NPASS Compound

Structure

CID228190 OpenBabel06191716022D 59 65 0 0 1 0 0 0 0 0999 V2000 0.2896 -1.3624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2731 -1.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3495 3.4074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8930 2.9150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4760 0.8424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3495 -0.5320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6437 2.4226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4966 2.9150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3124 -0.1210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0553 1.4377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0553 4.3923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2024 3.8999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2918 -0.0180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2024 0.9453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9290 1.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3400 0.3563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8153 7.6369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4006 2.0621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6437 1.4377 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9118 0.7787 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7550 0.8942 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3552 0.3563 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0835 6.9779 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0553 2.4226 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3495 2.4226 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9082 3.8999 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8627 -0.4966 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1468 7.2823 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8779 -0.4966 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4149 6.6233 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3855 0.3563 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6197 5.6599 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7035 -0.0893 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8779 1.2092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5563 5.3556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2310 1.9519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8260 -0.5364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2024 2.9150 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9082 2.9150 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4966 0.9453 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3495 1.4377 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0515 0.9835 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.8324 -0.4966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6106 8.6002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6325 1.3413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3552 -1.3495 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9420 8.2456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3855 -1.3495 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4783 6.9276 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4006 0.3563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8878 5.0009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5294 -0.6257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1594 2.2806 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5179 2.5915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3855 2.0621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8627 1.2092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2882 6.0146 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7611 4.3923 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 1 37 1 0 0 0 0 2 37 1 0 0 0 0 5 40 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 25 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 10 24 1 0 0 0 0 11 12 1 0 0 0 0 11 26 1 0 0 0 0 12 38 1 0 0 0 0 13 40 1 0 0 0 0 14 41 1 0 0 0 0 15 21 1 0 0 0 0 15 42 1 0 0 0 0 16 43 1 0 0 0 0 17 44 1 0 0 0 0 18 39 1 0 0 0 0 18 55 1 0 0 0 0 19 20 1 0 0 0 0 19 40 1 6 0 0 0 20 9 1 1 0 0 0 20 42 1 0 0 0 0 21 33 1 0 0 0 0 21 45 1 6 0 0 0 22 16 1 1 0 0 0 22 27 1 0 0 0 0 22 56 1 0 0 0 0 23 17 1 6 0 0 0 23 28 1 0 0 0 0 23 57 1 0 0 0 0 24 38 1 1 0 0 0 24 39 1 0 0 0 0 25 38 1 1 0 0 0 25 41 1 0 0 0 0 26 39 1 1 0 0 0 26 58 1 0 0 0 0 27 29 1 0 0 0 0 27 46 1 6 0 0 0 28 30 1 0 0 0 0 28 47 1 1 0 0 0 29 31 1 0 0 0 0 29 48 1 1 0 0 0 30 32 1 0 0 0 0 30 49 1 6 0 0 0 31 34 1 0 0 0 0 31 50 1 6 0 0 0 32 35 1 0 0 0 0 32 51 1 1 0 0 0 33 37 1 0 0 0 0 33 52 1 6 0 0 0 34 55 1 1 0 0 0 34 56 1 0 0 0 0 35 57 1 0 0 0 0 35 58 1 6 0 0 0 36 53 2 0 0 0 0 36 54 1 0 0 0 0 37 59 1 0 0 0 0 38 3 1 1 0 0 0 39 4 1 6 0 0 0 40 41 1 1 0 0 0 41 6 1 1 0 0 0 42 36 1 1 0 0 0 42 59 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	846.46
Volume:	821.89
LogP:	1.066
LogD:	1.642
LogS:	-2.746
# Rotatable Bonds:	9
TPSA:	285.75
# H-Bond Aceptor:	17
# H-Bond Donor:	11
# Rings:	7
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.129
Synthetic Accessibility Score:	6.194
Fsp3:	0.976
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.179
MDCK Permeability:	8.828726276988164e-05
Pgp-inhibitor:	0.68
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.981
20% Bioavailability (F20%):	0.946
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.111
Plasma Protein Binding (PPB):	67.24073791503906%
Volume Distribution (VD):	0.102
Pgp-substrate:	10.395588874816895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.407
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.314
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.013

ADMET: Excretion

Clearance (CL):	0.805
Half-life (T1/2):	0.781

ADMET: Toxicity

hERG Blockers:	0.229
Human Hepatotoxicity (H-HT):	0.234
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.101
Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.11
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC228190

Natural Product ID:	NPC228190
*Common Name:**	Gentirigeoside C
IUPAC Name:	(2S,4S,5S)-4,5-dihydroxy-6,6-dimethyl-2-[(3S,4S,5R,8R,9R,10R,13R,14R,17S)-4,8,10,14-tetramethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]oxane-2-carboxylic acid
Synonyms:	gentirigeoside C
Standard InCHIKey:	AQYVSJSIOILIQJ-CUWSSRGUSA-N
Standard InCHI:	InChI=1S/C42H70O17/c1-37(2)33(52)21(45)15-42(59-37,36(53)54)20-9-13-40(5)19(20)7-8-25-38(3)12-11-26(58-35-32(51)30(49)28(47)23(17-44)57-35)39(4,24(38)10-14-41(25,40)6)18-55-34-31(50)29(48)27(46)22(16-43)56-34/h19-35,43-52H,7-18H2,1-6H3,(H,53,54)/t19-,20+,21+,22-,23-,24-,25-,26+,27-,28-,29+,30+,31-,32-,33+,34-,35+,38+,39-,40-,41-,42+/m1/s1
SMILES:	CC1(C)[C@H]([C@H](C[C@]([C@H]2CC[C@]3(C)[C@@H]2CC[C@@H]2[C@@]4(C)CC[C@@H]([C@](C)(CO[C@H]5[C@@H]([C@H]([C@@H]([C@@H](CO)O5)O)O)O)[C@@H]4CC[C@@]32C)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)(C(=O)O)O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL373539
PubChem CID:	44422966
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	roots	n.a.	n.a.	PMID[17375953]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20813533]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21043460]
NPO27624	Swartzia simplex	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26654828]
NPO12009	Abies pinsapo	Species	Pinaceae	Eukaryota	Wood	n.a.	n.a.	PMID[7931362]
NPO16073	Sarcomelicope megistophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19120	Strychnos aculeata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16646	Artemisia campestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15856	Podocarpus hallii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17368	Erythrina senegalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18843	Antirrhinum majus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16073	Sarcomelicope megistophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16646	Artemisia campestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18843	Antirrhinum majus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19120	Strychnos aculeata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15856	Podocarpus hallii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16817	Aglaia argentea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17368	Erythrina senegalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15856	Podocarpus hallii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18843	Antirrhinum majus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16646	Artemisia campestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18372	Lobophytum crassospiculatum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15518	Streptomyces netropsis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18843	Antirrhinum majus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16817	Aglaia argentea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13251	Iris nertchinskia	Species	Tarachodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12009	Abies pinsapo	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19120	Strychnos aculeata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15856	Podocarpus hallii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18511	Latimeria chalumnae	Species	Coelacanthidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17368	Erythrina senegalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17711	Sphenoclea zeylanica	Species	Sphenocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27624	Swartzia simplex	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14721	Dentitheca habereri	Species	Plumulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16073	Sarcomelicope megistophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16646	Artemisia campestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3046	Schisandra bicolor	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17699	Solanum glaucophyllum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17054	Streptomyces gardneri	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16958	Jurinea albicaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18234	Gentiana rigescens	Species	Gentianaceae	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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	8.0	mm	PMID[503790]

☑ 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 NPC228190 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	557
0.1-0.2	3944
0.2-0.3	9397
0.3-0.4	12292
0.4-0.5	7154
0.5-0.6	4583
0.6-0.7	2573
0.7-0.8	1754
0.8-0.85	319
0.85-0.9	95
0.9-0.95	26
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC236753
0.98	High Similarity	NPC203974
0.9346	High Similarity	NPC179429
0.932	High Similarity	NPC469826
0.9238	High Similarity	NPC469824
0.9029	High Similarity	NPC469827
0.9	High Similarity	NPC472273
0.8952	High Similarity	NPC472079
0.8868	High Similarity	NPC469825
0.8857	High Similarity	NPC126753
0.8839	High Similarity	NPC470478
0.8835	High Similarity	NPC310031
0.8835	High Similarity	NPC80191
0.8807	High Similarity	NPC477465
0.8796	High Similarity	NPC477492
0.8796	High Similarity	NPC477489
0.8785	High Similarity	NPC470622
0.8774	High Similarity	NPC92890
0.8774	High Similarity	NPC475319
0.8774	High Similarity	NPC202898
0.8762	High Similarity	NPC215408
0.875	High Similarity	NPC34562
0.8692	High Similarity	NPC273002
0.8692	High Similarity	NPC208333
0.8692	High Similarity	NPC94086
0.8692	High Similarity	NPC220836
0.8692	High Similarity	NPC227879
0.8692	High Similarity	NPC233433
0.8692	High Similarity	NPC92297
0.8692	High Similarity	NPC473817
0.8641	High Similarity	NPC20028
0.8627	High Similarity	NPC470591
0.8624	High Similarity	NPC157571
0.8614	High Similarity	NPC94582
0.8614	High Similarity	NPC57964
0.8611	High Similarity	NPC471431
0.8598	High Similarity	NPC207693
0.8585	High Similarity	NPC119628
0.8585	High Similarity	NPC158051
0.8585	High Similarity	NPC158367
0.8558	High Similarity	NPC477172
0.8534	High Similarity	NPC273962
0.8532	High Similarity	NPC204392
0.8532	High Similarity	NPC275668
0.8532	High Similarity	NPC91838
0.8532	High Similarity	NPC473062
0.8532	High Similarity	NPC240734
0.8532	High Similarity	NPC1876
0.8529	High Similarity	NPC237071
0.8529	High Similarity	NPC238796
0.8529	High Similarity	NPC203434
0.8519	High Similarity	NPC22709
0.8519	High Similarity	NPC87393
0.8505	High Similarity	NPC475234
0.8505	High Similarity	NPC138219
0.8505	High Similarity	NPC40716
0.8505	High Similarity	NPC475630
0.8491	Intermediate Similarity	NPC267637
0.8468	Intermediate Similarity	NPC79193
0.8447	Intermediate Similarity	NPC210157
0.844	Intermediate Similarity	NPC66513
0.8431	Intermediate Similarity	NPC215570
0.8426	Intermediate Similarity	NPC231566
0.8426	Intermediate Similarity	NPC473688
0.8426	Intermediate Similarity	NPC262567
0.8426	Intermediate Similarity	NPC471626
0.8411	Intermediate Similarity	NPC184805
0.8411	Intermediate Similarity	NPC273189
0.8396	Intermediate Similarity	NPC107385
0.8381	Intermediate Similarity	NPC475574
0.8381	Intermediate Similarity	NPC476838
0.8381	Intermediate Similarity	NPC476839
0.8378	Intermediate Similarity	NPC146563
0.835	Intermediate Similarity	NPC296936
0.8349	Intermediate Similarity	NPC473844
0.8349	Intermediate Similarity	NPC51947
0.8333	Intermediate Similarity	NPC151214
0.8333	Intermediate Similarity	NPC287269
0.8333	Intermediate Similarity	NPC305418
0.8333	Intermediate Similarity	NPC192791
0.8333	Intermediate Similarity	NPC191915
0.8333	Intermediate Similarity	NPC471430
0.8318	Intermediate Similarity	NPC470167
0.8304	Intermediate Similarity	NPC54395
0.8304	Intermediate Similarity	NPC469821
0.8302	Intermediate Similarity	NPC470172
0.8302	Intermediate Similarity	NPC471254
0.8302	Intermediate Similarity	NPC80640
0.83	Intermediate Similarity	NPC131466
0.8291	Intermediate Similarity	NPC130229
0.8286	Intermediate Similarity	NPC41843
0.8269	Intermediate Similarity	NPC471241
0.8269	Intermediate Similarity	NPC470632
0.8269	Intermediate Similarity	NPC74466
0.8257	Intermediate Similarity	NPC88744
0.8235	Intermediate Similarity	NPC172838
0.8235	Intermediate Similarity	NPC137004
0.823	Intermediate Similarity	NPC469823
0.823	Intermediate Similarity	NPC472718
0.823	Intermediate Similarity	NPC469820
0.823	Intermediate Similarity	NPC137414
0.8224	Intermediate Similarity	NPC473406
0.8224	Intermediate Similarity	NPC471253
0.8214	Intermediate Similarity	NPC477074
0.8214	Intermediate Similarity	NPC97002
0.8208	Intermediate Similarity	NPC108227
0.8208	Intermediate Similarity	NPC476512
0.8208	Intermediate Similarity	NPC472081
0.8205	Intermediate Similarity	NPC30735
0.8205	Intermediate Similarity	NPC235405
0.8205	Intermediate Similarity	NPC281148
0.8198	Intermediate Similarity	NPC11035
0.8198	Intermediate Similarity	NPC274833
0.819	Intermediate Similarity	NPC169727
0.819	Intermediate Similarity	NPC86222
0.819	Intermediate Similarity	NPC31838
0.819	Intermediate Similarity	NPC471374
0.819	Intermediate Similarity	NPC194310
0.819	Intermediate Similarity	NPC159309
0.819	Intermediate Similarity	NPC471375
0.819	Intermediate Similarity	NPC301449
0.819	Intermediate Similarity	NPC11242
0.819	Intermediate Similarity	NPC62725
0.819	Intermediate Similarity	NPC223301
0.819	Intermediate Similarity	NPC297263
0.819	Intermediate Similarity	NPC114484
0.819	Intermediate Similarity	NPC104372
0.819	Intermediate Similarity	NPC258815
0.819	Intermediate Similarity	NPC64715
0.819	Intermediate Similarity	NPC171544
0.819	Intermediate Similarity	NPC258789
0.819	Intermediate Similarity	NPC241310
0.819	Intermediate Similarity	NPC131841
0.819	Intermediate Similarity	NPC222580
0.819	Intermediate Similarity	NPC209798
0.819	Intermediate Similarity	NPC47567
0.819	Intermediate Similarity	NPC412
0.819	Intermediate Similarity	NPC22956
0.8182	Intermediate Similarity	NPC91583
0.8182	Intermediate Similarity	NPC240125
0.8173	Intermediate Similarity	NPC139271
0.8173	Intermediate Similarity	NPC252056
0.8173	Intermediate Similarity	NPC475785
0.8173	Intermediate Similarity	NPC475765
0.8173	Intermediate Similarity	NPC304011
0.8158	Intermediate Similarity	NPC156651
0.8148	Intermediate Similarity	NPC327093
0.8137	Intermediate Similarity	NPC229801
0.8137	Intermediate Similarity	NPC210759
0.8137	Intermediate Similarity	NPC307167
0.8136	Intermediate Similarity	NPC470477
0.8131	Intermediate Similarity	NPC310138
0.8131	Intermediate Similarity	NPC114700
0.8131	Intermediate Similarity	NPC134967
0.8131	Intermediate Similarity	NPC470029
0.8125	Intermediate Similarity	NPC472719
0.8125	Intermediate Similarity	NPC207845
0.8125	Intermediate Similarity	NPC470543
0.812	Intermediate Similarity	NPC213952
0.812	Intermediate Similarity	NPC475591
0.812	Intermediate Similarity	NPC10607
0.812	Intermediate Similarity	NPC107966
0.812	Intermediate Similarity	NPC40775
0.812	Intermediate Similarity	NPC236870
0.812	Intermediate Similarity	NPC249848
0.812	Intermediate Similarity	NPC131824
0.812	Intermediate Similarity	NPC80986
0.812	Intermediate Similarity	NPC162574
0.812	Intermediate Similarity	NPC187290
0.812	Intermediate Similarity	NPC235438
0.812	Intermediate Similarity	NPC21691
0.812	Intermediate Similarity	NPC4749
0.8113	Intermediate Similarity	NPC471428
0.8113	Intermediate Similarity	NPC471426
0.8113	Intermediate Similarity	NPC80417
0.8113	Intermediate Similarity	NPC51579
0.8113	Intermediate Similarity	NPC471427
0.8103	Intermediate Similarity	NPC118440
0.8103	Intermediate Similarity	NPC236657
0.81	Intermediate Similarity	NPC140446
0.81	Intermediate Similarity	NPC43912
0.8091	Intermediate Similarity	NPC316930
0.8087	Intermediate Similarity	NPC469822
0.8087	Intermediate Similarity	NPC109588
0.8077	Intermediate Similarity	NPC477494
0.8073	Intermediate Similarity	NPC306776
0.8073	Intermediate Similarity	NPC166079
0.807	Intermediate Similarity	NPC475490
0.8067	Intermediate Similarity	NPC470218
0.8067	Intermediate Similarity	NPC469947
0.8067	Intermediate Similarity	NPC181066
0.8067	Intermediate Similarity	NPC104427
0.8056	Intermediate Similarity	NPC139181
0.8056	Intermediate Similarity	NPC476837
0.8056	Intermediate Similarity	NPC97260
0.8051	Intermediate Similarity	NPC302543
0.8051	Intermediate Similarity	NPC200049
0.8051	Intermediate Similarity	NPC257211
0.8051	Intermediate Similarity	NPC258617
0.8051	Intermediate Similarity	NPC228701

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 NPC228190 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	591
0.1-0.2	3920
0.2-0.3	3080
0.3-0.4	872
0.4-0.5	351
0.5-0.6	209
0.6-0.7	102
0.7-0.8	21
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD8170	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD8133	Approved
0.8158	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD8328	Phase 3
0.7885	Intermediate Similarity	NPD8171	Discontinued
0.7544	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7736	Approved
0.7339	Intermediate Similarity	NPD7507	Approved
0.7213	Intermediate Similarity	NPD8377	Approved
0.7213	Intermediate Similarity	NPD8294	Approved
0.72	Intermediate Similarity	NPD6118	Approved
0.72	Intermediate Similarity	NPD6115	Approved
0.72	Intermediate Similarity	NPD6114	Approved
0.72	Intermediate Similarity	NPD6697	Approved
0.7167	Intermediate Similarity	NPD6940	Discontinued
0.7165	Intermediate Similarity	NPD7319	Approved
0.7154	Intermediate Similarity	NPD8296	Approved
0.7154	Intermediate Similarity	NPD8380	Approved
0.7154	Intermediate Similarity	NPD8335	Approved
0.7154	Intermediate Similarity	NPD8379	Approved
0.7154	Intermediate Similarity	NPD8378	Approved
0.7143	Intermediate Similarity	NPD8293	Discontinued
0.71	Intermediate Similarity	NPD6116	Phase 1
0.7019	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3669	Approved
0.7016	Intermediate Similarity	NPD8033	Approved
0.7009	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6117	Approved
0.699	Remote Similarity	NPD1780	Approved
0.699	Remote Similarity	NPD1779	Approved
0.696	Remote Similarity	NPD6370	Approved
0.693	Remote Similarity	NPD1700	Approved
0.6917	Remote Similarity	NPD6882	Approved
0.6917	Remote Similarity	NPD8297	Approved
0.6897	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7492	Approved
0.6829	Remote Similarity	NPD6009	Approved
0.6818	Remote Similarity	NPD8034	Phase 2
0.6818	Remote Similarity	NPD8035	Phase 2
0.6807	Remote Similarity	NPD6372	Approved
0.6807	Remote Similarity	NPD6373	Approved
0.68	Remote Similarity	NPD6059	Approved
0.68	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6319	Approved
0.68	Remote Similarity	NPD6054	Approved
0.6797	Remote Similarity	NPD6616	Approved
0.6796	Remote Similarity	NPD7329	Approved
0.678	Remote Similarity	NPD6412	Phase 2
0.6774	Remote Similarity	NPD7328	Approved
0.6774	Remote Similarity	NPD7327	Approved
0.6746	Remote Similarity	NPD8515	Approved
0.6746	Remote Similarity	NPD8513	Phase 3
0.6746	Remote Similarity	NPD8516	Approved
0.6746	Remote Similarity	NPD8517	Approved
0.6744	Remote Similarity	NPD7078	Approved
0.6733	Remote Similarity	NPD3703	Phase 2
0.6731	Remote Similarity	NPD6928	Phase 2
0.672	Remote Similarity	NPD7516	Approved
0.6695	Remote Similarity	NPD7128	Approved
0.6695	Remote Similarity	NPD6402	Approved
0.6695	Remote Similarity	NPD6675	Approved
0.6695	Remote Similarity	NPD5739	Approved
0.6694	Remote Similarity	NPD6649	Approved
0.6694	Remote Similarity	NPD6650	Approved
0.6614	Remote Similarity	NPD6015	Approved
0.6614	Remote Similarity	NPD6016	Approved
0.6585	Remote Similarity	NPD4632	Approved
0.6583	Remote Similarity	NPD7320	Approved
0.6583	Remote Similarity	NPD6881	Approved
0.6583	Remote Similarity	NPD6899	Approved
0.6583	Remote Similarity	NPD6686	Approved
0.6569	Remote Similarity	NPD3702	Approved
0.6562	Remote Similarity	NPD5988	Approved
0.6557	Remote Similarity	NPD8130	Phase 1
0.65	Remote Similarity	NPD5701	Approved
0.65	Remote Similarity	NPD5697	Approved
0.6484	Remote Similarity	NPD6921	Approved
0.6484	Remote Similarity	NPD7503	Approved
0.6475	Remote Similarity	NPD7102	Approved
0.6475	Remote Similarity	NPD6883	Approved
0.6475	Remote Similarity	NPD7290	Approved
0.6441	Remote Similarity	NPD8084	Approved
0.6441	Remote Similarity	NPD8083	Approved
0.6441	Remote Similarity	NPD8086	Approved
0.6441	Remote Similarity	NPD8138	Approved
0.6441	Remote Similarity	NPD8082	Approved
0.6441	Remote Similarity	NPD8085	Approved
0.6441	Remote Similarity	NPD8139	Approved
0.6436	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6617	Approved
0.6423	Remote Similarity	NPD6869	Approved
0.6423	Remote Similarity	NPD6847	Approved
0.6422	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD8393	Approved
0.64	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6014	Approved
0.6393	Remote Similarity	NPD6013	Approved
0.6393	Remote Similarity	NPD6012	Approved
0.6387	Remote Similarity	NPD8275	Approved
0.6387	Remote Similarity	NPD8276	Approved
0.6385	Remote Similarity	NPD7604	Phase 2
0.6357	Remote Similarity	NPD5983	Phase 2
0.6337	Remote Similarity	NPD4789	Approved
0.6333	Remote Similarity	NPD8081	Approved
0.6316	Remote Similarity	NPD6033	Approved
0.6311	Remote Similarity	NPD1811	Approved
0.6311	Remote Similarity	NPD6011	Approved
0.6311	Remote Similarity	NPD1810	Approved
0.629	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD6336	Discontinued
0.6238	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5360	Phase 3
0.6134	Remote Similarity	NPD8418	Phase 2
0.6129	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6081	Approved
0.6117	Remote Similarity	NPD5777	Approved
0.6102	Remote Similarity	NPD4755	Approved
0.6102	Remote Similarity	NPD6084	Phase 2
0.6102	Remote Similarity	NPD6083	Phase 2
0.6102	Remote Similarity	NPD7902	Approved
0.6098	Remote Similarity	NPD8140	Approved
0.6098	Remote Similarity	NPD8307	Discontinued
0.6094	Remote Similarity	NPD6274	Approved
0.608	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.608	Remote Similarity	NPD4634	Approved
0.6077	Remote Similarity	NPD7101	Approved
0.6077	Remote Similarity	NPD7100	Approved
0.6068	Remote Similarity	NPD7991	Discontinued
0.6058	Remote Similarity	NPD3181	Approved
0.605	Remote Similarity	NPD7638	Approved
0.6047	Remote Similarity	NPD7115	Discovery
0.6034	Remote Similarity	NPD6399	Phase 3
0.6033	Remote Similarity	NPD8300	Approved
0.6033	Remote Similarity	NPD8301	Approved
0.6019	Remote Similarity	NPD4244	Approved
0.6019	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD2686	Approved
0.6019	Remote Similarity	NPD2687	Approved
0.6019	Remote Similarity	NPD2254	Approved
0.6019	Remote Similarity	NPD4245	Approved
0.6016	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD8306	Approved
0.6	Remote Similarity	NPD8305	Approved
0.6	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD6335	Approved
0.6	Remote Similarity	NPD7639	Approved
0.6	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD5285	Approved
0.5985	Remote Similarity	NPD6909	Approved
0.5985	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD6908	Approved
0.5983	Remote Similarity	NPD7748	Approved
0.5952	Remote Similarity	NPD8087	Discontinued
0.5941	Remote Similarity	NPD4224	Phase 2
0.594	Remote Similarity	NPD8080	Discontinued
0.5923	Remote Similarity	NPD6317	Approved
0.5922	Remote Similarity	NPD3698	Phase 2
0.592	Remote Similarity	NPD8174	Phase 2
0.5917	Remote Similarity	NPD5696	Approved
0.5902	Remote Similarity	NPD5211	Phase 2
0.5902	Remote Similarity	NPD4633	Approved
0.5902	Remote Similarity	NPD5224	Approved
0.5902	Remote Similarity	NPD5225	Approved
0.5902	Remote Similarity	NPD7632	Discontinued
0.5902	Remote Similarity	NPD5226	Approved
0.5896	Remote Similarity	NPD6067	Discontinued
0.5887	Remote Similarity	NPD4768	Approved
0.5887	Remote Similarity	NPD4767	Approved
0.5882	Remote Similarity	NPD4697	Phase 3
0.5882	Remote Similarity	NPD8074	Phase 3
0.5882	Remote Similarity	NPD897	Approved
0.5882	Remote Similarity	NPD896	Approved
0.5882	Remote Similarity	NPD898	Approved
0.5878	Remote Similarity	NPD6313	Approved
0.5878	Remote Similarity	NPD6314	Approved
0.5854	Remote Similarity	NPD5174	Approved
0.5854	Remote Similarity	NPD5175	Approved
0.5847	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD7900	Approved
0.5846	Remote Similarity	NPD6868	Approved
0.5842	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.584	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.582	Remote Similarity	NPD5223	Approved
0.5812	Remote Similarity	NPD7515	Phase 2
0.581	Remote Similarity	NPD4758	Discontinued
0.5806	Remote Similarity	NPD5141	Approved
0.5802	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD5695	Phase 3
0.5794	Remote Similarity	NPD4730	Approved
0.5794	Remote Similarity	NPD4729	Approved
0.5789	Remote Similarity	NPD8346	Approved
0.5789	Remote Similarity	NPD8347	Approved
0.5789	Remote Similarity	NPD8345	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