NPASS Compound

Structure

NPC67654 OpenBabel07101718192D 22 24 0 0 0 0 0 0 0 0999 V2000 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 -3.0878 -0.0570 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 1.8171 -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 0.3090 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 1.8171 1.8090 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 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 3.3122 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 21 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 10 1 0 0 0 0 4 8 2 0 0 0 0 4 12 1 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 9 1 0 0 0 0 6 14 2 0 0 0 0 7 11 1 0 0 0 0 7 17 2 0 0 0 0 8 18 1 0 0 0 0 9 21 1 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 15 1 0 0 0 0 11 16 2 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.06
Volume:	291.273
LogP:	3.616
LogD:	2.963
LogS:	-4.001
# Rotatable Bonds:	3
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.643
Synthetic Accessibility Score:	2.724
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.985
MDCK Permeability:	8.542131581634749e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.272
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.688
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	97.82869720458984%
Volume Distribution (VD):	0.618
Pgp-substrate:	3.751495361328125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.611
CYP2C19-inhibitor:	0.29
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.646
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.731
CYP2D6-substrate:	0.793
CYP3A4-inhibitor:	0.722
CYP3A4-substrate:	0.099

ADMET: Excretion

Clearance (CL):	9.185
Half-life (T1/2):	0.793

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.652
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.856
Skin Sensitization:	0.161
Carcinogencity:	0.048
Eye Corrosion:	0.101
Eye Irritation:	0.945
Respiratory Toxicity:	0.366

Download Data

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

Natural Product: NPC67654

Natural Product ID:	NPC67654
*Common Name:**	Ebenfuran Ii
IUPAC Name:	2-(2,4-dihydroxyphenyl)-4-hydroxy-6-methoxy-1-benzofuran-3-carbaldehyde
Synonyms:	Ebenfuran II
Standard InCHIKey:	MYAHOBWCBIQQLV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O6/c1-21-9-5-13(20)15-11(7-17)16(22-14(15)6-9)10-3-2-8(18)4-12(10)19/h2-7,18-20H,1H3
SMILES:	COc1cc(O)c2c(c1)oc(c2C=O)c1ccc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491705
PubChem CID:	10266789
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
IC50	1
Others	4

Activity Type	# Activity
Cell Line	3
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	RBA	=	0.28	n.a.	PMID[544903]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	IC50	=	43.0	nM	PMID[544903]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	111.0	%	PMID[544904]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	5500.0	nM	PMID[544904]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	64.0	%	PMID[544904]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	RBA	=	0.18	n.a.	PMID[544904]

☑ 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 NPC67654 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	409
0.1-0.2	1811
0.2-0.3	4201
0.3-0.4	10656
0.4-0.5	7582
0.5-0.6	4064
0.6-0.7	5854
0.7-0.8	4643
0.8-0.85	2123
0.85-0.9	1148
0.9-0.95	185
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC156244
0.9797	High Similarity	NPC160015
0.9797	High Similarity	NPC247677
0.9732	High Similarity	NPC260902
0.9732	High Similarity	NPC296957
0.9667	High Similarity	NPC476350
0.9667	High Similarity	NPC476349
0.9517	High Similarity	NPC230943
0.9463	High Similarity	NPC263676
0.9448	High Similarity	NPC302181
0.9408	High Similarity	NPC472877
0.94	High Similarity	NPC1477
0.94	High Similarity	NPC213608
0.9396	High Similarity	NPC116604
0.9396	High Similarity	NPC115324
0.9392	High Similarity	NPC226644
0.9392	High Similarity	NPC37226
0.9388	High Similarity	NPC17816
0.9379	High Similarity	NPC53192
0.9333	High Similarity	NPC207624
0.9333	High Similarity	NPC5871
0.9324	High Similarity	NPC135325
0.9272	High Similarity	NPC122365
0.9267	High Similarity	NPC106372
0.9267	High Similarity	NPC58668
0.9267	High Similarity	NPC170169
0.9267	High Similarity	NPC23668
0.9267	High Similarity	NPC193976
0.9262	High Similarity	NPC39929
0.9262	High Similarity	NPC296030
0.9257	High Similarity	NPC12148
0.9257	High Similarity	NPC130581
0.9252	High Similarity	NPC98926
0.9252	High Similarity	NPC155144
0.9231	High Similarity	NPC291110
0.9221	High Similarity	NPC260296
0.9221	High Similarity	NPC115432
0.9216	High Similarity	NPC65504
0.9211	High Similarity	NPC198490
0.9211	High Similarity	NPC148938
0.9205	High Similarity	NPC41326
0.9205	High Similarity	NPC253872
0.9205	High Similarity	NPC142308
0.92	High Similarity	NPC167576
0.92	High Similarity	NPC78335
0.92	High Similarity	NPC230713
0.9189	High Similarity	NPC51641
0.9189	High Similarity	NPC300267
0.9189	High Similarity	NPC210826
0.9184	High Similarity	NPC225884
0.9161	High Similarity	NPC304387
0.9156	High Similarity	NPC244750
0.9156	High Similarity	NPC40583
0.9145	High Similarity	NPC158261
0.9145	High Similarity	NPC235333
0.9145	High Similarity	NPC183874
0.9145	High Similarity	NPC42458
0.9133	High Similarity	NPC178202
0.9128	High Similarity	NPC198427
0.9122	High Similarity	NPC303185
0.9122	High Similarity	NPC184649
0.9108	High Similarity	NPC136641
0.9103	High Similarity	NPC193998
0.9091	High Similarity	NPC212967
0.9091	High Similarity	NPC246647
0.9091	High Similarity	NPC96342
0.9091	High Similarity	NPC164110
0.9091	High Similarity	NPC270044
0.9085	High Similarity	NPC99199
0.9085	High Similarity	NPC297531
0.9085	High Similarity	NPC213936
0.9085	High Similarity	NPC474542
0.9073	High Similarity	NPC135303
0.9073	High Similarity	NPC472406
0.9073	High Similarity	NPC148423
0.906	High Similarity	NPC299011
0.9054	High Similarity	NPC113770
0.9045	High Similarity	NPC155640
0.9045	High Similarity	NPC38591
0.9026	High Similarity	NPC180924
0.9026	High Similarity	NPC13879
0.902	High Similarity	NPC472462
0.902	High Similarity	NPC72370
0.9007	High Similarity	NPC221868
0.9007	High Similarity	NPC317492
0.9007	High Similarity	NPC37208
0.8994	High Similarity	NPC320789
0.8993	High Similarity	NPC311144
0.8986	High Similarity	NPC202981
0.8973	High Similarity	NPC124269
0.8968	High Similarity	NPC269495
0.8968	High Similarity	NPC268360
0.8954	High Similarity	NPC38361
0.8954	High Similarity	NPC130015
0.8951	High Similarity	NPC290304
0.8951	High Similarity	NPC236327
0.8947	High Similarity	NPC155882
0.894	High Similarity	NPC272194
0.894	High Similarity	NPC168085
0.894	High Similarity	NPC39195
0.894	High Similarity	NPC306788
0.8933	High Similarity	NPC190572
0.8924	High Similarity	NPC109180
0.8917	High Similarity	NPC188486
0.8904	High Similarity	NPC188879
0.8903	High Similarity	NPC137100
0.8903	High Similarity	NPC45131
0.8896	High Similarity	NPC41719
0.8889	High Similarity	NPC472407
0.8882	High Similarity	NPC120220
0.8882	High Similarity	NPC131866
0.8882	High Similarity	NPC88445
0.8874	High Similarity	NPC308200
0.8868	High Similarity	NPC38914
0.8861	High Similarity	NPC219861
0.8861	High Similarity	NPC84515
0.8861	High Similarity	NPC312056
0.8859	High Similarity	NPC96791
0.8859	High Similarity	NPC470636
0.8859	High Similarity	NPC226942
0.8854	High Similarity	NPC304839
0.8854	High Similarity	NPC220582
0.8854	High Similarity	NPC169
0.8844	High Similarity	NPC188947
0.8844	High Similarity	NPC55162
0.8844	High Similarity	NPC278323
0.8844	High Similarity	NPC12175
0.8844	High Similarity	NPC280284
0.8844	High Similarity	NPC309154
0.8844	High Similarity	NPC90665
0.8844	High Similarity	NPC279668
0.8844	High Similarity	NPC99333
0.8839	High Similarity	NPC233776
0.8836	High Similarity	NPC240593
0.8827	High Similarity	NPC472584
0.8824	High Similarity	NPC476185
0.8824	High Similarity	NPC267117
0.8824	High Similarity	NPC472421
0.8824	High Similarity	NPC321896
0.8824	High Similarity	NPC191104
0.882	High Similarity	NPC53252
0.8816	High Similarity	NPC145467
0.8812	High Similarity	NPC277480
0.8812	High Similarity	NPC53640
0.8808	High Similarity	NPC73320
0.8805	High Similarity	NPC472581
0.8797	High Similarity	NPC74854
0.8797	High Similarity	NPC30655
0.8797	High Similarity	NPC45124
0.8792	High Similarity	NPC3188
0.879	High Similarity	NPC16935
0.879	High Similarity	NPC196879
0.8784	High Similarity	NPC150648
0.8784	High Similarity	NPC316480
0.8784	High Similarity	NPC274784
0.8784	High Similarity	NPC329203
0.8784	High Similarity	NPC137009
0.8784	High Similarity	NPC265871
0.8784	High Similarity	NPC222342
0.8784	High Similarity	NPC225153
0.8784	High Similarity	NPC20709
0.8784	High Similarity	NPC310135
0.8784	High Similarity	NPC261234
0.8782	High Similarity	NPC474386
0.8776	High Similarity	NPC303644
0.8776	High Similarity	NPC275055
0.8776	High Similarity	NPC162680
0.8776	High Similarity	NPC290291
0.8776	High Similarity	NPC228661
0.8776	High Similarity	NPC209560
0.8776	High Similarity	NPC294409
0.8776	High Similarity	NPC250266
0.8776	High Similarity	NPC266597
0.8776	High Similarity	NPC181124
0.8776	High Similarity	NPC116632
0.8776	High Similarity	NPC7013
0.8766	High Similarity	NPC474772
0.8766	High Similarity	NPC472423
0.8766	High Similarity	NPC318424
0.8766	High Similarity	NPC474744
0.8766	High Similarity	NPC471229
0.8758	High Similarity	NPC277032
0.8758	High Similarity	NPC247973
0.8758	High Similarity	NPC476459
0.8758	High Similarity	NPC471114
0.8758	High Similarity	NPC50394
0.8758	High Similarity	NPC86477
0.8758	High Similarity	NPC241820
0.875	High Similarity	NPC304443
0.875	High Similarity	NPC29411
0.875	High Similarity	NPC74539
0.875	High Similarity	NPC37183
0.875	High Similarity	NPC474591
0.8742	High Similarity	NPC71210
0.8742	High Similarity	NPC311741
0.8742	High Similarity	NPC272722
0.8742	High Similarity	NPC234629
0.8742	High Similarity	NPC271288
0.8734	High Similarity	NPC49009
0.8733	High Similarity	NPC73028

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 NPC67654 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	980
0.2-0.3	1609
0.3-0.4	2637
0.4-0.5	1924
0.5-0.6	1114
0.6-0.7	337
0.7-0.8	107
0.8-0.85	45
0.85-0.9	16
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9034	High Similarity	NPD2344	Approved
0.8792	High Similarity	NPD2309	Approved
0.875	High Similarity	NPD920	Approved
0.8726	High Similarity	NPD3749	Approved
0.8716	High Similarity	NPD1549	Phase 2
0.8649	High Similarity	NPD1550	Clinical (unspecified phase)
0.8649	High Similarity	NPD1552	Clinical (unspecified phase)
0.8639	High Similarity	NPD1510	Phase 2
0.8621	High Similarity	NPD1240	Approved
0.8618	High Similarity	NPD4378	Clinical (unspecified phase)
0.8618	High Similarity	NPD642	Clinical (unspecified phase)
0.8533	High Similarity	NPD2800	Approved
0.8503	High Similarity	NPD1607	Approved
0.8487	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD2796	Approved
0.8428	Intermediate Similarity	NPD3882	Suspended
0.8377	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD1934	Approved
0.8344	Intermediate Similarity	NPD3926	Phase 2
0.8333	Intermediate Similarity	NPD1551	Phase 2
0.8323	Intermediate Similarity	NPD6559	Discontinued
0.8302	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD7411	Suspended
0.8289	Intermediate Similarity	NPD1243	Approved
0.8278	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD4380	Phase 2
0.8221	Intermediate Similarity	NPD1247	Approved
0.8199	Intermediate Similarity	NPD7768	Phase 2
0.8194	Intermediate Similarity	NPD1511	Approved
0.8194	Intermediate Similarity	NPD6799	Approved
0.8187	Intermediate Similarity	NPD2801	Approved
0.8187	Intermediate Similarity	NPD7819	Suspended
0.8182	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD7075	Discontinued
0.8137	Intermediate Similarity	NPD2296	Approved
0.8117	Intermediate Similarity	NPD3750	Approved
0.8113	Intermediate Similarity	NPD6599	Discontinued
0.811	Intermediate Similarity	NPD6959	Discontinued
0.8098	Intermediate Similarity	NPD919	Approved
0.8089	Intermediate Similarity	NPD1512	Approved
0.8084	Intermediate Similarity	NPD3818	Discontinued
0.8075	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD5494	Approved
0.8025	Intermediate Similarity	NPD2532	Approved
0.8025	Intermediate Similarity	NPD2534	Approved
0.8025	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6166	Phase 2
0.7964	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6232	Discontinued
0.7935	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7473	Discontinued
0.7901	Intermediate Similarity	NPD6280	Approved
0.7901	Intermediate Similarity	NPD6801	Discontinued
0.7901	Intermediate Similarity	NPD6279	Approved
0.7867	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD5953	Discontinued
0.7806	Intermediate Similarity	NPD1471	Phase 3
0.7805	Intermediate Similarity	NPD3817	Phase 2
0.7792	Intermediate Similarity	NPD2799	Discontinued
0.7792	Intermediate Similarity	NPD3748	Approved
0.7765	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2935	Discontinued
0.7738	Intermediate Similarity	NPD6808	Phase 2
0.7719	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7286	Phase 2
0.7716	Intermediate Similarity	NPD3226	Approved
0.7684	Intermediate Similarity	NPD4287	Approved
0.7677	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7074	Phase 3
0.7662	Intermediate Similarity	NPD6651	Approved
0.7658	Intermediate Similarity	NPD4628	Phase 3
0.7651	Intermediate Similarity	NPD1203	Approved
0.7647	Intermediate Similarity	NPD943	Approved
0.7632	Intermediate Similarity	NPD2313	Discontinued
0.7616	Intermediate Similarity	NPD5844	Phase 1
0.7616	Intermediate Similarity	NPD4908	Phase 1
0.7616	Intermediate Similarity	NPD7054	Approved
0.7593	Intermediate Similarity	NPD5403	Approved
0.759	Intermediate Similarity	NPD5402	Approved
0.7578	Intermediate Similarity	NPD5401	Approved
0.7572	Intermediate Similarity	NPD7472	Approved
0.7571	Intermediate Similarity	NPD8434	Phase 2
0.753	Intermediate Similarity	NPD1465	Phase 2
0.753	Intermediate Similarity	NPD5761	Phase 2
0.753	Intermediate Similarity	NPD5760	Phase 2
0.7529	Intermediate Similarity	NPD6797	Phase 2
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7251	Discontinued
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.745	Intermediate Similarity	NPD9717	Approved
0.7443	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7808	Phase 3
0.7429	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5711	Approved
0.7427	Intermediate Similarity	NPD5710	Approved
0.7427	Intermediate Similarity	NPD7229	Phase 3
0.7407	Intermediate Similarity	NPD7390	Discontinued
0.7405	Intermediate Similarity	NPD6099	Approved
0.7405	Intermediate Similarity	NPD6100	Approved
0.7378	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2654	Approved
0.7372	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD230	Phase 1
0.7371	Intermediate Similarity	NPD1729	Discontinued
0.7368	Intermediate Similarity	NPD2798	Approved
0.7362	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3751	Discontinued
0.7351	Intermediate Similarity	NPD1876	Approved
0.7347	Intermediate Similarity	NPD1548	Phase 1
0.7342	Intermediate Similarity	NPD7033	Discontinued
0.7333	Intermediate Similarity	NPD3972	Approved
0.729	Intermediate Similarity	NPD3268	Approved
0.7283	Intermediate Similarity	NPD4361	Phase 2
0.7283	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD422	Phase 1
0.7261	Intermediate Similarity	NPD447	Suspended
0.7241	Intermediate Similarity	NPD2403	Approved
0.7241	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4308	Phase 3
0.723	Intermediate Similarity	NPD9545	Approved
0.7228	Intermediate Similarity	NPD4363	Phase 3
0.7228	Intermediate Similarity	NPD4360	Phase 2
0.7222	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1608	Approved
0.7213	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2797	Approved
0.719	Intermediate Similarity	NPD1470	Approved
0.7176	Intermediate Similarity	NPD4288	Approved
0.7168	Intermediate Similarity	NPD7199	Phase 2
0.7151	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1019	Discontinued
0.7123	Intermediate Similarity	NPD1241	Discontinued
0.712	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD9494	Approved
0.7095	Intermediate Similarity	NPD9493	Approved
0.7091	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1613	Approved
0.7086	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3266	Approved
0.7078	Intermediate Similarity	NPD3267	Approved
0.7078	Intermediate Similarity	NPD1164	Approved
0.707	Intermediate Similarity	NPD411	Approved
0.7059	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1933	Approved
0.7044	Intermediate Similarity	NPD6355	Discontinued
0.7037	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3787	Discontinued
0.702	Intermediate Similarity	NPD17	Approved
0.7017	Intermediate Similarity	NPD8313	Approved
0.7017	Intermediate Similarity	NPD8312	Approved
0.7013	Intermediate Similarity	NPD3225	Approved
0.7012	Intermediate Similarity	NPD7003	Approved
0.7011	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4625	Phase 3
0.7	Intermediate Similarity	NPD6104	Discontinued
0.6987	Remote Similarity	NPD2861	Phase 2
0.6987	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7458	Discontinued
0.6981	Remote Similarity	NPD4307	Phase 2
0.6977	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5408	Approved
0.6975	Remote Similarity	NPD5404	Approved
0.6975	Remote Similarity	NPD5406	Approved
0.6975	Remote Similarity	NPD5405	Approved
0.6962	Remote Similarity	NPD1296	Phase 2
0.6962	Remote Similarity	NPD6798	Discontinued
0.6959	Remote Similarity	NPD6844	Discontinued
0.6959	Remote Similarity	NPD37	Approved
0.6954	Remote Similarity	NPD6234	Discontinued
0.6946	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD4967	Phase 2
0.6936	Remote Similarity	NPD4966	Approved
0.6936	Remote Similarity	NPD4965	Approved
0.6933	Remote Similarity	NPD6004	Phase 3
0.6933	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6002	Phase 3
0.6933	Remote Similarity	NPD6005	Phase 3
0.6933	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1201	Approved
0.6923	Remote Similarity	NPD8151	Discontinued
0.6899	Remote Similarity	NPD3027	Phase 3
0.6897	Remote Similarity	NPD6971	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