NPASS Compound

Structure

NPC67105 OpenBabel07101719252D 43 47 0 0 1 0 0 0 0 0999 V2000 5.1962 1.0000 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 -6.9282 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 -1.7321 -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 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 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 -1.7321 -2.0000 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 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 -0.0000 1.0000 0.0000 C 0 0 2 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 2.5000 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 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 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 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 1 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 -5.1962 -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 1 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 -8.6603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -2.0000 0.0000 O 0 0 0 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 5.1962 3.0000 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 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 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 -6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 1.7321 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 -0.8660 -1.5000 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 -0.0000 -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 11 1 0 0 0 0 4 9 2 0 0 0 0 4 12 1 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 10 1 0 0 0 0 6 14 2 0 0 0 0 7 39 1 0 0 0 0 8 1 1 1 0 0 0 8 17 1 0 0 0 0 8 40 1 0 0 0 0 9 25 1 0 0 0 0 10 41 1 0 0 0 0 11 12 2 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 16 2 0 0 0 0 13 30 1 0 0 0 0 14 16 1 0 0 0 0 14 42 1 0 0 0 0 15 7 1 1 0 0 0 15 18 1 0 0 0 0 15 43 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 17 31 1 6 0 0 0 18 21 1 0 0 0 0 18 32 1 1 0 0 0 19 22 1 0 0 0 0 19 33 2 0 0 0 0 20 23 1 0 0 0 0 20 34 1 1 0 0 0 21 24 1 0 0 0 0 21 35 1 1 0 0 0 22 25 2 0 0 0 0 22 36 1 0 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 42 1 0 0 0 0 26 39 1 6 0 0 0 26 40 1 0 0 0 0 27 41 1 1 0 0 0 27 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	610.15
Volume:	552.318
LogP:	-0.08
LogD:	-0.15
LogS:	-3.515
# Rotatable Bonds:	6
TPSA:	269.43
# H-Bond Aceptor:	16
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.14
Synthetic Accessibility Score:	4.79
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.553
MDCK Permeability:	1.5420482668559998e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.811
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	90.0309066772461%
Volume Distribution (VD):	0.695
Pgp-substrate:	11.296319961547852%

ADMET: Metabolism

CYP1A2-inhibitor:	0.088
CYP1A2-substrate:	0.042
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.056
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	1.161
Half-life (T1/2):	0.707

ADMET: Toxicity

hERG Blockers:	0.382
Human Hepatotoxicity (H-HT):	0.116
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.864
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.85
Carcinogencity:	0.12
Eye Corrosion:	0.003
Eye Irritation:	0.366
Respiratory Toxicity:	0.017

Download Data

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

Natural Product: NPC67105

Natural Product ID:	NPC67105
*Common Name:**	Quercetin-7-O-[R-L-Rhamnopyranosyl(1->6)-Beta-D-Galactopyranoside]
IUPAC Name:	2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	IVTMALDHFAHOGL-OJFLVKRKSA-N
Standard InCHI:	InChI=1S/C27H30O16/c1-8-17(31)20(34)23(37)26(40-8)39-7-15-18(32)21(35)24(38)27(43-15)41-10-5-13(30)16-14(6-10)42-25(22(36)19(16)33)9-2-3-11(28)12(29)4-9/h2-6,8,15,17-18,20-21,23-24,26-32,34-38H,7H2,1H3/t8-,15-,17-,18+,20+,21+,23+,24-,26+,27-/m1/s1
SMILES:	C[C@@H]1[C@H]([C@@H]([C@@H]([C@@H](OC[C@@H]2[C@@H]([C@@H]([C@H]([C@H](Oc3cc(c4c(c3)oc(c3ccc(c(c3)O)O)c(c4=O)O)O)O2)O)O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669715
PubChem CID:	53317755
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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
NPO32611	grevillea "poorinda queen"	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21155593]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	500000.0	nM	PMID[533368]

☑ 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 NPC67105 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	1837
0.2-0.3	4172
0.3-0.4	9736
0.4-0.5	8412
0.5-0.6	4554
0.6-0.7	5480
0.7-0.8	5267
0.8-0.85	1616
0.85-0.9	599
0.9-0.95	440
0.95-1	134

Similarity Score	Similarity Level	Natural Product ID
0.9938	High Similarity	NPC176740
0.9938	High Similarity	NPC33054
0.9938	High Similarity	NPC471748
0.9938	High Similarity	NPC471725
0.9938	High Similarity	NPC155877
0.9938	High Similarity	NPC134532
0.9938	High Similarity	NPC203259
0.9937	High Similarity	NPC227508
0.9875	High Similarity	NPC156869
0.9875	High Similarity	NPC136042
0.9875	High Similarity	NPC285197
0.9875	High Similarity	NPC254855
0.9875	High Similarity	NPC259896
0.9875	High Similarity	NPC255157
0.9875	High Similarity	NPC67326
0.9875	High Similarity	NPC95866
0.9875	High Similarity	NPC29958
0.9874	High Similarity	NPC275454
0.9815	High Similarity	NPC16194
0.9815	High Similarity	NPC476472
0.9815	High Similarity	NPC220173
0.9815	High Similarity	NPC473327
0.9815	High Similarity	NPC294815
0.9815	High Similarity	NPC19108
0.9814	High Similarity	NPC26230
0.9814	High Similarity	NPC60735
0.9811	High Similarity	NPC115674
0.9811	High Similarity	NPC8856
0.9811	High Similarity	NPC210073
0.9755	High Similarity	NPC89127
0.9755	High Similarity	NPC122467
0.9755	High Similarity	NPC470949
0.9755	High Similarity	NPC14187
0.9755	High Similarity	NPC202908
0.9755	High Similarity	NPC292019
0.9755	High Similarity	NPC471669
0.9755	High Similarity	NPC65563
0.9755	High Similarity	NPC169733
0.975	High Similarity	NPC84362
0.975	High Similarity	NPC173637
0.975	High Similarity	NPC52550
0.975	High Similarity	NPC317489
0.975	High Similarity	NPC127546
0.975	High Similarity	NPC223424
0.9748	High Similarity	NPC277205
0.9695	High Similarity	NPC89052
0.9695	High Similarity	NPC173837
0.9695	High Similarity	NPC251417
0.9693	High Similarity	NPC294629
0.9693	High Similarity	NPC253685
0.9689	High Similarity	NPC219904
0.9689	High Similarity	NPC86008
0.9689	High Similarity	NPC52382
0.9689	High Similarity	NPC225434
0.9689	High Similarity	NPC270578
0.9689	High Similarity	NPC209296
0.9689	High Similarity	NPC195257
0.9689	High Similarity	NPC120099
0.9689	High Similarity	NPC203050
0.9689	High Similarity	NPC223747
0.9688	High Similarity	NPC21100
0.9688	High Similarity	NPC145038
0.9688	High Similarity	NPC197285
0.9688	High Similarity	NPC88789
0.9688	High Similarity	NPC274618
0.9688	High Similarity	NPC56077
0.9688	High Similarity	NPC135599
0.9688	High Similarity	NPC113968
0.9688	High Similarity	NPC118284
0.9688	High Similarity	NPC277174
0.9688	High Similarity	NPC179950
0.9688	High Similarity	NPC73855
0.9688	High Similarity	NPC328940
0.9688	High Similarity	NPC281131
0.9688	High Similarity	NPC253662
0.9688	High Similarity	NPC276222
0.9688	High Similarity	NPC308404
0.9686	High Similarity	NPC19709
0.9636	High Similarity	NPC241423
0.9636	High Similarity	NPC192539
0.9636	High Similarity	NPC473682
0.9636	High Similarity	NPC470444
0.9636	High Similarity	NPC470443
0.9636	High Similarity	NPC110941
0.9636	High Similarity	NPC473571
0.9636	High Similarity	NPC126784
0.9634	High Similarity	NPC473862
0.9634	High Similarity	NPC219043
0.9634	High Similarity	NPC48984
0.9634	High Similarity	NPC8573
0.963	High Similarity	NPC218488
0.963	High Similarity	NPC206123
0.963	High Similarity	NPC150767
0.963	High Similarity	NPC231194
0.963	High Similarity	NPC244776
0.963	High Similarity	NPC116864
0.963	High Similarity	NPC78734
0.963	High Similarity	NPC51326
0.9627	High Similarity	NPC92565
0.9627	High Similarity	NPC265530
0.9627	High Similarity	NPC226304
0.9627	High Similarity	NPC325555
0.9627	High Similarity	NPC160156
0.9625	High Similarity	NPC55786
0.9625	High Similarity	NPC19388
0.9625	High Similarity	NPC240431
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
0.9578	High Similarity	NPC473073
0.9578	High Similarity	NPC473071
0.9573	High Similarity	NPC198199
0.9571	High Similarity	NPC180918
0.9571	High Similarity	NPC3583
0.9571	High Similarity	NPC190003
0.9571	High Similarity	NPC175107
0.9571	High Similarity	NPC245452
0.9571	High Similarity	NPC117260
0.9571	High Similarity	NPC259152
0.9571	High Similarity	NPC476405
0.9571	High Similarity	NPC153755
0.9571	High Similarity	NPC256760
0.9568	High Similarity	NPC43587
0.9568	High Similarity	NPC105283
0.9565	High Similarity	NPC236934
0.9565	High Similarity	NPC5778
0.9563	High Similarity	NPC222936
0.9563	High Similarity	NPC270335
0.9563	High Similarity	NPC284960
0.9563	High Similarity	NPC88023
0.9563	High Similarity	NPC243930
0.9563	High Similarity	NPC168822
0.9563	High Similarity	NPC309025
0.9563	High Similarity	NPC29830
0.9563	High Similarity	NPC191306
0.9521	High Similarity	NPC241781
0.9521	High Similarity	NPC162394
0.9521	High Similarity	NPC470445
0.9521	High Similarity	NPC470449
0.9521	High Similarity	NPC470447
0.9521	High Similarity	NPC470446
0.9521	High Similarity	NPC156785
0.9521	High Similarity	NPC473072
0.9512	High Similarity	NPC42773
0.9512	High Similarity	NPC204693
0.9512	High Similarity	NPC101026
0.9512	High Similarity	NPC45522
0.9512	High Similarity	NPC24043
0.9512	High Similarity	NPC25724
0.9512	High Similarity	NPC4390
0.9512	High Similarity	NPC169977
0.9512	High Similarity	NPC21666
0.9512	High Similarity	NPC208668
0.9509	High Similarity	NPC235260
0.9509	High Similarity	NPC20505
0.9509	High Similarity	NPC155763
0.9509	High Similarity	NPC245014
0.9509	High Similarity	NPC177731
0.9509	High Similarity	NPC84265
0.9509	High Similarity	NPC79056
0.9509	High Similarity	NPC105095
0.9509	High Similarity	NPC282987
0.9509	High Similarity	NPC44328
0.9506	High Similarity	NPC229729
0.9503	High Similarity	NPC475366
0.9503	High Similarity	NPC15358
0.9503	High Similarity	NPC475497
0.9503	High Similarity	NPC284277
0.95	High Similarity	NPC300537
0.95	High Similarity	NPC127782
0.9497	High Similarity	NPC136761
0.9497	High Similarity	NPC187379
0.9464	High Similarity	NPC249560
0.9464	High Similarity	NPC470717
0.9464	High Similarity	NPC148710
0.9464	High Similarity	NPC25946
0.9464	High Similarity	NPC460984
0.9464	High Similarity	NPC470720
0.9464	High Similarity	NPC470451
0.9464	High Similarity	NPC223860
0.9464	High Similarity	NPC275977
0.9464	High Similarity	NPC21359
0.9464	High Similarity	NPC470455
0.9464	High Similarity	NPC470713
0.9458	High Similarity	NPC120952
0.9458	High Similarity	NPC258044
0.9458	High Similarity	NPC139571
0.9458	High Similarity	NPC217520
0.9458	High Similarity	NPC35167
0.9458	High Similarity	NPC113836
0.9458	High Similarity	NPC267680
0.9458	High Similarity	NPC293626
0.9458	High Similarity	NPC253521
0.9458	High Similarity	NPC217387
0.9458	High Similarity	NPC37668
0.9458	High Similarity	NPC196127
0.9455	High Similarity	NPC223426
0.9455	High Similarity	NPC81042

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 NPC67105 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	402
0.1-0.2	947
0.2-0.3	1976
0.3-0.4	2733
0.4-0.5	1812
0.5-0.6	860
0.6-0.7	280
0.7-0.8	108
0.8-0.85	18
0.85-0.9	6
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9938	High Similarity	NPD6797	Phase 2
0.9876	High Similarity	NPD7251	Discontinued
0.9752	High Similarity	NPD7472	Approved
0.9693	High Similarity	NPD7808	Phase 3
0.9689	High Similarity	NPD7054	Approved
0.9509	High Similarity	NPD7074	Phase 3
0.9337	High Similarity	NPD4338	Clinical (unspecified phase)
0.9264	High Similarity	NPD6167	Clinical (unspecified phase)
0.9264	High Similarity	NPD6166	Phase 2
0.9264	High Similarity	NPD6168	Clinical (unspecified phase)
0.9212	High Similarity	NPD7804	Clinical (unspecified phase)
0.9152	High Similarity	NPD3818	Discontinued
0.913	High Similarity	NPD4381	Clinical (unspecified phase)
0.8882	High Similarity	NPD1934	Approved
0.8827	High Similarity	NPD2393	Clinical (unspecified phase)
0.8773	High Similarity	NPD3817	Phase 2
0.8742	High Similarity	NPD1512	Approved
0.8712	High Similarity	NPD2801	Approved
0.8655	High Similarity	NPD7993	Clinical (unspecified phase)
0.8616	High Similarity	NPD1511	Approved
0.8606	High Similarity	NPD3882	Suspended
0.8528	High Similarity	NPD4380	Phase 2
0.8494	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD7075	Discontinued
0.8391	Intermediate Similarity	NPD6559	Discontinued
0.8333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD5402	Approved
0.8313	Intermediate Similarity	NPD6801	Discontinued
0.8263	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD5403	Approved
0.816	Intermediate Similarity	NPD6799	Approved
0.8129	Intermediate Similarity	NPD5494	Approved
0.8125	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD5401	Approved
0.8081	Intermediate Similarity	NPD6959	Discontinued
0.8077	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD1549	Phase 2
0.8072	Intermediate Similarity	NPD1653	Approved
0.8057	Intermediate Similarity	NPD3751	Discontinued
0.8035	Intermediate Similarity	NPD3787	Discontinued
0.8	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD8313	Approved
0.7989	Intermediate Similarity	NPD8312	Approved
0.7955	Intermediate Similarity	NPD7228	Approved
0.795	Intermediate Similarity	NPD2796	Approved
0.7941	Intermediate Similarity	NPD7819	Suspended
0.7941	Intermediate Similarity	NPD1465	Phase 2
0.7929	Intermediate Similarity	NPD7411	Suspended
0.791	Intermediate Similarity	NPD5844	Phase 1
0.7892	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD1510	Phase 2
0.7877	Intermediate Similarity	NPD7685	Pre-registration
0.787	Intermediate Similarity	NPD6599	Discontinued
0.7829	Intermediate Similarity	NPD6232	Discontinued
0.7798	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7473	Discontinued
0.7791	Intermediate Similarity	NPD7266	Discontinued
0.7784	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6777	Approved
0.7778	Intermediate Similarity	NPD6776	Approved
0.7778	Intermediate Similarity	NPD6779	Approved
0.7778	Intermediate Similarity	NPD6778	Approved
0.7778	Intermediate Similarity	NPD6781	Approved
0.7778	Intermediate Similarity	NPD6782	Approved
0.7778	Intermediate Similarity	NPD6780	Approved
0.7771	Intermediate Similarity	NPD7199	Phase 2
0.775	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1613	Approved
0.774	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD8455	Phase 2
0.7732	Intermediate Similarity	NPD8151	Discontinued
0.7705	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD6234	Discontinued
0.7657	Intermediate Similarity	NPD919	Approved
0.7656	Intermediate Similarity	NPD7698	Approved
0.7656	Intermediate Similarity	NPD7697	Approved
0.7656	Intermediate Similarity	NPD7435	Discontinued
0.7656	Intermediate Similarity	NPD7696	Phase 3
0.7651	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1240	Approved
0.7636	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD7584	Approved
0.7605	Intermediate Similarity	NPD6190	Approved
0.759	Intermediate Similarity	NPD7701	Phase 2
0.7584	Intermediate Similarity	NPD3926	Phase 2
0.7582	Intermediate Similarity	NPD7240	Approved
0.7572	Intermediate Similarity	NPD37	Approved
0.7571	Intermediate Similarity	NPD1247	Approved
0.7546	Intermediate Similarity	NPD1607	Approved
0.7545	Intermediate Similarity	NPD3750	Approved
0.7543	Intermediate Similarity	NPD4965	Approved
0.7543	Intermediate Similarity	NPD4966	Approved
0.7543	Intermediate Similarity	NPD4967	Phase 2
0.7531	Intermediate Similarity	NPD943	Approved
0.7526	Intermediate Similarity	NPD7871	Phase 2
0.7526	Intermediate Similarity	NPD7870	Phase 2
0.7515	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD6535	Approved
0.7513	Intermediate Similarity	NPD6534	Approved
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7699	Phase 2
0.7487	Intermediate Similarity	NPD7700	Phase 2
0.7485	Intermediate Similarity	NPD230	Phase 1
0.7485	Intermediate Similarity	NPD1933	Approved
0.7475	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7783	Phase 2
0.7453	Intermediate Similarity	NPD3027	Phase 3
0.7443	Intermediate Similarity	NPD7768	Phase 2
0.744	Intermediate Similarity	NPD4628	Phase 3
0.7438	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD7874	Approved
0.7424	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1551	Phase 2
0.7407	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD3749	Approved
0.7387	Intermediate Similarity	NPD7801	Approved
0.7349	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD8319	Approved
0.7347	Intermediate Similarity	NPD8320	Phase 1
0.7333	Intermediate Similarity	NPD6823	Phase 2
0.7305	Intermediate Similarity	NPD2935	Discontinued
0.7287	Intermediate Similarity	NPD8150	Discontinued
0.7287	Intermediate Similarity	NPD8434	Phase 2
0.7278	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD447	Suspended
0.7267	Intermediate Similarity	NPD2534	Approved
0.7267	Intermediate Similarity	NPD2532	Approved
0.7267	Intermediate Similarity	NPD2533	Approved
0.7246	Intermediate Similarity	NPD3748	Approved
0.7236	Intermediate Similarity	NPD7585	Approved
0.72	Intermediate Similarity	NPD7458	Discontinued
0.7186	Intermediate Similarity	NPD7583	Approved
0.7184	Intermediate Similarity	NPD920	Approved
0.7179	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2800	Approved
0.717	Intermediate Similarity	NPD1091	Approved
0.7168	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5953	Discontinued
0.715	Intermediate Similarity	NPD4363	Phase 3
0.715	Intermediate Similarity	NPD4360	Phase 2
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7680	Approved
0.711	Intermediate Similarity	NPD7390	Discontinued
0.7102	Intermediate Similarity	NPD3226	Approved
0.7101	Intermediate Similarity	NPD6100	Approved
0.7101	Intermediate Similarity	NPD6099	Approved
0.7098	Intermediate Similarity	NPD6213	Phase 3
0.7098	Intermediate Similarity	NPD6212	Phase 3
0.7098	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6798	Discontinued
0.7081	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6844	Discontinued
0.7076	Intermediate Similarity	NPD6674	Discontinued
0.7076	Intermediate Similarity	NPD1652	Phase 2
0.7076	Intermediate Similarity	NPD1243	Approved
0.7073	Intermediate Similarity	NPD4908	Phase 1
0.7073	Intermediate Similarity	NPD6832	Phase 2
0.7069	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2798	Approved
0.7052	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6233	Phase 2
0.7043	Intermediate Similarity	NPD7286	Phase 2
0.7024	Intermediate Similarity	NPD6651	Approved
0.7012	Intermediate Similarity	NPD9494	Approved
0.6994	Remote Similarity	NPD1203	Approved
0.6988	Remote Similarity	NPD2313	Discontinued
0.6988	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6355	Discontinued
0.6964	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5124	Phase 1
0.6959	Remote Similarity	NPD2346	Discontinued
0.6959	Remote Similarity	NPD2344	Approved
0.6957	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2799	Discontinued
0.6936	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1548	Phase 1
0.691	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5353	Approved
0.6886	Remote Similarity	NPD3268	Approved
0.6875	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD5711	Approved
0.6865	Remote Similarity	NPD5710	Approved
0.686	Remote Similarity	NPD7930	Approved
0.6852	Remote Similarity	NPD1610	Phase 2
0.6852	Remote Similarity	NPD422	Phase 1
0.6842	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3225	Approved
0.6828	Remote Similarity	NPD5242	Approved
0.6816	Remote Similarity	NPD5006	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