NPASS Compound

Structure

CID23219 OpenBabel06191715352D 26 30 0 0 1 0 0 0 0 0999 V2000 -5.5718 2.1547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3472 -0.1900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8017 -1.3895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1231 0.7904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9413 1.2485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4979 -2.9489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3003 -3.4113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9207 -1.5501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3770 0.8468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1107 -0.1473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4931 -2.0132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9166 -0.6268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1131 -2.0164 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7472 0.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2959 -1.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3032 -0.6135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7348 -0.1687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6880 -1.5460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4917 -0.1568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6889 -0.6203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1031 -2.9478 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5595 1.2238 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5349 -0.6448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1137 -2.0089 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2989 0.7499 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 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 21 1 0 0 0 0 8 12 1 0 0 0 0 9 25 1 0 0 0 0 9 26 1 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 13 8 1 6 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 17 2 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 16 19 2 0 0 0 0 17 23 1 0 0 0 0 18 20 2 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	355.14
Volume:	350.823
LogP:	2.238
LogD:	2.284
LogS:	-1.975
# Rotatable Bonds:	3
TPSA:	58.18
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.914
Synthetic Accessibility Score:	3.408
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.011
MDCK Permeability:	2.053241041721776e-05
Pgp-inhibitor:	0.324
Pgp-substrate:	0.122
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.877
Plasma Protein Binding (PPB):	88.42620849609375%
Volume Distribution (VD):	1.608
Pgp-substrate:	6.60769510269165%

ADMET: Metabolism

CYP1A2-inhibitor:	0.408
CYP1A2-substrate:	0.941
CYP2C19-inhibitor:	0.357
CYP2C19-substrate:	0.88
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.868
CYP2D6-inhibitor:	0.309
CYP2D6-substrate:	0.922
CYP3A4-inhibitor:	0.644
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	4.342
Half-life (T1/2):	0.193

ADMET: Toxicity

hERG Blockers:	0.553
Human Hepatotoxicity (H-HT):	0.235
Drug-inuced Liver Injury (DILI):	0.072
AMES Toxicity:	0.283
Rat Oral Acute Toxicity:	0.587
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.125
Carcinogencity:	0.097
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.915

Download Data

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

Natural Product: NPC23219

Natural Product ID:	NPC23219
*Common Name:**	Desmorostratine
IUPAC Name:	n.a.
Synonyms:	Desmorostratine
Standard InCHIKey:	CUYKKCDYAVFQQG-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C20H21NO5/c1-22-14-5-4-10-12(17(14)23-2)8-13-15-11(6-7-21-13)18(24-3)20-19(16(10)15)25-9-26-20/h4-5,13,21H,6-9H2,1-3H3/t13-/m1/s1
SMILES:	COc1c(OC)ccc2c1C[C@H]1NCCc3c1c2c1OCOc1c3OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456407
PubChem CID:	25147609
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO32522	desmos rostrata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053513]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	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	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2400.0	nM	PMID[549956]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3600.0	nM	PMID[549956]

☑ 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 NPC23219 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	408
0.1-0.2	1972
0.2-0.3	9654
0.3-0.4	8602
0.4-0.5	6938
0.5-0.6	11310
0.6-0.7	3002
0.7-0.8	567
0.8-0.85	160
0.85-0.9	54
0.9-0.95	24
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC32413
0.9877	High Similarity	NPC474506
0.9816	High Similarity	NPC470879
0.9816	High Similarity	NPC258695
0.9815	High Similarity	NPC112575
0.9568	High Similarity	NPC6152
0.9524	High Similarity	NPC57036
0.9509	High Similarity	NPC19520
0.9509	High Similarity	NPC149090
0.9467	High Similarity	NPC186546
0.9467	High Similarity	NPC476576
0.9444	High Similarity	NPC204947
0.9383	High Similarity	NPC86144
0.9383	High Similarity	NPC304659
0.9302	High Similarity	NPC117717
0.9264	High Similarity	NPC24264
0.9264	High Similarity	NPC476432
0.9259	High Similarity	NPC189470
0.9226	High Similarity	NPC267408
0.9207	High Similarity	NPC247389
0.9202	High Similarity	NPC16805
0.9202	High Similarity	NPC302527
0.9202	High Similarity	NPC225774
0.9202	High Similarity	NPC167546
0.9176	High Similarity	NPC135772
0.9172	High Similarity	NPC155442
0.9172	High Similarity	NPC477561
0.9172	High Similarity	NPC312918
0.9172	High Similarity	NPC476574
0.9162	High Similarity	NPC477558
0.9146	High Similarity	NPC219341
0.9112	High Similarity	NPC474507
0.9091	High Similarity	NPC210918
0.9018	High Similarity	NPC306902
0.9018	High Similarity	NPC232924
0.9018	High Similarity	NPC477559
0.9018	High Similarity	NPC266753
0.9018	High Similarity	NPC160298
0.8994	High Similarity	NPC476577
0.8994	High Similarity	NPC173416
0.8994	High Similarity	NPC148709
0.8982	High Similarity	NPC152212
0.896	High Similarity	NPC214116
0.8951	High Similarity	NPC203784
0.8951	High Similarity	NPC126519
0.8951	High Similarity	NPC170503
0.8895	High Similarity	NPC476575
0.8857	High Similarity	NPC82763
0.883	High Similarity	NPC114364
0.883	High Similarity	NPC320223
0.8824	High Similarity	NPC199465
0.8824	High Similarity	NPC128560
0.8824	High Similarity	NPC229166
0.8807	High Similarity	NPC475754
0.8786	High Similarity	NPC275132
0.878	High Similarity	NPC476572
0.8773	High Similarity	NPC325871
0.8773	High Similarity	NPC99659
0.8765	High Similarity	NPC66341
0.8765	High Similarity	NPC192135
0.8765	High Similarity	NPC477020
0.8757	High Similarity	NPC26240
0.8757	High Similarity	NPC69712
0.8757	High Similarity	NPC477562
0.875	High Similarity	NPC281581
0.875	High Similarity	NPC298979
0.8727	High Similarity	NPC7393
0.8706	High Similarity	NPC239775
0.8703	High Similarity	NPC46990
0.8698	High Similarity	NPC241055
0.8678	High Similarity	NPC248642
0.8671	High Similarity	NPC126284
0.8647	High Similarity	NPC168753
0.8647	High Similarity	NPC118274
0.8631	High Similarity	NPC168409
0.8629	High Similarity	NPC156576
0.8589	High Similarity	NPC326316
0.8589	High Similarity	NPC81733
0.858	High Similarity	NPC81247
0.858	High Similarity	NPC35627
0.858	High Similarity	NPC476573
0.8571	High Similarity	NPC116284
0.8545	High Similarity	NPC244112
0.8537	High Similarity	NPC114124
0.8506	High Similarity	NPC294790
0.8506	High Similarity	NPC148693
0.8506	High Similarity	NPC118633
0.8483	Intermediate Similarity	NPC237579
0.8471	Intermediate Similarity	NPC223077
0.8471	Intermediate Similarity	NPC56887
0.8471	Intermediate Similarity	NPC193853
0.8466	Intermediate Similarity	NPC73492
0.8466	Intermediate Similarity	NPC299990
0.8434	Intermediate Similarity	NPC138487
0.8434	Intermediate Similarity	NPC216459
0.8434	Intermediate Similarity	NPC41178
0.843	Intermediate Similarity	NPC75958
0.8421	Intermediate Similarity	NPC117188
0.8421	Intermediate Similarity	NPC205421
0.8421	Intermediate Similarity	NPC12053
0.8421	Intermediate Similarity	NPC81218
0.8421	Intermediate Similarity	NPC474931
0.8421	Intermediate Similarity	NPC158376
0.8421	Intermediate Similarity	NPC306555
0.8421	Intermediate Similarity	NPC145832
0.8418	Intermediate Similarity	NPC302275
0.8412	Intermediate Similarity	NPC477563
0.8412	Intermediate Similarity	NPC196447
0.8412	Intermediate Similarity	NPC96603
0.8412	Intermediate Similarity	NPC78222
0.8412	Intermediate Similarity	NPC212794
0.8412	Intermediate Similarity	NPC13504
0.8412	Intermediate Similarity	NPC209377
0.8412	Intermediate Similarity	NPC306843
0.8412	Intermediate Similarity	NPC253043
0.8412	Intermediate Similarity	NPC136508
0.8405	Intermediate Similarity	NPC475959
0.8383	Intermediate Similarity	NPC146288
0.8353	Intermediate Similarity	NPC324144
0.8352	Intermediate Similarity	NPC475479
0.8352	Intermediate Similarity	NPC243454
0.8323	Intermediate Similarity	NPC123323
0.8305	Intermediate Similarity	NPC239584
0.8293	Intermediate Similarity	NPC59907
0.8293	Intermediate Similarity	NPC37144
0.8289	Intermediate Similarity	NPC244606
0.8289	Intermediate Similarity	NPC156728
0.8278	Intermediate Similarity	NPC312531
0.8274	Intermediate Similarity	NPC234392
0.8274	Intermediate Similarity	NPC31311
0.8246	Intermediate Similarity	NPC1229
0.8242	Intermediate Similarity	NPC211296
0.8235	Intermediate Similarity	NPC166014
0.8235	Intermediate Similarity	NPC27410
0.8222	Intermediate Similarity	NPC14507
0.8222	Intermediate Similarity	NPC47077
0.8216	Intermediate Similarity	NPC212163
0.8214	Intermediate Similarity	NPC76079
0.8204	Intermediate Similarity	NPC210148
0.8204	Intermediate Similarity	NPC233029
0.8202	Intermediate Similarity	NPC179704
0.8198	Intermediate Similarity	NPC180306
0.8197	Intermediate Similarity	NPC256124
0.8187	Intermediate Similarity	NPC475597
0.8187	Intermediate Similarity	NPC473716
0.8182	Intermediate Similarity	NPC130941
0.8182	Intermediate Similarity	NPC329969
0.8176	Intermediate Similarity	NPC477080
0.815	Intermediate Similarity	NPC264850
0.815	Intermediate Similarity	NPC195392
0.815	Intermediate Similarity	NPC13916
0.815	Intermediate Similarity	NPC68328
0.8146	Intermediate Similarity	NPC244554
0.8146	Intermediate Similarity	NPC220961
0.8142	Intermediate Similarity	NPC478093
0.8142	Intermediate Similarity	NPC24260
0.8136	Intermediate Similarity	NPC287588
0.8133	Intermediate Similarity	NPC219162
0.8129	Intermediate Similarity	NPC119649
0.8129	Intermediate Similarity	NPC235143
0.8129	Intermediate Similarity	NPC230956
0.8129	Intermediate Similarity	NPC205255
0.8129	Intermediate Similarity	NPC271388
0.8128	Intermediate Similarity	NPC295676
0.8125	Intermediate Similarity	NPC2314
0.8118	Intermediate Similarity	NPC79328
0.8107	Intermediate Similarity	NPC93593
0.8098	Intermediate Similarity	NPC478092
0.8098	Intermediate Similarity	NPC30182
0.8098	Intermediate Similarity	NPC478091
0.8098	Intermediate Similarity	NPC473589
0.8092	Intermediate Similarity	NPC238530
0.8092	Intermediate Similarity	NPC24465
0.8092	Intermediate Similarity	NPC232514
0.8092	Intermediate Similarity	NPC276944
0.8081	Intermediate Similarity	NPC79402
0.8081	Intermediate Similarity	NPC80759
0.807	Intermediate Similarity	NPC221864
0.8068	Intermediate Similarity	NPC63646
0.8068	Intermediate Similarity	NPC10908
0.8068	Intermediate Similarity	NPC65403
0.8068	Intermediate Similarity	NPC317439
0.8068	Intermediate Similarity	NPC76682
0.8068	Intermediate Similarity	NPC115284
0.8068	Intermediate Similarity	NPC198498
0.8068	Intermediate Similarity	NPC317145
0.8068	Intermediate Similarity	NPC276890
0.8068	Intermediate Similarity	NPC227060
0.8066	Intermediate Similarity	NPC9867
0.8056	Intermediate Similarity	NPC249405
0.8043	Intermediate Similarity	NPC302001
0.8033	Intermediate Similarity	NPC48490
0.8033	Intermediate Similarity	NPC82457
0.8033	Intermediate Similarity	NPC175890
0.8033	Intermediate Similarity	NPC274661
0.8033	Intermediate Similarity	NPC11296
0.8024	Intermediate Similarity	NPC207824
0.8024	Intermediate Similarity	NPC60538
0.8023	Intermediate Similarity	NPC251580
0.8023	Intermediate Similarity	NPC41376

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 NPC23219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	783
0.2-0.3	1158
0.3-0.4	2315
0.4-0.5	2672
0.5-0.6	1423
0.6-0.7	487
0.7-0.8	92
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8068	Intermediate Similarity	NPD8099	Discontinued
0.8068	Intermediate Similarity	NPD8251	Approved
0.8068	Intermediate Similarity	NPD8252	Approved
0.8023	Intermediate Similarity	NPD8156	Discontinued
0.8012	Intermediate Similarity	NPD4584	Approved
0.7975	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD6788	Approved
0.7904	Intermediate Similarity	NPD1424	Approved
0.7895	Intermediate Similarity	NPD7298	Approved
0.7853	Intermediate Similarity	NPD4481	Phase 3
0.7845	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD3051	Approved
0.7811	Intermediate Similarity	NPD6030	Approved
0.7811	Intermediate Similarity	NPD4727	Phase 1
0.7811	Intermediate Similarity	NPD6031	Approved
0.776	Intermediate Similarity	NPD8054	Approved
0.776	Intermediate Similarity	NPD8053	Approved
0.7725	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2969	Approved
0.7697	Intermediate Similarity	NPD2970	Approved
0.7634	Intermediate Similarity	NPD7906	Approved
0.7626	Intermediate Similarity	NPD7827	Phase 1
0.7617	Intermediate Similarity	NPD5006	Approved
0.7617	Intermediate Similarity	NPD5005	Approved
0.7593	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3383	Approved
0.7586	Intermediate Similarity	NPD3382	Approved
0.7586	Intermediate Similarity	NPD3384	Approved
0.7557	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD27	Approved
0.7556	Intermediate Similarity	NPD2489	Approved
0.7543	Intermediate Similarity	NPD2977	Approved
0.7543	Intermediate Similarity	NPD2978	Approved
0.7543	Intermediate Similarity	NPD4585	Approved
0.7529	Intermediate Similarity	NPD2421	Approved
0.7529	Intermediate Similarity	NPD2420	Approved
0.7514	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4578	Approved
0.7514	Intermediate Similarity	NPD4577	Approved
0.7514	Intermediate Similarity	NPD4055	Discovery
0.75	Intermediate Similarity	NPD4420	Approved
0.75	Intermediate Similarity	NPD5976	Discontinued
0.7487	Intermediate Similarity	NPD4663	Approved
0.7471	Intermediate Similarity	NPD3845	Phase 1
0.7471	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7313	Approved
0.7419	Intermediate Similarity	NPD7310	Approved
0.7419	Intermediate Similarity	NPD7311	Approved
0.7419	Intermediate Similarity	NPD7312	Approved
0.7419	Intermediate Similarity	NPD2968	Approved
0.7419	Intermediate Similarity	NPD2971	Approved
0.7414	Intermediate Similarity	NPD4017	Approved
0.7412	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7309	Approved
0.7337	Intermediate Similarity	NPD4859	Phase 1
0.7333	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6723	Discontinued
0.7293	Intermediate Similarity	NPD6107	Approved
0.7282	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8095	Phase 1
0.7268	Intermediate Similarity	NPD2973	Approved
0.7268	Intermediate Similarity	NPD2974	Approved
0.7268	Intermediate Similarity	NPD2975	Approved
0.7267	Intermediate Similarity	NPD7124	Phase 2
0.7258	Intermediate Similarity	NPD6297	Approved
0.7253	Intermediate Similarity	NPD6071	Discontinued
0.7253	Intermediate Similarity	NPD4166	Phase 2
0.7247	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3110	Approved
0.7229	Intermediate Similarity	NPD3109	Approved
0.7225	Intermediate Similarity	NPD7598	Phase 2
0.7209	Intermediate Similarity	NPD5241	Discontinued
0.7207	Intermediate Similarity	NPD2563	Approved
0.7207	Intermediate Similarity	NPD2560	Approved
0.72	Intermediate Similarity	NPD3639	Approved
0.72	Intermediate Similarity	NPD3640	Phase 3
0.72	Intermediate Similarity	NPD3641	Approved
0.7196	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2898	Approved
0.7166	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4580	Approved
0.7143	Intermediate Similarity	NPD5677	Discontinued
0.7127	Intermediate Similarity	NPD7833	Phase 2
0.7127	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7831	Phase 2
0.7121	Intermediate Similarity	NPD2494	Approved
0.7121	Intermediate Similarity	NPD2493	Approved
0.7121	Intermediate Similarity	NPD3452	Approved
0.7121	Intermediate Similarity	NPD3450	Approved
0.7119	Intermediate Similarity	NPD4005	Discontinued
0.7105	Intermediate Similarity	NPD6851	Approved
0.7105	Intermediate Similarity	NPD6853	Approved
0.7098	Intermediate Similarity	NPD2488	Approved
0.7098	Intermediate Similarity	NPD2490	Approved
0.7093	Intermediate Similarity	NPD3060	Approved
0.7052	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD5754	Discontinued
0.7048	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4773	Phase 2
0.7039	Intermediate Similarity	NPD4772	Phase 2
0.7033	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4582	Approved
0.7015	Intermediate Similarity	NPD4583	Approved
0.7011	Intermediate Similarity	NPD5160	Discontinued
0.7011	Intermediate Similarity	NPD7802	Discontinued
0.7006	Intermediate Similarity	NPD5718	Phase 2
0.7	Intermediate Similarity	NPD3515	Approved
0.7	Intermediate Similarity	NPD3516	Approved
0.6995	Remote Similarity	NPD3349	Phase 2
0.6995	Remote Similarity	NPD5709	Phase 3
0.6985	Remote Similarity	NPD5457	Discontinued
0.6973	Remote Similarity	NPD4010	Discontinued
0.6968	Remote Similarity	NPD42	Phase 2
0.6968	Remote Similarity	NPD6042	Phase 2
0.6965	Remote Similarity	NPD4002	Approved
0.6965	Remote Similarity	NPD4004	Approved
0.6964	Remote Similarity	NPD8153	Approved
0.6964	Remote Similarity	NPD8152	Approved
0.6959	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4666	Phase 3
0.694	Remote Similarity	NPD5604	Discontinued
0.6936	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6625	Approved
0.6905	Remote Similarity	NPD3763	Approved
0.6902	Remote Similarity	NPD7400	Phase 3
0.69	Remote Similarity	NPD4107	Approved
0.6897	Remote Similarity	NPD4162	Approved
0.6875	Remote Similarity	NPD7280	Phase 3
0.6875	Remote Similarity	NPD7281	Phase 3
0.6875	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD6037	Discontinued
0.6864	Remote Similarity	NPD4475	Approved
0.6864	Remote Similarity	NPD4474	Approved
0.6862	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4108	Discontinued
0.6857	Remote Similarity	NPD7466	Approved
0.6854	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD5090	Approved
0.6851	Remote Similarity	NPD5089	Approved
0.6847	Remote Similarity	NPD4040	Phase 1
0.6842	Remote Similarity	NPD7047	Phase 3
0.6839	Remote Similarity	NPD6618	Phase 2
0.6836	Remote Similarity	NPD3124	Discontinued
0.6825	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5708	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7549	Discontinued
0.6816	Remote Similarity	NPD6612	Phase 2
0.6813	Remote Similarity	NPD37	Approved
0.6813	Remote Similarity	NPD5720	Discontinued
0.6808	Remote Similarity	NPD6997	Phase 2
0.6802	Remote Similarity	NPD6896	Approved
0.6802	Remote Similarity	NPD2200	Suspended
0.6802	Remote Similarity	NPD6111	Discontinued
0.6802	Remote Similarity	NPD6895	Approved
0.68	Remote Similarity	NPD5177	Phase 3
0.6788	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4482	Phase 3
0.6755	Remote Similarity	NPD5242	Approved
0.6754	Remote Similarity	NPD7479	Phase 2
0.6744	Remote Similarity	NPD2492	Phase 1
0.6744	Remote Similarity	NPD2653	Approved
0.6743	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5297	Approved
0.674	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5977	Approved
0.6739	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5978	Approved
0.6735	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD3454	Phase 3
0.6723	Remote Similarity	NPD2677	Approved
0.6705	Remote Similarity	NPD4236	Phase 3
0.6705	Remote Similarity	NPD4237	Approved
0.6704	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7447	Phase 1
0.6703	Remote Similarity	NPD4965	Approved
0.6703	Remote Similarity	NPD4678	Approved
0.6703	Remote Similarity	NPD4967	Phase 2
0.6703	Remote Similarity	NPD4675	Approved
0.6703	Remote Similarity	NPD4966	Approved
0.6702	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5312	Approved
0.6702	Remote Similarity	NPD5313	Approved
0.6702	Remote Similarity	NPD4873	Discontinued
0.67	Remote Similarity	NPD5582	Discontinued
0.6699	Remote Similarity	NPD3815	Phase 1
0.6699	Remote Similarity	NPD3816	Phase 1
0.6686	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2120	Phase 2
0.6684	Remote Similarity	NPD3489	Phase 3
0.6682	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6687	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