NPASS Compound

Structure

CID192810 OpenBabel06191715582D 23 24 0 0 1 0 0 0 0 0999 V2000 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 20 1 0 0 0 0 2 21 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 6 1 0 0 0 0 4 8 2 0 0 0 0 5 15 1 0 0 0 0 6 22 1 0 0 0 0 7 10 2 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 8 21 1 0 0 0 0 9 5 1 6 0 0 0 9 11 1 0 0 0 0 9 23 1 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 1 0 0 0 12 13 1 0 0 0 0 12 18 1 6 0 0 0 13 14 1 0 0 0 0 13 19 1 1 0 0 0 14 22 1 6 0 0 0 14 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.11
Volume:	304.79
LogP:	-0.624
LogD:	-0.344
LogS:	-0.83
# Rotatable Bonds:	5
TPSA:	138.07
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.44
Synthetic Accessibility Score:	3.497
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.106
MDCK Permeability:	5.783678716397844e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.274
Human Intestinal Absorption (HIA):	0.719
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.809

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.449
Plasma Protein Binding (PPB):	44.266021728515625%
Volume Distribution (VD):	0.505
Pgp-substrate:	27.404048919677734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.589
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.808
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.308
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.365
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.033

ADMET: Excretion

Clearance (CL):	4.384
Half-life (T1/2):	0.898

ADMET: Toxicity

hERG Blockers:	0.171
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.172
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.7
Carcinogencity:	0.1
Eye Corrosion:	0.011
Eye Irritation:	0.118
Respiratory Toxicity:	0.045

Download Data

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

Natural Product: NPC192810

Natural Product ID:	NPC192810
*Common Name:**	Koaburaside
IUPAC Name:	(2S,3R,4S,5S,6R)-2-(4-hydroxy-3,5-dimethoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	Koaburaside
Standard InCHIKey:	SWHCKWOYUSDWOF-RGCYKPLRSA-N
Standard InCHI:	InChI=1S/C14H20O9/c1-20-7-3-6(4-8(21-2)10(7)16)22-14-13(19)12(18)11(17)9(5-15)23-14/h3-4,9,11-19H,5H2,1-2H3/t9-,11-,12+,13-,14-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(OC)c(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513117
PubChem CID:	5318820
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
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17124632]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17124632]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125236]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	roots	n.a.	n.a.	PMID[17125236]
NPO18521	Capparis flavicans	Species	Capparaceae	Eukaryota	aerial parts	Khon Kaen Province, Thailand	2006-Aug	PMID[19943620]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	bark	n.a.	PMID[26767291]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26767291]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27128895]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	Resinous Wood	n.a.	n.a.	PMID[29227647]
NPO16693	Byrsonima crassifolia	Species	Malpighiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16693	Byrsonima crassifolia	Species	Malpighiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16693	Byrsonima crassifolia	Species	Malpighiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2340	Caulis spatholobi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO277	Caulis millettiae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO2340	Caulis spatholobi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15954	Pyrenula japonica	Species	Pyrenulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16326	Scopolia parviflora	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11755	Banisteriopsis caapi	Species	Malpighiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15740	Garcinia purpurea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO619	Ankistrodesmus braunii	Species	Selenastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14507.1	Quercus ithaburensis subsp. macrolepis	Subspecies	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17141	Lonchocarpus longistylus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16049	Cryptocarya pleurosperma	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17600	Gnathotrichus sulcatus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16210	Androcymbium palaestinum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15594	Aplidiopsis confluata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16693	Byrsonima crassifolia	Species	Malpighiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16326	Scopolia parviflora	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17444	Gleichenia japonica	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15954	Pyrenula japonica	Species	Pyrenulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12630	Senecio oxyodontus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14001	Ceroplastes pseudoceriferus	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17757	Plectranthus saccatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18071	Euryops pedunculatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18521	Capparis flavicans	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10751	Bothriocline laxa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17917	Thamnophis sirtalis	Species	Colubridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5016	Glossogyne tenuifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11280	Aphanoascus terreus	Species	Onygenaceae	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	6
Others	7

Activity Type	# Activity
Cell Line	12
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[507873]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[507873]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[507873]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[507873]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[507873]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	<	0.1	uM	PMID[507874]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[507874]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	2.0	uM	PMID[507874]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	37.0	uM	PMID[507874]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	70.0	uM	PMID[507874]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	>	90.0	%	PMID[507874]
NPT2	Others	Unspecified		IC50	>	10.0	ug.mL-1	PMID[507875]

☑ 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 NPC192810 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	365
0.1-0.2	2356
0.2-0.3	8668
0.3-0.4	11477
0.4-0.5	5130
0.5-0.6	7495
0.6-0.7	5663
0.7-0.8	1414
0.8-0.85	89
0.85-0.9	21
0.9-0.95	9
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9915	High Similarity	NPC221090
0.9914	High Similarity	NPC152722
0.9748	High Similarity	NPC189589
0.9748	High Similarity	NPC469622
0.9741	High Similarity	NPC276195
0.9667	High Similarity	NPC37074
0.9583	High Similarity	NPC298845
0.9504	High Similarity	NPC469621
0.9496	High Similarity	NPC217854
0.9431	High Similarity	NPC208769
0.9417	High Similarity	NPC25817
0.9355	High Similarity	NPC287780
0.9274	High Similarity	NPC60756
0.9262	High Similarity	NPC171533
0.9231	High Similarity	NPC9248
0.9206	High Similarity	NPC60982
0.9113	High Similarity	NPC247146
0.8974	High Similarity	NPC142319
0.8833	High Similarity	NPC228907
0.8702	High Similarity	NPC104167
0.8682	High Similarity	NPC299144
0.8682	High Similarity	NPC470270
0.8615	High Similarity	NPC132895
0.8615	High Similarity	NPC49074
0.8571	High Similarity	NPC12308
0.8571	High Similarity	NPC212770
0.8571	High Similarity	NPC98777
0.855	High Similarity	NPC251981
0.855	High Similarity	NPC107478
0.855	High Similarity	NPC13745
0.855	High Similarity	NPC48863
0.8548	High Similarity	NPC57751
0.8538	High Similarity	NPC162093
0.8496	Intermediate Similarity	NPC65530
0.8496	Intermediate Similarity	NPC59324
0.8473	Intermediate Similarity	NPC69513
0.8473	Intermediate Similarity	NPC215833
0.8462	Intermediate Similarity	NPC166168
0.8456	Intermediate Similarity	NPC252169
0.8455	Intermediate Similarity	NPC214289
0.8448	Intermediate Similarity	NPC232654
0.8443	Intermediate Similarity	NPC76915
0.8443	Intermediate Similarity	NPC151617
0.8421	Intermediate Similarity	NPC242028
0.8421	Intermediate Similarity	NPC203230
0.8421	Intermediate Similarity	NPC164857
0.8382	Intermediate Similarity	NPC469559
0.8382	Intermediate Similarity	NPC189115
0.8382	Intermediate Similarity	NPC475084
0.8376	Intermediate Similarity	NPC124712
0.8358	Intermediate Similarity	NPC195196
0.8346	Intermediate Similarity	NPC470236
0.8345	Intermediate Similarity	NPC227902
0.8333	Intermediate Similarity	NPC126216
0.8333	Intermediate Similarity	NPC105147
0.8333	Intermediate Similarity	NPC228875
0.832	Intermediate Similarity	NPC205850
0.8319	Intermediate Similarity	NPC247871
0.8309	Intermediate Similarity	NPC469661
0.8308	Intermediate Similarity	NPC248355
0.8308	Intermediate Similarity	NPC166040
0.8308	Intermediate Similarity	NPC307110
0.8286	Intermediate Similarity	NPC478237
0.8286	Intermediate Similarity	NPC175976
0.8271	Intermediate Similarity	NPC87696
0.8261	Intermediate Similarity	NPC25292
0.8261	Intermediate Similarity	NPC473045
0.8244	Intermediate Similarity	NPC262606
0.8231	Intermediate Similarity	NPC302378
0.8231	Intermediate Similarity	NPC40377
0.8217	Intermediate Similarity	NPC233559
0.8205	Intermediate Similarity	NPC307875
0.8201	Intermediate Similarity	NPC475096
0.8201	Intermediate Similarity	NPC161700
0.8201	Intermediate Similarity	NPC277867
0.8195	Intermediate Similarity	NPC115022
0.8195	Intermediate Similarity	NPC294166
0.8188	Intermediate Similarity	NPC473044
0.8182	Intermediate Similarity	NPC65942
0.8182	Intermediate Similarity	NPC248307
0.8168	Intermediate Similarity	NPC218003
0.8154	Intermediate Similarity	NPC140750
0.8143	Intermediate Similarity	NPC125755
0.8143	Intermediate Similarity	NPC99515
0.8143	Intermediate Similarity	NPC190714
0.8134	Intermediate Similarity	NPC310854
0.812	Intermediate Similarity	NPC303422
0.812	Intermediate Similarity	NPC252833
0.812	Intermediate Similarity	NPC26080
0.812	Intermediate Similarity	NPC165686
0.812	Intermediate Similarity	NPC85799
0.8116	Intermediate Similarity	NPC5262
0.8116	Intermediate Similarity	NPC472714
0.8112	Intermediate Similarity	NPC213197
0.811	Intermediate Similarity	NPC226712
0.8106	Intermediate Similarity	NPC80600
0.8106	Intermediate Similarity	NPC472024
0.8102	Intermediate Similarity	NPC210478
0.8099	Intermediate Similarity	NPC313334
0.8099	Intermediate Similarity	NPC212670
0.8099	Intermediate Similarity	NPC206264
0.8092	Intermediate Similarity	NPC198487
0.8088	Intermediate Similarity	NPC138738
0.8088	Intermediate Similarity	NPC470413
0.8085	Intermediate Similarity	NPC39657
0.8077	Intermediate Similarity	NPC110677
0.8074	Intermediate Similarity	NPC185778
0.8074	Intermediate Similarity	NPC238243
0.806	Intermediate Similarity	NPC6836
0.806	Intermediate Similarity	NPC25821
0.8058	Intermediate Similarity	NPC37793
0.8045	Intermediate Similarity	NPC121376
0.8031	Intermediate Similarity	NPC269242
0.803	Intermediate Similarity	NPC97326
0.803	Intermediate Similarity	NPC270849
0.803	Intermediate Similarity	NPC26653
0.8029	Intermediate Similarity	NPC100389
0.8028	Intermediate Similarity	NPC248132
0.8028	Intermediate Similarity	NPC130449
0.8015	Intermediate Similarity	NPC172818
0.8015	Intermediate Similarity	NPC25695
0.8015	Intermediate Similarity	NPC138350
0.8015	Intermediate Similarity	NPC3293
0.8015	Intermediate Similarity	NPC40664
0.8015	Intermediate Similarity	NPC216836
0.8015	Intermediate Similarity	NPC165482
0.8015	Intermediate Similarity	NPC186418
0.8015	Intermediate Similarity	NPC197723
0.8	Intermediate Similarity	NPC187774
0.8	Intermediate Similarity	NPC168579
0.8	Intermediate Similarity	NPC472713
0.8	Intermediate Similarity	NPC35731
0.8	Intermediate Similarity	NPC469313
0.8	Intermediate Similarity	NPC170694
0.8	Intermediate Similarity	NPC188555
0.8	Intermediate Similarity	NPC297342
0.8	Intermediate Similarity	NPC470881
0.8	Intermediate Similarity	NPC473046
0.8	Intermediate Similarity	NPC138227
0.8	Intermediate Similarity	NPC78809
0.8	Intermediate Similarity	NPC76176
0.8	Intermediate Similarity	NPC118385
0.8	Intermediate Similarity	NPC130496
0.8	Intermediate Similarity	NPC472712
0.7985	Intermediate Similarity	NPC7903
0.7985	Intermediate Similarity	NPC16208
0.7985	Intermediate Similarity	NPC35932
0.7985	Intermediate Similarity	NPC160991
0.7985	Intermediate Similarity	NPC184447
0.7972	Intermediate Similarity	NPC106138
0.7972	Intermediate Similarity	NPC286235
0.7972	Intermediate Similarity	NPC51328
0.7972	Intermediate Similarity	NPC55158
0.797	Intermediate Similarity	NPC470079
0.7958	Intermediate Similarity	NPC473480
0.7958	Intermediate Similarity	NPC15538
0.7958	Intermediate Similarity	NPC41844
0.7956	Intermediate Similarity	NPC262328
0.7956	Intermediate Similarity	NPC87777
0.7956	Intermediate Similarity	NPC124149
0.7953	Intermediate Similarity	NPC469708
0.7953	Intermediate Similarity	NPC60589
0.7943	Intermediate Similarity	NPC307466
0.7941	Intermediate Similarity	NPC472337
0.7917	Intermediate Similarity	NPC472710
0.7917	Intermediate Similarity	NPC472709
0.791	Intermediate Similarity	NPC472597
0.791	Intermediate Similarity	NPC469698
0.791	Intermediate Similarity	NPC475067
0.791	Intermediate Similarity	NPC9912
0.791	Intermediate Similarity	NPC473412
0.7902	Intermediate Similarity	NPC96294
0.7895	Intermediate Similarity	NPC45824
0.7891	Intermediate Similarity	NPC469412
0.7891	Intermediate Similarity	NPC198734
0.7883	Intermediate Similarity	NPC37468
0.7883	Intermediate Similarity	NPC52277
0.7883	Intermediate Similarity	NPC472336
0.7883	Intermediate Similarity	NPC177035
0.7883	Intermediate Similarity	NPC199459
0.7883	Intermediate Similarity	NPC472334
0.7883	Intermediate Similarity	NPC157554
0.7868	Intermediate Similarity	NPC187194
0.7863	Intermediate Similarity	NPC470510
0.7857	Intermediate Similarity	NPC157816
0.7846	Intermediate Similarity	NPC220598
0.7846	Intermediate Similarity	NPC165375
0.7842	Intermediate Similarity	NPC202700
0.7842	Intermediate Similarity	NPC106944
0.7836	Intermediate Similarity	NPC469612
0.7836	Intermediate Similarity	NPC220935
0.7836	Intermediate Similarity	NPC472338
0.7836	Intermediate Similarity	NPC469614
0.7836	Intermediate Similarity	NPC214860
0.7836	Intermediate Similarity	NPC474491
0.7826	Intermediate Similarity	NPC102904
0.7826	Intermediate Similarity	NPC176051
0.7826	Intermediate Similarity	NPC107551
0.7826	Intermediate Similarity	NPC474039
0.7826	Intermediate Similarity	NPC326797

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 NPC192810 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	1100
0.2-0.3	2949
0.3-0.4	2585
0.4-0.5	1288
0.5-0.6	761
0.6-0.7	164
0.7-0.8	10
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.811	Intermediate Similarity	NPD1091	Approved
0.8099	Intermediate Similarity	NPD1653	Approved
0.7949	Intermediate Similarity	NPD291	Approved
0.7787	Intermediate Similarity	NPD556	Approved
0.763	Intermediate Similarity	NPD3027	Phase 3
0.7591	Intermediate Similarity	NPD1613	Approved
0.7591	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD3454	Phase 3
0.7442	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD9296	Approved
0.7353	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD9365	Approved
0.7125	Intermediate Similarity	NPD7054	Approved
0.7121	Intermediate Similarity	NPD7533	Approved
0.7121	Intermediate Similarity	NPD7534	Approved
0.7081	Intermediate Similarity	NPD7074	Phase 3
0.7081	Intermediate Similarity	NPD7472	Approved
0.7068	Intermediate Similarity	NPD1357	Approved
0.7055	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7266	Discontinued
0.7009	Intermediate Similarity	NPD9295	Approved
0.6957	Remote Similarity	NPD3818	Discontinued
0.6957	Remote Similarity	NPD7228	Approved
0.6943	Remote Similarity	NPD6234	Discontinued
0.6939	Remote Similarity	NPD6674	Discontinued
0.6933	Remote Similarity	NPD6797	Phase 2
0.6929	Remote Similarity	NPD290	Approved
0.6923	Remote Similarity	NPD9094	Approved
0.6912	Remote Similarity	NPD3705	Approved
0.689	Remote Similarity	NPD7251	Discontinued
0.6879	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1548	Phase 1
0.685	Remote Similarity	NPD968	Approved
0.6848	Remote Similarity	NPD7808	Phase 3
0.6839	Remote Similarity	NPD37	Approved
0.6824	Remote Similarity	NPD1652	Phase 2
0.6815	Remote Similarity	NPD4966	Approved
0.6815	Remote Similarity	NPD4965	Approved
0.6815	Remote Similarity	NPD4967	Phase 2
0.6812	Remote Similarity	NPD2982	Phase 2
0.6812	Remote Similarity	NPD2983	Phase 2
0.6809	Remote Similarity	NPD4908	Phase 1
0.6803	Remote Similarity	NPD521	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD9552	Approved
0.6788	Remote Similarity	NPD1610	Phase 2
0.6767	Remote Similarity	NPD191	Approved
0.6739	Remote Similarity	NPD2981	Phase 2
0.6731	Remote Similarity	NPD1934	Approved
0.6718	Remote Similarity	NPD228	Approved
0.6713	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD1797	Approved
0.6691	Remote Similarity	NPD1798	Approved
0.6691	Remote Similarity	NPD4749	Approved
0.6688	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD422	Phase 1
0.6667	Remote Similarity	NPD7843	Approved
0.6646	Remote Similarity	NPD7199	Phase 2
0.6626	Remote Similarity	NPD6166	Phase 2
0.6626	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.662	Remote Similarity	NPD3018	Phase 2
0.6615	Remote Similarity	NPD2684	Approved
0.6606	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5058	Phase 3
0.6567	Remote Similarity	NPD9299	Approved
0.6562	Remote Similarity	NPD9501	Approved
0.6544	Remote Similarity	NPD1103	Approved
0.6544	Remote Similarity	NPD1102	Approved
0.6519	Remote Similarity	NPD6671	Approved
0.6519	Remote Similarity	NPD3383	Approved
0.6519	Remote Similarity	NPD7157	Approved
0.6519	Remote Similarity	NPD3384	Approved
0.6519	Remote Similarity	NPD3382	Approved
0.6503	Remote Similarity	NPD2861	Phase 2
0.6488	Remote Similarity	NPD7240	Approved
0.6488	Remote Similarity	NPD6559	Discontinued
0.6483	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD9093	Approved
0.6463	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD230	Phase 1
0.6463	Remote Similarity	NPD5124	Phase 1
0.6463	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD6841	Approved
0.6453	Remote Similarity	NPD6843	Phase 3
0.6453	Remote Similarity	NPD6842	Approved
0.6438	Remote Similarity	NPD6233	Phase 2
0.6419	Remote Similarity	NPD2224	Approved
0.6419	Remote Similarity	NPD2223	Approved
0.6414	Remote Similarity	NPD4625	Phase 3
0.641	Remote Similarity	NPD9089	Approved
0.6407	Remote Similarity	NPD5844	Phase 1
0.6398	Remote Similarity	NPD3882	Suspended
0.6395	Remote Similarity	NPD1558	Phase 1
0.6392	Remote Similarity	NPD4675	Approved
0.6392	Remote Similarity	NPD4678	Approved
0.6391	Remote Similarity	NPD2673	Approved
0.6391	Remote Similarity	NPD2671	Approved
0.6391	Remote Similarity	NPD7685	Pre-registration
0.6389	Remote Similarity	NPD2250	Discontinued
0.6389	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD4538	Approved
0.6376	Remote Similarity	NPD4536	Approved
0.6376	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD2977	Approved
0.6375	Remote Similarity	NPD2978	Approved
0.6375	Remote Similarity	NPD8455	Phase 2
0.6358	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1375	Discontinued
0.6357	Remote Similarity	NPD915	Approved
0.6335	Remote Similarity	NPD5402	Approved
0.6335	Remote Similarity	NPD3817	Phase 2
0.6335	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD1511	Approved
0.6323	Remote Similarity	NPD1774	Approved
0.6319	Remote Similarity	NPD5647	Approved
0.6319	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5403	Approved
0.6303	Remote Similarity	NPD3787	Discontinued
0.6299	Remote Similarity	NPD6190	Approved
0.6289	Remote Similarity	NPD4380	Phase 2
0.6284	Remote Similarity	NPD3620	Phase 2
0.6284	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD1465	Phase 2
0.6267	Remote Similarity	NPD7097	Phase 1
0.6258	Remote Similarity	NPD7075	Discontinued
0.625	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD1933	Approved
0.6242	Remote Similarity	NPD1512	Approved
0.6241	Remote Similarity	NPD3496	Discontinued
0.6234	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD5960	Phase 3
0.6225	Remote Similarity	NPD5588	Approved
0.6224	Remote Similarity	NPD3685	Discontinued
0.6222	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7212	Phase 2
0.6218	Remote Similarity	NPD7213	Phase 3
0.6218	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD1549	Phase 2
0.6203	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6653	Approved
0.6194	Remote Similarity	NPD2219	Phase 1
0.619	Remote Similarity	NPD3179	Approved
0.619	Remote Similarity	NPD3180	Approved
0.6184	Remote Similarity	NPD1551	Phase 2
0.6181	Remote Similarity	NPD8651	Approved
0.6178	Remote Similarity	NPD5401	Approved
0.617	Remote Similarity	NPD5126	Approved
0.617	Remote Similarity	NPD5125	Phase 3
0.6169	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD1358	Approved
0.6164	Remote Similarity	NPD3686	Approved
0.6164	Remote Similarity	NPD3687	Approved
0.6159	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD3751	Discontinued
0.6149	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD1048	Approved
0.6144	Remote Similarity	NPD3540	Phase 1
0.6139	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD6362	Approved
0.6133	Remote Similarity	NPD447	Suspended
0.6131	Remote Similarity	NPD5283	Phase 1
0.6129	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4628	Phase 3
0.6127	Remote Similarity	NPD155	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD7033	Discontinued
0.6115	Remote Similarity	NPD6799	Approved
0.6115	Remote Similarity	NPD4357	Discontinued
0.6111	Remote Similarity	NPD6801	Discontinued
0.6107	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD2424	Discontinued
0.6096	Remote Similarity	NPD1469	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.609	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.609	Remote Similarity	NPD2677	Approved
0.6087	Remote Similarity	NPD7680	Approved
0.6084	Remote Similarity	NPD1535	Discovery
0.6084	Remote Similarity	NPD5494	Approved
0.6084	Remote Similarity	NPD776	Approved
0.6078	Remote Similarity	NPD3539	Phase 1
0.6078	Remote Similarity	NPD6099	Approved
0.6078	Remote Similarity	NPD6100	Approved
0.6076	Remote Similarity	NPD4123	Phase 3
0.6076	Remote Similarity	NPD7447	Phase 1
0.6074	Remote Similarity	NPD5772	Approved
0.6074	Remote Similarity	NPD5773	Approved
0.6074	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD6696	Suspended
0.6069	Remote Similarity	NPD7549	Discontinued
0.6068	Remote Similarity	NPD9088	Approved
0.6067	Remote Similarity	NPD4060	Phase 1

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