NPASS Compound

Structure

NPC58685 OpenBabel07101719132D 30 33 0 0 1 0 0 0 0 0999 V2000 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 7 2 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 10 2 0 0 0 0 8 17 1 0 0 0 0 9 11 2 0 0 0 0 9 18 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 23 2 0 0 0 0 14 24 2 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 25 2 0 0 0 0 18 20 1 0 0 0 0 18 26 2 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 27 2 0 0 0 0 22 28 2 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.11
Volume:	410.538
LogP:	5.201
LogD:	2.433
LogS:	-3.643
# Rotatable Bonds:	2
TPSA:	115.06
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.474
Synthetic Accessibility Score:	3.102
Fsp3:	0.083
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.838
MDCK Permeability:	1.1317488315398805e-05
Pgp-inhibitor:	0.103
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.181
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	99.07423400878906%
Volume Distribution (VD):	0.345
Pgp-substrate:	2.4534943103790283%

ADMET: Metabolism

CYP1A2-inhibitor:	0.835
CYP1A2-substrate:	0.444
CYP2C19-inhibitor:	0.453
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.685
CYP2C9-substrate:	0.216
CYP2D6-inhibitor:	0.201
CYP2D6-substrate:	0.157
CYP3A4-inhibitor:	0.16
CYP3A4-substrate:	0.135

ADMET: Excretion

Clearance (CL):	3.27
Half-life (T1/2):	0.084

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.796
Rat Oral Acute Toxicity:	0.442
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.941
Carcinogencity:	0.773
Eye Corrosion:	0.003
Eye Irritation:	0.859
Respiratory Toxicity:	0.095

Download Data

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

Natural Product: NPC58685

Natural Product ID:	NPC58685
*Common Name:**	Ethylidene-6,6'-Biplumbagin
IUPAC Name:	5-hydroxy-6-[1-(1-hydroxy-6-methyl-5,8-dioxonaphthalen-2-yl)ethyl]-2-methylnaphthalene-1,4-dione
Synonyms:	Ethylidene-6,6'-Biplumbagin
Standard InCHIKey:	QIJWTOJFMIXPTB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H18O6/c1-10-8-17(25)19-15(21(10)27)6-4-13(23(19)29)12(3)14-5-7-16-20(24(14)30)18(26)9-11(2)22(16)28/h4-9,12,29-30H,1-3H3
SMILES:	CC1=CC(=O)c2c(ccc(C(C)c3ccc4c(C(=O)C=C(C)C4=O)c3O)c2O)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2023570
PubChem CID:	14163338
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	bark	Indonesia	n.a.	PMID[15270571]
NPO33133	barleria alluaudii	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22313254]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22313254]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16657	Diospyros maritima	Species	Ebenaceae	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

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT369	Cell Line	ACHN	Homo sapiens	EC50	>	30000.0	nM	PMID[456416]

☑ 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 NPC58685 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	339
0.1-0.2	1500
0.2-0.3	3136
0.3-0.4	8728
0.4-0.5	10831
0.5-0.6	5683
0.6-0.7	8395
0.7-0.8	3557
0.8-0.85	360
0.85-0.9	122
0.9-0.95	38
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9603	High Similarity	NPC34414
0.9603	High Similarity	NPC146647
0.9528	High Similarity	NPC55949
0.9462	High Similarity	NPC283088
0.9457	High Similarity	NPC115458
0.937	High Similarity	NPC282923
0.9365	High Similarity	NPC3224
0.9308	High Similarity	NPC53896
0.9302	High Similarity	NPC244699
0.9242	High Similarity	NPC272268
0.9237	High Similarity	NPC50924
0.9219	High Similarity	NPC48248
0.9206	High Similarity	NPC142956
0.9173	High Similarity	NPC245923
0.9173	High Similarity	NPC305060
0.9154	High Similarity	NPC205992
0.9154	High Similarity	NPC17083
0.9147	High Similarity	NPC99731
0.9134	High Similarity	NPC103540
0.9098	High Similarity	NPC474813
0.9091	High Similarity	NPC287604
0.9091	High Similarity	NPC161964
0.9091	High Similarity	NPC472262
0.9055	High Similarity	NPC173978
0.9048	High Similarity	NPC307174
0.9015	High Similarity	NPC225051
0.8976	High Similarity	NPC375356
0.8971	High Similarity	NPC181560
0.8971	High Similarity	NPC169452
0.8963	High Similarity	NPC13715
0.8939	High Similarity	NPC70622
0.8915	High Similarity	NPC231774
0.8915	High Similarity	NPC306765
0.8898	High Similarity	NPC300274
0.8897	High Similarity	NPC138099
0.8897	High Similarity	NPC242994
0.8881	High Similarity	NPC80035
0.8872	High Similarity	NPC114183
0.8864	High Similarity	NPC474517
0.8864	High Similarity	NPC72669
0.8841	High Similarity	NPC193555
0.8841	High Similarity	NPC239136
0.8841	High Similarity	NPC19631
0.8832	High Similarity	NPC315578
0.8832	High Similarity	NPC225243
0.8815	High Similarity	NPC193358
0.8815	High Similarity	NPC155211
0.881	High Similarity	NPC285829
0.881	High Similarity	NPC206778
0.8806	High Similarity	NPC288089
0.8806	High Similarity	NPC270899
0.8806	High Similarity	NPC12070
0.8797	High Similarity	NPC246693
0.8797	High Similarity	NPC242358
0.8797	High Similarity	NPC110609
0.8788	High Similarity	NPC136588
0.8788	High Similarity	NPC31799
0.8788	High Similarity	NPC199253
0.8779	High Similarity	NPC96024
0.8777	High Similarity	NPC471682
0.8769	High Similarity	NPC96915
0.8759	High Similarity	NPC1268
0.8759	High Similarity	NPC26924
0.875	High Similarity	NPC53206
0.875	High Similarity	NPC53414
0.875	High Similarity	NPC471905
0.8741	High Similarity	NPC161632
0.8741	High Similarity	NPC249272
0.8712	High Similarity	NPC278928
0.8705	High Similarity	NPC257644
0.8702	High Similarity	NPC471530
0.8696	High Similarity	NPC96421
0.8686	High Similarity	NPC416
0.8686	High Similarity	NPC61398
0.8676	High Similarity	NPC315275
0.8676	High Similarity	NPC254847
0.8667	High Similarity	NPC282780
0.8667	High Similarity	NPC166480
0.8657	High Similarity	NPC309430
0.8652	High Similarity	NPC471683
0.8633	High Similarity	NPC124365
0.8633	High Similarity	NPC246638
0.8615	High Similarity	NPC199273
0.8615	High Similarity	NPC310540
0.8613	High Similarity	NPC53001
0.8613	High Similarity	NPC62272
0.8603	High Similarity	NPC258502
0.8593	High Similarity	NPC314048
0.8593	High Similarity	NPC52407
0.8593	High Similarity	NPC254603
0.8571	High Similarity	NPC474300
0.8571	High Similarity	NPC109123
0.8571	High Similarity	NPC135524
0.8561	High Similarity	NPC72667
0.8551	High Similarity	NPC87723
0.8551	High Similarity	NPC4214
0.854	High Similarity	NPC474311
0.854	High Similarity	NPC141934
0.854	High Similarity	NPC191976
0.8538	High Similarity	NPC275145
0.8529	High Similarity	NPC44437
0.8519	High Similarity	NPC175738
0.8511	High Similarity	NPC313047
0.8511	High Similarity	NPC474203
0.8511	High Similarity	NPC451542
0.8511	High Similarity	NPC295712
0.8511	High Similarity	NPC476473
0.8507	High Similarity	NPC475741
0.8507	High Similarity	NPC198305
0.85	High Similarity	NPC305845
0.85	High Similarity	NPC187843
0.85	High Similarity	NPC477275
0.85	High Similarity	NPC204045
0.8492	Intermediate Similarity	NPC108288
0.8492	Intermediate Similarity	NPC477453
0.8489	Intermediate Similarity	NPC143438
0.8489	Intermediate Similarity	NPC295339
0.8485	Intermediate Similarity	NPC1991
0.8485	Intermediate Similarity	NPC160499
0.8485	Intermediate Similarity	NPC254492
0.8483	Intermediate Similarity	NPC315520
0.8478	Intermediate Similarity	NPC36868
0.8473	Intermediate Similarity	NPC68756
0.8473	Intermediate Similarity	NPC234890
0.8473	Intermediate Similarity	NPC236189
0.8473	Intermediate Similarity	NPC152525
0.8473	Intermediate Similarity	NPC74507
0.8462	Intermediate Similarity	NPC85393
0.8462	Intermediate Similarity	NPC110882
0.8462	Intermediate Similarity	NPC282577
0.8462	Intermediate Similarity	NPC147250
0.8462	Intermediate Similarity	NPC271944
0.8456	Intermediate Similarity	NPC267205
0.8451	Intermediate Similarity	NPC29932
0.8451	Intermediate Similarity	NPC193703
0.8451	Intermediate Similarity	NPC477913
0.8451	Intermediate Similarity	NPC21599
0.8451	Intermediate Similarity	NPC10764
0.8444	Intermediate Similarity	NPC41847
0.8444	Intermediate Similarity	NPC85342
0.844	Intermediate Similarity	NPC69755
0.844	Intermediate Similarity	NPC469520
0.8433	Intermediate Similarity	NPC276238
0.8433	Intermediate Similarity	NPC25736
0.8433	Intermediate Similarity	NPC171460
0.8429	Intermediate Similarity	NPC241349
0.8429	Intermediate Similarity	NPC327916
0.8429	Intermediate Similarity	NPC42262
0.8429	Intermediate Similarity	NPC220496
0.8429	Intermediate Similarity	NPC32749
0.8429	Intermediate Similarity	NPC147542
0.8429	Intermediate Similarity	NPC37992
0.8421	Intermediate Similarity	NPC69424
0.8421	Intermediate Similarity	NPC176130
0.8421	Intermediate Similarity	NPC78364
0.8421	Intermediate Similarity	NPC84672
0.8417	Intermediate Similarity	NPC230811
0.8417	Intermediate Similarity	NPC61590
0.8413	Intermediate Similarity	NPC161304
0.8406	Intermediate Similarity	NPC472308
0.8406	Intermediate Similarity	NPC86524
0.8406	Intermediate Similarity	NPC118919
0.8403	Intermediate Similarity	NPC37709
0.8394	Intermediate Similarity	NPC1249
0.8392	Intermediate Similarity	NPC170055
0.8392	Intermediate Similarity	NPC34482
0.8385	Intermediate Similarity	NPC154696
0.838	Intermediate Similarity	NPC293545
0.838	Intermediate Similarity	NPC296752
0.838	Intermediate Similarity	NPC174905
0.837	Intermediate Similarity	NPC31539
0.837	Intermediate Similarity	NPC108129
0.8369	Intermediate Similarity	NPC106519
0.8369	Intermediate Similarity	NPC91019
0.8358	Intermediate Similarity	NPC237225
0.8358	Intermediate Similarity	NPC165257
0.8357	Intermediate Similarity	NPC111422
0.8357	Intermediate Similarity	NPC470407
0.8357	Intermediate Similarity	NPC216312
0.8357	Intermediate Similarity	NPC29771
0.8357	Intermediate Similarity	NPC190457
0.8357	Intermediate Similarity	NPC306835
0.8357	Intermediate Similarity	NPC476477
0.8357	Intermediate Similarity	NPC471602
0.8357	Intermediate Similarity	NPC256463
0.8357	Intermediate Similarity	NPC299405
0.8356	Intermediate Similarity	NPC205766
0.8346	Intermediate Similarity	NPC71610
0.8346	Intermediate Similarity	NPC49647
0.8346	Intermediate Similarity	NPC227741
0.8346	Intermediate Similarity	NPC474106
0.8346	Intermediate Similarity	NPC295202
0.8346	Intermediate Similarity	NPC136342
0.8345	Intermediate Similarity	NPC471452
0.8333	Intermediate Similarity	NPC290803
0.8333	Intermediate Similarity	NPC22222
0.8333	Intermediate Similarity	NPC470570
0.8333	Intermediate Similarity	NPC136878
0.8333	Intermediate Similarity	NPC281513
0.8333	Intermediate Similarity	NPC285122

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 NPC58685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	944
0.2-0.3	1238
0.3-0.4	2568
0.4-0.5	2352
0.5-0.6	1185
0.6-0.7	447
0.7-0.8	85
0.8-0.85	3
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9134	High Similarity	NPD1470	Approved
0.8819	High Similarity	NPD1201	Approved
0.8676	High Similarity	NPD1509	Clinical (unspecified phase)
0.8613	High Similarity	NPD5404	Approved
0.8613	High Similarity	NPD5405	Approved
0.8613	High Similarity	NPD5408	Approved
0.8613	High Similarity	NPD5406	Approved
0.8492	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD7390	Discontinued
0.8156	Intermediate Similarity	NPD2346	Discontinued
0.8125	Intermediate Similarity	NPD3300	Phase 2
0.8041	Intermediate Similarity	NPD3226	Approved
0.782	Intermediate Similarity	NPD2932	Approved
0.773	Intermediate Similarity	NPD943	Approved
0.7687	Intermediate Similarity	NPD3019	Approved
0.7681	Intermediate Similarity	NPD2798	Approved
0.7639	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD2799	Discontinued
0.7634	Intermediate Similarity	NPD5951	Approved
0.7615	Intermediate Similarity	NPD7635	Approved
0.7609	Intermediate Similarity	NPD1164	Approved
0.7589	Intermediate Similarity	NPD2313	Discontinued
0.7586	Intermediate Similarity	NPD2935	Discontinued
0.7562	Intermediate Similarity	NPD7473	Discontinued
0.7556	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2342	Discontinued
0.75	Intermediate Similarity	NPD7003	Approved
0.7484	Intermediate Similarity	NPD6232	Discontinued
0.7481	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD3764	Approved
0.7425	Intermediate Similarity	NPD8150	Discontinued
0.7417	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4878	Approved
0.7383	Intermediate Similarity	NPD3750	Approved
0.7379	Intermediate Similarity	NPD1607	Approved
0.7372	Intermediate Similarity	NPD7819	Suspended
0.7338	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6959	Discontinued
0.7303	Intermediate Similarity	NPD2532	Approved
0.7303	Intermediate Similarity	NPD2534	Approved
0.7303	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2533	Approved
0.7297	Intermediate Similarity	NPD2344	Approved
0.7279	Intermediate Similarity	NPD1510	Phase 2
0.7252	Intermediate Similarity	NPD4750	Phase 3
0.7246	Intermediate Similarity	NPD3023	Approved
0.7246	Intermediate Similarity	NPD3026	Approved
0.7246	Intermediate Similarity	NPD8312	Approved
0.7246	Intermediate Similarity	NPD8313	Approved
0.7241	Intermediate Similarity	NPD1240	Approved
0.7235	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5031	Approved
0.7229	Intermediate Similarity	NPD5029	Approved
0.7229	Intermediate Similarity	NPD5027	Approved
0.7226	Intermediate Similarity	NPD3025	Approved
0.7226	Intermediate Similarity	NPD3024	Approved
0.7215	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1930	Approved
0.7188	Intermediate Similarity	NPD1929	Approved
0.7188	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4380	Phase 2
0.7176	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD74	Approved
0.7176	Intermediate Similarity	NPD9266	Approved
0.7174	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1283	Approved
0.7152	Intermediate Similarity	NPD8166	Discontinued
0.7152	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD9493	Approved
0.7115	Intermediate Similarity	NPD7458	Discontinued
0.7105	Intermediate Similarity	NPD2309	Approved
0.7101	Intermediate Similarity	NPD1651	Approved
0.7099	Intermediate Similarity	NPD9267	Approved
0.7099	Intermediate Similarity	NPD9263	Approved
0.7099	Intermediate Similarity	NPD9264	Approved
0.7086	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4954	Approved
0.7083	Intermediate Similarity	NPD4955	Approved
0.7083	Intermediate Similarity	NPD36	Approved
0.7083	Intermediate Similarity	NPD5026	Approved
0.7083	Intermediate Similarity	NPD5028	Approved
0.7083	Intermediate Similarity	NPD5034	Approved
0.7067	Intermediate Similarity	NPD1471	Phase 3
0.7067	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD288	Approved
0.7063	Intermediate Similarity	NPD7768	Phase 2
0.7052	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3748	Approved
0.7042	Intermediate Similarity	NPD1876	Approved
0.7039	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7008	Discontinued
0.7034	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7411	Suspended
0.7024	Intermediate Similarity	NPD5030	Phase 2
0.702	Intermediate Similarity	NPD1549	Phase 2
0.7019	Intermediate Similarity	NPD3749	Approved
0.7018	Intermediate Similarity	NPD5037	Approved
0.7018	Intermediate Similarity	NPD5038	Approved
0.7007	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4879	Approved
0.7	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD1551	Phase 2
0.7	Intermediate Similarity	NPD6100	Approved
0.7	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1203	Approved
0.6984	Remote Similarity	NPD844	Approved
0.6977	Remote Similarity	NPD1932	Approved
0.6974	Remote Similarity	NPD2800	Approved
0.6971	Remote Similarity	NPD6535	Approved
0.6971	Remote Similarity	NPD6534	Approved
0.696	Remote Similarity	NPD845	Approved
0.6959	Remote Similarity	NPD5036	Approved
0.6954	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD2066	Phase 3
0.6953	Remote Similarity	NPD3020	Approved
0.695	Remote Similarity	NPD1281	Approved
0.695	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6020	Phase 2
0.6939	Remote Similarity	NPD6663	Approved
0.6937	Remote Similarity	NPD2801	Approved
0.6936	Remote Similarity	NPD6836	Approved
0.6933	Remote Similarity	NPD5494	Approved
0.6933	Remote Similarity	NPD4308	Phase 3
0.6929	Remote Similarity	NPD4626	Approved
0.6929	Remote Similarity	NPD3495	Discontinued
0.6923	Remote Similarity	NPD6273	Approved
0.6918	Remote Similarity	NPD4625	Phase 3
0.6917	Remote Similarity	NPD2329	Discontinued
0.6914	Remote Similarity	NPD6212	Phase 3
0.6914	Remote Similarity	NPD7075	Discontinued
0.6914	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6213	Phase 3
0.6913	Remote Similarity	NPD6651	Approved
0.6906	Remote Similarity	NPD7009	Phase 2
0.6903	Remote Similarity	NPD1511	Approved
0.6901	Remote Similarity	NPD3972	Approved
0.6897	Remote Similarity	NPD5736	Approved
0.6889	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2796	Approved
0.6886	Remote Similarity	NPD7177	Discontinued
0.6875	Remote Similarity	NPD2797	Approved
0.6875	Remote Similarity	NPD1934	Approved
0.6871	Remote Similarity	NPD411	Approved
0.6871	Remote Similarity	NPD3268	Approved
0.687	Remote Similarity	NPD1237	Approved
0.6867	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD3022	Approved
0.6866	Remote Similarity	NPD3021	Approved
0.6861	Remote Similarity	NPD9281	Approved
0.6854	Remote Similarity	NPD7700	Phase 2
0.6854	Remote Similarity	NPD7699	Phase 2
0.6853	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3882	Suspended
0.6845	Remote Similarity	NPD5844	Phase 1
0.6842	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7610	Discontinued
0.6832	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6559	Discontinued
0.6818	Remote Similarity	NPD4628	Phase 3
0.6815	Remote Similarity	NPD1512	Approved
0.6794	Remote Similarity	NPD9261	Approved
0.679	Remote Similarity	NPD5402	Approved
0.6786	Remote Similarity	NPD3091	Approved
0.6784	Remote Similarity	NPD5032	Approved
0.6783	Remote Similarity	NPD9717	Approved
0.6783	Remote Similarity	NPD1608	Approved
0.6779	Remote Similarity	NPD2979	Phase 3
0.6778	Remote Similarity	NPD6782	Approved
0.6778	Remote Similarity	NPD6779	Approved
0.6778	Remote Similarity	NPD6777	Approved
0.6778	Remote Similarity	NPD6776	Approved
0.6778	Remote Similarity	NPD6778	Approved
0.6778	Remote Similarity	NPD6781	Approved
0.6778	Remote Similarity	NPD6780	Approved
0.677	Remote Similarity	NPD6844	Discontinued
0.6761	Remote Similarity	NPD5968	Phase 3
0.6752	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6599	Discontinued
0.6747	Remote Similarity	NPD5710	Approved
0.6747	Remote Similarity	NPD5711	Approved
0.6746	Remote Similarity	NPD7631	Approved
0.6744	Remote Similarity	NPD5035	Approved
0.6739	Remote Similarity	NPD497	Approved
0.6735	Remote Similarity	NPD6832	Phase 2
0.6733	Remote Similarity	NPD447	Suspended
0.6731	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5033	Approved
0.6721	Remote Similarity	NPD8320	Phase 1
0.6721	Remote Similarity	NPD8319	Approved
0.6719	Remote Similarity	NPD2859	Approved
0.6719	Remote Similarity	NPD2860	Approved
0.6713	Remote Similarity	NPD3092	Approved
0.6712	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4381	Clinical (unspecified phase)

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