NPASS Compound

Structure

NPC187400 OpenBabel07101718322D 56 61 0 0 1 0 0 0 0 0999 V2000 -2.2382 -1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6984 -3.7985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9552 -4.4677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 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 -0.5909 -2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 -2.9543 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 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3509 -3.6089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6818 -2.8658 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2308 -3.6974 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9908 -1.9147 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3216 -1.1716 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3435 -1.3795 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0345 -2.3305 0.0000 C 0 0 1 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 0.7473 -3.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.5263 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0419 -4.5600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 -4.6485 0.0000 O 0 0 0 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 8.6603 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9689 -1.7068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6307 -0.2205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6744 -0.6363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7036 -3.0737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0563 -2.5385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 38 1 0 0 0 0 3 38 1 0 0 0 0 4 39 1 0 0 0 0 5 39 1 0 0 0 0 6 40 1 0 0 0 0 9 13 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 22 2 0 0 0 0 11 14 1 0 0 0 0 11 23 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 40 1 0 0 0 0 17 28 1 0 0 0 0 17 41 1 0 0 0 0 18 43 1 0 0 0 0 19 44 1 0 0 0 0 20 1 1 1 0 0 0 20 21 1 0 0 0 0 21 41 1 1 0 0 0 22 23 1 0 0 0 0 22 38 1 0 0 0 0 23 42 1 1 0 0 0 24 18 1 6 0 0 0 24 30 1 0 0 0 0 24 53 1 0 0 0 0 25 19 1 1 0 0 0 25 31 1 0 0 0 0 25 54 1 0 0 0 0 26 40 1 6 0 0 0 26 42 1 0 0 0 0 27 39 1 0 0 0 0 27 45 1 6 0 0 0 28 42 1 6 0 0 0 28 46 1 0 0 0 0 29 38 1 0 0 0 0 29 55 1 1 0 0 0 30 32 1 0 0 0 0 30 47 1 1 0 0 0 31 33 1 0 0 0 0 31 48 1 6 0 0 0 32 34 1 0 0 0 0 32 49 1 6 0 0 0 33 35 1 0 0 0 0 33 50 1 1 0 0 0 34 36 1 0 0 0 0 34 51 1 1 0 0 0 35 37 1 0 0 0 0 35 52 1 6 0 0 0 36 53 1 0 0 0 0 36 55 1 6 0 0 0 37 54 1 0 0 0 0 37 56 1 1 0 0 0 39 56 1 0 0 0 0 40 41 1 6 0 0 0 41 7 1 1 0 0 0 42 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	800.49
Volume:	804.076
LogP:	3.054
LogD:	2.881
LogS:	-3.321
# Rotatable Bonds:	11
TPSA:	239.22
# H-Bond Aceptor:	14
# H-Bond Donor:	10
# Rings:	6
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.132
Synthetic Accessibility Score:	6.111
Fsp3:	0.952
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.766
MDCK Permeability:	6.486355414381251e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.923
20% Bioavailability (F20%):	0.946
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	83.94927978515625%
Volume Distribution (VD):	0.29
Pgp-substrate:	8.080443382263184%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.058
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.417
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.057

ADMET: Excretion

Clearance (CL):	0.851
Half-life (T1/2):	0.523

ADMET: Toxicity

hERG Blockers:	0.118
Human Hepatotoxicity (H-HT):	0.202
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.093
Rat Oral Acute Toxicity:	0.204
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.24
Carcinogencity:	0.009
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC187400

Natural Product ID:	NPC187400
*Common Name:**	Mogroside Ii B
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[[(3S,8S,9R,10R,11R,13R,14S,17R)-11-hydroxy-17-[(2R,5R)-5-hydroxy-6-methyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	mogroside II B
Standard InCHIKey:	OMJOQOVMHUWPCF-VHLOEOCYSA-N
Standard InCHI:	InChI=1S/C42H72O14/c1-20(9-13-27(45)39(4,5)56-37-35(52)33(50)31(48)25(19-44)54-37)21-15-16-40(6)26-12-10-22-23(42(26,8)28(46)17-41(21,40)7)11-14-29(38(22,2)3)55-36-34(51)32(49)30(47)24(18-43)53-36/h10,20-21,23-37,43-52H,9,11-19H2,1-8H3/t20-,21-,23-,24-,25-,26+,27-,28-,29+,30-,31-,32+,33+,34-,35-,36+,37+,40+,41-,42+/m1/s1
SMILES:	C[C@H](CC[C@H](C(C)(C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)[C@H]1CC[C@@]2(C)[C@@H]3CC=C4[C@@H](CC[C@@H](C4(C)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)[C@]3(C)[C@@H](C[C@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL228083
PubChem CID:	44423068
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins [CHEMONTID:0001687] Cucurbitacin 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
NPO32612	siraitia gros venorii	Species	Cucurbitaceae	Eukaryota	fruits	n.a.	n.a.	PMID[17477572]

☑ 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	6

Activity Type	# Activity
Cell Line	1
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[481410]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	7.2	%	PMID[481410]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	26.0	%	PMID[481410]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	76.0	%	PMID[481410]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	100.0	%	PMID[481410]
NPT2	Others	Unspecified		Ratio	=	1.5	n.a.	PMID[481410]

☑ 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 NPC187400 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	254
0.1-0.2	1910
0.2-0.3	5960
0.3-0.4	12926
0.4-0.5	9389
0.5-0.6	5351
0.6-0.7	3707
0.7-0.8	2108
0.8-0.85	683
0.85-0.9	273
0.9-0.95	90
0.95-1	46

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470885
1.0	High Similarity	NPC221562
0.9796	High Similarity	NPC190395
0.9694	High Similarity	NPC309448
0.9694	High Similarity	NPC242748
0.9691	High Similarity	NPC286969
0.9691	High Similarity	NPC157659
0.9691	High Similarity	NPC473020
0.9691	High Similarity	NPC211879
0.9691	High Similarity	NPC16520
0.9691	High Similarity	NPC155010
0.9691	High Similarity	NPC120123
0.9691	High Similarity	NPC114874
0.9691	High Similarity	NPC8039
0.9691	High Similarity	NPC131479
0.9691	High Similarity	NPC189852
0.9691	High Similarity	NPC245280
0.9691	High Similarity	NPC31907
0.9691	High Similarity	NPC472252
0.96	High Similarity	NPC302057
0.9592	High Similarity	NPC273879
0.9592	High Similarity	NPC165033
0.9588	High Similarity	NPC272015
0.9588	High Similarity	NPC312553
0.9588	High Similarity	NPC288694
0.9588	High Similarity	NPC159036
0.9588	High Similarity	NPC136816
0.9495	High Similarity	NPC473476
0.9495	High Similarity	NPC152584
0.9495	High Similarity	NPC474569
0.9495	High Similarity	NPC69737
0.9495	High Similarity	NPC127801
0.9495	High Similarity	NPC194842
0.9495	High Similarity	NPC473923
0.9495	High Similarity	NPC269627
0.9495	High Similarity	NPC160816
0.9495	High Similarity	NPC208477
0.9495	High Similarity	NPC208594
0.949	High Similarity	NPC16573
0.9485	High Similarity	NPC47566
0.9485	High Similarity	NPC4831
0.9485	High Similarity	NPC129372
0.9485	High Similarity	NPC309425
0.9485	High Similarity	NPC88000
0.9485	High Similarity	NPC472023
0.9485	High Similarity	NPC160734
0.9412	High Similarity	NPC197231
0.94	High Similarity	NPC14946
0.94	High Similarity	NPC231340
0.94	High Similarity	NPC208650
0.94	High Similarity	NPC473469
0.94	High Similarity	NPC63368
0.94	High Similarity	NPC181467
0.9394	High Similarity	NPC75608
0.9381	High Similarity	NPC7341
0.9381	High Similarity	NPC473200
0.9381	High Similarity	NPC282669
0.9375	High Similarity	NPC243728
0.9375	High Similarity	NPC473890
0.932	High Similarity	NPC19888
0.9307	High Similarity	NPC7213
0.9307	High Similarity	NPC476538
0.9307	High Similarity	NPC6931
0.9307	High Similarity	NPC159005
0.9307	High Similarity	NPC472897
0.9307	High Similarity	NPC38217
0.9307	High Similarity	NPC476540
0.9307	High Similarity	NPC476541
0.9307	High Similarity	NPC180183
0.9307	High Similarity	NPC476539
0.9307	High Similarity	NPC246124
0.9307	High Similarity	NPC472896
0.9307	High Similarity	NPC220427
0.9307	High Similarity	NPC472988
0.93	High Similarity	NPC472900
0.93	High Similarity	NPC472898
0.93	High Similarity	NPC472899
0.93	High Similarity	NPC181845
0.9293	High Similarity	NPC473198
0.9293	High Similarity	NPC213190
0.9278	High Similarity	NPC234287
0.9278	High Similarity	NPC158088
0.9278	High Similarity	NPC280825
0.9223	High Similarity	NPC472987
0.9223	High Similarity	NPC473021
0.9223	High Similarity	NPC114188
0.9216	High Similarity	NPC70204
0.9216	High Similarity	NPC306131
0.9216	High Similarity	NPC51925
0.9216	High Similarity	NPC250089
0.9216	High Similarity	NPC157530
0.9216	High Similarity	NPC296761
0.9216	High Similarity	NPC477027
0.9216	High Similarity	NPC154085
0.9216	High Similarity	NPC476835
0.9216	High Similarity	NPC125361
0.9216	High Similarity	NPC475670
0.9216	High Similarity	NPC42482
0.9216	High Similarity	NPC43976
0.9216	High Similarity	NPC40440
0.9216	High Similarity	NPC477026
0.9216	High Similarity	NPC14630
0.9208	High Similarity	NPC94272
0.9208	High Similarity	NPC283829
0.9208	High Similarity	NPC33053
0.9208	High Similarity	NPC305423
0.9208	High Similarity	NPC226642
0.9208	High Similarity	NPC230507
0.9208	High Similarity	NPC234160
0.9208	High Similarity	NPC161676
0.9208	High Similarity	NPC470432
0.9208	High Similarity	NPC14704
0.9208	High Similarity	NPC113044
0.92	High Similarity	NPC93352
0.9143	High Similarity	NPC477810
0.9135	High Similarity	NPC474265
0.9135	High Similarity	NPC210420
0.9126	High Similarity	NPC472717
0.9118	High Similarity	NPC98696
0.9118	High Similarity	NPC235824
0.9118	High Similarity	NPC295980
0.9109	High Similarity	NPC26798
0.9109	High Similarity	NPC473199
0.9091	High Similarity	NPC470434
0.9091	High Similarity	NPC117714
0.9091	High Similarity	NPC263756
0.9091	High Similarity	NPC267510
0.9082	High Similarity	NPC5358
0.9082	High Similarity	NPC216260
0.9072	High Similarity	NPC472989
0.9072	High Similarity	NPC207617
0.9062	High Similarity	NPC72817
0.9062	High Similarity	NPC477927
0.9057	High Similarity	NPC146652
0.9048	High Similarity	NPC476671
0.9048	High Similarity	NPC476693
0.9038	High Similarity	NPC475247
0.9038	High Similarity	NPC294129
0.9038	High Similarity	NPC477032
0.9038	High Similarity	NPC477028
0.9038	High Similarity	NPC124677
0.9038	High Similarity	NPC472715
0.9038	High Similarity	NPC13190
0.9038	High Similarity	NPC476547
0.9038	High Similarity	NPC65167
0.9029	High Similarity	NPC208383
0.9029	High Similarity	NPC6806
0.9029	High Similarity	NPC171073
0.9029	High Similarity	NPC309278
0.9029	High Similarity	NPC249265
0.9029	High Similarity	NPC150372
0.9029	High Similarity	NPC470433
0.9029	High Similarity	NPC475333
0.9029	High Similarity	NPC477809
0.9029	High Similarity	NPC46190
0.9029	High Similarity	NPC475550
0.9029	High Similarity	NPC22779
0.9029	High Similarity	NPC224098
0.9029	High Similarity	NPC248746
0.9029	High Similarity	NPC472901
0.9029	High Similarity	NPC232054
0.9029	High Similarity	NPC84956
0.9029	High Similarity	NPC218571
0.9029	High Similarity	NPC102016
0.9029	High Similarity	NPC73243
0.9029	High Similarity	NPC95051
0.9029	High Similarity	NPC300557
0.9029	High Similarity	NPC194207
0.9029	High Similarity	NPC244086
0.901	High Similarity	NPC54521
0.901	High Similarity	NPC57065
0.901	High Similarity	NPC109792
0.901	High Similarity	NPC475521
0.9	High Similarity	NPC256133
0.9	High Similarity	NPC76497
0.9	High Similarity	NPC30289
0.9	High Similarity	NPC213674
0.899	High Similarity	NPC64348
0.899	High Similarity	NPC469942
0.898	High Similarity	NPC76486
0.8962	High Similarity	NPC474557
0.8962	High Similarity	NPC473882
0.8962	High Similarity	NPC167183
0.8962	High Similarity	NPC32707
0.8952	High Similarity	NPC263359
0.8952	High Similarity	NPC32361
0.8952	High Similarity	NPC472716
0.8952	High Similarity	NPC31896
0.8952	High Similarity	NPC254255
0.8952	High Similarity	NPC112274
0.8952	High Similarity	NPC210569
0.8952	High Similarity	NPC244431
0.8942	High Similarity	NPC154856
0.8942	High Similarity	NPC475317
0.8942	High Similarity	NPC52241
0.8942	High Similarity	NPC23808
0.8942	High Similarity	NPC170974
0.8942	High Similarity	NPC191439
0.8942	High Similarity	NPC141433
0.8942	High Similarity	NPC247037

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 NPC187400 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	2071
0.2-0.3	4237
0.3-0.4	1743
0.4-0.5	470
0.5-0.6	226
0.6-0.7	164
0.7-0.8	22
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8482	Intermediate Similarity	NPD8033	Approved
0.8393	Intermediate Similarity	NPD8294	Approved
0.8393	Intermediate Similarity	NPD8377	Approved
0.8319	Intermediate Similarity	NPD8296	Approved
0.8319	Intermediate Similarity	NPD8335	Approved
0.8319	Intermediate Similarity	NPD8380	Approved
0.8319	Intermediate Similarity	NPD8379	Approved
0.8319	Intermediate Similarity	NPD8378	Approved
0.8053	Intermediate Similarity	NPD7327	Approved
0.8053	Intermediate Similarity	NPD7328	Approved
0.8	Intermediate Similarity	NPD7503	Approved
0.7982	Intermediate Similarity	NPD7516	Approved
0.7963	Intermediate Similarity	NPD6412	Phase 2
0.7857	Intermediate Similarity	NPD8133	Approved
0.7843	Intermediate Similarity	NPD8171	Discontinued
0.7818	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD7507	Approved
0.7563	Intermediate Similarity	NPD8328	Phase 3
0.7526	Intermediate Similarity	NPD7525	Registered
0.75	Intermediate Similarity	NPD8449	Approved
0.744	Intermediate Similarity	NPD8450	Suspended
0.7398	Intermediate Similarity	NPD7319	Approved
0.7353	Intermediate Similarity	NPD7524	Approved
0.7333	Intermediate Similarity	NPD6370	Approved
0.7317	Intermediate Similarity	NPD7736	Approved
0.7257	Intermediate Similarity	NPD6686	Approved
0.7245	Intermediate Similarity	NPD7645	Phase 2
0.7236	Intermediate Similarity	NPD8293	Discontinued
0.7228	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6942	Approved
0.7188	Intermediate Similarity	NPD7339	Approved
0.7167	Intermediate Similarity	NPD6059	Approved
0.7167	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6695	Phase 3
0.7107	Intermediate Similarity	NPD8513	Phase 3
0.7107	Intermediate Similarity	NPD8517	Approved
0.7107	Intermediate Similarity	NPD8515	Approved
0.7107	Intermediate Similarity	NPD8516	Approved
0.7019	Intermediate Similarity	NPD7750	Discontinued
0.7009	Intermediate Similarity	NPD8297	Approved
0.7009	Intermediate Similarity	NPD6882	Approved
0.6967	Remote Similarity	NPD6015	Approved
0.6967	Remote Similarity	NPD6016	Approved
0.6939	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6933	Approved
0.6935	Remote Similarity	NPD7492	Approved
0.6917	Remote Similarity	NPD6009	Approved
0.6911	Remote Similarity	NPD5988	Approved
0.6885	Remote Similarity	NPD6319	Approved
0.688	Remote Similarity	NPD6616	Approved
0.6857	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6067	Discontinued
0.6852	Remote Similarity	NPD6399	Phase 3
0.6847	Remote Similarity	NPD7638	Approved
0.6832	Remote Similarity	NPD6930	Phase 2
0.6832	Remote Similarity	NPD6931	Approved
0.6832	Remote Similarity	NPD6928	Phase 2
0.6825	Remote Similarity	NPD7078	Approved
0.6807	Remote Similarity	NPD4632	Approved
0.6786	Remote Similarity	NPD7639	Approved
0.6786	Remote Similarity	NPD7640	Approved
0.6783	Remote Similarity	NPD5739	Approved
0.6783	Remote Similarity	NPD6675	Approved
0.6783	Remote Similarity	NPD7128	Approved
0.6783	Remote Similarity	NPD6402	Approved
0.6777	Remote Similarity	NPD7115	Discovery
0.6752	Remote Similarity	NPD6372	Approved
0.6752	Remote Similarity	NPD6373	Approved
0.6735	Remote Similarity	NPD6926	Approved
0.6735	Remote Similarity	NPD6924	Approved
0.6733	Remote Similarity	NPD6929	Approved
0.6731	Remote Similarity	NPD4786	Approved
0.67	Remote Similarity	NPD6932	Approved
0.6667	Remote Similarity	NPD7625	Phase 1
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6641	Remote Similarity	NPD6033	Approved
0.6639	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD8130	Phase 1
0.6639	Remote Similarity	NPD6649	Approved
0.6639	Remote Similarity	NPD6650	Approved
0.6636	Remote Similarity	NPD7748	Approved
0.6607	Remote Similarity	NPD4755	Approved
0.6607	Remote Similarity	NPD7902	Approved
0.6606	Remote Similarity	NPD7087	Discontinued
0.6606	Remote Similarity	NPD8035	Phase 2
0.6606	Remote Similarity	NPD8034	Phase 2
0.6581	Remote Similarity	NPD5697	Approved
0.6581	Remote Similarity	NPD5701	Approved
0.6574	Remote Similarity	NPD5328	Approved
0.6569	Remote Similarity	NPD6683	Phase 2
0.6566	Remote Similarity	NPD1810	Approved
0.6566	Remote Similarity	NPD1811	Approved
0.6566	Remote Similarity	NPD4785	Approved
0.6566	Remote Similarity	NPD4784	Approved
0.6555	Remote Similarity	NPD7102	Approved
0.6555	Remote Similarity	NPD7290	Approved
0.6555	Remote Similarity	NPD4634	Approved
0.6555	Remote Similarity	NPD6883	Approved
0.6545	Remote Similarity	NPD4202	Approved
0.6538	Remote Similarity	NPD3667	Approved
0.6535	Remote Similarity	NPD5776	Phase 2
0.6535	Remote Similarity	NPD6925	Approved
0.6531	Remote Similarity	NPD4243	Approved
0.6514	Remote Similarity	NPD3168	Discontinued
0.6509	Remote Similarity	NPD6893	Approved
0.6505	Remote Similarity	NPD7509	Discontinued
0.6505	Remote Similarity	NPD7514	Phase 3
0.6505	Remote Similarity	NPD4748	Discontinued
0.65	Remote Similarity	NPD6847	Approved
0.65	Remote Similarity	NPD6617	Approved
0.65	Remote Similarity	NPD6869	Approved
0.6496	Remote Similarity	NPD6008	Approved
0.6495	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4696	Approved
0.6491	Remote Similarity	NPD5286	Approved
0.6491	Remote Similarity	NPD5285	Approved
0.6491	Remote Similarity	NPD4700	Approved
0.6471	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6013	Approved
0.6471	Remote Similarity	NPD7145	Approved
0.6471	Remote Similarity	NPD6014	Approved
0.6471	Remote Similarity	NPD6012	Approved
0.646	Remote Similarity	NPD6083	Phase 2
0.646	Remote Similarity	NPD6084	Phase 2
0.6457	Remote Similarity	NPD7604	Phase 2
0.6455	Remote Similarity	NPD7515	Phase 2
0.6455	Remote Similarity	NPD6079	Approved
0.6449	Remote Similarity	NPD3618	Phase 1
0.6435	Remote Similarity	NPD4159	Approved
0.6429	Remote Similarity	NPD5983	Phase 2
0.6404	Remote Similarity	NPD4225	Approved
0.6387	Remote Similarity	NPD6011	Approved
0.6379	Remote Similarity	NPD5211	Phase 2
0.6379	Remote Similarity	NPD4633	Approved
0.6379	Remote Similarity	NPD5225	Approved
0.6379	Remote Similarity	NPD5224	Approved
0.6379	Remote Similarity	NPD5226	Approved
0.6364	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7151	Approved
0.6364	Remote Similarity	NPD7150	Approved
0.6364	Remote Similarity	NPD7152	Approved
0.6357	Remote Similarity	NPD6336	Discontinued
0.6356	Remote Similarity	NPD4768	Approved
0.6356	Remote Similarity	NPD4767	Approved
0.6355	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7332	Phase 2
0.6339	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7900	Approved
0.6327	Remote Similarity	NPD6923	Approved
0.6327	Remote Similarity	NPD6922	Approved
0.6325	Remote Similarity	NPD5175	Approved
0.6325	Remote Similarity	NPD5174	Approved
0.6308	Remote Similarity	NPD8074	Phase 3
0.6306	Remote Similarity	NPD7637	Suspended
0.6293	Remote Similarity	NPD5223	Approved
0.6293	Remote Similarity	NPD5344	Discontinued
0.6286	Remote Similarity	NPD6898	Phase 1
0.6286	Remote Similarity	NPD6902	Approved
0.6281	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4753	Phase 2
0.6273	Remote Similarity	NPD6051	Approved
0.6271	Remote Similarity	NPD5141	Approved
0.6263	Remote Similarity	NPD7144	Approved
0.6263	Remote Similarity	NPD2687	Approved
0.6263	Remote Similarity	NPD2686	Approved
0.6263	Remote Similarity	NPD2254	Approved
0.6263	Remote Similarity	NPD7143	Approved
0.6261	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4729	Approved
0.625	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4730	Approved
0.6239	Remote Similarity	NPD7632	Discontinued
0.6228	Remote Similarity	NPD5222	Approved
0.6228	Remote Similarity	NPD4697	Phase 3
0.6228	Remote Similarity	NPD5221	Approved
0.6228	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4754	Approved
0.6176	Remote Similarity	NPD5275	Approved
0.6176	Remote Similarity	NPD4190	Phase 3
0.6174	Remote Similarity	NPD5173	Approved
0.6168	Remote Similarity	NPD3669	Approved
0.6168	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD5956	Approved
0.616	Remote Similarity	NPD6274	Approved
0.6148	Remote Similarity	NPD5251	Approved
0.6148	Remote Similarity	NPD5247	Approved
0.6148	Remote Similarity	NPD5249	Phase 3
0.6148	Remote Similarity	NPD5248	Approved
0.6148	Remote Similarity	NPD5250	Approved
0.6142	Remote Similarity	NPD7100	Approved
0.6142	Remote Similarity	NPD7101	Approved
0.614	Remote Similarity	NPD7991	Discontinued
0.614	Remote Similarity	NPD5695	Phase 3
0.6121	Remote Similarity	NPD5696	Approved
0.6116	Remote Similarity	NPD5128	Approved
0.6111	Remote Similarity	NPD3666	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