NPASS Compound

Structure

NPC84999 OpenBabel07101719152D 27 29 0 0 1 0 0 0 0 0999 V2000 -0.8660 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 -1.7321 -3.0000 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 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 2.5981 1.5000 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 -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 0.8660 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 -1.7321 -2.0000 0.0000 C 0 0 1 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 4.3301 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 2 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 4.3301 2.5000 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 -0.5000 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 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 2 15 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 18 2 0 0 0 0 7 21 2 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 17 2 0 0 0 0 13 22 1 0 0 0 0 14 17 1 0 0 0 0 14 23 2 0 0 0 0 16 3 1 1 0 0 0 18 21 1 0 0 0 0 19 15 1 6 0 0 0 19 20 1 0 0 0 0 20 24 1 1 0 0 0 21 25 1 0 0 0 0 22 24 2 0 0 0 0 22 26 1 0 0 0 0 23 24 1 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.2
Volume:	403.27
LogP:	6.217
LogD:	4.364
LogS:	-3.449
# Rotatable Bonds:	4
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.456
Synthetic Accessibility Score:	3.659
Fsp3:	0.333
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:	-4.941
MDCK Permeability:	1.5102107681741472e-05
Pgp-inhibitor:	0.53
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.951
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	99.17867279052734%
Volume Distribution (VD):	2.463
Pgp-substrate:	0.5565930008888245%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.803
CYP2C19-inhibitor:	0.941
CYP2C19-substrate:	0.103
CYP2C9-inhibitor:	0.856
CYP2C9-substrate:	0.979
CYP2D6-inhibitor:	0.751
CYP2D6-substrate:	0.859
CYP3A4-inhibitor:	0.418
CYP3A4-substrate:	0.215

ADMET: Excretion

Clearance (CL):	10.736
Half-life (T1/2):	0.16

ADMET: Toxicity

hERG Blockers:	0.211
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.845
AMES Toxicity:	0.462
Rat Oral Acute Toxicity:	0.147
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.959
Carcinogencity:	0.529
Eye Corrosion:	0.035
Eye Irritation:	0.948
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC84999

Natural Product ID:	NPC84999
*Common Name:**	Machaeridiol B
IUPAC Name:	5-[(E)-2-(2-hydroxyphenyl)ethenyl]-2-[(1S,2S,5S)-5-methyl-2-prop-1-en-2-ylcyclohexyl]benzene-1,3-diol
Synonyms:	Machaeridiol B
Standard InCHIKey:	QZIGMIOMEWTNCH-VVNJCPJNSA-N
Standard InCHI:	InChI=1S/C24H28O3/c1-15(2)19-11-8-16(3)12-20(19)24-22(26)13-17(14-23(24)27)9-10-18-6-4-5-7-21(18)25/h4-7,9-10,13-14,16,19-20,25-27H,1,8,11-12H2,2-3H3/b10-9+/t16-,19+,20-/m0/s1
SMILES:	C[C@H]1CC[C@@H]([C@H](C1)c1c(O)cc(cc1O)/C=C/c1ccccc1O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467407
PubChem CID:	10361425
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
NPO33402	machaerium multiflorum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[11678659]
NPO33402	machaerium multiflorum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[12828466]

☑ 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	7
MIC	4
Others	5

Activity Type	# Activity
Organism	14
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug.mL-1	PMID[472763]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	10.0	ug.mL-1	PMID[472763]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	8.0	ug.mL-1	PMID[472763]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	6.25	ug ml-1	PMID[472763]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	2.0	ug.mL-1	PMID[472763]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	3.5	ug.mL-1	PMID[472763]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	2.6	ug.mL-1	PMID[472763]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	2.0	ug.mL-1	PMID[472763]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.64	ug.mL-1	PMID[472763]
NPT2	Others	Unspecified		Ratio IC50	>	7.4	n.a.	PMID[472763]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.22	ug.mL-1	PMID[472763]
NPT2	Others	Unspecified		Ratio IC50	>	22.0	n.a.	PMID[472763]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	0.9	ug.mL-1	PMID[472763]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	6.25	ug.mL-1	PMID[472763]

☑ 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 NPC84999 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	320
0.1-0.2	1653
0.2-0.3	3667
0.3-0.4	11397
0.4-0.5	8308
0.5-0.6	7412
0.6-0.7	7745
0.7-0.8	1871
0.8-0.85	233
0.85-0.9	76
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC246760
0.9626	High Similarity	NPC224527
0.9439	High Similarity	NPC19808
0.9439	High Similarity	NPC33728
0.9375	High Similarity	NPC206
0.9346	High Similarity	NPC174981
0.9273	High Similarity	NPC23804
0.9273	High Similarity	NPC117846
0.9259	High Similarity	NPC186385
0.9259	High Similarity	NPC299568
0.9189	High Similarity	NPC107240
0.9189	High Similarity	NPC249270
0.9182	High Similarity	NPC166995
0.9091	High Similarity	NPC225679
0.9091	High Similarity	NPC4493
0.9091	High Similarity	NPC165770
0.9091	High Similarity	NPC476632
0.9074	High Similarity	NPC204901
0.9074	High Similarity	NPC232523
0.9074	High Similarity	NPC158253
0.9065	High Similarity	NPC37802
0.9043	High Similarity	NPC69006
0.9009	High Similarity	NPC43525
0.8981	High Similarity	NPC99836
0.8981	High Similarity	NPC201662
0.8981	High Similarity	NPC12640
0.8972	High Similarity	NPC244513
0.8972	High Similarity	NPC218879
0.8972	High Similarity	NPC102216
0.8972	High Similarity	NPC241891
0.8972	High Similarity	NPC227458
0.8947	High Similarity	NPC470760
0.8929	High Similarity	NPC319803
0.8929	High Similarity	NPC261343
0.8929	High Similarity	NPC263753
0.8889	High Similarity	NPC134829
0.887	High Similarity	NPC9592
0.887	High Similarity	NPC48781
0.886	High Similarity	NPC115808
0.8839	High Similarity	NPC46940
0.8829	High Similarity	NPC224870
0.8824	High Similarity	NPC224342
0.8818	High Similarity	NPC61885
0.8818	High Similarity	NPC11554
0.8818	High Similarity	NPC63698
0.8807	High Similarity	NPC39097
0.8807	High Similarity	NPC118286
0.8807	High Similarity	NPC470700
0.8807	High Similarity	NPC248904
0.8807	High Similarity	NPC302681
0.8807	High Similarity	NPC39664
0.8807	High Similarity	NPC109691
0.8785	High Similarity	NPC100340
0.8785	High Similarity	NPC143659
0.877	High Similarity	NPC222108
0.877	High Similarity	NPC96719
0.8761	High Similarity	NPC715
0.875	High Similarity	NPC151537
0.875	High Similarity	NPC95716
0.875	High Similarity	NPC77772
0.8739	High Similarity	NPC202647
0.8727	High Similarity	NPC54844
0.8716	High Similarity	NPC117115
0.8716	High Similarity	NPC474839
0.8716	High Similarity	NPC246056
0.8707	High Similarity	NPC190514
0.8707	High Similarity	NPC144343
0.8704	High Similarity	NPC242342
0.8704	High Similarity	NPC168303
0.8704	High Similarity	NPC313030
0.8704	High Similarity	NPC85479
0.8704	High Similarity	NPC302219
0.8704	High Similarity	NPC106396
0.8704	High Similarity	NPC53051
0.8704	High Similarity	NPC94351
0.8704	High Similarity	NPC222522
0.8704	High Similarity	NPC71002
0.8704	High Similarity	NPC24404
0.8704	High Similarity	NPC146798
0.8704	High Similarity	NPC249828
0.8696	High Similarity	NPC141001
0.8692	High Similarity	NPC10588
0.8692	High Similarity	NPC166761
0.8684	High Similarity	NPC195922
0.8684	High Similarity	NPC471534
0.8678	High Similarity	NPC170485
0.8678	High Similarity	NPC9292
0.8678	High Similarity	NPC145659
0.8655	High Similarity	NPC120172
0.8644	High Similarity	NPC24125
0.8632	High Similarity	NPC191866
0.8632	High Similarity	NPC184302
0.8624	High Similarity	NPC119860
0.8624	High Similarity	NPC30506
0.8621	High Similarity	NPC304510
0.8621	High Similarity	NPC172219
0.8611	High Similarity	NPC147310
0.8611	High Similarity	NPC294186
0.8611	High Similarity	NPC137415
0.8611	High Similarity	NPC166313
0.8611	High Similarity	NPC192032
0.8611	High Similarity	NPC24407
0.8611	High Similarity	NPC284011
0.8611	High Similarity	NPC72947
0.8611	High Similarity	NPC11280
0.8595	High Similarity	NPC105031
0.8584	High Similarity	NPC266937
0.8584	High Similarity	NPC260323
0.8584	High Similarity	NPC470770
0.8584	High Similarity	NPC176279
0.8571	High Similarity	NPC237667
0.8571	High Similarity	NPC39029
0.8571	High Similarity	NPC58865
0.8559	High Similarity	NPC151477
0.8547	High Similarity	NPC471671
0.8545	High Similarity	NPC292452
0.8537	High Similarity	NPC215300
0.8532	High Similarity	NPC168393
0.8519	High Similarity	NPC72729
0.8512	High Similarity	NPC97578
0.8512	High Similarity	NPC138248
0.8512	High Similarity	NPC228503
0.8509	High Similarity	NPC473521
0.8509	High Similarity	NPC62867
0.8509	High Similarity	NPC250323
0.8509	High Similarity	NPC177962
0.8505	High Similarity	NPC79241
0.8505	High Similarity	NPC6597
0.8505	High Similarity	NPC291789
0.85	High Similarity	NPC122175
0.8496	Intermediate Similarity	NPC132720
0.8496	Intermediate Similarity	NPC141782
0.848	Intermediate Similarity	NPC8899
0.8475	Intermediate Similarity	NPC151197
0.8475	Intermediate Similarity	NPC121866
0.8475	Intermediate Similarity	NPC469644
0.8475	Intermediate Similarity	NPC217174
0.8468	Intermediate Similarity	NPC271274
0.8468	Intermediate Similarity	NPC16577
0.8462	Intermediate Similarity	NPC277588
0.8462	Intermediate Similarity	NPC69261
0.8462	Intermediate Similarity	NPC33270
0.8455	Intermediate Similarity	NPC238696
0.8455	Intermediate Similarity	NPC53781
0.8448	Intermediate Similarity	NPC469719
0.8448	Intermediate Similarity	NPC35797
0.8448	Intermediate Similarity	NPC192948
0.8448	Intermediate Similarity	NPC808
0.8443	Intermediate Similarity	NPC105718
0.8443	Intermediate Similarity	NPC113495
0.8443	Intermediate Similarity	NPC278955
0.844	Intermediate Similarity	NPC51015
0.843	Intermediate Similarity	NPC53567
0.8421	Intermediate Similarity	NPC469912
0.8413	Intermediate Similarity	NPC469611
0.8411	Intermediate Similarity	NPC259512
0.8411	Intermediate Similarity	NPC312132
0.8407	Intermediate Similarity	NPC314187
0.8403	Intermediate Similarity	NPC223451
0.8393	Intermediate Similarity	NPC66834
0.8393	Intermediate Similarity	NPC305603
0.8393	Intermediate Similarity	NPC61033
0.8393	Intermediate Similarity	NPC320439
0.839	Intermediate Similarity	NPC469609
0.8387	Intermediate Similarity	NPC38017
0.8376	Intermediate Similarity	NPC308311
0.8376	Intermediate Similarity	NPC92
0.8376	Intermediate Similarity	NPC38893
0.8376	Intermediate Similarity	NPC150624
0.8376	Intermediate Similarity	NPC261973
0.8376	Intermediate Similarity	NPC469663
0.8376	Intermediate Similarity	NPC471668
0.8376	Intermediate Similarity	NPC477137
0.8376	Intermediate Similarity	NPC219112
0.8362	Intermediate Similarity	NPC268160
0.8361	Intermediate Similarity	NPC174729
0.8361	Intermediate Similarity	NPC139774
0.8349	Intermediate Similarity	NPC248573
0.8349	Intermediate Similarity	NPC275053
0.8349	Intermediate Similarity	NPC161571
0.8348	Intermediate Similarity	NPC302371
0.8347	Intermediate Similarity	NPC71094
0.8347	Intermediate Similarity	NPC77789
0.8347	Intermediate Similarity	NPC18128
0.8346	Intermediate Similarity	NPC469610
0.8333	Intermediate Similarity	NPC282508
0.8333	Intermediate Similarity	NPC13482
0.8333	Intermediate Similarity	NPC472590
0.8333	Intermediate Similarity	NPC475018
0.8333	Intermediate Similarity	NPC296683
0.8333	Intermediate Similarity	NPC102639
0.8333	Intermediate Similarity	NPC471517
0.832	Intermediate Similarity	NPC471518
0.832	Intermediate Similarity	NPC471519
0.8319	Intermediate Similarity	NPC176893
0.8306	Intermediate Similarity	NPC473221
0.8306	Intermediate Similarity	NPC46978
0.8305	Intermediate Similarity	NPC477136
0.8305	Intermediate Similarity	NPC299180
0.8305	Intermediate Similarity	NPC50521

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 NPC84999 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	956
0.2-0.3	1140
0.3-0.4	3000
0.4-0.5	2028
0.5-0.6	1202
0.6-0.7	417
0.7-0.8	71
0.8-0.85	8
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9259	High Similarity	NPD4750	Phase 3
0.8559	High Similarity	NPD2342	Discontinued
0.8509	High Similarity	NPD7635	Approved
0.8468	Intermediate Similarity	NPD4625	Phase 3
0.844	Intermediate Similarity	NPD846	Approved
0.844	Intermediate Similarity	NPD940	Approved
0.8411	Intermediate Similarity	NPD288	Approved
0.8349	Intermediate Similarity	NPD1242	Phase 1
0.8318	Intermediate Similarity	NPD844	Approved
0.8279	Intermediate Similarity	NPD4749	Approved
0.8257	Intermediate Similarity	NPD3020	Approved
0.808	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD2859	Approved
0.7982	Intermediate Similarity	NPD2860	Approved
0.7969	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD845	Approved
0.7953	Intermediate Similarity	NPD4908	Phase 1
0.7934	Intermediate Similarity	NPD3091	Approved
0.7931	Intermediate Similarity	NPD3022	Approved
0.7931	Intermediate Similarity	NPD3021	Approved
0.789	Intermediate Similarity	NPD2934	Approved
0.789	Intermediate Similarity	NPD2933	Approved
0.7857	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD1610	Phase 2
0.7823	Intermediate Similarity	NPD3092	Approved
0.7823	Intermediate Similarity	NPD1201	Approved
0.7805	Intermediate Similarity	NPD3019	Approved
0.7805	Intermediate Similarity	NPD4059	Approved
0.7744	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD4093	Discontinued
0.7717	Intermediate Similarity	NPD3094	Phase 2
0.7687	Intermediate Similarity	NPD6100	Approved
0.7687	Intermediate Similarity	NPD6099	Approved
0.7661	Intermediate Similarity	NPD2932	Approved
0.7661	Intermediate Similarity	NPD2286	Discontinued
0.7627	Intermediate Similarity	NPD1792	Phase 2
0.7623	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1470	Approved
0.7568	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD7390	Discontinued
0.752	Intermediate Similarity	NPD3095	Discontinued
0.75	Intermediate Similarity	NPD1809	Phase 2
0.75	Intermediate Similarity	NPD1548	Phase 1
0.7463	Intermediate Similarity	NPD4097	Suspended
0.7459	Intermediate Similarity	NPD497	Approved
0.7442	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD5406	Approved
0.7426	Intermediate Similarity	NPD5408	Approved
0.7426	Intermediate Similarity	NPD5404	Approved
0.7426	Intermediate Similarity	NPD5405	Approved
0.7405	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD495	Approved
0.7377	Intermediate Similarity	NPD498	Approved
0.7377	Intermediate Similarity	NPD496	Approved
0.7373	Intermediate Similarity	NPD1445	Approved
0.7373	Intermediate Similarity	NPD1444	Approved
0.7348	Intermediate Similarity	NPD3027	Phase 3
0.7338	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD2861	Phase 2
0.7328	Intermediate Similarity	NPD5736	Approved
0.7317	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6671	Approved
0.7244	Intermediate Similarity	NPD4626	Approved
0.7244	Intermediate Similarity	NPD1751	Approved
0.7236	Intermediate Similarity	NPD2229	Approved
0.7236	Intermediate Similarity	NPD2234	Approved
0.7236	Intermediate Similarity	NPD2228	Approved
0.7231	Intermediate Similarity	NPD6696	Suspended
0.7226	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5304	Approved
0.7222	Intermediate Similarity	NPD5303	Approved
0.7218	Intermediate Similarity	NPD5156	Approved
0.7218	Intermediate Similarity	NPD5155	Approved
0.7188	Intermediate Similarity	NPD3026	Approved
0.7188	Intermediate Similarity	NPD3023	Approved
0.7185	Intermediate Similarity	NPD1613	Approved
0.7185	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD3025	Approved
0.7165	Intermediate Similarity	NPD3024	Approved
0.7143	Intermediate Similarity	NPD2605	Approved
0.7143	Intermediate Similarity	NPD2606	Approved
0.7132	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD4624	Approved
0.7111	Intermediate Similarity	NPD6663	Approved
0.7109	Intermediate Similarity	NPD4589	Approved
0.7109	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD9089	Approved
0.7097	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD2230	Approved
0.7077	Intermediate Similarity	NPD2233	Approved
0.7077	Intermediate Similarity	NPD2232	Approved
0.7068	Intermediate Similarity	NPD3635	Approved
0.7068	Intermediate Similarity	NPD3636	Approved
0.7068	Intermediate Similarity	NPD3637	Approved
0.7064	Intermediate Similarity	NPD111	Approved
0.7063	Intermediate Similarity	NPD7340	Approved
0.7059	Intermediate Similarity	NPD4060	Phase 1
0.7059	Intermediate Similarity	NPD943	Approved
0.7059	Intermediate Similarity	NPD2238	Phase 2
0.7045	Intermediate Similarity	NPD2797	Approved
0.7029	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD3594	Approved
0.7015	Intermediate Similarity	NPD3595	Approved
0.7009	Intermediate Similarity	NPD9093	Approved
0.7	Intermediate Similarity	NPD4725	Approved
0.7	Intermediate Similarity	NPD4726	Approved
0.7	Intermediate Similarity	NPD4721	Approved
0.7	Intermediate Similarity	NPD422	Phase 1
0.6992	Remote Similarity	NPD2194	Approved
0.6992	Remote Similarity	NPD2195	Approved
0.6984	Remote Similarity	NPD709	Approved
0.6972	Remote Similarity	NPD3892	Phase 2
0.697	Remote Similarity	NPD1283	Approved
0.696	Remote Similarity	NPD5283	Phase 1
0.696	Remote Similarity	NPD1398	Phase 1
0.6957	Remote Similarity	NPD1607	Approved
0.6957	Remote Similarity	NPD2568	Approved
0.6953	Remote Similarity	NPD7330	Discontinued
0.6953	Remote Similarity	NPD7741	Discontinued
0.6949	Remote Similarity	NPD3028	Approved
0.694	Remote Similarity	NPD3018	Phase 2
0.6935	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD3620	Phase 2
0.6923	Remote Similarity	NPD9273	Approved
0.6923	Remote Similarity	NPD1980	Approved
0.6923	Remote Similarity	NPD1983	Approved
0.6923	Remote Similarity	NPD1981	Approved
0.6913	Remote Similarity	NPD37	Approved
0.6899	Remote Similarity	NPD5691	Approved
0.6899	Remote Similarity	NPD1651	Approved
0.6897	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5327	Phase 3
0.6894	Remote Similarity	NPD4659	Approved
0.6884	Remote Similarity	NPD5735	Approved
0.6883	Remote Similarity	NPD6232	Discontinued
0.687	Remote Similarity	NPD1611	Approved
0.6866	Remote Similarity	NPD6584	Phase 3
0.6861	Remote Similarity	NPD6405	Approved
0.6861	Remote Similarity	NPD6407	Approved
0.6859	Remote Similarity	NPD7473	Discontinued
0.6857	Remote Similarity	NPD7743	Approved
0.6857	Remote Similarity	NPD7742	Approved
0.6853	Remote Similarity	NPD3750	Approved
0.6833	Remote Similarity	NPD9500	Approved
0.6831	Remote Similarity	NPD4257	Approved
0.6831	Remote Similarity	NPD4256	Phase 2
0.6828	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7041	Phase 2
0.6825	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1608	Approved
0.6812	Remote Similarity	NPD4140	Approved
0.6812	Remote Similarity	NPD1240	Approved
0.6812	Remote Similarity	NPD1555	Discontinued
0.6797	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6234	Discontinued
0.6791	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD1164	Approved
0.6791	Remote Similarity	NPD4103	Phase 2
0.6788	Remote Similarity	NPD3268	Approved
0.6788	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD7447	Phase 1
0.6776	Remote Similarity	NPD4966	Approved
0.6776	Remote Similarity	NPD4967	Phase 2
0.6776	Remote Similarity	NPD4965	Approved
0.6774	Remote Similarity	NPD5451	Approved
0.6772	Remote Similarity	NPD1793	Approved
0.6772	Remote Similarity	NPD5951	Approved
0.6772	Remote Similarity	NPD1791	Approved
0.6767	Remote Similarity	NPD2982	Phase 2
0.6767	Remote Similarity	NPD2983	Phase 2
0.6761	Remote Similarity	NPD5763	Approved
0.6761	Remote Similarity	NPD5762	Approved
0.6761	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1281	Approved
0.6741	Remote Similarity	NPD599	Approved
0.6741	Remote Similarity	NPD858	Approved
0.6741	Remote Similarity	NPD602	Approved
0.6741	Remote Similarity	NPD859	Approved
0.6738	Remote Similarity	NPD1510	Phase 2
0.6736	Remote Similarity	NPD7003	Approved
0.6726	Remote Similarity	NPD9094	Approved
0.6719	Remote Similarity	NPD6387	Discontinued
0.6718	Remote Similarity	NPD5126	Approved
0.6718	Remote Similarity	NPD5125	Phase 3
0.6714	Remote Similarity	NPD6353	Approved
0.6714	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD7037	Approved
0.6712	Remote Similarity	NPD2420	Approved
0.6712	Remote Similarity	NPD7212	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