NPASS Compound

Structure

CID228988 OpenBabel06191716022D 21 22 0 0 0 0 0 0 0 0999 V2000 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 -0.8660 -2.5000 0.0000 C 0 0 0 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 15 1 0 0 0 0 5 13 1 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 18 1 0 0 0 0 9 17 1 0 0 0 0 10 19 2 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 16 18 2 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	280.11
Volume:	305.414
LogP:	4.16
LogD:	3.387
LogS:	-3.693
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.499
Synthetic Accessibility Score:	2.601
Fsp3:	0.056
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.702
MDCK Permeability:	1.7604263121029362e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.598
30% Bioavailability (F30%):	0.413

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.135
Plasma Protein Binding (PPB):	100.4845199584961%
Volume Distribution (VD):	0.549
Pgp-substrate:	0.6453660130500793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.958
CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.572
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.54
CYP2C9-substrate:	0.832
CYP2D6-inhibitor:	0.794
CYP2D6-substrate:	0.929
CYP3A4-inhibitor:	0.504
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	6.626
Half-life (T1/2):	0.8

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.119
AMES Toxicity:	0.784
Rat Oral Acute Toxicity:	0.302
Maximum Recommended Daily Dose:	0.861
Skin Sensitization:	0.957
Carcinogencity:	0.687
Eye Corrosion:	0.004
Eye Irritation:	0.933
Respiratory Toxicity:	0.833

Download Data

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

Natural Product: NPC228988

Natural Product ID:	NPC228988
*Common Name:**	Magnaledehyde B
IUPAC Name:	(E)-3-[4-hydroxy-3-(4-hydroxy-3-prop-2-enylphenyl)phenyl]prop-2-enal
Synonyms:
Standard InCHIKey:	INTLXODHWXUPBA-HWKANZROSA-N
Standard InCHI:	InChI=1S/C18H16O3/c1-2-4-15-12-14(7-9-17(15)20)16-11-13(5-3-10-19)6-8-18(16)21/h2-3,5-12,20-21H,1,4H2/b5-3+
SMILES:	O=C/C=C/c1ccc(c(c1)c1ccc(c(c1)CC=C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL250885
PubChem CID:	5319187
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000041] Biphenyls 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
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1659613]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17918910]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	stem	n.a.	PMID[18175990]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[19086868]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	bark	n.a.	PMID[23823874]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2598	Maesa japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2598	Maesa japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2598	Maesa japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	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	6

Activity Type	# Activity
Cell Line	5
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[479113]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[479113]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[479113]
NPT2341	Cell Line	NCI-H1975	Homo sapiens	IC50	=	34120.0	nM	PMID[479114]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	32380.0	nM	PMID[479114]
NPT22158	CELL-LINE	HCC827	Homo sapiens	IC50	=	35480.0	nM	PMID[479114]

☑ 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 NPC228988 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	252
0.1-0.2	1740
0.2-0.3	3828
0.3-0.4	12563
0.4-0.5	6637
0.5-0.6	8169
0.6-0.7	7723
0.7-0.8	1624
0.8-0.85	126
0.85-0.9	28
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9204	High Similarity	NPC131868
0.9135	High Similarity	NPC168829
0.9123	High Similarity	NPC251259
0.9065	High Similarity	NPC262365
0.9048	High Similarity	NPC288411
0.9035	High Similarity	NPC216216
0.8962	High Similarity	NPC138942
0.8957	High Similarity	NPC295034
0.8899	High Similarity	NPC44732
0.8818	High Similarity	NPC308689
0.8739	High Similarity	NPC286222
0.8654	High Similarity	NPC283711
0.8611	High Similarity	NPC243677
0.8611	High Similarity	NPC303141
0.8609	High Similarity	NPC184527
0.8598	High Similarity	NPC470202
0.8598	High Similarity	NPC135784
0.8584	High Similarity	NPC473137
0.8584	High Similarity	NPC12656
0.8571	High Similarity	NPC201967
0.8559	High Similarity	NPC296683
0.8558	High Similarity	NPC286006
0.8545	High Similarity	NPC470039
0.8534	High Similarity	NPC182240
0.8532	High Similarity	NPC271274
0.8532	High Similarity	NPC54765
0.8496	Intermediate Similarity	NPC141003
0.8496	Intermediate Similarity	NPC35344
0.8491	Intermediate Similarity	NPC132078
0.8491	Intermediate Similarity	NPC130193
0.8491	Intermediate Similarity	NPC51333
0.8491	Intermediate Similarity	NPC128723
0.8491	Intermediate Similarity	NPC78119
0.8491	Intermediate Similarity	NPC216468
0.8482	Intermediate Similarity	NPC95716
0.8476	Intermediate Similarity	NPC216520
0.8476	Intermediate Similarity	NPC82664
0.8476	Intermediate Similarity	NPC132271
0.8476	Intermediate Similarity	NPC292730
0.8468	Intermediate Similarity	NPC75272
0.8468	Intermediate Similarity	NPC471954
0.8468	Intermediate Similarity	NPC98392
0.8462	Intermediate Similarity	NPC128062
0.8462	Intermediate Similarity	NPC151715
0.8462	Intermediate Similarity	NPC473136
0.8455	Intermediate Similarity	NPC245395
0.8411	Intermediate Similarity	NPC225506
0.8411	Intermediate Similarity	NPC213730
0.8407	Intermediate Similarity	NPC228425
0.8407	Intermediate Similarity	NPC46940
0.8396	Intermediate Similarity	NPC77492
0.8393	Intermediate Similarity	NPC183700
0.8381	Intermediate Similarity	NPC26244
0.8378	Intermediate Similarity	NPC95344
0.8365	Intermediate Similarity	NPC271440
0.8364	Intermediate Similarity	NPC69332
0.8364	Intermediate Similarity	NPC95178
0.8364	Intermediate Similarity	NPC29989
0.8333	Intermediate Similarity	NPC40258
0.8333	Intermediate Similarity	NPC7686
0.8333	Intermediate Similarity	NPC91461
0.8319	Intermediate Similarity	NPC31936
0.8318	Intermediate Similarity	NPC122005
0.8318	Intermediate Similarity	NPC252821
0.8318	Intermediate Similarity	NPC92730
0.8304	Intermediate Similarity	NPC58865
0.8304	Intermediate Similarity	NPC88141
0.8302	Intermediate Similarity	NPC473388
0.8288	Intermediate Similarity	NPC260952
0.8273	Intermediate Similarity	NPC219286
0.8273	Intermediate Similarity	NPC99557
0.8269	Intermediate Similarity	NPC45040
0.8261	Intermediate Similarity	NPC285350
0.8257	Intermediate Similarity	NPC68269
0.8241	Intermediate Similarity	NPC294741
0.8235	Intermediate Similarity	NPC71870
0.823	Intermediate Similarity	NPC471535
0.8224	Intermediate Similarity	NPC225464
0.8214	Intermediate Similarity	NPC63698
0.8214	Intermediate Similarity	NPC61885
0.8214	Intermediate Similarity	NPC206341
0.8208	Intermediate Similarity	NPC8392
0.8208	Intermediate Similarity	NPC274678
0.8205	Intermediate Similarity	NPC174087
0.8198	Intermediate Similarity	NPC70843
0.819	Intermediate Similarity	NPC322197
0.819	Intermediate Similarity	NPC23402
0.8182	Intermediate Similarity	NPC8931
0.8182	Intermediate Similarity	NPC261573
0.8182	Intermediate Similarity	NPC120693
0.8182	Intermediate Similarity	NPC323810
0.8174	Intermediate Similarity	NPC715
0.8167	Intermediate Similarity	NPC253627
0.8165	Intermediate Similarity	NPC51015
0.8158	Intermediate Similarity	NPC165770
0.8158	Intermediate Similarity	NPC4493
0.8158	Intermediate Similarity	NPC151537
0.8158	Intermediate Similarity	NPC476632
0.8158	Intermediate Similarity	NPC297657
0.8158	Intermediate Similarity	NPC225679
0.8158	Intermediate Similarity	NPC470355
0.8145	Intermediate Similarity	NPC3009
0.8142	Intermediate Similarity	NPC314187
0.813	Intermediate Similarity	NPC35341
0.813	Intermediate Similarity	NPC283508
0.8125	Intermediate Similarity	NPC228737
0.8125	Intermediate Similarity	NPC151477
0.8115	Intermediate Similarity	NPC231767
0.8113	Intermediate Similarity	NPC76938
0.8108	Intermediate Similarity	NPC233396
0.8108	Intermediate Similarity	NPC154899
0.8108	Intermediate Similarity	NPC474839
0.8103	Intermediate Similarity	NPC268160
0.8103	Intermediate Similarity	NPC195922
0.8103	Intermediate Similarity	NPC107240
0.8099	Intermediate Similarity	NPC11250
0.8095	Intermediate Similarity	NPC85342
0.8095	Intermediate Similarity	NPC204210
0.8087	Intermediate Similarity	NPC43525
0.807	Intermediate Similarity	NPC321252
0.807	Intermediate Similarity	NPC475018
0.807	Intermediate Similarity	NPC13482
0.807	Intermediate Similarity	NPC132720
0.807	Intermediate Similarity	NPC252544
0.807	Intermediate Similarity	NPC63345
0.8067	Intermediate Similarity	NPC151197
0.8067	Intermediate Similarity	NPC473767
0.8056	Intermediate Similarity	NPC32674
0.8056	Intermediate Similarity	NPC156313
0.8053	Intermediate Similarity	NPC11554
0.8053	Intermediate Similarity	NPC68260
0.8053	Intermediate Similarity	NPC279887
0.8051	Intermediate Similarity	NPC299180
0.8051	Intermediate Similarity	NPC477136
0.8051	Intermediate Similarity	NPC278652
0.8049	Intermediate Similarity	NPC127975
0.8037	Intermediate Similarity	NPC32714
0.8037	Intermediate Similarity	NPC246679
0.8037	Intermediate Similarity	NPC144682
0.8036	Intermediate Similarity	NPC135464
0.8036	Intermediate Similarity	NPC248904
0.8036	Intermediate Similarity	NPC19149
0.8036	Intermediate Similarity	NPC188677
0.8036	Intermediate Similarity	NPC92623
0.8034	Intermediate Similarity	NPC192948
0.8034	Intermediate Similarity	NPC35797
0.8034	Intermediate Similarity	NPC147179
0.8033	Intermediate Similarity	NPC12824
0.8019	Intermediate Similarity	NPC181709
0.8018	Intermediate Similarity	NPC238696
0.8018	Intermediate Similarity	NPC119860
0.8017	Intermediate Similarity	NPC242136
0.8017	Intermediate Similarity	NPC322239
0.8017	Intermediate Similarity	NPC117846
0.8017	Intermediate Similarity	NPC28784
0.8017	Intermediate Similarity	NPC296144
0.8	Intermediate Similarity	NPC96024
0.8	Intermediate Similarity	NPC177576
0.8	Intermediate Similarity	NPC300017
0.8	Intermediate Similarity	NPC12221
0.7984	Intermediate Similarity	NPC71610
0.7983	Intermediate Similarity	NPC249435
0.7982	Intermediate Similarity	NPC55617
0.7982	Intermediate Similarity	NPC62258
0.7982	Intermediate Similarity	NPC282855
0.7982	Intermediate Similarity	NPC26013
0.7967	Intermediate Similarity	NPC265413
0.7967	Intermediate Similarity	NPC10154
0.7966	Intermediate Similarity	NPC308311
0.7966	Intermediate Similarity	NPC38893
0.7966	Intermediate Similarity	NPC477137
0.7966	Intermediate Similarity	NPC308828
0.7966	Intermediate Similarity	NPC261973
0.7966	Intermediate Similarity	NPC219112
0.7965	Intermediate Similarity	NPC141523
0.7953	Intermediate Similarity	NPC41847
0.7951	Intermediate Similarity	NPC176208
0.7949	Intermediate Similarity	NPC473931
0.7949	Intermediate Similarity	NPC474114
0.7949	Intermediate Similarity	NPC474050
0.7946	Intermediate Similarity	NPC117115
0.7944	Intermediate Similarity	NPC289769
0.7944	Intermediate Similarity	NPC27323
0.7944	Intermediate Similarity	NPC81010
0.7944	Intermediate Similarity	NPC32977
0.7944	Intermediate Similarity	NPC152415
0.7944	Intermediate Similarity	NPC316301
0.7931	Intermediate Similarity	NPC199462
0.7931	Intermediate Similarity	NPC250323
0.7928	Intermediate Similarity	NPC168393
0.7928	Intermediate Similarity	NPC108497
0.7928	Intermediate Similarity	NPC233827
0.7925	Intermediate Similarity	NPC304541
0.7917	Intermediate Similarity	NPC141791
0.7917	Intermediate Similarity	NPC263386
0.7913	Intermediate Similarity	NPC116842
0.7913	Intermediate Similarity	NPC174096
0.7913	Intermediate Similarity	NPC141782
0.7913	Intermediate Similarity	NPC226401
0.7913	Intermediate Similarity	NPC79793

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 NPC228988 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	1076
0.2-0.3	1135
0.3-0.4	2784
0.4-0.5	2111
0.5-0.6	1227
0.6-0.7	508
0.7-0.8	63
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8491	Intermediate Similarity	NPD3020	Approved
0.8381	Intermediate Similarity	NPD2859	Approved
0.8381	Intermediate Similarity	NPD2860	Approved
0.8286	Intermediate Similarity	NPD2933	Approved
0.8286	Intermediate Similarity	NPD2934	Approved
0.8037	Intermediate Similarity	NPD1809	Phase 2
0.8019	Intermediate Similarity	NPD845	Approved
0.7965	Intermediate Similarity	NPD2342	Discontinued
0.7944	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7635	Approved
0.7903	Intermediate Similarity	NPD1164	Approved
0.7826	Intermediate Similarity	NPD3021	Approved
0.7826	Intermediate Similarity	NPD3022	Approved
0.7706	Intermediate Similarity	NPD844	Approved
0.7705	Intermediate Similarity	NPD4626	Approved
0.7692	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD940	Approved
0.7679	Intermediate Similarity	NPD846	Approved
0.7636	Intermediate Similarity	NPD288	Approved
0.7623	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4589	Approved
0.7541	Intermediate Similarity	NPD5304	Approved
0.7541	Intermediate Similarity	NPD3091	Approved
0.7541	Intermediate Similarity	NPD5303	Approved
0.75	Intermediate Similarity	NPD4208	Discontinued
0.7481	Intermediate Similarity	NPD4060	Phase 1
0.748	Intermediate Similarity	NPD5691	Approved
0.744	Intermediate Similarity	NPD1201	Approved
0.7434	Intermediate Similarity	NPD1242	Phase 1
0.7429	Intermediate Similarity	NPD111	Approved
0.7419	Intermediate Similarity	NPD2932	Approved
0.7419	Intermediate Similarity	NPD2286	Discontinued
0.7419	Intermediate Similarity	NPD3019	Approved
0.7417	Intermediate Similarity	NPD2229	Approved
0.7417	Intermediate Similarity	NPD2234	Approved
0.7417	Intermediate Similarity	NPD2228	Approved
0.7373	Intermediate Similarity	NPD4750	Phase 3
0.7344	Intermediate Similarity	NPD1470	Approved
0.7333	Intermediate Similarity	NPD5405	Approved
0.7333	Intermediate Similarity	NPD5406	Approved
0.7333	Intermediate Similarity	NPD5408	Approved
0.7333	Intermediate Similarity	NPD5404	Approved
0.7333	Intermediate Similarity	NPD2935	Discontinued
0.7328	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD3092	Approved
0.7302	Intermediate Similarity	NPD1610	Phase 2
0.7281	Intermediate Similarity	NPD3028	Approved
0.7246	Intermediate Similarity	NPD7003	Approved
0.7236	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD2861	Phase 2
0.7231	Intermediate Similarity	NPD5736	Approved
0.72	Intermediate Similarity	NPD4093	Discontinued
0.72	Intermediate Similarity	NPD1651	Approved
0.7188	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4908	Phase 1
0.7176	Intermediate Similarity	NPD4207	Discontinued
0.7163	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4059	Approved
0.7143	Intermediate Similarity	NPD6405	Approved
0.7143	Intermediate Similarity	NPD3095	Discontinued
0.7143	Intermediate Similarity	NPD6407	Approved
0.7143	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1283	Approved
0.7132	Intermediate Similarity	NPD2799	Discontinued
0.7131	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3400	Discontinued
0.712	Intermediate Similarity	NPD1548	Phase 1
0.712	Intermediate Similarity	NPD7330	Discontinued
0.7119	Intermediate Similarity	NPD968	Approved
0.7119	Intermediate Similarity	NPD3134	Approved
0.7099	Intermediate Similarity	NPD4212	Discontinued
0.7094	Intermediate Similarity	NPD1237	Approved
0.7083	Intermediate Similarity	NPD1792	Phase 2
0.7077	Intermediate Similarity	NPD3094	Phase 2
0.7077	Intermediate Similarity	NPD2797	Approved
0.7073	Intermediate Similarity	NPD497	Approved
0.7073	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3764	Approved
0.7059	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2344	Approved
0.7023	Intermediate Similarity	NPD2798	Approved
0.7016	Intermediate Similarity	NPD6671	Approved
0.7015	Intermediate Similarity	NPD6663	Approved
0.7007	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1510	Phase 2
0.7	Intermediate Similarity	NPD74	Approved
0.7	Intermediate Similarity	NPD9266	Approved
0.7	Intermediate Similarity	NPD2684	Approved
0.6992	Remote Similarity	NPD496	Approved
0.6992	Remote Similarity	NPD4625	Phase 3
0.6992	Remote Similarity	NPD5283	Phase 1
0.6992	Remote Similarity	NPD495	Approved
0.6992	Remote Similarity	NPD498	Approved
0.6984	Remote Similarity	NPD9545	Approved
0.6977	Remote Similarity	NPD3972	Approved
0.6975	Remote Similarity	NPD1445	Approved
0.6975	Remote Similarity	NPD1444	Approved
0.6963	Remote Similarity	NPD1240	Approved
0.6963	Remote Similarity	NPD943	Approved
0.696	Remote Similarity	NPD9493	Approved
0.6957	Remote Similarity	NPD4477	Approved
0.6957	Remote Similarity	NPD4476	Approved
0.6953	Remote Similarity	NPD3847	Discontinued
0.6953	Remote Similarity	NPD3496	Discontinued
0.6947	Remote Similarity	NPD4103	Phase 2
0.6947	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5451	Approved
0.6935	Remote Similarity	NPD5951	Approved
0.6929	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6583	Phase 3
0.6923	Remote Similarity	NPD4659	Approved
0.6923	Remote Similarity	NPD1669	Approved
0.6923	Remote Similarity	NPD6582	Phase 2
0.6917	Remote Similarity	NPD1358	Approved
0.6917	Remote Similarity	NPD9264	Approved
0.6917	Remote Similarity	NPD9267	Approved
0.6917	Remote Similarity	NPD9263	Approved
0.6912	Remote Similarity	NPD6355	Discontinued
0.6911	Remote Similarity	NPD5535	Approved
0.6905	Remote Similarity	NPD5536	Phase 2
0.6899	Remote Similarity	NPD1281	Approved
0.6899	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD422	Phase 1
0.6894	Remote Similarity	NPD6584	Phase 3
0.6884	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7157	Approved
0.6879	Remote Similarity	NPD8166	Discontinued
0.6875	Remote Similarity	NPD1751	Approved
0.6875	Remote Similarity	NPD2667	Approved
0.6875	Remote Similarity	NPD2668	Approved
0.687	Remote Similarity	NPD1876	Approved
0.6864	Remote Similarity	NPD1929	Approved
0.6864	Remote Similarity	NPD1930	Approved
0.6864	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD1607	Approved
0.6855	Remote Similarity	NPD1241	Discontinued
0.6853	Remote Similarity	NPD7390	Discontinued
0.685	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.685	Remote Similarity	NPD1894	Discontinued
0.6849	Remote Similarity	NPD7458	Discontinued
0.6846	Remote Similarity	NPD2561	Approved
0.6846	Remote Similarity	NPD2562	Approved
0.6831	Remote Similarity	NPD2309	Approved
0.6829	Remote Similarity	NPD228	Approved
0.6822	Remote Similarity	NPD3026	Approved
0.6822	Remote Similarity	NPD3023	Approved
0.6822	Remote Similarity	NPD3143	Discontinued
0.6822	Remote Similarity	NPD3421	Phase 3
0.6818	Remote Similarity	NPD1129	Approved
0.6818	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1134	Approved
0.6818	Remote Similarity	NPD1133	Approved
0.6818	Remote Similarity	NPD1131	Approved
0.6818	Remote Similarity	NPD1135	Approved
0.6815	Remote Similarity	NPD6798	Discontinued
0.6815	Remote Similarity	NPD2313	Discontinued
0.6815	Remote Similarity	NPD3268	Approved
0.6812	Remote Similarity	NPD3552	Approved
0.6812	Remote Similarity	NPD3555	Approved
0.6812	Remote Similarity	NPD3553	Approved
0.6812	Remote Similarity	NPD3554	Approved
0.681	Remote Similarity	NPD9273	Approved
0.6807	Remote Similarity	NPD9610	Approved
0.6807	Remote Similarity	NPD9608	Approved
0.6806	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4380	Phase 2
0.68	Remote Similarity	NPD7768	Phase 2
0.6797	Remote Similarity	NPD3024	Approved
0.6797	Remote Similarity	NPD3025	Approved
0.6786	Remote Similarity	NPD7266	Discontinued
0.6783	Remote Similarity	NPD6667	Approved
0.6783	Remote Similarity	NPD6666	Approved
0.6774	Remote Similarity	NPD7843	Approved
0.6769	Remote Similarity	NPD1611	Approved
0.6769	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD3690	Phase 2
0.6767	Remote Similarity	NPD3691	Phase 2
0.6761	Remote Similarity	NPD3750	Approved
0.6761	Remote Similarity	NPD4628	Phase 3
0.675	Remote Similarity	NPD9697	Approved
0.6746	Remote Similarity	NPD709	Approved
0.6746	Remote Similarity	NPD256	Approved
0.6746	Remote Similarity	NPD6387	Discontinued
0.6746	Remote Similarity	NPD255	Approved
0.6744	Remote Similarity	NPD5846	Approved
0.6744	Remote Similarity	NPD6516	Phase 2
0.6742	Remote Similarity	NPD8651	Approved
0.6741	Remote Similarity	NPD3027	Phase 3
0.6739	Remote Similarity	NPD4097	Suspended
0.6738	Remote Similarity	NPD2424	Discontinued
0.6738	Remote Similarity	NPD1549	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