NPASS Compound

Structure

CID259757 OpenBabel06191716062D 41 46 0 0 0 0 0 0 0 0999 V2000 1.7321 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 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 3.4641 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 1.7321 0.0000 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 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 6.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 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 0.8660 -0.5000 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 -4.3301 4.5000 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 -5.1962 4.0000 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 -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 -2.5981 -1.5000 0.0000 C 0 0 0 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 -5.1962 7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 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 -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 -3.4641 -2.0000 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 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 12 2 0 0 0 0 2 5 2 0 0 0 0 2 12 1 0 0 0 0 3 6 2 0 0 0 0 3 13 1 0 0 0 0 4 14 2 0 0 0 0 5 14 1 0 0 0 0 6 17 1 0 0 0 0 7 13 2 0 0 0 0 7 16 1 0 0 0 0 8 15 2 0 0 0 0 8 18 1 0 0 0 0 9 15 1 0 0 0 0 9 23 2 0 0 0 0 10 19 1 0 0 0 0 10 22 2 0 0 0 0 11 20 1 0 0 0 0 11 21 2 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 31 1 0 0 0 0 15 32 1 0 0 0 0 16 17 2 0 0 0 0 16 24 1 0 0 0 0 17 33 1 0 0 0 0 18 25 2 0 0 0 0 18 34 1 0 0 0 0 19 25 1 0 0 0 0 19 35 2 0 0 0 0 20 26 1 0 0 0 0 20 36 2 0 0 0 0 21 41 1 0 0 0 0 22 40 1 0 0 0 0 23 25 1 0 0 0 0 23 40 1 0 0 0 0 24 27 1 0 0 0 0 24 30 2 0 0 0 0 26 28 2 0 0 0 0 26 30 1 0 0 0 0 27 29 2 0 0 0 0 27 37 1 0 0 0 0 28 29 1 0 0 0 0 28 38 1 0 0 0 0 29 39 1 0 0 0 0 30 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	554.08
Volume:	530.606
LogP:	5.574
LogD:	2.257
LogS:	-4.43
# Rotatable Bonds:	3
TPSA:	202.03
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.148
Synthetic Accessibility Score:	3.133
Fsp3:	0.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.365
MDCK Permeability:	7.173892299761064e-06
Pgp-inhibitor:	0.023
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.675
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	98.0846939086914%
Volume Distribution (VD):	0.468
Pgp-substrate:	8.972540855407715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.817
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.144
CYP2C19-substrate:	0.033
CYP2C9-inhibitor:	0.541
CYP2C9-substrate:	0.6
CYP2D6-inhibitor:	0.042
CYP2D6-substrate:	0.188
CYP3A4-inhibitor:	0.089
CYP3A4-substrate:	0.039

ADMET: Excretion

Clearance (CL):	3.161
Half-life (T1/2):	0.826

ADMET: Toxicity

hERG Blockers:	0.15
Human Hepatotoxicity (H-HT):	0.124
Drug-inuced Liver Injury (DILI):	0.99
AMES Toxicity:	0.246
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.618
Skin Sensitization:	0.928
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.896
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC259757

Natural Product ID:	NPC259757
*Common Name:**	Sumaflavone
IUPAC Name:	8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-5,6,7-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms:	sumaflavone
Standard InCHIKey:	BCTLOSNRPJXRNV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H18O11/c31-14-4-1-12(2-5-14)21-11-20(36)26-28(38)29(39)27(37)24(30(26)41-21)16-7-13(3-6-17(16)33)22-10-19(35)25-18(34)8-15(32)9-23(25)40-22/h1-11,31-34,37-39H
SMILES:	Oc1ccc(cc1)c1cc(=O)c2c(o1)c(c1cc(ccc1O)c1cc(=O)c3c(o1)cc(cc3O)O)c(c(c2O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL270509
PubChem CID:	24936074
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
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20335035]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25559759]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29144743]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31244143]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	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
Others	2

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	50.0	%	PMID[497502]
NPT2	Others	Unspecified		IC50	=	780.0	nM	PMID[497502]

☑ 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 NPC259757 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	629
0.1-0.2	2332
0.2-0.3	5624
0.3-0.4	11642
0.4-0.5	5199
0.5-0.6	4317
0.6-0.7	5342
0.7-0.8	4608
0.8-0.85	1883
0.85-0.9	935
0.9-0.95	180
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC272560
0.9554	High Similarity	NPC196179
0.9554	High Similarity	NPC34089
0.9437	High Similarity	NPC171985
0.9437	High Similarity	NPC320741
0.9434	High Similarity	NPC272064
0.9363	High Similarity	NPC112954
0.9329	High Similarity	NPC99591
0.9321	High Similarity	NPC107627
0.9317	High Similarity	NPC224851
0.9299	High Similarity	NPC276444
0.929	High Similarity	NPC222713
0.929	High Similarity	NPC138299
0.929	High Similarity	NPC111112
0.929	High Similarity	NPC67322
0.9277	High Similarity	NPC324742
0.9273	High Similarity	NPC216307
0.9241	High Similarity	NPC476630
0.9241	High Similarity	NPC218871
0.9241	High Similarity	NPC185526
0.9236	High Similarity	NPC254351
0.9187	High Similarity	NPC198829
0.9187	High Similarity	NPC259456
0.9172	High Similarity	NPC72425
0.9172	High Similarity	NPC194593
0.9172	High Similarity	NPC303485
0.9172	High Similarity	NPC71061
0.9172	High Similarity	NPC290830
0.9172	High Similarity	NPC170492
0.9161	High Similarity	NPC291746
0.9161	High Similarity	NPC288840
0.9141	High Similarity	NPC50394
0.9136	High Similarity	NPC156432
0.913	High Similarity	NPC219927
0.913	High Similarity	NPC329760
0.913	High Similarity	NPC194427
0.9125	High Similarity	NPC204290
0.9119	High Similarity	NPC183
0.9114	High Similarity	NPC215203
0.9114	High Similarity	NPC52611
0.9114	High Similarity	NPC186227
0.9114	High Similarity	NPC150908
0.9114	High Similarity	NPC205026
0.9114	High Similarity	NPC14606
0.9114	High Similarity	NPC159707
0.9114	High Similarity	NPC158027
0.9114	High Similarity	NPC100049
0.9114	High Similarity	NPC265624
0.9114	High Similarity	NPC121649
0.9114	High Similarity	NPC248739
0.9108	High Similarity	NPC249570
0.9103	High Similarity	NPC88804
0.9103	High Similarity	NPC3825
0.9102	High Similarity	NPC265380
0.9091	High Similarity	NPC186847
0.9091	High Similarity	NPC472454
0.9091	High Similarity	NPC257667
0.9085	High Similarity	NPC475212
0.908	High Similarity	NPC472449
0.9074	High Similarity	NPC189473
0.9074	High Similarity	NPC207690
0.9074	High Similarity	NPC23298
0.9068	High Similarity	NPC167678
0.9068	High Similarity	NPC29876
0.9062	High Similarity	NPC172770
0.9062	High Similarity	NPC185258
0.9062	High Similarity	NPC177650
0.9062	High Similarity	NPC46736
0.9062	High Similarity	NPC469658
0.9062	High Similarity	NPC154304
0.9062	High Similarity	NPC55443
0.9062	High Similarity	NPC18699
0.9062	High Similarity	NPC190487
0.9057	High Similarity	NPC191146
0.9057	High Similarity	NPC471985
0.9057	High Similarity	NPC68093
0.9057	High Similarity	NPC142339
0.9051	High Similarity	NPC476631
0.9048	High Similarity	NPC185275
0.9036	High Similarity	NPC149846
0.9032	High Similarity	NPC275772
0.9032	High Similarity	NPC239312
0.9032	High Similarity	NPC130230
0.9024	High Similarity	NPC243877
0.9024	High Similarity	NPC260266
0.9018	High Similarity	NPC50960
0.9018	High Similarity	NPC275780
0.9018	High Similarity	NPC472450
0.9018	High Similarity	NPC239752
0.9012	High Similarity	NPC472448
0.9012	High Similarity	NPC206605
0.9012	High Similarity	NPC477841
0.9012	High Similarity	NPC83922
0.9012	High Similarity	NPC261470
0.9006	High Similarity	NPC188967
0.9006	High Similarity	NPC476280
0.9006	High Similarity	NPC235018
0.9006	High Similarity	NPC312993
0.9006	High Similarity	NPC297212
0.9006	High Similarity	NPC186325
0.9006	High Similarity	NPC45146
0.9006	High Similarity	NPC476980
0.9	High Similarity	NPC236796
0.9	High Similarity	NPC78225
0.9	High Similarity	NPC237418
0.9	High Similarity	NPC79053
0.8994	High Similarity	NPC183597
0.8994	High Similarity	NPC182555
0.8994	High Similarity	NPC163780
0.8994	High Similarity	NPC201136
0.8994	High Similarity	NPC128863
0.8994	High Similarity	NPC113906
0.8994	High Similarity	NPC227325
0.8994	High Similarity	NPC92659
0.8994	High Similarity	NPC167815
0.8994	High Similarity	NPC4455
0.8994	High Similarity	NPC2476
0.8994	High Similarity	NPC66441
0.8994	High Similarity	NPC146165
0.8994	High Similarity	NPC138360
0.8994	High Similarity	NPC280339
0.8994	High Similarity	NPC50715
0.8994	High Similarity	NPC196439
0.8988	High Similarity	NPC471789
0.8987	High Similarity	NPC37684
0.8987	High Similarity	NPC157784
0.8987	High Similarity	NPC63187
0.8981	High Similarity	NPC184136
0.8981	High Similarity	NPC77858
0.8976	High Similarity	NPC289396
0.8976	High Similarity	NPC174700
0.8976	High Similarity	NPC212038
0.8976	High Similarity	NPC248593
0.8976	High Similarity	NPC271848
0.8976	High Similarity	NPC28589
0.8976	High Similarity	NPC81332
0.8976	High Similarity	NPC262580
0.8974	High Similarity	NPC12367
0.8974	High Similarity	NPC276930
0.8974	High Similarity	NPC118726
0.897	High Similarity	NPC300307
0.897	High Similarity	NPC476637
0.8963	High Similarity	NPC277480
0.8963	High Similarity	NPC37870
0.8963	High Similarity	NPC39091
0.8957	High Similarity	NPC270837
0.8957	High Similarity	NPC303460
0.8957	High Similarity	NPC12461
0.8957	High Similarity	NPC306321
0.8951	High Similarity	NPC472275
0.8951	High Similarity	NPC258331
0.8951	High Similarity	NPC278427
0.8951	High Similarity	NPC273467
0.8951	High Similarity	NPC40037
0.8951	High Similarity	NPC142252
0.8951	High Similarity	NPC266314
0.8951	High Similarity	NPC189552
0.8951	High Similarity	NPC32694
0.8944	High Similarity	NPC197856
0.8944	High Similarity	NPC53545
0.8944	High Similarity	NPC117418
0.8944	High Similarity	NPC100123
0.8938	High Similarity	NPC138243
0.8938	High Similarity	NPC282307
0.8938	High Similarity	NPC32867
0.8938	High Similarity	NPC170026
0.8938	High Similarity	NPC3980
0.8931	High Similarity	NPC276409
0.8931	High Similarity	NPC145379
0.8931	High Similarity	NPC255350
0.8931	High Similarity	NPC75279
0.8931	High Similarity	NPC160951
0.8931	High Similarity	NPC176775
0.8931	High Similarity	NPC250822
0.8931	High Similarity	NPC231018
0.8931	High Similarity	NPC47781
0.8931	High Similarity	NPC274327
0.8931	High Similarity	NPC183878
0.8931	High Similarity	NPC69394
0.8931	High Similarity	NPC22519
0.8931	High Similarity	NPC89474
0.8924	High Similarity	NPC154345
0.8924	High Similarity	NPC304295
0.8924	High Similarity	NPC59162
0.8924	High Similarity	NPC205046
0.8922	High Similarity	NPC310794
0.8917	High Similarity	NPC195351
0.8917	High Similarity	NPC17286
0.8917	High Similarity	NPC296197
0.8917	High Similarity	NPC259713
0.8917	High Similarity	NPC216318
0.8916	High Similarity	NPC101107
0.8909	High Similarity	NPC295082
0.8909	High Similarity	NPC14662
0.8902	High Similarity	NPC37183
0.8902	High Similarity	NPC477840
0.8896	High Similarity	NPC25152
0.8896	High Similarity	NPC474150
0.8896	High Similarity	NPC78332
0.8896	High Similarity	NPC474162

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 NPC259757 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	533
0.1-0.2	1051
0.2-0.3	1966
0.3-0.4	2763
0.4-0.5	1590
0.5-0.6	865
0.6-0.7	240
0.7-0.8	98
0.8-0.85	35
0.85-0.9	7
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8931	High Similarity	NPD2801	Approved
0.8839	High Similarity	NPD1511	Approved
0.8812	High Similarity	NPD2393	Clinical (unspecified phase)
0.8726	High Similarity	NPD1512	Approved
0.8675	High Similarity	NPD6167	Clinical (unspecified phase)
0.8675	High Similarity	NPD6168	Clinical (unspecified phase)
0.8675	High Similarity	NPD6166	Phase 2
0.8606	High Similarity	NPD6959	Discontinued
0.8544	High Similarity	NPD7410	Clinical (unspecified phase)
0.8519	High Similarity	NPD1934	Approved
0.8476	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6232	Discontinued
0.8428	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD7473	Discontinued
0.8395	Intermediate Similarity	NPD4380	Phase 2
0.8353	Intermediate Similarity	NPD3818	Discontinued
0.8343	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD5494	Approved
0.8314	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD7054	Approved
0.8303	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD7472	Approved
0.8256	Intermediate Similarity	NPD7074	Phase 3
0.8253	Intermediate Similarity	NPD3882	Suspended
0.8208	Intermediate Similarity	NPD6797	Phase 2
0.8198	Intermediate Similarity	NPD5844	Phase 1
0.8193	Intermediate Similarity	NPD3817	Phase 2
0.8161	Intermediate Similarity	NPD7251	Discontinued
0.8146	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7768	Phase 2
0.8137	Intermediate Similarity	NPD7390	Discontinued
0.8133	Intermediate Similarity	NPD1465	Phase 2
0.8121	Intermediate Similarity	NPD7411	Suspended
0.8095	Intermediate Similarity	NPD3749	Approved
0.8095	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD5402	Approved
0.8024	Intermediate Similarity	NPD7819	Suspended
0.8011	Intermediate Similarity	NPD7808	Phase 3
0.7989	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7075	Discontinued
0.7987	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1510	Phase 2
0.7949	Intermediate Similarity	NPD943	Approved
0.7937	Intermediate Similarity	NPD1549	Phase 2
0.7857	Intermediate Similarity	NPD6801	Discontinued
0.7849	Intermediate Similarity	NPD1247	Approved
0.784	Intermediate Similarity	NPD3750	Approved
0.7812	Intermediate Similarity	NPD2796	Approved
0.7811	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2800	Approved
0.7759	Intermediate Similarity	NPD3926	Phase 2
0.7758	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6559	Discontinued
0.7722	Intermediate Similarity	NPD1240	Approved
0.7702	Intermediate Similarity	NPD2935	Discontinued
0.7679	Intermediate Similarity	NPD3226	Approved
0.7667	Intermediate Similarity	NPD8313	Approved
0.7667	Intermediate Similarity	NPD8312	Approved
0.7665	Intermediate Similarity	NPD5403	Approved
0.7663	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1607	Approved
0.7607	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3787	Discontinued
0.759	Intermediate Similarity	NPD6799	Approved
0.758	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2344	Approved
0.7545	Intermediate Similarity	NPD2534	Approved
0.7545	Intermediate Similarity	NPD2532	Approved
0.7545	Intermediate Similarity	NPD2533	Approved
0.7545	Intermediate Similarity	NPD5401	Approved
0.7531	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD3748	Approved
0.7531	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6599	Discontinued
0.7529	Intermediate Similarity	NPD919	Approved
0.7528	Intermediate Similarity	NPD3751	Discontinued
0.7516	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5404	Approved
0.7485	Intermediate Similarity	NPD5408	Approved
0.7485	Intermediate Similarity	NPD5406	Approved
0.7485	Intermediate Similarity	NPD5405	Approved
0.7484	Intermediate Similarity	NPD2313	Discontinued
0.7456	Intermediate Similarity	NPD920	Approved
0.7456	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1243	Approved
0.744	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2799	Discontinued
0.7399	Intermediate Similarity	NPD8455	Phase 2
0.7391	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1613	Approved
0.7382	Intermediate Similarity	NPD6781	Approved
0.7382	Intermediate Similarity	NPD6778	Approved
0.7382	Intermediate Similarity	NPD6779	Approved
0.7382	Intermediate Similarity	NPD6776	Approved
0.7382	Intermediate Similarity	NPD6780	Approved
0.7382	Intermediate Similarity	NPD6777	Approved
0.7382	Intermediate Similarity	NPD6782	Approved
0.7375	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2309	Approved
0.7347	Intermediate Similarity	NPD8151	Discontinued
0.7346	Intermediate Similarity	NPD230	Phase 1
0.7345	Intermediate Similarity	NPD7199	Phase 2
0.7333	Intermediate Similarity	NPD2346	Discontinued
0.733	Intermediate Similarity	NPD6234	Discontinued
0.7322	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5953	Discontinued
0.7301	Intermediate Similarity	NPD6651	Approved
0.7297	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6100	Approved
0.7273	Intermediate Similarity	NPD1551	Phase 2
0.7273	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7783	Phase 2
0.7273	Intermediate Similarity	NPD6099	Approved
0.7268	Intermediate Similarity	NPD7435	Discontinued
0.7263	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6190	Approved
0.725	Intermediate Similarity	NPD4908	Phase 1
0.7239	Intermediate Similarity	NPD447	Suspended
0.7238	Intermediate Similarity	NPD7228	Approved
0.7235	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7871	Phase 2
0.7231	Intermediate Similarity	NPD7870	Phase 2
0.7225	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1653	Approved
0.7207	Intermediate Similarity	NPD7229	Phase 3
0.7198	Intermediate Similarity	NPD7286	Phase 2
0.7181	Intermediate Similarity	NPD4287	Approved
0.7179	Intermediate Similarity	NPD7697	Approved
0.7179	Intermediate Similarity	NPD7698	Approved
0.7179	Intermediate Similarity	NPD7696	Phase 3
0.7176	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD8150	Discontinued
0.716	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD37	Approved
0.7128	Intermediate Similarity	NPD6823	Phase 2
0.7121	Intermediate Similarity	NPD7701	Phase 2
0.712	Intermediate Similarity	NPD4363	Phase 3
0.712	Intermediate Similarity	NPD4360	Phase 2
0.712	Intermediate Similarity	NPD6534	Approved
0.712	Intermediate Similarity	NPD6535	Approved
0.7119	Intermediate Similarity	NPD4965	Approved
0.7119	Intermediate Similarity	NPD4967	Phase 2
0.7119	Intermediate Similarity	NPD4966	Approved
0.7101	Intermediate Similarity	NPD7003	Approved
0.7101	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4628	Phase 3
0.7101	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4625	Phase 3
0.7099	Intermediate Similarity	NPD3027	Phase 3
0.7069	Intermediate Similarity	NPD7458	Discontinued
0.7063	Intermediate Similarity	NPD1470	Approved
0.7063	Intermediate Similarity	NPD1203	Approved
0.7055	Intermediate Similarity	NPD3268	Approved
0.705	Intermediate Similarity	NPD7874	Approved
0.705	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7177	Discontinued
0.7025	Intermediate Similarity	NPD1201	Approved
0.7019	Intermediate Similarity	NPD2798	Approved
0.7017	Intermediate Similarity	NPD5710	Approved
0.7017	Intermediate Similarity	NPD5711	Approved
0.7015	Intermediate Similarity	NPD7801	Approved
0.701	Intermediate Similarity	NPD7700	Phase 2
0.701	Intermediate Similarity	NPD7699	Phase 2
0.7	Intermediate Similarity	NPD3225	Approved
0.6989	Remote Similarity	NPD7685	Pre-registration
0.6984	Remote Similarity	NPD8434	Phase 2
0.6981	Remote Similarity	NPD9269	Phase 2
0.6966	Remote Similarity	NPD4288	Approved
0.6957	Remote Similarity	NPD2797	Approved
0.6952	Remote Similarity	NPD7549	Discontinued
0.6951	Remote Similarity	NPD3764	Approved
0.6949	Remote Similarity	NPD6844	Discontinued
0.6918	Remote Similarity	NPD1610	Phase 2
0.6907	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4361	Phase 2
0.6901	Remote Similarity	NPD8166	Discontinued
0.69	Remote Similarity	NPD7584	Approved
0.6891	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6213	Phase 3
0.6891	Remote Similarity	NPD6212	Phase 3
0.6879	Remote Similarity	NPD1548	Phase 1
0.6875	Remote Similarity	NPD1608	Approved
0.6872	Remote Similarity	NPD2296	Approved
0.6871	Remote Similarity	NPD9494	Approved
0.6871	Remote Similarity	NPD2861	Phase 2
0.684	Remote Similarity	NPD7654	Discontinued
0.6832	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6832	Phase 2
0.6826	Remote Similarity	NPD5124	Phase 1
0.6826	Remote Similarity	NPD1933	Approved
0.6826	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3300	Phase 2
0.6813	Remote Similarity	NPD1547	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