NPASS Compound

Structure

CID197107 OpenBabel06191715582D 21 24 0 0 1 0 0 0 0 0999 V2000 -2.9359 -1.1567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1053 1.7259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3056 -1.1627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3056 0.7318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4853 1.2054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0354 -0.4723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1260 -0.6890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1260 0.2582 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4853 -0.6890 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5898 -0.2153 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1787 0.6382 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1789 -1.0689 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2552 0.8488 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4853 0.2582 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3914 -0.2668 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2258 1.7960 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9359 0.7258 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4848 -0.2152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7367 1.3380 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 0.2554 -1.2795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 13 1 0 0 0 0 3 7 2 0 0 0 0 3 9 1 0 0 0 0 4 8 1 0 0 0 0 4 14 1 0 0 0 0 5 16 1 0 0 0 0 6 15 1 0 0 0 0 6 20 1 0 0 0 0 7 8 1 0 0 0 0 8 17 1 1 0 0 0 9 14 1 6 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 1 0 0 0 11 13 1 6 0 0 0 11 19 1 0 0 0 0 12 15 1 6 0 0 0 12 21 1 0 0 0 0 13 14 1 1 0 0 0 14 5 1 1 0 0 0 15 13 1 1 0 0 0 15 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.14
Volume:	283.875
LogP:	-0.102
LogD:	-0.49
LogS:	-2.87
# Rotatable Bonds:	1
TPSA:	102.68
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.364
Synthetic Accessibility Score:	6.382
Fsp3:	0.867
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:	-5.823
MDCK Permeability:	1.7366402971674688e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.109
20% Bioavailability (F20%):	0.065
30% Bioavailability (F30%):	0.092

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.207
Plasma Protein Binding (PPB):	22.537586212158203%
Volume Distribution (VD):	0.433
Pgp-substrate:	64.39009094238281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.7
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.771
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.132

ADMET: Excretion

Clearance (CL):	3.46
Half-life (T1/2):	0.83

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.488
Drug-inuced Liver Injury (DILI):	0.072
AMES Toxicity:	0.86
Rat Oral Acute Toxicity:	0.888
Maximum Recommended Daily Dose:	0.546
Skin Sensitization:	0.404
Carcinogencity:	0.232
Eye Corrosion:	0.005
Eye Irritation:	0.062
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC197107

Natural Product ID:	NPC197107
*Common Name:**	ZAXZBJSXSOISTF-LYFQSNBGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZAXZBJSXSOISTF-LYFQSNBGSA-N
Standard InCHI:	InChI=1S/C15H22O6/c1-7-3-9-14(5-16,4-8(7)17)13(2)11(19)10(18)12(21-9)15(13)6-20-15/h3,8-12,16-19H,4-6H2,1-2H3/t8-,9+,10+,11+,12+,13+,14+,15-/m0/s1
SMILES:	OC[C@]12C[C@H](O)C(=C[C@H]1O[C@H]1[C@@]3([C@]2(C)[C@H](O)[C@H]1O)OC3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL152377
PubChem CID:	9904331
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001789] Trichothecenes

*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
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO11911	Austroeupatorium inulifolium	Species	Asteraceae	Eukaryota	n.a.	leaf	n.a.	PMID[12116880]
NPO11911	Austroeupatorium inulifolium	Species	Asteraceae	Eukaryota	n.a.	stem	n.a.	PMID[12116880]
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800633]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800639]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[2347013]
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25475336]
NPO27814	Commiphora merkeri	Species	Burseraceae	Eukaryota	Roots	n.a.	n.a.	PMID[2607349]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3210017]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3734813]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4040956]
NPO15511	Fusarium heterosporum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264681]
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8289061]
NPO27267	Veratrum album	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27267	Veratrum album	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10844	Lactarius pergamenus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27267	Veratrum album	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27357	Artemisia ramosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27574	Nephromopsis endocrocea	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26940	Triplostegia grandiflora	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27610	Pseudomonas amygdali	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27159	Echiochilon fruticosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27490	Erythroxylum deciduum	Species	Erythroxylaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27342	Senecio kleinia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11911	Austroeupatorium inulifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15511	Fusarium heterosporum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4524	Bosistoa pentacocca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26968	Baccharis helichrysoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10844	Lactarius pergamenus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27814	Commiphora merkeri	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27267	Veratrum album	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20528	Ilex theizans	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27535	Bos moschatus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27235	Artemisia nitrosa	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
ED50	1
LD50	1
Others	3

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	LC50	=	0.1	ug.mL-1	PMID[473138]
NPT673	Organism	Gallus gallus	Gallus gallus	LD50	>	10.0	mg.kg-1	PMID[473139]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	ED50	>	1.28	ug	PMID[473139]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Ratio	=	4.3	n.a.	PMID[473140]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	=	4.3	n.a.	PMID[473140]

☑ 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 NPC197107 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	181
0.1-0.2	1517
0.2-0.3	5478
0.3-0.4	14431
0.4-0.5	10101
0.5-0.6	7315
0.6-0.7	3425
0.7-0.8	187
0.8-0.85	32
0.85-0.9	17
0.9-0.95	9
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC182811
0.9231	High Similarity	NPC274458
0.9121	High Similarity	NPC347923
0.9121	High Similarity	NPC476057
0.9111	High Similarity	NPC240838
0.9022	High Similarity	NPC79449
0.9022	High Similarity	NPC474957
0.883	High Similarity	NPC26557
0.8737	High Similarity	NPC214714
0.8737	High Similarity	NPC475986
0.8737	High Similarity	NPC200672
0.8737	High Similarity	NPC475956
0.8737	High Similarity	NPC252242
0.8723	High Similarity	NPC79631
0.8646	High Similarity	NPC260809
0.8646	High Similarity	NPC232515
0.8646	High Similarity	NPC474783
0.8384	Intermediate Similarity	NPC469957
0.8384	Intermediate Similarity	NPC108682
0.8384	Intermediate Similarity	NPC469959
0.8384	Intermediate Similarity	NPC472263
0.8352	Intermediate Similarity	NPC299527
0.8283	Intermediate Similarity	NPC469960
0.8283	Intermediate Similarity	NPC93026
0.8283	Intermediate Similarity	NPC265502
0.8283	Intermediate Similarity	NPC29389
0.8265	Intermediate Similarity	NPC123505
0.8222	Intermediate Similarity	NPC255143
0.8039	Intermediate Similarity	NPC77089
0.8	Intermediate Similarity	NPC83702
0.8	Intermediate Similarity	NPC305044
0.8	Intermediate Similarity	NPC265290
0.7961	Intermediate Similarity	NPC41551
0.7961	Intermediate Similarity	NPC50223
0.7957	Intermediate Similarity	NPC49783
0.7931	Intermediate Similarity	NPC477089
0.7857	Intermediate Similarity	NPC65700
0.7857	Intermediate Similarity	NPC177232
0.7857	Intermediate Similarity	NPC212465
0.7835	Intermediate Similarity	NPC72204
0.781	Intermediate Similarity	NPC98038
0.781	Intermediate Similarity	NPC313921
0.7802	Intermediate Similarity	NPC116613
0.7778	Intermediate Similarity	NPC13743
0.7778	Intermediate Similarity	NPC98813
0.7755	Intermediate Similarity	NPC261807
0.7736	Intermediate Similarity	NPC101400
0.7736	Intermediate Similarity	NPC101965
0.7736	Intermediate Similarity	NPC287075
0.7692	Intermediate Similarity	NPC260852
0.7692	Intermediate Similarity	NPC128133
0.7692	Intermediate Similarity	NPC471340
0.7667	Intermediate Similarity	NPC15978
0.7653	Intermediate Similarity	NPC210717
0.7653	Intermediate Similarity	NPC288970
0.7653	Intermediate Similarity	NPC103165
0.7642	Intermediate Similarity	NPC473567
0.7642	Intermediate Similarity	NPC216595
0.7634	Intermediate Similarity	NPC281316
0.7634	Intermediate Similarity	NPC477668
0.7615	Intermediate Similarity	NPC474286
0.7615	Intermediate Similarity	NPC475130
0.7614	Intermediate Similarity	NPC476703
0.76	Intermediate Similarity	NPC471242
0.7551	Intermediate Similarity	NPC8774
0.7528	Intermediate Similarity	NPC13823
0.7528	Intermediate Similarity	NPC68119
0.7526	Intermediate Similarity	NPC119379
0.7526	Intermediate Similarity	NPC137461
0.7526	Intermediate Similarity	NPC98193
0.7525	Intermediate Similarity	NPC476896
0.75	Intermediate Similarity	NPC126969
0.75	Intermediate Similarity	NPC170148
0.7477	Intermediate Similarity	NPC126691
0.7476	Intermediate Similarity	NPC169843
0.7476	Intermediate Similarity	NPC474464
0.7475	Intermediate Similarity	NPC227583
0.7475	Intermediate Similarity	NPC57664
0.7475	Intermediate Similarity	NPC12103
0.7475	Intermediate Similarity	NPC98457
0.7471	Intermediate Similarity	NPC190859
0.7449	Intermediate Similarity	NPC65402
0.7449	Intermediate Similarity	NPC127718
0.7449	Intermediate Similarity	NPC473258
0.7423	Intermediate Similarity	NPC302584
0.7423	Intermediate Similarity	NPC210268
0.7423	Intermediate Similarity	NPC114389
0.7416	Intermediate Similarity	NPC471454
0.7404	Intermediate Similarity	NPC474015
0.74	Intermediate Similarity	NPC205143
0.7383	Intermediate Similarity	NPC71680
0.7379	Intermediate Similarity	NPC475701
0.7379	Intermediate Similarity	NPC473523
0.7368	Intermediate Similarity	NPC476948
0.7363	Intermediate Similarity	NPC186072
0.7358	Intermediate Similarity	NPC472901
0.7358	Intermediate Similarity	NPC187876
0.7353	Intermediate Similarity	NPC475617
0.7353	Intermediate Similarity	NPC21568
0.7353	Intermediate Similarity	NPC285231
0.7347	Intermediate Similarity	NPC91654
0.7347	Intermediate Similarity	NPC474792
0.7347	Intermediate Similarity	NPC67398
0.734	Intermediate Similarity	NPC298595
0.7333	Intermediate Similarity	NPC33053
0.7327	Intermediate Similarity	NPC476895
0.732	Intermediate Similarity	NPC295668
0.7315	Intermediate Similarity	NPC477050
0.7312	Intermediate Similarity	NPC231601
0.7312	Intermediate Similarity	NPC477667
0.7308	Intermediate Similarity	NPC473543
0.7308	Intermediate Similarity	NPC471111
0.7308	Intermediate Similarity	NPC152966
0.7308	Intermediate Similarity	NPC93352
0.7292	Intermediate Similarity	NPC475991
0.7292	Intermediate Similarity	NPC248312
0.729	Intermediate Similarity	NPC15551
0.7283	Intermediate Similarity	NPC471661
0.7282	Intermediate Similarity	NPC470972
0.7273	Intermediate Similarity	NPC144202
0.7273	Intermediate Similarity	NPC472467
0.7264	Intermediate Similarity	NPC10150
0.7263	Intermediate Similarity	NPC293287
0.7263	Intermediate Similarity	NPC125399
0.7263	Intermediate Similarity	NPC152808
0.7255	Intermediate Similarity	NPC469942
0.7253	Intermediate Similarity	NPC476701
0.7248	Intermediate Similarity	NPC469348
0.7248	Intermediate Similarity	NPC317210
0.7248	Intermediate Similarity	NPC469347
0.7245	Intermediate Similarity	NPC97404
0.7245	Intermediate Similarity	NPC41554
0.7238	Intermediate Similarity	NPC475290
0.7238	Intermediate Similarity	NPC470980
0.7232	Intermediate Similarity	NPC278681
0.7228	Intermediate Similarity	NPC210337
0.7228	Intermediate Similarity	NPC476893
0.7222	Intermediate Similarity	NPC472987
0.7222	Intermediate Similarity	NPC473021
0.7216	Intermediate Similarity	NPC470361
0.7216	Intermediate Similarity	NPC115607
0.7212	Intermediate Similarity	NPC474124
0.7212	Intermediate Similarity	NPC472821
0.7207	Intermediate Similarity	NPC290693
0.7204	Intermediate Similarity	NPC259858
0.72	Intermediate Similarity	NPC220221
0.7188	Intermediate Similarity	NPC149224
0.7184	Intermediate Similarity	NPC470434
0.7184	Intermediate Similarity	NPC176406
0.7182	Intermediate Similarity	NPC216665
0.7172	Intermediate Similarity	NPC27531
0.717	Intermediate Similarity	NPC475781
0.717	Intermediate Similarity	NPC144459
0.717	Intermediate Similarity	NPC472820
0.7168	Intermediate Similarity	NPC112936
0.7159	Intermediate Similarity	NPC476709
0.7158	Intermediate Similarity	NPC474189
0.7158	Intermediate Similarity	NPC474349
0.7158	Intermediate Similarity	NPC266511
0.7158	Intermediate Similarity	NPC119001
0.7157	Intermediate Similarity	NPC312325
0.7157	Intermediate Similarity	NPC222303
0.7156	Intermediate Similarity	NPC241477
0.7143	Intermediate Similarity	NPC103298
0.7143	Intermediate Similarity	NPC191323
0.7143	Intermediate Similarity	NPC258532
0.7143	Intermediate Similarity	NPC475335
0.7143	Intermediate Similarity	NPC16701
0.7143	Intermediate Similarity	NPC204188
0.7143	Intermediate Similarity	NPC80809
0.7143	Intermediate Similarity	NPC470832
0.7143	Intermediate Similarity	NPC3345
0.7143	Intermediate Similarity	NPC201144
0.7143	Intermediate Similarity	NPC80561
0.7143	Intermediate Similarity	NPC181104
0.7143	Intermediate Similarity	NPC475331
0.7143	Intermediate Similarity	NPC200861
0.7143	Intermediate Similarity	NPC473577
0.7143	Intermediate Similarity	NPC475585
0.7143	Intermediate Similarity	NPC288502
0.7143	Intermediate Similarity	NPC474550
0.7143	Intermediate Similarity	NPC75608
0.7143	Intermediate Similarity	NPC291484
0.7143	Intermediate Similarity	NPC329596
0.7143	Intermediate Similarity	NPC121518
0.7143	Intermediate Similarity	NPC472822
0.7143	Intermediate Similarity	NPC11216
0.7143	Intermediate Similarity	NPC470817
0.713	Intermediate Similarity	NPC103627
0.713	Intermediate Similarity	NPC170974
0.713	Intermediate Similarity	NPC191439
0.713	Intermediate Similarity	NPC65155
0.7129	Intermediate Similarity	NPC88009
0.7129	Intermediate Similarity	NPC98165
0.7129	Intermediate Similarity	NPC90583
0.7126	Intermediate Similarity	NPC129630
0.7115	Intermediate Similarity	NPC476471
0.7115	Intermediate Similarity	NPC22634
0.7115	Intermediate Similarity	NPC475344
0.7113	Intermediate Similarity	NPC22376

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 NPC197107 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1819
0.2-0.3	4193
0.3-0.4	2142
0.4-0.5	485
0.5-0.6	276
0.6-0.7	67
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7188	Intermediate Similarity	NPD7524	Approved
0.7053	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6695	Phase 3
0.6857	Remote Similarity	NPD4159	Approved
0.6842	Remote Similarity	NPD7328	Approved
0.6842	Remote Similarity	NPD7327	Approved
0.6837	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7503	Approved
0.681	Remote Similarity	NPD8033	Approved
0.6783	Remote Similarity	NPD7516	Approved
0.6762	Remote Similarity	NPD7640	Approved
0.6762	Remote Similarity	NPD7639	Approved
0.6724	Remote Similarity	NPD8377	Approved
0.6724	Remote Similarity	NPD8294	Approved
0.6698	Remote Similarity	NPD5344	Discontinued
0.6697	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6634	Remote Similarity	NPD46	Approved
0.6634	Remote Similarity	NPD6698	Approved
0.6632	Remote Similarity	NPD6930	Phase 2
0.6632	Remote Similarity	NPD6931	Approved
0.6588	Remote Similarity	NPD368	Approved
0.6577	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6929	Approved
0.6518	Remote Similarity	NPD6371	Approved
0.6471	Remote Similarity	NPD7838	Discovery
0.6466	Remote Similarity	NPD7115	Discovery
0.6458	Remote Similarity	NPD7514	Phase 3
0.6458	Remote Similarity	NPD7525	Registered
0.6446	Remote Similarity	NPD7507	Approved
0.6408	Remote Similarity	NPD7087	Discontinued
0.6404	Remote Similarity	NPD6053	Discontinued
0.64	Remote Similarity	NPD4249	Approved
0.6392	Remote Similarity	NPD6902	Approved
0.6383	Remote Similarity	NPD6933	Approved
0.6373	Remote Similarity	NPD6051	Approved
0.6355	Remote Similarity	NPD4225	Approved
0.6339	Remote Similarity	NPD6686	Approved
0.6337	Remote Similarity	NPD4250	Approved
0.6337	Remote Similarity	NPD4251	Approved
0.6316	Remote Similarity	NPD5776	Phase 2
0.6316	Remote Similarity	NPD6925	Approved
0.6303	Remote Similarity	NPD6319	Approved
0.63	Remote Similarity	NPD6893	Approved
0.6296	Remote Similarity	NPD6648	Approved
0.629	Remote Similarity	NPD7319	Approved
0.6289	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4819	Approved
0.6289	Remote Similarity	NPD4821	Approved
0.6289	Remote Similarity	NPD7332	Phase 2
0.6289	Remote Similarity	NPD4822	Approved
0.6289	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD7145	Approved
0.6228	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD4634	Approved
0.6207	Remote Similarity	NPD4632	Approved
0.6182	Remote Similarity	NPD7632	Discontinued
0.6182	Remote Similarity	NPD5211	Phase 2
0.617	Remote Similarity	NPD6926	Approved
0.617	Remote Similarity	NPD6924	Approved
0.6167	Remote Similarity	NPD6059	Approved
0.6167	Remote Similarity	NPD6054	Approved
0.6161	Remote Similarity	NPD6640	Phase 3
0.6146	Remote Similarity	NPD6932	Approved
0.6139	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4243	Approved
0.6116	Remote Similarity	NPD6015	Approved
0.6116	Remote Similarity	NPD6016	Approved
0.6111	Remote Similarity	NPD4755	Approved
0.6106	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD7339	Approved
0.6105	Remote Similarity	NPD6942	Approved
0.6095	Remote Similarity	NPD7637	Suspended
0.6082	Remote Similarity	NPD4271	Approved
0.6082	Remote Similarity	NPD4268	Approved
0.6071	Remote Similarity	NPD5141	Approved
0.6066	Remote Similarity	NPD5988	Approved
0.6066	Remote Similarity	NPD6370	Approved
0.6061	Remote Similarity	NPD6898	Phase 1
0.6058	Remote Similarity	NPD4753	Phase 2
0.6055	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.604	Remote Similarity	NPD3666	Approved
0.604	Remote Similarity	NPD3665	Phase 1
0.604	Remote Similarity	NPD3133	Approved
0.6038	Remote Similarity	NPD4202	Approved
0.6034	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7645	Phase 2
0.602	Remote Similarity	NPD6683	Phase 2
0.6018	Remote Similarity	NPD6008	Approved
0.6018	Remote Similarity	NPD5739	Approved
0.6018	Remote Similarity	NPD7128	Approved
0.6018	Remote Similarity	NPD6675	Approved
0.6018	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD4784	Approved
0.6	Remote Similarity	NPD4785	Approved
0.6	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD5285	Approved
0.6	Remote Similarity	NPD3168	Discontinued
0.5984	Remote Similarity	NPD8517	Approved
0.5984	Remote Similarity	NPD8516	Approved
0.5984	Remote Similarity	NPD8515	Approved
0.5984	Remote Similarity	NPD8513	Phase 3
0.5983	Remote Similarity	NPD8297	Approved
0.5968	Remote Similarity	NPD7492	Approved
0.5965	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5701	Approved
0.5965	Remote Similarity	NPD5697	Approved
0.5963	Remote Similarity	NPD6083	Phase 2
0.5963	Remote Similarity	NPD6084	Phase 2
0.596	Remote Similarity	NPD4748	Discontinued
0.5938	Remote Similarity	NPD5275	Approved
0.5938	Remote Similarity	NPD4190	Phase 3
0.5932	Remote Similarity	NPD8133	Approved
0.5926	Remote Similarity	NPD5695	Phase 3
0.592	Remote Similarity	NPD6616	Approved
0.5918	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6009	Approved
0.5913	Remote Similarity	NPD6881	Approved
0.5913	Remote Similarity	NPD6899	Approved
0.5913	Remote Similarity	NPD7320	Approved
0.5905	Remote Similarity	NPD1695	Approved
0.5893	Remote Similarity	NPD4633	Approved
0.5893	Remote Similarity	NPD5224	Approved
0.5893	Remote Similarity	NPD5225	Approved
0.5893	Remote Similarity	NPD5226	Approved
0.5889	Remote Similarity	NPD371	Approved
0.5887	Remote Similarity	NPD7604	Phase 2
0.5882	Remote Similarity	NPD342	Phase 1
0.5873	Remote Similarity	NPD7078	Approved
0.5873	Remote Similarity	NPD8293	Discontinued
0.5872	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6012	Approved
0.5862	Remote Similarity	NPD6373	Approved
0.5862	Remote Similarity	NPD6014	Approved
0.5862	Remote Similarity	NPD6372	Approved
0.5862	Remote Similarity	NPD6013	Approved
0.5859	Remote Similarity	NPD4195	Approved
0.5854	Remote Similarity	NPD5983	Phase 2
0.5849	Remote Similarity	NPD5785	Approved
0.5842	Remote Similarity	NPD6435	Approved
0.5842	Remote Similarity	NPD3667	Approved
0.5841	Remote Similarity	NPD5174	Approved
0.5841	Remote Similarity	NPD5175	Approved
0.5833	Remote Similarity	NPD5282	Discontinued
0.5827	Remote Similarity	NPD7736	Approved
0.5812	Remote Similarity	NPD7102	Approved
0.5812	Remote Similarity	NPD7290	Approved
0.5812	Remote Similarity	NPD6883	Approved
0.5804	Remote Similarity	NPD5223	Approved
0.58	Remote Similarity	NPD7509	Discontinued
0.5794	Remote Similarity	NPD7983	Approved
0.5784	Remote Similarity	NPD7154	Phase 3
0.5784	Remote Similarity	NPD5362	Discontinued
0.578	Remote Similarity	NPD4629	Approved
0.578	Remote Similarity	NPD5210	Approved
0.5776	Remote Similarity	NPD6011	Approved
0.5776	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD8264	Approved
0.5769	Remote Similarity	NPD3618	Phase 1
0.5766	Remote Similarity	NPD5696	Approved
0.5763	Remote Similarity	NPD6650	Approved
0.5763	Remote Similarity	NPD6869	Approved
0.5763	Remote Similarity	NPD6847	Approved
0.5763	Remote Similarity	NPD8130	Phase 1
0.5763	Remote Similarity	NPD6649	Approved
0.5763	Remote Similarity	NPD6617	Approved
0.576	Remote Similarity	NPD6067	Discontinued
0.5748	Remote Similarity	NPD8074	Phase 3
0.5745	Remote Similarity	NPD6923	Approved
0.5745	Remote Similarity	NPD6922	Approved
0.5741	Remote Similarity	NPD6399	Phase 3
0.5741	Remote Similarity	NPD5779	Approved
0.5741	Remote Similarity	NPD5778	Approved
0.5739	Remote Similarity	NPD4767	Approved
0.5739	Remote Similarity	NPD4768	Approved
0.5729	Remote Similarity	NPD4732	Discontinued
0.5728	Remote Similarity	NPD4786	Approved
0.5714	Remote Similarity	NPD6882	Approved
0.5703	Remote Similarity	NPD6033	Approved
0.5702	Remote Similarity	NPD4754	Approved
0.5691	Remote Similarity	NPD4522	Approved
0.5686	Remote Similarity	NPD4221	Approved
0.5686	Remote Similarity	NPD4223	Phase 3
0.5684	Remote Similarity	NPD7143	Approved
0.5684	Remote Similarity	NPD7144	Approved
0.5682	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD1694	Approved
0.5673	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD6336	Discontinued
0.5652	Remote Similarity	NPD2685	Clinical (unspecified phase)

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