NPASS Compound

Structure

CID98305 OpenBabel06191715442D 26 27 0 0 1 0 0 0 0 0999 V2000 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 0.0000 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 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 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 2 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 -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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 -4.3301 -0.5000 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 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 6 1 0 0 0 0 2 13 1 0 0 0 0 3 7 1 0 0 0 0 3 14 1 0 0 0 0 4 8 2 0 0 0 0 4 13 1 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 19 1 0 0 0 0 11 14 2 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 0 0 0 0 15 21 2 0 0 0 0 16 7 1 6 0 0 0 16 26 1 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 20 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.16
Volume:	371.649
LogP:	1.779
LogD:	2.177
LogS:	-2.402
# Rotatable Bonds:	9
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.512
Synthetic Accessibility Score:	2.948
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.96
MDCK Permeability:	1.4082221241551451e-05
Pgp-inhibitor:	0.111
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.534
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	92.52090454101562%
Volume Distribution (VD):	0.612
Pgp-substrate:	4.634152889251709%

ADMET: Metabolism

CYP1A2-inhibitor:	0.188
CYP1A2-substrate:	0.8
CYP2C19-inhibitor:	0.186
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.572
CYP2C9-substrate:	0.799
CYP2D6-inhibitor:	0.57
CYP2D6-substrate:	0.767
CYP3A4-inhibitor:	0.179
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	21.36
Half-life (T1/2):	0.945

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.087
AMES Toxicity:	0.825
Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.95
Carcinogencity:	0.234
Eye Corrosion:	0.006
Eye Irritation:	0.92
Respiratory Toxicity:	0.103

Download Data

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

Natural Product: NPC98305

Natural Product ID:	NPC98305
*Common Name:**	(5R)-1,7-Bis(3,4-Dihydroxyphenyl)-5-Methoxyheptan-3-One
IUPAC Name:	(5R)-1,7-bis(3,4-dihydroxyphenyl)-5-methoxyheptan-3-one
Synonyms:
Standard InCHIKey:	KGQIYLSVVQCRJA-MRXNPFEDSA-N
Standard InCHI:	InChI=1S/C20H24O6/c1-26-16(7-3-14-5-9-18(23)20(25)11-14)12-15(21)6-2-13-4-8-17(22)19(24)10-13/h4-5,8-11,16,22-25H,2-3,6-7,12H2,1H3/t16-/m1/s1
SMILES:	CO[C@@H](CC(=O)CCc1ccc(c(c1)O)O)CCc1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774772
PubChem CID:	11667643
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO4971	Alnus firma	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21504848]
NPO12532	Amomum muricarpum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4971	Alnus firma	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12532	Amomum muricarpum	Species	Zingiberaceae	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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[500671]

☑ 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 NPC98305 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	232
0.1-0.2	1143
0.2-0.3	2961
0.3-0.4	8818
0.4-0.5	10783
0.5-0.6	5070
0.6-0.7	9764
0.7-0.8	3667
0.8-0.85	175
0.85-0.9	69
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9737	High Similarity	NPC34634
0.9737	High Similarity	NPC265454
0.9487	High Similarity	NPC86900
0.9187	High Similarity	NPC137427
0.9187	High Similarity	NPC123196
0.9187	High Similarity	NPC311419
0.9187	High Similarity	NPC215941
0.9187	High Similarity	NPC244246
0.9187	High Similarity	NPC319282
0.9187	High Similarity	NPC275724
0.9187	High Similarity	NPC65935
0.9052	High Similarity	NPC277394
0.9052	High Similarity	NPC299252
0.9052	High Similarity	NPC61062
0.8974	High Similarity	NPC200988
0.8974	High Similarity	NPC145023
0.8974	High Similarity	NPC175799
0.8974	High Similarity	NPC610
0.8966	High Similarity	NPC23402
0.8947	High Similarity	NPC177576
0.8943	High Similarity	NPC293641
0.8943	High Similarity	NPC20287
0.8943	High Similarity	NPC12022
0.8943	High Similarity	NPC20404
0.8934	High Similarity	NPC53305
0.8934	High Similarity	NPC257589
0.8917	High Similarity	NPC472271
0.8898	High Similarity	NPC86198
0.8871	High Similarity	NPC278308
0.8862	High Similarity	NPC92207
0.8862	High Similarity	NPC127937
0.886	High Similarity	NPC226401
0.886	High Similarity	NPC174096
0.886	High Similarity	NPC147634
0.886	High Similarity	NPC252544
0.886	High Similarity	NPC120982
0.886	High Similarity	NPC79793
0.886	High Similarity	NPC321252
0.8824	High Similarity	NPC109371
0.8824	High Similarity	NPC70084
0.8824	High Similarity	NPC470214
0.8824	High Similarity	NPC470215
0.8793	High Similarity	NPC148969
0.8783	High Similarity	NPC179002
0.8783	High Similarity	NPC187583
0.8783	High Similarity	NPC257430
0.8772	High Similarity	NPC62258
0.8772	High Similarity	NPC55617
0.872	High Similarity	NPC226661
0.8718	High Similarity	NPC285350
0.871	High Similarity	NPC303680
0.871	High Similarity	NPC84076
0.871	High Similarity	NPC90128
0.8699	High Similarity	NPC85565
0.8684	High Similarity	NPC317305
0.8682	High Similarity	NPC158325
0.8682	High Similarity	NPC180171
0.8682	High Similarity	NPC103398
0.8651	High Similarity	NPC304622
0.864	High Similarity	NPC5018
0.864	High Similarity	NPC123228
0.864	High Similarity	NPC151167
0.864	High Similarity	NPC123722
0.864	High Similarity	NPC276466
0.8621	High Similarity	NPC297657
0.8618	High Similarity	NPC163083
0.8618	High Similarity	NPC244876
0.8609	High Similarity	NPC228343
0.8609	High Similarity	NPC254833
0.8607	High Similarity	NPC201777
0.8605	High Similarity	NPC106406
0.8583	High Similarity	NPC195292
0.8583	High Similarity	NPC142985
0.8561	High Similarity	NPC474784
0.856	High Similarity	NPC179777
0.8559	High Similarity	NPC120280
0.8548	High Similarity	NPC288945
0.8547	High Similarity	NPC51698
0.8534	High Similarity	NPC222084
0.8525	High Similarity	NPC470848
0.8525	High Similarity	NPC294361
0.8525	High Similarity	NPC236520
0.8525	High Similarity	NPC470849
0.8516	High Similarity	NPC469480
0.8512	High Similarity	NPC182240
0.8509	High Similarity	NPC188677
0.8496	Intermediate Similarity	NPC261573
0.8496	Intermediate Similarity	NPC120693
0.8496	Intermediate Similarity	NPC8931
0.8496	Intermediate Similarity	NPC471511
0.848	Intermediate Similarity	NPC3221
0.8455	Intermediate Similarity	NPC322332
0.8438	Intermediate Similarity	NPC244441
0.843	Intermediate Similarity	NPC63126
0.8409	Intermediate Similarity	NPC308976
0.8409	Intermediate Similarity	NPC279676
0.8409	Intermediate Similarity	NPC67349
0.84	Intermediate Similarity	NPC231767
0.8385	Intermediate Similarity	NPC155209
0.8385	Intermediate Similarity	NPC168799
0.8385	Intermediate Similarity	NPC327410
0.8374	Intermediate Similarity	NPC207613
0.8372	Intermediate Similarity	NPC476407
0.8372	Intermediate Similarity	NPC198388
0.837	Intermediate Similarity	NPC285550
0.8361	Intermediate Similarity	NPC141791
0.8361	Intermediate Similarity	NPC263386
0.8361	Intermediate Similarity	NPC299406
0.8359	Intermediate Similarity	NPC241354
0.8348	Intermediate Similarity	NPC70843
0.8333	Intermediate Similarity	NPC127975
0.8333	Intermediate Similarity	NPC280767
0.8321	Intermediate Similarity	NPC5310
0.8321	Intermediate Similarity	NPC300776
0.8321	Intermediate Similarity	NPC176814
0.8321	Intermediate Similarity	NPC68779
0.8321	Intermediate Similarity	NPC4982
0.832	Intermediate Similarity	NPC242372
0.832	Intermediate Similarity	NPC257976
0.832	Intermediate Similarity	NPC4181
0.832	Intermediate Similarity	NPC164778
0.8309	Intermediate Similarity	NPC183824
0.8308	Intermediate Similarity	NPC18074
0.8308	Intermediate Similarity	NPC5419
0.8308	Intermediate Similarity	NPC61
0.8308	Intermediate Similarity	NPC25581
0.8306	Intermediate Similarity	NPC184651
0.8306	Intermediate Similarity	NPC324571
0.8306	Intermediate Similarity	NPC343720
0.8306	Intermediate Similarity	NPC262156
0.8306	Intermediate Similarity	NPC473853
0.8306	Intermediate Similarity	NPC470212
0.8306	Intermediate Similarity	NPC312675
0.8306	Intermediate Similarity	NPC54872
0.8306	Intermediate Similarity	NPC113865
0.8295	Intermediate Similarity	NPC172673
0.8291	Intermediate Similarity	NPC88141
0.8284	Intermediate Similarity	NPC179505
0.8284	Intermediate Similarity	NPC156709
0.8279	Intermediate Similarity	NPC309434
0.8279	Intermediate Similarity	NPC470626
0.8279	Intermediate Similarity	NPC249435
0.8268	Intermediate Similarity	NPC276014
0.8261	Intermediate Similarity	NPC239291
0.8258	Intermediate Similarity	NPC113295
0.8258	Intermediate Similarity	NPC152209
0.8258	Intermediate Similarity	NPC311742
0.8254	Intermediate Similarity	NPC273686
0.8254	Intermediate Similarity	NPC15127
0.8254	Intermediate Similarity	NPC312404
0.8246	Intermediate Similarity	NPC196479
0.8244	Intermediate Similarity	NPC471749
0.824	Intermediate Similarity	NPC114298
0.8231	Intermediate Similarity	NPC318799
0.823	Intermediate Similarity	NPC223393
0.8226	Intermediate Similarity	NPC158949
0.8209	Intermediate Similarity	NPC206207
0.8197	Intermediate Similarity	NPC293619
0.8197	Intermediate Similarity	NPC76308
0.8197	Intermediate Similarity	NPC150919
0.8197	Intermediate Similarity	NPC325295
0.8195	Intermediate Similarity	NPC264112
0.8195	Intermediate Similarity	NPC90431
0.8195	Intermediate Similarity	NPC324929
0.8195	Intermediate Similarity	NPC65005
0.8195	Intermediate Similarity	NPC194764
0.819	Intermediate Similarity	NPC29989
0.819	Intermediate Similarity	NPC95178
0.819	Intermediate Similarity	NPC69332
0.819	Intermediate Similarity	NPC477814
0.8182	Intermediate Similarity	NPC4665
0.8175	Intermediate Similarity	NPC471693
0.8175	Intermediate Similarity	NPC160900
0.8175	Intermediate Similarity	NPC46161
0.8175	Intermediate Similarity	NPC18984
0.8175	Intermediate Similarity	NPC229084
0.8175	Intermediate Similarity	NPC239608
0.8175	Intermediate Similarity	NPC106659
0.8174	Intermediate Similarity	NPC52087
0.8168	Intermediate Similarity	NPC239302
0.8167	Intermediate Similarity	NPC471485
0.8167	Intermediate Similarity	NPC264558
0.8162	Intermediate Similarity	NPC472904
0.816	Intermediate Similarity	NPC147654
0.816	Intermediate Similarity	NPC177291
0.816	Intermediate Similarity	NPC194416
0.8158	Intermediate Similarity	NPC110764
0.8154	Intermediate Similarity	NPC66905
0.8154	Intermediate Similarity	NPC233056
0.8145	Intermediate Similarity	NPC117780
0.8145	Intermediate Similarity	NPC56214
0.8145	Intermediate Similarity	NPC95614
0.8145	Intermediate Similarity	NPC232316
0.8145	Intermediate Similarity	NPC473136
0.8145	Intermediate Similarity	NPC227217
0.8145	Intermediate Similarity	NPC165133
0.8145	Intermediate Similarity	NPC242885
0.814	Intermediate Similarity	NPC158673
0.8134	Intermediate Similarity	NPC471152
0.8134	Intermediate Similarity	NPC290030

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 NPC98305 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	837
0.2-0.3	1342
0.3-0.4	2565
0.4-0.5	2200
0.5-0.6	1247
0.6-0.7	631
0.7-0.8	101
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8609	High Similarity	NPD3022	Approved
0.8609	High Similarity	NPD3021	Approved
0.8175	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD943	Approved
0.7899	Intermediate Similarity	NPD8166	Discontinued
0.7895	Intermediate Similarity	NPD825	Approved
0.7895	Intermediate Similarity	NPD826	Approved
0.7876	Intermediate Similarity	NPD2860	Approved
0.7876	Intermediate Similarity	NPD2859	Approved
0.7857	Intermediate Similarity	NPD2932	Approved
0.7857	Intermediate Similarity	NPD3019	Approved
0.7826	Intermediate Similarity	NPD3020	Approved
0.7803	Intermediate Similarity	NPD3027	Phase 3
0.7788	Intermediate Similarity	NPD2934	Approved
0.7788	Intermediate Similarity	NPD2933	Approved
0.774	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD257	Approved
0.771	Intermediate Similarity	NPD258	Approved
0.7705	Intermediate Similarity	NPD228	Approved
0.7671	Intermediate Similarity	NPD1934	Approved
0.7619	Intermediate Similarity	NPD5536	Phase 2
0.7589	Intermediate Similarity	NPD6190	Approved
0.7581	Intermediate Similarity	NPD5283	Phase 1
0.7574	Intermediate Similarity	NPD555	Phase 2
0.7556	Intermediate Similarity	NPD6663	Approved
0.7556	Intermediate Similarity	NPD259	Phase 1
0.7552	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD9494	Approved
0.7519	Intermediate Similarity	NPD5736	Approved
0.75	Intermediate Similarity	NPD1651	Approved
0.7482	Intermediate Similarity	NPD9570	Approved
0.7482	Intermediate Similarity	NPD2935	Discontinued
0.7481	Intermediate Similarity	NPD6798	Discontinued
0.7466	Intermediate Similarity	NPD3455	Phase 2
0.7462	Intermediate Similarity	NPD1201	Approved
0.7445	Intermediate Similarity	NPD6355	Discontinued
0.7429	Intermediate Similarity	NPD7266	Discontinued
0.74	Intermediate Similarity	NPD3882	Suspended
0.7394	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4110	Phase 3
0.7388	Intermediate Similarity	NPD9569	Approved
0.7385	Intermediate Similarity	NPD3026	Approved
0.7385	Intermediate Similarity	NPD3023	Approved
0.7383	Intermediate Similarity	NPD2801	Approved
0.7381	Intermediate Similarity	NPD2629	Approved
0.7368	Intermediate Similarity	NPD1470	Approved
0.7364	Intermediate Similarity	NPD3025	Approved
0.7364	Intermediate Similarity	NPD3024	Approved
0.7361	Intermediate Similarity	NPD1511	Approved
0.7328	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD3092	Approved
0.7319	Intermediate Similarity	NPD274	Approved
0.7319	Intermediate Similarity	NPD275	Approved
0.7319	Intermediate Similarity	NPD230	Phase 1
0.7299	Intermediate Similarity	NPD6233	Phase 2
0.7299	Intermediate Similarity	NPD4062	Phase 3
0.7293	Intermediate Similarity	NPD1283	Approved
0.729	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6166	Phase 2
0.7287	Intermediate Similarity	NPD3091	Approved
0.7286	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD844	Approved
0.726	Intermediate Similarity	NPD1512	Approved
0.7252	Intermediate Similarity	NPD3847	Discontinued
0.7246	Intermediate Similarity	NPD3062	Approved
0.7246	Intermediate Similarity	NPD3061	Approved
0.7246	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4060	Phase 1
0.7246	Intermediate Similarity	NPD3059	Approved
0.7246	Intermediate Similarity	NPD3620	Phase 2
0.7246	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1613	Approved
0.7241	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3053	Approved
0.7239	Intermediate Similarity	NPD3055	Approved
0.7239	Intermediate Similarity	NPD3094	Phase 2
0.7222	Intermediate Similarity	NPD9379	Approved
0.7222	Intermediate Similarity	NPD9377	Approved
0.7176	Intermediate Similarity	NPD9381	Approved
0.7176	Intermediate Similarity	NPD9384	Approved
0.7167	Intermediate Similarity	NPD1242	Phase 1
0.7164	Intermediate Similarity	NPD5311	Approved
0.7164	Intermediate Similarity	NPD5310	Approved
0.7163	Intermediate Similarity	NPD1510	Phase 2
0.7154	Intermediate Similarity	NPD1894	Discontinued
0.7153	Intermediate Similarity	NPD9537	Phase 1
0.7153	Intermediate Similarity	NPD4628	Phase 3
0.7153	Intermediate Similarity	NPD9536	Phase 1
0.7153	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7143	Intermediate Similarity	NPD5314	Approved
0.7131	Intermediate Similarity	NPD1237	Approved
0.7122	Intermediate Similarity	NPD1240	Approved
0.7111	Intermediate Similarity	NPD1164	Approved
0.7107	Intermediate Similarity	NPD7074	Phase 3
0.709	Intermediate Similarity	NPD9622	Approved
0.709	Intermediate Similarity	NPD1755	Approved
0.709	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3818	Discontinued
0.708	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6234	Discontinued
0.7073	Intermediate Similarity	NPD5048	Discontinued
0.7068	Intermediate Similarity	NPD1281	Approved
0.7068	Intermediate Similarity	NPD1535	Discovery
0.7067	Intermediate Similarity	NPD4380	Phase 2
0.7063	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5647	Approved
0.7059	Intermediate Similarity	NPD288	Approved
0.7059	Intermediate Similarity	NPD2798	Approved
0.7054	Intermediate Similarity	NPD255	Approved
0.7054	Intermediate Similarity	NPD256	Approved
0.7045	Intermediate Similarity	NPD3095	Discontinued
0.7044	Intermediate Similarity	NPD7054	Approved
0.7042	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD2799	Discontinued
0.704	Intermediate Similarity	NPD2684	Approved
0.7034	Intermediate Similarity	NPD3400	Discontinued
0.7031	Intermediate Similarity	NPD1241	Discontinued
0.7025	Intermediate Similarity	NPD3028	Approved
0.7025	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD9545	Approved
0.7021	Intermediate Similarity	NPD1607	Approved
0.7015	Intermediate Similarity	NPD1481	Phase 2
0.7015	Intermediate Similarity	NPD1608	Approved
0.7015	Intermediate Similarity	NPD3972	Approved
0.7014	Intermediate Similarity	NPD4534	Discontinued
0.7014	Intermediate Similarity	NPD1549	Phase 2
0.7007	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9493	Approved
0.7	Intermediate Similarity	NPD7472	Approved
0.7	Intermediate Similarity	NPD2979	Phase 3
0.7	Intermediate Similarity	NPD9495	Approved
0.6993	Remote Similarity	NPD2438	Suspended
0.6993	Remote Similarity	NPD5404	Approved
0.6993	Remote Similarity	NPD5405	Approved
0.6993	Remote Similarity	NPD3817	Phase 2
0.6993	Remote Similarity	NPD5408	Approved
0.6993	Remote Similarity	NPD5406	Approved
0.6991	Remote Similarity	NPD111	Approved
0.6978	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3764	Approved
0.6978	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD37	Approved
0.697	Remote Similarity	NPD1357	Approved
0.697	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD940	Approved
0.6967	Remote Similarity	NPD846	Approved
0.6959	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6797	Phase 2
0.6953	Remote Similarity	NPD7843	Approved
0.6953	Remote Similarity	NPD7635	Approved
0.6944	Remote Similarity	NPD2344	Approved
0.694	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD3300	Phase 2
0.6934	Remote Similarity	NPD9621	Approved
0.6934	Remote Similarity	NPD6584	Phase 3
0.6934	Remote Similarity	NPD9620	Approved
0.6934	Remote Similarity	NPD9619	Approved
0.6923	Remote Similarity	NPD7157	Approved
0.6923	Remote Similarity	NPD7033	Discontinued
0.6917	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7251	Discontinued
0.6912	Remote Similarity	NPD1876	Approved
0.6903	Remote Similarity	NPD7075	Discontinued
0.6899	Remote Similarity	NPD2229	Approved
0.6899	Remote Similarity	NPD5137	Approved
0.6899	Remote Similarity	NPD2234	Approved
0.6899	Remote Similarity	NPD2228	Approved
0.6897	Remote Similarity	NPD5958	Discontinued
0.6892	Remote Similarity	NPD7390	Discontinued
0.6889	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2861	Phase 2
0.6875	Remote Similarity	NPD2796	Approved
0.6871	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD2797	Approved
0.6857	Remote Similarity	NPD601	Approved
0.6857	Remote Similarity	NPD3268	Approved
0.6857	Remote Similarity	NPD598	Approved
0.6857	Remote Similarity	NPD597	Approved
0.685	Remote Similarity	NPD1792	Phase 2
0.685	Remote Similarity	NPD4750	Phase 3
0.6849	Remote Similarity	NPD3060	Approved
0.6849	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7028	Phase 2
0.6842	Remote Similarity	NPD9268	Approved
0.6842	Remote Similarity	NPD4093	Discontinued
0.6842	Remote Similarity	NPD5585	Approved
0.6839	Remote Similarity	NPD4967	Phase 2
0.6839	Remote Similarity	NPD4966	Approved
0.6839	Remote Similarity	NPD4965	Approved
0.6835	Remote Similarity	NPD6232	Discontinued
0.6833	Remote Similarity	NPD1809	Phase 2
0.6831	Remote Similarity	NPD447	Suspended
0.6825	Remote Similarity	NPD9265	Clinical (unspecified phase)

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