NPASS Compound

Structure

NPC93099 OpenBabel07101718272D 33 36 0 0 1 0 0 0 0 0999 V2000 -6.0622 1.5000 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 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 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 1.7321 -0.0000 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 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 -0.5000 0.0000 C 0 0 2 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 -4.3301 -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 2 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 -0.0000 -2.0000 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 -6.0622 -0.5000 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 -4.3301 -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 2 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 -6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 -3.0000 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 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 -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 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 29 1 0 0 0 0 2 30 1 0 0 0 0 3 4 2 0 0 0 0 3 7 1 0 0 0 0 4 9 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 22 1 0 0 0 0 7 12 2 0 0 0 0 7 23 1 0 0 0 0 8 13 1 0 0 0 0 8 24 1 0 0 0 0 9 18 2 0 0 0 0 9 29 1 0 0 0 0 10 19 2 0 0 0 0 10 31 1 0 0 0 0 11 6 1 6 0 0 0 11 14 1 0 0 0 0 11 32 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 20 2 0 0 0 0 14 16 1 0 0 0 0 14 25 1 1 0 0 0 15 26 2 0 0 0 0 16 17 1 0 0 0 0 16 27 1 6 0 0 0 17 21 1 0 0 0 0 17 28 1 1 0 0 0 18 33 1 0 0 0 0 19 20 1 0 0 0 0 19 30 1 0 0 0 0 20 33 1 0 0 0 0 21 31 1 6 0 0 0 21 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.11
Volume:	424.574
LogP:	0.535
LogD:	0.437
LogS:	-4.079
# Rotatable Bonds:	5
TPSA:	188.51
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.266
Synthetic Accessibility Score:	4.07
Fsp3:	0.381
Lipinski Rule-of-5:	Rejected
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:	-6.176
MDCK Permeability:	2.687346568563953e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.941
Human Intestinal Absorption (HIA):	0.593
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.865

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	74.41111755371094%
Volume Distribution (VD):	1.029
Pgp-substrate:	25.03548240661621%

ADMET: Metabolism

CYP1A2-inhibitor:	0.095
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.155
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.428
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.184
CYP3A4-inhibitor:	0.049
CYP3A4-substrate:	0.025

ADMET: Excretion

Clearance (CL):	4.334
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.39
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.811
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.205
Carcinogencity:	0.079
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC93099

Natural Product ID:	NPC93099
*Common Name:**	3-O-Beta-D-Glucopyranoside
IUPAC Name:	1,8-dihydroxy-4,5-dimethoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyxanthen-9-one
Synonyms:
Standard InCHIKey:	YYBFILICFFBVIZ-AAHOILBJSA-N
Standard InCHI:	InChI=1S/C21H22O12/c1-29-9-4-3-7(23)12-15(26)13-8(24)5-10(19(30-2)20(13)33-18(9)12)31-21-17(28)16(27)14(25)11(6-22)32-21/h3-5,11,14,16-17,21-25,27-28H,6H2,1-2H3/t11-,14-,16+,17-,21-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2OC)oc2c(c3=O)c(O)ccc2OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL466340
PubChem CID:	24878797
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO32688	gentianella amarella ssp. acuta	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18336006]

☑ 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
Others	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Inhibition	=	17.6	%	PMID[482946]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	Inhibition	=	40.2	%	PMID[482946]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	Inhibition	=	47.8	%	PMID[482946]

☑ 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 NPC93099 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	446
0.1-0.2	1811
0.2-0.3	4230
0.3-0.4	9919
0.4-0.5	8255
0.5-0.6	4276
0.6-0.7	5359
0.7-0.8	5156
0.8-0.85	1646
0.85-0.9	1045
0.9-0.95	408
0.95-1	146

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC210042
0.9937	High Similarity	NPC472383
0.9937	High Similarity	NPC472381
0.9937	High Similarity	NPC95855
0.9874	High Similarity	NPC474434
0.9874	High Similarity	NPC22195
0.9874	High Similarity	NPC44558
0.9874	High Similarity	NPC21190
0.9874	High Similarity	NPC183357
0.9812	High Similarity	NPC267254
0.9812	High Similarity	NPC472386
0.9812	High Similarity	NPC156977
0.9811	High Similarity	NPC471457
0.9811	High Similarity	NPC112755
0.9811	High Similarity	NPC170675
0.9811	High Similarity	NPC183036
0.9752	High Similarity	NPC51774
0.9752	High Similarity	NPC239549
0.9752	High Similarity	NPC236191
0.975	High Similarity	NPC105511
0.975	High Similarity	NPC471416
0.975	High Similarity	NPC34287
0.9691	High Similarity	NPC102028
0.9691	High Similarity	NPC142996
0.9689	High Similarity	NPC307518
0.9689	High Similarity	NPC48773
0.9689	High Similarity	NPC205076
0.9689	High Similarity	NPC301683
0.9688	High Similarity	NPC226294
0.9688	High Similarity	NPC105025
0.9688	High Similarity	NPC229687
0.9688	High Similarity	NPC201292
0.9688	High Similarity	NPC58053
0.9688	High Similarity	NPC475942
0.9688	High Similarity	NPC469931
0.9688	High Similarity	NPC186807
0.9688	High Similarity	NPC45638
0.9688	High Similarity	NPC93337
0.9686	High Similarity	NPC5778
0.9686	High Similarity	NPC236934
0.9632	High Similarity	NPC472384
0.9632	High Similarity	NPC472382
0.9632	High Similarity	NPC472380
0.963	High Similarity	NPC204693
0.9627	High Similarity	NPC224462
0.9627	High Similarity	NPC293004
0.9627	High Similarity	NPC194483
0.9625	High Similarity	NPC135345
0.9625	High Similarity	NPC146792
0.9625	High Similarity	NPC45400
0.9625	High Similarity	NPC58716
0.9625	High Similarity	NPC45618
0.9573	High Similarity	NPC472387
0.9568	High Similarity	NPC117260
0.9568	High Similarity	NPC475155
0.9568	High Similarity	NPC254540
0.9568	High Similarity	NPC476405
0.9568	High Similarity	NPC172807
0.9568	High Similarity	NPC3583
0.9568	High Similarity	NPC211594
0.9568	High Similarity	NPC259152
0.9565	High Similarity	NPC293629
0.9563	High Similarity	NPC99957
0.9563	High Similarity	NPC181616
0.956	High Similarity	NPC243930
0.956	High Similarity	NPC309025
0.956	High Similarity	NPC88023
0.956	High Similarity	NPC29830
0.956	High Similarity	NPC127415
0.9512	High Similarity	NPC169733
0.9512	High Similarity	NPC268533
0.9509	High Similarity	NPC169977
0.9509	High Similarity	NPC42773
0.9509	High Similarity	NPC45522
0.9509	High Similarity	NPC101026
0.9509	High Similarity	NPC21666
0.9509	High Similarity	NPC24043
0.9506	High Similarity	NPC84265
0.9506	High Similarity	NPC52353
0.9506	High Similarity	NPC51326
0.9506	High Similarity	NPC231194
0.9506	High Similarity	NPC79056
0.9506	High Similarity	NPC105095
0.9506	High Similarity	NPC282987
0.9506	High Similarity	NPC44328
0.9506	High Similarity	NPC245014
0.9506	High Similarity	NPC177731
0.9503	High Similarity	NPC477502
0.9503	High Similarity	NPC229729
0.95	High Similarity	NPC165720
0.95	High Similarity	NPC311830
0.95	High Similarity	NPC22832
0.9497	High Similarity	NPC127782
0.9497	High Similarity	NPC300537
0.9455	High Similarity	NPC476622
0.9455	High Similarity	NPC476620
0.9455	High Similarity	NPC476623
0.9455	High Similarity	NPC476618
0.9455	High Similarity	NPC476619
0.9455	High Similarity	NPC168584
0.9455	High Similarity	NPC476621
0.9451	High Similarity	NPC264735
0.9451	High Similarity	NPC477848
0.9451	High Similarity	NPC472607
0.9448	High Similarity	NPC261254
0.9448	High Similarity	NPC256760
0.9444	High Similarity	NPC52382
0.9444	High Similarity	NPC43587
0.9444	High Similarity	NPC61791
0.9444	High Similarity	NPC270578
0.9444	High Similarity	NPC195257
0.9444	High Similarity	NPC209296
0.9441	High Similarity	NPC210073
0.9441	High Similarity	NPC70441
0.9441	High Similarity	NPC115674
0.9437	High Similarity	NPC88043
0.9437	High Similarity	NPC19709
0.9437	High Similarity	NPC284960
0.9437	High Similarity	NPC94777
0.9437	High Similarity	NPC191306
0.9437	High Similarity	NPC270335
0.9437	High Similarity	NPC222936
0.9434	High Similarity	NPC182045
0.9398	High Similarity	NPC473571
0.9398	High Similarity	NPC126784
0.9398	High Similarity	NPC470444
0.9398	High Similarity	NPC470443
0.9398	High Similarity	NPC473682
0.9398	High Similarity	NPC110941
0.9398	High Similarity	NPC241423
0.9394	High Similarity	NPC472385
0.9394	High Similarity	NPC198324
0.9394	High Similarity	NPC470949
0.9394	High Similarity	NPC211532
0.9394	High Similarity	NPC8573
0.9394	High Similarity	NPC257714
0.9394	High Similarity	NPC233994
0.9394	High Similarity	NPC65563
0.939	High Similarity	NPC208668
0.9387	High Similarity	NPC150767
0.9387	High Similarity	NPC212748
0.9387	High Similarity	NPC78734
0.9383	High Similarity	NPC160156
0.9383	High Similarity	NPC116745
0.9383	High Similarity	NPC92565
0.9379	High Similarity	NPC284277
0.9379	High Similarity	NPC475497
0.9379	High Similarity	NPC475366
0.9375	High Similarity	NPC77660
0.9375	High Similarity	NPC189142
0.9375	High Similarity	NPC148273
0.9375	High Similarity	NPC473043
0.9371	High Similarity	NPC110349
0.9345	High Similarity	NPC148710
0.9341	High Similarity	NPC473071
0.9341	High Similarity	NPC473073
0.9337	High Similarity	NPC475261
0.9333	High Similarity	NPC115760
0.9333	High Similarity	NPC43211
0.9333	High Similarity	NPC237435
0.9333	High Similarity	NPC135277
0.9333	High Similarity	NPC49344
0.9333	High Similarity	NPC108202
0.9333	High Similarity	NPC101191
0.9333	High Similarity	NPC210094
0.9329	High Similarity	NPC235575
0.9325	High Similarity	NPC120099
0.9325	High Similarity	NPC105283
0.9325	High Similarity	NPC223747
0.9325	High Similarity	NPC203050
0.9325	High Similarity	NPC471287
0.9325	High Similarity	NPC219904
0.9325	High Similarity	NPC86008
0.9325	High Similarity	NPC225434
0.9321	High Similarity	NPC197285
0.9321	High Similarity	NPC21100
0.9321	High Similarity	NPC8856
0.9317	High Similarity	NPC168822
0.9317	High Similarity	NPC470178
0.9304	High Similarity	NPC206378
0.9286	High Similarity	NPC470449
0.9286	High Similarity	NPC470447
0.9286	High Similarity	NPC470445
0.9286	High Similarity	NPC473072
0.9286	High Similarity	NPC470446
0.9281	High Similarity	NPC473895
0.9277	High Similarity	NPC472992
0.9277	High Similarity	NPC472991
0.9273	High Similarity	NPC175230
0.9273	High Similarity	NPC172033
0.9273	High Similarity	NPC4390
0.9273	High Similarity	NPC88560
0.9268	High Similarity	NPC95866
0.9268	High Similarity	NPC218488
0.9268	High Similarity	NPC199079
0.9268	High Similarity	NPC206123
0.9268	High Similarity	NPC204937
0.9268	High Similarity	NPC210808
0.9268	High Similarity	NPC67105
0.9268	High Similarity	NPC285197

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 NPC93099 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	394
0.1-0.2	957
0.2-0.3	2033
0.3-0.4	2668
0.4-0.5	1768
0.5-0.6	888
0.6-0.7	287
0.7-0.8	117
0.8-0.85	17
0.85-0.9	14
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9506	High Similarity	NPD7074	Phase 3
0.9444	High Similarity	NPD7054	Approved
0.9387	High Similarity	NPD7472	Approved
0.9333	High Similarity	NPD4338	Clinical (unspecified phase)
0.9264	High Similarity	NPD3818	Discontinued
0.9217	High Similarity	NPD7808	Phase 3
0.9212	High Similarity	NPD6797	Phase 2
0.9157	High Similarity	NPD7251	Discontinued
0.9125	High Similarity	NPD4381	Clinical (unspecified phase)
0.9024	High Similarity	NPD6168	Clinical (unspecified phase)
0.9024	High Similarity	NPD6166	Phase 2
0.9024	High Similarity	NPD6167	Clinical (unspecified phase)
0.8994	High Similarity	NPD1934	Approved
0.8938	High Similarity	NPD2801	Approved
0.8862	High Similarity	NPD7804	Clinical (unspecified phase)
0.882	High Similarity	NPD2393	Clinical (unspecified phase)
0.8667	High Similarity	NPD5494	Approved
0.8598	High Similarity	NPD4868	Clinical (unspecified phase)
0.8537	High Similarity	NPD3817	Phase 2
0.8519	High Similarity	NPD4380	Phase 2
0.8488	Intermediate Similarity	NPD6559	Discontinued
0.8485	Intermediate Similarity	NPD3882	Suspended
0.8375	Intermediate Similarity	NPD1511	Approved
0.8324	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.8314	Intermediate Similarity	NPD5844	Phase 1
0.8313	Intermediate Similarity	NPD5402	Approved
0.8272	Intermediate Similarity	NPD1512	Approved
0.8253	Intermediate Similarity	NPD1465	Phase 2
0.8228	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6801	Discontinued
0.8176	Intermediate Similarity	NPD6959	Discontinued
0.8176	Intermediate Similarity	NPD1549	Phase 2
0.8171	Intermediate Similarity	NPD1653	Approved
0.8167	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6232	Discontinued
0.8098	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7473	Discontinued
0.8046	Intermediate Similarity	NPD7228	Approved
0.8036	Intermediate Similarity	NPD7819	Suspended
0.8024	Intermediate Similarity	NPD7411	Suspended
0.8	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD8313	Approved
0.7978	Intermediate Similarity	NPD8312	Approved
0.7965	Intermediate Similarity	NPD7199	Phase 2
0.7956	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD3751	Discontinued
0.7937	Intermediate Similarity	NPD2796	Approved
0.7927	Intermediate Similarity	NPD6799	Approved
0.7919	Intermediate Similarity	NPD3787	Discontinued
0.7892	Intermediate Similarity	NPD5403	Approved
0.7879	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD1510	Phase 2
0.787	Intermediate Similarity	NPD37	Approved
0.7865	Intermediate Similarity	NPD7685	Pre-registration
0.7861	Intermediate Similarity	NPD6777	Approved
0.7861	Intermediate Similarity	NPD6776	Approved
0.7861	Intermediate Similarity	NPD6779	Approved
0.7861	Intermediate Similarity	NPD6778	Approved
0.7861	Intermediate Similarity	NPD6782	Approved
0.7861	Intermediate Similarity	NPD6780	Approved
0.7861	Intermediate Similarity	NPD6781	Approved
0.7849	Intermediate Similarity	NPD6234	Discontinued
0.7836	Intermediate Similarity	NPD4965	Approved
0.7836	Intermediate Similarity	NPD4967	Phase 2
0.7836	Intermediate Similarity	NPD4966	Approved
0.779	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5401	Approved
0.7771	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD1247	Approved
0.7751	Intermediate Similarity	NPD6599	Discontinued
0.7737	Intermediate Similarity	NPD7698	Approved
0.7737	Intermediate Similarity	NPD7697	Approved
0.7737	Intermediate Similarity	NPD7696	Phase 3
0.7737	Intermediate Similarity	NPD7435	Discontinued
0.7736	Intermediate Similarity	NPD1240	Approved
0.7736	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1613	Approved
0.7732	Intermediate Similarity	NPD7783	Phase 2
0.7732	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.772	Intermediate Similarity	NPD8151	Discontinued
0.7711	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD3926	Phase 2
0.7669	Intermediate Similarity	NPD7266	Discontinued
0.7668	Intermediate Similarity	NPD7701	Phase 2
0.7667	Intermediate Similarity	NPD7240	Approved
0.764	Intermediate Similarity	NPD1607	Approved
0.7636	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD943	Approved
0.7617	Intermediate Similarity	NPD7584	Approved
0.7616	Intermediate Similarity	NPD8455	Phase 2
0.7607	Intermediate Similarity	NPD2935	Discontinued
0.7604	Intermediate Similarity	NPD7870	Phase 2
0.7604	Intermediate Similarity	NPD7871	Phase 2
0.7594	Intermediate Similarity	NPD6534	Approved
0.7594	Intermediate Similarity	NPD6535	Approved
0.7592	Intermediate Similarity	NPD6823	Phase 2
0.7586	Intermediate Similarity	NPD3749	Approved
0.7578	Intermediate Similarity	NPD1933	Approved
0.7566	Intermediate Similarity	NPD7699	Phase 2
0.7566	Intermediate Similarity	NPD7700	Phase 2
0.7547	Intermediate Similarity	NPD3027	Phase 3
0.7543	Intermediate Similarity	NPD919	Approved
0.753	Intermediate Similarity	NPD3750	Approved
0.753	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD7768	Phase 2
0.7515	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7874	Approved
0.7485	Intermediate Similarity	NPD6190	Approved
0.7484	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD2800	Approved
0.7469	Intermediate Similarity	NPD447	Suspended
0.7469	Intermediate Similarity	NPD230	Phase 1
0.7462	Intermediate Similarity	NPD7801	Approved
0.7456	Intermediate Similarity	NPD2533	Approved
0.7456	Intermediate Similarity	NPD2534	Approved
0.7456	Intermediate Similarity	NPD2532	Approved
0.7421	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1551	Phase 2
0.7391	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD920	Approved
0.7365	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD6212	Phase 3
0.7354	Intermediate Similarity	NPD6213	Phase 3
0.7354	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD5953	Discontinued
0.7308	Intermediate Similarity	NPD7286	Phase 2
0.7283	Intermediate Similarity	NPD3226	Approved
0.7273	Intermediate Similarity	NPD8150	Discontinued
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.7262	Intermediate Similarity	NPD6674	Discontinued
0.7257	Intermediate Similarity	NPD6844	Discontinued
0.7254	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD8320	Phase 1
0.7245	Intermediate Similarity	NPD8319	Approved
0.724	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3748	Approved
0.7222	Intermediate Similarity	NPD7585	Approved
0.7212	Intermediate Similarity	NPD6651	Approved
0.7194	Intermediate Similarity	NPD7680	Approved
0.7186	Intermediate Similarity	NPD6099	Approved
0.7186	Intermediate Similarity	NPD6100	Approved
0.7184	Intermediate Similarity	NPD7458	Discontinued
0.7172	Intermediate Similarity	NPD7583	Approved
0.716	Intermediate Similarity	NPD4908	Phase 1
0.7152	Intermediate Similarity	NPD1091	Approved
0.7151	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2346	Discontinued
0.7143	Intermediate Similarity	NPD2344	Approved
0.7136	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4360	Phase 2
0.7135	Intermediate Similarity	NPD4363	Phase 3
0.7126	Intermediate Similarity	NPD7033	Discontinued
0.7126	Intermediate Similarity	NPD2799	Discontinued
0.7126	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD9494	Approved
0.7093	Intermediate Similarity	NPD7390	Discontinued
0.7088	Intermediate Similarity	NPD5242	Approved
0.7079	Intermediate Similarity	NPD5353	Approved
0.7073	Intermediate Similarity	NPD2313	Discontinued
0.7073	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1243	Approved
0.7056	Intermediate Similarity	NPD5006	Approved
0.7056	Intermediate Similarity	NPD5005	Approved
0.7055	Intermediate Similarity	NPD6832	Phase 2
0.7044	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2798	Approved
0.7035	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5710	Approved
0.7033	Intermediate Similarity	NPD5711	Approved
0.703	Intermediate Similarity	NPD6233	Phase 2
0.7024	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2861	Phase 2
0.6989	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD8127	Discontinued
0.6977	Remote Similarity	NPD2309	Approved
0.6975	Remote Similarity	NPD1203	Approved
0.697	Remote Similarity	NPD6798	Discontinued
0.6968	Remote Similarity	NPD7549	Discontinued
0.6967	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD8059	Phase 3
0.6963	Remote Similarity	NPD6841	Approved
0.6963	Remote Similarity	NPD6843	Phase 3
0.6963	Remote Similarity	NPD6842	Approved
0.6959	Remote Similarity	NPD1652	Phase 2
0.6957	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5124	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