NPASS Compound

Structure

NPC195920 OpenBabel07101719142D 25 28 0 0 1 0 0 0 0 0999 V2000 6.4752 0.9012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6703 2.4349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4128 -1.3373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9839 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7446 -0.9709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1464 -2.0741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0815 1.7195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0828 0.7714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3307 -1.3855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7653 0.4832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6300 1.4357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7446 0.9709 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0815 -1.7195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9907 1.1157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1537 -1.9535 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1464 2.0741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3307 1.3855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4982 -0.9432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6049 -0.5038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8901 -0.0233 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5343 -1.0603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1537 1.9535 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 11 2 0 0 0 0 2 11 1 0 0 0 0 4 5 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 13 2 0 0 0 0 7 12 1 0 0 0 0 7 16 1 0 0 0 0 8 14 1 0 0 0 0 8 17 2 0 0 0 0 9 15 1 0 0 0 0 9 20 1 0 0 0 0 10 14 1 0 0 0 0 10 21 2 0 0 0 0 12 11 1 1 0 0 0 13 19 1 0 0 0 0 14 16 2 0 0 0 0 15 6 1 1 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 0 0 0 0 18 20 1 1 0 0 0 18 25 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 20 3 1 1 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.15
Volume:	348.383
LogP:	4.722
LogD:	3.468
LogS:	-4.655
# Rotatable Bonds:	2
TPSA:	76.11
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.504
Synthetic Accessibility Score:	6.209
Fsp3:	0.45
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.739
MDCK Permeability:	1.54669087351067e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.11

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	91.3907699584961%
Volume Distribution (VD):	1.489
Pgp-substrate:	7.852583885192871%

ADMET: Metabolism

CYP1A2-inhibitor:	0.342
CYP1A2-substrate:	0.848
CYP2C19-inhibitor:	0.122
CYP2C19-substrate:	0.53
CYP2C9-inhibitor:	0.387
CYP2C9-substrate:	0.437
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.159
CYP3A4-substrate:	0.295

ADMET: Excretion

Clearance (CL):	6.077
Half-life (T1/2):	0.219

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.939
Drug-inuced Liver Injury (DILI):	0.585
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.807
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.348
Carcinogencity:	0.913
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC195920

Natural Product ID:	NPC195920
*Common Name:**	Pukalide Aldehyde
IUPAC Name:	n.a.
Synonyms:	Pukalide Aldehyde
Standard InCHIKey:	CDYDRAISDJZNIZ-IBBHNLMTSA-N
Standard InCHI:	InChI=1S/C20H22O5/c1-11(2)12-4-5-13-6-15(23-19(13)22)9-20(3)18(25-20)17-8-14(10-21)16(7-12)24-17/h6,8,10,12,15,18H,1,4-5,7,9H2,2-3H3/t12-,15-,18-,20-/m0/s1
SMILES:	C=C(C)[C@H]1CCC2=C[C@@H](C[C@@]3(C)[C@H](c4cc(C=O)c(C1)o4)O3)OC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL300931
PubChem CID:	44296102
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO17857	Leptogorgia alba	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844963]
NPO32839	leptogorgia rigida	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844963]
NPO17857	Leptogorgia alba	Species	Gorgoniidae	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

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	134000.0	nM	PMID[473995]

☑ 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 NPC195920 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	395
0.1-0.2	1609
0.2-0.3	4501
0.3-0.4	9425
0.4-0.5	9954
0.5-0.6	6805
0.6-0.7	8410
0.7-0.8	1537
0.8-0.85	28
0.85-0.9	12
0.9-0.95	14
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9784	High Similarity	NPC475864
0.9712	High Similarity	NPC37488
0.9645	High Similarity	NPC471618
0.9645	High Similarity	NPC474255
0.9645	High Similarity	NPC474220
0.9577	High Similarity	NPC474270
0.9577	High Similarity	NPC475904
0.9437	High Similarity	NPC474317
0.9429	High Similarity	NPC110305
0.9379	High Similarity	NPC474378
0.9379	High Similarity	NPC474219
0.9353	High Similarity	NPC282973
0.9281	High Similarity	NPC474615
0.9014	High Similarity	NPC248795
0.8889	High Similarity	NPC254198
0.8865	High Similarity	NPC286130
0.8841	High Similarity	NPC136340
0.8836	High Similarity	NPC104924
0.8786	High Similarity	NPC200718
0.8759	High Similarity	NPC22248
0.8741	High Similarity	NPC107571
0.8592	High Similarity	NPC159786
0.8531	High Similarity	NPC303217
0.85	High Similarity	NPC45947
0.8487	Intermediate Similarity	NPC470380
0.8392	Intermediate Similarity	NPC106247
0.8333	Intermediate Similarity	NPC473368
0.8322	Intermediate Similarity	NPC267004
0.8322	Intermediate Similarity	NPC307346
0.8322	Intermediate Similarity	NPC218712
0.8322	Intermediate Similarity	NPC261733
0.8322	Intermediate Similarity	NPC86935
0.8286	Intermediate Similarity	NPC137570
0.825	Intermediate Similarity	NPC473753
0.825	Intermediate Similarity	NPC473766
0.8224	Intermediate Similarity	NPC19747
0.8219	Intermediate Similarity	NPC473268
0.8194	Intermediate Similarity	NPC474407
0.8194	Intermediate Similarity	NPC474425
0.8194	Intermediate Similarity	NPC474426
0.8188	Intermediate Similarity	NPC473152
0.8165	Intermediate Similarity	NPC333139
0.8148	Intermediate Similarity	NPC302392
0.8125	Intermediate Similarity	NPC261184
0.8092	Intermediate Similarity	NPC62799
0.8089	Intermediate Similarity	NPC107646
0.8089	Intermediate Similarity	NPC263265
0.8089	Intermediate Similarity	NPC278010
0.8089	Intermediate Similarity	NPC250769
0.8089	Intermediate Similarity	NPC60973
0.8089	Intermediate Similarity	NPC209364
0.8089	Intermediate Similarity	NPC295608
0.8086	Intermediate Similarity	NPC472895
0.8085	Intermediate Similarity	NPC216810
0.805	Intermediate Similarity	NPC305016
0.8038	Intermediate Similarity	NPC286722
0.8028	Intermediate Similarity	NPC184391
0.8025	Intermediate Similarity	NPC131725
0.8025	Intermediate Similarity	NPC279768
0.8012	Intermediate Similarity	NPC56358
0.8	Intermediate Similarity	NPC471544
0.8	Intermediate Similarity	NPC45358
0.8	Intermediate Similarity	NPC473344
0.8	Intermediate Similarity	NPC471545
0.7987	Intermediate Similarity	NPC473473
0.7987	Intermediate Similarity	NPC475295
0.7987	Intermediate Similarity	NPC237155
0.7975	Intermediate Similarity	NPC126723
0.7975	Intermediate Similarity	NPC474542
0.7962	Intermediate Similarity	NPC114880
0.7961	Intermediate Similarity	NPC84479
0.7952	Intermediate Similarity	NPC167340
0.7949	Intermediate Similarity	NPC18135
0.7939	Intermediate Similarity	NPC144288
0.7937	Intermediate Similarity	NPC25255
0.7937	Intermediate Similarity	NPC191828
0.7937	Intermediate Similarity	NPC287559
0.7937	Intermediate Similarity	NPC475381
0.7935	Intermediate Similarity	NPC211625
0.7931	Intermediate Similarity	NPC17681
0.7925	Intermediate Similarity	NPC81405
0.7922	Intermediate Similarity	NPC224418
0.7922	Intermediate Similarity	NPC221809
0.7914	Intermediate Similarity	NPC179015
0.7914	Intermediate Similarity	NPC173149
0.7914	Intermediate Similarity	NPC270312
0.7911	Intermediate Similarity	NPC75310
0.7904	Intermediate Similarity	NPC472665
0.7902	Intermediate Similarity	NPC476016
0.7901	Intermediate Similarity	NPC276735
0.7901	Intermediate Similarity	NPC123088
0.7895	Intermediate Similarity	NPC80635
0.7895	Intermediate Similarity	NPC223415
0.7888	Intermediate Similarity	NPC5079
0.7888	Intermediate Similarity	NPC193798
0.7888	Intermediate Similarity	NPC117986
0.7888	Intermediate Similarity	NPC197596
0.7888	Intermediate Similarity	NPC470939
0.7877	Intermediate Similarity	NPC97740
0.7875	Intermediate Similarity	NPC116639
0.7875	Intermediate Similarity	NPC140952
0.7862	Intermediate Similarity	NPC104736
0.7862	Intermediate Similarity	NPC21460
0.7857	Intermediate Similarity	NPC1848
0.7853	Intermediate Similarity	NPC121995
0.7852	Intermediate Similarity	NPC215109
0.7852	Intermediate Similarity	NPC170604
0.7847	Intermediate Similarity	NPC474279
0.7847	Intermediate Similarity	NPC474438
0.7843	Intermediate Similarity	NPC137295
0.7842	Intermediate Similarity	NPC67345
0.7842	Intermediate Similarity	NPC473969
0.7842	Intermediate Similarity	NPC244862
0.784	Intermediate Similarity	NPC14822
0.784	Intermediate Similarity	NPC283209
0.784	Intermediate Similarity	NPC234660
0.784	Intermediate Similarity	NPC475039
0.784	Intermediate Similarity	NPC14499
0.784	Intermediate Similarity	NPC476035
0.784	Intermediate Similarity	NPC51568
0.784	Intermediate Similarity	NPC285567
0.784	Intermediate Similarity	NPC469846
0.7838	Intermediate Similarity	NPC14650
0.7834	Intermediate Similarity	NPC191104
0.7832	Intermediate Similarity	NPC81912
0.7832	Intermediate Similarity	NPC329922
0.7832	Intermediate Similarity	NPC329694
0.7832	Intermediate Similarity	NPC474260
0.7826	Intermediate Similarity	NPC335761
0.7826	Intermediate Similarity	NPC472653
0.7823	Intermediate Similarity	NPC470740
0.7817	Intermediate Similarity	NPC188377
0.7817	Intermediate Similarity	NPC65735
0.7812	Intermediate Similarity	NPC304692
0.7812	Intermediate Similarity	NPC187149
0.7806	Intermediate Similarity	NPC71821
0.7805	Intermediate Similarity	NPC476850
0.7805	Intermediate Similarity	NPC476861
0.7799	Intermediate Similarity	NPC214541
0.7799	Intermediate Similarity	NPC44675
0.7792	Intermediate Similarity	NPC105381
0.7792	Intermediate Similarity	NPC10302
0.7791	Intermediate Similarity	NPC476860
0.7791	Intermediate Similarity	NPC476858
0.7791	Intermediate Similarity	NPC476856
0.7791	Intermediate Similarity	NPC472664
0.7791	Intermediate Similarity	NPC476857
0.7785	Intermediate Similarity	NPC475777
0.7785	Intermediate Similarity	NPC44577
0.7785	Intermediate Similarity	NPC146872
0.7785	Intermediate Similarity	NPC75906
0.7778	Intermediate Similarity	NPC470741
0.7778	Intermediate Similarity	NPC473355
0.7778	Intermediate Similarity	NPC303210
0.7778	Intermediate Similarity	NPC95472
0.7778	Intermediate Similarity	NPC188649
0.7778	Intermediate Similarity	NPC471573
0.7778	Intermediate Similarity	NPC474830
0.7778	Intermediate Similarity	NPC471501
0.7778	Intermediate Similarity	NPC471554
0.7778	Intermediate Similarity	NPC18986
0.7778	Intermediate Similarity	NPC239270
0.7778	Intermediate Similarity	NPC49009
0.7778	Intermediate Similarity	NPC68848
0.7778	Intermediate Similarity	NPC205071
0.7771	Intermediate Similarity	NPC88445
0.7771	Intermediate Similarity	NPC46551
0.777	Intermediate Similarity	NPC288209
0.7764	Intermediate Similarity	NPC477403
0.7762	Intermediate Similarity	NPC71274
0.7762	Intermediate Similarity	NPC474829
0.7762	Intermediate Similarity	NPC75557
0.7758	Intermediate Similarity	NPC67450
0.7758	Intermediate Similarity	NPC323137
0.7758	Intermediate Similarity	NPC193881
0.7758	Intermediate Similarity	NPC210460
0.7758	Intermediate Similarity	NPC155264
0.7754	Intermediate Similarity	NPC45536
0.775	Intermediate Similarity	NPC469485
0.775	Intermediate Similarity	NPC41880
0.7744	Intermediate Similarity	NPC475779
0.7744	Intermediate Similarity	NPC23387
0.7742	Intermediate Similarity	NPC233763
0.7742	Intermediate Similarity	NPC276676
0.7742	Intermediate Similarity	NPC294365
0.7742	Intermediate Similarity	NPC171656
0.7736	Intermediate Similarity	NPC288534
0.773	Intermediate Similarity	NPC88841
0.773	Intermediate Similarity	NPC302369
0.773	Intermediate Similarity	NPC288602
0.773	Intermediate Similarity	NPC216092
0.773	Intermediate Similarity	NPC134254
0.773	Intermediate Similarity	NPC39986
0.7725	Intermediate Similarity	NPC469848
0.7722	Intermediate Similarity	NPC475717
0.7712	Intermediate Similarity	NPC470856
0.7711	Intermediate Similarity	NPC470995
0.7708	Intermediate Similarity	NPC52035
0.7707	Intermediate Similarity	NPC329180
0.7703	Intermediate Similarity	NPC470859

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 NPC195920 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	1062
0.2-0.3	2212
0.3-0.4	2746
0.4-0.5	1773
0.5-0.6	752
0.6-0.7	253
0.7-0.8	20
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
0.8165	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD920	Approved
0.7607	Intermediate Similarity	NPD919	Approved
0.7564	Intermediate Similarity	NPD6799	Approved
0.7516	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.7469	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1247	Approved
0.7403	Intermediate Similarity	NPD1471	Phase 3
0.7391	Intermediate Similarity	NPD6599	Discontinued
0.7389	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7075	Discontinued
0.7308	Intermediate Similarity	NPD1243	Approved
0.7301	Intermediate Similarity	NPD6801	Discontinued
0.729	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2796	Approved
0.7225	Intermediate Similarity	NPD6765	Approved
0.7225	Intermediate Similarity	NPD6764	Approved
0.7219	Intermediate Similarity	NPD3926	Phase 2
0.7215	Intermediate Similarity	NPD3887	Approved
0.7212	Intermediate Similarity	NPD3817	Phase 2
0.7212	Intermediate Similarity	NPD5402	Approved
0.7205	Intermediate Similarity	NPD5403	Approved
0.7188	Intermediate Similarity	NPD5401	Approved
0.7169	Intermediate Similarity	NPD3882	Suspended
0.7152	Intermediate Similarity	NPD4628	Phase 3
0.7143	Intermediate Similarity	NPD5494	Approved
0.7114	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6832	Phase 2
0.707	Intermediate Similarity	NPD2344	Approved
0.7062	Intermediate Similarity	NPD6784	Approved
0.7062	Intermediate Similarity	NPD6785	Approved
0.7059	Intermediate Similarity	NPD6808	Phase 2
0.7048	Intermediate Similarity	NPD5761	Phase 2
0.7048	Intermediate Similarity	NPD5760	Phase 2
0.6977	Remote Similarity	NPD2403	Approved
0.6975	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2353	Approved
0.6962	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1019	Discontinued
0.6943	Remote Similarity	NPD2799	Discontinued
0.6932	Remote Similarity	NPD6559	Discontinued
0.6928	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3749	Approved
0.6899	Remote Similarity	NPD1551	Phase 2
0.6894	Remote Similarity	NPD2309	Approved
0.6883	Remote Similarity	NPD2313	Discontinued
0.6879	Remote Similarity	NPD2067	Discontinued
0.6875	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2534	Approved
0.6871	Remote Similarity	NPD2532	Approved
0.6871	Remote Similarity	NPD2533	Approved
0.6859	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD447	Suspended
0.6859	Remote Similarity	NPD6355	Discontinued
0.6849	Remote Similarity	NPD9092	Discovery
0.6846	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7819	Suspended
0.6835	Remote Similarity	NPD7033	Discontinued
0.6832	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7411	Suspended
0.6824	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD17	Approved
0.6813	Remote Similarity	NPD1549	Phase 2
0.6807	Remote Similarity	NPD3226	Approved
0.68	Remote Similarity	NPD3818	Discontinued
0.68	Remote Similarity	NPD9717	Approved
0.6795	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.679	Remote Similarity	NPD2354	Approved
0.6788	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6279	Approved
0.6786	Remote Similarity	NPD6280	Approved
0.6786	Remote Similarity	NPD1934	Approved
0.677	Remote Similarity	NPD2800	Approved
0.6766	Remote Similarity	NPD4380	Phase 2
0.6765	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1933	Approved
0.675	Remote Similarity	NPD6002	Phase 3
0.675	Remote Similarity	NPD6005	Phase 3
0.675	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6004	Phase 3
0.675	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD5647	Approved
0.6731	Remote Similarity	NPD6233	Phase 2
0.6708	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3751	Discontinued
0.6704	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1608	Approved
0.6686	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6166	Phase 2
0.6686	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6798	Discontinued
0.6647	Remote Similarity	NPD2801	Approved
0.6646	Remote Similarity	NPD2346	Discontinued
0.6644	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD1510	Phase 2
0.6625	Remote Similarity	NPD3748	Approved
0.6623	Remote Similarity	NPD2798	Approved
0.661	Remote Similarity	NPD2163	Approved
0.6608	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD5353	Approved
0.6601	Remote Similarity	NPD1876	Approved
0.6597	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6797	Phase 2
0.6584	Remote Similarity	NPD2935	Discontinued
0.6582	Remote Similarity	NPD1240	Approved
0.6582	Remote Similarity	NPD4307	Phase 2
0.6579	Remote Similarity	NPD3972	Approved
0.6577	Remote Similarity	NPD9545	Approved
0.6575	Remote Similarity	NPD1241	Discontinued
0.6571	Remote Similarity	NPD3787	Discontinued
0.6566	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD3146	Approved
0.6566	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD2654	Approved
0.6561	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD1203	Approved
0.6558	Remote Similarity	NPD3267	Approved
0.6558	Remote Similarity	NPD3266	Approved
0.6556	Remote Similarity	NPD7251	Discontinued
0.6554	Remote Similarity	NPD7473	Discontinued
0.6541	Remote Similarity	NPD230	Phase 1
0.6533	Remote Similarity	NPD8404	Phase 2
0.6529	Remote Similarity	NPD6386	Approved
0.6529	Remote Similarity	NPD6385	Approved
0.6527	Remote Similarity	NPD1512	Approved
0.6527	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7808	Phase 3
0.6519	Remote Similarity	NPD4062	Phase 3
0.65	Remote Similarity	NPD5953	Discontinued
0.65	Remote Similarity	NPD1607	Approved
0.6497	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD6190	Approved
0.6484	Remote Similarity	NPD8312	Approved
0.6484	Remote Similarity	NPD8313	Approved
0.6477	Remote Similarity	NPD6232	Discontinued
0.6474	Remote Similarity	NPD8285	Discontinued
0.6474	Remote Similarity	NPD7768	Phase 2
0.6467	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD7685	Pre-registration
0.6458	Remote Similarity	NPD2182	Approved
0.6456	Remote Similarity	NPD3268	Approved
0.6456	Remote Similarity	NPD3764	Approved
0.6456	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD411	Approved
0.6453	Remote Similarity	NPD7972	Discontinued
0.645	Remote Similarity	NPD957	Approved
0.6444	Remote Similarity	NPD7074	Phase 3
0.6441	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5049	Phase 3
0.6424	Remote Similarity	NPD5585	Approved
0.6424	Remote Similarity	NPD3750	Approved
0.6424	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4308	Phase 3
0.6416	Remote Similarity	NPD2296	Approved
0.641	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD1511	Approved
0.6402	Remote Similarity	NPD5958	Discontinued
0.6402	Remote Similarity	NPD2897	Discontinued
0.6398	Remote Similarity	NPD6653	Approved
0.6389	Remote Similarity	NPD7286	Phase 2
0.6389	Remote Similarity	NPD1358	Approved
0.6389	Remote Similarity	NPD7054	Approved
0.6389	Remote Similarity	NPD5844	Phase 1
0.6384	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD8150	Discontinued
0.6375	Remote Similarity	NPD3142	Approved
0.6375	Remote Similarity	NPD3140	Approved
0.6369	Remote Similarity	NPD4662	Approved
0.6369	Remote Similarity	NPD4661	Approved
0.6369	Remote Similarity	NPD9494	Approved
0.6358	Remote Similarity	NPD7097	Phase 1
0.6354	Remote Similarity	NPD7472	Approved
0.6354	Remote Similarity	NPD4107	Approved
0.6348	Remote Similarity	NPD5242	Approved
0.6347	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD2797	Approved
0.6341	Remote Similarity	NPD5762	Approved
0.6341	Remote Similarity	NPD5763	Approved
0.634	Remote Similarity	NPD7435	Discontinued
0.6337	Remote Similarity	NPD958	Approved
0.6337	Remote Similarity	NPD5890	Approved
0.6337	Remote Similarity	NPD5889	Approved
0.6333	Remote Similarity	NPD9493	Approved
0.6333	Remote Similarity	NPD7799	Discontinued
0.6331	Remote Similarity	NPD6273	Approved
0.6331	Remote Similarity	NPD2186	Approved
0.6328	Remote Similarity	NPD6959	Discontinued
0.6321	Remote Similarity	NPD4482	Phase 3

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