NPASS Compound

Structure

NPC473147 OpenBabel07101719512D 40 44 0 0 1 0 0 0 0 0999 V2000 4.5983 1.7682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0934 -0.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9683 -3.0036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4260 0.1353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2920 -1.3647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2920 0.6353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1580 -0.8647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0366 0.1325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5600 -1.3647 0.0000 C 0 0 0 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3036 0.8126 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 4.1506 -2.4280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4260 -0.8647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1580 0.1353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 0.6636 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 4.9619 -0.8647 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 6.6939 -0.8647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -0.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1356 -1.4281 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 -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 3.1801 -1.1333 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2043 -2.7512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 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 11.0241 0.6353 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6939 0.1353 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 2.9095 -3.7067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8279 -1.3647 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6045 -1.9510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 3 14 2 0 0 0 0 4 6 1 0 0 0 0 4 15 2 0 0 0 0 5 7 2 0 0 0 0 5 15 1 0 0 0 0 6 16 2 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 8 19 1 0 0 0 0 9 15 1 0 0 0 0 9 21 1 0 0 0 0 10 18 1 0 0 0 0 11 30 1 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 14 28 1 0 0 0 0 16 31 1 0 0 0 0 17 10 1 1 0 0 0 17 22 1 0 0 0 0 18 38 1 0 0 0 0 19 23 1 0 0 0 0 19 37 1 1 0 0 0 20 11 1 6 0 0 0 20 24 1 0 0 0 0 20 39 1 0 0 0 0 21 32 2 0 0 0 0 21 37 1 0 0 0 0 22 13 1 1 0 0 0 22 27 1 0 0 0 0 23 14 1 1 0 0 0 23 27 1 0 0 0 0 24 25 1 0 0 0 0 24 33 1 1 0 0 0 25 26 1 0 0 0 0 25 34 1 6 0 0 0 26 29 1 0 0 0 0 26 35 1 1 0 0 0 27 40 1 6 0 0 0 28 36 2 0 0 0 0 28 40 1 0 0 0 0 29 38 1 6 0 0 0 29 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	558.21
Volume:	542.959
LogP:	-0.029
LogD:	1.273
LogS:	-2.598
# Rotatable Bonds:	7
TPSA:	172.21
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.188
Synthetic Accessibility Score:	5.108
Fsp3:	0.517
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.233
MDCK Permeability:	4.98567933391314e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.077
Human Intestinal Absorption (HIA):	0.9
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	77.2568588256836%
Volume Distribution (VD):	0.352
Pgp-substrate:	18.569744110107422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.023
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.111
CYP2C9-inhibitor:	0.086
CYP2C9-substrate:	0.098
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.334
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	2.022
Half-life (T1/2):	0.871

ADMET: Toxicity

hERG Blockers:	0.163
Human Hepatotoxicity (H-HT):	0.949
Drug-inuced Liver Injury (DILI):	0.939
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.536
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.082
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC473147

Natural Product ID:	NPC473147
*Common Name:**	LQIMVHNPYMFGPH-ROXCMIAGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LQIMVHNPYMFGPH-ROXCMIAGSA-N
Standard InCHI:	InChI=1S/C29H34O11/c1-12-8-19(37-21(32)9-15-4-6-16(31)7-5-15)23-14(3)28(36)40-27(23)22-13(2)18(10-17(12)22)38-29-26(35)25(34)24(33)20(11-30)39-29/h4-7,17,19-20,22-27,29-31,33-35H,1,3,8-11H2,2H3/t17-,19+,20+,22-,23+,24+,25-,26+,27+,29+/m0/s1
SMILES:	OC[C@H]1O[C@@H](OC2=C(C)[C@H]3[C@@H](C2)C(=C)C[C@H]([C@@H]2[C@@H]3OC(=O)C2=C)OC(=O)Cc2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3622757
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides 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
NPO32813	ixeris dentata	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[26341134]

☑ 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
Others	4

Activity Type	# Activity
NON-MOLECULAR	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	18.2	uM	PMID[463439]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	9.3	uM	PMID[463439]
NPT27	Others	Unspecified		Activity	=	105.7	%	PMID[463439]
NPT27	Others	Unspecified		Activity	=	102.7	%	PMID[463439]

☑ 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 NPC473147 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	295
0.1-0.2	1046
0.2-0.3	2489
0.3-0.4	5119
0.4-0.5	10177
0.5-0.6	9407
0.6-0.7	11276
0.7-0.8	2746
0.8-0.85	108
0.85-0.9	28
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9571	High Similarity	NPC194938
0.931	High Similarity	NPC35097
0.9306	High Similarity	NPC120728
0.9161	High Similarity	NPC296659
0.9161	High Similarity	NPC202391
0.898	High Similarity	NPC96599
0.8944	High Similarity	NPC31745
0.8944	High Similarity	NPC220936
0.8919	High Similarity	NPC240592
0.8919	High Similarity	NPC117346
0.8828	High Similarity	NPC186296
0.8776	High Similarity	NPC143246
0.8776	High Similarity	NPC474268
0.8776	High Similarity	NPC119773
0.8776	High Similarity	NPC475539
0.8767	High Similarity	NPC77922
0.8767	High Similarity	NPC473281
0.8767	High Similarity	NPC251062
0.8767	High Similarity	NPC184464
0.8733	High Similarity	NPC289021
0.8733	High Similarity	NPC158546
0.8707	High Similarity	NPC210330
0.8707	High Similarity	NPC475528
0.8699	High Similarity	NPC293154
0.8699	High Similarity	NPC475213
0.8699	High Similarity	NPC152796
0.869	High Similarity	NPC154262
0.869	High Similarity	NPC137501
0.869	High Similarity	NPC159387
0.869	High Similarity	NPC7518
0.8662	High Similarity	NPC169398
0.8639	High Similarity	NPC63304
0.8627	High Similarity	NPC475484
0.8618	High Similarity	NPC257847
0.8609	High Similarity	NPC474620
0.8609	High Similarity	NPC475379
0.8591	High Similarity	NPC473149
0.8582	High Similarity	NPC281798
0.8582	High Similarity	NPC254819
0.8571	High Similarity	NPC475378
0.8553	High Similarity	NPC478235
0.8523	High Similarity	NPC212808
0.8483	Intermediate Similarity	NPC101686
0.8483	Intermediate Similarity	NPC65262
0.8483	Intermediate Similarity	NPC469364
0.8477	Intermediate Similarity	NPC161955
0.8477	Intermediate Similarity	NPC478236
0.8477	Intermediate Similarity	NPC478234
0.8446	Intermediate Similarity	NPC478250
0.8431	Intermediate Similarity	NPC203664
0.8429	Intermediate Similarity	NPC173150
0.8429	Intermediate Similarity	NPC471882
0.8429	Intermediate Similarity	NPC35288
0.8429	Intermediate Similarity	NPC45224
0.8429	Intermediate Similarity	NPC471881
0.8429	Intermediate Similarity	NPC156692
0.8421	Intermediate Similarity	NPC69367
0.8414	Intermediate Similarity	NPC471345
0.8411	Intermediate Similarity	NPC189631
0.8408	Intermediate Similarity	NPC130489
0.8408	Intermediate Similarity	NPC208676
0.8378	Intermediate Similarity	NPC296643
0.8377	Intermediate Similarity	NPC299706
0.8377	Intermediate Similarity	NPC115466
0.8377	Intermediate Similarity	NPC61604
0.8377	Intermediate Similarity	NPC245615
0.8377	Intermediate Similarity	NPC229354
0.8357	Intermediate Similarity	NPC61181
0.8344	Intermediate Similarity	NPC179914
0.8333	Intermediate Similarity	NPC114116
0.8322	Intermediate Similarity	NPC478255
0.8312	Intermediate Similarity	NPC194705
0.8302	Intermediate Similarity	NPC145847
0.8301	Intermediate Similarity	NPC229882
0.8301	Intermediate Similarity	NPC158635
0.8299	Intermediate Similarity	NPC220942
0.8299	Intermediate Similarity	NPC49597
0.8298	Intermediate Similarity	NPC103533
0.8278	Intermediate Similarity	NPC320734
0.8278	Intermediate Similarity	NPC473867
0.8269	Intermediate Similarity	NPC38699
0.8264	Intermediate Similarity	NPC471095
0.8264	Intermediate Similarity	NPC471066
0.825	Intermediate Similarity	NPC109990
0.8239	Intermediate Similarity	NPC225307
0.8228	Intermediate Similarity	NPC76211
0.8228	Intermediate Similarity	NPC469384
0.8217	Intermediate Similarity	NPC478055
0.8217	Intermediate Similarity	NPC163635
0.8207	Intermediate Similarity	NPC164172
0.8201	Intermediate Similarity	NPC52097
0.82	Intermediate Similarity	NPC242756
0.8194	Intermediate Similarity	NPC235294
0.8194	Intermediate Similarity	NPC46137
0.8188	Intermediate Similarity	NPC46644
0.8182	Intermediate Similarity	NPC267469
0.8182	Intermediate Similarity	NPC87630
0.8182	Intermediate Similarity	NPC179128
0.8182	Intermediate Similarity	NPC116292
0.8182	Intermediate Similarity	NPC469549
0.8176	Intermediate Similarity	NPC324262
0.8176	Intermediate Similarity	NPC62800
0.8169	Intermediate Similarity	NPC288416
0.8169	Intermediate Similarity	NPC106677
0.8165	Intermediate Similarity	NPC187205
0.8165	Intermediate Similarity	NPC49173
0.8165	Intermediate Similarity	NPC4747
0.8165	Intermediate Similarity	NPC475663
0.8165	Intermediate Similarity	NPC226759
0.8165	Intermediate Similarity	NPC104275
0.8165	Intermediate Similarity	NPC286919
0.8163	Intermediate Similarity	NPC472132
0.8163	Intermediate Similarity	NPC470572
0.8158	Intermediate Similarity	NPC208293
0.8151	Intermediate Similarity	NPC471883
0.8129	Intermediate Similarity	NPC11724
0.8125	Intermediate Similarity	NPC469705
0.8125	Intermediate Similarity	NPC17968
0.8125	Intermediate Similarity	NPC117943
0.8125	Intermediate Similarity	NPC470122
0.8125	Intermediate Similarity	NPC477627
0.8125	Intermediate Similarity	NPC293568
0.8117	Intermediate Similarity	NPC478242
0.8116	Intermediate Similarity	NPC469702
0.8116	Intermediate Similarity	NPC282409
0.8108	Intermediate Similarity	NPC469696
0.8101	Intermediate Similarity	NPC228357
0.8099	Intermediate Similarity	NPC471157
0.8095	Intermediate Similarity	NPC123988
0.8089	Intermediate Similarity	NPC478232
0.8086	Intermediate Similarity	NPC180586
0.8082	Intermediate Similarity	NPC136608
0.8082	Intermediate Similarity	NPC254398
0.8082	Intermediate Similarity	NPC38420
0.8079	Intermediate Similarity	NPC263397
0.8079	Intermediate Similarity	NPC302286
0.8079	Intermediate Similarity	NPC116104
0.8079	Intermediate Similarity	NPC237872
0.8079	Intermediate Similarity	NPC89317
0.8079	Intermediate Similarity	NPC88754
0.8079	Intermediate Similarity	NPC204644
0.8075	Intermediate Similarity	NPC476011
0.8069	Intermediate Similarity	NPC138777
0.8069	Intermediate Similarity	NPC246869
0.8069	Intermediate Similarity	NPC219677
0.8069	Intermediate Similarity	NPC225384
0.8065	Intermediate Similarity	NPC104172
0.8065	Intermediate Similarity	NPC12006
0.8065	Intermediate Similarity	NPC88886
0.8065	Intermediate Similarity	NPC35160
0.8065	Intermediate Similarity	NPC162569
0.8063	Intermediate Similarity	NPC138993
0.8063	Intermediate Similarity	NPC474936
0.8058	Intermediate Similarity	NPC476448
0.8058	Intermediate Similarity	NPC476872
0.8058	Intermediate Similarity	NPC469548
0.8058	Intermediate Similarity	NPC476445
0.8054	Intermediate Similarity	NPC171134
0.8054	Intermediate Similarity	NPC321184
0.8054	Intermediate Similarity	NPC321638
0.8054	Intermediate Similarity	NPC328273
0.8052	Intermediate Similarity	NPC473428
0.8052	Intermediate Similarity	NPC23677
0.805	Intermediate Similarity	NPC329997
0.8049	Intermediate Similarity	NPC21956
0.8039	Intermediate Similarity	NPC3982
0.8039	Intermediate Similarity	NPC291153
0.8038	Intermediate Similarity	NPC172920
0.8038	Intermediate Similarity	NPC156624
0.8038	Intermediate Similarity	NPC186316
0.8037	Intermediate Similarity	NPC469396
0.8037	Intermediate Similarity	NPC469458
0.8037	Intermediate Similarity	NPC149002
0.8037	Intermediate Similarity	NPC88176
0.8037	Intermediate Similarity	NPC469419
0.8037	Intermediate Similarity	NPC469459
0.8028	Intermediate Similarity	NPC123704
0.8028	Intermediate Similarity	NPC126991
0.8028	Intermediate Similarity	NPC83218
0.8026	Intermediate Similarity	NPC471028
0.8014	Intermediate Similarity	NPC473924
0.8013	Intermediate Similarity	NPC52664
0.8013	Intermediate Similarity	NPC469623
0.8013	Intermediate Similarity	NPC477700
0.8013	Intermediate Similarity	NPC148080
0.7987	Intermediate Similarity	NPC475195
0.7987	Intermediate Similarity	NPC470330
0.7987	Intermediate Similarity	NPC84789
0.7987	Intermediate Similarity	NPC310252
0.7987	Intermediate Similarity	NPC302583
0.7987	Intermediate Similarity	NPC100558
0.7986	Intermediate Similarity	NPC158673
0.7975	Intermediate Similarity	NPC136757
0.7975	Intermediate Similarity	NPC265600
0.7973	Intermediate Similarity	NPC263829
0.7972	Intermediate Similarity	NPC252114
0.7962	Intermediate Similarity	NPC478268
0.7962	Intermediate Similarity	NPC56184
0.7961	Intermediate Similarity	NPC469367
0.7961	Intermediate Similarity	NPC40305

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 NPC473147 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	696
0.2-0.3	1538
0.3-0.4	2655
0.4-0.5	2336
0.5-0.6	1201
0.6-0.7	444
0.7-0.8	39
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
0.7933	Intermediate Similarity	NPD7266	Discontinued
0.7824	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7685	Pre-registration
0.7771	Intermediate Similarity	NPD7228	Approved
0.7669	Intermediate Similarity	NPD6234	Discontinued
0.7654	Intermediate Similarity	NPD4965	Approved
0.7654	Intermediate Similarity	NPD4967	Phase 2
0.7654	Intermediate Similarity	NPD4966	Approved
0.764	Intermediate Similarity	NPD8455	Phase 2
0.7578	Intermediate Similarity	NPD37	Approved
0.7548	Intermediate Similarity	NPD4628	Phase 3
0.7533	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7199	Phase 2
0.74	Intermediate Similarity	NPD3764	Approved
0.7389	Intermediate Similarity	NPD6190	Approved
0.7384	Intermediate Similarity	NPD6559	Discontinued
0.7384	Intermediate Similarity	NPD7240	Approved
0.7368	Intermediate Similarity	NPD6355	Discontinued
0.7365	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6004	Phase 3
0.7355	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6002	Phase 3
0.7355	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6005	Phase 3
0.7353	Intermediate Similarity	NPD3818	Discontinued
0.7299	Intermediate Similarity	NPD8312	Approved
0.7299	Intermediate Similarity	NPD8313	Approved
0.7278	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD9545	Approved
0.7215	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6653	Approved
0.7186	Intermediate Similarity	NPD7075	Discontinued
0.7168	Intermediate Similarity	NPD7074	Phase 3
0.7161	Intermediate Similarity	NPD7097	Phase 1
0.7143	Intermediate Similarity	NPD1091	Approved
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7134	Intermediate Similarity	NPD4380	Phase 2
0.7133	Intermediate Similarity	NPD5647	Approved
0.7126	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6663	Approved
0.7117	Intermediate Similarity	NPD1653	Approved
0.7111	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7054	Approved
0.7073	Intermediate Similarity	NPD7458	Discontinued
0.7069	Intermediate Similarity	NPD7472	Approved
0.7059	Intermediate Similarity	NPD8127	Discontinued
0.7055	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6233	Phase 2
0.7006	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8166	Discontinued
0.6989	Remote Similarity	NPD7251	Discontinued
0.6974	Remote Similarity	NPD5736	Approved
0.6973	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7799	Discontinued
0.6949	Remote Similarity	NPD7808	Phase 3
0.6948	Remote Similarity	NPD6798	Discontinued
0.6948	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6797	Phase 2
0.6918	Remote Similarity	NPD5762	Approved
0.6918	Remote Similarity	NPD5763	Approved
0.6915	Remote Similarity	NPD7680	Approved
0.6899	Remote Similarity	NPD2799	Discontinued
0.6894	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5125	Phase 3
0.6892	Remote Similarity	NPD5126	Approved
0.6883	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2424	Discontinued
0.6872	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1608	Approved
0.6855	Remote Similarity	NPD2438	Suspended
0.6855	Remote Similarity	NPD2935	Discontinued
0.6853	Remote Similarity	NPD969	Suspended
0.6845	Remote Similarity	NPD6801	Discontinued
0.6842	Remote Similarity	NPD6362	Approved
0.6836	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7296	Approved
0.6829	Remote Similarity	NPD2533	Approved
0.6829	Remote Similarity	NPD2534	Approved
0.6829	Remote Similarity	NPD2532	Approved
0.6828	Remote Similarity	NPD2629	Approved
0.6826	Remote Similarity	NPD7028	Phase 2
0.6821	Remote Similarity	NPD7930	Approved
0.6813	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5058	Phase 3
0.6805	Remote Similarity	NPD7819	Suspended
0.68	Remote Similarity	NPD3705	Approved
0.6796	Remote Similarity	NPD8434	Phase 2
0.6795	Remote Similarity	NPD4062	Phase 3
0.6792	Remote Similarity	NPD7033	Discontinued
0.679	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4110	Phase 3
0.679	Remote Similarity	NPD3750	Approved
0.6788	Remote Similarity	NPD6273	Approved
0.6786	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD7157	Approved
0.6774	Remote Similarity	NPD3027	Phase 3
0.677	Remote Similarity	NPD970	Clinical (unspecified phase)
0.677	Remote Similarity	NPD5958	Discontinued
0.6768	Remote Similarity	NPD6799	Approved
0.6765	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5402	Approved
0.6754	Remote Similarity	NPD7999	Approved
0.6753	Remote Similarity	NPD2861	Phase 2
0.6752	Remote Similarity	NPD4060	Phase 1
0.6747	Remote Similarity	NPD5403	Approved
0.6746	Remote Similarity	NPD1934	Approved
0.6737	Remote Similarity	NPD7435	Discontinued
0.6732	Remote Similarity	NPD2797	Approved
0.6728	Remote Similarity	NPD6674	Discontinued
0.6726	Remote Similarity	NPD6599	Discontinued
0.6725	Remote Similarity	NPD7768	Phase 2
0.6725	Remote Similarity	NPD3882	Suspended
0.6723	Remote Similarity	NPD5844	Phase 1
0.6713	Remote Similarity	NPD2067	Discontinued
0.6712	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7473	Discontinued
0.6703	Remote Similarity	NPD8150	Discontinued
0.6702	Remote Similarity	NPD8319	Approved
0.6702	Remote Similarity	NPD8320	Phase 1
0.669	Remote Similarity	NPD7843	Approved
0.6686	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD4534	Discontinued
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6166	Phase 2
0.6646	Remote Similarity	NPD2979	Phase 3
0.6645	Remote Similarity	NPD1481	Phase 2
0.6643	Remote Similarity	NPD6647	Phase 2
0.6629	Remote Similarity	NPD6232	Discontinued
0.6629	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5401	Approved
0.6626	Remote Similarity	NPD1652	Phase 2
0.6624	Remote Similarity	NPD3268	Approved
0.6623	Remote Similarity	NPD3094	Phase 2
0.6622	Remote Similarity	NPD9493	Approved
0.662	Remote Similarity	NPD6685	Approved
0.6609	Remote Similarity	NPD5494	Approved
0.6608	Remote Similarity	NPD5761	Phase 2
0.6608	Remote Similarity	NPD5760	Phase 2
0.6608	Remote Similarity	NPD1465	Phase 2
0.6605	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5124	Phase 1
0.6603	Remote Similarity	NPD6832	Phase 2
0.6603	Remote Similarity	NPD4908	Phase 1
0.66	Remote Similarity	NPD1357	Approved
0.6597	Remote Similarity	NPD6823	Phase 2
0.659	Remote Similarity	NPD3749	Approved
0.6585	Remote Similarity	NPD3400	Discontinued
0.6584	Remote Similarity	NPD1510	Phase 2
0.6581	Remote Similarity	NPD2798	Approved
0.6579	Remote Similarity	NPD1535	Discovery
0.6579	Remote Similarity	NPD6781	Approved
0.6579	Remote Similarity	NPD6780	Approved
0.6579	Remote Similarity	NPD6779	Approved
0.6579	Remote Similarity	NPD6782	Approved
0.6579	Remote Similarity	NPD6778	Approved
0.6579	Remote Similarity	NPD6776	Approved
0.6579	Remote Similarity	NPD6777	Approved
0.6578	Remote Similarity	NPD6535	Approved
0.6578	Remote Similarity	NPD6534	Approved
0.6573	Remote Similarity	NPD1358	Approved
0.6573	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3751	Discontinued
0.657	Remote Similarity	NPD5353	Approved
0.657	Remote Similarity	NPD3817	Phase 2
0.6568	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD3455	Phase 2
0.6564	Remote Similarity	NPD8151	Discontinued
0.6561	Remote Similarity	NPD7700	Phase 2
0.6561	Remote Similarity	NPD7699	Phase 2
0.6556	Remote Similarity	NPD3019	Approved
0.6556	Remote Similarity	NPD2932	Approved
0.6554	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD1551	Phase 2
0.6543	Remote Similarity	NPD4476	Approved
0.6543	Remote Similarity	NPD4477	Approved
0.6541	Remote Similarity	NPD4140	Approved
0.6541	Remote Similarity	NPD1613	Approved
0.6541	Remote Similarity	NPD1240	Approved
0.6541	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD9494	Approved
0.6536	Remote Similarity	NPD9269	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