NPASS Compound

Structure

CID283088 OpenBabel06191716092D 28 31 0 0 0 0 0 0 0 0999 V2000 -3.4641 2.0000 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 0.0000 2.0000 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 5.1962 -1.0000 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 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 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 -0.8660 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 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 4.3301 -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 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 3.4641 -0.0000 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 3.4641 -1.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 2.5981 -2.5000 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 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 6 1 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 18 2 0 0 0 0 11 13 1 0 0 0 0 11 22 2 0 0 0 0 12 19 2 0 0 0 0 12 21 1 0 0 0 0 14 18 1 0 0 0 0 14 23 2 0 0 0 0 15 20 1 0 0 0 0 15 24 2 0 0 0 0 16 19 1 0 0 0 0 16 25 2 0 0 0 0 17 20 2 0 0 0 0 17 26 1 0 0 0 0 18 20 1 0 0 0 0 19 22 1 0 0 0 0 21 27 2 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.09
Volume:	378.583
LogP:	5.136
LogD:	2.851
LogS:	-5.04
# Rotatable Bonds:	1
TPSA:	115.06
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	2.924
Fsp3:	0.091
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:	-5.196
MDCK Permeability:	9.192169272864703e-06
Pgp-inhibitor:	0.019
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	100.4460220336914%
Volume Distribution (VD):	0.33
Pgp-substrate:	1.1317954063415527%

ADMET: Metabolism

CYP1A2-inhibitor:	0.955
CYP1A2-substrate:	0.224
CYP2C19-inhibitor:	0.55
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.771
CYP2C9-substrate:	0.629
CYP2D6-inhibitor:	0.252
CYP2D6-substrate:	0.195
CYP3A4-inhibitor:	0.17
CYP3A4-substrate:	0.102

ADMET: Excretion

Clearance (CL):	4.541
Half-life (T1/2):	0.294

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.088
Drug-inuced Liver Injury (DILI):	0.881
AMES Toxicity:	0.796
Rat Oral Acute Toxicity:	0.615
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.944
Carcinogencity:	0.751
Eye Corrosion:	0.006
Eye Irritation:	0.958
Respiratory Toxicity:	0.077

Download Data

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

Natural Product: NPC283088

Natural Product ID:	NPC283088
*Common Name:**	1',4-Dihydroxy-1,6'-Dimethyl-6,7-Dihydro-2,2'-Binaphthyl-5,5',8,8'-Tetraone
IUPAC Name:	5-hydroxy-6-(4-hydroxy-1-methyl-5,8-dioxo-6,7-dihydronaphthalen-2-yl)-2-methylnaphthalene-1,4-dione
Synonyms:
Standard InCHIKey:	BILDVPLFDVMZBG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H16O6/c1-9-7-16(25)19-12(21(9)27)4-3-11(22(19)28)13-8-17(26)20-15(24)6-5-14(23)18(20)10(13)2/h3-4,7-8,26,28H,5-6H2,1-2H3
SMILES:	O=C1C(=CC(=O)c2c1ccc(c2O)c1cc(O)c2c(c1C)C(=O)CCC2=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097168
PubChem CID:	46888888
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO22192	Cribraria cancellata	Species	Cribrariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695806]
NPO20721	Halichondria panicea	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20695474]
NPO22069	Persea major	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614421]
NPO20721	Halichondria panicea	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27035556]
NPO18256	Aconitum excelsum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23045	Lotus helleri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23045	Lotus helleri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18256	Aconitum excelsum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20721	Halichondria panicea	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22192	Cribraria cancellata	Species	Cribrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21383	Cnicothamnus lorentzii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9038	Aconitum burnatii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18921	Athrixia phylicoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13113	Ardisia kivuensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22831	Isodon angustifolius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20094	Loranthus micranthus	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22999	Cussonia spicata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22069	Persea major	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23432	Viguiera oaxacana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23045	Lotus helleri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19736	Haplopappus glutinosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23865	Scorzonera veratrifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23517	Heterotropa aspera	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18256	Aconitum excelsum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17645.1	Orobanche cernua var. cumana	Varieties	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18387	Sedum formosanum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22196	Kickxia ramosissima	Species	Plantaginaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1381	Organism	Aedes aegypti	Aedes aegypti	LC50	=	31.21	ug.mL-1	PMID[535969]
NPT1381	Organism	Aedes aegypti	Aedes aegypti	LC90	=	42.72	ug ml-1	PMID[535969]

☑ 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 NPC283088 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	360
0.1-0.2	1581
0.2-0.3	3336
0.3-0.4	9665
0.4-0.5	9502
0.5-0.6	5058
0.6-0.7	7992
0.7-0.8	4496
0.8-0.85	458
0.85-0.9	187
0.9-0.95	47
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9535	High Similarity	NPC244699
0.9531	High Similarity	NPC99731
0.9466	High Similarity	NPC50924
0.9462	High Similarity	NPC58685
0.9453	High Similarity	NPC282923
0.9453	High Similarity	NPC48248
0.9398	High Similarity	NPC245923
0.9389	High Similarity	NPC53896
0.9389	High Similarity	NPC115458
0.9385	High Similarity	NPC72669
0.9385	High Similarity	NPC474517
0.938	High Similarity	NPC34414
0.938	High Similarity	NPC146647
0.9338	High Similarity	NPC239136
0.9338	High Similarity	NPC19631
0.9328	High Similarity	NPC13715
0.9323	High Similarity	NPC474813
0.9308	High Similarity	NPC55949
0.9259	High Similarity	NPC242994
0.9259	High Similarity	NPC138099
0.9242	High Similarity	NPC225051
0.9237	High Similarity	NPC205992
0.9219	High Similarity	NPC103540
0.9191	High Similarity	NPC169452
0.9191	High Similarity	NPC181560
0.9179	High Similarity	NPC272268
0.9147	High Similarity	NPC3224
0.9141	High Similarity	NPC173978
0.9141	High Similarity	NPC142956
0.9124	High Similarity	NPC246638
0.9111	High Similarity	NPC471905
0.9111	High Similarity	NPC53414
0.9111	High Similarity	NPC53206
0.9104	High Similarity	NPC80035
0.9098	High Similarity	NPC314048
0.9062	High Similarity	NPC375356
0.9058	High Similarity	NPC193555
0.9044	High Similarity	NPC416
0.9044	High Similarity	NPC61398
0.9037	High Similarity	NPC155211
0.9037	High Similarity	NPC254847
0.903	High Similarity	NPC161964
0.903	High Similarity	NPC287604
0.903	High Similarity	NPC472262
0.9023	High Similarity	NPC70622
0.9008	High Similarity	NPC96024
0.8984	High Similarity	NPC300274
0.8984	High Similarity	NPC307174
0.8971	High Similarity	NPC305060
0.8971	High Similarity	NPC62272
0.8971	High Similarity	NPC53001
0.8955	High Similarity	NPC52407
0.8929	High Similarity	NPC10764
0.8921	High Similarity	NPC135524
0.8913	High Similarity	NPC96421
0.8913	High Similarity	NPC315578
0.8905	High Similarity	NPC4214
0.8905	High Similarity	NPC87723
0.8897	High Similarity	NPC191976
0.8889	High Similarity	NPC282780
0.8889	High Similarity	NPC166480
0.8889	High Similarity	NPC288089
0.8889	High Similarity	NPC44437
0.8889	High Similarity	NPC12070
0.8873	High Similarity	NPC37709
0.8872	High Similarity	NPC136588
0.8872	High Similarity	NPC199253
0.8857	High Similarity	NPC296752
0.8857	High Similarity	NPC471682
0.8855	High Similarity	NPC96915
0.8855	High Similarity	NPC231774
0.8855	High Similarity	NPC306765
0.8849	High Similarity	NPC305845
0.8849	High Similarity	NPC204045
0.8841	High Similarity	NPC143438
0.8841	High Similarity	NPC26924
0.8841	High Similarity	NPC1268
0.8824	High Similarity	NPC249272
0.8824	High Similarity	NPC258502
0.8819	High Similarity	NPC205766
0.8815	High Similarity	NPC114183
0.8815	High Similarity	NPC267205
0.8806	High Similarity	NPC17083
0.8803	High Similarity	NPC147250
0.8797	High Similarity	NPC276238
0.8794	High Similarity	NPC193703
0.8794	High Similarity	NPC21599
0.8786	High Similarity	NPC469520
0.8786	High Similarity	NPC257644
0.8777	High Similarity	NPC225243
0.8759	High Similarity	NPC193358
0.875	High Similarity	NPC206778
0.875	High Similarity	NPC285829
0.875	High Similarity	NPC270899
0.8741	High Similarity	NPC242358
0.8741	High Similarity	NPC110609
0.8741	High Similarity	NPC246693
0.8732	High Similarity	NPC471683
0.8732	High Similarity	NPC34482
0.8731	High Similarity	NPC31799
0.8723	High Similarity	NPC313047
0.8723	High Similarity	NPC474203
0.8723	High Similarity	NPC295712
0.8723	High Similarity	NPC451542
0.8714	High Similarity	NPC477275
0.8714	High Similarity	NPC124365
0.8714	High Similarity	NPC187843
0.8712	High Similarity	NPC254492
0.8705	High Similarity	NPC190457
0.8702	High Similarity	NPC164014
0.8702	High Similarity	NPC199273
0.8692	High Similarity	NPC91478
0.8692	High Similarity	NPC176208
0.8686	High Similarity	NPC161632
0.8676	High Similarity	NPC294226
0.8671	High Similarity	NPC85393
0.8671	High Similarity	NPC110882
0.8671	High Similarity	NPC470570
0.8671	High Similarity	NPC271944
0.8667	High Similarity	NPC41847
0.8667	High Similarity	NPC93015
0.8667	High Similarity	NPC85342
0.8662	High Similarity	NPC244691
0.8662	High Similarity	NPC471906
0.8662	High Similarity	NPC227841
0.8662	High Similarity	NPC48762
0.8662	High Similarity	NPC477913
0.8657	High Similarity	NPC278928
0.8652	High Similarity	NPC73061
0.8652	High Similarity	NPC85310
0.8652	High Similarity	NPC474961
0.8652	High Similarity	NPC69755
0.8647	High Similarity	NPC72667
0.8647	High Similarity	NPC176130
0.8647	High Similarity	NPC78364
0.8647	High Similarity	NPC471530
0.8647	High Similarity	NPC84672
0.8647	High Similarity	NPC69424
0.8623	High Similarity	NPC315275
0.8623	High Similarity	NPC118919
0.8623	High Similarity	NPC141934
0.8615	High Similarity	NPC120545
0.8611	High Similarity	NPC119767
0.8603	High Similarity	NPC309430
0.8603	High Similarity	NPC175738
0.8601	High Similarity	NPC12402
0.8593	High Similarity	NPC108129
0.8593	High Similarity	NPC27659
0.8592	High Similarity	NPC174905
0.8592	High Similarity	NPC66593
0.8592	High Similarity	NPC293545
0.8582	High Similarity	NPC106519
0.8582	High Similarity	NPC290550
0.8582	High Similarity	NPC91019
0.8581	High Similarity	NPC66029
0.8581	High Similarity	NPC66508
0.8581	High Similarity	NPC226656
0.8571	High Similarity	NPC160499
0.8562	High Similarity	NPC315520
0.8561	High Similarity	NPC310540
0.8561	High Similarity	NPC36868
0.8561	High Similarity	NPC147418
0.855	High Similarity	NPC282577
0.8542	High Similarity	NPC314437
0.8531	High Similarity	NPC79627
0.8521	High Similarity	NPC474300
0.8519	High Similarity	NPC92624
0.8519	High Similarity	NPC171460
0.8511	High Similarity	NPC203063
0.8503	High Similarity	NPC35
0.85	High Similarity	NPC141368
0.8489	Intermediate Similarity	NPC86524
0.8489	Intermediate Similarity	NPC474311
0.8483	Intermediate Similarity	NPC312929
0.8483	Intermediate Similarity	NPC472135
0.8483	Intermediate Similarity	NPC290194
0.8483	Intermediate Similarity	NPC190648
0.8483	Intermediate Similarity	NPC126767
0.8483	Intermediate Similarity	NPC289042
0.8483	Intermediate Similarity	NPC245584
0.8483	Intermediate Similarity	NPC118027
0.8483	Intermediate Similarity	NPC56433
0.8478	Intermediate Similarity	NPC202225
0.8478	Intermediate Similarity	NPC1249
0.8473	Intermediate Similarity	NPC154696
0.8472	Intermediate Similarity	NPC478019
0.8472	Intermediate Similarity	NPC68441
0.8462	Intermediate Similarity	NPC476473
0.8462	Intermediate Similarity	NPC53016
0.8456	Intermediate Similarity	NPC259942
0.8456	Intermediate Similarity	NPC31539
0.8456	Intermediate Similarity	NPC117609
0.8456	Intermediate Similarity	NPC198305
0.8456	Intermediate Similarity	NPC475741
0.8451	Intermediate Similarity	NPC110810
0.844	Intermediate Similarity	NPC295339
0.844	Intermediate Similarity	NPC470407
0.8438	Intermediate Similarity	NPC477453
0.8438	Intermediate Similarity	NPC108288
0.8435	Intermediate Similarity	NPC290954

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 NPC283088 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	958
0.2-0.3	1276
0.3-0.4	2621
0.4-0.5	2214
0.5-0.6	1167
0.6-0.7	475
0.7-0.8	100
0.8-0.85	3
0.85-0.9	2
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9219	High Similarity	NPD1470	Approved
0.9037	High Similarity	NPD1509	Clinical (unspecified phase)
0.8971	High Similarity	NPD5405	Approved
0.8971	High Similarity	NPD5408	Approved
0.8971	High Similarity	NPD5406	Approved
0.8971	High Similarity	NPD5404	Approved
0.8906	High Similarity	NPD1201	Approved
0.8662	High Similarity	NPD7390	Discontinued
0.8472	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD3226	Approved
0.7986	Intermediate Similarity	NPD2346	Discontinued
0.7956	Intermediate Similarity	NPD1164	Approved
0.7943	Intermediate Similarity	NPD943	Approved
0.791	Intermediate Similarity	NPD3019	Approved
0.791	Intermediate Similarity	NPD2932	Approved
0.7898	Intermediate Similarity	NPD6232	Discontinued
0.7862	Intermediate Similarity	NPD7473	Discontinued
0.7838	Intermediate Similarity	NPD3300	Phase 2
0.7823	Intermediate Similarity	NPD7003	Approved
0.7801	Intermediate Similarity	NPD3764	Approved
0.7793	Intermediate Similarity	NPD2935	Discontinued
0.7724	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD2799	Discontinued
0.7722	Intermediate Similarity	NPD6959	Discontinued
0.7619	Intermediate Similarity	NPD2344	Approved
0.7616	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2342	Discontinued
0.7594	Intermediate Similarity	NPD5951	Approved
0.7586	Intermediate Similarity	NPD1607	Approved
0.7584	Intermediate Similarity	NPD3750	Approved
0.7574	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD7819	Suspended
0.7518	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD2798	Approved
0.7515	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1510	Phase 2
0.7468	Intermediate Similarity	NPD7768	Phase 2
0.7464	Intermediate Similarity	NPD3023	Approved
0.7464	Intermediate Similarity	NPD3026	Approved
0.7448	Intermediate Similarity	NPD1240	Approved
0.7445	Intermediate Similarity	NPD1651	Approved
0.7445	Intermediate Similarity	NPD3024	Approved
0.7445	Intermediate Similarity	NPD3025	Approved
0.7444	Intermediate Similarity	NPD7635	Approved
0.7431	Intermediate Similarity	NPD2313	Discontinued
0.7421	Intermediate Similarity	NPD3749	Approved
0.7419	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD2309	Approved
0.7405	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2534	Approved
0.7386	Intermediate Similarity	NPD2533	Approved
0.7386	Intermediate Similarity	NPD2532	Approved
0.7376	Intermediate Similarity	NPD1283	Approved
0.7372	Intermediate Similarity	NPD4380	Phase 2
0.7351	Intermediate Similarity	NPD8166	Discontinued
0.7342	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7411	Suspended
0.7308	Intermediate Similarity	NPD7458	Discontinued
0.7294	Intermediate Similarity	NPD8150	Discontinued
0.7256	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3748	Approved
0.7234	Intermediate Similarity	NPD4878	Approved
0.7229	Intermediate Similarity	NPD5844	Phase 1
0.7225	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1549	Phase 2
0.7219	Intermediate Similarity	NPD8313	Approved
0.7219	Intermediate Similarity	NPD8312	Approved
0.7163	Intermediate Similarity	NPD1281	Approved
0.7152	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD9266	Approved
0.7143	Intermediate Similarity	NPD6663	Approved
0.7143	Intermediate Similarity	NPD74	Approved
0.7143	Intermediate Similarity	NPD2286	Discontinued
0.7143	Intermediate Similarity	NPD4626	Approved
0.7133	Intermediate Similarity	NPD1876	Approved
0.7125	Intermediate Similarity	NPD2801	Approved
0.7123	Intermediate Similarity	NPD7008	Discontinued
0.7115	Intermediate Similarity	NPD6273	Approved
0.7113	Intermediate Similarity	NPD3972	Approved
0.7103	Intermediate Similarity	NPD5736	Approved
0.7101	Intermediate Similarity	NPD6559	Discontinued
0.7101	Intermediate Similarity	NPD9493	Approved
0.7099	Intermediate Similarity	NPD7075	Discontinued
0.7097	Intermediate Similarity	NPD1511	Approved
0.709	Intermediate Similarity	NPD4750	Phase 3
0.7086	Intermediate Similarity	NPD2796	Approved
0.7081	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD9264	Approved
0.7068	Intermediate Similarity	NPD9267	Approved
0.7068	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD9263	Approved
0.7066	Intermediate Similarity	NPD7177	Discontinued
0.7063	Intermediate Similarity	NPD1934	Approved
0.7059	Intermediate Similarity	NPD2800	Approved
0.7054	Intermediate Similarity	NPD3020	Approved
0.7045	Intermediate Similarity	NPD6535	Approved
0.7045	Intermediate Similarity	NPD6534	Approved
0.7037	Intermediate Similarity	NPD3882	Suspended
0.7024	Intermediate Similarity	NPD6020	Phase 2
0.7019	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4628	Phase 3
0.7013	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5494	Approved
0.7007	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4625	Phase 3
0.7006	Intermediate Similarity	NPD1512	Approved
0.7	Intermediate Similarity	NPD5027	Approved
0.7	Intermediate Similarity	NPD3091	Approved
0.7	Intermediate Similarity	NPD5029	Approved
0.7	Intermediate Similarity	NPD5031	Approved
0.698	Remote Similarity	NPD2979	Phase 3
0.6974	Remote Similarity	NPD1551	Phase 2
0.6966	Remote Similarity	NPD1203	Approved
0.6963	Remote Similarity	NPD3022	Approved
0.6963	Remote Similarity	NPD3021	Approved
0.6953	Remote Similarity	NPD844	Approved
0.6953	Remote Similarity	NPD2859	Approved
0.6953	Remote Similarity	NPD2860	Approved
0.6947	Remote Similarity	NPD1932	Approved
0.6946	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6166	Phase 2
0.6944	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6782	Approved
0.6944	Remote Similarity	NPD6778	Approved
0.6944	Remote Similarity	NPD6777	Approved
0.6944	Remote Similarity	NPD6780	Approved
0.6944	Remote Similarity	NPD6776	Approved
0.6944	Remote Similarity	NPD6779	Approved
0.6944	Remote Similarity	NPD6781	Approved
0.6937	Remote Similarity	NPD6599	Discontinued
0.6928	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7699	Phase 2
0.6927	Remote Similarity	NPD7700	Phase 2
0.6923	Remote Similarity	NPD3092	Approved
0.6923	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4308	Phase 3
0.6903	Remote Similarity	NPD3400	Discontinued
0.6901	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4059	Approved
0.6899	Remote Similarity	NPD288	Approved
0.6894	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1930	Approved
0.6894	Remote Similarity	NPD1929	Approved
0.6893	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6212	Phase 3
0.6893	Remote Similarity	NPD6213	Phase 3
0.689	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6651	Approved
0.6884	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD9545	Approved
0.6875	Remote Similarity	NPD2934	Approved
0.6875	Remote Similarity	NPD2933	Approved
0.6871	Remote Similarity	NPD2296	Approved
0.6863	Remote Similarity	NPD6099	Approved
0.6863	Remote Similarity	NPD6100	Approved
0.686	Remote Similarity	NPD4955	Approved
0.686	Remote Similarity	NPD5034	Approved
0.686	Remote Similarity	NPD5028	Approved
0.686	Remote Similarity	NPD36	Approved
0.686	Remote Similarity	NPD5026	Approved
0.686	Remote Similarity	NPD4954	Approved
0.6853	Remote Similarity	NPD4879	Approved
0.6852	Remote Similarity	NPD6801	Discontinued
0.6849	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD3094	Phase 2
0.6846	Remote Similarity	NPD411	Approved
0.6835	Remote Similarity	NPD9281	Approved
0.6835	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD497	Approved
0.6831	Remote Similarity	NPD4093	Discontinued
0.6831	Remote Similarity	NPD7698	Approved
0.6831	Remote Similarity	NPD7696	Phase 3
0.6831	Remote Similarity	NPD7435	Discontinued
0.6831	Remote Similarity	NPD5691	Approved
0.6831	Remote Similarity	NPD7697	Approved
0.6829	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5711	Approved
0.6826	Remote Similarity	NPD5710	Approved
0.681	Remote Similarity	NPD1465	Phase 2
0.6809	Remote Similarity	NPD7610	Discontinued
0.6805	Remote Similarity	NPD5033	Approved
0.6802	Remote Similarity	NPD5030	Phase 2
0.68	Remote Similarity	NPD5037	Approved
0.68	Remote Similarity	NPD5038	Approved
0.6793	Remote Similarity	NPD7870	Phase 2
0.6793	Remote Similarity	NPD8320	Phase 1
0.6793	Remote Similarity	NPD8319	Approved
0.6793	Remote Similarity	NPD7871	Phase 2
0.6783	Remote Similarity	NPD3095	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