NPASS Compound

Structure

NPC65935 OpenBabel07101718302D 26 27 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 -7.7942 -0.5000 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 -9.5263 -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 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 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 -8.6603 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 -5.1962 0.0000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 1 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 -10.3923 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 -9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 -9.5263 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 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 7 16 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 1 1 0 0 0 16 22 2 0 0 0 0 17 19 2 0 0 0 0 17 23 1 0 0 0 0 18 20 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.16
Volume:	371.649
LogP:	1.651
LogD:	2.032
LogS:	-2.247
# 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:	2.78
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.919
MDCK Permeability:	1.3627257430925965e-05
Pgp-inhibitor:	0.036
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.068
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	92.0878677368164%
Volume Distribution (VD):	0.658
Pgp-substrate:	6.4640889167785645%

ADMET: Metabolism

CYP1A2-inhibitor:	0.519
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.515
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.646
CYP2C9-substrate:	0.884
CYP2D6-inhibitor:	0.675
CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	0.28
CYP3A4-substrate:	0.212

ADMET: Excretion

Clearance (CL):	18.024
Half-life (T1/2):	0.949

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.627
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.921
Carcinogencity:	0.083
Eye Corrosion:	0.006
Eye Irritation:	0.824
Respiratory Toxicity:	0.249

Download Data

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

Natural Product: NPC65935

Natural Product ID:	NPC65935
*Common Name:**	(5S)-7-(3,4-Dihydroxyphenyl)-5-Hydroxy-1-(4-Hydroxy-3-Methoxyphenyl)Heptan-3-One
IUPAC Name:	(5S)-7-(3,4-dihydroxyphenyl)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)heptan-3-one
Synonyms:
Standard InCHIKey:	MSLIBNPPWWCGPY-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C20H24O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)12-15(21)6-2-13-4-8-17(23)19(25)10-13/h4-5,8-11,15,21,23-25H,2-3,6-7,12H2,1H3/t15-/m0/s1
SMILES:	COc1cc(CCC(=O)C[C@H](CCc2ccc(c(c2)O)O)O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1824580
PubChem CID:	56675574
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
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1021/np100392m]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[20879743]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21807513]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22741	Curcuma kwangsiensis	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	9370.0	nM	PMID[485854]

☑ 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 NPC65935 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	287
0.1-0.2	1247
0.2-0.3	3426
0.3-0.4	9438
0.4-0.5	9405
0.5-0.6	3799
0.6-0.7	8105
0.7-0.8	6216
0.8-0.85	581
0.85-0.9	137
0.9-0.95	32
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC275724
1.0	High Similarity	NPC137427
1.0	High Similarity	NPC244246
1.0	High Similarity	NPC311419
1.0	High Similarity	NPC123196
1.0	High Similarity	NPC215941
1.0	High Similarity	NPC319282
0.9756	High Similarity	NPC293641
0.9756	High Similarity	NPC20287
0.9756	High Similarity	NPC20404
0.9756	High Similarity	NPC12022
0.9677	High Similarity	NPC278308
0.9593	High Similarity	NPC257589
0.9593	High Similarity	NPC53305
0.9516	High Similarity	NPC127937
0.9516	High Similarity	NPC92207
0.9431	High Similarity	NPC244876
0.937	High Similarity	NPC195292
0.9365	High Similarity	NPC226661
0.936	High Similarity	NPC303680
0.936	High Similarity	NPC84076
0.936	High Similarity	NPC90128
0.9318	High Similarity	NPC474784
0.9291	High Similarity	NPC304622
0.9286	High Similarity	NPC276466
0.9286	High Similarity	NPC5018
0.9286	High Similarity	NPC123722
0.9286	High Similarity	NPC123228
0.9286	High Similarity	NPC151167
0.9274	High Similarity	NPC163083
0.9268	High Similarity	NPC201777
0.9219	High Similarity	NPC142985
0.9206	High Similarity	NPC179777
0.9187	High Similarity	NPC98305
0.9187	High Similarity	NPC207613
0.9147	High Similarity	NPC469480
0.9127	High Similarity	NPC3221
0.9113	High Similarity	NPC262156
0.9113	High Similarity	NPC473853
0.9113	High Similarity	NPC312675
0.9113	High Similarity	NPC54872
0.9113	High Similarity	NPC184651
0.9113	High Similarity	NPC470212
0.9113	High Similarity	NPC324571
0.9113	High Similarity	NPC113865
0.9113	High Similarity	NPC343720
0.9106	High Similarity	NPC34634
0.9106	High Similarity	NPC265454
0.9024	High Similarity	NPC299406
0.9015	High Similarity	NPC113295
0.9008	High Similarity	NPC327410
0.8992	High Similarity	NPC241354
0.8976	High Similarity	NPC280767
0.8968	High Similarity	NPC471693
0.8968	High Similarity	NPC257976
0.8968	High Similarity	NPC242372
0.8968	High Similarity	NPC164778
0.8968	High Similarity	NPC4181
0.8943	High Similarity	NPC470626
0.8939	High Similarity	NPC5310
0.8939	High Similarity	NPC4982
0.8939	High Similarity	NPC300776
0.8939	High Similarity	NPC176814
0.8939	High Similarity	NPC68779
0.8923	High Similarity	NPC172673
0.8906	High Similarity	NPC276014
0.8905	High Similarity	NPC239608
0.8905	High Similarity	NPC46161
0.8898	High Similarity	NPC273686
0.8898	High Similarity	NPC312404
0.8889	High Similarity	NPC85488
0.8889	High Similarity	NPC114298
0.8889	High Similarity	NPC86900
0.888	High Similarity	NPC158949
0.8872	High Similarity	NPC470990
0.8872	High Similarity	NPC152209
0.8871	High Similarity	NPC24474
0.8871	High Similarity	NPC311595
0.8862	High Similarity	NPC164386
0.8862	High Similarity	NPC293619
0.8849	High Similarity	NPC208507
0.8849	High Similarity	NPC472333
0.8828	High Similarity	NPC148627
0.8824	High Similarity	NPC100675
0.8819	High Similarity	NPC229084
0.8819	High Similarity	NPC18984
0.8819	High Similarity	NPC106659
0.8819	High Similarity	NPC160900
0.8819	High Similarity	NPC280704
0.881	High Similarity	NPC194416
0.881	High Similarity	NPC290451
0.881	High Similarity	NPC127389
0.881	High Similarity	NPC177291
0.8806	High Similarity	NPC90431
0.88	High Similarity	NPC95614
0.88	High Similarity	NPC117780
0.88	High Similarity	NPC165133
0.88	High Similarity	NPC242885
0.88	High Similarity	NPC232316
0.88	High Similarity	NPC56214
0.88	High Similarity	NPC227217
0.8797	High Similarity	NPC471110
0.879	High Similarity	NPC474214
0.8788	High Similarity	NPC50763
0.8788	High Similarity	NPC239302
0.8779	High Similarity	NPC66905
0.875	High Similarity	NPC322021
0.873	High Similarity	NPC189844
0.873	High Similarity	NPC109083
0.873	High Similarity	NPC269843
0.873	High Similarity	NPC224814
0.873	High Similarity	NPC14007
0.873	High Similarity	NPC60962
0.872	High Similarity	NPC281298
0.872	High Similarity	NPC310338
0.872	High Similarity	NPC474320
0.8705	High Similarity	NPC53884
0.8705	High Similarity	NPC258671
0.8705	High Similarity	NPC223185
0.8692	High Similarity	NPC118533
0.8692	High Similarity	NPC165045
0.8686	High Similarity	NPC78987
0.8686	High Similarity	NPC82336
0.8682	High Similarity	NPC194519
0.8676	High Similarity	NPC284409
0.8672	High Similarity	NPC31344
0.8672	High Similarity	NPC317769
0.8661	High Similarity	NPC38996
0.8661	High Similarity	NPC160380
0.8652	High Similarity	NPC1580
0.8643	High Similarity	NPC474799
0.864	High Similarity	NPC474040
0.8633	High Similarity	NPC304956
0.8626	High Similarity	NPC206615
0.8626	High Similarity	NPC186843
0.8626	High Similarity	NPC245826
0.8626	High Similarity	NPC474178
0.8626	High Similarity	NPC470213
0.8626	High Similarity	NPC98631
0.8626	High Similarity	NPC252307
0.8623	High Similarity	NPC52664
0.8615	High Similarity	NPC213552
0.8615	High Similarity	NPC120225
0.8615	High Similarity	NPC191037
0.8615	High Similarity	NPC178284
0.8615	High Similarity	NPC58607
0.8613	High Similarity	NPC288452
0.8613	High Similarity	NPC289690
0.8605	High Similarity	NPC114901
0.8605	High Similarity	NPC48990
0.8605	High Similarity	NPC293701
0.8594	High Similarity	NPC286573
0.8592	High Similarity	NPC474903
0.8582	High Similarity	NPC143892
0.8582	High Similarity	NPC299090
0.8582	High Similarity	NPC221383
0.8582	High Similarity	NPC475468
0.8582	High Similarity	NPC283081
0.8561	High Similarity	NPC170844
0.8561	High Similarity	NPC476968
0.8561	High Similarity	NPC475875
0.8561	High Similarity	NPC212015
0.8551	High Similarity	NPC282291
0.8551	High Similarity	NPC19158
0.8551	High Similarity	NPC166137
0.8551	High Similarity	NPC29599
0.855	High Similarity	NPC111247
0.855	High Similarity	NPC41706
0.855	High Similarity	NPC183181
0.855	High Similarity	NPC319625
0.855	High Similarity	NPC163332
0.855	High Similarity	NPC5428
0.855	High Similarity	NPC292056
0.855	High Similarity	NPC118787
0.855	High Similarity	NPC147821
0.854	High Similarity	NPC325625
0.8538	High Similarity	NPC289459
0.8529	High Similarity	NPC324929
0.8516	High Similarity	NPC476343
0.8496	Intermediate Similarity	NPC153739
0.8496	Intermediate Similarity	NPC42300
0.8496	Intermediate Similarity	NPC242807
0.8496	Intermediate Similarity	NPC64201
0.8496	Intermediate Similarity	NPC92164
0.8496	Intermediate Similarity	NPC145305
0.8496	Intermediate Similarity	NPC241522
0.8496	Intermediate Similarity	NPC143483
0.8496	Intermediate Similarity	NPC77040
0.8496	Intermediate Similarity	NPC174495
0.8496	Intermediate Similarity	NPC187998
0.8496	Intermediate Similarity	NPC257582
0.8492	Intermediate Similarity	NPC255675
0.8492	Intermediate Similarity	NPC205502
0.8489	Intermediate Similarity	NPC472335
0.8489	Intermediate Similarity	NPC31751
0.8489	Intermediate Similarity	NPC253481
0.8489	Intermediate Similarity	NPC472332
0.8489	Intermediate Similarity	NPC472410
0.8489	Intermediate Similarity	NPC253722
0.8485	Intermediate Similarity	NPC282703

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 NPC65935 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	847
0.2-0.3	1498
0.3-0.4	2562
0.4-0.5	1949
0.5-0.6	1102
0.6-0.7	775
0.7-0.8	153
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8819	High Similarity	NPD4379	Clinical (unspecified phase)
0.8561	High Similarity	NPD3027	Phase 3
0.8374	Intermediate Similarity	NPD228	Approved
0.8268	Intermediate Similarity	NPD5536	Phase 2
0.824	Intermediate Similarity	NPD5283	Phase 1
0.8231	Intermediate Similarity	NPD1934	Approved
0.8134	Intermediate Similarity	NPD9494	Approved
0.8054	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD4110	Phase 3
0.7971	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD3620	Phase 2
0.7956	Intermediate Similarity	NPD6798	Discontinued
0.7947	Intermediate Similarity	NPD3882	Suspended
0.7935	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6166	Phase 2
0.7933	Intermediate Similarity	NPD2801	Approved
0.792	Intermediate Similarity	NPD3022	Approved
0.792	Intermediate Similarity	NPD3021	Approved
0.7914	Intermediate Similarity	NPD6355	Discontinued
0.7863	Intermediate Similarity	NPD1651	Approved
0.7842	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1613	Approved
0.7817	Intermediate Similarity	NPD2935	Discontinued
0.7808	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD4062	Phase 3
0.777	Intermediate Similarity	NPD6233	Phase 2
0.7736	Intermediate Similarity	NPD7074	Phase 3
0.7727	Intermediate Similarity	NPD1357	Approved
0.7724	Intermediate Similarity	NPD4628	Phase 3
0.7722	Intermediate Similarity	NPD3818	Discontinued
0.7714	Intermediate Similarity	NPD4060	Phase 1
0.7698	Intermediate Similarity	NPD2684	Approved
0.7687	Intermediate Similarity	NPD1511	Approved
0.7673	Intermediate Similarity	NPD7054	Approved
0.7664	Intermediate Similarity	NPD5647	Approved
0.7647	Intermediate Similarity	NPD1283	Approved
0.7632	Intermediate Similarity	NPD37	Approved
0.7626	Intermediate Similarity	NPD7095	Approved
0.7625	Intermediate Similarity	NPD7472	Approved
0.7616	Intermediate Similarity	NPD4380	Phase 2
0.7613	Intermediate Similarity	NPD6234	Discontinued
0.7612	Intermediate Similarity	NPD3847	Discontinued
0.7603	Intermediate Similarity	NPD8166	Discontinued
0.7597	Intermediate Similarity	NPD7843	Approved
0.7584	Intermediate Similarity	NPD1512	Approved
0.7557	Intermediate Similarity	NPD7157	Approved
0.7554	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6190	Approved
0.7534	Intermediate Similarity	NPD3060	Approved
0.7532	Intermediate Similarity	NPD3817	Phase 2
0.7519	Intermediate Similarity	NPD1894	Discontinued
0.75	Intermediate Similarity	NPD1510	Phase 2
0.7484	Intermediate Similarity	NPD4967	Phase 2
0.7484	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4965	Approved
0.7484	Intermediate Similarity	NPD4966	Approved
0.7482	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6797	Phase 2
0.7466	Intermediate Similarity	NPD4534	Discontinued
0.7465	Intermediate Similarity	NPD943	Approved
0.7465	Intermediate Similarity	NPD1240	Approved
0.7448	Intermediate Similarity	NPD2438	Suspended
0.7445	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD3455	Phase 2
0.7426	Intermediate Similarity	NPD1535	Discovery
0.7426	Intermediate Similarity	NPD1281	Approved
0.7423	Intermediate Similarity	NPD7251	Discontinued
0.7413	Intermediate Similarity	NPD447	Suspended
0.741	Intermediate Similarity	NPD2798	Approved
0.7405	Intermediate Similarity	NPD1241	Discontinued
0.7397	Intermediate Similarity	NPD7266	Discontinued
0.7397	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2674	Phase 3
0.7391	Intermediate Similarity	NPD7228	Approved
0.7386	Intermediate Similarity	NPD7028	Phase 2
0.7379	Intermediate Similarity	NPD2799	Discontinued
0.7379	Intermediate Similarity	NPD7033	Discontinued
0.7378	Intermediate Similarity	NPD7808	Phase 3
0.7378	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3972	Approved
0.7372	Intermediate Similarity	NPD1481	Phase 2
0.7372	Intermediate Similarity	NPD1608	Approved
0.7361	Intermediate Similarity	NPD6653	Approved
0.7361	Intermediate Similarity	NPD1607	Approved
0.7358	Intermediate Similarity	NPD6232	Discontinued
0.7347	Intermediate Similarity	NPD5958	Discontinued
0.7347	Intermediate Similarity	NPD1549	Phase 2
0.7343	Intermediate Similarity	NPD2979	Phase 3
0.7343	Intermediate Similarity	NPD826	Approved
0.7343	Intermediate Similarity	NPD1558	Phase 1
0.7343	Intermediate Similarity	NPD825	Approved
0.7329	Intermediate Similarity	NPD7473	Discontinued
0.7325	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7075	Discontinued
0.7324	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD2983	Phase 2
0.7319	Intermediate Similarity	NPD2982	Phase 2
0.7303	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4162	Approved
0.7296	Intermediate Similarity	NPD7199	Phase 2
0.7286	Intermediate Similarity	NPD6584	Phase 3
0.7285	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2344	Approved
0.7279	Intermediate Similarity	NPD3019	Approved
0.7279	Intermediate Similarity	NPD6516	Phase 2
0.7279	Intermediate Similarity	NPD5846	Approved
0.7279	Intermediate Similarity	NPD2932	Approved
0.7266	Intermediate Similarity	NPD1876	Approved
0.7246	Intermediate Similarity	NPD2981	Phase 2
0.7244	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD2859	Approved
0.7236	Intermediate Similarity	NPD2860	Approved
0.7234	Intermediate Similarity	NPD3018	Phase 2
0.7234	Intermediate Similarity	NPD2861	Phase 2
0.7233	Intermediate Similarity	NPD5494	Approved
0.723	Intermediate Similarity	NPD2424	Discontinued
0.7219	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6799	Approved
0.7214	Intermediate Similarity	NPD2797	Approved
0.7211	Intermediate Similarity	NPD2796	Approved
0.7211	Intermediate Similarity	NPD6032	Approved
0.7209	Intermediate Similarity	NPD290	Approved
0.7206	Intermediate Similarity	NPD5585	Approved
0.7203	Intermediate Similarity	NPD3268	Approved
0.7203	Intermediate Similarity	NPD5109	Approved
0.7203	Intermediate Similarity	NPD5111	Phase 2
0.7203	Intermediate Similarity	NPD5110	Phase 2
0.7203	Intermediate Similarity	NPD3144	Approved
0.7203	Intermediate Similarity	NPD3145	Approved
0.72	Intermediate Similarity	NPD5241	Discontinued
0.72	Intermediate Similarity	NPD3020	Approved
0.7197	Intermediate Similarity	NPD5535	Approved
0.7188	Intermediate Similarity	NPD8127	Discontinued
0.7183	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4236	Phase 3
0.7181	Intermediate Similarity	NPD4237	Approved
0.7181	Intermediate Similarity	NPD5177	Phase 3
0.7179	Intermediate Similarity	NPD6801	Discontinued
0.7174	Intermediate Similarity	NPD3705	Approved
0.7172	Intermediate Similarity	NPD1933	Approved
0.7172	Intermediate Similarity	NPD230	Phase 1
0.7171	Intermediate Similarity	NPD4662	Approved
0.7171	Intermediate Similarity	NPD4661	Approved
0.7164	Intermediate Similarity	NPD6671	Approved
0.7163	Intermediate Similarity	NPD257	Approved
0.7163	Intermediate Similarity	NPD258	Approved
0.7154	Intermediate Similarity	NPD2934	Approved
0.7154	Intermediate Similarity	NPD2933	Approved
0.7154	Intermediate Similarity	NPD9296	Approved
0.7153	Intermediate Similarity	NPD4626	Approved
0.7153	Intermediate Similarity	NPD17	Approved
0.7152	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2977	Approved
0.7134	Intermediate Similarity	NPD5844	Phase 1
0.7134	Intermediate Similarity	NPD2978	Approved
0.7133	Intermediate Similarity	NPD6331	Phase 2
0.7132	Intermediate Similarity	NPD968	Approved
0.7124	Intermediate Similarity	NPD6273	Approved
0.7108	Intermediate Similarity	NPD6559	Discontinued
0.7108	Intermediate Similarity	NPD7685	Pre-registration
0.7105	Intermediate Similarity	NPD4357	Discontinued
0.7103	Intermediate Similarity	NPD4140	Approved
0.7099	Intermediate Similarity	NPD5451	Approved
0.7099	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7458	Discontinued
0.7095	Intermediate Similarity	NPD4477	Approved
0.7095	Intermediate Similarity	NPD4476	Approved
0.7095	Intermediate Similarity	NPD2239	Approved
0.7095	Intermediate Similarity	NPD5712	Approved
0.7095	Intermediate Similarity	NPD9570	Approved
0.7095	Intermediate Similarity	NPD2531	Phase 2
0.7095	Intermediate Similarity	NPD2240	Approved
0.7095	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1203	Approved
0.709	Intermediate Similarity	NPD2629	Approved
0.7089	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5402	Approved
0.7087	Intermediate Similarity	NPD291	Approved
0.7086	Intermediate Similarity	NPD2309	Approved
0.7083	Intermediate Similarity	NPD2313	Discontinued
0.7078	Intermediate Similarity	NPD5403	Approved
0.7078	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD1358	Approved
0.7075	Intermediate Similarity	NPD7097	Phase 1
0.7075	Intermediate Similarity	NPD4536	Approved
0.7075	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4538	Approved
0.7071	Intermediate Similarity	NPD6583	Phase 3
0.7071	Intermediate Similarity	NPD6582	Phase 2
0.7067	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6832	Phase 2
0.7063	Intermediate Similarity	NPD2614	Approved
0.7063	Intermediate Similarity	NPD4908	Phase 1
0.7059	Intermediate Similarity	NPD7004	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