NPASS Compound

Structure

CID52598 OpenBabel06191715392D 34 38 0 0 1 0 0 0 0 0999 V2000 4.7376 1.2675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0140 -3.9833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1656 -4.4558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0289 -3.0124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3322 -3.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1955 -2.5139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6644 -2.9587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8103 -2.4656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5526 0.4540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9422 1.3831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8491 0.4765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3472 -2.9865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6915 -0.0223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5138 -2.4880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8232 -1.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3892 -0.0447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9290 0.4083 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6787 -0.9972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5268 -1.5074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7666 -0.0906 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7533 -1.0655 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9025 -1.5414 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3764 -1.0196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0129 -0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0649 -1.0425 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7931 1.8591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6175 0.3853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5910 -1.5644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8892 -2.5163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8670 -1.4469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2392 0.4308 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 5.0781 -0.0677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2140 -1.5185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 31 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 26 1 0 0 0 0 11 13 1 0 0 0 0 11 32 1 0 0 0 0 12 14 1 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 15 18 2 0 0 0 0 15 24 1 0 0 0 0 16 23 2 0 0 0 0 16 31 1 0 0 0 0 17 10 1 6 0 0 0 17 20 1 0 0 0 0 17 33 1 0 0 0 0 18 19 1 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 1 0 0 0 21 22 1 0 0 0 0 21 28 1 6 0 0 0 22 25 1 0 0 0 0 22 29 1 1 0 0 0 23 34 1 0 0 0 0 24 30 2 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 25 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.14
Volume:	453.558
LogP:	2.226
LogD:	2.217
LogS:	-4.408
# Rotatable Bonds:	5
TPSA:	134.91
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	3.907
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.752
MDCK Permeability:	2.4341257812920958e-05
Pgp-inhibitor:	0.042
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.161

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.293
Plasma Protein Binding (PPB):	90.5678482055664%
Volume Distribution (VD):	0.661
Pgp-substrate:	2.651108980178833%

ADMET: Metabolism

CYP1A2-inhibitor:	0.226
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.133
CYP2C9-substrate:	0.566
CYP2D6-inhibitor:	0.206
CYP2D6-substrate:	0.335
CYP3A4-inhibitor:	0.103
CYP3A4-substrate:	0.088

ADMET: Excretion

Clearance (CL):	5.634
Half-life (T1/2):	0.466

ADMET: Toxicity

hERG Blockers:	0.338
Human Hepatotoxicity (H-HT):	0.061
Drug-inuced Liver Injury (DILI):	0.727
AMES Toxicity:	0.763
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.313
Carcinogencity:	0.552
Eye Corrosion:	0.003
Eye Irritation:	0.122
Respiratory Toxicity:	0.017

Download Data

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

Natural Product: NPC52598

Natural Product ID:	NPC52598
*Common Name:**	Haemodorose
IUPAC Name:	n.a.
Synonyms:	haemodorose
Standard InCHIKey:	PZTAHEJWBGPZLJ-FHBCLOHASA-N
Standard InCHI:	InChI=1S/C25H24O9/c1-31-16-9-13-11-32-24(30)15-8-7-14(12-5-3-2-4-6-12)19(18(13)15)23(16)34-25-22(29)21(28)20(27)17(10-26)33-25/h2-9,17,20-22,25-29H,10-11H2,1H3/t17-,20-,21+,22-,25+/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2c(OC)cc3c4c2c(ccc4C(=O)OC3)c2ccccc2)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL552207
PubChem CID:	44179651
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754613]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	root	n.a.	PMID[14750033]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15482936]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	roots	n.a.	n.a.	PMID[18841903]
NPO7440	Elaphoglossum piloselloides	Species	Dryopteridaceae	Eukaryota	n.a.	La Banderita, Tucumn, Argentina	2005-DEC	PMID[19239238]
NPO6823	Haemodorum simplex	Species	Haemodoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19419186]
NPO7440	Elaphoglossum piloselloides	Species	Dryopteridaceae	Eukaryota	n.a.	La Banderita, Tucumn, Argentina	n.a.	PMID[20384357]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24359277]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[24387347]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO5095	Digitalis ferruginea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6654	Eucalyptus phellandra	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5095	Digitalis ferruginea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4260	Stelletta maxima	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5095	Digitalis ferruginea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7281	Veltheimia capensis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7440	Elaphoglossum piloselloides	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6654	Eucalyptus phellandra	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5785	Corymbium villosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6998	Lecanora polytropa	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7742	Eucalyptus caesia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6104	Solidago elongata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6823	Haemodorum simplex	Species	Haemodoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2101	Incisitermes immigrans	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5396	Clibadium laxum	Species	Asteraceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	26000.0	nM	PMID[504440]

☑ 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 NPC52598 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	384
0.1-0.2	1550
0.2-0.3	3252
0.3-0.4	7830
0.4-0.5	9491
0.5-0.6	5155
0.6-0.7	6054
0.7-0.8	7382
0.8-0.85	1370
0.85-0.9	198
0.9-0.95	30
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9341	High Similarity	NPC47191
0.9333	High Similarity	NPC471922
0.9333	High Similarity	NPC20114
0.9333	High Similarity	NPC471921
0.9333	High Similarity	NPC292712
0.9333	High Similarity	NPC474075
0.9333	High Similarity	NPC114550
0.9333	High Similarity	NPC471920
0.9333	High Similarity	NPC312006
0.9333	High Similarity	NPC129930
0.9286	High Similarity	NPC275690
0.9286	High Similarity	NPC161609
0.9222	High Similarity	NPC193377
0.9186	High Similarity	NPC205721
0.9162	High Similarity	NPC199357
0.9123	High Similarity	NPC114120
0.9123	High Similarity	NPC167045
0.9118	High Similarity	NPC208797
0.9118	High Similarity	NPC53680
0.9112	High Similarity	NPC35266
0.9053	High Similarity	NPC67629
0.9053	High Similarity	NPC79736
0.9053	High Similarity	NPC297574
0.9048	High Similarity	NPC316539
0.9048	High Similarity	NPC184624
0.9036	High Similarity	NPC298847
0.9017	High Similarity	NPC313063
0.9017	High Similarity	NPC105591
0.9017	High Similarity	NPC286301
0.9	High Similarity	NPC267549
0.8994	High Similarity	NPC470667
0.8994	High Similarity	NPC186800
0.8994	High Similarity	NPC146803
0.8988	High Similarity	NPC38438
0.8988	High Similarity	NPC473697
0.8976	High Similarity	NPC471923
0.8935	High Similarity	NPC219600
0.8935	High Similarity	NPC263119
0.8935	High Similarity	NPC203751
0.8935	High Similarity	NPC46640
0.8935	High Similarity	NPC34436
0.8935	High Similarity	NPC166674
0.8929	High Similarity	NPC313304
0.8922	High Similarity	NPC473531
0.8922	High Similarity	NPC475453
0.8896	High Similarity	NPC133984
0.8895	High Similarity	NPC475161
0.8895	High Similarity	NPC477860
0.8889	High Similarity	NPC472835
0.8882	High Similarity	NPC63105
0.8882	High Similarity	NPC137813
0.8864	High Similarity	NPC264302
0.8855	High Similarity	NPC121290
0.8851	High Similarity	NPC241847
0.8844	High Similarity	NPC123259
0.8844	High Similarity	NPC129533
0.8837	High Similarity	NPC212290
0.8837	High Similarity	NPC153578
0.8837	High Similarity	NPC80956
0.8837	High Similarity	NPC299149
0.8837	High Similarity	NPC277710
0.8837	High Similarity	NPC114257
0.8834	High Similarity	NPC109765
0.883	High Similarity	NPC475054
0.883	High Similarity	NPC289876
0.883	High Similarity	NPC475246
0.883	High Similarity	NPC102053
0.883	High Similarity	NPC472723
0.8824	High Similarity	NPC473550
0.8824	High Similarity	NPC85368
0.882	High Similarity	NPC36130
0.882	High Similarity	NPC134905
0.8817	High Similarity	NPC298778
0.8817	High Similarity	NPC181778
0.8802	High Similarity	NPC178281
0.8802	High Similarity	NPC99216
0.8788	High Similarity	NPC328093
0.878	High Similarity	NPC202495
0.878	High Similarity	NPC296044
0.878	High Similarity	NPC167098
0.8779	High Similarity	NPC472387
0.8773	High Similarity	NPC10205
0.8772	High Similarity	NPC3718
0.8772	High Similarity	NPC68381
0.8765	High Similarity	NPC67134
0.8765	High Similarity	NPC47140
0.875	High Similarity	NPC269046
0.875	High Similarity	NPC111785
0.8743	High Similarity	NPC17432
0.8743	High Similarity	NPC25889
0.8743	High Similarity	NPC87583
0.8736	High Similarity	NPC476203
0.8728	High Similarity	NPC58538
0.8728	High Similarity	NPC84494
0.8728	High Similarity	NPC245059
0.8721	High Similarity	NPC46958
0.872	High Similarity	NPC471405
0.8713	High Similarity	NPC213052
0.8713	High Similarity	NPC472993
0.8712	High Similarity	NPC191046
0.8712	High Similarity	NPC194095
0.8712	High Similarity	NPC327032
0.8706	High Similarity	NPC135370
0.8704	High Similarity	NPC118332
0.8696	High Similarity	NPC300983
0.8693	High Similarity	NPC237202
0.8686	High Similarity	NPC231254
0.8683	High Similarity	NPC146837
0.8683	High Similarity	NPC22130
0.8683	High Similarity	NPC212099
0.8683	High Similarity	NPC216752
0.8683	High Similarity	NPC187934
0.8683	High Similarity	NPC101116
0.8683	High Similarity	NPC278329
0.8683	High Similarity	NPC97637
0.8683	High Similarity	NPC33298
0.8683	High Similarity	NPC285108
0.8683	High Similarity	NPC116838
0.8678	High Similarity	NPC164047
0.8678	High Similarity	NPC470448
0.8678	High Similarity	NPC85316
0.8678	High Similarity	NPC197357
0.8678	High Similarity	NPC470452
0.8678	High Similarity	NPC8940
0.8678	High Similarity	NPC470453
0.8671	High Similarity	NPC476622
0.8671	High Similarity	NPC476621
0.8671	High Similarity	NPC476619
0.8671	High Similarity	NPC476618
0.8671	High Similarity	NPC476620
0.8671	High Similarity	NPC476623
0.8663	High Similarity	NPC470454
0.8663	High Similarity	NPC474345
0.8663	High Similarity	NPC199533
0.8655	High Similarity	NPC271385
0.8655	High Similarity	NPC5029
0.8655	High Similarity	NPC76128
0.8655	High Similarity	NPC30432
0.8655	High Similarity	NPC256760
0.8655	High Similarity	NPC111536
0.865	High Similarity	NPC157898
0.8647	High Similarity	NPC197708
0.8647	High Similarity	NPC61791
0.8647	High Similarity	NPC658
0.8647	High Similarity	NPC259905
0.8644	High Similarity	NPC173872
0.8644	High Similarity	NPC119094
0.8639	High Similarity	NPC178851
0.8636	High Similarity	NPC229817
0.8636	High Similarity	NPC111490
0.8636	High Similarity	NPC261623
0.8636	High Similarity	NPC475352
0.8636	High Similarity	NPC221140
0.8636	High Similarity	NPC473686
0.8636	High Similarity	NPC475220
0.8631	High Similarity	NPC45943
0.8629	High Similarity	NPC293227
0.8629	High Similarity	NPC475662
0.8629	High Similarity	NPC473717
0.8629	High Similarity	NPC473631
0.8623	High Similarity	NPC469889
0.8614	High Similarity	NPC125713
0.8613	High Similarity	NPC76112
0.8613	High Similarity	NPC196771
0.8613	High Similarity	NPC66820
0.8613	High Similarity	NPC170018
0.8613	High Similarity	NPC92403
0.8606	High Similarity	NPC115123
0.8606	High Similarity	NPC239113
0.8605	High Similarity	NPC175230
0.8605	High Similarity	NPC88560
0.8605	High Similarity	NPC172033
0.8605	High Similarity	NPC208668
0.8596	High Similarity	NPC231194
0.8596	High Similarity	NPC149011
0.8596	High Similarity	NPC93065
0.8596	High Similarity	NPC469652
0.8596	High Similarity	NPC472724
0.8596	High Similarity	NPC472721
0.8596	High Similarity	NPC314672
0.8596	High Similarity	NPC204937
0.8596	High Similarity	NPC160543
0.8596	High Similarity	NPC51326
0.8596	High Similarity	NPC78734
0.8596	High Similarity	NPC31208
0.8596	High Similarity	NPC472720
0.8596	High Similarity	NPC150767
0.8589	High Similarity	NPC474442
0.8588	High Similarity	NPC65489
0.8588	High Similarity	NPC469521
0.8588	High Similarity	NPC477502
0.8588	High Similarity	NPC473818
0.8588	High Similarity	NPC63470
0.858	High Similarity	NPC475497
0.858	High Similarity	NPC475366
0.858	High Similarity	NPC292706
0.858	High Similarity	NPC224557
0.858	High Similarity	NPC284277
0.8571	High Similarity	NPC61594
0.8571	High Similarity	NPC291957

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 NPC52598 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	915
0.2-0.3	1637
0.3-0.4	2590
0.4-0.5	1970
0.5-0.6	1049
0.6-0.7	477
0.7-0.8	155
0.8-0.85	21
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8982	High Similarity	NPD5844	Phase 1
0.8613	High Similarity	NPD8313	Approved
0.8613	High Similarity	NPD8312	Approved
0.8598	High Similarity	NPD8455	Phase 2
0.8488	Intermediate Similarity	NPD7074	Phase 3
0.8475	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.843	Intermediate Similarity	NPD7054	Approved
0.8383	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD7472	Approved
0.8353	Intermediate Similarity	NPD6232	Discontinued
0.8294	Intermediate Similarity	NPD7199	Phase 2
0.8286	Intermediate Similarity	NPD6559	Discontinued
0.8278	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD7228	Approved
0.8256	Intermediate Similarity	NPD6166	Phase 2
0.8256	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD7808	Phase 3
0.8229	Intermediate Similarity	NPD6797	Phase 2
0.8208	Intermediate Similarity	NPD7473	Discontinued
0.8187	Intermediate Similarity	NPD6959	Discontinued
0.8182	Intermediate Similarity	NPD7251	Discontinued
0.8161	Intermediate Similarity	NPD3818	Discontinued
0.8155	Intermediate Similarity	NPD1465	Phase 2
0.8137	Intermediate Similarity	NPD6674	Discontinued
0.8136	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD37	Approved
0.8092	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD4628	Phase 3
0.8079	Intermediate Similarity	NPD7240	Approved
0.8059	Intermediate Similarity	NPD4967	Phase 2
0.8059	Intermediate Similarity	NPD4965	Approved
0.8059	Intermediate Similarity	NPD4966	Approved
0.8049	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7819	Suspended
0.8024	Intermediate Similarity	NPD7458	Discontinued
0.8021	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD7783	Phase 2
0.8012	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.801	Intermediate Similarity	NPD8151	Discontinued
0.8	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD7685	Pre-registration
0.7965	Intermediate Similarity	NPD6234	Discontinued
0.7941	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD5494	Approved
0.7914	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3817	Phase 2
0.7892	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD1934	Approved
0.7842	Intermediate Similarity	NPD7435	Discontinued
0.7836	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7411	Suspended
0.7811	Intermediate Similarity	NPD3226	Approved
0.7803	Intermediate Similarity	NPD7075	Discontinued
0.7791	Intermediate Similarity	NPD7266	Discontinued
0.7778	Intermediate Similarity	NPD6779	Approved
0.7778	Intermediate Similarity	NPD6777	Approved
0.7778	Intermediate Similarity	NPD6776	Approved
0.7778	Intermediate Similarity	NPD6778	Approved
0.7778	Intermediate Similarity	NPD6781	Approved
0.7778	Intermediate Similarity	NPD6782	Approved
0.7778	Intermediate Similarity	NPD6780	Approved
0.7771	Intermediate Similarity	NPD8127	Discontinued
0.7765	Intermediate Similarity	NPD4380	Phase 2
0.7758	Intermediate Similarity	NPD7003	Approved
0.7753	Intermediate Similarity	NPD3751	Discontinued
0.774	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3787	Discontinued
0.7683	Intermediate Similarity	NPD2346	Discontinued
0.7674	Intermediate Similarity	NPD6801	Discontinued
0.7656	Intermediate Similarity	NPD7696	Phase 3
0.7656	Intermediate Similarity	NPD7698	Approved
0.7656	Intermediate Similarity	NPD7697	Approved
0.7654	Intermediate Similarity	NPD7177	Discontinued
0.7647	Intermediate Similarity	NPD1653	Approved
0.7633	Intermediate Similarity	NPD6273	Approved
0.7617	Intermediate Similarity	NPD7871	Phase 2
0.7617	Intermediate Similarity	NPD7870	Phase 2
0.7602	Intermediate Similarity	NPD7874	Approved
0.7602	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7701	Phase 2
0.7586	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD8150	Discontinued
0.7558	Intermediate Similarity	NPD6599	Discontinued
0.7543	Intermediate Similarity	NPD7768	Phase 2
0.7529	Intermediate Similarity	NPD2801	Approved
0.7526	Intermediate Similarity	NPD8320	Phase 1
0.7526	Intermediate Similarity	NPD8319	Approved
0.7513	Intermediate Similarity	NPD6535	Approved
0.7513	Intermediate Similarity	NPD6823	Phase 2
0.7513	Intermediate Similarity	NPD6534	Approved
0.7487	Intermediate Similarity	NPD7699	Phase 2
0.7487	Intermediate Similarity	NPD7700	Phase 2
0.7485	Intermediate Similarity	NPD1933	Approved
0.7474	Intermediate Similarity	NPD7680	Approved
0.7448	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD3882	Suspended
0.744	Intermediate Similarity	NPD3750	Approved
0.7412	Intermediate Similarity	NPD6799	Approved
0.741	Intermediate Similarity	NPD2438	Suspended
0.7407	Intermediate Similarity	NPD6798	Discontinued
0.7401	Intermediate Similarity	NPD3749	Approved
0.7398	Intermediate Similarity	NPD7999	Approved
0.7396	Intermediate Similarity	NPD6190	Approved
0.7391	Intermediate Similarity	NPD7039	Approved
0.7391	Intermediate Similarity	NPD7038	Approved
0.7387	Intermediate Similarity	NPD7801	Approved
0.7386	Intermediate Similarity	NPD5402	Approved
0.7381	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2533	Approved
0.7368	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6213	Phase 3
0.7368	Intermediate Similarity	NPD2534	Approved
0.7368	Intermediate Similarity	NPD6212	Phase 3
0.7368	Intermediate Similarity	NPD2532	Approved
0.736	Intermediate Similarity	NPD919	Approved
0.7349	Intermediate Similarity	NPD3748	Approved
0.7333	Intermediate Similarity	NPD7229	Phase 3
0.733	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1511	Approved
0.7305	Intermediate Similarity	NPD2935	Discontinued
0.7305	Intermediate Similarity	NPD5408	Approved
0.7305	Intermediate Similarity	NPD5405	Approved
0.7305	Intermediate Similarity	NPD5404	Approved
0.7305	Intermediate Similarity	NPD5406	Approved
0.7289	Intermediate Similarity	NPD7097	Phase 1
0.7287	Intermediate Similarity	NPD8434	Phase 2
0.7283	Intermediate Similarity	NPD5403	Approved
0.7267	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5401	Approved
0.7256	Intermediate Similarity	NPD6233	Phase 2
0.725	Intermediate Similarity	NPD1283	Approved
0.7246	Intermediate Similarity	NPD2799	Discontinued
0.7225	Intermediate Similarity	NPD1512	Approved
0.7219	Intermediate Similarity	NPD1549	Phase 2
0.7212	Intermediate Similarity	NPD4060	Phase 1
0.7212	Intermediate Similarity	NPD2979	Phase 3
0.7209	Intermediate Similarity	NPD7390	Discontinued
0.7202	Intermediate Similarity	NPD2796	Approved
0.7198	Intermediate Similarity	NPD3926	Phase 2
0.7195	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7583	Approved
0.7169	Intermediate Similarity	NPD447	Suspended
0.7169	Intermediate Similarity	NPD6355	Discontinued
0.716	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7585	Approved
0.7135	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8166	Discontinued
0.7135	Intermediate Similarity	NPD4110	Phase 3
0.7134	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1608	Approved
0.7119	Intermediate Similarity	NPD6385	Approved
0.7119	Intermediate Similarity	NPD6386	Approved
0.7118	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1613	Approved
0.7108	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7930	Approved
0.7092	Intermediate Similarity	NPD8285	Discontinued
0.7091	Intermediate Similarity	NPD3764	Approved
0.7091	Intermediate Similarity	NPD2313	Discontinued
0.7088	Intermediate Similarity	NPD1247	Approved
0.7066	Intermediate Similarity	NPD230	Phase 1
0.7063	Intermediate Similarity	NPD1281	Approved
0.7062	Intermediate Similarity	NPD7028	Phase 2
0.7059	Intermediate Similarity	NPD5763	Approved
0.7059	Intermediate Similarity	NPD5762	Approved
0.7041	Intermediate Similarity	NPD4308	Phase 3
0.7041	Intermediate Similarity	NPD7033	Discontinued
0.7026	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7584	Approved
0.7011	Intermediate Similarity	NPD5242	Approved
0.7	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4477	Approved
0.7	Intermediate Similarity	NPD1551	Phase 2
0.7	Intermediate Similarity	NPD4476	Approved
0.699	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD920	Approved
0.6989	Remote Similarity	NPD7427	Discontinued
0.6989	Remote Similarity	NPD7799	Discontinued
0.6989	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7549	Discontinued
0.6981	Remote Similarity	NPD5691	Approved
0.697	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6832	Phase 2
0.6965	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5710	Approved
0.6957	Remote Similarity	NPD5711	Approved
0.6957	Remote Similarity	NPD1091	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