NPASS Compound

Structure

NPC25639 OpenBabel07101719142D 29 32 0 0 1 0 0 0 0 0999 V2000 1.9657 -2.2614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3118 -1.1714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4563 0.3521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4417 -2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1481 -0.9531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4891 -2.6151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7820 -1.9080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0351 0.6901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0474 0.5337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6948 -0.5507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7351 -1.4080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2531 -1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4891 -0.2009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8718 -3.5390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3241 -1.3278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1473 -0.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7346 -1.4417 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4891 -2.6151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -0.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1962 -0.9080 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7820 -0.9080 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1473 -2.2170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4891 -0.2009 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8910 -0.4540 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1962 -1.9080 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8632 -3.6695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4563 -3.1681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1984 -1.8420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 6 7 1 0 0 0 0 6 18 2 0 0 0 0 7 21 1 0 0 0 0 8 9 1 0 0 0 0 8 23 1 0 0 0 0 10 15 2 0 0 0 0 11 16 2 0 0 0 0 11 22 1 0 0 0 0 12 17 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 26 2 0 0 0 0 16 20 1 0 0 0 0 17 24 1 6 0 0 0 18 25 1 0 0 0 0 19 10 1 1 0 0 0 19 29 1 0 0 0 0 20 25 1 1 0 0 0 21 23 1 6 0 0 0 21 24 1 0 0 0 0 22 25 1 0 0 0 0 22 27 2 0 0 0 0 23 5 1 6 0 0 0 24 9 1 6 0 0 0 24 29 1 0 0 0 0 25 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.25
Volume:	428.709
LogP:	4.691
LogD:	4.77
LogS:	-4.94
# Rotatable Bonds:	2
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.55
Synthetic Accessibility Score:	5.787
Fsp3:	0.68
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:	-5.012
MDCK Permeability:	2.2255428120843135e-05
Pgp-inhibitor:	0.937
Pgp-substrate:	0.327
Human Intestinal Absorption (HIA):	0.179
20% Bioavailability (F20%):	0.177
30% Bioavailability (F30%):	0.606

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.701
Plasma Protein Binding (PPB):	86.9476318359375%
Volume Distribution (VD):	2.214
Pgp-substrate:	5.709959506988525%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.28
CYP2C19-inhibitor:	0.425
CYP2C19-substrate:	0.841
CYP2C9-inhibitor:	0.19
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.681
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	3.152
Half-life (T1/2):	0.322

ADMET: Toxicity

hERG Blockers:	0.148
Human Hepatotoxicity (H-HT):	0.931
Drug-inuced Liver Injury (DILI):	0.123
AMES Toxicity:	0.789
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.941
Carcinogencity:	0.129
Eye Corrosion:	0.605
Eye Irritation:	0.439
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC25639

Natural Product ID:	NPC25639
*Common Name:**	MNTJKNWRCITJMY-JCBJYGFASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MNTJKNWRCITJMY-JCBJYGFASA-N
Standard InCHI:	InChI=1S/C25H34O4/c1-15(2)10-19-12-17(4)24(29-19)9-8-23(5)13-20-16(3)11-22(27)25(20,28)18(14-26)6-7-21(23)24/h6,10-11,14,17,19-21,28H,7-9,12-13H2,1-5H3/b18-6-/t17-,19-,20+,21+,23+,24-,25-/m0/s1
SMILES:	O=CC1=CC[C@@H]2[C@](C[C@H]3[C@]1(O)C(=O)C=C3C)(C)CC[C@]12O[C@H](C[C@@H]1C)C=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2393051
PubChem CID:	71655010
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002882] Ophiobolane sesterterpenoids

*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
NPO385	Bipolaris oryzae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23668986]
NPO385	Bipolaris oryzae	Species	Pleosporaceae	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	2
MIC	6
Others	17

Activity Type	# Activity
Cell Line	19
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	Activity	=	96.58	%	PMID[531277]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	91.28	%	PMID[531277]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	88.27	%	PMID[531277]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	87.51	%	PMID[531277]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	69.67	%	PMID[531277]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	62.78	%	PMID[531277]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	61.48	%	PMID[531277]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	56.03	%	PMID[531277]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	50.2	%	PMID[531277]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	49.62	%	PMID[531277]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	32.65	%	PMID[531277]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	27.51	%	PMID[531277]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	26.91	%	PMID[531277]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	25.93	%	PMID[531277]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	6490.0	nM	PMID[531277]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	5.86	%	PMID[531277]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	4060.0	nM	PMID[531277]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	2.45	%	PMID[531277]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	1.78	%	PMID[531277]
NPT1548	Organism	Pseudomonas aeruginosa PAO1	Pseudomonas aeruginosa PAO1	MIC	>	100.0	ug.mL-1	PMID[531277]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	50.0	ug.mL-1	PMID[531277]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[531277]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	12.5	ug.mL-1	PMID[531277]
NPT1108	Organism	Mycobacterium bovis BCG	Mycobacterium bovis BCG	MIC	=	12.5	ug.mL-1	PMID[531277]

☑ 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 NPC25639 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	239
0.1-0.2	1495
0.2-0.3	6063
0.3-0.4	14555
0.4-0.5	10832
0.5-0.6	6567
0.6-0.7	2744
0.7-0.8	176
0.8-0.85	8
0.85-0.9	15
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9082	High Similarity	NPC195192
0.9082	High Similarity	NPC304738
0.8936	High Similarity	NPC306168
0.8936	High Similarity	NPC49946
0.875	High Similarity	NPC37816
0.8351	Intermediate Similarity	NPC477711
0.8163	Intermediate Similarity	NPC2946
0.8144	Intermediate Similarity	NPC477710
0.8137	Intermediate Similarity	NPC471610
0.8061	Intermediate Similarity	NPC41217
0.7895	Intermediate Similarity	NPC256750
0.7895	Intermediate Similarity	NPC20262
0.7879	Intermediate Similarity	NPC170775
0.7788	Intermediate Similarity	NPC109556
0.7766	Intermediate Similarity	NPC301769
0.7757	Intermediate Similarity	NPC294259
0.7745	Intermediate Similarity	NPC167219
0.77	Intermediate Similarity	NPC476388
0.77	Intermediate Similarity	NPC477215
0.7692	Intermediate Similarity	NPC477949
0.767	Intermediate Similarity	NPC476488
0.767	Intermediate Similarity	NPC476487
0.7664	Intermediate Similarity	NPC168575
0.7579	Intermediate Similarity	NPC32758
0.7576	Intermediate Similarity	NPC261721
0.7573	Intermediate Similarity	NPC469632
0.7573	Intermediate Similarity	NPC298919
0.7573	Intermediate Similarity	NPC90453
0.7573	Intermediate Similarity	NPC53685
0.757	Intermediate Similarity	NPC118405
0.7549	Intermediate Similarity	NPC261607
0.7549	Intermediate Similarity	NPC111114
0.7549	Intermediate Similarity	NPC300312
0.7549	Intermediate Similarity	NPC144629
0.7524	Intermediate Similarity	NPC213947
0.7524	Intermediate Similarity	NPC108475
0.7524	Intermediate Similarity	NPC170143
0.75	Intermediate Similarity	NPC474490
0.7477	Intermediate Similarity	NPC477950
0.7477	Intermediate Similarity	NPC475099
0.7476	Intermediate Similarity	NPC125180
0.7476	Intermediate Similarity	NPC469692
0.7476	Intermediate Similarity	NPC469645
0.7476	Intermediate Similarity	NPC229976
0.7475	Intermediate Similarity	NPC125290
0.7455	Intermediate Similarity	NPC26617
0.7453	Intermediate Similarity	NPC222011
0.7453	Intermediate Similarity	NPC141191
0.7434	Intermediate Similarity	NPC69291
0.7429	Intermediate Similarity	NPC121036
0.7429	Intermediate Similarity	NPC472674
0.7404	Intermediate Similarity	NPC121825
0.7387	Intermediate Similarity	NPC220155
0.7387	Intermediate Similarity	NPC177064
0.7379	Intermediate Similarity	NPC290651
0.7379	Intermediate Similarity	NPC221282
0.7379	Intermediate Similarity	NPC190442
0.7358	Intermediate Similarity	NPC69385
0.7358	Intermediate Similarity	NPC169205
0.7339	Intermediate Similarity	NPC472755
0.7333	Intermediate Similarity	NPC67584
0.7333	Intermediate Similarity	NPC469873
0.7327	Intermediate Similarity	NPC72513
0.7327	Intermediate Similarity	NPC201658
0.7321	Intermediate Similarity	NPC47951
0.7315	Intermediate Similarity	NPC110443
0.7315	Intermediate Similarity	NPC185141
0.7315	Intermediate Similarity	NPC46998
0.7315	Intermediate Similarity	NPC133907
0.7315	Intermediate Similarity	NPC171759
0.7315	Intermediate Similarity	NPC128733
0.7315	Intermediate Similarity	NPC206079
0.73	Intermediate Similarity	NPC179006
0.73	Intermediate Similarity	NPC474853
0.73	Intermediate Similarity	NPC96621
0.729	Intermediate Similarity	NPC470541
0.729	Intermediate Similarity	NPC477355
0.7282	Intermediate Similarity	NPC37607
0.7282	Intermediate Similarity	NPC145666
0.7282	Intermediate Similarity	NPC301969
0.7281	Intermediate Similarity	NPC191620
0.7273	Intermediate Similarity	NPC309190
0.7273	Intermediate Similarity	NPC472868
0.7264	Intermediate Similarity	NPC185553
0.7264	Intermediate Similarity	NPC213078
0.7257	Intermediate Similarity	NPC257240
0.7257	Intermediate Similarity	NPC179642
0.7255	Intermediate Similarity	NPC471047
0.7255	Intermediate Similarity	NPC469631
0.7255	Intermediate Similarity	NPC475906
0.7255	Intermediate Similarity	NPC469653
0.7255	Intermediate Similarity	NPC469628
0.7248	Intermediate Similarity	NPC87351
0.7238	Intermediate Similarity	NPC323008
0.7238	Intermediate Similarity	NPC470013
0.7238	Intermediate Similarity	NPC470010
0.7238	Intermediate Similarity	NPC198853
0.7238	Intermediate Similarity	NPC65829
0.7238	Intermediate Similarity	NPC262133
0.7238	Intermediate Similarity	NPC477131
0.7234	Intermediate Similarity	NPC206875
0.7228	Intermediate Similarity	NPC38576
0.7228	Intermediate Similarity	NPC279859
0.7222	Intermediate Similarity	NPC174314
0.7207	Intermediate Similarity	NPC60681
0.7203	Intermediate Similarity	NPC477092
0.7196	Intermediate Similarity	NPC161493
0.7196	Intermediate Similarity	NPC87090
0.7193	Intermediate Similarity	NPC470961
0.7184	Intermediate Similarity	NPC232747
0.7184	Intermediate Similarity	NPC268298
0.7184	Intermediate Similarity	NPC123912
0.7182	Intermediate Similarity	NPC470839
0.7182	Intermediate Similarity	NPC111323
0.7182	Intermediate Similarity	NPC311612
0.7182	Intermediate Similarity	NPC176883
0.7179	Intermediate Similarity	NPC239273
0.7179	Intermediate Similarity	NPC475305
0.717	Intermediate Similarity	NPC193645
0.717	Intermediate Similarity	NPC279313
0.717	Intermediate Similarity	NPC275960
0.717	Intermediate Similarity	NPC52044
0.717	Intermediate Similarity	NPC48803
0.717	Intermediate Similarity	NPC90121
0.717	Intermediate Similarity	NPC91408
0.7168	Intermediate Similarity	NPC475941
0.7168	Intermediate Similarity	NPC477102
0.7168	Intermediate Similarity	NPC474901
0.7158	Intermediate Similarity	NPC251435
0.7157	Intermediate Similarity	NPC45957
0.7157	Intermediate Similarity	NPC471657
0.7156	Intermediate Similarity	NPC472753
0.7156	Intermediate Similarity	NPC477356
0.7156	Intermediate Similarity	NPC99411
0.7156	Intermediate Similarity	NPC150923
0.7154	Intermediate Similarity	NPC172823
0.7143	Intermediate Similarity	NPC473234
0.7143	Intermediate Similarity	NPC475294
0.7143	Intermediate Similarity	NPC308656
0.7143	Intermediate Similarity	NPC473263
0.7143	Intermediate Similarity	NPC91034
0.7143	Intermediate Similarity	NPC473273
0.7143	Intermediate Similarity	NPC60386
0.713	Intermediate Similarity	NPC475524
0.713	Intermediate Similarity	NPC138757
0.713	Intermediate Similarity	NPC76550
0.713	Intermediate Similarity	NPC54843
0.713	Intermediate Similarity	NPC221615
0.713	Intermediate Similarity	NPC64742
0.713	Intermediate Similarity	NPC100267
0.713	Intermediate Similarity	NPC123855
0.713	Intermediate Similarity	NPC221144
0.7129	Intermediate Similarity	NPC245434
0.7129	Intermediate Similarity	NPC33570
0.7129	Intermediate Similarity	NPC261380
0.7129	Intermediate Similarity	NPC21471
0.7119	Intermediate Similarity	NPC475372
0.7119	Intermediate Similarity	NPC475401
0.7117	Intermediate Similarity	NPC13385
0.7117	Intermediate Similarity	NPC100487
0.7115	Intermediate Similarity	NPC106510
0.7115	Intermediate Similarity	NPC77337
0.7115	Intermediate Similarity	NPC129419
0.7115	Intermediate Similarity	NPC71533
0.7105	Intermediate Similarity	NPC477103
0.7105	Intermediate Similarity	NPC99760
0.7105	Intermediate Similarity	NPC29133
0.7103	Intermediate Similarity	NPC9812
0.7103	Intermediate Similarity	NPC184065
0.7103	Intermediate Similarity	NPC18019
0.7103	Intermediate Similarity	NPC24956
0.71	Intermediate Similarity	NPC62214
0.71	Intermediate Similarity	NPC215294
0.7094	Intermediate Similarity	NPC148458
0.7091	Intermediate Similarity	NPC86077
0.7091	Intermediate Similarity	NPC472754
0.7087	Intermediate Similarity	NPC58532
0.7087	Intermediate Similarity	NPC91248
0.7087	Intermediate Similarity	NPC472677
0.7087	Intermediate Similarity	NPC476708
0.7083	Intermediate Similarity	NPC215481
0.7083	Intermediate Similarity	NPC271070
0.7075	Intermediate Similarity	NPC127019
0.7075	Intermediate Similarity	NPC473331
0.7075	Intermediate Similarity	NPC148463
0.7071	Intermediate Similarity	NPC59994
0.7071	Intermediate Similarity	NPC325031
0.7071	Intermediate Similarity	NPC78677
0.7069	Intermediate Similarity	NPC106395
0.7069	Intermediate Similarity	NPC46269
0.7064	Intermediate Similarity	NPC469872
0.7064	Intermediate Similarity	NPC469864
0.7063	Intermediate Similarity	NPC469673
0.7059	Intermediate Similarity	NPC107787
0.7059	Intermediate Similarity	NPC261253
0.7059	Intermediate Similarity	NPC312536
0.7059	Intermediate Similarity	NPC474045
0.7054	Intermediate Similarity	NPC1679
0.7054	Intermediate Similarity	NPC179891
0.7049	Intermediate Similarity	NPC144625

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 NPC25639 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	2148
0.2-0.3	4007
0.3-0.4	2020
0.4-0.5	408
0.5-0.6	219
0.6-0.7	124
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.78	Intermediate Similarity	NPD5785	Approved
0.7455	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5363	Approved
0.7273	Intermediate Similarity	NPD5362	Discontinued
0.7257	Intermediate Similarity	NPD6371	Approved
0.7238	Intermediate Similarity	NPD5282	Discontinued
0.717	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5786	Approved
0.7	Intermediate Similarity	NPD4269	Approved
0.7	Intermediate Similarity	NPD4270	Approved
0.69	Remote Similarity	NPD5369	Approved
0.6881	Remote Similarity	NPD6083	Phase 2
0.6881	Remote Similarity	NPD6084	Phase 2
0.6857	Remote Similarity	NPD4753	Phase 2
0.6852	Remote Similarity	NPD5695	Phase 3
0.68	Remote Similarity	NPD4252	Approved
0.6796	Remote Similarity	NPD5329	Approved
0.6786	Remote Similarity	NPD5211	Phase 2
0.6768	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7115	Discovery
0.6733	Remote Similarity	NPD4790	Discontinued
0.6731	Remote Similarity	NPD5690	Phase 2
0.6729	Remote Similarity	NPD5693	Phase 1
0.6699	Remote Similarity	NPD4197	Approved
0.6697	Remote Similarity	NPD4629	Approved
0.6697	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5141	Approved
0.6638	Remote Similarity	NPD6881	Approved
0.6638	Remote Similarity	NPD7320	Approved
0.6638	Remote Similarity	NPD6899	Approved
0.6636	Remote Similarity	NPD4697	Phase 3
0.6635	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6649	Approved
0.661	Remote Similarity	NPD6650	Approved
0.6609	Remote Similarity	NPD5739	Approved
0.6609	Remote Similarity	NPD6675	Approved
0.6609	Remote Similarity	NPD7128	Approved
0.6609	Remote Similarity	NPD6402	Approved
0.6607	Remote Similarity	NPD5286	Approved
0.6607	Remote Similarity	NPD5285	Approved
0.6607	Remote Similarity	NPD4696	Approved
0.6602	Remote Similarity	NPD7154	Phase 3
0.6602	Remote Similarity	NPD5332	Approved
0.6602	Remote Similarity	NPD5331	Approved
0.6585	Remote Similarity	NPD6054	Approved
0.6581	Remote Similarity	NPD6372	Approved
0.6581	Remote Similarity	NPD6373	Approved
0.6577	Remote Similarity	NPD4755	Approved
0.6571	Remote Similarity	NPD5280	Approved
0.6571	Remote Similarity	NPD5279	Phase 3
0.6571	Remote Similarity	NPD4694	Approved
0.6552	Remote Similarity	NPD5697	Approved
0.6549	Remote Similarity	NPD5223	Approved
0.6542	Remote Similarity	NPD1695	Approved
0.6542	Remote Similarity	NPD6080	Approved
0.6542	Remote Similarity	NPD6904	Approved
0.6542	Remote Similarity	NPD6673	Approved
0.6538	Remote Similarity	NPD3665	Phase 1
0.6538	Remote Similarity	NPD3666	Approved
0.6538	Remote Similarity	NPD3133	Approved
0.6525	Remote Similarity	NPD6883	Approved
0.6525	Remote Similarity	NPD7290	Approved
0.6525	Remote Similarity	NPD7102	Approved
0.6518	Remote Similarity	NPD4225	Approved
0.6514	Remote Similarity	NPD6399	Phase 3
0.6505	Remote Similarity	NPD4223	Phase 3
0.6505	Remote Similarity	NPD4221	Approved
0.6496	Remote Similarity	NPD6011	Approved
0.6491	Remote Similarity	NPD5226	Approved
0.6491	Remote Similarity	NPD4633	Approved
0.6491	Remote Similarity	NPD5224	Approved
0.6491	Remote Similarity	NPD5225	Approved
0.648	Remote Similarity	NPD6370	Approved
0.6471	Remote Similarity	NPD6847	Approved
0.6471	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6617	Approved
0.6471	Remote Similarity	NPD4820	Approved
0.6471	Remote Similarity	NPD6869	Approved
0.6471	Remote Similarity	NPD4822	Approved
0.6471	Remote Similarity	NPD4821	Approved
0.6471	Remote Similarity	NPD4819	Approved
0.6471	Remote Similarity	NPD8130	Phase 1
0.646	Remote Similarity	NPD7640	Approved
0.646	Remote Similarity	NPD4700	Approved
0.646	Remote Similarity	NPD7639	Approved
0.6452	Remote Similarity	NPD6059	Approved
0.6449	Remote Similarity	NPD6672	Approved
0.6449	Remote Similarity	NPD6903	Approved
0.6449	Remote Similarity	NPD5737	Approved
0.6441	Remote Similarity	NPD6014	Approved
0.6441	Remote Similarity	NPD6013	Approved
0.6441	Remote Similarity	NPD6012	Approved
0.6435	Remote Similarity	NPD5174	Approved
0.6435	Remote Similarity	NPD5175	Approved
0.6422	Remote Similarity	NPD6050	Approved
0.6417	Remote Similarity	NPD6882	Approved
0.6417	Remote Similarity	NPD6053	Discontinued
0.6417	Remote Similarity	NPD8297	Approved
0.6415	Remote Similarity	NPD7146	Approved
0.6415	Remote Similarity	NPD7521	Approved
0.6415	Remote Similarity	NPD7334	Approved
0.6415	Remote Similarity	NPD6409	Approved
0.6415	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5330	Approved
0.6415	Remote Similarity	NPD6684	Approved
0.641	Remote Similarity	NPD5701	Approved
0.6406	Remote Similarity	NPD7078	Approved
0.64	Remote Similarity	NPD6016	Approved
0.64	Remote Similarity	NPD6015	Approved
0.6396	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4634	Approved
0.6381	Remote Similarity	NPD4786	Approved
0.6378	Remote Similarity	NPD7492	Approved
0.6372	Remote Similarity	NPD7638	Approved
0.6364	Remote Similarity	NPD4202	Approved
0.6355	Remote Similarity	NPD4251	Approved
0.6355	Remote Similarity	NPD4250	Approved
0.6349	Remote Similarity	NPD5988	Approved
0.6346	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6435	Approved
0.6339	Remote Similarity	NPD5221	Approved
0.6339	Remote Similarity	NPD5222	Approved
0.6339	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5692	Phase 3
0.6328	Remote Similarity	NPD6616	Approved
0.6321	Remote Similarity	NPD1694	Approved
0.6311	Remote Similarity	NPD4695	Discontinued
0.6308	Remote Similarity	NPD7319	Approved
0.6296	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4518	Approved
0.6293	Remote Similarity	NPD4754	Approved
0.6286	Remote Similarity	NPD4788	Approved
0.6283	Remote Similarity	NPD5173	Approved
0.6275	Remote Similarity	NPD4268	Approved
0.6275	Remote Similarity	NPD4271	Approved
0.6273	Remote Similarity	NPD7637	Suspended
0.6273	Remote Similarity	NPD6079	Approved
0.6273	Remote Similarity	NPD5694	Approved
0.6262	Remote Similarity	NPD5205	Approved
0.6262	Remote Similarity	NPD4690	Approved
0.6262	Remote Similarity	NPD4688	Approved
0.6262	Remote Similarity	NPD6098	Approved
0.6262	Remote Similarity	NPD4249	Approved
0.6262	Remote Similarity	NPD4693	Phase 3
0.6262	Remote Similarity	NPD4138	Approved
0.6262	Remote Similarity	NPD4689	Approved
0.6239	Remote Similarity	NPD5328	Approved
0.6231	Remote Similarity	NPD7736	Approved
0.6218	Remote Similarity	NPD4730	Approved
0.6218	Remote Similarity	NPD4729	Approved
0.6218	Remote Similarity	NPD5128	Approved
0.6202	Remote Similarity	NPD7507	Approved
0.619	Remote Similarity	NPD6319	Approved
0.619	Remote Similarity	NPD3667	Approved
0.6186	Remote Similarity	NPD4767	Approved
0.6186	Remote Similarity	NPD4768	Approved
0.6186	Remote Similarity	NPD6008	Approved
0.6182	Remote Similarity	NPD5207	Approved
0.6168	Remote Similarity	NPD1696	Phase 3
0.616	Remote Similarity	NPD6335	Approved
0.6154	Remote Similarity	NPD5368	Approved
0.6154	Remote Similarity	NPD8293	Discontinued
0.6142	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6695	Phase 3
0.6129	Remote Similarity	NPD6274	Approved
0.6126	Remote Similarity	NPD5281	Approved
0.6126	Remote Similarity	NPD5284	Approved
0.6116	Remote Similarity	NPD5249	Phase 3
0.6116	Remote Similarity	NPD5248	Approved
0.6116	Remote Similarity	NPD5247	Approved
0.6116	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD5251	Approved
0.6116	Remote Similarity	NPD5250	Approved
0.6116	Remote Similarity	NPD5169	Approved
0.6116	Remote Similarity	NPD5135	Approved
0.6111	Remote Similarity	NPD4623	Approved
0.6111	Remote Similarity	NPD4519	Discontinued
0.6111	Remote Similarity	NPD3618	Phase 1
0.6111	Remote Similarity	NPD7100	Approved
0.6111	Remote Similarity	NPD7101	Approved
0.6107	Remote Similarity	NPD6033	Approved
0.6098	Remote Similarity	NPD4632	Approved
0.6091	Remote Similarity	NPD6051	Approved
0.608	Remote Similarity	NPD6317	Approved
0.6075	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5779	Approved
0.6071	Remote Similarity	NPD5778	Approved
0.6071	Remote Similarity	NPD5133	Approved
0.6068	Remote Similarity	NPD5091	Approved
0.6066	Remote Similarity	NPD5215	Approved
0.6066	Remote Similarity	NPD5127	Approved
0.6066	Remote Similarity	NPD5217	Approved
0.6066	Remote Similarity	NPD5216	Approved
0.6058	Remote Similarity	NPD4195	Approved
0.6036	Remote Similarity	NPD46	Approved
0.6036	Remote Similarity	NPD4096	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