NPASS Compound

Structure

CID38898 OpenBabel06191715372D 23 24 0 0 0 0 0 0 0 0999 V2000 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -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 -4.3301 -1.5000 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 -6.0622 -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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 8 1 0 0 0 0 4 10 2 0 0 0 0 5 8 1 0 0 0 0 5 11 1 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 14 2 0 0 0 0 9 11 1 0 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.07
Volume:	308.619
LogP:	2.166
LogD:	1.255
LogS:	-2.869
# Rotatable Bonds:	5
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.49
Synthetic Accessibility Score:	2.349
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	3
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.852
MDCK Permeability:	5.4176434787223116e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.181
20% Bioavailability (F20%):	0.91
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	95.50348663330078%
Volume Distribution (VD):	0.417
Pgp-substrate:	5.041820049285889%

ADMET: Metabolism

CYP1A2-inhibitor:	0.145
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.548
CYP2C9-substrate:	0.093
CYP2D6-inhibitor:	0.144
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.071

ADMET: Excretion

Clearance (CL):	6.849
Half-life (T1/2):	0.941

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.327
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.157
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.427
Carcinogencity:	0.075
Eye Corrosion:	0.003
Eye Irritation:	0.34
Respiratory Toxicity:	0.254

Download Data

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

Natural Product: NPC38898

Natural Product ID:	NPC38898
*Common Name:**	2-[2-(3,4-Dihydroxy-5-Methoxyphenyl)-2-Oxoethyl]-6-Hydroxybenzoic Acid
IUPAC Name:	2-[2-(3,4-dihydroxy-5-methoxyphenyl)-2-oxoethyl]-6-hydroxybenzoic acid
Synonyms:
Standard InCHIKey:	RQTLRWYINSEUHU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O7/c1-23-13-7-9(6-12(19)15(13)20)11(18)5-8-3-2-4-10(17)14(8)16(21)22/h2-4,6-7,17,19-20H,5H2,1H3,(H,21,22)
SMILES:	COc1cc(cc(c1O)O)C(=O)Cc1cccc(c1C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813262
PubChem CID:	53359460
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	roots	Daba desert reserve (50 km South of Amman), Jordan	2009-APR	PMID[21650157]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21650157]
NPO16745	Scorzonera judaica	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
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	100000.0	nM	PMID[524846]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	100000.0	nM	PMID[524846]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	100000.0	nM	PMID[524846]

☑ 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 NPC38898 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	378
0.1-0.2	1749
0.2-0.3	4304
0.3-0.4	9869
0.4-0.5	8018
0.5-0.6	3386
0.6-0.7	5145
0.7-0.8	6196
0.8-0.85	2620
0.85-0.9	942
0.9-0.95	89
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9324	High Similarity	NPC138978
0.932	High Similarity	NPC142165
0.9281	High Similarity	NPC227062
0.9267	High Similarity	NPC264289
0.9267	High Similarity	NPC139293
0.9267	High Similarity	NPC333691
0.9267	High Similarity	NPC142876
0.9267	High Similarity	NPC200060
0.9267	High Similarity	NPC40290
0.9267	High Similarity	NPC264550
0.9267	High Similarity	NPC69430
0.9267	High Similarity	NPC195763
0.9252	High Similarity	NPC254659
0.9252	High Similarity	NPC287722
0.9221	High Similarity	NPC178976
0.9211	High Similarity	NPC312338
0.9211	High Similarity	NPC149889
0.9205	High Similarity	NPC472279
0.9205	High Similarity	NPC85131
0.92	High Similarity	NPC254702
0.92	High Similarity	NPC139364
0.92	High Similarity	NPC287395
0.92	High Similarity	NPC203747
0.92	High Similarity	NPC183655
0.92	High Similarity	NPC194653
0.92	High Similarity	NPC80710
0.9189	High Similarity	NPC207732
0.9184	High Similarity	NPC312256
0.9184	High Similarity	NPC284556
0.9184	High Similarity	NPC301178
0.9156	High Similarity	NPC77807
0.9156	High Similarity	NPC54928
0.9156	High Similarity	NPC5379
0.9156	High Similarity	NPC14561
0.9145	High Similarity	NPC78505
0.9139	High Similarity	NPC92722
0.9139	High Similarity	NPC102003
0.9133	High Similarity	NPC188074
0.9133	High Similarity	NPC125449
0.9122	High Similarity	NPC471417
0.9122	High Similarity	NPC119663
0.9116	High Similarity	NPC110419
0.9114	High Similarity	NPC8070
0.9097	High Similarity	NPC472963
0.9097	High Similarity	NPC199463
0.9097	High Similarity	NPC37543
0.9091	High Similarity	NPC16082
0.9091	High Similarity	NPC234485
0.9091	High Similarity	NPC82592
0.9091	High Similarity	NPC20541
0.9091	High Similarity	NPC79998
0.9085	High Similarity	NPC35763
0.9085	High Similarity	NPC216769
0.9085	High Similarity	NPC474993
0.9085	High Similarity	NPC181209
0.9085	High Similarity	NPC131266
0.9085	High Similarity	NPC295646
0.9085	High Similarity	NPC269451
0.9085	High Similarity	NPC100971
0.9085	High Similarity	NPC245382
0.9085	High Similarity	NPC100263
0.9085	High Similarity	NPC291802
0.9085	High Similarity	NPC121522
0.9085	High Similarity	NPC209487
0.9079	High Similarity	NPC29231
0.9079	High Similarity	NPC151473
0.9073	High Similarity	NPC131451
0.9073	High Similarity	NPC474903
0.9073	High Similarity	NPC15329
0.9067	High Similarity	NPC12377
0.9054	High Similarity	NPC49108
0.9054	High Similarity	NPC250755
0.9048	High Similarity	NPC50823
0.9045	High Similarity	NPC311740
0.9038	High Similarity	NPC45846
0.9032	High Similarity	NPC150227
0.9032	High Similarity	NPC472907
0.9026	High Similarity	NPC127172
0.9026	High Similarity	NPC124714
0.9026	High Similarity	NPC281477
0.9026	High Similarity	NPC107109
0.9026	High Similarity	NPC472905
0.9026	High Similarity	NPC469550
0.902	High Similarity	NPC204350
0.902	High Similarity	NPC256406
0.902	High Similarity	NPC31363
0.902	High Similarity	NPC45291
0.902	High Similarity	NPC272566
0.902	High Similarity	NPC19980
0.9007	High Similarity	NPC119660
0.9007	High Similarity	NPC93034
0.9	High Similarity	NPC157133
0.8994	High Similarity	NPC267153
0.8987	High Similarity	NPC93739
0.8981	High Similarity	NPC474960
0.8981	High Similarity	NPC200594
0.8981	High Similarity	NPC84571
0.8974	High Similarity	NPC35598
0.8974	High Similarity	NPC300727
0.8974	High Similarity	NPC136674
0.8974	High Similarity	NPC129684
0.8974	High Similarity	NPC241904
0.8974	High Similarity	NPC84935
0.8974	High Similarity	NPC190020
0.8974	High Similarity	NPC222689
0.8974	High Similarity	NPC299520
0.8974	High Similarity	NPC77679
0.8968	High Similarity	NPC199926
0.8968	High Similarity	NPC472048
0.8968	High Similarity	NPC168247
0.8968	High Similarity	NPC57674
0.8968	High Similarity	NPC39184
0.8968	High Similarity	NPC230149
0.8968	High Similarity	NPC152951
0.8968	High Similarity	NPC117992
0.8961	High Similarity	NPC257648
0.8961	High Similarity	NPC260979
0.8961	High Similarity	NPC39732
0.8961	High Similarity	NPC60972
0.8961	High Similarity	NPC477231
0.8954	High Similarity	NPC10467
0.8954	High Similarity	NPC156953
0.8954	High Similarity	NPC96501
0.8947	High Similarity	NPC172329
0.8947	High Similarity	NPC196277
0.8947	High Similarity	NPC2569
0.8947	High Similarity	NPC272721
0.8947	High Similarity	NPC43669
0.8944	High Similarity	NPC165979
0.8944	High Similarity	NPC163130
0.894	High Similarity	NPC472033
0.894	High Similarity	NPC165389
0.8933	High Similarity	NPC105213
0.8933	High Similarity	NPC242893
0.8933	High Similarity	NPC38065
0.8931	High Similarity	NPC284007
0.8931	High Similarity	NPC300984
0.8924	High Similarity	NPC303565
0.8924	High Similarity	NPC258331
0.8917	High Similarity	NPC476242
0.8917	High Similarity	NPC238381
0.8917	High Similarity	NPC55738
0.8917	High Similarity	NPC235448
0.891	High Similarity	NPC274730
0.891	High Similarity	NPC472455
0.8903	High Similarity	NPC271779
0.8903	High Similarity	NPC273462
0.8903	High Similarity	NPC206238
0.8903	High Similarity	NPC33051
0.8903	High Similarity	NPC227337
0.8903	High Similarity	NPC88645
0.8903	High Similarity	NPC167091
0.8903	High Similarity	NPC250557
0.8903	High Similarity	NPC292214
0.8903	High Similarity	NPC70433
0.8903	High Similarity	NPC475895
0.8903	High Similarity	NPC93552
0.8903	High Similarity	NPC49402
0.8896	High Similarity	NPC262623
0.8896	High Similarity	NPC302783
0.8896	High Similarity	NPC473201
0.8889	High Similarity	NPC137062
0.8889	High Similarity	NPC134293
0.8889	High Similarity	NPC223579
0.8889	High Similarity	NPC124470
0.8889	High Similarity	NPC183950
0.8889	High Similarity	NPC109827
0.8889	High Similarity	NPC287101
0.8889	High Similarity	NPC52005
0.8889	High Similarity	NPC38545
0.8889	High Similarity	NPC171916
0.8882	High Similarity	NPC168803
0.8882	High Similarity	NPC77378
0.8882	High Similarity	NPC77598
0.8882	High Similarity	NPC234331
0.8874	High Similarity	NPC472034
0.8868	High Similarity	NPC472964
0.8861	High Similarity	NPC471973
0.8861	High Similarity	NPC130955
0.8861	High Similarity	NPC472902
0.8861	High Similarity	NPC14353
0.8861	High Similarity	NPC56085
0.8861	High Similarity	NPC139036
0.8861	High Similarity	NPC24627
0.8861	High Similarity	NPC36217
0.8861	High Similarity	NPC228785
0.8854	High Similarity	NPC180011
0.8854	High Similarity	NPC210084
0.8854	High Similarity	NPC304008
0.8854	High Similarity	NPC99597
0.8854	High Similarity	NPC111969
0.8854	High Similarity	NPC179732
0.8854	High Similarity	NPC161960
0.8854	High Similarity	NPC219867
0.8854	High Similarity	NPC187745
0.8851	High Similarity	NPC471819
0.8846	High Similarity	NPC256612
0.8846	High Similarity	NPC20830
0.8846	High Similarity	NPC255807
0.8846	High Similarity	NPC472280

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 NPC38898 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	349
0.1-0.2	1002
0.2-0.3	1733
0.3-0.4	2660
0.4-0.5	1767
0.5-0.6	1027
0.6-0.7	423
0.7-0.8	140
0.8-0.85	38
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8868	High Similarity	NPD6232	Discontinued
0.8839	High Similarity	NPD1934	Approved
0.882	High Similarity	NPD7473	Discontinued
0.879	High Similarity	NPD3882	Suspended
0.8782	High Similarity	NPD2801	Approved
0.86	High Similarity	NPD970	Clinical (unspecified phase)
0.8562	High Similarity	NPD1511	Approved
0.8544	High Similarity	NPD1465	Phase 2
0.8544	High Similarity	NPD2393	Clinical (unspecified phase)
0.8503	High Similarity	NPD943	Approved
0.8503	High Similarity	NPD1240	Approved
0.8491	Intermediate Similarity	NPD3817	Phase 2
0.8452	Intermediate Similarity	NPD1512	Approved
0.8438	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD7819	Suspended
0.8424	Intermediate Similarity	NPD3818	Discontinued
0.84	Intermediate Similarity	NPD1510	Phase 2
0.8389	Intermediate Similarity	NPD1607	Approved
0.8323	Intermediate Similarity	NPD6799	Approved
0.8303	Intermediate Similarity	NPD6166	Phase 2
0.8303	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD7075	Discontinued
0.8247	Intermediate Similarity	NPD3750	Approved
0.8239	Intermediate Similarity	NPD6599	Discontinued
0.8214	Intermediate Similarity	NPD7074	Phase 3
0.82	Intermediate Similarity	NPD230	Phase 1
0.8199	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7411	Suspended
0.8176	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD3749	Approved
0.8158	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD5844	Phase 1
0.8155	Intermediate Similarity	NPD7054	Approved
0.8153	Intermediate Similarity	NPD2532	Approved
0.8153	Intermediate Similarity	NPD2533	Approved
0.8153	Intermediate Similarity	NPD2534	Approved
0.8125	Intermediate Similarity	NPD4380	Phase 2
0.8117	Intermediate Similarity	NPD1549	Phase 2
0.8107	Intermediate Similarity	NPD7472	Approved
0.8105	Intermediate Similarity	NPD2935	Discontinued
0.8063	Intermediate Similarity	NPD3226	Approved
0.8061	Intermediate Similarity	NPD5494	Approved
0.8052	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6801	Discontinued
0.8013	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD919	Approved
0.7976	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD447	Suspended
0.7953	Intermediate Similarity	NPD6797	Phase 2
0.7953	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD3748	Approved
0.7917	Intermediate Similarity	NPD3926	Phase 2
0.7907	Intermediate Similarity	NPD7251	Discontinued
0.7904	Intermediate Similarity	NPD1247	Approved
0.7898	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6234	Discontinued
0.7871	Intermediate Similarity	NPD2796	Approved
0.7871	Intermediate Similarity	NPD1551	Phase 2
0.7861	Intermediate Similarity	NPD7808	Phase 3
0.7834	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5402	Approved
0.7812	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD37	Approved
0.78	Intermediate Similarity	NPD9494	Approved
0.7798	Intermediate Similarity	NPD7199	Phase 2
0.7785	Intermediate Similarity	NPD4628	Phase 3
0.7771	Intermediate Similarity	NPD7768	Phase 2
0.775	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD5403	Approved
0.7707	Intermediate Similarity	NPD2346	Discontinued
0.7706	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD9269	Phase 2
0.7702	Intermediate Similarity	NPD5401	Approved
0.7697	Intermediate Similarity	NPD3027	Phase 3
0.7692	Intermediate Similarity	NPD6959	Discontinued
0.7692	Intermediate Similarity	NPD2799	Discontinued
0.7665	Intermediate Similarity	NPD4967	Phase 2
0.7665	Intermediate Similarity	NPD4966	Approved
0.7665	Intermediate Similarity	NPD4965	Approved
0.7651	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1933	Approved
0.7611	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1243	Approved
0.761	Intermediate Similarity	NPD2800	Approved
0.7607	Intermediate Similarity	NPD920	Approved
0.7602	Intermediate Similarity	NPD5242	Approved
0.76	Intermediate Similarity	NPD6559	Discontinued
0.7595	Intermediate Similarity	NPD2344	Approved
0.7572	Intermediate Similarity	NPD7228	Approved
0.755	Intermediate Similarity	NPD1203	Approved
0.7544	Intermediate Similarity	NPD5711	Approved
0.7544	Intermediate Similarity	NPD5710	Approved
0.7543	Intermediate Similarity	NPD5953	Discontinued
0.7532	Intermediate Similarity	NPD3764	Approved
0.7529	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6190	Approved
0.7485	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7469	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6651	Approved
0.7451	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1613	Approved
0.7436	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1470	Approved
0.7432	Intermediate Similarity	NPD9268	Approved
0.7429	Intermediate Similarity	NPD7286	Phase 2
0.7423	Intermediate Similarity	NPD7390	Discontinued
0.7421	Intermediate Similarity	NPD5406	Approved
0.7421	Intermediate Similarity	NPD5408	Approved
0.7421	Intermediate Similarity	NPD5404	Approved
0.7421	Intermediate Similarity	NPD5405	Approved
0.7419	Intermediate Similarity	NPD3268	Approved
0.7419	Intermediate Similarity	NPD2313	Discontinued
0.7407	Intermediate Similarity	NPD2309	Approved
0.7401	Intermediate Similarity	NPD7685	Pre-registration
0.7386	Intermediate Similarity	NPD2798	Approved
0.7351	Intermediate Similarity	NPD9717	Approved
0.7351	Intermediate Similarity	NPD1608	Approved
0.7347	Intermediate Similarity	NPD9493	Approved
0.7346	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6386	Approved
0.7321	Intermediate Similarity	NPD6385	Approved
0.7318	Intermediate Similarity	NPD8312	Approved
0.7318	Intermediate Similarity	NPD8313	Approved
0.7312	Intermediate Similarity	NPD6100	Approved
0.7312	Intermediate Similarity	NPD6099	Approved
0.7305	Intermediate Similarity	NPD7458	Discontinued
0.7294	Intermediate Similarity	NPD4288	Approved
0.7294	Intermediate Similarity	NPD5353	Approved
0.7293	Intermediate Similarity	NPD8150	Discontinued
0.7293	Intermediate Similarity	NPD8434	Phase 2
0.7292	Intermediate Similarity	NPD8151	Discontinued
0.729	Intermediate Similarity	NPD6832	Phase 2
0.7285	Intermediate Similarity	NPD1201	Approved
0.7278	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1471	Phase 3
0.7255	Intermediate Similarity	NPD1283	Approved
0.7248	Intermediate Similarity	NPD9545	Approved
0.7246	Intermediate Similarity	NPD1653	Approved
0.7241	Intermediate Similarity	NPD3787	Discontinued
0.7239	Intermediate Similarity	NPD7003	Approved
0.7215	Intermediate Similarity	NPD4060	Phase 1
0.7213	Intermediate Similarity	NPD4287	Approved
0.7212	Intermediate Similarity	NPD4357	Discontinued
0.7211	Intermediate Similarity	NPD7435	Discontinued
0.7208	Intermediate Similarity	NPD1164	Approved
0.7208	Intermediate Similarity	NPD3267	Approved
0.7208	Intermediate Similarity	NPD3266	Approved
0.7197	Intermediate Similarity	NPD411	Approved
0.7182	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5536	Phase 2
0.7171	Intermediate Similarity	NPD422	Phase 1
0.7152	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD1876	Approved
0.7143	Intermediate Similarity	NPD6782	Approved
0.7143	Intermediate Similarity	NPD6780	Approved
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD6779	Approved
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD6776	Approved
0.7143	Intermediate Similarity	NPD6778	Approved
0.7143	Intermediate Similarity	NPD6781	Approved
0.7143	Intermediate Similarity	NPD6777	Approved
0.7134	Intermediate Similarity	NPD8166	Discontinued
0.7124	Intermediate Similarity	NPD3972	Approved
0.7115	Intermediate Similarity	NPD3018	Phase 2
0.7114	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7240	Approved
0.7101	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2797	Approved
0.7091	Intermediate Similarity	NPD2354	Approved
0.7074	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2654	Approved
0.7072	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.7062	Intermediate Similarity	NPD2403	Approved
0.7059	Intermediate Similarity	NPD1281	Approved
0.7039	Intermediate Similarity	NPD4626	Approved
0.7037	Intermediate Similarity	NPD7033	Discontinued
0.7032	Intermediate Similarity	NPD3225	Approved
0.7024	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD228	Approved
0.7	Intermediate Similarity	NPD3455	Phase 2
0.6994	Remote Similarity	NPD5978	Approved
0.6994	Remote Similarity	NPD5977	Approved
0.699	Remote Similarity	NPD7874	Approved
0.699	Remote Similarity	NPD7875	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