NPASS Compound

Structure

CID200761 OpenBabel06191715592D 27 29 0 0 1 0 0 0 0 0999 V2000 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 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 -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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 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 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 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 -6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 26 1 0 0 0 0 4 5 1 0 0 0 0 4 11 2 0 0 0 0 5 12 1 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 13 2 0 0 0 0 7 19 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 14 1 0 0 0 0 9 18 2 0 0 0 0 10 16 1 0 0 0 0 10 17 1 0 0 0 0 12 21 1 0 0 0 0 14 22 1 0 0 0 0 15 20 2 0 0 0 0 15 23 1 0 0 0 0 16 20 1 0 0 0 0 16 24 2 0 0 0 0 17 13 1 6 0 0 0 17 27 1 0 0 0 0 18 20 1 0 0 0 0 18 27 1 0 0 0 0 19 21 2 0 0 0 0 19 26 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.14
Volume:	377.752
LogP:	4.246
LogD:	3.265
LogS:	-3.959
# Rotatable Bonds:	4
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.703
Synthetic Accessibility Score:	3.269
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.792
MDCK Permeability:	1.1902881851710845e-05
Pgp-inhibitor:	0.116
Pgp-substrate:	0.337
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.633
30% Bioavailability (F30%):	0.902

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	92.46883392333984%
Volume Distribution (VD):	0.924
Pgp-substrate:	8.082469940185547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.583
CYP1A2-substrate:	0.834
CYP2C19-inhibitor:	0.889
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.872
CYP2C9-substrate:	0.91
CYP2D6-inhibitor:	0.88
CYP2D6-substrate:	0.55
CYP3A4-inhibitor:	0.708
CYP3A4-substrate:	0.166

ADMET: Excretion

Clearance (CL):	17.671
Half-life (T1/2):	0.664

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.672
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.755
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.932
Carcinogencity:	0.247
Eye Corrosion:	0.004
Eye Irritation:	0.883
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC200761

Natural Product ID:	NPC200761
*Common Name:**	Abyssinin Ii
IUPAC Name:	(2S)-5,7-dihydroxy-2-[4-hydroxy-3-methoxy-5-(3-methylbut-2-enyl)phenyl]-2,3-dihydrochromen-4-one
Synonyms:	Abyssinin II
Standard InCHIKey:	UQFQODVSORPELA-KRWDZBQOSA-N
Standard InCHI:	InChI=1S/C21H22O6/c1-11(2)4-5-12-6-13(7-19(26-3)21(12)25)17-10-16(24)20-15(23)8-14(22)9-18(20)27-17/h4,6-9,17,22-23,25H,5,10H2,1-3H3/t17-/m0/s1
SMILES:	COc1cc(cc(c1O)CC=C(C)C)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL388722
PubChem CID:	442457
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003643] 3'-prenylated flavans [CHEMONTID:0003506] 3'-prenylated flavanones

*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
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11524125]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11524125]
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	root barks	n.a.	n.a.	PMID[15689169]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17489632]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[18484536]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	Mukono, Uganda	2005-JUN	PMID[19008110]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19836230]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337486]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21116437]
NPO7457	Erythrina berteroana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7457	Erythrina berteroana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22444	Ceramium boydenii	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3174	Sulfolobus shibatae	Species	Sulfolobaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27459	Balanophora tobiracola	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24842	Bulla gouldiana	Species	Bullidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7457	Erythrina berteroana	Species	Fabaceae	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

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	17300.0	nM	PMID[547458]

☑ 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 NPC200761 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	406
0.1-0.2	1548
0.2-0.3	4055
0.3-0.4	9743
0.4-0.5	8522
0.5-0.6	3268
0.6-0.7	4597
0.7-0.8	5317
0.8-0.85	2881
0.85-0.9	1704
0.9-0.95	551
0.95-1	105

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC45849
1.0	High Similarity	NPC470327
1.0	High Similarity	NPC477503
0.9932	High Similarity	NPC35038
0.9932	High Similarity	NPC291878
0.9932	High Similarity	NPC470328
0.9932	High Similarity	NPC209614
0.9932	High Similarity	NPC278778
0.9932	High Similarity	NPC472626
0.9932	High Similarity	NPC195796
0.9866	High Similarity	NPC27337
0.9866	High Similarity	NPC223787
0.9866	High Similarity	NPC291508
0.9866	High Similarity	NPC472598
0.9866	High Similarity	NPC474055
0.9864	High Similarity	NPC106976
0.9797	High Similarity	NPC192083
0.9797	High Similarity	NPC298692
0.9797	High Similarity	NPC18727
0.9797	High Similarity	NPC213896
0.9797	High Similarity	NPC74924
0.9735	High Similarity	NPC287328
0.9735	High Similarity	NPC472624
0.9735	High Similarity	NPC174953
0.9735	High Similarity	NPC472630
0.9735	High Similarity	NPC470326
0.9735	High Similarity	NPC36217
0.9735	High Similarity	NPC472631
0.9735	High Similarity	NPC282009
0.9735	High Similarity	NPC119209
0.9735	High Similarity	NPC118256
0.9735	High Similarity	NPC192686
0.9732	High Similarity	NPC321779
0.9732	High Similarity	NPC226025
0.973	High Similarity	NPC471982
0.973	High Similarity	NPC219582
0.973	High Similarity	NPC302950
0.973	High Similarity	NPC236637
0.9728	High Similarity	NPC338131
0.9671	High Similarity	NPC471499
0.9671	High Similarity	NPC471212
0.9671	High Similarity	NPC134783
0.9671	High Similarity	NPC474038
0.9671	High Similarity	NPC471211
0.9671	High Similarity	NPC472634
0.9671	High Similarity	NPC26326
0.9671	High Similarity	NPC472632
0.9671	High Similarity	NPC471210
0.9669	High Similarity	NPC473990
0.9669	High Similarity	NPC95936
0.9669	High Similarity	NPC250214
0.9669	High Similarity	NPC22192
0.9608	High Similarity	NPC201800
0.9608	High Similarity	NPC474034
0.9608	High Similarity	NPC476247
0.9608	High Similarity	NPC474033
0.9608	High Similarity	NPC472635
0.9605	High Similarity	NPC475784
0.9603	High Similarity	NPC36852
0.9603	High Similarity	NPC471479
0.9603	High Similarity	NPC471515
0.9603	High Similarity	NPC262286
0.9603	High Similarity	NPC48208
0.9603	High Similarity	NPC474208
0.9603	High Similarity	NPC475267
0.9603	High Similarity	NPC474836
0.9603	High Similarity	NPC52889
0.9603	High Similarity	NPC162869
0.9603	High Similarity	NPC284820
0.9603	High Similarity	NPC471209
0.9603	High Similarity	NPC156057
0.9603	High Similarity	NPC78225
0.9603	High Similarity	NPC473272
0.96	High Similarity	NPC117992
0.96	High Similarity	NPC152951
0.96	High Similarity	NPC230149
0.96	High Similarity	NPC168247
0.96	High Similarity	NPC57674
0.9597	High Similarity	NPC472912
0.9545	High Similarity	NPC124038
0.9545	High Similarity	NPC186686
0.9545	High Similarity	NPC472625
0.9545	High Similarity	NPC18100
0.9542	High Similarity	NPC266314
0.9542	High Similarity	NPC142252
0.9539	High Similarity	NPC117418
0.9539	High Similarity	NPC210459
0.9539	High Similarity	NPC85121
0.9539	High Similarity	NPC53545
0.9536	High Similarity	NPC326037
0.9536	High Similarity	NPC138243
0.9536	High Similarity	NPC250922
0.9536	High Similarity	NPC13858
0.9536	High Similarity	NPC255106
0.9536	High Similarity	NPC235165
0.9536	High Similarity	NPC191146
0.9536	High Similarity	NPC471500
0.9536	High Similarity	NPC320825
0.9536	High Similarity	NPC68093
0.9533	High Similarity	NPC33051
0.9533	High Similarity	NPC49402
0.9533	High Similarity	NPC273462
0.9533	High Similarity	NPC70433
0.9533	High Similarity	NPC227337
0.9527	High Similarity	NPC177298
0.9527	High Similarity	NPC48479
0.9484	High Similarity	NPC300053
0.9484	High Similarity	NPC475888
0.9484	High Similarity	NPC108433
0.9484	High Similarity	NPC326520
0.9484	High Similarity	NPC472277
0.9484	High Similarity	NPC62261
0.9484	High Similarity	NPC293319
0.9481	High Similarity	NPC211107
0.9481	High Similarity	NPC81679
0.9481	High Similarity	NPC474150
0.9481	High Similarity	NPC474162
0.9477	High Similarity	NPC328102
0.9477	High Similarity	NPC228785
0.9477	High Similarity	NPC14353
0.9477	High Similarity	NPC56085
0.9477	High Similarity	NPC321399
0.9477	High Similarity	NPC299436
0.9474	High Similarity	NPC52530
0.9474	High Similarity	NPC469584
0.9474	High Similarity	NPC129684
0.9474	High Similarity	NPC472913
0.9474	High Similarity	NPC472910
0.9474	High Similarity	NPC222814
0.9474	High Similarity	NPC67876
0.9474	High Similarity	NPC96167
0.9474	High Similarity	NPC472914
0.9474	High Similarity	NPC299520
0.9474	High Similarity	NPC99597
0.9474	High Similarity	NPC245758
0.9474	High Similarity	NPC472911
0.9474	High Similarity	NPC210084
0.947	High Similarity	NPC256925
0.947	High Similarity	NPC113906
0.947	High Similarity	NPC234255
0.947	High Similarity	NPC67396
0.947	High Similarity	NPC37392
0.9467	High Similarity	NPC257648
0.9467	High Similarity	NPC477231
0.9467	High Similarity	NPC260979
0.9463	High Similarity	NPC3825
0.9463	High Similarity	NPC88804
0.9459	High Similarity	NPC321011
0.9459	High Similarity	NPC120464
0.9459	High Similarity	NPC476342
0.9459	High Similarity	NPC188679
0.9459	High Similarity	NPC294852
0.9456	High Similarity	NPC290133
0.9456	High Similarity	NPC24136
0.9456	High Similarity	NPC187282
0.9423	High Similarity	NPC471213
0.9423	High Similarity	NPC170245
0.9423	High Similarity	NPC43319
0.9419	High Similarity	NPC205265
0.9419	High Similarity	NPC41301
0.9419	High Similarity	NPC474240
0.9419	High Similarity	NPC7483
0.9419	High Similarity	NPC472281
0.9416	High Similarity	NPC40491
0.9416	High Similarity	NPC158188
0.9416	High Similarity	NPC61010
0.9416	High Similarity	NPC289771
0.9416	High Similarity	NPC474186
0.9416	High Similarity	NPC278052
0.9412	High Similarity	NPC204879
0.9412	High Similarity	NPC100123
0.9412	High Similarity	NPC184755
0.9412	High Similarity	NPC469658
0.9412	High Similarity	NPC74178
0.9408	High Similarity	NPC472455
0.9408	High Similarity	NPC24640
0.9408	High Similarity	NPC471985
0.9408	High Similarity	NPC472916
0.9404	High Similarity	NPC469550
0.94	High Similarity	NPC256406
0.94	High Similarity	NPC31363
0.94	High Similarity	NPC205046
0.94	High Similarity	NPC304295
0.94	High Similarity	NPC59162
0.9396	High Similarity	NPC137062
0.9396	High Similarity	NPC183950
0.9396	High Similarity	NPC183959
0.9396	High Similarity	NPC52005
0.9396	High Similarity	NPC1612
0.9396	High Similarity	NPC287101
0.9396	High Similarity	NPC223579
0.9392	High Similarity	NPC62536
0.9392	High Similarity	NPC33265
0.9363	High Similarity	NPC477154
0.9363	High Similarity	NPC6588
0.9363	High Similarity	NPC117854
0.9363	High Similarity	NPC218226
0.9363	High Similarity	NPC474024
0.9363	High Similarity	NPC477502
0.9359	High Similarity	NPC470457

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 NPC200761 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	930
0.2-0.3	1809
0.3-0.4	2608
0.4-0.5	1763
0.5-0.6	987
0.6-0.7	506
0.7-0.8	135
0.8-0.85	33
0.85-0.9	20
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9797	High Similarity	NPD2393	Clinical (unspecified phase)
0.973	High Similarity	NPD1934	Approved
0.9276	High Similarity	NPD2801	Approved
0.9236	High Similarity	NPD6168	Clinical (unspecified phase)
0.9236	High Similarity	NPD6167	Clinical (unspecified phase)
0.9236	High Similarity	NPD6166	Phase 2
0.906	High Similarity	NPD1511	Approved
0.9032	High Similarity	NPD3882	Suspended
0.9006	High Similarity	NPD7074	Phase 3
0.8954	High Similarity	NPD4380	Phase 2
0.8944	High Similarity	NPD7054	Approved
0.894	High Similarity	NPD1512	Approved
0.891	High Similarity	NPD4868	Clinical (unspecified phase)
0.8889	High Similarity	NPD7472	Approved
0.8882	High Similarity	NPD3818	Discontinued
0.8874	High Similarity	NPD4378	Clinical (unspecified phase)
0.8861	High Similarity	NPD5494	Approved
0.8854	High Similarity	NPD7075	Discontinued
0.8846	High Similarity	NPD3817	Phase 2
0.8784	High Similarity	NPD1550	Clinical (unspecified phase)
0.8784	High Similarity	NPD1552	Clinical (unspecified phase)
0.8782	High Similarity	NPD7096	Clinical (unspecified phase)
0.8725	High Similarity	NPD1549	Phase 2
0.872	High Similarity	NPD6797	Phase 2
0.8667	High Similarity	NPD7251	Discontinued
0.8616	High Similarity	NPD4381	Clinical (unspecified phase)
0.8614	High Similarity	NPD4338	Clinical (unspecified phase)
0.8614	High Similarity	NPD7808	Phase 3
0.8608	High Similarity	NPD8443	Clinical (unspecified phase)
0.8571	High Similarity	NPD6959	Discontinued
0.8544	High Similarity	NPD7819	Suspended
0.8519	High Similarity	NPD6232	Discontinued
0.8485	Intermediate Similarity	NPD5844	Phase 1
0.8485	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD6801	Discontinued
0.8476	Intermediate Similarity	NPD7473	Discontinued
0.8467	Intermediate Similarity	NPD2796	Approved
0.8418	Intermediate Similarity	NPD7411	Suspended
0.84	Intermediate Similarity	NPD1510	Phase 2
0.8387	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6559	Discontinued
0.8323	Intermediate Similarity	NPD6799	Approved
0.8313	Intermediate Similarity	NPD1465	Phase 2
0.8255	Intermediate Similarity	NPD1613	Approved
0.8255	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1240	Approved
0.8163	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1607	Approved
0.8133	Intermediate Similarity	NPD943	Approved
0.8125	Intermediate Similarity	NPD6599	Discontinued
0.8121	Intermediate Similarity	NPD1247	Approved
0.811	Intermediate Similarity	NPD919	Approved
0.8108	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD2800	Approved
0.8054	Intermediate Similarity	NPD3027	Phase 3
0.8038	Intermediate Similarity	NPD2533	Approved
0.8038	Intermediate Similarity	NPD2534	Approved
0.8038	Intermediate Similarity	NPD2532	Approved
0.8037	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7768	Phase 2
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7961	Intermediate Similarity	NPD230	Phase 1
0.7949	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD5403	Approved
0.7917	Intermediate Similarity	NPD3926	Phase 2
0.7892	Intermediate Similarity	NPD6234	Discontinued
0.7826	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5401	Approved
0.7802	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6651	Approved
0.7785	Intermediate Similarity	NPD3750	Approved
0.7785	Intermediate Similarity	NPD4628	Phase 3
0.7763	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6099	Approved
0.7756	Intermediate Similarity	NPD6100	Approved
0.7756	Intermediate Similarity	NPD1551	Phase 2
0.7727	Intermediate Similarity	NPD447	Suspended
0.7725	Intermediate Similarity	NPD3749	Approved
0.7722	Intermediate Similarity	NPD1243	Approved
0.7716	Intermediate Similarity	NPD920	Approved
0.7697	Intermediate Similarity	NPD37	Approved
0.7692	Intermediate Similarity	NPD7199	Phase 2
0.7692	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7228	Approved
0.7669	Intermediate Similarity	NPD1653	Approved
0.7665	Intermediate Similarity	NPD4966	Approved
0.7665	Intermediate Similarity	NPD4967	Phase 2
0.7665	Intermediate Similarity	NPD4965	Approved
0.7657	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD5953	Discontinued
0.764	Intermediate Similarity	NPD7390	Discontinued
0.764	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7286	Phase 2
0.7627	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3226	Approved
0.7613	Intermediate Similarity	NPD1933	Approved
0.7611	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2346	Discontinued
0.7593	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2799	Discontinued
0.7578	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD3751	Discontinued
0.7566	Intermediate Similarity	NPD9494	Approved
0.7562	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5711	Approved
0.7544	Intermediate Similarity	NPD5710	Approved
0.7544	Intermediate Similarity	NPD3787	Discontinued
0.7533	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.7527	Intermediate Similarity	NPD4360	Phase 2
0.7527	Intermediate Similarity	NPD4363	Phase 3
0.7517	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6190	Approved
0.7516	Intermediate Similarity	NPD4908	Phase 1
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.7485	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2344	Approved
0.7468	Intermediate Similarity	NPD3748	Approved
0.7453	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7685	Pre-registration
0.74	Intermediate Similarity	NPD1610	Phase 2
0.7396	Intermediate Similarity	NPD5353	Approved
0.7382	Intermediate Similarity	NPD8151	Discontinued
0.7378	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7584	Approved
0.7358	Intermediate Similarity	NPD7033	Discontinued
0.7355	Intermediate Similarity	NPD4625	Phase 3
0.7329	Intermediate Similarity	NPD2424	Discontinued
0.7326	Intermediate Similarity	NPD6777	Approved
0.7326	Intermediate Similarity	NPD6776	Approved
0.7326	Intermediate Similarity	NPD6780	Approved
0.7326	Intermediate Similarity	NPD6781	Approved
0.7326	Intermediate Similarity	NPD6778	Approved
0.7326	Intermediate Similarity	NPD6779	Approved
0.7326	Intermediate Similarity	NPD6782	Approved
0.732	Intermediate Similarity	NPD1203	Approved
0.7308	Intermediate Similarity	NPD6798	Discontinued
0.7305	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2309	Approved
0.7299	Intermediate Similarity	NPD5242	Approved
0.7293	Intermediate Similarity	NPD8434	Phase 2
0.7293	Intermediate Similarity	NPD8150	Discontinued
0.729	Intermediate Similarity	NPD6832	Phase 2
0.7278	Intermediate Similarity	NPD5124	Phase 1
0.7278	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1548	Phase 1
0.7241	Intermediate Similarity	NPD7229	Phase 3
0.7237	Intermediate Similarity	NPD9269	Phase 2
0.7235	Intermediate Similarity	NPD8455	Phase 2
0.7226	Intermediate Similarity	NPD2861	Phase 2
0.7215	Intermediate Similarity	NPD4060	Phase 1
0.7211	Intermediate Similarity	NPD7435	Discontinued
0.7207	Intermediate Similarity	NPD7240	Approved
0.7204	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4361	Phase 2
0.7202	Intermediate Similarity	NPD7458	Discontinued
0.7197	Intermediate Similarity	NPD3268	Approved
0.7197	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4749	Approved
0.7178	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1652	Phase 2
0.7178	Intermediate Similarity	NPD2654	Approved
0.7178	Intermediate Similarity	NPD6674	Discontinued
0.7176	Intermediate Similarity	NPD6844	Discontinued
0.717	Intermediate Similarity	NPD6355	Discontinued
0.7161	Intermediate Similarity	NPD2798	Approved
0.716	Intermediate Similarity	NPD7266	Discontinued
0.7159	Intermediate Similarity	NPD2403	Approved
0.7152	Intermediate Similarity	NPD6233	Phase 2
0.7151	Intermediate Similarity	NPD3823	Discontinued
0.7128	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7783	Phase 2
0.7124	Intermediate Similarity	NPD9717	Approved
0.7124	Intermediate Similarity	NPD1608	Approved
0.712	Intermediate Similarity	NPD7697	Approved
0.712	Intermediate Similarity	NPD7698	Approved
0.712	Intermediate Similarity	NPD7696	Phase 3
0.7118	Intermediate Similarity	NPD6385	Approved
0.7118	Intermediate Similarity	NPD6386	Approved
0.7115	Intermediate Similarity	NPD3018	Phase 2
0.7097	Intermediate Similarity	NPD2797	Approved
0.7095	Intermediate Similarity	NPD1729	Discontinued
0.7086	Intermediate Similarity	NPD8127	Discontinued
0.7083	Intermediate Similarity	NPD7871	Phase 2
0.7083	Intermediate Similarity	NPD7870	Phase 2
0.7068	Intermediate Similarity	NPD6823	Phase 2
0.7067	Intermediate Similarity	NPD5536	Phase 2
0.7066	Intermediate Similarity	NPD4661	Approved
0.7066	Intermediate Similarity	NPD4662	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