NPASS Compound

Structure

NPC474010 OpenBabel07101718232D 34 37 0 0 1 0 0 0 0 0999 V2000 -4.5069 2.6509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5069 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1108 1.7614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1108 -0.7877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4752 2.7527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4752 -1.7790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6832 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6832 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0475 1.9650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0475 -0.9913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6515 1.0755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6515 -0.1018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6865 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1848 2.0623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1848 -1.0886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -0.4868 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.6865 0.9737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8713 3.6422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8713 -2.6685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0159 2.0667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0159 -1.0931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 2.4342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7961 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2238 0.6859 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1848 3.0360 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1848 -2.0623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2588 1.7614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2588 -0.7877 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 6 1 0 0 0 0 2 5 2 0 0 0 0 2 7 1 0 0 0 0 3 21 1 0 0 0 0 4 9 1 0 0 0 0 4 18 1 0 0 0 0 5 10 1 0 0 0 0 5 19 1 0 0 0 0 6 11 2 0 0 0 0 6 22 1 0 0 0 0 7 12 2 0 0 0 0 7 23 1 0 0 0 0 8 3 1 1 0 0 0 8 13 1 0 0 0 0 8 32 1 0 0 0 0 9 10 1 0 0 0 0 9 14 2 0 0 0 0 10 15 2 0 0 0 0 11 14 1 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 12 25 1 0 0 0 0 13 16 1 0 0 0 0 13 26 1 6 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 33 1 1 0 0 0 17 20 1 0 0 0 0 17 34 1 6 0 0 0 18 29 2 0 0 0 0 18 33 1 0 0 0 0 19 30 2 0 0 0 0 19 34 1 0 0 0 0 20 31 1 0 0 0 0 20 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.07
Volume:	422.222
LogP:	-0.409
LogD:	-0.208
LogS:	-0.825
# Rotatable Bonds:	1
TPSA:	243.9
# H-Bond Aceptor:	14
# H-Bond Donor:	9
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.17
Synthetic Accessibility Score:	4.912
Fsp3:	0.3
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.705
MDCK Permeability:	9.0977264335379e-06
Pgp-inhibitor:	0.024
Pgp-substrate:	0.197
Human Intestinal Absorption (HIA):	0.977
20% Bioavailability (F20%):	0.893
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	91.42011260986328%
Volume Distribution (VD):	0.735
Pgp-substrate:	15.299521446228027%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.012
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	5.963
Half-life (T1/2):	0.948

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.148
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.278
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.863
Carcinogencity:	0.012
Eye Corrosion:	0.003
Eye Irritation:	0.275
Respiratory Toxicity:	0.018

Download Data

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

Natural Product: NPC474010

Natural Product ID:	NPC474010
*Common Name:**	GEAGRKQCZVLNAU-NNIZZFLASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GEAGRKQCZVLNAU-NNIZZFLASA-N
Standard InCHI:	InChI=1S/C20H18O14/c21-3-8-13(26)16-17(20(31)32-8)34-19(30)5-2-7(23)12(25)15(28)10(5)9-4(18(29)33-16)1-6(22)11(24)14(9)27/h1-2,8,13,16-17,20-28,31H,3H2/t8-,13-,16+,17-,20?/m1/s1
SMILES:	c1c2c(-c3c(cc(c(c3O)O)O)C(=O)O[C@@H]3[C@H]([C@@H]([C@@H](CO)OC3O)O)OC2=O)c(c(c1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458193
PubChem CID:	14035453
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1021/np50028a032]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[10993241]
NPO40375	Terminalia macroptera	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277742]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[8759159]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759159]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834152]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3129	Geum japonicum	Species	Rosaceae	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	5
IC50	3
Others	4

Activity Type	# Activity
Cell Line	5
Individual Protein	3
NON-MOLECULAR	1
Tissue	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2295	Cell Line	5637	Homo sapiens	LC50	=	84660.0	nM	PMID[463400]
NPT326	Individual Protein	Squalene monooxygenase	Rattus norvegicus	IC50	=	32000.0	nM	PMID[463401]
NPT672	Cell Line	TE-671	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[463402]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[463402]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[463402]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[463402]
NPT2534	Individual Protein	Thrombin	Bos taurus	IC50	>	200000.0	nM	PMID[463403]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	10.0	ug ml-1	PMID[463402]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	APTT	=	39.9	s	PMID[463403]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	TT	=	9.43	s	PMID[463403]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	PT	=	10.0	s	PMID[463403]

☑ 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 NPC474010 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	374
0.1-0.2	1560
0.2-0.3	3472
0.3-0.4	8017
0.4-0.5	10124
0.5-0.6	4790
0.6-0.7	6182
0.7-0.8	7095
0.8-0.85	882
0.85-0.9	165
0.9-0.95	34
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC135222
0.949	High Similarity	NPC31034
0.9484	High Similarity	NPC291957
0.9484	High Similarity	NPC14030
0.9423	High Similarity	NPC470898
0.9304	High Similarity	NPC175793
0.9267	High Similarity	NPC248257
0.9267	High Similarity	NPC120621
0.925	High Similarity	NPC47521
0.9245	High Similarity	NPC470271
0.9245	High Similarity	NPC311389
0.9211	High Similarity	NPC140151
0.9205	High Similarity	NPC92117
0.92	High Similarity	NPC268366
0.913	High Similarity	NPC470272
0.9125	High Similarity	NPC190204
0.9125	High Similarity	NPC43918
0.9125	High Similarity	NPC261411
0.9119	High Similarity	NPC162169
0.9119	High Similarity	NPC166851
0.9062	High Similarity	NPC142707
0.9062	High Similarity	NPC26536
0.9062	High Similarity	NPC317671
0.9062	High Similarity	NPC49983
0.9018	High Similarity	NPC263119
0.9018	High Similarity	NPC166674
0.9018	High Similarity	NPC46640
0.9018	High Similarity	NPC219600
0.9018	High Similarity	NPC34436
0.9012	High Similarity	NPC181778
0.9006	High Similarity	NPC217781
0.9	High Similarity	NPC226738
0.9	High Similarity	NPC190587
0.9	High Similarity	NPC229036
0.9	High Similarity	NPC22176
0.9	High Similarity	NPC121573
0.8987	High Similarity	NPC24627
0.8968	High Similarity	NPC3746
0.8968	High Similarity	NPC44260
0.8968	High Similarity	NPC205037
0.8968	High Similarity	NPC61152
0.8968	High Similarity	NPC16024
0.8954	High Similarity	NPC75945
0.894	High Similarity	NPC108455
0.891	High Similarity	NPC144801
0.891	High Similarity	NPC291510
0.891	High Similarity	NPC43872
0.891	High Similarity	NPC116850
0.891	High Similarity	NPC197188
0.891	High Similarity	NPC238672
0.8909	High Similarity	NPC472723
0.8909	High Similarity	NPC297574
0.8902	High Similarity	NPC473550
0.8889	High Similarity	NPC81835
0.8861	High Similarity	NPC472860
0.8854	High Similarity	NPC156624
0.8854	High Similarity	NPC172920
0.8848	High Similarity	NPC171706
0.8802	High Similarity	NPC80956
0.8797	High Similarity	NPC239019
0.8797	High Similarity	NPC247629
0.8795	High Similarity	NPC473713
0.879	High Similarity	NPC125487
0.879	High Similarity	NPC281703
0.8782	High Similarity	NPC228662
0.8766	High Similarity	NPC142528
0.8766	High Similarity	NPC476463
0.8765	High Similarity	NPC237202
0.8758	High Similarity	NPC474465
0.875	High Similarity	NPC239966
0.875	High Similarity	NPC203020
0.875	High Similarity	NPC53680
0.875	High Similarity	NPC208797
0.8742	High Similarity	NPC257309
0.8742	High Similarity	NPC4747
0.8742	High Similarity	NPC238419
0.8742	High Similarity	NPC104275
0.8742	High Similarity	NPC172419
0.8742	High Similarity	NPC1913
0.8734	High Similarity	NPC203757
0.8733	High Similarity	NPC12218
0.8733	High Similarity	NPC105525
0.8733	High Similarity	NPC75763
0.8733	High Similarity	NPC225036
0.8727	High Similarity	NPC38438
0.8713	High Similarity	NPC269046
0.8704	High Similarity	NPC469651
0.8698	High Similarity	NPC129533
0.8698	High Similarity	NPC123259
0.869	High Similarity	NPC198902
0.8688	High Similarity	NPC37502
0.8688	High Similarity	NPC267627
0.8688	High Similarity	NPC160780
0.8688	High Similarity	NPC40702
0.8688	High Similarity	NPC74319
0.8688	High Similarity	NPC287872
0.8688	High Similarity	NPC289811
0.8683	High Similarity	NPC79736
0.8683	High Similarity	NPC67629
0.8679	High Similarity	NPC104983
0.8679	High Similarity	NPC250436
0.8679	High Similarity	NPC291948
0.8679	High Similarity	NPC88803
0.8679	High Similarity	NPC300845
0.8662	High Similarity	NPC227485
0.8659	High Similarity	NPC116745
0.865	High Similarity	NPC165720
0.8647	High Similarity	NPC231254
0.8645	High Similarity	NPC43123
0.8639	High Similarity	NPC8940
0.8639	High Similarity	NPC170203
0.8634	High Similarity	NPC24164
0.8634	High Similarity	NPC289346
0.8634	High Similarity	NPC119125
0.8634	High Similarity	NPC166277
0.8634	High Similarity	NPC474770
0.8631	High Similarity	NPC267549
0.8625	High Similarity	NPC49173
0.8625	High Similarity	NPC114179
0.8625	High Similarity	NPC289322
0.8625	High Similarity	NPC160512
0.8625	High Similarity	NPC156818
0.8625	High Similarity	NPC68324
0.8625	High Similarity	NPC247713
0.8625	High Similarity	NPC38779
0.8616	High Similarity	NPC82592
0.8616	High Similarity	NPC16082
0.8596	High Similarity	NPC111490
0.8596	High Similarity	NPC469650
0.8596	High Similarity	NPC261623
0.859	High Similarity	NPC42464
0.8589	High Similarity	NPC121290
0.8589	High Similarity	NPC88043
0.858	High Similarity	NPC472859
0.858	High Similarity	NPC25389
0.858	High Similarity	NPC311803
0.8571	High Similarity	NPC141331
0.8571	High Similarity	NPC104222
0.8571	High Similarity	NPC318826
0.8571	High Similarity	NPC210501
0.8571	High Similarity	NPC114791
0.8571	High Similarity	NPC87317
0.8562	High Similarity	NPC318432
0.8562	High Similarity	NPC227062
0.8554	High Similarity	NPC149011
0.8554	High Similarity	NPC204937
0.8553	High Similarity	NPC178134
0.8553	High Similarity	NPC281477
0.8547	High Similarity	NPC65489
0.8545	High Similarity	NPC107009
0.8545	High Similarity	NPC45400
0.8545	High Similarity	NPC298847
0.8545	High Similarity	NPC311912
0.8543	High Similarity	NPC239943
0.8537	High Similarity	NPC7752
0.8537	High Similarity	NPC475738
0.8535	High Similarity	NPC306343
0.8529	High Similarity	NPC125352
0.8528	High Similarity	NPC41009
0.8528	High Similarity	NPC300537
0.8528	High Similarity	NPC90905
0.8528	High Similarity	NPC285108
0.8528	High Similarity	NPC33298
0.8528	High Similarity	NPC4013
0.8528	High Similarity	NPC22324
0.8528	High Similarity	NPC127782
0.8521	High Similarity	NPC260300
0.8521	High Similarity	NPC80360
0.8521	High Similarity	NPC469418
0.8519	High Similarity	NPC53889
0.8516	High Similarity	NPC473867
0.8512	High Similarity	NPC469354
0.8509	High Similarity	NPC84935
0.8509	High Similarity	NPC190020
0.8509	High Similarity	NPC77679
0.8506	High Similarity	NPC97924
0.8506	High Similarity	NPC114242
0.8506	High Similarity	NPC40078
0.8506	High Similarity	NPC50221
0.8506	High Similarity	NPC471091
0.8503	High Similarity	NPC67134
0.8503	High Similarity	NPC260263
0.8503	High Similarity	NPC471181
0.8503	High Similarity	NPC47140
0.85	High Similarity	NPC472835
0.8497	Intermediate Similarity	NPC173872
0.8497	Intermediate Similarity	NPC477081
0.8497	Intermediate Similarity	NPC477083
0.8497	Intermediate Similarity	NPC119094
0.8494	Intermediate Similarity	NPC88557
0.8494	Intermediate Similarity	NPC229687
0.8494	Intermediate Similarity	NPC183036
0.8494	Intermediate Similarity	NPC476017
0.8494	Intermediate Similarity	NPC138927
0.8491	Intermediate Similarity	NPC105827
0.8491	Intermediate Similarity	NPC310661
0.8476	Intermediate Similarity	NPC29830
0.8476	Intermediate Similarity	NPC168822
0.8471	Intermediate Similarity	NPC212290
0.8471	Intermediate Similarity	NPC195114

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 NPC474010 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	912
0.2-0.3	1875
0.3-0.4	2720
0.4-0.5	1897
0.5-0.6	1003
0.6-0.7	299
0.7-0.8	119
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8679	High Similarity	NPD4868	Clinical (unspecified phase)
0.8553	High Similarity	NPD1465	Phase 2
0.8434	Intermediate Similarity	NPD3818	Discontinued
0.8294	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD7074	Phase 3
0.8212	Intermediate Similarity	NPD230	Phase 1
0.8176	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD7054	Approved
0.8166	Intermediate Similarity	NPD5844	Phase 1
0.8121	Intermediate Similarity	NPD6234	Discontinued
0.8118	Intermediate Similarity	NPD7472	Approved
0.8107	Intermediate Similarity	NPD7228	Approved
0.8089	Intermediate Similarity	NPD6190	Approved
0.8084	Intermediate Similarity	NPD6232	Discontinued
0.807	Intermediate Similarity	NPD6797	Phase 2
0.8037	Intermediate Similarity	NPD1934	Approved
0.8037	Intermediate Similarity	NPD37	Approved
0.8023	Intermediate Similarity	NPD7251	Discontinued
0.8	Intermediate Similarity	NPD4967	Phase 2
0.8	Intermediate Similarity	NPD4966	Approved
0.8	Intermediate Similarity	NPD4965	Approved
0.7988	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7266	Discontinued
0.7941	Intermediate Similarity	NPD7473	Discontinued
0.7914	Intermediate Similarity	NPD4380	Phase 2
0.7882	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6166	Phase 2
0.7874	Intermediate Similarity	NPD7808	Phase 3
0.7816	Intermediate Similarity	NPD7685	Pre-registration
0.7816	Intermediate Similarity	NPD6559	Discontinued
0.7811	Intermediate Similarity	NPD7199	Phase 2
0.7791	Intermediate Similarity	NPD1653	Approved
0.7771	Intermediate Similarity	NPD7819	Suspended
0.7771	Intermediate Similarity	NPD2801	Approved
0.7738	Intermediate Similarity	NPD7075	Discontinued
0.773	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD3817	Phase 2
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD3882	Suspended
0.7677	Intermediate Similarity	NPD943	Approved
0.7654	Intermediate Similarity	NPD1511	Approved
0.7644	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7240	Approved
0.7611	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6801	Discontinued
0.7602	Intermediate Similarity	NPD6959	Discontinued
0.76	Intermediate Similarity	NPD9269	Phase 2
0.7579	Intermediate Similarity	NPD8151	Discontinued
0.7578	Intermediate Similarity	NPD3750	Approved
0.7562	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1512	Approved
0.756	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD8313	Approved
0.7528	Intermediate Similarity	NPD8312	Approved
0.7515	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2533	Approved
0.7486	Intermediate Similarity	NPD3751	Discontinued
0.7484	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD4628	Phase 3
0.7453	Intermediate Similarity	NPD1549	Phase 2
0.7452	Intermediate Similarity	NPD1613	Approved
0.7452	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5494	Approved
0.7439	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3764	Approved
0.7427	Intermediate Similarity	NPD3749	Approved
0.7403	Intermediate Similarity	NPD8150	Discontinued
0.7391	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1510	Phase 2
0.7356	Intermediate Similarity	NPD3787	Discontinued
0.7353	Intermediate Similarity	NPD8455	Phase 2
0.7351	Intermediate Similarity	NPD6535	Approved
0.7351	Intermediate Similarity	NPD6534	Approved
0.7337	Intermediate Similarity	NPD7411	Suspended
0.7333	Intermediate Similarity	NPD9268	Approved
0.7333	Intermediate Similarity	NPD6799	Approved
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7305	Intermediate Similarity	NPD5403	Approved
0.7289	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6599	Discontinued
0.7277	Intermediate Similarity	NPD8320	Phase 1
0.7277	Intermediate Similarity	NPD8319	Approved
0.7273	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3748	Approved
0.7261	Intermediate Similarity	NPD3027	Phase 3
0.7249	Intermediate Similarity	NPD6777	Approved
0.7249	Intermediate Similarity	NPD6776	Approved
0.7249	Intermediate Similarity	NPD6782	Approved
0.7249	Intermediate Similarity	NPD6780	Approved
0.7249	Intermediate Similarity	NPD6778	Approved
0.7249	Intermediate Similarity	NPD6781	Approved
0.7249	Intermediate Similarity	NPD6779	Approved
0.7244	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7700	Phase 2
0.7234	Intermediate Similarity	NPD7699	Phase 2
0.7229	Intermediate Similarity	NPD7390	Discontinued
0.7219	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5401	Approved
0.7186	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7768	Phase 2
0.7152	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7783	Phase 2
0.7143	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7680	Approved
0.7125	Intermediate Similarity	NPD1240	Approved
0.7119	Intermediate Similarity	NPD5242	Approved
0.7117	Intermediate Similarity	NPD5406	Approved
0.7117	Intermediate Similarity	NPD5404	Approved
0.7117	Intermediate Similarity	NPD2935	Discontinued
0.7117	Intermediate Similarity	NPD5405	Approved
0.7117	Intermediate Similarity	NPD2796	Approved
0.7117	Intermediate Similarity	NPD5408	Approved
0.7112	Intermediate Similarity	NPD6212	Phase 3
0.7112	Intermediate Similarity	NPD6213	Phase 3
0.7112	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5353	Approved
0.7107	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7874	Approved
0.7092	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5710	Approved
0.7062	Intermediate Similarity	NPD5711	Approved
0.7048	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD8166	Discontinued
0.7047	Intermediate Similarity	NPD7696	Phase 3
0.7047	Intermediate Similarity	NPD7698	Approved
0.7047	Intermediate Similarity	NPD7697	Approved
0.7039	Intermediate Similarity	NPD9545	Approved
0.7037	Intermediate Similarity	NPD1607	Approved
0.7022	Intermediate Similarity	NPD3926	Phase 2
0.7018	Intermediate Similarity	NPD3455	Phase 2
0.7018	Intermediate Similarity	NPD7458	Discontinued
0.7018	Intermediate Similarity	NPD3226	Approved
0.7012	Intermediate Similarity	NPD1551	Phase 2
0.701	Intermediate Similarity	NPD7870	Phase 2
0.701	Intermediate Similarity	NPD7871	Phase 2
0.6995	Remote Similarity	NPD6823	Phase 2
0.699	Remote Similarity	NPD7701	Phase 2
0.6989	Remote Similarity	NPD919	Approved
0.6982	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7229	Phase 3
0.6935	Remote Similarity	NPD8434	Phase 2
0.6918	Remote Similarity	NPD9494	Approved
0.6909	Remote Similarity	NPD6100	Approved
0.6909	Remote Similarity	NPD6099	Approved
0.6904	Remote Similarity	NPD7585	Approved
0.6901	Remote Similarity	NPD920	Approved
0.6891	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6674	Discontinued
0.6884	Remote Similarity	NPD7801	Approved
0.6871	Remote Similarity	NPD1933	Approved
0.6871	Remote Similarity	NPD447	Suspended
0.6867	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2346	Discontinued
0.6866	Remote Similarity	NPD7930	Approved
0.6853	Remote Similarity	NPD7583	Approved
0.6839	Remote Similarity	NPD6385	Approved
0.6839	Remote Similarity	NPD6386	Approved
0.6821	Remote Similarity	NPD5006	Approved
0.6821	Remote Similarity	NPD5005	Approved
0.6818	Remote Similarity	NPD4288	Approved
0.6816	Remote Similarity	NPD1247	Approved
0.6816	Remote Similarity	NPD8127	Discontinued
0.6802	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD5953	Discontinued
0.6792	Remote Similarity	NPD1470	Approved
0.6786	Remote Similarity	NPD2800	Approved
0.6784	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7286	Phase 2
0.6768	Remote Similarity	NPD7584	Approved
0.6748	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7003	Approved
0.6744	Remote Similarity	NPD6273	Approved
0.6743	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6842	Approved
0.672	Remote Similarity	NPD6841	Approved
0.672	Remote Similarity	NPD6843	Phase 3
0.6717	Remote Similarity	NPD7999	Approved
0.6707	Remote Similarity	NPD2438	Suspended
0.6707	Remote Similarity	NPD4060	Phase 1
0.6701	Remote Similarity	NPD4420	Approved
0.6687	Remote Similarity	NPD1164	Approved
0.6687	Remote Similarity	NPD6798	Discontinued
0.6686	Remote Similarity	NPD1652	Phase 2
0.6686	Remote Similarity	NPD1243	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