NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	204.04
Volume:	201.042
LogP:	1.82
LogD:	1.589
LogS:	-2.445
# Rotatable Bonds:	0
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.627
Synthetic Accessibility Score:	2.452
Fsp3:	0.091
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	3

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.737
MDCK Permeability:	1.5776249711052515e-05
Pgp-inhibitor:	0.069
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.689

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	96.37571716308594%
Volume Distribution (VD):	0.415
Pgp-substrate:	3.268918514251709%

ADMET: Metabolism

CYP1A2-inhibitor:	0.925
CYP1A2-substrate:	0.269
CYP2C19-inhibitor:	0.253
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.601
CYP2C9-substrate:	0.451
CYP2D6-inhibitor:	0.683
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.631
CYP3A4-substrate:	0.156

ADMET: Excretion

Clearance (CL):	8.771
Half-life (T1/2):	0.822

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.202
Drug-inuced Liver Injury (DILI):	0.483
AMES Toxicity:	0.896
Rat Oral Acute Toxicity:	0.881
Maximum Recommended Daily Dose:	0.893
Skin Sensitization:	0.914
Carcinogencity:	0.772
Eye Corrosion:	0.102
Eye Irritation:	0.972
Respiratory Toxicity:	0.376

Download Data

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

Natural Product: NPC117609

Natural Product ID:	NPC117609
*Common Name:**	6-Hydroxy Plumbagin
IUPAC Name:	5,6-dihydroxy-2-methylnaphthalene-1,4-dione
Synonyms:	6-Hydroxy Plumbagin
Standard InCHIKey:	HWWWTOHAFWXPCB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H8O4/c1-5-4-8(13)9-6(10(5)14)2-3-7(12)11(9)15/h2-4,12,15H,1H3
SMILES:	CC1=CC(=O)c2c(C1=O)ccc(c2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094243
PubChem CID:	13468231
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
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1007/s004360050318]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1007/s004360050318]
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]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22019229]
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]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[9371362]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[9371362]
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]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13113	Ardisia kivuensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22192	Cribraria cancellata	Species	Cribrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22999	Cussonia spicata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18921	Athrixia phylicoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22069	Persea major	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23045	Lotus helleri	Species	Fabaceae	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]
NPO19736	Haplopappus glutinosus	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]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23432	Viguiera oaxacana	Species	Asteraceae	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]
NPO23865	Scorzonera veratrifolia	Species	Asteraceae	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]
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]
NPO20721	Halichondria panicea	Species	Halichondriidae	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
Others	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	EC50	=	100000.0	nM	PMID[468495]
NPT1381	Organism	Aedes aegypti	Aedes aegypti	LC50	=	13.64	ug.mL-1	PMID[468494]
NPT1381	Organism	Aedes aegypti	Aedes aegypti	LC90	=	19.28	ug ml-1	PMID[468494]
NPT1381	Organism	Aedes aegypti	Aedes aegypti	Activity	=	100.0	%	PMID[468494]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	75000.0	nM	PMID[468495]

☑ 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 NPC117609 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	345
0.1-0.2	1692
0.2-0.3	4385
0.3-0.4	11678
0.4-0.5	6777
0.5-0.6	5574
0.6-0.7	7950
0.7-0.8	3871
0.8-0.85	357
0.85-0.9	54
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9453	High Similarity	NPC294226
0.9308	High Similarity	NPC258502
0.9242	High Similarity	NPC61398
0.9242	High Similarity	NPC416
0.9179	High Similarity	NPC84273
0.9134	High Similarity	NPC324209
0.9134	High Similarity	NPC473787
0.9106	High Similarity	NPC285829
0.9106	High Similarity	NPC206778
0.9062	High Similarity	NPC234175
0.9048	High Similarity	NPC310540
0.9023	High Similarity	NPC147418
0.8963	High Similarity	NPC203063
0.8906	High Similarity	NPC231774
0.8889	High Similarity	NPC307174
0.8872	High Similarity	NPC72918
0.8862	High Similarity	NPC150919
0.8832	High Similarity	NPC291078
0.8806	High Similarity	NPC7464
0.8797	High Similarity	NPC50924
0.878	High Similarity	NPC108288
0.8777	High Similarity	NPC160777
0.8777	High Similarity	NPC73416
0.8769	High Similarity	NPC237225
0.8768	High Similarity	NPC238629
0.876	High Similarity	NPC306765
0.876	High Similarity	NPC3224
0.8741	High Similarity	NPC290030
0.8722	High Similarity	NPC138472
0.8712	High Similarity	NPC469526
0.8712	High Similarity	NPC34070
0.8712	High Similarity	NPC244699
0.8702	High Similarity	NPC99731
0.8676	High Similarity	NPC297797
0.8676	High Similarity	NPC5014
0.8676	High Similarity	NPC46242
0.8676	High Similarity	NPC165191
0.8676	High Similarity	NPC477849
0.8676	High Similarity	NPC157284
0.8676	High Similarity	NPC473779
0.8676	High Similarity	NPC42384
0.8676	High Similarity	NPC114333
0.8676	High Similarity	NPC91887
0.8676	High Similarity	NPC50615
0.8676	High Similarity	NPC149773
0.8676	High Similarity	NPC28592
0.8676	High Similarity	NPC289358
0.8676	High Similarity	NPC469857
0.8676	High Similarity	NPC51531
0.8676	High Similarity	NPC23667
0.8676	High Similarity	NPC245760
0.8676	High Similarity	NPC473479
0.8672	High Similarity	NPC375356
0.8667	High Similarity	NPC315275
0.8652	High Similarity	NPC476821
0.8647	High Similarity	NPC135801
0.8636	High Similarity	NPC26697
0.8626	High Similarity	NPC767
0.8626	High Similarity	NPC247250
0.8615	High Similarity	NPC51037
0.8615	High Similarity	NPC1991
0.8613	High Similarity	NPC472903
0.8613	High Similarity	NPC294330
0.8603	High Similarity	NPC264022
0.8594	High Similarity	NPC91478
0.8594	High Similarity	NPC282577
0.8594	High Similarity	NPC300274
0.8593	High Similarity	NPC129752
0.8582	High Similarity	NPC52407
0.8582	High Similarity	NPC53896
0.8582	High Similarity	NPC111845
0.8582	High Similarity	NPC4170
0.8582	High Similarity	NPC171968
0.8571	High Similarity	NPC232178
0.8561	High Similarity	NPC11314
0.8561	High Similarity	NPC146647
0.8561	High Similarity	NPC34414
0.8551	High Similarity	NPC473527
0.8542	High Similarity	NPC144283
0.854	High Similarity	NPC230811
0.854	High Similarity	NPC206207
0.854	High Similarity	NPC123714
0.8538	High Similarity	NPC103540
0.8529	High Similarity	NPC194764
0.8529	High Similarity	NPC65005
0.8529	High Similarity	NPC264112
0.8519	High Similarity	NPC44437
0.8516	High Similarity	NPC120545
0.8496	Intermediate Similarity	NPC233056
0.8496	Intermediate Similarity	NPC198305
0.8489	Intermediate Similarity	NPC472904
0.8485	Intermediate Similarity	NPC282923
0.8485	Intermediate Similarity	NPC165257
0.8485	Intermediate Similarity	NPC179898
0.8473	Intermediate Similarity	NPC15837
0.8473	Intermediate Similarity	NPC96915
0.8467	Intermediate Similarity	NPC53206
0.8467	Intermediate Similarity	NPC277559
0.8467	Intermediate Similarity	NPC53414
0.8462	Intermediate Similarity	NPC142956
0.8456	Intermediate Similarity	NPC283088
0.8456	Intermediate Similarity	NPC80035
0.8456	Intermediate Similarity	NPC153088
0.8456	Intermediate Similarity	NPC14377
0.8455	Intermediate Similarity	NPC231717
0.8444	Intermediate Similarity	NPC225051
0.8444	Intermediate Similarity	NPC474715
0.8438	Intermediate Similarity	NPC190971
0.8429	Intermediate Similarity	NPC469855
0.8429	Intermediate Similarity	NPC471971
0.8429	Intermediate Similarity	NPC30846
0.8429	Intermediate Similarity	NPC471972
0.8421	Intermediate Similarity	NPC278928
0.8414	Intermediate Similarity	NPC473201
0.8414	Intermediate Similarity	NPC302783
0.8414	Intermediate Similarity	NPC118427
0.8406	Intermediate Similarity	NPC13715
0.8406	Intermediate Similarity	NPC141368
0.8406	Intermediate Similarity	NPC4214
0.8403	Intermediate Similarity	NPC134293
0.84	Intermediate Similarity	NPC161304
0.8397	Intermediate Similarity	NPC123506
0.8394	Intermediate Similarity	NPC254847
0.8394	Intermediate Similarity	NPC86524
0.8394	Intermediate Similarity	NPC223836
0.8392	Intermediate Similarity	NPC10842
0.8382	Intermediate Similarity	NPC282780
0.8382	Intermediate Similarity	NPC166480
0.837	Intermediate Similarity	NPC246693
0.837	Intermediate Similarity	NPC110609
0.837	Intermediate Similarity	NPC17843
0.837	Intermediate Similarity	NPC309430
0.837	Intermediate Similarity	NPC242358
0.8369	Intermediate Similarity	NPC199936
0.8358	Intermediate Similarity	NPC136588
0.8358	Intermediate Similarity	NPC55949
0.8358	Intermediate Similarity	NPC199253
0.8356	Intermediate Similarity	NPC312338
0.8356	Intermediate Similarity	NPC149889
0.8356	Intermediate Similarity	NPC164912
0.8346	Intermediate Similarity	NPC96024
0.8346	Intermediate Similarity	NPC48248
0.8346	Intermediate Similarity	NPC95537
0.8345	Intermediate Similarity	NPC242994
0.8345	Intermediate Similarity	NPC138099
0.8333	Intermediate Similarity	NPC471905
0.8333	Intermediate Similarity	NPC49911
0.8333	Intermediate Similarity	NPC471452
0.8333	Intermediate Similarity	NPC160499
0.8333	Intermediate Similarity	NPC254492
0.8333	Intermediate Similarity	NPC477453
0.8333	Intermediate Similarity	NPC471907
0.8321	Intermediate Similarity	NPC74507
0.8321	Intermediate Similarity	NPC234890
0.8321	Intermediate Similarity	NPC199273
0.831	Intermediate Similarity	NPC79627
0.831	Intermediate Similarity	NPC145301
0.831	Intermediate Similarity	NPC469854
0.831	Intermediate Similarity	NPC469375
0.831	Intermediate Similarity	NPC144247
0.831	Intermediate Similarity	NPC469856
0.831	Intermediate Similarity	NPC294679
0.831	Intermediate Similarity	NPC8493
0.8298	Intermediate Similarity	NPC314271
0.8296	Intermediate Similarity	NPC205992
0.8296	Intermediate Similarity	NPC93015
0.8296	Intermediate Similarity	NPC205360
0.8295	Intermediate Similarity	NPC236520
0.8295	Intermediate Similarity	NPC294361
0.8286	Intermediate Similarity	NPC471853
0.8286	Intermediate Similarity	NPC156872
0.8286	Intermediate Similarity	NPC169452
0.8286	Intermediate Similarity	NPC181560
0.8273	Intermediate Similarity	NPC469681
0.8273	Intermediate Similarity	NPC173980
0.8273	Intermediate Similarity	NPC469680
0.8273	Intermediate Similarity	NPC112135
0.8273	Intermediate Similarity	NPC471974
0.8271	Intermediate Similarity	NPC72667
0.8271	Intermediate Similarity	NPC107672
0.8271	Intermediate Similarity	NPC471530
0.8268	Intermediate Similarity	NPC28169
0.8261	Intermediate Similarity	NPC155211
0.8261	Intermediate Similarity	NPC324929
0.8254	Intermediate Similarity	NPC240163
0.8235	Intermediate Similarity	NPC70622
0.8235	Intermediate Similarity	NPC50763
0.8235	Intermediate Similarity	NPC477406
0.8235	Intermediate Similarity	NPC58685
0.8231	Intermediate Similarity	NPC198336
0.8222	Intermediate Similarity	NPC31799
0.8222	Intermediate Similarity	NPC475741
0.8222	Intermediate Similarity	NPC244441
0.8219	Intermediate Similarity	NPC48949
0.8219	Intermediate Similarity	NPC280295
0.8217	Intermediate Similarity	NPC260837
0.8217	Intermediate Similarity	NPC473662
0.8217	Intermediate Similarity	NPC216297
0.8217	Intermediate Similarity	NPC7151
0.8214	Intermediate Similarity	NPC114620

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 NPC117609 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	994
0.2-0.3	1522
0.3-0.4	2952
0.4-0.5	1866
0.5-0.6	1030
0.6-0.7	391
0.7-0.8	62
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.878	High Similarity	NPD405	Clinical (unspecified phase)
0.8667	High Similarity	NPD651	Clinical (unspecified phase)
0.8647	High Similarity	NPD943	Approved
0.8538	High Similarity	NPD1470	Approved
0.8394	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD1201	Approved
0.7877	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD9269	Phase 2
0.774	Intermediate Similarity	NPD3300	Phase 2
0.7737	Intermediate Similarity	NPD9494	Approved
0.7687	Intermediate Similarity	NPD1511	Approved
0.7594	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD1164	Approved
0.7584	Intermediate Similarity	NPD1512	Approved
0.7569	Intermediate Similarity	NPD5404	Approved
0.7569	Intermediate Similarity	NPD5408	Approved
0.7569	Intermediate Similarity	NPD5406	Approved
0.7569	Intermediate Similarity	NPD5405	Approved
0.7568	Intermediate Similarity	NPD7390	Discontinued
0.7537	Intermediate Similarity	NPD2932	Approved
0.7535	Intermediate Similarity	NPD230	Phase 1
0.7517	Intermediate Similarity	NPD2344	Approved
0.7484	Intermediate Similarity	NPD3882	Suspended
0.7483	Intermediate Similarity	NPD8166	Discontinued
0.7468	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2801	Approved
0.7468	Intermediate Similarity	NPD6232	Discontinued
0.7466	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD9268	Approved
0.7438	Intermediate Similarity	NPD7473	Discontinued
0.7422	Intermediate Similarity	NPD9266	Approved
0.7422	Intermediate Similarity	NPD74	Approved
0.7413	Intermediate Similarity	NPD447	Suspended
0.7407	Intermediate Similarity	NPD3019	Approved
0.7403	Intermediate Similarity	NPD1934	Approved
0.7397	Intermediate Similarity	NPD2346	Discontinued
0.7368	Intermediate Similarity	NPD9493	Approved
0.7364	Intermediate Similarity	NPD3022	Approved
0.7364	Intermediate Similarity	NPD3021	Approved
0.7361	Intermediate Similarity	NPD1607	Approved
0.7344	Intermediate Similarity	NPD9267	Approved
0.7344	Intermediate Similarity	NPD9263	Approved
0.7344	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD9264	Approved
0.7343	Intermediate Similarity	NPD1240	Approved
0.7329	Intermediate Similarity	NPD2935	Discontinued
0.732	Intermediate Similarity	NPD3226	Approved
0.7315	Intermediate Similarity	NPD2309	Approved
0.7279	Intermediate Similarity	NPD1471	Phase 3
0.726	Intermediate Similarity	NPD1510	Phase 2
0.726	Intermediate Similarity	NPD2799	Discontinued
0.7194	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD9545	Approved
0.7118	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD9281	Approved
0.7083	Intermediate Similarity	NPD3764	Approved
0.7059	Intermediate Similarity	NPD2532	Approved
0.7059	Intermediate Similarity	NPD2534	Approved
0.7059	Intermediate Similarity	NPD2533	Approved
0.7042	Intermediate Similarity	NPD2798	Approved
0.7042	Intermediate Similarity	NPD258	Approved
0.7042	Intermediate Similarity	NPD257	Approved
0.7031	Intermediate Similarity	NPD9261	Approved
0.7025	Intermediate Similarity	NPD7819	Suspended
0.7025	Intermediate Similarity	NPD1465	Phase 2
0.7	Intermediate Similarity	NPD9717	Approved
0.7	Intermediate Similarity	NPD1549	Phase 2
0.6992	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3026	Approved
0.6978	Remote Similarity	NPD3023	Approved
0.6972	Remote Similarity	NPD1203	Approved
0.697	Remote Similarity	NPD3818	Discontinued
0.6966	Remote Similarity	NPD2313	Discontinued
0.6966	Remote Similarity	NPD411	Approved
0.6957	Remote Similarity	NPD3025	Approved
0.6957	Remote Similarity	NPD3024	Approved
0.6954	Remote Similarity	NPD2800	Approved
0.6951	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6166	Phase 2
0.6948	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4380	Phase 2
0.6933	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3750	Approved
0.6905	Remote Similarity	NPD288	Approved
0.6901	Remote Similarity	NPD1283	Approved
0.6901	Remote Similarity	NPD1876	Approved
0.6879	Remote Similarity	NPD3972	Approved
0.6875	Remote Similarity	NPD3817	Phase 2
0.6875	Remote Similarity	NPD9569	Approved
0.6866	Remote Similarity	NPD228	Approved
0.6863	Remote Similarity	NPD6190	Approved
0.6839	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1651	Approved
0.6832	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1755	Approved
0.6826	Remote Similarity	NPD7054	Approved
0.6825	Remote Similarity	NPD844	Approved
0.681	Remote Similarity	NPD5494	Approved
0.6805	Remote Similarity	NPD5031	Approved
0.6805	Remote Similarity	NPD5027	Approved
0.6805	Remote Similarity	NPD5029	Approved
0.6803	Remote Similarity	NPD259	Phase 1
0.6802	Remote Similarity	NPD8150	Discontinued
0.6797	Remote Similarity	NPD7003	Approved
0.6797	Remote Similarity	NPD4628	Phase 3
0.6791	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.679	Remote Similarity	NPD3749	Approved
0.679	Remote Similarity	NPD7075	Discontinued
0.6786	Remote Similarity	NPD4626	Approved
0.6786	Remote Similarity	NPD7472	Approved
0.6786	Remote Similarity	NPD7074	Phase 3
0.6774	Remote Similarity	NPD6799	Approved
0.6772	Remote Similarity	NPD7458	Discontinued
0.6772	Remote Similarity	NPD3455	Phase 2
0.677	Remote Similarity	NPD2296	Approved
0.6768	Remote Similarity	NPD6959	Discontinued
0.6767	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD36	Approved
0.6765	Remote Similarity	NPD4955	Approved
0.6765	Remote Similarity	NPD1241	Discontinued
0.6765	Remote Similarity	NPD5028	Approved
0.6765	Remote Similarity	NPD4954	Approved
0.6765	Remote Similarity	NPD5026	Approved
0.6765	Remote Similarity	NPD5034	Approved
0.6757	Remote Similarity	NPD825	Approved
0.6757	Remote Similarity	NPD826	Approved
0.6746	Remote Similarity	NPD6797	Phase 2
0.6744	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6599	Discontinued
0.6726	Remote Similarity	NPD5844	Phase 1
0.6725	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD5951	Approved
0.6711	Remote Similarity	NPD275	Approved
0.6711	Remote Similarity	NPD555	Phase 2
0.6711	Remote Similarity	NPD274	Approved
0.6708	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5030	Phase 2
0.6706	Remote Similarity	NPD7251	Discontinued
0.6692	Remote Similarity	NPD2342	Discontinued
0.6691	Remote Similarity	NPD9377	Approved
0.6691	Remote Similarity	NPD7635	Approved
0.6691	Remote Similarity	NPD9379	Approved
0.6691	Remote Similarity	NPD5536	Phase 2
0.669	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1281	Approved
0.6689	Remote Similarity	NPD520	Approved
0.6689	Remote Similarity	NPD6663	Approved
0.6687	Remote Similarity	NPD3926	Phase 2
0.6667	Remote Similarity	NPD824	Approved
0.6667	Remote Similarity	NPD1247	Approved
0.6667	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3020	Approved
0.6667	Remote Similarity	NPD6651	Approved
0.6667	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9536	Phase 1
0.6667	Remote Similarity	NPD9537	Phase 1
0.6648	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD919	Approved
0.6645	Remote Similarity	NPD2796	Approved
0.6645	Remote Similarity	NPD1551	Phase 2
0.6645	Remote Similarity	NPD9570	Approved
0.6644	Remote Similarity	NPD5736	Approved
0.6643	Remote Similarity	NPD4878	Approved
0.6627	Remote Similarity	NPD1221	Approved
0.6614	Remote Similarity	NPD2933	Approved
0.6614	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD2934	Approved
0.6609	Remote Similarity	NPD5038	Approved
0.6609	Remote Similarity	NPD5037	Approved
0.66	Remote Similarity	NPD1933	Approved
0.6593	Remote Similarity	NPD4750	Phase 3
0.6591	Remote Similarity	NPD164	Approved
0.6591	Remote Similarity	NPD1237	Approved
0.6585	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD650	Approved
0.6584	Remote Similarity	NPD7411	Suspended
0.6579	Remote Similarity	NPD3748	Approved
0.6573	Remote Similarity	NPD3092	Approved
0.657	Remote Similarity	NPD7808	Phase 3
0.6568	Remote Similarity	NPD3751	Discontinued
0.6562	Remote Similarity	NPD2859	Approved
0.6562	Remote Similarity	NPD2860	Approved
0.6562	Remote Similarity	NPD1809	Phase 2
0.6561	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD5968	Phase 3
0.6552	Remote Similarity	NPD5036	Approved
0.6552	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD1220	Phase 1
0.6544	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6801	Discontinued
0.6535	Remote Similarity	NPD845	Approved
0.6534	Remote Similarity	NPD6836	Approved
0.6533	Remote Similarity	NPD4060	Phase 1
0.6528	Remote Similarity	NPD1608	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