NPASS Compound

Structure

CID276674 OpenBabel06191716082D 21 24 0 0 0 0 0 0 0 0999 V2000 1.6877 -3.8337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1394 1.4277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4944 -2.4445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5121 -1.4770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6476 -2.9128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6831 -0.9779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4993 -1.4333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5034 -2.3889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0068 -2.8895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6561 0.0099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8187 -2.4137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6631 -0.9506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 -1.4463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8376 -2.4041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8259 0.4825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 -1.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0056 -0.9609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6775 -2.8714 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8380 0.4721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8158 1.4377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 11 2 0 0 0 0 6 13 2 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 14 2 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 18 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	279.13
Volume:	295.78
LogP:	4.77
LogD:	3.499
LogS:	-5.886
# Rotatable Bonds:	1
TPSA:	32.7
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.689
Synthetic Accessibility Score:	2.441
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.78
MDCK Permeability:	1.9295019228593446e-05
Pgp-inhibitor:	0.133
Pgp-substrate:	0.961
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.126

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.545
Plasma Protein Binding (PPB):	94.2786865234375%
Volume Distribution (VD):	0.722
Pgp-substrate:	2.6404027938842773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.945
CYP2C19-inhibitor:	0.822
CYP2C19-substrate:	0.528
CYP2C9-inhibitor:	0.462
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.702
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.291
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	7.007
Half-life (T1/2):	0.367

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.907
AMES Toxicity:	0.812
Rat Oral Acute Toxicity:	0.181
Maximum Recommended Daily Dose:	0.757
Skin Sensitization:	0.952
Carcinogencity:	0.857
Eye Corrosion:	0.047
Eye Irritation:	0.942
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC276674

Natural Product ID:	NPC276674
*Common Name:**	Dehydrolirinidine
IUPAC Name:	n.a.
Synonyms:	Dehydrolirinidine
Standard InCHIKey:	MHVZRDIFMMTICK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H17NO2/c1-19-8-7-12-10-15(21-2)18(20)17-13-6-4-3-5-11(13)9-14(19)16(12)17/h3-6,9-10,20H,7-8H2,1-2H3
SMILES:	CN1CCc2cc(c(c3c4ccccc4cc1c23)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464773
PubChem CID:	10423732
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]
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	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	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]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[9599253]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868142]
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]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO11053	Annona purpurea	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]
NPO11053	Annona purpurea	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]
NPO11053	Annona purpurea	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
Others	7

Activity Type	# Activity
CELL-LINE	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	86.3	%	PMID[493501]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	0.0	%	PMID[493501]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	51.7	%	PMID[493501]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	23.8	%	PMID[493501]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	77.6	%	PMID[493501]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	82.8	%	PMID[493501]

☑ 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 NPC276674 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	424
0.1-0.2	2370
0.2-0.3	12098
0.3-0.4	5423
0.4-0.5	8260
0.5-0.6	11309
0.6-0.7	2168
0.7-0.8	507
0.8-0.85	111
0.85-0.9	19
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC33902
0.9762	High Similarity	NPC320088
0.9576	High Similarity	NPC285941
0.936	High Similarity	NPC474904
0.929	High Similarity	NPC190461
0.9128	High Similarity	NPC249405
0.9091	High Similarity	NPC78284
0.8994	High Similarity	NPC17677
0.892	High Similarity	NPC312531
0.8916	High Similarity	NPC166014
0.8916	High Similarity	NPC27410
0.8851	High Similarity	NPC179704
0.8786	High Similarity	NPC287588
0.8743	High Similarity	NPC471489
0.8698	High Similarity	NPC324144
0.8674	High Similarity	NPC162653
0.8655	High Similarity	NPC117188
0.8655	High Similarity	NPC205421
0.8655	High Similarity	NPC474931
0.8655	High Similarity	NPC12053
0.8655	High Similarity	NPC306555
0.8655	High Similarity	NPC145832
0.8655	High Similarity	NPC81218
0.8655	High Similarity	NPC158376
0.8647	High Similarity	NPC477563
0.8647	High Similarity	NPC96603
0.8647	High Similarity	NPC253043
0.8647	High Similarity	NPC212794
0.8647	High Similarity	NPC306843
0.8647	High Similarity	NPC78222
0.8647	High Similarity	NPC13504
0.8647	High Similarity	NPC196447
0.8647	High Similarity	NPC136508
0.8596	High Similarity	NPC476573
0.8596	High Similarity	NPC81247
0.8596	High Similarity	NPC35627
0.8588	High Similarity	NPC1229
0.8547	High Similarity	NPC477186
0.8529	High Similarity	NPC60186
0.8494	Intermediate Similarity	NPC326316
0.8494	Intermediate Similarity	NPC81733
0.8475	Intermediate Similarity	NPC311936
0.8466	Intermediate Similarity	NPC100573
0.8466	Intermediate Similarity	NPC207873
0.8462	Intermediate Similarity	NPC302001
0.8448	Intermediate Similarity	NPC168753
0.8448	Intermediate Similarity	NPC118274
0.8439	Intermediate Similarity	NPC298979
0.8427	Intermediate Similarity	NPC119579
0.84	Intermediate Similarity	NPC239775
0.838	Intermediate Similarity	NPC28425
0.8352	Intermediate Similarity	NPC192135
0.8352	Intermediate Similarity	NPC477020
0.8352	Intermediate Similarity	NPC66341
0.8343	Intermediate Similarity	NPC26240
0.8343	Intermediate Similarity	NPC69712
0.8343	Intermediate Similarity	NPC477562
0.8333	Intermediate Similarity	NPC212163
0.8315	Intermediate Similarity	NPC114364
0.8315	Intermediate Similarity	NPC320223
0.8314	Intermediate Similarity	NPC24954
0.8305	Intermediate Similarity	NPC229166
0.8305	Intermediate Similarity	NPC128560
0.8305	Intermediate Similarity	NPC199465
0.8294	Intermediate Similarity	NPC186063
0.8289	Intermediate Similarity	NPC25897
0.828	Intermediate Similarity	NPC193906
0.828	Intermediate Similarity	NPC23080
0.8268	Intermediate Similarity	NPC192939
0.8268	Intermediate Similarity	NPC215747
0.8263	Intermediate Similarity	NPC477565
0.8263	Intermediate Similarity	NPC103379
0.8258	Intermediate Similarity	NPC265383
0.8253	Intermediate Similarity	NPC179825
0.8253	Intermediate Similarity	NPC321505
0.8253	Intermediate Similarity	NPC191376
0.8246	Intermediate Similarity	NPC476572
0.8245	Intermediate Similarity	NPC295676
0.8235	Intermediate Similarity	NPC172765
0.8235	Intermediate Similarity	NPC184026
0.8235	Intermediate Similarity	NPC189266
0.8235	Intermediate Similarity	NPC207757
0.8235	Intermediate Similarity	NPC204828
0.8235	Intermediate Similarity	NPC110416
0.8235	Intermediate Similarity	NPC295691
0.8235	Intermediate Similarity	NPC469817
0.8235	Intermediate Similarity	NPC54379
0.8235	Intermediate Similarity	NPC278799
0.8235	Intermediate Similarity	NPC99659
0.8235	Intermediate Similarity	NPC2413
0.8235	Intermediate Similarity	NPC127674
0.8235	Intermediate Similarity	NPC276588
0.8235	Intermediate Similarity	NPC193949
0.8235	Intermediate Similarity	NPC5238
0.8235	Intermediate Similarity	NPC39701
0.8235	Intermediate Similarity	NPC325871
0.8235	Intermediate Similarity	NPC249797
0.8229	Intermediate Similarity	NPC210140
0.8225	Intermediate Similarity	NPC26601
0.8212	Intermediate Similarity	NPC260118
0.8205	Intermediate Similarity	NPC298449
0.8204	Intermediate Similarity	NPC147390
0.8204	Intermediate Similarity	NPC24233
0.8204	Intermediate Similarity	NPC246587
0.8204	Intermediate Similarity	NPC428
0.8204	Intermediate Similarity	NPC476571
0.8204	Intermediate Similarity	NPC135538
0.8187	Intermediate Similarity	NPC170503
0.8187	Intermediate Similarity	NPC126519
0.8187	Intermediate Similarity	NPC203784
0.8177	Intermediate Similarity	NPC90185
0.8167	Intermediate Similarity	NPC474507
0.8156	Intermediate Similarity	NPC476577
0.8156	Intermediate Similarity	NPC173416
0.8156	Intermediate Similarity	NPC148709
0.815	Intermediate Similarity	NPC477559
0.815	Intermediate Similarity	NPC160298
0.815	Intermediate Similarity	NPC232924
0.815	Intermediate Similarity	NPC306902
0.815	Intermediate Similarity	NPC266753
0.8144	Intermediate Similarity	NPC476151
0.8142	Intermediate Similarity	NPC22928
0.8133	Intermediate Similarity	NPC185838
0.8125	Intermediate Similarity	NPC308943
0.8115	Intermediate Similarity	NPC244606
0.8115	Intermediate Similarity	NPC156728
0.8114	Intermediate Similarity	NPC134858
0.8107	Intermediate Similarity	NPC88249
0.8107	Intermediate Similarity	NPC192768
0.8107	Intermediate Similarity	NPC220858
0.8107	Intermediate Similarity	NPC151895
0.8107	Intermediate Similarity	NPC97221
0.8087	Intermediate Similarity	NPC180253
0.8087	Intermediate Similarity	NPC219170
0.8077	Intermediate Similarity	NPC116284
0.8057	Intermediate Similarity	NPC233650
0.8047	Intermediate Similarity	NPC92541
0.8047	Intermediate Similarity	NPC219162
0.8045	Intermediate Similarity	NPC477187
0.8034	Intermediate Similarity	NPC152212
0.8033	Intermediate Similarity	NPC135772
0.8022	Intermediate Similarity	NPC477561
0.8022	Intermediate Similarity	NPC155442
0.8022	Intermediate Similarity	NPC476574
0.8022	Intermediate Similarity	NPC312918
0.8011	Intermediate Similarity	NPC225774
0.7978	Intermediate Similarity	NPC276060
0.7968	Intermediate Similarity	NPC478093
0.7967	Intermediate Similarity	NPC126284
0.7966	Intermediate Similarity	NPC476432
0.7966	Intermediate Similarity	NPC24264
0.7966	Intermediate Similarity	NPC219341
0.7965	Intermediate Similarity	NPC2295
0.7965	Intermediate Similarity	NPC477564
0.7953	Intermediate Similarity	NPC76213
0.7953	Intermediate Similarity	NPC277669
0.7929	Intermediate Similarity	NPC144863
0.7929	Intermediate Similarity	NPC95075
0.7929	Intermediate Similarity	NPC253883
0.7929	Intermediate Similarity	NPC90844
0.7926	Intermediate Similarity	NPC30182
0.7926	Intermediate Similarity	NPC473589
0.7926	Intermediate Similarity	NPC478091
0.7926	Intermediate Similarity	NPC478092
0.7921	Intermediate Similarity	NPC150879
0.7921	Intermediate Similarity	NPC247389
0.7919	Intermediate Similarity	NPC244112
0.7914	Intermediate Similarity	NPC79213
0.7914	Intermediate Similarity	NPC294244
0.791	Intermediate Similarity	NPC167546
0.791	Intermediate Similarity	NPC238530
0.791	Intermediate Similarity	NPC16805
0.791	Intermediate Similarity	NPC302527
0.791	Intermediate Similarity	NPC232514
0.791	Intermediate Similarity	NPC276944
0.7903	Intermediate Similarity	NPC112676
0.7903	Intermediate Similarity	NPC296742
0.7901	Intermediate Similarity	NPC477558
0.7892	Intermediate Similarity	NPC470925
0.7892	Intermediate Similarity	NPC69213
0.7886	Intermediate Similarity	NPC221864
0.7882	Intermediate Similarity	NPC130941
0.788	Intermediate Similarity	NPC248642
0.7877	Intermediate Similarity	NPC241055
0.7877	Intermediate Similarity	NPC477185
0.7865	Intermediate Similarity	NPC317272
0.7865	Intermediate Similarity	NPC86144
0.7865	Intermediate Similarity	NPC240841
0.7865	Intermediate Similarity	NPC42549
0.7865	Intermediate Similarity	NPC268503
0.7865	Intermediate Similarity	NPC250846
0.7865	Intermediate Similarity	NPC13916
0.7865	Intermediate Similarity	NPC304659
0.7865	Intermediate Similarity	NPC264850
0.7865	Intermediate Similarity	NPC256012
0.7861	Intermediate Similarity	NPC82763
0.7849	Intermediate Similarity	NPC224293
0.7846	Intermediate Similarity	NPC222561
0.7841	Intermediate Similarity	NPC205255
0.7841	Intermediate Similarity	NPC271388

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 NPC276674 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	811
0.2-0.3	1046
0.3-0.4	1426
0.4-0.5	2724
0.5-0.6	2150
0.6-0.7	674
0.7-0.8	76
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8202	Intermediate Similarity	NPD7479	Phase 2
0.8193	Intermediate Similarity	NPD2421	Approved
0.8193	Intermediate Similarity	NPD2420	Approved
0.8162	Intermediate Similarity	NPD7262	Phase 1
0.7933	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD4584	Approved
0.7784	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2489	Approved
0.7778	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD27	Approved
0.7766	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD5938	Phase 3
0.773	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD2898	Approved
0.7667	Intermediate Similarity	NPD3051	Approved
0.7647	Intermediate Similarity	NPD3301	Approved
0.7624	Intermediate Similarity	NPD2969	Approved
0.7624	Intermediate Similarity	NPD4083	Discontinued
0.7624	Intermediate Similarity	NPD2970	Approved
0.7602	Intermediate Similarity	NPD3845	Phase 1
0.7594	Intermediate Similarity	NPD8053	Approved
0.7594	Intermediate Similarity	NPD8054	Approved
0.7565	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5241	Discontinued
0.7542	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7833	Phase 2
0.7542	Intermediate Similarity	NPD7831	Phase 2
0.7525	Intermediate Similarity	NPD5530	Phase 1
0.7514	Intermediate Similarity	NPD3920	Phase 2
0.75	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7906	Approved
0.7473	Intermediate Similarity	NPD4010	Discontinued
0.7459	Intermediate Similarity	NPD6037	Discontinued
0.7447	Intermediate Similarity	NPD4577	Approved
0.7447	Intermediate Similarity	NPD4578	Approved
0.7432	Intermediate Similarity	NPD3975	Discontinued
0.7429	Intermediate Similarity	NPD6030	Approved
0.7429	Intermediate Similarity	NPD6031	Approved
0.7427	Intermediate Similarity	NPD3763	Approved
0.7389	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD3398	Discontinued
0.738	Intermediate Similarity	NPD6496	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD5810	Discontinued
0.7366	Intermediate Similarity	NPD8149	Discontinued
0.7363	Intermediate Similarity	NPD4859	Phase 1
0.736	Intermediate Similarity	NPD6612	Phase 2
0.7358	Intermediate Similarity	NPD3924	Approved
0.7358	Intermediate Similarity	NPD3922	Approved
0.7358	Intermediate Similarity	NPD3923	Approved
0.7358	Intermediate Similarity	NPD3921	Approved
0.7354	Intermediate Similarity	NPD7311	Approved
0.7354	Intermediate Similarity	NPD7310	Approved
0.7354	Intermediate Similarity	NPD7313	Approved
0.7354	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD7312	Approved
0.7351	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD4017	Approved
0.7345	Intermediate Similarity	NPD6357	Discontinued
0.7336	Intermediate Similarity	NPD7922	Phase 1
0.733	Intermediate Similarity	NPD4663	Approved
0.7326	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7309	Approved
0.7314	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD2490	Approved
0.7306	Intermediate Similarity	NPD5641	Discontinued
0.7306	Intermediate Similarity	NPD2488	Approved
0.7273	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD4773	Phase 2
0.7263	Intermediate Similarity	NPD4772	Phase 2
0.7254	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4986	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7298	Approved
0.7219	Intermediate Similarity	NPD8099	Discontinued
0.7219	Intermediate Similarity	NPD8251	Approved
0.7219	Intermediate Similarity	NPD8252	Approved
0.7208	Intermediate Similarity	NPD6284	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6527	Approved
0.7208	Intermediate Similarity	NPD7034	Discontinued
0.7198	Intermediate Similarity	NPD6788	Approved
0.7193	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8156	Discontinued
0.716	Intermediate Similarity	NPD3110	Approved
0.716	Intermediate Similarity	NPD3109	Approved
0.7157	Intermediate Similarity	NPD5582	Discontinued
0.7143	Intermediate Similarity	NPD7222	Phase 2
0.7143	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD3815	Phase 1
0.7136	Intermediate Similarity	NPD3816	Phase 1
0.7136	Intermediate Similarity	NPD7225	Discontinued
0.7135	Intermediate Similarity	NPD3640	Phase 3
0.7135	Intermediate Similarity	NPD3641	Approved
0.7135	Intermediate Similarity	NPD3639	Approved
0.7128	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3515	Approved
0.7114	Intermediate Similarity	NPD3516	Approved
0.7112	Intermediate Similarity	NPD4481	Phase 3
0.7111	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6723	Discontinued
0.7097	Intermediate Similarity	NPD6071	Discontinued
0.709	Intermediate Similarity	NPD5600	Discontinued
0.7088	Intermediate Similarity	NPD6737	Phase 2
0.7088	Intermediate Similarity	NPD6738	Phase 2
0.7085	Intermediate Similarity	NPD5071	Phase 2
0.7065	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7263	Phase 2
0.7056	Intermediate Similarity	NPD6526	Approved
0.7056	Intermediate Similarity	NPD6046	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2560	Approved
0.7049	Intermediate Similarity	NPD2563	Approved
0.7049	Intermediate Similarity	NPD6063	Approved
0.7045	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD3983	Phase 3
0.7043	Intermediate Similarity	NPD7802	Discontinued
0.7043	Intermediate Similarity	NPD3984	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5718	Phase 2
0.7029	Intermediate Similarity	NPD5177	Phase 3
0.7024	Intermediate Similarity	NPD5658	Approved
0.702	Intermediate Similarity	NPD7686	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6494	Phase 2
0.7017	Intermediate Similarity	NPD5617	Suspended
0.7016	Intermediate Similarity	NPD6211	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2674	Phase 3
0.7	Intermediate Similarity	NPD2883	Discontinued
0.6995	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6090	Discontinued
0.6982	Remote Similarity	NPD5155	Approved
0.6982	Remote Similarity	NPD5156	Approved
0.698	Remote Similarity	NPD2493	Approved
0.698	Remote Similarity	NPD3452	Approved
0.698	Remote Similarity	NPD3450	Approved
0.698	Remote Similarity	NPD2494	Approved
0.6979	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4951	Discontinued
0.6968	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.694	Remote Similarity	NPD3784	Discontinued
0.6936	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3595	Approved
0.6923	Remote Similarity	NPD3594	Approved
0.6923	Remote Similarity	NPD2606	Approved
0.6923	Remote Similarity	NPD6340	Approved
0.6923	Remote Similarity	NPD2605	Approved
0.6923	Remote Similarity	NPD6339	Approved
0.6923	Remote Similarity	NPD4502	Phase 2
0.6923	Remote Similarity	NPD3296	Phase 1
0.6911	Remote Similarity	NPD3793	Phase 3
0.691	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD2971	Approved
0.6907	Remote Similarity	NPD2968	Approved
0.6904	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD2845	Phase 2
0.6904	Remote Similarity	NPD2843	Phase 2
0.6901	Remote Similarity	NPD4474	Approved
0.6901	Remote Similarity	NPD4475	Approved
0.69	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1753	Discontinued
0.6893	Remote Similarity	NPD7452	Approved
0.6893	Remote Similarity	NPD7453	Approved
0.6886	Remote Similarity	NPD6320	Approved
0.6882	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD3453	Discontinued
0.6878	Remote Similarity	NPD4583	Approved
0.6878	Remote Similarity	NPD4582	Approved
0.6875	Remote Similarity	NPD4597	Approved
0.6875	Remote Similarity	NPD4598	Approved
0.6872	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4605	Approved
0.6866	Remote Similarity	NPD4604	Approved
0.6864	Remote Similarity	NPD3635	Approved
0.6864	Remote Similarity	NPD3636	Approved
0.6864	Remote Similarity	NPD3637	Approved
0.6854	Remote Similarity	NPD2899	Discontinued
0.6853	Remote Similarity	NPD3349	Phase 2
0.685	Remote Similarity	NPD6493	Phase 3
0.6845	Remote Similarity	NPD4796	Discontinued
0.6842	Remote Similarity	NPD3144	Approved
0.6842	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3145	Approved
0.6839	Remote Similarity	NPD6184	Discontinued
0.6839	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6297	Approved
0.6829	Remote Similarity	NPD4002	Approved
0.6829	Remote Similarity	NPD4004	Approved
0.6828	Remote Similarity	NPD19	Approved
0.6828	Remote Similarity	NPD1743	Approved
0.6828	Remote Similarity	NPD1742	Approved
0.6825	Remote Similarity	NPD5186	Approved
0.6825	Remote Similarity	NPD6747	Phase 1
0.6825	Remote Similarity	NPD5183	Approved
0.6824	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD4873	Discontinued

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