NPASS Compound

Structure

CID211777 OpenBabel06191716002D 38 42 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 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 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9757 -3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6449 -3.8364 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 5.1962 -2.0000 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 6.1667 -4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 1 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 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 -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 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 -4.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 34 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 2 0 0 0 0 6 18 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 35 1 0 0 0 0 9 15 1 0 0 0 0 9 19 1 0 0 0 0 10 16 1 0 0 0 0 10 26 1 0 0 0 0 11 28 1 0 0 0 0 12 13 2 0 0 0 0 12 35 1 0 0 0 0 14 23 1 0 0 0 0 14 27 1 0 0 0 0 15 24 1 0 0 0 0 15 26 1 6 0 0 0 16 13 1 1 0 0 0 16 36 1 0 0 0 0 17 11 1 1 0 0 0 17 20 1 0 0 0 0 17 37 1 0 0 0 0 18 26 1 1 0 0 0 18 27 1 0 0 0 0 19 27 1 1 0 0 0 19 38 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 6 0 0 0 21 22 1 0 0 0 0 21 30 1 1 0 0 0 22 25 1 0 0 0 0 22 31 1 6 0 0 0 23 32 2 0 0 0 0 23 34 1 0 0 0 0 24 33 2 0 0 0 0 24 36 1 0 0 0 0 25 37 1 0 0 0 0 25 38 1 1 0 0 0 26 1 1 1 0 0 0 27 2 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	536.23
Volume:	516.276
LogP:	1.555
LogD:	1.256
LogS:	-3.855
# Rotatable Bonds:	6
TPSA:	165.12
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	5.17
Fsp3:	0.704
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.291
MDCK Permeability:	8.311322017107159e-05
Pgp-inhibitor:	0.734
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.621
20% Bioavailability (F20%):	0.174
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	72.2745590209961%
Volume Distribution (VD):	1.316
Pgp-substrate:	19.062915802001953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.147
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.402
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.286
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	7.206
Half-life (T1/2):	0.713

ADMET: Toxicity

hERG Blockers:	0.123
Human Hepatotoxicity (H-HT):	0.273
Drug-inuced Liver Injury (DILI):	0.122
AMES Toxicity:	0.088
Rat Oral Acute Toxicity:	0.643
Maximum Recommended Daily Dose:	0.838
Skin Sensitization:	0.106
Carcinogencity:	0.729
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC211777

Natural Product ID:	NPC211777
*Common Name:**	Borapetoside C
IUPAC Name:	methyl (2S,4aR,6R,6aR,10aS,10bS)-2-(furan-3-yl)-6a,10b-dimethyl-4-oxo-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,4a,5,6,9,10,10a-octahydrobenzo[f]isochromene-7-carboxylate
Synonyms:	Borapetoside C
Standard InCHIKey:	RBPCODNTTHTSFN-ZDMQDBCMSA-N
Standard InCHI:	InChI=1S/C27H36O11/c1-26-10-16(13-7-8-35-12-13)36-24(33)15(26)9-19(27(2)14(23(32)34-3)5-4-6-18(26)27)38-25-22(31)21(30)20(29)17(11-28)37-25/h5,7-8,12,15-22,25,28-31H,4,6,9-11H2,1-3H3/t15-,16-,17+,18-,19+,20+,21-,22+,25-,26+,27-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2C[C@H]3C(=O)O[C@@H](C[C@]3([C@H]3[C@]2(C)C(=CCC3)C(=O)OC)C)c2cocc2)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097581
PubChem CID:	15934414
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene 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
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20356064]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22283497]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	leaf	Putz City, Chiayi County, Taiwan	2009-Nov	PMID[25999202]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28742368]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29397715]
NPO25761	Thalictrum microgynum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25761	Thalictrum microgynum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25989	Calea berteriana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25761	Thalictrum microgynum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24853	Unio tumidus	Species	Unionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25964	Amsinckia lycopsoides	Species	Boraginaceae	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	2
Others	17

Activity Type	# Activity
Cell Line	2
Organism	17

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[504771]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	>	10000.0	nM	PMID[504771]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	71.5	pmol/L	PMID[504772]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	70.7	pmol/L	PMID[504772]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	63.0	pmol/L	PMID[504772]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	142.6	pmol/L	PMID[504772]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	149.6	pmol/L	PMID[504772]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	16.3	pmol/L	PMID[504772]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	15.7	pmol/L	PMID[504772]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	15.9	pmol/L	PMID[504772]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	14.8	pmol/L	PMID[504772]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	14.3	pmol/L	PMID[504772]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	111.3	pmol/L	PMID[504772]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	170.8	pmol/L	PMID[504772]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	173.0	pmol/L	PMID[504772]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	253.9	pmol/L	PMID[504772]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	257.6	pmol/L	PMID[504772]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	293.0	mg/dl	PMID[504772]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	343.0	mg/dl	PMID[504772]

☑ 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 NPC211777 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	346
0.1-0.2	1369
0.2-0.3	3040
0.3-0.4	5277
0.4-0.5	9439
0.5-0.6	9771
0.6-0.7	9729
0.7-0.8	3278
0.8-0.85	252
0.85-0.9	154
0.9-0.95	34
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC198047
0.9742	High Similarity	NPC100333
0.9739	High Similarity	NPC207978
0.9737	High Similarity	NPC262872
0.9677	High Similarity	NPC93172
0.9677	High Similarity	NPC97574
0.9557	High Similarity	NPC160818
0.9557	High Similarity	NPC169299
0.9494	High Similarity	NPC82602
0.9481	High Similarity	NPC307383
0.9363	High Similarity	NPC470182
0.9281	High Similarity	NPC476940
0.9281	High Similarity	NPC476939
0.9281	High Similarity	NPC469503
0.9259	High Similarity	NPC262386
0.9241	High Similarity	NPC146991
0.9236	High Similarity	NPC69028
0.9236	High Similarity	NPC200782
0.9177	High Similarity	NPC477405
0.9167	High Similarity	NPC45101
0.9161	High Similarity	NPC469336
0.9161	High Similarity	NPC35000
0.9156	High Similarity	NPC147168
0.9119	High Similarity	NPC276551
0.9097	High Similarity	NPC178932
0.9097	High Similarity	NPC282445
0.9097	High Similarity	NPC30222
0.9062	High Similarity	NPC470875
0.9057	High Similarity	NPC292389
0.9057	High Similarity	NPC469338
0.9051	High Similarity	NPC477402
0.9045	High Similarity	NPC472778
0.9045	High Similarity	NPC472777
0.9045	High Similarity	NPC472776
0.9038	High Similarity	NPC214541
0.9038	High Similarity	NPC44675
0.9038	High Similarity	NPC264943
0.9032	High Similarity	NPC476201
0.902	High Similarity	NPC7388
0.902	High Similarity	NPC476942
0.902	High Similarity	NPC476941
0.9	High Similarity	NPC271657
0.9	High Similarity	NPC470940
0.9	High Similarity	NPC469849
0.8994	High Similarity	NPC82851
0.8994	High Similarity	NPC5079
0.8994	High Similarity	NPC149896
0.8954	High Similarity	NPC476937
0.8954	High Similarity	NPC476938
0.8951	High Similarity	NPC471397
0.8938	High Similarity	NPC134254
0.8938	High Similarity	NPC39986
0.8938	High Similarity	NPC234660
0.8938	High Similarity	NPC472773
0.8938	High Similarity	NPC51568
0.8938	High Similarity	NPC302369
0.8931	High Similarity	NPC335761
0.8924	High Similarity	NPC261597
0.8924	High Similarity	NPC249021
0.8924	High Similarity	NPC36655
0.8917	High Similarity	NPC476262
0.891	High Similarity	NPC44577
0.8903	High Similarity	NPC159927
0.8903	High Similarity	NPC476122
0.8903	High Similarity	NPC469335
0.8889	High Similarity	NPC173516
0.8889	High Similarity	NPC472282
0.8875	High Similarity	NPC18347
0.8875	High Similarity	NPC472771
0.8875	High Similarity	NPC263432
0.8868	High Similarity	NPC475967
0.8868	High Similarity	NPC477403
0.8854	High Similarity	NPC57998
0.8834	High Similarity	NPC271235
0.8831	High Similarity	NPC470941
0.8831	High Similarity	NPC250228
0.8827	High Similarity	NPC472141
0.882	High Similarity	NPC419
0.882	High Similarity	NPC472139
0.8812	High Similarity	NPC472653
0.8805	High Similarity	NPC187149
0.8805	High Similarity	NPC472283
0.8805	High Similarity	NPC286722
0.8805	High Similarity	NPC299038
0.8805	High Similarity	NPC472772
0.8797	High Similarity	NPC281258
0.8782	High Similarity	NPC477404
0.8782	High Similarity	NPC476936
0.8782	High Similarity	NPC196864
0.8773	High Similarity	NPC472775
0.8773	High Similarity	NPC472774
0.8773	High Similarity	NPC472651
0.8765	High Similarity	NPC476857
0.8765	High Similarity	NPC476856
0.8765	High Similarity	NPC476858
0.8758	High Similarity	NPC329938
0.8758	High Similarity	NPC476944
0.8758	High Similarity	NPC290400
0.8758	High Similarity	NPC117986
0.8758	High Similarity	NPC96443
0.875	High Similarity	NPC475295
0.875	High Similarity	NPC473473
0.8742	High Similarity	NPC469485
0.8742	High Similarity	NPC209364
0.872	High Similarity	NPC160651
0.872	High Similarity	NPC472652
0.8718	High Similarity	NPC472654
0.8718	High Similarity	NPC125182
0.8718	High Similarity	NPC69647
0.8718	High Similarity	NPC195325
0.8712	High Similarity	NPC307781
0.8712	High Similarity	NPC472670
0.8712	High Similarity	NPC475779
0.8701	High Similarity	NPC41182
0.8696	High Similarity	NPC25255
0.8688	High Similarity	NPC173544
0.8679	High Similarity	NPC469850
0.8659	High Similarity	NPC476850
0.8659	High Similarity	NPC476853
0.8659	High Similarity	NPC476861
0.865	High Similarity	NPC123088
0.8645	High Similarity	NPC346
0.8642	High Similarity	NPC193798
0.8642	High Similarity	NPC188649
0.8639	High Similarity	NPC470938
0.8636	High Similarity	NPC137295
0.8634	High Similarity	NPC474611
0.8634	High Similarity	NPC475226
0.8625	High Similarity	NPC107646
0.8625	High Similarity	NPC126723
0.8608	High Similarity	NPC18135
0.8606	High Similarity	NPC472673
0.8598	High Similarity	NPC23387
0.859	High Similarity	NPC255414
0.8589	High Similarity	NPC288602
0.8589	High Similarity	NPC88841
0.8589	High Similarity	NPC165218
0.858	High Similarity	NPC470789
0.858	High Similarity	NPC475381
0.8571	High Similarity	NPC197137
0.8571	High Similarity	NPC167142
0.8562	High Similarity	NPC141538
0.8562	High Similarity	NPC296807
0.8562	High Similarity	NPC92979
0.8562	High Similarity	NPC155939
0.8553	High Similarity	NPC33938
0.8544	High Similarity	NPC470997
0.8543	High Similarity	NPC310830
0.8537	High Similarity	NPC476860
0.8528	High Similarity	NPC470792
0.8528	High Similarity	NPC470939
0.8512	High Similarity	NPC94763
0.8512	High Similarity	NPC236004
0.8509	High Similarity	NPC60973
0.8506	High Similarity	NPC121158
0.8503	High Similarity	NPC159232
0.85	High Similarity	NPC253201
0.85	High Similarity	NPC302054
0.8494	Intermediate Similarity	NPC472766
0.8494	Intermediate Similarity	NPC296558
0.8494	Intermediate Similarity	NPC472765
0.8485	Intermediate Similarity	NPC121995
0.8485	Intermediate Similarity	NPC478178
0.8485	Intermediate Similarity	NPC214600
0.8481	Intermediate Similarity	NPC234494
0.8476	Intermediate Similarity	NPC469846
0.8476	Intermediate Similarity	NPC476197
0.8471	Intermediate Similarity	NPC221809
0.8471	Intermediate Similarity	NPC471174
0.8471	Intermediate Similarity	NPC10088
0.8466	Intermediate Similarity	NPC305016
0.8462	Intermediate Similarity	NPC5676
0.8457	Intermediate Similarity	NPC194499
0.8457	Intermediate Similarity	NPC88007
0.8457	Intermediate Similarity	NPC470118
0.8452	Intermediate Similarity	NPC223415
0.8452	Intermediate Similarity	NPC476946
0.8438	Intermediate Similarity	NPC472672
0.8438	Intermediate Similarity	NPC294511
0.8438	Intermediate Similarity	NPC268905
0.8438	Intermediate Similarity	NPC121615
0.8438	Intermediate Similarity	NPC75906
0.8434	Intermediate Similarity	NPC472764
0.8434	Intermediate Similarity	NPC473766
0.8434	Intermediate Similarity	NPC473753
0.8428	Intermediate Similarity	NPC46551
0.8424	Intermediate Similarity	NPC472664
0.8415	Intermediate Similarity	NPC18986
0.8415	Intermediate Similarity	NPC472767
0.8415	Intermediate Similarity	NPC68848
0.8412	Intermediate Similarity	NPC478177
0.8405	Intermediate Similarity	NPC472671
0.8405	Intermediate Similarity	NPC472779
0.8405	Intermediate Similarity	NPC237155
0.8397	Intermediate Similarity	NPC251865
0.8397	Intermediate Similarity	NPC142113
0.8387	Intermediate Similarity	NPC62103
0.8387	Intermediate Similarity	NPC20578
0.8385	Intermediate Similarity	NPC34421
0.8385	Intermediate Similarity	NPC237259

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 NPC211777 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	981
0.2-0.3	2110
0.3-0.4	2621
0.4-0.5	1912
0.5-0.6	904
0.6-0.7	270
0.7-0.8	55
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD5761	Phase 2
0.8333	Intermediate Similarity	NPD5760	Phase 2
0.8114	Intermediate Similarity	NPD8434	Phase 2
0.7931	Intermediate Similarity	NPD6559	Discontinued
0.7811	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD8313	Approved
0.774	Intermediate Similarity	NPD8312	Approved
0.7647	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD3818	Discontinued
0.7485	Intermediate Similarity	NPD4628	Phase 3
0.7458	Intermediate Similarity	NPD7054	Approved
0.743	Intermediate Similarity	NPD6764	Approved
0.743	Intermediate Similarity	NPD6765	Approved
0.7416	Intermediate Similarity	NPD7472	Approved
0.7401	Intermediate Similarity	NPD7228	Approved
0.7368	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8455	Phase 2
0.7368	Intermediate Similarity	NPD7819	Suspended
0.7341	Intermediate Similarity	NPD7075	Discontinued
0.7333	Intermediate Similarity	NPD7251	Discontinued
0.7303	Intermediate Similarity	NPD7799	Discontinued
0.7293	Intermediate Similarity	NPD7808	Phase 3
0.7293	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6797	Phase 2
0.7268	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6785	Approved
0.7268	Intermediate Similarity	NPD6784	Approved
0.7257	Intermediate Similarity	NPD5494	Approved
0.7238	Intermediate Similarity	NPD7685	Pre-registration
0.7238	Intermediate Similarity	NPD7240	Approved
0.7236	Intermediate Similarity	NPD8404	Phase 2
0.7235	Intermediate Similarity	NPD7458	Discontinued
0.7209	Intermediate Similarity	NPD37	Approved
0.7202	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4380	Phase 2
0.7193	Intermediate Similarity	NPD6599	Discontinued
0.7192	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4966	Approved
0.7184	Intermediate Similarity	NPD4967	Phase 2
0.7184	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4965	Approved
0.7167	Intermediate Similarity	NPD5844	Phase 1
0.715	Intermediate Similarity	NPD7435	Discontinued
0.7119	Intermediate Similarity	NPD7199	Phase 2
0.7119	Intermediate Similarity	NPD8127	Discontinued
0.7118	Intermediate Similarity	NPD920	Approved
0.711	Intermediate Similarity	NPD6801	Discontinued
0.7102	Intermediate Similarity	NPD6234	Discontinued
0.7071	Intermediate Similarity	NPD7783	Phase 2
0.7071	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6273	Approved
0.7059	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7411	Suspended
0.7045	Intermediate Similarity	NPD3749	Approved
0.7029	Intermediate Similarity	NPD5402	Approved
0.7029	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD3751	Discontinued
0.7	Intermediate Similarity	NPD2533	Approved
0.7	Intermediate Similarity	NPD6166	Phase 2
0.7	Intermediate Similarity	NPD2534	Approved
0.7	Intermediate Similarity	NPD2532	Approved
0.7	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6777	Approved
0.6995	Remote Similarity	NPD6778	Approved
0.6995	Remote Similarity	NPD6782	Approved
0.6995	Remote Similarity	NPD6779	Approved
0.6995	Remote Similarity	NPD6780	Approved
0.6995	Remote Similarity	NPD6781	Approved
0.6995	Remote Similarity	NPD6776	Approved
0.6988	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7697	Approved
0.6974	Remote Similarity	NPD7698	Approved
0.6974	Remote Similarity	NPD7696	Phase 3
0.6971	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.697	Remote Similarity	NPD8151	Discontinued
0.6961	Remote Similarity	NPD7473	Discontinued
0.6952	Remote Similarity	NPD8150	Discontinued
0.6944	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6799	Approved
0.6939	Remote Similarity	NPD8320	Phase 1
0.6939	Remote Similarity	NPD8319	Approved
0.6936	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD3226	Approved
0.6935	Remote Similarity	NPD7874	Approved
0.6935	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD8407	Phase 2
0.6932	Remote Similarity	NPD3817	Phase 2
0.6927	Remote Similarity	NPD6959	Discontinued
0.6919	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5403	Approved
0.6919	Remote Similarity	NPD7701	Phase 2
0.6914	Remote Similarity	NPD1934	Approved
0.691	Remote Similarity	NPD919	Approved
0.6902	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5401	Approved
0.6889	Remote Similarity	NPD6232	Discontinued
0.6889	Remote Similarity	NPD3787	Discontinued
0.6886	Remote Similarity	NPD2346	Discontinued
0.6885	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1465	Phase 2
0.6865	Remote Similarity	NPD8368	Discontinued
0.6853	Remote Similarity	NPD7870	Phase 2
0.6853	Remote Similarity	NPD7871	Phase 2
0.6842	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6823	Phase 2
0.6829	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7801	Approved
0.6813	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7097	Phase 1
0.6805	Remote Similarity	NPD2800	Approved
0.6805	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7699	Phase 2
0.6804	Remote Similarity	NPD7700	Phase 2
0.6798	Remote Similarity	NPD3882	Suspended
0.6798	Remote Similarity	NPD7768	Phase 2
0.6786	Remote Similarity	NPD7266	Discontinued
0.6784	Remote Similarity	NPD7236	Approved
0.6766	Remote Similarity	NPD2799	Discontinued
0.6765	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3750	Approved
0.6746	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1549	Phase 2
0.674	Remote Similarity	NPD1247	Approved
0.6736	Remote Similarity	NPD6535	Approved
0.6736	Remote Similarity	NPD6534	Approved
0.6726	Remote Similarity	NPD1551	Phase 2
0.6726	Remote Similarity	NPD2796	Approved
0.6717	Remote Similarity	NPD7680	Approved
0.6716	Remote Similarity	NPD7930	Approved
0.6706	Remote Similarity	NPD1243	Approved
0.6706	Remote Similarity	NPD6674	Discontinued
0.6705	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1933	Approved
0.6687	Remote Similarity	NPD6355	Discontinued
0.6687	Remote Similarity	NPD6832	Phase 2
0.6686	Remote Similarity	NPD7239	Suspended
0.6686	Remote Similarity	NPD1653	Approved
0.6686	Remote Similarity	NPD1471	Phase 3
0.6686	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2801	Approved
0.6684	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3748	Approved
0.6667	Remote Similarity	NPD7033	Discontinued
0.665	Remote Similarity	NPD7999	Approved
0.6649	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6100	Approved
0.6627	Remote Similarity	NPD2935	Discontinued
0.6627	Remote Similarity	NPD6099	Approved
0.6617	Remote Similarity	NPD7584	Approved
0.6617	Remote Similarity	NPD7583	Approved
0.6615	Remote Similarity	NPD8360	Approved
0.6615	Remote Similarity	NPD8361	Approved
0.6615	Remote Similarity	NPD8435	Approved
0.6612	Remote Similarity	NPD7229	Phase 3
0.6612	Remote Similarity	NPD5711	Approved
0.6612	Remote Similarity	NPD5710	Approved
0.661	Remote Similarity	NPD7028	Phase 2
0.6609	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD2313	Discontinued
0.6605	Remote Similarity	NPD7319	Approved
0.6603	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD7907	Approved
0.6598	Remote Similarity	NPD6212	Phase 3
0.6598	Remote Similarity	NPD6213	Phase 3
0.6598	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD2344	Approved
0.6588	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6004	Phase 3
0.6588	Remote Similarity	NPD6005	Phase 3
0.6588	Remote Similarity	NPD5762	Approved
0.6588	Remote Similarity	NPD6002	Phase 3
0.6588	Remote Similarity	NPD5763	Approved
0.6588	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD447	Suspended
0.6587	Remote Similarity	NPD4665	Approved
0.6587	Remote Similarity	NPD4111	Phase 1
0.6584	Remote Similarity	NPD7585	Approved
0.6583	Remote Similarity	NPD3057	Approved
0.6582	Remote Similarity	NPD8516	Approved
0.6582	Remote Similarity	NPD8515	Approved
0.6582	Remote Similarity	NPD8517	Approved
0.6582	Remote Similarity	NPD8513	Phase 3
0.6576	Remote Similarity	NPD3926	Phase 2
0.657	Remote Similarity	NPD7003	Approved
0.6566	Remote Similarity	NPD4107	Approved
0.6562	Remote Similarity	NPD1091	Approved
0.655	Remote Similarity	NPD7497	Discontinued
0.6522	Remote Similarity	NPD1608	Approved
0.6522	Remote Similarity	NPD7507	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