NPASS Compound

Structure

CID278476 OpenBabel06191716082D 31 33 0 0 1 0 0 0 0 0999 V2000 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 3.4641 -3.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 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 1.7321 -0.0000 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 2.5981 0.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 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 3.4641 -0.0000 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 0.0000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 7 1 0 0 0 0 5 13 2 0 0 0 0 6 9 1 0 0 0 0 6 14 2 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 15 18 1 0 0 0 0 17 19 1 0 0 0 0 17 25 2 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 21 2 0 0 0 0 20 28 1 0 0 0 0 21 22 1 0 0 0 0 21 25 1 0 0 0 0 22 23 1 0 0 0 0 22 29 2 0 0 0 0 23 24 1 0 0 0 0 23 30 1 1 0 0 0 24 16 1 6 0 0 0 24 31 1 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.19
Volume:	444.3
LogP:	5.688
LogD:	3.674
LogS:	-2.72
# Rotatable Bonds:	5
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.527
Synthetic Accessibility Score:	3.863
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.937
MDCK Permeability:	1.313045959250303e-05
Pgp-inhibitor:	0.631
Pgp-substrate:	0.118
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.939
30% Bioavailability (F30%):	0.165

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	95.67901611328125%
Volume Distribution (VD):	0.691
Pgp-substrate:	4.549530982971191%

ADMET: Metabolism

CYP1A2-inhibitor:	0.193
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.684
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.862
CYP2C9-substrate:	0.901
CYP2D6-inhibitor:	0.934
CYP2D6-substrate:	0.27
CYP3A4-inhibitor:	0.389
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	10.453
Half-life (T1/2):	0.16

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.423
Drug-inuced Liver Injury (DILI):	0.859
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.269
Maximum Recommended Daily Dose:	0.087
Skin Sensitization:	0.83
Carcinogencity:	0.056
Eye Corrosion:	0.003
Eye Irritation:	0.416
Respiratory Toxicity:	0.112

Download Data

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

Natural Product: NPC278476

Natural Product ID:	NPC278476
*Common Name:**	(2R,3R)-Lespedezaflavanone C
IUPAC Name:	(2R,3R)-3,5,7-trihydroxy-2-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Synonyms:	(2R,3R)-Lespedezaflavanone C
Standard InCHIKey:	WFHBGCVPESHDKZ-BJKOFHAPSA-N
Standard InCHI:	InChI=1S/C25H28O6/c1-13(2)5-7-15-11-16(8-10-18(15)26)24-23(30)22(29)21-20(28)12-19(27)17(25(21)31-24)9-6-14(3)4/h5-6,8,10-12,23-24,26-28,30H,7,9H2,1-4H3/t23-,24+/m0/s1
SMILES:	CC(=CCc1cc(ccc1O)[C@@H]1[C@H](C(=O)c2c(cc(c(CC=C(C)C)c2O1)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463256
PubChem CID:	14542252
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003642] 8-prenylated flavans [CHEMONTID:0003508] 8-prenylated flavanones

*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
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[11395279]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	n.a.	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	Shawnee National Forest, Harrisburg, IL, US	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12419367]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	leaves	Kaohsiung, Taiwan	2006-SEP	PMID[18986201]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[19296617]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5495	Broussonetia papyrifera	Species	Moraceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	>	40.0	ug.mL-1	PMID[571185]

☑ 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 NPC278476 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	380
0.1-0.2	1405
0.2-0.3	3588
0.3-0.4	8679
0.4-0.5	9761
0.5-0.6	3646
0.6-0.7	5131
0.7-0.8	5287
0.8-0.85	2754
0.85-0.9	1422
0.9-0.95	552
0.95-1	92

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC254412
1.0	High Similarity	NPC262039
1.0	High Similarity	NPC319910
1.0	High Similarity	NPC262038
0.9931	High Similarity	NPC105136
0.9931	High Similarity	NPC35567
0.9931	High Similarity	NPC216035
0.9931	High Similarity	NPC171651
0.9931	High Similarity	NPC243171
0.9931	High Similarity	NPC217149
0.9931	High Similarity	NPC138288
0.9863	High Similarity	NPC293286
0.9796	High Similarity	NPC304207
0.9796	High Similarity	NPC111341
0.9796	High Similarity	NPC48579
0.9796	High Similarity	NPC207809
0.9796	High Similarity	NPC217706
0.9796	High Similarity	NPC304745
0.9796	High Similarity	NPC259710
0.973	High Similarity	NPC215917
0.973	High Similarity	NPC10754
0.973	High Similarity	NPC20530
0.9728	High Similarity	NPC244250
0.9728	High Similarity	NPC248793
0.9728	High Similarity	NPC268193
0.9728	High Similarity	NPC20907
0.9728	High Similarity	NPC180301
0.9726	High Similarity	NPC471677
0.9726	High Similarity	NPC263384
0.9726	High Similarity	NPC472420
0.9726	High Similarity	NPC472422
0.9726	High Similarity	NPC471676
0.9726	High Similarity	NPC244577
0.9722	High Similarity	NPC476182
0.9722	High Similarity	NPC40086
0.9722	High Similarity	NPC44721
0.9722	High Similarity	NPC211466
0.9722	High Similarity	NPC176869
0.9722	High Similarity	NPC3779
0.9722	High Similarity	NPC122828
0.966	High Similarity	NPC161881
0.966	High Similarity	NPC10807
0.966	High Similarity	NPC56232
0.966	High Similarity	NPC150123
0.966	High Similarity	NPC244583
0.966	High Similarity	NPC210597
0.966	High Similarity	NPC475790
0.9653	High Similarity	NPC472629
0.96	High Similarity	NPC22192
0.9595	High Similarity	NPC472583
0.9595	High Similarity	NPC7989
0.9595	High Similarity	NPC100134
0.9595	High Similarity	NPC209760
0.9595	High Similarity	NPC236756
0.9595	High Similarity	NPC311579
0.9595	High Similarity	NPC223701
0.9592	High Similarity	NPC472636
0.9592	High Similarity	NPC328740
0.9592	High Similarity	NPC289774
0.9592	High Similarity	NPC209846
0.9592	High Similarity	NPC477897
0.9592	High Similarity	NPC474021
0.9592	High Similarity	NPC474023
0.9589	High Similarity	NPC472628
0.9589	High Similarity	NPC89442
0.9586	High Similarity	NPC472918
0.9586	High Similarity	NPC472627
0.9583	High Similarity	NPC279417
0.9583	High Similarity	NPC470890
0.9583	High Similarity	NPC49130
0.9583	High Similarity	NPC326506
0.9583	High Similarity	NPC142731
0.9583	High Similarity	NPC124780
0.9583	High Similarity	NPC306607
0.9583	High Similarity	NPC62290
0.9583	High Similarity	NPC87486
0.9583	High Similarity	NPC4152
0.9583	High Similarity	NPC208176
0.9536	High Similarity	NPC282009
0.9536	High Similarity	NPC287328
0.953	High Similarity	NPC476169
0.953	High Similarity	NPC471116
0.953	High Similarity	NPC477958
0.9527	High Similarity	NPC473996
0.9524	High Similarity	NPC61258
0.9521	High Similarity	NPC218569
0.9521	High Similarity	NPC10097
0.9517	High Similarity	NPC148011
0.9517	High Similarity	NPC1940
0.9474	High Similarity	NPC471499
0.947	High Similarity	NPC123544
0.9467	High Similarity	NPC78492
0.9467	High Similarity	NPC208152
0.9463	High Similarity	NPC112701
0.9463	High Similarity	NPC88983
0.9463	High Similarity	NPC326592
0.9463	High Similarity	NPC469405
0.9463	High Similarity	NPC109594
0.9459	High Similarity	NPC474772
0.9459	High Similarity	NPC474744
0.9459	High Similarity	NPC472423
0.9459	High Similarity	NPC472580
0.9459	High Similarity	NPC471229
0.9459	High Similarity	NPC471675
0.9456	High Similarity	NPC277032
0.9456	High Similarity	NPC470461
0.9456	High Similarity	NPC307052
0.9456	High Similarity	NPC139966
0.9452	High Similarity	NPC47388
0.9452	High Similarity	NPC21835
0.9452	High Similarity	NPC470670
0.9452	High Similarity	NPC473133
0.9452	High Similarity	NPC85773
0.9452	High Similarity	NPC91902
0.9448	High Similarity	NPC273538
0.9448	High Similarity	NPC216538
0.9448	High Similarity	NPC224714
0.9444	High Similarity	NPC66515
0.9444	High Similarity	NPC296917
0.9444	High Similarity	NPC306829
0.9444	High Similarity	NPC32739
0.9444	High Similarity	NPC76372
0.9444	High Similarity	NPC107572
0.9444	High Similarity	NPC324134
0.9444	High Similarity	NPC166934
0.9444	High Similarity	NPC324436
0.9444	High Similarity	NPC194432
0.9444	High Similarity	NPC161506
0.9444	High Similarity	NPC265040
0.9444	High Similarity	NPC227579
0.9444	High Similarity	NPC37496
0.9444	High Similarity	NPC167624
0.9444	High Similarity	NPC228504
0.9444	High Similarity	NPC220998
0.9444	High Similarity	NPC76338
0.9444	High Similarity	NPC78
0.9444	High Similarity	NPC166482
0.9444	High Similarity	NPC223500
0.9444	High Similarity	NPC10937
0.9444	High Similarity	NPC177354
0.9444	High Similarity	NPC40833
0.9444	High Similarity	NPC64915
0.9444	High Similarity	NPC328164
0.9444	High Similarity	NPC182852
0.9444	High Similarity	NPC1089
0.9444	High Similarity	NPC125855
0.9444	High Similarity	NPC148757
0.9412	High Similarity	NPC131745
0.9412	High Similarity	NPC259834
0.9408	High Similarity	NPC470326
0.9408	High Similarity	NPC306978
0.9404	High Similarity	NPC474055
0.9404	High Similarity	NPC472598
0.94	High Similarity	NPC321779
0.94	High Similarity	NPC470681
0.9396	High Similarity	NPC285623
0.9396	High Similarity	NPC327269
0.9396	High Similarity	NPC477957
0.9396	High Similarity	NPC476238
0.9396	High Similarity	NPC31627
0.9392	High Similarity	NPC124478
0.9392	High Similarity	NPC177308
0.9392	High Similarity	NPC472421
0.9392	High Similarity	NPC267117
0.9388	High Similarity	NPC470460
0.9388	High Similarity	NPC296869
0.9384	High Similarity	NPC290133
0.9384	High Similarity	NPC5820
0.9384	High Similarity	NPC316769
0.9384	High Similarity	NPC187282
0.9384	High Similarity	NPC474302
0.9384	High Similarity	NPC470458
0.9384	High Similarity	NPC229190
0.9384	High Similarity	NPC124729
0.9384	High Similarity	NPC306488
0.9384	High Similarity	NPC24136
0.9384	High Similarity	NPC178343
0.9379	High Similarity	NPC149026
0.9379	High Similarity	NPC310130
0.9379	High Similarity	NPC257097
0.9379	High Similarity	NPC81697
0.9379	High Similarity	NPC85162
0.9379	High Similarity	NPC150408
0.9379	High Similarity	NPC68104
0.9379	High Similarity	NPC9117
0.9379	High Similarity	NPC278249
0.9379	High Similarity	NPC143896
0.9379	High Similarity	NPC190637
0.9379	High Similarity	NPC24821
0.9379	High Similarity	NPC185276
0.9379	High Similarity	NPC212932
0.9379	High Similarity	NPC301751
0.9379	High Similarity	NPC214166
0.9379	High Similarity	NPC175504
0.9379	High Similarity	NPC478086
0.9379	High Similarity	NPC75049
0.9379	High Similarity	NPC221432
0.9379	High Similarity	NPC91560
0.9379	High Similarity	NPC125894
0.9379	High Similarity	NPC107177

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 NPC278476 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	861
0.2-0.3	1656
0.3-0.4	2577
0.4-0.5	1892
0.5-0.6	1107
0.6-0.7	495
0.7-0.8	171
0.8-0.85	36
0.85-0.9	12
0.9-0.95	11
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9448	High Similarity	NPD4378	Clinical (unspecified phase)
0.9404	High Similarity	NPD7075	Discontinued
0.9392	High Similarity	NPD4380	Phase 2
0.9333	High Similarity	NPD7096	Clinical (unspecified phase)
0.9333	High Similarity	NPD2393	Clinical (unspecified phase)
0.9139	High Similarity	NPD6801	Discontinued
0.9139	High Similarity	NPD1934	Approved
0.9114	High Similarity	NPD7804	Clinical (unspecified phase)
0.9097	High Similarity	NPD1552	Clinical (unspecified phase)
0.9097	High Similarity	NPD1550	Clinical (unspecified phase)
0.9045	High Similarity	NPD6168	Clinical (unspecified phase)
0.9045	High Similarity	NPD6167	Clinical (unspecified phase)
0.9045	High Similarity	NPD6166	Phase 2
0.9034	High Similarity	NPD1549	Phase 2
0.9026	High Similarity	NPD4381	Clinical (unspecified phase)
0.8896	High Similarity	NPD8443	Clinical (unspecified phase)
0.8859	High Similarity	NPD6799	Approved
0.8767	High Similarity	NPD2796	Approved
0.8742	High Similarity	NPD1512	Approved
0.8718	High Similarity	NPD3882	Suspended
0.871	High Similarity	NPD2801	Approved
0.8701	High Similarity	NPD7411	Suspended
0.8699	High Similarity	NPD1510	Phase 2
0.8675	High Similarity	NPD7410	Clinical (unspecified phase)
0.8654	High Similarity	NPD3817	Phase 2
0.865	High Similarity	NPD6797	Phase 2
0.8636	High Similarity	NPD6599	Discontinued
0.8609	High Similarity	NPD1511	Approved
0.8598	High Similarity	NPD7251	Discontinued
0.859	High Similarity	NPD7819	Suspended
0.8589	High Similarity	NPD7074	Phase 3
0.8562	High Similarity	NPD5403	Approved
0.8552	High Similarity	NPD1240	Approved
0.8545	High Similarity	NPD7808	Phase 3
0.8528	High Similarity	NPD7054	Approved
0.85	High Similarity	NPD6959	Discontinued
0.8485	Intermediate Similarity	NPD6559	Discontinued
0.8476	Intermediate Similarity	NPD7472	Approved
0.8466	Intermediate Similarity	NPD3818	Discontinued
0.8438	Intermediate Similarity	NPD5494	Approved
0.8435	Intermediate Similarity	NPD1607	Approved
0.8434	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD5401	Approved
0.8418	Intermediate Similarity	NPD5402	Approved
0.8365	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD7768	Phase 2
0.8224	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD2800	Approved
0.8204	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD5844	Phase 1
0.817	Intermediate Similarity	NPD4628	Phase 3
0.811	Intermediate Similarity	NPD6232	Discontinued
0.8072	Intermediate Similarity	NPD7473	Discontinued
0.8052	Intermediate Similarity	NPD3750	Approved
0.8041	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1551	Phase 2
0.8026	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3749	Approved
0.7975	Intermediate Similarity	NPD920	Approved
0.7966	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD2534	Approved
0.7962	Intermediate Similarity	NPD2533	Approved
0.7962	Intermediate Similarity	NPD2532	Approved
0.7947	Intermediate Similarity	NPD6651	Approved
0.7943	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD1247	Approved
0.7933	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD1613	Approved
0.7927	Intermediate Similarity	NPD919	Approved
0.7922	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD5953	Discontinued
0.7871	Intermediate Similarity	NPD1243	Approved
0.787	Intermediate Similarity	NPD7286	Phase 2
0.7853	Intermediate Similarity	NPD4363	Phase 3
0.7853	Intermediate Similarity	NPD4360	Phase 2
0.7848	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD2799	Discontinued
0.7834	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3751	Discontinued
0.78	Intermediate Similarity	NPD2313	Discontinued
0.78	Intermediate Similarity	NPD6798	Discontinued
0.7793	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD4908	Phase 1
0.7784	Intermediate Similarity	NPD3787	Discontinued
0.7742	Intermediate Similarity	NPD2344	Approved
0.7738	Intermediate Similarity	NPD3926	Phase 2
0.7727	Intermediate Similarity	NPD3748	Approved
0.7727	Intermediate Similarity	NPD7033	Discontinued
0.7697	Intermediate Similarity	NPD943	Approved
0.7692	Intermediate Similarity	NPD2424	Discontinued
0.7683	Intermediate Similarity	NPD1465	Phase 2
0.7677	Intermediate Similarity	NPD6100	Approved
0.7677	Intermediate Similarity	NPD6099	Approved
0.7676	Intermediate Similarity	NPD7584	Approved
0.7671	Intermediate Similarity	NPD1610	Phase 2
0.7669	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3226	Approved
0.7647	Intermediate Similarity	NPD5124	Phase 1
0.7647	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6355	Discontinued
0.7644	Intermediate Similarity	NPD8312	Approved
0.7644	Intermediate Similarity	NPD8313	Approved
0.7637	Intermediate Similarity	NPD6782	Approved
0.7637	Intermediate Similarity	NPD6778	Approved
0.7637	Intermediate Similarity	NPD6777	Approved
0.7637	Intermediate Similarity	NPD6776	Approved
0.7637	Intermediate Similarity	NPD6781	Approved
0.7637	Intermediate Similarity	NPD6779	Approved
0.7637	Intermediate Similarity	NPD6780	Approved
0.7632	Intermediate Similarity	NPD6233	Phase 2
0.7628	Intermediate Similarity	NPD2346	Discontinued
0.7616	Intermediate Similarity	NPD3027	Phase 3
0.7614	Intermediate Similarity	NPD8434	Phase 2
0.7613	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1203	Approved
0.7576	Intermediate Similarity	NPD8455	Phase 2
0.7562	Intermediate Similarity	NPD7390	Discontinued
0.755	Intermediate Similarity	NPD6832	Phase 2
0.7547	Intermediate Similarity	NPD2309	Approved
0.7532	Intermediate Similarity	NPD1652	Phase 2
0.7517	Intermediate Similarity	NPD1548	Phase 1
0.7516	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8150	Discontinued
0.7514	Intermediate Similarity	NPD7435	Discontinued
0.7514	Intermediate Similarity	NPD4361	Phase 2
0.7514	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5710	Approved
0.7471	Intermediate Similarity	NPD5711	Approved
0.7471	Intermediate Similarity	NPD3823	Discontinued
0.7468	Intermediate Similarity	NPD4060	Phase 1
0.7451	Intermediate Similarity	NPD3268	Approved
0.7446	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7458	Discontinued
0.7439	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6190	Approved
0.7427	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7698	Approved
0.7419	Intermediate Similarity	NPD7697	Approved
0.7419	Intermediate Similarity	NPD7696	Phase 3
0.7419	Intermediate Similarity	NPD1933	Approved
0.7419	Intermediate Similarity	NPD230	Phase 1
0.7417	Intermediate Similarity	NPD2798	Approved
0.7412	Intermediate Similarity	NPD7199	Phase 2
0.7407	Intermediate Similarity	NPD4662	Approved
0.7407	Intermediate Similarity	NPD4661	Approved
0.7389	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4625	Phase 3
0.7384	Intermediate Similarity	NPD2403	Approved
0.7384	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD9717	Approved
0.738	Intermediate Similarity	NPD7871	Phase 2
0.738	Intermediate Similarity	NPD7870	Phase 2
0.7363	Intermediate Similarity	NPD6535	Approved
0.7363	Intermediate Similarity	NPD6534	Approved
0.7362	Intermediate Similarity	NPD5049	Phase 3
0.736	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD7701	Phase 2
0.7351	Intermediate Similarity	NPD2797	Approved
0.7333	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3887	Approved
0.7329	Intermediate Similarity	NPD2354	Approved
0.7325	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4536	Approved
0.7325	Intermediate Similarity	NPD4538	Approved
0.7316	Intermediate Similarity	NPD8151	Discontinued
0.7315	Intermediate Similarity	NPD422	Phase 1
0.7314	Intermediate Similarity	NPD1729	Discontinued
0.7312	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2654	Approved
0.7308	Intermediate Similarity	NPD447	Suspended
0.7308	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6844	Discontinued
0.7305	Intermediate Similarity	NPD37	Approved
0.7294	Intermediate Similarity	NPD6234	Discontinued
0.729	Intermediate Similarity	NPD4062	Phase 3
0.7283	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4967	Phase 2
0.7278	Intermediate Similarity	NPD4965	Approved
0.7278	Intermediate Similarity	NPD4308	Phase 3
0.7278	Intermediate Similarity	NPD4966	Approved
0.7277	Intermediate Similarity	NPD7874	Approved
0.7277	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1653	Approved
0.7267	Intermediate Similarity	NPD7229	Phase 3
0.7263	Intermediate Similarity	NPD7585	Approved
0.7255	Intermediate Similarity	NPD2861	Phase 2
0.7243	Intermediate Similarity	NPD7699	Phase 2
0.7243	Intermediate Similarity	NPD7700	Phase 2
0.724	Intermediate Similarity	NPD7783	Phase 2
0.724	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7801	Approved
0.7239	Intermediate Similarity	NPD6143	Clinical (unspecified phase)

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