NPASS Compound

Structure

NPC476350 OpenBabel07101719242D 28 30 0 0 1 0 0 0 0 0999 V2000 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 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 -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 3.5491 1.8090 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 4.4152 1.3090 0.0000 C 0 0 3 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 -2.0878 -0.0570 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 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 4.4152 0.3090 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 1.8171 2.8090 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 10 1 0 0 0 0 3 27 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 11 2 0 0 0 0 6 17 1 0 0 0 0 7 13 1 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 8 18 1 0 0 0 0 9 14 1 0 0 0 0 9 22 2 0 0 0 0 10 15 1 0 0 0 0 11 23 1 0 0 0 0 12 17 2 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 20 2 0 0 0 0 14 19 1 0 0 0 0 14 21 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 27 1 0 0 0 0 18 19 2 0 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 20 26 1 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.12
Volume:	383.906
LogP:	3.601
LogD:	2.436
LogS:	-3.716
# Rotatable Bonds:	6
TPSA:	117.2
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.553
Synthetic Accessibility Score:	3.069
Fsp3:	0.238
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:	-4.895
MDCK Permeability:	1.2331281141086947e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.968
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.142
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	97.9520492553711%
Volume Distribution (VD):	0.552
Pgp-substrate:	2.2843103408813477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.801
CYP1A2-substrate:	0.859
CYP2C19-inhibitor:	0.202
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.819
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.589
CYP2D6-substrate:	0.472
CYP3A4-inhibitor:	0.46
CYP3A4-substrate:	0.202

ADMET: Excretion

Clearance (CL):	10.687
Half-life (T1/2):	0.882

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.222
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.508
Rat Oral Acute Toxicity:	0.068
Maximum Recommended Daily Dose:	0.385
Skin Sensitization:	0.221
Carcinogencity:	0.029
Eye Corrosion:	0.004
Eye Irritation:	0.433
Respiratory Toxicity:	0.242

Download Data

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

Natural Product: NPC476350

Natural Product ID:	NPC476350
*Common Name:**	Ebenfuran Viii
IUPAC Name:	4,6-dihydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-(2-hydroxy-3-methylbut-3-enyl)-1-benzofuran-3-carbaldehyde
Synonyms:	Ebenfuran VIII
Standard InCHIKey:	ONCAJIQSAVIIRM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H20O7/c1-10(2)15(24)7-13-16(25)8-18-19(20(13)26)14(9-22)21(28-18)12-5-4-11(23)6-17(12)27-3/h4-6,8-9,15,23-26H,1,7H2,2-3H3
SMILES:	O=Cc1c(oc2c1c(O)c(c(c2)O)CC(C(=C)C)O)c1ccc(cc1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL574555
PubChem CID:	45481959
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	=	5200.0	nM	PMID[468060]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	155.0	%	PMID[468060]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	98.0	%	PMID[468060]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	RBA	=	0.04	n.a.	PMID[468060]

☑ 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 NPC476350 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	1662
0.2-0.3	3825
0.3-0.4	9664
0.4-0.5	8989
0.5-0.6	3919
0.6-0.7	5649
0.7-0.8	4761
0.8-0.85	2442
0.85-0.9	1183
0.9-0.95	190
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476349
0.9867	High Similarity	NPC247677
0.9867	High Similarity	NPC160015
0.9801	High Similarity	NPC296957
0.9801	High Similarity	NPC260902
0.9667	High Similarity	NPC67654
0.96	High Similarity	NPC156244
0.9474	High Similarity	NPC1477
0.9474	High Similarity	NPC213608
0.9474	High Similarity	NPC122365
0.9467	High Similarity	NPC39929
0.9467	High Similarity	NPC296030
0.9467	High Similarity	NPC37226
0.9467	High Similarity	NPC226644
0.9427	High Similarity	NPC136641
0.9408	High Similarity	NPC5871
0.9408	High Similarity	NPC263676
0.94	High Similarity	NPC135325
0.9355	High Similarity	NPC40583
0.9342	High Similarity	NPC116604
0.9342	High Similarity	NPC170169
0.9333	High Similarity	NPC12148
0.9333	High Similarity	NPC130581
0.9295	High Similarity	NPC115432
0.9295	High Similarity	NPC260296
0.929	High Similarity	NPC65504
0.929	High Similarity	NPC269495
0.9286	High Similarity	NPC198490
0.9286	High Similarity	NPC148938
0.9276	High Similarity	NPC230713
0.9276	High Similarity	NPC78335
0.9267	High Similarity	NPC51641
0.9267	High Similarity	NPC300267
0.9267	High Similarity	NPC210826
0.9241	High Similarity	NPC38591
0.9231	High Similarity	NPC244750
0.9221	High Similarity	NPC42458
0.9221	High Similarity	NPC235333
0.9221	High Similarity	NPC183874
0.9221	High Similarity	NPC158261
0.9211	High Similarity	NPC317492
0.9211	High Similarity	NPC178202
0.92	High Similarity	NPC230943
0.9167	High Similarity	NPC96342
0.9167	High Similarity	NPC212967
0.9167	High Similarity	NPC246647
0.9167	High Similarity	NPC164110
0.9161	High Similarity	NPC297531
0.9161	High Similarity	NPC213936
0.9156	High Similarity	NPC253872
0.9156	High Similarity	NPC207624
0.915	High Similarity	NPC472406
0.9145	High Similarity	NPC168085
0.9136	High Similarity	NPC472584
0.9133	High Similarity	NPC225884
0.9133	High Similarity	NPC302181
0.913	High Similarity	NPC53252
0.9119	High Similarity	NPC155640
0.9114	High Similarity	NPC304387
0.9114	High Similarity	NPC74854
0.9114	High Similarity	NPC45124
0.9114	High Similarity	NPC30655
0.9108	High Similarity	NPC472877
0.9103	High Similarity	NPC180924
0.9103	High Similarity	NPC474386
0.9097	High Similarity	NPC472462
0.9091	High Similarity	NPC193976
0.9091	High Similarity	NPC106372
0.9091	High Similarity	NPC23668
0.9091	High Similarity	NPC472423
0.9091	High Similarity	NPC58668
0.9091	High Similarity	NPC474772
0.9091	High Similarity	NPC474744
0.9091	High Similarity	NPC115324
0.9085	High Similarity	NPC37208
0.9085	High Similarity	NPC221868
0.9079	High Similarity	NPC198427
0.9079	High Similarity	NPC17816
0.9074	High Similarity	NPC120220
0.9068	High Similarity	NPC320789
0.9068	High Similarity	NPC476459
0.9067	High Similarity	NPC53192
0.9062	High Similarity	NPC291110
0.9057	High Similarity	NPC193998
0.9051	High Similarity	NPC220582
0.9051	High Similarity	NPC49009
0.9051	High Similarity	NPC304839
0.9051	High Similarity	NPC169
0.9045	High Similarity	NPC270044
0.9045	High Similarity	NPC268360
0.9032	High Similarity	NPC142308
0.9026	High Similarity	NPC472421
0.9026	High Similarity	NPC148423
0.9026	High Similarity	NPC321896
0.9026	High Similarity	NPC167576
0.9026	High Similarity	NPC135303
0.9026	High Similarity	NPC476185
0.902	High Similarity	NPC272194
0.902	High Similarity	NPC39195
0.9013	High Similarity	NPC472629
0.9006	High Similarity	NPC53640
0.9	High Similarity	NPC109180
0.9	High Similarity	NPC321980
0.9	High Similarity	NPC470087
0.9	High Similarity	NPC472581
0.8994	High Similarity	NPC14822
0.8994	High Similarity	NPC472346
0.8957	High Similarity	NPC131866
0.8954	High Similarity	NPC308200
0.8951	High Similarity	NPC247973
0.8947	High Similarity	NPC155144
0.8947	High Similarity	NPC98926
0.8947	High Similarity	NPC87486
0.8947	High Similarity	NPC124780
0.8947	High Similarity	NPC470890
0.8947	High Similarity	NPC224714
0.894	High Similarity	NPC470636
0.894	High Similarity	NPC226942
0.894	High Similarity	NPC96791
0.8938	High Similarity	NPC219861
0.8931	High Similarity	NPC95472
0.8931	High Similarity	NPC239270
0.8931	High Similarity	NPC303210
0.8917	High Similarity	NPC99199
0.8917	High Similarity	NPC474542
0.891	High Similarity	NPC31627
0.891	High Similarity	NPC38361
0.891	High Similarity	NPC327269
0.891	High Similarity	NPC41326
0.891	High Similarity	NPC473996
0.891	High Similarity	NPC130015
0.891	High Similarity	NPC476238
0.891	High Similarity	NPC285623
0.8903	High Similarity	NPC155882
0.8903	High Similarity	NPC191104
0.8903	High Similarity	NPC61258
0.8896	High Similarity	NPC306788
0.8896	High Similarity	NPC145467
0.8889	High Similarity	NPC73320
0.8889	High Similarity	NPC299011
0.8889	High Similarity	NPC190572
0.8889	High Similarity	NPC277480
0.8882	High Similarity	NPC117836
0.8882	High Similarity	NPC91560
0.8882	High Similarity	NPC175504
0.8882	High Similarity	NPC164980
0.8882	High Similarity	NPC75049
0.8882	High Similarity	NPC475705
0.8882	High Similarity	NPC310130
0.8882	High Similarity	NPC471621
0.8882	High Similarity	NPC245482
0.8882	High Similarity	NPC169591
0.8882	High Similarity	NPC68104
0.8882	High Similarity	NPC301751
0.8882	High Similarity	NPC149026
0.8882	High Similarity	NPC150408
0.8882	High Similarity	NPC476178
0.8882	High Similarity	NPC39329
0.8882	High Similarity	NPC143896
0.8882	High Similarity	NPC221432
0.8882	High Similarity	NPC257097
0.8882	High Similarity	NPC51887
0.8874	High Similarity	NPC470089
0.8867	High Similarity	NPC470211
0.8867	High Similarity	NPC137009
0.8867	High Similarity	NPC37206
0.8854	High Similarity	NPC72370
0.8854	High Similarity	NPC41719
0.8846	High Similarity	NPC472580
0.8846	High Similarity	NPC472636
0.8846	High Similarity	NPC318424
0.8846	High Similarity	NPC472407
0.8846	High Similarity	NPC471676
0.8846	High Similarity	NPC263384
0.8846	High Similarity	NPC471675
0.8846	High Similarity	NPC472422
0.8846	High Similarity	NPC244577
0.8846	High Similarity	NPC472420
0.8839	High Similarity	NPC214493
0.8839	High Similarity	NPC471114
0.8839	High Similarity	NPC88445
0.8839	High Similarity	NPC5173
0.8834	High Similarity	NPC186392
0.8834	High Similarity	NPC50394
0.8831	High Similarity	NPC300988
0.8831	High Similarity	NPC10990
0.8831	High Similarity	NPC14875
0.8827	High Similarity	NPC474591
0.8827	High Similarity	NPC38914
0.8827	High Similarity	NPC37183
0.8824	High Similarity	NPC473015
0.8824	High Similarity	NPC311144
0.8824	High Similarity	NPC234629
0.8824	High Similarity	NPC184649
0.8824	High Similarity	NPC473013
0.8824	High Similarity	NPC303185
0.8824	High Similarity	NPC197252
0.8824	High Similarity	NPC271288
0.8824	High Similarity	NPC236766
0.8824	High Similarity	NPC209040

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 NPC476350 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	962
0.2-0.3	1598
0.3-0.4	2636
0.4-0.5	1977
0.5-0.6	1108
0.6-0.7	342
0.7-0.8	125
0.8-0.85	41
0.85-0.9	14
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8733	High Similarity	NPD2344	Approved
0.871	High Similarity	NPD920	Approved
0.8701	High Similarity	NPD4378	Clinical (unspecified phase)
0.8623	High Similarity	NPD6559	Discontinued
0.8581	High Similarity	NPD642	Clinical (unspecified phase)
0.8562	High Similarity	NPD8443	Clinical (unspecified phase)
0.8553	High Similarity	NPD1549	Phase 2
0.8544	High Similarity	NPD4380	Phase 2
0.8506	High Similarity	NPD2309	Approved
0.85	High Similarity	NPD2393	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD2800	Approved
0.8487	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD3749	Approved
0.8452	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD2796	Approved
0.8375	Intermediate Similarity	NPD7411	Suspended
0.8355	Intermediate Similarity	NPD1510	Phase 2
0.8344	Intermediate Similarity	NPD7075	Discontinued
0.8333	Intermediate Similarity	NPD1240	Approved
0.8303	Intermediate Similarity	NPD6959	Discontinued
0.8282	Intermediate Similarity	NPD7768	Phase 2
0.8282	Intermediate Similarity	NPD3882	Suspended
0.8272	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD7819	Suspended
0.8263	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD1243	Approved
0.8247	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD5494	Approved
0.8232	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1607	Approved
0.821	Intermediate Similarity	NPD6801	Discontinued
0.821	Intermediate Similarity	NPD1934	Approved
0.8204	Intermediate Similarity	NPD3926	Phase 2
0.8193	Intermediate Similarity	NPD1247	Approved
0.8166	Intermediate Similarity	NPD3818	Discontinued
0.8113	Intermediate Similarity	NPD2532	Approved
0.8113	Intermediate Similarity	NPD2534	Approved
0.8113	Intermediate Similarity	NPD2533	Approved
0.8072	Intermediate Similarity	NPD919	Approved
0.8065	Intermediate Similarity	NPD1551	Phase 2
0.805	Intermediate Similarity	NPD6799	Approved
0.8049	Intermediate Similarity	NPD2801	Approved
0.8047	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6166	Phase 2
0.8036	Intermediate Similarity	NPD6232	Discontinued
0.8025	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7473	Discontinued
0.7975	Intermediate Similarity	NPD6599	Discontinued
0.7953	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD1511	Approved
0.7931	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD5953	Discontinued
0.7907	Intermediate Similarity	NPD5844	Phase 1
0.7892	Intermediate Similarity	NPD2296	Approved
0.7885	Intermediate Similarity	NPD2799	Discontinued
0.7862	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD3750	Approved
0.7844	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1512	Approved
0.7834	Intermediate Similarity	NPD2935	Discontinued
0.7803	Intermediate Similarity	NPD7286	Phase 2
0.7771	Intermediate Similarity	NPD6279	Approved
0.7771	Intermediate Similarity	NPD6280	Approved
0.7759	Intermediate Similarity	NPD7074	Phase 3
0.7756	Intermediate Similarity	NPD6651	Approved
0.7753	Intermediate Similarity	NPD8434	Phase 2
0.775	Intermediate Similarity	NPD4628	Phase 3
0.7736	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD5760	Phase 2
0.7725	Intermediate Similarity	NPD5761	Phase 2
0.7719	Intermediate Similarity	NPD6808	Phase 2
0.7701	Intermediate Similarity	NPD7054	Approved
0.7697	Intermediate Similarity	NPD3226	Approved
0.7683	Intermediate Similarity	NPD5403	Approved
0.7679	Intermediate Similarity	NPD3817	Phase 2
0.7679	Intermediate Similarity	NPD5402	Approved
0.7673	Intermediate Similarity	NPD1471	Phase 3
0.7658	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD7472	Approved
0.7614	Intermediate Similarity	NPD6797	Phase 2
0.7613	Intermediate Similarity	NPD2313	Discontinued
0.7613	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7251	Discontinued
0.7561	Intermediate Similarity	NPD5401	Approved
0.7547	Intermediate Similarity	NPD3748	Approved
0.7528	Intermediate Similarity	NPD7808	Phase 3
0.7528	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5711	Approved
0.7514	Intermediate Similarity	NPD5710	Approved
0.7514	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7229	Phase 3
0.75	Intermediate Similarity	NPD4360	Phase 2
0.75	Intermediate Similarity	NPD4363	Phase 3
0.75	Intermediate Similarity	NPD7390	Discontinued
0.7484	Intermediate Similarity	NPD4908	Phase 1
0.7473	Intermediate Similarity	NPD4287	Approved
0.7459	Intermediate Similarity	NPD4361	Phase 2
0.7459	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD1729	Discontinued
0.7455	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2346	Discontinued
0.7438	Intermediate Similarity	NPD7033	Discontinued
0.7405	Intermediate Similarity	NPD943	Approved
0.7403	Intermediate Similarity	NPD1203	Approved
0.7391	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6832	Phase 2
0.7368	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD3751	Discontinued
0.733	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1465	Phase 2
0.7294	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD8312	Approved
0.7293	Intermediate Similarity	NPD8313	Approved
0.7284	Intermediate Similarity	NPD6099	Approved
0.7284	Intermediate Similarity	NPD6100	Approved
0.7278	Intermediate Similarity	NPD3764	Approved
0.7262	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2654	Approved
0.7255	Intermediate Similarity	NPD1610	Phase 2
0.7244	Intermediate Similarity	NPD2798	Approved
0.7241	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6005	Phase 3
0.7239	Intermediate Similarity	NPD6004	Phase 3
0.7239	Intermediate Similarity	NPD6002	Phase 3
0.7239	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3972	Approved
0.7208	Intermediate Similarity	NPD9717	Approved
0.7195	Intermediate Similarity	NPD2424	Discontinued
0.7189	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD8151	Discontinued
0.717	Intermediate Similarity	NPD3268	Approved
0.7159	Intermediate Similarity	NPD7199	Phase 2
0.7151	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5124	Phase 1
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7143	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2403	Approved
0.7126	Intermediate Similarity	NPD4965	Approved
0.7126	Intermediate Similarity	NPD4967	Phase 2
0.7126	Intermediate Similarity	NPD4966	Approved
0.712	Intermediate Similarity	NPD6776	Approved
0.712	Intermediate Similarity	NPD6778	Approved
0.712	Intermediate Similarity	NPD6777	Approved
0.712	Intermediate Similarity	NPD6782	Approved
0.712	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6780	Approved
0.712	Intermediate Similarity	NPD6781	Approved
0.712	Intermediate Similarity	NPD6779	Approved
0.7119	Intermediate Similarity	NPD3787	Discontinued
0.7115	Intermediate Similarity	NPD1876	Approved
0.7112	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD8455	Phase 2
0.7108	Intermediate Similarity	NPD7003	Approved
0.7107	Intermediate Similarity	NPD4625	Phase 3
0.7105	Intermediate Similarity	NPD1548	Phase 1
0.7088	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1613	Approved
0.7077	Intermediate Similarity	NPD7584	Approved
0.7076	Intermediate Similarity	NPD7458	Discontinued
0.7073	Intermediate Similarity	NPD5408	Approved
0.7073	Intermediate Similarity	NPD5405	Approved
0.7073	Intermediate Similarity	NPD5406	Approved
0.7073	Intermediate Similarity	NPD5404	Approved
0.707	Intermediate Similarity	NPD2797	Approved
0.707	Intermediate Similarity	NPD1164	Approved
0.707	Intermediate Similarity	NPD1470	Approved
0.7062	Intermediate Similarity	NPD7871	Phase 2
0.7062	Intermediate Similarity	NPD7870	Phase 2
0.7052	Intermediate Similarity	NPD6844	Discontinued
0.7045	Intermediate Similarity	NPD6234	Discontinued
0.7041	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6355	Discontinued
0.7037	Intermediate Similarity	NPD447	Suspended
0.7032	Intermediate Similarity	NPD422	Phase 1
0.7012	Intermediate Similarity	NPD4308	Phase 3
0.7012	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7696	Phase 3
0.701	Intermediate Similarity	NPD7435	Discontinued
0.701	Intermediate Similarity	NPD7698	Approved
0.701	Intermediate Similarity	NPD7697	Approved
0.7	Intermediate Similarity	NPD6273	Approved
0.7	Intermediate Similarity	NPD3027	Phase 3
0.6993	Remote Similarity	NPD9545	Approved
0.6987	Remote Similarity	NPD1608	Approved
0.6983	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2861	Phase 2
0.6971	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD4288	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