NPASS Compound

Structure

NPC247677 OpenBabel07101719142D 27 29 0 0 0 0 0 0 0 0999 V2000 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 2.7770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 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 11 1 0 0 0 0 3 26 1 0 0 0 0 4 6 1 0 0 0 0 4 11 2 0 0 0 0 5 7 2 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 10 22 2 0 0 0 0 12 23 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 20 2 0 0 0 0 15 19 1 0 0 0 0 15 21 2 0 0 0 0 16 24 1 0 0 0 0 17 26 1 0 0 0 0 18 19 2 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 20 25 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.13
Volume:	375.116
LogP:	5.233
LogD:	3.365
LogS:	-3.664
# Rotatable Bonds:	5
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.451
Synthetic Accessibility Score:	3.033
Fsp3:	0.19
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.921
MDCK Permeability:	1.1587204426177777e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.288
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.765
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	96.28888702392578%
Volume Distribution (VD):	0.706
Pgp-substrate:	4.776064872741699%

ADMET: Metabolism

CYP1A2-inhibitor:	0.898
CYP1A2-substrate:	0.405
CYP2C19-inhibitor:	0.806
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.832
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.835
CYP2D6-substrate:	0.456
CYP3A4-inhibitor:	0.518
CYP3A4-substrate:	0.1

ADMET: Excretion

Clearance (CL):	10.386
Half-life (T1/2):	0.605

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.534
Drug-inuced Liver Injury (DILI):	0.942
AMES Toxicity:	0.585
Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.582
Skin Sensitization:	0.184
Carcinogencity:	0.178
Eye Corrosion:	0.003
Eye Irritation:	0.785
Respiratory Toxicity:	0.431

Download Data

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

Natural Product: NPC247677

Natural Product ID:	NPC247677
*Common Name:**	Ebenfuran Iii
IUPAC Name:	2-(2,4-dihydroxyphenyl)-4-hydroxy-6-methoxy-5-(3-methylbut-2-enyl)-1-benzofuran-3-carbaldehyde
Synonyms:	Ebenfuran III
Standard InCHIKey:	PXSWSGDFRGTMGP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H20O6/c1-11(2)4-6-14-17(26-3)9-18-19(20(14)25)15(10-22)21(27-18)13-7-5-12(23)8-16(13)24/h4-5,7-10,23-25H,6H2,1-3H3
SMILES:	O=Cc1c(oc2c1c(O)c(c(c2)OC)CC=C(C)C)c1ccc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL579049
PubChem CID:	10090417
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO12804	Onobrychis ebenoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141112]
NPO12804	Onobrychis ebenoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18986200]
NPO12804	Onobrychis ebenoides	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
EC50	2
Others	3

Activity Type	# Activity
Cell Line	4
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	2600.0	nM	PMID[513992]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	47.0	%	PMID[513992]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	2900.0	nM	PMID[513992]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	31.0	%	PMID[513992]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	RBA	=	0.09	n.a.	PMID[513992]

☑ 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 NPC247677 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	390
0.1-0.2	1730
0.2-0.3	3994
0.3-0.4	10337
0.4-0.5	8116
0.5-0.6	3946
0.6-0.7	5753
0.7-0.8	4590
0.8-0.85	2241
0.85-0.9	1336
0.9-0.95	219
0.95-1	45

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC160015
0.9933	High Similarity	NPC296957
0.9933	High Similarity	NPC260902
0.9867	High Similarity	NPC476350
0.9867	High Similarity	NPC476349
0.9797	High Similarity	NPC67654
0.973	High Similarity	NPC156244
0.96	High Similarity	NPC1477
0.96	High Similarity	NPC213608
0.9595	High Similarity	NPC37226
0.9595	High Similarity	NPC226644
0.9533	High Similarity	NPC5871
0.9533	High Similarity	NPC263676
0.9527	High Similarity	NPC135325
0.947	High Similarity	NPC122365
0.9467	High Similarity	NPC170169
0.9467	High Similarity	NPC116604
0.9463	High Similarity	NPC296030
0.9463	High Similarity	NPC39929
0.9459	High Similarity	NPC12148
0.9459	High Similarity	NPC130581
0.9416	High Similarity	NPC260296
0.9416	High Similarity	NPC115432
0.9412	High Similarity	NPC65504
0.9408	High Similarity	NPC148938
0.9408	High Similarity	NPC198490
0.94	High Similarity	NPC78335
0.94	High Similarity	NPC230713
0.9392	High Similarity	NPC300267
0.9392	High Similarity	NPC210826
0.9392	High Similarity	NPC51641
0.9351	High Similarity	NPC40583
0.9351	High Similarity	NPC244750
0.9342	High Similarity	NPC183874
0.9342	High Similarity	NPC235333
0.9333	High Similarity	NPC178202
0.9324	High Similarity	NPC230943
0.9299	High Similarity	NPC136641
0.9286	High Similarity	NPC96342
0.9286	High Similarity	NPC246647
0.9286	High Similarity	NPC212967
0.9286	High Similarity	NPC164110
0.9281	High Similarity	NPC297531
0.9281	High Similarity	NPC213936
0.9276	High Similarity	NPC253872
0.9276	High Similarity	NPC207624
0.9272	High Similarity	NPC472406
0.9257	High Similarity	NPC302181
0.9257	High Similarity	NPC225884
0.9236	High Similarity	NPC155640
0.9236	High Similarity	NPC38591
0.9231	High Similarity	NPC304387
0.9226	High Similarity	NPC472877
0.9221	High Similarity	NPC180924
0.9216	High Similarity	NPC472462
0.9211	High Similarity	NPC58668
0.9211	High Similarity	NPC193976
0.9211	High Similarity	NPC23668
0.9211	High Similarity	NPC106372
0.9211	High Similarity	NPC115324
0.9205	High Similarity	NPC221868
0.9205	High Similarity	NPC317492
0.9205	High Similarity	NPC37208
0.92	High Similarity	NPC198427
0.92	High Similarity	NPC17816
0.9189	High Similarity	NPC53192
0.9177	High Similarity	NPC291110
0.9172	High Similarity	NPC193998
0.9161	High Similarity	NPC270044
0.9161	High Similarity	NPC268360
0.9161	High Similarity	NPC269495
0.915	High Similarity	NPC142308
0.9145	High Similarity	NPC135303
0.9145	High Similarity	NPC167576
0.9145	High Similarity	NPC148423
0.9139	High Similarity	NPC272194
0.9139	High Similarity	NPC39195
0.9139	High Similarity	NPC168085
0.9091	High Similarity	NPC42458
0.9091	High Similarity	NPC158261
0.9073	High Similarity	NPC308200
0.9068	High Similarity	NPC131866
0.9068	High Similarity	NPC120220
0.9067	High Similarity	NPC155144
0.9067	High Similarity	NPC98926
0.9062	High Similarity	NPC320789
0.906	High Similarity	NPC470636
0.906	High Similarity	NPC226942
0.906	High Similarity	NPC96791
0.9051	High Similarity	NPC219861
0.9045	High Similarity	NPC220582
0.9045	High Similarity	NPC304839
0.9032	High Similarity	NPC99199
0.9032	High Similarity	NPC474542
0.9026	High Similarity	NPC38361
0.9026	High Similarity	NPC41326
0.9026	High Similarity	NPC130015
0.902	High Similarity	NPC321896
0.902	High Similarity	NPC476185
0.902	High Similarity	NPC155882
0.902	High Similarity	NPC472421
0.902	High Similarity	NPC191104
0.9013	High Similarity	NPC306788
0.9013	High Similarity	NPC145467
0.9012	High Similarity	NPC472584
0.9007	High Similarity	NPC190572
0.9007	High Similarity	NPC299011
0.9006	High Similarity	NPC53252
0.9	High Similarity	NPC53640
0.9	High Similarity	NPC277480
0.8994	High Similarity	NPC472581
0.8994	High Similarity	NPC109180
0.8987	High Similarity	NPC74854
0.8987	High Similarity	NPC30655
0.8987	High Similarity	NPC45124
0.8974	High Similarity	NPC474386
0.8968	High Similarity	NPC72370
0.8968	High Similarity	NPC41719
0.8961	High Similarity	NPC474744
0.8961	High Similarity	NPC472407
0.8961	High Similarity	NPC318424
0.8961	High Similarity	NPC474772
0.8961	High Similarity	NPC472423
0.8954	High Similarity	NPC471114
0.8954	High Similarity	NPC88445
0.8944	High Similarity	NPC476459
0.8944	High Similarity	NPC247973
0.8944	High Similarity	NPC50394
0.894	High Similarity	NPC271288
0.894	High Similarity	NPC311144
0.894	High Similarity	NPC311741
0.894	High Similarity	NPC234629
0.894	High Similarity	NPC303185
0.894	High Similarity	NPC184649
0.8938	High Similarity	NPC37183
0.8938	High Similarity	NPC38914
0.8924	High Similarity	NPC49009
0.8924	High Similarity	NPC169
0.8919	High Similarity	NPC471620
0.8919	High Similarity	NPC124269
0.891	High Similarity	NPC233776
0.8903	High Similarity	NPC473996
0.8903	High Similarity	NPC327269
0.8903	High Similarity	NPC476238
0.8903	High Similarity	NPC31627
0.8896	High Similarity	NPC29777
0.8896	High Similarity	NPC13282
0.8896	High Similarity	NPC471115
0.8889	High Similarity	NPC266572
0.8882	High Similarity	NPC323137
0.8882	High Similarity	NPC477955
0.8882	High Similarity	NPC472629
0.8882	High Similarity	NPC73320
0.8874	High Similarity	NPC169591
0.8874	High Similarity	NPC75049
0.8874	High Similarity	NPC68104
0.8874	High Similarity	NPC150408
0.8874	High Similarity	NPC172182
0.8874	High Similarity	NPC310130
0.8874	High Similarity	NPC106985
0.8874	High Similarity	NPC257097
0.8874	High Similarity	NPC262935
0.8874	High Similarity	NPC164980
0.8874	High Similarity	NPC251182
0.8874	High Similarity	NPC221432
0.8874	High Similarity	NPC175504
0.8874	High Similarity	NPC113770
0.8874	High Similarity	NPC91560
0.8874	High Similarity	NPC39329
0.8874	High Similarity	NPC166138
0.8874	High Similarity	NPC17262
0.8874	High Similarity	NPC149026
0.8874	High Similarity	NPC18585
0.8874	High Similarity	NPC143896
0.8868	High Similarity	NPC472346
0.8868	High Similarity	NPC14822
0.8867	High Similarity	NPC52789
0.8867	High Similarity	NPC3188
0.8867	High Similarity	NPC110969
0.8867	High Similarity	NPC268204
0.8867	High Similarity	NPC321980
0.8867	High Similarity	NPC55832
0.8867	High Similarity	NPC26051
0.8867	High Similarity	NPC470087
0.8867	High Similarity	NPC470089
0.8867	High Similarity	NPC469404
0.8859	High Similarity	NPC477956
0.8859	High Similarity	NPC137009
0.8854	High Similarity	NPC137100
0.8854	High Similarity	NPC13879
0.8851	High Similarity	NPC62735
0.8851	High Similarity	NPC188879
0.8851	High Similarity	NPC472419
0.8841	High Similarity	NPC261471
0.8839	High Similarity	NPC471675
0.8839	High Similarity	NPC472580
0.8839	High Similarity	NPC472636
0.8831	High Similarity	NPC266499
0.8831	High Similarity	NPC214493
0.8827	High Similarity	NPC241820

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 NPC247677 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	998
0.2-0.3	1551
0.3-0.4	2655
0.4-0.5	1950
0.5-0.6	1128
0.6-0.7	349
0.7-0.8	108
0.8-0.85	49
0.85-0.9	18
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8851	High Similarity	NPD2344	Approved
0.8824	High Similarity	NPD920	Approved
0.8816	High Similarity	NPD4378	Clinical (unspecified phase)
0.8693	High Similarity	NPD642	Clinical (unspecified phase)
0.8618	High Similarity	NPD2309	Approved
0.8609	High Similarity	NPD2800	Approved
0.8571	High Similarity	NPD7410	Clinical (unspecified phase)
0.8562	High Similarity	NPD3749	Approved
0.8562	High Similarity	NPD643	Clinical (unspecified phase)
0.8553	High Similarity	NPD8443	Clinical (unspecified phase)
0.8543	High Similarity	NPD1549	Phase 2
0.8503	High Similarity	NPD6559	Discontinued
0.8491	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD7411	Suspended
0.8477	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1510	Phase 2
0.8446	Intermediate Similarity	NPD1240	Approved
0.8418	Intermediate Similarity	NPD4380	Phase 2
0.8411	Intermediate Similarity	NPD2796	Approved
0.8385	Intermediate Similarity	NPD7768	Phase 2
0.8385	Intermediate Similarity	NPD3882	Suspended
0.8375	Intermediate Similarity	NPD7819	Suspended
0.8366	Intermediate Similarity	NPD1243	Approved
0.8364	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1607	Approved
0.8333	Intermediate Similarity	NPD7075	Discontinued
0.8303	Intermediate Similarity	NPD3926	Phase 2
0.8293	Intermediate Similarity	NPD1247	Approved
0.8293	Intermediate Similarity	NPD6959	Discontinued
0.8261	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD5494	Approved
0.8217	Intermediate Similarity	NPD2533	Approved
0.8217	Intermediate Similarity	NPD2534	Approved
0.8217	Intermediate Similarity	NPD2532	Approved
0.8199	Intermediate Similarity	NPD1934	Approved
0.8171	Intermediate Similarity	NPD919	Approved
0.817	Intermediate Similarity	NPD1551	Phase 2
0.8153	Intermediate Similarity	NPD6799	Approved
0.8148	Intermediate Similarity	NPD2801	Approved
0.8133	Intermediate Similarity	NPD6232	Discontinued
0.8129	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7473	Discontinued
0.8086	Intermediate Similarity	NPD6801	Discontinued
0.8075	Intermediate Similarity	NPD6599	Discontinued
0.8047	Intermediate Similarity	NPD3818	Discontinued
0.8038	Intermediate Similarity	NPD1511	Approved
0.8012	Intermediate Similarity	NPD5953	Discontinued
0.7988	Intermediate Similarity	NPD2296	Approved
0.7987	Intermediate Similarity	NPD2799	Discontinued
0.7962	Intermediate Similarity	NPD3750	Approved
0.7941	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD1512	Approved
0.7935	Intermediate Similarity	NPD2935	Discontinued
0.7929	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD6166	Phase 2
0.7919	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7286	Phase 2
0.7866	Intermediate Similarity	NPD6280	Approved
0.7866	Intermediate Similarity	NPD6279	Approved
0.7857	Intermediate Similarity	NPD6651	Approved
0.7848	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5844	Phase 1
0.7791	Intermediate Similarity	NPD3226	Approved
0.7771	Intermediate Similarity	NPD3817	Phase 2
0.7771	Intermediate Similarity	NPD1471	Phase 3
0.7756	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2313	Discontinued
0.7706	Intermediate Similarity	NPD6808	Phase 2
0.7644	Intermediate Similarity	NPD7074	Phase 3
0.7643	Intermediate Similarity	NPD3748	Approved
0.764	Intermediate Similarity	NPD8434	Phase 2
0.7625	Intermediate Similarity	NPD4628	Phase 3
0.7605	Intermediate Similarity	NPD5761	Phase 2
0.7605	Intermediate Similarity	NPD5760	Phase 2
0.7602	Intermediate Similarity	NPD5710	Approved
0.7602	Intermediate Similarity	NPD5711	Approved
0.7602	Intermediate Similarity	NPD7229	Phase 3
0.7593	Intermediate Similarity	NPD7390	Discontinued
0.7586	Intermediate Similarity	NPD7054	Approved
0.7582	Intermediate Similarity	NPD4908	Phase 1
0.7561	Intermediate Similarity	NPD5403	Approved
0.756	Intermediate Similarity	NPD5402	Approved
0.7556	Intermediate Similarity	NPD4287	Approved
0.7547	Intermediate Similarity	NPD2346	Discontinued
0.7543	Intermediate Similarity	NPD1729	Discontinued
0.7543	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7468	Intermediate Similarity	NPD6832	Phase 2
0.7458	Intermediate Similarity	NPD7251	Discontinued
0.7446	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD4361	Phase 2
0.7439	Intermediate Similarity	NPD5401	Approved
0.7416	Intermediate Similarity	NPD7808	Phase 3
0.7416	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1465	Phase 2
0.7391	Intermediate Similarity	NPD4360	Phase 2
0.7391	Intermediate Similarity	NPD4363	Phase 3
0.7375	Intermediate Similarity	NPD6100	Approved
0.7375	Intermediate Similarity	NPD6099	Approved
0.7372	Intermediate Similarity	NPD3764	Approved
0.7351	Intermediate Similarity	NPD1610	Phase 2
0.7351	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2654	Approved
0.7338	Intermediate Similarity	NPD2798	Approved
0.7333	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7033	Discontinued
0.7303	Intermediate Similarity	NPD9717	Approved
0.7303	Intermediate Similarity	NPD3972	Approved
0.7301	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD3268	Approved
0.7233	Intermediate Similarity	NPD230	Phase 1
0.7233	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD3751	Discontinued
0.7225	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD2403	Approved
0.7216	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1876	Approved
0.72	Intermediate Similarity	NPD1548	Phase 1
0.7197	Intermediate Similarity	NPD4625	Phase 3
0.7196	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7003	Approved
0.7189	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8313	Approved
0.7182	Intermediate Similarity	NPD8312	Approved
0.7174	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1470	Approved
0.7161	Intermediate Similarity	NPD1164	Approved
0.7161	Intermediate Similarity	NPD2797	Approved
0.716	Intermediate Similarity	NPD5405	Approved
0.716	Intermediate Similarity	NPD7458	Discontinued
0.716	Intermediate Similarity	NPD5408	Approved
0.716	Intermediate Similarity	NPD5406	Approved
0.716	Intermediate Similarity	NPD5404	Approved
0.7143	Intermediate Similarity	NPD7199	Phase 2
0.7126	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD447	Suspended
0.7124	Intermediate Similarity	NPD422	Phase 1
0.7117	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6004	Phase 3
0.7117	Intermediate Similarity	NPD6005	Phase 3
0.7117	Intermediate Similarity	NPD6002	Phase 3
0.7099	Intermediate Similarity	NPD4308	Phase 3
0.7099	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD9545	Approved
0.7078	Intermediate Similarity	NPD1608	Approved
0.7077	Intermediate Similarity	NPD8151	Discontinued
0.7073	Intermediate Similarity	NPD2424	Discontinued
0.7066	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4288	Approved
0.7039	Intermediate Similarity	NPD7177	Discontinued
0.7035	Intermediate Similarity	NPD37	Approved
0.7029	Intermediate Similarity	NPD6234	Discontinued
0.7019	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6355	Discontinued
0.7019	Intermediate Similarity	NPD5124	Phase 1
0.7016	Intermediate Similarity	NPD6779	Approved
0.7016	Intermediate Similarity	NPD6778	Approved
0.7016	Intermediate Similarity	NPD6782	Approved
0.7016	Intermediate Similarity	NPD6780	Approved
0.7016	Intermediate Similarity	NPD6776	Approved
0.7016	Intermediate Similarity	NPD6777	Approved
0.7016	Intermediate Similarity	NPD6781	Approved
0.7011	Intermediate Similarity	NPD4967	Phase 2
0.7011	Intermediate Similarity	NPD4965	Approved
0.7011	Intermediate Similarity	NPD4966	Approved
0.7006	Intermediate Similarity	NPD3787	Discontinued
0.7006	Intermediate Similarity	NPD1019	Discontinued
0.6994	Remote Similarity	NPD8455	Phase 2
0.698	Remote Similarity	NPD1241	Discontinued
0.6978	Remote Similarity	NPD6104	Discontinued
0.6974	Remote Similarity	NPD7584	Approved
0.6962	Remote Similarity	NPD9494	Approved
0.6962	Remote Similarity	NPD2861	Phase 2
0.6959	Remote Similarity	NPD7871	Phase 2
0.6959	Remote Similarity	NPD7870	Phase 2
0.6957	Remote Similarity	NPD1613	Approved
0.6957	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD9493	Approved
0.6951	Remote Similarity	NPD4477	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