NPASS Compound

Structure

NPC475508 OpenBabel07101719252D 46 49 0 0 1 0 0 0 0 0999 V2000 -2.0970 -3.5918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2057 1.0030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9797 1.4152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8802 -4.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2313 -2.2828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5203 2.2813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5287 0.7888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6850 -1.6556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5427 -2.6455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8363 -2.2304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9609 -2.7138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8553 -1.2306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1045 -2.1974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9990 -0.7142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7567 -2.0273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.4776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4759 0.5746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3413 -2.9369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4499 0.3481 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4797 0.5492 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0917 -5.1608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0420 -3.2647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4797 2.2813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6190 0.3734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1236 -1.1976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6144 -1.0375 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 -3.4776 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3413 -2.9369 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5355 -0.6482 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9595 -0.2817 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4797 0.5492 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6144 -1.0375 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2672 -0.6812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7567 -2.0273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9595 -0.2817 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3734 -6.1203 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7978 -3.9196 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9797 3.1473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8045 0.9535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2863 0.3186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7817 -4.4371 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0970 -3.5918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9797 1.4152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5240 -0.6221 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3918 -1.1646 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 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 23 1 0 0 0 0 7 24 1 0 0 0 0 8 34 1 0 0 0 0 9 34 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 2 0 0 0 0 13 25 2 0 0 0 0 14 25 1 0 0 0 0 15 18 2 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 16 28 1 0 0 0 0 17 19 1 0 0 0 0 18 27 1 0 0 0 0 19 2 1 1 0 0 0 19 29 1 0 0 0 0 20 3 1 1 0 0 0 20 30 1 0 0 0 0 20 31 1 0 0 0 0 21 36 2 0 0 0 0 21 41 1 0 0 0 0 22 37 2 0 0 0 0 22 42 1 0 0 0 0 23 38 2 0 0 0 0 23 43 1 0 0 0 0 24 39 2 0 0 0 0 24 44 1 0 0 0 0 25 33 1 0 0 0 0 26 29 1 0 0 0 0 26 35 1 1 0 0 0 27 41 1 1 0 0 0 28 34 1 0 0 0 0 28 42 1 6 0 0 0 29 45 1 1 0 0 0 30 32 1 0 0 0 0 30 46 1 1 0 0 0 31 35 1 1 0 0 0 31 43 1 0 0 0 0 32 34 1 0 0 0 0 32 44 1 1 0 0 0 33 40 2 0 0 0 0 33 45 1 0 0 0 0 35 17 1 1 0 0 0 35 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	642.3
Volume:	652.654
LogP:	4.514
LogD:	2.907
LogS:	-4.571
# Rotatable Bonds:	11
TPSA:	140.73
# H-Bond Aceptor:	11
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.241
Synthetic Accessibility Score:	6.652
Fsp3:	0.629
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:	-5.071
MDCK Permeability:	7.715302490396425e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.103
20% Bioavailability (F20%):	0.705
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	88.00806427001953%
Volume Distribution (VD):	2.185
Pgp-substrate:	9.134650230407715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.013
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.284
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.195
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.456
CYP3A4-substrate:	0.353

ADMET: Excretion

Clearance (CL):	3.573
Half-life (T1/2):	0.174

ADMET: Toxicity

hERG Blockers:	0.53
Human Hepatotoxicity (H-HT):	0.962
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.561
Maximum Recommended Daily Dose:	0.225
Skin Sensitization:	0.311
Carcinogencity:	0.028
Eye Corrosion:	0.006
Eye Irritation:	0.043
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC475508

Natural Product ID:	NPC475508
*Common Name:**	IUFJHIRZJMZTIU-UGNKFOPQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IUFJHIRZJMZTIU-UGNKFOPQSA-N
Standard InCHI:	InChI=1S/C35H46O11/c1-18-15-26-29(45-33(40)25-13-11-10-12-14-25)19(2)17-35(26)31(43-23(6)38)20(3)30(46-35)32(44-24(7)39)34(8,9)28(42-22(5)37)16-27(18)41-21(4)36/h10-15,19-20,26-32H,16-17H2,1-9H3/b18-15+/t19-,20-,26-,27+,28+,29-,30-,31-,32+,35+/m0/s1
SMILES:	CC(=O)O[C@H]1[C@@H](C)[C@@H]2O[C@]31C[C@@H]([C@@H]([C@@H]3/C=C(C)/[C@@H](C[C@H](C([C@@H]2OC(=O)C)(C)C)OC(=O)C)OC(=O)C)OC(=O)c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507009
PubChem CID:	44567567
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
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18321057]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19099222]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30724086]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31550154]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12682	Euphorbia helioscopia	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
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[542359]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[542359]

☑ 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 NPC475508 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	313
0.1-0.2	1094
0.2-0.3	2267
0.3-0.4	6023
0.4-0.5	11637
0.5-0.6	15839
0.6-0.7	4690
0.7-0.8	649
0.8-0.85	76
0.85-0.9	61
0.9-0.95	45
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9683	High Similarity	NPC134937
0.9683	High Similarity	NPC298547
0.9683	High Similarity	NPC324898
0.9606	High Similarity	NPC149401
0.9606	High Similarity	NPC279637
0.9606	High Similarity	NPC200154
0.9524	High Similarity	NPC233860
0.9457	High Similarity	NPC327511
0.9457	High Similarity	NPC205305
0.9449	High Similarity	NPC472248
0.9385	High Similarity	NPC121268
0.9385	High Similarity	NPC53361
0.9375	High Similarity	NPC28836
0.9375	High Similarity	NPC472250
0.9375	High Similarity	NPC153617
0.937	High Similarity	NPC239358
0.9302	High Similarity	NPC79699
0.9302	High Similarity	NPC265459
0.9302	High Similarity	NPC475262
0.9302	High Similarity	NPC290833
0.9242	High Similarity	NPC187566
0.9231	High Similarity	NPC194769
0.9231	High Similarity	NPC202729
0.9231	High Similarity	NPC285221
0.9225	High Similarity	NPC311492
0.9219	High Similarity	NPC233692
0.916	High Similarity	NPC86772
0.916	High Similarity	NPC27721
0.9104	High Similarity	NPC131966
0.9104	High Similarity	NPC191387
0.9091	High Similarity	NPC272523
0.9091	High Similarity	NPC325805
0.9091	High Similarity	NPC473301
0.9023	High Similarity	NPC475660
0.9023	High Similarity	NPC251294
0.9008	High Similarity	NPC270364
0.8955	High Similarity	NPC473497
0.8955	High Similarity	NPC475413
0.8955	High Similarity	NPC474303
0.8955	High Similarity	NPC242355
0.8905	High Similarity	NPC170668
0.8824	High Similarity	NPC477096
0.8824	High Similarity	NPC153214
0.8824	High Similarity	NPC477094
0.8824	High Similarity	NPC45307
0.8824	High Similarity	NPC82467
0.8806	High Similarity	NPC276652
0.8676	High Similarity	NPC473654
0.8633	High Similarity	NPC477095
0.8626	High Similarity	NPC42234
0.8626	High Similarity	NPC272946
0.8613	High Similarity	NPC475135
0.8582	High Similarity	NPC472247
0.8571	High Similarity	NPC205389
0.8496	Intermediate Similarity	NPC477360
0.8467	Intermediate Similarity	NPC162613
0.8467	Intermediate Similarity	NPC87934
0.8451	Intermediate Similarity	NPC232583
0.8451	Intermediate Similarity	NPC25484
0.8451	Intermediate Similarity	NPC477099
0.8451	Intermediate Similarity	NPC477101
0.8451	Intermediate Similarity	NPC477097
0.8444	Intermediate Similarity	NPC291638
0.8444	Intermediate Similarity	NPC17877
0.8444	Intermediate Similarity	NPC195647
0.8444	Intermediate Similarity	NPC472577
0.8444	Intermediate Similarity	NPC66761
0.8406	Intermediate Similarity	NPC266374
0.8397	Intermediate Similarity	NPC472706
0.8394	Intermediate Similarity	NPC9905
0.8382	Intermediate Similarity	NPC477358
0.837	Intermediate Similarity	NPC477368
0.837	Intermediate Similarity	NPC477359
0.837	Intermediate Similarity	NPC474608
0.8369	Intermediate Similarity	NPC240115
0.8369	Intermediate Similarity	NPC478263
0.8346	Intermediate Similarity	NPC147561
0.8346	Intermediate Similarity	NPC475671
0.8346	Intermediate Similarity	NPC475452
0.8346	Intermediate Similarity	NPC122504
0.8346	Intermediate Similarity	NPC3450
0.8345	Intermediate Similarity	NPC192658
0.8333	Intermediate Similarity	NPC473613
0.8333	Intermediate Similarity	NPC473112
0.8333	Intermediate Similarity	NPC200592
0.8333	Intermediate Similarity	NPC473085
0.8333	Intermediate Similarity	NPC147880
0.8333	Intermediate Similarity	NPC184747
0.8333	Intermediate Similarity	NPC473109
0.8333	Intermediate Similarity	NPC4341
0.8333	Intermediate Similarity	NPC211137
0.8333	Intermediate Similarity	NPC43241
0.8333	Intermediate Similarity	NPC473758
0.8333	Intermediate Similarity	NPC48017
0.8333	Intermediate Similarity	NPC476094
0.8333	Intermediate Similarity	NPC473081
0.8333	Intermediate Similarity	NPC473060
0.8321	Intermediate Similarity	NPC475373
0.8309	Intermediate Similarity	NPC232888
0.8309	Intermediate Similarity	NPC477367
0.8298	Intermediate Similarity	NPC478264
0.8296	Intermediate Similarity	NPC477364
0.8288	Intermediate Similarity	NPC70344
0.8276	Intermediate Similarity	NPC477098
0.8276	Intermediate Similarity	NPC477100
0.8273	Intermediate Similarity	NPC16912
0.8261	Intermediate Similarity	NPC210591
0.8261	Intermediate Similarity	NPC475652
0.8261	Intermediate Similarity	NPC214550
0.8239	Intermediate Similarity	NPC312393
0.8231	Intermediate Similarity	NPC472703
0.8227	Intermediate Similarity	NPC34943
0.8222	Intermediate Similarity	NPC472394
0.8201	Intermediate Similarity	NPC90614
0.8201	Intermediate Similarity	NPC171207
0.8201	Intermediate Similarity	NPC183270
0.8201	Intermediate Similarity	NPC97667
0.8201	Intermediate Similarity	NPC477904
0.8197	Intermediate Similarity	NPC469636
0.8195	Intermediate Similarity	NPC472707
0.8194	Intermediate Similarity	NPC125033
0.8188	Intermediate Similarity	NPC183122
0.8188	Intermediate Similarity	NPC283375
0.8182	Intermediate Similarity	NPC121272
0.8182	Intermediate Similarity	NPC327031
0.8175	Intermediate Similarity	NPC473399
0.8175	Intermediate Similarity	NPC473216
0.8169	Intermediate Similarity	NPC134131
0.8169	Intermediate Similarity	NPC25043
0.8169	Intermediate Similarity	NPC125882
0.8168	Intermediate Similarity	NPC8990
0.8168	Intermediate Similarity	NPC472704
0.816	Intermediate Similarity	NPC307651
0.8156	Intermediate Similarity	NPC177340
0.8156	Intermediate Similarity	NPC147217
0.8156	Intermediate Similarity	NPC95449
0.8156	Intermediate Similarity	NPC475429
0.8156	Intermediate Similarity	NPC139067
0.8156	Intermediate Similarity	NPC270498
0.8156	Intermediate Similarity	NPC191082
0.8156	Intermediate Similarity	NPC473673
0.8156	Intermediate Similarity	NPC246480
0.8151	Intermediate Similarity	NPC472657
0.8151	Intermediate Similarity	NPC472658
0.8151	Intermediate Similarity	NPC471135
0.8148	Intermediate Similarity	NPC470278
0.8148	Intermediate Similarity	NPC72915
0.8143	Intermediate Similarity	NPC27377
0.8143	Intermediate Similarity	NPC118080
0.8143	Intermediate Similarity	NPC291599
0.8143	Intermediate Similarity	NPC41481
0.8143	Intermediate Similarity	NPC87448
0.8143	Intermediate Similarity	NPC472576
0.8143	Intermediate Similarity	NPC97947
0.8138	Intermediate Similarity	NPC96308
0.8138	Intermediate Similarity	NPC161955
0.8133	Intermediate Similarity	NPC55744
0.8125	Intermediate Similarity	NPC76103
0.8112	Intermediate Similarity	NPC48599
0.8112	Intermediate Similarity	NPC473602
0.8112	Intermediate Similarity	NPC209592
0.8112	Intermediate Similarity	NPC20255
0.8106	Intermediate Similarity	NPC477369
0.8102	Intermediate Similarity	NPC4242
0.8102	Intermediate Similarity	NPC471911
0.8099	Intermediate Similarity	NPC188865
0.8099	Intermediate Similarity	NPC476974
0.8099	Intermediate Similarity	NPC25768
0.8099	Intermediate Similarity	NPC95265
0.8099	Intermediate Similarity	NPC95810
0.8099	Intermediate Similarity	NPC57628
0.8099	Intermediate Similarity	NPC472570
0.8099	Intermediate Similarity	NPC470231
0.8099	Intermediate Similarity	NPC11685
0.8099	Intermediate Similarity	NPC67777
0.8099	Intermediate Similarity	NPC472573
0.8099	Intermediate Similarity	NPC163719
0.8099	Intermediate Similarity	NPC472569
0.8099	Intermediate Similarity	NPC51314
0.8099	Intermediate Similarity	NPC70716
0.8099	Intermediate Similarity	NPC125106
0.8095	Intermediate Similarity	NPC469456
0.8088	Intermediate Similarity	NPC238370
0.8077	Intermediate Similarity	NPC50872
0.8071	Intermediate Similarity	NPC472547
0.8071	Intermediate Similarity	NPC275592
0.8071	Intermediate Similarity	NPC100913
0.8069	Intermediate Similarity	NPC476173
0.8056	Intermediate Similarity	NPC473760
0.8042	Intermediate Similarity	NPC473088
0.8042	Intermediate Similarity	NPC96903
0.8042	Intermediate Similarity	NPC472568
0.8042	Intermediate Similarity	NPC158663
0.8042	Intermediate Similarity	NPC171525
0.8042	Intermediate Similarity	NPC200471
0.8042	Intermediate Similarity	NPC470157
0.8042	Intermediate Similarity	NPC92867
0.8042	Intermediate Similarity	NPC184817
0.8042	Intermediate Similarity	NPC470159
0.8042	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 NPC475508 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	734
0.2-0.3	1627
0.3-0.4	2959
0.4-0.5	2281
0.5-0.6	1072
0.6-0.7	196
0.7-0.8	18
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
0.812	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD7236	Approved
0.7669	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD7799	Discontinued
0.7619	Intermediate Similarity	NPD2182	Approved
0.7533	Intermediate Similarity	NPD7239	Suspended
0.746	Intermediate Similarity	NPD6685	Approved
0.7429	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6004	Phase 3
0.7329	Intermediate Similarity	NPD6002	Phase 3
0.7329	Intermediate Similarity	NPD6005	Phase 3
0.7302	Intermediate Similarity	NPD164	Approved
0.7287	Intermediate Similarity	NPD2067	Discontinued
0.7222	Intermediate Similarity	NPD5765	Approved
0.7185	Intermediate Similarity	NPD7741	Discontinued
0.7176	Intermediate Similarity	NPD6912	Phase 3
0.7143	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7137	Phase 2
0.7121	Intermediate Similarity	NPD6858	Approved
0.7121	Intermediate Similarity	NPD7094	Approved
0.712	Intermediate Similarity	NPD1238	Approved
0.7101	Intermediate Similarity	NPD6287	Discontinued
0.7089	Intermediate Similarity	NPD7058	Phase 2
0.7089	Intermediate Similarity	NPD7057	Phase 3
0.7087	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4628	Phase 3
0.7015	Intermediate Similarity	NPD2629	Approved
0.6972	Remote Similarity	NPD6085	Phase 2
0.6972	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7685	Pre-registration
0.6939	Remote Similarity	NPD6653	Approved
0.6897	Remote Similarity	NPD3764	Approved
0.6855	Remote Similarity	NPD5761	Phase 2
0.6855	Remote Similarity	NPD5760	Phase 2
0.6849	Remote Similarity	NPD7961	Discontinued
0.6839	Remote Similarity	NPD6273	Approved
0.6838	Remote Similarity	NPD4198	Discontinued
0.6828	Remote Similarity	NPD7008	Discontinued
0.6822	Remote Similarity	NPD6647	Phase 2
0.6812	Remote Similarity	NPD9545	Approved
0.681	Remote Similarity	NPD8127	Discontinued
0.6783	Remote Similarity	NPD6362	Approved
0.6779	Remote Similarity	NPD2569	Approved
0.6779	Remote Similarity	NPD2567	Approved
0.6766	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4766	Approved
0.6759	Remote Similarity	NPD6832	Phase 2
0.6755	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6765	Approved
0.6746	Remote Similarity	NPD6764	Approved
0.6735	Remote Similarity	NPD6663	Approved
0.6725	Remote Similarity	NPD8407	Phase 2
0.6719	Remote Similarity	NPD7798	Approved
0.6713	Remote Similarity	NPD1876	Approved
0.669	Remote Similarity	NPD3663	Approved
0.669	Remote Similarity	NPD6637	Approved
0.669	Remote Similarity	NPD3664	Approved
0.669	Remote Similarity	NPD3661	Approved
0.669	Remote Similarity	NPD3662	Phase 3
0.6687	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD969	Suspended
0.6647	Remote Similarity	NPD8434	Phase 2
0.6647	Remote Similarity	NPD8368	Discontinued
0.6644	Remote Similarity	NPD6355	Discontinued
0.6644	Remote Similarity	NPD7055	Discontinued
0.6642	Remote Similarity	NPD4234	Approved
0.6642	Remote Similarity	NPD5951	Approved
0.6642	Remote Similarity	NPD4233	Approved
0.6622	Remote Similarity	NPD7713	Phase 3
0.6621	Remote Similarity	NPD5647	Approved
0.6604	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD5667	Approved
0.6596	Remote Similarity	NPD5125	Phase 3
0.6596	Remote Similarity	NPD5126	Approved
0.659	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.659	Remote Similarity	NPD6785	Approved
0.659	Remote Similarity	NPD6784	Approved
0.6587	Remote Similarity	NPD1202	Approved
0.6582	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD5736	Approved
0.6565	Remote Similarity	NPD1930	Approved
0.6565	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD1929	Approved
0.6562	Remote Similarity	NPD6599	Discontinued
0.6557	Remote Similarity	NPD9259	Approved
0.6557	Remote Similarity	NPD9257	Approved
0.6547	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD5763	Approved
0.6536	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD5762	Approved
0.6533	Remote Similarity	NPD230	Phase 1
0.6516	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD5909	Discontinued
0.651	Remote Similarity	NPD8032	Phase 2
0.6503	Remote Similarity	NPD4806	Approved
0.6503	Remote Similarity	NPD4807	Approved
0.6484	Remote Similarity	NPD1989	Approved
0.6483	Remote Similarity	NPD2198	Approved
0.6483	Remote Similarity	NPD2199	Approved
0.648	Remote Similarity	NPD3672	Approved
0.648	Remote Similarity	NPD3673	Approved
0.6479	Remote Similarity	NPD17	Approved
0.6479	Remote Similarity	NPD5305	Approved
0.6479	Remote Similarity	NPD5306	Approved
0.6471	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2438	Suspended
0.6462	Remote Similarity	NPD2066	Phase 3
0.646	Remote Similarity	NPD7028	Phase 2
0.6458	Remote Similarity	NPD3972	Approved
0.6457	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD7009	Phase 2
0.6449	Remote Similarity	NPD2650	Approved
0.6449	Remote Similarity	NPD2652	Approved
0.6442	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7819	Suspended
0.6429	Remote Similarity	NPD9493	Approved
0.6424	Remote Similarity	NPD7075	Discontinued
0.6418	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7497	Discontinued
0.641	Remote Similarity	NPD4110	Phase 3
0.641	Remote Similarity	NPD2575	Approved
0.641	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.641	Remote Similarity	NPD8166	Discontinued
0.6408	Remote Similarity	NPD5585	Approved
0.6406	Remote Similarity	NPD1693	Approved
0.6405	Remote Similarity	NPD7305	Phase 1
0.6405	Remote Similarity	NPD3748	Approved
0.6398	Remote Similarity	NPD7458	Discontinued
0.6395	Remote Similarity	NPD1019	Discontinued
0.6392	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6799	Approved
0.6391	Remote Similarity	NPD1237	Approved
0.6385	Remote Similarity	NPD9495	Approved
0.6384	Remote Similarity	NPD8361	Approved
0.6384	Remote Similarity	NPD8360	Approved
0.6384	Remote Similarity	NPD8435	Approved
0.6383	Remote Similarity	NPD7610	Discontinued
0.6378	Remote Similarity	NPD1088	Approved
0.6376	Remote Similarity	NPD6039	Approved
0.6375	Remote Similarity	NPD5403	Approved
0.6371	Remote Similarity	NPD1087	Approved
0.637	Remote Similarity	NPD1358	Approved
0.6369	Remote Similarity	NPD3887	Approved
0.6369	Remote Similarity	NPD6190	Approved
0.6364	Remote Similarity	NPD2796	Approved
0.6364	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD4307	Phase 2
0.6352	Remote Similarity	NPD2533	Approved
0.6352	Remote Similarity	NPD2534	Approved
0.6352	Remote Similarity	NPD5401	Approved
0.6352	Remote Similarity	NPD2532	Approved
0.6351	Remote Similarity	NPD5204	Approved
0.6351	Remote Similarity	NPD7084	Phase 3
0.6349	Remote Similarity	NPD9258	Approved
0.6349	Remote Similarity	NPD9256	Approved
0.6347	Remote Similarity	NPD5494	Approved
0.6346	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD1608	Approved
0.6343	Remote Similarity	NPD5048	Discontinued
0.6329	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD4106	Approved
0.6319	Remote Similarity	NPD6386	Approved
0.6319	Remote Similarity	NPD4136	Approved
0.6319	Remote Similarity	NPD6385	Approved
0.6319	Remote Similarity	NPD4135	Approved
0.6316	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7199	Phase 2
0.6309	Remote Similarity	NPD2613	Approved
0.6303	Remote Similarity	NPD5353	Approved
0.6303	Remote Similarity	NPD5402	Approved
0.6299	Remote Similarity	NPD7033	Discontinued
0.6299	Remote Similarity	NPD2799	Discontinued
0.6296	Remote Similarity	NPD3134	Approved
0.6291	Remote Similarity	NPD7715	Approved
0.6291	Remote Similarity	NPD7714	Approved
0.6284	Remote Similarity	NPD2798	Approved
0.628	Remote Similarity	NPD6801	Discontinued
0.6277	Remote Similarity	NPD5235	Approved
0.6277	Remote Similarity	NPD5237	Approved
0.6277	Remote Similarity	NPD5240	Approved
0.6277	Remote Similarity	NPD5236	Approved
0.6277	Remote Similarity	NPD5239	Approved
0.6275	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD920	Approved
0.6271	Remote Similarity	NPD8150	Discontinued
0.6265	Remote Similarity	NPD7768	Phase 2
0.6265	Remote Similarity	NPD4965	Approved
0.6265	Remote Similarity	NPD4966	Approved
0.6265	Remote Similarity	NPD4868	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