NPASS Compound

Structure

CID219927 OpenBabel06191716012D 40 45 0 0 1 0 0 0 0 0999 V2000 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 0.8660 -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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 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 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 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 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 0.5000 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 8.6603 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 2.5981 3.5000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 1 14 2 0 0 0 0 2 5 2 0 0 0 0 2 14 1 0 0 0 0 3 6 2 0 0 0 0 3 15 1 0 0 0 0 4 18 2 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 15 2 0 0 0 0 7 26 1 0 0 0 0 8 16 2 0 0 0 0 8 20 1 0 0 0 0 9 17 2 0 0 0 0 9 21 1 0 0 0 0 10 16 1 0 0 0 0 10 27 2 0 0 0 0 11 17 1 0 0 0 0 11 28 2 0 0 0 0 12 22 1 0 0 0 0 12 24 1 0 0 0 0 13 23 1 0 0 0 0 13 25 2 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 31 1 0 0 0 0 17 32 1 0 0 0 0 18 38 1 0 0 0 0 19 26 2 0 0 0 0 19 33 1 0 0 0 0 20 29 2 0 0 0 0 20 34 1 0 0 0 0 21 30 2 0 0 0 0 21 35 1 0 0 0 0 22 29 1 0 0 0 0 22 36 2 0 0 0 0 23 30 1 0 0 0 0 23 37 2 0 0 0 0 24 39 1 0 0 0 0 25 40 1 0 0 0 0 26 38 1 0 0 0 0 27 29 1 0 0 0 0 27 39 1 0 0 0 0 28 30 1 0 0 0 0 28 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.11
Volume:	524.453
LogP:	5.373
LogD:	2.994
LogS:	-5.457
# Rotatable Bonds:	4
TPSA:	166.89
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.197
Synthetic Accessibility Score:	3.409
Fsp3:	0.067
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.159
MDCK Permeability:	8.906235052563716e-06
Pgp-inhibitor:	0.022
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.418
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	98.07007598876953%
Volume Distribution (VD):	0.417
Pgp-substrate:	2.479520320892334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.781
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.943
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.846
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.116
CYP2D6-substrate:	0.682
CYP3A4-inhibitor:	0.513
CYP3A4-substrate:	0.101

ADMET: Excretion

Clearance (CL):	6.344
Half-life (T1/2):	0.599

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.496
Rat Oral Acute Toxicity:	0.925
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.959
Carcinogencity:	0.428
Eye Corrosion:	0.003
Eye Irritation:	0.905
Respiratory Toxicity:	0.251

Download Data

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

Natural Product: NPC219927

Natural Product ID:	NPC219927
*Common Name:**	2'',3''-Dihydroochnaflavone
IUPAC Name:	2-[3-[4-(5,7-dihydroxy-4-oxo-2,3-dihydrochromen-2-yl)phenoxy]-4-hydroxyphenyl]-5,7-dihydroxychromen-4-one
Synonyms:	2',3'-Dihydroochnaflavone
Standard InCHIKey:	VNCWZYPKAQUABQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H20O10/c31-16-8-20(34)29-22(36)12-24(39-27(29)10-16)14-1-4-18(5-2-14)38-26-7-15(3-6-19(26)33)25-13-23(37)30-21(35)9-17(32)11-28(30)40-25/h1-11,13,24,31-35H,12H2
SMILES:	Oc1cc2OC(CC(=O)c2c(c1)O)c1ccc(cc1)Oc1cc(ccc1O)c1cc(=O)c2c(o1)cc(cc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516700
PubChem CID:	10437291
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO21239	Quintinia acutifolia	Species	Paracryphiaceae	Eukaryota	Leaves	Charleston, New Zealand	1997-JAN	PMID[15104507]
NPO27822	Ochna integerrima	Species	Ochnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO27822	Ochna integerrima	Species	Ochnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21239	Quintinia acutifolia	Species	Paracryphiaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	3.1	ug.mL-1	PMID[558210]

☑ 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 NPC219927 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	504
0.1-0.2	1968
0.2-0.3	5005
0.3-0.4	10992
0.4-0.5	6437
0.5-0.6	3913
0.6-0.7	5096
0.7-0.8	4796
0.8-0.85	2022
0.85-0.9	1505
0.9-0.95	433
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.987	High Similarity	NPC477841
0.9744	High Similarity	NPC477840
0.9684	High Similarity	NPC475212
0.9677	High Similarity	NPC165970
0.9677	High Similarity	NPC288131
0.9677	High Similarity	NPC305987
0.9677	High Similarity	NPC66618
0.9677	High Similarity	NPC84324
0.9677	High Similarity	NPC113163
0.9613	High Similarity	NPC101731
0.961	High Similarity	NPC112954
0.9557	High Similarity	NPC171985
0.9557	High Similarity	NPC320741
0.9551	High Similarity	NPC158188
0.9548	High Similarity	NPC172202
0.9548	High Similarity	NPC284127
0.9548	High Similarity	NPC476410
0.95	High Similarity	NPC476365
0.9497	High Similarity	NPC243877
0.9494	High Similarity	NPC7154
0.9494	High Similarity	NPC36
0.9494	High Similarity	NPC58223
0.9494	High Similarity	NPC125039
0.9494	High Similarity	NPC36916
0.9494	High Similarity	NPC7688
0.9494	High Similarity	NPC72787
0.9484	High Similarity	NPC183
0.9484	High Similarity	NPC183851
0.9484	High Similarity	NPC63454
0.9437	High Similarity	NPC107627
0.9434	High Similarity	NPC224851
0.943	High Similarity	NPC272064
0.9427	High Similarity	NPC196179
0.9427	High Similarity	NPC26326
0.9427	High Similarity	NPC142252
0.9427	High Similarity	NPC34089
0.9423	High Similarity	NPC53545
0.9423	High Similarity	NPC117418
0.9416	High Similarity	NPC18727
0.9375	High Similarity	NPC260266
0.9375	High Similarity	NPC14662
0.9375	High Similarity	NPC295082
0.9367	High Similarity	NPC476247
0.9363	High Similarity	NPC118256
0.9363	High Similarity	NPC192686
0.9363	High Similarity	NPC119209
0.9351	High Similarity	NPC219582
0.9351	High Similarity	NPC236637
0.9351	High Similarity	NPC302950
0.9321	High Similarity	NPC186847
0.9321	High Similarity	NPC257667
0.9321	High Similarity	NPC472454
0.9304	High Similarity	NPC289771
0.9304	High Similarity	NPC474038
0.9295	High Similarity	NPC195796
0.9295	High Similarity	NPC278778
0.9295	High Similarity	NPC291878
0.9295	High Similarity	NPC35038
0.9273	High Similarity	NPC324742
0.9241	High Similarity	NPC475784
0.9236	High Similarity	NPC472598
0.9236	High Similarity	NPC156057
0.9236	High Similarity	NPC284820
0.9236	High Similarity	NPC474836
0.9236	High Similarity	NPC27337
0.9236	High Similarity	NPC48208
0.9236	High Similarity	NPC473272
0.9236	High Similarity	NPC291508
0.9236	High Similarity	NPC471515
0.9236	High Similarity	NPC475267
0.9236	High Similarity	NPC185526
0.9236	High Similarity	NPC162869
0.9236	High Similarity	NPC474055
0.9236	High Similarity	NPC471479
0.9236	High Similarity	NPC474208
0.9231	High Similarity	NPC200761
0.9231	High Similarity	NPC470327
0.9231	High Similarity	NPC45849
0.9231	High Similarity	NPC477503
0.9226	High Similarity	NPC472912
0.9221	High Similarity	NPC338131
0.9216	High Similarity	NPC188679
0.9216	High Similarity	NPC294852
0.9216	High Similarity	NPC321011
0.9202	High Similarity	NPC4200
0.9198	High Similarity	NPC188079
0.9193	High Similarity	NPC272560
0.9187	High Similarity	NPC186686
0.9187	High Similarity	NPC270335
0.9187	High Similarity	NPC472625
0.9187	High Similarity	NPC191306
0.9182	High Similarity	NPC472632
0.9182	High Similarity	NPC471212
0.9182	High Similarity	NPC471210
0.9182	High Similarity	NPC472634
0.9182	High Similarity	NPC471211
0.9182	High Similarity	NPC471499
0.9177	High Similarity	NPC123544
0.9177	High Similarity	NPC190487
0.9177	High Similarity	NPC154304
0.9172	High Similarity	NPC470328
0.9172	High Similarity	NPC235165
0.9172	High Similarity	NPC209614
0.9172	High Similarity	NPC250922
0.9172	High Similarity	NPC326037
0.9172	High Similarity	NPC255106
0.9172	High Similarity	NPC13858
0.9172	High Similarity	NPC471500
0.9172	High Similarity	NPC320825
0.9172	High Similarity	NPC472626
0.9167	High Similarity	NPC213896
0.9167	High Similarity	NPC192083
0.9157	High Similarity	NPC471030
0.9156	High Similarity	NPC183959
0.9156	High Similarity	NPC1612
0.9156	High Similarity	NPC287101
0.9156	High Similarity	NPC48479
0.9156	High Similarity	NPC183950
0.9156	High Similarity	NPC52005
0.9156	High Similarity	NPC177298
0.9156	High Similarity	NPC223579
0.9156	High Similarity	NPC137062
0.9146	High Similarity	NPC472993
0.9141	High Similarity	NPC279209
0.9141	High Similarity	NPC231194
0.9141	High Similarity	NPC102277
0.9141	High Similarity	NPC51326
0.9136	High Similarity	NPC473818
0.9136	High Similarity	NPC229729
0.913	High Similarity	NPC22832
0.913	High Similarity	NPC259757
0.913	High Similarity	NPC311830
0.9125	High Similarity	NPC77660
0.9125	High Similarity	NPC189142
0.9125	High Similarity	NPC474034
0.9125	High Similarity	NPC472635
0.9125	High Similarity	NPC474162
0.9125	High Similarity	NPC474150
0.9125	High Similarity	NPC474033
0.9119	High Similarity	NPC472630
0.9119	High Similarity	NPC287328
0.9119	High Similarity	NPC470326
0.9119	High Similarity	NPC174953
0.9119	High Similarity	NPC474960
0.9119	High Similarity	NPC282009
0.9119	High Similarity	NPC53889
0.9119	High Similarity	NPC472631
0.9119	High Similarity	NPC472624
0.9119	High Similarity	NPC36217
0.9119	High Similarity	NPC188967
0.9114	High Similarity	NPC38779
0.9114	High Similarity	NPC472914
0.9114	High Similarity	NPC223787
0.9114	High Similarity	NPC245758
0.9114	High Similarity	NPC470402
0.9114	High Similarity	NPC129684
0.9114	High Similarity	NPC52530
0.9114	High Similarity	NPC52889
0.9114	High Similarity	NPC472911
0.9114	High Similarity	NPC160512
0.9114	High Similarity	NPC68324
0.9114	High Similarity	NPC210084
0.9114	High Similarity	NPC222814
0.9114	High Similarity	NPC472910
0.9114	High Similarity	NPC299520
0.9114	High Similarity	NPC67876
0.9114	High Similarity	NPC114179
0.9114	High Similarity	NPC289322
0.9114	High Similarity	NPC156818
0.9114	High Similarity	NPC99597
0.9114	High Similarity	NPC471209
0.9114	High Similarity	NPC472913
0.9114	High Similarity	NPC96167
0.9108	High Similarity	NPC37392
0.9108	High Similarity	NPC183597
0.9108	High Similarity	NPC182555
0.9108	High Similarity	NPC66441
0.9108	High Similarity	NPC163780
0.9108	High Similarity	NPC196439
0.9108	High Similarity	NPC226025
0.9108	High Similarity	NPC128863
0.9108	High Similarity	NPC92659
0.9108	High Similarity	NPC50715
0.9108	High Similarity	NPC227325
0.9108	High Similarity	NPC146165
0.9108	High Similarity	NPC2476
0.9108	High Similarity	NPC201136
0.9108	High Similarity	NPC167815
0.9108	High Similarity	NPC67396
0.9108	High Similarity	NPC4455
0.9108	High Similarity	NPC138360
0.9108	High Similarity	NPC213622
0.9108	High Similarity	NPC280339
0.9108	High Similarity	NPC321779
0.9103	High Similarity	NPC471982
0.9103	High Similarity	NPC9743
0.9103	High Similarity	NPC39732
0.9103	High Similarity	NPC246162
0.9103	High Similarity	NPC106976
0.9103	High Similarity	NPC36835

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 NPC219927 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	465
0.1-0.2	966
0.2-0.3	1979
0.3-0.4	2635
0.4-0.5	1702
0.5-0.6	920
0.6-0.7	325
0.7-0.8	106
0.8-0.85	23
0.85-0.9	20
0.9-0.95	9
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9494	High Similarity	NPD6167	Clinical (unspecified phase)
0.9494	High Similarity	NPD6168	Clinical (unspecified phase)
0.9494	High Similarity	NPD6166	Phase 2
0.9351	High Similarity	NPD1934	Approved
0.9167	High Similarity	NPD2393	Clinical (unspecified phase)
0.908	High Similarity	NPD7054	Approved
0.9051	High Similarity	NPD4868	Clinical (unspecified phase)
0.9045	High Similarity	NPD2801	Approved
0.9024	High Similarity	NPD7472	Approved
0.9024	High Similarity	NPD7074	Phase 3
0.8954	High Similarity	NPD1511	Approved
0.8902	High Similarity	NPD3818	Discontinued
0.8855	High Similarity	NPD7993	Clinical (unspecified phase)
0.8855	High Similarity	NPD6797	Phase 2
0.8854	High Similarity	NPD4380	Phase 2
0.8839	High Similarity	NPD1512	Approved
0.8802	High Similarity	NPD7251	Discontinued
0.8758	High Similarity	NPD4381	Clinical (unspecified phase)
0.875	High Similarity	NPD4338	Clinical (unspecified phase)
0.875	High Similarity	NPD3817	Phase 2
0.875	High Similarity	NPD7808	Phase 3
0.8712	High Similarity	NPD6959	Discontinued
0.8696	High Similarity	NPD3882	Suspended
0.8562	High Similarity	NPD1552	Clinical (unspecified phase)
0.8562	High Similarity	NPD1550	Clinical (unspecified phase)
0.8519	High Similarity	NPD8443	Clinical (unspecified phase)
0.8506	High Similarity	NPD1549	Phase 2
0.8424	Intermediate Similarity	NPD5494	Approved
0.8418	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7075	Discontinued
0.8402	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7411	Suspended
0.8323	Intermediate Similarity	NPD6232	Discontinued
0.8312	Intermediate Similarity	NPD1510	Phase 2
0.8294	Intermediate Similarity	NPD5844	Phase 1
0.8284	Intermediate Similarity	NPD7473	Discontinued
0.8258	Intermediate Similarity	NPD2796	Approved
0.8232	Intermediate Similarity	NPD1465	Phase 2
0.8232	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5402	Approved
0.8171	Intermediate Similarity	NPD6801	Discontinued
0.8121	Intermediate Similarity	NPD7819	Suspended
0.8086	Intermediate Similarity	NPD5403	Approved
0.8052	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1613	Approved
0.8046	Intermediate Similarity	NPD6559	Discontinued
0.8034	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7768	Phase 2
0.8012	Intermediate Similarity	NPD6799	Approved
0.7976	Intermediate Similarity	NPD3749	Approved
0.7963	Intermediate Similarity	NPD5401	Approved
0.7935	Intermediate Similarity	NPD943	Approved
0.7935	Intermediate Similarity	NPD1240	Approved
0.7908	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD8312	Approved
0.7853	Intermediate Similarity	NPD8313	Approved
0.7849	Intermediate Similarity	NPD3926	Phase 2
0.7843	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1607	Approved
0.7831	Intermediate Similarity	NPD6599	Discontinued
0.7826	Intermediate Similarity	NPD3750	Approved
0.7791	Intermediate Similarity	NPD7390	Discontinued
0.7791	Intermediate Similarity	NPD3787	Discontinued
0.7742	Intermediate Similarity	NPD3027	Phase 3
0.7733	Intermediate Similarity	NPD1247	Approved
0.7733	Intermediate Similarity	NPD7199	Phase 2
0.7719	Intermediate Similarity	NPD919	Approved
0.7714	Intermediate Similarity	NPD3751	Discontinued
0.7711	Intermediate Similarity	NPD1653	Approved
0.7702	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6234	Discontinued
0.7614	Intermediate Similarity	NPD7228	Approved
0.7588	Intermediate Similarity	NPD8455	Phase 2
0.7578	Intermediate Similarity	NPD1551	Phase 2
0.7576	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4908	Phase 1
0.7561	Intermediate Similarity	NPD6190	Approved
0.7547	Intermediate Similarity	NPD230	Phase 1
0.753	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7487	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2935	Discontinued
0.7468	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7685	Pre-registration
0.7439	Intermediate Similarity	NPD2800	Approved
0.7438	Intermediate Similarity	NPD447	Suspended
0.7427	Intermediate Similarity	NPD37	Approved
0.7425	Intermediate Similarity	NPD2532	Approved
0.7425	Intermediate Similarity	NPD2534	Approved
0.7425	Intermediate Similarity	NPD2533	Approved
0.7423	Intermediate Similarity	NPD8151	Discontinued
0.7407	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4966	Approved
0.7399	Intermediate Similarity	NPD4965	Approved
0.7399	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD6777	Approved
0.7368	Intermediate Similarity	NPD6780	Approved
0.7368	Intermediate Similarity	NPD6778	Approved
0.7368	Intermediate Similarity	NPD6781	Approved
0.7368	Intermediate Similarity	NPD6782	Approved
0.7368	Intermediate Similarity	NPD6779	Approved
0.7368	Intermediate Similarity	NPD6776	Approved
0.7362	Intermediate Similarity	NPD6099	Approved
0.7362	Intermediate Similarity	NPD6100	Approved
0.7353	Intermediate Similarity	NPD3226	Approved
0.7338	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD920	Approved
0.7329	Intermediate Similarity	NPD1933	Approved
0.7321	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2344	Approved
0.7308	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD5953	Discontinued
0.7289	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4363	Phase 3
0.7287	Intermediate Similarity	NPD4360	Phase 2
0.7284	Intermediate Similarity	NPD6651	Approved
0.7278	Intermediate Similarity	NPD9494	Approved
0.7254	Intermediate Similarity	NPD7435	Discontinued
0.7251	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6798	Discontinued
0.725	Intermediate Similarity	NPD2313	Discontinued
0.7244	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD8150	Discontinued
0.7231	Intermediate Similarity	NPD7584	Approved
0.7229	Intermediate Similarity	NPD1243	Approved
0.7226	Intermediate Similarity	NPD1610	Phase 2
0.7216	Intermediate Similarity	NPD7870	Phase 2
0.7216	Intermediate Similarity	NPD7871	Phase 2
0.7213	Intermediate Similarity	NPD7549	Discontinued
0.7195	Intermediate Similarity	NPD7033	Discontinued
0.7195	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1548	Phase 1
0.7182	Intermediate Similarity	NPD7286	Phase 2
0.7172	Intermediate Similarity	NPD7783	Phase 2
0.7172	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7698	Approved
0.7165	Intermediate Similarity	NPD7697	Approved
0.7165	Intermediate Similarity	NPD7696	Phase 3
0.7158	Intermediate Similarity	NPD7240	Approved
0.7152	Intermediate Similarity	NPD5404	Approved
0.7152	Intermediate Similarity	NPD5406	Approved
0.7152	Intermediate Similarity	NPD5405	Approved
0.7152	Intermediate Similarity	NPD5408	Approved
0.7152	Intermediate Similarity	NPD1203	Approved
0.7151	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD2309	Approved
0.7135	Intermediate Similarity	NPD8127	Discontinued
0.7126	Intermediate Similarity	NPD6844	Discontinued
0.7125	Intermediate Similarity	NPD6832	Phase 2
0.7113	Intermediate Similarity	NPD6823	Phase 2
0.7108	Intermediate Similarity	NPD2346	Discontinued
0.7108	Intermediate Similarity	NPD7266	Discontinued
0.7107	Intermediate Similarity	NPD7701	Phase 2
0.7105	Intermediate Similarity	NPD6534	Approved
0.7105	Intermediate Similarity	NPD6535	Approved
0.7099	Intermediate Similarity	NPD6233	Phase 2
0.7091	Intermediate Similarity	NPD2799	Discontinued
0.7083	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD4287	Approved
0.7063	Intermediate Similarity	NPD2861	Phase 2
0.7059	Intermediate Similarity	NPD7212	Phase 2
0.7059	Intermediate Similarity	NPD7213	Phase 3
0.7059	Intermediate Similarity	NPD8434	Phase 2
0.7056	Intermediate Similarity	NPD5242	Approved
0.7045	Intermediate Similarity	NPD5353	Approved
0.7037	Intermediate Similarity	NPD3268	Approved
0.7035	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7874	Approved
0.7024	Intermediate Similarity	NPD1652	Phase 2
0.7018	Intermediate Similarity	NPD7447	Phase 1
0.7017	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5124	Phase 1
0.7	Intermediate Similarity	NPD5710	Approved
0.7	Intermediate Similarity	NPD7229	Phase 3
0.7	Intermediate Similarity	NPD2798	Approved
0.7	Intermediate Similarity	NPD7801	Approved
0.7	Intermediate Similarity	NPD5711	Approved
0.6995	Remote Similarity	NPD7699	Phase 2
0.6995	Remote Similarity	NPD7700	Phase 2
0.6982	Remote Similarity	NPD8166	Discontinued
0.6981	Remote Similarity	NPD3225	Approved
0.6973	Remote Similarity	NPD7038	Approved
0.6973	Remote Similarity	NPD7039	Approved
0.6971	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD9269	Phase 2
0.6957	Remote Similarity	NPD3018	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