NPASS Compound

Structure

CID304745 OpenBabel06191716112D 33 36 0 0 1 0 0 0 0 0999 V2000 -0.0000 1.0000 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 -6.0622 2.5000 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 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 1.7321 0.0000 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 -7.7942 2.5000 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 -3.4641 1.0000 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 -3.4641 -0.0000 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 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 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 -0.8660 -1.5000 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 -0.8660 -0.5000 0.0000 C 0 0 1 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 -8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 -3.0000 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 -1.7321 -2.0000 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 1 31 1 0 0 0 0 2 4 1 0 0 0 0 2 8 2 0 0 0 0 3 5 2 0 0 0 0 3 8 1 0 0 0 0 4 9 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 23 1 0 0 0 0 8 21 1 0 0 0 0 9 24 1 0 0 0 0 10 14 1 0 0 0 0 10 31 1 0 0 0 0 11 13 2 0 0 0 0 11 32 1 0 0 0 0 12 7 1 6 0 0 0 12 15 1 0 0 0 0 12 33 1 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 16 2 0 0 0 0 15 18 1 0 0 0 0 15 25 1 1 0 0 0 16 26 1 0 0 0 0 17 19 1 0 0 0 0 17 27 2 0 0 0 0 18 20 1 0 0 0 0 18 28 1 6 0 0 0 19 21 2 0 0 0 0 19 29 1 0 0 0 0 20 22 1 0 0 0 0 20 30 1 1 0 0 0 21 32 1 0 0 0 0 22 14 1 6 0 0 0 22 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.12
Volume:	430.443
LogP:	0.784
LogD:	0.148
LogS:	-3.036
# Rotatable Bonds:	4
TPSA:	190.28
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.278
Synthetic Accessibility Score:	4.003
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:	-6.216
MDCK Permeability:	6.250594651646679e-06
Pgp-inhibitor:	0.031
Pgp-substrate:	0.974
Human Intestinal Absorption (HIA):	0.76
20% Bioavailability (F20%):	0.072
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	88.16536712646484%
Volume Distribution (VD):	0.956
Pgp-substrate:	11.63354778289795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.064
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.418
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.019

ADMET: Excretion

Clearance (CL):	3.028
Half-life (T1/2):	0.86

ADMET: Toxicity

hERG Blockers:	0.115
Human Hepatotoxicity (H-HT):	0.11
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.786
Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.253
Carcinogencity:	0.033
Eye Corrosion:	0.003
Eye Irritation:	0.082
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC304745

Natural Product ID:	NPC304745
*Common Name:**	Keyakinin
IUPAC Name:	3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
Synonyms:	Keyakinin
Standard InCHIKey:	FWCFJKZMFJQKIT-WXZPSOLRSA-N
Standard InCHI:	InChI=1S/C22H22O11/c1-31-10-6-11-13(17(27)19(29)21(32-11)8-2-4-9(24)5-3-8)16(26)14(10)22-20(30)18(28)15(25)12(7-23)33-22/h2-6,12,15,18,20,22-26,28-30H,7H2,1H3/t12-,15-,18+,20-,22+/m1/s1
SMILES:	OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)c1c(OC)cc2c(c1O)c(=O)c(c(o2)c1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520545
PubChem CID:	44559819
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
NPO10904	Panax arboreus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15288	Zelkova serrata	Species	Ulmaceae	Eukaryota	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	0.0	%	PMID[571186]

☑ 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 NPC304745 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	427
0.1-0.2	1666
0.2-0.3	3878
0.3-0.4	9624
0.4-0.5	8870
0.5-0.6	4039
0.6-0.7	5434
0.7-0.8	4447
0.8-0.85	2113
0.85-0.9	1824
0.9-0.95	358
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC111341
0.9932	High Similarity	NPC268193
0.9865	High Similarity	NPC48579
0.9865	High Similarity	NPC304207
0.9865	High Similarity	NPC207809
0.9865	High Similarity	NPC217706
0.9865	High Similarity	NPC259710
0.9864	High Similarity	NPC10807
0.9864	High Similarity	NPC150123
0.9864	High Similarity	NPC56232
0.9864	High Similarity	NPC244583
0.9864	High Similarity	NPC161881
0.9797	High Similarity	NPC180301
0.9797	High Similarity	NPC248793
0.9796	High Similarity	NPC477897
0.9796	High Similarity	NPC262039
0.9796	High Similarity	NPC289774
0.9796	High Similarity	NPC278476
0.9796	High Similarity	NPC328740
0.9796	High Similarity	NPC254412
0.9796	High Similarity	NPC319910
0.9796	High Similarity	NPC209846
0.9796	High Similarity	NPC262038
0.973	High Similarity	NPC216035
0.973	High Similarity	NPC138288
0.973	High Similarity	NPC171651
0.973	High Similarity	NPC243171
0.973	High Similarity	NPC217149
0.973	High Similarity	NPC35567
0.9728	High Similarity	NPC105136
0.9667	High Similarity	NPC215917
0.9667	High Similarity	NPC10754
0.9667	High Similarity	NPC20530
0.9664	High Similarity	NPC223701
0.9664	High Similarity	NPC7989
0.9664	High Similarity	NPC109594
0.9664	High Similarity	NPC244250
0.9664	High Similarity	NPC236756
0.9664	High Similarity	NPC311579
0.9664	High Similarity	NPC112701
0.9664	High Similarity	NPC20907
0.9664	High Similarity	NPC472583
0.9664	High Similarity	NPC293286
0.9664	High Similarity	NPC326592
0.9608	High Similarity	NPC131745
0.96	High Similarity	NPC476169
0.96	High Similarity	NPC470681
0.9597	High Similarity	NPC475790
0.9595	High Similarity	NPC177308
0.9595	High Similarity	NPC124478
0.9592	High Similarity	NPC10097
0.9545	High Similarity	NPC183672
0.9545	High Similarity	NPC179198
0.9545	High Similarity	NPC66087
0.9545	High Similarity	NPC278419
0.9542	High Similarity	NPC289771
0.9539	High Similarity	NPC123544
0.9533	High Similarity	NPC469405
0.9533	High Similarity	NPC88983
0.953	High Similarity	NPC472420
0.953	High Similarity	NPC263384
0.953	High Similarity	NPC244577
0.953	High Similarity	NPC472422
0.953	High Similarity	NPC471676
0.953	High Similarity	NPC474023
0.953	High Similarity	NPC474021
0.953	High Similarity	NPC471677
0.9527	High Similarity	NPC89442
0.9527	High Similarity	NPC307052
0.9527	High Similarity	NPC139966
0.9524	High Similarity	NPC211466
0.9524	High Similarity	NPC176869
0.9524	High Similarity	NPC476182
0.9524	High Similarity	NPC40086
0.9524	High Similarity	NPC122828
0.9524	High Similarity	NPC44721
0.9524	High Similarity	NPC3779
0.9481	High Similarity	NPC259834
0.947	High Similarity	NPC477958
0.9467	High Similarity	NPC210597
0.9463	High Similarity	NPC61258
0.9459	High Similarity	NPC296869
0.9456	High Similarity	NPC472629
0.9419	High Similarity	NPC472625
0.9416	High Similarity	NPC471499
0.9416	High Similarity	NPC26326
0.9412	High Similarity	NPC117418
0.9412	High Similarity	NPC22192
0.9412	High Similarity	NPC53545
0.9408	High Similarity	NPC78492
0.9408	High Similarity	NPC208152
0.9404	High Similarity	NPC100134
0.9404	High Similarity	NPC209760
0.94	High Similarity	NPC472636
0.94	High Similarity	NPC471675
0.9396	High Similarity	NPC472628
0.9396	High Similarity	NPC5173
0.9396	High Similarity	NPC470461
0.9392	High Similarity	NPC472918
0.9392	High Similarity	NPC473077
0.9392	High Similarity	NPC85773
0.9392	High Similarity	NPC472627
0.9392	High Similarity	NPC296998
0.9388	High Similarity	NPC124780
0.9388	High Similarity	NPC208176
0.9388	High Similarity	NPC62290
0.9388	High Similarity	NPC49130
0.9388	High Similarity	NPC273538
0.9388	High Similarity	NPC216538
0.9388	High Similarity	NPC224714
0.9388	High Similarity	NPC326506
0.9388	High Similarity	NPC470890
0.9388	High Similarity	NPC87486
0.9388	High Similarity	NPC4152
0.9388	High Similarity	NPC142731
0.9388	High Similarity	NPC279417
0.9388	High Similarity	NPC306607
0.9355	High Similarity	NPC44947
0.9351	High Similarity	NPC470326
0.9351	High Similarity	NPC306978
0.9351	High Similarity	NPC475784
0.9351	High Similarity	NPC282009
0.9351	High Similarity	NPC287328
0.9346	High Similarity	NPC282390
0.9346	High Similarity	NPC281137
0.9346	High Similarity	NPC108831
0.9346	High Similarity	NPC182634
0.9342	High Similarity	NPC471116
0.9342	High Similarity	NPC477530
0.9338	High Similarity	NPC476238
0.9338	High Similarity	NPC31627
0.9338	High Similarity	NPC473996
0.9338	High Similarity	NPC327269
0.9338	High Similarity	NPC285623
0.9333	High Similarity	NPC472633
0.9329	High Similarity	NPC218569
0.9329	High Similarity	NPC244407
0.9329	High Similarity	NPC470460
0.9324	High Similarity	NPC111786
0.9324	High Similarity	NPC148011
0.9324	High Similarity	NPC20488
0.9324	High Similarity	NPC195621
0.9324	High Similarity	NPC5820
0.9324	High Similarity	NPC124729
0.9324	High Similarity	NPC176229
0.9324	High Similarity	NPC470458
0.9324	High Similarity	NPC267375
0.9324	High Similarity	NPC214774
0.9324	High Similarity	NPC88964
0.9324	High Similarity	NPC470647
0.9324	High Similarity	NPC142405
0.9324	High Similarity	NPC474302
0.9324	High Similarity	NPC312973
0.9324	High Similarity	NPC1940
0.9324	High Similarity	NPC475052
0.9324	High Similarity	NPC54577
0.9324	High Similarity	NPC178343
0.9324	High Similarity	NPC83357
0.9324	High Similarity	NPC246948
0.9324	High Similarity	NPC67805
0.9324	High Similarity	NPC306488
0.9324	High Similarity	NPC301276
0.932	High Similarity	NPC190637
0.932	High Similarity	NPC212932
0.932	High Similarity	NPC293053
0.932	High Similarity	NPC24821
0.932	High Similarity	NPC9117
0.9304	High Similarity	NPC5319
0.9299	High Similarity	NPC471213
0.9295	High Similarity	NPC257566
0.9295	High Similarity	NPC124155
0.9295	High Similarity	NPC63438
0.929	High Similarity	NPC142252
0.929	High Similarity	NPC47923
0.929	High Similarity	NPC474038
0.9286	High Similarity	NPC472459
0.9286	High Similarity	NPC41121
0.9286	High Similarity	NPC320283
0.9286	High Similarity	NPC73511
0.9286	High Similarity	NPC111929
0.9281	High Similarity	NPC323593
0.9281	High Similarity	NPC471787
0.9281	High Similarity	NPC307938
0.9281	High Similarity	NPC203500
0.9281	High Similarity	NPC146636
0.9276	High Similarity	NPC193200
0.9276	High Similarity	NPC203080
0.9272	High Similarity	NPC472580
0.9272	High Similarity	NPC472423
0.9272	High Similarity	NPC471229
0.9272	High Similarity	NPC474772
0.9272	High Similarity	NPC474744
0.9267	High Similarity	NPC277032
0.9262	High Similarity	NPC283234
0.9262	High Similarity	NPC23728
0.9262	High Similarity	NPC91902
0.9262	High Similarity	NPC14001
0.9262	High Similarity	NPC51070
0.9262	High Similarity	NPC21835
0.9262	High Similarity	NPC166757

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 NPC304745 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	888
0.2-0.3	1748
0.3-0.4	2657
0.4-0.5	1963
0.5-0.6	982
0.6-0.7	349
0.7-0.8	122
0.8-0.85	28
0.85-0.9	25
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9595	High Similarity	NPD4380	Phase 2
0.9388	High Similarity	NPD4378	Clinical (unspecified phase)
0.9346	High Similarity	NPD7075	Discontinued
0.9304	High Similarity	NPD7804	Clinical (unspecified phase)
0.9221	High Similarity	NPD4381	Clinical (unspecified phase)
0.9211	High Similarity	NPD6801	Discontinued
0.915	High Similarity	NPD7096	Clinical (unspecified phase)
0.915	High Similarity	NPD2393	Clinical (unspecified phase)
0.9114	High Similarity	NPD6166	Phase 2
0.9114	High Similarity	NPD6168	Clinical (unspecified phase)
0.9114	High Similarity	NPD6167	Clinical (unspecified phase)
0.8968	High Similarity	NPD8443	Clinical (unspecified phase)
0.8961	High Similarity	NPD1934	Approved
0.8912	High Similarity	NPD1552	Clinical (unspecified phase)
0.8912	High Similarity	NPD1550	Clinical (unspecified phase)
0.8874	High Similarity	NPD7410	Clinical (unspecified phase)
0.8851	High Similarity	NPD1549	Phase 2
0.8834	High Similarity	NPD6797	Phase 2
0.878	High Similarity	NPD7251	Discontinued
0.8774	High Similarity	NPD7411	Suspended
0.8758	High Similarity	NPD5403	Approved
0.8727	High Similarity	NPD7808	Phase 3
0.8726	High Similarity	NPD3817	Phase 2
0.8716	High Similarity	NPD2796	Approved
0.8712	High Similarity	NPD7054	Approved
0.8693	High Similarity	NPD1512	Approved
0.8684	High Similarity	NPD6799	Approved
0.8662	High Similarity	NPD2801	Approved
0.8659	High Similarity	NPD7074	Phase 3
0.8659	High Similarity	NPD7472	Approved
0.8649	High Similarity	NPD1510	Phase 2
0.8627	High Similarity	NPD5401	Approved
0.8614	High Similarity	NPD4338	Clinical (unspecified phase)
0.8608	High Similarity	NPD5402	Approved
0.8571	High Similarity	NPD6959	Discontinued
0.8562	High Similarity	NPD1511	Approved
0.8553	High Similarity	NPD3882	Suspended
0.8544	High Similarity	NPD7819	Suspended
0.8537	High Similarity	NPD3818	Discontinued
0.8471	Intermediate Similarity	NPD6599	Discontinued
0.8443	Intermediate Similarity	NPD6559	Discontinued
0.8438	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD5494	Approved
0.8378	Intermediate Similarity	NPD1240	Approved
0.8274	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1607	Approved
0.821	Intermediate Similarity	NPD7768	Phase 2
0.8155	Intermediate Similarity	NPD5844	Phase 1
0.8136	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD3750	Approved
0.8072	Intermediate Similarity	NPD6232	Discontinued
0.8065	Intermediate Similarity	NPD2800	Approved
0.8065	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7473	Discontinued
0.8013	Intermediate Similarity	NPD4628	Phase 3
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD3749	Approved
0.7937	Intermediate Similarity	NPD920	Approved
0.7921	Intermediate Similarity	NPD4360	Phase 2
0.7921	Intermediate Similarity	NPD4363	Phase 3
0.7908	Intermediate Similarity	NPD6651	Approved
0.7904	Intermediate Similarity	NPD1247	Approved
0.7892	Intermediate Similarity	NPD919	Approved
0.7885	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD2935	Discontinued
0.7871	Intermediate Similarity	NPD1551	Phase 2
0.7849	Intermediate Similarity	NPD5953	Discontinued
0.7838	Intermediate Similarity	NPD7584	Approved
0.7834	Intermediate Similarity	NPD1243	Approved
0.7812	Intermediate Similarity	NPD2533	Approved
0.7812	Intermediate Similarity	NPD2532	Approved
0.7812	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2534	Approved
0.7806	Intermediate Similarity	NPD3748	Approved
0.7799	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3751	Discontinued
0.7778	Intermediate Similarity	NPD1613	Approved
0.7778	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2313	Discontinued
0.7758	Intermediate Similarity	NPD1465	Phase 2
0.7751	Intermediate Similarity	NPD3787	Discontinued
0.7748	Intermediate Similarity	NPD4908	Phase 1
0.7733	Intermediate Similarity	NPD7286	Phase 2
0.7727	Intermediate Similarity	NPD5124	Phase 1
0.7727	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD8312	Approved
0.7714	Intermediate Similarity	NPD8313	Approved
0.7706	Intermediate Similarity	NPD3926	Phase 2
0.7705	Intermediate Similarity	NPD6782	Approved
0.7705	Intermediate Similarity	NPD6778	Approved
0.7705	Intermediate Similarity	NPD6781	Approved
0.7705	Intermediate Similarity	NPD6777	Approved
0.7705	Intermediate Similarity	NPD6776	Approved
0.7705	Intermediate Similarity	NPD6779	Approved
0.7705	Intermediate Similarity	NPD6780	Approved
0.7692	Intermediate Similarity	NPD7033	Discontinued
0.7692	Intermediate Similarity	NPD2799	Discontinued
0.7651	Intermediate Similarity	NPD8455	Phase 2
0.7647	Intermediate Similarity	NPD6798	Discontinued
0.764	Intermediate Similarity	NPD7390	Discontinued
0.7635	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3226	Approved
0.7595	Intermediate Similarity	NPD2344	Approved
0.7584	Intermediate Similarity	NPD8150	Discontinued
0.7584	Intermediate Similarity	NPD8434	Phase 2
0.7581	Intermediate Similarity	NPD7435	Discontinued
0.7558	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD943	Approved
0.7547	Intermediate Similarity	NPD2424	Discontinued
0.7532	Intermediate Similarity	NPD6100	Approved
0.7532	Intermediate Similarity	NPD6099	Approved
0.753	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1610	Phase 2
0.7516	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD6355	Discontinued
0.75	Intermediate Similarity	NPD1652	Phase 2
0.7487	Intermediate Similarity	NPD7697	Approved
0.7487	Intermediate Similarity	NPD7698	Approved
0.7487	Intermediate Similarity	NPD7696	Phase 3
0.7486	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4361	Phase 2
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6233	Phase 2
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7483	Intermediate Similarity	NPD1548	Phase 1
0.7468	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3027	Phase 3
0.7451	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7870	Phase 2
0.7447	Intermediate Similarity	NPD7871	Phase 2
0.7434	Intermediate Similarity	NPD1203	Approved
0.7432	Intermediate Similarity	NPD6534	Approved
0.7432	Intermediate Similarity	NPD6535	Approved
0.743	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7701	Phase 2
0.7421	Intermediate Similarity	NPD7585	Approved
0.7419	Intermediate Similarity	NPD3268	Approved
0.7419	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7458	Discontinued
0.741	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6190	Approved
0.7407	Intermediate Similarity	NPD2309	Approved
0.7403	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2798	Approved
0.7384	Intermediate Similarity	NPD7199	Phase 2
0.7382	Intermediate Similarity	NPD8151	Discontinued
0.7381	Intermediate Similarity	NPD6844	Discontinued
0.7368	Intermediate Similarity	NPD7583	Approved
0.7349	Intermediate Similarity	NPD1653	Approved
0.7346	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD3823	Discontinued
0.7344	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7874	Approved
0.7341	Intermediate Similarity	NPD5710	Approved
0.7341	Intermediate Similarity	NPD5711	Approved
0.7325	Intermediate Similarity	NPD4060	Phase 1
0.732	Intermediate Similarity	NPD2797	Approved
0.7312	Intermediate Similarity	NPD7699	Phase 2
0.7312	Intermediate Similarity	NPD7700	Phase 2
0.7306	Intermediate Similarity	NPD7801	Approved
0.7306	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7783	Phase 2
0.7285	Intermediate Similarity	NPD422	Phase 1
0.7278	Intermediate Similarity	NPD230	Phase 1
0.7278	Intermediate Similarity	NPD37	Approved
0.7278	Intermediate Similarity	NPD1933	Approved
0.7273	Intermediate Similarity	NPD7228	Approved
0.7273	Intermediate Similarity	NPD4662	Approved
0.7273	Intermediate Similarity	NPD4661	Approved
0.7267	Intermediate Similarity	NPD6234	Discontinued
0.7257	Intermediate Similarity	NPD2403	Approved
0.7255	Intermediate Similarity	NPD3225	Approved
0.7251	Intermediate Similarity	NPD4966	Approved
0.7251	Intermediate Similarity	NPD4965	Approved
0.7251	Intermediate Similarity	NPD4967	Phase 2
0.725	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4308	Phase 3
0.7249	Intermediate Similarity	NPD6823	Phase 2
0.7244	Intermediate Similarity	NPD4625	Phase 3
0.7237	Intermediate Similarity	NPD9717	Approved
0.7229	Intermediate Similarity	NPD5049	Phase 3
0.7219	Intermediate Similarity	NPD5889	Approved
0.7219	Intermediate Similarity	NPD5890	Approved
0.7207	Intermediate Similarity	NPD7685	Pre-registration
0.7195	Intermediate Similarity	NPD2354	Approved
0.7195	Intermediate Similarity	NPD3887	Approved
0.7193	Intermediate Similarity	NPD4288	Approved
0.7191	Intermediate Similarity	NPD1729	Discontinued
0.7188	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4538	Approved
0.7188	Intermediate Similarity	NPD4536	Approved
0.7178	Intermediate Similarity	NPD2654	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