NPASS Compound

Structure

CID301910 OpenBabel06191716112D 36 40 0 0 1 0 0 0 0 0999 V2000 7.2235 -1.2758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2891 -0.6521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2672 -0.8600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2514 -3.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6146 -3.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9290 -2.3463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8108 -1.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4062 -0.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6199 -1.3952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2514 -2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9071 -2.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5762 -1.8111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9448 -2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6146 -1.8917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9448 -3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0787 -3.8917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2127 -3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9945 -1.7226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6418 -1.1873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4807 -2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2127 -2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6768 -2.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9349 -0.0982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2161 -3.5053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8108 -3.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0787 -4.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3467 -3.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3328 -0.2363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5544 -2.0190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4807 -3.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0787 -1.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9727 -1.9305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3467 -1.8917 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 31 1 0 0 0 0 2 3 2 0 0 0 0 2 9 1 0 0 0 0 3 12 1 0 0 0 0 4 5 2 0 0 0 0 5 32 1 0 0 0 0 6 9 2 0 0 0 0 6 11 1 0 0 0 0 7 24 1 0 0 0 0 8 25 1 0 0 0 0 9 20 1 0 0 0 0 10 4 1 6 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 12 2 0 0 0 0 11 26 1 0 0 0 0 12 31 1 0 0 0 0 13 7 1 1 0 0 0 13 15 1 0 0 0 0 13 33 1 0 0 0 0 14 21 1 0 0 0 0 14 23 1 6 0 0 0 15 16 1 0 0 0 0 15 27 1 6 0 0 0 16 17 1 0 0 0 0 16 28 1 1 0 0 0 17 22 1 0 0 0 0 17 29 1 6 0 0 0 18 19 1 0 0 0 0 18 34 1 1 0 0 0 19 23 1 6 0 0 0 19 36 1 0 0 0 0 20 30 2 0 0 0 0 20 34 1 0 0 0 0 21 32 1 0 0 0 0 21 35 1 1 0 0 0 22 33 1 0 0 0 0 22 35 1 1 0 0 0 23 8 1 6 0 0 0 23 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.15
Volume:	464.672
LogP:	0.3
LogD:	0.052
LogS:	-2.956
# Rotatable Bonds:	8
TPSA:	197.13
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.173
Synthetic Accessibility Score:	4.937
Fsp3:	0.609
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.43
MDCK Permeability:	8.798504859441891e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.487
Human Intestinal Absorption (HIA):	0.893
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.2
Plasma Protein Binding (PPB):	34.36820983886719%
Volume Distribution (VD):	0.363
Pgp-substrate:	35.10115432739258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.1
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.079
CYP3A4-substrate:	0.06

ADMET: Excretion

Clearance (CL):	3.499
Half-life (T1/2):	0.907

ADMET: Toxicity

hERG Blockers:	0.143
Human Hepatotoxicity (H-HT):	0.238
Drug-inuced Liver Injury (DILI):	0.714
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.112
Carcinogencity:	0.454
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.877

Download Data

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

Natural Product: NPC301910

Natural Product ID:	NPC301910
*Common Name:**	Isovanillyl Catapol
IUPAC Name:	[(1aS,1bS,2S,5aR,6S,6aS)-1a-(hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-6-yl] 3-hydroxy-4-methoxybenzoate
Synonyms:	Isovanillyl Catapol
Standard InCHIKey:	DSVKJARKMOAAKJ-NUGKWEEESA-N
Standard InCHI:	InChI=1S/C23H28O13/c1-31-12-3-2-9(6-11(12)26)20(30)34-18-10-4-5-32-21(14(10)23(8-25)19(18)36-23)35-22-17(29)16(28)15(27)13(7-24)33-22/h2-6,10,13-19,21-22,24-29H,7-8H2,1H3/t10-,13-,14-,15-,16+,17-,18+,19+,21+,22+,23-/m1/s1
SMILES:	COc1ccc(cc1O)C(=O)O[C@H]1[C@@H]2C=CO[C@H]([C@@H]2[C@]2(CO)[C@H]1O2)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2059077
PubChem CID:	12002014
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:0002207] O-glycosyl compounds

*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
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(79)80020-5]
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[10328294]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568764]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	pericarp	n.a.	n.a.	PMID[16038565]
NPO12653	Diacarnus levii	Species	Podospongiidae	Eukaryota	n.a.	at a depth of -10 M off the coast of Papua New Guinea	1998-JUN	PMID[17253866]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18166016]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20232858]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	xylem	n.a.	Database[Article]
NPO2289	Vicia hirsuta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3671	Rhodiola coccinea	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2289	Vicia hirsuta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3671	Rhodiola coccinea	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9254	Scutellaria racemosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11674	Viburnum lantanoides	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2576	Eusideroxylon zwageri	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO396	Ventilago goughii	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26737	Solanum mauritianum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14776	Petrosia weinbergi	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7006	Garcinia subelliptica	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3671	Rhodiola coccinea	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5311	Isertia haenkeana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12047	Solanum unguiculatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12762	Elattostachys apetala	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4923	Ononis hircina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2289	Vicia hirsuta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5173	Antidesma pentandrum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10102	Pithecellobium albicans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1455	Aspergillus caelatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7648	Geigeria plumosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11397	Cladophora rupestris	Species	Cladophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12653	Diacarnus levii	Species	Podospongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12526	Veronica turrilliana	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9561	Preussia australis	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7323	Lindera pipericarpa	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13096	Lecidea kochiana	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10553	Heterophyllaea pustulata	Species	Rubiaceae	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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	103.2	%	PMID[483656]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	102.5	%	PMID[483656]

☑ 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 NPC301910 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	364
0.1-0.2	1503
0.2-0.3	3257
0.3-0.4	7223
0.4-0.5	10429
0.5-0.6	6864
0.6-0.7	8882
0.7-0.8	3961
0.8-0.85	163
0.85-0.9	38
0.9-0.95	8
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC130730
0.9808	High Similarity	NPC206815
0.9808	High Similarity	NPC476011
0.9679	High Similarity	NPC138993
0.9554	High Similarity	NPC474936
0.9359	High Similarity	NPC478232
0.9295	High Similarity	NPC89693
0.9295	High Similarity	NPC229548
0.9295	High Similarity	NPC478241
0.9264	High Similarity	NPC21956
0.9259	High Similarity	NPC282551
0.9245	High Similarity	NPC179914
0.9231	High Similarity	NPC194705
0.9057	High Similarity	NPC475484
0.9045	High Similarity	NPC269914
0.9045	High Similarity	NPC478249
0.9038	High Similarity	NPC478236
0.9038	High Similarity	NPC478234
0.9036	High Similarity	NPC470685
0.9018	High Similarity	NPC109990
0.9	High Similarity	NPC478248
0.8987	High Similarity	NPC203664
0.8981	High Similarity	NPC147224
0.8963	High Similarity	NPC180586
0.8957	High Similarity	NPC145847
0.8951	High Similarity	NPC478265
0.8944	High Similarity	NPC226759
0.8931	High Similarity	NPC229354
0.8924	High Similarity	NPC289021
0.8924	High Similarity	NPC158546
0.891	High Similarity	NPC18789
0.8875	High Similarity	NPC327032
0.8875	High Similarity	NPC191046
0.8875	High Similarity	NPC194095
0.8854	High Similarity	NPC308178
0.8846	High Similarity	NPC474234
0.8827	High Similarity	NPC187205
0.8827	High Similarity	NPC286919
0.8827	High Similarity	NPC475663
0.8805	High Similarity	NPC475379
0.879	High Similarity	NPC473149
0.8773	High Similarity	NPC469384
0.8765	High Similarity	NPC471405
0.8765	High Similarity	NPC475378
0.875	High Similarity	NPC36130
0.875	High Similarity	NPC134905
0.8742	High Similarity	NPC240592
0.8742	High Similarity	NPC117346
0.8727	High Similarity	NPC41009
0.8726	High Similarity	NPC473867
0.8718	High Similarity	NPC478240
0.8712	High Similarity	NPC472860
0.8712	High Similarity	NPC133984
0.8704	High Similarity	NPC10205
0.8679	High Similarity	NPC96599
0.8659	High Similarity	NPC289811
0.8659	High Similarity	NPC160780
0.865	High Similarity	NPC478266
0.8634	High Similarity	NPC289438
0.8634	High Similarity	NPC478235
0.8625	High Similarity	NPC205054
0.8606	High Similarity	NPC239966
0.8606	High Similarity	NPC203020
0.8599	High Similarity	NPC473281
0.8599	High Similarity	NPC77922
0.8598	High Similarity	NPC1913
0.858	High Similarity	NPC105827
0.858	High Similarity	NPC137813
0.858	High Similarity	NPC310661
0.858	High Similarity	NPC157898
0.8562	High Similarity	NPC478242
0.8562	High Similarity	NPC111785
0.8554	High Similarity	NPC311803
0.8554	High Similarity	NPC472859
0.8554	High Similarity	NPC25389
0.8545	High Similarity	NPC76211
0.8539	High Similarity	NPC475299
0.8535	High Similarity	NPC237872
0.8535	High Similarity	NPC302286
0.8535	High Similarity	NPC263397
0.8535	High Similarity	NPC116104
0.8535	High Similarity	NPC88754
0.8526	High Similarity	NPC46644
0.8509	High Similarity	NPC227980
0.8503	High Similarity	NPC285108
0.8503	High Similarity	NPC33298
0.8494	Intermediate Similarity	NPC166277
0.8494	Intermediate Similarity	NPC119125
0.8488	Intermediate Similarity	NPC469438
0.8485	Intermediate Similarity	NPC4747
0.8485	Intermediate Similarity	NPC49173
0.8485	Intermediate Similarity	NPC104275
0.8476	Intermediate Similarity	NPC156624
0.8476	Intermediate Similarity	NPC172920
0.8466	Intermediate Similarity	NPC96194
0.8466	Intermediate Similarity	NPC299855
0.8466	Intermediate Similarity	NPC44730
0.8452	Intermediate Similarity	NPC100420
0.8447	Intermediate Similarity	NPC98809
0.8447	Intermediate Similarity	NPC476394
0.8434	Intermediate Similarity	NPC74319
0.8434	Intermediate Similarity	NPC287872
0.843	Intermediate Similarity	NPC316539
0.8418	Intermediate Similarity	NPC189704
0.8418	Intermediate Similarity	NPC152796
0.8418	Intermediate Similarity	NPC475213
0.8415	Intermediate Similarity	NPC472128
0.8415	Intermediate Similarity	NPC472127
0.8405	Intermediate Similarity	NPC267091
0.8402	Intermediate Similarity	NPC475738
0.8397	Intermediate Similarity	NPC49597
0.8395	Intermediate Similarity	NPC69367
0.8385	Intermediate Similarity	NPC472969
0.8383	Intermediate Similarity	NPC289346
0.8382	Intermediate Similarity	NPC84482
0.8382	Intermediate Similarity	NPC169645
0.8382	Intermediate Similarity	NPC469354
0.8375	Intermediate Similarity	NPC37838
0.8371	Intermediate Similarity	NPC476067
0.8371	Intermediate Similarity	NPC475121
0.8365	Intermediate Similarity	NPC251062
0.8365	Intermediate Similarity	NPC296659
0.8365	Intermediate Similarity	NPC202391
0.8365	Intermediate Similarity	NPC184464
0.8364	Intermediate Similarity	NPC38699
0.8354	Intermediate Similarity	NPC299706
0.8354	Intermediate Similarity	NPC61604
0.8354	Intermediate Similarity	NPC245615
0.8354	Intermediate Similarity	NPC115466
0.8344	Intermediate Similarity	NPC140151
0.8344	Intermediate Similarity	NPC243891
0.8333	Intermediate Similarity	NPC92117
0.8313	Intermediate Similarity	NPC163635
0.8313	Intermediate Similarity	NPC108455
0.8304	Intermediate Similarity	NPC116745
0.8304	Intermediate Similarity	NPC208818
0.8303	Intermediate Similarity	NPC476364
0.8302	Intermediate Similarity	NPC186296
0.8302	Intermediate Similarity	NPC242756
0.8295	Intermediate Similarity	NPC188217
0.8294	Intermediate Similarity	NPC472130
0.8294	Intermediate Similarity	NPC472131
0.8291	Intermediate Similarity	NPC154262
0.8291	Intermediate Similarity	NPC7518
0.8291	Intermediate Similarity	NPC159387
0.8291	Intermediate Similarity	NPC137501
0.8284	Intermediate Similarity	NPC246024
0.8284	Intermediate Similarity	NPC4013
0.8284	Intermediate Similarity	NPC90905
0.828	Intermediate Similarity	NPC226005
0.828	Intermediate Similarity	NPC220936
0.828	Intermediate Similarity	NPC31745
0.8272	Intermediate Similarity	NPC120621
0.8272	Intermediate Similarity	NPC248257
0.8269	Intermediate Similarity	NPC157554
0.8261	Intermediate Similarity	NPC98356
0.8256	Intermediate Similarity	NPC658
0.8256	Intermediate Similarity	NPC197708
0.8253	Intermediate Similarity	NPC145425
0.825	Intermediate Similarity	NPC229036
0.825	Intermediate Similarity	NPC110063
0.8249	Intermediate Similarity	NPC473776
0.8249	Intermediate Similarity	NPC473205
0.8239	Intermediate Similarity	NPC140502
0.8239	Intermediate Similarity	NPC296643
0.8232	Intermediate Similarity	NPC474620
0.8229	Intermediate Similarity	NPC473713
0.8222	Intermediate Similarity	NPC71385
0.8222	Intermediate Similarity	NPC230670
0.8221	Intermediate Similarity	NPC161955
0.8221	Intermediate Similarity	NPC75945
0.8218	Intermediate Similarity	NPC163165
0.8218	Intermediate Similarity	NPC195972
0.8208	Intermediate Similarity	NPC472129
0.8208	Intermediate Similarity	NPC212748
0.8208	Intermediate Similarity	NPC43434
0.8204	Intermediate Similarity	NPC478055
0.8199	Intermediate Similarity	NPC469683
0.8198	Intermediate Similarity	NPC298847
0.8187	Intermediate Similarity	NPC478239
0.8182	Intermediate Similarity	NPC75695
0.8177	Intermediate Similarity	NPC112708
0.8176	Intermediate Similarity	NPC148273
0.8176	Intermediate Similarity	NPC80098
0.8176	Intermediate Similarity	NPC22324
0.8171	Intermediate Similarity	NPC158635
0.8171	Intermediate Similarity	NPC229882
0.8166	Intermediate Similarity	NPC239818
0.8166	Intermediate Similarity	NPC476337
0.8166	Intermediate Similarity	NPC218471
0.8166	Intermediate Similarity	NPC44507
0.8165	Intermediate Similarity	NPC100389
0.8161	Intermediate Similarity	NPC5786
0.8161	Intermediate Similarity	NPC235575
0.8161	Intermediate Similarity	NPC254540
0.8161	Intermediate Similarity	NPC172807
0.8161	Intermediate Similarity	NPC102851
0.8161	Intermediate Similarity	NPC211594
0.816	Intermediate Similarity	NPC98009
0.8155	Intermediate Similarity	NPC223335

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 NPC301910 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	865
0.2-0.3	1955
0.3-0.4	2654
0.4-0.5	2022
0.5-0.6	987
0.6-0.7	312
0.7-0.8	50
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9689	High Similarity	NPD7685	Pre-registration
0.8092	Intermediate Similarity	NPD3818	Discontinued
0.8034	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7054	Approved
0.7898	Intermediate Similarity	NPD7472	Approved
0.7797	Intermediate Similarity	NPD7074	Phase 3
0.7784	Intermediate Similarity	NPD1653	Approved
0.7778	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6797	Phase 2
0.7744	Intermediate Similarity	NPD6190	Approved
0.7716	Intermediate Similarity	NPD7266	Discontinued
0.7709	Intermediate Similarity	NPD7251	Discontinued
0.7701	Intermediate Similarity	NPD7199	Phase 2
0.7688	Intermediate Similarity	NPD6234	Discontinued
0.7684	Intermediate Similarity	NPD7228	Approved
0.7667	Intermediate Similarity	NPD7808	Phase 3
0.763	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD230	Phase 1
0.7619	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD37	Approved
0.7572	Intermediate Similarity	NPD4966	Approved
0.7572	Intermediate Similarity	NPD4965	Approved
0.7572	Intermediate Similarity	NPD4967	Phase 2
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1934	Approved
0.747	Intermediate Similarity	NPD4628	Phase 3
0.7468	Intermediate Similarity	NPD9494	Approved
0.7457	Intermediate Similarity	NPD2801	Approved
0.7414	Intermediate Similarity	NPD3817	Phase 2
0.7374	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6166	Phase 2
0.7371	Intermediate Similarity	NPD3882	Suspended
0.7363	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD1465	Phase 2
0.7348	Intermediate Similarity	NPD5844	Phase 1
0.734	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD6559	Discontinued
0.7303	Intermediate Similarity	NPD8127	Discontinued
0.7283	Intermediate Similarity	NPD7028	Phase 2
0.7283	Intermediate Similarity	NPD4380	Phase 2
0.7263	Intermediate Similarity	NPD6232	Discontinued
0.7256	Intermediate Similarity	NPD6653	Approved
0.7253	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD8312	Approved
0.7243	Intermediate Similarity	NPD8313	Approved
0.7238	Intermediate Similarity	NPD7473	Discontinued
0.7228	Intermediate Similarity	NPD7240	Approved
0.7216	Intermediate Similarity	NPD5353	Approved
0.7151	Intermediate Similarity	NPD5494	Approved
0.7151	Intermediate Similarity	NPD6273	Approved
0.7143	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7075	Discontinued
0.7135	Intermediate Similarity	NPD1511	Approved
0.7104	Intermediate Similarity	NPD3751	Discontinued
0.7091	Intermediate Similarity	NPD447	Suspended
0.7062	Intermediate Similarity	NPD8455	Phase 2
0.7059	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD1512	Approved
0.7051	Intermediate Similarity	NPD9545	Approved
0.7045	Intermediate Similarity	NPD6386	Approved
0.7045	Intermediate Similarity	NPD6385	Approved
0.7044	Intermediate Similarity	NPD7930	Approved
0.7029	Intermediate Similarity	NPD7458	Discontinued
0.7022	Intermediate Similarity	NPD5402	Approved
0.7011	Intermediate Similarity	NPD7799	Discontinued
0.7006	Intermediate Similarity	NPD6801	Discontinued
0.7	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1933	Approved
0.6985	Remote Similarity	NPD7999	Approved
0.6982	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6004	Phase 3
0.6982	Remote Similarity	NPD6005	Phase 3
0.6982	Remote Similarity	NPD6002	Phase 3
0.6978	Remote Similarity	NPD3787	Discontinued
0.6975	Remote Similarity	NPD5647	Approved
0.697	Remote Similarity	NPD7435	Discontinued
0.6966	Remote Similarity	NPD5761	Phase 2
0.6966	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7819	Suspended
0.6966	Remote Similarity	NPD5760	Phase 2
0.6959	Remote Similarity	NPD4110	Phase 3
0.6959	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3027	Phase 3
0.6947	Remote Similarity	NPD8434	Phase 2
0.6939	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD9269	Phase 2
0.6928	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3620	Phase 2
0.6909	Remote Similarity	NPD3764	Approved
0.6904	Remote Similarity	NPD6781	Approved
0.6904	Remote Similarity	NPD6782	Approved
0.6904	Remote Similarity	NPD6780	Approved
0.6904	Remote Similarity	NPD6777	Approved
0.6904	Remote Similarity	NPD6778	Approved
0.6904	Remote Similarity	NPD6776	Approved
0.6904	Remote Similarity	NPD6779	Approved
0.6901	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2534	Approved
0.6897	Remote Similarity	NPD2532	Approved
0.6897	Remote Similarity	NPD2533	Approved
0.6884	Remote Similarity	NPD7680	Approved
0.6884	Remote Similarity	NPD7497	Discontinued
0.6875	Remote Similarity	NPD3705	Approved
0.6871	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7033	Discontinued
0.6848	Remote Similarity	NPD5242	Approved
0.6842	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6799	Approved
0.6824	Remote Similarity	NPD2935	Discontinued
0.6818	Remote Similarity	NPD5403	Approved
0.6802	Remote Similarity	NPD6674	Discontinued
0.6798	Remote Similarity	NPD8151	Discontinued
0.6792	Remote Similarity	NPD1357	Approved
0.6786	Remote Similarity	NPD6355	Discontinued
0.6784	Remote Similarity	NPD5762	Approved
0.6784	Remote Similarity	NPD5763	Approved
0.6777	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6765	Approved
0.6772	Remote Similarity	NPD7038	Approved
0.6772	Remote Similarity	NPD7039	Approved
0.6772	Remote Similarity	NPD6764	Approved
0.6771	Remote Similarity	NPD8150	Discontinued
0.677	Remote Similarity	NPD1091	Approved
0.6765	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1510	Phase 2
0.6765	Remote Similarity	NPD7874	Approved
0.6763	Remote Similarity	NPD8166	Discontinued
0.6763	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3750	Approved
0.676	Remote Similarity	NPD7411	Suspended
0.6744	Remote Similarity	NPD1549	Phase 2
0.6742	Remote Similarity	NPD3455	Phase 2
0.674	Remote Similarity	NPD5977	Approved
0.674	Remote Similarity	NPD5978	Approved
0.674	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7783	Phase 2
0.6732	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1608	Approved
0.6726	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1613	Approved
0.6721	Remote Similarity	NPD919	Approved
0.6716	Remote Similarity	NPD7696	Phase 3
0.6716	Remote Similarity	NPD7698	Approved
0.6716	Remote Similarity	NPD7697	Approved
0.6707	Remote Similarity	NPD6362	Approved
0.6706	Remote Similarity	NPD7097	Phase 1
0.6705	Remote Similarity	NPD5401	Approved
0.6705	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD6599	Discontinued
0.6687	Remote Similarity	NPD9268	Approved
0.6686	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7236	Approved
0.6686	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD8320	Phase 1
0.6683	Remote Similarity	NPD8319	Approved
0.6683	Remote Similarity	NPD7871	Phase 2
0.6683	Remote Similarity	NPD7870	Phase 2
0.6667	Remote Similarity	NPD6823	Phase 2
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD7701	Phase 2
0.6667	Remote Similarity	NPD7585	Approved
0.665	Remote Similarity	NPD7801	Approved
0.665	Remote Similarity	NPD6535	Approved
0.665	Remote Similarity	NPD6534	Approved
0.6648	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD3226	Approved
0.6633	Remote Similarity	NPD7296	Approved
0.6632	Remote Similarity	NPD6785	Approved
0.6632	Remote Similarity	NPD6784	Approved
0.6631	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD2796	Approved
0.6627	Remote Similarity	NPD4140	Approved
0.6627	Remote Similarity	NPD2861	Phase 2
0.6618	Remote Similarity	NPD7583	Approved
0.661	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD7239	Suspended
0.6578	Remote Similarity	NPD3926	Phase 2
0.657	Remote Similarity	NPD2799	Discontinued
0.6568	Remote Similarity	NPD6663	Approved
0.6566	Remote Similarity	NPD2798	Approved
0.6562	Remote Similarity	NPD5536	Phase 2
0.6559	Remote Similarity	NPD1247	Approved
0.6559	Remote Similarity	NPD6959	Discontinued
0.6556	Remote Similarity	NPD824	Approved
0.655	Remote Similarity	NPD7699	Phase 2
0.655	Remote Similarity	NPD4420	Approved
0.655	Remote Similarity	NPD7700	Phase 2
0.6545	Remote Similarity	NPD1876	Approved
0.6543	Remote Similarity	NPD17	Approved
0.6537	Remote Similarity	NPD7584	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