NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.07
Volume:	273.692
LogP:	3.075
LogD:	2.703
LogS:	-5.161
# Rotatable Bonds:	2
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.716
Synthetic Accessibility Score:	1.87
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.649
MDCK Permeability:	3.143825597362593e-05
Pgp-inhibitor:	0.965
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.589

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.298
Plasma Protein Binding (PPB):	95.45861053466797%
Volume Distribution (VD):	0.512
Pgp-substrate:	1.984214425086975%

ADMET: Metabolism

CYP1A2-inhibitor:	0.943
CYP1A2-substrate:	0.905
CYP2C19-inhibitor:	0.655
CYP2C19-substrate:	0.26
CYP2C9-inhibitor:	0.724
CYP2C9-substrate:	0.855
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.6
CYP3A4-inhibitor:	0.76
CYP3A4-substrate:	0.366

ADMET: Excretion

Clearance (CL):	6.427
Half-life (T1/2):	0.126

ADMET: Toxicity

hERG Blockers:	0.089
Human Hepatotoxicity (H-HT):	0.098
Drug-inuced Liver Injury (DILI):	0.856
AMES Toxicity:	0.8
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.279
Skin Sensitization:	0.07
Carcinogencity:	0.953
Eye Corrosion:	0.004
Eye Irritation:	0.925
Respiratory Toxicity:	0.106

Download Data

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

Natural Product: NPC223330

Natural Product ID:	NPC223330
*Common Name:**	11Beta,13-Dihydroreynosin
IUPAC Name:	(3S,3aS,5aR,6R,9aS,9bS)-6-hydroxy-3,5a-dimethyl-9-methylidene-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran-2-one
Synonyms:	11Beta,13-Dihydro-Reynosin; 11Beta,13-Dihydroreynosin
Standard InCHIKey:	JWBPWNWPEVPCMJ-DMLGPZFASA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h9-13,16H,1,4-7H2,2-3H3/t9-,10-,11+,12+,13-,15-/m0/s1
SMILES:	C=C1CC[C@H]([C@]2([C@H]1[C@H]1OC(=O)[C@H]([C@@H]1CC2)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL272177
PubChem CID:	189086
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO19178	Justicia hyssopifolia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11312930]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[14510592]
NPO14250	Schisandra henryi	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[14661856]
NPO15563	Valeriana prionophylla	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270567]
NPO2890	Scrophularia lepidota	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572418]
NPO16933	Halichondria cylindrata	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8991950]
NPO13812	Illicium floridanum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548851]
NPO11474	Ligusticum jeholense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2890	Scrophularia lepidota	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19178	Justicia hyssopifolia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11474	Ligusticum jeholense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2890	Scrophularia lepidota	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19178	Justicia hyssopifolia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27265	Hopea parviflora	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14250	Schisandra henryi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14250	Schisandra henryi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11474	Ligusticum jeholense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11474	Ligusticum jeholense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27155	Aconitum nasutum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27227	Matricaria occidentalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16046	Buchnerodendron speciosum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO22448	Helichrysum nanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15563	Valeriana prionophylla	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23695	Setosphaeria turcica	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14245.1	Veratrum album subsp. lobelianum	Subspecies	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27554	Doryanthes palmeri	Species	Doryanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18226	Ajuga chia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27073	Poranthera corymbosa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16268	Blattella germanica	Species	Ectobiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18776	Erlangea fusca	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27533	Senecio bergii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26926	Montanoa frutescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27137	Ocotea usambarensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12395	Cardamine impatiens	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27447	Yucca aloifolia	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27265	Hopea parviflora	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17818	Acrantophis dumerili	Species	Boidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21638	Attalea cohune	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18627	Cardamine komarovii	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18565	Penicillium striatisporum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13812	Illicium floridanum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27836	Gymnodinium microadriaticum	Species	Gymnodiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16933	Halichondria cylindrata	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5306	Infundibulicybe catinus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27355	Pseudokeronopsis rubra	Species	Pseudokeronopsidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19178	Justicia hyssopifolia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2890	Scrophularia lepidota	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27708	Mythimna separata	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11474	Ligusticum jeholense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14250	Schisandra henryi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27304	Stevia sanguinea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27519	Alternaria chrysanthemi	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18294	Anacyclus clavatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18501	Salvia carduacea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18969	Dysidea etheria	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6164	Lasiosiphon eriocephalus	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10635	Schkuhria pusilla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27409	Scabiosa atropurpurea	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15831	Panicum dichotomiflorum	Species	Poaceae	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	3

Activity Type	# Activity
Cell Line	3
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT377	Cell Line	OVCAR-3	Homo sapiens	CD50	=	95.0	ug ml-1	PMID[452125]
NPT165	Cell Line	HeLa	Homo sapiens	CD50	>	100.0	ug ml-1	PMID[452125]
NPT65	Cell Line	HepG2	Homo sapiens	CD50	>	100.0	ug ml-1	PMID[452125]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	>	209700.0	nM	PMID[452124]

☑ 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 NPC223330 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	152
0.1-0.2	1294
0.2-0.3	5515
0.3-0.4	14959
0.4-0.5	7025
0.5-0.6	5938
0.6-0.7	5697
0.7-0.8	1982
0.8-0.85	103
0.85-0.9	21
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC209318
0.9375	High Similarity	NPC85698
0.9367	High Similarity	NPC97505
0.9259	High Similarity	NPC305029
0.9136	High Similarity	NPC6979
0.9079	High Similarity	NPC92489
0.9036	High Similarity	NPC194642
0.9024	High Similarity	NPC181103
0.8987	High Similarity	NPC475951
0.8902	High Similarity	NPC185638
0.8902	High Similarity	NPC9231
0.8831	High Similarity	NPC476601
0.881	High Similarity	NPC116620
0.8765	High Similarity	NPC470948
0.8721	High Similarity	NPC147272
0.8675	High Similarity	NPC477920
0.8642	High Similarity	NPC226988
0.8621	High Similarity	NPC148000
0.8621	High Similarity	NPC225474
0.8621	High Similarity	NPC469596
0.8621	High Similarity	NPC24861
0.8605	High Similarity	NPC233345
0.8605	High Similarity	NPC186363
0.8588	High Similarity	NPC253618
0.8588	High Similarity	NPC77001
0.8571	High Similarity	NPC470012
0.8554	High Similarity	NPC52628
0.8554	High Similarity	NPC329738
0.8537	High Similarity	NPC471037
0.8523	High Similarity	NPC157686
0.8523	High Similarity	NPC259042
0.8488	Intermediate Similarity	NPC153853
0.8481	Intermediate Similarity	NPC474433
0.8471	Intermediate Similarity	NPC277771
0.8452	Intermediate Similarity	NPC250981
0.8427	Intermediate Similarity	NPC93245
0.8427	Intermediate Similarity	NPC256227
0.8333	Intermediate Similarity	NPC136781
0.8333	Intermediate Similarity	NPC473963
0.8333	Intermediate Similarity	NPC476602
0.8315	Intermediate Similarity	NPC90014
0.8313	Intermediate Similarity	NPC243347
0.8295	Intermediate Similarity	NPC470224
0.8295	Intermediate Similarity	NPC63118
0.8295	Intermediate Similarity	NPC49776
0.8295	Intermediate Similarity	NPC474436
0.8293	Intermediate Similarity	NPC38642
0.8293	Intermediate Similarity	NPC473420
0.825	Intermediate Similarity	NPC307865
0.825	Intermediate Similarity	NPC238227
0.8235	Intermediate Similarity	NPC12774
0.8235	Intermediate Similarity	NPC325594
0.8222	Intermediate Similarity	NPC473964
0.8214	Intermediate Similarity	NPC139566
0.8202	Intermediate Similarity	NPC303863
0.8182	Intermediate Similarity	NPC160506
0.8182	Intermediate Similarity	NPC91369
0.8182	Intermediate Similarity	NPC250753
0.8152	Intermediate Similarity	NPC47024
0.8148	Intermediate Similarity	NPC247783
0.8148	Intermediate Similarity	NPC35574
0.8148	Intermediate Similarity	NPC269543
0.814	Intermediate Similarity	NPC33768
0.814	Intermediate Similarity	NPC175293
0.8118	Intermediate Similarity	NPC264317
0.8118	Intermediate Similarity	NPC294438
0.8111	Intermediate Similarity	NPC183012
0.8111	Intermediate Similarity	NPC210214
0.8111	Intermediate Similarity	NPC98639
0.8095	Intermediate Similarity	NPC245866
0.8095	Intermediate Similarity	NPC312480
0.8095	Intermediate Similarity	NPC194637
0.809	Intermediate Similarity	NPC294263
0.8072	Intermediate Similarity	NPC232625
0.8072	Intermediate Similarity	NPC475665
0.8068	Intermediate Similarity	NPC475776
0.8065	Intermediate Similarity	NPC475958
0.8049	Intermediate Similarity	NPC263951
0.8046	Intermediate Similarity	NPC4309
0.8046	Intermediate Similarity	NPC477128
0.8046	Intermediate Similarity	NPC255176
0.8046	Intermediate Similarity	NPC474719
0.8043	Intermediate Similarity	NPC473155
0.8043	Intermediate Similarity	NPC216478
0.8043	Intermediate Similarity	NPC476807
0.8043	Intermediate Similarity	NPC164349
0.8043	Intermediate Similarity	NPC476806
0.8023	Intermediate Similarity	NPC82979
0.8023	Intermediate Similarity	NPC473226
0.8023	Intermediate Similarity	NPC2783
0.8023	Intermediate Similarity	NPC73038
0.8023	Intermediate Similarity	NPC329692
0.8022	Intermediate Similarity	NPC327179
0.8022	Intermediate Similarity	NPC165528
0.8022	Intermediate Similarity	NPC284518
0.8022	Intermediate Similarity	NPC29410
0.8022	Intermediate Similarity	NPC104568
0.8022	Intermediate Similarity	NPC200054
0.8022	Intermediate Similarity	NPC13949
0.8022	Intermediate Similarity	NPC228766
0.8	Intermediate Similarity	NPC263974
0.8	Intermediate Similarity	NPC219011
0.8	Intermediate Similarity	NPC2728
0.8	Intermediate Similarity	NPC39362
0.8	Intermediate Similarity	NPC470011
0.8	Intermediate Similarity	NPC60837
0.8	Intermediate Similarity	NPC282619
0.8	Intermediate Similarity	NPC130966
0.8	Intermediate Similarity	NPC172613
0.8	Intermediate Similarity	NPC11555
0.8	Intermediate Similarity	NPC208198
0.8	Intermediate Similarity	NPC250075
0.7978	Intermediate Similarity	NPC38754
0.7978	Intermediate Similarity	NPC475416
0.7978	Intermediate Similarity	NPC187722
0.7978	Intermediate Similarity	NPC198054
0.7976	Intermediate Similarity	NPC123880
0.7976	Intermediate Similarity	NPC471159
0.7976	Intermediate Similarity	NPC110780
0.7976	Intermediate Similarity	NPC170985
0.7957	Intermediate Similarity	NPC477655
0.7957	Intermediate Similarity	NPC267921
0.7955	Intermediate Similarity	NPC470588
0.7955	Intermediate Similarity	NPC128496
0.7952	Intermediate Similarity	NPC170038
0.7935	Intermediate Similarity	NPC10864
0.7935	Intermediate Similarity	NPC253586
0.7931	Intermediate Similarity	NPC269360
0.7931	Intermediate Similarity	NPC477926
0.7931	Intermediate Similarity	NPC167877
0.7931	Intermediate Similarity	NPC264005
0.7931	Intermediate Similarity	NPC142361
0.7931	Intermediate Similarity	NPC474684
0.7912	Intermediate Similarity	NPC69548
0.7912	Intermediate Similarity	NPC205173
0.7912	Intermediate Similarity	NPC184848
0.7907	Intermediate Similarity	NPC102292
0.7901	Intermediate Similarity	NPC41017
0.7895	Intermediate Similarity	NPC61442
0.7889	Intermediate Similarity	NPC287118
0.7889	Intermediate Similarity	NPC229281
0.7889	Intermediate Similarity	NPC107674
0.7889	Intermediate Similarity	NPC202728
0.7889	Intermediate Similarity	NPC199543
0.7889	Intermediate Similarity	NPC473690
0.7889	Intermediate Similarity	NPC170220
0.7889	Intermediate Similarity	NPC470375
0.7889	Intermediate Similarity	NPC158059
0.7889	Intermediate Similarity	NPC118519
0.7889	Intermediate Similarity	NPC141497
0.7889	Intermediate Similarity	NPC471902
0.7889	Intermediate Similarity	NPC470376
0.7882	Intermediate Similarity	NPC118800
0.7875	Intermediate Similarity	NPC102313
0.7875	Intermediate Similarity	NPC199316
0.7872	Intermediate Similarity	NPC81530
0.7872	Intermediate Similarity	NPC39683
0.7865	Intermediate Similarity	NPC210037
0.7865	Intermediate Similarity	NPC474728
0.7865	Intermediate Similarity	NPC158488
0.7865	Intermediate Similarity	NPC290614
0.7865	Intermediate Similarity	NPC18872
0.7865	Intermediate Similarity	NPC193750
0.7865	Intermediate Similarity	NPC44240
0.7865	Intermediate Similarity	NPC471896
0.7865	Intermediate Similarity	NPC120968
0.7865	Intermediate Similarity	NPC477872
0.7865	Intermediate Similarity	NPC7260
0.7865	Intermediate Similarity	NPC273621
0.7865	Intermediate Similarity	NPC227467
0.7857	Intermediate Similarity	NPC475743
0.7857	Intermediate Similarity	NPC328264
0.7849	Intermediate Similarity	NPC26270
0.7849	Intermediate Similarity	NPC471038
0.7849	Intermediate Similarity	NPC162459
0.7849	Intermediate Similarity	NPC28864
0.7849	Intermediate Similarity	NPC89099
0.7849	Intermediate Similarity	NPC38471
0.7849	Intermediate Similarity	NPC98837
0.7849	Intermediate Similarity	NPC38296
0.7849	Intermediate Similarity	NPC78427
0.7849	Intermediate Similarity	NPC20479
0.7849	Intermediate Similarity	NPC16911
0.7848	Intermediate Similarity	NPC72343
0.7841	Intermediate Similarity	NPC254572
0.7841	Intermediate Similarity	NPC40552
0.7841	Intermediate Similarity	NPC474845
0.7841	Intermediate Similarity	NPC215831
0.7841	Intermediate Similarity	NPC250687
0.7841	Intermediate Similarity	NPC56413
0.7841	Intermediate Similarity	NPC242864
0.7841	Intermediate Similarity	NPC48824
0.7841	Intermediate Similarity	NPC146937
0.7841	Intermediate Similarity	NPC473242
0.7841	Intermediate Similarity	NPC473229
0.7841	Intermediate Similarity	NPC229407
0.7841	Intermediate Similarity	NPC17733
0.7841	Intermediate Similarity	NPC470629
0.7841	Intermediate Similarity	NPC181225
0.7841	Intermediate Similarity	NPC471900

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 NPC223330 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1716
0.2-0.3	3980
0.3-0.4	2230
0.4-0.5	597
0.5-0.6	189
0.6-0.7	206
0.7-0.8	80
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD8034	Phase 2
0.8182	Intermediate Similarity	NPD8035	Phase 2
0.8118	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD6399	Phase 3
0.7614	Intermediate Similarity	NPD3618	Phase 1
0.7558	Intermediate Similarity	NPD3667	Approved
0.7553	Intermediate Similarity	NPD7902	Approved
0.7419	Intermediate Similarity	NPD7748	Approved
0.7391	Intermediate Similarity	NPD7515	Phase 2
0.7386	Intermediate Similarity	NPD4786	Approved
0.7381	Intermediate Similarity	NPD6116	Phase 1
0.7303	Intermediate Similarity	NPD1694	Approved
0.7292	Intermediate Similarity	NPD4225	Approved
0.7262	Intermediate Similarity	NPD6117	Approved
0.7234	Intermediate Similarity	NPD7900	Approved
0.7234	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5330	Approved
0.7222	Intermediate Similarity	NPD6684	Approved
0.7222	Intermediate Similarity	NPD7334	Approved
0.7222	Intermediate Similarity	NPD7521	Approved
0.7222	Intermediate Similarity	NPD7146	Approved
0.7222	Intermediate Similarity	NPD6409	Approved
0.72	Intermediate Similarity	NPD5739	Approved
0.72	Intermediate Similarity	NPD7128	Approved
0.72	Intermediate Similarity	NPD6675	Approved
0.72	Intermediate Similarity	NPD6402	Approved
0.7191	Intermediate Similarity	NPD3133	Approved
0.7191	Intermediate Similarity	NPD3666	Approved
0.7191	Intermediate Similarity	NPD3665	Phase 1
0.7174	Intermediate Similarity	NPD5328	Approved
0.7157	Intermediate Similarity	NPD6373	Approved
0.7157	Intermediate Similarity	NPD6372	Approved
0.7129	Intermediate Similarity	NPD5701	Approved
0.7129	Intermediate Similarity	NPD5697	Approved
0.7128	Intermediate Similarity	NPD4202	Approved
0.7113	Intermediate Similarity	NPD7638	Approved
0.7093	Intermediate Similarity	NPD6115	Approved
0.7093	Intermediate Similarity	NPD6118	Approved
0.7093	Intermediate Similarity	NPD6114	Approved
0.7093	Intermediate Similarity	NPD6697	Approved
0.7079	Intermediate Similarity	NPD4788	Approved
0.7065	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6903	Approved
0.7059	Intermediate Similarity	NPD6899	Approved
0.7059	Intermediate Similarity	NPD7320	Approved
0.7059	Intermediate Similarity	NPD6881	Approved
0.7059	Intermediate Similarity	NPD6011	Approved
0.7041	Intermediate Similarity	NPD7639	Approved
0.7041	Intermediate Similarity	NPD7640	Approved
0.703	Intermediate Similarity	NPD6008	Approved
0.7021	Intermediate Similarity	NPD6411	Approved
0.7021	Intermediate Similarity	NPD6079	Approved
0.7019	Intermediate Similarity	NPD6649	Approved
0.7019	Intermediate Similarity	NPD6650	Approved
0.701	Intermediate Similarity	NPD6084	Phase 2
0.701	Intermediate Similarity	NPD6083	Phase 2
0.699	Remote Similarity	NPD6012	Approved
0.699	Remote Similarity	NPD6014	Approved
0.699	Remote Similarity	NPD6013	Approved
0.6979	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3702	Approved
0.6939	Remote Similarity	NPD5696	Approved
0.6923	Remote Similarity	NPD7102	Approved
0.6923	Remote Similarity	NPD6883	Approved
0.6923	Remote Similarity	NPD7290	Approved
0.6907	Remote Similarity	NPD4697	Phase 3
0.6882	Remote Similarity	NPD5737	Approved
0.6882	Remote Similarity	NPD6672	Approved
0.6875	Remote Similarity	NPD6001	Approved
0.6875	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8130	Phase 1
0.6857	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6617	Approved
0.6857	Remote Similarity	NPD6869	Approved
0.6857	Remote Similarity	NPD6847	Approved
0.6837	Remote Similarity	NPD4755	Approved
0.6813	Remote Similarity	NPD3668	Phase 3
0.6809	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6101	Approved
0.6804	Remote Similarity	NPD5695	Phase 3
0.6804	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6882	Approved
0.6792	Remote Similarity	NPD8297	Approved
0.679	Remote Similarity	NPD4224	Phase 2
0.6786	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5777	Approved
0.6774	Remote Similarity	NPD3573	Approved
0.6747	Remote Similarity	NPD3698	Phase 2
0.6744	Remote Similarity	NPD3703	Phase 2
0.6742	Remote Similarity	NPD7525	Registered
0.6735	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5222	Approved
0.6735	Remote Similarity	NPD5221	Approved
0.6731	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5285	Approved
0.67	Remote Similarity	NPD4696	Approved
0.67	Remote Similarity	NPD5286	Approved
0.67	Remote Similarity	NPD4700	Approved
0.6697	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD4244	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD4245	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5223	Approved
0.6632	Remote Similarity	NPD4753	Phase 2
0.6629	Remote Similarity	NPD7645	Phase 2
0.6607	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6274	Approved
0.6604	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5779	Approved
0.6598	Remote Similarity	NPD5778	Approved
0.6593	Remote Similarity	NPD4223	Phase 3
0.6593	Remote Similarity	NPD4221	Approved
0.6574	Remote Similarity	NPD4632	Approved
0.6574	Remote Similarity	NPD8133	Approved
0.6571	Remote Similarity	NPD6686	Approved
0.6569	Remote Similarity	NPD5224	Approved
0.6569	Remote Similarity	NPD4633	Approved
0.6569	Remote Similarity	NPD5211	Phase 2
0.6569	Remote Similarity	NPD5226	Approved
0.6569	Remote Similarity	NPD7632	Discontinued
0.6569	Remote Similarity	NPD5225	Approved
0.6562	Remote Similarity	NPD5207	Approved
0.6556	Remote Similarity	NPD4695	Discontinued
0.6552	Remote Similarity	NPD6942	Approved
0.6552	Remote Similarity	NPD7339	Approved
0.6545	Remote Similarity	NPD6317	Approved
0.6526	Remote Similarity	NPD5208	Approved
0.6517	Remote Similarity	NPD3617	Approved
0.6505	Remote Similarity	NPD5175	Approved
0.6505	Remote Similarity	NPD4754	Approved
0.6505	Remote Similarity	NPD5174	Approved
0.6495	Remote Similarity	NPD7637	Suspended
0.6486	Remote Similarity	NPD6313	Approved
0.6486	Remote Similarity	NPD6314	Approved
0.6486	Remote Similarity	NPD6335	Approved
0.6484	Remote Similarity	NPD5369	Approved
0.6476	Remote Similarity	NPD6412	Phase 2
0.6471	Remote Similarity	NPD4789	Approved
0.6465	Remote Similarity	NPD4629	Approved
0.6465	Remote Similarity	NPD5210	Approved
0.6458	Remote Similarity	NPD6904	Approved
0.6458	Remote Similarity	NPD6080	Approved
0.6458	Remote Similarity	NPD6673	Approved
0.6458	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6868	Approved
0.6452	Remote Similarity	NPD4197	Approved
0.6442	Remote Similarity	NPD5141	Approved
0.6437	Remote Similarity	NPD6924	Approved
0.6437	Remote Similarity	NPD6926	Approved
0.6429	Remote Similarity	NPD229	Approved
0.6429	Remote Similarity	NPD7101	Approved
0.6429	Remote Similarity	NPD7100	Approved
0.6413	Remote Similarity	NPD6435	Approved
0.64	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6009	Approved
0.6395	Remote Similarity	NPD6081	Approved
0.6383	Remote Similarity	NPD5329	Approved
0.6381	Remote Similarity	NPD4767	Approved
0.6381	Remote Similarity	NPD4768	Approved
0.6374	Remote Similarity	NPD7509	Discontinued
0.6372	Remote Similarity	NPD6319	Approved
0.6364	Remote Similarity	NPD5282	Discontinued
0.6344	Remote Similarity	NPD7154	Phase 3
0.6344	Remote Similarity	NPD5362	Discontinued
0.6333	Remote Similarity	NPD3671	Phase 1
0.6333	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5693	Phase 1
0.6321	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4519	Discontinued
0.6316	Remote Similarity	NPD4623	Approved
0.6316	Remote Similarity	NPD4693	Phase 3
0.6316	Remote Similarity	NPD6909	Approved
0.6316	Remote Similarity	NPD5983	Phase 2
0.6316	Remote Similarity	NPD4138	Approved
0.6316	Remote Similarity	NPD4688	Approved
0.6316	Remote Similarity	NPD4689	Approved
0.6316	Remote Similarity	NPD4690	Approved
0.6316	Remote Similarity	NPD5205	Approved
0.6316	Remote Similarity	NPD6908	Approved
0.6293	Remote Similarity	NPD7492	Approved
0.6292	Remote Similarity	NPD6933	Approved
0.6277	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5128	Approved
0.6262	Remote Similarity	NPD4729	Approved
0.6262	Remote Similarity	NPD4730	Approved
0.6239	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