NPASS Compound

Structure

CID59162 OpenBabel06191715392D 32 34 0 0 0 0 0 0 0 0999 V2000 -6.0622 -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 3.4641 3.0000 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 -4.3301 -1.5000 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 -4.3301 -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 -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 2.5981 -1.5000 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 2.5981 2.5000 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 -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 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 -1.5000 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 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 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 0.8660 -0.5000 0.0000 C 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 -2.5981 2.5000 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 -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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 13 1 0 0 0 0 5 7 1 0 0 0 0 5 12 2 0 0 0 0 6 8 1 0 0 0 0 6 13 2 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 15 2 0 0 0 0 10 19 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 14 21 1 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 25 2 0 0 0 0 17 26 1 0 0 0 0 18 20 2 0 0 0 0 18 27 1 0 0 0 0 19 21 2 0 0 0 0 19 28 1 0 0 0 0 20 22 1 0 0 0 0 20 25 1 0 0 0 0 21 29 1 0 0 0 0 22 23 1 0 0 0 0 22 30 2 0 0 0 0 23 24 2 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.17
Volume:	450.454
LogP:	5.947
LogD:	2.967
LogS:	-2.961
# Rotatable Bonds:	5
TPSA:	131.36
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.274
Synthetic Accessibility Score:	3.323
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.149
MDCK Permeability:	1.2860297829320189e-05
Pgp-inhibitor:	0.319
Pgp-substrate:	0.06
Human Intestinal Absorption (HIA):	0.043
20% Bioavailability (F20%):	0.139
30% Bioavailability (F30%):	0.732

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	97.95970916748047%
Volume Distribution (VD):	0.621
Pgp-substrate:	3.769685745239258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.735
CYP1A2-substrate:	0.173
CYP2C19-inhibitor:	0.246
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.784
CYP2C9-substrate:	0.465
CYP2D6-inhibitor:	0.447
CYP2D6-substrate:	0.166
CYP3A4-inhibitor:	0.132
CYP3A4-substrate:	0.079

ADMET: Excretion

Clearance (CL):	6.836
Half-life (T1/2):	0.776

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.817
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.629
Rat Oral Acute Toxicity:	0.19
Maximum Recommended Daily Dose:	0.85
Skin Sensitization:	0.935
Carcinogencity:	0.122
Eye Corrosion:	0.003
Eye Irritation:	0.877
Respiratory Toxicity:	0.27

Download Data

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

Natural Product: NPC59162

Natural Product ID:	NPC59162
*Common Name:**	Broussonol D
IUPAC Name:	2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-3,5,7-trihydroxy-8-(3-methylbut-2-enyl)chromen-4-one
Synonyms:	Broussonol D
Standard InCHIKey:	XFBBCGNJNJKLKS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H26O7/c1-12(2)5-7-14-9-15(10-19(28)21(14)29)24-23(31)22(30)20-18(27)11-17(26)16(25(20)32-24)8-6-13(3)4/h5-6,9-11,26-29,31H,7-8H2,1-4H3
SMILES:	CC(=CCc1cc(cc(c1O)O)c1oc2c(CC=C(C)C)c(O)cc(c2c(=O)c1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458762
PubChem CID:	10365850
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003504] 8-prenylated flavones

*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
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[11575957]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19046886]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20493686]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917310]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[468106]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[468106]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	4.15	ug ml-1	PMID[468106]

☑ 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 NPC59162 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	446
0.1-0.2	1891
0.2-0.3	4802
0.3-0.4	11128
0.4-0.5	6501
0.5-0.6	3839
0.6-0.7	4902
0.7-0.8	4722
0.8-0.85	2335
0.85-0.9	1329
0.9-0.95	663
0.95-1	139

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC304295
1.0	High Similarity	NPC205046
0.9931	High Similarity	NPC157784
0.9931	High Similarity	NPC63187
0.9931	High Similarity	NPC37684
0.9796	High Similarity	NPC133392
0.9793	High Similarity	NPC88804
0.9793	High Similarity	NPC3825
0.973	High Similarity	NPC475799
0.973	High Similarity	NPC13779
0.973	High Similarity	NPC3980
0.9664	High Similarity	NPC237418
0.9664	High Similarity	NPC273843
0.966	High Similarity	NPC471982
0.966	High Similarity	NPC249570
0.9595	High Similarity	NPC170492
0.9595	High Similarity	NPC476631
0.9592	High Similarity	NPC154345
0.9589	High Similarity	NPC87125
0.9589	High Similarity	NPC270465
0.9536	High Similarity	NPC246478
0.9527	High Similarity	NPC106976
0.9524	High Similarity	NPC286342
0.9524	High Similarity	NPC149127
0.9524	High Similarity	NPC188871
0.9517	High Similarity	NPC169749
0.9517	High Similarity	NPC179271
0.9517	High Similarity	NPC20791
0.9474	High Similarity	NPC187354
0.947	High Similarity	NPC22192
0.9467	High Similarity	NPC276444
0.9467	High Similarity	NPC471985
0.9463	High Similarity	NPC179126
0.9463	High Similarity	NPC270620
0.9463	High Similarity	NPC162351
0.9463	High Similarity	NPC78326
0.9463	High Similarity	NPC213896
0.9463	High Similarity	NPC74924
0.9463	High Similarity	NPC236223
0.9463	High Similarity	NPC192083
0.9463	High Similarity	NPC58382
0.9463	High Similarity	NPC189130
0.9463	High Similarity	NPC298692
0.9459	High Similarity	NPC260895
0.9459	High Similarity	NPC54394
0.9459	High Similarity	NPC28274
0.9459	High Similarity	NPC50403
0.9459	High Similarity	NPC200740
0.9459	High Similarity	NPC133953
0.9459	High Similarity	NPC125062
0.9459	High Similarity	NPC252933
0.9456	High Similarity	NPC177298
0.9456	High Similarity	NPC48479
0.9452	High Similarity	NPC108406
0.9452	High Similarity	NPC51443
0.9452	High Similarity	NPC74881
0.9444	High Similarity	NPC175013
0.9412	High Similarity	NPC78332
0.9408	High Similarity	NPC470326
0.9408	High Similarity	NPC287328
0.9408	High Similarity	NPC282009
0.9404	High Similarity	NPC218871
0.9404	High Similarity	NPC476630
0.94	High Similarity	NPC321779
0.94	High Similarity	NPC80534
0.94	High Similarity	NPC113906
0.94	High Similarity	NPC470327
0.94	High Similarity	NPC234255
0.94	High Similarity	NPC472280
0.94	High Similarity	NPC45849
0.94	High Similarity	NPC200761
0.94	High Similarity	NPC56786
0.94	High Similarity	NPC477503
0.9396	High Similarity	NPC123886
0.9396	High Similarity	NPC55205
0.9396	High Similarity	NPC237994
0.9396	High Similarity	NPC279989
0.9396	High Similarity	NPC82325
0.9392	High Similarity	NPC219330
0.9392	High Similarity	NPC50728
0.9392	High Similarity	NPC166753
0.9388	High Similarity	NPC166036
0.9388	High Similarity	NPC203077
0.9388	High Similarity	NPC120464
0.9388	High Similarity	NPC238279
0.9379	High Similarity	NPC279121
0.9379	High Similarity	NPC190637
0.9379	High Similarity	NPC24821
0.9379	High Similarity	NPC212932
0.9379	High Similarity	NPC9117
0.9379	High Similarity	NPC293053
0.9351	High Similarity	NPC472625
0.9351	High Similarity	NPC470459
0.9346	High Similarity	NPC289771
0.9346	High Similarity	NPC471499
0.9342	High Similarity	NPC469658
0.9342	High Similarity	NPC46736
0.9342	High Similarity	NPC197856
0.9338	High Similarity	NPC100916
0.9338	High Similarity	NPC191146
0.9338	High Similarity	NPC278778
0.9338	High Similarity	NPC291878
0.9338	High Similarity	NPC55619
0.9338	High Similarity	NPC472626
0.9338	High Similarity	NPC265511
0.9338	High Similarity	NPC209614
0.9338	High Similarity	NPC49824
0.9338	High Similarity	NPC474520
0.9338	High Similarity	NPC200388
0.9338	High Similarity	NPC282307
0.9338	High Similarity	NPC471500
0.9338	High Similarity	NPC470328
0.9338	High Similarity	NPC170026
0.9338	High Similarity	NPC195796
0.9338	High Similarity	NPC35038
0.9338	High Similarity	NPC68093
0.9338	High Similarity	NPC138243
0.9338	High Similarity	NPC142339
0.9338	High Similarity	NPC472455
0.9333	High Similarity	NPC227337
0.9333	High Similarity	NPC49402
0.9333	High Similarity	NPC70433
0.9333	High Similarity	NPC273462
0.9333	High Similarity	NPC33051
0.9329	High Similarity	NPC76376
0.9329	High Similarity	NPC236769
0.9324	High Similarity	NPC287101
0.9324	High Similarity	NPC52005
0.9324	High Similarity	NPC269420
0.9324	High Similarity	NPC38545
0.9324	High Similarity	NPC223579
0.9324	High Similarity	NPC171916
0.9324	High Similarity	NPC137062
0.9324	High Similarity	NPC159103
0.9324	High Similarity	NPC183950
0.9324	High Similarity	NPC195351
0.932	High Similarity	NPC33265
0.932	High Similarity	NPC62536
0.9315	High Similarity	NPC70136
0.9315	High Similarity	NPC216538
0.9315	High Similarity	NPC326500
0.9315	High Similarity	NPC273538
0.931	High Similarity	NPC200694
0.931	High Similarity	NPC473042
0.929	High Similarity	NPC470457
0.9286	High Similarity	NPC211107
0.9281	High Similarity	NPC476283
0.9281	High Similarity	NPC476980
0.9281	High Similarity	NPC204290
0.9281	High Similarity	NPC328102
0.9281	High Similarity	NPC476280
0.9281	High Similarity	NPC119209
0.9281	High Similarity	NPC192686
0.9281	High Similarity	NPC118256
0.9281	High Similarity	NPC297212
0.9276	High Similarity	NPC218313
0.9276	High Similarity	NPC7973
0.9276	High Similarity	NPC472438
0.9276	High Similarity	NPC227192
0.9276	High Similarity	NPC262286
0.9276	High Similarity	NPC203891
0.9276	High Similarity	NPC36852
0.9276	High Similarity	NPC75215
0.9276	High Similarity	NPC101830
0.9276	High Similarity	NPC27337
0.9276	High Similarity	NPC189179
0.9276	High Similarity	NPC223787
0.9276	High Similarity	NPC52889
0.9276	High Similarity	NPC471515
0.9276	High Similarity	NPC291508
0.9276	High Similarity	NPC29841
0.9276	High Similarity	NPC474681
0.9276	High Similarity	NPC236796
0.9276	High Similarity	NPC67876
0.9276	High Similarity	NPC110070
0.9276	High Similarity	NPC471209
0.9276	High Similarity	NPC78302
0.9276	High Similarity	NPC235215
0.9276	High Similarity	NPC474055
0.9276	High Similarity	NPC224137
0.9276	High Similarity	NPC78225
0.9276	High Similarity	NPC471479
0.9276	High Similarity	NPC93376
0.9276	High Similarity	NPC472598
0.9272	High Similarity	NPC214138
0.9272	High Similarity	NPC168247
0.9272	High Similarity	NPC26227
0.9272	High Similarity	NPC117992
0.9272	High Similarity	NPC152951
0.9272	High Similarity	NPC201451
0.9272	High Similarity	NPC230149
0.9272	High Similarity	NPC57674
0.9272	High Similarity	NPC44079
0.9267	High Similarity	NPC323626
0.9267	High Similarity	NPC39732
0.9267	High Similarity	NPC60972
0.9267	High Similarity	NPC324233
0.9262	High Similarity	NPC77858
0.9262	High Similarity	NPC184136
0.9257	High Similarity	NPC119059

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 NPC59162 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	999
0.2-0.3	1858
0.3-0.4	2671
0.4-0.5	1728
0.5-0.6	980
0.6-0.7	347
0.7-0.8	112
0.8-0.85	36
0.85-0.9	11
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9517	High Similarity	NPD1512	Approved
0.9463	High Similarity	NPD2393	Clinical (unspecified phase)
0.9379	High Similarity	NPD1511	Approved
0.9315	High Similarity	NPD4378	Clinical (unspecified phase)
0.9205	High Similarity	NPD2801	Approved
0.9139	High Similarity	NPD1934	Approved
0.8961	High Similarity	NPD3882	Suspended
0.8924	High Similarity	NPD6167	Clinical (unspecified phase)
0.8924	High Similarity	NPD6166	Phase 2
0.8924	High Similarity	NPD6168	Clinical (unspecified phase)
0.8896	High Similarity	NPD3817	Phase 2
0.8675	High Similarity	NPD7410	Clinical (unspecified phase)
0.8662	High Similarity	NPD7075	Discontinued
0.865	High Similarity	NPD6797	Phase 2
0.8636	High Similarity	NPD4380	Phase 2
0.8598	High Similarity	NPD7251	Discontinued
0.859	High Similarity	NPD7096	Clinical (unspecified phase)
0.858	High Similarity	NPD3818	Discontinued
0.8528	High Similarity	NPD7054	Approved
0.8526	High Similarity	NPD6801	Discontinued
0.8481	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD7472	Approved
0.8476	Intermediate Similarity	NPD7074	Phase 3
0.8456	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1510	Phase 2
0.8434	Intermediate Similarity	NPD7808	Phase 3
0.8434	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1549	Phase 2
0.8389	Intermediate Similarity	NPD2796	Approved
0.8366	Intermediate Similarity	NPD6799	Approved
0.8354	Intermediate Similarity	NPD7819	Suspended
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8323	Intermediate Similarity	NPD5494	Approved
0.8313	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD943	Approved
0.8299	Intermediate Similarity	NPD1240	Approved
0.8293	Intermediate Similarity	NPD7473	Discontinued
0.8272	Intermediate Similarity	NPD6959	Discontinued
0.8228	Intermediate Similarity	NPD7411	Suspended
0.8224	Intermediate Similarity	NPD2800	Approved
0.8204	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD1607	Approved
0.8165	Intermediate Similarity	NPD6599	Discontinued
0.816	Intermediate Similarity	NPD1247	Approved
0.8158	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD919	Approved
0.8125	Intermediate Similarity	NPD1465	Phase 2
0.8082	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD5402	Approved
0.8052	Intermediate Similarity	NPD3750	Approved
0.8027	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD2935	Discontinued
0.7987	Intermediate Similarity	NPD1243	Approved
0.7976	Intermediate Similarity	NPD5844	Phase 1
0.7975	Intermediate Similarity	NPD5403	Approved
0.7962	Intermediate Similarity	NPD2533	Approved
0.7962	Intermediate Similarity	NPD2532	Approved
0.7962	Intermediate Similarity	NPD2534	Approved
0.7961	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD3926	Phase 2
0.7941	Intermediate Similarity	NPD6559	Discontinued
0.7914	Intermediate Similarity	NPD7768	Phase 2
0.7904	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD230	Phase 1
0.7871	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD5401	Approved
0.7843	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6651	Approved
0.7815	Intermediate Similarity	NPD1613	Approved
0.7815	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD2313	Discontinued
0.7792	Intermediate Similarity	NPD6100	Approved
0.7792	Intermediate Similarity	NPD6099	Approved
0.7785	Intermediate Similarity	NPD7390	Discontinued
0.7764	Intermediate Similarity	NPD3226	Approved
0.7758	Intermediate Similarity	NPD3749	Approved
0.775	Intermediate Similarity	NPD920	Approved
0.7727	Intermediate Similarity	NPD2799	Discontinued
0.7727	Intermediate Similarity	NPD3748	Approved
0.7688	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1551	Phase 2
0.7647	Intermediate Similarity	NPD447	Suspended
0.764	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2346	Discontinued
0.7628	Intermediate Similarity	NPD2344	Approved
0.7625	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3027	Phase 3
0.761	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD5953	Discontinued
0.7558	Intermediate Similarity	NPD7286	Phase 2
0.7529	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7484	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.7473	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1203	Approved
0.7453	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD3268	Approved
0.7446	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2309	Approved
0.7438	Intermediate Similarity	NPD6190	Approved
0.743	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD2798	Approved
0.7412	Intermediate Similarity	NPD7199	Phase 2
0.7407	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD3751	Discontinued
0.7386	Intermediate Similarity	NPD4625	Phase 3
0.7383	Intermediate Similarity	NPD9269	Phase 2
0.7368	Intermediate Similarity	NPD5711	Approved
0.7368	Intermediate Similarity	NPD5710	Approved
0.7368	Intermediate Similarity	NPD3787	Discontinued
0.7363	Intermediate Similarity	NPD4363	Phase 3
0.7363	Intermediate Similarity	NPD4360	Phase 2
0.736	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2797	Approved
0.7333	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4908	Phase 1
0.7315	Intermediate Similarity	NPD422	Phase 1
0.7308	Intermediate Similarity	NPD1933	Approved
0.7305	Intermediate Similarity	NPD37	Approved
0.7283	Intermediate Similarity	NPD2403	Approved
0.7279	Intermediate Similarity	NPD1548	Phase 1
0.7278	Intermediate Similarity	NPD4967	Phase 2
0.7278	Intermediate Similarity	NPD7033	Discontinued
0.7278	Intermediate Similarity	NPD4965	Approved
0.7278	Intermediate Similarity	NPD4966	Approved
0.7278	Intermediate Similarity	NPD4308	Phase 3
0.7273	Intermediate Similarity	NPD1653	Approved
0.7267	Intermediate Similarity	NPD1608	Approved
0.7267	Intermediate Similarity	NPD9717	Approved
0.7255	Intermediate Similarity	NPD9494	Approved
0.7244	Intermediate Similarity	NPD4060	Phase 1
0.7228	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4361	Phase 2
0.7226	Intermediate Similarity	NPD6798	Discontinued
0.7222	Intermediate Similarity	NPD8434	Phase 2
0.7219	Intermediate Similarity	NPD4749	Approved
0.7208	Intermediate Similarity	NPD6832	Phase 2
0.7205	Intermediate Similarity	NPD2654	Approved
0.72	Intermediate Similarity	NPD1201	Approved
0.72	Intermediate Similarity	NPD1610	Phase 2
0.72	Intermediate Similarity	NPD7228	Approved
0.72	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1471	Phase 3
0.7171	Intermediate Similarity	NPD3225	Approved
0.7168	Intermediate Similarity	NPD7229	Phase 3
0.7166	Intermediate Similarity	NPD6777	Approved
0.7166	Intermediate Similarity	NPD6776	Approved
0.7166	Intermediate Similarity	NPD6780	Approved
0.7166	Intermediate Similarity	NPD6782	Approved
0.7166	Intermediate Similarity	NPD6779	Approved
0.7166	Intermediate Similarity	NPD6778	Approved
0.7166	Intermediate Similarity	NPD6781	Approved
0.7152	Intermediate Similarity	NPD5049	Phase 3
0.7151	Intermediate Similarity	NPD8313	Approved
0.7151	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD8150	Discontinued
0.7125	Intermediate Similarity	NPD5405	Approved
0.7125	Intermediate Similarity	NPD5406	Approved
0.7125	Intermediate Similarity	NPD5404	Approved
0.7125	Intermediate Similarity	NPD5408	Approved
0.7124	Intermediate Similarity	NPD3266	Approved
0.7124	Intermediate Similarity	NPD1470	Approved
0.7124	Intermediate Similarity	NPD3267	Approved
0.712	Intermediate Similarity	NPD7584	Approved
0.7118	Intermediate Similarity	NPD4288	Approved
0.7117	Intermediate Similarity	NPD2354	Approved
0.7115	Intermediate Similarity	NPD411	Approved
0.7114	Intermediate Similarity	NPD9268	Approved
0.7091	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6355	Discontinued
0.7089	Intermediate Similarity	NPD5124	Phase 1
0.7073	Intermediate Similarity	NPD3300	Phase 2
0.707	Intermediate Similarity	NPD6233	Phase 2
0.7067	Intermediate Similarity	NPD17	Approved
0.7053	Intermediate Similarity	NPD7435	Discontinued
0.7051	Intermediate Similarity	NPD7095	Approved
0.7047	Intermediate Similarity	NPD8151	Discontinued
0.7039	Intermediate Similarity	NPD7685	Pre-registration
0.7029	Intermediate Similarity	NPD5242	Approved
0.7025	Intermediate Similarity	NPD4307	Phase 2
0.7024	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7458	Discontinued
0.7022	Intermediate Similarity	NPD1729	Discontinued
0.7006	Intermediate Similarity	NPD1296	Phase 2
0.7006	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6844	Discontinued
0.6989	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7697	Approved
0.6963	Remote Similarity	NPD7696	Phase 3

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