NPASS Compound

Structure

CID109061 OpenBabel06191715462D 36 40 0 0 1 0 0 0 0 0999 V2000 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 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 -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 1.0000 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 0.0000 -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 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 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 2.5000 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 -3.4641 -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 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 3.4641 1.0000 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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 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 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -1.7321 -2.0000 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 4.0000 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 3.4641 0.0000 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 33 1 0 0 0 0 2 34 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 15 1 0 0 0 0 5 12 2 0 0 0 0 5 17 1 0 0 0 0 6 12 1 0 0 0 0 6 18 2 0 0 0 0 7 11 2 0 0 0 0 7 20 1 0 0 0 0 8 14 1 0 0 0 0 8 19 1 0 0 0 0 9 13 1 0 0 0 0 9 22 1 0 0 0 0 10 16 2 0 0 0 0 10 21 1 0 0 0 0 13 11 1 1 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 25 2 0 0 0 0 15 20 2 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 26 2 0 0 0 0 17 29 1 0 0 0 0 18 26 1 0 0 0 0 18 30 1 0 0 0 0 19 24 1 0 0 0 0 19 31 1 6 0 0 0 20 33 1 0 0 0 0 21 23 2 0 0 0 0 21 35 1 0 0 0 0 22 32 2 0 0 0 0 22 35 1 0 0 0 0 23 25 1 0 0 0 0 24 12 1 1 0 0 0 24 36 1 0 0 0 0 25 36 1 0 0 0 0 26 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.14
Volume:	477.007
LogP:	2.511
LogD:	2.484
LogS:	-4.059
# Rotatable Bonds:	4
TPSA:	155.14
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.269
Synthetic Accessibility Score:	4.081
Fsp3:	0.269
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.992
MDCK Permeability:	8.244383934652433e-06
Pgp-inhibitor:	0.132
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.237

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	94.14054107666016%
Volume Distribution (VD):	0.468
Pgp-substrate:	8.904592514038086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.621
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.758
CYP2C9-substrate:	0.901
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.22
CYP3A4-inhibitor:	0.361
CYP3A4-substrate:	0.786

ADMET: Excretion

Clearance (CL):	9.422
Half-life (T1/2):	0.757

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.021
Drug-inuced Liver Injury (DILI):	0.386
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.843
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.91
Carcinogencity:	0.06
Eye Corrosion:	0.003
Eye Irritation:	0.804
Respiratory Toxicity:	0.24

Download Data

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

Natural Product: NPC109061

Natural Product ID:	NPC109061
*Common Name:**	4',3''-Di-O-Methylapocynin-B
IUPAC Name:	(2R,3S,10R)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,5-dihydroxy-10-(4-hydroxy-3-methoxyphenyl)-3,4,9,10-tetrahydro-2H-pyrano[2,3-f]chromen-8-one
Synonyms:
Standard InCHIKey:	GWDMTADRTCKKKV-ZXWJAXLNSA-N
Standard InCHI:	InChI=1S/C26H24O10/c1-33-20-7-11(3-4-15(20)27)13-9-22(32)35-21-10-16(28)14-8-19(31)24(36-25(14)23(13)21)12-5-17(29)26(34-2)18(30)6-12/h3-7,10,13,19,24,27-31H,8-9H2,1-2H3/t13-,19+,24-/m1/s1
SMILES:	COc1c(O)cc(cc1O)[C@H]1Oc2c(C[C@@H]1O)c(O)cc1c2[C@H](CC(=O)O1)c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651277
PubChem CID:	50908213
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003012] Flavan-3-ols [CHEMONTID:0001584] Catechins [CHEMONTID:0001594] Epigallocatechins

*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
NPO23452	Parapiptadenia rigida	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[21080642]
NPO23452	Parapiptadenia rigida	Species	Fabaceae	Eukaryota	bark	Santa Maria, Rio Grande do Sul, Brazil	2007-OCT	PMID[21080642]
NPO23452	Parapiptadenia rigida	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[21553897]
NPO21327	Ramalina stenospora	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23452	Parapiptadenia rigida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23614	Ovophis okinavensis	Species	Viperidae	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	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	Activity	=	11.0	%	PMID[524842]
NPT283	Individual Protein	MAP kinase p38 alpha	Homo sapiens	IC50	=	50800.0	nM	PMID[524842]

☑ 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 NPC109061 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	364
0.1-0.2	1450
0.2-0.3	3360
0.3-0.4	8140
0.4-0.5	10454
0.5-0.6	3726
0.6-0.7	5281
0.7-0.8	7576
0.8-0.85	1998
0.85-0.9	323
0.9-0.95	13
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9868	High Similarity	NPC98083
0.9868	High Similarity	NPC166456
0.9868	High Similarity	NPC94220
0.9868	High Similarity	NPC24339
0.9868	High Similarity	NPC7543
0.974	High Similarity	NPC124747
0.974	High Similarity	NPC155754
0.9737	High Similarity	NPC165483
0.9494	High Similarity	NPC9309
0.9487	High Similarity	NPC177100
0.9487	High Similarity	NPC139540
0.9057	High Similarity	NPC53889
0.9057	High Similarity	NPC24164
0.9026	High Similarity	NPC211561
0.9024	High Similarity	NPC65333
0.8994	High Similarity	NPC87317
0.8981	High Similarity	NPC8712
0.897	High Similarity	NPC98583
0.8963	High Similarity	NPC180768
0.8951	High Similarity	NPC142614
0.8944	High Similarity	NPC55121
0.8931	High Similarity	NPC114179
0.8931	High Similarity	NPC156818
0.8931	High Similarity	NPC160512
0.8931	High Similarity	NPC68324
0.8931	High Similarity	NPC289322
0.8931	High Similarity	NPC38779
0.8909	High Similarity	NPC271848
0.8909	High Similarity	NPC100251
0.8909	High Similarity	NPC81332
0.8909	High Similarity	NPC262580
0.8909	High Similarity	NPC289396
0.8909	High Similarity	NPC212038
0.8896	High Similarity	NPC170103
0.8896	High Similarity	NPC471823
0.8896	High Similarity	NPC204770
0.8896	High Similarity	NPC82917
0.8896	High Similarity	NPC236202
0.8896	High Similarity	NPC108811
0.8896	High Similarity	NPC202742
0.8896	High Similarity	NPC262911
0.8896	High Similarity	NPC70409
0.8896	High Similarity	NPC58190
0.8896	High Similarity	NPC294558
0.8896	High Similarity	NPC18185
0.8896	High Similarity	NPC263940
0.8882	High Similarity	NPC142252
0.8868	High Similarity	NPC250436
0.8868	High Similarity	NPC88803
0.8868	High Similarity	NPC300845
0.8868	High Similarity	NPC104983
0.8868	High Similarity	NPC291948
0.8868	High Similarity	NPC318432
0.8862	High Similarity	NPC67629
0.8862	High Similarity	NPC79736
0.8861	High Similarity	NPC268484
0.8848	High Similarity	NPC279209
0.8848	High Similarity	NPC102277
0.8846	High Similarity	NPC477612
0.8841	High Similarity	NPC473818
0.8834	High Similarity	NPC7154
0.8834	High Similarity	NPC36916
0.8834	High Similarity	NPC7688
0.8834	High Similarity	NPC36
0.8834	High Similarity	NPC72787
0.8834	High Similarity	NPC471788
0.8834	High Similarity	NPC58223
0.8834	High Similarity	NPC125039
0.8831	High Similarity	NPC96576
0.8827	High Similarity	NPC476372
0.8827	High Similarity	NPC174311
0.8827	High Similarity	NPC476247
0.8827	High Similarity	NPC476371
0.882	High Similarity	NPC24627
0.8817	High Similarity	NPC117668
0.8817	High Similarity	NPC53680
0.8817	High Similarity	NPC208797
0.881	High Similarity	NPC267549
0.8805	High Similarity	NPC292385
0.8805	High Similarity	NPC155015
0.8805	High Similarity	NPC142479
0.8805	High Similarity	NPC125709
0.8797	High Similarity	NPC474656
0.8797	High Similarity	NPC223720
0.8797	High Similarity	NPC178574
0.8797	High Similarity	NPC65591
0.8795	High Similarity	NPC186847
0.8795	High Similarity	NPC472454
0.8795	High Similarity	NPC257667
0.8788	High Similarity	NPC475212
0.878	High Similarity	NPC224851
0.878	High Similarity	NPC43065
0.878	High Similarity	NPC207575
0.878	High Similarity	NPC13481
0.8773	High Similarity	NPC121290
0.8773	High Similarity	NPC45943
0.8765	High Similarity	NPC113163
0.8765	High Similarity	NPC84324
0.8765	High Similarity	NPC165970
0.8765	High Similarity	NPC103201
0.8765	High Similarity	NPC288131
0.8765	High Similarity	NPC469889
0.8765	High Similarity	NPC305987
0.8765	High Similarity	NPC473106
0.8765	High Similarity	NPC26326
0.8765	High Similarity	NPC66618
0.8765	High Similarity	NPC158188
0.8765	High Similarity	NPC472632
0.875	High Similarity	NPC297574
0.875	High Similarity	NPC178054
0.8742	High Similarity	NPC7178
0.8742	High Similarity	NPC62903
0.8735	High Similarity	NPC91043
0.8735	High Similarity	NPC476365
0.8734	High Similarity	NPC272552
0.8734	High Similarity	NPC322899
0.8734	High Similarity	NPC264875
0.8734	High Similarity	NPC120774
0.8734	High Similarity	NPC476434
0.8734	High Similarity	NPC226108
0.8734	High Similarity	NPC46283
0.8734	High Similarity	NPC163598
0.8734	High Similarity	NPC44192
0.8734	High Similarity	NPC134911
0.8734	High Similarity	NPC469944
0.8727	High Similarity	NPC14662
0.872	High Similarity	NPC477840
0.8718	High Similarity	NPC187398
0.8718	High Similarity	NPC476348
0.8718	High Similarity	NPC227516
0.8718	High Similarity	NPC20757
0.8712	High Similarity	NPC474034
0.8712	High Similarity	NPC477841
0.8712	High Similarity	NPC474033
0.8712	High Similarity	NPC12326
0.8712	High Similarity	NPC140346
0.8712	High Similarity	NPC476200
0.8712	High Similarity	NPC192258
0.871	High Similarity	NPC268515
0.871	High Similarity	NPC260397
0.871	High Similarity	NPC40222
0.8706	High Similarity	NPC125352
0.8704	High Similarity	NPC476373
0.8704	High Similarity	NPC174953
0.8704	High Similarity	NPC292415
0.8704	High Similarity	NPC101731
0.8701	High Similarity	NPC171932
0.8701	High Similarity	NPC28440
0.8701	High Similarity	NPC473108
0.8696	High Similarity	NPC472598
0.8696	High Similarity	NPC125495
0.8696	High Similarity	NPC108456
0.8696	High Similarity	NPC36077
0.8696	High Similarity	NPC474055
0.8683	High Similarity	NPC4200
0.8683	High Similarity	NPC256760
0.8683	High Similarity	NPC67134
0.8683	High Similarity	NPC47140
0.8679	High Similarity	NPC306267
0.8679	High Similarity	NPC473236
0.8679	High Similarity	NPC476154
0.8679	High Similarity	NPC20050
0.8675	High Similarity	NPC188079
0.8667	High Similarity	NPC320741
0.8667	High Similarity	NPC171985
0.8667	High Similarity	NPC471213
0.8662	High Similarity	NPC113790
0.8659	High Similarity	NPC67959
0.8655	High Similarity	NPC123259
0.8655	High Similarity	NPC129533
0.8654	High Similarity	NPC476347
0.865	High Similarity	NPC97812
0.865	High Similarity	NPC471210
0.865	High Similarity	NPC471499
0.865	High Similarity	NPC216916
0.865	High Similarity	NPC349525
0.865	High Similarity	NPC471211
0.865	High Similarity	NPC471212
0.865	High Similarity	NPC474038
0.865	High Similarity	NPC472634
0.8647	High Similarity	NPC324742
0.8642	High Similarity	NPC37502
0.8642	High Similarity	NPC172202
0.8642	High Similarity	NPC40702
0.8642	High Similarity	NPC53545
0.8642	High Similarity	NPC36354
0.8642	High Similarity	NPC284127
0.8642	High Similarity	NPC473990
0.8642	High Similarity	NPC476410
0.8642	High Similarity	NPC117418
0.8642	High Similarity	NPC267627
0.8634	High Similarity	NPC195796
0.8634	High Similarity	NPC291878
0.8634	High Similarity	NPC35038
0.8634	High Similarity	NPC278778
0.8631	High Similarity	NPC219600
0.8631	High Similarity	NPC166674
0.8631	High Similarity	NPC263119
0.8631	High Similarity	NPC208668
0.8631	High Similarity	NPC46640

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 NPC109061 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	892
0.2-0.3	1764
0.3-0.4	2608
0.4-0.5	1827
0.5-0.6	988
0.6-0.7	582
0.7-0.8	147
0.8-0.85	27
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8868	High Similarity	NPD4868	Clinical (unspecified phase)
0.8834	High Similarity	NPD6166	Phase 2
0.8834	High Similarity	NPD6168	Clinical (unspecified phase)
0.8834	High Similarity	NPD6167	Clinical (unspecified phase)
0.8788	High Similarity	NPD5844	Phase 1
0.8614	High Similarity	NPD7228	Approved
0.8571	High Similarity	NPD7993	Clinical (unspecified phase)
0.8537	High Similarity	NPD7199	Phase 2
0.8512	High Similarity	NPD7074	Phase 3
0.8509	High Similarity	NPD2393	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7054	Approved
0.8447	Intermediate Similarity	NPD1934	Approved
0.8415	Intermediate Similarity	NPD6234	Discontinued
0.8402	Intermediate Similarity	NPD7472	Approved
0.8395	Intermediate Similarity	NPD1465	Phase 2
0.8333	Intermediate Similarity	NPD37	Approved
0.8323	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD4965	Approved
0.8293	Intermediate Similarity	NPD4966	Approved
0.8293	Intermediate Similarity	NPD4967	Phase 2
0.8263	Intermediate Similarity	NPD6232	Discontinued
0.8246	Intermediate Similarity	NPD6797	Phase 2
0.8225	Intermediate Similarity	NPD7473	Discontinued
0.8224	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1613	Approved
0.8198	Intermediate Similarity	NPD7251	Discontinued
0.8171	Intermediate Similarity	NPD8455	Phase 2
0.815	Intermediate Similarity	NPD7808	Phase 3
0.815	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD5494	Approved
0.8133	Intermediate Similarity	NPD7075	Discontinued
0.8125	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD3817	Phase 2
0.8098	Intermediate Similarity	NPD4380	Phase 2
0.8095	Intermediate Similarity	NPD6959	Discontinued
0.8092	Intermediate Similarity	NPD7240	Approved
0.8092	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD3818	Discontinued
0.8061	Intermediate Similarity	NPD2801	Approved
0.8049	Intermediate Similarity	NPD7411	Suspended
0.8026	Intermediate Similarity	NPD3027	Phase 3
0.8023	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1653	Approved
0.7974	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD4908	Phase 1
0.7961	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7819	Suspended
0.7917	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6801	Discontinued
0.7857	Intermediate Similarity	NPD3882	Suspended
0.784	Intermediate Similarity	NPD1511	Approved
0.7836	Intermediate Similarity	NPD7229	Phase 3
0.7826	Intermediate Similarity	NPD6190	Approved
0.7784	Intermediate Similarity	NPD6559	Discontinued
0.7778	Intermediate Similarity	NPD8127	Discontinued
0.7778	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD7680	Approved
0.7751	Intermediate Similarity	NPD7768	Phase 2
0.7744	Intermediate Similarity	NPD1512	Approved
0.7742	Intermediate Similarity	NPD6798	Discontinued
0.7733	Intermediate Similarity	NPD3787	Discontinued
0.773	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD5124	Phase 1
0.7702	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8312	Approved
0.7697	Intermediate Similarity	NPD8313	Approved
0.7697	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4628	Phase 3
0.7643	Intermediate Similarity	NPD4060	Phase 1
0.764	Intermediate Similarity	NPD7549	Discontinued
0.7625	Intermediate Similarity	NPD6099	Approved
0.7625	Intermediate Similarity	NPD6100	Approved
0.7605	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6355	Discontinued
0.7593	Intermediate Similarity	NPD6674	Discontinued
0.7588	Intermediate Similarity	NPD5402	Approved
0.7584	Intermediate Similarity	NPD7685	Pre-registration
0.758	Intermediate Similarity	NPD6233	Phase 2
0.7578	Intermediate Similarity	NPD7266	Discontinued
0.7578	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD3751	Discontinued
0.7546	Intermediate Similarity	NPD3750	Approved
0.7531	Intermediate Similarity	NPD1549	Phase 2
0.7515	Intermediate Similarity	NPD6799	Approved
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7097	Phase 1
0.75	Intermediate Similarity	NPD3749	Approved
0.75	Intermediate Similarity	NPD1610	Phase 2
0.7485	Intermediate Similarity	NPD5403	Approved
0.7484	Intermediate Similarity	NPD230	Phase 1
0.7457	Intermediate Similarity	NPD919	Approved
0.7456	Intermediate Similarity	NPD6599	Discontinued
0.7453	Intermediate Similarity	NPD7033	Discontinued
0.7451	Intermediate Similarity	NPD1608	Approved
0.7439	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4110	Phase 3
0.7423	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2797	Approved
0.7405	Intermediate Similarity	NPD3268	Approved
0.7385	Intermediate Similarity	NPD7783	Phase 2
0.7385	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1652	Phase 2
0.7371	Intermediate Similarity	NPD8151	Discontinued
0.7365	Intermediate Similarity	NPD5401	Approved
0.7365	Intermediate Similarity	NPD2533	Approved
0.7365	Intermediate Similarity	NPD2534	Approved
0.7365	Intermediate Similarity	NPD2532	Approved
0.7363	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6004	Phase 3
0.7362	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6002	Phase 3
0.7362	Intermediate Similarity	NPD6005	Phase 3
0.7342	Intermediate Similarity	NPD4625	Phase 3
0.7333	Intermediate Similarity	NPD8166	Discontinued
0.7325	Intermediate Similarity	NPD2861	Phase 2
0.7301	Intermediate Similarity	NPD2796	Approved
0.7301	Intermediate Similarity	NPD2935	Discontinued
0.7296	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3226	Approved
0.7294	Intermediate Similarity	NPD7458	Discontinued
0.7283	Intermediate Similarity	NPD8150	Discontinued
0.7273	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD17	Approved
0.7249	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1510	Phase 2
0.7239	Intermediate Similarity	NPD3748	Approved
0.7233	Intermediate Similarity	NPD7095	Approved
0.7219	Intermediate Similarity	NPD6273	Approved
0.7195	Intermediate Similarity	NPD2438	Suspended
0.7191	Intermediate Similarity	NPD3926	Phase 2
0.7179	Intermediate Similarity	NPD4749	Approved
0.7161	Intermediate Similarity	NPD422	Phase 1
0.716	Intermediate Similarity	NPD447	Suspended
0.7152	Intermediate Similarity	NPD5762	Approved
0.7152	Intermediate Similarity	NPD5763	Approved
0.7134	Intermediate Similarity	NPD3225	Approved
0.7126	Intermediate Similarity	NPD7003	Approved
0.7124	Intermediate Similarity	NPD1548	Phase 1
0.7119	Intermediate Similarity	NPD6746	Phase 2
0.7118	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6653	Approved
0.7113	Intermediate Similarity	NPD7435	Discontinued
0.7107	Intermediate Similarity	NPD3018	Phase 2
0.7105	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7039	Approved
0.7104	Intermediate Similarity	NPD7038	Approved
0.7101	Intermediate Similarity	NPD7213	Phase 3
0.7101	Intermediate Similarity	NPD7390	Discontinued
0.7101	Intermediate Similarity	NPD7212	Phase 2
0.7099	Intermediate Similarity	NPD4140	Approved
0.7099	Intermediate Similarity	NPD1240	Approved
0.7099	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3620	Phase 2
0.7098	Intermediate Similarity	NPD2494	Approved
0.7098	Intermediate Similarity	NPD2493	Approved
0.7097	Intermediate Similarity	NPD8434	Phase 2
0.7095	Intermediate Similarity	NPD5242	Approved
0.7093	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1551	Phase 2
0.7089	Intermediate Similarity	NPD3266	Approved
0.7089	Intermediate Similarity	NPD3267	Approved
0.7086	Intermediate Similarity	NPD5353	Approved
0.7081	Intermediate Similarity	NPD8054	Approved
0.7081	Intermediate Similarity	NPD8053	Approved
0.7079	Intermediate Similarity	NPD1247	Approved
0.7077	Intermediate Similarity	NPD4583	Approved
0.7077	Intermediate Similarity	NPD4582	Approved
0.7076	Intermediate Similarity	NPD7427	Discontinued
0.7076	Intermediate Similarity	NPD920	Approved
0.7074	Intermediate Similarity	NPD2490	Approved
0.7074	Intermediate Similarity	NPD2488	Approved
0.707	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7447	Phase 1
0.7059	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7585	Approved
0.7049	Intermediate Similarity	NPD5953	Discontinued
0.7047	Intermediate Similarity	NPD6782	Approved
0.7047	Intermediate Similarity	NPD6777	Approved
0.7047	Intermediate Similarity	NPD6779	Approved
0.7047	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6780	Approved
0.7047	Intermediate Similarity	NPD6778	Approved
0.7047	Intermediate Similarity	NPD6781	Approved
0.7047	Intermediate Similarity	NPD6776	Approved
0.7041	Intermediate Similarity	NPD6666	Approved
0.7041	Intermediate Similarity	NPD6667	Approved
0.7037	Intermediate Similarity	NPD4062	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