NPASS Compound

Structure

NPC472000 OpenBabel07101719512D 28 31 0 0 1 0 0 0 0 0999 V2000 2.6654 4.0850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8123 -1.4070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3828 3.2327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9076 2.9666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3155 2.4225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5513 0.1791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0016 3.2093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8123 -0.4690 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6971 1.5656 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9567 2.0298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6246 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6246 0.9380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8123 1.4070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7483 -0.1474 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4907 2.4227 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3301 0.3458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6173 2.3245 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9380 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2117 -1.5347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7434 1.5190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4370 -0.4690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4370 1.4070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9843 -1.0552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1870 -0.0357 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1831 -0.9200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3073 1.1081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0810 1.6937 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 4 7 2 0 0 0 0 4 10 1 0 0 0 0 5 9 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 6 20 1 0 0 0 0 8 11 1 0 0 0 0 8 19 1 1 0 0 0 9 18 1 6 0 0 0 9 27 1 0 0 0 0 10 21 2 0 0 0 0 10 28 1 0 0 0 0 11 12 1 0 0 0 0 11 22 2 0 0 0 0 12 13 2 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 1 0 0 0 14 24 1 0 0 0 0 15 7 1 1 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 25 2 0 0 0 0 16 27 1 0 0 0 0 17 3 1 1 0 0 0 18 19 1 6 0 0 0 19 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.13
Volume:	368.884
LogP:	0.877
LogD:	-0.026
LogS:	-3.084
# Rotatable Bonds:	2
TPSA:	154.5
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.378
Synthetic Accessibility Score:	5.472
Fsp3:	0.632
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.83
MDCK Permeability:	5.8290759625378996e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.94
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.563
30% Bioavailability (F30%):	0.664

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.106
Plasma Protein Binding (PPB):	73.82415008544922%
Volume Distribution (VD):	0.542
Pgp-substrate:	29.77225112915039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.798
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.117
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.145
CYP3A4-inhibitor:	0.072
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	3.071
Half-life (T1/2):	0.445

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.755
AMES Toxicity:	0.171
Rat Oral Acute Toxicity:	0.232
Maximum Recommended Daily Dose:	0.489
Skin Sensitization:	0.286
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.841

Download Data

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

Natural Product: NPC472000

Natural Product ID:	NPC472000
*Common Name:**	KFTXUZYEPRMYJV-HTPTWFILSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KFTXUZYEPRMYJV-HTPTWFILSA-N
Standard InCHI:	InChI=1S/C19H22O9/c1-7-4-10(21)28-15(7)17(3)5-9-18(6-20)13(17)12(23)11(22)8(2)19(18,26)14(24)16(25)27-9/h4,8-9,14-15,20,23-24,26H,5-6H2,1-3H3/t8-,9-,14+,15-,17+,18-,19+/m1/s1
SMILES:	OC[C@@]12[C@@H]3OC(=O)[C@@H]([C@@]2(O)[C@@H](C(=O)C(=C1[C@@](C3)(C)[C@@H]1OC(=O)C=C1C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3317739
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	Roots	n.a.	n.a.	PMID[14575431]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	root	n.a.	PMID[1800638]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919052]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24467387]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[25066952]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25905468]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	Activity	=	104.4	%	PMID[508857]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	101.1	%	PMID[508857]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	103.9	%	PMID[508857]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	102.5	%	PMID[508857]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	104.0	%	PMID[508857]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	105.6	%	PMID[508857]

☑ 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 NPC472000 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	225
0.1-0.2	1274
0.2-0.3	4228
0.3-0.4	7599
0.4-0.5	13116
0.5-0.6	8100
0.6-0.7	5864
0.7-0.8	2179
0.8-0.85	105
0.85-0.9	3
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471999
0.9646	High Similarity	NPC472001
0.9099	High Similarity	NPC206595
0.8889	High Similarity	NPC472004
0.8621	High Similarity	NPC178289
0.8468	Intermediate Similarity	NPC231529
0.8443	Intermediate Similarity	NPC24651
0.843	Intermediate Similarity	NPC312833
0.8387	Intermediate Similarity	NPC311534
0.8361	Intermediate Similarity	NPC105926
0.8361	Intermediate Similarity	NPC91693
0.8361	Intermediate Similarity	NPC18945
0.8361	Intermediate Similarity	NPC265557
0.8347	Intermediate Similarity	NPC470921
0.8333	Intermediate Similarity	NPC19028
0.8333	Intermediate Similarity	NPC9674
0.8319	Intermediate Similarity	NPC239273
0.8306	Intermediate Similarity	NPC470882
0.8306	Intermediate Similarity	NPC476008
0.8306	Intermediate Similarity	NPC473265
0.8293	Intermediate Similarity	NPC476729
0.8279	Intermediate Similarity	NPC222688
0.8279	Intermediate Similarity	NPC269642
0.8276	Intermediate Similarity	NPC99760
0.8264	Intermediate Similarity	NPC109973
0.8254	Intermediate Similarity	NPC241935
0.8254	Intermediate Similarity	NPC279478
0.825	Intermediate Similarity	NPC251310
0.825	Intermediate Similarity	NPC470420
0.8235	Intermediate Similarity	NPC54739
0.8226	Intermediate Similarity	NPC477745
0.822	Intermediate Similarity	NPC194100
0.8211	Intermediate Similarity	NPC67251
0.8203	Intermediate Similarity	NPC471234
0.8197	Intermediate Similarity	NPC46570
0.8197	Intermediate Similarity	NPC310511
0.819	Intermediate Similarity	NPC101018
0.8189	Intermediate Similarity	NPC34963
0.8175	Intermediate Similarity	NPC476851
0.8175	Intermediate Similarity	NPC472770
0.8175	Intermediate Similarity	NPC35109
0.8175	Intermediate Similarity	NPC470880
0.8167	Intermediate Similarity	NPC470854
0.8167	Intermediate Similarity	NPC97908
0.8167	Intermediate Similarity	NPC287343
0.8167	Intermediate Similarity	NPC122033
0.8167	Intermediate Similarity	NPC474654
0.816	Intermediate Similarity	NPC287423
0.816	Intermediate Similarity	NPC473253
0.8145	Intermediate Similarity	NPC473255
0.8136	Intermediate Similarity	NPC126691
0.8136	Intermediate Similarity	NPC317687
0.813	Intermediate Similarity	NPC107493
0.8125	Intermediate Similarity	NPC58029
0.8125	Intermediate Similarity	NPC469673
0.812	Intermediate Similarity	NPC50223
0.812	Intermediate Similarity	NPC5103
0.811	Intermediate Similarity	NPC220757
0.811	Intermediate Similarity	NPC476852
0.811	Intermediate Similarity	NPC213634
0.811	Intermediate Similarity	NPC196921
0.8099	Intermediate Similarity	NPC17772
0.8095	Intermediate Similarity	NPC476859
0.8083	Intermediate Similarity	NPC138372
0.8083	Intermediate Similarity	NPC148458
0.8083	Intermediate Similarity	NPC106228
0.8067	Intermediate Similarity	NPC7921
0.8067	Intermediate Similarity	NPC9848
0.8067	Intermediate Similarity	NPC208998
0.8067	Intermediate Similarity	NPC312017
0.8065	Intermediate Similarity	NPC471392
0.8065	Intermediate Similarity	NPC473979
0.8065	Intermediate Similarity	NPC472399
0.8062	Intermediate Similarity	NPC476823
0.8051	Intermediate Similarity	NPC317107
0.8049	Intermediate Similarity	NPC470779
0.8047	Intermediate Similarity	NPC472769
0.8047	Intermediate Similarity	NPC471855
0.8034	Intermediate Similarity	NPC470257
0.8034	Intermediate Similarity	NPC77089
0.8033	Intermediate Similarity	NPC5292
0.8033	Intermediate Similarity	NPC472933
0.8033	Intermediate Similarity	NPC470777
0.8033	Intermediate Similarity	NPC475041
0.8031	Intermediate Similarity	NPC476854
0.8031	Intermediate Similarity	NPC175186
0.8031	Intermediate Similarity	NPC104382
0.8031	Intermediate Similarity	NPC221414
0.8017	Intermediate Similarity	NPC176513
0.8017	Intermediate Similarity	NPC472934
0.8017	Intermediate Similarity	NPC470775
0.8016	Intermediate Similarity	NPC146456
0.8016	Intermediate Similarity	NPC469757
0.8016	Intermediate Similarity	NPC117702
0.8016	Intermediate Similarity	NPC471357
0.8	Intermediate Similarity	NPC470104
0.8	Intermediate Similarity	NPC470922
0.8	Intermediate Similarity	NPC473898
0.8	Intermediate Similarity	NPC258532
0.8	Intermediate Similarity	NPC472756
0.8	Intermediate Similarity	NPC299849
0.7984	Intermediate Similarity	NPC470419
0.7984	Intermediate Similarity	NPC88668
0.7984	Intermediate Similarity	NPC168879
0.7984	Intermediate Similarity	NPC469674
0.7983	Intermediate Similarity	NPC221144
0.7983	Intermediate Similarity	NPC100267
0.7983	Intermediate Similarity	NPC66108
0.7983	Intermediate Similarity	NPC475524
0.7969	Intermediate Similarity	NPC473838
0.7969	Intermediate Similarity	NPC476863
0.7969	Intermediate Similarity	NPC173347
0.7969	Intermediate Similarity	NPC476862
0.7969	Intermediate Similarity	NPC475389
0.7969	Intermediate Similarity	NPC476855
0.7969	Intermediate Similarity	NPC471170
0.7967	Intermediate Similarity	NPC112038
0.7967	Intermediate Similarity	NPC79579
0.7967	Intermediate Similarity	NPC474585
0.7966	Intermediate Similarity	NPC41551
0.7953	Intermediate Similarity	NPC236999
0.7951	Intermediate Similarity	NPC204552
0.7951	Intermediate Similarity	NPC153440
0.7951	Intermediate Similarity	NPC311554
0.7951	Intermediate Similarity	NPC475401
0.7951	Intermediate Similarity	NPC188667
0.7951	Intermediate Similarity	NPC470776
0.7951	Intermediate Similarity	NPC257457
0.7949	Intermediate Similarity	NPC151393
0.7946	Intermediate Similarity	NPC69385
0.7937	Intermediate Similarity	NPC222307
0.7937	Intermediate Similarity	NPC15095
0.7934	Intermediate Similarity	NPC213084
0.7934	Intermediate Similarity	NPC207217
0.7934	Intermediate Similarity	NPC49492
0.7934	Intermediate Similarity	NPC190286
0.7934	Intermediate Similarity	NPC266728
0.7934	Intermediate Similarity	NPC190185
0.7934	Intermediate Similarity	NPC270478
0.792	Intermediate Similarity	NPC27363
0.792	Intermediate Similarity	NPC472768
0.792	Intermediate Similarity	NPC469789
0.792	Intermediate Similarity	NPC473802
0.792	Intermediate Similarity	NPC129992
0.792	Intermediate Similarity	NPC120724
0.7917	Intermediate Similarity	NPC469454
0.7917	Intermediate Similarity	NPC250109
0.7917	Intermediate Similarity	NPC469463
0.7917	Intermediate Similarity	NPC469496
0.7917	Intermediate Similarity	NPC962
0.7917	Intermediate Similarity	NPC49451
0.7913	Intermediate Similarity	NPC159533
0.7913	Intermediate Similarity	NPC474775
0.7913	Intermediate Similarity	NPC475321
0.7907	Intermediate Similarity	NPC475139
0.7907	Intermediate Similarity	NPC180902
0.7903	Intermediate Similarity	NPC470418
0.7903	Intermediate Similarity	NPC102822
0.7903	Intermediate Similarity	NPC472401
0.7903	Intermediate Similarity	NPC477046
0.7899	Intermediate Similarity	NPC171888
0.7899	Intermediate Similarity	NPC472003
0.7899	Intermediate Similarity	NPC146945
0.7899	Intermediate Similarity	NPC304180
0.7899	Intermediate Similarity	NPC179798
0.7895	Intermediate Similarity	NPC475099
0.7891	Intermediate Similarity	NPC471407
0.7891	Intermediate Similarity	NPC471360
0.7891	Intermediate Similarity	NPC180079
0.7891	Intermediate Similarity	NPC471359
0.7891	Intermediate Similarity	NPC219085
0.7891	Intermediate Similarity	NPC70542
0.7891	Intermediate Similarity	NPC17896
0.7891	Intermediate Similarity	NPC197707
0.7891	Intermediate Similarity	NPC10823
0.7891	Intermediate Similarity	NPC469754
0.7891	Intermediate Similarity	NPC9499
0.7891	Intermediate Similarity	NPC469751
0.7891	Intermediate Similarity	NPC86159
0.7891	Intermediate Similarity	NPC471358
0.7891	Intermediate Similarity	NPC89514
0.7891	Intermediate Similarity	NPC6108
0.7891	Intermediate Similarity	NPC469755
0.7891	Intermediate Similarity	NPC471361
0.7891	Intermediate Similarity	NPC284406
0.7891	Intermediate Similarity	NPC13071
0.7891	Intermediate Similarity	NPC251866
0.7891	Intermediate Similarity	NPC471352
0.7891	Intermediate Similarity	NPC469753
0.7891	Intermediate Similarity	NPC469752
0.7886	Intermediate Similarity	NPC305260
0.7886	Intermediate Similarity	NPC475775
0.7886	Intermediate Similarity	NPC268958
0.7886	Intermediate Similarity	NPC477092
0.7886	Intermediate Similarity	NPC319570
0.7886	Intermediate Similarity	NPC476529
0.7886	Intermediate Similarity	NPC270850
0.7881	Intermediate Similarity	NPC304495
0.7881	Intermediate Similarity	NPC471400
0.7881	Intermediate Similarity	NPC470615

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 NPC472000 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1629
0.2-0.3	3712
0.3-0.4	2322
0.4-0.5	779
0.5-0.6	257
0.6-0.7	197
0.7-0.8	62
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7967	Intermediate Similarity	NPD6319	Approved
0.7891	Intermediate Similarity	NPD7319	Approved
0.7795	Intermediate Similarity	NPD7507	Approved
0.7686	Intermediate Similarity	NPD6053	Discontinued
0.7623	Intermediate Similarity	NPD4632	Approved
0.7583	Intermediate Similarity	NPD6373	Approved
0.7583	Intermediate Similarity	NPD6372	Approved
0.7578	Intermediate Similarity	NPD7492	Approved
0.7563	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD8297	Approved
0.754	Intermediate Similarity	NPD6059	Approved
0.754	Intermediate Similarity	NPD6054	Approved
0.7521	Intermediate Similarity	NPD6371	Approved
0.7519	Intermediate Similarity	NPD6616	Approved
0.75	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD6015	Approved
0.748	Intermediate Similarity	NPD6016	Approved
0.7479	Intermediate Similarity	NPD5739	Approved
0.7479	Intermediate Similarity	NPD7128	Approved
0.7479	Intermediate Similarity	NPD6402	Approved
0.7479	Intermediate Similarity	NPD6675	Approved
0.7462	Intermediate Similarity	NPD7078	Approved
0.7462	Intermediate Similarity	NPD8293	Discontinued
0.7459	Intermediate Similarity	NPD6650	Approved
0.7459	Intermediate Similarity	NPD6649	Approved
0.744	Intermediate Similarity	NPD7115	Discovery
0.7422	Intermediate Similarity	NPD5988	Approved
0.7422	Intermediate Similarity	NPD6370	Approved
0.7417	Intermediate Similarity	NPD5701	Approved
0.7417	Intermediate Similarity	NPD5697	Approved
0.7414	Intermediate Similarity	NPD5696	Approved
0.7405	Intermediate Similarity	NPD7736	Approved
0.7381	Intermediate Similarity	NPD7327	Approved
0.7381	Intermediate Similarity	NPD7328	Approved
0.7377	Intermediate Similarity	NPD4634	Approved
0.7368	Intermediate Similarity	NPD7260	Phase 2
0.7355	Intermediate Similarity	NPD6899	Approved
0.7355	Intermediate Similarity	NPD6881	Approved
0.7355	Intermediate Similarity	NPD6686	Approved
0.7333	Intermediate Similarity	NPD6008	Approved
0.7323	Intermediate Similarity	NPD7516	Approved
0.7302	Intermediate Similarity	NPD6009	Approved
0.7295	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD6013	Approved
0.7295	Intermediate Similarity	NPD6014	Approved
0.7295	Intermediate Similarity	NPD6012	Approved
0.7258	Intermediate Similarity	NPD6882	Approved
0.7236	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7102	Approved
0.7236	Intermediate Similarity	NPD6883	Approved
0.7236	Intermediate Similarity	NPD7290	Approved
0.7231	Intermediate Similarity	NPD8328	Phase 3
0.7217	Intermediate Similarity	NPD5282	Discontinued
0.7213	Intermediate Similarity	NPD6011	Approved
0.7209	Intermediate Similarity	NPD8033	Approved
0.7209	Intermediate Similarity	NPD5983	Phase 2
0.7185	Intermediate Similarity	NPD6845	Suspended
0.7179	Intermediate Similarity	NPD4755	Approved
0.7179	Intermediate Similarity	NPD6084	Phase 2
0.7179	Intermediate Similarity	NPD6083	Phase 2
0.7177	Intermediate Similarity	NPD6869	Approved
0.7177	Intermediate Similarity	NPD6847	Approved
0.7177	Intermediate Similarity	NPD8130	Phase 1
0.7177	Intermediate Similarity	NPD6617	Approved
0.7155	Intermediate Similarity	NPD5695	Phase 3
0.7132	Intermediate Similarity	NPD8377	Approved
0.7132	Intermediate Similarity	NPD8294	Approved
0.7131	Intermediate Similarity	NPD6412	Phase 2
0.7119	Intermediate Similarity	NPD4225	Approved
0.7105	Intermediate Similarity	NPD46	Approved
0.7105	Intermediate Similarity	NPD6698	Approved
0.7099	Intermediate Similarity	NPD7604	Phase 2
0.7083	Intermediate Similarity	NPD5211	Phase 2
0.7077	Intermediate Similarity	NPD8379	Approved
0.7077	Intermediate Similarity	NPD8296	Approved
0.7077	Intermediate Similarity	NPD8378	Approved
0.7077	Intermediate Similarity	NPD8380	Approved
0.7077	Intermediate Similarity	NPD8335	Approved
0.7077	Intermediate Similarity	NPD7503	Approved
0.7059	Intermediate Similarity	NPD4700	Approved
0.7059	Intermediate Similarity	NPD5286	Approved
0.7059	Intermediate Similarity	NPD5285	Approved
0.7059	Intermediate Similarity	NPD4696	Approved
0.704	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6033	Approved
0.7009	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5210	Approved
0.7009	Intermediate Similarity	NPD4629	Approved
0.6992	Remote Similarity	NPD6336	Discontinued
0.6992	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7638	Approved
0.6967	Remote Similarity	NPD5141	Approved
0.6953	Remote Similarity	NPD6274	Approved
0.6947	Remote Similarity	NPD8515	Approved
0.6947	Remote Similarity	NPD8517	Approved
0.6947	Remote Similarity	NPD6921	Approved
0.6947	Remote Similarity	NPD8513	Phase 3
0.6947	Remote Similarity	NPD8516	Approved
0.6942	Remote Similarity	NPD5226	Approved
0.6942	Remote Similarity	NPD5225	Approved
0.6942	Remote Similarity	NPD4633	Approved
0.6942	Remote Similarity	NPD5224	Approved
0.6917	Remote Similarity	NPD7640	Approved
0.6917	Remote Similarity	NPD7639	Approved
0.6911	Remote Similarity	NPD4767	Approved
0.6911	Remote Similarity	NPD4768	Approved
0.6899	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5693	Phase 1
0.6885	Remote Similarity	NPD5175	Approved
0.6885	Remote Similarity	NPD5174	Approved
0.687	Remote Similarity	NPD4753	Phase 2
0.686	Remote Similarity	NPD5223	Approved
0.6838	Remote Similarity	NPD5779	Approved
0.6838	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5785	Approved
0.68	Remote Similarity	NPD4729	Approved
0.68	Remote Similarity	NPD4730	Approved
0.6797	Remote Similarity	NPD8133	Approved
0.6794	Remote Similarity	NPD7100	Approved
0.6794	Remote Similarity	NPD7101	Approved
0.6772	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6317	Approved
0.6752	Remote Similarity	NPD6411	Approved
0.6752	Remote Similarity	NPD7983	Approved
0.6748	Remote Similarity	NPD4754	Approved
0.6718	Remote Similarity	NPD6314	Approved
0.6718	Remote Similarity	NPD6335	Approved
0.6718	Remote Similarity	NPD6313	Approved
0.6695	Remote Similarity	NPD6399	Phase 3
0.6693	Remote Similarity	NPD5251	Approved
0.6693	Remote Similarity	NPD5248	Approved
0.6693	Remote Similarity	NPD5249	Phase 3
0.6693	Remote Similarity	NPD5247	Approved
0.6693	Remote Similarity	NPD5250	Approved
0.6692	Remote Similarity	NPD6909	Approved
0.6692	Remote Similarity	NPD6908	Approved
0.6691	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD5956	Approved
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD4697	Phase 3
0.661	Remote Similarity	NPD5284	Approved
0.661	Remote Similarity	NPD5281	Approved
0.6583	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6904	Approved
0.6581	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6673	Approved
0.6581	Remote Similarity	NPD6080	Approved
0.6581	Remote Similarity	NPD6101	Approved
0.6573	Remote Similarity	NPD6334	Approved
0.6573	Remote Similarity	NPD6333	Approved
0.6555	Remote Similarity	NPD4202	Approved
0.6541	Remote Similarity	NPD4522	Approved
0.6529	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5221	Approved
0.6529	Remote Similarity	NPD5222	Approved
0.6525	Remote Similarity	NPD5692	Phase 3
0.6512	Remote Similarity	NPD5215	Approved
0.6512	Remote Similarity	NPD5217	Approved
0.6512	Remote Similarity	NPD5216	Approved
0.6503	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6903	Approved
0.6496	Remote Similarity	NPD6672	Approved
0.6496	Remote Similarity	NPD5737	Approved
0.6484	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD5173	Approved
0.6471	Remote Similarity	NPD6050	Approved
0.6471	Remote Similarity	NPD5694	Approved
0.6466	Remote Similarity	NPD7146	Approved
0.6466	Remote Similarity	NPD7521	Approved
0.6466	Remote Similarity	NPD6684	Approved
0.6466	Remote Similarity	NPD5786	Approved
0.6466	Remote Similarity	NPD5330	Approved
0.6466	Remote Similarity	NPD7334	Approved
0.6466	Remote Similarity	NPD6409	Approved
0.6452	Remote Similarity	NPD1700	Approved
0.6452	Remote Similarity	NPD5344	Discontinued
0.6441	Remote Similarity	NPD5328	Approved
0.6435	Remote Similarity	NPD3665	Phase 1
0.6435	Remote Similarity	NPD4197	Approved
0.6435	Remote Similarity	NPD3133	Approved
0.6435	Remote Similarity	NPD3666	Approved
0.6434	Remote Similarity	NPD5169	Approved
0.6434	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD5135	Approved
0.6423	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD8336	Approved
0.6403	Remote Similarity	NPD8337	Approved
0.64	Remote Similarity	NPD7632	Discontinued
0.6397	Remote Similarity	NPD8080	Discontinued
0.6387	Remote Similarity	NPD7838	Discovery
0.6387	Remote Similarity	NPD5207	Approved
0.6385	Remote Similarity	NPD5127	Approved
0.6379	Remote Similarity	NPD5329	Approved
0.6379	Remote Similarity	NPD5363	Approved
0.6379	Remote Similarity	NPD1694	Approved
0.6364	Remote Similarity	NPD6001	Approved
0.6356	Remote Similarity	NPD7513	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