NPASS Compound

Structure

CID255807 OpenBabel06191716062D 24 26 0 0 1 0 0 0 0 0999 V2000 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 0.8660 -1.5000 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 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -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 -4.3301 -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 3 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 -4.3301 -1.5000 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 -0.8660 -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 -6.9282 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 14 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 24 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 17 2 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 16 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 15 24 1 0 0 0 0 16 20 2 0 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.11
Volume:	328.501
LogP:	2.411
LogD:	2.505
LogS:	-3.878
# Rotatable Bonds:	4
TPSA:	74.22
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.929
Synthetic Accessibility Score:	2.844
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.652
MDCK Permeability:	3.2639636629028246e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	97.53911590576172%
Volume Distribution (VD):	0.505
Pgp-substrate:	5.0561089515686035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.664
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.886
CYP2C19-substrate:	0.869
CYP2C9-inhibitor:	0.769
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.383
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.854
CYP3A4-substrate:	0.867

ADMET: Excretion

Clearance (CL):	5.816
Half-life (T1/2):	0.461

ADMET: Toxicity

hERG Blockers:	0.111
Human Hepatotoxicity (H-HT):	0.19
Drug-inuced Liver Injury (DILI):	0.34
AMES Toxicity:	0.203
Rat Oral Acute Toxicity:	0.345
Maximum Recommended Daily Dose:	0.366
Skin Sensitization:	0.309
Carcinogencity:	0.179
Eye Corrosion:	0.003
Eye Irritation:	0.05
Respiratory Toxicity:	0.105

Download Data

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

Natural Product: NPC255807

Natural Product ID:	NPC255807
*Common Name:**	(3R,3S)-3-O-Methylviolanone
IUPAC Name:	7-hydroxy-3-(2,3,4-trimethoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	IFIRIIBDWLSFFH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H18O6/c1-21-14-7-6-11(17(22-2)18(14)23-3)13-9-24-15-8-10(19)4-5-12(15)16(13)20/h4-8,13,19H,9H2,1-3H3
SMILES:	COc1c(ccc(c1OC)OC)C1COc2c(C1=O)ccc(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1086619
PubChem CID:	5319813
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids

*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
NPO14114	Dalbergia parviflora	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19928832]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23743282]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9525107]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14114	Dalbergia parviflora	Species	Fabaceae	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
Others	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	Activity	>	100.0	uM	PMID[492562]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	3.3	uM	PMID[492562]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[492562]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	6.1	uM	PMID[492562]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	46.3	uM	PMID[492562]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	2.5	uM	PMID[492562]

☑ 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 NPC255807 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	401
0.1-0.2	1622
0.2-0.3	3956
0.3-0.4	9600
0.4-0.5	8480
0.5-0.6	3239
0.6-0.7	4667
0.7-0.8	5588
0.8-0.85	2606
0.85-0.9	1965
0.9-0.95	526
0.95-1	47

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC31018
0.9866	High Similarity	NPC181960
0.9866	High Similarity	NPC299520
0.9866	High Similarity	NPC129684
0.9732	High Similarity	NPC472909
0.9664	High Similarity	NPC472915
0.9664	High Similarity	NPC469550
0.9603	High Similarity	NPC96167
0.9603	High Similarity	NPC469584
0.9603	High Similarity	NPC472913
0.9603	High Similarity	NPC472911
0.9603	High Similarity	NPC472910
0.9603	High Similarity	NPC222814
0.9603	High Similarity	NPC245758
0.9603	High Similarity	NPC472914
0.96	High Similarity	NPC37392
0.9597	High Similarity	NPC477231
0.9597	High Similarity	NPC472912
0.9597	High Similarity	NPC257648
0.9597	High Similarity	NPC260979
0.9595	High Similarity	NPC338131
0.9539	High Similarity	NPC55738
0.9536	High Similarity	NPC472916
0.9533	High Similarity	NPC280937
0.9533	High Similarity	NPC18727
0.953	High Similarity	NPC149614
0.953	High Similarity	NPC117579
0.953	High Similarity	NPC31363
0.9524	High Similarity	NPC470511
0.9481	High Similarity	NPC474150
0.9481	High Similarity	NPC474162
0.9474	High Similarity	NPC474836
0.9474	High Similarity	NPC67876
0.9474	High Similarity	NPC48208
0.9474	High Similarity	NPC291508
0.9474	High Similarity	NPC99597
0.9474	High Similarity	NPC162869
0.9474	High Similarity	NPC156057
0.9474	High Similarity	NPC474208
0.9474	High Similarity	NPC108456
0.9474	High Similarity	NPC210084
0.9474	High Similarity	NPC475267
0.947	High Similarity	NPC117992
0.947	High Similarity	NPC152951
0.947	High Similarity	NPC226025
0.947	High Similarity	NPC2928
0.947	High Similarity	NPC168247
0.947	High Similarity	NPC230149
0.947	High Similarity	NPC57674
0.9467	High Similarity	NPC60972
0.9467	High Similarity	NPC219582
0.9467	High Similarity	NPC302950
0.9467	High Similarity	NPC39732
0.9467	High Similarity	NPC236637
0.9463	High Similarity	NPC179183
0.9463	High Similarity	NPC29231
0.9459	High Similarity	NPC195202
0.9456	High Similarity	NPC299011
0.9423	High Similarity	NPC235610
0.9416	High Similarity	NPC266314
0.9416	High Similarity	NPC474187
0.9412	High Similarity	NPC152904
0.9408	High Similarity	NPC474638
0.9408	High Similarity	NPC291878
0.9408	High Similarity	NPC255106
0.9408	High Similarity	NPC35038
0.9408	High Similarity	NPC278778
0.9408	High Similarity	NPC235165
0.9408	High Similarity	NPC195796
0.9404	High Similarity	NPC206238
0.9404	High Similarity	NPC49402
0.9404	High Similarity	NPC70433
0.9404	High Similarity	NPC167091
0.9404	High Similarity	NPC88645
0.9404	High Similarity	NPC292214
0.9404	High Similarity	NPC227337
0.9404	High Similarity	NPC271779
0.9404	High Similarity	NPC273462
0.9404	High Similarity	NPC33051
0.94	High Similarity	NPC262623
0.94	High Similarity	NPC208043
0.94	High Similarity	NPC226973
0.94	High Similarity	NPC308451
0.9396	High Similarity	NPC105512
0.9396	High Similarity	NPC238366
0.9392	High Similarity	NPC12200
0.9392	High Similarity	NPC33265
0.9392	High Similarity	NPC62536
0.9388	High Similarity	NPC311144
0.9388	High Similarity	NPC184649
0.9388	High Similarity	NPC303185
0.9359	High Similarity	NPC234052
0.9359	High Similarity	NPC472277
0.9355	High Similarity	NPC472964
0.9351	High Similarity	NPC474287
0.9351	High Similarity	NPC36217
0.9351	High Similarity	NPC474960
0.9351	High Similarity	NPC472902
0.9351	High Similarity	NPC475886
0.9351	High Similarity	NPC299436
0.9346	High Similarity	NPC165977
0.9346	High Similarity	NPC180011
0.9346	High Similarity	NPC27337
0.9346	High Similarity	NPC161960
0.9346	High Similarity	NPC304008
0.9346	High Similarity	NPC472598
0.9346	High Similarity	NPC187745
0.9346	High Similarity	NPC219867
0.9346	High Similarity	NPC300727
0.9346	High Similarity	NPC284820
0.9346	High Similarity	NPC78225
0.9346	High Similarity	NPC217677
0.9346	High Similarity	NPC471479
0.9346	High Similarity	NPC241904
0.9346	High Similarity	NPC52530
0.9346	High Similarity	NPC471515
0.9346	High Similarity	NPC262286
0.9346	High Similarity	NPC474055
0.9346	High Similarity	NPC472963
0.9346	High Similarity	NPC473272
0.9346	High Similarity	NPC476981
0.9346	High Similarity	NPC36852
0.9342	High Similarity	NPC67396
0.9342	High Similarity	NPC213622
0.9342	High Similarity	NPC256925
0.9342	High Similarity	NPC45849
0.9342	High Similarity	NPC20830
0.9342	High Similarity	NPC477503
0.9342	High Similarity	NPC256612
0.9342	High Similarity	NPC470327
0.9342	High Similarity	NPC200761
0.9338	High Similarity	NPC199100
0.9338	High Similarity	NPC101996
0.9338	High Similarity	NPC180234
0.9338	High Similarity	NPC120537
0.9338	High Similarity	NPC39007
0.9338	High Similarity	NPC161277
0.9333	High Similarity	NPC50728
0.9333	High Similarity	NPC239363
0.9333	High Similarity	NPC156953
0.9333	High Similarity	NPC306821
0.9333	High Similarity	NPC166753
0.9329	High Similarity	NPC10304
0.9329	High Similarity	NPC43669
0.9329	High Similarity	NPC272721
0.9329	High Similarity	NPC39195
0.9329	High Similarity	NPC3036
0.9329	High Similarity	NPC63256
0.9329	High Similarity	NPC196277
0.9324	High Similarity	NPC12377
0.932	High Similarity	NPC113770
0.932	High Similarity	NPC293201
0.9299	High Similarity	NPC128293
0.9299	High Similarity	NPC477517
0.9299	High Similarity	NPC120593
0.9295	High Similarity	NPC472281
0.9295	High Similarity	NPC18100
0.9295	High Similarity	NPC273959
0.9295	High Similarity	NPC205265
0.9295	High Similarity	NPC124038
0.929	High Similarity	NPC474351
0.929	High Similarity	NPC475883
0.929	High Similarity	NPC134783
0.929	High Similarity	NPC474186
0.929	High Similarity	NPC173137
0.929	High Similarity	NPC472275
0.929	High Similarity	NPC308992
0.9286	High Similarity	NPC476242
0.9286	High Similarity	NPC250214
0.9286	High Similarity	NPC95936
0.9286	High Similarity	NPC204879
0.9281	High Similarity	NPC472907
0.9281	High Similarity	NPC472626
0.9281	High Similarity	NPC326037
0.9281	High Similarity	NPC68093
0.9281	High Similarity	NPC274730
0.9281	High Similarity	NPC470328
0.9281	High Similarity	NPC115853
0.9281	High Similarity	NPC24640
0.9281	High Similarity	NPC13858
0.9281	High Similarity	NPC471500
0.9281	High Similarity	NPC138243
0.9281	High Similarity	NPC209614
0.9281	High Similarity	NPC472455
0.9281	High Similarity	NPC320825
0.9281	High Similarity	NPC303255
0.9281	High Similarity	NPC191146
0.9281	High Similarity	NPC265511
0.9276	High Similarity	NPC124714
0.9276	High Similarity	NPC274327
0.9276	High Similarity	NPC141212
0.9276	High Similarity	NPC231018
0.9276	High Similarity	NPC145379
0.9276	High Similarity	NPC192083
0.9276	High Similarity	NPC183878
0.9276	High Similarity	NPC86485
0.9276	High Similarity	NPC472905
0.9276	High Similarity	NPC213896
0.9276	High Similarity	NPC255350
0.9276	High Similarity	NPC160951

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 NPC255807 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	949
0.2-0.3	1661
0.3-0.4	2582
0.4-0.5	1785
0.5-0.6	1065
0.6-0.7	523
0.7-0.8	153
0.8-0.85	43
0.85-0.9	17
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9467	High Similarity	NPD1934	Approved
0.9276	High Similarity	NPD2801	Approved
0.9276	High Similarity	NPD2393	Clinical (unspecified phase)
0.9156	High Similarity	NPD3882	Suspended
0.9103	High Similarity	NPD5494	Approved
0.8994	High Similarity	NPD6168	Clinical (unspecified phase)
0.8994	High Similarity	NPD6167	Clinical (unspecified phase)
0.8994	High Similarity	NPD6166	Phase 2
0.8933	High Similarity	NPD1511	Approved
0.8882	High Similarity	NPD3818	Discontinued
0.8851	High Similarity	NPD1549	Phase 2
0.8846	High Similarity	NPD3817	Phase 2
0.8816	High Similarity	NPD1512	Approved
0.879	High Similarity	NPD4868	Clinical (unspecified phase)
0.8784	High Similarity	NPD1550	Clinical (unspecified phase)
0.8784	High Similarity	NPD1552	Clinical (unspecified phase)
0.8773	High Similarity	NPD7074	Phase 3
0.875	High Similarity	NPD4378	Clinical (unspecified phase)
0.8712	High Similarity	NPD7054	Approved
0.871	High Similarity	NPD4380	Phase 2
0.8704	High Similarity	NPD7473	Discontinued
0.8662	High Similarity	NPD7819	Suspended
0.8659	High Similarity	NPD7472	Approved
0.8649	High Similarity	NPD1510	Phase 2
0.8634	High Similarity	NPD6232	Discontinued
0.8616	High Similarity	NPD7075	Discontinued
0.8616	High Similarity	NPD4381	Clinical (unspecified phase)
0.8608	High Similarity	NPD8443	Clinical (unspecified phase)
0.8591	High Similarity	NPD2796	Approved
0.8544	High Similarity	NPD7096	Clinical (unspecified phase)
0.8503	High Similarity	NPD4338	Clinical (unspecified phase)
0.8503	High Similarity	NPD7808	Phase 3
0.8503	High Similarity	NPD1240	Approved
0.8494	Intermediate Similarity	NPD6797	Phase 2
0.8485	Intermediate Similarity	NPD5844	Phase 1
0.8443	Intermediate Similarity	NPD7251	Discontinued
0.8442	Intermediate Similarity	NPD6799	Approved
0.8428	Intermediate Similarity	NPD1465	Phase 2
0.8418	Intermediate Similarity	NPD7411	Suspended
0.8389	Intermediate Similarity	NPD1607	Approved
0.8387	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD3926	Phase 2
0.8354	Intermediate Similarity	NPD6599	Discontinued
0.8344	Intermediate Similarity	NPD6959	Discontinued
0.8274	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD943	Approved
0.825	Intermediate Similarity	NPD6801	Discontinued
0.8235	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD1247	Approved
0.8193	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD3749	Approved
0.8155	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD5402	Approved
0.8129	Intermediate Similarity	NPD3750	Approved
0.8118	Intermediate Similarity	NPD6559	Discontinued
0.811	Intermediate Similarity	NPD919	Approved
0.8098	Intermediate Similarity	NPD7768	Phase 2
0.8079	Intermediate Similarity	NPD447	Suspended
0.8065	Intermediate Similarity	NPD2800	Approved
0.805	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD2534	Approved
0.8038	Intermediate Similarity	NPD2533	Approved
0.8038	Intermediate Similarity	NPD2532	Approved
0.8013	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1613	Approved
0.8	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1551	Phase 2
0.7987	Intermediate Similarity	NPD6099	Approved
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7987	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6100	Approved
0.7961	Intermediate Similarity	NPD230	Phase 1
0.7949	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD5403	Approved
0.7935	Intermediate Similarity	NPD2344	Approved
0.7922	Intermediate Similarity	NPD2799	Discontinued
0.7919	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7199	Phase 2
0.7898	Intermediate Similarity	NPD4628	Phase 3
0.7881	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD4908	Phase 1
0.7843	Intermediate Similarity	NPD1933	Approved
0.784	Intermediate Similarity	NPD3226	Approved
0.7826	Intermediate Similarity	NPD920	Approved
0.7821	Intermediate Similarity	NPD2346	Discontinued
0.7815	Intermediate Similarity	NPD3027	Phase 3
0.7812	Intermediate Similarity	NPD5401	Approved
0.7811	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD3748	Approved
0.7805	Intermediate Similarity	NPD37	Approved
0.7785	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6234	Discontinued
0.7778	Intermediate Similarity	NPD3751	Discontinued
0.7771	Intermediate Similarity	NPD4966	Approved
0.7771	Intermediate Similarity	NPD4967	Phase 2
0.7771	Intermediate Similarity	NPD4965	Approved
0.7763	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1610	Phase 2
0.775	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD5953	Discontinued
0.7736	Intermediate Similarity	NPD2309	Approved
0.7733	Intermediate Similarity	NPD7286	Phase 2
0.7727	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD5242	Approved
0.7702	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD9494	Approved
0.7677	Intermediate Similarity	NPD6651	Approved
0.7647	Intermediate Similarity	NPD2313	Discontinued
0.7647	Intermediate Similarity	NPD3787	Discontinued
0.7635	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2798	Approved
0.7614	Intermediate Similarity	NPD8312	Approved
0.7614	Intermediate Similarity	NPD8313	Approved
0.7611	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1243	Approved
0.7605	Intermediate Similarity	NPD5353	Approved
0.76	Intermediate Similarity	NPD7685	Pre-registration
0.7593	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7228	Approved
0.7561	Intermediate Similarity	NPD1653	Approved
0.755	Intermediate Similarity	NPD1203	Approved
0.7544	Intermediate Similarity	NPD5710	Approved
0.7544	Intermediate Similarity	NPD5711	Approved
0.7533	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3268	Approved
0.7531	Intermediate Similarity	NPD7390	Discontinued
0.7527	Intermediate Similarity	NPD4360	Phase 2
0.7527	Intermediate Similarity	NPD4363	Phase 3
0.7516	Intermediate Similarity	NPD6190	Approved
0.7516	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7467	Intermediate Similarity	NPD1608	Approved
0.7457	Intermediate Similarity	NPD2403	Approved
0.7451	Intermediate Similarity	NPD2861	Phase 2
0.7442	Intermediate Similarity	NPD7229	Phase 3
0.7434	Intermediate Similarity	NPD2797	Approved
0.7425	Intermediate Similarity	NPD6386	Approved
0.7425	Intermediate Similarity	NPD6385	Approved
0.7425	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD4749	Approved
0.741	Intermediate Similarity	NPD7458	Discontinued
0.741	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8150	Discontinued
0.7381	Intermediate Similarity	NPD6844	Discontinued
0.7378	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1548	Phase 1
0.736	Intermediate Similarity	NPD7549	Discontinued
0.7358	Intermediate Similarity	NPD7033	Discontinued
0.7355	Intermediate Similarity	NPD4625	Phase 3
0.7353	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD9717	Approved
0.7326	Intermediate Similarity	NPD6776	Approved
0.7326	Intermediate Similarity	NPD6779	Approved
0.7326	Intermediate Similarity	NPD6780	Approved
0.7326	Intermediate Similarity	NPD6777	Approved
0.7326	Intermediate Similarity	NPD6781	Approved
0.7326	Intermediate Similarity	NPD6778	Approved
0.7326	Intermediate Similarity	NPD6782	Approved
0.732	Intermediate Similarity	NPD1470	Approved
0.7317	Intermediate Similarity	NPD4357	Discontinued
0.7308	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5536	Phase 2
0.7297	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4361	Phase 2
0.7292	Intermediate Similarity	NPD8151	Discontinued
0.7283	Intermediate Similarity	NPD8127	Discontinued
0.7278	Intermediate Similarity	NPD6355	Discontinued
0.7267	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD17	Approved
0.7258	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4308	Phase 3
0.7239	Intermediate Similarity	NPD4110	Phase 3
0.7239	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD9269	Phase 2
0.7237	Intermediate Similarity	NPD3972	Approved
0.7235	Intermediate Similarity	NPD5761	Phase 2
0.7235	Intermediate Similarity	NPD5760	Phase 2
0.7226	Intermediate Similarity	NPD3018	Phase 2
0.7215	Intermediate Similarity	NPD4060	Phase 1
0.7213	Intermediate Similarity	NPD4287	Approved
0.7211	Intermediate Similarity	NPD7696	Phase 3
0.7211	Intermediate Similarity	NPD7698	Approved
0.7211	Intermediate Similarity	NPD7435	Discontinued
0.7211	Intermediate Similarity	NPD7697	Approved
0.7208	Intermediate Similarity	NPD3267	Approved
0.7208	Intermediate Similarity	NPD3266	Approved
0.7207	Intermediate Similarity	NPD7240	Approved
0.72	Intermediate Similarity	NPD9268	Approved
0.7197	Intermediate Similarity	NPD6798	Discontinued
0.7197	Intermediate Similarity	NPD3764	Approved
0.7197	Intermediate Similarity	NPD411	Approved
0.7193	Intermediate Similarity	NPD4288	Approved
0.7193	Intermediate Similarity	NPD5977	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