NPASS Compound

Structure

CID25043 OpenBabel06191715352D 41 46 0 0 1 0 0 0 0 0999 V2000 2.1005 0.3648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1707 1.9004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6935 3.5029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3031 2.7386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8710 -2.8328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8587 -4.1479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4969 -1.9296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2759 -3.6085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9024 -3.9446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5128 -3.4214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5276 -1.8020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3066 -3.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6003 -3.0149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2107 -2.4916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3920 2.4472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7616 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6940 0.9552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6198 -1.4192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1229 0.3648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2175 1.6828 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9325 -2.5776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2545 -2.2883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2457 -0.5160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7616 0.7297 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3696 2.4472 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9792 1.6828 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5160 -0.5160 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8808 0.3055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6940 -0.2255 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9632 -2.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9524 -1.3585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3364 2.5929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.7297 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 -0.1418 -1.4192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8808 -1.6498 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3680 -3.2256 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6065 -0.6320 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9755 0.0645 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5891 -1.5468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9961 -1.1553 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 32 1 0 0 0 0 4 32 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 21 2 0 0 0 0 12 21 1 0 0 0 0 13 22 2 0 0 0 0 14 22 1 0 0 0 0 15 20 1 0 0 0 0 16 23 2 0 0 0 0 17 19 2 0 0 0 0 17 33 1 0 0 0 0 18 23 1 0 0 0 0 18 40 1 0 0 0 0 19 29 1 0 0 0 0 20 33 1 1 0 0 0 21 30 1 0 0 0 0 22 31 1 0 0 0 0 23 27 1 0 0 0 0 24 16 1 1 0 0 0 24 26 1 0 0 0 0 24 28 1 0 0 0 0 25 15 1 6 0 0 0 25 26 1 0 0 0 0 25 32 1 0 0 0 0 26 32 1 6 0 0 0 27 34 1 6 0 0 0 27 35 1 0 0 0 0 28 33 1 0 0 0 0 28 36 2 0 0 0 0 29 34 1 6 0 0 0 29 41 1 0 0 0 0 30 37 2 0 0 0 0 30 40 1 0 0 0 0 31 38 2 0 0 0 0 31 41 1 0 0 0 0 33 34 1 6 0 0 0 34 39 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	556.25
Volume:	577.812
LogP:	5.641
LogD:	4.255
LogS:	-4.614
# Rotatable Bonds:	7
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.411
Synthetic Accessibility Score:	5.88
Fsp3:	0.441
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:	-5.172
MDCK Permeability:	3.786438173847273e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	97.99593353271484%
Volume Distribution (VD):	1.812
Pgp-substrate:	4.5419921875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.143
CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.71
CYP2C19-substrate:	0.082
CYP2C9-inhibitor:	0.864
CYP2C9-substrate:	0.102
CYP2D6-inhibitor:	0.311
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.804
CYP3A4-substrate:	0.456

ADMET: Excretion

Clearance (CL):	10.64
Half-life (T1/2):	0.052

ADMET: Toxicity

hERG Blockers:	0.33
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.722
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.227
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.848
Carcinogencity:	0.196
Eye Corrosion:	0.003
Eye Irritation:	0.038
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC25043

Natural Product ID:	NPC25043
*Common Name:**	GIMKEHNOTHXONN-NXBFFCPZSA-N
IUPAC Name:	n.a.
Synonyms:	Ingenol 3,20-Dibenzoate
Standard InCHIKey:	GIMKEHNOTHXONN-NXBFFCPZSA-N
Standard InCHI:	InChI=1S/C34H36O7/c1-19-17-33-20(2)15-25-26(32(25,3)4)24(28(33)36)16-23(18-40-30(37)21-11-7-5-8-12-21)27(35)34(33,39)29(19)41-31(38)22-13-9-6-10-14-22/h5-14,16-17,20,24-27,29,35,39H,15,18H2,1-4H3/t20-,24+,25-,26+,27-,29+,33+,34+/m1/s1
SMILES:	O=C(c1ccccc1)OCC1=C[C@H]2[C@H]3[C@H](C3(C)C)C[C@H]([C@]3([C@@]([C@@H]1O)(O)[C@@H](OC(=O)c1ccccc1)C(=C3)C)C2=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2165713
PubChem CID:	442043
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane 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
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21612217]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21612217]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27447736]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32233482]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	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	3
Others	5

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	1
Organism	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-0.16	%	PMID[479214]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	1.0	%	PMID[479214]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	3396.0	n.a.	PMID[479215]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	6.4	n.a.	PMID[479215]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	1200.0	nM	PMID[479215]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	27.0	nM	PMID[479215]
NPT332	Organism	Human immunodeficiency virus type 2 (ISOLATE ROD)	Human immunodeficiency virus type 2 (ISOLATE ROD)	EC50	=	9.0	nM	PMID[479215]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	6049.0	n.a.	PMID[479215]

☑ 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 NPC25043 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	307
0.1-0.2	1056
0.2-0.3	2394
0.3-0.4	5851
0.4-0.5	11205
0.5-0.6	10848
0.6-0.7	10009
0.7-0.8	948
0.8-0.85	62
0.85-0.9	12
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC134131
0.9412	High Similarity	NPC217673
0.9412	High Similarity	NPC52523
0.9007	High Similarity	NPC242355
0.8897	High Similarity	NPC132652
0.8865	High Similarity	NPC473301
0.8859	High Similarity	NPC11410
0.8851	High Similarity	NPC477098
0.8851	High Similarity	NPC477100
0.8776	High Similarity	NPC25484
0.8776	High Similarity	NPC232583
0.8767	High Similarity	NPC205389
0.8714	High Similarity	NPC153617
0.8714	High Similarity	NPC28836
0.8705	High Similarity	NPC233692
0.8681	High Similarity	NPC192658
0.8671	High Similarity	NPC87934
0.8671	High Similarity	NPC162613
0.8658	High Similarity	NPC469648
0.8658	High Similarity	NPC22571
0.8658	High Similarity	NPC233581
0.8658	High Similarity	NPC138641
0.8658	High Similarity	NPC469647
0.8658	High Similarity	NPC145649
0.8658	High Similarity	NPC283875
0.8649	High Similarity	NPC477101
0.8649	High Similarity	NPC477099
0.8649	High Similarity	NPC477097
0.8643	High Similarity	NPC472248
0.8621	High Similarity	NPC95449
0.8601	High Similarity	NPC9905
0.8582	High Similarity	NPC311492
0.8571	High Similarity	NPC233860
0.8571	High Similarity	NPC239358
0.8562	High Similarity	NPC34943
0.8543	High Similarity	NPC251139
0.8531	High Similarity	NPC27721
0.8521	High Similarity	NPC200154
0.8493	Intermediate Similarity	NPC45307
0.8493	Intermediate Similarity	NPC82467
0.8483	Intermediate Similarity	NPC474303
0.8483	Intermediate Similarity	NPC475413
0.8483	Intermediate Similarity	NPC266374
0.8483	Intermediate Similarity	NPC187566
0.8483	Intermediate Similarity	NPC473497
0.8467	Intermediate Similarity	NPC472398
0.8462	Intermediate Similarity	NPC202729
0.8446	Intermediate Similarity	NPC20255
0.8446	Intermediate Similarity	NPC240115
0.8446	Intermediate Similarity	NPC477095
0.8425	Intermediate Similarity	NPC140021
0.8425	Intermediate Similarity	NPC183540
0.8403	Intermediate Similarity	NPC205305
0.8403	Intermediate Similarity	NPC327511
0.8378	Intermediate Similarity	NPC311825
0.8378	Intermediate Similarity	NPC125882
0.8378	Intermediate Similarity	NPC92867
0.8345	Intermediate Similarity	NPC121268
0.8345	Intermediate Similarity	NPC276652
0.8345	Intermediate Similarity	NPC53361
0.8322	Intermediate Similarity	NPC134937
0.8322	Intermediate Similarity	NPC298547
0.8322	Intermediate Similarity	NPC170668
0.8322	Intermediate Similarity	NPC324898
0.8322	Intermediate Similarity	NPC312393
0.8288	Intermediate Similarity	NPC475660
0.8278	Intermediate Similarity	NPC125033
0.8276	Intermediate Similarity	NPC86772
0.8267	Intermediate Similarity	NPC473760
0.8264	Intermediate Similarity	NPC279637
0.8264	Intermediate Similarity	NPC232888
0.8264	Intermediate Similarity	NPC472247
0.8264	Intermediate Similarity	NPC149401
0.8264	Intermediate Similarity	NPC79699
0.8264	Intermediate Similarity	NPC477367
0.8243	Intermediate Similarity	NPC131966
0.8243	Intermediate Similarity	NPC153214
0.8243	Intermediate Similarity	NPC477096
0.8243	Intermediate Similarity	NPC477094
0.8243	Intermediate Similarity	NPC191387
0.8231	Intermediate Similarity	NPC473654
0.8219	Intermediate Similarity	NPC325805
0.8219	Intermediate Similarity	NPC272523
0.8217	Intermediate Similarity	NPC55744
0.82	Intermediate Similarity	NPC473602
0.82	Intermediate Similarity	NPC48599
0.82	Intermediate Similarity	NPC209592
0.8194	Intermediate Similarity	NPC477368
0.8169	Intermediate Similarity	NPC475508
0.8138	Intermediate Similarity	NPC270364
0.8138	Intermediate Similarity	NPC265459
0.8138	Intermediate Similarity	NPC475262
0.8138	Intermediate Similarity	NPC290833
0.8133	Intermediate Similarity	NPC472556
0.8125	Intermediate Similarity	NPC477364
0.8105	Intermediate Similarity	NPC470153
0.8101	Intermediate Similarity	NPC43304
0.8101	Intermediate Similarity	NPC477188
0.8101	Intermediate Similarity	NPC477190
0.8085	Intermediate Similarity	NPC472706
0.8082	Intermediate Similarity	NPC194769
0.8082	Intermediate Similarity	NPC285221
0.8082	Intermediate Similarity	NPC477358
0.8079	Intermediate Similarity	NPC478263
0.8069	Intermediate Similarity	NPC477359
0.8069	Intermediate Similarity	NPC472250
0.8067	Intermediate Similarity	NPC475122
0.8065	Intermediate Similarity	NPC21410
0.8065	Intermediate Similarity	NPC473670
0.8063	Intermediate Similarity	NPC61891
0.8052	Intermediate Similarity	NPC477905
0.8052	Intermediate Similarity	NPC472548
0.805	Intermediate Similarity	NPC66193
0.8041	Intermediate Similarity	NPC251294
0.8041	Intermediate Similarity	NPC100913
0.8041	Intermediate Similarity	NPC472547
0.8041	Intermediate Similarity	NPC275592
0.8039	Intermediate Similarity	NPC7095
0.8039	Intermediate Similarity	NPC31829
0.8028	Intermediate Similarity	NPC472707
0.8027	Intermediate Similarity	NPC39549
0.8026	Intermediate Similarity	NPC217918
0.8026	Intermediate Similarity	NPC327031
0.8014	Intermediate Similarity	NPC476033
0.8014	Intermediate Similarity	NPC477896
0.8014	Intermediate Similarity	NPC79608
0.8014	Intermediate Similarity	NPC477893
0.8013	Intermediate Similarity	NPC472571
0.8013	Intermediate Similarity	NPC106895
0.8013	Intermediate Similarity	NPC478264
0.8013	Intermediate Similarity	NPC127857
0.8013	Intermediate Similarity	NPC476973
0.8013	Intermediate Similarity	NPC472568
0.8013	Intermediate Similarity	NPC29704
0.8013	Intermediate Similarity	NPC174982
0.8013	Intermediate Similarity	NPC177940
0.8013	Intermediate Similarity	NPC472572
0.8013	Intermediate Similarity	NPC472575
0.8013	Intermediate Similarity	NPC471104
0.8013	Intermediate Similarity	NPC96903
0.8013	Intermediate Similarity	NPC171525
0.8013	Intermediate Similarity	NPC470157
0.8013	Intermediate Similarity	NPC184817
0.8013	Intermediate Similarity	NPC158663
0.8013	Intermediate Similarity	NPC200471
0.8013	Intermediate Similarity	NPC473088
0.8013	Intermediate Similarity	NPC470159
0.8013	Intermediate Similarity	NPC70403
0.8013	Intermediate Similarity	NPC469349
0.8	Intermediate Similarity	NPC237549
0.8	Intermediate Similarity	NPC256142
0.8	Intermediate Similarity	NPC249471
0.8	Intermediate Similarity	NPC471134
0.8	Intermediate Similarity	NPC257213
0.8	Intermediate Similarity	NPC477894
0.8	Intermediate Similarity	NPC473414
0.8	Intermediate Similarity	NPC265395
0.8	Intermediate Similarity	NPC472005
0.8	Intermediate Similarity	NPC1173
0.8	Intermediate Similarity	NPC158333
0.8	Intermediate Similarity	NPC472030
0.8	Intermediate Similarity	NPC304876
0.8	Intermediate Similarity	NPC472022
0.8	Intermediate Similarity	NPC242262
0.7987	Intermediate Similarity	NPC97947
0.7987	Intermediate Similarity	NPC51602
0.7987	Intermediate Similarity	NPC291599
0.7987	Intermediate Similarity	NPC87448
0.7987	Intermediate Similarity	NPC197037
0.7987	Intermediate Similarity	NPC224491
0.7987	Intermediate Similarity	NPC118080
0.7987	Intermediate Similarity	NPC41481
0.7987	Intermediate Similarity	NPC472576
0.7987	Intermediate Similarity	NPC471103
0.7987	Intermediate Similarity	NPC27377
0.7987	Intermediate Similarity	NPC16912
0.7974	Intermediate Similarity	NPC473215
0.7974	Intermediate Similarity	NPC81698
0.7974	Intermediate Similarity	NPC250046
0.7974	Intermediate Similarity	NPC60509
0.7973	Intermediate Similarity	NPC475195
0.7963	Intermediate Similarity	NPC40138
0.7959	Intermediate Similarity	NPC472551
0.7959	Intermediate Similarity	NPC472372
0.7959	Intermediate Similarity	NPC472374
0.7959	Intermediate Similarity	NPC472545
0.7949	Intermediate Similarity	NPC228204
0.7949	Intermediate Similarity	NPC112523
0.7949	Intermediate Similarity	NPC469456
0.7949	Intermediate Similarity	NPC26033
0.7949	Intermediate Similarity	NPC472549
0.7949	Intermediate Similarity	NPC282239
0.7949	Intermediate Similarity	NPC114410
0.7947	Intermediate Similarity	NPC188865
0.7947	Intermediate Similarity	NPC11685
0.7947	Intermediate Similarity	NPC57628
0.7947	Intermediate Similarity	NPC95810
0.7947	Intermediate Similarity	NPC475759
0.7947	Intermediate Similarity	NPC472573
0.7947	Intermediate Similarity	NPC70716

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 NPC25043 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	755
0.2-0.3	1588
0.3-0.4	2792
0.4-0.5	2422
0.5-0.6	1004
0.6-0.7	327
0.7-0.8	7
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
0.7586	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7236	Approved
0.7517	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7799	Discontinued
0.7432	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6371	Approved
0.7419	Intermediate Similarity	NPD4628	Phase 3
0.7312	Intermediate Similarity	NPD7239	Suspended
0.7286	Intermediate Similarity	NPD2629	Approved
0.7159	Intermediate Similarity	NPD8434	Phase 2
0.7122	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6085	Phase 2
0.7114	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7741	Discontinued
0.7069	Intermediate Similarity	NPD7685	Pre-registration
0.7069	Intermediate Similarity	NPD8368	Discontinued
0.7045	Intermediate Similarity	NPD8407	Phase 2
0.7042	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3764	Approved
0.7006	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6647	Phase 2
0.6983	Remote Similarity	NPD8361	Approved
0.6983	Remote Similarity	NPD8360	Approved
0.6978	Remote Similarity	NPD2182	Approved
0.6974	Remote Similarity	NPD7008	Discontinued
0.6966	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6599	Discontinued
0.6905	Remote Similarity	NPD7057	Phase 3
0.6905	Remote Similarity	NPD7058	Phase 2
0.6899	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6287	Discontinued
0.6889	Remote Similarity	NPD8435	Approved
0.6887	Remote Similarity	NPD5647	Approved
0.6886	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5048	Discontinued
0.6879	Remote Similarity	NPD2799	Discontinued
0.6875	Remote Similarity	NPD4198	Discontinued
0.6872	Remote Similarity	NPD8150	Discontinued
0.6864	Remote Similarity	NPD7075	Discontinued
0.6857	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5402	Approved
0.6835	Remote Similarity	NPD6685	Approved
0.6829	Remote Similarity	NPD5403	Approved
0.6824	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1237	Approved
0.681	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4380	Phase 2
0.6806	Remote Similarity	NPD5951	Approved
0.68	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8313	Approved
0.6798	Remote Similarity	NPD8312	Approved
0.6786	Remote Similarity	NPD5760	Phase 2
0.6786	Remote Similarity	NPD5761	Phase 2
0.6774	Remote Similarity	NPD7961	Discontinued
0.677	Remote Similarity	NPD2575	Approved
0.677	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6273	Approved
0.6765	Remote Similarity	NPD1238	Approved
0.6757	Remote Similarity	NPD8485	Approved
0.6757	Remote Similarity	NPD5126	Approved
0.6757	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5125	Phase 3
0.6748	Remote Similarity	NPD6799	Approved
0.6747	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1930	Approved
0.6739	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1929	Approved
0.6728	Remote Similarity	NPD6190	Approved
0.6726	Remote Similarity	NPD6801	Discontinued
0.671	Remote Similarity	NPD2313	Discontinued
0.6707	Remote Similarity	NPD5401	Approved
0.6691	Remote Similarity	NPD164	Approved
0.669	Remote Similarity	NPD2067	Discontinued
0.6688	Remote Similarity	NPD6355	Discontinued
0.6687	Remote Similarity	NPD6002	Phase 3
0.6687	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6004	Phase 3
0.6687	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6005	Phase 3
0.6686	Remote Similarity	NPD7819	Suspended
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4807	Approved
0.6667	Remote Similarity	NPD4806	Approved
0.6667	Remote Similarity	NPD8166	Discontinued
0.6649	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7458	Discontinued
0.6646	Remote Similarity	NPD6653	Approved
0.6644	Remote Similarity	NPD5306	Approved
0.6644	Remote Similarity	NPD5305	Approved
0.6643	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD2935	Discontinued
0.6622	Remote Similarity	NPD9545	Approved
0.6619	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD5765	Approved
0.6608	Remote Similarity	NPD7768	Phase 2
0.6606	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4136	Approved
0.66	Remote Similarity	NPD4135	Approved
0.66	Remote Similarity	NPD4106	Approved
0.6584	Remote Similarity	NPD2346	Discontinued
0.6582	Remote Similarity	NPD230	Phase 1
0.6581	Remote Similarity	NPD6832	Phase 2
0.6571	Remote Similarity	NPD5909	Discontinued
0.6562	Remote Similarity	NPD7305	Phase 1
0.6561	Remote Similarity	NPD7714	Approved
0.6561	Remote Similarity	NPD7715	Approved
0.6558	Remote Similarity	NPD2798	Approved
0.6554	Remote Similarity	NPD3818	Discontinued
0.6552	Remote Similarity	NPD6858	Approved
0.6552	Remote Similarity	NPD8127	Discontinued
0.6552	Remote Similarity	NPD7094	Approved
0.655	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD3226	Approved
0.6541	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD1934	Approved
0.6522	Remote Similarity	NPD7137	Phase 2
0.6522	Remote Similarity	NPD1551	Phase 2
0.6522	Remote Similarity	NPD2066	Phase 3
0.6517	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD5204	Approved
0.6512	Remote Similarity	NPD3882	Suspended
0.6512	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6764	Approved
0.65	Remote Similarity	NPD6559	Discontinued
0.65	Remote Similarity	NPD6765	Approved
0.6497	Remote Similarity	NPD7473	Discontinued
0.6491	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD9493	Approved
0.6483	Remote Similarity	NPD6912	Phase 3
0.6481	Remote Similarity	NPD7266	Discontinued
0.6481	Remote Similarity	NPD5763	Approved
0.6481	Remote Similarity	NPD5762	Approved
0.6479	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7411	Suspended
0.6467	Remote Similarity	NPD4102	Approved
0.6467	Remote Similarity	NPD4105	Approved
0.6463	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3750	Approved
0.646	Remote Similarity	NPD1510	Phase 2
0.6456	Remote Similarity	NPD7713	Phase 3
0.6456	Remote Similarity	NPD6663	Approved
0.6453	Remote Similarity	NPD3817	Phase 2
0.6449	Remote Similarity	NPD9495	Approved
0.6442	Remote Similarity	NPD1549	Phase 2
0.6432	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1932	Approved
0.6424	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.642	Remote Similarity	NPD2796	Approved
0.6415	Remote Similarity	NPD1240	Approved
0.641	Remote Similarity	NPD5736	Approved
0.6407	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD2532	Approved
0.6407	Remote Similarity	NPD2534	Approved
0.6407	Remote Similarity	NPD2533	Approved
0.6405	Remote Similarity	NPD1608	Approved
0.6403	Remote Similarity	NPD7798	Approved
0.64	Remote Similarity	NPD5494	Approved
0.6398	Remote Similarity	NPD2569	Approved
0.6398	Remote Similarity	NPD2567	Approved
0.6395	Remote Similarity	NPD8455	Phase 2
0.6395	Remote Similarity	NPD2801	Approved
0.6392	Remote Similarity	NPD3268	Approved
0.6389	Remote Similarity	NPD7074	Phase 3
0.6389	Remote Similarity	NPD2329	Discontinued
0.6387	Remote Similarity	NPD1203	Approved
0.6387	Remote Similarity	NPD2797	Approved
0.638	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.638	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD3749	Approved
0.6375	Remote Similarity	NPD4684	Phase 3
0.6375	Remote Similarity	NPD4686	Approved
0.6375	Remote Similarity	NPD447	Suspended
0.6375	Remote Similarity	NPD4685	Phase 3
0.637	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD2613	Approved
0.6369	Remote Similarity	NPD5201	Approved
0.6369	Remote Similarity	NPD4617	Approved
0.6369	Remote Similarity	NPD4620	Approved
0.6369	Remote Similarity	NPD5203	Approved
0.6364	Remote Similarity	NPD7003	Approved
0.6359	Remote Similarity	NPD6785	Approved
0.6359	Remote Similarity	NPD6784	Approved
0.6358	Remote Similarity	NPD4308	Phase 3
0.6358	Remote Similarity	NPD5585	Approved
0.6353	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD4745	Approved
0.6352	Remote Similarity	NPD3089	Approved
0.6352	Remote Similarity	NPD4746	Phase 3
0.6352	Remote Similarity	NPD2566	Approved
0.6352	Remote Similarity	NPD2570	Approved
0.6352	Remote Similarity	NPD2574	Discontinued
0.6352	Remote Similarity	NPD3087	Approved
0.6352	Remote Similarity	NPD3088	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