NPASS Compound

Structure

CID127172 OpenBabel06191715482D 24 25 0 0 0 0 0 0 0 0999 V2000 -7.7942 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 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 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 -4.3301 0.5000 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 -6.0622 0.5000 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 -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 -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 -3.4641 -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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 24 1 0 0 0 0 3 4 1 0 0 0 0 4 8 1 0 0 0 0 5 6 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 18 2 0 0 0 0 9 13 1 0 0 0 0 9 14 2 0 0 0 0 10 12 1 0 0 0 0 10 15 1 0 0 0 0 11 17 2 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 16 2 0 0 0 0 13 20 2 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 22 2 0 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.11
Volume:	328.552
LogP:	2.918
LogD:	1.817
LogS:	-3.022
# Rotatable Bonds:	5
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.323
Synthetic Accessibility Score:	3.108
Fsp3:	0.235
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	3
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.213
MDCK Permeability:	1.1549848750291858e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.137
20% Bioavailability (F20%):	0.086
30% Bioavailability (F30%):	0.276

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	97.76123809814453%
Volume Distribution (VD):	0.423
Pgp-substrate:	6.897458553314209%

ADMET: Metabolism

CYP1A2-inhibitor:	0.846
CYP1A2-substrate:	0.854
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.404
CYP2C9-substrate:	0.575
CYP2D6-inhibitor:	0.28
CYP2D6-substrate:	0.215
CYP3A4-inhibitor:	0.114
CYP3A4-substrate:	0.066

ADMET: Excretion

Clearance (CL):	7.726
Half-life (T1/2):	0.905

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.357
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.667
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.637
Skin Sensitization:	0.958
Carcinogencity:	0.271
Eye Corrosion:	0.004
Eye Irritation:	0.906
Respiratory Toxicity:	0.39

Download Data

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

Natural Product: NPC127172

Natural Product ID:	NPC127172
*Common Name:**	GGNMTYGXUUGJFT-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GGNMTYGXUUGJFT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H18O7/c1-3-4-8(18)5-6-9-13(20)12-10(15(22)14(9)21)7-11(19)17(24-2)16(12)23/h7,19,21,23H,3-6H2,1-2H3
SMILES:	CCCC(=O)CCC1=C(O)C(=O)c2c(C1=O)c(O)c(c(c2)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511693
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO9271	Lindbladia tubulina	Species	Cribrariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880324]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9271	Lindbladia tubulina	Species	Cribrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	50.0	ug.mL-1	PMID[478331]
NPT168	Cell Line	P388	Mus musculus	IC50	=	13.8	ug.mL-1	PMID[478331]

☑ 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 NPC127172 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	416
0.1-0.2	1790
0.2-0.3	4977
0.3-0.4	11242
0.4-0.5	6500
0.5-0.6	3900
0.6-0.7	5240
0.7-0.8	6479
0.8-0.85	1824
0.85-0.9	301
0.9-0.95	22
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC234485
0.9474	High Similarity	NPC477410
0.9459	High Similarity	NPC134293
0.9276	High Similarity	NPC472048
0.9247	High Similarity	NPC291078
0.9231	High Similarity	NPC476822
0.9156	High Similarity	NPC37543
0.9156	High Similarity	NPC199463
0.9145	High Similarity	NPC149889
0.9145	High Similarity	NPC312338
0.9139	High Similarity	NPC103509
0.9091	High Similarity	NPC77807
0.9091	High Similarity	NPC5379
0.9091	High Similarity	NPC14561
0.9032	High Similarity	NPC179732
0.9032	High Similarity	NPC178976
0.9026	High Similarity	NPC38898
0.8974	High Similarity	NPC245891
0.8974	High Similarity	NPC104876
0.8961	High Similarity	NPC107109
0.894	High Similarity	NPC77598
0.8933	High Similarity	NPC28632
0.8919	High Similarity	NPC84273
0.8917	High Similarity	NPC84571
0.8896	High Similarity	NPC245975
0.8889	High Similarity	NPC472279
0.8868	High Similarity	NPC249181
0.8867	High Similarity	NPC142165
0.8861	High Similarity	NPC311740
0.8851	High Similarity	NPC50823
0.8839	High Similarity	NPC93552
0.8834	High Similarity	NPC30550
0.8831	High Similarity	NPC46882
0.8831	High Similarity	NPC132990
0.8831	High Similarity	NPC78505
0.882	High Similarity	NPC95715
0.8812	High Similarity	NPC191930
0.88	High Similarity	NPC254659
0.8797	High Similarity	NPC155302
0.8797	High Similarity	NPC161947
0.879	High Similarity	NPC474637
0.878	High Similarity	NPC289244
0.8774	High Similarity	NPC164912
0.8766	High Similarity	NPC85131
0.8758	High Similarity	NPC20237
0.8742	High Similarity	NPC207732
0.8742	High Similarity	NPC87431
0.8734	High Similarity	NPC45846
0.8733	High Similarity	NPC11314
0.8726	High Similarity	NPC474167
0.8726	High Similarity	NPC470762
0.8726	High Similarity	NPC472050
0.872	High Similarity	NPC277510
0.8718	High Similarity	NPC472905
0.8718	High Similarity	NPC477047
0.8718	High Similarity	NPC477048
0.8718	High Similarity	NPC155686
0.8712	High Similarity	NPC28042
0.871	High Similarity	NPC118427
0.871	High Similarity	NPC256406
0.871	High Similarity	NPC302783
0.871	High Similarity	NPC473201
0.871	High Similarity	NPC144283
0.871	High Similarity	NPC272566
0.8704	High Similarity	NPC283041
0.8701	High Similarity	NPC200060
0.8701	High Similarity	NPC92722
0.8701	High Similarity	NPC264550
0.8701	High Similarity	NPC264289
0.8701	High Similarity	NPC333691
0.8701	High Similarity	NPC139293
0.8701	High Similarity	NPC69430
0.8701	High Similarity	NPC40290
0.8701	High Similarity	NPC195763
0.8701	High Similarity	NPC142876
0.8701	High Similarity	NPC102003
0.8696	High Similarity	NPC26386
0.8684	High Similarity	NPC157133
0.8684	High Similarity	NPC160777
0.8684	High Similarity	NPC73416
0.8679	High Similarity	NPC14353
0.8679	High Similarity	NPC56085
0.8679	High Similarity	NPC228785
0.8675	High Similarity	NPC471417
0.8675	High Similarity	NPC119663
0.8675	High Similarity	NPC221820
0.8675	High Similarity	NPC287722
0.8675	High Similarity	NPC77179
0.8675	High Similarity	NPC23553
0.8671	High Similarity	NPC241904
0.8671	High Similarity	NPC136674
0.8671	High Similarity	NPC201127
0.8671	High Similarity	NPC180011
0.8671	High Similarity	NPC300727
0.8671	High Similarity	NPC472963
0.8671	High Similarity	NPC219867
0.8662	High Similarity	NPC168247
0.8662	High Similarity	NPC16082
0.8662	High Similarity	NPC117992
0.8662	High Similarity	NPC256925
0.8662	High Similarity	NPC79998
0.8662	High Similarity	NPC57674
0.8662	High Similarity	NPC134287
0.8662	High Similarity	NPC152951
0.8662	High Similarity	NPC130589
0.8662	High Similarity	NPC82592
0.8662	High Similarity	NPC230149
0.8654	High Similarity	NPC474993
0.8654	High Similarity	NPC470340
0.8645	High Similarity	NPC151473
0.8645	High Similarity	NPC216917
0.8645	High Similarity	NPC280295
0.8642	High Similarity	NPC477517
0.8636	High Similarity	NPC287395
0.8636	High Similarity	NPC131451
0.8636	High Similarity	NPC183655
0.8636	High Similarity	NPC203077
0.8636	High Similarity	NPC238279
0.8636	High Similarity	NPC194653
0.8636	High Similarity	NPC139364
0.8636	High Similarity	NPC254702
0.8636	High Similarity	NPC203747
0.8636	High Similarity	NPC80710
0.8636	High Similarity	NPC166036
0.8636	High Similarity	NPC15329
0.8636	High Similarity	NPC474903
0.8634	High Similarity	NPC101769
0.8634	High Similarity	NPC270837
0.8634	High Similarity	NPC236132
0.8631	High Similarity	NPC8927
0.8631	High Similarity	NPC228209
0.8631	High Similarity	NPC182693
0.8627	High Similarity	NPC226987
0.8627	High Similarity	NPC143903
0.8625	High Similarity	NPC258331
0.8625	High Similarity	NPC117985
0.8625	High Similarity	NPC201560
0.8625	High Similarity	NPC40491
0.8625	High Similarity	NPC278052
0.8625	High Similarity	NPC61010
0.8618	High Similarity	NPC19896
0.8618	High Similarity	NPC475201
0.8618	High Similarity	NPC105213
0.8616	High Similarity	NPC100123
0.8616	High Similarity	NPC55738
0.8616	High Similarity	NPC235448
0.8616	High Similarity	NPC476242
0.8609	High Similarity	NPC284556
0.8609	High Similarity	NPC49108
0.8609	High Similarity	NPC301178
0.8609	High Similarity	NPC312256
0.8608	High Similarity	NPC279605
0.8608	High Similarity	NPC115853
0.8608	High Similarity	NPC274730
0.8608	High Similarity	NPC475799
0.8608	High Similarity	NPC472907
0.8608	High Similarity	NPC13779
0.8608	High Similarity	NPC150227
0.8608	High Similarity	NPC265511
0.8608	High Similarity	NPC472455
0.8599	High Similarity	NPC281477
0.8599	High Similarity	NPC250557
0.8599	High Similarity	NPC227337
0.8599	High Similarity	NPC33051
0.8599	High Similarity	NPC124714
0.8599	High Similarity	NPC70433
0.8599	High Similarity	NPC273462
0.8599	High Similarity	NPC192189
0.8599	High Similarity	NPC49402
0.859	High Similarity	NPC45291
0.859	High Similarity	NPC19980
0.859	High Similarity	NPC474414
0.8581	High Similarity	NPC171916
0.8581	High Similarity	NPC38545
0.858	High Similarity	NPC472049
0.858	High Similarity	NPC303174
0.858	High Similarity	NPC475888
0.8571	High Similarity	NPC190648
0.8571	High Similarity	NPC93034
0.8571	High Similarity	NPC215612
0.8571	High Similarity	NPC119660
0.8571	High Similarity	NPC188074
0.8571	High Similarity	NPC118027
0.8571	High Similarity	NPC125449
0.8571	High Similarity	NPC211107
0.8571	High Similarity	NPC56433
0.8571	High Similarity	NPC48860
0.8571	High Similarity	NPC312929
0.8571	High Similarity	NPC245584
0.8571	High Similarity	NPC294965
0.8571	High Similarity	NPC126767
0.8571	High Similarity	NPC191360
0.8571	High Similarity	NPC289042
0.8571	High Similarity	NPC149389
0.8571	High Similarity	NPC58373
0.8562	High Similarity	NPC471973
0.8562	High Similarity	NPC246478
0.8562	High Similarity	NPC320359
0.8562	High Similarity	NPC474960
0.8562	High Similarity	NPC475107

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 NPC127172 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	1060
0.2-0.3	1974
0.3-0.4	2730
0.4-0.5	1589
0.5-0.6	936
0.6-0.7	342
0.7-0.8	119
0.8-0.85	19
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8608	High Similarity	NPD3882	Suspended
0.8457	Intermediate Similarity	NPD6232	Discontinued
0.8415	Intermediate Similarity	NPD7473	Discontinued
0.8365	Intermediate Similarity	NPD2801	Approved
0.8302	Intermediate Similarity	NPD1934	Approved
0.825	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD1512	Approved
0.8133	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6166	Phase 2
0.8067	Intermediate Similarity	NPD943	Approved
0.8052	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1511	Approved
0.7975	Intermediate Similarity	NPD2532	Approved
0.7975	Intermediate Similarity	NPD2534	Approved
0.7975	Intermediate Similarity	NPD2533	Approved
0.7975	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3817	Phase 2
0.7974	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1607	Approved
0.7947	Intermediate Similarity	NPD1240	Approved
0.7929	Intermediate Similarity	NPD3818	Discontinued
0.7914	Intermediate Similarity	NPD1465	Phase 2
0.7879	Intermediate Similarity	NPD7075	Discontinued
0.7857	Intermediate Similarity	NPD1510	Phase 2
0.7857	Intermediate Similarity	NPD3926	Phase 2
0.7844	Intermediate Similarity	NPD1247	Approved
0.784	Intermediate Similarity	NPD4380	Phase 2
0.784	Intermediate Similarity	NPD6599	Discontinued
0.7818	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7819	Suspended
0.7805	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD6799	Approved
0.7784	Intermediate Similarity	NPD5494	Approved
0.7771	Intermediate Similarity	NPD2800	Approved
0.7744	Intermediate Similarity	NPD6801	Discontinued
0.7738	Intermediate Similarity	NPD6959	Discontinued
0.7733	Intermediate Similarity	NPD7074	Phase 3
0.7727	Intermediate Similarity	NPD6651	Approved
0.7701	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6797	Phase 2
0.7674	Intermediate Similarity	NPD7054	Approved
0.7674	Intermediate Similarity	NPD5844	Phase 1
0.7662	Intermediate Similarity	NPD230	Phase 1
0.7651	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7251	Discontinued
0.763	Intermediate Similarity	NPD7472	Approved
0.7619	Intermediate Similarity	NPD919	Approved
0.7616	Intermediate Similarity	NPD9494	Approved
0.76	Intermediate Similarity	NPD7808	Phase 3
0.7595	Intermediate Similarity	NPD1549	Phase 2
0.7586	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2935	Discontinued
0.7576	Intermediate Similarity	NPD7411	Suspended
0.7561	Intermediate Similarity	NPD3226	Approved
0.7554	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7390	Discontinued
0.7468	Intermediate Similarity	NPD2796	Approved
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD447	Suspended
0.7425	Intermediate Similarity	NPD37	Approved
0.7421	Intermediate Similarity	NPD1471	Phase 3
0.7399	Intermediate Similarity	NPD2403	Approved
0.7399	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5711	Approved
0.7384	Intermediate Similarity	NPD5710	Approved
0.7374	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1470	Approved
0.7353	Intermediate Similarity	NPD3749	Approved
0.7351	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD5402	Approved
0.7317	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD3751	Discontinued
0.7312	Intermediate Similarity	NPD2344	Approved
0.7294	Intermediate Similarity	NPD4967	Phase 2
0.7294	Intermediate Similarity	NPD4965	Approved
0.7294	Intermediate Similarity	NPD4966	Approved
0.729	Intermediate Similarity	NPD3027	Phase 3
0.7285	Intermediate Similarity	NPD9269	Phase 2
0.7284	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6100	Approved
0.725	Intermediate Similarity	NPD6099	Approved
0.7247	Intermediate Similarity	NPD6559	Discontinued
0.7241	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8434	Phase 2
0.7229	Intermediate Similarity	NPD5403	Approved
0.7222	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7228	Approved
0.7205	Intermediate Similarity	NPD2346	Discontinued
0.7193	Intermediate Similarity	NPD7768	Phase 2
0.7188	Intermediate Similarity	NPD3748	Approved
0.7188	Intermediate Similarity	NPD2799	Discontinued
0.7181	Intermediate Similarity	NPD6777	Approved
0.7181	Intermediate Similarity	NPD6781	Approved
0.7181	Intermediate Similarity	NPD6778	Approved
0.7181	Intermediate Similarity	NPD6782	Approved
0.7181	Intermediate Similarity	NPD6776	Approved
0.7181	Intermediate Similarity	NPD6780	Approved
0.7181	Intermediate Similarity	NPD6779	Approved
0.7178	Intermediate Similarity	NPD4628	Phase 3
0.7167	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD8150	Discontinued
0.7134	Intermediate Similarity	NPD2309	Approved
0.7126	Intermediate Similarity	NPD920	Approved
0.7126	Intermediate Similarity	NPD7199	Phase 2
0.7117	Intermediate Similarity	NPD1243	Approved
0.7108	Intermediate Similarity	NPD5401	Approved
0.7105	Intermediate Similarity	NPD1201	Approved
0.7095	Intermediate Similarity	NPD5953	Discontinued
0.7091	Intermediate Similarity	NPD3300	Phase 2
0.7068	Intermediate Similarity	NPD7435	Discontinued
0.7062	Intermediate Similarity	NPD8151	Discontinued
0.7059	Intermediate Similarity	NPD5090	Approved
0.7059	Intermediate Similarity	NPD5089	Approved
0.7051	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5408	Approved
0.7037	Intermediate Similarity	NPD5405	Approved
0.7037	Intermediate Similarity	NPD5404	Approved
0.7037	Intermediate Similarity	NPD5406	Approved
0.703	Intermediate Similarity	NPD6190	Approved
0.702	Intermediate Similarity	NPD9268	Approved
0.7012	Intermediate Similarity	NPD2654	Approved
0.7011	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3787	Discontinued
0.6987	Remote Similarity	NPD2798	Approved
0.6983	Remote Similarity	NPD7286	Phase 2
0.6979	Remote Similarity	NPD7697	Approved
0.6979	Remote Similarity	NPD7696	Phase 3
0.6979	Remote Similarity	NPD7698	Approved
0.697	Remote Similarity	NPD8166	Discontinued
0.6949	Remote Similarity	NPD5242	Approved
0.6948	Remote Similarity	NPD3972	Approved
0.6943	Remote Similarity	NPD7871	Phase 2
0.6943	Remote Similarity	NPD7870	Phase 2
0.6941	Remote Similarity	NPD7458	Discontinued
0.6937	Remote Similarity	NPD4060	Phase 1
0.6937	Remote Similarity	NPD1613	Approved
0.6937	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5353	Approved
0.6923	Remote Similarity	NPD7701	Phase 2
0.6918	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6534	Approved
0.6915	Remote Similarity	NPD6535	Approved
0.6905	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1933	Approved
0.6887	Remote Similarity	NPD5536	Phase 2
0.6886	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8312	Approved
0.6885	Remote Similarity	NPD8313	Approved
0.6879	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7003	Approved
0.6863	Remote Similarity	NPD4626	Approved
0.6859	Remote Similarity	NPD1876	Approved
0.6853	Remote Similarity	NPD7874	Approved
0.6853	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7907	Approved
0.6845	Remote Similarity	NPD4357	Discontinued
0.6839	Remote Similarity	NPD9717	Approved
0.6832	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4665	Approved
0.6832	Remote Similarity	NPD4111	Phase 1
0.6832	Remote Similarity	NPD3620	Phase 2
0.6831	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD228	Approved
0.6821	Remote Similarity	NPD9493	Approved
0.6818	Remote Similarity	NPD7801	Approved
0.6815	Remote Similarity	NPD1203	Approved
0.6813	Remote Similarity	NPD2313	Discontinued
0.6813	Remote Similarity	NPD3268	Approved
0.6813	Remote Similarity	NPD411	Approved
0.6806	Remote Similarity	NPD7699	Phase 2
0.6806	Remote Similarity	NPD7700	Phase 2
0.6802	Remote Similarity	NPD7028	Phase 2
0.6797	Remote Similarity	NPD1651	Approved
0.6795	Remote Similarity	NPD4749	Approved
0.6784	Remote Similarity	NPD1653	Approved
0.6782	Remote Similarity	NPD4585	Approved
0.6776	Remote Similarity	NPD7685	Pre-registration
0.6776	Remote Similarity	NPD7240	Approved
0.6754	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2491	Approved
0.6752	Remote Similarity	NPD1283	Approved
0.675	Remote Similarity	NPD4625	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