NPASS Compound

Structure

NPC296957 OpenBabel07101718252D 29 31 0 0 0 0 0 0 0 0999 V2000 5.7812 2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7812 2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -1.7891 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 -3.0878 1.6750 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 3.5491 1.8090 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 -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 -3.5878 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 -1.5878 0.8090 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 5.2812 1.8090 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 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 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 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 22 1 0 0 0 0 2 22 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 22 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 23 2 0 0 0 0 12 24 1 0 0 0 0 13 17 1 0 0 0 0 13 20 2 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 19 1 0 0 0 0 15 21 2 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 19 2 0 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 20 25 1 0 0 0 0 21 29 1 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.15
Volume:	403.839
LogP:	3.67
LogD:	2.874
LogS:	-4.189
# Rotatable Bonds:	7
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.513
Synthetic Accessibility Score:	2.979
Fsp3:	0.318
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:	-4.817
MDCK Permeability:	1.3508692973118741e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.06
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	95.45077514648438%
Volume Distribution (VD):	0.932
Pgp-substrate:	6.742221832275391%

ADMET: Metabolism

CYP1A2-inhibitor:	0.776
CYP1A2-substrate:	0.915
CYP2C19-inhibitor:	0.24
CYP2C19-substrate:	0.163
CYP2C9-inhibitor:	0.714
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.541
CYP2D6-substrate:	0.712
CYP3A4-inhibitor:	0.502
CYP3A4-substrate:	0.154

ADMET: Excretion

Clearance (CL):	10.581
Half-life (T1/2):	0.653

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.047
Drug-inuced Liver Injury (DILI):	0.834
AMES Toxicity:	0.535
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.157
Skin Sensitization:	0.09
Carcinogencity:	0.027
Eye Corrosion:	0.004
Eye Irritation:	0.183
Respiratory Toxicity:	0.352

Download Data

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

Natural Product: NPC296957

Natural Product ID:	NPC296957
*Common Name:**	Ebenfuran Vi
IUPAC Name:	4-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-(3-hydroxy-3-methylbutyl)-6-methoxy-1-benzofuran-3-carbaldehyde
Synonyms:	Ebenfuran VI
Standard InCHIKey:	DVCUSBGWKAJHOB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H24O7/c1-22(2,26)8-7-13-17(28-4)10-18-19(20(13)25)15(11-23)21(29-18)14-6-5-12(24)9-16(14)27-3/h5-6,9-11,24-26H,7-8H2,1-4H3
SMILES:	CC(C)(CCc1c(cc2c(c(C=O)c(c3ccc(cc3OC)O)o2)c1O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL578016
PubChem CID:	25157567
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	1
Others	3

Activity Type	# Activity
Cell Line	3
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	=	4800.0	nM	PMID[556290]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	154.0	%	PMID[556290]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	118.0	%	PMID[556290]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	RBA	=	0.06	n.a.	PMID[556290]

☑ 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 NPC296957 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	394
0.1-0.2	1619
0.2-0.3	3798
0.3-0.4	9899
0.4-0.5	8797
0.5-0.6	3937
0.6-0.7	5654
0.7-0.8	4788
0.8-0.85	2327
0.85-0.9	1242
0.9-0.95	211
0.95-1	31

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC260902
0.9933	High Similarity	NPC160015
0.9933	High Similarity	NPC247677
0.9801	High Similarity	NPC476350
0.9801	High Similarity	NPC476349
0.9732	High Similarity	NPC67654
0.9664	High Similarity	NPC156244
0.9536	High Similarity	NPC213608
0.9536	High Similarity	NPC1477
0.953	High Similarity	NPC226644
0.953	High Similarity	NPC37226
0.9477	High Similarity	NPC65504
0.947	High Similarity	NPC5871
0.947	High Similarity	NPC263676
0.9463	High Similarity	NPC135325
0.9408	High Similarity	NPC122365
0.9404	High Similarity	NPC170169
0.9404	High Similarity	NPC116604
0.94	High Similarity	NPC296030
0.94	High Similarity	NPC39929
0.9396	High Similarity	NPC12148
0.9396	High Similarity	NPC130581
0.9363	High Similarity	NPC136641
0.9355	High Similarity	NPC115432
0.9355	High Similarity	NPC260296
0.9346	High Similarity	NPC198490
0.9346	High Similarity	NPC148938
0.9338	High Similarity	NPC230713
0.9338	High Similarity	NPC78335
0.9329	High Similarity	NPC51641
0.9329	High Similarity	NPC300267
0.9329	High Similarity	NPC210826
0.9299	High Similarity	NPC155640
0.929	High Similarity	NPC40583
0.929	High Similarity	NPC244750
0.9281	High Similarity	NPC472462
0.9281	High Similarity	NPC235333
0.9281	High Similarity	NPC183874
0.9272	High Similarity	NPC178202
0.9272	High Similarity	NPC37208
0.9272	High Similarity	NPC221868
0.9262	High Similarity	NPC230943
0.9226	High Similarity	NPC246647
0.9226	High Similarity	NPC268360
0.9226	High Similarity	NPC164110
0.9226	High Similarity	NPC96342
0.9226	High Similarity	NPC212967
0.9221	High Similarity	NPC213936
0.9221	High Similarity	NPC297531
0.9216	High Similarity	NPC207624
0.9216	High Similarity	NPC253872
0.9211	High Similarity	NPC472406
0.9205	High Similarity	NPC272194
0.9195	High Similarity	NPC225884
0.9195	High Similarity	NPC302181
0.9177	High Similarity	NPC38591
0.9172	High Similarity	NPC304387
0.9167	High Similarity	NPC472877
0.9161	High Similarity	NPC180924
0.915	High Similarity	NPC193976
0.915	High Similarity	NPC115324
0.915	High Similarity	NPC23668
0.915	High Similarity	NPC58668
0.915	High Similarity	NPC106372
0.9145	High Similarity	NPC317492
0.9139	High Similarity	NPC198427
0.9139	High Similarity	NPC17816
0.913	High Similarity	NPC120220
0.9128	High Similarity	NPC53192
0.9119	High Similarity	NPC291110
0.9114	High Similarity	NPC193998
0.9114	High Similarity	NPC219861
0.9108	High Similarity	NPC304839
0.9108	High Similarity	NPC220582
0.9103	High Similarity	NPC270044
0.9103	High Similarity	NPC269495
0.9097	High Similarity	NPC474542
0.9097	High Similarity	NPC99199
0.9091	High Similarity	NPC142308
0.9085	High Similarity	NPC167576
0.9085	High Similarity	NPC148423
0.9085	High Similarity	NPC472421
0.9085	High Similarity	NPC135303
0.9079	High Similarity	NPC168085
0.9079	High Similarity	NPC39195
0.9074	High Similarity	NPC472584
0.9062	High Similarity	NPC53640
0.9057	High Similarity	NPC472581
0.9051	High Similarity	NPC30655
0.9051	High Similarity	NPC45124
0.9051	High Similarity	NPC74854
0.9032	High Similarity	NPC72370
0.9032	High Similarity	NPC42458
0.9032	High Similarity	NPC158261
0.9026	High Similarity	NPC472423
0.9026	High Similarity	NPC474772
0.9026	High Similarity	NPC474744
0.9013	High Similarity	NPC308200
0.9012	High Similarity	NPC131866
0.9007	High Similarity	NPC311741
0.9007	High Similarity	NPC234629
0.9007	High Similarity	NPC98926
0.9007	High Similarity	NPC155144
0.9006	High Similarity	NPC320789
0.9006	High Similarity	NPC476459
0.9	High Similarity	NPC96791
0.9	High Similarity	NPC470636
0.9	High Similarity	NPC226942
0.8987	High Similarity	NPC49009
0.8968	High Similarity	NPC31627
0.8968	High Similarity	NPC41326
0.8968	High Similarity	NPC38361
0.8968	High Similarity	NPC130015
0.8968	High Similarity	NPC473996
0.8968	High Similarity	NPC327269
0.8968	High Similarity	NPC476238
0.8961	High Similarity	NPC321896
0.8961	High Similarity	NPC476185
0.8961	High Similarity	NPC29777
0.8961	High Similarity	NPC155882
0.8961	High Similarity	NPC471115
0.8961	High Similarity	NPC191104
0.8954	High Similarity	NPC145467
0.8954	High Similarity	NPC266572
0.8954	High Similarity	NPC306788
0.8951	High Similarity	NPC53252
0.8947	High Similarity	NPC299011
0.8947	High Similarity	NPC190572
0.8947	High Similarity	NPC477955
0.8944	High Similarity	NPC323137
0.8944	High Similarity	NPC277480
0.894	High Similarity	NPC17262
0.894	High Similarity	NPC18585
0.894	High Similarity	NPC166138
0.894	High Similarity	NPC106985
0.8938	High Similarity	NPC109180
0.8931	High Similarity	NPC14822
0.8931	High Similarity	NPC472346
0.8917	High Similarity	NPC474386
0.891	High Similarity	NPC41719
0.8903	High Similarity	NPC472580
0.8903	High Similarity	NPC472636
0.8903	High Similarity	NPC472407
0.8903	High Similarity	NPC471675
0.8903	High Similarity	NPC318424
0.8896	High Similarity	NPC471114
0.8896	High Similarity	NPC88445
0.8889	High Similarity	NPC237635
0.8889	High Similarity	NPC79469
0.8889	High Similarity	NPC24673
0.8889	High Similarity	NPC247973
0.8889	High Similarity	NPC14875
0.8889	High Similarity	NPC50394
0.8889	High Similarity	NPC97716
0.8889	High Similarity	NPC201731
0.8889	High Similarity	NPC104406
0.8882	High Similarity	NPC259007
0.8882	High Similarity	NPC303185
0.8882	High Similarity	NPC38914
0.8882	High Similarity	NPC184649
0.8882	High Similarity	NPC204088
0.8882	High Similarity	NPC209040
0.8882	High Similarity	NPC329215
0.8882	High Similarity	NPC37183
0.8882	High Similarity	NPC271288
0.8882	High Similarity	NPC311144
0.8874	High Similarity	NPC11561
0.8874	High Similarity	NPC226636
0.8874	High Similarity	NPC144499
0.8868	High Similarity	NPC95472
0.8868	High Similarity	NPC303210
0.8868	High Similarity	NPC169
0.8868	High Similarity	NPC239270
0.8861	High Similarity	NPC196448
0.8859	High Similarity	NPC124269
0.8859	High Similarity	NPC471620
0.8859	High Similarity	NPC21350
0.8854	High Similarity	NPC233776
0.8846	High Similarity	NPC210597
0.8846	High Similarity	NPC285623
0.8846	High Similarity	NPC477957
0.8839	High Similarity	NPC61258
0.8839	High Similarity	NPC13282
0.8831	High Similarity	NPC6511
0.8824	High Similarity	NPC472629
0.8824	High Similarity	NPC124729
0.8824	High Similarity	NPC73320
0.882	High Similarity	NPC159508
0.8816	High Similarity	NPC169591
0.8816	High Similarity	NPC68104
0.8816	High Similarity	NPC149026
0.8816	High Similarity	NPC113770
0.8816	High Similarity	NPC316816
0.8816	High Similarity	NPC214166
0.8816	High Similarity	NPC221432
0.8816	High Similarity	NPC175504
0.8816	High Similarity	NPC150408
0.8816	High Similarity	NPC172182
0.8816	High Similarity	NPC262935
0.8816	High Similarity	NPC251182

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 NPC296957 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	974
0.2-0.3	1553
0.3-0.4	2628
0.4-0.5	1987
0.5-0.6	1130
0.6-0.7	355
0.7-0.8	119
0.8-0.85	46
0.85-0.9	12
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8792	High Similarity	NPD2344	Approved
0.8766	High Similarity	NPD920	Approved
0.8758	High Similarity	NPD4378	Clinical (unspecified phase)
0.8636	High Similarity	NPD642	Clinical (unspecified phase)
0.8636	High Similarity	NPD7410	Clinical (unspecified phase)
0.8625	High Similarity	NPD3749	Approved
0.8562	High Similarity	NPD2309	Approved
0.8553	High Similarity	NPD2800	Approved
0.8506	High Similarity	NPD643	Clinical (unspecified phase)
0.85	High Similarity	NPD8443	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD1549	Phase 2
0.8452	Intermediate Similarity	NPD6559	Discontinued
0.8438	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD7411	Suspended
0.8421	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1510	Phase 2
0.8389	Intermediate Similarity	NPD1240	Approved
0.8365	Intermediate Similarity	NPD4380	Phase 2
0.8355	Intermediate Similarity	NPD2796	Approved
0.8333	Intermediate Similarity	NPD7768	Phase 2
0.8333	Intermediate Similarity	NPD3882	Suspended
0.8323	Intermediate Similarity	NPD7819	Suspended
0.8313	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD1243	Approved
0.8301	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD7075	Discontinued
0.8278	Intermediate Similarity	NPD1607	Approved
0.8253	Intermediate Similarity	NPD3926	Phase 2
0.8242	Intermediate Similarity	NPD1247	Approved
0.8242	Intermediate Similarity	NPD6959	Discontinued
0.821	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5494	Approved
0.8165	Intermediate Similarity	NPD2533	Approved
0.8165	Intermediate Similarity	NPD2532	Approved
0.8165	Intermediate Similarity	NPD2534	Approved
0.8148	Intermediate Similarity	NPD1934	Approved
0.8121	Intermediate Similarity	NPD919	Approved
0.8117	Intermediate Similarity	NPD1551	Phase 2
0.8101	Intermediate Similarity	NPD6799	Approved
0.8098	Intermediate Similarity	NPD2801	Approved
0.8084	Intermediate Similarity	NPD6232	Discontinued
0.8077	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7473	Discontinued
0.8037	Intermediate Similarity	NPD6801	Discontinued
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD3818	Discontinued
0.7987	Intermediate Similarity	NPD1511	Approved
0.7965	Intermediate Similarity	NPD5953	Discontinued
0.7939	Intermediate Similarity	NPD2296	Approved
0.7935	Intermediate Similarity	NPD2799	Discontinued
0.7911	Intermediate Similarity	NPD3750	Approved
0.7895	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD1512	Approved
0.7885	Intermediate Similarity	NPD2935	Discontinued
0.7882	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6166	Phase 2
0.7874	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7286	Phase 2
0.7818	Intermediate Similarity	NPD6279	Approved
0.7818	Intermediate Similarity	NPD6280	Approved
0.7806	Intermediate Similarity	NPD6651	Approved
0.7799	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD5844	Phase 1
0.7744	Intermediate Similarity	NPD3226	Approved
0.7725	Intermediate Similarity	NPD3817	Phase 2
0.7722	Intermediate Similarity	NPD1471	Phase 3
0.7707	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8434	Phase 2
0.7665	Intermediate Similarity	NPD5760	Phase 2
0.7665	Intermediate Similarity	NPD5761	Phase 2
0.7662	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2313	Discontinued
0.7661	Intermediate Similarity	NPD6808	Phase 2
0.7611	Intermediate Similarity	NPD4287	Approved
0.76	Intermediate Similarity	NPD7074	Phase 3
0.7595	Intermediate Similarity	NPD3748	Approved
0.7578	Intermediate Similarity	NPD4628	Phase 3
0.7558	Intermediate Similarity	NPD5711	Approved
0.7558	Intermediate Similarity	NPD7229	Phase 3
0.7558	Intermediate Similarity	NPD5710	Approved
0.7546	Intermediate Similarity	NPD7390	Discontinued
0.7543	Intermediate Similarity	NPD7054	Approved
0.7532	Intermediate Similarity	NPD4908	Phase 1
0.7515	Intermediate Similarity	NPD5402	Approved
0.7515	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD1729	Discontinued
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD7472	Approved
0.7458	Intermediate Similarity	NPD6797	Phase 2
0.7452	Intermediate Similarity	NPD943	Approved
0.7451	Intermediate Similarity	NPD1203	Approved
0.7438	Intermediate Similarity	NPD6100	Approved
0.7438	Intermediate Similarity	NPD6099	Approved
0.7436	Intermediate Similarity	NPD3764	Approved
0.7419	Intermediate Similarity	NPD6832	Phase 2
0.7416	Intermediate Similarity	NPD7251	Discontinued
0.7405	Intermediate Similarity	NPD4361	Phase 2
0.7405	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5401	Approved
0.7375	Intermediate Similarity	NPD7033	Discontinued
0.7374	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7808	Phase 3
0.7362	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1465	Phase 2
0.7351	Intermediate Similarity	NPD4363	Phase 3
0.7351	Intermediate Similarity	NPD4360	Phase 2
0.7337	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1610	Phase 2
0.7303	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2654	Approved
0.729	Intermediate Similarity	NPD2798	Approved
0.7289	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD3751	Discontinued
0.7273	Intermediate Similarity	NPD2403	Approved
0.7261	Intermediate Similarity	NPD4625	Phase 3
0.7255	Intermediate Similarity	NPD3972	Approved
0.7255	Intermediate Similarity	NPD9717	Approved
0.7235	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3268	Approved
0.7188	Intermediate Similarity	NPD230	Phase 1
0.7188	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1876	Approved
0.716	Intermediate Similarity	NPD4308	Phase 3
0.7158	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1548	Phase 1
0.7152	Intermediate Similarity	NPD7003	Approved
0.7151	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8313	Approved
0.7143	Intermediate Similarity	NPD8312	Approved
0.7135	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2424	Discontinued
0.7127	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7458	Discontinued
0.7117	Intermediate Similarity	NPD5404	Approved
0.7117	Intermediate Similarity	NPD5406	Approved
0.7117	Intermediate Similarity	NPD5405	Approved
0.7117	Intermediate Similarity	NPD5408	Approved
0.7115	Intermediate Similarity	NPD2797	Approved
0.7115	Intermediate Similarity	NPD1470	Approved
0.7115	Intermediate Similarity	NPD1164	Approved
0.7102	Intermediate Similarity	NPD7199	Phase 2
0.7083	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD447	Suspended
0.7081	Intermediate Similarity	NPD5124	Phase 1
0.7078	Intermediate Similarity	NPD422	Phase 1
0.7073	Intermediate Similarity	NPD6002	Phase 3
0.7073	Intermediate Similarity	NPD6005	Phase 3
0.7073	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6004	Phase 3
0.7068	Intermediate Similarity	NPD6781	Approved
0.7068	Intermediate Similarity	NPD6780	Approved
0.7068	Intermediate Similarity	NPD6778	Approved
0.7068	Intermediate Similarity	NPD6782	Approved
0.7068	Intermediate Similarity	NPD6777	Approved
0.7068	Intermediate Similarity	NPD6776	Approved
0.7068	Intermediate Similarity	NPD6779	Approved
0.7062	Intermediate Similarity	NPD3787	Discontinued
0.7055	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD8151	Discontinued
0.7039	Intermediate Similarity	NPD9545	Approved
0.7032	Intermediate Similarity	NPD1608	Approved
0.7026	Intermediate Similarity	NPD7584	Approved
0.7024	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4288	Approved
0.701	Intermediate Similarity	NPD7870	Phase 2
0.701	Intermediate Similarity	NPD7871	Phase 2
0.7	Intermediate Similarity	NPD7177	Discontinued
0.6994	Remote Similarity	NPD37	Approved
0.6989	Remote Similarity	NPD6234	Discontinued
0.6975	Remote Similarity	NPD6355	Discontinued
0.6973	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD4965	Approved
0.6971	Remote Similarity	NPD4967	Phase 2
0.6971	Remote Similarity	NPD4966	Approved
0.6962	Remote Similarity	NPD1019	Discontinued
0.6959	Remote Similarity	NPD7696	Phase 3
0.6959	Remote Similarity	NPD7697	Approved
0.6959	Remote Similarity	NPD7435	Discontinued
0.6959	Remote Similarity	NPD7698	Approved
0.6954	Remote Similarity	NPD8455	Phase 2
0.6944	Remote Similarity	NPD3446	Phase 1
0.694	Remote Similarity	NPD6104	Discontinued
0.6933	Remote Similarity	NPD1241	Discontinued

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