NPASS Compound

Structure

CID242748 OpenBabel06191716042D 54 59 0 0 1 0 0 0 0 0999 V2000 1.0627 -3.1029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3330 -2.7460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8217 -1.7342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2587 -3.2145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6352 -2.9244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5616 -3.7255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7071 -4.2188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7382 -3.9047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5611 -0.7664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7069 -1.2592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4158 -2.2459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1442 -5.6978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1442 -2.7391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2687 1.1423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5055 1.2411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3683 -1.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2653 -2.5235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4360 -3.7263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5616 -2.7388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4156 -1.2598 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8526 -3.7255 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9981 -4.2188 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6386 -4.3056 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2902 -5.2048 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9987 -2.2457 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3046 0.9374 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4863 1.1381 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2896 -4.2191 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8527 -2.7388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3549 1.6699 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0659 1.9360 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3190 1.4650 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0467 1.8331 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6237 0.5276 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4479 0.9322 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9641 -0.2049 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.8683 0.1343 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7072 -2.2454 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1442 -3.7258 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9283 0.4098 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1043 2.1420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7416 -5.2859 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4243 -5.7050 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9987 -1.2457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0503 2.6073 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6647 2.8369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9786 2.1975 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6262 2.6310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5878 0.3227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4287 0.8292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2687 -1.1423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2696 -0.7666 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 -7.8875 0.2373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 8 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 19 2 0 0 0 0 8 23 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 38 1 0 0 0 0 11 19 1 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 13 39 1 0 0 0 0 14 40 1 0 0 0 0 15 41 1 0 0 0 0 16 17 1 0 0 0 0 16 51 1 0 0 0 0 17 1 1 6 0 0 0 18 2 1 6 0 0 0 18 23 1 0 0 0 0 18 28 1 0 0 0 0 19 38 1 0 0 0 0 20 52 1 1 0 0 0 21 7 1 6 0 0 0 21 22 1 0 0 0 0 21 29 1 0 0 0 0 22 39 1 1 0 0 0 23 42 1 6 0 0 0 24 28 1 0 0 0 0 24 43 1 1 0 0 0 25 29 1 0 0 0 0 25 44 1 6 0 0 0 26 14 1 6 0 0 0 26 30 1 0 0 0 0 26 53 1 0 0 0 0 27 15 1 1 0 0 0 27 31 1 0 0 0 0 27 54 1 0 0 0 0 28 39 1 1 0 0 0 29 38 1 1 0 0 0 30 32 1 0 0 0 0 30 45 1 1 0 0 0 31 33 1 0 0 0 0 31 46 1 6 0 0 0 32 34 1 0 0 0 0 32 47 1 6 0 0 0 33 35 1 0 0 0 0 33 48 1 1 0 0 0 34 36 1 0 0 0 0 34 49 1 1 0 0 0 35 37 1 0 0 0 0 35 50 1 6 0 0 0 36 51 1 6 0 0 0 36 53 1 0 0 0 0 37 52 1 1 0 0 0 37 54 1 0 0 0 0 38 3 1 1 0 0 0 39 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	774.44
Volume:	760.978
LogP:	0.96
LogD:	1.813
LogS:	-2.949
# Rotatable Bonds:	12
TPSA:	259.45
# H-Bond Aceptor:	15
# H-Bond Donor:	11
# Rings:	6
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.106
Synthetic Accessibility Score:	5.976
Fsp3:	0.949
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.329
MDCK Permeability:	0.00012813968351110816
Pgp-inhibitor:	0.084
Pgp-substrate:	0.752
Human Intestinal Absorption (HIA):	0.995
20% Bioavailability (F20%):	0.957
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.106
Plasma Protein Binding (PPB):	51.64851379394531%
Volume Distribution (VD):	0.2
Pgp-substrate:	14.691330909729004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.041
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	0.75
Half-life (T1/2):	0.83

ADMET: Toxicity

hERG Blockers:	0.26
Human Hepatotoxicity (H-HT):	0.231
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.055
Skin Sensitization:	0.621
Carcinogencity:	0.239
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC242748

Natural Product ID:	NPC242748
*Common Name:**	Heloside A
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[(2R,5S,6S)-6-[(3S,8S,9S,10R,11R,13S,14S,16S,17R)-11,16-dihydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-2-methylheptoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	Heloside A
Standard InCHIKey:	LXXFNSODUDJHAV-WHHFEMLGSA-N
Standard InCHI:	InChI=1S/C39H66O15/c1-17(16-51-36-34(49)32(47)30(45)26(14-40)53-36)5-8-23(42)18(2)28-24(43)12-22-21-7-6-19-11-20(52-37-35(50)33(48)31(46)27(15-41)54-37)9-10-38(19,3)29(21)25(44)13-39(22,28)4/h6,17-18,20-37,40-50H,5,7-16H2,1-4H3/t17-,18-,20+,21+,22+,23+,24+,25-,26-,27-,28+,29-,30-,31-,32+,33+,34-,35-,36-,37-,38+,39+/m1/s1
SMILES:	C[C@H](CC[C@@H]([C@@H](C)[C@H]1[C@H](C[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3[C@@H](C[C@]12C)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2088129
PubChem CID:	53466475
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO33234	chamaellirium luteum	Species	n.a.	n.a.	roots	sourced from Botanical Liaisons Ltd. (USA) and Blessed Herbs Ltd. (USA)	n.a.	PMID[22880631]
NPO11520	Homalanthus acuminatus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11520	Homalanthus acuminatus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2470	Abies spectabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11520	Homalanthus acuminatus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10817	Perilla ocymoides	Species	Araneidae	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1523	Cell Line	NFF	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[544902]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[544902]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[544902]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[544902]
NPT1524	Cell Line	MM96L	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[544902]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[544902]

☑ 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 NPC242748 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	260
0.1-0.2	1950
0.2-0.3	6127
0.3-0.4	13230
0.4-0.5	9171
0.5-0.6	5374
0.6-0.7	3521
0.7-0.8	1983
0.8-0.85	670
0.85-0.9	224
0.9-0.95	173
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9796	High Similarity	NPC473923
0.9796	High Similarity	NPC473476
0.9697	High Similarity	NPC473469
0.9694	High Similarity	NPC470885
0.9694	High Similarity	NPC221562
0.9694	High Similarity	NPC187400
0.96	High Similarity	NPC476539
0.96	High Similarity	NPC476538
0.96	High Similarity	NPC476540
0.96	High Similarity	NPC476541
0.96	High Similarity	NPC7213
0.9596	High Similarity	NPC181845
0.9596	High Similarity	NPC474569
0.951	High Similarity	NPC197231
0.951	High Similarity	NPC114188
0.9505	High Similarity	NPC477027
0.9505	High Similarity	NPC70204
0.9505	High Similarity	NPC306131
0.9505	High Similarity	NPC475670
0.9505	High Similarity	NPC477026
0.95	High Similarity	NPC190395
0.95	High Similarity	NPC470432
0.95	High Similarity	NPC230507
0.95	High Similarity	NPC161676
0.95	High Similarity	NPC305423
0.95	High Similarity	NPC283829
0.95	High Similarity	NPC113044
0.95	High Similarity	NPC94272
0.95	High Similarity	NPC14704
0.949	High Similarity	NPC288694
0.949	High Similarity	NPC159036
0.949	High Similarity	NPC312553
0.949	High Similarity	NPC272015
0.9417	High Similarity	NPC19888
0.9406	High Similarity	NPC295980
0.9406	High Similarity	NPC98696
0.94	High Similarity	NPC309448
0.9394	High Similarity	NPC245280
0.9394	High Similarity	NPC131479
0.9394	High Similarity	NPC189852
0.9394	High Similarity	NPC157659
0.9394	High Similarity	NPC8039
0.9394	High Similarity	NPC114874
0.9394	High Similarity	NPC120123
0.9394	High Similarity	NPC16573
0.9394	High Similarity	NPC31907
0.9394	High Similarity	NPC472252
0.9394	High Similarity	NPC286969
0.9394	High Similarity	NPC211879
0.9394	High Similarity	NPC16520
0.9394	High Similarity	NPC155010
0.9394	High Similarity	NPC473020
0.932	High Similarity	NPC294129
0.932	High Similarity	NPC475247
0.932	High Similarity	NPC476547
0.932	High Similarity	NPC13190
0.9314	High Similarity	NPC194207
0.9314	High Similarity	NPC477809
0.9314	High Similarity	NPC73243
0.9314	High Similarity	NPC476835
0.9314	High Similarity	NPC300557
0.9314	High Similarity	NPC208383
0.9314	High Similarity	NPC475550
0.9314	High Similarity	NPC84956
0.9314	High Similarity	NPC244086
0.9314	High Similarity	NPC249265
0.9314	High Similarity	NPC302057
0.9314	High Similarity	NPC102016
0.9314	High Similarity	NPC46190
0.9314	High Similarity	NPC232054
0.9314	High Similarity	NPC6806
0.9314	High Similarity	NPC475333
0.9314	High Similarity	NPC95051
0.9314	High Similarity	NPC42482
0.9314	High Similarity	NPC150372
0.9314	High Similarity	NPC248746
0.9314	High Similarity	NPC22779
0.9314	High Similarity	NPC218571
0.9314	High Similarity	NPC171073
0.9314	High Similarity	NPC40440
0.9314	High Similarity	NPC224098
0.9314	High Similarity	NPC470433
0.9314	High Similarity	NPC309278
0.9307	High Similarity	NPC226642
0.93	High Similarity	NPC165033
0.93	High Similarity	NPC75608
0.93	High Similarity	NPC273879
0.9293	High Similarity	NPC136816
0.9286	High Similarity	NPC282669
0.9286	High Similarity	NPC7341
0.9286	High Similarity	NPC473200
0.9278	High Similarity	NPC76486
0.9278	High Similarity	NPC243728
0.9278	High Similarity	NPC473890
0.9238	High Similarity	NPC477810
0.9231	High Similarity	NPC32361
0.9231	High Similarity	NPC210569
0.9231	High Similarity	NPC263359
0.9231	High Similarity	NPC31896
0.9231	High Similarity	NPC244431
0.9231	High Similarity	NPC112274
0.9223	High Similarity	NPC87998
0.9223	High Similarity	NPC477811
0.9223	High Similarity	NPC23808
0.9223	High Similarity	NPC224314
0.9223	High Similarity	NPC269297
0.9223	High Similarity	NPC141433
0.9223	High Similarity	NPC222202
0.9223	High Similarity	NPC247037
0.9208	High Similarity	NPC127801
0.9208	High Similarity	NPC160816
0.9208	High Similarity	NPC208477
0.9208	High Similarity	NPC194842
0.9208	High Similarity	NPC269627
0.9208	High Similarity	NPC152584
0.9208	High Similarity	NPC208594
0.9208	High Similarity	NPC69737
0.9208	High Similarity	NPC26798
0.92	High Similarity	NPC473198
0.9192	High Similarity	NPC129372
0.9192	High Similarity	NPC47566
0.9192	High Similarity	NPC4831
0.9192	High Similarity	NPC309425
0.9192	High Similarity	NPC160734
0.9192	High Similarity	NPC472023
0.9192	High Similarity	NPC88000
0.9184	High Similarity	NPC280825
0.9184	High Similarity	NPC158088
0.9184	High Similarity	NPC234287
0.9143	High Similarity	NPC51154
0.9143	High Similarity	NPC79900
0.9143	High Similarity	NPC307642
0.9143	High Similarity	NPC476693
0.9143	High Similarity	NPC144068
0.9143	High Similarity	NPC476546
0.9135	High Similarity	NPC477032
0.9135	High Similarity	NPC470748
0.9135	High Similarity	NPC124677
0.9135	High Similarity	NPC477028
0.9135	High Similarity	NPC13193
0.9126	High Similarity	NPC14630
0.9126	High Similarity	NPC250089
0.9126	High Similarity	NPC157530
0.9118	High Similarity	NPC208650
0.9118	High Similarity	NPC63368
0.9118	High Similarity	NPC14946
0.9118	High Similarity	NPC181467
0.9118	High Similarity	NPC231340
0.9118	High Similarity	NPC234160
0.9109	High Similarity	NPC312774
0.9109	High Similarity	NPC93352
0.9109	High Similarity	NPC475365
0.9109	High Similarity	NPC475521
0.9091	High Similarity	NPC91497
0.9057	High Similarity	NPC11548
0.9057	High Similarity	NPC32707
0.9057	High Similarity	NPC167183
0.9057	High Similarity	NPC208832
0.9048	High Similarity	NPC254255
0.9048	High Similarity	NPC308140
0.9048	High Similarity	NPC42171
0.9029	High Similarity	NPC159005
0.9029	High Similarity	NPC180183
0.9029	High Similarity	NPC246124
0.9029	High Similarity	NPC472897
0.9029	High Similarity	NPC472988
0.9029	High Similarity	NPC220427
0.9029	High Similarity	NPC6931
0.9029	High Similarity	NPC472896
0.9029	High Similarity	NPC38217
0.902	High Similarity	NPC472899
0.902	High Similarity	NPC472898
0.902	High Similarity	NPC472900
0.901	High Similarity	NPC475701
0.901	High Similarity	NPC213190
0.9	High Similarity	NPC470434
0.9	High Similarity	NPC267510
0.9	High Similarity	NPC263756
0.9	High Similarity	NPC117714
0.898	High Similarity	NPC207617
0.8972	High Similarity	NPC63609
0.8972	High Similarity	NPC148965
0.8972	High Similarity	NPC477030
0.8972	High Similarity	NPC477029
0.8969	High Similarity	NPC72817
0.8969	High Similarity	NPC477927
0.8952	High Similarity	NPC472987
0.8952	High Similarity	NPC473021
0.8942	High Similarity	NPC154085
0.8942	High Similarity	NPC125361
0.8942	High Similarity	NPC43976
0.8942	High Similarity	NPC51925
0.8942	High Similarity	NPC296761
0.8932	High Similarity	NPC33053
0.8922	High Similarity	NPC474464
0.8922	High Similarity	NPC109792
0.8922	High Similarity	NPC57065
0.8922	High Similarity	NPC54521
0.8911	High Similarity	NPC30289
0.8911	High Similarity	NPC213674

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 NPC242748 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	2107
0.2-0.3	4261
0.3-0.4	1703
0.4-0.5	444
0.5-0.6	223
0.6-0.7	167
0.7-0.8	22
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD8033	Approved
0.8482	Intermediate Similarity	NPD8377	Approved
0.8482	Intermediate Similarity	NPD8294	Approved
0.8407	Intermediate Similarity	NPD8379	Approved
0.8407	Intermediate Similarity	NPD8296	Approved
0.8407	Intermediate Similarity	NPD8380	Approved
0.8407	Intermediate Similarity	NPD8335	Approved
0.8407	Intermediate Similarity	NPD8378	Approved
0.8224	Intermediate Similarity	NPD6412	Phase 2
0.8142	Intermediate Similarity	NPD7328	Approved
0.8142	Intermediate Similarity	NPD7327	Approved
0.8119	Intermediate Similarity	NPD8171	Discontinued
0.8087	Intermediate Similarity	NPD7503	Approved
0.807	Intermediate Similarity	NPD7516	Approved
0.7788	Intermediate Similarity	NPD8133	Approved
0.7748	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD8449	Approved
0.7667	Intermediate Similarity	NPD7507	Approved
0.7661	Intermediate Similarity	NPD8450	Suspended
0.7586	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8328	Phase 3
0.748	Intermediate Similarity	NPD7319	Approved
0.7417	Intermediate Similarity	NPD6370	Approved
0.7398	Intermediate Similarity	NPD7736	Approved
0.7387	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD8293	Discontinued
0.7273	Intermediate Similarity	NPD7525	Registered
0.725	Intermediate Similarity	NPD6054	Approved
0.725	Intermediate Similarity	NPD6059	Approved
0.7216	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6686	Approved
0.7172	Intermediate Similarity	NPD7645	Phase 2
0.7115	Intermediate Similarity	NPD7524	Approved
0.7113	Intermediate Similarity	NPD7339	Approved
0.7113	Intermediate Similarity	NPD6942	Approved
0.71	Intermediate Similarity	NPD6928	Phase 2
0.7094	Intermediate Similarity	NPD8297	Approved
0.7094	Intermediate Similarity	NPD6882	Approved
0.7073	Intermediate Similarity	NPD6067	Discontinued
0.7049	Intermediate Similarity	NPD6015	Approved
0.7049	Intermediate Similarity	NPD6016	Approved
0.7016	Intermediate Similarity	NPD7492	Approved
0.7	Intermediate Similarity	NPD6009	Approved
0.6992	Remote Similarity	NPD5988	Approved
0.699	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6319	Approved
0.696	Remote Similarity	NPD6616	Approved
0.6952	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7638	Approved
0.6911	Remote Similarity	NPD8515	Approved
0.6911	Remote Similarity	NPD8516	Approved
0.6911	Remote Similarity	NPD8517	Approved
0.6911	Remote Similarity	NPD8513	Phase 3
0.6905	Remote Similarity	NPD7078	Approved
0.6893	Remote Similarity	NPD6695	Phase 3
0.6891	Remote Similarity	NPD4632	Approved
0.6875	Remote Similarity	NPD7639	Approved
0.6875	Remote Similarity	NPD7640	Approved
0.687	Remote Similarity	NPD7128	Approved
0.687	Remote Similarity	NPD6402	Approved
0.687	Remote Similarity	NPD6675	Approved
0.687	Remote Similarity	NPD5739	Approved
0.6838	Remote Similarity	NPD6373	Approved
0.6838	Remote Similarity	NPD6372	Approved
0.6792	Remote Similarity	NPD7750	Discontinued
0.6789	Remote Similarity	NPD6399	Phase 3
0.6752	Remote Similarity	NPD7320	Approved
0.6752	Remote Similarity	NPD6881	Approved
0.6752	Remote Similarity	NPD6899	Approved
0.6739	Remote Similarity	NPD7625	Phase 1
0.6723	Remote Similarity	NPD8130	Phase 1
0.6723	Remote Similarity	NPD6649	Approved
0.6723	Remote Similarity	NPD6650	Approved
0.6719	Remote Similarity	NPD6033	Approved
0.67	Remote Similarity	NPD6933	Approved
0.6696	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD4784	Approved
0.6667	Remote Similarity	NPD6929	Approved
0.6639	Remote Similarity	NPD7102	Approved
0.6639	Remote Similarity	NPD4634	Approved
0.6639	Remote Similarity	NPD7290	Approved
0.6639	Remote Similarity	NPD6883	Approved
0.6636	Remote Similarity	NPD4202	Approved
0.6633	Remote Similarity	NPD4243	Approved
0.6602	Remote Similarity	NPD4748	Discontinued
0.6602	Remote Similarity	NPD6931	Approved
0.6602	Remote Similarity	NPD6930	Phase 2
0.6585	Remote Similarity	NPD7115	Discovery
0.6583	Remote Similarity	NPD6847	Approved
0.6583	Remote Similarity	NPD6869	Approved
0.6583	Remote Similarity	NPD6617	Approved
0.6581	Remote Similarity	NPD6008	Approved
0.6579	Remote Similarity	NPD5286	Approved
0.6579	Remote Similarity	NPD4700	Approved
0.6579	Remote Similarity	NPD5285	Approved
0.6579	Remote Similarity	NPD4696	Approved
0.6577	Remote Similarity	NPD7748	Approved
0.6555	Remote Similarity	NPD6012	Approved
0.6555	Remote Similarity	NPD6014	Approved
0.6555	Remote Similarity	NPD6013	Approved
0.6549	Remote Similarity	NPD7902	Approved
0.6549	Remote Similarity	NPD6083	Phase 2
0.6549	Remote Similarity	NPD6084	Phase 2
0.6545	Remote Similarity	NPD8035	Phase 2
0.6545	Remote Similarity	NPD8034	Phase 2
0.6535	Remote Similarity	NPD7604	Phase 2
0.6522	Remote Similarity	NPD4159	Approved
0.6514	Remote Similarity	NPD5328	Approved
0.6508	Remote Similarity	NPD5983	Phase 2
0.65	Remote Similarity	NPD6926	Approved
0.65	Remote Similarity	NPD6924	Approved
0.6476	Remote Similarity	NPD3667	Approved
0.6471	Remote Similarity	NPD5776	Phase 2
0.6471	Remote Similarity	NPD6011	Approved
0.6471	Remote Similarity	NPD6925	Approved
0.6471	Remote Similarity	NPD6932	Approved
0.6466	Remote Similarity	NPD4633	Approved
0.6466	Remote Similarity	NPD5225	Approved
0.6466	Remote Similarity	NPD5224	Approved
0.6466	Remote Similarity	NPD5226	Approved
0.6466	Remote Similarity	NPD5211	Phase 2
0.6446	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD4768	Approved
0.6441	Remote Similarity	NPD4767	Approved
0.6434	Remote Similarity	NPD6336	Discontinued
0.641	Remote Similarity	NPD5175	Approved
0.641	Remote Similarity	NPD5174	Approved
0.6408	Remote Similarity	NPD7145	Approved
0.6396	Remote Similarity	NPD7515	Phase 2
0.6396	Remote Similarity	NPD7087	Discontinued
0.6396	Remote Similarity	NPD6079	Approved
0.6389	Remote Similarity	NPD3618	Phase 1
0.6379	Remote Similarity	NPD5223	Approved
0.6372	Remote Similarity	NPD7991	Discontinued
0.6364	Remote Similarity	NPD4753	Phase 2
0.6364	Remote Similarity	NPD6051	Approved
0.6356	Remote Similarity	NPD5141	Approved
0.6355	Remote Similarity	NPD3133	Approved
0.6355	Remote Similarity	NPD3666	Approved
0.6355	Remote Similarity	NPD3665	Phase 1
0.6348	Remote Similarity	NPD4225	Approved
0.6346	Remote Similarity	NPD6683	Phase 2
0.6337	Remote Similarity	NPD1811	Approved
0.6337	Remote Similarity	NPD1810	Approved
0.6333	Remote Similarity	NPD4730	Approved
0.6333	Remote Similarity	NPD4729	Approved
0.6325	Remote Similarity	NPD7632	Discontinued
0.6306	Remote Similarity	NPD3168	Discontinued
0.63	Remote Similarity	NPD7152	Approved
0.63	Remote Similarity	NPD7151	Approved
0.63	Remote Similarity	NPD7150	Approved
0.6296	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6893	Approved
0.6286	Remote Similarity	NPD7514	Phase 3
0.6286	Remote Similarity	NPD7509	Discontinued
0.6283	Remote Similarity	NPD7900	Approved
0.6283	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4190	Phase 3
0.6275	Remote Similarity	NPD5275	Approved
0.6273	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD4754	Approved
0.6263	Remote Similarity	NPD6922	Approved
0.6263	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6923	Approved
0.625	Remote Similarity	NPD7637	Suspended
0.6241	Remote Similarity	NPD5956	Approved
0.624	Remote Similarity	NPD6274	Approved
0.6239	Remote Similarity	NPD6684	Approved
0.6239	Remote Similarity	NPD7521	Approved
0.6239	Remote Similarity	NPD7334	Approved
0.6239	Remote Similarity	NPD7146	Approved
0.6239	Remote Similarity	NPD6409	Approved
0.6239	Remote Similarity	NPD5330	Approved
0.623	Remote Similarity	NPD5250	Approved
0.623	Remote Similarity	NPD5248	Approved
0.623	Remote Similarity	NPD5249	Phase 3
0.623	Remote Similarity	NPD5247	Approved
0.623	Remote Similarity	NPD5251	Approved
0.6228	Remote Similarity	NPD5695	Phase 3
0.6226	Remote Similarity	NPD6902	Approved
0.622	Remote Similarity	NPD7100	Approved
0.622	Remote Similarity	NPD7101	Approved
0.6207	Remote Similarity	NPD5696	Approved
0.62	Remote Similarity	NPD7144	Approved
0.62	Remote Similarity	NPD7143	Approved
0.6198	Remote Similarity	NPD5128	Approved
0.619	Remote Similarity	NPD4195	Approved
0.6174	Remote Similarity	NPD5221	Approved
0.6174	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD4697	Phase 3
0.6174	Remote Similarity	NPD5222	Approved
0.6142	Remote Similarity	NPD6335	Approved
0.6136	Remote Similarity	NPD8074	Phase 3
0.6132	Remote Similarity	NPD7332	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