NPASS Compound

Structure

CID284472 OpenBabel06191716092D 24 24 0 0 1 0 0 0 0 0999 V2000 10.1749 -7.4883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 0.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4563 -0.0526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5816 -6.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9938 -5.7658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9993 -5.8703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4115 -5.0613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4170 -5.1658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8292 -4.3568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8347 -4.4613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2469 -3.6523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2524 -3.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6646 -2.9478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6701 -3.0523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0823 -2.2433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 -2.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0878 -2.3479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -0.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7872 -0.7957 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 4 1 0 0 0 0 3 23 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 1 0 0 0 18 21 1 0 0 0 0 19 22 2 0 0 0 0 19 24 1 0 0 0 0 20 2 1 1 0 0 0 20 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.26
Volume:	375.808
LogP:	6.078
LogD:	3.705
LogS:	-4.257
# Rotatable Bonds:	13
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.299
Synthetic Accessibility Score:	3.833
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.669
MDCK Permeability:	2.358222809561994e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.456
Plasma Protein Binding (PPB):	97.42198181152344%
Volume Distribution (VD):	1.617
Pgp-substrate:	1.9822958707809448%

ADMET: Metabolism

CYP1A2-inhibitor:	0.244
CYP1A2-substrate:	0.354
CYP2C19-inhibitor:	0.411
CYP2C19-substrate:	0.313
CYP2C9-inhibitor:	0.475
CYP2C9-substrate:	0.872
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.715
CYP3A4-substrate:	0.108

ADMET: Excretion

Clearance (CL):	6.87
Half-life (T1/2):	0.102

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.156
Drug-inuced Liver Injury (DILI):	0.241
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.19
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.768
Carcinogencity:	0.057
Eye Corrosion:	0.032
Eye Irritation:	0.113
Respiratory Toxicity:	0.605

Download Data

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

Natural Product: NPC284472

Natural Product ID:	NPC284472
*Common Name:**	Subamolide A
IUPAC Name:	(3Z,4R,5R)-4-hydroxy-5-methoxy-5-methyl-3-tetradecylideneoxolan-2-one
Synonyms:
Standard InCHIKey:	YLCXJNOKPGBEPM-NBVPMNRZSA-N
Standard InCHI:	InChI=1S/C20H36O4/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(21)20(2,23-3)24-19(17)22/h16,18,21H,4-15H2,1-3H3/b17-16-/t18-,20-/m1/s1
SMILES:	CCCCCCCCCCCCC/C=C/1C(=O)O[C@@]([C@@H]1O)(C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL218924
PubChem CID:	16104909
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0001656] Acetals [CHEMONTID:0004472] Ketals

*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
NPO9305	Iotrochota purpurea	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924179]
NPO8035	Tylophora tanakae	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350151]
NPO10900	Cinnamomum subavenium	Species	Lauraceae	Eukaryota	stems	Wulai Hsiang, Taipei County, Taiwan	2005-MAY	PMID[17253858]
NPO2298	Streptomyces platensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19581087]
NPO2298	Streptomyces platensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20299229]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[20363129]
NPO2298	Streptomyces platensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21214253]
NPO10900	Cinnamomum subavenium	Species	Lauraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23025417]
NPO9305	Iotrochota purpurea	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23131412]
NPO10900	Cinnamomum subavenium	Species	Lauraceae	Eukaryota	stem bark	Laifeng, Hubei Province, China	2012-JUL	PMID[26087384]
NPO11699	Ecballium elaterium	Species	Cucurbitaceae	Eukaryota	Fruit juice	n.a.	n.a.	PMID[3404148]
NPO11699	Ecballium elaterium	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11699	Ecballium elaterium	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5823	Helichrysum auriceps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10900	Cinnamomum subavenium	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9922	Myelobia smerintha	Species	Crambidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11553	Phebalium dentatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3736	Scrophularia koelzii	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7709	Spiracantha cornifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12188	Datisca glomerata	Species	Datiscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9672	Lotus ucrainicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7045	Viviparus japonicus	Species	Viviparidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8035	Tylophora tanakae	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2608	Solanum andigena	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9509	Charpentiera obovata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10393	Ophidiaster ophidianus	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5008	Hubertia tomentosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15252	Clathria prolifera	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4493	Polygonum flaccidum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8477	Myristica cagayanensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3378	Alstonia undulifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11811	Capparis ovata	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO761	Fagus fusca	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12888	Echinus microtuberculatus	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1182	Croton montevidensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12436	Quercus imbricaria	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12308	Metridium senile	Species	Metridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11699	Ecballium elaterium	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12669	Cassine papillosa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6253	Conus pulicarius	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2298	Streptomyces platensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5384	Ligustrum obtusifolium	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12544	Dioscorea olfersiana	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20291	Phyllanthus oligospermus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11256	Pseudowintera colorata	Species	Winteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10737	Asteriscus aquaticus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9305	Iotrochota purpurea	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	19

Activity Type	# Activity
Cell Line	16
Individual Protein	3
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	8.5	%	PMID[461248]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	25.4	%	PMID[461248]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	27.3	%	PMID[461248]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	64.4	%	PMID[461248]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	48.2	%	PMID[461248]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	46.3	%	PMID[461248]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	45.0	%	PMID[461248]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	52.6	%	PMID[461248]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	39.6	%	PMID[461248]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	41.0	%	PMID[461248]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	42.0	%	PMID[461248]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	29.8	%	PMID[461248]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	12.2	%	PMID[461248]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	12.8	%	PMID[461248]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	13.0	%	PMID[461248]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	17.7	%	PMID[461248]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Inhibition	=	50.0	%	PMID[461249]
NPT23875	SINGLE PROTEIN	Tyrosinase	Danio rerio	Inhibition	=	25.0	%	PMID[461249]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Inhibition	=	40.0	%	PMID[461249]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	IC50	=	1000.0	nM	PMID[461250]

☑ 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 NPC284472 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	170
0.1-0.2	1556
0.2-0.3	6260
0.3-0.4	14913
0.4-0.5	11210
0.5-0.6	6033
0.6-0.7	1965
0.7-0.8	479
0.8-0.85	91
0.85-0.9	13
0.9-0.95	0
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC229799
1.0	High Similarity	NPC286770
0.987	High Similarity	NPC11383
0.987	High Similarity	NPC474959
0.987	High Similarity	NPC475046
0.987	High Similarity	NPC310450
0.8974	High Similarity	NPC49302
0.8974	High Similarity	NPC125365
0.8974	High Similarity	NPC176329
0.8974	High Similarity	NPC51809
0.8974	High Similarity	NPC474818
0.8861	High Similarity	NPC221095
0.8861	High Similarity	NPC473471
0.8861	High Similarity	NPC279214
0.8846	High Similarity	NPC301207
0.8765	High Similarity	NPC150502
0.8608	High Similarity	NPC209113
0.8608	High Similarity	NPC127118
0.8452	Intermediate Similarity	NPC41856
0.8391	Intermediate Similarity	NPC139418
0.8295	Intermediate Similarity	NPC473904
0.825	Intermediate Similarity	NPC161038
0.8182	Intermediate Similarity	NPC14901
0.8182	Intermediate Similarity	NPC130359
0.8161	Intermediate Similarity	NPC178215
0.8148	Intermediate Similarity	NPC205615
0.8148	Intermediate Similarity	NPC16279
0.8148	Intermediate Similarity	NPC256640
0.814	Intermediate Similarity	NPC110710
0.814	Intermediate Similarity	NPC473669
0.814	Intermediate Similarity	NPC132496
0.814	Intermediate Similarity	NPC1083
0.814	Intermediate Similarity	NPC66346
0.814	Intermediate Similarity	NPC223871
0.814	Intermediate Similarity	NPC107986
0.814	Intermediate Similarity	NPC283085
0.814	Intermediate Similarity	NPC231009
0.814	Intermediate Similarity	NPC286338
0.814	Intermediate Similarity	NPC473651
0.814	Intermediate Similarity	NPC82795
0.814	Intermediate Similarity	NPC103284
0.814	Intermediate Similarity	NPC473478
0.8111	Intermediate Similarity	NPC473663
0.8111	Intermediate Similarity	NPC11456
0.8111	Intermediate Similarity	NPC473723
0.8111	Intermediate Similarity	NPC473561
0.8111	Intermediate Similarity	NPC475173
0.8072	Intermediate Similarity	NPC99651
0.8068	Intermediate Similarity	NPC280621
0.8068	Intermediate Similarity	NPC40376
0.8068	Intermediate Similarity	NPC233551
0.8068	Intermediate Similarity	NPC20339
0.8068	Intermediate Similarity	NPC21208
0.8068	Intermediate Similarity	NPC48338
0.8049	Intermediate Similarity	NPC275530
0.8046	Intermediate Similarity	NPC69082
0.8046	Intermediate Similarity	NPC62118
0.8046	Intermediate Similarity	NPC308412
0.8046	Intermediate Similarity	NPC475581
0.8046	Intermediate Similarity	NPC134885
0.8046	Intermediate Similarity	NPC134807
0.8046	Intermediate Similarity	NPC231096
0.8046	Intermediate Similarity	NPC473687
0.8046	Intermediate Similarity	NPC240695
0.8046	Intermediate Similarity	NPC112685
0.8046	Intermediate Similarity	NPC114694
0.8046	Intermediate Similarity	NPC219498
0.8046	Intermediate Similarity	NPC107717
0.8046	Intermediate Similarity	NPC469910
0.8046	Intermediate Similarity	NPC210218
0.8046	Intermediate Similarity	NPC134865
0.8046	Intermediate Similarity	NPC103523
0.8046	Intermediate Similarity	NPC204686
0.8046	Intermediate Similarity	NPC171174
0.8046	Intermediate Similarity	NPC232555
0.8046	Intermediate Similarity	NPC142117
0.8046	Intermediate Similarity	NPC279267
0.8023	Intermediate Similarity	NPC163093
0.8	Intermediate Similarity	NPC473707
0.7975	Intermediate Similarity	NPC202011
0.7931	Intermediate Similarity	NPC470755
0.7931	Intermediate Similarity	NPC471567
0.7931	Intermediate Similarity	NPC182383
0.7931	Intermediate Similarity	NPC477014
0.7931	Intermediate Similarity	NPC477013
0.7931	Intermediate Similarity	NPC120398
0.7927	Intermediate Similarity	NPC68819
0.7912	Intermediate Similarity	NPC469692
0.7912	Intermediate Similarity	NPC469645
0.7901	Intermediate Similarity	NPC114727
0.7901	Intermediate Similarity	NPC476590
0.7889	Intermediate Similarity	NPC473311
0.7889	Intermediate Similarity	NPC239517
0.7889	Intermediate Similarity	NPC474232
0.7865	Intermediate Similarity	NPC39754
0.7865	Intermediate Similarity	NPC100454
0.7865	Intermediate Similarity	NPC234077
0.7865	Intermediate Similarity	NPC151403
0.7865	Intermediate Similarity	NPC169511
0.7865	Intermediate Similarity	NPC242364
0.7865	Intermediate Similarity	NPC171135
0.7865	Intermediate Similarity	NPC133730
0.7865	Intermediate Similarity	NPC287164
0.7865	Intermediate Similarity	NPC61257
0.7865	Intermediate Similarity	NPC81045
0.7865	Intermediate Similarity	NPC261952
0.7865	Intermediate Similarity	NPC476803
0.7865	Intermediate Similarity	NPC287089
0.7865	Intermediate Similarity	NPC191929
0.7865	Intermediate Similarity	NPC172821
0.7865	Intermediate Similarity	NPC274446
0.7865	Intermediate Similarity	NPC320569
0.7848	Intermediate Similarity	NPC475982
0.7841	Intermediate Similarity	NPC47937
0.7841	Intermediate Similarity	NPC477015
0.7841	Intermediate Similarity	NPC469483
0.7826	Intermediate Similarity	NPC121825
0.7816	Intermediate Similarity	NPC158756
0.7816	Intermediate Similarity	NPC156804
0.7805	Intermediate Similarity	NPC478193
0.7805	Intermediate Similarity	NPC478192
0.7805	Intermediate Similarity	NPC478191
0.7805	Intermediate Similarity	NPC260396
0.7805	Intermediate Similarity	NPC478194
0.7805	Intermediate Similarity	NPC478196
0.7805	Intermediate Similarity	NPC478195
0.7791	Intermediate Similarity	NPC329829
0.7791	Intermediate Similarity	NPC473529
0.7791	Intermediate Similarity	NPC145914
0.7791	Intermediate Similarity	NPC131002
0.7791	Intermediate Similarity	NPC475159
0.7791	Intermediate Similarity	NPC65930
0.7791	Intermediate Similarity	NPC94875
0.7791	Intermediate Similarity	NPC473780
0.7791	Intermediate Similarity	NPC11332
0.7791	Intermediate Similarity	NPC180363
0.7791	Intermediate Similarity	NPC73310
0.7791	Intermediate Similarity	NPC473712
0.7778	Intermediate Similarity	NPC318963
0.7778	Intermediate Similarity	NPC20621
0.7778	Intermediate Similarity	NPC40066
0.7778	Intermediate Similarity	NPC473504
0.7778	Intermediate Similarity	NPC280612
0.7778	Intermediate Similarity	NPC93794
0.7778	Intermediate Similarity	NPC42598
0.7778	Intermediate Similarity	NPC81778
0.7778	Intermediate Similarity	NPC477011
0.7778	Intermediate Similarity	NPC91067
0.7765	Intermediate Similarity	NPC47653
0.7738	Intermediate Similarity	NPC182292
0.7727	Intermediate Similarity	NPC329838
0.7727	Intermediate Similarity	NPC470124
0.7727	Intermediate Similarity	NPC322529
0.7727	Intermediate Similarity	NPC329615
0.7717	Intermediate Similarity	NPC295204
0.7717	Intermediate Similarity	NPC473520
0.7717	Intermediate Similarity	NPC288240
0.7717	Intermediate Similarity	NPC162205
0.7717	Intermediate Similarity	NPC273579
0.7701	Intermediate Similarity	NPC116543
0.7701	Intermediate Similarity	NPC144415
0.7701	Intermediate Similarity	NPC161045
0.7701	Intermediate Similarity	NPC40746
0.7701	Intermediate Similarity	NPC169575
0.7701	Intermediate Similarity	NPC253801
0.7684	Intermediate Similarity	NPC187268
0.7674	Intermediate Similarity	NPC297440
0.7667	Intermediate Similarity	NPC89001
0.7667	Intermediate Similarity	NPC320458
0.7667	Intermediate Similarity	NPC473905
0.7667	Intermediate Similarity	NPC475819
0.7667	Intermediate Similarity	NPC476805
0.766	Intermediate Similarity	NPC477921
0.764	Intermediate Similarity	NPC293136
0.764	Intermediate Similarity	NPC475461
0.764	Intermediate Similarity	NPC132940
0.764	Intermediate Similarity	NPC241360
0.764	Intermediate Similarity	NPC305475
0.7609	Intermediate Similarity	NPC472010
0.7609	Intermediate Similarity	NPC9447
0.7609	Intermediate Similarity	NPC473321
0.7582	Intermediate Similarity	NPC477016
0.7582	Intermediate Similarity	NPC477017
0.7582	Intermediate Similarity	NPC79027
0.7579	Intermediate Similarity	NPC266842
0.7564	Intermediate Similarity	NPC19769
0.7564	Intermediate Similarity	NPC282760
0.7564	Intermediate Similarity	NPC470123
0.7561	Intermediate Similarity	NPC470435
0.7561	Intermediate Similarity	NPC144419
0.7561	Intermediate Similarity	NPC284006
0.7556	Intermediate Similarity	NPC476583
0.7556	Intermediate Similarity	NPC45409
0.7556	Intermediate Similarity	NPC475037
0.7556	Intermediate Similarity	NPC258068
0.7556	Intermediate Similarity	NPC20533
0.7553	Intermediate Similarity	NPC36954
0.7553	Intermediate Similarity	NPC477922
0.7553	Intermediate Similarity	NPC471142
0.7529	Intermediate Similarity	NPC248775

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 NPC284472 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	2271
0.2-0.3	4058
0.3-0.4	1886
0.4-0.5	578
0.5-0.6	166
0.6-0.7	40
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.732	Intermediate Similarity	NPD4225	Approved
0.7143	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD46	Approved
0.7128	Intermediate Similarity	NPD6698	Approved
0.7033	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6371	Approved
0.6947	Remote Similarity	NPD7838	Discovery
0.6947	Remote Similarity	NPD5785	Approved
0.6875	Remote Similarity	NPD7983	Approved
0.6837	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5363	Approved
0.6762	Remote Similarity	NPD6686	Approved
0.6729	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4252	Approved
0.6559	Remote Similarity	NPD7154	Phase 3
0.6556	Remote Similarity	NPD4271	Approved
0.6556	Remote Similarity	NPD4268	Approved
0.6491	Remote Similarity	NPD8517	Approved
0.6491	Remote Similarity	NPD8513	Phase 3
0.6491	Remote Similarity	NPD8515	Approved
0.6491	Remote Similarity	NPD8516	Approved
0.6458	Remote Similarity	NPD4251	Approved
0.6458	Remote Similarity	NPD4250	Approved
0.6452	Remote Similarity	NPD5209	Approved
0.6452	Remote Similarity	NPD4269	Approved
0.6452	Remote Similarity	NPD4270	Approved
0.6429	Remote Similarity	NPD7115	Discovery
0.6421	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4820	Approved
0.6413	Remote Similarity	NPD4822	Approved
0.6413	Remote Similarity	NPD4819	Approved
0.6413	Remote Similarity	NPD4821	Approved
0.6354	Remote Similarity	NPD5786	Approved
0.6354	Remote Similarity	NPD4249	Approved
0.6346	Remote Similarity	NPD5344	Discontinued
0.6275	Remote Similarity	NPD7839	Suspended
0.6264	Remote Similarity	NPD4756	Discovery
0.625	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD8074	Phase 3
0.6211	Remote Similarity	NPD5362	Discontinued
0.62	Remote Similarity	NPD7637	Suspended
0.619	Remote Similarity	NPD3197	Phase 1
0.6173	Remote Similarity	NPD9119	Approved
0.6173	Remote Similarity	NPD6109	Phase 1
0.6173	Remote Similarity	NPD69	Approved
0.617	Remote Similarity	NPD5369	Approved
0.6163	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5370	Suspended
0.6139	Remote Similarity	NPD5779	Approved
0.6139	Remote Similarity	NPD5778	Approved
0.6118	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD6927	Phase 3
0.6102	Remote Similarity	NPD7830	Approved
0.6102	Remote Similarity	NPD7642	Approved
0.6102	Remote Similarity	NPD7829	Approved
0.6049	Remote Similarity	NPD9118	Approved
0.6042	Remote Similarity	NPD5332	Approved
0.6042	Remote Similarity	NPD6110	Phase 1
0.6042	Remote Similarity	NPD5331	Approved
0.604	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4790	Discontinued
0.5976	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD6648	Approved
0.5943	Remote Similarity	NPD7639	Approved
0.5943	Remote Similarity	NPD7640	Approved
0.5938	Remote Similarity	NPD6435	Approved
0.5906	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD7319	Approved
0.5849	Remote Similarity	NPD7638	Approved
0.5842	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6101	Approved
0.5842	Remote Similarity	NPD1695	Approved
0.5841	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD2204	Approved
0.5812	Remote Similarity	NPD7641	Discontinued
0.581	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD8444	Approved
0.5773	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5282	Discontinued
0.5766	Remote Similarity	NPD6412	Phase 2
0.5758	Remote Similarity	NPD1694	Approved
0.5738	Remote Similarity	NPD8451	Approved
0.5738	Remote Similarity	NPD7507	Approved
0.5729	Remote Similarity	NPD5368	Approved
0.5728	Remote Similarity	NPD6411	Approved
0.5726	Remote Similarity	NPD7500	Approved
0.5691	Remote Similarity	NPD8448	Approved
0.5679	Remote Similarity	NPD3728	Approved
0.5679	Remote Similarity	NPD3730	Approved
0.5678	Remote Similarity	NPD7328	Approved
0.5678	Remote Similarity	NPD7327	Approved
0.5667	Remote Similarity	NPD8033	Approved
0.5667	Remote Similarity	NPD7503	Approved
0.5656	Remote Similarity	NPD7492	Approved
0.5656	Remote Similarity	NPD8340	Approved
0.5656	Remote Similarity	NPD8299	Approved
0.5656	Remote Similarity	NPD8341	Approved
0.5656	Remote Similarity	NPD8342	Approved
0.5652	Remote Similarity	NPD6053	Discontinued
0.5647	Remote Similarity	NPD9120	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6647	Phase 2
0.563	Remote Similarity	NPD7516	Approved
0.561	Remote Similarity	NPD6616	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