NPASS Compound

Structure

CID280704 OpenBabel06191716092D 27 28 0 0 1 0 0 0 0 0999 V2000 -5.1962 -3.0000 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 -2.5981 -0.5000 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 -3.4641 -0.0000 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 -3.4641 -2.0000 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 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 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 -0.8660 -1.5000 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 -1.7321 -3.0000 0.0000 C 0 0 1 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 0.8660 -0.5000 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 0.0000 -0.0000 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 -1.7321 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 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 1 26 1 0 0 0 0 2 27 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 12 2 0 0 0 0 7 18 1 0 0 0 0 8 13 2 0 0 0 0 8 19 1 0 0 0 0 9 14 1 0 0 0 0 9 21 1 0 0 0 0 10 14 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 20 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 15 11 1 1 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 19 2 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.17
Volume:	383.076
LogP:	0.515
LogD:	1.306
LogS:	-1.854
# Rotatable Bonds:	9
TPSA:	119.61
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	3.23
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.053
MDCK Permeability:	6.169477273942903e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.278
Human Intestinal Absorption (HIA):	0.706
20% Bioavailability (F20%):	0.81
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.103
Plasma Protein Binding (PPB):	58.081451416015625%
Volume Distribution (VD):	0.642
Pgp-substrate:	21.890361785888672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.43
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.54
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.405
CYP2D6-inhibitor:	0.109
CYP2D6-substrate:	0.66
CYP3A4-inhibitor:	0.222
CYP3A4-substrate:	0.864

ADMET: Excretion

Clearance (CL):	11.427
Half-life (T1/2):	0.844

ADMET: Toxicity

hERG Blockers:	0.078
Human Hepatotoxicity (H-HT):	0.328
Drug-inuced Liver Injury (DILI):	0.083
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.26
Skin Sensitization:	0.201
Carcinogencity:	0.07
Eye Corrosion:	0.003
Eye Irritation:	0.194
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC280704

Natural Product ID:	NPC280704
*Common Name:**	Daphneresinol
IUPAC Name:	(2R)-2-[bis(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)butane-1,4-diol
Synonyms:	Daphneresinol
Standard InCHIKey:	YGZVYTHCDLUFFA-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C20H26O7/c1-26-18-7-12(3-5-16(18)24)20(15(11-23)14(9-21)10-22)13-4-6-17(25)19(8-13)27-2/h3-8,14-15,20-25H,9-11H2,1-2H3/t15-/m0/s1
SMILES:	OC[C@H](C(c1ccc(c(c1)OC)O)c1ccc(c(c1)OC)O)C(CO)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL574120
PubChem CID:	45481969
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	stem bark	Kunming, Yunnan Province, China	n.a.	PMID[18986199]
NPO23754	Solanum aculeatissimum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21329	Ilyonectria destructans	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23754	Solanum aculeatissimum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10211	Pajanelia multijuga	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12339	Daphne feddei	Species	Thymelaeaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	300000.0	nM	PMID[550269]

☑ 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 NPC280704 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	325
0.1-0.2	1372
0.2-0.3	4042
0.3-0.4	11939
0.4-0.5	6597
0.5-0.6	4987
0.6-0.7	8696
0.7-0.8	3405
0.8-0.85	763
0.85-0.9	435
0.9-0.95	112
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
0.9914	High Similarity	NPC85488
0.9667	High Similarity	NPC118533
0.9667	High Similarity	NPC165045
0.9667	High Similarity	NPC5428
0.9658	High Similarity	NPC473853
0.9658	High Similarity	NPC262156
0.9658	High Similarity	NPC113865
0.9658	High Similarity	NPC312675
0.9658	High Similarity	NPC343720
0.9658	High Similarity	NPC470212
0.9658	High Similarity	NPC184651
0.9658	High Similarity	NPC324571
0.9658	High Similarity	NPC54872
0.9655	High Similarity	NPC232316
0.9655	High Similarity	NPC165133
0.9655	High Similarity	NPC117780
0.9655	High Similarity	NPC56214
0.9655	High Similarity	NPC227217
0.9655	High Similarity	NPC242885
0.9655	High Similarity	NPC95614
0.9573	High Similarity	NPC207613
0.9569	High Similarity	NPC281298
0.9569	High Similarity	NPC310338
0.9508	High Similarity	NPC475875
0.95	High Similarity	NPC148627
0.9496	High Similarity	NPC317769
0.9496	High Similarity	NPC31344
0.9492	High Similarity	NPC38996
0.9492	High Similarity	NPC160380
0.9483	High Similarity	NPC474040
0.9483	High Similarity	NPC470626
0.9431	High Similarity	NPC187998
0.9431	High Similarity	NPC257582
0.9431	High Similarity	NPC77040
0.9431	High Similarity	NPC174495
0.9431	High Similarity	NPC153739
0.9431	High Similarity	NPC42300
0.9431	High Similarity	NPC242807
0.9431	High Similarity	NPC241522
0.9431	High Similarity	NPC92164
0.9431	High Similarity	NPC64201
0.9431	High Similarity	NPC145305
0.9426	High Similarity	NPC307050
0.9426	High Similarity	NPC277458
0.9402	High Similarity	NPC24474
0.9402	High Similarity	NPC311595
0.9397	High Similarity	NPC293619
0.9355	High Similarity	NPC277804
0.9355	High Similarity	NPC474017
0.9333	High Similarity	NPC471693
0.9328	High Similarity	NPC476343
0.9316	High Similarity	NPC474214
0.9274	High Similarity	NPC173308
0.9274	High Similarity	NPC181079
0.9268	High Similarity	NPC128208
0.9268	High Similarity	NPC184733
0.9268	High Similarity	NPC282703
0.9268	High Similarity	NPC474178
0.9268	High Similarity	NPC21867
0.9268	High Similarity	NPC11258
0.9268	High Similarity	NPC129570
0.9268	High Similarity	NPC252307
0.9268	High Similarity	NPC245826
0.9268	High Similarity	NPC45774
0.9268	High Similarity	NPC470084
0.9237	High Similarity	NPC474320
0.9231	High Similarity	NPC164386
0.92	High Similarity	NPC161557
0.92	High Similarity	NPC27843
0.92	High Similarity	NPC40432
0.92	High Similarity	NPC7171
0.92	High Similarity	NPC158079
0.92	High Similarity	NPC115207
0.92	High Similarity	NPC228346
0.9194	High Similarity	NPC170844
0.9194	High Similarity	NPC476968
0.9187	High Similarity	NPC183181
0.9187	High Similarity	NPC127587
0.9187	High Similarity	NPC319625
0.9187	High Similarity	NPC118787
0.9187	High Similarity	NPC41706
0.9187	High Similarity	NPC111247
0.9187	High Similarity	NPC163332
0.9187	High Similarity	NPC147821
0.9187	High Similarity	NPC292056
0.918	High Similarity	NPC228771
0.918	High Similarity	NPC29008
0.918	High Similarity	NPC9067
0.918	High Similarity	NPC266705
0.9167	High Similarity	NPC127389
0.9167	High Similarity	NPC290451
0.9145	High Similarity	NPC9341
0.9145	High Similarity	NPC81067
0.9134	High Similarity	NPC311256
0.9134	High Similarity	NPC287745
0.9127	High Similarity	NPC106739
0.9127	High Similarity	NPC181049
0.9127	High Similarity	NPC207400
0.912	High Similarity	NPC275950
0.912	High Similarity	NPC143483
0.9113	High Similarity	NPC470213
0.9113	High Similarity	NPC206615
0.9113	High Similarity	NPC186843
0.9113	High Similarity	NPC472968
0.9113	High Similarity	NPC98631
0.9106	High Similarity	NPC76451
0.9106	High Similarity	NPC206882
0.9106	High Similarity	NPC178284
0.9106	High Similarity	NPC191037
0.9106	High Similarity	NPC274356
0.9106	High Similarity	NPC58607
0.9098	High Similarity	NPC114901
0.9098	High Similarity	NPC293701
0.9098	High Similarity	NPC48990
0.9062	High Similarity	NPC101624
0.9062	High Similarity	NPC113295
0.9062	High Similarity	NPC184938
0.9055	High Similarity	NPC169973
0.9055	High Similarity	NPC158331
0.9052	High Similarity	NPC165106
0.9048	High Similarity	NPC476345
0.9048	High Similarity	NPC232275
0.904	High Similarity	NPC5851
0.904	High Similarity	NPC86030
0.904	High Similarity	NPC212015
0.9032	High Similarity	NPC106511
0.9032	High Similarity	NPC21563
0.9024	High Similarity	NPC472093
0.9024	High Similarity	NPC208950
0.9024	High Similarity	NPC17943
0.9024	High Similarity	NPC57490
0.9024	High Similarity	NPC194519
0.9024	High Similarity	NPC475169
0.9024	High Similarity	NPC221077
0.9024	High Similarity	NPC116907
0.9024	High Similarity	NPC298757
0.9024	High Similarity	NPC251855
0.9024	High Similarity	NPC117214
0.9024	High Similarity	NPC203133
0.9024	High Similarity	NPC233410
0.9024	High Similarity	NPC193544
0.9016	High Similarity	NPC197757
0.9016	High Similarity	NPC228922
0.9008	High Similarity	NPC470804
0.9	High Similarity	NPC148615
0.9	High Similarity	NPC35071
0.9	High Similarity	NPC177475
0.8992	High Similarity	NPC177160
0.8992	High Similarity	NPC10737
0.8992	High Similarity	NPC263367
0.8992	High Similarity	NPC29799
0.8992	High Similarity	NPC209985
0.8992	High Similarity	NPC54743
0.8992	High Similarity	NPC477939
0.8992	High Similarity	NPC156502
0.8984	High Similarity	NPC478085
0.8984	High Similarity	NPC244983
0.8984	High Similarity	NPC67247
0.8984	High Similarity	NPC326095
0.8976	High Similarity	NPC471505
0.8976	High Similarity	NPC4940
0.8976	High Similarity	NPC253105
0.8976	High Similarity	NPC201587
0.8976	High Similarity	NPC204215
0.8976	High Similarity	NPC6451
0.8976	High Similarity	NPC175067
0.896	High Similarity	NPC72529
0.8943	High Similarity	NPC109822
0.8943	High Similarity	NPC94276
0.8934	High Similarity	NPC41562
0.8934	High Similarity	NPC30462
0.8917	High Similarity	NPC135961
0.8917	High Similarity	NPC181969
0.8917	High Similarity	NPC320987
0.8915	High Similarity	NPC126409
0.8915	High Similarity	NPC256262
0.8915	High Similarity	NPC99572
0.8908	High Similarity	NPC86947
0.8898	High Similarity	NPC472597
0.8898	High Similarity	NPC474356
0.8898	High Similarity	NPC45715
0.8898	High Similarity	NPC470096
0.8898	High Similarity	NPC470095
0.8898	High Similarity	NPC47194
0.8898	High Similarity	NPC473264
0.8898	High Similarity	NPC12275
0.8898	High Similarity	NPC475815
0.888	High Similarity	NPC324112
0.888	High Similarity	NPC293054
0.888	High Similarity	NPC246620
0.888	High Similarity	NPC74817
0.888	High Similarity	NPC282000
0.888	High Similarity	NPC236791
0.888	High Similarity	NPC124452
0.888	High Similarity	NPC169474
0.888	High Similarity	NPC159968
0.888	High Similarity	NPC82679
0.8879	High Similarity	NPC8547
0.8879	High Similarity	NPC139617
0.8879	High Similarity	NPC257124

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 NPC280704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	848
0.2-0.3	1647
0.3-0.4	2651
0.4-0.5	1822
0.5-0.6	982
0.6-0.7	716
0.7-0.8	175
0.8-0.85	9
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9194	High Similarity	NPD3027	Phase 3
0.9052	High Similarity	NPD5283	Phase 1
0.8879	High Similarity	NPD228	Approved
0.8707	High Similarity	NPD3022	Approved
0.8707	High Similarity	NPD3021	Approved
0.856	High Similarity	NPD4379	Clinical (unspecified phase)
0.8538	High Similarity	NPD3620	Phase 2
0.8538	High Similarity	NPD3619	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD1613	Approved
0.8397	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD2684	Approved
0.813	Intermediate Similarity	NPD7157	Approved
0.8125	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD4060	Phase 1
0.8033	Intermediate Similarity	NPD7843	Approved
0.8016	Intermediate Similarity	NPD1357	Approved
0.8	Intermediate Similarity	NPD5536	Phase 2
0.7931	Intermediate Similarity	NPD3020	Approved
0.7879	Intermediate Similarity	NPD2861	Phase 2
0.7846	Intermediate Similarity	NPD2982	Phase 2
0.7846	Intermediate Similarity	NPD2983	Phase 2
0.7836	Intermediate Similarity	NPD5111	Phase 2
0.7836	Intermediate Similarity	NPD5109	Approved
0.7836	Intermediate Similarity	NPD5110	Phase 2
0.7829	Intermediate Similarity	NPD3705	Approved
0.782	Intermediate Similarity	NPD4908	Phase 1
0.7786	Intermediate Similarity	NPD3060	Approved
0.7786	Intermediate Similarity	NPD5177	Phase 3
0.7778	Intermediate Similarity	NPD2674	Phase 3
0.7769	Intermediate Similarity	NPD2981	Phase 2
0.7744	Intermediate Similarity	NPD3018	Phase 2
0.7721	Intermediate Similarity	NPD1558	Phase 1
0.7704	Intermediate Similarity	NPD3144	Approved
0.7704	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD3145	Approved
0.7698	Intermediate Similarity	NPD6671	Approved
0.7692	Intermediate Similarity	NPD1610	Phase 2
0.7686	Intermediate Similarity	NPD968	Approved
0.7674	Intermediate Similarity	NPD6516	Phase 2
0.7674	Intermediate Similarity	NPD5846	Approved
0.7672	Intermediate Similarity	NPD2860	Approved
0.7672	Intermediate Similarity	NPD2859	Approved
0.7669	Intermediate Similarity	NPD6584	Phase 3
0.766	Intermediate Similarity	NPD6674	Discontinued
0.7643	Intermediate Similarity	NPD7266	Discontinued
0.7634	Intermediate Similarity	NPD2232	Approved
0.7634	Intermediate Similarity	NPD2230	Approved
0.7634	Intermediate Similarity	NPD2233	Approved
0.763	Intermediate Similarity	NPD7095	Approved
0.7623	Intermediate Similarity	NPD290	Approved
0.7612	Intermediate Similarity	NPD9494	Approved
0.7606	Intermediate Similarity	NPD6331	Phase 2
0.7606	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD4110	Phase 3
0.7594	Intermediate Similarity	NPD3094	Phase 2
0.7591	Intermediate Similarity	NPD2238	Phase 2
0.7586	Intermediate Similarity	NPD2934	Approved
0.7586	Intermediate Similarity	NPD9296	Approved
0.7586	Intermediate Similarity	NPD2933	Approved
0.7556	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6895	Approved
0.7554	Intermediate Similarity	NPD4538	Approved
0.7554	Intermediate Similarity	NPD6896	Approved
0.7554	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD4536	Approved
0.7552	Intermediate Similarity	NPD5241	Discontinued
0.7538	Intermediate Similarity	NPD2667	Approved
0.7538	Intermediate Similarity	NPD2668	Approved
0.7536	Intermediate Similarity	NPD5735	Approved
0.7536	Intermediate Similarity	NPD3657	Discovery
0.7536	Intermediate Similarity	NPD6355	Discontinued
0.7535	Intermediate Similarity	NPD4162	Approved
0.7535	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD37	Approved
0.7517	Intermediate Similarity	NPD1934	Approved
0.75	Intermediate Similarity	NPD5451	Approved
0.75	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2235	Phase 2
0.75	Intermediate Similarity	NPD2231	Phase 2
0.75	Intermediate Similarity	NPD291	Approved
0.7482	Intermediate Similarity	NPD6653	Approved
0.7467	Intermediate Similarity	NPD2977	Approved
0.7467	Intermediate Similarity	NPD2978	Approved
0.7466	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD52	Approved
0.7466	Intermediate Similarity	NPD7526	Approved
0.7447	Intermediate Similarity	NPD2161	Phase 2
0.7444	Intermediate Similarity	NPD6583	Phase 3
0.7444	Intermediate Similarity	NPD6582	Phase 2
0.7431	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD3092	Approved
0.7413	Intermediate Similarity	NPD4237	Approved
0.7413	Intermediate Similarity	NPD4236	Phase 3
0.7407	Intermediate Similarity	NPD4624	Approved
0.7407	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4626	Approved
0.7394	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6233	Phase 2
0.7388	Intermediate Similarity	NPD8651	Approved
0.7388	Intermediate Similarity	NPD1283	Approved
0.7388	Intermediate Similarity	NPD2922	Phase 1
0.7385	Intermediate Similarity	NPD1548	Phase 1
0.7385	Intermediate Similarity	NPD3091	Approved
0.7376	Intermediate Similarity	NPD5588	Approved
0.7376	Intermediate Similarity	NPD5960	Phase 3
0.7368	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD4966	Approved
0.7368	Intermediate Similarity	NPD4965	Approved
0.7351	Intermediate Similarity	NPD2801	Approved
0.7351	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD3847	Discontinued
0.7338	Intermediate Similarity	NPD4140	Approved
0.7338	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD5585	Approved
0.7328	Intermediate Similarity	NPD1651	Approved
0.7324	Intermediate Similarity	NPD2935	Discontinued
0.7323	Intermediate Similarity	NPD5535	Approved
0.7319	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD6798	Discontinued
0.7319	Intermediate Similarity	NPD5718	Phase 2
0.7315	Intermediate Similarity	NPD4005	Discontinued
0.7313	Intermediate Similarity	NPD5327	Phase 3
0.7313	Intermediate Similarity	NPD4749	Approved
0.7313	Intermediate Similarity	NPD1669	Approved
0.7293	Intermediate Similarity	NPD1091	Approved
0.7288	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4123	Phase 3
0.7279	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7228	Approved
0.7273	Intermediate Similarity	NPD5763	Approved
0.7273	Intermediate Similarity	NPD1375	Discontinued
0.7273	Intermediate Similarity	NPD5762	Approved
0.7266	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6166	Phase 2
0.7261	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7124	Phase 2
0.7255	Intermediate Similarity	NPD3882	Suspended
0.7254	Intermediate Similarity	NPD4108	Discontinued
0.7248	Intermediate Similarity	NPD1653	Approved
0.7246	Intermediate Similarity	NPD4625	Phase 3
0.7241	Intermediate Similarity	NPD8166	Discontinued
0.7241	Intermediate Similarity	NPD4535	Phase 3
0.7241	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4628	Phase 3
0.7234	Intermediate Similarity	NPD4097	Suspended
0.723	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD3496	Discontinued
0.7214	Intermediate Similarity	NPD2979	Phase 3
0.7214	Intermediate Similarity	NPD3062	Approved
0.7214	Intermediate Similarity	NPD3059	Approved
0.7214	Intermediate Similarity	NPD3061	Approved
0.7211	Intermediate Similarity	NPD7041	Phase 2
0.7211	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2438	Suspended
0.72	Intermediate Similarity	NPD1358	Approved
0.7197	Intermediate Similarity	NPD5691	Approved
0.7192	Intermediate Similarity	NPD2677	Approved
0.7192	Intermediate Similarity	NPD6190	Approved
0.7188	Intermediate Similarity	NPD7635	Approved
0.7188	Intermediate Similarity	NPD821	Approved
0.7185	Intermediate Similarity	NPD3685	Discontinued
0.7179	Intermediate Similarity	NPD7199	Phase 2
0.7167	Intermediate Similarity	NPD288	Approved
0.7164	Intermediate Similarity	NPD1281	Approved
0.7154	Intermediate Similarity	NPD709	Approved
0.7153	Intermediate Similarity	NPD3540	Phase 1
0.7152	Intermediate Similarity	NPD4678	Approved
0.7152	Intermediate Similarity	NPD4675	Approved
0.7143	Intermediate Similarity	NPD9381	Approved
0.7143	Intermediate Similarity	NPD4062	Phase 3
0.7143	Intermediate Similarity	NPD5058	Phase 3
0.7143	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3095	Discontinued
0.7143	Intermediate Similarity	NPD9384	Approved
0.7131	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD1242	Phase 1
0.7124	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1182	Approved
0.712	Intermediate Similarity	NPD3134	Approved
0.7113	Intermediate Similarity	NPD5314	Approved
0.7113	Intermediate Similarity	NPD6353	Approved
0.7111	Intermediate Similarity	NPD1840	Phase 2
0.7111	Intermediate Similarity	NPD1608	Approved
0.7103	Intermediate Similarity	NPD2424	Discontinued
0.7103	Intermediate Similarity	NPD2808	Discontinued
0.7103	Intermediate Similarity	NPD7037	Approved
0.7099	Intermediate Similarity	NPD3596	Phase 2
0.7097	Intermediate Similarity	NPD7833	Phase 2
0.7097	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7831	Phase 2
0.7095	Intermediate Similarity	NPD4357	Discontinued
0.7095	Intermediate Similarity	NPD1511	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