NPASS Compound

Structure

NPC185624 OpenBabel07101718192D 32 33 0 0 1 0 0 0 0 0999 V2000 8.4055 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8406 -2.4265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3622 -4.8529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0433 -4.8529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8839 1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 -2.4265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5650 1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8406 -1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2028 -3.3971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0433 -2.9118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5217 0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2028 -4.3676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7244 0.9706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8406 -1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0433 -1.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2028 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8839 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7244 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2028 -1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8839 -1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0433 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5650 -0.4853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5217 -1.4559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3622 -1.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7244 -1.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0433 0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 1.4559 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 12 1 0 0 0 0 4 12 1 0 0 0 0 6 14 1 0 0 0 0 7 13 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 12 2 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 13 5 1 1 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 15 22 2 0 0 0 0 15 23 1 0 0 0 0 16 22 1 0 0 0 0 16 24 2 0 0 0 0 17 21 2 0 0 0 0 17 25 1 0 0 0 0 18 32 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 30 1 0 0 0 0 25 31 2 0 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.21
Volume:	464.283
LogP:	5.36
LogD:	2.454
LogS:	-4.152
# Rotatable Bonds:	8
TPSA:	128.2
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.344
Synthetic Accessibility Score:	3.751
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:	-4.933
MDCK Permeability:	1.4409833966055885e-05
Pgp-inhibitor:	0.789
Pgp-substrate:	0.965
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.836
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	99.72587585449219%
Volume Distribution (VD):	0.419
Pgp-substrate:	1.3923205137252808%

ADMET: Metabolism

CYP1A2-inhibitor:	0.237
CYP1A2-substrate:	0.905
CYP2C19-inhibitor:	0.329
CYP2C19-substrate:	0.125
CYP2C9-inhibitor:	0.841
CYP2C9-substrate:	0.856
CYP2D6-inhibitor:	0.219
CYP2D6-substrate:	0.199
CYP3A4-inhibitor:	0.192
CYP3A4-substrate:	0.225

ADMET: Excretion

Clearance (CL):	5.122
Half-life (T1/2):	0.197

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.948
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.093
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.931
Carcinogencity:	0.054
Eye Corrosion:	0.003
Eye Irritation:	0.2
Respiratory Toxicity:	0.147

Download Data

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

Natural Product: NPC185624

Natural Product ID:	NPC185624
*Common Name:**	DLHQNTDXVXYMRV-ZDUSSCGKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DLHQNTDXVXYMRV-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C25H32O7/c1-7-13(5)20(26)19-23(29)15(10-9-12(3)4)22(28)16(24(19)30)11-17-21(27)14(6)18(8-2)32-25(17)31/h9,13,27-30H,7-8,10-11H2,1-6H3/t13-/m0/s1
SMILES:	CC[C@@H](C(=O)c1c(O)c(Cc2c(=O)oc(c(c2O)C)CC)c(c(c1O)CC=C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3359528
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128000.0	nM	PMID[528190]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8000.0	nM	PMID[528190]
NPT1204	Organism	Enterococcus faecalis ATCC 29212	Enterococcus faecalis ATCC 29212	MIC	=	64000.0	nM	PMID[528190]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	128000.0	nM	PMID[528190]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	128000.0	nM	PMID[528190]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	>	128000.0	nM	PMID[528190]

☑ 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 NPC185624 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	341
0.1-0.2	1548
0.2-0.3	4179
0.3-0.4	9717
0.4-0.5	9417
0.5-0.6	4514
0.6-0.7	6048
0.7-0.8	4760
0.8-0.85	1366
0.85-0.9	710
0.9-0.95	76
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9843	High Similarity	NPC470984
0.984	High Similarity	NPC470987
0.984	High Similarity	NPC21378
0.9764	High Similarity	NPC470988
0.9615	High Similarity	NPC470989
0.9615	High Similarity	NPC470985
0.947	High Similarity	NPC219584
0.947	High Similarity	NPC470083
0.9398	High Similarity	NPC241975
0.9398	High Similarity	NPC470986
0.9398	High Similarity	NPC19476
0.9394	High Similarity	NPC138047
0.9394	High Similarity	NPC131782
0.9394	High Similarity	NPC474624
0.9323	High Similarity	NPC199458
0.9323	High Similarity	NPC183639
0.9124	High Similarity	NPC307895
0.9124	High Similarity	NPC470553
0.9118	High Similarity	NPC470555
0.9111	High Similarity	NPC472343
0.907	High Similarity	NPC470981
0.9058	High Similarity	NPC178627
0.9058	High Similarity	NPC288910
0.9058	High Similarity	NPC470554
0.9058	High Similarity	NPC118059
0.9058	High Similarity	NPC469935
0.9058	High Similarity	NPC133060
0.9051	High Similarity	NPC470556
0.9051	High Similarity	NPC112829
0.9044	High Similarity	NPC221173
0.8993	High Similarity	NPC470910
0.8993	High Similarity	NPC181388
0.8986	High Similarity	NPC96216
0.8986	High Similarity	NPC188632
0.8986	High Similarity	NPC87609
0.8986	High Similarity	NPC94794
0.8986	High Similarity	NPC474939
0.8986	High Similarity	NPC184738
0.8986	High Similarity	NPC470909
0.8986	High Similarity	NPC196459
0.8986	High Similarity	NPC112791
0.8986	High Similarity	NPC33653
0.8986	High Similarity	NPC470296
0.8955	High Similarity	NPC101752
0.8947	High Similarity	NPC16197
0.8921	High Similarity	NPC1886
0.8921	High Similarity	NPC196137
0.8913	High Similarity	NPC472344
0.8913	High Similarity	NPC36181
0.8913	High Similarity	NPC294432
0.8897	High Similarity	NPC470669
0.8897	High Similarity	NPC470668
0.8889	High Similarity	NPC470983
0.8889	High Similarity	NPC174999
0.8889	High Similarity	NPC470982
0.8872	High Similarity	NPC215875
0.8872	High Similarity	NPC15834
0.8872	High Similarity	NPC285054
0.8865	High Similarity	NPC469933
0.8857	High Similarity	NPC154217
0.8857	High Similarity	NPC470322
0.8828	High Similarity	NPC472029
0.8828	High Similarity	NPC65761
0.8824	High Similarity	NPC255801
0.8824	High Similarity	NPC322301
0.8815	High Similarity	NPC50455
0.8806	High Similarity	NPC108113
0.8806	High Similarity	NPC93756
0.8803	High Similarity	NPC469932
0.8794	High Similarity	NPC249942
0.8794	High Similarity	NPC297886
0.8786	High Similarity	NPC469953
0.8769	High Similarity	NPC328983
0.8768	High Similarity	NPC471587
0.8768	High Similarity	NPC307990
0.8768	High Similarity	NPC16455
0.8768	High Similarity	NPC477272
0.8759	High Similarity	NPC474504
0.8759	High Similarity	NPC474487
0.8759	High Similarity	NPC131130
0.8759	High Similarity	NPC470672
0.8759	High Similarity	NPC19622
0.8759	High Similarity	NPC470671
0.8759	High Similarity	NPC112789
0.875	High Similarity	NPC91105
0.875	High Similarity	NPC194579
0.875	High Similarity	NPC156910
0.8741	High Similarity	NPC103842
0.8741	High Similarity	NPC125920
0.8732	High Similarity	NPC161864
0.8732	High Similarity	NPC208303
0.8731	High Similarity	NPC10971
0.8723	High Similarity	NPC57470
0.8722	High Similarity	NPC324482
0.8722	High Similarity	NPC279566
0.8722	High Similarity	NPC250057
0.8705	High Similarity	NPC316560
0.8705	High Similarity	NPC316911
0.8705	High Similarity	NPC282300
0.8702	High Similarity	NPC329205
0.8702	High Similarity	NPC116513
0.8702	High Similarity	NPC316625
0.8696	High Similarity	NPC23257
0.8696	High Similarity	NPC96565
0.8696	High Similarity	NPC303633
0.8696	High Similarity	NPC217186
0.8696	High Similarity	NPC220062
0.8696	High Similarity	NPC275903
0.8696	High Similarity	NPC139554
0.8696	High Similarity	NPC301217
0.8696	High Similarity	NPC216978
0.8696	High Similarity	NPC240305
0.8696	High Similarity	NPC53181
0.8696	High Similarity	NPC55018
0.8692	High Similarity	NPC475733
0.8686	High Similarity	NPC332594
0.8686	High Similarity	NPC153979
0.8676	High Similarity	NPC156092
0.8676	High Similarity	NPC13575
0.8676	High Similarity	NPC60667
0.8672	High Similarity	NPC215392
0.8671	High Similarity	NPC19238
0.8671	High Similarity	NPC164205
0.8671	High Similarity	NPC104236
0.8667	High Similarity	NPC175943
0.8662	High Similarity	NPC285748
0.8662	High Similarity	NPC177995
0.8662	High Similarity	NPC474108
0.8662	High Similarity	NPC140120
0.8662	High Similarity	NPC180477
0.8657	High Similarity	NPC27490
0.8652	High Similarity	NPC206212
0.8652	High Similarity	NPC71184
0.8647	High Similarity	NPC84772
0.8647	High Similarity	NPC186628
0.8643	High Similarity	NPC326193
0.8643	High Similarity	NPC323884
0.8643	High Similarity	NPC321148
0.8643	High Similarity	NPC204469
0.8643	High Similarity	NPC321629
0.8636	High Similarity	NPC473017
0.8633	High Similarity	NPC270883
0.8633	High Similarity	NPC241100
0.8633	High Similarity	NPC159275
0.8633	High Similarity	NPC472603
0.8633	High Similarity	NPC172986
0.8633	High Similarity	NPC261227
0.8626	High Similarity	NPC267846
0.8623	High Similarity	NPC54820
0.8623	High Similarity	NPC268178
0.8623	High Similarity	NPC477056
0.8623	High Similarity	NPC180501
0.8623	High Similarity	NPC272844
0.8623	High Similarity	NPC201395
0.8623	High Similarity	NPC254168
0.8623	High Similarity	NPC248995
0.8623	High Similarity	NPC477055
0.8613	High Similarity	NPC268081
0.8613	High Similarity	NPC168105
0.8613	High Similarity	NPC150399
0.8613	High Similarity	NPC186838
0.8613	High Similarity	NPC41461
0.8613	High Similarity	NPC477243
0.8613	High Similarity	NPC25287
0.8613	High Similarity	NPC477244
0.8613	High Similarity	NPC98115
0.8613	High Similarity	NPC249606
0.8613	High Similarity	NPC274109
0.8613	High Similarity	NPC477242
0.8613	High Similarity	NPC12165
0.8613	High Similarity	NPC66349
0.8613	High Similarity	NPC1486
0.8611	High Similarity	NPC474735
0.8611	High Similarity	NPC158866
0.8611	High Similarity	NPC321387
0.8611	High Similarity	NPC470908
0.8611	High Similarity	NPC327059
0.8603	High Similarity	NPC236974
0.8603	High Similarity	NPC144027
0.8594	High Similarity	NPC229649
0.8594	High Similarity	NPC149246
0.8593	High Similarity	NPC25937
0.8593	High Similarity	NPC103105
0.8592	High Similarity	NPC25844
0.8582	High Similarity	NPC5515
0.8582	High Similarity	NPC270369
0.8571	High Similarity	NPC147688
0.8571	High Similarity	NPC156590
0.8571	High Similarity	NPC118840
0.8571	High Similarity	NPC205006
0.8571	High Similarity	NPC212379
0.8571	High Similarity	NPC476508
0.8571	High Similarity	NPC230818
0.8571	High Similarity	NPC69235
0.8571	High Similarity	NPC64908
0.8571	High Similarity	NPC110969
0.8561	High Similarity	NPC472600
0.8561	High Similarity	NPC72158
0.8561	High Similarity	NPC78913
0.8561	High Similarity	NPC472601

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 NPC185624 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	991
0.2-0.3	1812
0.3-0.4	2711
0.4-0.5	1865
0.5-0.6	1015
0.6-0.7	304
0.7-0.8	96
0.8-0.85	37
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD6651	Approved
0.8489	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD2534	Approved
0.8392	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD2532	Approved
0.8392	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD2533	Approved
0.8298	Intermediate Similarity	NPD2800	Approved
0.8248	Intermediate Similarity	NPD1240	Approved
0.8176	Intermediate Similarity	NPD7411	Suspended
0.8146	Intermediate Similarity	NPD7075	Discontinued
0.8143	Intermediate Similarity	NPD1510	Phase 2
0.8129	Intermediate Similarity	NPD1607	Approved
0.8067	Intermediate Similarity	NPD7819	Suspended
0.8067	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD1243	Approved
0.8028	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6801	Discontinued
0.7987	Intermediate Similarity	NPD4380	Phase 2
0.7972	Intermediate Similarity	NPD1549	Phase 2
0.7945	Intermediate Similarity	NPD6799	Approved
0.7862	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD3750	Approved
0.7843	Intermediate Similarity	NPD7768	Phase 2
0.7842	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD2935	Discontinued
0.7832	Intermediate Similarity	NPD2796	Approved
0.7829	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7473	Discontinued
0.7762	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD2799	Discontinued
0.7748	Intermediate Similarity	NPD6599	Discontinued
0.7722	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD5711	Approved
0.7707	Intermediate Similarity	NPD5710	Approved
0.7703	Intermediate Similarity	NPD1511	Approved
0.7676	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD5124	Phase 1
0.7669	Intermediate Similarity	NPD9545	Approved
0.7667	Intermediate Similarity	NPD920	Approved
0.7652	Intermediate Similarity	NPD9493	Approved
0.7635	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD943	Approved
0.76	Intermediate Similarity	NPD1512	Approved
0.7597	Intermediate Similarity	NPD2801	Approved
0.7595	Intermediate Similarity	NPD6232	Discontinued
0.7589	Intermediate Similarity	NPD2313	Discontinued
0.7586	Intermediate Similarity	NPD1551	Phase 2
0.7584	Intermediate Similarity	NPD7390	Discontinued
0.7578	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7286	Phase 2
0.7574	Intermediate Similarity	NPD422	Phase 1
0.7564	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD3749	Approved
0.7552	Intermediate Similarity	NPD230	Phase 1
0.7548	Intermediate Similarity	NPD3817	Phase 2
0.7533	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1934	Approved
0.7518	Intermediate Similarity	NPD9717	Approved
0.7517	Intermediate Similarity	NPD3748	Approved
0.7485	Intermediate Similarity	NPD5953	Discontinued
0.7482	Intermediate Similarity	NPD1164	Approved
0.7482	Intermediate Similarity	NPD1203	Approved
0.7481	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD5405	Approved
0.7466	Intermediate Similarity	NPD5406	Approved
0.7466	Intermediate Similarity	NPD5404	Approved
0.7466	Intermediate Similarity	NPD5408	Approved
0.7465	Intermediate Similarity	NPD3268	Approved
0.7434	Intermediate Similarity	NPD5403	Approved
0.7421	Intermediate Similarity	NPD6959	Discontinued
0.7389	Intermediate Similarity	NPD3882	Suspended
0.7357	Intermediate Similarity	NPD2797	Approved
0.7347	Intermediate Similarity	NPD6099	Approved
0.7347	Intermediate Similarity	NPD6100	Approved
0.7324	Intermediate Similarity	NPD6832	Phase 2
0.7315	Intermediate Similarity	NPD2654	Approved
0.7308	Intermediate Similarity	NPD9266	Approved
0.7308	Intermediate Similarity	NPD74	Approved
0.7305	Intermediate Similarity	NPD2798	Approved
0.7303	Intermediate Similarity	NPD5401	Approved
0.7296	Intermediate Similarity	NPD919	Approved
0.7289	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7054	Approved
0.7231	Intermediate Similarity	NPD9263	Approved
0.7231	Intermediate Similarity	NPD9267	Approved
0.7231	Intermediate Similarity	NPD9264	Approved
0.7231	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3226	Approved
0.7222	Intermediate Similarity	NPD3764	Approved
0.7222	Intermediate Similarity	NPD1296	Phase 2
0.7212	Intermediate Similarity	NPD7472	Approved
0.7212	Intermediate Similarity	NPD7074	Phase 3
0.7195	Intermediate Similarity	NPD3818	Discontinued
0.7181	Intermediate Similarity	NPD2346	Discontinued
0.7181	Intermediate Similarity	NPD2344	Approved
0.7178	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6166	Phase 2
0.7178	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7033	Discontinued
0.7162	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4628	Phase 3
0.7143	Intermediate Similarity	NPD5494	Approved
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7134	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7251	Discontinued
0.7126	Intermediate Similarity	NPD6559	Discontinued
0.7115	Intermediate Similarity	NPD7458	Discontinued
0.7113	Intermediate Similarity	NPD3267	Approved
0.7113	Intermediate Similarity	NPD3266	Approved
0.7107	Intermediate Similarity	NPD5402	Approved
0.7101	Intermediate Similarity	NPD9268	Approved
0.7086	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7808	Phase 3
0.7083	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1201	Approved
0.7066	Intermediate Similarity	NPD6797	Phase 2
0.7048	Intermediate Similarity	NPD5844	Phase 1
0.7047	Intermediate Similarity	NPD4308	Phase 3
0.7042	Intermediate Similarity	NPD3225	Approved
0.7021	Intermediate Similarity	NPD1608	Approved
0.6993	Remote Similarity	NPD2309	Approved
0.6993	Remote Similarity	NPD1470	Approved
0.6987	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD411	Approved
0.6986	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD9281	Approved
0.6977	Remote Similarity	NPD846	Approved
0.6977	Remote Similarity	NPD940	Approved
0.6959	Remote Similarity	NPD447	Suspended
0.6944	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1465	Phase 2
0.6928	Remote Similarity	NPD7003	Approved
0.6923	Remote Similarity	NPD9261	Approved
0.6917	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4288	Approved
0.689	Remote Similarity	NPD1247	Approved
0.6875	Remote Similarity	NPD4363	Phase 3
0.6875	Remote Similarity	NPD4360	Phase 2
0.6864	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6585	Discontinued
0.6849	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4908	Phase 1
0.6848	Remote Similarity	NPD7229	Phase 3
0.6842	Remote Similarity	NPD6002	Phase 3
0.6842	Remote Similarity	NPD6004	Phase 3
0.6842	Remote Similarity	NPD6005	Phase 3
0.6842	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD4361	Phase 2
0.6828	Remote Similarity	NPD1019	Discontinued
0.6824	Remote Similarity	NPD520	Approved
0.6821	Remote Similarity	NPD8150	Discontinued
0.6815	Remote Similarity	NPD5049	Phase 3
0.6813	Remote Similarity	NPD5890	Approved
0.6813	Remote Similarity	NPD5889	Approved
0.6809	Remote Similarity	NPD17	Approved
0.6805	Remote Similarity	NPD1729	Discontinued
0.6795	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.679	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1548	Phase 1
0.6783	Remote Similarity	NPD3972	Approved
0.6779	Remote Similarity	NPD4307	Phase 2
0.6763	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD4287	Approved
0.6742	Remote Similarity	NPD5909	Discontinued
0.6741	Remote Similarity	NPD4750	Phase 3
0.6736	Remote Similarity	NPD4749	Approved
0.6733	Remote Similarity	NPD6355	Discontinued
0.6733	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD1933	Approved
0.6725	Remote Similarity	NPD6104	Discontinued
0.6713	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1610	Phase 2
0.671	Remote Similarity	NPD8166	Discontinued
0.6707	Remote Similarity	NPD3926	Phase 2
0.669	Remote Similarity	NPD4626	Approved
0.669	Remote Similarity	NPD1283	Approved
0.6687	Remote Similarity	NPD5353	Approved
0.6687	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2403	Approved
0.6667	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6234	Discontinued
0.6667	Remote Similarity	NPD37	Approved
0.6667	Remote Similarity	NPD1481	Phase 2
0.6667	Remote Similarity	NPD6190	Approved
0.6667	Remote Similarity	NPD2354	Approved
0.6648	Remote Similarity	NPD8397	Clinical (unspecified phase)

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