NPASS Compound

Structure

CID270335 OpenBabel06191716072D 34 37 0 0 1 0 0 0 0 0999 V2000 2.5981 -0.5000 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 3.4641 1.0000 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 5.1962 -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 -0.8660 -1.5000 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 6.0622 -3.5000 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 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 1.7321 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 -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 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 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 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 8 1 0 0 0 0 2 13 1 0 0 0 0 3 8 2 0 0 0 0 3 11 1 0 0 0 0 4 9 2 0 0 0 0 4 12 1 0 0 0 0 5 9 1 0 0 0 0 5 14 2 0 0 0 0 6 10 1 0 0 0 0 6 23 1 0 0 0 0 7 24 1 0 0 0 0 8 21 1 0 0 0 0 9 25 1 0 0 0 0 10 17 1 0 0 0 0 10 21 2 0 0 0 0 11 13 2 0 0 0 0 11 26 1 0 0 0 0 12 16 2 0 0 0 0 12 27 1 0 0 0 0 13 33 1 0 0 0 0 14 16 1 0 0 0 0 14 32 1 0 0 0 0 15 7 1 6 0 0 0 15 18 1 0 0 0 0 15 34 1 0 0 0 0 16 17 1 0 0 0 0 17 28 2 0 0 0 0 18 19 1 0 0 0 0 18 29 1 1 0 0 0 19 20 1 0 0 0 0 19 30 1 6 0 0 0 20 22 1 0 0 0 0 20 31 1 1 0 0 0 21 32 1 0 0 0 0 22 33 1 6 0 0 0 22 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.11
Volume:	439.233
LogP:	-0.13
LogD:	-0.214
LogS:	-4.049
# Rotatable Bonds:	5
TPSA:	210.51
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.228
Synthetic Accessibility Score:	4.128
Fsp3:	0.318
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.274
MDCK Permeability:	9.64163973549148e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.858
Human Intestinal Absorption (HIA):	0.722
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	87.21158599853516%
Volume Distribution (VD):	0.913
Pgp-substrate:	15.391868591308594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.196
CYP1A2-substrate:	0.046
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.173
CYP2D6-inhibitor:	0.094
CYP2D6-substrate:	0.166
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	2.289
Half-life (T1/2):	0.954

ADMET: Toxicity

hERG Blockers:	0.074
Human Hepatotoxicity (H-HT):	0.229
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.802
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.267
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.06
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC270335

Natural Product ID:	NPC270335
*Common Name:**	Ophioglonol 4'-O-Beta-D-Glucopyranoside
IUPAC Name:	5,7-dihydroxy-3-(hydroxymethyl)-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
Synonyms:
Standard InCHIKey:	XTPXAOSAGWJNDB-VQIXPAPJSA-N
Standard InCHI:	InChI=1S/C22H22O12/c23-6-10-17(28)16-12(27)4-9(25)5-14(16)32-21(10)8-1-2-13(11(26)3-8)33-22-20(31)19(30)18(29)15(7-24)34-22/h1-5,15,18-20,22-27,29-31H,6-7H2/t15-,18-,19+,20-,22-/m1/s1
SMILES:	c1cc(c(cc1c1c(CO)c(=O)c2c(cc(cc2o1)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1773609
PubChem CID:	54582243
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-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
NPO31176	Ophioglossum pedunculosum	Species	Ophioglossaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21401115]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		CC50	=	19700.0	nM	PMID[484300]

☑ 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 NPC270335 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	450
0.1-0.2	1852
0.2-0.3	4210
0.3-0.4	9902
0.4-0.5	8175
0.5-0.6	4054
0.6-0.7	5090
0.7-0.8	5301
0.8-0.85	1762
0.85-0.9	1329
0.9-0.95	402
0.95-1	170

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC191306
0.9935	High Similarity	NPC22832
0.9935	High Similarity	NPC189142
0.9935	High Similarity	NPC311830
0.9935	High Similarity	NPC77660
0.9872	High Similarity	NPC21100
0.9872	High Similarity	NPC197285
0.9871	High Similarity	NPC168822
0.9871	High Similarity	NPC88023
0.9871	High Similarity	NPC19709
0.9871	High Similarity	NPC309025
0.9871	High Similarity	NPC243930
0.9871	High Similarity	NPC284960
0.9871	High Similarity	NPC222936
0.9809	High Similarity	NPC146792
0.9809	High Similarity	NPC58716
0.9809	High Similarity	NPC45618
0.9809	High Similarity	NPC229729
0.9808	High Similarity	NPC277205
0.9806	High Similarity	NPC473043
0.9747	High Similarity	NPC45638
0.9747	High Similarity	NPC93337
0.9747	High Similarity	NPC203050
0.9747	High Similarity	NPC469931
0.9747	High Similarity	NPC58053
0.9747	High Similarity	NPC120099
0.9747	High Similarity	NPC219904
0.9747	High Similarity	NPC225434
0.9747	High Similarity	NPC475942
0.9747	High Similarity	NPC226294
0.9747	High Similarity	NPC186807
0.9747	High Similarity	NPC201292
0.9747	High Similarity	NPC209296
0.9747	High Similarity	NPC195257
0.9747	High Similarity	NPC223747
0.9747	High Similarity	NPC105025
0.9747	High Similarity	NPC86008
0.9745	High Similarity	NPC5778
0.9745	High Similarity	NPC281131
0.9745	High Similarity	NPC88789
0.9745	High Similarity	NPC145038
0.9745	High Similarity	NPC8856
0.9745	High Similarity	NPC274618
0.9745	High Similarity	NPC253662
0.9745	High Similarity	NPC179950
0.9745	High Similarity	NPC115674
0.9745	High Similarity	NPC56077
0.9745	High Similarity	NPC308404
0.9745	High Similarity	NPC210073
0.9745	High Similarity	NPC118284
0.9745	High Similarity	NPC236934
0.9745	High Similarity	NPC276222
0.9744	High Similarity	NPC29830
0.9744	High Similarity	NPC88043
0.9742	High Similarity	NPC182045
0.9686	High Similarity	NPC51326
0.9686	High Similarity	NPC245014
0.9686	High Similarity	NPC285197
0.9686	High Similarity	NPC206123
0.9686	High Similarity	NPC282987
0.9686	High Similarity	NPC231194
0.9686	High Similarity	NPC84265
0.9684	High Similarity	NPC173637
0.9684	High Similarity	NPC127546
0.9684	High Similarity	NPC45400
0.9684	High Similarity	NPC52550
0.9684	High Similarity	NPC226304
0.9684	High Similarity	NPC325555
0.9684	High Similarity	NPC84362
0.9684	High Similarity	NPC223424
0.9684	High Similarity	NPC317489
0.9684	High Similarity	NPC265530
0.9682	High Similarity	NPC240431
0.9682	High Similarity	NPC55786
0.9682	High Similarity	NPC19388
0.9682	High Similarity	NPC165720
0.9679	High Similarity	NPC300537
0.9679	High Similarity	NPC127782
0.9677	High Similarity	NPC110349
0.9625	High Similarity	NPC153755
0.9625	High Similarity	NPC254540
0.9625	High Similarity	NPC48773
0.9625	High Similarity	NPC172807
0.9625	High Similarity	NPC235575
0.9625	High Similarity	NPC180918
0.9625	High Similarity	NPC259152
0.9625	High Similarity	NPC26230
0.9625	High Similarity	NPC205076
0.9625	High Similarity	NPC256760
0.9625	High Similarity	NPC60735
0.9625	High Similarity	NPC476405
0.9625	High Similarity	NPC3583
0.9625	High Similarity	NPC211594
0.9625	High Similarity	NPC117260
0.9625	High Similarity	NPC307518
0.9623	High Similarity	NPC471457
0.9623	High Similarity	NPC229687
0.9623	High Similarity	NPC170675
0.9623	High Similarity	NPC112755
0.962	High Similarity	NPC73855
0.962	High Similarity	NPC277174
0.962	High Similarity	NPC135599
0.962	High Similarity	NPC113968
0.962	High Similarity	NPC328940
0.962	High Similarity	NPC254306
0.961	High Similarity	NPC261866
0.9565	High Similarity	NPC24043
0.9565	High Similarity	NPC101026
0.9565	High Similarity	NPC169977
0.9565	High Similarity	NPC204693
0.9565	High Similarity	NPC42773
0.9565	High Similarity	NPC208668
0.9565	High Similarity	NPC472993
0.9565	High Similarity	NPC4390
0.9565	High Similarity	NPC45522
0.9565	High Similarity	NPC21666
0.9563	High Similarity	NPC149011
0.9563	High Similarity	NPC34287
0.9563	High Similarity	NPC255157
0.9563	High Similarity	NPC20505
0.9563	High Similarity	NPC183357
0.9563	High Similarity	NPC67105
0.9563	High Similarity	NPC155763
0.9563	High Similarity	NPC471416
0.9563	High Similarity	NPC235260
0.9563	High Similarity	NPC177731
0.9563	High Similarity	NPC204937
0.9563	High Similarity	NPC21190
0.9563	High Similarity	NPC254855
0.9563	High Similarity	NPC67326
0.9563	High Similarity	NPC29958
0.9563	High Similarity	NPC150767
0.9563	High Similarity	NPC78734
0.9563	High Similarity	NPC105511
0.9563	High Similarity	NPC156869
0.9563	High Similarity	NPC259896
0.9563	High Similarity	NPC244776
0.9563	High Similarity	NPC224462
0.9563	High Similarity	NPC105095
0.9563	High Similarity	NPC218488
0.9563	High Similarity	NPC22195
0.9563	High Similarity	NPC116864
0.9563	High Similarity	NPC79056
0.9563	High Similarity	NPC136042
0.9563	High Similarity	NPC95866
0.9563	High Similarity	NPC44328
0.956	High Similarity	NPC160156
0.956	High Similarity	NPC275454
0.956	High Similarity	NPC116745
0.956	High Similarity	NPC92565
0.956	High Similarity	NPC477502
0.9557	High Similarity	NPC284277
0.9557	High Similarity	NPC475366
0.9557	High Similarity	NPC475497
0.9506	High Similarity	NPC198199
0.9506	High Similarity	NPC210094
0.9506	High Similarity	NPC135277
0.9506	High Similarity	NPC101191
0.9506	High Similarity	NPC294815
0.9506	High Similarity	NPC19108
0.9506	High Similarity	NPC49344
0.9506	High Similarity	NPC477848
0.9506	High Similarity	NPC220173
0.9506	High Similarity	NPC237435
0.9506	High Similarity	NPC472607
0.9506	High Similarity	NPC115760
0.9506	High Similarity	NPC476472
0.9506	High Similarity	NPC43211
0.9506	High Similarity	NPC473327
0.9506	High Similarity	NPC16194
0.9503	High Similarity	NPC33054
0.9503	High Similarity	NPC203259
0.9503	High Similarity	NPC471748
0.9503	High Similarity	NPC176740
0.9503	High Similarity	NPC245452
0.9503	High Similarity	NPC261254
0.9503	High Similarity	NPC155877
0.9503	High Similarity	NPC190003
0.9503	High Similarity	NPC471725
0.9503	High Similarity	NPC175107
0.9503	High Similarity	NPC134532
0.95	High Similarity	NPC43587
0.95	High Similarity	NPC293629
0.95	High Similarity	NPC52382
0.95	High Similarity	NPC227508
0.95	High Similarity	NPC270578
0.95	High Similarity	NPC472383
0.95	High Similarity	NPC95855
0.95	High Similarity	NPC210042
0.95	High Similarity	NPC105283
0.95	High Similarity	NPC138927
0.95	High Similarity	NPC472381
0.9497	High Similarity	NPC67037
0.9497	High Similarity	NPC99957
0.9497	High Similarity	NPC181616
0.9497	High Similarity	NPC255615
0.9494	High Similarity	NPC94777
0.9481	High Similarity	NPC143851
0.9481	High Similarity	NPC29763
0.9481	High Similarity	NPC210003

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 NPC270335 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	417
0.1-0.2	944
0.2-0.3	1929
0.3-0.4	2694
0.4-0.5	1779
0.5-0.6	909
0.6-0.7	298
0.7-0.8	136
0.8-0.85	17
0.85-0.9	17
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9747	High Similarity	NPD7054	Approved
0.9686	High Similarity	NPD7472	Approved
0.9563	High Similarity	NPD7074	Phase 3
0.956	High Similarity	NPD3818	Discontinued
0.9506	High Similarity	NPD4338	Clinical (unspecified phase)
0.9503	High Similarity	NPD6797	Phase 2
0.9444	High Similarity	NPD7251	Discontinued
0.9423	High Similarity	NPD4381	Clinical (unspecified phase)
0.9387	High Similarity	NPD7808	Phase 3
0.9167	High Similarity	NPD1934	Approved
0.9074	High Similarity	NPD6168	Clinical (unspecified phase)
0.9074	High Similarity	NPD6167	Clinical (unspecified phase)
0.9074	High Similarity	NPD6166	Phase 2
0.8987	High Similarity	NPD2801	Approved
0.8987	High Similarity	NPD2393	Clinical (unspecified phase)
0.8909	High Similarity	NPD7804	Clinical (unspecified phase)
0.8896	High Similarity	NPD1511	Approved
0.8812	High Similarity	NPD3817	Phase 2
0.8797	High Similarity	NPD4380	Phase 2
0.8782	High Similarity	NPD1512	Approved
0.8758	High Similarity	NPD4868	Clinical (unspecified phase)
0.8642	High Similarity	NPD3882	Suspended
0.8529	High Similarity	NPD6559	Discontinued
0.8438	Intermediate Similarity	NPD1653	Approved
0.8387	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD7075	Discontinued
0.8363	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD5402	Approved
0.8333	Intermediate Similarity	NPD1549	Phase 2
0.8263	Intermediate Similarity	NPD5494	Approved
0.8261	Intermediate Similarity	NPD5403	Approved
0.825	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6801	Discontinued
0.8182	Intermediate Similarity	NPD1465	Phase 2
0.8182	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD1510	Phase 2
0.814	Intermediate Similarity	NPD5844	Phase 1
0.8137	Intermediate Similarity	NPD5401	Approved
0.8133	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD7685	Pre-registration
0.8089	Intermediate Similarity	NPD2796	Approved
0.8075	Intermediate Similarity	NPD6799	Approved
0.8072	Intermediate Similarity	NPD7819	Suspended
0.8061	Intermediate Similarity	NPD7411	Suspended
0.8059	Intermediate Similarity	NPD6232	Discontinued
0.8037	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD7199	Phase 2
0.8	Intermediate Similarity	NPD1613	Approved
0.7977	Intermediate Similarity	NPD3751	Discontinued
0.7977	Intermediate Similarity	NPD7228	Approved
0.7953	Intermediate Similarity	NPD3787	Discontinued
0.791	Intermediate Similarity	NPD8313	Approved
0.791	Intermediate Similarity	NPD8312	Approved
0.7901	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6234	Discontinued
0.7812	Intermediate Similarity	NPD7266	Discontinued
0.7803	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD37	Approved
0.779	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6599	Discontinued
0.7778	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3750	Approved
0.7771	Intermediate Similarity	NPD943	Approved
0.7771	Intermediate Similarity	NPD1240	Approved
0.7765	Intermediate Similarity	NPD4965	Approved
0.7765	Intermediate Similarity	NPD4967	Phase 2
0.7765	Intermediate Similarity	NPD4966	Approved
0.7764	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD7584	Approved
0.7722	Intermediate Similarity	NPD1933	Approved
0.7722	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3027	Phase 3
0.7677	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD919	Approved
0.7673	Intermediate Similarity	NPD1607	Approved
0.7647	Intermediate Similarity	NPD8455	Phase 2
0.764	Intermediate Similarity	NPD1551	Phase 2
0.7622	Intermediate Similarity	NPD6190	Approved
0.7616	Intermediate Similarity	NPD3749	Approved
0.761	Intermediate Similarity	NPD230	Phase 1
0.7606	Intermediate Similarity	NPD6777	Approved
0.7606	Intermediate Similarity	NPD6779	Approved
0.7606	Intermediate Similarity	NPD6778	Approved
0.7606	Intermediate Similarity	NPD6776	Approved
0.7606	Intermediate Similarity	NPD6782	Approved
0.7606	Intermediate Similarity	NPD6781	Approved
0.7606	Intermediate Similarity	NPD6780	Approved
0.76	Intermediate Similarity	NPD3926	Phase 2
0.7586	Intermediate Similarity	NPD1247	Approved
0.7565	Intermediate Similarity	NPD8151	Discontinued
0.7561	Intermediate Similarity	NPD4628	Phase 3
0.7558	Intermediate Similarity	NPD7768	Phase 2
0.7532	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD7240	Approved
0.7487	Intermediate Similarity	NPD7435	Discontinued
0.7469	Intermediate Similarity	NPD3748	Approved
0.7423	Intermediate Similarity	NPD2935	Discontinued
0.7403	Intermediate Similarity	NPD1091	Approved
0.7398	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7783	Phase 2
0.7396	Intermediate Similarity	NPD7698	Approved
0.7396	Intermediate Similarity	NPD7696	Phase 3
0.7396	Intermediate Similarity	NPD7697	Approved
0.7394	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2534	Approved
0.7381	Intermediate Similarity	NPD2533	Approved
0.7381	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2532	Approved
0.7362	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7870	Phase 2
0.7358	Intermediate Similarity	NPD7871	Phase 2
0.7354	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6823	Phase 2
0.734	Intermediate Similarity	NPD6534	Approved
0.734	Intermediate Similarity	NPD6535	Approved
0.7333	Intermediate Similarity	NPD7701	Phase 2
0.7333	Intermediate Similarity	NPD7585	Approved
0.733	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD920	Approved
0.7289	Intermediate Similarity	NPD2800	Approved
0.7289	Intermediate Similarity	NPD6674	Discontinued
0.7282	Intermediate Similarity	NPD7583	Approved
0.7278	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7874	Approved
0.7259	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7033	Discontinued
0.7253	Intermediate Similarity	NPD5953	Discontinued
0.7249	Intermediate Similarity	NPD4360	Phase 2
0.7249	Intermediate Similarity	NPD4363	Phase 3
0.7233	Intermediate Similarity	NPD9494	Approved
0.7225	Intermediate Similarity	NPD7700	Phase 2
0.7225	Intermediate Similarity	NPD7699	Phase 2
0.7222	Intermediate Similarity	NPD7801	Approved
0.7215	Intermediate Similarity	NPD1203	Approved
0.7212	Intermediate Similarity	NPD6099	Approved
0.7212	Intermediate Similarity	NPD6100	Approved
0.7209	Intermediate Similarity	NPD7458	Discontinued
0.7209	Intermediate Similarity	NPD3226	Approved
0.7205	Intermediate Similarity	NPD2313	Discontinued
0.7197	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6832	Phase 2
0.7188	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4908	Phase 1
0.7186	Intermediate Similarity	NPD1243	Approved
0.7186	Intermediate Similarity	NPD1652	Phase 2
0.7184	Intermediate Similarity	NPD6844	Discontinued
0.7179	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2798	Approved
0.7143	Intermediate Similarity	NPD7286	Phase 2
0.7143	Intermediate Similarity	NPD1548	Phase 1
0.7134	Intermediate Similarity	NPD6651	Approved
0.7128	Intermediate Similarity	NPD7680	Approved
0.7118	Intermediate Similarity	NPD7390	Discontinued
0.7112	Intermediate Similarity	NPD8434	Phase 2
0.7112	Intermediate Similarity	NPD8150	Discontinued
0.711	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6212	Phase 3
0.7105	Intermediate Similarity	NPD6213	Phase 3
0.7102	Intermediate Similarity	NPD5353	Approved
0.7099	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD8319	Approved
0.7092	Intermediate Similarity	NPD8320	Phase 1
0.7073	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5124	Phase 1
0.7072	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1610	Phase 2
0.7066	Intermediate Similarity	NPD2344	Approved
0.7066	Intermediate Similarity	NPD2346	Discontinued
0.7048	Intermediate Similarity	NPD2799	Discontinued
0.7044	Intermediate Similarity	NPD3225	Approved
0.7041	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD9269	Phase 2
0.7017	Intermediate Similarity	NPD5242	Approved
0.7	Intermediate Similarity	NPD8127	Discontinued
0.6994	Remote Similarity	NPD3268	Approved
0.6994	Remote Similarity	NPD6798	Discontinued
0.699	Remote Similarity	NPD5006	Approved
0.699	Remote Similarity	NPD5005	Approved
0.6984	Remote Similarity	NPD6842	Approved
0.6984	Remote Similarity	NPD6841	Approved
0.6984	Remote Similarity	NPD6843	Phase 3
0.6977	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD422	Phase 1
0.6961	Remote Similarity	NPD5710	Approved
0.6961	Remote Similarity	NPD5711	Approved
0.6951	Remote Similarity	NPD6233	Phase 2
0.6946	Remote Similarity	NPD1509	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data