NPASS Compound

Structure

NPC289423 OpenBabel07101718222D 57 62 0 0 1 0 0 0 0 0999 V2000 3.8046 -2.6939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1497 4.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8535 -2.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7429 3.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6456 -1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.2429 2.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5738 1.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3147 -0.6636 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.5619 4.9250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1104 -3.0540 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2375 2.2319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7817 0.6151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7648 2.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 35 1 0 0 0 0 7 36 1 0 0 0 0 8 13 1 0 0 0 0 8 48 1 0 0 0 0 9 16 1 0 0 0 0 9 37 2 0 0 0 0 10 2 1 1 0 0 0 10 17 1 0 0 0 0 10 49 1 0 0 0 0 11 3 1 1 0 0 0 11 18 1 0 0 0 0 11 50 1 0 0 0 0 12 4 1 1 0 0 0 12 26 1 0 0 0 0 12 51 1 0 0 0 0 13 19 1 0 0 0 0 13 38 1 1 0 0 0 14 16 2 0 0 0 0 14 52 1 0 0 0 0 15 7 1 6 0 0 0 15 20 1 0 0 0 0 15 53 1 0 0 0 0 16 35 1 0 0 0 0 17 21 1 0 0 0 0 17 39 1 6 0 0 0 18 27 1 0 0 0 0 18 40 1 1 0 0 0 19 28 1 0 0 0 0 19 41 1 1 0 0 0 20 22 1 0 0 0 0 20 42 1 1 0 0 0 21 23 1 0 0 0 0 21 43 1 1 0 0 0 22 31 1 0 0 0 0 22 44 1 6 0 0 0 23 30 1 0 0 0 0 23 45 1 6 0 0 0 24 26 1 0 0 0 0 24 29 1 0 0 0 0 24 46 1 1 0 0 0 25 27 1 0 0 0 0 25 32 1 0 0 0 0 25 47 1 6 0 0 0 26 54 1 6 0 0 0 27 55 1 1 0 0 0 28 33 1 0 0 0 0 28 56 1 6 0 0 0 29 34 1 0 0 0 0 29 57 1 6 0 0 0 30 49 1 0 0 0 0 30 57 1 1 0 0 0 31 53 1 0 0 0 0 31 55 1 1 0 0 0 32 50 1 0 0 0 0 32 56 1 1 0 0 0 33 48 1 0 0 0 0 33 54 1 6 0 0 0 34 51 1 0 0 0 0 34 52 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	827.31
Volume:	741.754
LogP:	-1.766
LogD:	-0.67
LogS:	-2.684
# Rotatable Bonds:	12
TPSA:	347.69
# H-Bond Aceptor:	23
# H-Bond Donor:	12
# Rings:	6
# Heavy Atoms:	23

MedChem Properties

QED Drug-Likeness Score:	0.087
Synthetic Accessibility Score:	6.05
Fsp3:	0.853
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:	-6.573
MDCK Permeability:	0.00028242269763723016
Pgp-inhibitor:	0.001
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.237
Plasma Protein Binding (PPB):	23.06353759765625%
Volume Distribution (VD):	0.225
Pgp-substrate:	33.48731231689453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.037
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	0.391
Half-life (T1/2):	0.89

ADMET: Toxicity

hERG Blockers:	0.352
Human Hepatotoxicity (H-HT):	0.145
Drug-inuced Liver Injury (DILI):	0.85
AMES Toxicity:	0.073
Rat Oral Acute Toxicity:	0.18
Maximum Recommended Daily Dose:	0.0
Skin Sensitization:	0.343
Carcinogencity:	0.055
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.15

Download Data

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

Natural Product: NPC289423

Natural Product ID:	NPC289423
*Common Name:**	Astebatherioside B
IUPAC Name:	1-[3-[(2S,3R,4S,5S,6R)-5-[(2R,3R,4S,5S)-3-[(2S,3R,4S,5S,6R)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-4-hydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-1H-pyrrol-2-yl]ethanone
Synonyms:	Astebatherioside B
Standard InCHIKey:	FKEQSFSUQODGOX-PXQGXXGMSA-N
Standard InCHI:	InChI=1S/C34H53NO22/c1-9(37)16-14(5-6-35-16)52-34-29(57-30-23(45)21(43)17(39)10(2)49-30)24(46)26(12(4)51-34)54-33-28(19(41)13(38)8-48-33)56-32-25(47)27(18(40)11(3)50-32)55-31-22(44)20(42)15(7-36)53-31/h5-6,10-13,15,17-36,38-47H,7-8H2,1-4H3/t10-,11-,12-,13+,15+,17-,18+,19+,20+,21+,22-,23-,24+,25-,26-,27+,28-,29-,30+,31+,32+,33-,34+/m1/s1
SMILES:	OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)O[C@@H]1[C@@H](O)[C@H](O[C@H]2[C@H](OC[C@@H]([C@@H]2O)O)O[C@@H]2[C@@H](C)O[C@H]([C@@H]([C@H]2O)O[C@@H]2O[C@H](C)[C@H]([C@@H]([C@H]2O)O)O)Oc2cc[nH]c2C(=O)C)O[C@@H]([C@@H]1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333841
PubChem CID:	71568187
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

*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
NPO33245	asterina batheri	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[23395633]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	36400.0	nM	PMID[522903]

☑ 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 NPC289423 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	444
0.1-0.2	2994
0.2-0.3	11959
0.3-0.4	15227
0.4-0.5	9009
0.5-0.6	2618
0.6-0.7	433
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC212766
0.9849	High Similarity	NPC90019
0.9548	High Similarity	NPC153452
0.7568	Intermediate Similarity	NPC288349
0.7206	Intermediate Similarity	NPC472436
0.7171	Intermediate Similarity	NPC314222
0.7171	Intermediate Similarity	NPC196449
0.7085	Intermediate Similarity	NPC472435
0.7037	Intermediate Similarity	NPC472434
0.7023	Intermediate Similarity	NPC209917
0.6996	Remote Similarity	NPC316224
0.6892	Remote Similarity	NPC258048
0.6833	Remote Similarity	NPC77061
0.6804	Remote Similarity	NPC127647
0.6787	Remote Similarity	NPC476516
0.6754	Remote Similarity	NPC156044
0.6743	Remote Similarity	NPC328798
0.6725	Remote Similarity	NPC308392
0.6712	Remote Similarity	NPC182814
0.6694	Remote Similarity	NPC476090
0.6681	Remote Similarity	NPC475271
0.668	Remote Similarity	NPC478045
0.6667	Remote Similarity	NPC12944
0.6667	Remote Similarity	NPC25442
0.6651	Remote Similarity	NPC318020
0.664	Remote Similarity	NPC37473
0.6637	Remote Similarity	NPC20593
0.6637	Remote Similarity	NPC79223
0.6628	Remote Similarity	NPC152620
0.6626	Remote Similarity	NPC196718
0.661	Remote Similarity	NPC309919
0.6591	Remote Similarity	NPC325775
0.6588	Remote Similarity	NPC53534
0.6565	Remote Similarity	NPC309498
0.6561	Remote Similarity	NPC473800
0.656	Remote Similarity	NPC325093
0.6557	Remote Similarity	NPC102593
0.6555	Remote Similarity	NPC54066
0.6552	Remote Similarity	NPC477548
0.6549	Remote Similarity	NPC320748
0.6549	Remote Similarity	NPC324245
0.6545	Remote Similarity	NPC57453
0.6541	Remote Similarity	NPC172355
0.654	Remote Similarity	NPC82070
0.6537	Remote Similarity	NPC474905
0.6535	Remote Similarity	NPC32451
0.6535	Remote Similarity	NPC328559
0.6534	Remote Similarity	NPC310618
0.6529	Remote Similarity	NPC244536
0.6525	Remote Similarity	NPC471978
0.6522	Remote Similarity	NPC165964
0.652	Remote Similarity	NPC160127
0.652	Remote Similarity	NPC50997
0.6513	Remote Similarity	NPC168209
0.6512	Remote Similarity	NPC473833
0.6506	Remote Similarity	NPC99891
0.6498	Remote Similarity	NPC476514
0.6494	Remote Similarity	NPC148896
0.6494	Remote Similarity	NPC476517
0.6494	Remote Similarity	NPC180668
0.6494	Remote Similarity	NPC471736
0.6494	Remote Similarity	NPC471013
0.6484	Remote Similarity	NPC475301
0.6484	Remote Similarity	NPC53255
0.6484	Remote Similarity	NPC327373
0.6484	Remote Similarity	NPC326930
0.6484	Remote Similarity	NPC85879
0.6483	Remote Similarity	NPC313640
0.648	Remote Similarity	NPC124300
0.6476	Remote Similarity	NPC59033
0.6468	Remote Similarity	NPC111732
0.6466	Remote Similarity	NPC316403
0.6462	Remote Similarity	NPC328928
0.646	Remote Similarity	NPC292361
0.6459	Remote Similarity	NPC13603
0.6454	Remote Similarity	NPC291609
0.6447	Remote Similarity	NPC474767
0.6445	Remote Similarity	NPC471015
0.6444	Remote Similarity	NPC226202
0.6444	Remote Similarity	NPC52254
0.6437	Remote Similarity	NPC182222
0.6432	Remote Similarity	NPC175150
0.6432	Remote Similarity	NPC243633
0.6432	Remote Similarity	NPC329024
0.6419	Remote Similarity	NPC253810
0.6409	Remote Similarity	NPC322043
0.6403	Remote Similarity	NPC475533
0.6402	Remote Similarity	NPC314270
0.6392	Remote Similarity	NPC10904
0.6388	Remote Similarity	NPC471979
0.6387	Remote Similarity	NPC476114
0.6386	Remote Similarity	NPC477589
0.6386	Remote Similarity	NPC477587
0.6378	Remote Similarity	NPC475315
0.6378	Remote Similarity	NPC324619
0.6375	Remote Similarity	NPC148889
0.6372	Remote Similarity	NPC84853
0.6364	Remote Similarity	NPC33229
0.6356	Remote Similarity	NPC146418
0.6352	Remote Similarity	NPC472287
0.6352	Remote Similarity	NPC472286
0.6336	Remote Similarity	NPC476115
0.6335	Remote Similarity	NPC477585
0.6335	Remote Similarity	NPC477590
0.6335	Remote Similarity	NPC477588
0.6335	Remote Similarity	NPC477586
0.6332	Remote Similarity	NPC317672
0.632	Remote Similarity	NPC15801
0.632	Remote Similarity	NPC184680
0.6307	Remote Similarity	NPC313804
0.6307	Remote Similarity	NPC315804
0.6304	Remote Similarity	NPC220408
0.6304	Remote Similarity	NPC187558
0.6295	Remote Similarity	NPC166722
0.6295	Remote Similarity	NPC470785
0.6292	Remote Similarity	NPC472285
0.6289	Remote Similarity	NPC63971
0.6289	Remote Similarity	NPC91868
0.6288	Remote Similarity	NPC74153
0.6286	Remote Similarity	NPC473506
0.6271	Remote Similarity	NPC472752
0.6267	Remote Similarity	NPC75544
0.6261	Remote Similarity	NPC477041
0.6261	Remote Similarity	NPC477044
0.626	Remote Similarity	NPC186351
0.625	Remote Similarity	NPC161801
0.625	Remote Similarity	NPC260434
0.6245	Remote Similarity	NPC473850
0.6245	Remote Similarity	NPC475137
0.6245	Remote Similarity	NPC475498
0.624	Remote Similarity	NPC476515
0.6235	Remote Similarity	NPC470486
0.6235	Remote Similarity	NPC194740
0.6235	Remote Similarity	NPC471190
0.6235	Remote Similarity	NPC471977
0.6235	Remote Similarity	NPC475644
0.623	Remote Similarity	NPC470784
0.623	Remote Similarity	NPC101350
0.6228	Remote Similarity	NPC473821
0.6225	Remote Similarity	NPC469554
0.6224	Remote Similarity	NPC162812
0.6223	Remote Similarity	NPC476874
0.622	Remote Similarity	NPC472762
0.6219	Remote Similarity	NPC291517
0.6204	Remote Similarity	NPC76565
0.6204	Remote Similarity	NPC250807
0.6204	Remote Similarity	NPC57797
0.6202	Remote Similarity	NPC26543
0.6198	Remote Similarity	NPC174788
0.6198	Remote Similarity	NPC197141
0.6194	Remote Similarity	NPC477787
0.6194	Remote Similarity	NPC122968
0.6194	Remote Similarity	NPC328186
0.6194	Remote Similarity	NPC87152
0.6194	Remote Similarity	NPC476110
0.6194	Remote Similarity	NPC475600
0.6194	Remote Similarity	NPC475631
0.6194	Remote Similarity	NPC228377
0.6192	Remote Similarity	NPC314882
0.619	Remote Similarity	NPC235685
0.6181	Remote Similarity	NPC475844
0.6181	Remote Similarity	NPC210296
0.6181	Remote Similarity	NPC119134
0.6179	Remote Similarity	NPC233727
0.6179	Remote Similarity	NPC477902
0.6178	Remote Similarity	NPC77878
0.6178	Remote Similarity	NPC183537
0.6175	Remote Similarity	NPC35208
0.6175	Remote Similarity	NPC475426
0.617	Remote Similarity	NPC477043
0.6169	Remote Similarity	NPC475362
0.6167	Remote Similarity	NPC229348
0.6164	Remote Similarity	NPC477045
0.6164	Remote Similarity	NPC103361
0.616	Remote Similarity	NPC30456
0.616	Remote Similarity	NPC478006
0.6157	Remote Similarity	NPC471014
0.6157	Remote Similarity	NPC475408
0.6151	Remote Similarity	NPC108342
0.6148	Remote Similarity	NPC107123
0.6147	Remote Similarity	NPC473814
0.6147	Remote Similarity	NPC78767
0.6143	Remote Similarity	NPC219963
0.6143	Remote Similarity	NPC161887
0.6142	Remote Similarity	NPC253482
0.6141	Remote Similarity	NPC50562
0.6138	Remote Similarity	NPC122436
0.6136	Remote Similarity	NPC472846
0.6135	Remote Similarity	NPC237702
0.6133	Remote Similarity	NPC295158
0.6132	Remote Similarity	NPC144779
0.6132	Remote Similarity	NPC469594
0.6132	Remote Similarity	NPC294579
0.6132	Remote Similarity	NPC281049
0.613	Remote Similarity	NPC93390
0.6129	Remote Similarity	NPC211920
0.6129	Remote Similarity	NPC146824
0.6129	Remote Similarity	NPC124029
0.6126	Remote Similarity	NPC189903
0.6126	Remote Similarity	NPC182907

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 NPC289423 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	631
0.2-0.3	1316
0.3-0.4	2752
0.4-0.5	2839
0.5-0.6	1297
0.6-0.7	108
0.7-0.8	0
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
0.6835	Remote Similarity	NPD5640	Discontinued
0.672	Remote Similarity	NPD5482	Discontinued
0.6682	Remote Similarity	NPD565	Phase 2
0.6624	Remote Similarity	NPD8479	Phase 2
0.6611	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD5532	Phase 2
0.657	Remote Similarity	NPD8421	Discontinued
0.656	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7853	Phase 2
0.6543	Remote Similarity	NPD1659	Phase 1
0.6543	Remote Similarity	NPD5022	Discontinued
0.6531	Remote Similarity	NPD7558	Phase 2
0.6529	Remote Similarity	NPD4086	Phase 1
0.6522	Remote Similarity	NPD7396	Approved
0.651	Remote Similarity	NPD8370	Discontinued
0.6498	Remote Similarity	NPD8325	Phase 3
0.6498	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD8326	Phase 3
0.6478	Remote Similarity	NPD3006	Discontinued
0.6475	Remote Similarity	NPD5450	Discontinued
0.6466	Remote Similarity	NPD1392	Approved
0.6457	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD5066	Phase 2
0.6426	Remote Similarity	NPD5067	Phase 2
0.6414	Remote Similarity	NPD2547	Discontinued
0.6414	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD5632	Approved
0.6398	Remote Similarity	NPD5866	Approved
0.6386	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD6974	Phase 3
0.6368	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD1034	Phase 3
0.6368	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8356	Approved
0.6352	Remote Similarity	NPD3263	Phase 3
0.6341	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6298	Discontinued
0.6303	Remote Similarity	NPD3945	Discontinued
0.6292	Remote Similarity	NPD4989	Phase 2
0.6292	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7031	Phase 1
0.629	Remote Similarity	NPD3178	Discontinued
0.6275	Remote Similarity	NPD8468	Phase 2
0.6266	Remote Similarity	NPD5948	Phase 2
0.626	Remote Similarity	NPD8430	Approved
0.6255	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD3569	Discontinued
0.6231	Remote Similarity	NPD5922	Phase 3
0.6224	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.622	Remote Similarity	NPD8289	Discontinued
0.6218	Remote Similarity	NPD4131	Phase 3
0.6216	Remote Similarity	NPD7859	Phase 2
0.6215	Remote Similarity	NPD4454	Phase 2
0.6214	Remote Similarity	NPD7180	Phase 3
0.6206	Remote Similarity	NPD7886	Phase 2
0.6206	Remote Similarity	NPD7885	Phase 2
0.6198	Remote Similarity	NPD6531	Approved
0.6198	Remote Similarity	NPD6530	Approved
0.6198	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.619	Remote Similarity	NPD772	Phase 3
0.6183	Remote Similarity	NPD5612	Discontinued
0.6183	Remote Similarity	NPD3389	Approved
0.6183	Remote Similarity	NPD3393	Approved
0.6183	Remote Similarity	NPD3394	Approved
0.6173	Remote Similarity	NPD2785	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD1768	Approved
0.6157	Remote Similarity	NPD7022	Phase 2
0.615	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD5479	Discontinued
0.6144	Remote Similarity	NPD3003	Approved
0.6141	Remote Similarity	NPD5902	Approved
0.6141	Remote Similarity	NPD5149	Phase 2
0.6141	Remote Similarity	NPD5903	Approved
0.6141	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD4429	Discontinued
0.6129	Remote Similarity	NPD7994	Phase 2
0.6128	Remote Similarity	NPD6669	Phase 2
0.6125	Remote Similarity	NPD7069	Discontinued
0.6123	Remote Similarity	NPD4021	Phase 2
0.612	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD6569	Phase 2
0.6113	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD8442	Discontinued
0.6105	Remote Similarity	NPD7803	Approved
0.6104	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD3477	Phase 2
0.6094	Remote Similarity	NPD1483	Discontinued
0.6094	Remote Similarity	NPD2958	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD1418	Phase 2
0.6092	Remote Similarity	NPD2510	Approved
0.6092	Remote Similarity	NPD7467	Discontinued
0.6092	Remote Similarity	NPD2509	Approved
0.6082	Remote Similarity	NPD6242	Discontinued
0.608	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7708	Approved
0.6063	Remote Similarity	NPD946	Discontinued
0.6063	Remote Similarity	NPD4368	Phase 2
0.6059	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD3074	Discontinued
0.604	Remote Similarity	NPD8104	Phase 3
0.6039	Remote Similarity	NPD6825	Phase 1
0.6038	Remote Similarity	NPD7955	Approved
0.6038	Remote Similarity	NPD7956	Approved
0.6034	Remote Similarity	NPD2831	Approved
0.6033	Remote Similarity	NPD2314	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD2772	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD7603	Discontinued
0.6024	Remote Similarity	NPD7426	Phase 1
0.6018	Remote Similarity	NPD1096	Discontinued
0.6017	Remote Similarity	NPD3570	Phase 2
0.6017	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5416	Discontinued
0.6017	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD8512	Phase 3
0.6016	Remote Similarity	NPD8374	Phase 3
0.6009	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6008	Remote Similarity	NPD5293	Phase 2
0.6008	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6008	Remote Similarity	NPD1638	Discovery
0.6008	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.5992	Remote Similarity	NPD5513	Phase 2
0.5985	Remote Similarity	NPD7967	Discontinued
0.5984	Remote Similarity	NPD8329	Phase 3
0.5984	Remote Similarity	NPD2951	Discontinued
0.5984	Remote Similarity	NPD7788	Phase 2
0.5982	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD3402	Phase 1
0.5968	Remote Similarity	NPD4885	Approved
0.5968	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD6209	Approved
0.5967	Remote Similarity	NPD3795	Approved
0.5967	Remote Similarity	NPD3794	Approved
0.5966	Remote Similarity	NPD4036	Approved
0.5966	Remote Similarity	NPD4037	Approved
0.5966	Remote Similarity	NPD31	Approved
0.5966	Remote Similarity	NPD4035	Approved
0.5966	Remote Similarity	NPD4039	Approved
0.5966	Remote Similarity	NPD4033	Approved
0.5966	Remote Similarity	NPD32	Approved
0.5966	Remote Similarity	NPD4038	Approved
0.5966	Remote Similarity	NPD4122	Approved
0.5966	Remote Similarity	NPD4034	Approved
0.5965	Remote Similarity	NPD5256	Discontinued
0.5957	Remote Similarity	NPD8063	Discontinued
0.5956	Remote Similarity	NPD9510	Approved
0.5953	Remote Similarity	NPD1927	Discontinued
0.595	Remote Similarity	NPD7470	Discontinued
0.5947	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.5945	Remote Similarity	NPD4373	Phase 2
0.5941	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD4072	Approved
0.5938	Remote Similarity	NPD4071	Approved
0.5935	Remote Similarity	NPD6568	Discontinued
0.5935	Remote Similarity	NPD6985	Discontinued
0.5932	Remote Similarity	NPD5228	Phase 3
0.5932	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD5320	Approved
0.5928	Remote Similarity	NPD5319	Approved
0.5926	Remote Similarity	NPD6286	Phase 3
0.5922	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.5916	Remote Similarity	NPD4887	Discontinued
0.5914	Remote Similarity	NPD4313	Approved
0.5914	Remote Similarity	NPD4314	Approved
0.5914	Remote Similarity	NPD3781	Phase 2
0.5912	Remote Similarity	NPD5018	Phase 3
0.5911	Remote Similarity	NPD7194	Discontinued
0.5907	Remote Similarity	NPD7727	Phase 2
0.5907	Remote Similarity	NPD6716	Phase 1
0.5906	Remote Similarity	NPD8465	Approved
0.5906	Remote Similarity	NPD8466	Approved
0.5906	Remote Similarity	NPD8467	Approved
0.5905	Remote Similarity	NPD4372	Phase 1
0.5902	Remote Similarity	NPD8255	Phase 2
0.5901	Remote Similarity	NPD9548	Phase 2
0.59	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.59	Remote Similarity	NPD8375	Approved
0.5899	Remote Similarity	NPD604	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD5116	Phase 1
0.589	Remote Similarity	NPD3825	Phase 3
0.589	Remote Similarity	NPD863	Approved
0.589	Remote Similarity	NPD861	Approved
0.589	Remote Similarity	NPD862	Approved
0.5887	Remote Similarity	NPD5850	Phase 3
0.5885	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD2779	Approved
0.5882	Remote Similarity	NPD6494	Phase 2
0.588	Remote Similarity	NPD1038	Approved
0.5878	Remote Similarity	NPD6205	Discontinued
0.5875	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD7957	Phase 1
0.5875	Remote Similarity	NPD8409	Suspended

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