NPASS Compound

Structure

CID13408 OpenBabel06191715342D 31 33 0 0 0 0 0 0 0 0999 V2000 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 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 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 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 3.4641 -0.0000 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 2.5981 -0.5000 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 -2.5981 -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 1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 -2.5981 -0.5000 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 0.8660 -1.5000 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 -2.0000 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 -0.8660 -1.5000 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 0.8660 -0.5000 0.0000 C 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 -3.4641 0.0000 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 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 2 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 18 1 0 0 0 0 11 16 2 0 0 0 0 11 20 1 0 0 0 0 12 17 2 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 22 2 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 20 2 0 0 0 0 18 25 1 0 0 0 0 19 24 1 0 0 0 0 19 25 2 0 0 0 0 20 28 1 0 0 0 0 21 23 2 0 0 0 0 21 29 1 0 0 0 0 22 23 1 0 0 0 0 22 31 1 0 0 0 0 23 24 1 0 0 0 0 24 30 2 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.17
Volume:	441.663
LogP:	5.577
LogD:	3.723
LogS:	-3.038
# Rotatable Bonds:	6
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.389
Synthetic Accessibility Score:	3.036
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.97
MDCK Permeability:	1.4140756320557557e-05
Pgp-inhibitor:	0.087
Pgp-substrate:	0.762
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	97.63115692138672%
Volume Distribution (VD):	0.414
Pgp-substrate:	1.3852461576461792%

ADMET: Metabolism

CYP1A2-inhibitor:	0.954
CYP1A2-substrate:	0.194
CYP2C19-inhibitor:	0.943
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.88
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.951
CYP2D6-substrate:	0.67
CYP3A4-inhibitor:	0.6
CYP3A4-substrate:	0.077

ADMET: Excretion

Clearance (CL):	6.107
Half-life (T1/2):	0.753

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.725
Drug-inuced Liver Injury (DILI):	0.867
AMES Toxicity:	0.434
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.908
Carcinogencity:	0.047
Eye Corrosion:	0.005
Eye Irritation:	0.92
Respiratory Toxicity:	0.134

Download Data

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

Natural Product: NPC13408

Natural Product ID:	NPC13408
*Common Name:**	5,7,2',4'-Tetrahydroxy-3-Geranylflavone
IUPAC Name:	2-(2,4-dihydroxyphenyl)-3-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxychromen-4-one
Synonyms:
Standard InCHIKey:	GRRICQNASNJYBZ-VIZOYTHASA-N
Standard InCHI:	InChI=1S/C25H26O6/c1-14(2)5-4-6-15(3)7-9-19-24(30)23-21(29)12-17(27)13-22(23)31-25(19)18-10-8-16(26)11-20(18)28/h5,7-8,10-13,26-29H,4,6,9H2,1-3H3/b15-7+
SMILES:	CC(=CCC/C(=C/Cc1c(=O)c2c(cc(cc2oc1c1ccc(cc1O)O)O)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458187
PubChem CID:	10295791
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003501] 3-prenylated flavones

*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
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[11395279]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	Shawnee National Forest, Harrisburg, IL, US	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	n.a.	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12419367]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	leaves	Kaohsiung, Taiwan	2006-SEP	PMID[18986201]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[19296617]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5495	Broussonetia papyrifera	Species	Moraceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	24000.0	nM	PMID[486330]

☑ 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 NPC13408 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	384
0.1-0.2	1628
0.2-0.3	4392
0.3-0.4	11385
0.4-0.5	6644
0.5-0.6	4021
0.6-0.7	5921
0.7-0.8	4309
0.8-0.85	1864
0.85-0.9	1501
0.9-0.95	576
0.95-1	72

Similarity Score	Similarity Level	Natural Product ID
0.9847	High Similarity	NPC194281
0.9847	High Similarity	NPC124784
0.9847	High Similarity	NPC127447
0.9847	High Similarity	NPC231772
0.9847	High Similarity	NPC47815
0.9847	High Similarity	NPC234133
0.9847	High Similarity	NPC473887
0.9847	High Similarity	NPC29353
0.9774	High Similarity	NPC220062
0.9774	High Similarity	NPC96565
0.9774	High Similarity	NPC301217
0.9774	High Similarity	NPC303633
0.9774	High Similarity	NPC216978
0.9774	High Similarity	NPC55018
0.9773	High Similarity	NPC266597
0.9773	High Similarity	NPC250266
0.9769	High Similarity	NPC274121
0.9769	High Similarity	NPC50898
0.9769	High Similarity	NPC78540
0.9769	High Similarity	NPC213216
0.9701	High Similarity	NPC172986
0.9701	High Similarity	NPC159275
0.9701	High Similarity	NPC241100
0.9701	High Similarity	NPC270883
0.9701	High Similarity	NPC261227
0.9699	High Similarity	NPC201395
0.9695	High Similarity	NPC172262
0.9692	High Similarity	NPC10971
0.963	High Similarity	NPC90582
0.963	High Similarity	NPC205006
0.963	High Similarity	NPC262094
0.963	High Similarity	NPC64908
0.963	High Similarity	NPC147688
0.963	High Similarity	NPC110969
0.963	High Similarity	NPC282300
0.963	High Similarity	NPC156590
0.963	High Similarity	NPC118840
0.9627	High Similarity	NPC143799
0.9627	High Similarity	NPC53181
0.9627	High Similarity	NPC152042
0.9627	High Similarity	NPC78913
0.9627	High Similarity	NPC18260
0.9627	High Similarity	NPC217186
0.9627	High Similarity	NPC241838
0.9624	High Similarity	NPC228661
0.9624	High Similarity	NPC188879
0.9618	High Similarity	NPC57601
0.9615	High Similarity	NPC113006
0.9559	High Similarity	NPC293852
0.9559	High Similarity	NPC78803
0.9559	High Similarity	NPC214236
0.9559	High Similarity	NPC217083
0.9559	High Similarity	NPC62840
0.9559	High Similarity	NPC226636
0.9559	High Similarity	NPC59739
0.9559	High Similarity	NPC299080
0.9559	High Similarity	NPC200694
0.9559	High Similarity	NPC11561
0.9556	High Similarity	NPC103904
0.9556	High Similarity	NPC188243
0.9556	High Similarity	NPC230285
0.9556	High Similarity	NPC6407
0.9556	High Similarity	NPC184536
0.9556	High Similarity	NPC305355
0.9556	High Similarity	NPC284550
0.9556	High Similarity	NPC69769
0.9556	High Similarity	NPC129853
0.9556	High Similarity	NPC150522
0.9556	High Similarity	NPC76445
0.9556	High Similarity	NPC110228
0.9556	High Similarity	NPC269652
0.9556	High Similarity	NPC281207
0.9556	High Similarity	NPC103342
0.9556	High Similarity	NPC235239
0.9556	High Similarity	NPC146679
0.9556	High Similarity	NPC59951
0.9556	High Similarity	NPC475680
0.9552	High Similarity	NPC188947
0.9552	High Similarity	NPC124269
0.9552	High Similarity	NPC280284
0.9552	High Similarity	NPC276905
0.9552	High Similarity	NPC99333
0.9549	High Similarity	NPC240593
0.9549	High Similarity	NPC187432
0.9549	High Similarity	NPC256042
0.9549	High Similarity	NPC281917
0.9549	High Similarity	NPC216361
0.9549	High Similarity	NPC116775
0.9542	High Similarity	NPC101294
0.9542	High Similarity	NPC473655
0.9538	High Similarity	NPC137264
0.9538	High Similarity	NPC270369
0.9538	High Similarity	NPC5515
0.9489	High Similarity	NPC293053
0.9489	High Similarity	NPC24821
0.9489	High Similarity	NPC11700
0.9489	High Similarity	NPC219915
0.9489	High Similarity	NPC212932
0.9489	High Similarity	NPC190637
0.9489	High Similarity	NPC9117
0.9489	High Similarity	NPC38219
0.9485	High Similarity	NPC136840
0.9485	High Similarity	NPC14871
0.9485	High Similarity	NPC103362
0.9481	High Similarity	NPC329203
0.9481	High Similarity	NPC310135
0.9481	High Similarity	NPC225153
0.9481	High Similarity	NPC20709
0.9481	High Similarity	NPC140890
0.9481	High Similarity	NPC274784
0.9481	High Similarity	NPC265871
0.9481	High Similarity	NPC222342
0.9481	High Similarity	NPC150648
0.9478	High Similarity	NPC299379
0.9478	High Similarity	NPC290291
0.9478	High Similarity	NPC275055
0.9474	High Similarity	NPC239495
0.9474	High Similarity	NPC9985
0.947	High Similarity	NPC242294
0.947	High Similarity	NPC175098
0.947	High Similarity	NPC144051
0.947	High Similarity	NPC204960
0.947	High Similarity	NPC294593
0.947	High Similarity	NPC312318
0.947	High Similarity	NPC20560
0.947	High Similarity	NPC139813
0.947	High Similarity	NPC337373
0.947	High Similarity	NPC159623
0.947	High Similarity	NPC82225
0.947	High Similarity	NPC188646
0.947	High Similarity	NPC18877
0.947	High Similarity	NPC56031
0.947	High Similarity	NPC472365
0.947	High Similarity	NPC28753
0.947	High Similarity	NPC263670
0.947	High Similarity	NPC192304
0.9466	High Similarity	NPC278556
0.9466	High Similarity	NPC31872
0.9466	High Similarity	NPC473584
0.9466	High Similarity	NPC475589
0.9462	High Similarity	NPC115998
0.9462	High Similarity	NPC39753
0.942	High Similarity	NPC319752
0.942	High Similarity	NPC311741
0.942	High Similarity	NPC273538
0.942	High Similarity	NPC326500
0.942	High Similarity	NPC234629
0.942	High Similarity	NPC216538
0.9416	High Similarity	NPC167624
0.9416	High Similarity	NPC76338
0.9416	High Similarity	NPC220998
0.9416	High Similarity	NPC228504
0.9416	High Similarity	NPC78
0.9416	High Similarity	NPC10937
0.9416	High Similarity	NPC223500
0.9416	High Similarity	NPC328164
0.9416	High Similarity	NPC177354
0.9416	High Similarity	NPC64915
0.9416	High Similarity	NPC40833
0.9416	High Similarity	NPC1089
0.9416	High Similarity	NPC125855
0.9416	High Similarity	NPC182852
0.9416	High Similarity	NPC296917
0.9416	High Similarity	NPC306829
0.9416	High Similarity	NPC66515
0.9416	High Similarity	NPC76372
0.9416	High Similarity	NPC148757
0.9416	High Similarity	NPC32739
0.9416	High Similarity	NPC166482
0.9416	High Similarity	NPC473042
0.9416	High Similarity	NPC324134
0.9416	High Similarity	NPC107572
0.9416	High Similarity	NPC144499
0.9416	High Similarity	NPC265040
0.9416	High Similarity	NPC161506
0.9416	High Similarity	NPC37496
0.9416	High Similarity	NPC36181
0.9416	High Similarity	NPC166934
0.9416	High Similarity	NPC194432
0.9416	High Similarity	NPC324436
0.9416	High Similarity	NPC227579
0.9407	High Similarity	NPC118813
0.9407	High Similarity	NPC470669
0.9407	High Similarity	NPC470668
0.9403	High Similarity	NPC174999
0.9398	High Similarity	NPC248872
0.9398	High Similarity	NPC286336
0.9394	High Similarity	NPC205468
0.9394	High Similarity	NPC87231
0.9394	High Similarity	NPC212631
0.9394	High Similarity	NPC129132
0.9394	High Similarity	NPC203817
0.9394	High Similarity	NPC257756
0.9394	High Similarity	NPC25937
0.9385	High Similarity	NPC187907
0.9385	High Similarity	NPC197425
0.9353	High Similarity	NPC153758
0.9353	High Similarity	NPC88964
0.9353	High Similarity	NPC470647
0.9353	High Similarity	NPC312973

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 NPC13408 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	947
0.2-0.3	1448
0.3-0.4	2657
0.4-0.5	1949
0.5-0.6	1217
0.6-0.7	382
0.7-0.8	130
0.8-0.85	33
0.85-0.9	28
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.942	High Similarity	NPD4378	Clinical (unspecified phase)
0.9333	High Similarity	NPD1552	Clinical (unspecified phase)
0.9333	High Similarity	NPD1550	Clinical (unspecified phase)
0.9281	High Similarity	NPD7410	Clinical (unspecified phase)
0.9265	High Similarity	NPD1549	Phase 2
0.9185	High Similarity	NPD1510	Phase 2
0.9173	High Similarity	NPD1240	Approved
0.9118	High Similarity	NPD2796	Approved
0.9071	High Similarity	NPD1511	Approved
0.9037	High Similarity	NPD1607	Approved
0.8944	High Similarity	NPD1512	Approved
0.8904	High Similarity	NPD2801	Approved
0.8803	High Similarity	NPD6799	Approved
0.8776	High Similarity	NPD2393	Clinical (unspecified phase)
0.8767	High Similarity	NPD7411	Suspended
0.8723	High Similarity	NPD3750	Approved
0.8716	High Similarity	NPD8443	Clinical (unspecified phase)
0.8707	High Similarity	NPD1934	Approved
0.8699	High Similarity	NPD4380	Phase 2
0.8603	High Similarity	NPD6859	Clinical (unspecified phase)
0.86	High Similarity	NPD4381	Clinical (unspecified phase)
0.86	High Similarity	NPD7075	Discontinued
0.8582	High Similarity	NPD970	Clinical (unspecified phase)
0.8581	High Similarity	NPD6801	Discontinued
0.8533	High Similarity	NPD3882	Suspended
0.8523	High Similarity	NPD7096	Clinical (unspecified phase)
0.8523	High Similarity	NPD7819	Suspended
0.8467	Intermediate Similarity	NPD3817	Phase 2
0.8446	Intermediate Similarity	NPD6599	Discontinued
0.844	Intermediate Similarity	NPD1551	Phase 2
0.8392	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD2800	Approved
0.837	Intermediate Similarity	NPD1203	Approved
0.8369	Intermediate Similarity	NPD3748	Approved
0.8367	Intermediate Similarity	NPD5403	Approved
0.8355	Intermediate Similarity	NPD3749	Approved
0.8289	Intermediate Similarity	NPD7768	Phase 2
0.8269	Intermediate Similarity	NPD6166	Phase 2
0.8269	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD1243	Approved
0.8252	Intermediate Similarity	NPD2344	Approved
0.8231	Intermediate Similarity	NPD5401	Approved
0.8228	Intermediate Similarity	NPD7054	Approved
0.8228	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD6651	Approved
0.8209	Intermediate Similarity	NPD422	Phase 1
0.8207	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD3268	Approved
0.8194	Intermediate Similarity	NPD6959	Discontinued
0.8182	Intermediate Similarity	NPD1548	Phase 1
0.8176	Intermediate Similarity	NPD7472	Approved
0.8165	Intermediate Similarity	NPD3818	Discontinued
0.8148	Intermediate Similarity	NPD9717	Approved
0.8125	Intermediate Similarity	NPD6797	Phase 2
0.8112	Intermediate Similarity	NPD2799	Discontinued
0.8102	Intermediate Similarity	NPD2797	Approved
0.8075	Intermediate Similarity	NPD7251	Discontinued
0.8071	Intermediate Similarity	NPD2313	Discontinued
0.8063	Intermediate Similarity	NPD7074	Phase 3
0.8058	Intermediate Similarity	NPD6832	Phase 2
0.8056	Intermediate Similarity	NPD2935	Discontinued
0.8056	Intermediate Similarity	NPD6100	Approved
0.8056	Intermediate Similarity	NPD6099	Approved
0.8043	Intermediate Similarity	NPD2798	Approved
0.8029	Intermediate Similarity	NPD3225	Approved
0.8027	Intermediate Similarity	NPD2309	Approved
0.8025	Intermediate Similarity	NPD7808	Phase 3
0.8025	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD920	Approved
0.7987	Intermediate Similarity	NPD5402	Approved
0.7986	Intermediate Similarity	NPD7033	Discontinued
0.7973	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD943	Approved
0.7941	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD4908	Phase 1
0.7914	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD6232	Discontinued
0.7901	Intermediate Similarity	NPD5953	Discontinued
0.7898	Intermediate Similarity	NPD5494	Approved
0.7891	Intermediate Similarity	NPD2654	Approved
0.7888	Intermediate Similarity	NPD7286	Phase 2
0.7875	Intermediate Similarity	NPD7473	Discontinued
0.7867	Intermediate Similarity	NPD2532	Approved
0.7867	Intermediate Similarity	NPD2534	Approved
0.7867	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD2533	Approved
0.7862	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4308	Phase 3
0.7842	Intermediate Similarity	NPD3267	Approved
0.7842	Intermediate Similarity	NPD3266	Approved
0.7838	Intermediate Similarity	NPD4628	Phase 3
0.7817	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1610	Phase 2
0.7778	Intermediate Similarity	NPD3226	Approved
0.7744	Intermediate Similarity	NPD6559	Discontinued
0.7718	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1296	Phase 2
0.7682	Intermediate Similarity	NPD7390	Discontinued
0.7655	Intermediate Similarity	NPD1933	Approved
0.7647	Intermediate Similarity	NPD9545	Approved
0.7643	Intermediate Similarity	NPD4288	Approved
0.764	Intermediate Similarity	NPD3926	Phase 2
0.7635	Intermediate Similarity	NPD2346	Discontinued
0.763	Intermediate Similarity	NPD9493	Approved
0.7626	Intermediate Similarity	NPD1608	Approved
0.7626	Intermediate Similarity	NPD3972	Approved
0.761	Intermediate Similarity	NPD919	Approved
0.7586	Intermediate Similarity	NPD4307	Phase 2
0.758	Intermediate Similarity	NPD1465	Phase 2
0.7569	Intermediate Similarity	NPD411	Approved
0.7561	Intermediate Similarity	NPD5844	Phase 1
0.7558	Intermediate Similarity	NPD4363	Phase 3
0.7558	Intermediate Similarity	NPD4360	Phase 2
0.7552	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD1241	Discontinued
0.7534	Intermediate Similarity	NPD5124	Phase 1
0.7534	Intermediate Similarity	NPD447	Suspended
0.7534	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1247	Approved
0.7514	Intermediate Similarity	NPD4361	Phase 2
0.7514	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD1481	Phase 2
0.7483	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6798	Discontinued
0.7448	Intermediate Similarity	NPD3764	Approved
0.7447	Intermediate Similarity	NPD4749	Approved
0.7431	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1535	Discovery
0.7429	Intermediate Similarity	NPD1201	Approved
0.7421	Intermediate Similarity	NPD2296	Approved
0.7415	Intermediate Similarity	NPD230	Phase 1
0.7413	Intermediate Similarity	NPD1019	Discontinued
0.741	Intermediate Similarity	NPD17	Approved
0.741	Intermediate Similarity	NPD1729	Discontinued
0.7403	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1613	Approved
0.7347	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1470	Approved
0.7338	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4287	Approved
0.7321	Intermediate Similarity	NPD6104	Discontinued
0.732	Intermediate Similarity	NPD2354	Approved
0.7303	Intermediate Similarity	NPD1652	Phase 2
0.7296	Intermediate Similarity	NPD6844	Discontinued
0.7289	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1471	Phase 3
0.7279	Intermediate Similarity	NPD6233	Phase 2
0.7278	Intermediate Similarity	NPD6585	Discontinued
0.7266	Intermediate Similarity	NPD1894	Discontinued
0.7256	Intermediate Similarity	NPD5711	Approved
0.7256	Intermediate Similarity	NPD5710	Approved
0.7233	Intermediate Similarity	NPD5890	Approved
0.7233	Intermediate Similarity	NPD5889	Approved
0.723	Intermediate Similarity	NPD3142	Approved
0.723	Intermediate Similarity	NPD3140	Approved
0.7226	Intermediate Similarity	NPD7212	Phase 2
0.7226	Intermediate Similarity	NPD7213	Phase 3
0.7222	Intermediate Similarity	NPD1164	Approved
0.7222	Intermediate Similarity	NPD6971	Discontinued
0.7219	Intermediate Similarity	NPD5408	Approved
0.7219	Intermediate Similarity	NPD5405	Approved
0.7219	Intermediate Similarity	NPD5404	Approved
0.7219	Intermediate Similarity	NPD5406	Approved
0.7215	Intermediate Similarity	NPD7458	Discontinued
0.7206	Intermediate Similarity	NPD5535	Approved
0.7195	Intermediate Similarity	NPD7199	Phase 2
0.7186	Intermediate Similarity	NPD3751	Discontinued
0.7181	Intermediate Similarity	NPD6355	Discontinued
0.7179	Intermediate Similarity	NPD7447	Phase 1
0.7179	Intermediate Similarity	NPD4662	Approved
0.7179	Intermediate Similarity	NPD4661	Approved
0.7171	Intermediate Similarity	NPD2353	Approved
0.7171	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2403	Approved
0.7164	Intermediate Similarity	NPD9266	Approved
0.7164	Intermediate Similarity	NPD74	Approved
0.7161	Intermediate Similarity	NPD7440	Discontinued
0.7153	Intermediate Similarity	NPD1876	Approved
0.7152	Intermediate Similarity	NPD7229	Phase 3
0.7152	Intermediate Similarity	NPD3787	Discontinued
0.7151	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD7003	Approved
0.7134	Intermediate Similarity	NPD5049	Phase 3
0.7123	Intermediate Similarity	NPD2861	Phase 2
0.7108	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7584	Approved
0.7099	Intermediate Similarity	NPD846	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