NPASS Compound

Structure

NPC227508 OpenBabel07101718232D 44 48 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 6.9282 2.0000 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 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 1 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 2.5981 3.5000 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 -0.0000 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 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 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 0.8660 -1.5000 0.0000 C 0 0 2 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 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 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 2 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 2 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 4.5000 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 6.9282 -1.0000 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 8.6603 0.0000 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 8 2 0 0 0 0 2 11 1 0 0 0 0 3 8 1 0 0 0 0 3 12 2 0 0 0 0 4 9 2 0 0 0 0 4 10 1 0 0 0 0 5 9 1 0 0 0 0 5 13 2 0 0 0 0 6 40 1 0 0 0 0 7 1 1 6 0 0 0 7 16 1 0 0 0 0 7 41 1 0 0 0 0 8 25 1 0 0 0 0 9 42 1 0 0 0 0 10 15 2 0 0 0 0 10 28 1 0 0 0 0 11 17 2 0 0 0 0 11 29 1 0 0 0 0 12 17 1 0 0 0 0 12 30 1 0 0 0 0 13 15 1 0 0 0 0 13 43 1 0 0 0 0 14 6 1 1 0 0 0 14 18 1 0 0 0 0 14 44 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 16 31 1 1 0 0 0 17 32 1 0 0 0 0 18 21 1 0 0 0 0 18 33 1 6 0 0 0 19 22 1 0 0 0 0 19 34 2 0 0 0 0 20 23 1 0 0 0 0 20 35 1 6 0 0 0 21 24 1 0 0 0 0 21 36 1 1 0 0 0 22 25 2 0 0 0 0 22 37 1 0 0 0 0 23 26 1 0 0 0 0 23 38 1 6 0 0 0 24 27 1 0 0 0 0 24 39 1 6 0 0 0 25 43 1 0 0 0 0 26 40 1 1 0 0 0 26 41 1 0 0 0 0 27 42 1 1 0 0 0 27 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	626.15
Volume:	561.108
LogP:	-0.142
LogD:	-0.356
LogS:	-2.51
# Rotatable Bonds:	6
TPSA:	289.66
# H-Bond Aceptor:	17
# H-Bond Donor:	11
# Rings:	5
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.132
Synthetic Accessibility Score:	4.904
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.604
MDCK Permeability:	1.8808905224432237e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.921
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	88.6240005493164%
Volume Distribution (VD):	0.661
Pgp-substrate:	17.21441078186035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.103
CYP1A2-substrate:	0.036
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	1.288
Half-life (T1/2):	0.79

ADMET: Toxicity

hERG Blockers:	0.307
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.855
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.944
Carcinogencity:	0.068
Eye Corrosion:	0.003
Eye Irritation:	0.585
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC227508

Natural Product ID:	NPC227508
*Common Name:**	Myricetin 7-O-Alpha-L-Rhamnopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name:	3,5-dihydroxy-2-(3,4,5-trihydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	MASOGOGVWNFCIB-YCAHXHNPSA-N
Standard InCHI:	InChI=1S/C27H30O17/c1-7-16(31)20(35)23(38)26(41-7)40-6-14-18(33)21(36)24(39)27(44-14)42-9-4-10(28)15-13(5-9)43-25(22(37)19(15)34)8-2-11(29)17(32)12(30)3-8/h2-5,7,14,16,18,20-21,23-24,26-33,35-39H,6H2,1H3/t7-,14+,16-,18+,20+,21-,23+,24+,26+,27+/m0/s1
SMILES:	O[C@H]1[C@@H](O[C@@H]([C@H]([C@@H]1O)O)CO[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)Oc1cc(O)c2c(c1)oc(c(c2=O)O)c1cc(O)c(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451090
PubChem CID:	10031889
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
NPO11248	Tachigalia paniculata	n.a.	n.a.	n.a.	leaves	n.a.	n.a.	PMID[12444671]
NPO11248	Tachigalia paniculata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		Activity	=	1.42	mM	PMID[533204]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	IC50	=	6130.0	nM	PMID[533204]

☑ 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 NPC227508 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	458
0.1-0.2	1887
0.2-0.3	4287
0.3-0.4	9837
0.4-0.5	8347
0.5-0.6	4622
0.6-0.7	5600
0.7-0.8	5116
0.8-0.85	1519
0.85-0.9	511
0.9-0.95	405
0.95-1	108

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC275454
0.9937	High Similarity	NPC67105
0.9875	High Similarity	NPC471748
0.9875	High Similarity	NPC134532
0.9875	High Similarity	NPC203259
0.9875	High Similarity	NPC33054
0.9875	High Similarity	NPC176740
0.9875	High Similarity	NPC471725
0.9875	High Similarity	NPC155877
0.9812	High Similarity	NPC67326
0.9812	High Similarity	NPC136042
0.9812	High Similarity	NPC285197
0.9812	High Similarity	NPC95866
0.9812	High Similarity	NPC254855
0.9812	High Similarity	NPC259896
0.9812	High Similarity	NPC156869
0.9812	High Similarity	NPC29958
0.9812	High Similarity	NPC255157
0.9753	High Similarity	NPC294815
0.9753	High Similarity	NPC220173
0.9753	High Similarity	NPC19108
0.9753	High Similarity	NPC476472
0.9753	High Similarity	NPC16194
0.9753	High Similarity	NPC473327
0.9752	High Similarity	NPC26230
0.9752	High Similarity	NPC60735
0.9748	High Similarity	NPC8856
0.9748	High Similarity	NPC113968
0.9748	High Similarity	NPC115674
0.9748	High Similarity	NPC210073
0.9748	High Similarity	NPC135599
0.9748	High Similarity	NPC277174
0.9748	High Similarity	NPC73855
0.9748	High Similarity	NPC328940
0.9693	High Similarity	NPC470949
0.9693	High Similarity	NPC122467
0.9693	High Similarity	NPC292019
0.9693	High Similarity	NPC89127
0.9693	High Similarity	NPC471669
0.9693	High Similarity	NPC202908
0.9693	High Similarity	NPC65563
0.9693	High Similarity	NPC14187
0.9693	High Similarity	NPC169733
0.9688	High Similarity	NPC265530
0.9688	High Similarity	NPC173637
0.9688	High Similarity	NPC127546
0.9688	High Similarity	NPC52550
0.9688	High Similarity	NPC226304
0.9688	High Similarity	NPC325555
0.9688	High Similarity	NPC84362
0.9688	High Similarity	NPC223424
0.9688	High Similarity	NPC317489
0.9686	High Similarity	NPC19388
0.9686	High Similarity	NPC277205
0.9686	High Similarity	NPC55786
0.9686	High Similarity	NPC240431
0.9684	High Similarity	NPC473043
0.9634	High Similarity	NPC89052
0.9634	High Similarity	NPC173837
0.9634	High Similarity	NPC251417
0.9632	High Similarity	NPC294629
0.9632	High Similarity	NPC253685
0.9627	High Similarity	NPC52382
0.9627	High Similarity	NPC195257
0.9627	High Similarity	NPC219904
0.9627	High Similarity	NPC223747
0.9627	High Similarity	NPC86008
0.9627	High Similarity	NPC120099
0.9627	High Similarity	NPC209296
0.9627	High Similarity	NPC270578
0.9627	High Similarity	NPC225434
0.9627	High Similarity	NPC203050
0.9625	High Similarity	NPC88789
0.9625	High Similarity	NPC145038
0.9625	High Similarity	NPC197285
0.9625	High Similarity	NPC274618
0.9625	High Similarity	NPC276222
0.9625	High Similarity	NPC253662
0.9625	High Similarity	NPC179950
0.9625	High Similarity	NPC118284
0.9625	High Similarity	NPC21100
0.9625	High Similarity	NPC281131
0.9625	High Similarity	NPC308404
0.9625	High Similarity	NPC56077
0.9623	High Similarity	NPC284960
0.9623	High Similarity	NPC19709
0.9623	High Similarity	NPC222936
0.9576	High Similarity	NPC126784
0.9576	High Similarity	NPC470444
0.9576	High Similarity	NPC473571
0.9576	High Similarity	NPC470443
0.9576	High Similarity	NPC241423
0.9576	High Similarity	NPC110941
0.9576	High Similarity	NPC192539
0.9576	High Similarity	NPC473682
0.9573	High Similarity	NPC48984
0.9573	High Similarity	NPC473862
0.9573	High Similarity	NPC8573
0.9573	High Similarity	NPC219043
0.9571	High Similarity	NPC25724
0.9568	High Similarity	NPC206123
0.9568	High Similarity	NPC231194
0.9568	High Similarity	NPC150767
0.9568	High Similarity	NPC78734
0.9568	High Similarity	NPC116864
0.9568	High Similarity	NPC244776
0.9568	High Similarity	NPC51326
0.9568	High Similarity	NPC218488
0.9565	High Similarity	NPC160156
0.9565	High Similarity	NPC92565
0.9563	High Similarity	NPC311830
0.9563	High Similarity	NPC15358
0.9563	High Similarity	NPC22832
0.956	High Similarity	NPC77660
0.956	High Similarity	NPC189142
0.9518	High Similarity	NPC473073
0.9518	High Similarity	NPC473071
0.9515	High Similarity	NPC217387
0.9515	High Similarity	NPC258044
0.9515	High Similarity	NPC196127
0.9515	High Similarity	NPC267680
0.9515	High Similarity	NPC293626
0.9512	High Similarity	NPC198199
0.9509	High Similarity	NPC259152
0.9509	High Similarity	NPC245452
0.9509	High Similarity	NPC256760
0.9509	High Similarity	NPC476405
0.9509	High Similarity	NPC153755
0.9509	High Similarity	NPC175107
0.9509	High Similarity	NPC180918
0.9509	High Similarity	NPC190003
0.9509	High Similarity	NPC3583
0.9509	High Similarity	NPC117260
0.9506	High Similarity	NPC43587
0.9506	High Similarity	NPC138927
0.9506	High Similarity	NPC105283
0.9503	High Similarity	NPC236934
0.9503	High Similarity	NPC5778
0.95	High Similarity	NPC191306
0.95	High Similarity	NPC270335
0.95	High Similarity	NPC29830
0.95	High Similarity	NPC309025
0.95	High Similarity	NPC168822
0.95	High Similarity	NPC243930
0.95	High Similarity	NPC88023
0.9461	High Similarity	NPC156785
0.9461	High Similarity	NPC241781
0.9461	High Similarity	NPC470447
0.9461	High Similarity	NPC162394
0.9461	High Similarity	NPC470445
0.9461	High Similarity	NPC470449
0.9461	High Similarity	NPC470446
0.9461	High Similarity	NPC473072
0.9455	High Similarity	NPC255799
0.9451	High Similarity	NPC101026
0.9451	High Similarity	NPC42773
0.9451	High Similarity	NPC4390
0.9451	High Similarity	NPC45522
0.9451	High Similarity	NPC21666
0.9451	High Similarity	NPC24043
0.9451	High Similarity	NPC208668
0.9451	High Similarity	NPC169977
0.9451	High Similarity	NPC204693
0.9448	High Similarity	NPC20505
0.9448	High Similarity	NPC79056
0.9448	High Similarity	NPC44328
0.9448	High Similarity	NPC245014
0.9448	High Similarity	NPC177731
0.9448	High Similarity	NPC155763
0.9448	High Similarity	NPC282987
0.9448	High Similarity	NPC105095
0.9448	High Similarity	NPC84265
0.9448	High Similarity	NPC235260
0.9444	High Similarity	NPC229729
0.9444	High Similarity	NPC477502
0.9441	High Similarity	NPC475497
0.9441	High Similarity	NPC34531
0.9441	High Similarity	NPC284277
0.9441	High Similarity	NPC475366
0.9437	High Similarity	NPC127782
0.9437	High Similarity	NPC300537
0.9434	High Similarity	NPC136761
0.9434	High Similarity	NPC110349
0.9434	High Similarity	NPC187379
0.9405	High Similarity	NPC148710
0.9405	High Similarity	NPC25946
0.9405	High Similarity	NPC460984
0.9405	High Similarity	NPC470720
0.9405	High Similarity	NPC470713
0.9405	High Similarity	NPC470451
0.9405	High Similarity	NPC223860
0.9405	High Similarity	NPC470717
0.9405	High Similarity	NPC21359
0.9405	High Similarity	NPC275977
0.9405	High Similarity	NPC470455
0.9405	High Similarity	NPC249560
0.9398	High Similarity	NPC139571
0.9398	High Similarity	NPC253521
0.9398	High Similarity	NPC120952
0.9398	High Similarity	NPC35167

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 NPC227508 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	407
0.1-0.2	972
0.2-0.3	2070
0.3-0.4	2716
0.4-0.5	1794
0.5-0.6	805
0.6-0.7	256
0.7-0.8	100
0.8-0.85	16
0.85-0.9	6
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9875	High Similarity	NPD6797	Phase 2
0.9814	High Similarity	NPD7251	Discontinued
0.9689	High Similarity	NPD7472	Approved
0.9632	High Similarity	NPD7808	Phase 3
0.9627	High Similarity	NPD7054	Approved
0.9448	High Similarity	NPD7074	Phase 3
0.9277	High Similarity	NPD4338	Clinical (unspecified phase)
0.9202	High Similarity	NPD6166	Phase 2
0.9202	High Similarity	NPD6168	Clinical (unspecified phase)
0.9202	High Similarity	NPD6167	Clinical (unspecified phase)
0.9152	High Similarity	NPD7804	Clinical (unspecified phase)
0.9091	High Similarity	NPD3818	Discontinued
0.9068	High Similarity	NPD4381	Clinical (unspecified phase)
0.882	High Similarity	NPD1934	Approved
0.8765	High Similarity	NPD2393	Clinical (unspecified phase)
0.8712	High Similarity	NPD3817	Phase 2
0.8706	High Similarity	NPD7993	Clinical (unspecified phase)
0.8679	High Similarity	NPD1512	Approved
0.865	High Similarity	NPD2801	Approved
0.8553	High Similarity	NPD1511	Approved
0.8545	High Similarity	NPD3882	Suspended
0.8545	High Similarity	NPD4868	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD4380	Phase 2
0.8383	Intermediate Similarity	NPD7075	Discontinued
0.8333	Intermediate Similarity	NPD6559	Discontinued
0.8272	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD5402	Approved
0.8253	Intermediate Similarity	NPD6801	Discontinued
0.8204	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD5403	Approved
0.8129	Intermediate Similarity	NPD6959	Discontinued
0.8098	Intermediate Similarity	NPD6799	Approved
0.807	Intermediate Similarity	NPD5494	Approved
0.8063	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD5401	Approved
0.8022	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1549	Phase 2
0.8012	Intermediate Similarity	NPD1653	Approved
0.8	Intermediate Similarity	NPD3751	Discontinued
0.8	Intermediate Similarity	NPD7228	Approved
0.7988	Intermediate Similarity	NPD1465	Phase 2
0.7977	Intermediate Similarity	NPD3787	Discontinued
0.7941	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD8313	Approved
0.7933	Intermediate Similarity	NPD8312	Approved
0.7888	Intermediate Similarity	NPD2796	Approved
0.7882	Intermediate Similarity	NPD7819	Suspended
0.787	Intermediate Similarity	NPD7411	Suspended
0.7853	Intermediate Similarity	NPD5844	Phase 1
0.7831	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1510	Phase 2
0.7821	Intermediate Similarity	NPD7685	Pre-registration
0.7811	Intermediate Similarity	NPD6599	Discontinued
0.7772	Intermediate Similarity	NPD8151	Discontinued
0.7771	Intermediate Similarity	NPD6232	Discontinued
0.774	Intermediate Similarity	NPD7473	Discontinued
0.7738	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7266	Discontinued
0.7727	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6781	Approved
0.7725	Intermediate Similarity	NPD6779	Approved
0.7725	Intermediate Similarity	NPD6780	Approved
0.7725	Intermediate Similarity	NPD6782	Approved
0.7725	Intermediate Similarity	NPD6778	Approved
0.7725	Intermediate Similarity	NPD6776	Approved
0.7725	Intermediate Similarity	NPD6777	Approved
0.7714	Intermediate Similarity	NPD7199	Phase 2
0.7701	Intermediate Similarity	NPD6234	Discontinued
0.7688	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1613	Approved
0.7684	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD8455	Phase 2
0.765	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD7240	Approved
0.7622	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD37	Approved
0.7604	Intermediate Similarity	NPD7698	Approved
0.7604	Intermediate Similarity	NPD7696	Phase 3
0.7604	Intermediate Similarity	NPD7435	Discontinued
0.7604	Intermediate Similarity	NPD7697	Approved
0.76	Intermediate Similarity	NPD919	Approved
0.759	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4965	Approved
0.7586	Intermediate Similarity	NPD4967	Phase 2
0.7586	Intermediate Similarity	NPD4966	Approved
0.7578	Intermediate Similarity	NPD1240	Approved
0.7577	Intermediate Similarity	NPD7584	Approved
0.7545	Intermediate Similarity	NPD6190	Approved
0.7538	Intermediate Similarity	NPD7701	Phase 2
0.7531	Intermediate Similarity	NPD230	Phase 1
0.7528	Intermediate Similarity	NPD3926	Phase 2
0.7514	Intermediate Similarity	NPD1247	Approved
0.7485	Intermediate Similarity	NPD1607	Approved
0.7485	Intermediate Similarity	NPD3750	Approved
0.7484	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7871	Phase 2
0.7474	Intermediate Similarity	NPD7870	Phase 2
0.7469	Intermediate Similarity	NPD943	Approved
0.746	Intermediate Similarity	NPD6534	Approved
0.746	Intermediate Similarity	NPD6535	Approved
0.7456	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7700	Phase 2
0.7435	Intermediate Similarity	NPD7699	Phase 2
0.7424	Intermediate Similarity	NPD7783	Phase 2
0.7424	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1933	Approved
0.7391	Intermediate Similarity	NPD3027	Phase 3
0.7386	Intermediate Similarity	NPD7768	Phase 2
0.7382	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4628	Phase 3
0.7374	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7874	Approved
0.7349	Intermediate Similarity	NPD1551	Phase 2
0.7346	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD3749	Approved
0.7337	Intermediate Similarity	NPD7801	Approved
0.731	Intermediate Similarity	NPD2533	Approved
0.731	Intermediate Similarity	NPD2534	Approved
0.731	Intermediate Similarity	NPD2532	Approved
0.7296	Intermediate Similarity	NPD8319	Approved
0.7296	Intermediate Similarity	NPD8320	Phase 1
0.7289	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6823	Phase 2
0.7246	Intermediate Similarity	NPD2935	Discontinued
0.7234	Intermediate Similarity	NPD8434	Phase 2
0.7234	Intermediate Similarity	NPD8150	Discontinued
0.7219	Intermediate Similarity	NPD2800	Approved
0.7219	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD447	Suspended
0.7186	Intermediate Similarity	NPD7585	Approved
0.7186	Intermediate Similarity	NPD3748	Approved
0.7151	Intermediate Similarity	NPD7390	Discontinued
0.7143	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD6100	Approved
0.7136	Intermediate Similarity	NPD7583	Approved
0.7126	Intermediate Similarity	NPD920	Approved
0.7118	Intermediate Similarity	NPD6674	Discontinued
0.7118	Intermediate Similarity	NPD1243	Approved
0.7112	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1091	Approved
0.7104	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4360	Phase 2
0.7098	Intermediate Similarity	NPD4363	Phase 3
0.7097	Intermediate Similarity	NPD5953	Discontinued
0.7092	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7033	Discontinued
0.7071	Intermediate Similarity	NPD7680	Approved
0.7066	Intermediate Similarity	NPD6651	Approved
0.7047	Intermediate Similarity	NPD6213	Phase 3
0.7047	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6212	Phase 3
0.7045	Intermediate Similarity	NPD3226	Approved
0.7033	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6798	Discontinued
0.7022	Intermediate Similarity	NPD6844	Discontinued
0.7019	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1652	Phase 2
0.7012	Intermediate Similarity	NPD6832	Phase 2
0.7012	Intermediate Similarity	NPD4908	Phase 1
0.7011	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2798	Approved
0.6989	Remote Similarity	NPD7286	Phase 2
0.6988	Remote Similarity	NPD6233	Phase 2
0.6977	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD9494	Approved
0.6944	Remote Similarity	NPD5353	Approved
0.6933	Remote Similarity	NPD1203	Approved
0.6928	Remote Similarity	NPD2313	Discontinued
0.6928	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5124	Phase 1
0.6905	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6355	Discontinued
0.6905	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD5710	Approved
0.6902	Remote Similarity	NPD5711	Approved
0.6901	Remote Similarity	NPD2346	Discontinued
0.6901	Remote Similarity	NPD2344	Approved
0.6894	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2799	Discontinued
0.6882	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1548	Phase 1
0.6854	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD9269	Phase 2
0.6839	Remote Similarity	NPD6843	Phase 3
0.6839	Remote Similarity	NPD6842	Approved
0.6839	Remote Similarity	NPD6841	Approved
0.6828	Remote Similarity	NPD2403	Approved
0.6826	Remote Similarity	NPD3268	Approved
0.6812	Remote Similarity	NPD7930	Approved
0.679	Remote Similarity	NPD1610	Phase 2

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