NPASS Compound

Structure

CID214246 OpenBabel06191716002D 24 26 0 0 1 0 0 0 0 0999 V2000 2.8147 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9013 -1.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0823 -0.1615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8958 -1.9886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0768 -0.2661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4836 -1.1796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0388 -2.5873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 0.2976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4781 -1.2841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9898 -2.8963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7044 -3.2564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 0.4612 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 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 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 1 0 0 0 16 11 1 6 0 0 0 16 24 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.08
Volume:	323.228
LogP:	3.13
LogD:	2.251
LogS:	-3.008
# Rotatable Bonds:	4
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.585
Synthetic Accessibility Score:	2.456
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:	-5.699
MDCK Permeability:	8.327974683197681e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.101
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	99.53533172607422%
Volume Distribution (VD):	0.346
Pgp-substrate:	0.8696855902671814%

ADMET: Metabolism

CYP1A2-inhibitor:	0.179
CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.532
CYP2C9-substrate:	0.421
CYP2D6-inhibitor:	0.375
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.1

ADMET: Excretion

Clearance (CL):	7.697
Half-life (T1/2):	0.926

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.385
Drug-inuced Liver Injury (DILI):	0.991
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.177
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.184
Carcinogencity:	0.387
Eye Corrosion:	0.003
Eye Irritation:	0.077
Respiratory Toxicity:	0.627

Download Data

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

Natural Product: NPC214246

Natural Product ID:	NPC214246
*Common Name:**	(2R,3R,4E)-2-(4-Hydroxyphenyl)-4-[(4-Hydroxyphenyl)Methylidene]-5-Oxooxolane-3-Carboxylic Acid
IUPAC Name:	(2R,3R,4E)-2-(4-hydroxyphenyl)-4-[(4-hydroxyphenyl)methylidene]-5-oxooxolane-3-carboxylic acid
Synonyms:
Standard InCHIKey:	VCGDDWQSRJLRHG-MMJTVPDGSA-N
Standard InCHI:	InChI=1S/C18H14O6/c19-12-5-1-10(2-6-12)9-14-15(17(21)22)16(24-18(14)23)11-3-7-13(20)8-4-11/h1-9,15-16,19-20H,(H,21,22)/b14-9+/t15-,16+/m1/s1
SMILES:	Oc1ccc(cc1)/C=C1/C(=O)O[C@H]([C@@H]1C(=O)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458256
PubChem CID:	11381796
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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]
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]
NPO18250	Conus tessulatus	Species	Conidae	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	=	11300.0	nM	PMID[511220]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	36000.0	nM	PMID[511220]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	13900.0	nM	PMID[511220]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	40000.0	nM	PMID[511220]

☑ 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 NPC214246 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	290
0.1-0.2	1089
0.2-0.3	2632
0.3-0.4	6054
0.4-0.5	11085
0.5-0.6	6166
0.6-0.7	10441
0.7-0.8	4841
0.8-0.85	94
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8923	High Similarity	NPC318799
0.8806	High Similarity	NPC308976
0.8779	High Similarity	NPC108553
0.8722	High Similarity	NPC106406
0.8561	High Similarity	NPC183824
0.8548	High Similarity	NPC128249
0.854	High Similarity	NPC156709
0.854	High Similarity	NPC179505
0.8489	Intermediate Similarity	NPC285550
0.8478	Intermediate Similarity	NPC9218
0.8409	Intermediate Similarity	NPC79332
0.8394	Intermediate Similarity	NPC279676
0.8394	Intermediate Similarity	NPC67349
0.838	Intermediate Similarity	NPC229264
0.8372	Intermediate Similarity	NPC68167
0.8369	Intermediate Similarity	NPC210330
0.8369	Intermediate Similarity	NPC223185
0.8333	Intermediate Similarity	NPC325295
0.8333	Intermediate Similarity	NPC476266
0.8333	Intermediate Similarity	NPC76308
0.8321	Intermediate Similarity	NPC476033
0.8321	Intermediate Similarity	NPC79608
0.8321	Intermediate Similarity	NPC223616
0.832	Intermediate Similarity	NPC23402
0.8308	Intermediate Similarity	NPC236981
0.8298	Intermediate Similarity	NPC474692
0.8271	Intermediate Similarity	NPC2596
0.8261	Intermediate Similarity	NPC301915
0.8261	Intermediate Similarity	NPC261292
0.8258	Intermediate Similarity	NPC204579
0.8258	Intermediate Similarity	NPC110211
0.8252	Intermediate Similarity	NPC283081
0.8252	Intermediate Similarity	NPC143892
0.8252	Intermediate Similarity	NPC221383
0.8252	Intermediate Similarity	NPC299090
0.824	Intermediate Similarity	NPC285350
0.8231	Intermediate Similarity	NPC469927
0.8222	Intermediate Similarity	NPC198388
0.8222	Intermediate Similarity	NPC281798
0.8214	Intermediate Similarity	NPC100675
0.8211	Intermediate Similarity	NPC183700
0.8207	Intermediate Similarity	NPC32197
0.8197	Intermediate Similarity	NPC206341
0.8194	Intermediate Similarity	NPC1580
0.8188	Intermediate Similarity	NPC90431
0.8188	Intermediate Similarity	NPC471345
0.8182	Intermediate Similarity	NPC49938
0.8182	Intermediate Similarity	NPC137416
0.8175	Intermediate Similarity	NPC68517
0.8169	Intermediate Similarity	NPC304956
0.8169	Intermediate Similarity	NPC32
0.8169	Intermediate Similarity	NPC476473
0.8169	Intermediate Similarity	NPC122491
0.8162	Intermediate Similarity	NPC25581
0.8162	Intermediate Similarity	NPC323379
0.8162	Intermediate Similarity	NPC327204
0.8162	Intermediate Similarity	NPC18074
0.8162	Intermediate Similarity	NPC5419
0.8162	Intermediate Similarity	NPC61
0.816	Intermediate Similarity	NPC123175
0.816	Intermediate Similarity	NPC176730
0.8154	Intermediate Similarity	NPC322332
0.814	Intermediate Similarity	NPC233282
0.8134	Intermediate Similarity	NPC473744
0.8134	Intermediate Similarity	NPC469930
0.8125	Intermediate Similarity	NPC27633
0.8125	Intermediate Similarity	NPC104514
0.8125	Intermediate Similarity	NPC311091
0.8125	Intermediate Similarity	NPC94298
0.8125	Intermediate Similarity	NPC471033
0.8116	Intermediate Similarity	NPC70680
0.8116	Intermediate Similarity	NPC233350
0.8116	Intermediate Similarity	NPC182217
0.8112	Intermediate Similarity	NPC258671
0.8112	Intermediate Similarity	NPC53884
0.8106	Intermediate Similarity	NPC288945
0.8102	Intermediate Similarity	NPC168799
0.8102	Intermediate Similarity	NPC477281
0.8102	Intermediate Similarity	NPC19719
0.8102	Intermediate Similarity	NPC477280
0.8102	Intermediate Similarity	NPC155209
0.8102	Intermediate Similarity	NPC472591
0.8099	Intermediate Similarity	NPC474300
0.8099	Intermediate Similarity	NPC478250
0.8099	Intermediate Similarity	NPC89317
0.8095	Intermediate Similarity	NPC476434
0.8095	Intermediate Similarity	NPC95498
0.8095	Intermediate Similarity	NPC246566
0.8088	Intermediate Similarity	NPC7012
0.8085	Intermediate Similarity	NPC147542
0.8085	Intermediate Similarity	NPC155205
0.8085	Intermediate Similarity	NPC37992
0.8085	Intermediate Similarity	NPC327916
0.8085	Intermediate Similarity	NPC241349
0.8085	Intermediate Similarity	NPC42262
0.8085	Intermediate Similarity	NPC220496
0.8085	Intermediate Similarity	NPC32749
0.808	Intermediate Similarity	NPC17693
0.8074	Intermediate Similarity	NPC94810
0.8074	Intermediate Similarity	NPC194979
0.8071	Intermediate Similarity	NPC24295
0.8071	Intermediate Similarity	NPC283560
0.8071	Intermediate Similarity	NPC61590
0.8069	Intermediate Similarity	NPC192568
0.8069	Intermediate Similarity	NPC471076
0.8069	Intermediate Similarity	NPC119767
0.8069	Intermediate Similarity	NPC120728
0.8056	Intermediate Similarity	NPC208293
0.8056	Intermediate Similarity	NPC30890
0.8047	Intermediate Similarity	NPC122117
0.8043	Intermediate Similarity	NPC194970
0.8043	Intermediate Similarity	NPC474895
0.8043	Intermediate Similarity	NPC248150
0.8042	Intermediate Similarity	NPC470130
0.8042	Intermediate Similarity	NPC194938
0.8042	Intermediate Similarity	NPC21873
0.803	Intermediate Similarity	NPC212541
0.803	Intermediate Similarity	NPC14141
0.8029	Intermediate Similarity	NPC471095
0.8029	Intermediate Similarity	NPC471066
0.8028	Intermediate Similarity	NPC253722
0.8028	Intermediate Similarity	NPC253481
0.8028	Intermediate Similarity	NPC31751
0.8028	Intermediate Similarity	NPC257003
0.8027	Intermediate Similarity	NPC243891
0.8016	Intermediate Similarity	NPC87069
0.8015	Intermediate Similarity	NPC217052
0.8015	Intermediate Similarity	NPC472271
0.8015	Intermediate Similarity	NPC32626
0.8015	Intermediate Similarity	NPC147654
0.8015	Intermediate Similarity	NPC237506
0.8015	Intermediate Similarity	NPC329344
0.8014	Intermediate Similarity	NPC471602
0.8014	Intermediate Similarity	NPC256463
0.8014	Intermediate Similarity	NPC59775
0.8014	Intermediate Similarity	NPC111422
0.8014	Intermediate Similarity	NPC256162
0.8014	Intermediate Similarity	NPC125570
0.8014	Intermediate Similarity	NPC299405
0.8014	Intermediate Similarity	NPC29771
0.8014	Intermediate Similarity	NPC476477
0.8014	Intermediate Similarity	NPC306835
0.8014	Intermediate Similarity	NPC216312
0.8014	Intermediate Similarity	NPC295339
0.8	Intermediate Similarity	NPC177576
0.8	Intermediate Similarity	NPC219923
0.8	Intermediate Similarity	NPC51513
0.8	Intermediate Similarity	NPC322660
0.8	Intermediate Similarity	NPC170718
0.8	Intermediate Similarity	NPC73320
0.8	Intermediate Similarity	NPC281780
0.8	Intermediate Similarity	NPC202112
0.8	Intermediate Similarity	NPC147250
0.7987	Intermediate Similarity	NPC477299
0.7986	Intermediate Similarity	NPC475528
0.7985	Intermediate Similarity	NPC475236
0.7984	Intermediate Similarity	NPC79543
0.7973	Intermediate Similarity	NPC290671
0.7973	Intermediate Similarity	NPC267091
0.7973	Intermediate Similarity	NPC151425
0.7972	Intermediate Similarity	NPC106920
0.7972	Intermediate Similarity	NPC273657
0.7971	Intermediate Similarity	NPC164172
0.7971	Intermediate Similarity	NPC471749
0.797	Intermediate Similarity	NPC184219
0.7969	Intermediate Similarity	NPC131192
0.7967	Intermediate Similarity	NPC260952
0.7959	Intermediate Similarity	NPC317492
0.7959	Intermediate Similarity	NPC116292
0.7959	Intermediate Similarity	NPC162569
0.7959	Intermediate Similarity	NPC267469
0.7959	Intermediate Similarity	NPC35097
0.7959	Intermediate Similarity	NPC35160
0.7959	Intermediate Similarity	NPC87630
0.7959	Intermediate Similarity	NPC179128
0.7958	Intermediate Similarity	NPC310370
0.7958	Intermediate Similarity	NPC469911
0.7958	Intermediate Similarity	NPC183642
0.7956	Intermediate Similarity	NPC478255
0.7956	Intermediate Similarity	NPC473777
0.7955	Intermediate Similarity	NPC132518
0.7955	Intermediate Similarity	NPC477151
0.7953	Intermediate Similarity	NPC221870
0.7945	Intermediate Similarity	NPC81835
0.7943	Intermediate Similarity	NPC302857
0.7943	Intermediate Similarity	NPC221104
0.7943	Intermediate Similarity	NPC278068
0.7943	Intermediate Similarity	NPC220942
0.7943	Intermediate Similarity	NPC472602
0.7943	Intermediate Similarity	NPC152942
0.7943	Intermediate Similarity	NPC142703
0.7943	Intermediate Similarity	NPC324262
0.7943	Intermediate Similarity	NPC62800
0.7943	Intermediate Similarity	NPC37250
0.7943	Intermediate Similarity	NPC219428
0.7941	Intermediate Similarity	NPC226855
0.7937	Intermediate Similarity	NPC290353
0.7937	Intermediate Similarity	NPC153795
0.7937	Intermediate Similarity	NPC42911
0.7933	Intermediate Similarity	NPC203757

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 NPC214246 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	720
0.2-0.3	1440
0.3-0.4	2403
0.4-0.5	2324
0.5-0.6	1324
0.6-0.7	592
0.7-0.8	111
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8561	High Similarity	NPD3764	Approved
0.8125	Intermediate Similarity	NPD9545	Approved
0.7872	Intermediate Similarity	NPD2935	Discontinued
0.7847	Intermediate Similarity	NPD6190	Approved
0.7801	Intermediate Similarity	NPD1510	Phase 2
0.7778	Intermediate Similarity	NPD4628	Phase 3
0.7762	Intermediate Similarity	NPD1549	Phase 2
0.7746	Intermediate Similarity	NPD1551	Phase 2
0.7714	Intermediate Similarity	NPD230	Phase 1
0.7692	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD9493	Approved
0.7676	Intermediate Similarity	NPD7033	Discontinued
0.7676	Intermediate Similarity	NPD2799	Discontinued
0.7655	Intermediate Similarity	NPD3750	Approved
0.7655	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1203	Approved
0.7643	Intermediate Similarity	NPD1240	Approved
0.7626	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD2313	Discontinued
0.7612	Intermediate Similarity	NPD1535	Discovery
0.7591	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6355	Discontinued
0.7586	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1894	Discontinued
0.7569	Intermediate Similarity	NPD2344	Approved
0.7569	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD1608	Approved
0.7556	Intermediate Similarity	NPD1481	Phase 2
0.755	Intermediate Similarity	NPD4380	Phase 2
0.7535	Intermediate Similarity	NPD1607	Approved
0.7518	Intermediate Similarity	NPD1164	Approved
0.7518	Intermediate Similarity	NPD2797	Approved
0.7517	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7075	Discontinued
0.7484	Intermediate Similarity	NPD3749	Approved
0.745	Intermediate Similarity	NPD2534	Approved
0.745	Intermediate Similarity	NPD2532	Approved
0.745	Intermediate Similarity	NPD2533	Approved
0.745	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6002	Phase 3
0.7448	Intermediate Similarity	NPD6005	Phase 3
0.7448	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6004	Phase 3
0.7448	Intermediate Similarity	NPD7266	Discontinued
0.7447	Intermediate Similarity	NPD6233	Phase 2
0.7419	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7768	Phase 2
0.7403	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1470	Approved
0.7386	Intermediate Similarity	NPD7411	Suspended
0.7383	Intermediate Similarity	NPD6799	Approved
0.7379	Intermediate Similarity	NPD2796	Approved
0.7376	Intermediate Similarity	NPD3268	Approved
0.7376	Intermediate Similarity	NPD6798	Discontinued
0.7372	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3226	Approved
0.7365	Intermediate Similarity	NPD2309	Approved
0.7361	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD6832	Phase 2
0.7351	Intermediate Similarity	NPD920	Approved
0.7338	Intermediate Similarity	NPD37	Approved
0.7338	Intermediate Similarity	NPD1934	Approved
0.7333	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD17	Approved
0.7329	Intermediate Similarity	NPD3818	Discontinued
0.7325	Intermediate Similarity	NPD6234	Discontinued
0.7324	Intermediate Similarity	NPD6663	Approved
0.7319	Intermediate Similarity	NPD1876	Approved
0.7319	Intermediate Similarity	NPD1283	Approved
0.7319	Intermediate Similarity	NPD3225	Approved
0.731	Intermediate Similarity	NPD3748	Approved
0.7308	Intermediate Similarity	NPD4967	Phase 2
0.7308	Intermediate Similarity	NPD3882	Suspended
0.7308	Intermediate Similarity	NPD4965	Approved
0.7308	Intermediate Similarity	NPD4966	Approved
0.7299	Intermediate Similarity	NPD9717	Approved
0.7297	Intermediate Similarity	NPD8166	Discontinued
0.7297	Intermediate Similarity	NPD3400	Discontinued
0.729	Intermediate Similarity	NPD7819	Suspended
0.729	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5736	Approved
0.7286	Intermediate Similarity	NPD2861	Phase 2
0.7279	Intermediate Similarity	NPD3847	Discontinued
0.7273	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD943	Approved
0.7273	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5406	Approved
0.726	Intermediate Similarity	NPD5408	Approved
0.726	Intermediate Similarity	NPD5405	Approved
0.726	Intermediate Similarity	NPD5404	Approved
0.7244	Intermediate Similarity	NPD5402	Approved
0.7244	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5048	Discontinued
0.7237	Intermediate Similarity	NPD5403	Approved
0.7231	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1610	Phase 2
0.7226	Intermediate Similarity	NPD422	Phase 1
0.7226	Intermediate Similarity	NPD6801	Discontinued
0.7226	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5401	Approved
0.7214	Intermediate Similarity	NPD5647	Approved
0.7214	Intermediate Similarity	NPD2798	Approved
0.7211	Intermediate Similarity	NPD2346	Discontinued
0.7209	Intermediate Similarity	NPD9266	Approved
0.7209	Intermediate Similarity	NPD74	Approved
0.7208	Intermediate Similarity	NPD6599	Discontinued
0.7203	Intermediate Similarity	NPD4062	Phase 3
0.72	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1241	Discontinued
0.7192	Intermediate Similarity	NPD4308	Phase 3
0.7188	Intermediate Similarity	NPD3134	Approved
0.7188	Intermediate Similarity	NPD6232	Discontinued
0.7181	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6273	Approved
0.7162	Intermediate Similarity	NPD5958	Discontinued
0.716	Intermediate Similarity	NPD7473	Discontinued
0.7153	Intermediate Similarity	NPD2979	Phase 3
0.7152	Intermediate Similarity	NPD6559	Discontinued
0.7152	Intermediate Similarity	NPD1511	Approved
0.7143	Intermediate Similarity	NPD3267	Approved
0.7143	Intermediate Similarity	NPD3266	Approved
0.7132	Intermediate Similarity	NPD9267	Approved
0.7132	Intermediate Similarity	NPD9264	Approved
0.7132	Intermediate Similarity	NPD9263	Approved
0.7123	Intermediate Similarity	NPD7097	Phase 1
0.712	Intermediate Similarity	NPD1238	Approved
0.712	Intermediate Similarity	NPD3020	Approved
0.7114	Intermediate Similarity	NPD2800	Approved
0.7114	Intermediate Similarity	NPD1243	Approved
0.7113	Intermediate Similarity	NPD4908	Phase 1
0.7113	Intermediate Similarity	NPD2614	Approved
0.7105	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD447	Suspended
0.7101	Intermediate Similarity	NPD1201	Approved
0.7101	Intermediate Similarity	NPD1281	Approved
0.7099	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5953	Discontinued
0.7086	Intermediate Similarity	NPD7440	Discontinued
0.7083	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD2182	Approved
0.7075	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2801	Approved
0.7067	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4110	Phase 3
0.7067	Intermediate Similarity	NPD7003	Approved
0.7063	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3027	Phase 3
0.7063	Intermediate Similarity	NPD5494	Approved
0.7059	Intermediate Similarity	NPD1512	Approved
0.7059	Intermediate Similarity	NPD1548	Phase 1
0.705	Intermediate Similarity	NPD9269	Phase 2
0.7041	Intermediate Similarity	NPD8434	Phase 2
0.7037	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4060	Phase 1
0.7032	Intermediate Similarity	NPD3455	Phase 2
0.7032	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5909	Discontinued
0.7027	Intermediate Similarity	NPD2438	Suspended
0.7025	Intermediate Similarity	NPD3817	Phase 2
0.7023	Intermediate Similarity	NPD2067	Discontinued
0.7016	Intermediate Similarity	NPD2859	Approved
0.7016	Intermediate Similarity	NPD2860	Approved
0.7014	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1296	Phase 2
0.7014	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7228	Approved
0.7007	Intermediate Similarity	NPD5585	Approved
0.7007	Intermediate Similarity	NPD9268	Approved
0.7	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1358	Approved
0.6992	Remote Similarity	NPD5535	Approved
0.6986	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4340	Discontinued
0.6986	Remote Similarity	NPD5124	Phase 1
0.6975	Remote Similarity	NPD7229	Phase 3
0.6972	Remote Similarity	NPD1019	Discontinued
0.697	Remote Similarity	NPD7286	Phase 2
0.6966	Remote Similarity	NPD520	Approved
0.6964	Remote Similarity	NPD8312	Approved
0.6964	Remote Similarity	NPD8313	Approved
0.6962	Remote Similarity	NPD8455	Phase 2
0.6957	Remote Similarity	NPD3019	Approved
0.6957	Remote Similarity	NPD2932	Approved
0.6946	Remote Similarity	NPD7685	Pre-registration
0.6939	Remote Similarity	NPD6653	Approved
0.6935	Remote Similarity	NPD2933	Approved
0.6935	Remote Similarity	NPD2934	Approved
0.6933	Remote Similarity	NPD4534	Discontinued
0.6929	Remote Similarity	NPD3972	Approved
0.6923	Remote Similarity	NPD7458	Discontinued
0.6923	Remote Similarity	NPD968	Approved
0.6918	Remote Similarity	NPD1613	Approved
0.6918	Remote Similarity	NPD4307	Phase 2

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