NPASS Compound

Structure

CID195351 OpenBabel06191715582D 22 24 0 0 0 0 0 0 0 0999 V2000 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 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 2.5981 -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 -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 -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 3.4641 -2.0000 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 3 1 0 0 0 0 1 6 2 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 2 0 0 0 0 4 7 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 8 17 1 0 0 0 0 9 10 2 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 11 12 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 20 2 0 0 0 0 14 15 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.04
Volume:	282.767
LogP:	2.08
LogD:	1.067
LogS:	-3.487
# Rotatable Bonds:	1
TPSA:	131.36
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	2.524
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.255
MDCK Permeability:	7.4695403782243375e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.743
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	97.9475326538086%
Volume Distribution (VD):	0.516
Pgp-substrate:	8.224775314331055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.872
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.601
CYP2C9-substrate:	0.41
CYP2D6-inhibitor:	0.42
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.161
CYP3A4-substrate:	0.043

ADMET: Excretion

Clearance (CL):	6.077
Half-life (T1/2):	0.936

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.087
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.718
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.045
Skin Sensitization:	0.93
Carcinogencity:	0.097
Eye Corrosion:	0.005
Eye Irritation:	0.923
Respiratory Toxicity:	0.058

Download Data

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

Natural Product: NPC195351

Natural Product ID:	NPC195351
*Common Name:**	6-Hydroxykaempferol
IUPAC Name:	3,5,6,7-tetrahydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms:	6-Hydroxykaempferol
Standard InCHIKey:	LFPHMXIOQBBTSS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O7/c16-7-3-1-6(2-4-7)15-14(21)13(20)10-9(22-15)5-8(17)11(18)12(10)19/h1-5,16-19,21H
SMILES:	Oc1ccc(cc1)c1oc2cc(O)c(c(c2c(=O)c1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455504
PubChem CID:	5281638
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001136] Flavonols

*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
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22060189]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[22723874]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23371463]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Flowers	Lasa, China	n.a.	PMID[24621197]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27748595]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Bud	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18311	Carthamus tinctorius	Species	Asteraceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1380	Individual Protein	Avian myoblastosis virus polyprotein II	Avian myeloblastosis virus	Inhibition	=	97.2	%	PMID[463227]

☑ 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 NPC195351 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	588
0.1-0.2	2324
0.2-0.3	6102
0.3-0.4	11571
0.4-0.5	4598
0.5-0.6	4286
0.6-0.7	5206
0.7-0.8	4747
0.8-0.85	1653
0.85-0.9	918
0.9-0.95	455
0.95-1	249

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC77858
0.9861	High Similarity	NPC225731
0.9859	High Similarity	NPC130230
0.9859	High Similarity	NPC275772
0.9859	High Similarity	NPC239312
0.9793	High Similarity	NPC27208
0.979	High Similarity	NPC12367
0.979	High Similarity	NPC118726
0.9789	High Similarity	NPC179271
0.9789	High Similarity	NPC20791
0.9722	High Similarity	NPC296197
0.9722	High Similarity	NPC216318
0.9722	High Similarity	NPC17286
0.9722	High Similarity	NPC259713
0.972	High Similarity	NPC74881
0.972	High Similarity	NPC51443
0.966	High Similarity	NPC26227
0.966	High Similarity	NPC44079
0.966	High Similarity	NPC214138
0.966	High Similarity	NPC201451
0.9655	High Similarity	NPC45873
0.9655	High Similarity	NPC184136
0.9653	High Similarity	NPC276930
0.965	High Similarity	NPC169749
0.9648	High Similarity	NPC279121
0.9595	High Similarity	NPC43243
0.9595	High Similarity	NPC98661
0.9595	High Similarity	NPC245546
0.9595	High Similarity	NPC49824
0.9595	High Similarity	NPC266960
0.9595	High Similarity	NPC247017
0.9586	High Similarity	NPC270465
0.9586	High Similarity	NPC87125
0.958	High Similarity	NPC70136
0.9577	High Similarity	NPC175013
0.953	High Similarity	NPC110070
0.953	High Similarity	NPC287979
0.953	High Similarity	NPC163524
0.953	High Similarity	NPC93376
0.953	High Similarity	NPC224137
0.953	High Similarity	NPC203891
0.953	High Similarity	NPC75215
0.953	High Similarity	NPC305663
0.953	High Similarity	NPC101830
0.953	High Similarity	NPC176665
0.953	High Similarity	NPC189179
0.953	High Similarity	NPC227192
0.9524	High Similarity	NPC239128
0.9524	High Similarity	NPC256283
0.9524	High Similarity	NPC71334
0.9524	High Similarity	NPC301123
0.9524	High Similarity	NPC120163
0.9524	High Similarity	NPC187498
0.9524	High Similarity	NPC222830
0.9524	High Similarity	NPC188203
0.9524	High Similarity	NPC275836
0.9524	High Similarity	NPC275722
0.9524	High Similarity	NPC241498
0.9524	High Similarity	NPC100887
0.9524	High Similarity	NPC131624
0.9524	High Similarity	NPC198826
0.9524	High Similarity	NPC293183
0.9524	High Similarity	NPC83508
0.9524	High Similarity	NPC212678
0.9524	High Similarity	NPC57030
0.9524	High Similarity	NPC301323
0.9524	High Similarity	NPC162313
0.9524	High Similarity	NPC25270
0.9524	High Similarity	NPC156222
0.9521	High Similarity	NPC286342
0.9521	High Similarity	NPC149127
0.9521	High Similarity	NPC62042
0.9521	High Similarity	NPC61620
0.9521	High Similarity	NPC188871
0.9517	High Similarity	NPC194856
0.9467	High Similarity	NPC7846
0.9467	High Similarity	NPC300943
0.9467	High Similarity	NPC288669
0.9467	High Similarity	NPC176300
0.9467	High Similarity	NPC253634
0.9467	High Similarity	NPC191459
0.9467	High Similarity	NPC4481
0.9467	High Similarity	NPC25495
0.9467	High Similarity	NPC9609
0.9467	High Similarity	NPC152166
0.9467	High Similarity	NPC261004
0.9467	High Similarity	NPC19687
0.9467	High Similarity	NPC18772
0.9467	High Similarity	NPC143828
0.9467	High Similarity	NPC204854
0.9467	High Similarity	NPC115798
0.9467	High Similarity	NPC18607
0.9467	High Similarity	NPC22472
0.9467	High Similarity	NPC105242
0.9467	High Similarity	NPC130894
0.9463	High Similarity	NPC292107
0.9463	High Similarity	NPC474520
0.9463	High Similarity	NPC201837
0.9459	High Similarity	NPC145379
0.9459	High Similarity	NPC22519
0.9459	High Similarity	NPC69394
0.9459	High Similarity	NPC255350
0.9459	High Similarity	NPC183878
0.9459	High Similarity	NPC86485
0.9459	High Similarity	NPC231018
0.9459	High Similarity	NPC47781
0.9459	High Similarity	NPC176775
0.9459	High Similarity	NPC274327
0.9459	High Similarity	NPC160951
0.9456	High Similarity	NPC260895
0.9456	High Similarity	NPC54394
0.9456	High Similarity	NPC204515
0.9456	High Similarity	NPC251110
0.9456	High Similarity	NPC200740
0.9456	High Similarity	NPC125062
0.9456	High Similarity	NPC252933
0.9448	High Similarity	NPC207729
0.9448	High Similarity	NPC168803
0.9448	High Similarity	NPC108406
0.94	High Similarity	NPC78302
0.94	High Similarity	NPC472438
0.94	High Similarity	NPC235215
0.94	High Similarity	NPC7973
0.94	High Similarity	NPC29841
0.9396	High Similarity	NPC213622
0.9396	High Similarity	NPC32557
0.9396	High Similarity	NPC256612
0.9396	High Similarity	NPC167815
0.9396	High Similarity	NPC20830
0.9396	High Similarity	NPC183597
0.9396	High Similarity	NPC50715
0.9396	High Similarity	NPC163780
0.9396	High Similarity	NPC2476
0.9396	High Similarity	NPC227325
0.9396	High Similarity	NPC201136
0.9396	High Similarity	NPC196439
0.9396	High Similarity	NPC128863
0.9396	High Similarity	NPC4455
0.9396	High Similarity	NPC138360
0.9396	High Similarity	NPC280339
0.9396	High Similarity	NPC146165
0.9396	High Similarity	NPC92659
0.9396	High Similarity	NPC189960
0.9392	High Similarity	NPC37684
0.9392	High Similarity	NPC199100
0.9392	High Similarity	NPC120537
0.9392	High Similarity	NPC180234
0.9392	High Similarity	NPC82325
0.9392	High Similarity	NPC279989
0.9392	High Similarity	NPC55205
0.9392	High Similarity	NPC142540
0.9392	High Similarity	NPC157784
0.9392	High Similarity	NPC63187
0.9388	High Similarity	NPC306821
0.9388	High Similarity	NPC248102
0.9384	High Similarity	NPC218490
0.9384	High Similarity	NPC119059
0.9384	High Similarity	NPC19545
0.9338	High Similarity	NPC193842
0.9333	High Similarity	NPC200388
0.9333	High Similarity	NPC268161
0.9333	High Similarity	NPC55619
0.9333	High Similarity	NPC100916
0.9333	High Similarity	NPC178854
0.9333	High Similarity	NPC265511
0.9329	High Similarity	NPC206238
0.9329	High Similarity	NPC167091
0.9329	High Similarity	NPC292214
0.9329	High Similarity	NPC276409
0.9329	High Similarity	NPC75279
0.9329	High Similarity	NPC270620
0.9329	High Similarity	NPC271779
0.9329	High Similarity	NPC88645
0.9329	High Similarity	NPC250822
0.9329	High Similarity	NPC236223
0.9329	High Similarity	NPC179126
0.9329	High Similarity	NPC78326
0.9324	High Similarity	NPC59162
0.9324	High Similarity	NPC304295
0.9324	High Similarity	NPC28274
0.9324	High Similarity	NPC226973
0.9324	High Similarity	NPC202157
0.9324	High Similarity	NPC50403
0.9324	High Similarity	NPC208043
0.9324	High Similarity	NPC133953
0.9324	High Similarity	NPC205046
0.932	High Similarity	NPC52005
0.932	High Similarity	NPC159103
0.932	High Similarity	NPC137062
0.932	High Similarity	NPC287101
0.932	High Similarity	NPC223579
0.932	High Similarity	NPC183950
0.9315	High Similarity	NPC55557
0.9315	High Similarity	NPC30647
0.9315	High Similarity	NPC86847
0.9315	High Similarity	NPC61871
0.9315	High Similarity	NPC140840
0.9276	High Similarity	NPC263449
0.9276	High Similarity	NPC246478
0.9272	High Similarity	NPC470402

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 NPC195351 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	507
0.1-0.2	1069
0.2-0.3	2006
0.3-0.4	2680
0.4-0.5	1551
0.5-0.6	920
0.6-0.7	280
0.7-0.8	91
0.8-0.85	27
0.85-0.9	12
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9789	High Similarity	NPD1512	Approved
0.9648	High Similarity	NPD1511	Approved
0.9459	High Similarity	NPD2801	Approved
0.9007	High Similarity	NPD1934	Approved
0.8954	High Similarity	NPD3882	Suspended
0.8947	High Similarity	NPD2393	Clinical (unspecified phase)
0.8792	High Similarity	NPD4378	Clinical (unspecified phase)
0.8766	High Similarity	NPD3817	Phase 2
0.8765	High Similarity	NPD4338	Clinical (unspecified phase)
0.8679	High Similarity	NPD6167	Clinical (unspecified phase)
0.8679	High Similarity	NPD6168	Clinical (unspecified phase)
0.8679	High Similarity	NPD6166	Phase 2
0.8571	High Similarity	NPD3818	Discontinued
0.8571	High Similarity	NPD1552	Clinical (unspecified phase)
0.8571	High Similarity	NPD1550	Clinical (unspecified phase)
0.8562	High Similarity	NPD1510	Phase 2
0.8542	High Similarity	NPD943	Approved
0.8528	High Similarity	NPD6797	Phase 2
0.8514	High Similarity	NPD1549	Phase 2
0.8476	Intermediate Similarity	NPD7251	Discontinued
0.8408	Intermediate Similarity	NPD5402	Approved
0.8405	Intermediate Similarity	NPD7054	Approved
0.8354	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7472	Approved
0.8313	Intermediate Similarity	NPD7808	Phase 3
0.8311	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD1240	Approved
0.8269	Intermediate Similarity	NPD4380	Phase 2
0.8261	Intermediate Similarity	NPD1247	Approved
0.8242	Intermediate Similarity	NPD7074	Phase 3
0.8235	Intermediate Similarity	NPD6799	Approved
0.8228	Intermediate Similarity	NPD1465	Phase 2
0.8199	Intermediate Similarity	NPD5494	Approved
0.8187	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7075	Discontinued
0.8182	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1607	Approved
0.8146	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD2796	Approved
0.8113	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD6801	Discontinued
0.8039	Intermediate Similarity	NPD3750	Approved
0.7988	Intermediate Similarity	NPD6232	Discontinued
0.7987	Intermediate Similarity	NPD230	Phase 1
0.7964	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD5403	Approved
0.7952	Intermediate Similarity	NPD7473	Discontinued
0.7949	Intermediate Similarity	NPD5401	Approved
0.7925	Intermediate Similarity	NPD6599	Discontinued
0.7919	Intermediate Similarity	NPD1613	Approved
0.7919	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD919	Approved
0.7895	Intermediate Similarity	NPD1551	Phase 2
0.7888	Intermediate Similarity	NPD7819	Suspended
0.7867	Intermediate Similarity	NPD447	Suspended
0.7857	Intermediate Similarity	NPD2800	Approved
0.7853	Intermediate Similarity	NPD3749	Approved
0.784	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD3926	Phase 2
0.7778	Intermediate Similarity	NPD2935	Discontinued
0.7764	Intermediate Similarity	NPD7411	Suspended
0.7751	Intermediate Similarity	NPD5844	Phase 1
0.7712	Intermediate Similarity	NPD3748	Approved
0.7711	Intermediate Similarity	NPD6959	Discontinued
0.7692	Intermediate Similarity	NPD3751	Discontinued
0.7687	Intermediate Similarity	NPD1203	Approved
0.7667	Intermediate Similarity	NPD2313	Discontinued
0.7643	Intermediate Similarity	NPD6190	Approved
0.7628	Intermediate Similarity	NPD1243	Approved
0.7625	Intermediate Similarity	NPD920	Approved
0.7613	Intermediate Similarity	NPD2344	Approved
0.761	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD9269	Phase 2
0.7597	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1653	Approved
0.756	Intermediate Similarity	NPD3787	Discontinued
0.755	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD3226	Approved
0.7514	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD1548	Phase 1
0.75	Intermediate Similarity	NPD2533	Approved
0.7484	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7768	Phase 2
0.7467	Intermediate Similarity	NPD9494	Approved
0.7436	Intermediate Similarity	NPD6100	Approved
0.7436	Intermediate Similarity	NPD6099	Approved
0.7421	Intermediate Similarity	NPD2309	Approved
0.7415	Intermediate Similarity	NPD422	Phase 1
0.7407	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2346	Discontinued
0.7372	Intermediate Similarity	NPD2799	Discontinued
0.7368	Intermediate Similarity	NPD3027	Phase 3
0.7365	Intermediate Similarity	NPD9717	Approved
0.7333	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD9268	Approved
0.7318	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1610	Phase 2
0.7297	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1933	Approved
0.7273	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3225	Approved
0.7257	Intermediate Similarity	NPD5953	Discontinued
0.725	Intermediate Similarity	NPD4628	Phase 3
0.7248	Intermediate Similarity	NPD1608	Approved
0.7248	Intermediate Similarity	NPD1481	Phase 2
0.7247	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6651	Approved
0.7241	Intermediate Similarity	NPD7286	Phase 2
0.7222	Intermediate Similarity	NPD7390	Discontinued
0.7222	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1470	Approved
0.7208	Intermediate Similarity	NPD3268	Approved
0.7208	Intermediate Similarity	NPD411	Approved
0.72	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7199	Phase 2
0.7186	Intermediate Similarity	NPD6844	Discontinued
0.7181	Intermediate Similarity	NPD1535	Discovery
0.7181	Intermediate Similarity	NPD1201	Approved
0.7179	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6234	Discontinued
0.7171	Intermediate Similarity	NPD2798	Approved
0.717	Intermediate Similarity	NPD1471	Phase 3
0.7161	Intermediate Similarity	NPD6233	Phase 2
0.7152	Intermediate Similarity	NPD4308	Phase 3
0.7151	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8434	Phase 2
0.7105	Intermediate Similarity	NPD2797	Approved
0.7101	Intermediate Similarity	NPD4288	Approved
0.7097	Intermediate Similarity	NPD1296	Phase 2
0.7081	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4908	Phase 1
0.7078	Intermediate Similarity	NPD6832	Phase 2
0.7069	Intermediate Similarity	NPD2403	Approved
0.7059	Intermediate Similarity	NPD6778	Approved
0.7059	Intermediate Similarity	NPD6780	Approved
0.7059	Intermediate Similarity	NPD6781	Approved
0.7059	Intermediate Similarity	NPD6782	Approved
0.7059	Intermediate Similarity	NPD6776	Approved
0.7059	Intermediate Similarity	NPD6779	Approved
0.7059	Intermediate Similarity	NPD6777	Approved
0.7047	Intermediate Similarity	NPD17	Approved
0.7044	Intermediate Similarity	NPD7033	Discontinued
0.7022	Intermediate Similarity	NPD7685	Pre-registration
0.7013	Intermediate Similarity	NPD2861	Phase 2
0.6994	Remote Similarity	NPD2354	Approved
0.6993	Remote Similarity	NPD3267	Approved
0.6993	Remote Similarity	NPD3266	Approved
0.6987	Remote Similarity	NPD6798	Discontinued
0.6987	Remote Similarity	NPD3764	Approved
0.6987	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD37	Approved
0.6975	Remote Similarity	NPD2654	Approved
0.6973	Remote Similarity	NPD4360	Phase 2
0.6973	Remote Similarity	NPD4363	Phase 3
0.697	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4966	Approved
0.6959	Remote Similarity	NPD4965	Approved
0.6959	Remote Similarity	NPD4967	Phase 2
0.6954	Remote Similarity	NPD5710	Approved
0.6954	Remote Similarity	NPD5711	Approved
0.6951	Remote Similarity	NPD3300	Phase 2
0.6947	Remote Similarity	NPD7435	Discontinued
0.6944	Remote Similarity	NPD8313	Approved
0.6944	Remote Similarity	NPD8312	Approved
0.694	Remote Similarity	NPD4287	Approved
0.6923	Remote Similarity	NPD4625	Phase 3
0.6923	Remote Similarity	NPD8150	Discontinued
0.6914	Remote Similarity	NPD5242	Approved
0.6913	Remote Similarity	NPD9545	Approved
0.6901	Remote Similarity	NPD2296	Approved
0.6899	Remote Similarity	NPD4307	Phase 2
0.6893	Remote Similarity	NPD7228	Approved
0.6892	Remote Similarity	NPD9493	Approved
0.6892	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1652	Phase 2
0.6863	Remote Similarity	NPD4749	Approved
0.6859	Remote Similarity	NPD7696	Phase 3
0.6859	Remote Similarity	NPD7698	Approved
0.6859	Remote Similarity	NPD7697	Approved
0.6857	Remote Similarity	NPD7229	Phase 3
0.6855	Remote Similarity	NPD6355	Discontinued
0.6845	Remote Similarity	NPD4361	Phase 2
0.6845	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1019	Discontinued
0.6824	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6386	Approved
0.6824	Remote Similarity	NPD6385	Approved
0.6823	Remote Similarity	NPD7871	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