NPASS Compound

Structure

CID78332 OpenBabel06191715412D 32 35 0 0 0 0 0 0 0 0999 V2000 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 1.7321 -2.0000 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 6.9282 -3.0000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 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 -0.5000 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 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 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 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 24 1 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 25 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 17 1 0 0 0 0 14 26 1 0 0 0 0 15 18 2 0 0 0 0 15 27 1 0 0 0 0 16 21 2 0 0 0 0 16 28 1 0 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 18 23 1 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 29 2 0 0 0 0 20 22 2 0 0 0 0 20 30 1 0 0 0 0 21 32 1 0 0 0 0 22 31 1 0 0 0 0 23 31 1 0 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.15
Volume:	441.897
LogP:	5.542
LogD:	3.349
LogS:	-3.121
# Rotatable Bonds:	3
TPSA:	120.36
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.43
Synthetic Accessibility Score:	3.539
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.025
MDCK Permeability:	1.5527210052823648e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.188
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	99.40619659423828%
Volume Distribution (VD):	0.652
Pgp-substrate:	4.651216506958008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.835
CYP1A2-substrate:	0.24
CYP2C19-inhibitor:	0.307
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.8
CYP2C9-substrate:	0.755
CYP2D6-inhibitor:	0.361
CYP2D6-substrate:	0.161
CYP3A4-inhibitor:	0.37
CYP3A4-substrate:	0.131

ADMET: Excretion

Clearance (CL):	1.096
Half-life (T1/2):	0.508

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.331
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.405
Rat Oral Acute Toxicity:	0.176
Maximum Recommended Daily Dose:	0.838
Skin Sensitization:	0.713
Carcinogencity:	0.53
Eye Corrosion:	0.003
Eye Irritation:	0.838
Respiratory Toxicity:	0.551

Download Data

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

Natural Product: NPC78332

Natural Product ID:	NPC78332
*Common Name:**	Broussonol A
IUPAC Name:	3,5,7-trihydroxy-2-(8-hydroxy-2,2-dimethylchromen-6-yl)-8-(2-methylbut-3-en-2-yl)chromen-4-one
Synonyms:
Standard InCHIKey:	PSJXCDCTKCAYCB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H24O7/c1-6-24(2,3)18-15(27)11-14(26)17-19(29)20(30)22(31-23(17)18)13-9-12-7-8-25(4,5)32-21(12)16(28)10-13/h6-11,26-28,30H,1H2,2-5H3
SMILES:	C=CC(C)(C)c1c(cc(c2c(=O)c(c(c3cc4C=CC(C)(C)Oc4c(c3)O)oc12)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457085
PubChem CID:	10342975
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0003520] Pyranoflavonoids

*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	=	8.74	ug ml-1	PMID[575297]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	=	9.1	ug ml-1	PMID[575297]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[575297]

☑ 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 NPC78332 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	466
0.1-0.2	1876
0.2-0.3	4253
0.3-0.4	10395
0.4-0.5	7627
0.5-0.6	3719
0.6-0.7	5234
0.7-0.8	4964
0.8-0.85	2333
0.85-0.9	1221
0.9-0.95	535
0.95-1	74

Similarity Score	Similarity Level	Natural Product ID
0.9684	High Similarity	NPC165456
0.9673	High Similarity	NPC471985
0.9673	High Similarity	NPC3980
0.961	High Similarity	NPC237418
0.9551	High Similarity	NPC234644
0.9548	High Similarity	NPC280680
0.9542	High Similarity	NPC170492
0.9497	High Similarity	NPC476306
0.9487	High Similarity	NPC476280
0.9487	High Similarity	NPC188433
0.9477	High Similarity	NPC157784
0.9477	High Similarity	NPC37684
0.9477	High Similarity	NPC63187
0.943	High Similarity	NPC306321
0.943	High Similarity	NPC303460
0.943	High Similarity	NPC472625
0.9427	High Similarity	NPC259456
0.9427	High Similarity	NPC57715
0.9423	High Similarity	NPC46736
0.9423	High Similarity	NPC197856
0.9423	High Similarity	NPC184755
0.9423	High Similarity	NPC74178
0.9419	High Similarity	NPC276444
0.9412	High Similarity	NPC304295
0.9412	High Similarity	NPC205046
0.9412	High Similarity	NPC59162
0.9371	High Similarity	NPC62261
0.9367	High Similarity	NPC474150
0.9367	High Similarity	NPC474162
0.9367	High Similarity	NPC206605
0.9363	High Similarity	NPC297212
0.9363	High Similarity	NPC118256
0.9363	High Similarity	NPC192686
0.9363	High Similarity	NPC28241
0.9363	High Similarity	NPC471973
0.9363	High Similarity	NPC204290
0.9363	High Similarity	NPC119209
0.9359	High Similarity	NPC474681
0.9359	High Similarity	NPC218313
0.9359	High Similarity	NPC273843
0.9359	High Similarity	NPC304008
0.9359	High Similarity	NPC161960
0.9359	High Similarity	NPC187745
0.9359	High Similarity	NPC476630
0.9359	High Similarity	NPC218871
0.9355	High Similarity	NPC133392
0.9355	High Similarity	NPC234255
0.9355	High Similarity	NPC472280
0.9351	High Similarity	NPC471982
0.9351	High Similarity	NPC237994
0.9346	High Similarity	NPC3825
0.9346	High Similarity	NPC88804
0.9317	High Similarity	NPC288813
0.9308	High Similarity	NPC189473
0.9308	High Similarity	NPC23298
0.9308	High Similarity	NPC186686
0.9308	High Similarity	NPC12461
0.9304	High Similarity	NPC29876
0.9304	High Similarity	NPC474038
0.9304	High Similarity	NPC167678
0.9304	High Similarity	NPC187354
0.9299	High Similarity	NPC235448
0.9299	High Similarity	NPC204879
0.9295	High Similarity	NPC6633
0.9295	High Similarity	NPC472455
0.9295	High Similarity	NPC282307
0.9295	High Similarity	NPC170026
0.9295	High Similarity	NPC115853
0.9295	High Similarity	NPC133970
0.9295	High Similarity	NPC475799
0.9295	High Similarity	NPC13779
0.9295	High Similarity	NPC5322
0.929	High Similarity	NPC78326
0.929	High Similarity	NPC236223
0.929	High Similarity	NPC270620
0.929	High Similarity	NPC179126
0.9286	High Similarity	NPC154345
0.9286	High Similarity	NPC54394
0.9286	High Similarity	NPC200740
0.9286	High Similarity	NPC125062
0.9286	High Similarity	NPC252933
0.925	High Similarity	NPC239752
0.925	High Similarity	NPC303174
0.925	High Similarity	NPC275780
0.925	High Similarity	NPC472450
0.9245	High Similarity	NPC83922
0.9245	High Similarity	NPC472448
0.9245	High Similarity	NPC261470
0.9241	High Similarity	NPC475784
0.9241	High Similarity	NPC476980
0.9241	High Similarity	NPC246478
0.9241	High Similarity	NPC282009
0.9241	High Similarity	NPC476283
0.9241	High Similarity	NPC287328
0.9236	High Similarity	NPC219867
0.9236	High Similarity	NPC27337
0.9236	High Similarity	NPC473272
0.9236	High Similarity	NPC136674
0.9236	High Similarity	NPC52889
0.9236	High Similarity	NPC67876
0.9236	High Similarity	NPC284820
0.9236	High Similarity	NPC180011
0.9231	High Similarity	NPC200246
0.9226	High Similarity	NPC279989
0.9226	High Similarity	NPC82325
0.9226	High Similarity	NPC55205
0.9221	High Similarity	NPC166753
0.9221	High Similarity	NPC50728
0.9198	High Similarity	NPC476637
0.9193	High Similarity	NPC471213
0.9193	High Similarity	NPC43319
0.9193	High Similarity	NPC39091
0.9193	High Similarity	NPC37870
0.9193	High Similarity	NPC472449
0.9187	High Similarity	NPC476295
0.9187	High Similarity	NPC220313
0.9187	High Similarity	NPC41301
0.9182	High Similarity	NPC472632
0.9182	High Similarity	NPC289771
0.9182	High Similarity	NPC472906
0.9182	High Similarity	NPC471210
0.9182	High Similarity	NPC198829
0.9182	High Similarity	NPC26326
0.9182	High Similarity	NPC471499
0.9182	High Similarity	NPC173137
0.9177	High Similarity	NPC172770
0.9177	High Similarity	NPC22192
0.9177	High Similarity	NPC55738
0.9177	High Similarity	NPC185258
0.9172	High Similarity	NPC195796
0.9172	High Similarity	NPC191146
0.9172	High Similarity	NPC470600
0.9172	High Similarity	NPC35038
0.9172	High Similarity	NPC68093
0.9172	High Similarity	NPC278778
0.9172	High Similarity	NPC265511
0.9172	High Similarity	NPC291878
0.9172	High Similarity	NPC49824
0.9167	High Similarity	NPC58382
0.9167	High Similarity	NPC162351
0.9167	High Similarity	NPC227337
0.9167	High Similarity	NPC273462
0.9167	High Similarity	NPC49402
0.9167	High Similarity	NPC33051
0.9167	High Similarity	NPC70433
0.9161	High Similarity	NPC50403
0.9161	High Similarity	NPC133953
0.9161	High Similarity	NPC236769
0.9161	High Similarity	NPC28274
0.9161	High Similarity	NPC81474
0.9156	High Similarity	NPC270465
0.9156	High Similarity	NPC159103
0.9156	High Similarity	NPC48479
0.9156	High Similarity	NPC183950
0.9156	High Similarity	NPC52005
0.9156	High Similarity	NPC287101
0.9156	High Similarity	NPC177298
0.9156	High Similarity	NPC223579
0.9156	High Similarity	NPC137062
0.9156	High Similarity	NPC87125
0.915	High Similarity	NPC14001
0.915	High Similarity	NPC166757
0.9141	High Similarity	NPC472276
0.9141	High Similarity	NPC101107
0.9136	High Similarity	NPC218226
0.913	High Similarity	NPC293319
0.913	High Similarity	NPC50960
0.913	High Similarity	NPC130920
0.913	High Similarity	NPC85057
0.913	High Similarity	NPC156432
0.913	High Similarity	NPC224280
0.913	High Similarity	NPC472277
0.9125	High Similarity	NPC329760
0.9125	High Similarity	NPC229632
0.9125	High Similarity	NPC474034
0.9125	High Similarity	NPC25152
0.9125	High Similarity	NPC194427
0.9125	High Similarity	NPC474033
0.9119	High Similarity	NPC328102
0.9119	High Similarity	NPC470326
0.9119	High Similarity	NPC174953
0.9119	High Similarity	NPC45146
0.9119	High Similarity	NPC235018
0.9119	High Similarity	NPC139036
0.9119	High Similarity	NPC80375
0.9119	High Similarity	NPC472624
0.9119	High Similarity	NPC470183
0.9119	High Similarity	NPC36217
0.9119	High Similarity	NPC474960
0.9114	High Similarity	NPC476981
0.9114	High Similarity	NPC227192
0.9114	High Similarity	NPC471515
0.9114	High Similarity	NPC203891
0.9114	High Similarity	NPC224137
0.9114	High Similarity	NPC75215
0.9114	High Similarity	NPC93376
0.9114	High Similarity	NPC78071
0.9114	High Similarity	NPC110070
0.9114	High Similarity	NPC471479
0.9114	High Similarity	NPC78225

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 NPC78332 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	414
0.1-0.2	1004
0.2-0.3	1772
0.3-0.4	2654
0.4-0.5	1832
0.5-0.6	935
0.6-0.7	373
0.7-0.8	115
0.8-0.85	34
0.85-0.9	11
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9085	High Similarity	NPD1512	Approved
0.9045	High Similarity	NPD2801	Approved
0.9045	High Similarity	NPD2393	Clinical (unspecified phase)
0.8981	High Similarity	NPD1934	Approved
0.8954	High Similarity	NPD1511	Approved
0.8896	High Similarity	NPD4378	Clinical (unspecified phase)
0.8896	High Similarity	NPD6166	Phase 2
0.8896	High Similarity	NPD6168	Clinical (unspecified phase)
0.8896	High Similarity	NPD6167	Clinical (unspecified phase)
0.8812	High Similarity	NPD3882	Suspended
0.875	High Similarity	NPD3817	Phase 2
0.8535	High Similarity	NPD7410	Clinical (unspecified phase)
0.8521	High Similarity	NPD6797	Phase 2
0.8512	High Similarity	NPD7054	Approved
0.85	High Similarity	NPD4380	Phase 2
0.8471	Intermediate Similarity	NPD7251	Discontinued
0.8462	Intermediate Similarity	NPD7472	Approved
0.8462	Intermediate Similarity	NPD7074	Phase 3
0.8452	Intermediate Similarity	NPD3818	Discontinued
0.8424	Intermediate Similarity	NPD5494	Approved
0.8421	Intermediate Similarity	NPD7808	Phase 3
0.8421	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7075	Discontinued
0.8344	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6232	Discontinued
0.8294	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7473	Discontinued
0.8282	Intermediate Similarity	NPD6801	Discontinued
0.8272	Intermediate Similarity	NPD6599	Discontinued
0.8242	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6799	Approved
0.8121	Intermediate Similarity	NPD7819	Suspended
0.8121	Intermediate Similarity	NPD1465	Phase 2
0.8101	Intermediate Similarity	NPD2800	Approved
0.8089	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD5844	Phase 1
0.8077	Intermediate Similarity	NPD1510	Phase 2
0.8072	Intermediate Similarity	NPD5402	Approved
0.8047	Intermediate Similarity	NPD1247	Approved
0.8047	Intermediate Similarity	NPD6959	Discontinued
0.8038	Intermediate Similarity	NPD1549	Phase 2
0.8036	Intermediate Similarity	NPD919	Approved
0.8025	Intermediate Similarity	NPD2796	Approved
0.8	Intermediate Similarity	NPD7411	Suspended
0.7989	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD5403	Approved
0.7953	Intermediate Similarity	NPD3926	Phase 2
0.7937	Intermediate Similarity	NPD3750	Approved
0.7935	Intermediate Similarity	NPD943	Approved
0.7935	Intermediate Similarity	NPD1240	Approved
0.7853	Intermediate Similarity	NPD5401	Approved
0.7834	Intermediate Similarity	NPD1607	Approved
0.7812	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7768	Phase 2
0.7803	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD6100	Approved
0.7799	Intermediate Similarity	NPD6099	Approved
0.7792	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD3749	Approved
0.774	Intermediate Similarity	NPD6559	Discontinued
0.7736	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD2935	Discontinued
0.7636	Intermediate Similarity	NPD2533	Approved
0.7636	Intermediate Similarity	NPD2534	Approved
0.7636	Intermediate Similarity	NPD2532	Approved
0.7625	Intermediate Similarity	NPD3748	Approved
0.761	Intermediate Similarity	NPD6651	Approved
0.7607	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD4628	Phase 3
0.7595	Intermediate Similarity	NPD1613	Approved
0.7595	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7390	Discontinued
0.7569	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD3226	Approved
0.7554	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD447	Suspended
0.7546	Intermediate Similarity	NPD1243	Approved
0.7546	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3027	Phase 3
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7514	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD3787	Discontinued
0.7468	Intermediate Similarity	NPD2313	Discontinued
0.746	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD920	Approved
0.7438	Intermediate Similarity	NPD230	Phase 1
0.7432	Intermediate Similarity	NPD8434	Phase 2
0.7429	Intermediate Similarity	NPD7199	Phase 2
0.7423	Intermediate Similarity	NPD2346	Discontinued
0.7423	Intermediate Similarity	NPD2344	Approved
0.7414	Intermediate Similarity	NPD6234	Discontinued
0.7394	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1551	Phase 2
0.7358	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6190	Approved
0.7321	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4625	Phase 3
0.7296	Intermediate Similarity	NPD7095	Approved
0.7293	Intermediate Similarity	NPD5953	Discontinued
0.7287	Intermediate Similarity	NPD4360	Phase 2
0.7287	Intermediate Similarity	NPD4363	Phase 3
0.7278	Intermediate Similarity	NPD7286	Phase 2
0.7277	Intermediate Similarity	NPD6778	Approved
0.7277	Intermediate Similarity	NPD6779	Approved
0.7277	Intermediate Similarity	NPD6776	Approved
0.7277	Intermediate Similarity	NPD6782	Approved
0.7277	Intermediate Similarity	NPD6780	Approved
0.7277	Intermediate Similarity	NPD6777	Approved
0.7277	Intermediate Similarity	NPD6781	Approved
0.7253	Intermediate Similarity	NPD7685	Pre-registration
0.7251	Intermediate Similarity	NPD7458	Discontinued
0.725	Intermediate Similarity	NPD3268	Approved
0.7246	Intermediate Similarity	NPD2309	Approved
0.7244	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD8150	Discontinued
0.7233	Intermediate Similarity	NPD4908	Phase 1
0.7225	Intermediate Similarity	NPD37	Approved
0.7222	Intermediate Similarity	NPD7228	Approved
0.7222	Intermediate Similarity	NPD1933	Approved
0.7219	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2798	Approved
0.7207	Intermediate Similarity	NPD2403	Approved
0.72	Intermediate Similarity	NPD4967	Phase 2
0.72	Intermediate Similarity	NPD4966	Approved
0.72	Intermediate Similarity	NPD4965	Approved
0.7193	Intermediate Similarity	NPD1653	Approved
0.7186	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD8312	Approved
0.7174	Intermediate Similarity	NPD8313	Approved
0.717	Intermediate Similarity	NPD9494	Approved
0.7165	Intermediate Similarity	NPD7435	Discontinued
0.716	Intermediate Similarity	NPD4060	Phase 1
0.7152	Intermediate Similarity	NPD1203	Approved
0.7152	Intermediate Similarity	NPD2797	Approved
0.715	Intermediate Similarity	NPD2493	Approved
0.715	Intermediate Similarity	NPD2494	Approved
0.7143	Intermediate Similarity	NPD7584	Approved
0.7117	Intermediate Similarity	NPD5124	Phase 1
0.7117	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3300	Phase 2
0.7095	Intermediate Similarity	NPD5711	Approved
0.7095	Intermediate Similarity	NPD5710	Approved
0.7091	Intermediate Similarity	NPD4308	Phase 3
0.7091	Intermediate Similarity	NPD7033	Discontinued
0.7089	Intermediate Similarity	NPD3225	Approved
0.7077	Intermediate Similarity	NPD7697	Approved
0.7077	Intermediate Similarity	NPD7698	Approved
0.7077	Intermediate Similarity	NPD7696	Phase 3
0.7076	Intermediate Similarity	NPD5049	Phase 3
0.707	Intermediate Similarity	NPD1608	Approved
0.7068	Intermediate Similarity	NPD4361	Phase 2
0.7068	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3450	Approved
0.7062	Intermediate Similarity	NPD3452	Approved
0.7056	Intermediate Similarity	NPD5242	Approved
0.7048	Intermediate Similarity	NPD5406	Approved
0.7048	Intermediate Similarity	NPD5404	Approved
0.7048	Intermediate Similarity	NPD5405	Approved
0.7048	Intermediate Similarity	NPD5408	Approved
0.7045	Intermediate Similarity	NPD4288	Approved
0.7041	Intermediate Similarity	NPD4583	Approved
0.7041	Intermediate Similarity	NPD7871	Phase 2
0.7041	Intermediate Similarity	NPD7870	Phase 2
0.7041	Intermediate Similarity	NPD4582	Approved
0.7041	Intermediate Similarity	NPD2354	Approved
0.7039	Intermediate Similarity	NPD8127	Discontinued
0.7037	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6798	Discontinued
0.7025	Intermediate Similarity	NPD4749	Approved
0.7024	Intermediate Similarity	NPD7907	Approved
0.702	Intermediate Similarity	NPD7701	Phase 2
0.7017	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6535	Approved
0.7016	Intermediate Similarity	NPD6534	Approved
0.7012	Intermediate Similarity	NPD6355	Discontinued
0.701	Intermediate Similarity	NPD4111	Phase 1
0.701	Intermediate Similarity	NPD4665	Approved
0.7006	Intermediate Similarity	NPD1610	Phase 2
0.7006	Intermediate Similarity	NPD422	Phase 1
0.7006	Intermediate Similarity	NPD1471	Phase 3
0.7006	Intermediate Similarity	NPD1201	Approved
0.7	Intermediate Similarity	NPD7229	Phase 3
0.699	Remote Similarity	NPD4002	Approved
0.699	Remote Similarity	NPD4004	Approved
0.6989	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD8151	Discontinued
0.6982	Remote Similarity	NPD7003	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data