NPASS Compound

Structure

NPC472370 OpenBabel07101719252D 42 46 0 0 0 0 0 0 0 0999 V2000 -2.4898 3.3542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1497 -2.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9796 -0.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3198 -0.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4375 -2.7466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4375 -1.0867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 -3.3542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8299 -3.3542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9796 -2.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8096 -1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3958 -2.7466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3958 -1.0867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8299 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4898 -1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6599 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6599 -0.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3198 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6599 1.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1497 -1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8299 1.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9583 -1.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8096 -2.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8750 -1.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3198 -0.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8299 0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6599 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4898 0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6395 -2.8750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8333 -1.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -5.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1497 -1.4375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4898 1.4375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9583 -1.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6599 2.8750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 42 1 0 0 0 0 2 10 1 0 0 0 0 2 22 2 0 0 0 0 3 11 2 0 0 0 0 3 22 1 0 0 0 0 4 17 3 0 0 0 0 4 22 1 0 0 0 0 5 18 2 0 0 0 0 5 23 1 0 0 0 0 6 12 1 0 0 0 0 6 24 2 0 0 0 0 7 13 2 0 0 0 0 7 24 1 0 0 0 0 8 14 1 0 0 0 0 8 25 2 0 0 0 0 9 15 2 0 0 0 0 9 25 1 0 0 0 0 10 26 2 0 0 0 0 11 26 1 0 0 0 0 12 27 2 0 0 0 0 13 27 1 0 0 0 0 14 28 2 0 0 0 0 15 28 1 0 0 0 0 16 19 2 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 32 1 0 0 0 0 19 31 1 0 0 0 0 20 29 2 0 0 0 0 20 33 1 0 0 0 0 21 23 1 0 0 0 0 21 42 1 0 0 0 0 23 30 2 0 0 0 0 24 35 1 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 27 37 1 0 0 0 0 28 38 1 0 0 0 0 29 39 1 0 0 0 0 30 34 1 0 0 0 0 31 32 1 0 0 0 0 31 33 2 0 0 0 0 32 34 2 0 0 0 0 33 40 1 0 0 0 0 34 35 1 0 0 0 0 35 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	560.18
Volume:	587.845
LogP:	4.823
LogD:	3.214
LogS:	-4.074
# Rotatable Bonds:	6
TPSA:	130.61
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.116
Synthetic Accessibility Score:	3.06
Fsp3:	0.086
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.604
MDCK Permeability:	7.469048341590678e-06
Pgp-inhibitor:	0.553
Pgp-substrate:	0.092
Human Intestinal Absorption (HIA):	0.628
20% Bioavailability (F20%):	0.795
30% Bioavailability (F30%):	0.142

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	98.70000457763672%
Volume Distribution (VD):	0.523
Pgp-substrate:	1.9276723861694336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.232
CYP1A2-substrate:	0.082
CYP2C19-inhibitor:	0.884
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.739
CYP2C9-substrate:	0.97
CYP2D6-inhibitor:	0.788
CYP2D6-substrate:	0.634
CYP3A4-inhibitor:	0.766
CYP3A4-substrate:	0.844

ADMET: Excretion

Clearance (CL):	3.024
Half-life (T1/2):	0.757

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.009
Drug-inuced Liver Injury (DILI):	0.922
AMES Toxicity:	0.673
Rat Oral Acute Toxicity:	0.151
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.963
Carcinogencity:	0.75
Eye Corrosion:	0.003
Eye Irritation:	0.945
Respiratory Toxicity:	0.053

Download Data

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

Natural Product: NPC472370

Natural Product ID:	NPC472370
*Common Name:**	VUZJHKHDRPDRJZ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VUZJHKHDRPDRJZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C35H28O7/c1-42-21-23-5-18-32(31-19-16-29(39)20-33(31)40)34(30(23)17-4-22-2-10-26(36)11-3-22)35(41,24-6-12-27(37)13-7-24)25-8-14-28(38)15-9-25/h2-3,5-16,18-20,36-41H,21H2,1H3
SMILES:	COCC1=C(C(=C(C=C1)C2=C(C=C(C=C2)O)O)C(C3=CC=C(C=C3)O)(C4=CC=C(C=C4)O)O)C#CC5=CC=C(C=C5)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3394772
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0004524] Triphenyl compounds

*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
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25559759]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31244143]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	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	1
Ki	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	19400.0	nM	PMID[473491]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Ki	=	15100.0	nM	PMID[473491]

☑ 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 NPC472370 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	423
0.1-0.2	1853
0.2-0.3	4340
0.3-0.4	12893
0.4-0.5	6182
0.5-0.6	5894
0.6-0.7	8935
0.7-0.8	1919
0.8-0.85	213
0.85-0.9	41
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9457	High Similarity	NPC472369
0.9111	High Similarity	NPC71465
0.9111	High Similarity	NPC472646
0.9104	High Similarity	NPC37410
0.9037	High Similarity	NPC472647
0.9037	High Similarity	NPC191462
0.9037	High Similarity	NPC472648
0.9037	High Similarity	NPC472649
0.9037	High Similarity	NPC170328
0.9037	High Similarity	NPC206525
0.9037	High Similarity	NPC133463
0.8978	High Similarity	NPC273623
0.8963	High Similarity	NPC258780
0.8806	High Similarity	NPC282508
0.8731	High Similarity	NPC254000
0.8582	High Similarity	NPC215300
0.8529	High Similarity	NPC471517
0.8529	High Similarity	NPC238168
0.8529	High Similarity	NPC237424
0.8529	High Similarity	NPC473309
0.8519	High Similarity	NPC471519
0.8519	High Similarity	NPC471518
0.8507	High Similarity	NPC53781
0.8489	Intermediate Similarity	NPC471522
0.8472	Intermediate Similarity	NPC126291
0.8451	Intermediate Similarity	NPC183709
0.8444	Intermediate Similarity	NPC38017
0.8444	Intermediate Similarity	NPC471064
0.8433	Intermediate Similarity	NPC170485
0.8429	Intermediate Similarity	NPC470307
0.8429	Intermediate Similarity	NPC470308
0.8414	Intermediate Similarity	NPC153182
0.8414	Intermediate Similarity	NPC174251
0.8414	Intermediate Similarity	NPC262297
0.8358	Intermediate Similarity	NPC105031
0.8358	Intermediate Similarity	NPC113495
0.8345	Intermediate Similarity	NPC274454
0.8345	Intermediate Similarity	NPC476615
0.8345	Intermediate Similarity	NPC476617
0.8345	Intermediate Similarity	NPC476616
0.8345	Intermediate Similarity	NPC215678
0.8298	Intermediate Similarity	NPC266006
0.8296	Intermediate Similarity	NPC9292
0.8296	Intermediate Similarity	NPC145659
0.8286	Intermediate Similarity	NPC35630
0.8284	Intermediate Similarity	NPC138248
0.8284	Intermediate Similarity	NPC228503
0.8273	Intermediate Similarity	NPC469610
0.8252	Intermediate Similarity	NPC472089
0.8243	Intermediate Similarity	NPC205501
0.8243	Intermediate Similarity	NPC162976
0.8243	Intermediate Similarity	NPC118000
0.8239	Intermediate Similarity	NPC132804
0.8239	Intermediate Similarity	NPC220344
0.8239	Intermediate Similarity	NPC275061
0.8239	Intermediate Similarity	NPC243996
0.8235	Intermediate Similarity	NPC473221
0.8222	Intermediate Similarity	NPC278955
0.8222	Intermediate Similarity	NPC105718
0.8219	Intermediate Similarity	NPC14468
0.8207	Intermediate Similarity	NPC475492
0.8201	Intermediate Similarity	NPC469611
0.8194	Intermediate Similarity	NPC472088
0.8194	Intermediate Similarity	NPC472087
0.8182	Intermediate Similarity	NPC69006
0.8182	Intermediate Similarity	NPC12668
0.8182	Intermediate Similarity	NPC308768
0.8169	Intermediate Similarity	NPC266453
0.8169	Intermediate Similarity	NPC200935
0.8169	Intermediate Similarity	NPC242715
0.8169	Intermediate Similarity	NPC56329
0.8169	Intermediate Similarity	NPC22902
0.8169	Intermediate Similarity	NPC230919
0.8163	Intermediate Similarity	NPC6702
0.8163	Intermediate Similarity	NPC111134
0.8163	Intermediate Similarity	NPC133209
0.8163	Intermediate Similarity	NPC112819
0.8162	Intermediate Similarity	NPC283508
0.8162	Intermediate Similarity	NPC82299
0.8162	Intermediate Similarity	NPC35341
0.8156	Intermediate Similarity	NPC11727
0.8156	Intermediate Similarity	NPC15109
0.8156	Intermediate Similarity	NPC125579
0.8154	Intermediate Similarity	NPC261973
0.8143	Intermediate Similarity	NPC77196
0.8134	Intermediate Similarity	NPC174977
0.8134	Intermediate Similarity	NPC255026
0.8134	Intermediate Similarity	NPC71094
0.8133	Intermediate Similarity	NPC476391
0.8133	Intermediate Similarity	NPC473018
0.8133	Intermediate Similarity	NPC120633
0.8129	Intermediate Similarity	NPC160623
0.8129	Intermediate Similarity	NPC244888
0.8129	Intermediate Similarity	NPC118683
0.8129	Intermediate Similarity	NPC211413
0.8129	Intermediate Similarity	NPC68205
0.8129	Intermediate Similarity	NPC164804
0.8129	Intermediate Similarity	NPC293203
0.8129	Intermediate Similarity	NPC8899
0.8121	Intermediate Similarity	NPC218801
0.8116	Intermediate Similarity	NPC16577
0.8116	Intermediate Similarity	NPC134360
0.8112	Intermediate Similarity	NPC243759
0.8112	Intermediate Similarity	NPC105847
0.8112	Intermediate Similarity	NPC24635
0.8112	Intermediate Similarity	NPC218131
0.8099	Intermediate Similarity	NPC30632
0.8099	Intermediate Similarity	NPC141717
0.8092	Intermediate Similarity	NPC299180
0.8088	Intermediate Similarity	NPC476653
0.8085	Intermediate Similarity	NPC473107
0.8074	Intermediate Similarity	NPC12824
0.8069	Intermediate Similarity	NPC175838
0.806	Intermediate Similarity	NPC476633
0.8056	Intermediate Similarity	NPC472090
0.8056	Intermediate Similarity	NPC472091
0.8056	Intermediate Similarity	NPC472092
0.8054	Intermediate Similarity	NPC180605
0.8054	Intermediate Similarity	NPC122980
0.8054	Intermediate Similarity	NPC107862
0.8054	Intermediate Similarity	NPC177172
0.8054	Intermediate Similarity	NPC148516
0.8045	Intermediate Similarity	NPC282255
0.8043	Intermediate Similarity	NPC38664
0.8043	Intermediate Similarity	NPC53986
0.8042	Intermediate Similarity	NPC151656
0.803	Intermediate Similarity	NPC131118
0.8028	Intermediate Similarity	NPC200557
0.8028	Intermediate Similarity	NPC108198
0.8028	Intermediate Similarity	NPC69029
0.8028	Intermediate Similarity	NPC158142
0.8028	Intermediate Similarity	NPC294884
0.8028	Intermediate Similarity	NPC241241
0.8028	Intermediate Similarity	NPC10314
0.8027	Intermediate Similarity	NPC149633
0.8015	Intermediate Similarity	NPC224342
0.8014	Intermediate Similarity	NPC185777
0.8014	Intermediate Similarity	NPC92805
0.8014	Intermediate Similarity	NPC473665
0.8	Intermediate Similarity	NPC249270
0.8	Intermediate Similarity	NPC100482
0.8	Intermediate Similarity	NPC120172
0.8	Intermediate Similarity	NPC471983
0.8	Intermediate Similarity	NPC277331
0.8	Intermediate Similarity	NPC149337
0.8	Intermediate Similarity	NPC191395
0.8	Intermediate Similarity	NPC472590
0.8	Intermediate Similarity	NPC107240
0.7986	Intermediate Similarity	NPC222108
0.7986	Intermediate Similarity	NPC96719
0.7986	Intermediate Similarity	NPC93962
0.7985	Intermediate Similarity	NPC102639
0.7973	Intermediate Similarity	NPC176804
0.7973	Intermediate Similarity	NPC71686
0.7972	Intermediate Similarity	NPC202846
0.7972	Intermediate Similarity	NPC143139
0.7972	Intermediate Similarity	NPC205442
0.7971	Intermediate Similarity	NPC149796
0.7971	Intermediate Similarity	NPC46978
0.797	Intermediate Similarity	NPC121866
0.7958	Intermediate Similarity	NPC115335
0.7958	Intermediate Similarity	NPC296915
0.7958	Intermediate Similarity	NPC198154
0.7958	Intermediate Similarity	NPC225696
0.7958	Intermediate Similarity	NPC223008
0.7958	Intermediate Similarity	NPC71372
0.7958	Intermediate Similarity	NPC97834
0.7958	Intermediate Similarity	NPC125649
0.7956	Intermediate Similarity	NPC102540
0.7956	Intermediate Similarity	NPC188022
0.7956	Intermediate Similarity	NPC285040
0.7956	Intermediate Similarity	NPC103420
0.7956	Intermediate Similarity	NPC17809
0.7956	Intermediate Similarity	NPC293801
0.7955	Intermediate Similarity	NPC470760
0.7947	Intermediate Similarity	NPC233886
0.7947	Intermediate Similarity	NPC224528
0.7947	Intermediate Similarity	NPC157081
0.7947	Intermediate Similarity	NPC105073
0.7945	Intermediate Similarity	NPC186033
0.7943	Intermediate Similarity	NPC13005
0.7943	Intermediate Similarity	NPC303144
0.7941	Intermediate Similarity	NPC474160
0.7939	Intermediate Similarity	NPC246760
0.7939	Intermediate Similarity	NPC84999
0.7931	Intermediate Similarity	NPC165026
0.7931	Intermediate Similarity	NPC213607
0.7931	Intermediate Similarity	NPC295719
0.7931	Intermediate Similarity	NPC174787
0.7931	Intermediate Similarity	NPC182509
0.7931	Intermediate Similarity	NPC73505
0.7931	Intermediate Similarity	NPC34431
0.7929	Intermediate Similarity	NPC315769
0.7923	Intermediate Similarity	NPC322239
0.7923	Intermediate Similarity	NPC321589
0.7923	Intermediate Similarity	NPC117846
0.7919	Intermediate Similarity	NPC224921
0.7919	Intermediate Similarity	NPC231712
0.7919	Intermediate Similarity	NPC242774
0.7919	Intermediate Similarity	NPC237546

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 NPC472370 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	1039
0.2-0.3	1506
0.3-0.4	2976
0.4-0.5	1747
0.5-0.6	1096
0.6-0.7	379
0.7-0.8	34
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8321	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD4908	Phase 1
0.8116	Intermediate Similarity	NPD4625	Phase 3
0.7667	Intermediate Similarity	NPD7390	Discontinued
0.7664	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD1548	Phase 1
0.75	Intermediate Similarity	NPD6959	Discontinued
0.7468	Intermediate Similarity	NPD7768	Phase 2
0.7462	Intermediate Similarity	NPD2342	Discontinued
0.7431	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4749	Approved
0.7394	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7003	Approved
0.7348	Intermediate Similarity	NPD4750	Phase 3
0.7344	Intermediate Similarity	NPD940	Approved
0.7344	Intermediate Similarity	NPD846	Approved
0.7315	Intermediate Similarity	NPD5404	Approved
0.7315	Intermediate Similarity	NPD5406	Approved
0.7315	Intermediate Similarity	NPD5405	Approved
0.7315	Intermediate Similarity	NPD5408	Approved
0.7305	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7447	Phase 1
0.7259	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3027	Phase 3
0.7208	Intermediate Similarity	NPD7213	Phase 3
0.7208	Intermediate Similarity	NPD7212	Phase 2
0.7188	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD7635	Approved
0.7171	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4624	Approved
0.7143	Intermediate Similarity	NPD4059	Approved
0.7134	Intermediate Similarity	NPD6232	Discontinued
0.7122	Intermediate Similarity	NPD7741	Discontinued
0.7114	Intermediate Similarity	NPD4097	Suspended
0.7095	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1613	Approved
0.7055	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD3020	Approved
0.7051	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5124	Phase 1
0.7024	Intermediate Similarity	NPD5844	Phase 1
0.7021	Intermediate Similarity	NPD2286	Discontinued
0.7021	Intermediate Similarity	NPD4626	Approved
0.702	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3750	Approved
0.7006	Intermediate Similarity	NPD7473	Discontinued
0.7	Intermediate Similarity	NPD1242	Phase 1
0.7	Intermediate Similarity	NPD3091	Approved
0.6987	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7041	Phase 2
0.6986	Remote Similarity	NPD2861	Phase 2
0.6986	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4060	Phase 1
0.6974	Remote Similarity	NPD6100	Approved
0.6974	Remote Similarity	NPD6099	Approved
0.6966	Remote Similarity	NPD3094	Phase 2
0.6959	Remote Similarity	NPD3764	Approved
0.6959	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD2859	Approved
0.6953	Remote Similarity	NPD2860	Approved
0.6943	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3092	Approved
0.6914	Remote Similarity	NPD8455	Phase 2
0.6914	Remote Similarity	NPD7819	Suspended
0.6908	Remote Similarity	NPD1510	Phase 2
0.6903	Remote Similarity	NPD7466	Approved
0.6901	Remote Similarity	NPD5126	Approved
0.6901	Remote Similarity	NPD5125	Phase 3
0.6897	Remote Similarity	NPD8651	Approved
0.6897	Remote Similarity	NPD6696	Suspended
0.6894	Remote Similarity	NPD7411	Suspended
0.689	Remote Similarity	NPD3749	Approved
0.6887	Remote Similarity	NPD6353	Approved
0.6887	Remote Similarity	NPD1607	Approved
0.6875	Remote Similarity	NPD2934	Approved
0.6875	Remote Similarity	NPD2933	Approved
0.6852	Remote Similarity	NPD37	Approved
0.6849	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4380	Phase 2
0.6831	Remote Similarity	NPD1651	Approved
0.6831	Remote Similarity	NPD5691	Approved
0.6826	Remote Similarity	NPD7229	Phase 3
0.6806	Remote Similarity	NPD422	Phase 1
0.6795	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD8166	Discontinued
0.6783	Remote Similarity	NPD3095	Discontinued
0.6781	Remote Similarity	NPD1283	Approved
0.6774	Remote Similarity	NPD7037	Approved
0.677	Remote Similarity	NPD7458	Discontinued
0.677	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3018	Phase 2
0.6755	Remote Similarity	NPD1240	Approved
0.6747	Remote Similarity	NPD6234	Discontinued
0.6738	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6674	Discontinued
0.673	Remote Similarity	NPD2532	Approved
0.673	Remote Similarity	NPD2534	Approved
0.673	Remote Similarity	NPD2533	Approved
0.6727	Remote Similarity	NPD4966	Approved
0.6727	Remote Similarity	NPD4965	Approved
0.6727	Remote Similarity	NPD4967	Phase 2
0.6723	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD3021	Approved
0.6715	Remote Similarity	NPD3022	Approved
0.6715	Remote Similarity	NPD5451	Approved
0.6712	Remote Similarity	NPD6582	Phase 2
0.6712	Remote Similarity	NPD6583	Phase 3
0.671	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.671	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.671	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1809	Phase 2
0.6692	Remote Similarity	NPD844	Approved
0.6689	Remote Similarity	NPD6405	Approved
0.6689	Remote Similarity	NPD6584	Phase 3
0.6689	Remote Similarity	NPD6407	Approved
0.6688	Remote Similarity	NPD3748	Approved
0.6688	Remote Similarity	NPD3892	Phase 2
0.6686	Remote Similarity	NPD8054	Approved
0.6686	Remote Similarity	NPD8053	Approved
0.6667	Remote Similarity	NPD845	Approved
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD3019	Approved
0.6667	Remote Similarity	NPD7228	Approved
0.6645	Remote Similarity	NPD3620	Phase 2
0.6645	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2238	Phase 2
0.6644	Remote Similarity	NPD5736	Approved
0.6642	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD288	Approved
0.6629	Remote Similarity	NPD8312	Approved
0.6629	Remote Similarity	NPD8313	Approved
0.6619	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6746	Phase 2
0.6604	Remote Similarity	NPD6815	Approved
0.6601	Remote Similarity	NPD5735	Approved
0.6599	Remote Similarity	NPD5327	Phase 3
0.6599	Remote Similarity	NPD1669	Approved
0.6599	Remote Similarity	NPD2983	Phase 2
0.6599	Remote Similarity	NPD2982	Phase 2
0.6597	Remote Similarity	NPD4093	Discontinued
0.6596	Remote Similarity	NPD497	Approved
0.6588	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7075	Discontinued
0.6585	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD4108	Discontinued
0.6575	Remote Similarity	NPD1611	Approved
0.6575	Remote Similarity	NPD1201	Approved
0.6575	Remote Similarity	NPD1281	Approved
0.657	Remote Similarity	NPD7177	Discontinued
0.6568	Remote Similarity	NPD7199	Phase 2
0.6564	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7008	Discontinued
0.6552	Remote Similarity	NPD2932	Approved
0.655	Remote Similarity	NPD6166	Phase 2
0.655	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.655	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6671	Approved
0.6538	Remote Similarity	NPD2935	Discontinued
0.6538	Remote Similarity	NPD1551	Phase 2
0.6538	Remote Similarity	NPD2796	Approved
0.6536	Remote Similarity	NPD4140	Approved
0.6536	Remote Similarity	NPD2979	Phase 3
0.6532	Remote Similarity	NPD8156	Discontinued
0.6532	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD2981	Phase 2
0.6529	Remote Similarity	NPD3787	Discontinued
0.6527	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD7773	Phase 2
0.6525	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD498	Approved
0.6525	Remote Similarity	NPD5283	Phase 1
0.6525	Remote Similarity	NPD496	Approved
0.6525	Remote Similarity	NPD1398	Phase 1
0.6525	Remote Similarity	NPD495	Approved
0.6516	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD7097	Phase 1
0.6516	Remote Similarity	NPD4538	Approved
0.6516	Remote Similarity	NPD4536	Approved
0.6516	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6559	Discontinued
0.6513	Remote Similarity	NPD7294	Phase 1
0.6513	Remote Similarity	NPD6798	Discontinued
0.651	Remote Similarity	NPD1470	Approved
0.6506	Remote Similarity	NPD5929	Approved
0.6506	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7340	Approved
0.6497	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6002	Phase 3

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