NPASS Compound

Structure

CID33265 OpenBabel06191715362D 26 28 0 0 0 0 0 0 0 0999 V2000 6.9282 -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 -0.0000 -2.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 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 1.7321 1.0000 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 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 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 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 10 2 0 0 0 0 5 16 1 0 0 0 0 6 10 1 0 0 0 0 6 17 2 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 11 1 0 0 0 0 8 15 2 0 0 0 0 9 13 1 0 0 0 0 9 14 2 0 0 0 0 10 14 1 0 0 0 0 11 22 1 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 21 2 0 0 0 0 14 26 1 0 0 0 0 15 18 1 0 0 0 0 15 26 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 17 24 1 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.11
Volume:	351.951
LogP:	3.501
LogD:	2.828
LogS:	-4.374
# Rotatable Bonds:	5
TPSA:	87.36
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.749
Synthetic Accessibility Score:	2.296
Fsp3:	0.211
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:	-4.756
MDCK Permeability:	4.0642076783115044e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.086

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	78.77901458740234%
Volume Distribution (VD):	0.818
Pgp-substrate:	19.179262161254883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.828
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.586
CYP2C19-substrate:	0.662
CYP2C9-inhibitor:	0.593
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.181
CYP2D6-substrate:	0.932
CYP3A4-inhibitor:	0.734
CYP3A4-substrate:	0.421

ADMET: Excretion

Clearance (CL):	6.2
Half-life (T1/2):	0.538

ADMET: Toxicity

hERG Blockers:	0.123
Human Hepatotoxicity (H-HT):	0.137
Drug-inuced Liver Injury (DILI):	0.733
AMES Toxicity:	0.27
Rat Oral Acute Toxicity:	0.106
Maximum Recommended Daily Dose:	0.456
Skin Sensitization:	0.726
Carcinogencity:	0.022
Eye Corrosion:	0.004
Eye Irritation:	0.285
Respiratory Toxicity:	0.455

Download Data

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

Natural Product: NPC33265

Natural Product ID:	NPC33265
*Common Name:**	Corymbosin
IUPAC Name:	5-hydroxy-7-methoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
Synonyms:	Corymbosin
Standard InCHIKey:	FLCVGMVLNHYJAW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O7/c1-22-11-7-12(20)18-13(21)9-14(26-15(18)8-11)10-5-16(23-2)19(25-4)17(6-10)24-3/h5-9,20H,1-4H3
SMILES:	COc1cc(O)c2c(c1)oc(cc2=O)c1cc(OC)c(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511257
PubChem CID:	10970376
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO33004	lethedon tannaensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075750]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO33004	lethedon tannaensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759170]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	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
NPT91	Cell Line	KB	Homo sapiens	IC50	=	19.4	ug.mL-1	PMID[528508]

☑ 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 NPC33265 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	413
0.1-0.2	1848
0.2-0.3	4646
0.3-0.4	11068
0.4-0.5	6618
0.5-0.6	3655
0.6-0.7	4891
0.7-0.8	4819
0.8-0.85	2361
0.85-0.9	1530
0.9-0.95	727
0.95-1	121

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC62536
0.9929	High Similarity	NPC195202
0.9859	High Similarity	NPC328119
0.9859	High Similarity	NPC48479
0.9859	High Similarity	NPC177298
0.9858	High Similarity	NPC12200
0.979	High Similarity	NPC50728
0.979	High Similarity	NPC219330
0.979	High Similarity	NPC166753
0.9789	High Similarity	NPC120464
0.9722	High Similarity	NPC236769
0.9722	High Similarity	NPC76376
0.9722	High Similarity	NPC208043
0.9722	High Similarity	NPC226973
0.9722	High Similarity	NPC308451
0.972	High Similarity	NPC137062
0.972	High Similarity	NPC223579
0.972	High Similarity	NPC159103
0.972	High Similarity	NPC287101
0.972	High Similarity	NPC52005
0.972	High Similarity	NPC183950
0.9655	High Similarity	NPC60972
0.9655	High Similarity	NPC39732
0.9655	High Similarity	NPC471982
0.9653	High Similarity	NPC306821
0.9653	High Similarity	NPC338131
0.965	High Similarity	NPC261548
0.9643	High Similarity	NPC29536
0.9589	High Similarity	NPC250822
0.9589	High Similarity	NPC276409
0.9589	High Similarity	NPC179126
0.9589	High Similarity	NPC22519
0.9589	High Similarity	NPC69394
0.9589	High Similarity	NPC274327
0.9589	High Similarity	NPC183878
0.9589	High Similarity	NPC145379
0.9589	High Similarity	NPC75279
0.9589	High Similarity	NPC160951
0.9589	High Similarity	NPC162351
0.9589	High Similarity	NPC86485
0.9589	High Similarity	NPC246204
0.9589	High Similarity	NPC58382
0.9589	High Similarity	NPC236223
0.9589	High Similarity	NPC255350
0.9589	High Similarity	NPC176775
0.9589	High Similarity	NPC270620
0.9589	High Similarity	NPC280937
0.9589	High Similarity	NPC78326
0.9589	High Similarity	NPC231018
0.9589	High Similarity	NPC47781
0.9586	High Similarity	NPC28274
0.9586	High Similarity	NPC133953
0.9586	High Similarity	NPC252933
0.9586	High Similarity	NPC54394
0.9586	High Similarity	NPC50403
0.9586	High Similarity	NPC200740
0.9586	High Similarity	NPC125062
0.958	High Similarity	NPC108406
0.9574	High Similarity	NPC70853
0.9574	High Similarity	NPC9966
0.9524	High Similarity	NPC2476
0.9524	High Similarity	NPC138360
0.9524	High Similarity	NPC280339
0.9524	High Similarity	NPC4455
0.9524	High Similarity	NPC189960
0.9524	High Similarity	NPC163780
0.9524	High Similarity	NPC50715
0.9524	High Similarity	NPC227325
0.9524	High Similarity	NPC32557
0.9524	High Similarity	NPC20830
0.9524	High Similarity	NPC183597
0.9524	High Similarity	NPC128863
0.9524	High Similarity	NPC201136
0.9524	High Similarity	NPC146165
0.9524	High Similarity	NPC256612
0.9524	High Similarity	NPC92659
0.9524	High Similarity	NPC213622
0.9524	High Similarity	NPC196439
0.9524	High Similarity	NPC167815
0.9524	High Similarity	NPC208197
0.9521	High Similarity	NPC82325
0.9521	High Similarity	NPC256283
0.9521	High Similarity	NPC71334
0.9521	High Similarity	NPC198826
0.9521	High Similarity	NPC188203
0.9521	High Similarity	NPC120163
0.9521	High Similarity	NPC275722
0.9521	High Similarity	NPC275836
0.9521	High Similarity	NPC241498
0.9521	High Similarity	NPC162313
0.9521	High Similarity	NPC100887
0.9521	High Similarity	NPC222830
0.9521	High Similarity	NPC83508
0.9521	High Similarity	NPC55205
0.9521	High Similarity	NPC131624
0.9521	High Similarity	NPC301123
0.9521	High Similarity	NPC239128
0.9521	High Similarity	NPC293183
0.9521	High Similarity	NPC187498
0.9521	High Similarity	NPC212678
0.9521	High Similarity	NPC57030
0.9521	High Similarity	NPC301323
0.9521	High Similarity	NPC25270
0.9521	High Similarity	NPC279989
0.9521	High Similarity	NPC123886
0.9521	High Similarity	NPC156222
0.9507	High Similarity	NPC113089
0.9459	High Similarity	NPC474520
0.9459	High Similarity	NPC178854
0.9459	High Similarity	NPC100916
0.9459	High Similarity	NPC55619
0.9459	High Similarity	NPC200388
0.9459	High Similarity	NPC49824
0.9459	High Similarity	NPC265511
0.9456	High Similarity	NPC472915
0.9456	High Similarity	NPC18727
0.9452	High Similarity	NPC117579
0.9448	High Similarity	NPC87125
0.9448	High Similarity	NPC270465
0.9441	High Similarity	NPC136278
0.9437	High Similarity	NPC175013
0.9437	High Similarity	NPC119663
0.9396	High Similarity	NPC183
0.9396	High Similarity	NPC110070
0.9396	High Similarity	NPC227192
0.9396	High Similarity	NPC203891
0.9396	High Similarity	NPC189179
0.9396	High Similarity	NPC29841
0.9396	High Similarity	NPC470402
0.9396	High Similarity	NPC75215
0.9396	High Similarity	NPC284820
0.9396	High Similarity	NPC101830
0.9396	High Similarity	NPC476981
0.9396	High Similarity	NPC472438
0.9396	High Similarity	NPC7973
0.9396	High Similarity	NPC183851
0.9396	High Similarity	NPC473272
0.9396	High Similarity	NPC224137
0.9396	High Similarity	NPC78302
0.9396	High Similarity	NPC63454
0.9396	High Similarity	NPC93376
0.9396	High Similarity	NPC235215
0.9392	High Similarity	NPC31018
0.9392	High Similarity	NPC255807
0.9392	High Similarity	NPC37392
0.9392	High Similarity	NPC45849
0.9392	High Similarity	NPC470327
0.9392	High Similarity	NPC200761
0.9392	High Similarity	NPC234255
0.9392	High Similarity	NPC472909
0.9392	High Similarity	NPC44079
0.9392	High Similarity	NPC226025
0.9392	High Similarity	NPC477503
0.9392	High Similarity	NPC201451
0.9392	High Similarity	NPC26227
0.9388	High Similarity	NPC477231
0.9388	High Similarity	NPC302950
0.9388	High Similarity	NPC236637
0.9388	High Similarity	NPC134677
0.9388	High Similarity	NPC142540
0.9388	High Similarity	NPC257648
0.9388	High Similarity	NPC219582
0.9388	High Similarity	NPC472912
0.9384	High Similarity	NPC88804
0.9384	High Similarity	NPC179183
0.9384	High Similarity	NPC3825
0.9384	High Similarity	NPC184136
0.9384	High Similarity	NPC149127
0.9384	High Similarity	NPC286342
0.9384	High Similarity	NPC239363
0.9384	High Similarity	NPC188871
0.9379	High Similarity	NPC119059
0.9375	High Similarity	NPC283002
0.9375	High Similarity	NPC40818
0.9375	High Similarity	NPC302408
0.9375	High Similarity	NPC310259
0.9375	High Similarity	NPC12377
0.9375	High Similarity	NPC110639
0.9375	High Similarity	NPC106461
0.9375	High Similarity	NPC215932
0.9375	High Similarity	NPC14958
0.9371	High Similarity	NPC279121
0.9333	High Similarity	NPC204854
0.9333	High Similarity	NPC261004
0.9333	High Similarity	NPC19687
0.9333	High Similarity	NPC143828
0.9333	High Similarity	NPC105242
0.9333	High Similarity	NPC4481
0.9333	High Similarity	NPC284127
0.9333	High Similarity	NPC172202
0.9333	High Similarity	NPC476410
0.9333	High Similarity	NPC22472
0.9333	High Similarity	NPC152166
0.9333	High Similarity	NPC18772
0.9333	High Similarity	NPC176300
0.9333	High Similarity	NPC253634
0.9333	High Similarity	NPC191459
0.9333	High Similarity	NPC288669
0.9333	High Similarity	NPC130894
0.9333	High Similarity	NPC7846

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 NPC33265 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	968
0.2-0.3	1786
0.3-0.4	2660
0.4-0.5	1759
0.5-0.6	1025
0.6-0.7	391
0.7-0.8	110
0.8-0.85	39
0.85-0.9	19
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9589	High Similarity	NPD2801	Approved
0.9388	High Similarity	NPD1934	Approved
0.9371	High Similarity	NPD1511	Approved
0.9241	High Similarity	NPD1512	Approved
0.9195	High Similarity	NPD2393	Clinical (unspecified phase)
0.9133	High Similarity	NPD3817	Phase 2
0.9073	High Similarity	NPD3882	Suspended
0.9041	High Similarity	NPD4378	Clinical (unspecified phase)
0.891	High Similarity	NPD6166	Phase 2
0.891	High Similarity	NPD6168	Clinical (unspecified phase)
0.891	High Similarity	NPD6167	Clinical (unspecified phase)
0.8861	High Similarity	NPD7054	Approved
0.8805	High Similarity	NPD7472	Approved
0.8797	High Similarity	NPD3818	Discontinued
0.869	High Similarity	NPD1550	Clinical (unspecified phase)
0.869	High Similarity	NPD1552	Clinical (unspecified phase)
0.8688	High Similarity	NPD7074	Phase 3
0.8681	High Similarity	NPD1510	Phase 2
0.8642	High Similarity	NPD7808	Phase 3
0.8634	High Similarity	NPD6797	Phase 2
0.863	High Similarity	NPD1549	Phase 2
0.8621	High Similarity	NPD2796	Approved
0.8618	High Similarity	NPD4380	Phase 2
0.8581	High Similarity	NPD4868	Clinical (unspecified phase)
0.858	High Similarity	NPD7251	Discontinued
0.8544	High Similarity	NPD6232	Discontinued
0.8535	High Similarity	NPD5494	Approved
0.8533	High Similarity	NPD7410	Clinical (unspecified phase)
0.8531	High Similarity	NPD1240	Approved
0.8528	High Similarity	NPD4338	Clinical (unspecified phase)
0.8526	High Similarity	NPD4381	Clinical (unspecified phase)
0.8503	High Similarity	NPD970	Clinical (unspecified phase)
0.85	High Similarity	NPD7473	Discontinued
0.8467	Intermediate Similarity	NPD6799	Approved
0.8414	Intermediate Similarity	NPD1607	Approved
0.8408	Intermediate Similarity	NPD7075	Discontinued
0.8333	Intermediate Similarity	NPD7819	Suspended
0.8333	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD6801	Discontinued
0.825	Intermediate Similarity	NPD6959	Discontinued
0.8217	Intermediate Similarity	NPD1465	Phase 2
0.8205	Intermediate Similarity	NPD7411	Suspended
0.8171	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD5844	Phase 1
0.8165	Intermediate Similarity	NPD5402	Approved
0.8151	Intermediate Similarity	NPD943	Approved
0.8148	Intermediate Similarity	NPD3926	Phase 2
0.8146	Intermediate Similarity	NPD3750	Approved
0.8141	Intermediate Similarity	NPD6599	Discontinued
0.8137	Intermediate Similarity	NPD1247	Approved
0.8125	Intermediate Similarity	NPD919	Approved
0.8095	Intermediate Similarity	NPD447	Suspended
0.8079	Intermediate Similarity	NPD2800	Approved
0.8072	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD5403	Approved
0.8056	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD1551	Phase 2
0.8	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD230	Phase 1
0.7935	Intermediate Similarity	NPD2532	Approved
0.7935	Intermediate Similarity	NPD2533	Approved
0.7935	Intermediate Similarity	NPD2534	Approved
0.7935	Intermediate Similarity	NPD5401	Approved
0.7917	Intermediate Similarity	NPD6559	Discontinued
0.7905	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1613	Approved
0.7888	Intermediate Similarity	NPD7768	Phase 2
0.7881	Intermediate Similarity	NPD6099	Approved
0.7881	Intermediate Similarity	NPD6100	Approved
0.7879	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1933	Approved
0.7843	Intermediate Similarity	NPD1243	Approved
0.7843	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD3749	Approved
0.7823	Intermediate Similarity	NPD3027	Phase 3
0.7815	Intermediate Similarity	NPD3748	Approved
0.78	Intermediate Similarity	NPD6651	Approved
0.7792	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD920	Approved
0.7712	Intermediate Similarity	NPD2344	Approved
0.7697	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7199	Phase 2
0.7697	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4628	Phase 3
0.7671	Intermediate Similarity	NPD1203	Approved
0.7661	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2313	Discontinued
0.7643	Intermediate Similarity	NPD7390	Discontinued
0.7625	Intermediate Similarity	NPD3226	Approved
0.7611	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD1548	Phase 1
0.7605	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD37	Approved
0.7582	Intermediate Similarity	NPD2799	Discontinued
0.758	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6234	Discontinued
0.7568	Intermediate Similarity	NPD9494	Approved
0.7564	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1653	Approved
0.7561	Intermediate Similarity	NPD4967	Phase 2
0.7561	Intermediate Similarity	NPD4965	Approved
0.7561	Intermediate Similarity	NPD4966	Approved
0.7544	Intermediate Similarity	NPD5953	Discontinued
0.7533	Intermediate Similarity	NPD3268	Approved
0.7529	Intermediate Similarity	NPD7286	Phase 2
0.7517	Intermediate Similarity	NPD422	Phase 1
0.7517	Intermediate Similarity	NPD6832	Phase 2
0.7517	Intermediate Similarity	NPD4908	Phase 1
0.7516	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD2654	Approved
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7468	Intermediate Similarity	NPD7033	Discontinued
0.7466	Intermediate Similarity	NPD9717	Approved
0.745	Intermediate Similarity	NPD3018	Phase 2
0.744	Intermediate Similarity	NPD3787	Discontinued
0.7432	Intermediate Similarity	NPD2797	Approved
0.7417	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD5536	Phase 2
0.7405	Intermediate Similarity	NPD6190	Approved
0.7401	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1610	Phase 2
0.7397	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5242	Approved
0.7394	Intermediate Similarity	NPD5353	Approved
0.7365	Intermediate Similarity	NPD3225	Approved
0.7355	Intermediate Similarity	NPD4308	Phase 3
0.7353	Intermediate Similarity	NPD2403	Approved
0.7347	Intermediate Similarity	NPD9269	Phase 2
0.7347	Intermediate Similarity	NPD1608	Approved
0.7337	Intermediate Similarity	NPD5710	Approved
0.7337	Intermediate Similarity	NPD5711	Approved
0.7333	Intermediate Similarity	NPD4363	Phase 3
0.7333	Intermediate Similarity	NPD4360	Phase 2
0.7317	Intermediate Similarity	NPD6385	Approved
0.7317	Intermediate Similarity	NPD6386	Approved
0.7312	Intermediate Similarity	NPD4357	Discontinued
0.731	Intermediate Similarity	NPD9268	Approved
0.7303	Intermediate Similarity	NPD411	Approved
0.7299	Intermediate Similarity	NPD7685	Pre-registration
0.7297	Intermediate Similarity	NPD4749	Approved
0.7297	Intermediate Similarity	NPD2983	Phase 2
0.7297	Intermediate Similarity	NPD2982	Phase 2
0.7273	Intermediate Similarity	NPD6844	Discontinued
0.7267	Intermediate Similarity	NPD7228	Approved
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4625	Phase 3
0.7232	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2981	Phase 2
0.7222	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3267	Approved
0.72	Intermediate Similarity	NPD3266	Approved
0.7198	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD4361	Phase 2
0.719	Intermediate Similarity	NPD6798	Discontinued
0.7186	Intermediate Similarity	NPD4288	Approved
0.717	Intermediate Similarity	NPD1652	Phase 2
0.7162	Intermediate Similarity	NPD1201	Approved
0.716	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD17	Approved
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7123	Intermediate Similarity	NPD9545	Approved
0.7119	Intermediate Similarity	NPD8313	Approved
0.7119	Intermediate Similarity	NPD8312	Approved
0.7114	Intermediate Similarity	NPD3972	Approved
0.7108	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2861	Phase 2
0.7103	Intermediate Similarity	NPD9493	Approved
0.7102	Intermediate Similarity	NPD7038	Approved
0.7102	Intermediate Similarity	NPD7039	Approved
0.7101	Intermediate Similarity	NPD6971	Discontinued
0.7097	Intermediate Similarity	NPD4307	Phase 2
0.7095	Intermediate Similarity	NPD8434	Phase 2
0.7091	Intermediate Similarity	NPD7458	Discontinued
0.709	Intermediate Similarity	NPD7584	Approved
0.7086	Intermediate Similarity	NPD1470	Approved
0.7078	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1296	Phase 2
0.7062	Intermediate Similarity	NPD7549	Discontinued
0.7051	Intermediate Similarity	NPD5124	Phase 1
0.7051	Intermediate Similarity	NPD6355	Discontinued
0.7051	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1019	Discontinued
0.7019	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4110	Phase 3
0.7016	Intermediate Similarity	NPD8151	Discontinued
0.7014	Intermediate Similarity	NPD5283	Phase 1

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