NPASS Compound

Structure

NPC472344 OpenBabel07101718232D 32 34 0 0 1 0 0 0 0 0999 V2000 -7.5715 2.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5238 0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8316 -2.3787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3745 -3.2200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7303 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6826 1.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5715 1.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6826 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6826 1.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4084 -1.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8602 -2.3787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7303 0.9714 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8413 1.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3651 0.9714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2064 -0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8413 1.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8413 0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3745 -1.5375 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0477 0.9714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8890 1.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3651 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2064 1.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0477 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8413 0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8890 2.4286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5238 -0.4857 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2064 2.4286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6826 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7696 -0.6500 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 7 1 0 0 0 0 2 8 1 0 0 0 0 3 11 2 0 0 0 0 4 11 1 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 8 17 1 0 0 0 0 9 14 1 0 0 0 0 9 16 1 0 0 0 0 10 15 1 0 0 0 0 10 18 1 0 0 0 0 12 5 1 1 0 0 0 12 20 1 0 0 0 0 13 17 2 0 0 0 0 13 21 1 0 0 0 0 14 22 2 0 0 0 0 14 23 1 0 0 0 0 15 22 1 0 0 0 0 15 24 2 0 0 0 0 16 21 2 0 0 0 0 16 25 1 0 0 0 0 17 32 1 0 0 0 0 18 11 1 1 0 0 0 18 31 1 0 0 0 0 19 20 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 26 2 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 24 31 1 0 0 0 0 25 30 2 0 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.2
Volume:	455.727
LogP:	4.748
LogD:	2.645
LogS:	-3.765
# Rotatable Bonds:	7
TPSA:	117.2
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.432
Synthetic Accessibility Score:	4.225
Fsp3:	0.44
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:	-4.809
MDCK Permeability:	1.912556581373792e-05
Pgp-inhibitor:	0.488
Pgp-substrate:	0.859
Human Intestinal Absorption (HIA):	0.042
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	99.0162124633789%
Volume Distribution (VD):	0.317
Pgp-substrate:	1.2329460382461548%

ADMET: Metabolism

CYP1A2-inhibitor:	0.168
CYP1A2-substrate:	0.949
CYP2C19-inhibitor:	0.255
CYP2C19-substrate:	0.407
CYP2C9-inhibitor:	0.81
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.063
CYP2D6-substrate:	0.318
CYP3A4-inhibitor:	0.294
CYP3A4-substrate:	0.535

ADMET: Excretion

Clearance (CL):	4.328
Half-life (T1/2):	0.069

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.979
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.703
Maximum Recommended Daily Dose:	0.221
Skin Sensitization:	0.934
Carcinogencity:	0.158
Eye Corrosion:	0.003
Eye Irritation:	0.169
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC472344

Natural Product ID:	NPC472344
*Common Name:**	WKTCTHHJINXGSJ-SGTLLEGYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WKTCTHHJINXGSJ-SGTLLEGYSA-N
Standard InCHI:	InChI=1S/C25H30O7/c1-7-12(5)20(26)19-23(29)14(22(28)15-10-18(11(3)4)31-24(15)19)9-16-21(27)13(6)17(8-2)32-25(16)30/h12,18,27-29H,3,7-10H2,1-2,4-6H3/t12-,18-/m0/s1
SMILES:	CC[C@@H](C(=O)c1c(O)c(Cc2c(=O)oc(c(c2O)C)CC)c(c2c1O[C@@H](C2)C(=C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3359525
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000350] Butyrophenones

*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
NPO29471	Achyrocline satureioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858757]
NPO29471	Achyrocline satureioides	Species	Asteraceae	Eukaryota	aerial parts	Alpa Corral, Cordoba, Argentina	2008-Aug	PMID[25517209]
NPO29471	Achyrocline satureioides	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
MIC	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64000.0	nM	PMID[544328]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128000.0	nM	PMID[544328]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32000.0	nM	PMID[544328]
NPT1204	Organism	Enterococcus faecalis ATCC 29212	Enterococcus faecalis ATCC 29212	MIC	=	64000.0	nM	PMID[544328]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	128000.0	nM	PMID[544328]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	128000.0	nM	PMID[544328]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	>	128000.0	nM	PMID[544328]

☑ 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 NPC472344 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	322
0.1-0.2	1472
0.2-0.3	3768
0.3-0.4	8264
0.4-0.5	11118
0.5-0.6	4193
0.6-0.7	6155
0.7-0.8	5342
0.8-0.85	1483
0.85-0.9	519
0.9-0.95	60
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.971	High Similarity	NPC470556
0.964	High Similarity	NPC96216
0.964	High Similarity	NPC470553
0.964	High Similarity	NPC470909
0.964	High Similarity	NPC474939
0.964	High Similarity	NPC307895
0.9571	High Similarity	NPC133060
0.9571	High Similarity	NPC118059
0.9571	High Similarity	NPC470554
0.9571	High Similarity	NPC288910
0.9568	High Similarity	NPC294432
0.9568	High Similarity	NPC112829
0.951	High Similarity	NPC470908
0.951	High Similarity	NPC321387
0.951	High Similarity	NPC327059
0.9504	High Similarity	NPC470910
0.95	High Similarity	NPC33653
0.95	High Similarity	NPC184738
0.9444	High Similarity	NPC290671
0.942	High Similarity	NPC183639
0.942	High Similarity	NPC199458
0.9353	High Similarity	NPC241975
0.9353	High Similarity	NPC19476
0.9348	High Similarity	NPC131782
0.9348	High Similarity	NPC474624
0.9348	High Similarity	NPC138047
0.9301	High Similarity	NPC285748
0.9281	High Similarity	NPC470083
0.9281	High Similarity	NPC219584
0.9241	High Similarity	NPC474735
0.922	High Similarity	NPC74397
0.9189	High Similarity	NPC109967
0.9189	High Similarity	NPC78554
0.9189	High Similarity	NPC321372
0.9189	High Similarity	NPC474738
0.9189	High Similarity	NPC475797
0.9189	High Similarity	NPC474609
0.9189	High Similarity	NPC469936
0.9189	High Similarity	NPC129053
0.9167	High Similarity	NPC474108
0.9167	High Similarity	NPC177995
0.9137	High Similarity	NPC470982
0.9137	High Similarity	NPC470983
0.9122	High Similarity	NPC108937
0.9122	High Similarity	NPC279218
0.911	High Similarity	NPC180351
0.9103	High Similarity	NPC168085
0.9103	High Similarity	NPC472345
0.9097	High Similarity	NPC470322
0.9091	High Similarity	NPC18886
0.9085	High Similarity	NPC470555
0.9078	High Similarity	NPC139554
0.9078	High Similarity	NPC472343
0.9065	High Similarity	NPC101752
0.9041	High Similarity	NPC104236
0.9041	High Similarity	NPC164205
0.9041	High Similarity	NPC19238
0.9041	High Similarity	NPC317492
0.9034	High Similarity	NPC202494
0.9028	High Similarity	NPC224714
0.9028	High Similarity	NPC297788
0.9028	High Similarity	NPC1886
0.9028	High Similarity	NPC196137
0.9021	High Similarity	NPC276565
0.9014	High Similarity	NPC307990
0.9014	High Similarity	NPC16455
0.9014	High Similarity	NPC221173
0.9007	High Similarity	NPC131130
0.9	High Similarity	NPC174999
0.9	High Similarity	NPC156910
0.8986	High Similarity	NPC470988
0.8986	High Similarity	NPC256141
0.898	High Similarity	NPC476509
0.898	High Similarity	NPC321896
0.898	High Similarity	NPC476185
0.8966	High Similarity	NPC154217
0.8966	High Similarity	NPC181388
0.8958	High Similarity	NPC112791
0.8958	High Similarity	NPC94794
0.8958	High Similarity	NPC196459
0.8958	High Similarity	NPC470296
0.8958	High Similarity	NPC188632
0.8958	High Similarity	NPC87609
0.8951	High Similarity	NPC111201
0.8951	High Similarity	NPC171870
0.8944	High Similarity	NPC37206
0.8944	High Similarity	NPC23257
0.8944	High Similarity	NPC137009
0.8944	High Similarity	NPC270913
0.8929	High Similarity	NPC60667
0.8921	High Similarity	NPC470984
0.8919	High Similarity	NPC471675
0.8919	High Similarity	NPC209142
0.8919	High Similarity	NPC312549
0.8913	High Similarity	NPC185624
0.8912	High Similarity	NPC139966
0.8912	High Similarity	NPC307052
0.8905	High Similarity	NPC21378
0.8905	High Similarity	NPC470987
0.8904	High Similarity	NPC8817
0.8904	High Similarity	NPC473133
0.8904	High Similarity	NPC47388
0.8904	High Similarity	NPC470670
0.8897	High Similarity	NPC470890
0.8897	High Similarity	NPC178627
0.8897	High Similarity	NPC469935
0.8897	High Similarity	NPC294365
0.8897	High Similarity	NPC469953
0.8897	High Similarity	NPC75694
0.8897	High Similarity	NPC316535
0.8889	High Similarity	NPC36181
0.8881	High Similarity	NPC471587
0.8881	High Similarity	NPC289660
0.8881	High Similarity	NPC164697
0.8881	High Similarity	NPC470856
0.8881	High Similarity	NPC82920
0.8874	High Similarity	NPC269495
0.8873	High Similarity	NPC470668
0.8873	High Similarity	NPC470671
0.8873	High Similarity	NPC474487
0.8873	High Similarity	NPC474504
0.8873	High Similarity	NPC470672
0.8873	High Similarity	NPC470669
0.8867	High Similarity	NPC469934
0.8865	High Similarity	NPC470397
0.8865	High Similarity	NPC470398
0.8859	High Similarity	NPC31627
0.8859	High Similarity	NPC476238
0.8859	High Similarity	NPC327269
0.8857	High Similarity	NPC144027
0.8857	High Similarity	NPC125920
0.8857	High Similarity	NPC236974
0.8851	High Similarity	NPC472421
0.8849	High Similarity	NPC285054
0.8844	High Similarity	NPC10097
0.8844	High Similarity	NPC208303
0.8844	High Similarity	NPC470460
0.8844	High Similarity	NPC161864
0.8836	High Similarity	NPC470357
0.8836	High Similarity	NPC290133
0.8836	High Similarity	NPC24136
0.8836	High Similarity	NPC476088
0.8836	High Similarity	NPC187282
0.8836	High Similarity	NPC474161
0.8836	High Similarity	NPC472629
0.8828	High Similarity	NPC77794
0.8828	High Similarity	NPC223812
0.8828	High Similarity	NPC81697
0.8828	High Similarity	NPC278249
0.8828	High Similarity	NPC107177
0.8828	High Similarity	NPC85162
0.8828	High Similarity	NPC125894
0.8824	High Similarity	NPC92589
0.8819	High Similarity	NPC248372
0.8819	High Similarity	NPC96408
0.8819	High Similarity	NPC279650
0.8819	High Similarity	NPC258630
0.8819	High Similarity	NPC476508
0.8819	High Similarity	NPC201820
0.8819	High Similarity	NPC110038
0.8819	High Similarity	NPC282300
0.8819	High Similarity	NPC17170
0.8819	High Similarity	NPC166689
0.8819	High Similarity	NPC156190
0.8811	High Similarity	NPC53181
0.8811	High Similarity	NPC240305
0.8811	High Similarity	NPC217186
0.8794	High Similarity	NPC84699
0.8792	High Similarity	NPC316960
0.8792	High Similarity	NPC204561
0.8792	High Similarity	NPC472636
0.8792	High Similarity	NPC474744
0.8792	High Similarity	NPC148945
0.8792	High Similarity	NPC474772
0.8792	High Similarity	NPC309512
0.8792	High Similarity	NPC317715
0.8792	High Similarity	NPC472423
0.8792	High Similarity	NPC78835
0.8792	High Similarity	NPC318424
0.8786	High Similarity	NPC108113
0.8786	High Similarity	NPC93756
0.8784	High Similarity	NPC469932
0.8784	High Similarity	NPC5173
0.8784	High Similarity	NPC470461
0.8776	High Similarity	NPC85773
0.8776	High Similarity	NPC91902
0.8776	High Similarity	NPC249942
0.8776	High Similarity	NPC137296
0.8776	High Similarity	NPC473077
0.8776	High Similarity	NPC296998
0.8776	High Similarity	NPC140120
0.8776	High Similarity	NPC308200
0.8776	High Similarity	NPC297886
0.8767	High Similarity	NPC235217
0.8767	High Similarity	NPC473013
0.8767	High Similarity	NPC473014
0.8767	High Similarity	NPC87486
0.8767	High Similarity	NPC131579
0.8767	High Similarity	NPC171656
0.8767	High Similarity	NPC71184

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 NPC472344 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	965
0.2-0.3	1971
0.3-0.4	2587
0.4-0.5	1937
0.5-0.6	978
0.6-0.7	291
0.7-0.8	110
0.8-0.85	27
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8897	High Similarity	NPD2534	Approved
0.8897	High Similarity	NPD2533	Approved
0.8897	High Similarity	NPD2532	Approved
0.8811	High Similarity	NPD2800	Approved
0.8767	High Similarity	NPD4378	Clinical (unspecified phase)
0.8521	High Similarity	NPD6651	Approved
0.8506	High Similarity	NPD7075	Discontinued
0.8483	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD1243	Approved
0.8421	Intermediate Similarity	NPD7411	Suspended
0.8414	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD920	Approved
0.8389	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD6801	Discontinued
0.8356	Intermediate Similarity	NPD1549	Phase 2
0.8355	Intermediate Similarity	NPD4380	Phase 2
0.8345	Intermediate Similarity	NPD2796	Approved
0.8312	Intermediate Similarity	NPD7819	Suspended
0.8276	Intermediate Similarity	NPD1510	Phase 2
0.8267	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD6799	Approved
0.8176	Intermediate Similarity	NPD5710	Approved
0.8176	Intermediate Similarity	NPD5711	Approved
0.8153	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1934	Approved
0.8125	Intermediate Similarity	NPD1240	Approved
0.8089	Intermediate Similarity	NPD7768	Phase 2
0.8075	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD5124	Phase 1
0.8069	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD3817	Phase 2
0.8014	Intermediate Similarity	NPD1607	Approved
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD3750	Approved
0.7986	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3818	Discontinued
0.7975	Intermediate Similarity	NPD3882	Suspended
0.7973	Intermediate Similarity	NPD2935	Discontinued
0.7973	Intermediate Similarity	NPD1551	Phase 2
0.7962	Intermediate Similarity	NPD2801	Approved
0.7961	Intermediate Similarity	NPD1511	Approved
0.7937	Intermediate Similarity	NPD5494	Approved
0.7925	Intermediate Similarity	NPD3749	Approved
0.7905	Intermediate Similarity	NPD2799	Discontinued
0.7892	Intermediate Similarity	NPD6559	Discontinued
0.7875	Intermediate Similarity	NPD919	Approved
0.7862	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2313	Discontinued
0.7857	Intermediate Similarity	NPD1512	Approved
0.7844	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD5953	Discontinued
0.7818	Intermediate Similarity	NPD7286	Phase 2
0.7806	Intermediate Similarity	NPD5403	Approved
0.7805	Intermediate Similarity	NPD7473	Discontinued
0.7744	Intermediate Similarity	NPD6166	Phase 2
0.7744	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6232	Discontinued
0.7711	Intermediate Similarity	NPD7054	Approved
0.7688	Intermediate Similarity	NPD5402	Approved
0.7682	Intermediate Similarity	NPD6002	Phase 3
0.7682	Intermediate Similarity	NPD6005	Phase 3
0.7682	Intermediate Similarity	NPD6004	Phase 3
0.7682	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5401	Approved
0.7667	Intermediate Similarity	NPD3748	Approved
0.7667	Intermediate Similarity	NPD7033	Discontinued
0.7665	Intermediate Similarity	NPD7472	Approved
0.7665	Intermediate Similarity	NPD7074	Phase 3
0.7647	Intermediate Similarity	NPD4628	Phase 3
0.7647	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6797	Phase 2
0.7606	Intermediate Similarity	NPD422	Phase 1
0.7605	Intermediate Similarity	NPD5844	Phase 1
0.7574	Intermediate Similarity	NPD7251	Discontinued
0.7566	Intermediate Similarity	NPD2344	Approved
0.7566	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1247	Approved
0.7552	Intermediate Similarity	NPD9717	Approved
0.7529	Intermediate Similarity	NPD7808	Phase 3
0.7517	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3268	Approved
0.7484	Intermediate Similarity	NPD3226	Approved
0.7483	Intermediate Similarity	NPD6832	Phase 2
0.7468	Intermediate Similarity	NPD2654	Approved
0.7467	Intermediate Similarity	NPD230	Phase 1
0.7451	Intermediate Similarity	NPD2346	Discontinued
0.7412	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7229	Phase 3
0.7401	Intermediate Similarity	NPD4363	Phase 3
0.7401	Intermediate Similarity	NPD4360	Phase 2
0.7397	Intermediate Similarity	NPD2797	Approved
0.7386	Intermediate Similarity	NPD6099	Approved
0.7386	Intermediate Similarity	NPD6100	Approved
0.7383	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2309	Approved
0.736	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4361	Phase 2
0.7342	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD9545	Approved
0.7318	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1296	Phase 2
0.7251	Intermediate Similarity	NPD1729	Discontinued
0.725	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4908	Phase 1
0.7239	Intermediate Similarity	NPD37	Approved
0.7237	Intermediate Similarity	NPD447	Suspended
0.7237	Intermediate Similarity	NPD6355	Discontinued
0.7237	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2798	Approved
0.723	Intermediate Similarity	NPD1019	Discontinued
0.7229	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6234	Discontinued
0.7219	Intermediate Similarity	NPD2403	Approved
0.7212	Intermediate Similarity	NPD4966	Approved
0.7212	Intermediate Similarity	NPD4965	Approved
0.7212	Intermediate Similarity	NPD4967	Phase 2
0.7208	Intermediate Similarity	NPD4308	Phase 3
0.7208	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD1465	Phase 2
0.7192	Intermediate Similarity	NPD1608	Approved
0.7183	Intermediate Similarity	NPD9493	Approved
0.717	Intermediate Similarity	NPD7390	Discontinued
0.7162	Intermediate Similarity	NPD3267	Approved
0.7162	Intermediate Similarity	NPD3266	Approved
0.716	Intermediate Similarity	NPD7458	Discontinued
0.716	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3926	Phase 2
0.7159	Intermediate Similarity	NPD8434	Phase 2
0.7152	Intermediate Similarity	NPD411	Approved
0.7143	Intermediate Similarity	NPD7199	Phase 2
0.7134	Intermediate Similarity	NPD1652	Phase 2
0.7123	Intermediate Similarity	NPD1610	Phase 2
0.7123	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3225	Approved
0.7095	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD8312	Approved
0.7086	Intermediate Similarity	NPD8313	Approved
0.7083	Intermediate Similarity	NPD1548	Phase 1
0.7079	Intermediate Similarity	NPD4287	Approved
0.7073	Intermediate Similarity	NPD5889	Approved
0.7073	Intermediate Similarity	NPD5890	Approved
0.707	Intermediate Similarity	NPD2424	Discontinued
0.7063	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD943	Approved
0.7059	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4288	Approved
0.7039	Intermediate Similarity	NPD6798	Discontinued
0.7039	Intermediate Similarity	NPD3764	Approved
0.7	Intermediate Similarity	NPD6808	Phase 2
0.7	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5761	Phase 2
0.6988	Remote Similarity	NPD5760	Phase 2
0.6986	Remote Similarity	NPD17	Approved
0.6981	Remote Similarity	NPD7003	Approved
0.6975	Remote Similarity	NPD6273	Approved
0.6968	Remote Similarity	NPD7584	Approved
0.6948	Remote Similarity	NPD4307	Phase 2
0.6948	Remote Similarity	NPD4060	Phase 1
0.6946	Remote Similarity	NPD5353	Approved
0.6943	Remote Similarity	NPD5404	Approved
0.6943	Remote Similarity	NPD5405	Approved
0.6943	Remote Similarity	NPD5406	Approved
0.6943	Remote Similarity	NPD4476	Approved
0.6943	Remote Similarity	NPD5408	Approved
0.6943	Remote Similarity	NPD4477	Approved
0.6936	Remote Similarity	NPD7228	Approved
0.6933	Remote Similarity	NPD1164	Approved
0.6928	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4749	Approved
0.691	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6585	Discontinued
0.6908	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1933	Approved
0.689	Remote Similarity	NPD1653	Approved
0.6889	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5647	Approved
0.6886	Remote Similarity	NPD8455	Phase 2
0.6883	Remote Similarity	NPD6233	Phase 2
0.6875	Remote Similarity	NPD6104	Discontinued
0.6871	Remote Similarity	NPD1778	Approved
0.6871	Remote Similarity	NPD5049	Phase 3
0.6853	Remote Similarity	NPD1241	Discontinued
0.6853	Remote Similarity	NPD8366	Approved
0.6849	Remote Similarity	NPD1894	Discontinued

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