High Similarity	NPC470455
0.8814	High Similarity	NPC292706
0.8814	High Similarity	NPC106700
0.8814	High Similarity	NPC470451
0.8814	High Similarity	NPC224557
0.881	High Similarity	NPC246469
0.881	High Similarity	NPC472320
0.881	High Similarity	NPC97285
0.881	High Similarity	NPC271270
0.881	High Similarity	NPC473623
0.881	High Similarity	NPC142860
0.8807	High Similarity	NPC315221
0.8807	High Similarity	NPC208797
0.8807	High Similarity	NPC208069

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 NPC245059 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	995
0.2-0.3	1984
0.3-0.4	2719
0.4-0.5	1858
0.5-0.6	801
0.6-0.7	248
0.7-0.8	121
0.8-0.85	19
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD7804	Clinical (unspecified phase)
0.882	High Similarity	NPD7879	Clinical (unspecified phase)
0.8779	High Similarity	NPD7054	Approved
0.8728	High Similarity	NPD7074	Phase 3
0.8728	High Similarity	NPD7472	Approved
0.869	High Similarity	NPD4381	Clinical (unspecified phase)
0.8686	High Similarity	NPD4338	Clinical (unspecified phase)
0.8647	High Similarity	NPD6959	Discontinued
0.8636	High Similarity	NPD8313	Approved
0.8636	High Similarity	NPD8312	Approved
0.8629	High Similarity	NPD7251	Discontinued
0.8629	High Similarity	NPD6559	Discontinued
0.858	High Similarity	NPD7808	Phase 3
0.8571	High Similarity	NPD6797	Phase 2
0.8563	High Similarity	NPD5844	Phase 1
0.8526	High Similarity	NPD7783	Phase 2
0.8526	High Similarity	NPD7782	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD8151	Discontinued
0.8402	Intermediate Similarity	NPD7819	Suspended
0.84	Intermediate Similarity	NPD3818	Discontinued
0.8382	Intermediate Similarity	NPD6232	Discontinued
0.8363	Intermediate Similarity	NPD7075	Discontinued
0.8351	Intermediate Similarity	NPD7435	Discontinued
0.8343	Intermediate Similarity	NPD7473	Discontinued
0.8333	Intermediate Similarity	NPD4380	Phase 2
0.8297	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD7228	Approved
0.8198	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8191	Intermediate Similarity	NPD6779	Approved
0.8191	Intermediate Similarity	NPD6782	Approved
0.8191	Intermediate Similarity	NPD6781	Approved
0.8191	Intermediate Similarity	NPD6778	Approved
0.8191	Intermediate Similarity	NPD6776	Approved
0.8191	Intermediate Similarity	NPD6780	Approved
0.8191	Intermediate Similarity	NPD6777	Approved
0.8187	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6166	Phase 2
0.8182	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD7698	Approved
0.8158	Intermediate Similarity	NPD7697	Approved
0.8158	Intermediate Similarity	NPD7696	Phase 3
0.8144	Intermediate Similarity	NPD2532	Approved
0.8144	Intermediate Similarity	NPD2534	Approved
0.8144	Intermediate Similarity	NPD2533	Approved
0.814	Intermediate Similarity	NPD5402	Approved
0.8129	Intermediate Similarity	NPD6801	Discontinued
0.8093	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8093	Intermediate Similarity	NPD7874	Approved
0.8083	Intermediate Similarity	NPD7701	Phase 2
0.8081	Intermediate Similarity	NPD8455	Phase 2
0.8081	Intermediate Similarity	NPD2801	Approved
0.8081	Intermediate Similarity	NPD1465	Phase 2
0.8057	Intermediate Similarity	NPD5494	Approved
0.8035	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD1934	Approved
0.8021	Intermediate Similarity	NPD7871	Phase 2
0.8021	Intermediate Similarity	NPD7870	Phase 2
0.801	Intermediate Similarity	NPD6823	Phase 2
0.7989	Intermediate Similarity	NPD7700	Phase 2
0.7989	Intermediate Similarity	NPD7699	Phase 2
0.7978	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD7411	Suspended
0.7956	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD3817	Phase 2
0.7929	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD6534	Approved
0.7926	Intermediate Similarity	NPD6535	Approved
0.7919	Intermediate Similarity	NPD37	Approved
0.7912	Intermediate Similarity	NPD7240	Approved
0.7898	Intermediate Similarity	NPD6234	Discontinued
0.7892	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD3751	Discontinued
0.7886	Intermediate Similarity	NPD4967	Phase 2
0.7886	Intermediate Similarity	NPD4965	Approved
0.7886	Intermediate Similarity	NPD4966	Approved
0.7886	Intermediate Similarity	NPD7768	Phase 2
0.7868	Intermediate Similarity	NPD7801	Approved
0.7865	Intermediate Similarity	NPD3787	Discontinued
0.7835	Intermediate Similarity	NPD8320	Phase 1
0.7835	Intermediate Similarity	NPD8319	Approved
0.7803	Intermediate Similarity	NPD6599	Discontinued
0.7796	Intermediate Similarity	NPD8150	Discontinued
0.7746	Intermediate Similarity	NPD3226	Approved
0.774	Intermediate Similarity	NPD3749	Approved
0.7733	Intermediate Similarity	NPD5403	Approved
0.7725	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7199	Phase 2
0.7696	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3750	Approved
0.7692	Intermediate Similarity	NPD4628	Phase 3
0.7688	Intermediate Similarity	NPD1653	Approved
0.7684	Intermediate Similarity	NPD6213	Phase 3
0.7684	Intermediate Similarity	NPD6212	Phase 3
0.7684	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD1549	Phase 2
0.7667	Intermediate Similarity	NPD5710	Approved
0.7667	Intermediate Similarity	NPD5711	Approved
0.7665	Intermediate Similarity	NPD2935	Discontinued
0.7661	Intermediate Similarity	NPD7390	Discontinued
0.7661	Intermediate Similarity	NPD1511	Approved
0.7661	Intermediate Similarity	NPD6799	Approved
0.7647	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7458	Discontinued
0.7644	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7685	Pre-registration
0.7619	Intermediate Similarity	NPD2346	Discontinued
0.7616	Intermediate Similarity	NPD5401	Approved
0.7584	Intermediate Similarity	NPD3882	Suspended
0.7576	Intermediate Similarity	NPD7584	Approved
0.7572	Intermediate Similarity	NPD1512	Approved
0.756	Intermediate Similarity	NPD2796	Approved
0.7527	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1510	Phase 2
0.7487	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD1551	Phase 2
0.745	Intermediate Similarity	NPD7585	Approved
0.7429	Intermediate Similarity	NPD920	Approved
0.7427	Intermediate Similarity	NPD6674	Discontinued
0.7421	Intermediate Similarity	NPD8434	Phase 2
0.7402	Intermediate Similarity	NPD7930	Approved
0.74	Intermediate Similarity	NPD7583	Approved
0.7396	Intermediate Similarity	NPD3748	Approved
0.7396	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1607	Approved
0.7377	Intermediate Similarity	NPD7229	Phase 3
0.7353	Intermediate Similarity	NPD6100	Approved
0.7353	Intermediate Similarity	NPD6099	Approved
0.735	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD8059	Phase 3
0.7337	Intermediate Similarity	NPD7680	Approved
0.733	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD1243	Approved
0.7326	Intermediate Similarity	NPD2800	Approved
0.7322	Intermediate Similarity	NPD1247	Approved
0.7314	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7266	Discontinued
0.7308	Intermediate Similarity	NPD919	Approved
0.7287	Intermediate Similarity	NPD5953	Discontinued
0.7273	Intermediate Similarity	NPD7286	Phase 2
0.7262	Intermediate Similarity	NPD1240	Approved
0.7251	Intermediate Similarity	NPD5406	Approved
0.7251	Intermediate Similarity	NPD5404	Approved
0.7251	Intermediate Similarity	NPD5405	Approved
0.7251	Intermediate Similarity	NPD5408	Approved
0.7222	Intermediate Similarity	NPD8285	Discontinued
0.7216	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2799	Discontinued
0.7186	Intermediate Similarity	NPD4625	Phase 3
0.7186	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7003	Approved
0.7178	Intermediate Similarity	NPD7999	Approved
0.7167	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD8067	Phase 3
0.7159	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7177	Discontinued
0.712	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5124	Phase 1
0.7118	Intermediate Similarity	NPD230	Phase 1
0.7118	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4360	Phase 2
0.7107	Intermediate Similarity	NPD4363	Phase 3
0.7093	Intermediate Similarity	NPD7033	Discontinued
0.7079	Intermediate Similarity	NPD6273	Approved
0.7076	Intermediate Similarity	NPD6651	Approved
0.7059	Intermediate Similarity	NPD3926	Phase 2
0.7059	Intermediate Similarity	NPD4060	Phase 1
0.7059	Intermediate Similarity	NPD1613	Approved
0.7059	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD2438	Suspended
0.7047	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6190	Approved
0.7042	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7097	Phase 1
0.7033	Intermediate Similarity	NPD6844	Discontinued
0.7029	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6832	Phase 2
0.7018	Intermediate Similarity	NPD1933	Approved
0.6957	Remote Similarity	NPD4288	Approved
0.6952	Remote Similarity	NPD8127	Discontinued
0.6948	Remote Similarity	NPD8366	Approved
0.6947	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7985	Registered
0.6932	Remote Similarity	NPD1652	Phase 2
0.6923	Remote Similarity	NPD4908	Phase 1

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