NPASS Compound

Structure

NPC133392 OpenBabel07101718302D 33 35 0 0 0 0 0 0 0 0999 V2000 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -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 -2.5981 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 6.9282 -0.0000 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 4.3301 1.5000 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 3.4641 2.0000 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 -1.7321 -1.0000 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 6.9282 -1.0000 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 -1.7321 0.0000 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 -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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 0.0000 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 -0.8660 1.5000 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 -2.5981 -2.5000 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 -1.7321 2.0000 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 32 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 14 2 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 13 19 2 0 0 0 0 13 21 1 0 0 0 0 16 25 1 0 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 18 20 2 0 0 0 0 18 27 1 0 0 0 0 19 28 1 0 0 0 0 20 29 1 0 0 0 0 21 22 2 0 0 0 0 21 33 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 31 2 0 0 0 0 25 26 2 0 0 0 0 25 33 1 0 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.18
Volume:	467.75
LogP:	5.553
LogD:	3.347
LogS:	-2.772
# Rotatable Bonds:	7
TPSA:	120.36
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.275
Synthetic Accessibility Score:	3.041
Fsp3:	0.269
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.923
MDCK Permeability:	1.3146024684829172e-05
Pgp-inhibitor:	0.773
Pgp-substrate:	0.374
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.396
30% Bioavailability (F30%):	0.334

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	95.17107391357422%
Volume Distribution (VD):	0.435
Pgp-substrate:	2.9840269088745117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.785
CYP1A2-substrate:	0.361
CYP2C19-inhibitor:	0.858
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.862
CYP2C9-substrate:	0.87
CYP2D6-inhibitor:	0.828
CYP2D6-substrate:	0.31
CYP3A4-inhibitor:	0.17
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	5.667
Half-life (T1/2):	0.755

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.341
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.405
Rat Oral Acute Toxicity:	0.093
Maximum Recommended Daily Dose:	0.541
Skin Sensitization:	0.919
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.905
Respiratory Toxicity:	0.116

Download Data

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

Natural Product: NPC133392

Natural Product ID:	NPC133392
*Common Name:**	5,7,3',4'-Tetrahydroxy-3-Methoxy-6-Geranylflavone
IUPAC Name:	2-(3,4-dihydroxyphenyl)-6-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxy-3-methoxychromen-4-one
Synonyms:
Standard InCHIKey:	SFMXXEOUUFGNQC-OVCLIPMQSA-N
Standard InCHI:	InChI=1S/C26H28O7/c1-14(2)6-5-7-15(3)8-10-17-19(28)13-21-22(23(17)30)24(31)26(32-4)25(33-21)16-9-11-18(27)20(29)12-16/h6,8-9,11-13,27-30H,5,7,10H2,1-4H3/b15-8+
SMILES:	CC(=CCC/C(=C/Cc1c(cc2c(c1O)c(=O)c(c(c1ccc(c(c1)O)O)o2)OC)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457262
PubChem CID:	11015855
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003503] 6-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	>	40.0	ug.mL-1	PMID[505107]

☑ 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 NPC133392 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	447
0.1-0.2	1790
0.2-0.3	4641
0.3-0.4	10863
0.4-0.5	6852
0.5-0.6	3684
0.6-0.7	5007
0.7-0.8	4752
0.8-0.85	2277
0.85-0.9	1513
0.9-0.95	644
0.95-1	227

Similarity Score	Similarity Level	Natural Product ID
0.9864	High Similarity	NPC37684
0.9864	High Similarity	NPC63187
0.9864	High Similarity	NPC157784
0.9796	High Similarity	NPC304295
0.9796	High Similarity	NPC205046
0.9796	High Similarity	NPC59162
0.9728	High Similarity	NPC3825
0.9728	High Similarity	NPC188871
0.9728	High Similarity	NPC286342
0.9728	High Similarity	NPC88804
0.9728	High Similarity	NPC149127
0.9667	High Similarity	NPC3980
0.9664	High Similarity	NPC270620
0.9664	High Similarity	NPC236223
0.9664	High Similarity	NPC179126
0.9664	High Similarity	NPC78326
0.9662	High Similarity	NPC260895
0.966	High Similarity	NPC270465
0.966	High Similarity	NPC87125
0.9605	High Similarity	NPC246478
0.9603	High Similarity	NPC237418
0.9603	High Similarity	NPC273843
0.96	High Similarity	NPC80534
0.96	High Similarity	NPC56786
0.9597	High Similarity	NPC279989
0.9597	High Similarity	NPC471982
0.9597	High Similarity	NPC82325
0.9539	High Similarity	NPC22192
0.9536	High Similarity	NPC13779
0.9536	High Similarity	NPC471500
0.9536	High Similarity	NPC265511
0.9536	High Similarity	NPC475799
0.9533	High Similarity	NPC189130
0.9533	High Similarity	NPC58382
0.9533	High Similarity	NPC213896
0.9533	High Similarity	NPC162351
0.9533	High Similarity	NPC192083
0.9533	High Similarity	NPC170492
0.953	High Similarity	NPC236769
0.953	High Similarity	NPC252933
0.953	High Similarity	NPC125062
0.953	High Similarity	NPC200740
0.953	High Similarity	NPC54394
0.953	High Similarity	NPC154345
0.9524	High Similarity	NPC108406
0.9477	High Similarity	NPC282009
0.9477	High Similarity	NPC287328
0.9474	High Similarity	NPC471515
0.9474	High Similarity	NPC203891
0.9474	High Similarity	NPC101830
0.9474	High Similarity	NPC471479
0.9474	High Similarity	NPC110070
0.947	High Similarity	NPC234255
0.947	High Similarity	NPC321779
0.947	High Similarity	NPC214138
0.9467	High Similarity	NPC249570
0.9467	High Similarity	NPC123886
0.9467	High Similarity	NPC106976
0.9467	High Similarity	NPC55205
0.9463	High Similarity	NPC50728
0.9463	High Similarity	NPC166753
0.9456	High Similarity	NPC306488
0.9456	High Similarity	NPC20791
0.9456	High Similarity	NPC179271
0.9456	High Similarity	NPC178343
0.9456	High Similarity	NPC5820
0.9419	High Similarity	NPC470459
0.9419	High Similarity	NPC472625
0.9416	High Similarity	NPC471499
0.9416	High Similarity	NPC187354
0.9416	High Similarity	NPC289771
0.9412	High Similarity	NPC143828
0.9412	High Similarity	NPC152166
0.9412	High Similarity	NPC22472
0.9412	High Similarity	NPC204854
0.9412	High Similarity	NPC191459
0.9412	High Similarity	NPC115798
0.9412	High Similarity	NPC25495
0.9412	High Similarity	NPC18772
0.9412	High Similarity	NPC130894
0.9412	High Similarity	NPC18607
0.9412	High Similarity	NPC7846
0.9412	High Similarity	NPC300943
0.9412	High Similarity	NPC253634
0.9412	High Similarity	NPC105242
0.9412	High Similarity	NPC19687
0.9412	High Similarity	NPC4481
0.9412	High Similarity	NPC288669
0.9412	High Similarity	NPC176300
0.9412	High Similarity	NPC261004
0.9412	High Similarity	NPC9609
0.9408	High Similarity	NPC170026
0.9408	High Similarity	NPC291878
0.9408	High Similarity	NPC200388
0.9408	High Similarity	NPC49824
0.9408	High Similarity	NPC472455
0.9408	High Similarity	NPC35038
0.9408	High Similarity	NPC266960
0.9408	High Similarity	NPC292107
0.9408	High Similarity	NPC471985
0.9408	High Similarity	NPC282307
0.9408	High Similarity	NPC276444
0.9408	High Similarity	NPC55619
0.9408	High Similarity	NPC245546
0.9408	High Similarity	NPC100916
0.9408	High Similarity	NPC195796
0.9408	High Similarity	NPC278778
0.9408	High Similarity	NPC43243
0.9404	High Similarity	NPC476631
0.9404	High Similarity	NPC298692
0.9404	High Similarity	NPC74924
0.94	High Similarity	NPC76376
0.94	High Similarity	NPC133953
0.94	High Similarity	NPC50403
0.94	High Similarity	NPC28274
0.9396	High Similarity	NPC48479
0.9396	High Similarity	NPC137062
0.9396	High Similarity	NPC183950
0.9396	High Similarity	NPC52005
0.9396	High Similarity	NPC159103
0.9396	High Similarity	NPC177298
0.9396	High Similarity	NPC287101
0.9396	High Similarity	NPC38545
0.9396	High Similarity	NPC171916
0.9396	High Similarity	NPC223579
0.9392	High Similarity	NPC51443
0.9392	High Similarity	NPC74881
0.9388	High Similarity	NPC273538
0.9388	High Similarity	NPC216538
0.9359	High Similarity	NPC470457
0.9355	High Similarity	NPC78332
0.9351	High Similarity	NPC476980
0.9351	High Similarity	NPC470326
0.9351	High Similarity	NPC328102
0.9351	High Similarity	NPC119209
0.9351	High Similarity	NPC297212
0.9351	High Similarity	NPC476283
0.9351	High Similarity	NPC118256
0.9351	High Similarity	NPC192686
0.9346	High Similarity	NPC176665
0.9346	High Similarity	NPC224137
0.9346	High Similarity	NPC29841
0.9346	High Similarity	NPC27337
0.9346	High Similarity	NPC67876
0.9346	High Similarity	NPC235215
0.9346	High Similarity	NPC472598
0.9346	High Similarity	NPC93376
0.9346	High Similarity	NPC218871
0.9346	High Similarity	NPC78225
0.9346	High Similarity	NPC476630
0.9346	High Similarity	NPC189179
0.9346	High Similarity	NPC227192
0.9346	High Similarity	NPC305663
0.9346	High Similarity	NPC287979
0.9346	High Similarity	NPC7973
0.9346	High Similarity	NPC474055
0.9346	High Similarity	NPC291508
0.9346	High Similarity	NPC472438
0.9346	High Similarity	NPC75215
0.9346	High Similarity	NPC471209
0.9346	High Similarity	NPC78302
0.9346	High Similarity	NPC163524
0.9342	High Similarity	NPC32557
0.9342	High Similarity	NPC472280
0.9342	High Similarity	NPC200761
0.9342	High Similarity	NPC152951
0.9342	High Similarity	NPC201451
0.9342	High Similarity	NPC57674
0.9342	High Similarity	NPC230149
0.9342	High Similarity	NPC113906
0.9342	High Similarity	NPC117992
0.9342	High Similarity	NPC189960
0.9342	High Similarity	NPC477503
0.9342	High Similarity	NPC26227
0.9342	High Similarity	NPC44079
0.9342	High Similarity	NPC168247
0.9342	High Similarity	NPC470327
0.9342	High Similarity	NPC45849
0.9338	High Similarity	NPC60972
0.9338	High Similarity	NPC324233
0.9338	High Similarity	NPC237994
0.9338	High Similarity	NPC39732
0.9338	High Similarity	NPC323626
0.9333	High Similarity	NPC219330
0.9333	High Similarity	NPC184136
0.9329	High Similarity	NPC238279
0.9329	High Similarity	NPC119059
0.9329	High Similarity	NPC261548
0.9329	High Similarity	NPC166036
0.9329	High Similarity	NPC203077
0.9329	High Similarity	NPC195202
0.9329	High Similarity	NPC120464
0.9324	High Similarity	NPC124729
0.9324	High Similarity	NPC169749
0.932	High Similarity	NPC158874
0.932	High Similarity	NPC279121
0.932	High Similarity	NPC212932
0.932	High Similarity	NPC293053
0.932	High Similarity	NPC190637
0.932	High Similarity	NPC24821

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 NPC133392 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	975
0.2-0.3	1779
0.3-0.4	2666
0.4-0.5	1785
0.5-0.6	990
0.6-0.7	382
0.7-0.8	123
0.8-0.85	30
0.85-0.9	17
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9533	High Similarity	NPD2393	Clinical (unspecified phase)
0.9456	High Similarity	NPD1512	Approved
0.9388	High Similarity	NPD4378	Clinical (unspecified phase)
0.932	High Similarity	NPD1511	Approved
0.9276	High Similarity	NPD2801	Approved
0.9211	High Similarity	NPD1934	Approved
0.9156	High Similarity	NPD3882	Suspended
0.9091	High Similarity	NPD3817	Phase 2
0.8994	High Similarity	NPD6168	Clinical (unspecified phase)
0.8994	High Similarity	NPD6167	Clinical (unspecified phase)
0.8994	High Similarity	NPD6166	Phase 2
0.8854	High Similarity	NPD7075	Discontinued
0.8834	High Similarity	NPD6797	Phase 2
0.8782	High Similarity	NPD7096	Clinical (unspecified phase)
0.878	High Similarity	NPD7251	Discontinued
0.8718	High Similarity	NPD6801	Discontinued
0.871	High Similarity	NPD4380	Phase 2
0.865	High Similarity	NPD3818	Discontinued
0.8627	High Similarity	NPD7410	Clinical (unspecified phase)
0.8614	High Similarity	NPD7808	Phase 3
0.8614	High Similarity	NPD4338	Clinical (unspecified phase)
0.8598	High Similarity	NPD7804	Clinical (unspecified phase)
0.8598	High Similarity	NPD7054	Approved
0.8562	High Similarity	NPD6799	Approved
0.8545	High Similarity	NPD7074	Phase 3
0.8545	High Similarity	NPD7472	Approved
0.8533	High Similarity	NPD1550	Clinical (unspecified phase)
0.8533	High Similarity	NPD1552	Clinical (unspecified phase)
0.8523	High Similarity	NPD1510	Phase 2
0.8477	Intermediate Similarity	NPD1549	Phase 2
0.8467	Intermediate Similarity	NPD2796	Approved
0.8438	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD7819	Suspended
0.8405	Intermediate Similarity	NPD6232	Discontinued
0.8395	Intermediate Similarity	NPD5494	Approved
0.8385	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD1240	Approved
0.8375	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD7473	Discontinued
0.8354	Intermediate Similarity	NPD6599	Discontinued
0.8344	Intermediate Similarity	NPD1247	Approved
0.8333	Intermediate Similarity	NPD919	Approved
0.8302	Intermediate Similarity	NPD7411	Suspended
0.8267	Intermediate Similarity	NPD1607	Approved
0.8261	Intermediate Similarity	NPD5402	Approved
0.8255	Intermediate Similarity	NPD943	Approved
0.8232	Intermediate Similarity	NPD6959	Discontinued
0.8166	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD5403	Approved
0.8117	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD2935	Discontinued
0.8065	Intermediate Similarity	NPD2800	Approved
0.8047	Intermediate Similarity	NPD5844	Phase 1
0.8038	Intermediate Similarity	NPD5401	Approved
0.8024	Intermediate Similarity	NPD3926	Phase 2
0.8013	Intermediate Similarity	NPD3750	Approved
0.8012	Intermediate Similarity	NPD6559	Discontinued
0.7988	Intermediate Similarity	NPD7768	Phase 2
0.7987	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1465	Phase 2
0.7949	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD2533	Approved
0.7925	Intermediate Similarity	NPD2532	Approved
0.7925	Intermediate Similarity	NPD2534	Approved
0.7922	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1613	Approved
0.7843	Intermediate Similarity	NPD230	Phase 1
0.7834	Intermediate Similarity	NPD1243	Approved
0.7826	Intermediate Similarity	NPD920	Approved
0.7792	Intermediate Similarity	NPD6651	Approved
0.7763	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2313	Discontinued
0.7759	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1551	Phase 2
0.773	Intermediate Similarity	NPD3226	Approved
0.7725	Intermediate Similarity	NPD3749	Approved
0.7716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3027	Phase 3
0.7692	Intermediate Similarity	NPD3748	Approved
0.7692	Intermediate Similarity	NPD2799	Discontinued
0.7692	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD5953	Discontinued
0.7643	Intermediate Similarity	NPD6100	Approved
0.7643	Intermediate Similarity	NPD6099	Approved
0.764	Intermediate Similarity	NPD7390	Discontinued
0.7637	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7286	Phase 2
0.7625	Intermediate Similarity	NPD6190	Approved
0.7613	Intermediate Similarity	NPD447	Suspended
0.7611	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2344	Approved
0.7595	Intermediate Similarity	NPD2346	Discontinued
0.7572	Intermediate Similarity	NPD3751	Discontinued
0.7562	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD4628	Phase 3
0.7544	Intermediate Similarity	NPD3787	Discontinued
0.7532	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7471	Intermediate Similarity	NPD6234	Discontinued
0.7453	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4060	Phase 1
0.7434	Intermediate Similarity	NPD1203	Approved
0.7432	Intermediate Similarity	NPD4360	Phase 2
0.7432	Intermediate Similarity	NPD4363	Phase 3
0.743	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3268	Approved
0.7419	Intermediate Similarity	NPD6798	Discontinued
0.7417	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2309	Approved
0.7403	Intermediate Similarity	NPD4908	Phase 1
0.7389	Intermediate Similarity	NPD1933	Approved
0.7386	Intermediate Similarity	NPD2798	Approved
0.7378	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1548	Phase 1
0.7358	Intermediate Similarity	NPD7033	Discontinued
0.7356	Intermediate Similarity	NPD2403	Approved
0.7355	Intermediate Similarity	NPD4625	Phase 3
0.7349	Intermediate Similarity	NPD1653	Approved
0.7341	Intermediate Similarity	NPD5711	Approved
0.7341	Intermediate Similarity	NPD5710	Approved
0.7338	Intermediate Similarity	NPD9494	Approved
0.732	Intermediate Similarity	NPD2797	Approved
0.7297	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4361	Phase 2
0.7293	Intermediate Similarity	NPD8434	Phase 2
0.729	Intermediate Similarity	NPD6832	Phase 2
0.7285	Intermediate Similarity	NPD422	Phase 1
0.7285	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1610	Phase 2
0.7278	Intermediate Similarity	NPD6355	Discontinued
0.7278	Intermediate Similarity	NPD37	Approved
0.7278	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1471	Phase 3
0.7261	Intermediate Similarity	NPD6233	Phase 2
0.7251	Intermediate Similarity	NPD4967	Phase 2
0.7251	Intermediate Similarity	NPD4965	Approved
0.7251	Intermediate Similarity	NPD4966	Approved
0.725	Intermediate Similarity	NPD4308	Phase 3
0.7241	Intermediate Similarity	NPD7229	Phase 3
0.7237	Intermediate Similarity	NPD9717	Approved
0.7237	Intermediate Similarity	NPD9269	Phase 2
0.7237	Intermediate Similarity	NPD1608	Approved
0.7234	Intermediate Similarity	NPD6782	Approved
0.7234	Intermediate Similarity	NPD6776	Approved
0.7234	Intermediate Similarity	NPD6781	Approved
0.7234	Intermediate Similarity	NPD6780	Approved
0.7234	Intermediate Similarity	NPD6777	Approved
0.7234	Intermediate Similarity	NPD6778	Approved
0.7234	Intermediate Similarity	NPD6779	Approved
0.7229	Intermediate Similarity	NPD5049	Phase 3
0.7222	Intermediate Similarity	NPD8312	Approved
0.7222	Intermediate Similarity	NPD8313	Approved
0.7219	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7435	Discontinued
0.7198	Intermediate Similarity	NPD8150	Discontinued
0.7195	Intermediate Similarity	NPD2354	Approved
0.7188	Intermediate Similarity	NPD7584	Approved
0.7178	Intermediate Similarity	NPD2654	Approved
0.7175	Intermediate Similarity	NPD7228	Approved
0.7171	Intermediate Similarity	NPD1201	Approved
0.717	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5124	Phase 1
0.7169	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3225	Approved
0.7134	Intermediate Similarity	NPD7095	Approved
0.7111	Intermediate Similarity	NPD7685	Pre-registration
0.7102	Intermediate Similarity	NPD5242	Approved
0.7101	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7458	Discontinued
0.7099	Intermediate Similarity	NPD5406	Approved
0.7099	Intermediate Similarity	NPD5405	Approved
0.7099	Intermediate Similarity	NPD5404	Approved
0.7099	Intermediate Similarity	NPD5408	Approved
0.7097	Intermediate Similarity	NPD3266	Approved
0.7097	Intermediate Similarity	NPD3267	Approved
0.7097	Intermediate Similarity	NPD1470	Approved
0.7095	Intermediate Similarity	NPD1729	Discontinued
0.7093	Intermediate Similarity	NPD4288	Approved
0.7089	Intermediate Similarity	NPD411	Approved
0.7078	Intermediate Similarity	NPD4749	Approved
0.7076	Intermediate Similarity	NPD6844	Discontinued
0.7048	Intermediate Similarity	NPD3300	Phase 2
0.7039	Intermediate Similarity	NPD17	Approved
0.7031	Intermediate Similarity	NPD7696	Phase 3
0.7031	Intermediate Similarity	NPD7698	Approved
0.7031	Intermediate Similarity	NPD7697	Approved
0.7026	Intermediate Similarity	NPD8151	Discontinued
0.7013	Intermediate Similarity	NPD3972	Approved
0.7012	Intermediate Similarity	NPD2424	Discontinued
0.7006	Intermediate Similarity	NPD2861	Phase 2

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