NPASS Compound

Structure

NPC294512 OpenBabel07101719512D 46 50 0 0 1 0 0 0 0 0999 V2000 -3.8201 -4.6561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4245 -5.1462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2734 -4.1660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4245 1.2253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4245 1.7154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4047 -1.2253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8201 1.7154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9712 2.2055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8201 0.7352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1223 1.7154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9712 0.2451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6131 0.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3102 1.7535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1223 0.2451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4245 -2.2055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0271 0.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9712 -2.2055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8201 -3.6759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4245 -4.1660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1223 -3.6759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1223 0.7352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8201 0.2451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2734 0.7352 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4245 -2.6957 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1223 -0.7352 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4245 0.2451 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2734 -2.2055 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2734 0.2451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8201 -0.7352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4245 0.7352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4245 -1.2253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2734 -1.2253 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4245 -0.7352 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6690 -3.1858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2734 -3.6759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9712 -4.1660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2734 -0.7352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6690 -1.2253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9146 -0.3764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3300 1.7535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9712 -3.1858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4245 -3.6759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1223 -2.6957 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9712 -1.2253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4245 0.7352 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 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 30 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 21 2 0 0 0 0 11 21 1 0 0 0 0 12 13 2 0 0 0 0 12 22 1 0 0 0 0 13 40 1 0 0 0 0 14 25 1 0 0 0 0 15 24 1 0 0 0 0 15 31 1 0 0 0 0 16 22 2 0 0 0 0 16 40 1 0 0 0 0 17 32 1 0 0 0 0 17 41 1 0 0 0 0 18 34 2 0 0 0 0 18 41 1 0 0 0 0 19 35 2 0 0 0 0 19 42 1 0 0 0 0 20 36 2 0 0 0 0 20 43 1 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 23 14 1 1 0 0 0 23 26 1 0 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 42 1 6 0 0 0 25 32 1 1 0 0 0 25 44 1 0 0 0 0 26 33 1 1 0 0 0 26 45 1 0 0 0 0 27 32 1 6 0 0 0 27 43 1 0 0 0 0 28 37 2 0 0 0 0 28 45 1 0 0 0 0 29 38 2 0 0 0 0 29 44 1 0 0 0 0 30 46 1 0 0 0 0 31 33 1 6 0 0 0 31 39 1 0 0 0 0 32 33 1 6 0 0 0 33 46 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	642.23
Volume:	624.45
LogP:	3.536
LogD:	2.007
LogS:	-4.059
# Rotatable Bonds:	13
TPSA:	174.1
# H-Bond Aceptor:	13
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.329
Synthetic Accessibility Score:	6.039
Fsp3:	0.545
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:	-5.301
MDCK Permeability:	5.120140849612653e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.7
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.501
Plasma Protein Binding (PPB):	78.77045440673828%
Volume Distribution (VD):	1.824
Pgp-substrate:	11.74893856048584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.025
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.09
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.778
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.559
CYP3A4-substrate:	0.314

ADMET: Excretion

Clearance (CL):	5.395
Half-life (T1/2):	0.816

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.61
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.098
Rat Oral Acute Toxicity:	0.858
Maximum Recommended Daily Dose:	0.537
Skin Sensitization:	0.104
Carcinogencity:	0.782
Eye Corrosion:	0.003
Eye Irritation:	0.069
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC294512

Natural Product ID:	NPC294512
*Common Name:**	ZOEKVOBAKUWQID-IAXXPUDGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZOEKVOBAKUWQID-IAXXPUDGSA-N
Standard InCHI:	InChI=1S/C33H38O13/c1-18(34)41-17-32-25(44-29(38)22-12-13-40-16-22)14-23-26(45-28(37)21-10-8-7-9-11-21)33(32,46-30(23,4)5)31(6,39)15-24(42-19(2)35)27(32)43-20(3)36/h7-13,16,23-27,39H,14-15,17H2,1-6H3/t23-,24+,25+,26-,27+,31+,32-,33+/m1/s1
SMILES:	CC(=O)OC[C@@]12[C@H](C[C@@H]3[C@H]([C@@]2([C@](C)(C[C@@H]([C@@H]1OC(=O)C)OC(=O)C)O)OC3(C)C)OC(=O)c1ccccc1)OC(=O)c1ccoc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1829397
PubChem CID:	56642788
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

*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
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20146433]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	fruits	n.a.	n.a.	PMID[21856049]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27541714]
NPO26437	Maytenus jelskii	Species	Celastraceae	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
Ki	1
Others	10

Activity Type	# Activity
Cell Line	2
Individual Protein	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT886	Cell Line	NIH3T3	Mus musculus	Activity	=	92.36	%	PMID[496684]
NPT886	Cell Line	NIH3T3	Mus musculus	Activity	=	87.84	%	PMID[496684]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Inhibition	=	70.0	%	PMID[496684]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ki	=	590.0	nM	PMID[496684]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Imax	>	90.0	%	PMID[496684]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	4.5	n.a.	PMID[496684]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	11.97	n.a.	PMID[496684]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	13.27	n.a.	PMID[496684]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	7.51	n.a.	PMID[496684]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	13.21	n.a.	PMID[496684]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	58.13	n.a.	PMID[496684]

☑ 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 NPC294512 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	367
0.1-0.2	1380
0.2-0.3	2752
0.3-0.4	5547
0.4-0.5	10847
0.5-0.6	7891
0.6-0.7	6932
0.7-0.8	6410
0.8-0.85	457
0.85-0.9	92
0.9-0.95	14
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9814	High Similarity	NPC56953
0.9814	High Similarity	NPC176413
0.9747	High Similarity	NPC86800
0.9684	High Similarity	NPC276735
0.9202	High Similarity	NPC270312
0.9193	High Similarity	NPC188649
0.9152	High Similarity	NPC475641
0.9152	High Similarity	NPC475237
0.9146	High Similarity	NPC296558
0.9136	High Similarity	NPC88841
0.9136	High Similarity	NPC288602
0.9136	High Similarity	NPC285567
0.908	High Similarity	NPC56358
0.9074	High Similarity	NPC68848
0.9024	High Similarity	NPC121995
0.9018	High Similarity	NPC283209
0.9006	High Similarity	NPC195954
0.9006	High Similarity	NPC88007
0.897	High Similarity	NPC310572
0.8909	High Similarity	NPC472141
0.8902	High Similarity	NPC476035
0.8902	High Similarity	NPC475039
0.8902	High Similarity	NPC14499
0.8896	High Similarity	NPC8389
0.8896	High Similarity	NPC287559
0.8889	High Similarity	NPC194499
0.8862	High Similarity	NPC118086
0.8841	High Similarity	NPC79571
0.8841	High Similarity	NPC18986
0.8827	High Similarity	NPC41880
0.8827	High Similarity	NPC104736
0.8795	High Similarity	NPC277618
0.8788	High Similarity	NPC472139
0.8773	High Similarity	NPC81405
0.8773	High Similarity	NPC472776
0.8773	High Similarity	NPC304692
0.8773	High Similarity	NPC472777
0.8773	High Similarity	NPC7059
0.8773	High Similarity	NPC299038
0.8773	High Similarity	NPC472778
0.875	High Similarity	NPC88593
0.8735	High Similarity	NPC27541
0.8735	High Similarity	NPC62692
0.8735	High Similarity	NPC126984
0.8735	High Similarity	NPC61967
0.8727	High Similarity	NPC200782
0.872	High Similarity	NPC140952
0.872	High Similarity	NPC474611
0.872	High Similarity	NPC475967
0.8713	High Similarity	NPC472665
0.8704	High Similarity	NPC302054
0.8704	High Similarity	NPC253201
0.869	High Similarity	NPC271235
0.8663	High Similarity	NPC11062
0.865	High Similarity	NPC476262
0.8642	High Similarity	NPC268905
0.8642	High Similarity	NPC294511
0.8642	High Similarity	NPC472672
0.8642	High Similarity	NPC121615
0.8634	High Similarity	NPC294803
0.8634	High Similarity	NPC212257
0.8634	High Similarity	NPC228842
0.8634	High Similarity	NPC6815
0.8614	High Similarity	NPC470792
0.8606	High Similarity	NPC475226
0.8589	High Similarity	NPC98206
0.8589	High Similarity	NPC237259
0.8589	High Similarity	NPC34421
0.858	High Similarity	NPC147340
0.858	High Similarity	NPC271460
0.858	High Similarity	NPC472652
0.858	High Similarity	NPC160651
0.858	High Similarity	NPC291742
0.858	High Similarity	NPC18135
0.8571	High Similarity	NPC211625
0.8571	High Similarity	NPC125182
0.8571	High Similarity	NPC69647
0.8563	High Similarity	NPC472773
0.8563	High Similarity	NPC469846
0.8562	High Similarity	NPC255414
0.8554	High Similarity	NPC472653
0.8545	High Similarity	NPC261597
0.8545	High Similarity	NPC36655
0.8537	High Similarity	NPC44675
0.8537	High Similarity	NPC214541
0.8529	High Similarity	NPC302392
0.8528	High Similarity	NPC476201
0.8523	High Similarity	NPC472662
0.8523	High Similarity	NPC472663
0.8521	High Similarity	NPC472651
0.8521	High Similarity	NPC472774
0.8521	High Similarity	NPC472775
0.8512	High Similarity	NPC469849
0.8512	High Similarity	NPC472664
0.8512	High Similarity	NPC470182
0.8503	High Similarity	NPC82851
0.8503	High Similarity	NPC329938
0.8503	High Similarity	NPC471003
0.8503	High Similarity	NPC472771
0.8476	Intermediate Similarity	NPC282445
0.8462	Intermediate Similarity	NPC308156
0.8462	Intermediate Similarity	NPC93172
0.8462	Intermediate Similarity	NPC470875
0.8462	Intermediate Similarity	NPC97574
0.8452	Intermediate Similarity	NPC469338
0.8452	Intermediate Similarity	NPC302369
0.8452	Intermediate Similarity	NPC134254
0.8452	Intermediate Similarity	NPC39986
0.8452	Intermediate Similarity	NPC292389
0.8447	Intermediate Similarity	NPC71821
0.8434	Intermediate Similarity	NPC469847
0.8434	Intermediate Similarity	NPC187149
0.8434	Intermediate Similarity	NPC167142
0.8424	Intermediate Similarity	NPC264943
0.8421	Intermediate Similarity	NPC82602
0.8415	Intermediate Similarity	NPC469503
0.8412	Intermediate Similarity	NPC472282
0.8412	Intermediate Similarity	NPC476861
0.8412	Intermediate Similarity	NPC476850
0.8412	Intermediate Similarity	NPC173516
0.8405	Intermediate Similarity	NPC476122
0.8402	Intermediate Similarity	NPC276551
0.8402	Intermediate Similarity	NPC470940
0.8402	Intermediate Similarity	NPC271657
0.8393	Intermediate Similarity	NPC149896
0.8393	Intermediate Similarity	NPC263432
0.8393	Intermediate Similarity	NPC18347
0.8385	Intermediate Similarity	NPC62799
0.8383	Intermediate Similarity	NPC472671
0.8375	Intermediate Similarity	NPC251865
0.8364	Intermediate Similarity	NPC57998
0.8364	Intermediate Similarity	NPC114880
0.8363	Intermediate Similarity	NPC255787
0.8363	Intermediate Similarity	NPC471397
0.8362	Intermediate Similarity	NPC475656
0.8362	Intermediate Similarity	NPC475148
0.8354	Intermediate Similarity	NPC16912
0.8353	Intermediate Similarity	NPC475779
0.8352	Intermediate Similarity	NPC254588
0.8344	Intermediate Similarity	NPC195325
0.8343	Intermediate Similarity	NPC476197
0.8343	Intermediate Similarity	NPC477405
0.8333	Intermediate Similarity	NPC191828
0.8333	Intermediate Similarity	NPC335761
0.8333	Intermediate Similarity	NPC221809
0.8333	Intermediate Similarity	NPC470789
0.8324	Intermediate Similarity	NPC120220
0.8323	Intermediate Similarity	NPC470118
0.8323	Intermediate Similarity	NPC246841
0.8323	Intermediate Similarity	NPC472772
0.8323	Intermediate Similarity	NPC214495
0.8323	Intermediate Similarity	NPC1408
0.8323	Intermediate Similarity	NPC249021
0.8323	Intermediate Similarity	NPC475066
0.8323	Intermediate Similarity	NPC470119
0.8323	Intermediate Similarity	NPC45101
0.8323	Intermediate Similarity	NPC5676
0.8314	Intermediate Similarity	NPC44602
0.8314	Intermediate Similarity	NPC470995
0.8314	Intermediate Similarity	NPC472660
0.8313	Intermediate Similarity	NPC57628
0.8313	Intermediate Similarity	NPC188865
0.8313	Intermediate Similarity	NPC25768
0.8313	Intermediate Similarity	NPC472569
0.8313	Intermediate Similarity	NPC472573
0.8313	Intermediate Similarity	NPC11685
0.8313	Intermediate Similarity	NPC95810
0.8313	Intermediate Similarity	NPC95265
0.8313	Intermediate Similarity	NPC163719
0.8313	Intermediate Similarity	NPC70716
0.8313	Intermediate Similarity	NPC476946
0.8313	Intermediate Similarity	NPC125106
0.8313	Intermediate Similarity	NPC472570
0.8313	Intermediate Similarity	NPC476974
0.8304	Intermediate Similarity	NPC473766
0.8304	Intermediate Similarity	NPC100333
0.8304	Intermediate Similarity	NPC473753
0.8295	Intermediate Similarity	NPC470938
0.8294	Intermediate Similarity	NPC123088
0.8294	Intermediate Similarity	NPC476856
0.8294	Intermediate Similarity	NPC476858
0.8294	Intermediate Similarity	NPC476857
0.8291	Intermediate Similarity	NPC97667
0.8291	Intermediate Similarity	NPC171207
0.8284	Intermediate Similarity	NPC69028
0.8282	Intermediate Similarity	NPC19747
0.8282	Intermediate Similarity	NPC471007
0.8276	Intermediate Similarity	NPC472584
0.8276	Intermediate Similarity	NPC94763
0.8276	Intermediate Similarity	NPC148185
0.8274	Intermediate Similarity	NPC84349
0.8274	Intermediate Similarity	NPC307383
0.8266	Intermediate Similarity	NPC160818
0.8266	Intermediate Similarity	NPC169299
0.8261	Intermediate Similarity	NPC472568
0.8261	Intermediate Similarity	NPC96903
0.8261	Intermediate Similarity	NPC472571
0.8261	Intermediate Similarity	NPC472572
0.8261	Intermediate Similarity	NPC471104
0.8261	Intermediate Similarity	NPC476973

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 NPC294512 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	793
0.2-0.3	1639
0.3-0.4	2595
0.4-0.5	2255
0.5-0.6	1070
0.6-0.7	379
0.7-0.8	96
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8837	High Similarity	NPD8434	Phase 2
0.8095	Intermediate Similarity	NPD5761	Phase 2
0.8095	Intermediate Similarity	NPD5760	Phase 2
0.8012	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD6559	Discontinued
0.7882	Intermediate Similarity	NPD7819	Suspended
0.7778	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7075	Discontinued
0.774	Intermediate Similarity	NPD7473	Discontinued
0.773	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6599	Discontinued
0.7701	Intermediate Similarity	NPD6234	Discontinued
0.7697	Intermediate Similarity	NPD4628	Phase 3
0.7688	Intermediate Similarity	NPD4965	Approved
0.7688	Intermediate Similarity	NPD4966	Approved
0.7688	Intermediate Similarity	NPD4967	Phase 2
0.7677	Intermediate Similarity	NPD8404	Phase 2
0.767	Intermediate Similarity	NPD6232	Discontinued
0.7657	Intermediate Similarity	NPD5494	Approved
0.7647	Intermediate Similarity	NPD3226	Approved
0.7637	Intermediate Similarity	NPD8312	Approved
0.7637	Intermediate Similarity	NPD8313	Approved
0.763	Intermediate Similarity	NPD5402	Approved
0.7622	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD8127	Discontinued
0.7586	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7768	Phase 2
0.7556	Intermediate Similarity	NPD5844	Phase 1
0.7543	Intermediate Similarity	NPD3749	Approved
0.7529	Intermediate Similarity	NPD920	Approved
0.7529	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3817	Phase 2
0.7527	Intermediate Similarity	NPD6765	Approved
0.7527	Intermediate Similarity	NPD6764	Approved
0.7514	Intermediate Similarity	NPD37	Approved
0.7514	Intermediate Similarity	NPD6801	Discontinued
0.75	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD7228	Approved
0.7471	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6273	Approved
0.7457	Intermediate Similarity	NPD7411	Suspended
0.7456	Intermediate Similarity	NPD6799	Approved
0.7455	Intermediate Similarity	NPD1551	Phase 2
0.7433	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5403	Approved
0.7419	Intermediate Similarity	NPD8150	Discontinued
0.7414	Intermediate Similarity	NPD1934	Approved
0.7412	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5401	Approved
0.741	Intermediate Similarity	NPD2346	Discontinued
0.7401	Intermediate Similarity	NPD919	Approved
0.7399	Intermediate Similarity	NPD4380	Phase 2
0.7394	Intermediate Similarity	NPD2799	Discontinued
0.7386	Intermediate Similarity	NPD3882	Suspended
0.7381	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD2801	Approved
0.7366	Intermediate Similarity	NPD6784	Approved
0.7366	Intermediate Similarity	NPD6785	Approved
0.7349	Intermediate Similarity	NPD2935	Discontinued
0.7345	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7240	Approved
0.7333	Intermediate Similarity	NPD3926	Phase 2
0.7329	Intermediate Similarity	NPD6832	Phase 2
0.7318	Intermediate Similarity	NPD7199	Phase 2
0.7318	Intermediate Similarity	NPD1247	Approved
0.731	Intermediate Similarity	NPD2533	Approved
0.731	Intermediate Similarity	NPD2534	Approved
0.731	Intermediate Similarity	NPD2532	Approved
0.731	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1471	Phase 3
0.7294	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6166	Phase 2
0.7293	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2796	Approved
0.7245	Intermediate Similarity	NPD7435	Discontinued
0.7241	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2313	Discontinued
0.7238	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7074	Phase 3
0.7222	Intermediate Similarity	NPD6959	Discontinued
0.7219	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD3751	Discontinued
0.7212	Intermediate Similarity	NPD6355	Discontinued
0.7209	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2344	Approved
0.7189	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3750	Approved
0.7175	Intermediate Similarity	NPD8455	Phase 2
0.7174	Intermediate Similarity	NPD7054	Approved
0.716	Intermediate Similarity	NPD1549	Phase 2
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7135	Intermediate Similarity	NPD7472	Approved
0.7134	Intermediate Similarity	NPD3764	Approved
0.7128	Intermediate Similarity	NPD8407	Phase 2
0.7126	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7097	Phase 1
0.712	Intermediate Similarity	NPD7799	Discontinued
0.7118	Intermediate Similarity	NPD2800	Approved
0.7118	Intermediate Similarity	NPD1243	Approved
0.7114	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7874	Approved
0.7112	Intermediate Similarity	NPD7808	Phase 3
0.7108	Intermediate Similarity	NPD447	Suspended
0.7101	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6777	Approved
0.7092	Intermediate Similarity	NPD6779	Approved
0.7092	Intermediate Similarity	NPD6782	Approved
0.7092	Intermediate Similarity	NPD6781	Approved
0.7092	Intermediate Similarity	NPD6780	Approved
0.7092	Intermediate Similarity	NPD6776	Approved
0.7092	Intermediate Similarity	NPD6778	Approved
0.7091	Intermediate Similarity	NPD6233	Phase 2
0.7088	Intermediate Similarity	NPD3787	Discontinued
0.7088	Intermediate Similarity	NPD7229	Phase 3
0.7083	Intermediate Similarity	NPD3748	Approved
0.7079	Intermediate Similarity	NPD1465	Phase 2
0.7076	Intermediate Similarity	NPD7003	Approved
0.7073	Intermediate Similarity	NPD7095	Approved
0.7071	Intermediate Similarity	NPD7697	Approved
0.7071	Intermediate Similarity	NPD7497	Discontinued
0.7071	Intermediate Similarity	NPD7698	Approved
0.7071	Intermediate Similarity	NPD7696	Phase 3
0.7059	Intermediate Similarity	NPD8368	Discontinued
0.7059	Intermediate Similarity	NPD7251	Discontinued
0.7059	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7685	Pre-registration
0.7052	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD1511	Approved
0.7035	Intermediate Similarity	NPD2309	Approved
0.7035	Intermediate Similarity	NPD7870	Phase 2
0.7035	Intermediate Similarity	NPD6190	Approved
0.7035	Intermediate Similarity	NPD7871	Phase 2
0.703	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6798	Discontinued
0.702	Intermediate Similarity	NPD6823	Phase 2
0.7015	Intermediate Similarity	NPD7701	Phase 2
0.7006	Intermediate Similarity	NPD1933	Approved
0.7006	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6797	Phase 2
0.6995	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7801	Approved
0.6995	Remote Similarity	NPD7783	Phase 2
0.6988	Remote Similarity	NPD8032	Phase 2
0.6982	Remote Similarity	NPD7033	Discontinued
0.6982	Remote Similarity	NPD1510	Phase 2
0.6982	Remote Similarity	NPD4308	Phase 3
0.698	Remote Similarity	NPD8151	Discontinued
0.6979	Remote Similarity	NPD8360	Approved
0.6979	Remote Similarity	NPD8435	Approved
0.6979	Remote Similarity	NPD8361	Approved
0.6977	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8166	Discontinued
0.6977	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4110	Phase 3
0.6971	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD1512	Approved
0.697	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8285	Discontinued
0.695	Remote Similarity	NPD8320	Phase 1
0.695	Remote Similarity	NPD8319	Approved
0.6941	Remote Similarity	NPD6099	Approved
0.6941	Remote Similarity	NPD6100	Approved
0.6933	Remote Similarity	NPD1203	Approved
0.6933	Remote Similarity	NPD2797	Approved
0.6928	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5953	Discontinued
0.6914	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7700	Phase 2
0.6904	Remote Similarity	NPD7699	Phase 2
0.6902	Remote Similarity	NPD6808	Phase 2
0.6901	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6004	Phase 3
0.6901	Remote Similarity	NPD5763	Approved
0.6901	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5762	Approved
0.6901	Remote Similarity	NPD6002	Phase 3
0.6901	Remote Similarity	NPD6005	Phase 3
0.69	Remote Similarity	NPD7680	Approved
0.6898	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7236	Approved
0.689	Remote Similarity	NPD2798	Approved
0.6872	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1607	Approved
0.686	Remote Similarity	NPD7047	Phase 3
0.6859	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7907	Approved
0.6853	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD9717	Approved
0.6852	Remote Similarity	NPD1608	Approved
0.6845	Remote Similarity	NPD4140	Approved
0.6845	Remote Similarity	NPD1240	Approved
0.6845	Remote Similarity	NPD4307	Phase 2

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