NPASS Compound

Structure

NPC472646 OpenBabel07101718222D 38 43 0 0 0 0 0 0 0 0999 V2000 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 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 0.8660 2.5000 0.0000 C 0 0 0 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 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 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 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 -6.9282 -3.0000 0.0000 C 0 0 0 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 -2.5981 -0.5000 0.0000 C 0 0 0 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -3.5000 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 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 35 1 0 0 0 0 2 36 1 0 0 0 0 3 37 1 0 0 0 0 4 38 1 0 0 0 0 5 6 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 9 2 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 21 2 0 0 0 0 9 23 1 0 0 0 0 10 22 2 0 0 0 0 11 19 2 0 0 0 0 11 20 1 0 0 0 0 12 17 2 0 0 0 0 12 21 1 0 0 0 0 13 18 2 0 0 0 0 13 25 1 0 0 0 0 14 20 2 0 0 0 0 14 28 1 0 0 0 0 15 24 2 0 0 0 0 15 27 1 0 0 0 0 16 26 2 0 0 0 0 16 29 1 0 0 0 0 17 22 1 0 0 0 0 18 24 1 0 0 0 0 19 30 1 0 0 0 0 20 33 1 0 0 0 0 21 35 1 0 0 0 0 22 32 1 0 0 0 0 23 31 2 0 0 0 0 23 32 1 0 0 0 0 24 30 1 0 0 0 0 25 27 2 0 0 0 0 25 31 1 0 0 0 0 26 31 1 0 0 0 0 26 34 1 0 0 0 0 27 36 1 0 0 0 0 28 30 2 0 0 0 0 28 37 1 0 0 0 0 29 32 2 0 0 0 0 29 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	508.19
Volume:	529.157
LogP:	6.955
LogD:	4.055
LogS:	-8.051
# Rotatable Bonds:	5
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.252
Synthetic Accessibility Score:	2.804
Fsp3:	0.188
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:	-5.675
MDCK Permeability:	3.3825552236521617e-05
Pgp-inhibitor:	0.758
Pgp-substrate:	0.152
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.515
30% Bioavailability (F30%):	0.822

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	83.83438873291016%
Volume Distribution (VD):	0.651
Pgp-substrate:	2.430220127105713%

ADMET: Metabolism

CYP1A2-inhibitor:	0.707
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.927
CYP2C19-substrate:	0.074
CYP2C9-inhibitor:	0.605
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.085
CYP2D6-substrate:	0.971
CYP3A4-inhibitor:	0.409
CYP3A4-substrate:	0.275

ADMET: Excretion

Clearance (CL):	7.172
Half-life (T1/2):	0.082

ADMET: Toxicity

hERG Blockers:	0.169
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.322
Rat Oral Acute Toxicity:	0.15
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.631
Carcinogencity:	0.048
Eye Corrosion:	0.003
Eye Irritation:	0.569
Respiratory Toxicity:	0.423

Download Data

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

Natural Product: NPC472646

Natural Product ID:	NPC472646
*Common Name:**	PJPNKQNHGYEFTE-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PJPNKQNHGYEFTE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H28O6/c1-35-21-8-10-22-17(12-21)7-9-23-31(26(34)16-29(38-4)32(22)23)25-13-18-5-6-19-11-20(33)14-28(37-3)30(19)24(18)15-27(25)36-2/h7-16,33-34H,5-6H2,1-4H3
SMILES:	COc1ccc2c(c1)ccc1c2c(OC)cc(c1c1cc2CCc3c(c2cc1OC)c(OC)cc(c3)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581372
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0003007] Phenanthrols

*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
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15686910]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	Fibrous Roots	n.a.	n.a.	PMID[25760525]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31415170]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10780	Bletilla striata	Species	Orchidaceae	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
MIC	8

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[479132]
NPT1204	Organism	Enterococcus faecalis ATCC 29212	Enterococcus faecalis ATCC 29212	MIC	>	128.0	ug.mL-1	PMID[479132]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	128.0	ug.mL-1	PMID[479132]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	128.0	ug.mL-1	PMID[479132]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[479132]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	128.0	ug.mL-1	PMID[479132]

☑ 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 NPC472646 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	484
0.1-0.2	2009
0.2-0.3	4963
0.3-0.4	12570
0.4-0.5	5312
0.5-0.6	4422
0.6-0.7	8224
0.7-0.8	3995
0.8-0.85	497
0.85-0.9	152
0.9-0.95	39
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC71465
0.9923	High Similarity	NPC191462
0.9923	High Similarity	NPC472648
0.9923	High Similarity	NPC170328
0.9923	High Similarity	NPC472649
0.9923	High Similarity	NPC472647
0.9923	High Similarity	NPC133463
0.9923	High Similarity	NPC206525
0.9848	High Similarity	NPC273623
0.9846	High Similarity	NPC37410
0.9846	High Similarity	NPC258780
0.9538	High Similarity	NPC282508
0.9462	High Similarity	NPC254000
0.9308	High Similarity	NPC215300
0.9308	High Similarity	NPC38017
0.9281	High Similarity	NPC126291
0.9242	High Similarity	NPC471517
0.9242	High Similarity	NPC473309
0.9237	High Similarity	NPC471519
0.9237	High Similarity	NPC471518
0.9231	High Similarity	NPC53781
0.9214	High Similarity	NPC262297
0.9154	High Similarity	NPC170485
0.913	High Similarity	NPC183709
0.9118	High Similarity	NPC266006
0.9111	High Similarity	NPC472370
0.9084	High Similarity	NPC473221
0.9078	High Similarity	NPC153182
0.9078	High Similarity	NPC174251
0.9077	High Similarity	NPC105718
0.9077	High Similarity	NPC278955
0.9077	High Similarity	NPC105031
0.9077	High Similarity	NPC113495
0.9008	High Similarity	NPC82299
0.9007	High Similarity	NPC215678
0.9007	High Similarity	NPC274454
0.9	High Similarity	NPC138248
0.9	High Similarity	NPC228503
0.8986	High Similarity	NPC12668
0.8986	High Similarity	NPC308768
0.8921	High Similarity	NPC472089
0.8913	High Similarity	NPC218131
0.8913	High Similarity	NPC132804
0.8913	High Similarity	NPC105847
0.8913	High Similarity	NPC243996
0.8913	High Similarity	NPC220344
0.8913	High Similarity	NPC243759
0.8913	High Similarity	NPC275061
0.8889	High Similarity	NPC118000
0.8889	High Similarity	NPC205501
0.8889	High Similarity	NPC162976
0.8873	High Similarity	NPC14468
0.8857	High Similarity	NPC472087
0.8857	High Similarity	NPC472088
0.8857	High Similarity	NPC175838
0.8841	High Similarity	NPC230919
0.8841	High Similarity	NPC200935
0.8841	High Similarity	NPC266453
0.8841	High Similarity	NPC22902
0.8841	High Similarity	NPC56329
0.8841	High Similarity	NPC151656
0.8841	High Similarity	NPC242715
0.8824	High Similarity	NPC469610
0.8815	High Similarity	NPC160623
0.8815	High Similarity	NPC8899
0.8769	High Similarity	NPC476633
0.8768	High Similarity	NPC143139
0.8768	High Similarity	NPC141717
0.8768	High Similarity	NPC205442
0.8768	High Similarity	NPC202846
0.8768	High Similarity	NPC30632
0.8768	High Similarity	NPC471522
0.8767	High Similarity	NPC473018
0.8767	High Similarity	NPC476391
0.8767	High Similarity	NPC120633
0.875	High Similarity	NPC469611
0.875	High Similarity	NPC303144
0.8714	High Similarity	NPC295719
0.8714	High Similarity	NPC165026
0.8714	High Similarity	NPC34431
0.8714	High Similarity	NPC73505
0.8714	High Similarity	NPC472091
0.8714	High Similarity	NPC472090
0.8714	High Similarity	NPC472092
0.8705	High Similarity	NPC470308
0.8705	High Similarity	NPC470307
0.8696	High Similarity	NPC241241
0.8696	High Similarity	NPC294884
0.8696	High Similarity	NPC69029
0.8696	High Similarity	NPC11727
0.8696	High Similarity	NPC10314
0.8696	High Similarity	NPC108198
0.8696	High Similarity	NPC125579
0.8696	High Similarity	NPC158142
0.8696	High Similarity	NPC111655
0.8696	High Similarity	NPC15109
0.8696	High Similarity	NPC200557
0.8692	High Similarity	NPC102639
0.8681	High Similarity	NPC6702
0.8681	High Similarity	NPC112819
0.8681	High Similarity	NPC133209
0.8681	High Similarity	NPC111134
0.8676	High Similarity	NPC471983
0.8676	High Similarity	NPC149337
0.8667	High Similarity	NPC16577
0.8643	High Similarity	NPC29868
0.8643	High Similarity	NPC79622
0.8643	High Similarity	NPC212942
0.863	High Similarity	NPC218801
0.8623	High Similarity	NPC160697
0.8623	High Similarity	NPC125649
0.8623	High Similarity	NPC473107
0.8623	High Similarity	NPC476616
0.8623	High Similarity	NPC476617
0.8623	High Similarity	NPC476615
0.8623	High Similarity	NPC71372
0.8615	High Similarity	NPC103916
0.8603	High Similarity	NPC472369
0.8582	High Similarity	NPC213607
0.8582	High Similarity	NPC182509
0.8582	High Similarity	NPC174787
0.8582	High Similarity	NPC20520
0.8582	High Similarity	NPC61783
0.8571	High Similarity	NPC6262
0.8571	High Similarity	NPC272157
0.8571	High Similarity	NPC73535
0.8571	High Similarity	NPC201145
0.8571	High Similarity	NPC25111
0.8571	High Similarity	NPC90615
0.8562	High Similarity	NPC148516
0.8562	High Similarity	NPC107862
0.8562	High Similarity	NPC180605
0.8562	High Similarity	NPC177172
0.8562	High Similarity	NPC122980
0.8561	High Similarity	NPC77789
0.8561	High Similarity	NPC313081
0.8561	High Similarity	NPC18128
0.8542	High Similarity	NPC149633
0.854	High Similarity	NPC15543
0.854	High Similarity	NPC238168
0.854	High Similarity	NPC237424
0.854	High Similarity	NPC472590
0.8538	High Similarity	NPC184302
0.8529	High Similarity	NPC222108
0.8529	High Similarity	NPC96719
0.8521	High Similarity	NPC265075
0.8519	High Similarity	NPC46978
0.8511	High Similarity	NPC55947
0.8511	High Similarity	NPC184613
0.8507	High Similarity	NPC293801
0.85	High Similarity	NPC300846
0.85	High Similarity	NPC114155
0.85	High Similarity	NPC476639
0.8487	Intermediate Similarity	NPC472060
0.8487	Intermediate Similarity	NPC470342
0.8487	Intermediate Similarity	NPC472052
0.8483	Intermediate Similarity	NPC176804
0.8483	Intermediate Similarity	NPC71686
0.8478	Intermediate Similarity	NPC218884
0.8478	Intermediate Similarity	NPC228843
0.8472	Intermediate Similarity	NPC36732
0.8472	Intermediate Similarity	NPC475492
0.8462	Intermediate Similarity	NPC63010
0.8462	Intermediate Similarity	NPC131118
0.8462	Intermediate Similarity	NPC186033
0.8462	Intermediate Similarity	NPC190514
0.8456	Intermediate Similarity	NPC53986
0.8456	Intermediate Similarity	NPC38664
0.8446	Intermediate Similarity	NPC105073
0.8446	Intermediate Similarity	NPC233886
0.8446	Intermediate Similarity	NPC157081
0.8446	Intermediate Similarity	NPC224528
0.8444	Intermediate Similarity	NPC9292
0.8444	Intermediate Similarity	NPC145659
0.8435	Intermediate Similarity	NPC476969
0.8435	Intermediate Similarity	NPC321657
0.8435	Intermediate Similarity	NPC318373
0.8429	Intermediate Similarity	NPC261873
0.8429	Intermediate Similarity	NPC283009
0.8425	Intermediate Similarity	NPC242774
0.8425	Intermediate Similarity	NPC224921
0.8425	Intermediate Similarity	NPC237546
0.8425	Intermediate Similarity	NPC231712
0.8417	Intermediate Similarity	NPC77196
0.8409	Intermediate Similarity	NPC129176
0.8409	Intermediate Similarity	NPC277798
0.8409	Intermediate Similarity	NPC100108
0.8406	Intermediate Similarity	NPC211413
0.8406	Intermediate Similarity	NPC68205
0.8406	Intermediate Similarity	NPC118683
0.8406	Intermediate Similarity	NPC164804
0.8406	Intermediate Similarity	NPC293203
0.8406	Intermediate Similarity	NPC244888
0.8403	Intermediate Similarity	NPC173203
0.8403	Intermediate Similarity	NPC163508
0.84	Intermediate Similarity	NPC157333
0.8394	Intermediate Similarity	NPC134360
0.8394	Intermediate Similarity	NPC93962
0.8392	Intermediate Similarity	NPC277331
0.8392	Intermediate Similarity	NPC100482

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 NPC472646 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	425
0.1-0.2	1034
0.2-0.3	1556
0.3-0.4	2816
0.4-0.5	1713
0.5-0.6	989
0.6-0.7	518
0.7-0.8	94
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD4625	Phase 3
0.8603	High Similarity	NPD4907	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD4908	Phase 1
0.8077	Intermediate Similarity	NPD6959	Discontinued
0.7956	Intermediate Similarity	NPD4749	Approved
0.7956	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD1610	Phase 2
0.7919	Intermediate Similarity	NPD7390	Discontinued
0.7914	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD3027	Phase 3
0.7817	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD6232	Discontinued
0.7778	Intermediate Similarity	NPD1548	Phase 1
0.777	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD4097	Suspended
0.7718	Intermediate Similarity	NPD7003	Approved
0.7708	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1613	Approved
0.7707	Intermediate Similarity	NPD7768	Phase 2
0.7664	Intermediate Similarity	NPD4626	Approved
0.7654	Intermediate Similarity	NPD7473	Discontinued
0.7615	Intermediate Similarity	NPD2342	Discontinued
0.7606	Intermediate Similarity	NPD2861	Phase 2
0.7561	Intermediate Similarity	NPD5844	Phase 1
0.7518	Intermediate Similarity	NPD6696	Suspended
0.7516	Intermediate Similarity	NPD7447	Phase 1
0.75	Intermediate Similarity	NPD4750	Phase 3
0.7485	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD4060	Phase 1
0.7464	Intermediate Similarity	NPD1651	Approved
0.7463	Intermediate Similarity	NPD7635	Approved
0.7451	Intermediate Similarity	NPD7041	Phase 2
0.7451	Intermediate Similarity	NPD7212	Phase 2
0.7451	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7213	Phase 3
0.745	Intermediate Similarity	NPD5405	Approved
0.745	Intermediate Similarity	NPD5404	Approved
0.745	Intermediate Similarity	NPD6100	Approved
0.745	Intermediate Similarity	NPD5406	Approved
0.745	Intermediate Similarity	NPD5408	Approved
0.745	Intermediate Similarity	NPD6099	Approved
0.7421	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD37	Approved
0.7403	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1283	Approved
0.7368	Intermediate Similarity	NPD3750	Approved
0.7362	Intermediate Similarity	NPD7229	Phase 3
0.7361	Intermediate Similarity	NPD3018	Phase 2
0.7358	Intermediate Similarity	NPD7819	Suspended
0.7338	Intermediate Similarity	NPD5691	Approved
0.7329	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1611	Approved
0.7303	Intermediate Similarity	NPD6674	Discontinued
0.7292	Intermediate Similarity	NPD4624	Approved
0.729	Intermediate Similarity	NPD2534	Approved
0.729	Intermediate Similarity	NPD2532	Approved
0.729	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2533	Approved
0.729	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6234	Discontinued
0.7267	Intermediate Similarity	NPD4967	Phase 2
0.7267	Intermediate Similarity	NPD4966	Approved
0.7267	Intermediate Similarity	NPD4965	Approved
0.7255	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD8455	Phase 2
0.7248	Intermediate Similarity	NPD1607	Approved
0.7237	Intermediate Similarity	NPD7037	Approved
0.7231	Intermediate Similarity	NPD940	Approved
0.7231	Intermediate Similarity	NPD846	Approved
0.7225	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2935	Discontinued
0.7215	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1669	Approved
0.7203	Intermediate Similarity	NPD2983	Phase 2
0.7203	Intermediate Similarity	NPD2982	Phase 2
0.7193	Intermediate Similarity	NPD8053	Approved
0.7193	Intermediate Similarity	NPD8054	Approved
0.7186	Intermediate Similarity	NPD7228	Approved
0.7183	Intermediate Similarity	NPD1281	Approved
0.7183	Intermediate Similarity	NPD422	Phase 1
0.7181	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5124	Phase 1
0.7174	Intermediate Similarity	NPD6671	Approved
0.7172	Intermediate Similarity	NPD6584	Phase 3
0.717	Intermediate Similarity	NPD4380	Phase 2
0.7163	Intermediate Similarity	NPD2286	Discontinued
0.7154	Intermediate Similarity	NPD1242	Phase 1
0.7153	Intermediate Similarity	NPD8651	Approved
0.7153	Intermediate Similarity	NPD5283	Phase 1
0.7153	Intermediate Similarity	NPD1398	Phase 1
0.7153	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1510	Phase 2
0.7152	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3892	Phase 2
0.7135	Intermediate Similarity	NPD8312	Approved
0.7135	Intermediate Similarity	NPD8313	Approved
0.7134	Intermediate Similarity	NPD6746	Phase 2
0.7133	Intermediate Similarity	NPD2981	Phase 2
0.7125	Intermediate Similarity	NPD7411	Suspended
0.7124	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD7340	Approved
0.7117	Intermediate Similarity	NPD3749	Approved
0.7114	Intermediate Similarity	NPD1240	Approved
0.7114	Intermediate Similarity	NPD3620	Phase 2
0.7114	Intermediate Similarity	NPD2979	Phase 3
0.7114	Intermediate Similarity	NPD2238	Phase 2
0.7114	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5451	Approved
0.7103	Intermediate Similarity	NPD3094	Phase 2
0.7083	Intermediate Similarity	NPD5327	Phase 3
0.707	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5735	Approved
0.7066	Intermediate Similarity	NPD6166	Phase 2
0.7066	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD709	Approved
0.7039	Intermediate Similarity	NPD3748	Approved
0.7039	Intermediate Similarity	NPD4108	Discontinued
0.7032	Intermediate Similarity	NPD7466	Approved
0.7021	Intermediate Similarity	NPD3091	Approved
0.7018	Intermediate Similarity	NPD6559	Discontinued
0.7014	Intermediate Similarity	NPD2233	Approved
0.7014	Intermediate Similarity	NPD2232	Approved
0.7014	Intermediate Similarity	NPD2230	Approved
0.7	Intermediate Similarity	NPD3226	Approved
0.7	Intermediate Similarity	NPD4140	Approved
0.7	Intermediate Similarity	NPD7458	Discontinued
0.6988	Remote Similarity	NPD7199	Phase 2
0.6982	Remote Similarity	NPD8099	Discontinued
0.6982	Remote Similarity	NPD7177	Discontinued
0.6982	Remote Similarity	NPD8252	Approved
0.6982	Remote Similarity	NPD8251	Approved
0.6975	Remote Similarity	NPD1934	Approved
0.6968	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6582	Phase 2
0.6966	Remote Similarity	NPD6583	Phase 3
0.6962	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3020	Approved
0.6946	Remote Similarity	NPD3787	Discontinued
0.6944	Remote Similarity	NPD3092	Approved
0.6941	Remote Similarity	NPD8156	Discontinued
0.6933	Remote Similarity	NPD2801	Approved
0.6933	Remote Similarity	NPD5929	Approved
0.6914	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6353	Approved
0.6905	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1549	Phase 2
0.6899	Remote Similarity	NPD1511	Approved
0.6894	Remote Similarity	NPD4005	Discontinued
0.6884	Remote Similarity	NPD228	Approved
0.6883	Remote Similarity	NPD2438	Suspended
0.6871	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4538	Approved
0.6863	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4536	Approved
0.6861	Remote Similarity	NPD3022	Approved
0.6861	Remote Similarity	NPD3021	Approved
0.6857	Remote Similarity	NPD497	Approved
0.6855	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2859	Approved
0.6846	Remote Similarity	NPD2860	Approved
0.6846	Remote Similarity	NPD844	Approved
0.6845	Remote Similarity	NPD8151	Discontinued
0.6842	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2346	Discontinued
0.6839	Remote Similarity	NPD5762	Approved
0.6839	Remote Similarity	NPD5763	Approved
0.6839	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3540	Phase 1
0.6835	Remote Similarity	NPD5535	Approved
0.6829	Remote Similarity	NPD1465	Phase 2
0.6828	Remote Similarity	NPD3705	Approved
0.6821	Remote Similarity	NPD7240	Approved
0.6815	Remote Similarity	NPD8166	Discontinued
0.6813	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6090	Discontinued
0.6813	Remote Similarity	NPD4319	Phase 2
0.6813	Remote Similarity	NPD1512	Approved
0.6807	Remote Similarity	NPD7075	Discontinued
0.6807	Remote Similarity	NPD4055	Discovery
0.6806	Remote Similarity	NPD3019	Approved
0.6806	Remote Similarity	NPD5125	Phase 3
0.6806	Remote Similarity	NPD4059	Approved
0.6806	Remote Similarity	NPD3095	Discontinued
0.6806	Remote Similarity	NPD5126	Approved
0.68	Remote Similarity	NPD7095	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