NPASS Compound

Structure

CID78734 OpenBabel06191715412D 42 46 0 0 1 0 0 0 0 0999 V2000 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 0.5000 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 -6.9282 -1.0000 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 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 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 -9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 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 -3.4641 -0.0000 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 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 1 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 2 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 -0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 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 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 -4.3301 -2.5000 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 0.0000 -1.0000 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 0.0000 0.0000 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 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 9 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 5 14 2 0 0 0 0 6 13 2 0 0 0 0 6 15 1 0 0 0 0 7 28 1 0 0 0 0 8 1 1 6 0 0 0 8 19 1 0 0 0 0 8 39 1 0 0 0 0 9 14 1 0 0 0 0 10 11 2 0 0 0 0 10 29 1 0 0 0 0 11 30 1 0 0 0 0 12 17 1 0 0 0 0 12 31 2 0 0 0 0 13 18 1 0 0 0 0 13 32 1 0 0 0 0 14 40 1 0 0 0 0 15 17 2 0 0 0 0 15 40 1 0 0 0 0 16 7 1 1 0 0 0 16 20 1 0 0 0 0 16 41 1 0 0 0 0 17 21 1 0 0 0 0 18 21 2 0 0 0 0 19 22 1 0 0 0 0 19 33 1 1 0 0 0 20 23 1 0 0 0 0 20 34 1 6 0 0 0 21 35 1 0 0 0 0 22 24 1 0 0 0 0 22 36 1 6 0 0 0 23 26 1 0 0 0 0 23 37 1 1 0 0 0 24 27 1 0 0 0 0 24 38 1 6 0 0 0 25 18 1 1 0 0 0 25 26 1 0 0 0 0 25 41 1 0 0 0 0 26 42 1 6 0 0 0 27 39 1 0 0 0 0 27 42 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.16
Volume:	543.527
LogP:	0.385
LogD:	-0.249
LogS:	-3.131
# Rotatable Bonds:	5
TPSA:	260.2
# H-Bond Aceptor:	15
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.153
Synthetic Accessibility Score:	4.822
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.424
MDCK Permeability:	1.247993714059703e-05
Pgp-inhibitor:	0.032
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.976
20% Bioavailability (F20%):	0.288
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	87.03007507324219%
Volume Distribution (VD):	0.608
Pgp-substrate:	18.04615020751953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.038
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.151
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.005

ADMET: Excretion

Clearance (CL):	1.888
Half-life (T1/2):	0.686

ADMET: Toxicity

hERG Blockers:	0.297
Human Hepatotoxicity (H-HT):	0.173
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.78
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.923
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.305
Respiratory Toxicity:	0.055

Download Data

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

Natural Product: NPC78734

Natural Product ID:	NPC78734
*Common Name:**	2''-O-Rhamnosylisoorietin
IUPAC Name:	6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
Synonyms:	2'-O-Rhamnosylisoorietin
Standard InCHIKey:	IUYFTHKQEWZTHY-QMVGNYJJSA-N
Standard InCHI:	InChI=1S/C27H30O15/c1-8-19(33)22(36)24(38)27(39-8)42-26-23(37)20(34)16(7-28)41-25(26)18-13(32)6-15-17(21(18)35)12(31)5-14(40-15)9-2-3-10(29)11(30)4-9/h2-6,8,16,19-20,22-30,32-38H,7H2,1H3/t8-,16+,19-,20+,22+,23-,24+,25-,26+,27-/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1c1c(cc2c(c(=O)cc(c3ccc(c(c3)O)O)o2)c1O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651280
PubChem CID:	50993776
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001737] Flavonoid C-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
NPO30102	Petrorhagia velutina	Species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[21080643]
NPO30102	Petrorhagia velutina	Species	Caryophyllaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21080643]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	74.9	%	PMID[528163]

☑ 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 NPC78734 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	444
0.1-0.2	1824
0.2-0.3	3992
0.3-0.4	9579
0.4-0.5	8636
0.5-0.6	4531
0.6-0.7	5399
0.7-0.8	5287
0.8-0.85	1868
0.85-0.9	659
0.9-0.95	406
0.95-1	72

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC150767
0.9938	High Similarity	NPC256760
0.9876	High Similarity	NPC208668
0.9875	High Similarity	NPC218488
0.9815	High Similarity	NPC294629
0.9811	High Similarity	NPC115674
0.9811	High Similarity	NPC210073
0.9753	High Similarity	NPC25724
0.9752	High Similarity	NPC51326
0.9752	High Similarity	NPC231194
0.975	High Similarity	NPC477502
0.9689	High Similarity	NPC43587
0.9689	High Similarity	NPC209296
0.9689	High Similarity	NPC195257
0.9688	High Similarity	NPC5778
0.9688	High Similarity	NPC236934
0.9688	High Similarity	NPC8856
0.9686	High Similarity	NPC29830
0.9686	High Similarity	NPC19709
0.9634	High Similarity	NPC255799
0.963	High Similarity	NPC44328
0.963	High Similarity	NPC67105
0.963	High Similarity	NPC105095
0.963	High Similarity	NPC95866
0.963	High Similarity	NPC79056
0.963	High Similarity	NPC177731
0.9627	High Similarity	NPC229729
0.9625	High Similarity	NPC311830
0.9625	High Similarity	NPC22832
0.9623	High Similarity	NPC77660
0.9623	High Similarity	NPC189142
0.9623	High Similarity	NPC473043
0.9623	High Similarity	NPC44947
0.9623	High Similarity	NPC300537
0.9623	High Similarity	NPC127782
0.9571	High Similarity	NPC176740
0.9571	High Similarity	NPC155877
0.9571	High Similarity	NPC301683
0.9571	High Similarity	NPC471725
0.9571	High Similarity	NPC134532
0.9571	High Similarity	NPC203259
0.9571	High Similarity	NPC33054
0.9571	High Similarity	NPC471748
0.9568	High Similarity	NPC86008
0.9568	High Similarity	NPC52382
0.9568	High Similarity	NPC229687
0.9568	High Similarity	NPC293629
0.9568	High Similarity	NPC270578
0.9568	High Similarity	NPC105283
0.9568	High Similarity	NPC227508
0.9563	High Similarity	NPC88023
0.9563	High Similarity	NPC222936
0.9563	High Similarity	NPC124155
0.9563	High Similarity	NPC257566
0.9563	High Similarity	NPC270335
0.9563	High Similarity	NPC243930
0.9563	High Similarity	NPC284960
0.9563	High Similarity	NPC168822
0.9563	High Similarity	NPC309025
0.9563	High Similarity	NPC191306
0.956	High Similarity	NPC47923
0.9512	High Similarity	NPC204693
0.9512	High Similarity	NPC51774
0.9512	High Similarity	NPC239549
0.9512	High Similarity	NPC236191
0.9509	High Similarity	NPC255157
0.9509	High Similarity	NPC285197
0.9509	High Similarity	NPC254855
0.9509	High Similarity	NPC67326
0.9509	High Similarity	NPC29958
0.9509	High Similarity	NPC259896
0.9509	High Similarity	NPC156869
0.9509	High Similarity	NPC183357
0.9509	High Similarity	NPC22195
0.9509	High Similarity	NPC21190
0.9509	High Similarity	NPC136042
0.9506	High Similarity	NPC223424
0.9506	High Similarity	NPC52550
0.9506	High Similarity	NPC160156
0.9506	High Similarity	NPC92565
0.9506	High Similarity	NPC275454
0.9506	High Similarity	NPC317489
0.9506	High Similarity	NPC127546
0.9506	High Similarity	NPC173637
0.9506	High Similarity	NPC45400
0.9506	High Similarity	NPC84362
0.9503	High Similarity	NPC475366
0.9503	High Similarity	NPC277205
0.9503	High Similarity	NPC475497
0.9503	High Similarity	NPC284277
0.9464	High Similarity	NPC148710
0.9458	High Similarity	NPC168584
0.9455	High Similarity	NPC294815
0.9455	High Similarity	NPC220173
0.9455	High Similarity	NPC19108
0.9455	High Similarity	NPC16194
0.9455	High Similarity	NPC473327
0.9455	High Similarity	NPC198199
0.9455	High Similarity	NPC108202
0.9455	High Similarity	NPC472607
0.9455	High Similarity	NPC476472
0.9451	High Similarity	NPC235575
0.9451	High Similarity	NPC3583
0.9451	High Similarity	NPC261254
0.9451	High Similarity	NPC307518
0.9451	High Similarity	NPC267254
0.9451	High Similarity	NPC180918
0.9451	High Similarity	NPC60735
0.9451	High Similarity	NPC259152
0.9451	High Similarity	NPC47140
0.9451	High Similarity	NPC48773
0.9451	High Similarity	NPC26230
0.9451	High Similarity	NPC67134
0.9451	High Similarity	NPC205076
0.9448	High Similarity	NPC472383
0.9448	High Similarity	NPC226294
0.9448	High Similarity	NPC112755
0.9448	High Similarity	NPC203050
0.9448	High Similarity	NPC219904
0.9448	High Similarity	NPC58053
0.9448	High Similarity	NPC186807
0.9448	High Similarity	NPC475942
0.9448	High Similarity	NPC471457
0.9448	High Similarity	NPC105025
0.9448	High Similarity	NPC223747
0.9448	High Similarity	NPC472381
0.9448	High Similarity	NPC469931
0.9448	High Similarity	NPC210042
0.9448	High Similarity	NPC45638
0.9448	High Similarity	NPC95855
0.9448	High Similarity	NPC170675
0.9448	High Similarity	NPC120099
0.9448	High Similarity	NPC225434
0.9448	High Similarity	NPC201292
0.9448	High Similarity	NPC93337
0.9444	High Similarity	NPC56077
0.9444	High Similarity	NPC197285
0.9444	High Similarity	NPC145038
0.9444	High Similarity	NPC281131
0.9444	High Similarity	NPC179950
0.9444	High Similarity	NPC21100
0.9444	High Similarity	NPC253662
0.9444	High Similarity	NPC328940
0.9444	High Similarity	NPC274618
0.9444	High Similarity	NPC135599
0.9444	High Similarity	NPC113968
0.9444	High Similarity	NPC276222
0.9444	High Similarity	NPC277174
0.9444	High Similarity	NPC308404
0.9444	High Similarity	NPC73855
0.9444	High Similarity	NPC88789
0.9444	High Similarity	NPC118284
0.9437	High Similarity	NPC303913
0.9437	High Similarity	NPC26326
0.9437	High Similarity	NPC182045
0.9434	High Similarity	NPC117418
0.9434	High Similarity	NPC53545
0.9405	High Similarity	NPC132111
0.9398	High Similarity	NPC292019
0.9398	High Similarity	NPC169733
0.9398	High Similarity	NPC470949
0.9398	High Similarity	NPC14187
0.9398	High Similarity	NPC122467
0.9398	High Similarity	NPC471669
0.9398	High Similarity	NPC202908
0.9398	High Similarity	NPC89127
0.9398	High Similarity	NPC65563
0.9394	High Similarity	NPC472993
0.939	High Similarity	NPC44558
0.939	High Similarity	NPC116864
0.939	High Similarity	NPC105511
0.939	High Similarity	NPC471416
0.939	High Similarity	NPC474434
0.939	High Similarity	NPC34287
0.939	High Similarity	NPC206123
0.939	High Similarity	NPC244776
0.939	High Similarity	NPC224462
0.9387	High Similarity	NPC226304
0.9387	High Similarity	NPC325555
0.9387	High Similarity	NPC93099
0.9387	High Similarity	NPC58716
0.9387	High Similarity	NPC45618
0.9387	High Similarity	NPC265530
0.9387	High Similarity	NPC146792
0.9383	High Similarity	NPC165720
0.9383	High Similarity	NPC470773
0.9383	High Similarity	NPC19388
0.9383	High Similarity	NPC55786
0.9383	High Similarity	NPC15358
0.9383	High Similarity	NPC240431
0.9379	High Similarity	NPC190450
0.9379	High Similarity	NPC259834
0.9379	High Similarity	NPC131745
0.9375	High Similarity	NPC472320
0.9375	High Similarity	NPC110349
0.9371	High Similarity	NPC129827
0.9371	High Similarity	NPC65003
0.9371	High Similarity	NPC473512
0.9371	High Similarity	NPC44931
0.9353	High Similarity	NPC64755

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 NPC78734 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	945
0.2-0.3	1908
0.3-0.4	2743
0.4-0.5	1841
0.5-0.6	881
0.6-0.7	271
0.7-0.8	123
0.8-0.85	24
0.85-0.9	6
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9689	High Similarity	NPD7054	Approved
0.963	High Similarity	NPD7074	Phase 3
0.963	High Similarity	NPD7472	Approved
0.9571	High Similarity	NPD6797	Phase 2
0.9512	High Similarity	NPD7251	Discontinued
0.9337	High Similarity	NPD7808	Phase 3
0.9329	High Similarity	NPD7804	Clinical (unspecified phase)
0.9268	High Similarity	NPD3818	Discontinued
0.925	High Similarity	NPD4381	Clinical (unspecified phase)
0.9182	High Similarity	NPD2393	Clinical (unspecified phase)
0.9146	High Similarity	NPD6166	Phase 2
0.9146	High Similarity	NPD6168	Clinical (unspecified phase)
0.9146	High Similarity	NPD6167	Clinical (unspecified phase)
0.9107	High Similarity	NPD4338	Clinical (unspecified phase)
0.9	High Similarity	NPD1934	Approved
0.8875	High Similarity	NPD4380	Phase 2
0.8713	High Similarity	NPD6559	Discontinued
0.8712	High Similarity	NPD2801	Approved
0.8616	High Similarity	NPD1511	Approved
0.8606	High Similarity	NPD4868	Clinical (unspecified phase)
0.8554	High Similarity	NPD7075	Discontinued
0.8545	High Similarity	NPD3817	Phase 2
0.8509	High Similarity	NPD1512	Approved
0.8452	Intermediate Similarity	NPD5494	Approved
0.8447	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8439	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD6801	Discontinued
0.8402	Intermediate Similarity	NPD6959	Discontinued
0.8383	Intermediate Similarity	NPD3882	Suspended
0.8373	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7819	Suspended
0.8253	Intermediate Similarity	NPD7411	Suspended
0.8239	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD5844	Phase 1
0.8192	Intermediate Similarity	NPD8312	Approved
0.8192	Intermediate Similarity	NPD8313	Approved
0.8187	Intermediate Similarity	NPD1549	Phase 2
0.8177	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7228	Approved
0.814	Intermediate Similarity	NPD6232	Discontinued
0.8107	Intermediate Similarity	NPD5402	Approved
0.8103	Intermediate Similarity	NPD7473	Discontinued
0.8072	Intermediate Similarity	NPD1653	Approved
0.8063	Intermediate Similarity	NPD2796	Approved
0.8047	Intermediate Similarity	NPD1465	Phase 2
0.8046	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD1510	Phase 2
0.7967	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD8455	Phase 2
0.7939	Intermediate Similarity	NPD6799	Approved
0.7917	Intermediate Similarity	NPD8151	Discontinued
0.7906	Intermediate Similarity	NPD7584	Approved
0.7904	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD5401	Approved
0.7877	Intermediate Similarity	NPD7685	Pre-registration
0.7874	Intermediate Similarity	NPD7199	Phase 2
0.7872	Intermediate Similarity	NPD6778	Approved
0.7872	Intermediate Similarity	NPD6781	Approved
0.7872	Intermediate Similarity	NPD6777	Approved
0.7872	Intermediate Similarity	NPD6782	Approved
0.7872	Intermediate Similarity	NPD6779	Approved
0.7872	Intermediate Similarity	NPD6780	Approved
0.7872	Intermediate Similarity	NPD6776	Approved
0.7862	Intermediate Similarity	NPD1613	Approved
0.7862	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6234	Discontinued
0.7853	Intermediate Similarity	NPD3751	Discontinued
0.7829	Intermediate Similarity	NPD3787	Discontinued
0.7791	Intermediate Similarity	NPD7266	Discontinued
0.7778	Intermediate Similarity	NPD37	Approved
0.7765	Intermediate Similarity	NPD6599	Discontinued
0.7759	Intermediate Similarity	NPD919	Approved
0.775	Intermediate Similarity	NPD1240	Approved
0.7749	Intermediate Similarity	NPD7696	Phase 3
0.7749	Intermediate Similarity	NPD7435	Discontinued
0.7749	Intermediate Similarity	NPD7697	Approved
0.7749	Intermediate Similarity	NPD7698	Approved
0.7746	Intermediate Similarity	NPD7768	Phase 2
0.7746	Intermediate Similarity	NPD4966	Approved
0.7746	Intermediate Similarity	NPD4965	Approved
0.7746	Intermediate Similarity	NPD4967	Phase 2
0.7744	Intermediate Similarity	NPD7783	Phase 2
0.7744	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7240	Approved
0.768	Intermediate Similarity	NPD7701	Phase 2
0.767	Intermediate Similarity	NPD1247	Approved
0.7654	Intermediate Similarity	NPD1607	Approved
0.7651	Intermediate Similarity	NPD3750	Approved
0.7651	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD943	Approved
0.7636	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2935	Discontinued
0.7619	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD7871	Phase 2
0.7617	Intermediate Similarity	NPD7870	Phase 2
0.761	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6534	Approved
0.7606	Intermediate Similarity	NPD6535	Approved
0.7604	Intermediate Similarity	NPD6823	Phase 2
0.759	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD7700	Phase 2
0.7579	Intermediate Similarity	NPD7699	Phase 2
0.7574	Intermediate Similarity	NPD2534	Approved
0.7574	Intermediate Similarity	NPD2532	Approved
0.7574	Intermediate Similarity	NPD2533	Approved
0.7562	Intermediate Similarity	NPD3027	Phase 3
0.7547	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4628	Phase 3
0.7526	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7874	Approved
0.7513	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7585	Approved
0.75	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD3749	Approved
0.7486	Intermediate Similarity	NPD3926	Phase 2
0.7485	Intermediate Similarity	NPD230	Phase 1
0.7485	Intermediate Similarity	NPD2800	Approved
0.7485	Intermediate Similarity	NPD920	Approved
0.7485	Intermediate Similarity	NPD1933	Approved
0.7475	Intermediate Similarity	NPD7801	Approved
0.7449	Intermediate Similarity	NPD7583	Approved
0.7446	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD8319	Approved
0.7436	Intermediate Similarity	NPD8320	Phase 1
0.7432	Intermediate Similarity	NPD5953	Discontinued
0.7421	Intermediate Similarity	NPD4360	Phase 2
0.7421	Intermediate Similarity	NPD4363	Phase 3
0.7412	Intermediate Similarity	NPD7390	Discontinued
0.741	Intermediate Similarity	NPD1551	Phase 2
0.7409	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD3226	Approved
0.7396	Intermediate Similarity	NPD6190	Approved
0.7381	Intermediate Similarity	NPD6674	Discontinued
0.7381	Intermediate Similarity	NPD1243	Approved
0.738	Intermediate Similarity	NPD8150	Discontinued
0.7368	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6212	Phase 3
0.7368	Intermediate Similarity	NPD6213	Phase 3
0.7358	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3748	Approved
0.7333	Intermediate Similarity	NPD6651	Approved
0.7322	Intermediate Similarity	NPD7286	Phase 2
0.7301	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2313	Discontinued
0.7296	Intermediate Similarity	NPD7680	Approved
0.7273	Intermediate Similarity	NPD447	Suspended
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2346	Discontinued
0.7246	Intermediate Similarity	NPD7033	Discontinued
0.7246	Intermediate Similarity	NPD2799	Discontinued
0.7202	Intermediate Similarity	NPD6100	Approved
0.7202	Intermediate Similarity	NPD6099	Approved
0.72	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD8434	Phase 2
0.7178	Intermediate Similarity	NPD4908	Phase 1
0.717	Intermediate Similarity	NPD1091	Approved
0.7168	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2798	Approved
0.715	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5710	Approved
0.7143	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7930	Approved
0.7081	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6844	Discontinued
0.7076	Intermediate Similarity	NPD1652	Phase 2
0.7073	Intermediate Similarity	NPD6832	Phase 2
0.7063	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2344	Approved
0.705	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD4361	Phase 2
0.7018	Intermediate Similarity	NPD2424	Discontinued
0.7012	Intermediate Similarity	NPD9494	Approved
0.6995	Remote Similarity	NPD8127	Discontinued
0.6994	Remote Similarity	NPD1203	Approved
0.6988	Remote Similarity	NPD6798	Discontinued
0.6988	Remote Similarity	NPD3268	Approved
0.6982	Remote Similarity	NPD7097	Phase 1
0.6981	Remote Similarity	NPD8059	Phase 3
0.6981	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1610	Phase 2
0.6957	Remote Similarity	NPD7229	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