NPASS Compound

Structure

NPC473301 OpenBabel07101719252D 49 52 0 0 1 0 0 0 0 0999 V2000 -1.0863 -3.2691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4909 -0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0492 0.4064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4649 -2.5539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3554 0.6938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6093 -0.2539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6465 2.0340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2848 -6.3661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 -5.2208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3371 -6.1122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9786 -5.6724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1459 -5.0168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7621 -4.4916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0832 -5.1645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7247 -4.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8427 -4.0837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4589 -3.5585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1711 0.8497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3214 1.3403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4906 -1.8308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1711 -1.8308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3403 -2.3214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5098 -0.4906 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3031 -0.5413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0646 -1.3246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7770 -4.4707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4992 -3.3545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9811 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3214 -2.3214 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6616 -0.9811 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9331 -1.2843 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9331 0.3032 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5230 -3.5230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1960 -2.4214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4906 0.8497 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6616 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3403 1.3403 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2508 -0.7952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9793 -1.6795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2363 1.2363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2168 -2.8293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8525 -1.6923 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2032 1.5435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5942 2.2880 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6093 -1.2351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5753 -3.2691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2363 -2.2174 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9147 -0.3550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 36 1 0 0 0 0 6 36 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 16 1 0 0 0 0 13 17 2 0 0 0 0 14 26 2 0 0 0 0 15 26 1 0 0 0 0 16 27 2 0 0 0 0 17 27 1 0 0 0 0 18 19 2 0 0 0 0 18 36 1 0 0 0 0 19 37 1 0 0 0 0 20 22 2 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 21 30 1 0 0 0 0 22 29 1 0 0 0 0 23 2 1 6 0 0 0 23 31 1 0 0 0 0 23 32 1 0 0 0 0 24 39 2 0 0 0 0 24 46 1 0 0 0 0 25 40 2 0 0 0 0 25 49 1 0 0 0 0 26 33 1 0 0 0 0 27 34 1 0 0 0 0 28 31 1 0 0 0 0 28 38 1 6 0 0 0 29 47 1 6 0 0 0 30 36 1 0 0 0 0 30 46 1 6 0 0 0 31 48 1 6 0 0 0 32 38 1 1 0 0 0 32 41 1 0 0 0 0 33 42 2 0 0 0 0 33 47 1 0 0 0 0 34 43 2 0 0 0 0 34 48 1 0 0 0 0 35 37 1 1 0 0 0 35 38 1 0 0 0 0 35 44 1 0 0 0 0 37 7 1 1 0 0 0 37 45 1 0 0 0 0 38 49 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	678.3
Volume:	696.633
LogP:	4.608
LogD:	2.841
LogS:	-4.184
# Rotatable Bonds:	10
TPSA:	165.89
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.226
Synthetic Accessibility Score:	5.529
Fsp3:	0.474
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:	-5.34
MDCK Permeability:	7.486618414986879e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.044
Human Intestinal Absorption (HIA):	0.204
20% Bioavailability (F20%):	0.844
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.292
Plasma Protein Binding (PPB):	97.57975006103516%
Volume Distribution (VD):	1.898
Pgp-substrate:	6.331311225891113%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.568
CYP2C9-substrate:	0.359
CYP2D6-inhibitor:	0.245
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.844
CYP3A4-substrate:	0.353

ADMET: Excretion

Clearance (CL):	4.219
Half-life (T1/2):	0.326

ADMET: Toxicity

hERG Blockers:	0.821
Human Hepatotoxicity (H-HT):	0.987
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.45
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.127
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC473301

Natural Product ID:	NPC473301
*Common Name:**	1Alpha,13Beta,14Alpha-Trihydroxy-3Beta,7Beta-Dibenzoyloxy-9Beta,15Beta-Diacetoxyjatropha-5,11 E-Diene
IUPAC Name:	[(1S,2S,3S,3aS,4R,5S,6E,9S,11R,12Z,13aS)-3a,9-diacetyloxy-1-benzoyloxy-3,4,5-trihydroxy-2,5,8,8,12-pentamethyl-1,2,3,4,9,10,11,13a-octahydrocyclopenta[12]annulen-11-yl] benzoate
Synonyms:
Standard InCHIKey:	IRMXGIKDWJKAIM-SXCTYVFVSA-N
Standard InCHI:	InChI=1S/C38H46O11/c1-22-20-28-31(48-34(43)27-16-12-9-13-17-27)23(2)32(41)38(28,49-25(4)40)35(44)37(7,45)19-18-36(5,6)30(46-24(3)39)21-29(22)47-33(42)26-14-10-8-11-15-26/h8-20,23,28-32,35,41,44-45H,21H2,1-7H3/b19-18+,22-20-/t23-,28+,29-,30+,31+,32+,35-,37+,38+/m1/s1
SMILES:	CC1C(C2C=C(C(CC(C(C=CC(C(C2(C1O)OC(=O)C)O)(C)O)(C)C)OC(=O)C)OC(=O)C3=CC=CC=C3)C)OC(=O)C4=CC=CC=C4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL398938
PubChem CID:	23642402
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002877] Jatrophane and cyclojatrophane diterpenoids

*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
NPO31109	Pedilanthus tithymaloides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17844996]
NPO31109	Pedilanthus tithymaloides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31109	Pedilanthus tithymaloides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
MIC	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5900.0	nM	PMID[475951]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	12.5	ug.mL-1	PMID[475951]

☑ 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 NPC473301 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	267
0.1-0.2	921
0.2-0.3	2126
0.3-0.4	4636
0.4-0.5	9990
0.5-0.6	13598
0.6-0.7	9719
0.7-0.8	1127
0.8-0.85	199
0.85-0.9	67
0.9-0.95	29
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9692	High Similarity	NPC311492
0.9692	High Similarity	NPC28836
0.9621	High Similarity	NPC27721
0.9615	High Similarity	NPC472248
0.9552	High Similarity	NPC242355
0.9545	High Similarity	NPC202729
0.9538	High Similarity	NPC233692
0.9538	High Similarity	NPC239358
0.9538	High Similarity	NPC233860
0.947	High Similarity	NPC200154
0.9281	High Similarity	NPC205389
0.9248	High Similarity	NPC153617
0.9149	High Similarity	NPC232583
0.9149	High Similarity	NPC25484
0.9118	High Similarity	NPC121268
0.9118	High Similarity	NPC53361
0.9091	High Similarity	NPC477100
0.9091	High Similarity	NPC475508
0.9091	High Similarity	NPC477098
0.9051	High Similarity	NPC475660
0.9044	High Similarity	NPC327511
0.9044	High Similarity	NPC205305
0.9037	High Similarity	NPC149401
0.9037	High Similarity	NPC279637
0.8993	High Similarity	NPC45307
0.8986	High Similarity	NPC474303
0.8986	High Similarity	NPC475413
0.8963	High Similarity	NPC298547
0.8963	High Similarity	NPC324898
0.8963	High Similarity	NPC134937
0.8936	High Similarity	NPC312393
0.8921	High Similarity	NPC192658
0.8913	High Similarity	NPC162613
0.8913	High Similarity	NPC87934
0.8897	High Similarity	NPC79699
0.8881	High Similarity	NPC477097
0.8881	High Similarity	NPC477099
0.8881	High Similarity	NPC477101
0.8865	High Similarity	NPC25043
0.8865	High Similarity	NPC134131
0.8849	High Similarity	NPC473497
0.8841	High Similarity	NPC9905
0.8832	High Similarity	NPC194769
0.8832	High Similarity	NPC285221
0.8824	High Similarity	NPC472250
0.8794	High Similarity	NPC34943
0.8759	High Similarity	NPC290833
0.8759	High Similarity	NPC475262
0.8759	High Similarity	NPC472247
0.8759	High Similarity	NPC265459
0.8741	High Similarity	NPC327031
0.8723	High Similarity	NPC82467
0.8714	High Similarity	NPC266374
0.8705	High Similarity	NPC276652
0.8705	High Similarity	NPC325805
0.8705	High Similarity	NPC272523
0.8671	High Similarity	NPC240115
0.8671	High Similarity	NPC170668
0.8671	High Similarity	NPC477095
0.8671	High Similarity	NPC478263
0.8671	High Similarity	NPC20255
0.8633	High Similarity	NPC86772
0.8601	High Similarity	NPC311825
0.8601	High Similarity	NPC478264
0.8601	High Similarity	NPC92867
0.8601	High Similarity	NPC472556
0.8601	High Similarity	NPC125882
0.8592	High Similarity	NPC153214
0.8592	High Similarity	NPC131966
0.8592	High Similarity	NPC191387
0.8592	High Similarity	NPC95449
0.8582	High Similarity	NPC187566
0.8582	High Similarity	NPC473654
0.8562	High Similarity	NPC96308
0.8552	High Similarity	NPC76103
0.8542	High Similarity	NPC473602
0.8529	High Similarity	NPC272946
0.8514	High Similarity	NPC469456
0.8511	High Similarity	NPC472547
0.8493	Intermediate Similarity	NPC476173
0.8489	Intermediate Similarity	NPC232888
0.8489	Intermediate Similarity	NPC477367
0.8489	Intermediate Similarity	NPC270364
0.8483	Intermediate Similarity	NPC473760
0.8472	Intermediate Similarity	NPC184817
0.8472	Intermediate Similarity	NPC470157
0.8472	Intermediate Similarity	NPC470159
0.8472	Intermediate Similarity	NPC96903
0.8472	Intermediate Similarity	NPC469349
0.8472	Intermediate Similarity	NPC174982
0.8472	Intermediate Similarity	NPC171525
0.8472	Intermediate Similarity	NPC177940
0.8472	Intermediate Similarity	NPC70403
0.8472	Intermediate Similarity	NPC476973
0.8472	Intermediate Similarity	NPC471104
0.8472	Intermediate Similarity	NPC29704
0.8472	Intermediate Similarity	NPC473088
0.8472	Intermediate Similarity	NPC472571
0.8472	Intermediate Similarity	NPC472568
0.8472	Intermediate Similarity	NPC158663
0.8472	Intermediate Similarity	NPC472575
0.8472	Intermediate Similarity	NPC200471
0.8472	Intermediate Similarity	NPC472572
0.8467	Intermediate Similarity	NPC72915
0.8467	Intermediate Similarity	NPC319404
0.8462	Intermediate Similarity	NPC477094
0.8462	Intermediate Similarity	NPC477096
0.8456	Intermediate Similarity	NPC70344
0.8451	Intermediate Similarity	NPC41481
0.8451	Intermediate Similarity	NPC97947
0.8451	Intermediate Similarity	NPC291599
0.8451	Intermediate Similarity	NPC87448
0.8451	Intermediate Similarity	NPC472576
0.8451	Intermediate Similarity	NPC118080
0.8451	Intermediate Similarity	NPC16912
0.8451	Intermediate Similarity	NPC27377
0.8446	Intermediate Similarity	NPC471135
0.8444	Intermediate Similarity	NPC472706
0.8429	Intermediate Similarity	NPC472372
0.8429	Intermediate Similarity	NPC472374
0.8417	Intermediate Similarity	NPC477368
0.8414	Intermediate Similarity	NPC209592
0.8414	Intermediate Similarity	NPC48599
0.8403	Intermediate Similarity	NPC475759
0.8403	Intermediate Similarity	NPC11685
0.8403	Intermediate Similarity	NPC25768
0.8403	Intermediate Similarity	NPC95810
0.8403	Intermediate Similarity	NPC57628
0.8403	Intermediate Similarity	NPC188865
0.8403	Intermediate Similarity	NPC476974
0.8403	Intermediate Similarity	NPC472569
0.8403	Intermediate Similarity	NPC472573
0.8403	Intermediate Similarity	NPC475122
0.8403	Intermediate Similarity	NPC163719
0.8403	Intermediate Similarity	NPC470152
0.8403	Intermediate Similarity	NPC70716
0.8403	Intermediate Similarity	NPC95265
0.8403	Intermediate Similarity	NPC241951
0.8403	Intermediate Similarity	NPC125106
0.8403	Intermediate Similarity	NPC472570
0.84	Intermediate Similarity	NPC322048
0.84	Intermediate Similarity	NPC318447
0.8392	Intermediate Similarity	NPC475135
0.8392	Intermediate Similarity	NPC34012
0.8382	Intermediate Similarity	NPC472707
0.838	Intermediate Similarity	NPC171207
0.838	Intermediate Similarity	NPC251294
0.838	Intermediate Similarity	NPC275592
0.838	Intermediate Similarity	NPC100913
0.838	Intermediate Similarity	NPC90614
0.838	Intermediate Similarity	NPC97667
0.8369	Intermediate Similarity	NPC39549
0.8367	Intermediate Similarity	NPC125033
0.8345	Intermediate Similarity	NPC477364
0.8344	Intermediate Similarity	NPC476784
0.8333	Intermediate Similarity	NPC475638
0.8333	Intermediate Similarity	NPC475548
0.8333	Intermediate Similarity	NPC323001
0.8333	Intermediate Similarity	NPC163087
0.8333	Intermediate Similarity	NPC326235
0.8333	Intermediate Similarity	NPC290683
0.8322	Intermediate Similarity	NPC472657
0.8322	Intermediate Similarity	NPC472658
0.8322	Intermediate Similarity	NPC224491
0.8311	Intermediate Similarity	NPC470153
0.831	Intermediate Similarity	NPC475195
0.8301	Intermediate Similarity	NPC55744
0.8299	Intermediate Similarity	NPC476975
0.8299	Intermediate Similarity	NPC270590
0.8299	Intermediate Similarity	NPC471101
0.8299	Intermediate Similarity	NPC266265
0.8299	Intermediate Similarity	NPC92293
0.8299	Intermediate Similarity	NPC301556
0.8298	Intermediate Similarity	NPC472551
0.8298	Intermediate Similarity	NPC472545
0.8298	Intermediate Similarity	NPC217673
0.8298	Intermediate Similarity	NPC477358
0.8298	Intermediate Similarity	NPC52523
0.8289	Intermediate Similarity	NPC323356
0.8289	Intermediate Similarity	NPC326328
0.8289	Intermediate Similarity	NPC471138
0.8289	Intermediate Similarity	NPC309991
0.8288	Intermediate Similarity	NPC474935
0.8286	Intermediate Similarity	NPC48929
0.8286	Intermediate Similarity	NPC38420
0.8286	Intermediate Similarity	NPC136608
0.8286	Intermediate Similarity	NPC477359
0.8276	Intermediate Similarity	NPC38696
0.8264	Intermediate Similarity	NPC472546
0.8258	Intermediate Similarity	NPC475567
0.8258	Intermediate Similarity	NPC473468
0.8258	Intermediate Similarity	NPC473557
0.8255	Intermediate Similarity	NPC469648
0.8255	Intermediate Similarity	NPC22571
0.8255	Intermediate Similarity	NPC138641
0.8255	Intermediate Similarity	NPC145649
0.8255	Intermediate Similarity	NPC283875
0.8255	Intermediate Similarity	NPC233581
0.8255	Intermediate Similarity	NPC469647
0.8252	Intermediate Similarity	NPC473440

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 NPC473301 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	650
0.2-0.3	1456
0.3-0.4	2698
0.4-0.5	2318
0.5-0.6	1405
0.6-0.7	363
0.7-0.8	36
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8309	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD7236	Approved
0.7829	Intermediate Similarity	NPD7239	Suspended
0.7826	Intermediate Similarity	NPD7799	Discontinued
0.7746	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD4628	Phase 3
0.7647	Intermediate Similarity	NPD7741	Discontinued
0.7636	Intermediate Similarity	NPD7685	Pre-registration
0.7612	Intermediate Similarity	NPD2629	Approved
0.7586	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD6685	Approved
0.7375	Intermediate Similarity	NPD7058	Phase 2
0.7375	Intermediate Similarity	NPD7057	Phase 3
0.7313	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5765	Approved
0.7308	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6004	Phase 3
0.7285	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6002	Phase 3
0.7285	Intermediate Similarity	NPD6005	Phase 3
0.726	Intermediate Similarity	NPD7008	Discontinued
0.7259	Intermediate Similarity	NPD6912	Phase 3
0.7248	Intermediate Similarity	NPD6653	Approved
0.7244	Intermediate Similarity	NPD6273	Approved
0.7234	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7137	Phase 2
0.7211	Intermediate Similarity	NPD3764	Approved
0.7174	Intermediate Similarity	NPD4198	Discontinued
0.7172	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6085	Phase 2
0.7164	Intermediate Similarity	NPD2182	Approved
0.7164	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD8434	Phase 2
0.7101	Intermediate Similarity	NPD5951	Approved
0.7091	Intermediate Similarity	NPD8127	Discontinued
0.7077	Intermediate Similarity	NPD1238	Approved
0.7067	Intermediate Similarity	NPD6355	Discontinued
0.7063	Intermediate Similarity	NPD6287	Discontinued
0.7059	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7961	Discontinued
0.7045	Intermediate Similarity	NPD6647	Phase 2
0.7042	Intermediate Similarity	NPD5125	Phase 3
0.7042	Intermediate Similarity	NPD5126	Approved
0.7037	Intermediate Similarity	NPD5760	Phase 2
0.7037	Intermediate Similarity	NPD5761	Phase 2
0.7018	Intermediate Similarity	NPD8368	Discontinued
0.6994	Remote Similarity	NPD8407	Phase 2
0.6992	Remote Similarity	NPD1237	Approved
0.6987	Remote Similarity	NPD6190	Approved
0.6962	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6858	Approved
0.6957	Remote Similarity	NPD7094	Approved
0.6948	Remote Similarity	NPD5762	Approved
0.6948	Remote Similarity	NPD5763	Approved
0.6944	Remote Similarity	NPD4806	Approved
0.6944	Remote Similarity	NPD4807	Approved
0.694	Remote Similarity	NPD5048	Discontinued
0.6939	Remote Similarity	NPD5647	Approved
0.6933	Remote Similarity	NPD6663	Approved
0.6932	Remote Similarity	NPD8360	Approved
0.6932	Remote Similarity	NPD8361	Approved
0.6923	Remote Similarity	NPD5305	Approved
0.6923	Remote Similarity	NPD5306	Approved
0.6917	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1930	Approved
0.6917	Remote Similarity	NPD1929	Approved
0.6914	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7075	Discontinued
0.6901	Remote Similarity	NPD9545	Approved
0.6894	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5736	Approved
0.6875	Remote Similarity	NPD4136	Approved
0.6875	Remote Similarity	NPD5403	Approved
0.6875	Remote Similarity	NPD4135	Approved
0.6875	Remote Similarity	NPD4106	Approved
0.6871	Remote Similarity	NPD6362	Approved
0.6866	Remote Similarity	NPD164	Approved
0.6866	Remote Similarity	NPD5909	Discontinued
0.6861	Remote Similarity	NPD2067	Discontinued
0.6857	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6599	Discontinued
0.6852	Remote Similarity	NPD4380	Phase 2
0.6839	Remote Similarity	NPD7266	Discontinued
0.6836	Remote Similarity	NPD8435	Approved
0.6829	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7715	Approved
0.6821	Remote Similarity	NPD6764	Approved
0.6821	Remote Similarity	NPD6765	Approved
0.6821	Remote Similarity	NPD7714	Approved
0.6818	Remote Similarity	NPD8150	Discontinued
0.6818	Remote Similarity	NPD7305	Phase 1
0.6818	Remote Similarity	NPD7033	Discontinued
0.6815	Remote Similarity	NPD8166	Discontinued
0.6812	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7458	Discontinued
0.6788	Remote Similarity	NPD5402	Approved
0.6779	Remote Similarity	NPD5204	Approved
0.6768	Remote Similarity	NPD6801	Discontinued
0.6757	Remote Similarity	NPD3094	Phase 2
0.6752	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5401	Approved
0.6747	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD8312	Approved
0.6743	Remote Similarity	NPD8313	Approved
0.6742	Remote Similarity	NPD9495	Approved
0.6736	Remote Similarity	NPD4105	Approved
0.6736	Remote Similarity	NPD4102	Approved
0.6733	Remote Similarity	NPD6832	Phase 2
0.6732	Remote Similarity	NPD230	Phase 1
0.6731	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8455	Phase 2
0.6727	Remote Similarity	NPD7819	Suspended
0.6709	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2575	Approved
0.6707	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD8485	Approved
0.6692	Remote Similarity	NPD7798	Approved
0.6692	Remote Similarity	NPD2066	Phase 3
0.6689	Remote Similarity	NPD1876	Approved
0.6687	Remote Similarity	NPD6799	Approved
0.6667	Remote Similarity	NPD3661	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6785	Approved
0.6667	Remote Similarity	NPD7497	Discontinued
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD3662	Phase 3
0.6667	Remote Similarity	NPD7009	Phase 2
0.6667	Remote Similarity	NPD3664	Approved
0.6667	Remote Similarity	NPD6784	Approved
0.6667	Remote Similarity	NPD3663	Approved
0.6647	Remote Similarity	NPD7768	Phase 2
0.6644	Remote Similarity	NPD2797	Approved
0.6623	Remote Similarity	NPD4617	Approved
0.6623	Remote Similarity	NPD4620	Approved
0.6623	Remote Similarity	NPD5203	Approved
0.6623	Remote Similarity	NPD5201	Approved
0.6604	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD3750	Approved
0.6604	Remote Similarity	NPD4110	Phase 3
0.6604	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7003	Approved
0.6603	Remote Similarity	NPD2799	Discontinued
0.6603	Remote Similarity	NPD4308	Phase 3
0.6601	Remote Similarity	NPD6233	Phase 2
0.6601	Remote Similarity	NPD7713	Phase 3
0.6597	Remote Similarity	NPD7610	Discontinued
0.6595	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7199	Phase 2
0.6587	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7095	Approved
0.6577	Remote Similarity	NPD5667	Approved
0.6575	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD37	Approved
0.6565	Remote Similarity	NPD1202	Approved
0.6561	Remote Similarity	NPD1551	Phase 2
0.6558	Remote Similarity	NPD5119	Approved
0.6558	Remote Similarity	NPD4140	Approved
0.6558	Remote Similarity	NPD5121	Approved
0.6558	Remote Similarity	NPD5120	Approved
0.6552	Remote Similarity	NPD5844	Phase 1
0.6552	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4965	Approved
0.6548	Remote Similarity	NPD4967	Phase 2
0.6548	Remote Similarity	NPD4966	Approved
0.6536	Remote Similarity	NPD6798	Discontinued
0.6536	Remote Similarity	NPD4621	Approved
0.6536	Remote Similarity	NPD4619	Approved
0.6536	Remote Similarity	NPD3268	Approved
0.6536	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD2313	Discontinued
0.6534	Remote Similarity	NPD6559	Discontinued
0.6528	Remote Similarity	NPD9493	Approved
0.6528	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD969	Suspended
0.6516	Remote Similarity	NPD5735	Approved
0.6513	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD7411	Suspended
0.65	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3818	Discontinued
0.649	Remote Similarity	NPD2798	Approved
0.6488	Remote Similarity	NPD3817	Phase 2
0.6486	Remote Similarity	NPD3092	Approved
0.6485	Remote Similarity	NPD3226	Approved
0.6485	Remote Similarity	NPD3455	Phase 2
0.6478	Remote Similarity	NPD5958	Discontinued
0.6478	Remote Similarity	NPD4534	Discontinued
0.6477	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1932	Approved
0.6471	Remote Similarity	NPD6234	Discontinued

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