NPASS Compound

Structure

CID33728 OpenBabel06191715362D 26 27 0 0 0 0 0 0 0 0999 V2000 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 -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 4.3301 -1.5000 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 -0.5000 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 0.0000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 18 2 0 0 0 0 9 19 1 0 0 0 0 10 20 2 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 19 2 0 0 0 0 13 14 2 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 21 2 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 17 24 2 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.21
Volume:	400.4
LogP:	6.388
LogD:	4.738
LogS:	-3.917
# Rotatable Bonds:	7
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.442
Synthetic Accessibility Score:	2.623
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.974
MDCK Permeability:	2.1787252990179695e-05
Pgp-inhibitor:	0.931
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.737
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	100.42288970947266%
Volume Distribution (VD):	1.686
Pgp-substrate:	0.38025715947151184%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.181
CYP2C19-inhibitor:	0.96
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.797
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.805
CYP2D6-substrate:	0.731
CYP3A4-inhibitor:	0.498
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	7.921
Half-life (T1/2):	0.263

ADMET: Toxicity

hERG Blockers:	0.214
Human Hepatotoxicity (H-HT):	0.396
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.2
Skin Sensitization:	0.951
Carcinogencity:	0.053
Eye Corrosion:	0.005
Eye Irritation:	0.934
Respiratory Toxicity:	0.183

Download Data

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

Natural Product: NPC33728

Natural Product ID:	NPC33728
*Common Name:**	Amorphastilbol
IUPAC Name:	2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-[(E)-2-phenylethenyl]benzene-1,3-diol
Synonyms:	Amorphastilbol
Standard InCHIKey:	YPGQBVBJFQCVKA-ORSZPIRQSA-N
Standard InCHI:	InChI=1S/C24H28O2/c1-18(2)8-7-9-19(3)12-15-22-23(25)16-21(17-24(22)26)14-13-20-10-5-4-6-11-20/h4-6,8,10-14,16-17,25-26H,7,9,15H2,1-3H3/b14-13+,19-12+
SMILES:	CC(=CCC/C(=C/Cc1c(cc(/C=C/c2ccccc2)cc1O)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500257
PubChem CID:	6440462
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18841906]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28075580]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326318]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350086]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14929	Helichrysum umbraculigerum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16886	Amorpha fruticosa	Species	Fabaceae	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
EC50	2
IC50	6
MIC	8
Others	3

Activity Type	# Activity
Cell Line	2
Individual Protein	7
Organism	8
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Emax	=	21.0	%	PMID[549884]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	50000.0	nM	PMID[549885]
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	25000.0	nM	PMID[549885]
NPT2	Others	Unspecified		IC50	=	260.0	nM	PMID[549883]
NPT2	Others	Unspecified		IC50	=	680.0	nM	PMID[549883]
NPT866	Individual Protein	Peroxisome proliferator-activated receptor alpha	Homo sapiens	EC50	=	12000.0	nM	PMID[549884]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	EC50	=	5000.0	nM	PMID[549884]
NPT866	Individual Protein	Peroxisome proliferator-activated receptor alpha	Homo sapiens	Emax	=	66.0	%	PMID[549884]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	Emax	=	83.0	%	PMID[549884]
NPT866	Individual Protein	Peroxisome proliferator-activated receptor alpha	Homo sapiens	IC50	=	1520.0	nM	PMID[549884]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	IC50	=	850.0	nM	PMID[549884]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6300.0	nM	PMID[549885]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3100.0	nM	PMID[549885]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	12500.0	nM	PMID[549885]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	6300.0	nM	PMID[549885]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	6300.0	nM	PMID[549885]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	50000.0	nM	PMID[549885]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	MIC	>	50000.0	nM	PMID[549885]

☑ 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 NPC33728 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	300
0.1-0.2	1702
0.2-0.3	4640
0.3-0.4	14196
0.4-0.5	5000
0.5-0.6	7429
0.6-0.7	7115
0.7-0.8	1917
0.8-0.85	228
0.85-0.9	79
0.9-0.95	73
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC19808
0.9901	High Similarity	NPC174981
0.9806	High Similarity	NPC224527
0.9712	High Similarity	NPC166995
0.9619	High Similarity	NPC117846
0.9608	High Similarity	NPC232523
0.9608	High Similarity	NPC204901
0.9608	High Similarity	NPC158253
0.9604	High Similarity	NPC37802
0.951	High Similarity	NPC201662
0.951	High Similarity	NPC99836
0.951	High Similarity	NPC12640
0.9505	High Similarity	NPC102216
0.9505	High Similarity	NPC241891
0.9505	High Similarity	NPC218879
0.9505	High Similarity	NPC227458
0.9505	High Similarity	NPC244513
0.9439	High Similarity	NPC246760
0.9439	High Similarity	NPC84999
0.9434	High Similarity	NPC23804
0.9434	High Similarity	NPC261343
0.9429	High Similarity	NPC476632
0.9429	High Similarity	NPC165770
0.9429	High Similarity	NPC4493
0.9429	High Similarity	NPC225679
0.9423	High Similarity	NPC299568
0.9423	High Similarity	NPC186385
0.9412	High Similarity	NPC134829
0.934	High Similarity	NPC43525
0.932	High Similarity	NPC470700
0.932	High Similarity	NPC39097
0.932	High Similarity	NPC39664
0.932	High Similarity	NPC302681
0.932	High Similarity	NPC118286
0.932	High Similarity	NPC109691
0.9307	High Similarity	NPC143659
0.9307	High Similarity	NPC100340
0.9231	High Similarity	NPC54844
0.9223	High Similarity	NPC246056
0.9223	High Similarity	NPC474839
0.9216	High Similarity	NPC24404
0.9216	High Similarity	NPC222522
0.9216	High Similarity	NPC94351
0.9216	High Similarity	NPC313030
0.9216	High Similarity	NPC146798
0.9216	High Similarity	NPC249828
0.9216	High Similarity	NPC85479
0.9216	High Similarity	NPC71002
0.9216	High Similarity	NPC168303
0.9216	High Similarity	NPC53051
0.9216	High Similarity	NPC302219
0.9216	High Similarity	NPC106396
0.9216	High Similarity	NPC242342
0.9208	High Similarity	NPC10588
0.9208	High Similarity	NPC166761
0.9182	High Similarity	NPC144343
0.9182	High Similarity	NPC190514
0.9167	High Similarity	NPC107240
0.9143	High Similarity	NPC61885
0.9143	High Similarity	NPC63698
0.9126	High Similarity	NPC119860
0.9126	High Similarity	NPC30506
0.9118	High Similarity	NPC284011
0.9118	High Similarity	NPC147310
0.9118	High Similarity	NPC24407
0.9118	High Similarity	NPC192032
0.9118	High Similarity	NPC137415
0.9118	High Similarity	NPC72947
0.9118	High Similarity	NPC166313
0.9118	High Similarity	NPC11280
0.9118	High Similarity	NPC294186
0.9099	High Similarity	NPC184302
0.9091	High Similarity	NPC470760
0.9074	High Similarity	NPC319803
0.9038	High Similarity	NPC292452
0.901	High Similarity	NPC291789
0.9009	High Similarity	NPC9592
0.9009	High Similarity	NPC48781
0.9	High Similarity	NPC115808
0.8952	High Similarity	NPC248904
0.8938	High Similarity	NPC24125
0.8929	High Similarity	NPC191866
0.8919	High Similarity	NPC69261
0.8919	High Similarity	NPC33270
0.8909	High Similarity	NPC808
0.8899	High Similarity	NPC263753
0.8879	High Similarity	NPC202647
0.8868	High Similarity	NPC61033
0.8868	High Similarity	NPC305603
0.885	High Similarity	NPC69006
0.8839	High Similarity	NPC206
0.8835	High Similarity	NPC161571
0.8835	High Similarity	NPC275053
0.8835	High Similarity	NPC248573
0.8829	High Similarity	NPC150624
0.8818	High Similarity	NPC249270
0.8796	High Similarity	NPC224870
0.8796	High Similarity	NPC475018
0.8783	High Similarity	NPC77789
0.8783	High Similarity	NPC18128
0.875	High Similarity	NPC277588
0.8739	High Similarity	NPC232165
0.8739	High Similarity	NPC53906
0.8738	High Similarity	NPC80027
0.8713	High Similarity	NPC76938
0.8696	High Similarity	NPC39029
0.8684	High Similarity	NPC223451
0.8667	High Similarity	NPC168393
0.8654	High Similarity	NPC72729
0.8649	High Similarity	NPC276737
0.8649	High Similarity	NPC22610
0.8641	High Similarity	NPC79241
0.8641	High Similarity	NPC6597
0.8627	High Similarity	NPC32714
0.8621	High Similarity	NPC122175
0.8614	High Similarity	NPC295295
0.8609	High Similarity	NPC218753
0.8596	High Similarity	NPC121866
0.8596	High Similarity	NPC217174
0.8584	High Similarity	NPC221549
0.8584	High Similarity	NPC127894
0.8584	High Similarity	NPC474933
0.8584	High Similarity	NPC470759
0.8584	High Similarity	NPC15860
0.8584	High Similarity	NPC244816
0.8584	High Similarity	NPC219070
0.8584	High Similarity	NPC50521
0.8571	High Similarity	NPC252105
0.8571	High Similarity	NPC477685
0.8559	High Similarity	NPC105031
0.8558	High Similarity	NPC33675
0.8558	High Similarity	NPC299762
0.8545	High Similarity	NPC268032
0.8545	High Similarity	NPC151537
0.8544	High Similarity	NPC259512
0.8544	High Similarity	NPC312132
0.8534	High Similarity	NPC237667
0.8534	High Similarity	NPC476633
0.8519	High Similarity	NPC66834
0.8515	High Similarity	NPC231150
0.8505	High Similarity	NPC47284
0.8505	High Similarity	NPC117115
0.8496	Intermediate Similarity	NPC114064
0.8496	Intermediate Similarity	NPC54507
0.8496	Intermediate Similarity	NPC229147
0.8496	Intermediate Similarity	NPC141090
0.8496	Intermediate Similarity	NPC85292
0.8491	Intermediate Similarity	NPC471228
0.8491	Intermediate Similarity	NPC235762
0.8476	Intermediate Similarity	NPC129373
0.8476	Intermediate Similarity	NPC174911
0.8476	Intermediate Similarity	NPC294741
0.8476	Intermediate Similarity	NPC248396
0.8476	Intermediate Similarity	NPC48730
0.8475	Intermediate Similarity	NPC139774
0.8475	Intermediate Similarity	NPC224342
0.8475	Intermediate Similarity	NPC174729
0.8468	Intermediate Similarity	NPC473521
0.8468	Intermediate Similarity	NPC46940
0.8462	Intermediate Similarity	NPC152097
0.8448	Intermediate Similarity	NPC102639
0.8447	Intermediate Similarity	NPC274678
0.8447	Intermediate Similarity	NPC26244
0.844	Intermediate Similarity	NPC306295
0.8435	Intermediate Similarity	NPC137294
0.8435	Intermediate Similarity	NPC85895
0.8431	Intermediate Similarity	NPC162314
0.8431	Intermediate Similarity	NPC306884
0.8431	Intermediate Similarity	NPC94139
0.8431	Intermediate Similarity	NPC3358
0.8431	Intermediate Similarity	NPC210497
0.8431	Intermediate Similarity	NPC147284
0.8426	Intermediate Similarity	NPC67250
0.8426	Intermediate Similarity	NPC53740
0.8417	Intermediate Similarity	NPC46978
0.8417	Intermediate Similarity	NPC236760
0.8417	Intermediate Similarity	NPC473221
0.8416	Intermediate Similarity	NPC192
0.8411	Intermediate Similarity	NPC475225
0.8411	Intermediate Similarity	NPC238696
0.8407	Intermediate Similarity	NPC464
0.8407	Intermediate Similarity	NPC167934
0.8407	Intermediate Similarity	NPC185541
0.8396	Intermediate Similarity	NPC12221
0.8396	Intermediate Similarity	NPC80800
0.839	Intermediate Similarity	NPC53567
0.8381	Intermediate Similarity	NPC260775
0.8378	Intermediate Similarity	NPC54373
0.8378	Intermediate Similarity	NPC95716
0.8365	Intermediate Similarity	NPC473388
0.8364	Intermediate Similarity	NPC58865
0.835	Intermediate Similarity	NPC151715
0.835	Intermediate Similarity	NPC128062
0.8349	Intermediate Similarity	NPC320439
0.8349	Intermediate Similarity	NPC176527
0.8349	Intermediate Similarity	NPC151477
0.8348	Intermediate Similarity	NPC131118
0.8333	Intermediate Similarity	NPC471350
0.8333	Intermediate Similarity	NPC203113
0.8333	Intermediate Similarity	NPC91204

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 NPC33728 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	1034
0.2-0.3	1293
0.3-0.4	2961
0.4-0.5	1868
0.5-0.6	1186
0.6-0.7	437
0.7-0.8	63
0.8-0.85	10
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9423	High Similarity	NPD4750	Phase 3
0.8932	High Similarity	NPD940	Approved
0.8932	High Similarity	NPD846	Approved
0.8835	High Similarity	NPD1242	Phase 1
0.8812	High Similarity	NPD844	Approved
0.8544	High Similarity	NPD288	Approved
0.8447	Intermediate Similarity	NPD2860	Approved
0.8447	Intermediate Similarity	NPD2859	Approved
0.8381	Intermediate Similarity	NPD3020	Approved
0.835	Intermediate Similarity	NPD2934	Approved
0.835	Intermediate Similarity	NPD2933	Approved
0.8304	Intermediate Similarity	NPD7635	Approved
0.8279	Intermediate Similarity	NPD4625	Phase 3
0.8235	Intermediate Similarity	NPD4749	Approved
0.8182	Intermediate Similarity	NPD2342	Discontinued
0.8131	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD3021	Approved
0.8036	Intermediate Similarity	NPD3022	Approved
0.7905	Intermediate Similarity	NPD845	Approved
0.7886	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD1610	Phase 2
0.776	Intermediate Similarity	NPD4908	Phase 1
0.7731	Intermediate Similarity	NPD1548	Phase 1
0.7698	Intermediate Similarity	NPD3027	Phase 3
0.7638	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD6671	Approved
0.7619	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1809	Phase 2
0.7565	Intermediate Similarity	NPD1792	Phase 2
0.754	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD9089	Approved
0.75	Intermediate Similarity	NPD6099	Approved
0.75	Intermediate Similarity	NPD6100	Approved
0.748	Intermediate Similarity	NPD1201	Approved
0.7476	Intermediate Similarity	NPD111	Approved
0.7456	Intermediate Similarity	NPD1445	Approved
0.7456	Intermediate Similarity	NPD1444	Approved
0.7438	Intermediate Similarity	NPD3091	Approved
0.7426	Intermediate Similarity	NPD9093	Approved
0.7424	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD497	Approved
0.7395	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD1613	Approved
0.7385	Intermediate Similarity	NPD943	Approved
0.736	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD422	Phase 1
0.7339	Intermediate Similarity	NPD3092	Approved
0.7321	Intermediate Similarity	NPD3028	Approved
0.7317	Intermediate Similarity	NPD2286	Discontinued
0.7317	Intermediate Similarity	NPD2932	Approved
0.7317	Intermediate Similarity	NPD3019	Approved
0.7317	Intermediate Similarity	NPD4059	Approved
0.7311	Intermediate Similarity	NPD2234	Approved
0.7311	Intermediate Similarity	NPD2229	Approved
0.7311	Intermediate Similarity	NPD2228	Approved
0.7311	Intermediate Similarity	NPD496	Approved
0.7311	Intermediate Similarity	NPD495	Approved
0.7311	Intermediate Similarity	NPD498	Approved
0.7297	Intermediate Similarity	NPD9273	Approved
0.7295	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1607	Approved
0.7273	Intermediate Similarity	NPD2568	Approved
0.7266	Intermediate Similarity	NPD3018	Phase 2
0.7266	Intermediate Similarity	NPD2861	Phase 2
0.7258	Intermediate Similarity	NPD1983	Approved
0.7258	Intermediate Similarity	NPD1980	Approved
0.7258	Intermediate Similarity	NPD1981	Approved
0.7246	Intermediate Similarity	NPD7390	Discontinued
0.7244	Intermediate Similarity	NPD3094	Phase 2
0.7244	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1470	Approved
0.7236	Intermediate Similarity	NPD4093	Discontinued
0.7177	Intermediate Similarity	NPD4626	Approved
0.7177	Intermediate Similarity	NPD4589	Approved
0.7177	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6696	Suspended
0.7154	Intermediate Similarity	NPD5304	Approved
0.7154	Intermediate Similarity	NPD5303	Approved
0.7153	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1240	Approved
0.7111	Intermediate Similarity	NPD5404	Approved
0.7111	Intermediate Similarity	NPD5406	Approved
0.7111	Intermediate Similarity	NPD5405	Approved
0.7111	Intermediate Similarity	NPD5408	Approved
0.7103	Intermediate Similarity	NPD9094	Approved
0.7099	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD2983	Phase 2
0.7087	Intermediate Similarity	NPD2982	Phase 2
0.7063	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD599	Approved
0.7054	Intermediate Similarity	NPD858	Approved
0.7054	Intermediate Similarity	NPD602	Approved
0.7054	Intermediate Similarity	NPD859	Approved
0.7049	Intermediate Similarity	NPD709	Approved
0.7045	Intermediate Similarity	NPD6407	Approved
0.7045	Intermediate Similarity	NPD6405	Approved
0.7043	Intermediate Similarity	NPD9500	Approved
0.7043	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD1751	Approved
0.704	Intermediate Similarity	NPD3095	Discontinued
0.7025	Intermediate Similarity	NPD5283	Phase 1
0.7016	Intermediate Similarity	NPD7330	Discontinued
0.7015	Intermediate Similarity	NPD4097	Suspended
0.7009	Intermediate Similarity	NPD968	Approved
0.7008	Intermediate Similarity	NPD2230	Approved
0.7008	Intermediate Similarity	NPD2233	Approved
0.7008	Intermediate Similarity	NPD2981	Phase 2
0.7008	Intermediate Similarity	NPD2232	Approved
0.7	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD228	Approved
0.6992	Remote Similarity	NPD1555	Discontinued
0.6992	Remote Similarity	NPD2238	Phase 2
0.6977	Remote Similarity	NPD2797	Approved
0.6967	Remote Similarity	NPD1791	Approved
0.6967	Remote Similarity	NPD1793	Approved
0.6953	Remote Similarity	NPD4659	Approved
0.6923	Remote Similarity	NPD6584	Phase 3
0.6912	Remote Similarity	NPD1510	Phase 2
0.6906	Remote Similarity	NPD3892	Phase 2
0.6905	Remote Similarity	NPD1778	Approved
0.6885	Remote Similarity	NPD1398	Phase 1
0.6885	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2561	Approved
0.6875	Remote Similarity	NPD1608	Approved
0.6875	Remote Similarity	NPD2562	Approved
0.687	Remote Similarity	NPD5736	Approved
0.687	Remote Similarity	NPD1616	Discontinued
0.6866	Remote Similarity	NPD4060	Phase 1
0.6861	Remote Similarity	NPD2935	Discontinued
0.6861	Remote Similarity	NPD1551	Phase 2
0.6855	Remote Similarity	NPD7340	Approved
0.6855	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3055	Approved
0.6846	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1133	Approved
0.6846	Remote Similarity	NPD1134	Approved
0.6846	Remote Similarity	NPD3053	Approved
0.6846	Remote Similarity	NPD1135	Approved
0.6846	Remote Similarity	NPD1129	Approved
0.6846	Remote Similarity	NPD1164	Approved
0.6846	Remote Similarity	NPD4103	Phase 2
0.6846	Remote Similarity	NPD1131	Approved
0.6838	Remote Similarity	NPD3554	Approved
0.6838	Remote Similarity	NPD3553	Approved
0.6838	Remote Similarity	NPD9608	Approved
0.6838	Remote Similarity	NPD3555	Approved
0.6838	Remote Similarity	NPD9610	Approved
0.6838	Remote Similarity	NPD3552	Approved
0.6835	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5451	Approved
0.6831	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7447	Phase 1
0.6829	Remote Similarity	NPD9618	Approved
0.6829	Remote Similarity	NPD9614	Approved
0.6825	Remote Similarity	NPD5691	Approved
0.6825	Remote Similarity	NPD1651	Approved
0.6807	Remote Similarity	NPD290	Approved
0.6803	Remote Similarity	NPD9377	Approved
0.6803	Remote Similarity	NPD9379	Approved
0.6797	Remote Similarity	NPD1611	Approved
0.6794	Remote Similarity	NPD2195	Approved
0.6794	Remote Similarity	NPD2194	Approved
0.6788	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3750	Approved
0.6777	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5311	Approved
0.6769	Remote Similarity	NPD1283	Approved
0.6769	Remote Similarity	NPD5310	Approved
0.6767	Remote Similarity	NPD5156	Approved
0.6767	Remote Similarity	NPD5155	Approved
0.6761	Remote Similarity	NPD7212	Phase 2
0.6761	Remote Similarity	NPD7213	Phase 3
0.675	Remote Similarity	NPD9266	Approved
0.675	Remote Similarity	NPD74	Approved
0.675	Remote Similarity	NPD2684	Approved
0.6748	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1759	Phase 1
0.6742	Remote Similarity	NPD3637	Approved
0.6742	Remote Similarity	NPD3635	Approved
0.6742	Remote Similarity	NPD3636	Approved
0.6733	Remote Similarity	NPD9087	Approved
0.672	Remote Similarity	NPD9493	Approved
0.6719	Remote Similarity	NPD3026	Approved
0.6719	Remote Similarity	NPD3496	Discontinued
0.6719	Remote Similarity	NPD3023	Approved
0.6716	Remote Similarity	NPD3268	Approved
0.6715	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD3025	Approved
0.6693	Remote Similarity	NPD3024	Approved
0.6692	Remote Similarity	NPD2605	Approved
0.6692	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6583	Phase 3
0.6692	Remote Similarity	NPD2606	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