NPASS Compound

Structure

NPC152796 OpenBabel07101718222D 40 43 0 0 1 0 0 0 0 0999 V2000 -7.9851 -1.0091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2648 -4.3975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9777 -3.2386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6176 -4.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9340 -3.6544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6468 -2.4954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6394 -4.7248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 -1.7399 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 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2867 -4.1896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6249 -2.7033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -4.3090 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 -3.9703 -5.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 1 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 1.7321 -1.0000 0.0000 C 0 0 1 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 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 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 -2.3230 -0.9968 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 -4.2793 -6.4190 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 2.5981 -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 -1.7321 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2941 -1.9602 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 -5.2601 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 1 35 1 0 0 0 0 2 36 1 0 0 0 0 3 6 1 0 0 0 0 3 13 2 0 0 0 0 4 7 2 0 0 0 0 4 13 1 0 0 0 0 5 8 2 0 0 0 0 5 13 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 28 1 0 0 0 0 11 29 1 0 0 0 0 12 16 2 0 0 0 0 12 37 1 0 0 0 0 15 35 1 0 0 0 0 16 25 1 0 0 0 0 17 21 1 0 0 0 0 17 38 1 6 0 0 0 18 11 1 6 0 0 0 18 22 1 0 0 0 0 18 39 1 0 0 0 0 19 30 2 0 0 0 0 19 38 1 0 0 0 0 20 14 1 1 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 16 1 1 0 0 0 22 23 1 0 0 0 0 22 31 1 1 0 0 0 23 24 1 0 0 0 0 23 32 1 6 0 0 0 24 27 1 0 0 0 0 24 33 1 1 0 0 0 25 34 2 0 0 0 0 25 36 1 0 0 0 0 26 37 1 0 0 0 0 26 40 1 6 0 0 0 27 39 1 0 0 0 0 27 40 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	564.18
Volume:	534.504
LogP:	0.839
LogD:	0.875
LogS:	-2.547
# Rotatable Bonds:	11
TPSA:	190.67
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.14
Synthetic Accessibility Score:	4.786
Fsp3:	0.481
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:	-5.787
MDCK Permeability:	7.938593626022339e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.545
Human Intestinal Absorption (HIA):	0.716
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.2
Plasma Protein Binding (PPB):	37.573974609375%
Volume Distribution (VD):	0.467
Pgp-substrate:	22.444318771362305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.135
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.071
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.328
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	2.412
Half-life (T1/2):	0.812

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.586
Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.321
Carcinogencity:	0.839
Eye Corrosion:	0.003
Eye Irritation:	0.067
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC152796

Natural Product ID:	NPC152796
*Common Name:**	6-O-E-P-Methoxycinnamoyl Scandoside Methyl Ester
IUPAC Name:	methyl (1S,4aS,5R,7aS)-7-(hydroxymethyl)-5-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Synonyms:
Standard InCHIKey:	VBHBNHXZBKWQNO-BIIYMWGFSA-N
Standard InCHI:	InChI=1S/C27H32O13/c1-35-15-6-3-13(4-7-15)5-8-19(30)38-17-9-14(10-28)20-21(17)16(25(34)36-2)12-37-26(20)40-27-24(33)23(32)22(31)18(11-29)39-27/h3-9,12,17-18,20-24,26-29,31-33H,10-11H2,1-2H3/b8-5+/t17-,18-,20-,21+,22-,23+,24-,26+,27+/m1/s1
SMILES:	COc1ccc(cc1)/C=C/C(=O)O[C@@H]1C=C(CO)[C@@H]2[C@H]1C(=CO[C@H]2O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447012
PubChem CID:	44584782
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-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
NPO32921	hedyotis diffusa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170670]
NPO32921	hedyotis diffusa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20004577]

☑ 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
Others	8

Activity Type	# Activity
Individual Protein	6
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	Inhibition	=	19.1	%	PMID[542220]
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	Inhibition	=	36.6	%	PMID[542220]
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	Inhibition	=	46.3	%	PMID[542220]
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	Inhibition	=	63.0	%	PMID[542220]
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	Inhibition	=	81.2	%	PMID[542220]
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	IC50	=	18000.0	nM	PMID[542220]
NPT2	Others	Unspecified		Activity	=	65.4	%	PMID[542219]
NPT2	Others	Unspecified		Activity	=	71.8	%	PMID[542219]
NPT2	Others	Unspecified		Activity	=	52.8	%	PMID[542219]

☑ 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 NPC152796 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	289
0.1-0.2	1106
0.2-0.3	2858
0.3-0.4	6519
0.4-0.5	10766
0.5-0.6	6683
0.6-0.7	10468
0.7-0.8	3706
0.8-0.85	254
0.85-0.9	37
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475213
0.9559	High Similarity	NPC31745
0.9559	High Similarity	NPC220936
0.9433	High Similarity	NPC473149
0.9375	High Similarity	NPC203664
0.9286	High Similarity	NPC293154
0.9172	High Similarity	NPC475379
0.9085	High Similarity	NPC202391
0.9085	High Similarity	NPC296659
0.9085	High Similarity	NPC77922
0.9085	High Similarity	NPC473281
0.9044	High Similarity	NPC254819
0.9014	High Similarity	NPC263397
0.9014	High Similarity	NPC237872
0.9014	High Similarity	NPC116104
0.9014	High Similarity	NPC302286
0.9014	High Similarity	NPC88754
0.8951	High Similarity	NPC63304
0.8904	High Similarity	NPC96599
0.8849	High Similarity	NPC169398
0.8844	High Similarity	NPC117346
0.8844	High Similarity	NPC69367
0.8844	High Similarity	NPC240592
0.8828	High Similarity	NPC37838
0.8776	High Similarity	NPC478234
0.8759	High Similarity	NPC295970
0.875	High Similarity	NPC179914
0.875	High Similarity	NPC469367
0.8733	High Similarity	NPC478232
0.8723	High Similarity	NPC472132
0.8699	High Similarity	NPC143246
0.8699	High Similarity	NPC474268
0.8699	High Similarity	NPC473147
0.8699	High Similarity	NPC475539
0.8699	High Similarity	NPC119773
0.8693	High Similarity	NPC474936
0.869	High Similarity	NPC184464
0.869	High Similarity	NPC251062
0.869	High Similarity	NPC478240
0.8662	High Similarity	NPC469364
0.8662	High Similarity	NPC101686
0.8662	High Similarity	NPC65262
0.8658	High Similarity	NPC289021
0.8658	High Similarity	NPC158546
0.8649	High Similarity	NPC478236
0.8633	High Similarity	NPC281798
0.863	High Similarity	NPC475528
0.8627	High Similarity	NPC469384
0.8621	High Similarity	NPC186296
0.8611	High Similarity	NPC80098
0.8601	High Similarity	NPC49597
0.8591	High Similarity	NPC147224
0.8581	High Similarity	NPC476011
0.8581	High Similarity	NPC308178
0.8571	High Similarity	NPC291153
0.8562	High Similarity	NPC471028
0.8562	High Similarity	NPC286919
0.8562	High Similarity	NPC475663
0.8553	High Similarity	NPC475484
0.8533	High Similarity	NPC478249
0.8533	High Similarity	NPC269914
0.8523	High Similarity	NPC478242
0.8483	Intermediate Similarity	NPC154262
0.8483	Intermediate Similarity	NPC7518
0.8483	Intermediate Similarity	NPC79908
0.8483	Intermediate Similarity	NPC159387
0.8483	Intermediate Similarity	NPC137501
0.8478	Intermediate Similarity	NPC471882
0.8478	Intermediate Similarity	NPC45224
0.8478	Intermediate Similarity	NPC471881
0.8478	Intermediate Similarity	NPC106677
0.8478	Intermediate Similarity	NPC156692
0.8478	Intermediate Similarity	NPC173150
0.8478	Intermediate Similarity	NPC35288
0.8477	Intermediate Similarity	NPC194705
0.8467	Intermediate Similarity	NPC182350
0.8462	Intermediate Similarity	NPC206815
0.8451	Intermediate Similarity	NPC471029
0.8446	Intermediate Similarity	NPC212808
0.8425	Intermediate Similarity	NPC296643
0.8418	Intermediate Similarity	NPC130730
0.8418	Intermediate Similarity	NPC282551
0.8418	Intermediate Similarity	NPC301910
0.8417	Intermediate Similarity	NPC225307
0.8411	Intermediate Similarity	NPC474620
0.8406	Intermediate Similarity	NPC471157
0.8382	Intermediate Similarity	NPC52097
0.838	Intermediate Similarity	NPC114116
0.8377	Intermediate Similarity	NPC475378
0.8369	Intermediate Similarity	NPC246869
0.8369	Intermediate Similarity	NPC138777
0.8369	Intermediate Similarity	NPC225384
0.8367	Intermediate Similarity	NPC478250
0.8367	Intermediate Similarity	NPC242756
0.8357	Intermediate Similarity	NPC253595
0.8356	Intermediate Similarity	NPC46644
0.8355	Intermediate Similarity	NPC134905
0.8355	Intermediate Similarity	NPC36130
0.8354	Intermediate Similarity	NPC180586
0.8345	Intermediate Similarity	NPC226005
0.8344	Intermediate Similarity	NPC158635
0.8344	Intermediate Similarity	NPC229882
0.8333	Intermediate Similarity	NPC157554
0.8333	Intermediate Similarity	NPC294470
0.8333	Intermediate Similarity	NPC83218
0.8333	Intermediate Similarity	NPC37468
0.8333	Intermediate Similarity	NPC166180
0.8333	Intermediate Similarity	NPC471345
0.8333	Intermediate Similarity	NPC189631
0.8333	Intermediate Similarity	NPC126991
0.8323	Intermediate Similarity	NPC226759
0.8322	Intermediate Similarity	NPC34456
0.8313	Intermediate Similarity	NPC21956
0.8311	Intermediate Similarity	NPC110063
0.8311	Intermediate Similarity	NPC194938
0.8309	Intermediate Similarity	NPC11724
0.8301	Intermediate Similarity	NPC61604
0.8301	Intermediate Similarity	NPC245615
0.8301	Intermediate Similarity	NPC229548
0.8301	Intermediate Similarity	NPC89693
0.8301	Intermediate Similarity	NPC478241
0.8301	Intermediate Similarity	NPC246893
0.8301	Intermediate Similarity	NPC299706
0.8301	Intermediate Similarity	NPC115466
0.8299	Intermediate Similarity	NPC31081
0.8299	Intermediate Similarity	NPC245219
0.8299	Intermediate Similarity	NPC65833
0.8286	Intermediate Similarity	NPC146540
0.8278	Intermediate Similarity	NPC111785
0.8273	Intermediate Similarity	NPC61181
0.8273	Intermediate Similarity	NPC252114
0.8269	Intermediate Similarity	NPC76211
0.8267	Intermediate Similarity	NPC97240
0.8264	Intermediate Similarity	NPC212729
0.8255	Intermediate Similarity	NPC287615
0.8255	Intermediate Similarity	NPC83743
0.8255	Intermediate Similarity	NPC262182
0.8255	Intermediate Similarity	NPC210330
0.8255	Intermediate Similarity	NPC216819
0.8247	Intermediate Similarity	NPC191046
0.8247	Intermediate Similarity	NPC327032
0.8247	Intermediate Similarity	NPC194095
0.8239	Intermediate Similarity	NPC46137
0.8239	Intermediate Similarity	NPC235294
0.8239	Intermediate Similarity	NPC478255
0.8235	Intermediate Similarity	NPC478235
0.8235	Intermediate Similarity	NPC476872
0.8231	Intermediate Similarity	NPC476442
0.8231	Intermediate Similarity	NPC215512
0.8228	Intermediate Similarity	NPC145847
0.8224	Intermediate Similarity	NPC100818
0.8224	Intermediate Similarity	NPC35097
0.8219	Intermediate Similarity	NPC220942
0.8219	Intermediate Similarity	NPC100389
0.8217	Intermediate Similarity	NPC138993
0.8214	Intermediate Similarity	NPC103533
0.8214	Intermediate Similarity	NPC288416
0.8212	Intermediate Similarity	NPC473428
0.8212	Intermediate Similarity	NPC120728
0.821	Intermediate Similarity	NPC470685
0.8207	Intermediate Similarity	NPC103409
0.8205	Intermediate Similarity	NPC187205
0.8194	Intermediate Similarity	NPC10205
0.8194	Intermediate Similarity	NPC38699
0.8188	Intermediate Similarity	NPC297342
0.8182	Intermediate Similarity	NPC229354
0.8182	Intermediate Similarity	NPC269421
0.8182	Intermediate Similarity	NPC257847
0.8182	Intermediate Similarity	NPC469699
0.8182	Intermediate Similarity	NPC137813
0.8182	Intermediate Similarity	NPC157898
0.8182	Intermediate Similarity	NPC44730
0.8176	Intermediate Similarity	NPC140502
0.8176	Intermediate Similarity	NPC157816
0.8176	Intermediate Similarity	NPC109990
0.8163	Intermediate Similarity	NPC202700
0.8146	Intermediate Similarity	NPC175275
0.8143	Intermediate Similarity	NPC233559
0.8141	Intermediate Similarity	NPC471405
0.8141	Intermediate Similarity	NPC163635
0.8141	Intermediate Similarity	NPC478248
0.8141	Intermediate Similarity	NPC228357
0.8138	Intermediate Similarity	NPC185778
0.8133	Intermediate Similarity	NPC34587
0.8133	Intermediate Similarity	NPC100998
0.8133	Intermediate Similarity	NPC476382
0.8133	Intermediate Similarity	NPC252292
0.8133	Intermediate Similarity	NPC34927
0.8125	Intermediate Similarity	NPC28637
0.8121	Intermediate Similarity	NPC478239
0.8117	Intermediate Similarity	NPC478268
0.8116	Intermediate Similarity	NPC476142
0.8108	Intermediate Similarity	NPC186406
0.8105	Intermediate Similarity	NPC107197
0.8105	Intermediate Similarity	NPC104172
0.8105	Intermediate Similarity	NPC88886
0.8105	Intermediate Similarity	NPC227980
0.8101	Intermediate Similarity	NPC208676
0.8101	Intermediate Similarity	NPC478265
0.8101	Intermediate Similarity	NPC130489

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 NPC152796 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	237
0.1-0.2	714
0.2-0.3	1611
0.3-0.4	2644
0.4-0.5	2196
0.5-0.6	1203
0.6-0.7	489
0.7-0.8	56
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
0.8272	Intermediate Similarity	NPD7685	Pre-registration
0.7852	Intermediate Similarity	NPD7266	Discontinued
0.775	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4628	Phase 3
0.7692	Intermediate Similarity	NPD1653	Approved
0.7673	Intermediate Similarity	NPD8455	Phase 2
0.766	Intermediate Similarity	NPD1091	Approved
0.7647	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD37	Approved
0.759	Intermediate Similarity	NPD7228	Approved
0.7578	Intermediate Similarity	NPD4966	Approved
0.7578	Intermediate Similarity	NPD4967	Phase 2
0.7578	Intermediate Similarity	NPD4965	Approved
0.7548	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD7097	Phase 1
0.7517	Intermediate Similarity	NPD5647	Approved
0.75	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD3818	Discontinued
0.7485	Intermediate Similarity	NPD6234	Discontinued
0.7467	Intermediate Similarity	NPD6653	Approved
0.744	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7054	Approved
0.7419	Intermediate Similarity	NPD6190	Approved
0.74	Intermediate Similarity	NPD6355	Discontinued
0.7396	Intermediate Similarity	NPD7472	Approved
0.7383	Intermediate Similarity	NPD6233	Phase 2
0.7375	Intermediate Similarity	NPD4380	Phase 2
0.7368	Intermediate Similarity	NPD7033	Discontinued
0.7368	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1358	Approved
0.7326	Intermediate Similarity	NPD8312	Approved
0.7326	Intermediate Similarity	NPD8313	Approved
0.7317	Intermediate Similarity	NPD7075	Discontinued
0.7315	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7458	Discontinued
0.731	Intermediate Similarity	NPD7240	Approved
0.731	Intermediate Similarity	NPD7251	Discontinued
0.731	Intermediate Similarity	NPD6559	Discontinued
0.7305	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7074	Phase 3
0.729	Intermediate Similarity	NPD1652	Phase 2
0.7289	Intermediate Similarity	NPD8127	Discontinued
0.7284	Intermediate Similarity	NPD6801	Discontinued
0.7267	Intermediate Similarity	NPD7808	Phase 3
0.7259	Intermediate Similarity	NPD3134	Approved
0.7256	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD9545	Approved
0.7251	Intermediate Similarity	NPD6797	Phase 2
0.7244	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6362	Approved
0.7211	Intermediate Similarity	NPD2797	Approved
0.72	Intermediate Similarity	NPD3268	Approved
0.72	Intermediate Similarity	NPD6798	Discontinued
0.7188	Intermediate Similarity	NPD5403	Approved
0.7188	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD5124	Phase 1
0.7161	Intermediate Similarity	NPD6002	Phase 3
0.7161	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6004	Phase 3
0.7161	Intermediate Similarity	NPD6005	Phase 3
0.7161	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3225	Approved
0.7115	Intermediate Similarity	NPD2424	Discontinued
0.7107	Intermediate Similarity	NPD6799	Approved
0.7091	Intermediate Similarity	NPD5402	Approved
0.7063	Intermediate Similarity	NPD5401	Approved
0.7063	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD230	Phase 1
0.7059	Intermediate Similarity	NPD4340	Discontinued
0.7051	Intermediate Similarity	NPD5763	Approved
0.7051	Intermediate Similarity	NPD5762	Approved
0.7039	Intermediate Similarity	NPD4062	Phase 3
0.703	Intermediate Similarity	NPD7819	Suspended
0.7025	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7411	Suspended
0.7012	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3817	Phase 2
0.6977	Remote Similarity	NPD3751	Discontinued
0.6974	Remote Similarity	NPD3764	Approved
0.6968	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1357	Approved
0.6962	Remote Similarity	NPD6674	Discontinued
0.6959	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6599	Discontinued
0.695	Remote Similarity	NPD7843	Approved
0.6948	Remote Similarity	NPD1933	Approved
0.6939	Remote Similarity	NPD3705	Approved
0.6939	Remote Similarity	NPD422	Phase 1
0.6937	Remote Similarity	NPD5058	Phase 3
0.6936	Remote Similarity	NPD5844	Phase 1
0.6927	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7157	Approved
0.6918	Remote Similarity	NPD3750	Approved
0.6914	Remote Similarity	NPD6273	Approved
0.691	Remote Similarity	NPD8434	Phase 2
0.6908	Remote Similarity	NPD7095	Approved
0.6899	Remote Similarity	NPD1549	Phase 2
0.6892	Remote Similarity	NPD1608	Approved
0.6887	Remote Similarity	NPD9494	Approved
0.6887	Remote Similarity	NPD2861	Phase 2
0.6886	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5353	Approved
0.6879	Remote Similarity	NPD969	Suspended
0.6867	Remote Similarity	NPD1934	Approved
0.6867	Remote Similarity	NPD3266	Approved
0.6867	Remote Similarity	NPD3267	Approved
0.6857	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7028	Phase 2
0.6845	Remote Similarity	NPD7435	Discontinued
0.6842	Remote Similarity	NPD3787	Discontinued
0.6842	Remote Similarity	NPD6832	Phase 2
0.6835	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2801	Approved
0.6821	Remote Similarity	NPD7473	Discontinued
0.6821	Remote Similarity	NPD2798	Approved
0.6821	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2799	Discontinued
0.6815	Remote Similarity	NPD1510	Phase 2
0.6813	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4110	Phase 3
0.6811	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1778	Approved
0.6797	Remote Similarity	NPD3027	Phase 3
0.6792	Remote Similarity	NPD5958	Discontinued
0.6786	Remote Similarity	NPD2684	Approved
0.6783	Remote Similarity	NPD1241	Discontinued
0.6781	Remote Similarity	NPD1894	Discontinued
0.6779	Remote Similarity	NPD9717	Approved
0.6774	Remote Similarity	NPD4060	Phase 1
0.6774	Remote Similarity	NPD4140	Approved
0.6772	Remote Similarity	NPD2935	Discontinued
0.6772	Remote Similarity	NPD2438	Suspended
0.6772	Remote Similarity	NPD7999	Approved
0.6772	Remote Similarity	NPD2796	Approved
0.6763	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6166	Phase 2
0.6757	Remote Similarity	NPD3847	Discontinued
0.6755	Remote Similarity	NPD7680	Approved
0.6753	Remote Similarity	NPD7930	Approved
0.6748	Remote Similarity	NPD2532	Approved
0.6748	Remote Similarity	NPD2534	Approved
0.6748	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2533	Approved
0.6746	Remote Similarity	NPD7768	Phase 2
0.6746	Remote Similarity	NPD3882	Suspended
0.6744	Remote Similarity	NPD6232	Discontinued
0.6737	Remote Similarity	NPD7583	Approved
0.6735	Remote Similarity	NPD5585	Approved
0.6732	Remote Similarity	NPD4908	Phase 1
0.6731	Remote Similarity	NPD447	Suspended
0.6728	Remote Similarity	NPD7440	Discontinued
0.6726	Remote Similarity	NPD7972	Discontinued
0.6726	Remote Similarity	NPD1465	Phase 2
0.6725	Remote Similarity	NPD5494	Approved
0.6714	Remote Similarity	NPD290	Approved
0.6712	Remote Similarity	NPD5536	Phase 2
0.6711	Remote Similarity	NPD1535	Discovery
0.6709	Remote Similarity	NPD3748	Approved
0.6708	Remote Similarity	NPD8166	Discontinued
0.6707	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6385	Approved
0.6707	Remote Similarity	NPD6386	Approved
0.6704	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7585	Approved
0.6689	Remote Similarity	NPD5125	Phase 3
0.6689	Remote Similarity	NPD8651	Approved
0.6689	Remote Similarity	NPD5126	Approved
0.6689	Remote Similarity	NPD1876	Approved
0.6689	Remote Similarity	NPD17	Approved
0.6687	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4534	Discontinued
0.6687	Remote Similarity	NPD3226	Approved
0.6686	Remote Similarity	NPD7799	Discontinued
0.6684	Remote Similarity	NPD6781	Approved
0.6684	Remote Similarity	NPD6780	Approved
0.6684	Remote Similarity	NPD6782	Approved
0.6684	Remote Similarity	NPD6777	Approved
0.6684	Remote Similarity	NPD6778	Approved
0.6684	Remote Similarity	NPD6776	Approved
0.6684	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD2240	Approved
0.6667	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD1613	Approved
0.6667	Remote Similarity	NPD6647	Phase 2
0.6667	Remote Similarity	NPD5712	Approved
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD2239	Approved
0.6667	Remote Similarity	NPD1481	Phase 2
0.6667	Remote Similarity	NPD1240	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data