NPASS Compound

Structure

CID165456 OpenBabel06191715532D 32 36 0 0 1 0 0 0 0 0999 V2000 -7.7646 0.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3190 -0.2128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.4563 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 -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 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2646 -0.4173 0.0000 C 0 0 3 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 -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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2701 -0.5219 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 -0.0000 -2.0000 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 -7.6713 -1.3309 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 11 1 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 7 2 0 0 0 0 6 12 1 0 0 0 0 7 24 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 25 1 0 0 0 0 11 30 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 21 2 0 0 0 0 15 27 1 0 0 0 0 16 18 2 0 0 0 0 16 30 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 25 1 0 0 0 0 19 20 1 0 0 0 0 19 28 2 0 0 0 0 20 22 2 0 0 0 0 20 29 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 24 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.15
Volume:	435.977
LogP:	5.429
LogD:	3.61
LogS:	-3.252
# Rotatable Bonds:	1
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.502
Synthetic Accessibility Score:	3.987
Fsp3:	0.32
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:	-4.93
MDCK Permeability:	1.487992540205596e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.079
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	98.31317138671875%
Volume Distribution (VD):	0.579
Pgp-substrate:	4.25582218170166%

ADMET: Metabolism

CYP1A2-inhibitor:	0.617
CYP1A2-substrate:	0.533
CYP2C19-inhibitor:	0.436
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.843
CYP2C9-substrate:	0.744
CYP2D6-inhibitor:	0.317
CYP2D6-substrate:	0.194
CYP3A4-inhibitor:	0.323
CYP3A4-substrate:	0.293

ADMET: Excretion

Clearance (CL):	1.707
Half-life (T1/2):	0.281

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.711
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.291
Rat Oral Acute Toxicity:	0.49
Maximum Recommended Daily Dose:	0.86
Skin Sensitization:	0.627
Carcinogencity:	0.662
Eye Corrosion:	0.003
Eye Irritation:	0.717
Respiratory Toxicity:	0.713

Download Data

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

Natural Product: NPC165456

Natural Product ID:	NPC165456
*Common Name:**	Broussonol B
IUPAC Name:	3,5-dihydroxy-2-(8-hydroxy-2,2-dimethylchromen-6-yl)-8,9,9-trimethyl-8H-furo[2,3-h]chromen-4-one
Synonyms:
Standard InCHIKey:	WYEJSRSJEMZHNA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H24O7/c1-11-25(4,5)18-16(30-11)10-14(26)17-19(28)20(29)22(31-23(17)18)13-8-12-6-7-24(2,3)32-21(12)15(27)9-13/h6-11,26-27,29H,1-5H3
SMILES:	CC1C(C)(C)c2c(cc(c3c(=O)c(c(c4cc5C=CC(C)(C)Oc5c(c4)O)oc23)O)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457086
PubChem CID:	10320815
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	=	5.52	ug ml-1	PMID[492206]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	=	8.8	ug ml-1	PMID[492206]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[492206]

☑ 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 NPC165456 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	455
0.1-0.2	1750
0.2-0.3	3801
0.3-0.4	9582
0.4-0.5	8800
0.5-0.6	3869
0.6-0.7	5347
0.7-0.8	5015
0.8-0.85	2374
0.85-0.9	1408
0.9-0.95	279
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9684	High Similarity	NPC78332
0.9627	High Similarity	NPC288813
0.962	High Similarity	NPC187354
0.9557	High Similarity	NPC476283
0.95	High Similarity	NPC472625
0.9448	High Similarity	NPC472276
0.9441	High Similarity	NPC62261
0.9441	High Similarity	NPC472277
0.9434	High Similarity	NPC118256
0.9434	High Similarity	NPC328102
0.9434	High Similarity	NPC192686
0.9434	High Similarity	NPC119209
0.9434	High Similarity	NPC472624
0.9379	High Similarity	NPC186686
0.9379	High Similarity	NPC205265
0.9379	High Similarity	NPC472281
0.9379	High Similarity	NPC18100
0.9375	High Similarity	NPC474038
0.9371	High Similarity	NPC184755
0.9371	High Similarity	NPC74178
0.9367	High Similarity	NPC3980
0.9367	High Similarity	NPC471985
0.9329	High Similarity	NPC102277
0.9329	High Similarity	NPC279209
0.9325	High Similarity	NPC150131
0.9317	High Similarity	NPC474162
0.9317	High Similarity	NPC472635
0.9317	High Similarity	NPC474150
0.9313	High Similarity	NPC287328
0.9313	High Similarity	NPC475784
0.9313	High Similarity	NPC282009
0.9313	High Similarity	NPC28241
0.9308	High Similarity	NPC27337
0.9308	High Similarity	NPC284820
0.9308	High Similarity	NPC473272
0.9308	High Similarity	NPC237418
0.9268	High Similarity	NPC152477
0.9264	High Similarity	NPC471213
0.9264	High Similarity	NPC43319
0.9259	High Similarity	NPC124038
0.9259	High Similarity	NPC472582
0.9259	High Similarity	NPC476295
0.9255	High Similarity	NPC472632
0.9255	High Similarity	NPC471210
0.9255	High Similarity	NPC234644
0.9255	High Similarity	NPC173137
0.9255	High Similarity	NPC471499
0.9255	High Similarity	NPC57715
0.9255	High Similarity	NPC289771
0.9255	High Similarity	NPC26326
0.925	High Similarity	NPC22192
0.925	High Similarity	NPC280680
0.9245	High Similarity	NPC35038
0.9245	High Similarity	NPC195796
0.9245	High Similarity	NPC170026
0.9245	High Similarity	NPC282307
0.9245	High Similarity	NPC278778
0.9245	High Similarity	NPC291878
0.9241	High Similarity	NPC170492
0.9207	High Similarity	NPC476306
0.9207	High Similarity	NPC218226
0.9202	High Similarity	NPC293319
0.9202	High Similarity	NPC300053
0.9202	High Similarity	NPC108433
0.9202	High Similarity	NPC224280
0.9202	High Similarity	NPC303174
0.9198	High Similarity	NPC474034
0.9198	High Similarity	NPC474033
0.9198	High Similarity	NPC194427
0.9198	High Similarity	NPC81679
0.9198	High Similarity	NPC261470
0.9193	High Similarity	NPC470326
0.9193	High Similarity	NPC174953
0.9193	High Similarity	NPC297212
0.9193	High Similarity	NPC470183
0.9193	High Similarity	NPC476280
0.9193	High Similarity	NPC188433
0.9193	High Similarity	NPC36217
0.9187	High Similarity	NPC471515
0.9187	High Similarity	NPC471209
0.9187	High Similarity	NPC67876
0.9187	High Similarity	NPC472598
0.9187	High Similarity	NPC474055
0.9187	High Similarity	NPC52889
0.9187	High Similarity	NPC291508
0.9187	High Similarity	NPC78071
0.9187	High Similarity	NPC471479
0.9182	High Similarity	NPC234255
0.9182	High Similarity	NPC470327
0.9182	High Similarity	NPC45849
0.9182	High Similarity	NPC200761
0.9182	High Similarity	NPC477503
0.9182	High Similarity	NPC133392
0.9177	High Similarity	NPC37684
0.9177	High Similarity	NPC157784
0.9177	High Similarity	NPC471982
0.9177	High Similarity	NPC63187
0.9157	High Similarity	NPC121333
0.9152	High Similarity	NPC177480
0.9152	High Similarity	NPC242395
0.9146	High Similarity	NPC170245
0.9146	High Similarity	NPC235610
0.9146	High Similarity	NPC272502
0.9141	High Similarity	NPC473313
0.9141	High Similarity	NPC12461
0.9141	High Similarity	NPC306321
0.9141	High Similarity	NPC329669
0.9141	High Similarity	NPC472278
0.9141	High Similarity	NPC41301
0.9141	High Similarity	NPC303460
0.9136	High Similarity	NPC471211
0.9136	High Similarity	NPC471212
0.9136	High Similarity	NPC134783
0.9136	High Similarity	NPC472634
0.9136	High Similarity	NPC198829
0.9136	High Similarity	NPC259456
0.913	High Similarity	NPC46736
0.913	High Similarity	NPC117418
0.913	High Similarity	NPC204879
0.913	High Similarity	NPC55738
0.913	High Similarity	NPC53545
0.913	High Similarity	NPC187792
0.913	High Similarity	NPC473990
0.913	High Similarity	NPC197856
0.913	High Similarity	NPC469658
0.9125	High Similarity	NPC209614
0.9125	High Similarity	NPC326037
0.9125	High Similarity	NPC320825
0.9125	High Similarity	NPC472626
0.9125	High Similarity	NPC470328
0.9125	High Similarity	NPC471500
0.9125	High Similarity	NPC472455
0.9125	High Similarity	NPC13858
0.9125	High Similarity	NPC276444
0.9119	High Similarity	NPC192083
0.9119	High Similarity	NPC18727
0.9119	High Similarity	NPC213896
0.9119	High Similarity	NPC270620
0.9119	High Similarity	NPC78326
0.9119	High Similarity	NPC74924
0.9119	High Similarity	NPC236223
0.9119	High Similarity	NPC179126
0.9114	High Similarity	NPC252933
0.9114	High Similarity	NPC59162
0.9114	High Similarity	NPC200740
0.9114	High Similarity	NPC54394
0.9114	High Similarity	NPC471675
0.9114	High Similarity	NPC304295
0.9114	High Similarity	NPC205046
0.9114	High Similarity	NPC125062
0.9102	High Similarity	NPC310794
0.9096	High Similarity	NPC101107
0.9091	High Similarity	NPC158761
0.9091	High Similarity	NPC8965
0.9085	High Similarity	NPC470457
0.9085	High Similarity	NPC234052
0.9085	High Similarity	NPC275780
0.9085	High Similarity	NPC239752
0.9085	High Similarity	NPC326520
0.9085	High Similarity	NPC472450
0.9085	High Similarity	NPC475888
0.9085	High Similarity	NPC473286
0.9085	High Similarity	NPC50960
0.908	High Similarity	NPC206605
0.908	High Similarity	NPC211107
0.908	High Similarity	NPC201800
0.908	High Similarity	NPC83922
0.908	High Similarity	NPC476247
0.908	High Similarity	NPC472448
0.9074	High Similarity	NPC204290
0.9074	High Similarity	NPC476980
0.9074	High Similarity	NPC474960
0.9074	High Similarity	NPC472630
0.9074	High Similarity	NPC472631
0.9074	High Similarity	NPC246478
0.9074	High Similarity	NPC471973
0.9068	High Similarity	NPC187745
0.9068	High Similarity	NPC161960
0.9068	High Similarity	NPC304008
0.9068	High Similarity	NPC180011
0.9068	High Similarity	NPC52530
0.9068	High Similarity	NPC273843
0.9068	High Similarity	NPC218871
0.9068	High Similarity	NPC218313
0.9068	High Similarity	NPC223787
0.9068	High Similarity	NPC476630
0.9068	High Similarity	NPC474681
0.9068	High Similarity	NPC219867
0.9062	High Similarity	NPC304207
0.9062	High Similarity	NPC259710
0.9062	High Similarity	NPC321779
0.9062	High Similarity	NPC476169
0.9062	High Similarity	NPC207809
0.9062	High Similarity	NPC217706
0.9062	High Similarity	NPC472280
0.9062	High Similarity	NPC226025
0.9062	High Similarity	NPC471116
0.9062	High Similarity	NPC48579
0.9057	High Similarity	NPC236637
0.9057	High Similarity	NPC55205

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 NPC165456 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	940
0.2-0.3	1789
0.3-0.4	2664
0.4-0.5	1867
0.5-0.6	946
0.6-0.7	375
0.7-0.8	126
0.8-0.85	27
0.85-0.9	20
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9119	High Similarity	NPD2393	Clinical (unspecified phase)
0.9057	High Similarity	NPD1934	Approved
0.9006	High Similarity	NPD3882	Suspended
0.897	High Similarity	NPD6166	Phase 2
0.897	High Similarity	NPD6167	Clinical (unspecified phase)
0.897	High Similarity	NPD6168	Clinical (unspecified phase)
0.8882	High Similarity	NPD2801	Approved
0.8797	High Similarity	NPD1512	Approved
0.875	High Similarity	NPD3818	Discontinued
0.8734	High Similarity	NPD4378	Clinical (unspecified phase)
0.8727	High Similarity	NPD5494	Approved
0.8712	High Similarity	NPD3817	Phase 2
0.8671	High Similarity	NPD1511	Approved
0.8596	High Similarity	NPD6797	Phase 2
0.8588	High Similarity	NPD7054	Approved
0.858	High Similarity	NPD4380	Phase 2
0.8547	High Similarity	NPD7251	Discontinued
0.8538	High Similarity	NPD7472	Approved
0.8538	High Similarity	NPD7074	Phase 3
0.8497	Intermediate Similarity	NPD7808	Phase 3
0.8497	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD7075	Discontinued
0.8424	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD6801	Discontinued
0.8323	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6599	Discontinued
0.8235	Intermediate Similarity	NPD1247	Approved
0.8225	Intermediate Similarity	NPD919	Approved
0.8187	Intermediate Similarity	NPD6232	Discontinued
0.8176	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD5844	Phase 1
0.8155	Intermediate Similarity	NPD5402	Approved
0.815	Intermediate Similarity	NPD7473	Discontinued
0.8129	Intermediate Similarity	NPD6959	Discontinued
0.8125	Intermediate Similarity	NPD1549	Phase 2
0.8113	Intermediate Similarity	NPD2796	Approved
0.8098	Intermediate Similarity	NPD6799	Approved
0.8095	Intermediate Similarity	NPD7819	Suspended
0.8075	Intermediate Similarity	NPD2800	Approved
0.8068	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD5403	Approved
0.805	Intermediate Similarity	NPD1510	Phase 2
0.8035	Intermediate Similarity	NPD3926	Phase 2
0.8023	Intermediate Similarity	NPD6559	Discontinued
0.7976	Intermediate Similarity	NPD7411	Suspended
0.7939	Intermediate Similarity	NPD5401	Approved
0.7882	Intermediate Similarity	NPD1465	Phase 2
0.7845	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD2532	Approved
0.7831	Intermediate Similarity	NPD2534	Approved
0.7831	Intermediate Similarity	NPD2533	Approved
0.7799	Intermediate Similarity	NPD1240	Approved
0.7791	Intermediate Similarity	NPD7768	Phase 2
0.7784	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD3749	Approved
0.7727	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD8434	Phase 2
0.7702	Intermediate Similarity	NPD1607	Approved
0.7701	Intermediate Similarity	NPD6234	Discontinued
0.7697	Intermediate Similarity	NPD3750	Approved
0.7697	Intermediate Similarity	NPD4628	Phase 3
0.7688	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1613	Approved
0.7688	Intermediate Similarity	NPD943	Approved
0.7683	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD920	Approved
0.7633	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7199	Phase 2
0.761	Intermediate Similarity	NPD3027	Phase 3
0.7598	Intermediate Similarity	NPD3751	Discontinued
0.7571	Intermediate Similarity	NPD3787	Discontinued
0.7561	Intermediate Similarity	NPD2935	Discontinued
0.7561	Intermediate Similarity	NPD6099	Approved
0.7561	Intermediate Similarity	NPD6100	Approved
0.7547	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD1243	Approved
0.753	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4965	Approved
0.7486	Intermediate Similarity	NPD4967	Phase 2
0.7486	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD6651	Approved
0.7484	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6190	Approved
0.7432	Intermediate Similarity	NPD7685	Pre-registration
0.7423	Intermediate Similarity	NPD230	Phase 1
0.7412	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2344	Approved
0.7409	Intermediate Similarity	NPD2493	Approved
0.7409	Intermediate Similarity	NPD2494	Approved
0.7394	Intermediate Similarity	NPD3748	Approved
0.7381	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4363	Phase 3
0.7368	Intermediate Similarity	NPD4360	Phase 2
0.7358	Intermediate Similarity	NPD6778	Approved
0.7358	Intermediate Similarity	NPD6779	Approved
0.7358	Intermediate Similarity	NPD6782	Approved
0.7358	Intermediate Similarity	NPD6776	Approved
0.7358	Intermediate Similarity	NPD6781	Approved
0.7358	Intermediate Similarity	NPD6777	Approved
0.7358	Intermediate Similarity	NPD6780	Approved
0.7353	Intermediate Similarity	NPD7390	Discontinued
0.7349	Intermediate Similarity	NPD1551	Phase 2
0.7346	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD3226	Approved
0.7326	Intermediate Similarity	NPD8150	Discontinued
0.732	Intermediate Similarity	NPD3450	Approved
0.732	Intermediate Similarity	NPD3452	Approved
0.7317	Intermediate Similarity	NPD447	Suspended
0.7296	Intermediate Similarity	NPD4582	Approved
0.7296	Intermediate Similarity	NPD4583	Approved
0.7293	Intermediate Similarity	NPD2403	Approved
0.7289	Intermediate Similarity	NPD2799	Discontinued
0.7289	Intermediate Similarity	NPD7033	Discontinued
0.7289	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD1653	Approved
0.7283	Intermediate Similarity	NPD5953	Discontinued
0.7278	Intermediate Similarity	NPD5710	Approved
0.7278	Intermediate Similarity	NPD5711	Approved
0.7268	Intermediate Similarity	NPD7286	Phase 2
0.7268	Intermediate Similarity	NPD7907	Approved
0.7258	Intermediate Similarity	NPD8312	Approved
0.7258	Intermediate Similarity	NPD8313	Approved
0.7255	Intermediate Similarity	NPD4665	Approved
0.7255	Intermediate Similarity	NPD4111	Phase 1
0.7245	Intermediate Similarity	NPD4002	Approved
0.7245	Intermediate Similarity	NPD4004	Approved
0.7245	Intermediate Similarity	NPD7435	Discontinued
0.7241	Intermediate Similarity	NPD7458	Discontinued
0.724	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD4361	Phase 2
0.7239	Intermediate Similarity	NPD2313	Discontinued
0.7235	Intermediate Similarity	NPD2309	Approved
0.7222	Intermediate Similarity	NPD8127	Discontinued
0.7222	Intermediate Similarity	NPD7584	Approved
0.7222	Intermediate Similarity	NPD4908	Phase 1
0.7212	Intermediate Similarity	NPD6355	Discontinued
0.7212	Intermediate Similarity	NPD5124	Phase 1
0.7212	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2488	Approved
0.7211	Intermediate Similarity	NPD2490	Approved
0.7209	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2974	Approved
0.7202	Intermediate Similarity	NPD2975	Approved
0.7202	Intermediate Similarity	NPD2346	Discontinued
0.7202	Intermediate Similarity	NPD2973	Approved
0.7182	Intermediate Similarity	NPD7229	Phase 3
0.7176	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5761	Phase 2
0.7175	Intermediate Similarity	NPD5760	Phase 2
0.716	Intermediate Similarity	NPD9494	Approved
0.7157	Intermediate Similarity	NPD7698	Approved
0.7157	Intermediate Similarity	NPD7697	Approved
0.7157	Intermediate Similarity	NPD7696	Phase 3
0.7152	Intermediate Similarity	NPD4060	Phase 1
0.7134	Intermediate Similarity	NPD6798	Discontinued
0.7125	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7871	Phase 2
0.7121	Intermediate Similarity	NPD7870	Phase 2
0.7108	Intermediate Similarity	NPD1933	Approved
0.7104	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7701	Phase 2
0.7098	Intermediate Similarity	NPD6534	Approved
0.7098	Intermediate Similarity	NPD6535	Approved
0.7092	Intermediate Similarity	NPD4580	Approved
0.7076	Intermediate Similarity	NPD4110	Phase 3
0.7076	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7095	Approved
0.7073	Intermediate Similarity	NPD4625	Phase 3
0.7069	Intermediate Similarity	NPD6273	Approved
0.7065	Intermediate Similarity	NPD8151	Discontinued
0.7059	Intermediate Similarity	NPD2424	Discontinued
0.7059	Intermediate Similarity	NPD7240	Approved
0.7049	Intermediate Similarity	NPD5242	Approved
0.7045	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7874	Approved
0.703	Intermediate Similarity	NPD3268	Approved
0.703	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2163	Approved
0.702	Intermediate Similarity	NPD2491	Approved
0.702	Intermediate Similarity	NPD3057	Approved
0.7006	Intermediate Similarity	NPD7028	Phase 2
0.7	Intermediate 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