NPASS Compound

Structure

NPC163693 OpenBabel07101719512D 41 47 0 0 1 0 0 0 0 0999 V2000 5.9694 -1.2562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0186 -3.5291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6835 0.9523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1416 1.8498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1642 2.0614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0423 -2.1139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5661 -0.3411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0144 -0.9626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5795 0.9823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9870 -0.9315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4004 -0.3573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3495 -2.7860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3745 0.0012 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9003 0.1315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3412 0.3249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2420 1.2058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5837 -0.0164 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9812 -1.0397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5574 -1.8078 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8299 0.8272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4234 -0.3078 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4234 -1.3078 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6914 -1.3078 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3550 -2.8905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3577 0.3066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9623 -0.8078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4697 1.1092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0518 -1.9770 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7065 -0.2712 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6914 -0.3078 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3651 2.1982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3845 -1.9548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1450 -3.7565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8802 1.1593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9623 -0.8078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5720 -0.2329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3745 -1.6168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9356 0.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5574 0.1922 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 7 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 37 1 0 0 0 0 8 9 1 0 0 0 0 8 29 1 0 0 0 0 9 30 1 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 30 1 0 0 0 0 13 2 1 1 0 0 0 13 20 1 0 0 0 0 13 25 1 0 0 0 0 14 3 1 1 0 0 0 14 22 1 0 0 0 0 14 27 1 0 0 0 0 15 18 1 0 0 0 0 15 21 2 0 0 0 0 16 26 1 0 0 0 0 16 30 1 0 0 0 0 17 21 1 0 0 0 0 17 32 2 0 0 0 0 18 11 1 6 0 0 0 18 39 1 0 0 0 0 19 33 2 0 0 0 0 19 37 1 0 0 0 0 20 23 1 0 0 0 0 20 24 1 0 0 0 0 21 28 1 0 0 0 0 22 23 1 0 0 0 0 22 40 1 0 0 0 0 23 38 1 0 0 0 0 24 29 1 0 0 0 0 24 31 1 0 0 0 0 25 29 1 0 0 0 0 25 34 2 0 0 0 0 26 31 1 0 0 0 0 26 35 2 0 0 0 0 27 36 2 0 0 0 0 27 38 1 0 0 0 0 28 39 1 0 0 0 0 30 41 1 0 0 0 0 31 40 1 0 0 0 0 31 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	568.23
Volume:	554.284
LogP:	3.079
LogD:	2.443
LogS:	-4.724
# Rotatable Bonds:	3
TPSA:	131.5
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.362
Synthetic Accessibility Score:	7.154
Fsp3:	0.71
Lipinski Rule-of-5:	Accepted
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:	-5.252
MDCK Permeability:	7.100997027009726e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.815
Plasma Protein Binding (PPB):	90.58780670166016%
Volume Distribution (VD):	2.077
Pgp-substrate:	13.495491027832031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.651
CYP2C19-substrate:	0.606
CYP2C9-inhibitor:	0.267
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.026
CYP3A4-inhibitor:	0.937
CYP3A4-substrate:	0.612

ADMET: Excretion

Clearance (CL):	13.235
Half-life (T1/2):	0.023

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.505
Drug-inuced Liver Injury (DILI):	0.848
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.941
Maximum Recommended Daily Dose:	0.418
Skin Sensitization:	0.264
Carcinogencity:	0.721
Eye Corrosion:	0.006
Eye Irritation:	0.01
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC163693

Natural Product ID:	NPC163693
*Common Name:**	Rubriflorin C
IUPAC Name:	n.a.
Synonyms:	Rubriflorin C
Standard InCHIKey:	NGRMPILGZOCJFL-KWPZRPCSSA-N
Standard InCHI:	InChI=1S/C31H36O10/c1-7-37-19(33)11-18-15-12-30-9-8-29(6)24-20(13(2)25(29)34)23-22(14(3)27(36)38-23)40-31(24,41-30)26(35)16(30)10-17(32)21(15)28(4,5)39-18/h10,13-14,18,20,22-24H,7-9,11-12H2,1-6H3/t13-,14-,18+,20+,22+,23+,24-,29-,30-,31-/m0/s1
SMILES:	CCOC(=O)C[C@@H]1C2=C(C(=O)C=C3C(=O)[C@@]45[C@H]6[C@H]([C@H](C)C(=O)[C@@]6(C)CC[C@@]3(C2)O5)[C@@H]2[C@@H]([C@H](C)C(=O)O2)O4)C(C)(C)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL387967
PubChem CID:	16736658
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001818] Furopyrans

*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
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16494492]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[16494492]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17489633]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	leaves and stems	n.a.	n.a.	PMID[20146529]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	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
EC50	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	200.0	ug.mL-1	PMID[545637]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	81.3	ug.mL-1	PMID[545637]

☑ 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 NPC163693 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	326
0.1-0.2	2135
0.2-0.3	6847
0.3-0.4	11823
0.4-0.5	11518
0.5-0.6	7172
0.6-0.7	2676
0.7-0.8	186
0.8-0.85	5
0.85-0.9	6
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC147635
0.9316	High Similarity	NPC11732
0.9224	High Similarity	NPC42747
0.9083	High Similarity	NPC469351
0.8974	High Similarity	NPC192309
0.8917	High Similarity	NPC172823
0.8898	High Similarity	NPC1538
0.8739	High Similarity	NPC186339
0.8689	High Similarity	NPC13071
0.8629	High Similarity	NPC224623
0.8362	Intermediate Similarity	NPC471570
0.8361	Intermediate Similarity	NPC144625
0.7815	Intermediate Similarity	NPC475495
0.7812	Intermediate Similarity	NPC472770
0.7787	Intermediate Similarity	NPC471145
0.775	Intermediate Similarity	NPC473522
0.775	Intermediate Similarity	NPC475277
0.775	Intermediate Similarity	NPC477093
0.7739	Intermediate Similarity	NPC105725
0.7705	Intermediate Similarity	NPC277583
0.7692	Intermediate Similarity	NPC472769
0.7692	Intermediate Similarity	NPC469401
0.7686	Intermediate Similarity	NPC209058
0.768	Intermediate Similarity	NPC473228
0.768	Intermediate Similarity	NPC470829
0.7672	Intermediate Similarity	NPC469350
0.7661	Intermediate Similarity	NPC158963
0.7652	Intermediate Similarity	NPC162024
0.7642	Intermediate Similarity	NPC471146
0.7632	Intermediate Similarity	NPC54843
0.7627	Intermediate Similarity	NPC470192
0.7607	Intermediate Similarity	NPC472748
0.7607	Intermediate Similarity	NPC472756
0.7586	Intermediate Similarity	NPC49393
0.7581	Intermediate Similarity	NPC13710
0.7576	Intermediate Similarity	NPC471234
0.7565	Intermediate Similarity	NPC280963
0.7563	Intermediate Similarity	NPC475960
0.7559	Intermediate Similarity	NPC472768
0.7542	Intermediate Similarity	NPC472749
0.7542	Intermediate Similarity	NPC291643
0.7542	Intermediate Similarity	NPC472751
0.754	Intermediate Similarity	NPC471999
0.754	Intermediate Similarity	NPC472001
0.754	Intermediate Similarity	NPC472000
0.7521	Intermediate Similarity	NPC472750
0.7521	Intermediate Similarity	NPC472755
0.7521	Intermediate Similarity	NPC474750
0.7521	Intermediate Similarity	NPC472747
0.75	Intermediate Similarity	NPC475323
0.75	Intermediate Similarity	NPC475305
0.7481	Intermediate Similarity	NPC476852
0.7481	Intermediate Similarity	NPC476855
0.7479	Intermediate Similarity	NPC469787
0.7479	Intermediate Similarity	NPC290247
0.7479	Intermediate Similarity	NPC469788
0.7478	Intermediate Similarity	NPC470188
0.7458	Intermediate Similarity	NPC307846
0.7458	Intermediate Similarity	NPC305157
0.744	Intermediate Similarity	NPC475401
0.7438	Intermediate Similarity	NPC477103
0.7438	Intermediate Similarity	NPC471884
0.7436	Intermediate Similarity	NPC78127
0.7436	Intermediate Similarity	NPC472754
0.7436	Intermediate Similarity	NPC471757
0.7422	Intermediate Similarity	NPC129992
0.7414	Intermediate Similarity	NPC469402
0.7405	Intermediate Similarity	NPC476851
0.7405	Intermediate Similarity	NPC476854
0.7398	Intermediate Similarity	NPC473535
0.7395	Intermediate Similarity	NPC314244
0.7391	Intermediate Similarity	NPC47834
0.7381	Intermediate Similarity	NPC477092
0.7377	Intermediate Similarity	NPC470246
0.7373	Intermediate Similarity	NPC475871
0.7373	Intermediate Similarity	NPC475873
0.7373	Intermediate Similarity	NPC475945
0.736	Intermediate Similarity	NPC473656
0.736	Intermediate Similarity	NPC36754
0.7355	Intermediate Similarity	NPC477102
0.7355	Intermediate Similarity	NPC217041
0.735	Intermediate Similarity	NPC15993
0.735	Intermediate Similarity	NPC474742
0.735	Intermediate Similarity	NPC477511
0.735	Intermediate Similarity	NPC472753
0.735	Intermediate Similarity	NPC264477
0.7333	Intermediate Similarity	NPC26617
0.7328	Intermediate Similarity	NPC476859
0.7323	Intermediate Similarity	NPC151616
0.7323	Intermediate Similarity	NPC4548
0.7317	Intermediate Similarity	NPC471933
0.7317	Intermediate Similarity	NPC265391
0.7311	Intermediate Similarity	NPC100487
0.7311	Intermediate Similarity	NPC474917
0.7311	Intermediate Similarity	NPC203659
0.7311	Intermediate Similarity	NPC474741
0.7304	Intermediate Similarity	NPC17585
0.7304	Intermediate Similarity	NPC476275
0.7302	Intermediate Similarity	NPC475372
0.7302	Intermediate Similarity	NPC161060
0.7302	Intermediate Similarity	NPC473720
0.7302	Intermediate Similarity	NPC475309
0.7302	Intermediate Similarity	NPC470420
0.7295	Intermediate Similarity	NPC182185
0.7293	Intermediate Similarity	NPC100390
0.7293	Intermediate Similarity	NPC254614
0.7288	Intermediate Similarity	NPC324017
0.7288	Intermediate Similarity	NPC149371
0.7288	Intermediate Similarity	NPC474747
0.7288	Intermediate Similarity	NPC320019
0.728	Intermediate Similarity	NPC54739
0.7273	Intermediate Similarity	NPC264192
0.7273	Intermediate Similarity	NPC10150
0.7258	Intermediate Similarity	NPC470120
0.7257	Intermediate Similarity	NPC221282
0.7257	Intermediate Similarity	NPC20713
0.7252	Intermediate Similarity	NPC42399
0.7252	Intermediate Similarity	NPC287423
0.725	Intermediate Similarity	NPC103088
0.725	Intermediate Similarity	NPC470975
0.725	Intermediate Similarity	NPC469441
0.725	Intermediate Similarity	NPC41674
0.725	Intermediate Similarity	NPC228311
0.725	Intermediate Similarity	NPC470979
0.7244	Intermediate Similarity	NPC19028
0.7244	Intermediate Similarity	NPC475520
0.7244	Intermediate Similarity	NPC9674
0.7244	Intermediate Similarity	NPC312536
0.7241	Intermediate Similarity	NPC213947
0.7241	Intermediate Similarity	NPC170143
0.7241	Intermediate Similarity	NPC108475
0.7239	Intermediate Similarity	NPC88668
0.7239	Intermediate Similarity	NPC168879
0.7231	Intermediate Similarity	NPC470922
0.7227	Intermediate Similarity	NPC19239
0.7227	Intermediate Similarity	NPC110989
0.7227	Intermediate Similarity	NPC474166
0.7218	Intermediate Similarity	NPC476863
0.7218	Intermediate Similarity	NPC213634
0.7218	Intermediate Similarity	NPC476862
0.7217	Intermediate Similarity	NPC474490
0.7217	Intermediate Similarity	NPC167893
0.7213	Intermediate Similarity	NPC471934
0.7213	Intermediate Similarity	NPC38154
0.7213	Intermediate Similarity	NPC187876
0.7206	Intermediate Similarity	NPC243014
0.7203	Intermediate Similarity	NPC185141
0.7203	Intermediate Similarity	NPC476270
0.7203	Intermediate Similarity	NPC133907
0.7203	Intermediate Similarity	NPC171759
0.7203	Intermediate Similarity	NPC47880
0.7203	Intermediate Similarity	NPC471767
0.7203	Intermediate Similarity	NPC128733
0.7203	Intermediate Similarity	NPC46998
0.7203	Intermediate Similarity	NPC110443
0.72	Intermediate Similarity	NPC90472
0.7197	Intermediate Similarity	NPC188291
0.7197	Intermediate Similarity	NPC473620
0.7197	Intermediate Similarity	NPC311534
0.7194	Intermediate Similarity	NPC470426
0.719	Intermediate Similarity	NPC474716
0.7179	Intermediate Similarity	NPC208233
0.7179	Intermediate Similarity	NPC279561
0.7177	Intermediate Similarity	NPC98870
0.7176	Intermediate Similarity	NPC222307
0.7168	Intermediate Similarity	NPC469718
0.7168	Intermediate Similarity	NPC80875
0.7168	Intermediate Similarity	NPC475748
0.7168	Intermediate Similarity	NPC329857
0.7167	Intermediate Similarity	NPC471143
0.7167	Intermediate Similarity	NPC477510
0.7167	Intermediate Similarity	NPC309190
0.7165	Intermediate Similarity	NPC288679
0.7164	Intermediate Similarity	NPC102316
0.7164	Intermediate Similarity	NPC475139
0.7164	Intermediate Similarity	NPC6274
0.7164	Intermediate Similarity	NPC254146
0.7164	Intermediate Similarity	NPC180902
0.7164	Intermediate Similarity	NPC33378
0.7163	Intermediate Similarity	NPC48813
0.7163	Intermediate Similarity	NPC194854
0.7154	Intermediate Similarity	NPC206595
0.7154	Intermediate Similarity	NPC257240
0.7154	Intermediate Similarity	NPC472399
0.7154	Intermediate Similarity	NPC471392
0.7143	Intermediate Similarity	NPC66110
0.7143	Intermediate Similarity	NPC313569
0.7143	Intermediate Similarity	NPC469628
0.7143	Intermediate Similarity	NPC250594
0.7143	Intermediate Similarity	NPC469631
0.7143	Intermediate Similarity	NPC471047
0.7143	Intermediate Similarity	NPC469653
0.7143	Intermediate Similarity	NPC225353
0.7143	Intermediate Similarity	NPC471171
0.7143	Intermediate Similarity	NPC470851
0.7143	Intermediate Similarity	NPC475906
0.7143	Intermediate Similarity	NPC86077
0.7132	Intermediate Similarity	NPC171619
0.7132	Intermediate Similarity	NPC204731
0.7131	Intermediate Similarity	NPC329876

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 NPC163693 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	2528
0.2-0.3	4021
0.3-0.4	1554
0.4-0.5	484
0.5-0.6	229
0.6-0.7	45
0.7-0.8	2
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
0.7333	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6371	Approved
0.6992	Remote Similarity	NPD7078	Approved
0.697	Remote Similarity	NPD7492	Approved
0.6923	Remote Similarity	NPD6054	Approved
0.6917	Remote Similarity	NPD6616	Approved
0.6889	Remote Similarity	NPD7319	Approved
0.6855	Remote Similarity	NPD6686	Approved
0.6818	Remote Similarity	NPD6370	Approved
0.6815	Remote Similarity	NPD7736	Approved
0.6794	Remote Similarity	NPD6059	Approved
0.6791	Remote Similarity	NPD7507	Approved
0.678	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6015	Approved
0.6742	Remote Similarity	NPD6016	Approved
0.6741	Remote Similarity	NPD8293	Discontinued
0.6695	Remote Similarity	NPD5282	Discontinued
0.6692	Remote Similarity	NPD5988	Approved
0.6638	Remote Similarity	NPD1695	Approved
0.6619	Remote Similarity	NPD6845	Suspended
0.6562	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD7260	Phase 2
0.6541	Remote Similarity	NPD6319	Approved
0.6512	Remote Similarity	NPD6882	Approved
0.6512	Remote Similarity	NPD6053	Discontinued
0.648	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.648	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6698	Approved
0.6441	Remote Similarity	NPD46	Approved
0.6439	Remote Similarity	NPD6009	Approved
0.6435	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6008	Approved
0.6397	Remote Similarity	NPD8328	Phase 3
0.6385	Remote Similarity	NPD8297	Approved
0.637	Remote Similarity	NPD8513	Phase 3
0.637	Remote Similarity	NPD8515	Approved
0.637	Remote Similarity	NPD8517	Approved
0.637	Remote Similarity	NPD8516	Approved
0.6341	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD6033	Approved
0.6331	Remote Similarity	NPD8337	Approved
0.6331	Remote Similarity	NPD8336	Approved
0.6316	Remote Similarity	NPD7115	Discovery
0.6308	Remote Similarity	NPD6650	Approved
0.6308	Remote Similarity	NPD6649	Approved
0.6303	Remote Similarity	NPD5785	Approved
0.6279	Remote Similarity	NPD6373	Approved
0.6279	Remote Similarity	NPD6372	Approved
0.6277	Remote Similarity	NPD7642	Approved
0.6269	Remote Similarity	NPD7328	Approved
0.6269	Remote Similarity	NPD7327	Approved
0.625	Remote Similarity	NPD8033	Approved
0.625	Remote Similarity	NPD8267	Approved
0.625	Remote Similarity	NPD8269	Approved
0.625	Remote Similarity	NPD8268	Approved
0.625	Remote Similarity	NPD8266	Approved
0.6222	Remote Similarity	NPD7516	Approved
0.621	Remote Similarity	NPD5696	Approved
0.6204	Remote Similarity	NPD8080	Discontinued
0.6202	Remote Similarity	NPD6881	Approved
0.6202	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD6899	Approved
0.6202	Remote Similarity	NPD7320	Approved
0.6194	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD8377	Approved
0.6176	Remote Similarity	NPD8294	Approved
0.6172	Remote Similarity	NPD6402	Approved
0.6172	Remote Similarity	NPD7128	Approved
0.6172	Remote Similarity	NPD5739	Approved
0.6172	Remote Similarity	NPD6675	Approved
0.6154	Remote Similarity	NPD1694	Approved
0.6154	Remote Similarity	NPD8338	Approved
0.6143	Remote Similarity	NPD8074	Phase 3
0.6134	Remote Similarity	NPD5737	Approved
0.6134	Remote Similarity	NPD6672	Approved
0.6131	Remote Similarity	NPD8378	Approved
0.6131	Remote Similarity	NPD8296	Approved
0.6131	Remote Similarity	NPD8380	Approved
0.6131	Remote Similarity	NPD8335	Approved
0.6131	Remote Similarity	NPD8379	Approved
0.6127	Remote Similarity	NPD5956	Approved
0.6124	Remote Similarity	NPD5697	Approved
0.6124	Remote Similarity	NPD6412	Phase 2
0.6124	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD5693	Phase 1
0.6116	Remote Similarity	NPD7983	Approved
0.6107	Remote Similarity	NPD7290	Approved
0.6107	Remote Similarity	NPD6883	Approved
0.6107	Remote Similarity	NPD7102	Approved
0.609	Remote Similarity	NPD4632	Approved
0.608	Remote Similarity	NPD4225	Approved
0.6061	Remote Similarity	NPD8130	Phase 1
0.6061	Remote Similarity	NPD6869	Approved
0.6061	Remote Similarity	NPD6847	Approved
0.6061	Remote Similarity	NPD6617	Approved
0.6043	Remote Similarity	NPD7604	Phase 2
0.6034	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD6012	Approved
0.6031	Remote Similarity	NPD6014	Approved
0.6031	Remote Similarity	NPD6013	Approved
0.6014	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD7503	Approved
0.6014	Remote Similarity	NPD8444	Approved
0.6014	Remote Similarity	NPD5983	Phase 2
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD5701	Approved
0.5985	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD5695	Phase 3
0.5957	Remote Similarity	NPD6336	Discontinued
0.5954	Remote Similarity	NPD6011	Approved
0.595	Remote Similarity	NPD6904	Approved
0.595	Remote Similarity	NPD6080	Approved
0.595	Remote Similarity	NPD6673	Approved
0.5929	Remote Similarity	NPD7829	Approved
0.5929	Remote Similarity	NPD7830	Approved
0.592	Remote Similarity	NPD7839	Suspended
0.5902	Remote Similarity	NPD7838	Discovery
0.5882	Remote Similarity	NPD5363	Approved
0.5865	Remote Similarity	NPD4634	Approved
0.5859	Remote Similarity	NPD1700	Approved
0.5854	Remote Similarity	NPD6050	Approved
0.5852	Remote Similarity	NPD8133	Approved
0.5845	Remote Similarity	NPD8451	Approved
0.584	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5786	Approved
0.5827	Remote Similarity	NPD7638	Approved
0.5821	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD5779	Approved
0.5806	Remote Similarity	NPD6399	Phase 3
0.5806	Remote Similarity	NPD5778	Approved
0.5804	Remote Similarity	NPD8448	Approved
0.5799	Remote Similarity	NPD7799	Discontinued
0.5797	Remote Similarity	NPD7641	Discontinued
0.5789	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5786	Remote Similarity	NPD6921	Approved
0.5781	Remote Similarity	NPD7639	Approved
0.5781	Remote Similarity	NPD7640	Approved
0.5772	Remote Similarity	NPD5692	Phase 3
0.5766	Remote Similarity	NPD6274	Approved
0.5763	Remote Similarity	NPD5209	Approved
0.5758	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD6614	Approved
0.5755	Remote Similarity	NPD7100	Approved
0.5755	Remote Similarity	NPD7101	Approved
0.5738	Remote Similarity	NPD6903	Approved
0.5726	Remote Similarity	NPD6411	Approved
0.5726	Remote Similarity	NPD7637	Suspended
0.5726	Remote Similarity	NPD5694	Approved
0.5725	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD5210	Approved
0.5702	Remote Similarity	NPD6409	Approved
0.5702	Remote Similarity	NPD7146	Approved
0.5702	Remote Similarity	NPD6098	Approved
0.5702	Remote Similarity	NPD6684	Approved
0.5702	Remote Similarity	NPD7521	Approved
0.5702	Remote Similarity	NPD5330	Approved
0.5702	Remote Similarity	NPD7334	Approved
0.5692	Remote Similarity	NPD5211	Phase 2
0.5685	Remote Similarity	NPD8390	Approved
0.5685	Remote Similarity	NPD8391	Approved
0.5685	Remote Similarity	NPD8392	Approved
0.5683	Remote Similarity	NPD6335	Approved
0.5678	Remote Similarity	NPD5369	Approved
0.5674	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD8342	Approved
0.5664	Remote Similarity	NPD8340	Approved
0.5664	Remote Similarity	NPD8341	Approved
0.5664	Remote Similarity	NPD8299	Approved
0.5659	Remote Similarity	NPD5286	Approved
0.5659	Remote Similarity	NPD4696	Approved
0.5659	Remote Similarity	NPD6648	Approved
0.5659	Remote Similarity	NPD5285	Approved
0.5656	Remote Similarity	NPD4251	Approved
0.5656	Remote Similarity	NPD4250	Approved
0.5645	Remote Similarity	NPD5207	Approved
0.563	Remote Similarity	NPD4270	Approved
0.563	Remote Similarity	NPD6435	Approved
0.563	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.563	Remote Similarity	NPD4269	Approved
0.5625	Remote Similarity	NPD4755	Approved
0.562	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5615	Remote Similarity	NPD5344	Discontinued
0.5612	Remote Similarity	NPD6317	Approved
0.561	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD5141	Approved
0.56	Remote Similarity	NPD8387	Clinical (unspecified phase)

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