NPASS Compound

Structure

NPC475017 OpenBabel07101719132D 28 29 0 0 0 0 0 0 0 0999 V2000 -11.2583 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 1.7321 -2.0000 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 -4.3301 -0.5000 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 -6.9282 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -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 0.8660 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 -9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 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 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 19 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 23 2 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 20 2 0 0 0 0 18 20 1 0 0 0 0 20 26 1 0 0 0 0 21 24 1 0 0 0 0 21 25 2 0 0 0 0 22 24 2 0 0 0 0 22 27 1 0 0 0 0 23 24 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.23
Volume:	423.253
LogP:	5.79
LogD:	4.397
LogS:	-6.578
# Rotatable Bonds:	13
TPSA:	44.76
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.32
Synthetic Accessibility Score:	1.953
Fsp3:	0.458
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:	-4.821
MDCK Permeability:	1.5333298506448045e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.967
30% Bioavailability (F30%):	0.605

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.234
Plasma Protein Binding (PPB):	93.1108627319336%
Volume Distribution (VD):	0.845
Pgp-substrate:	0.6891902089118958%

ADMET: Metabolism

CYP1A2-inhibitor:	0.7
CYP1A2-substrate:	0.949
CYP2C19-inhibitor:	0.881
CYP2C19-substrate:	0.506
CYP2C9-inhibitor:	0.864
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.448
CYP2D6-substrate:	0.934
CYP3A4-inhibitor:	0.837
CYP3A4-substrate:	0.575

ADMET: Excretion

Clearance (CL):	7.574
Half-life (T1/2):	0.118

ADMET: Toxicity

hERG Blockers:	0.72
Human Hepatotoxicity (H-HT):	0.056
Drug-inuced Liver Injury (DILI):	0.893
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.038
Skin Sensitization:	0.94
Carcinogencity:	0.078
Eye Corrosion:	0.004
Eye Irritation:	0.841
Respiratory Toxicity:	0.708

Download Data

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

Natural Product: NPC475017

Natural Product ID:	NPC475017
*Common Name:**	1-(2,6-Dimethoxyphenyl)-9-(4-Methoxyphenyl)Nonan-1-One
IUPAC Name:	1-(2,6-dimethoxyphenyl)-9-(4-methoxyphenyl)nonan-1-one
Synonyms:
Standard InCHIKey:	DBXOINQVJUWNRR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H32O4/c1-26-20-17-15-19(16-18-20)11-8-6-4-5-7-9-12-21(25)24-22(27-2)13-10-14-23(24)28-3/h10,13-18H,4-9,11-12H2,1-3H3
SMILES:	COc1ccc(cc1)CCCCCCCCC(=O)c1c(OC)cccc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491993
PubChem CID:	13965863
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17998162]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955885]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20879744]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27419473]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Aril	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5241	Myristica fragrans	Species	Myristicaceae	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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	<	32.0	ug.mL-1	PMID[527951]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	<	32.0	ug.mL-1	PMID[527951]
NPT3730	Organism	Enterococcus durans	Enterococcus durans	MIC	<	32.0	ug.mL-1	PMID[527951]
NPT20	Organism	Candida albicans	Candida albicans	MIC	<	32.0	ug.mL-1	PMID[527951]

☑ 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 NPC475017 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	386
0.1-0.2	1574
0.2-0.3	4488
0.3-0.4	12080
0.4-0.5	5891
0.5-0.6	4260
0.6-0.7	6777
0.7-0.8	5504
0.8-0.85	1189
0.85-0.9	463
0.9-0.95	79
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9597	High Similarity	NPC211120
0.9524	High Similarity	NPC475008
0.9524	High Similarity	NPC186097
0.9524	High Similarity	NPC475009
0.9375	High Similarity	NPC204960
0.9375	High Similarity	NPC144051
0.9375	High Similarity	NPC159623
0.9375	High Similarity	NPC28753
0.9375	High Similarity	NPC294593
0.9375	High Similarity	NPC20560
0.9375	High Similarity	NPC18877
0.9375	High Similarity	NPC223354
0.9375	High Similarity	NPC82225
0.9302	High Similarity	NPC286336
0.9297	High Similarity	NPC101294
0.9297	High Similarity	NPC473655
0.9297	High Similarity	NPC182428
0.9274	High Similarity	NPC65041
0.9231	High Similarity	NPC13575
0.9231	High Similarity	NPC99854
0.9225	High Similarity	NPC312318
0.9225	High Similarity	NPC472365
0.9225	High Similarity	NPC242294
0.9225	High Similarity	NPC337373
0.9225	High Similarity	NPC56031
0.9225	High Similarity	NPC175098
0.9225	High Similarity	NPC192304
0.9225	High Similarity	NPC263670
0.9225	High Similarity	NPC139813
0.9225	High Similarity	NPC188646
0.9219	High Similarity	NPC278556
0.916	High Similarity	NPC254741
0.916	High Similarity	NPC477242
0.916	High Similarity	NPC150399
0.916	High Similarity	NPC98115
0.916	High Similarity	NPC477244
0.916	High Similarity	NPC1486
0.916	High Similarity	NPC274109
0.916	High Similarity	NPC249606
0.916	High Similarity	NPC66349
0.916	High Similarity	NPC477243
0.916	High Similarity	NPC25287
0.916	High Similarity	NPC161196
0.916	High Similarity	NPC12165
0.916	High Similarity	NPC41461
0.916	High Similarity	NPC186838
0.916	High Similarity	NPC168105
0.9154	High Similarity	NPC103842
0.9154	High Similarity	NPC125269
0.9147	High Similarity	NPC87231
0.9147	High Similarity	NPC129132
0.9147	High Similarity	NPC212631
0.9147	High Similarity	NPC257756
0.9147	High Similarity	NPC205468
0.9127	High Similarity	NPC264428
0.9127	High Similarity	NPC41721
0.9091	High Similarity	NPC153979
0.9091	High Similarity	NPC472419
0.9091	High Similarity	NPC259685
0.9091	High Similarity	NPC317119
0.9084	High Similarity	NPC131039
0.9084	High Similarity	NPC156092
0.9077	High Similarity	NPC292998
0.907	High Similarity	NPC284424
0.907	High Similarity	NPC112192
0.907	High Similarity	NPC262359
0.907	High Similarity	NPC189106
0.907	High Similarity	NPC309717
0.907	High Similarity	NPC64359
0.907	High Similarity	NPC66384
0.907	High Similarity	NPC164236
0.907	High Similarity	NPC313618
0.907	High Similarity	NPC308037
0.907	High Similarity	NPC128348
0.9062	High Similarity	NPC228184
0.9055	High Similarity	NPC473907
0.9023	High Similarity	NPC124269
0.9023	High Similarity	NPC251681
0.9023	High Similarity	NPC21350
0.9023	High Similarity	NPC17848
0.9023	High Similarity	NPC472368
0.9023	High Similarity	NPC243528
0.9015	High Similarity	NPC61546
0.9015	High Similarity	NPC72452
0.9015	High Similarity	NPC476333
0.9015	High Similarity	NPC473391
0.9015	High Similarity	NPC213603
0.9015	High Similarity	NPC472364
0.9015	High Similarity	NPC472367
0.8984	High Similarity	NPC473894
0.8976	High Similarity	NPC49852
0.8976	High Similarity	NPC475496
0.8955	High Similarity	NPC470211
0.8955	High Similarity	NPC472366
0.8955	High Similarity	NPC477956
0.8955	High Similarity	NPC11566
0.8947	High Similarity	NPC303644
0.8947	High Similarity	NPC294409
0.8947	High Similarity	NPC116632
0.8947	High Similarity	NPC44573
0.8947	High Similarity	NPC188879
0.8947	High Similarity	NPC162680
0.8947	High Similarity	NPC7013
0.8947	High Similarity	NPC209560
0.8947	High Similarity	NPC181124
0.8939	High Similarity	NPC46869
0.8931	High Similarity	NPC27643
0.8931	High Similarity	NPC16197
0.8915	High Similarity	NPC247779
0.8897	High Similarity	NPC297600
0.8889	High Similarity	NPC219917
0.8889	High Similarity	NPC80962
0.8889	High Similarity	NPC284550
0.8889	High Similarity	NPC144118
0.8889	High Similarity	NPC259166
0.8889	High Similarity	NPC188243
0.8889	High Similarity	NPC326109
0.8889	High Similarity	NPC48624
0.8889	High Similarity	NPC6407
0.8889	High Similarity	NPC172250
0.8889	High Similarity	NPC213659
0.8889	High Similarity	NPC204985
0.8889	High Similarity	NPC171094
0.8889	High Similarity	NPC76445
0.8889	High Similarity	NPC241100
0.8889	High Similarity	NPC159275
0.8889	High Similarity	NPC150522
0.8889	High Similarity	NPC265178
0.8889	High Similarity	NPC215311
0.8889	High Similarity	NPC11056
0.8889	High Similarity	NPC129853
0.8889	High Similarity	NPC110228
0.8881	High Similarity	NPC276905
0.8881	High Similarity	NPC309154
0.8881	High Similarity	NPC55162
0.8881	High Similarity	NPC279668
0.8881	High Similarity	NPC12175
0.8881	High Similarity	NPC278323
0.8881	High Similarity	NPC90665
0.8881	High Similarity	NPC471620
0.8872	High Similarity	NPC29353
0.8872	High Similarity	NPC47815
0.8872	High Similarity	NPC194281
0.8872	High Similarity	NPC13408
0.8872	High Similarity	NPC124784
0.8872	High Similarity	NPC473887
0.8872	High Similarity	NPC231772
0.8872	High Similarity	NPC240593
0.8872	High Similarity	NPC234133
0.8872	High Similarity	NPC127447
0.8864	High Similarity	NPC66705
0.8855	High Similarity	NPC229646
0.8855	High Similarity	NPC215875
0.8855	High Similarity	NPC15834
0.8837	High Similarity	NPC212379
0.8837	High Similarity	NPC69235
0.8832	High Similarity	NPC185276
0.8828	High Similarity	NPC305518
0.8828	High Similarity	NPC128428
0.8824	High Similarity	NPC40118
0.8824	High Similarity	NPC49108
0.8824	High Similarity	NPC52789
0.8824	High Similarity	NPC110969
0.8824	High Similarity	NPC26238
0.8824	High Similarity	NPC185607
0.8824	High Similarity	NPC103362
0.8824	High Similarity	NPC22467
0.8824	High Similarity	NPC282300
0.8824	High Similarity	NPC268204
0.8824	High Similarity	NPC470087
0.8824	High Similarity	NPC321980
0.8824	High Similarity	NPC55832
0.8824	High Similarity	NPC469404
0.8824	High Similarity	NPC232021
0.8824	High Similarity	NPC126534
0.8824	High Similarity	NPC470089
0.8824	High Similarity	NPC26051
0.8819	High Similarity	NPC2771
0.8815	High Similarity	NPC295384
0.8815	High Similarity	NPC225153
0.8815	High Similarity	NPC136095
0.8815	High Similarity	NPC53181
0.8815	High Similarity	NPC329203
0.8815	High Similarity	NPC96565
0.8815	High Similarity	NPC216978
0.8815	High Similarity	NPC222342
0.8815	High Similarity	NPC265871
0.8815	High Similarity	NPC20709
0.8815	High Similarity	NPC274784
0.8815	High Similarity	NPC220062
0.8815	High Similarity	NPC217186
0.8815	High Similarity	NPC303633
0.8815	High Similarity	NPC18260
0.8815	High Similarity	NPC78913
0.8815	High Similarity	NPC140890
0.8815	High Similarity	NPC150648
0.8815	High Similarity	NPC283429
0.8815	High Similarity	NPC109232
0.8815	High Similarity	NPC301217
0.8815	High Similarity	NPC310135

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 NPC475017 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	969
0.2-0.3	1389
0.3-0.4	2665
0.4-0.5	1920
0.5-0.6	1230
0.6-0.7	445
0.7-0.8	146
0.8-0.85	23
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.907	High Similarity	NPD1240	Approved
0.9015	High Similarity	NPD2796	Approved
0.8931	High Similarity	NPD1607	Approved
0.8797	High Similarity	NPD1510	Phase 2
0.8667	High Similarity	NPD1550	Clinical (unspecified phase)
0.8667	High Similarity	NPD1552	Clinical (unspecified phase)
0.8633	High Similarity	NPD4378	Clinical (unspecified phase)
0.8603	High Similarity	NPD1549	Phase 2
0.8561	High Similarity	NPD6799	Approved
0.8473	Intermediate Similarity	NPD6832	Phase 2
0.8382	Intermediate Similarity	NPD3748	Approved
0.8369	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6599	Discontinued
0.8288	Intermediate Similarity	NPD7819	Suspended
0.8288	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD7411	Suspended
0.8273	Intermediate Similarity	NPD2654	Approved
0.8235	Intermediate Similarity	NPD6651	Approved
0.8231	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD4380	Phase 2
0.8188	Intermediate Similarity	NPD2935	Discontinued
0.8182	Intermediate Similarity	NPD2798	Approved
0.8163	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD3972	Approved
0.8143	Intermediate Similarity	NPD1243	Approved
0.8121	Intermediate Similarity	NPD7075	Discontinued
0.8095	Intermediate Similarity	NPD6801	Discontinued
0.8095	Intermediate Similarity	NPD1934	Approved
0.8085	Intermediate Similarity	NPD3750	Approved
0.8085	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD1551	Phase 2
0.8054	Intermediate Similarity	NPD7768	Phase 2
0.8042	Intermediate Similarity	NPD1511	Approved
0.8041	Intermediate Similarity	NPD2801	Approved
0.8	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD920	Approved
0.7987	Intermediate Similarity	NPD3817	Phase 2
0.7986	Intermediate Similarity	NPD5401	Approved
0.7986	Intermediate Similarity	NPD2799	Discontinued
0.7972	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD3882	Suspended
0.7931	Intermediate Similarity	NPD1512	Approved
0.7895	Intermediate Similarity	NPD1876	Approved
0.7895	Intermediate Similarity	NPD5494	Approved
0.7887	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD1203	Approved
0.781	Intermediate Similarity	NPD1296	Phase 2
0.7795	Intermediate Similarity	NPD1241	Discontinued
0.777	Intermediate Similarity	NPD1933	Approved
0.777	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD2800	Approved
0.7756	Intermediate Similarity	NPD7473	Discontinued
0.7744	Intermediate Similarity	NPD9717	Approved
0.7742	Intermediate Similarity	NPD3926	Phase 2
0.7704	Intermediate Similarity	NPD3267	Approved
0.7704	Intermediate Similarity	NPD3266	Approved
0.7698	Intermediate Similarity	NPD943	Approved
0.7692	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6166	Phase 2
0.7692	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD2313	Discontinued
0.7677	Intermediate Similarity	NPD6232	Discontinued
0.7658	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3749	Approved
0.7647	Intermediate Similarity	NPD1019	Discontinued
0.7632	Intermediate Similarity	NPD5402	Approved
0.7622	Intermediate Similarity	NPD2344	Approved
0.7619	Intermediate Similarity	NPD2534	Approved
0.7619	Intermediate Similarity	NPD2532	Approved
0.7619	Intermediate Similarity	NPD2533	Approved
0.7615	Intermediate Similarity	NPD9493	Approved
0.7613	Intermediate Similarity	NPD6959	Discontinued
0.761	Intermediate Similarity	NPD7074	Phase 3
0.7597	Intermediate Similarity	NPD919	Approved
0.7576	Intermediate Similarity	NPD1651	Approved
0.7574	Intermediate Similarity	NPD2797	Approved
0.7571	Intermediate Similarity	NPD4307	Phase 2
0.7554	Intermediate Similarity	NPD3268	Approved
0.7547	Intermediate Similarity	NPD7286	Phase 2
0.7547	Intermediate Similarity	NPD7054	Approved
0.7537	Intermediate Similarity	NPD422	Phase 1
0.7536	Intermediate Similarity	NPD4908	Phase 1
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD1548	Phase 1
0.75	Intermediate Similarity	NPD7472	Approved
0.7484	Intermediate Similarity	NPD3818	Discontinued
0.7483	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD4628	Phase 3
0.7453	Intermediate Similarity	NPD5953	Discontinued
0.7431	Intermediate Similarity	NPD6100	Approved
0.7431	Intermediate Similarity	NPD6099	Approved
0.7429	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD5536	Phase 2
0.7415	Intermediate Similarity	NPD2309	Approved
0.741	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7251	Discontinued
0.7407	Intermediate Similarity	NPD6559	Discontinued
0.7407	Intermediate Similarity	NPD1610	Phase 2
0.7388	Intermediate Similarity	NPD17	Approved
0.7379	Intermediate Similarity	NPD2346	Discontinued
0.7362	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7808	Phase 3
0.7361	Intermediate Similarity	NPD7033	Discontinued
0.7361	Intermediate Similarity	NPD4308	Phase 3
0.7355	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6797	Phase 2
0.7338	Intermediate Similarity	NPD3018	Phase 2
0.7333	Intermediate Similarity	NPD3847	Discontinued
0.732	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7390	Discontinued
0.7308	Intermediate Similarity	NPD5535	Approved
0.7305	Intermediate Similarity	NPD6798	Discontinued
0.7303	Intermediate Similarity	NPD3226	Approved
0.729	Intermediate Similarity	NPD4288	Approved
0.728	Intermediate Similarity	NPD9261	Approved
0.7279	Intermediate Similarity	NPD1201	Approved
0.7279	Intermediate Similarity	NPD1281	Approved
0.7273	Intermediate Similarity	NPD6355	Discontinued
0.7267	Intermediate Similarity	NPD4661	Approved
0.7267	Intermediate Similarity	NPD4662	Approved
0.726	Intermediate Similarity	NPD1471	Phase 3
0.725	Intermediate Similarity	NPD2403	Approved
0.7246	Intermediate Similarity	NPD3225	Approved
0.7239	Intermediate Similarity	NPD9545	Approved
0.7234	Intermediate Similarity	NPD3027	Phase 3
0.723	Intermediate Similarity	NPD7003	Approved
0.7226	Intermediate Similarity	NPD2981	Phase 2
0.7226	Intermediate Similarity	NPD1608	Approved
0.7209	Intermediate Similarity	NPD5451	Approved
0.7208	Intermediate Similarity	NPD5889	Approved
0.7208	Intermediate Similarity	NPD5890	Approved
0.7203	Intermediate Similarity	NPD3140	Approved
0.7203	Intermediate Similarity	NPD3142	Approved
0.7195	Intermediate Similarity	NPD6104	Discontinued
0.7194	Intermediate Similarity	NPD1470	Approved
0.7194	Intermediate Similarity	NPD1164	Approved
0.719	Intermediate Similarity	NPD7458	Discontinued
0.7183	Intermediate Similarity	NPD411	Approved
0.7183	Intermediate Similarity	NPD3764	Approved
0.7181	Intermediate Similarity	NPD3887	Approved
0.7181	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2982	Phase 2
0.7174	Intermediate Similarity	NPD2983	Phase 2
0.7161	Intermediate Similarity	NPD6279	Approved
0.7161	Intermediate Similarity	NPD6280	Approved
0.716	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5124	Phase 1
0.7153	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD447	Suspended
0.7152	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2353	Approved
0.7143	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6585	Discontinued
0.7122	Intermediate Similarity	NPD1283	Approved
0.7121	Intermediate Similarity	NPD5283	Phase 1
0.7117	Intermediate Similarity	NPD5844	Phase 1
0.7111	Intermediate Similarity	NPD1894	Discontinued
0.7109	Intermediate Similarity	NPD3134	Approved
0.7086	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2979	Phase 3
0.7081	Intermediate Similarity	NPD5242	Approved
0.7075	Intermediate Similarity	NPD5408	Approved
0.7075	Intermediate Similarity	NPD5405	Approved
0.7075	Intermediate Similarity	NPD5406	Approved
0.7075	Intermediate Similarity	NPD5404	Approved
0.7063	Intermediate Similarity	NPD940	Approved
0.7063	Intermediate Similarity	NPD846	Approved
0.7059	Intermediate Similarity	NPD5691	Approved
0.7054	Intermediate Similarity	NPD1358	Approved
0.7054	Intermediate Similarity	NPD9267	Approved
0.7054	Intermediate Similarity	NPD9263	Approved
0.7054	Intermediate Similarity	NPD9264	Approved
0.7051	Intermediate Similarity	NPD6844	Discontinued
0.705	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD230	Phase 1
0.7027	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5710	Approved
0.7019	Intermediate Similarity	NPD6808	Phase 2
0.7019	Intermediate Similarity	NPD5711	Approved
0.7014	Intermediate Similarity	NPD6233	Phase 2
0.7007	Intermediate Similarity	NPD4626	Approved
0.7007	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD74	Approved
0.7	Intermediate Similarity	NPD9266	Approved
0.6993	Remote Similarity	NPD4625	Phase 3
0.6993	Remote Similarity	NPD5049	Phase 3
0.6987	Remote Similarity	NPD6385	Approved
0.6987	Remote Similarity	NPD6386	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