NPASS Compound

Structure

CID18789 OpenBabel06191715342D 37 41 0 0 1 0 0 0 0 0999 V2000 5.9364 -0.1169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2891 -0.6521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9145 -0.3248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6199 -1.3952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2514 -3.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6146 -3.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5762 -1.8111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8108 -1.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4062 -0.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2672 -0.8600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2514 -2.3917 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.2235 -1.2758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5544 -2.0190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9448 -2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6418 -1.1873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6146 -1.8917 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.9448 -3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0787 -3.8917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2127 -3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9945 -1.7226 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4807 -2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2127 -2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6768 -2.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9349 -0.0982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2017 -1.4837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8634 -2.9700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3328 -0.2363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8108 -3.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0787 -4.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3467 -3.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4807 -3.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0787 -1.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9727 -1.9305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3467 -1.8917 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 3 2 0 0 0 0 1 10 1 0 0 0 0 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 12 1 0 0 0 0 4 15 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 33 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 25 1 0 0 0 0 9 26 1 0 0 0 0 11 16 1 0 0 0 0 11 20 1 0 0 0 0 12 13 2 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 8 1 1 0 0 0 14 17 1 0 0 0 0 14 34 1 0 0 0 0 15 29 2 0 0 0 0 15 35 1 0 0 0 0 16 22 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 30 1 6 0 0 0 18 19 1 0 0 0 0 18 31 1 1 0 0 0 19 23 1 0 0 0 0 19 32 1 6 0 0 0 20 21 1 0 0 0 0 20 35 1 6 0 0 0 21 24 1 1 0 0 0 21 37 1 0 0 0 0 22 33 1 0 0 0 0 22 36 1 6 0 0 0 23 34 1 0 0 0 0 23 36 1 1 0 0 0 24 9 1 1 0 0 0 24 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	524.15
Volume:	479.332
LogP:	-0.173
LogD:	-0.252
LogS:	-1.938
# Rotatable Bonds:	8
TPSA:	208.13
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.09
Synthetic Accessibility Score:	5.09
Fsp3:	0.542
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.492
MDCK Permeability:	7.020681368885562e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.922
Human Intestinal Absorption (HIA):	0.907
20% Bioavailability (F20%):	0.748
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117
Plasma Protein Binding (PPB):	74.29605102539062%
Volume Distribution (VD):	0.399
Pgp-substrate:	24.866825103759766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.022
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.155
CYP3A4-inhibitor:	0.163
CYP3A4-substrate:	0.106

ADMET: Excretion

Clearance (CL):	1.415
Half-life (T1/2):	0.86

ADMET: Toxicity

hERG Blockers:	0.412
Human Hepatotoxicity (H-HT):	0.831
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.112
Rat Oral Acute Toxicity:	0.158
Maximum Recommended Daily Dose:	0.096
Skin Sensitization:	0.699
Carcinogencity:	0.222
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.74

Download Data

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

Natural Product: NPC18789

Natural Product ID:	NPC18789
*Common Name:**	Verminoside
IUPAC Name:	[(1aR,2R,6R,6aR)-1a-(hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-6-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:	Verminoside
Standard InCHIKey:	MZQXNUBTVLKMLP-VXPVLMLZSA-N
Standard InCHI:	InChI=1S/C24H28O13/c25-8-14-17(30)18(31)19(32)23(34-14)36-22-16-11(5-6-33-22)20(21-24(16,9-26)37-21)35-15(29)4-2-10-1-3-12(27)13(28)7-10/h1-7,11,14,16-23,25-28,30-32H,8-9H2/b4-2+/t11?,14-,16?,17-,18+,19-,20-,21-,22-,23+,24+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2OC=CC3C2[C@]2(CO)O[C@@H]2[C@@H]3OC(=O)/C=C/c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462888
PubChem CID:	11948660
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric 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
NPO16767	Kigelia pinnata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000047]
NPO16767	Kigelia pinnata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309308]
NPO4129	Veronica persica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16767	Kigelia pinnata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4129	Veronica persica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16767	Kigelia pinnata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4129	Veronica persica	Species	Plantaginaceae	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	1
Kd	1

Activity Type	# Activity
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	0.0995	ug.mL-1	PMID[469833]
NPT918	Individual Protein	Heat shock protein HSP 90-alpha	Homo sapiens	Kd	=	348.0	nM	PMID[469834]

☑ 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 NPC18789 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	351
0.1-0.2	1409
0.2-0.3	3266
0.3-0.4	7882
0.4-0.5	10418
0.5-0.6	10575
0.6-0.7	7214
0.7-0.8	1406
0.8-0.85	121
0.85-0.9	44
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9586	High Similarity	NPC229548
0.9586	High Similarity	NPC478241
0.9586	High Similarity	NPC89693
0.9568	High Similarity	NPC46644
0.9315	High Similarity	NPC269914
0.9315	High Similarity	NPC478249
0.9286	High Similarity	NPC49597
0.9262	High Similarity	NPC478248
0.9247	High Similarity	NPC147224
0.9205	High Similarity	NPC138993
0.9205	High Similarity	NPC478265
0.911	High Similarity	NPC308178
0.9103	High Similarity	NPC474234
0.9097	High Similarity	NPC478240
0.8966	High Similarity	NPC184464
0.8966	High Similarity	NPC251062
0.894	High Similarity	NPC475484
0.8921	High Similarity	NPC475824
0.891	High Similarity	NPC301910
0.891	High Similarity	NPC130730
0.8897	High Similarity	NPC302286
0.8897	High Similarity	NPC116104
0.8897	High Similarity	NPC237872
0.8897	High Similarity	NPC263397
0.8897	High Similarity	NPC88754
0.8889	High Similarity	NPC159387
0.8889	High Similarity	NPC154262
0.8889	High Similarity	NPC137501
0.8889	High Similarity	NPC7518
0.8882	High Similarity	NPC478266
0.8867	High Similarity	NPC194705
0.8857	High Similarity	NPC473924
0.8803	High Similarity	NPC476870
0.8794	High Similarity	NPC254398
0.8786	High Similarity	NPC219677
0.8786	High Similarity	NPC254819
0.8777	High Similarity	NPC229784
0.8777	High Similarity	NPC477294
0.8777	High Similarity	NPC477293
0.8767	High Similarity	NPC186296
0.875	High Similarity	NPC321638
0.875	High Similarity	NPC321184
0.875	High Similarity	NPC171134
0.875	High Similarity	NPC328273
0.8732	High Similarity	NPC287597
0.8732	High Similarity	NPC886
0.8732	High Similarity	NPC34293
0.8723	High Similarity	NPC473285
0.8718	High Similarity	NPC206815
0.8718	High Similarity	NPC476011
0.8716	High Similarity	NPC37838
0.8705	High Similarity	NPC232880
0.8667	High Similarity	NPC478236
0.8645	High Similarity	NPC179914
0.8636	High Similarity	NPC475378
0.8633	High Similarity	NPC175333
0.8633	High Similarity	NPC476873
0.8609	High Similarity	NPC117346
0.8609	High Similarity	NPC69367
0.8609	High Similarity	NPC240592
0.8601	High Similarity	NPC471883
0.8571	High Similarity	NPC296643
0.8562	High Similarity	NPC229354
0.8552	High Similarity	NPC78363
0.8552	High Similarity	NPC260425
0.8552	High Similarity	NPC476376
0.8544	High Similarity	NPC109990
0.8543	High Similarity	NPC96599
0.8543	High Similarity	NPC478234
0.8514	High Similarity	NPC105005
0.8514	High Similarity	NPC40305
0.8506	High Similarity	NPC478232
0.8503	High Similarity	NPC186406
0.85	High Similarity	NPC208818
0.8497	Intermediate Similarity	NPC203664
0.8493	Intermediate Similarity	NPC68092
0.8493	Intermediate Similarity	NPC197316
0.8493	Intermediate Similarity	NPC89105
0.8493	Intermediate Similarity	NPC226005
0.8493	Intermediate Similarity	NPC476383
0.8493	Intermediate Similarity	NPC472350
0.8493	Intermediate Similarity	NPC64141
0.8493	Intermediate Similarity	NPC81515
0.8493	Intermediate Similarity	NPC205195
0.8483	Intermediate Similarity	NPC470572
0.8483	Intermediate Similarity	NPC157554
0.8481	Intermediate Similarity	NPC145847
0.8471	Intermediate Similarity	NPC474936
0.8462	Intermediate Similarity	NPC187205
0.8456	Intermediate Similarity	NPC110063
0.8456	Intermediate Similarity	NPC296659
0.8456	Intermediate Similarity	NPC202391
0.8456	Intermediate Similarity	NPC296954
0.8456	Intermediate Similarity	NPC300894
0.8456	Intermediate Similarity	NPC141455
0.8456	Intermediate Similarity	NPC196063
0.8446	Intermediate Similarity	NPC140502
0.8435	Intermediate Similarity	NPC202700
0.8431	Intermediate Similarity	NPC158546
0.8431	Intermediate Similarity	NPC289021
0.8429	Intermediate Similarity	NPC267733
0.8429	Intermediate Similarity	NPC276047
0.8389	Intermediate Similarity	NPC478239
0.8378	Intermediate Similarity	NPC134405
0.8378	Intermediate Similarity	NPC47471
0.8378	Intermediate Similarity	NPC476377
0.8378	Intermediate Similarity	NPC476385
0.8367	Intermediate Similarity	NPC100389
0.8367	Intermediate Similarity	NPC220936
0.8367	Intermediate Similarity	NPC31745
0.8367	Intermediate Similarity	NPC220942
0.8357	Intermediate Similarity	NPC83218
0.8357	Intermediate Similarity	NPC126991
0.8356	Intermediate Similarity	NPC186418
0.8345	Intermediate Similarity	NPC224208
0.8345	Intermediate Similarity	NPC474275
0.8344	Intermediate Similarity	NPC229505
0.8333	Intermediate Similarity	NPC232228
0.8333	Intermediate Similarity	NPC292443
0.8333	Intermediate Similarity	NPC21956
0.8322	Intermediate Similarity	NPC265648
0.8322	Intermediate Similarity	NPC222433
0.8322	Intermediate Similarity	NPC157816
0.8311	Intermediate Similarity	NPC475530
0.8311	Intermediate Similarity	NPC473799
0.8298	Intermediate Similarity	NPC252114
0.8298	Intermediate Similarity	NPC471157
0.8286	Intermediate Similarity	NPC145287
0.8278	Intermediate Similarity	NPC287615
0.8278	Intermediate Similarity	NPC100998
0.8278	Intermediate Similarity	NPC476382
0.8278	Intermediate Similarity	NPC83743
0.8278	Intermediate Similarity	NPC252292
0.8278	Intermediate Similarity	NPC34587
0.8278	Intermediate Similarity	NPC262182
0.8278	Intermediate Similarity	NPC216819
0.8278	Intermediate Similarity	NPC34927
0.8273	Intermediate Similarity	NPC52097
0.8272	Intermediate Similarity	NPC286809
0.8267	Intermediate Similarity	NPC269141
0.8267	Intermediate Similarity	NPC119537
0.8267	Intermediate Similarity	NPC112
0.8267	Intermediate Similarity	NPC476384
0.8267	Intermediate Similarity	NPC298257
0.8267	Intermediate Similarity	NPC96795
0.8267	Intermediate Similarity	NPC247032
0.8267	Intermediate Similarity	NPC264632
0.8267	Intermediate Similarity	NPC476378
0.8267	Intermediate Similarity	NPC76406
0.8267	Intermediate Similarity	NPC476375
0.8267	Intermediate Similarity	NPC205864
0.8267	Intermediate Similarity	NPC476397
0.8267	Intermediate Similarity	NPC476381
0.8267	Intermediate Similarity	NPC175214
0.8267	Intermediate Similarity	NPC476380
0.8264	Intermediate Similarity	NPC478255
0.8258	Intermediate Similarity	NPC478235
0.8258	Intermediate Similarity	NPC478268
0.8252	Intermediate Similarity	NPC253595
0.8247	Intermediate Similarity	NPC188393
0.8247	Intermediate Similarity	NPC470934
0.8239	Intermediate Similarity	NPC288416
0.8239	Intermediate Similarity	NPC106677
0.8235	Intermediate Similarity	NPC23677
0.8231	Intermediate Similarity	NPC472132
0.8231	Intermediate Similarity	NPC37468
0.8228	Intermediate Similarity	NPC475663
0.8228	Intermediate Similarity	NPC286919
0.8227	Intermediate Similarity	NPC90318
0.8224	Intermediate Similarity	NPC473867
0.8224	Intermediate Similarity	NPC199928
0.8212	Intermediate Similarity	NPC77922
0.8212	Intermediate Similarity	NPC297342
0.8212	Intermediate Similarity	NPC473281
0.8212	Intermediate Similarity	NPC64195
0.8212	Intermediate Similarity	NPC476867
0.821	Intermediate Similarity	NPC282551
0.8201	Intermediate Similarity	NPC11724
0.8194	Intermediate Similarity	NPC475379
0.8182	Intermediate Similarity	NPC225307
0.8182	Intermediate Similarity	NPC478242
0.8176	Intermediate Similarity	NPC469384
0.817	Intermediate Similarity	NPC232992
0.817	Intermediate Similarity	NPC41844
0.8158	Intermediate Similarity	NPC476866
0.8158	Intermediate Similarity	NPC476868
0.8158	Intermediate Similarity	NPC476864
0.8158	Intermediate Similarity	NPC475528
0.8158	Intermediate Similarity	NPC476869
0.8151	Intermediate Similarity	NPC6836
0.8146	Intermediate Similarity	NPC293154
0.8129	Intermediate Similarity	NPC12006
0.8129	Intermediate Similarity	NPC476872
0.8117	Intermediate Similarity	NPC192763
0.8117	Intermediate Similarity	NPC215095
0.8117	Intermediate Similarity	NPC261122
0.8117	Intermediate Similarity	NPC199311
0.8117	Intermediate Similarity	NPC28651
0.8117	Intermediate Similarity	NPC300262
0.8117	Intermediate Similarity	NPC80732

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 NPC18789 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	796
0.2-0.3	1956
0.3-0.4	2979
0.4-0.5	1910
0.5-0.6	1045
0.6-0.7	175
0.7-0.8	11
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8634	High Similarity	NPD7685	Pre-registration
0.8493	Intermediate Similarity	NPD7266	Discontinued
0.8065	Intermediate Similarity	NPD1653	Approved
0.7677	Intermediate Similarity	NPD6190	Approved
0.7273	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7228	Approved
0.7209	Intermediate Similarity	NPD3818	Discontinued
0.7202	Intermediate Similarity	NPD6234	Discontinued
0.7161	Intermediate Similarity	NPD6653	Approved
0.7133	Intermediate Similarity	NPD3094	Phase 2
0.7118	Intermediate Similarity	NPD7199	Phase 2
0.7108	Intermediate Similarity	NPD37	Approved
0.7102	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1091	Approved
0.7083	Intermediate Similarity	NPD4967	Phase 2
0.7083	Intermediate Similarity	NPD4965	Approved
0.7083	Intermediate Similarity	NPD4966	Approved
0.7069	Intermediate Similarity	NPD7054	Approved
0.7059	Intermediate Similarity	NPD3027	Phase 3
0.7037	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1613	Approved
0.7032	Intermediate Similarity	NPD3620	Phase 2
0.7032	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7472	Approved
0.6989	Remote Similarity	NPD6797	Phase 2
0.6987	Remote Similarity	NPD230	Phase 1
0.6982	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5762	Approved
0.6981	Remote Similarity	NPD5763	Approved
0.698	Remote Similarity	NPD3705	Approved
0.6949	Remote Similarity	NPD7251	Discontinued
0.6941	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7074	Phase 3
0.6928	Remote Similarity	NPD2861	Phase 2
0.6919	Remote Similarity	NPD8127	Discontinued
0.6894	Remote Similarity	NPD6674	Discontinued
0.6892	Remote Similarity	NPD1357	Approved
0.6887	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7028	Phase 2
0.6867	Remote Similarity	NPD3092	Approved
0.6852	Remote Similarity	NPD8166	Discontinued
0.6818	Remote Similarity	NPD5736	Approved
0.6816	Remote Similarity	NPD7808	Phase 3
0.6815	Remote Similarity	NPD4140	Approved
0.6774	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD8455	Phase 2
0.676	Remote Similarity	NPD6559	Discontinued
0.676	Remote Similarity	NPD7240	Approved
0.6753	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.671	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.669	Remote Similarity	NPD969	Suspended
0.6687	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1652	Phase 2
0.6685	Remote Similarity	NPD8312	Approved
0.6685	Remote Similarity	NPD8313	Approved
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD3021	Approved
0.6667	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5735	Approved
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD5124	Phase 1
0.6667	Remote Similarity	NPD6004	Phase 3
0.6667	Remote Similarity	NPD3022	Approved
0.6647	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6663	Approved
0.6646	Remote Similarity	NPD4628	Phase 3
0.6629	Remote Similarity	NPD3751	Discontinued
0.6611	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD1934	Approved
0.6604	Remote Similarity	NPD4060	Phase 1
0.66	Remote Similarity	NPD3091	Approved
0.6588	Remote Similarity	NPD4380	Phase 2
0.6584	Remote Similarity	NPD7097	Phase 1
0.6582	Remote Similarity	NPD3764	Approved
0.6581	Remote Similarity	NPD6362	Approved
0.6575	Remote Similarity	NPD228	Approved
0.657	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5058	Phase 3
0.6564	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4340	Discontinued
0.6548	Remote Similarity	NPD6273	Approved
0.6545	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4110	Phase 3
0.6538	Remote Similarity	NPD5647	Approved
0.6536	Remote Similarity	NPD7799	Discontinued
0.6532	Remote Similarity	NPD3817	Phase 2
0.6528	Remote Similarity	NPD1358	Approved
0.6524	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6166	Phase 2
0.6513	Remote Similarity	NPD5125	Phase 3
0.6513	Remote Similarity	NPD5126	Approved
0.6505	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5844	Phase 1
0.6497	Remote Similarity	NPD3787	Discontinued
0.6494	Remote Similarity	NPD9269	Phase 2
0.6492	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.649	Remote Similarity	NPD9545	Approved
0.6488	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2977	Approved
0.6474	Remote Similarity	NPD1465	Phase 2
0.6474	Remote Similarity	NPD2978	Approved
0.6474	Remote Similarity	NPD2801	Approved
0.646	Remote Similarity	NPD6355	Discontinued
0.6458	Remote Similarity	NPD3134	Approved
0.6448	Remote Similarity	NPD7549	Discontinued
0.6446	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD7680	Approved
0.6442	Remote Similarity	NPD7033	Discontinued
0.6437	Remote Similarity	NPD5402	Approved
0.6433	Remote Similarity	NPD3455	Phase 2
0.6429	Remote Similarity	NPD422	Phase 1
0.6429	Remote Similarity	NPD1511	Approved
0.6424	Remote Similarity	NPD5536	Phase 2
0.6415	Remote Similarity	NPD7095	Approved
0.6405	Remote Similarity	NPD3095	Discontinued
0.64	Remote Similarity	NPD3882	Suspended
0.6392	Remote Similarity	NPD9494	Approved
0.6391	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD5283	Phase 1
0.6374	Remote Similarity	NPD3687	Approved
0.6374	Remote Similarity	NPD3686	Approved
0.6368	Remote Similarity	NPD7930	Approved
0.6364	Remote Similarity	NPD3496	Discontinued
0.6364	Remote Similarity	NPD6841	Approved
0.6364	Remote Similarity	NPD7075	Discontinued
0.6364	Remote Similarity	NPD6843	Phase 3
0.6364	Remote Similarity	NPD6842	Approved
0.6364	Remote Similarity	NPD1375	Discontinued
0.6353	Remote Similarity	NPD1512	Approved
0.6352	Remote Similarity	NPD4908	Phase 1
0.6347	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.634	Remote Similarity	NPD7503	Approved
0.6335	Remote Similarity	NPD6233	Phase 2
0.6329	Remote Similarity	NPD4624	Approved
0.6325	Remote Similarity	NPD2424	Discontinued
0.6325	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD1610	Phase 2
0.6319	Remote Similarity	NPD6353	Approved
0.6319	Remote Similarity	NPD2492	Phase 1
0.6316	Remote Similarity	NPD5403	Approved
0.6313	Remote Similarity	NPD6232	Discontinued
0.6303	Remote Similarity	NPD9570	Approved
0.6299	Remote Similarity	NPD4626	Approved
0.6299	Remote Similarity	NPD9384	Approved
0.6299	Remote Similarity	NPD4059	Approved
0.6299	Remote Similarity	NPD9381	Approved
0.6298	Remote Similarity	NPD7473	Discontinued
0.6294	Remote Similarity	NPD7999	Approved
0.6291	Remote Similarity	NPD7157	Approved
0.6287	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7741	Discontinued
0.6273	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD3657	Discovery
0.6258	Remote Similarity	NPD447	Suspended
0.6258	Remote Similarity	NPD1933	Approved
0.625	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5353	Approved
0.625	Remote Similarity	NPD3750	Approved
0.6243	Remote Similarity	NPD7458	Discontinued
0.6242	Remote Similarity	NPD2983	Phase 2
0.6242	Remote Similarity	NPD5588	Approved
0.6242	Remote Similarity	NPD4749	Approved
0.6242	Remote Similarity	NPD5327	Phase 3
0.6242	Remote Similarity	NPD2982	Phase 2
0.6242	Remote Similarity	NPD5960	Phase 3
0.6242	Remote Similarity	NPD4108	Discontinued
0.6235	Remote Similarity	NPD4357	Discontinued
0.6234	Remote Similarity	NPD5691	Approved
0.6234	Remote Similarity	NPD9268	Approved
0.6234	Remote Similarity	NPD5585	Approved
0.6233	Remote Similarity	NPD6685	Approved
0.6229	Remote Similarity	NPD6801	Discontinued
0.6223	Remote Similarity	NPD8150	Discontinued
0.6205	Remote Similarity	NPD2935	Discontinued
0.6203	Remote Similarity	NPD3225	Approved
0.6201	Remote Similarity	NPD5494	Approved
0.62	Remote Similarity	NPD7843	Approved
0.6199	Remote Similarity	NPD5401	Approved
0.6199	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD826	Approved
0.6196	Remote Similarity	NPD3062	Approved
0.6196	Remote Similarity	NPD3061	Approved
0.6196	Remote Similarity	NPD3059	Approved
0.6196	Remote Similarity	NPD825	Approved
0.6193	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD7819	Suspended
0.6193	Remote Similarity	NPD7435	Discontinued
0.6193	Remote Similarity	NPD7497	Discontinued
0.6193	Remote Similarity	NPD5563	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