NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.06
Volume:	256.396
LogP:	3.793
LogD:	2.304
LogS:	-3.758
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.354
Synthetic Accessibility Score:	2.475
Fsp3:	0.0
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:	-5.09
MDCK Permeability:	7.628893399669323e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.956
20% Bioavailability (F20%):	0.879
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	97.7530288696289%
Volume Distribution (VD):	0.41
Pgp-substrate:	3.5276412963867188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.101
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.44
CYP2C9-substrate:	0.531
CYP2D6-inhibitor:	0.63
CYP2D6-substrate:	0.21
CYP3A4-inhibitor:	0.135
CYP3A4-substrate:	0.061

ADMET: Excretion

Clearance (CL):	3.473
Half-life (T1/2):	0.657

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.017
Drug-inuced Liver Injury (DILI):	0.805
AMES Toxicity:	0.632
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.556
Skin Sensitization:	0.943
Carcinogencity:	0.863
Eye Corrosion:	0.006
Eye Irritation:	0.945
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC31799

Natural Product ID:	NPC31799
*Common Name:**	Digiferruginol
IUPAC Name:	1-hydroxy-2-(hydroxymethyl)anthracene-9,10-dione
Synonyms:	Digiferruginol
Standard InCHIKey:	JCZCSQSSSAHDCB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O4/c16-7-8-5-6-11-12(13(8)17)15(19)10-4-2-1-3-9(10)14(11)18/h1-6,16-17H,7H2
SMILES:	c1ccc2c(c1)C(=O)c1ccc(CO)c(c1C2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495276
PubChem CID:	32209
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754604]
NPO25089	Cinchona calisaya	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11992775]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18078747]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	Roots	Simao city, Yunnan Province, China	2007-MAY	PMID[19374435]
NPO30900	Morinda parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7097296]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882438]
NPO30377	Cinchona ledgeriana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3942	Geranium pratense	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5095	Digitalis ferruginea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15699	Damnacanthus indicus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3011	Rubia wallichiana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30972	Morinda officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30900	Morinda parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23213	Bistorta officinalis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11242	Gynochthodes parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15699	Damnacanthus indicus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5095	Digitalis ferruginea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3942	Geranium pratense	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3011	Rubia wallichiana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13324	Euphorbia ingens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16138	Cinchona sp.	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25089	Cinchona calisaya	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30900	Morinda parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30972	Morinda officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15699	Damnacanthus indicus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3942	Geranium pratense	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30377	Cinchona ledgeriana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23213	Bistorta officinalis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3942	Geranium pratense	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13446	Stachys recta	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2868	Perna viridis	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11734	Chara corallina	Species	Characeae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3011	Rubia wallichiana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO861	Siphonaria funiculata	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15917	Monilinia fructigena	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5095	Digitalis ferruginea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15699	Damnacanthus indicus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26859	Solanum curtipes	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25089	Cinchona calisaya	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11242	Gynochthodes parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13324	Euphorbia ingens	Species	Euphorbiaceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.09	ug ml-1	PMID[499299]

☑ 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 NPC31799 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	366
0.1-0.2	1630
0.2-0.3	3655
0.3-0.4	10127
0.4-0.5	9272
0.5-0.6	5733
0.6-0.7	7986
0.7-0.8	3471
0.8-0.85	319
0.85-0.9	118
0.9-0.95	16
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.968	High Similarity	NPC199253
0.968	High Similarity	NPC136588
0.9528	High Similarity	NPC70622
0.9453	High Similarity	NPC52407
0.9449	High Similarity	NPC93015
0.9355	High Similarity	NPC142956
0.9274	High Similarity	NPC375356
0.9213	High Similarity	NPC282923
0.9194	High Similarity	NPC300274
0.9173	High Similarity	NPC190457
0.9127	High Similarity	NPC103540
0.9062	High Similarity	NPC48248
0.9055	High Similarity	NPC96915
0.9037	High Similarity	NPC305845
0.9037	High Similarity	NPC204045
0.9023	High Similarity	NPC53414
0.9023	High Similarity	NPC53206
0.9008	High Similarity	NPC225051
0.9	High Similarity	NPC205992
0.8992	High Similarity	NPC146647
0.8992	High Similarity	NPC34414
0.8992	High Similarity	NPC99731
0.8971	High Similarity	NPC73061
0.8971	High Similarity	NPC135524
0.8955	High Similarity	NPC4214
0.8947	High Similarity	NPC254847
0.8939	High Similarity	NPC288089
0.8939	High Similarity	NPC44437
0.8923	High Similarity	NPC55949
0.8906	High Similarity	NPC160499
0.8898	High Similarity	NPC152525
0.8898	High Similarity	NPC236189
0.8898	High Similarity	NPC68756
0.8898	High Similarity	NPC173978
0.8889	High Similarity	NPC242994
0.8889	High Similarity	NPC138099
0.8889	High Similarity	NPC307174
0.8881	High Similarity	NPC471905
0.8872	High Similarity	NPC258502
0.8872	High Similarity	NPC80035
0.8864	High Similarity	NPC115458
0.8864	High Similarity	NPC314048
0.8849	High Similarity	NPC314437
0.8849	High Similarity	NPC300540
0.8841	High Similarity	NPC471906
0.8841	High Similarity	NPC21599
0.8841	High Similarity	NPC244691
0.8841	High Similarity	NPC193703
0.8824	High Similarity	NPC169452
0.8824	High Similarity	NPC183345
0.8824	High Similarity	NPC181560
0.8806	High Similarity	NPC155211
0.8806	High Similarity	NPC315275
0.8797	High Similarity	NPC50924
0.8788	High Similarity	NPC58685
0.8779	High Similarity	NPC31539
0.8777	High Similarity	NPC478019
0.8768	High Similarity	NPC66593
0.876	High Similarity	NPC3224
0.875	High Similarity	NPC26924
0.875	High Similarity	NPC143438
0.875	High Similarity	NPC234890
0.875	High Similarity	NPC74507
0.8741	High Similarity	NPC305060
0.874	High Similarity	NPC91478
0.8731	High Similarity	NPC283088
0.8731	High Similarity	NPC161632
0.8722	High Similarity	NPC294226
0.8722	High Similarity	NPC267205
0.8722	High Similarity	NPC53896
0.8712	High Similarity	NPC244699
0.8705	High Similarity	NPC79627
0.8705	High Similarity	NPC48762
0.8696	High Similarity	NPC193555
0.8696	High Similarity	NPC474961
0.8696	High Similarity	NPC257644
0.8686	High Similarity	NPC315578
0.8676	High Similarity	NPC61398
0.8676	High Similarity	NPC416
0.8676	High Similarity	NPC13715
0.8667	High Similarity	NPC272268
0.8667	High Similarity	NPC474813
0.8661	High Similarity	NPC120545
0.8651	High Similarity	NPC285829
0.8651	High Similarity	NPC216297
0.8651	High Similarity	NPC473662
0.8651	High Similarity	NPC7151
0.8651	High Similarity	NPC206778
0.8643	High Similarity	NPC34482
0.8636	High Similarity	NPC198305
0.8633	High Similarity	NPC471682
0.8623	High Similarity	NPC246638
0.8623	High Similarity	NPC290550
0.8615	High Similarity	NPC231774
0.8615	High Similarity	NPC472047
0.8613	High Similarity	NPC1268
0.8605	High Similarity	NPC310540
0.8603	High Similarity	NPC245923
0.8601	High Similarity	NPC290954
0.8601	High Similarity	NPC255641
0.8582	High Similarity	NPC470570
0.8582	High Similarity	NPC114183
0.8561	High Similarity	NPC469520
0.8561	High Similarity	NPC69755
0.8551	High Similarity	NPC96421
0.8551	High Similarity	NPC203063
0.854	High Similarity	NPC173980
0.8537	High Similarity	NPC196673
0.8529	High Similarity	NPC141934
0.8529	High Similarity	NPC191976
0.8519	High Similarity	NPC12070
0.8519	High Similarity	NPC166480
0.8519	High Similarity	NPC202225
0.8519	High Similarity	NPC282780
0.8519	High Similarity	NPC270899
0.8511	High Similarity	NPC471683
0.8507	High Similarity	NPC246693
0.8507	High Similarity	NPC110609
0.8507	High Similarity	NPC242358
0.8507	High Similarity	NPC309430
0.8492	Intermediate Similarity	NPC41567
0.8489	Intermediate Similarity	NPC106519
0.8489	Intermediate Similarity	NPC124365
0.8489	Intermediate Similarity	NPC187843
0.8489	Intermediate Similarity	NPC91019
0.8485	Intermediate Similarity	NPC237225
0.8485	Intermediate Similarity	NPC95537
0.848	Intermediate Similarity	NPC108288
0.8473	Intermediate Similarity	NPC306765
0.8472	Intermediate Similarity	NPC147735
0.8467	Intermediate Similarity	NPC62272
0.8456	Intermediate Similarity	NPC249272
0.8451	Intermediate Similarity	NPC143685
0.8451	Intermediate Similarity	NPC285122
0.8451	Intermediate Similarity	NPC147250
0.845	Intermediate Similarity	NPC283514
0.8444	Intermediate Similarity	NPC254603
0.844	Intermediate Similarity	NPC300684
0.844	Intermediate Similarity	NPC218866
0.844	Intermediate Similarity	NPC84568
0.844	Intermediate Similarity	NPC48130
0.8438	Intermediate Similarity	NPC472046
0.8433	Intermediate Similarity	NPC471851
0.8433	Intermediate Similarity	NPC17083
0.8433	Intermediate Similarity	NPC85342
0.8433	Intermediate Similarity	NPC72669
0.8433	Intermediate Similarity	NPC474517
0.8429	Intermediate Similarity	NPC85310
0.8429	Intermediate Similarity	NPC239136
0.8429	Intermediate Similarity	NPC19631
0.8429	Intermediate Similarity	NPC137649
0.8425	Intermediate Similarity	NPC218870
0.8425	Intermediate Similarity	NPC470408
0.8425	Intermediate Similarity	NPC474824
0.8425	Intermediate Similarity	NPC182921
0.8421	Intermediate Similarity	NPC57552
0.8421	Intermediate Similarity	NPC278928
0.8414	Intermediate Similarity	NPC470569
0.8414	Intermediate Similarity	NPC118427
0.84	Intermediate Similarity	NPC161304
0.8394	Intermediate Similarity	NPC193358
0.8392	Intermediate Similarity	NPC119767
0.8392	Intermediate Similarity	NPC126767
0.8392	Intermediate Similarity	NPC190648
0.8392	Intermediate Similarity	NPC312929
0.8392	Intermediate Similarity	NPC245584
0.8392	Intermediate Similarity	NPC289042
0.8392	Intermediate Similarity	NPC56433
0.8392	Intermediate Similarity	NPC118027
0.8382	Intermediate Similarity	NPC287604
0.8382	Intermediate Similarity	NPC161964
0.8382	Intermediate Similarity	NPC472262
0.838	Intermediate Similarity	NPC170055
0.8372	Intermediate Similarity	NPC198336
0.8369	Intermediate Similarity	NPC238629
0.8358	Intermediate Similarity	NPC27659
0.8358	Intermediate Similarity	NPC147757
0.8358	Intermediate Similarity	NPC475741
0.8356	Intermediate Similarity	NPC164912
0.8346	Intermediate Similarity	NPC767
0.8346	Intermediate Similarity	NPC234175
0.8346	Intermediate Similarity	NPC96024
0.8346	Intermediate Similarity	NPC247250
0.8345	Intermediate Similarity	NPC205766
0.8345	Intermediate Similarity	NPC470568
0.8333	Intermediate Similarity	NPC475957
0.8333	Intermediate Similarity	NPC227741
0.8333	Intermediate Similarity	NPC295202
0.8333	Intermediate Similarity	NPC51037
0.8333	Intermediate Similarity	NPC136342
0.8333	Intermediate Similarity	NPC8745
0.8333	Intermediate Similarity	NPC49647
0.8333	Intermediate Similarity	NPC147418
0.8333	Intermediate Similarity	NPC53001
0.8322	Intermediate Similarity	NPC136878
0.8311	Intermediate Similarity	NPC474861
0.831	Intermediate Similarity	NPC29932
0.831	Intermediate Similarity	NPC19896
0.8309	Intermediate Similarity	NPC171968
0.8309	Intermediate Similarity	NPC78307

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 NPC31799 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	949
0.2-0.3	1382
0.3-0.4	2737
0.4-0.5	2173
0.5-0.6	1099
0.6-0.7	371
0.7-0.8	79
0.8-0.85	2
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9127	High Similarity	NPD1470	Approved
0.8947	High Similarity	NPD1509	Clinical (unspecified phase)
0.881	High Similarity	NPD1201	Approved
0.848	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD5406	Approved
0.8467	Intermediate Similarity	NPD5404	Approved
0.8467	Intermediate Similarity	NPD5405	Approved
0.8467	Intermediate Similarity	NPD5408	Approved
0.8056	Intermediate Similarity	NPD7390	Discontinued
0.8014	Intermediate Similarity	NPD2346	Discontinued
0.7985	Intermediate Similarity	NPD1164	Approved
0.7971	Intermediate Similarity	NPD943	Approved
0.7905	Intermediate Similarity	NPD3226	Approved
0.7877	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1510	Phase 2
0.7692	Intermediate Similarity	NPD2935	Discontinued
0.7667	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2342	Discontinued
0.7606	Intermediate Similarity	NPD1607	Approved
0.758	Intermediate Similarity	NPD6232	Discontinued
0.7571	Intermediate Similarity	NPD2313	Discontinued
0.7559	Intermediate Similarity	NPD74	Approved
0.7559	Intermediate Similarity	NPD9266	Approved
0.7547	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD3300	Phase 2
0.75	Intermediate Similarity	NPD9493	Approved
0.75	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD5951	Approved
0.748	Intermediate Similarity	NPD9263	Approved
0.748	Intermediate Similarity	NPD9267	Approved
0.748	Intermediate Similarity	NPD9264	Approved
0.7468	Intermediate Similarity	NPD7819	Suspended
0.7466	Intermediate Similarity	NPD1549	Phase 2
0.7465	Intermediate Similarity	NPD1240	Approved
0.7407	Intermediate Similarity	NPD3019	Approved
0.7405	Intermediate Similarity	NPD6959	Discontinued
0.74	Intermediate Similarity	NPD2532	Approved
0.74	Intermediate Similarity	NPD2534	Approved
0.74	Intermediate Similarity	NPD2533	Approved
0.7397	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4380	Phase 2
0.7381	Intermediate Similarity	NPD1237	Approved
0.7338	Intermediate Similarity	NPD1203	Approved
0.7333	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1551	Phase 2
0.7324	Intermediate Similarity	NPD3764	Approved
0.7305	Intermediate Similarity	NPD8150	Discontinued
0.7299	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD2798	Approved
0.7285	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2344	Approved
0.7279	Intermediate Similarity	NPD2932	Approved
0.726	Intermediate Similarity	NPD2799	Discontinued
0.7248	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7003	Approved
0.7244	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD8312	Approved
0.7229	Intermediate Similarity	NPD8313	Approved
0.7218	Intermediate Similarity	NPD9281	Approved
0.7197	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7635	Approved
0.7193	Intermediate Similarity	NPD6213	Phase 3
0.7193	Intermediate Similarity	NPD6212	Phase 3
0.7193	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD9261	Approved
0.7162	Intermediate Similarity	NPD1471	Phase 3
0.7153	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6535	Approved
0.7151	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD1283	Approved
0.7133	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3750	Approved
0.7122	Intermediate Similarity	NPD4878	Approved
0.7115	Intermediate Similarity	NPD7411	Suspended
0.7107	Intermediate Similarity	NPD3749	Approved
0.7105	Intermediate Similarity	NPD1511	Approved
0.7097	Intermediate Similarity	NPD7458	Discontinued
0.7086	Intermediate Similarity	NPD2309	Approved
0.7083	Intermediate Similarity	NPD411	Approved
0.708	Intermediate Similarity	NPD1651	Approved
0.707	Intermediate Similarity	NPD1934	Approved
0.7067	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7768	Phase 2
0.7034	Intermediate Similarity	NPD520	Approved
0.703	Intermediate Similarity	NPD5844	Phase 1
0.7029	Intermediate Similarity	NPD7700	Phase 2
0.7029	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7699	Phase 2
0.7027	Intermediate Similarity	NPD4308	Phase 3
0.7014	Intermediate Similarity	NPD7008	Discontinued
0.7013	Intermediate Similarity	NPD1512	Approved
0.7	Intermediate Similarity	NPD9717	Approved
0.7	Intermediate Similarity	NPD7075	Discontinued
0.698	Remote Similarity	NPD2796	Approved
0.6978	Remote Similarity	NPD3026	Approved
0.6978	Remote Similarity	NPD3023	Approved
0.6957	Remote Similarity	NPD3025	Approved
0.6957	Remote Similarity	NPD3024	Approved
0.6953	Remote Similarity	NPD1932	Approved
0.6951	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6782	Approved
0.6949	Remote Similarity	NPD6778	Approved
0.6949	Remote Similarity	NPD6780	Approved
0.6949	Remote Similarity	NPD6776	Approved
0.6949	Remote Similarity	NPD6777	Approved
0.6949	Remote Similarity	NPD6779	Approved
0.6949	Remote Similarity	NPD6781	Approved
0.6948	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6832	Phase 2
0.6939	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD447	Suspended
0.6937	Remote Similarity	NPD3882	Suspended
0.6929	Remote Similarity	NPD1281	Approved
0.6919	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2801	Approved
0.6918	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6663	Approved
0.6908	Remote Similarity	NPD8166	Discontinued
0.6905	Remote Similarity	NPD6559	Discontinued
0.6905	Remote Similarity	NPD288	Approved
0.6903	Remote Similarity	NPD6273	Approved
0.6901	Remote Similarity	NPD1876	Approved
0.6899	Remote Similarity	NPD1930	Approved
0.6899	Remote Similarity	NPD1929	Approved
0.6899	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3091	Approved
0.6879	Remote Similarity	NPD3972	Approved
0.6875	Remote Similarity	NPD5736	Approved
0.6875	Remote Similarity	NPD5402	Approved
0.6875	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3818	Discontinued
0.6866	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5026	Approved
0.6864	Remote Similarity	NPD4955	Approved
0.6864	Remote Similarity	NPD5028	Approved
0.6864	Remote Similarity	NPD5034	Approved
0.6864	Remote Similarity	NPD4954	Approved
0.6864	Remote Similarity	NPD36	Approved
0.6855	Remote Similarity	NPD6801	Discontinued
0.6849	Remote Similarity	NPD3268	Approved
0.6848	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6166	Phase 2
0.6842	Remote Similarity	NPD2800	Approved
0.6835	Remote Similarity	NPD6599	Discontinued
0.6833	Remote Similarity	NPD7696	Phase 3
0.6833	Remote Similarity	NPD7435	Discontinued
0.6833	Remote Similarity	NPD7697	Approved
0.6833	Remote Similarity	NPD7698	Approved
0.6829	Remote Similarity	NPD5711	Approved
0.6829	Remote Similarity	NPD5710	Approved
0.6825	Remote Similarity	NPD844	Approved
0.6818	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5494	Approved
0.6805	Remote Similarity	NPD5030	Phase 2
0.68	Remote Similarity	NPD3748	Approved
0.6797	Remote Similarity	NPD4628	Phase 3
0.6796	Remote Similarity	NPD7870	Phase 2
0.6796	Remote Similarity	NPD7871	Phase 2
0.6796	Remote Similarity	NPD8320	Phase 1
0.6796	Remote Similarity	NPD8319	Approved
0.6786	Remote Similarity	NPD2286	Discontinued
0.6786	Remote Similarity	NPD4626	Approved
0.6767	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD3751	Discontinued
0.6766	Remote Similarity	NPD7177	Discontinued
0.6765	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD9545	Approved
0.6761	Remote Similarity	NPD9269	Phase 2
0.6757	Remote Similarity	NPD4307	Phase 2
0.6755	Remote Similarity	NPD6099	Approved
0.6755	Remote Similarity	NPD6100	Approved
0.6752	Remote Similarity	NPD5403	Approved
0.675	Remote Similarity	NPD6844	Discontinued
0.6738	Remote Similarity	NPD4879	Approved
0.6736	Remote Similarity	NPD3094	Phase 2
0.6736	Remote Similarity	NPD2797	Approved
0.6731	Remote Similarity	NPD5401	Approved
0.6728	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6020	Phase 2
0.6716	Remote Similarity	NPD4750	Phase 3
0.6715	Remote Similarity	NPD497	Approved
0.6714	Remote Similarity	NPD9268	Approved
0.6711	Remote Similarity	NPD230	Phase 1
0.6705	Remote Similarity	NPD5037	Approved
0.6705	Remote Similarity	NPD5038	Approved
0.669	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3092	Approved
0.6688	Remote Similarity	NPD3400	Discontinued
0.6688	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6823	Phase 2
0.6685	Remote Similarity	NPD7701	Phase 2

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