NPASS Compound

Structure

CID68167 OpenBabel06191715402D 25 26 0 0 1 0 0 0 0 0999 V2000 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 1 10 2 0 0 0 0 2 6 2 0 0 0 0 2 10 1 0 0 0 0 3 7 1 0 0 0 0 3 11 2 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 9 14 2 0 0 0 0 11 16 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 15 14 1 6 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 21 2 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.07
Volume:	337.938
LogP:	2.058
LogD:	2.273
LogS:	-3.414
# Rotatable Bonds:	6
TPSA:	132.13
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.359
Synthetic Accessibility Score:	2.952
Fsp3:	0.056
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.955
MDCK Permeability:	8.115345735859592e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.067
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	98.12158203125%
Volume Distribution (VD):	0.216
Pgp-substrate:	1.9775331020355225%

ADMET: Metabolism

CYP1A2-inhibitor:	0.101
CYP1A2-substrate:	0.03
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.038
CYP2C9-inhibitor:	0.18
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.268
CYP3A4-substrate:	0.05

ADMET: Excretion

Clearance (CL):	1.079
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.176
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.216
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.585
Carcinogencity:	0.051
Eye Corrosion:	0.004
Eye Irritation:	0.113
Respiratory Toxicity:	0.775

Download Data

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

Natural Product: NPC68167

Natural Product ID:	NPC68167
*Common Name:**	2-(4-Hydroxybenzeoyl)-3-[(E)-1-(4-Hydroxyphenyl)Methylidene]Succinic Acid
IUPAC Name:	(2R,3E)-2-(4-hydroxybenzoyl)-3-[(4-hydroxyphenyl)methylidene]butanedioic acid
Synonyms:
Standard InCHIKey:	TUOXWFIJOOGTSU-AAWPKVBNSA-N
Standard InCHI:	InChI=1S/C18H14O7/c19-12-5-1-10(2-6-12)9-14(17(22)23)15(18(24)25)16(21)11-3-7-13(20)8-4-11/h1-9,15,19-20H,(H,22,23)(H,24,25)/b14-9+/t15-/m1/s1
SMILES:	c1cc(ccc1/C=C([C@H](C(=O)c1ccc(cc1)O)C(=O)O)/C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458257
PubChem CID:	11336803
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	tenerife	n.a.	PMID[10924166]
NPO17504	Chaerophyllum hirsutum	Species	Apiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15387667]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309323]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22220686]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24279991]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24784222]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18250	Conus tessulatus	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18716	Parmelia caraccensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19061	Ceratozamia kuesteriana	Species	Zamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17504	Chaerophyllum hirsutum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17281	Echinaster echinophorus	Species	Echinasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17606	Millettia ichthyochtona	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16201	Pteris altissima	Species	Pteridaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	11500.0	nM	PMID[448247]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	30600.0	nM	PMID[448247]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	16400.0	nM	PMID[448247]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	19600.0	nM	PMID[448247]

☑ 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 NPC68167 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	315
0.1-0.2	1468
0.2-0.3	3775
0.3-0.4	9298
0.4-0.5	9905
0.5-0.6	5773
0.6-0.7	8896
0.7-0.8	3081
0.8-0.85	175
0.85-0.9	9
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8974	High Similarity	NPC322197
0.875	High Similarity	NPC249435
0.8707	High Similarity	NPC116842
0.8696	High Similarity	NPC17525
0.8629	High Similarity	NPC477153
0.8621	High Similarity	NPC88141
0.8583	High Similarity	NPC95537
0.8548	High Similarity	NPC91478
0.8475	Intermediate Similarity	NPC268388
0.8475	Intermediate Similarity	NPC114682
0.8468	Intermediate Similarity	NPC120545
0.8462	Intermediate Similarity	NPC95172
0.8448	Intermediate Similarity	NPC226699
0.8425	Intermediate Similarity	NPC8745
0.8425	Intermediate Similarity	NPC473751
0.8417	Intermediate Similarity	NPC285350
0.84	Intermediate Similarity	NPC133909
0.84	Intermediate Similarity	NPC283514
0.84	Intermediate Similarity	NPC32032
0.8387	Intermediate Similarity	NPC248363
0.8372	Intermediate Similarity	NPC214246
0.8362	Intermediate Similarity	NPC69332
0.8362	Intermediate Similarity	NPC95178
0.8362	Intermediate Similarity	NPC6984
0.8362	Intermediate Similarity	NPC70843
0.8362	Intermediate Similarity	NPC188677
0.8362	Intermediate Similarity	NPC29989
0.8358	Intermediate Similarity	NPC4214
0.8347	Intermediate Similarity	NPC23402
0.8346	Intermediate Similarity	NPC10926
0.832	Intermediate Similarity	NPC267552
0.832	Intermediate Similarity	NPC45438
0.832	Intermediate Similarity	NPC115159
0.832	Intermediate Similarity	NPC295034
0.832	Intermediate Similarity	NPC198336
0.832	Intermediate Similarity	NPC156139
0.832	Intermediate Similarity	NPC224273
0.832	Intermediate Similarity	NPC242895
0.832	Intermediate Similarity	NPC143427
0.832	Intermediate Similarity	NPC73532
0.832	Intermediate Similarity	NPC19174
0.8306	Intermediate Similarity	NPC159525
0.8295	Intermediate Similarity	NPC221777
0.8295	Intermediate Similarity	NPC473017
0.8293	Intermediate Similarity	NPC474890
0.8293	Intermediate Similarity	NPC161943
0.8293	Intermediate Similarity	NPC273282
0.8291	Intermediate Similarity	NPC29883
0.8291	Intermediate Similarity	NPC141523
0.8271	Intermediate Similarity	NPC72918
0.8268	Intermediate Similarity	NPC13238
0.8264	Intermediate Similarity	NPC221870
0.8258	Intermediate Similarity	NPC52407
0.8254	Intermediate Similarity	NPC139171
0.824	Intermediate Similarity	NPC216216
0.824	Intermediate Similarity	NPC297186
0.8235	Intermediate Similarity	NPC21162
0.8231	Intermediate Similarity	NPC474998
0.8226	Intermediate Similarity	NPC158222
0.8217	Intermediate Similarity	NPC100067
0.8217	Intermediate Similarity	NPC103356
0.8217	Intermediate Similarity	NPC266689
0.8217	Intermediate Similarity	NPC23126
0.8217	Intermediate Similarity	NPC30501
0.8217	Intermediate Similarity	NPC98254
0.8217	Intermediate Similarity	NPC105157
0.8217	Intermediate Similarity	NPC72158
0.8217	Intermediate Similarity	NPC190043
0.8217	Intermediate Similarity	NPC169250
0.8217	Intermediate Similarity	NPC162612
0.8211	Intermediate Similarity	NPC160199
0.8209	Intermediate Similarity	NPC474726
0.8209	Intermediate Similarity	NPC475955
0.8205	Intermediate Similarity	NPC187913
0.8205	Intermediate Similarity	NPC184658
0.8195	Intermediate Similarity	NPC50924
0.8195	Intermediate Similarity	NPC288089
0.819	Intermediate Similarity	NPC120693
0.819	Intermediate Similarity	NPC261573
0.819	Intermediate Similarity	NPC8931
0.8189	Intermediate Similarity	NPC375356
0.8182	Intermediate Similarity	NPC242136
0.8175	Intermediate Similarity	NPC196976
0.8167	Intermediate Similarity	NPC212718
0.8167	Intermediate Similarity	NPC177576
0.8154	Intermediate Similarity	NPC234175
0.8154	Intermediate Similarity	NPC21305
0.8154	Intermediate Similarity	NPC229894
0.8145	Intermediate Similarity	NPC184527
0.814	Intermediate Similarity	NPC96915
0.814	Intermediate Similarity	NPC62952
0.814	Intermediate Similarity	NPC267846
0.8136	Intermediate Similarity	NPC34715
0.813	Intermediate Similarity	NPC83718
0.813	Intermediate Similarity	NPC128249
0.812	Intermediate Similarity	NPC294226
0.812	Intermediate Similarity	NPC13495
0.812	Intermediate Similarity	NPC139074
0.812	Intermediate Similarity	NPC213485
0.812	Intermediate Similarity	NPC40524
0.812	Intermediate Similarity	NPC474715
0.811	Intermediate Similarity	NPC244351
0.811	Intermediate Similarity	NPC300274
0.811	Intermediate Similarity	NPC475192
0.8106	Intermediate Similarity	NPC244699
0.8106	Intermediate Similarity	NPC108553
0.8103	Intermediate Similarity	NPC68269
0.8099	Intermediate Similarity	NPC231717
0.8095	Intermediate Similarity	NPC146642
0.8092	Intermediate Similarity	NPC117899
0.8092	Intermediate Similarity	NPC109123
0.8092	Intermediate Similarity	NPC102829
0.8092	Intermediate Similarity	NPC120488
0.8092	Intermediate Similarity	NPC99731
0.8092	Intermediate Similarity	NPC94810
0.8092	Intermediate Similarity	NPC25736
0.8087	Intermediate Similarity	NPC52472
0.8083	Intermediate Similarity	NPC321252
0.8083	Intermediate Similarity	NPC252544
0.808	Intermediate Similarity	NPC473767
0.808	Intermediate Similarity	NPC156654
0.8077	Intermediate Similarity	NPC116513
0.8077	Intermediate Similarity	NPC107672
0.8074	Intermediate Similarity	NPC7464
0.8067	Intermediate Similarity	NPC224584
0.8065	Intermediate Similarity	NPC150919
0.8065	Intermediate Similarity	NPC269414
0.8062	Intermediate Similarity	NPC103540
0.806	Intermediate Similarity	NPC44437
0.806	Intermediate Similarity	NPC282780
0.806	Intermediate Similarity	NPC166480
0.8058	Intermediate Similarity	NPC66593
0.8058	Intermediate Similarity	NPC474692
0.8049	Intermediate Similarity	NPC240163
0.8049	Intermediate Similarity	NPC161304
0.8047	Intermediate Similarity	NPC275145
0.8047	Intermediate Similarity	NPC174991
0.8045	Intermediate Similarity	NPC175738
0.8045	Intermediate Similarity	NPC135801
0.8043	Intermediate Similarity	NPC290550
0.8033	Intermediate Similarity	NPC11824
0.8031	Intermediate Similarity	NPC25168
0.803	Intermediate Similarity	NPC199253
0.803	Intermediate Similarity	NPC31539
0.803	Intermediate Similarity	NPC136588
0.8029	Intermediate Similarity	NPC26924
0.8016	Intermediate Similarity	NPC294037
0.8015	Intermediate Similarity	NPC471236
0.8015	Intermediate Similarity	NPC96024
0.8015	Intermediate Similarity	NPC197766
0.8015	Intermediate Similarity	NPC2596
0.8015	Intermediate Similarity	NPC193203
0.8	Intermediate Similarity	NPC306765
0.8	Intermediate Similarity	NPC80035
0.8	Intermediate Similarity	NPC283590
0.8	Intermediate Similarity	NPC15837
0.8	Intermediate Similarity	NPC3224
0.8	Intermediate Similarity	NPC104514
0.8	Intermediate Similarity	NPC61153
0.8	Intermediate Similarity	NPC241089
0.8	Intermediate Similarity	NPC245561
0.8	Intermediate Similarity	NPC311091
0.8	Intermediate Similarity	NPC161632
0.8	Intermediate Similarity	NPC130899
0.8	Intermediate Similarity	NPC471033
0.8	Intermediate Similarity	NPC70859
0.8	Intermediate Similarity	NPC477596
0.7985	Intermediate Similarity	NPC225051
0.7985	Intermediate Similarity	NPC53896
0.7984	Intermediate Similarity	NPC312800
0.7984	Intermediate Similarity	NPC108288
0.7984	Intermediate Similarity	NPC28951
0.7984	Intermediate Similarity	NPC277394
0.7984	Intermediate Similarity	NPC61062
0.7984	Intermediate Similarity	NPC299252
0.7984	Intermediate Similarity	NPC131192
0.7984	Intermediate Similarity	NPC325646
0.7984	Intermediate Similarity	NPC310540
0.7971	Intermediate Similarity	NPC169452
0.7971	Intermediate Similarity	NPC315578
0.7971	Intermediate Similarity	NPC181560
0.797	Intermediate Similarity	NPC198249
0.797	Intermediate Similarity	NPC93015
0.797	Intermediate Similarity	NPC469526
0.797	Intermediate Similarity	NPC18798
0.797	Intermediate Similarity	NPC34070
0.797	Intermediate Similarity	NPC475042
0.7969	Intermediate Similarity	NPC86900
0.7967	Intermediate Similarity	NPC81808
0.7958	Intermediate Similarity	NPC119767
0.7956	Intermediate Similarity	NPC289358
0.7956	Intermediate Similarity	NPC245760
0.7956	Intermediate Similarity	NPC165191
0.7956	Intermediate Similarity	NPC114333
0.7956	Intermediate Similarity	NPC46242
0.7956	Intermediate Similarity	NPC473479
0.7956	Intermediate Similarity	NPC477849
0.7956	Intermediate Similarity	NPC23667
0.7956	Intermediate Similarity	NPC297797
0.7956	Intermediate Similarity	NPC51531

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 NPC68167 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	910
0.2-0.3	1350
0.3-0.4	2585
0.4-0.5	2281
0.5-0.6	1191
0.6-0.7	431
0.7-0.8	101
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8291	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8203	Intermediate Similarity	NPD1164	Approved
0.8062	Intermediate Similarity	NPD1470	Approved
0.8045	Intermediate Similarity	NPD943	Approved
0.803	Intermediate Similarity	NPD3764	Approved
0.7984	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD2344	Approved
0.7941	Intermediate Similarity	NPD2799	Discontinued
0.7917	Intermediate Similarity	NPD74	Approved
0.7917	Intermediate Similarity	NPD9266	Approved
0.7895	Intermediate Similarity	NPD2313	Discontinued
0.7883	Intermediate Similarity	NPD2935	Discontinued
0.7857	Intermediate Similarity	NPD9545	Approved
0.7833	Intermediate Similarity	NPD9264	Approved
0.7833	Intermediate Similarity	NPD9267	Approved
0.7833	Intermediate Similarity	NPD9263	Approved
0.781	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD1201	Approved
0.773	Intermediate Similarity	NPD2309	Approved
0.7698	Intermediate Similarity	NPD9493	Approved
0.7692	Intermediate Similarity	NPD9269	Phase 2
0.7681	Intermediate Similarity	NPD1510	Phase 2
0.7656	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD9268	Approved
0.7652	Intermediate Similarity	NPD1203	Approved
0.7647	Intermediate Similarity	NPD1930	Approved
0.7647	Intermediate Similarity	NPD1240	Approved
0.7647	Intermediate Similarity	NPD1929	Approved
0.7647	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD5404	Approved
0.7626	Intermediate Similarity	NPD5408	Approved
0.7626	Intermediate Similarity	NPD5405	Approved
0.7626	Intermediate Similarity	NPD5406	Approved
0.7594	Intermediate Similarity	NPD2798	Approved
0.7576	Intermediate Similarity	NPD1876	Approved
0.7563	Intermediate Similarity	NPD1932	Approved
0.7557	Intermediate Similarity	NPD3972	Approved
0.7542	Intermediate Similarity	NPD3020	Approved
0.754	Intermediate Similarity	NPD9281	Approved
0.7536	Intermediate Similarity	NPD1607	Approved
0.75	Intermediate Similarity	NPD9261	Approved
0.7465	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD2346	Discontinued
0.7438	Intermediate Similarity	NPD1237	Approved
0.7436	Intermediate Similarity	NPD2859	Approved
0.7436	Intermediate Similarity	NPD2860	Approved
0.7429	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD1481	Phase 2
0.7414	Intermediate Similarity	NPD1202	Approved
0.7413	Intermediate Similarity	NPD4628	Phase 3
0.7413	Intermediate Similarity	NPD3750	Approved
0.7394	Intermediate Similarity	NPD1549	Phase 2
0.7365	Intermediate Similarity	NPD3226	Approved
0.735	Intermediate Similarity	NPD2933	Approved
0.735	Intermediate Similarity	NPD2934	Approved
0.7348	Intermediate Similarity	NPD1535	Discovery
0.7339	Intermediate Similarity	NPD2329	Discontinued
0.7339	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD230	Phase 1
0.7329	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD2932	Approved
0.7328	Intermediate Similarity	NPD3019	Approved
0.7324	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD9256	Approved
0.7304	Intermediate Similarity	NPD9258	Approved
0.7293	Intermediate Similarity	NPD9717	Approved
0.7293	Intermediate Similarity	NPD1608	Approved
0.7292	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD5951	Approved
0.726	Intermediate Similarity	NPD7390	Discontinued
0.7255	Intermediate Similarity	NPD3749	Approved
0.725	Intermediate Similarity	NPD2066	Phase 3
0.7248	Intermediate Similarity	NPD7458	Discontinued
0.7246	Intermediate Similarity	NPD3268	Approved
0.7241	Intermediate Similarity	NPD2354	Approved
0.7209	Intermediate Similarity	NPD255	Approved
0.7209	Intermediate Similarity	NPD256	Approved
0.72	Intermediate Similarity	NPD4380	Phase 2
0.7185	Intermediate Similarity	NPD1283	Approved
0.7183	Intermediate Similarity	NPD4308	Phase 3
0.7172	Intermediate Similarity	NPD7003	Approved
0.7152	Intermediate Similarity	NPD7411	Suspended
0.7152	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD3022	Approved
0.7143	Intermediate Similarity	NPD7075	Discontinued
0.7143	Intermediate Similarity	NPD3021	Approved
0.7143	Intermediate Similarity	NPD6799	Approved
0.7143	Intermediate Similarity	NPD1511	Approved
0.7133	Intermediate Similarity	NPD1551	Phase 2
0.7132	Intermediate Similarity	NPD2797	Approved
0.7124	Intermediate Similarity	NPD2296	Approved
0.7123	Intermediate Similarity	NPD6190	Approved
0.7101	Intermediate Similarity	NPD6832	Phase 2
0.7095	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD447	Suspended
0.709	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1471	Phase 3
0.7083	Intermediate Similarity	NPD2353	Approved
0.7075	Intermediate Similarity	NPD3300	Phase 2
0.7071	Intermediate Similarity	NPD520	Approved
0.707	Intermediate Similarity	NPD6232	Discontinued
0.7068	Intermediate Similarity	NPD17	Approved
0.7063	Intermediate Similarity	NPD3748	Approved
0.7059	Intermediate Similarity	NPD7819	Suspended
0.7059	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD8166	Discontinued
0.7047	Intermediate Similarity	NPD1512	Approved
0.7045	Intermediate Similarity	NPD1894	Discontinued
0.7037	Intermediate Similarity	NPD4878	Approved
0.7032	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD9494	Approved
0.7023	Intermediate Similarity	NPD9568	Approved
0.7016	Intermediate Similarity	NPD164	Approved
0.7015	Intermediate Similarity	NPD3847	Discontinued
0.7014	Intermediate Similarity	NPD2796	Approved
0.7007	Intermediate Similarity	NPD3266	Approved
0.7007	Intermediate Similarity	NPD3267	Approved
0.6993	Remote Similarity	NPD1934	Approved
0.6986	Remote Similarity	NPD2800	Approved
0.6985	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6599	Discontinued
0.6972	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD1238	Approved
0.6963	Remote Similarity	NPD1281	Approved
0.6959	Remote Similarity	NPD7440	Discontinued
0.6957	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9257	Approved
0.6957	Remote Similarity	NPD9259	Approved
0.695	Remote Similarity	NPD6663	Approved
0.6948	Remote Similarity	NPD2801	Approved
0.6948	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD3400	Discontinued
0.6929	Remote Similarity	NPD2182	Approved
0.6923	Remote Similarity	NPD1241	Discontinued
0.6917	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5736	Approved
0.6903	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4307	Phase 2
0.6892	Remote Similarity	NPD3887	Approved
0.6889	Remote Similarity	NPD3023	Approved
0.6889	Remote Similarity	NPD3026	Approved
0.6887	Remote Similarity	NPD920	Approved
0.6883	Remote Similarity	NPD6801	Discontinued
0.688	Remote Similarity	NPD5909	Discontinued
0.6879	Remote Similarity	NPD411	Approved
0.6879	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1317	Discontinued
0.6875	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1243	Approved
0.6871	Remote Similarity	NPD5953	Discontinued
0.6867	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2533	Approved
0.6867	Remote Similarity	NPD2534	Approved
0.6867	Remote Similarity	NPD2532	Approved
0.6866	Remote Similarity	NPD3024	Approved
0.6866	Remote Similarity	NPD3025	Approved
0.6861	Remote Similarity	NPD1755	Approved
0.6859	Remote Similarity	NPD7768	Phase 2
0.6859	Remote Similarity	NPD3882	Suspended
0.6857	Remote Similarity	NPD2614	Approved
0.6853	Remote Similarity	NPD6355	Discontinued
0.6835	Remote Similarity	NPD257	Approved
0.6835	Remote Similarity	NPD258	Approved
0.6825	Remote Similarity	NPD5048	Discontinued
0.6824	Remote Similarity	NPD1196	Approved
0.6821	Remote Similarity	NPD6273	Approved
0.6812	Remote Similarity	NPD3225	Approved
0.6807	Remote Similarity	NPD1239	Approved
0.6806	Remote Similarity	NPD6651	Approved
0.68	Remote Similarity	NPD1543	Discontinued
0.6797	Remote Similarity	NPD3455	Phase 2
0.6795	Remote Similarity	NPD3817	Phase 2
0.6791	Remote Similarity	NPD1759	Phase 1
0.679	Remote Similarity	NPD3818	Discontinued
0.6783	Remote Similarity	NPD2979	Phase 3
0.6777	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1242	Phase 1
0.6769	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6798	Discontinued
0.6757	Remote Similarity	NPD1195	Approved
0.675	Remote Similarity	NPD6808	Phase 2
0.6748	Remote Similarity	NPD9495	Approved
0.6748	Remote Similarity	NPD7286	Phase 2
0.6742	Remote Similarity	NPD2629	Approved
0.6742	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1933	Approved
0.6733	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1465	Phase 2
0.6724	Remote Similarity	NPD111	Approved

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