NPASS Compound

Structure

NPC146355 OpenBabel07101718322D 24 27 0 0 1 0 0 0 0 0999 V2000 -3.2577 -0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1237 -0.9351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1237 1.0649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 0.9945 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 -1.3090 2.2673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2577 0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 0.6581 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9898 -0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9898 0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3917 1.0649 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8558 -0.9351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 2.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8558 1.0649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2872 2.0594 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 3 2 0 0 0 0 1 9 1 0 0 0 0 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 9 2 0 0 0 0 5 15 1 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 24 1 0 0 0 0 8 23 1 0 0 0 0 11 7 1 1 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 8 1 1 0 0 0 12 18 1 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 14 16 2 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 9 1 6 0 0 0 17 23 1 0 0 0 0 18 10 1 6 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.11
Volume:	322.581
LogP:	1.852
LogD:	2.253
LogS:	-3.256
# Rotatable Bonds:	2
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.632
Synthetic Accessibility Score:	3.856
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.551
MDCK Permeability:	5.88864986639237e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.312
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	91.85865020751953%
Volume Distribution (VD):	0.806
Pgp-substrate:	10.208918571472168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.181
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.089
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.49
CYP2C9-substrate:	0.501
CYP2D6-inhibitor:	0.347
CYP2D6-substrate:	0.28
CYP3A4-inhibitor:	0.254
CYP3A4-substrate:	0.188

ADMET: Excretion

Clearance (CL):	17.96
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.08
Drug-inuced Liver Injury (DILI):	0.193
AMES Toxicity:	0.623
Rat Oral Acute Toxicity:	0.347
Maximum Recommended Daily Dose:	0.346
Skin Sensitization:	0.959
Carcinogencity:	0.637
Eye Corrosion:	0.005
Eye Irritation:	0.964
Respiratory Toxicity:	0.774

Download Data

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

Natural Product: NPC146355

Natural Product ID:	NPC146355
*Common Name:**	(-)-3,3'-Bisdemethylpinoresinol
IUPAC Name:	4-[(3R,3aS,6R,6aS)-3-(3,4-dihydroxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]benzene-1,2-diol
Synonyms:
Standard InCHIKey:	OQSOTSIYXPYTRE-VVDPLQPHSA-N
Standard InCHI:	InChI=1S/C18H18O6/c19-13-3-1-9(5-15(13)21)17-11-7-24-18(12(11)8-23-17)10-2-4-14(20)16(22)6-10/h1-6,11-12,17-22H,7-8H2/t11-,12-,17+,18+/m1/s1
SMILES:	c1cc(c(cc1[C@H]1[C@@H]2CO[C@@H](c3ccc(c(c3)O)O)[C@@H]2CO1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227187
PubChem CID:	24992964
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans

*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
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11348221]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[15844957]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378361]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	Tahiti	n.a.	PMID[17378609]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17480098]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[18076142]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24224843]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27196335]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[32083868]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4323	Morinda citrifolia	Species	Rubiaceae	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
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	5900.0	nM	PMID[559635]
NPT257	Individual Protein	Arachidonate 15-lipoxygenase	Oryctolagus cuniculus	IC50	=	520.0	nM	PMID[559635]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	100000.0	nM	PMID[559635]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	30000.0	nM	PMID[559636]

☑ 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 NPC146355 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	395
0.1-0.2	1321
0.2-0.3	3588
0.3-0.4	10471
0.4-0.5	8979
0.5-0.6	7171
0.6-0.7	8149
0.7-0.8	2329
0.8-0.85	211
0.85-0.9	66
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC131747
1.0	High Similarity	NPC257682
0.9746	High Similarity	NPC473451
0.9435	High Similarity	NPC40432
0.9435	High Similarity	NPC161557
0.9435	High Similarity	NPC7171
0.9435	High Similarity	NPC158079
0.9435	High Similarity	NPC228346
0.9435	High Similarity	NPC27843
0.9435	High Similarity	NPC115207
0.936	High Similarity	NPC207400
0.936	High Similarity	NPC181049
0.9206	High Similarity	NPC4940
0.92	High Similarity	NPC145305
0.92	High Similarity	NPC92164
0.92	High Similarity	NPC187998
0.92	High Similarity	NPC42300
0.92	High Similarity	NPC77040
0.92	High Similarity	NPC64201
0.92	High Similarity	NPC257582
0.92	High Similarity	NPC241522
0.92	High Similarity	NPC242807
0.92	High Similarity	NPC174495
0.92	High Similarity	NPC153739
0.9194	High Similarity	NPC129570
0.9194	High Similarity	NPC128208
0.9194	High Similarity	NPC282703
0.9194	High Similarity	NPC21867
0.9194	High Similarity	NPC184733
0.9194	High Similarity	NPC11258
0.9194	High Similarity	NPC45774
0.9141	High Similarity	NPC99572
0.9141	High Similarity	NPC126409
0.9127	High Similarity	NPC277804
0.912	High Similarity	NPC475875
0.904	High Similarity	NPC470084
0.9008	High Similarity	NPC470414
0.9	High Similarity	NPC308976
0.8992	High Similarity	NPC142547
0.8992	High Similarity	NPC141765
0.8992	High Similarity	NPC135777
0.8992	High Similarity	NPC24490
0.8992	High Similarity	NPC476266
0.8992	High Similarity	NPC165155
0.8992	High Similarity	NPC34103
0.8984	High Similarity	NPC158331
0.896	High Similarity	NPC165045
0.896	High Similarity	NPC118533
0.8931	High Similarity	NPC193666
0.8931	High Similarity	NPC123526
0.8931	High Similarity	NPC88640
0.8915	High Similarity	NPC67247
0.8915	High Similarity	NPC287745
0.8906	High Similarity	NPC204215
0.8906	High Similarity	NPC175067
0.8898	High Similarity	NPC120280
0.888	High Similarity	NPC206882
0.8871	High Similarity	NPC121783
0.8871	High Similarity	NPC34902
0.8871	High Similarity	NPC18449
0.8864	High Similarity	NPC55793
0.8814	High Similarity	NPC123175
0.8814	High Similarity	NPC176730
0.881	High Similarity	NPC5428
0.88	High Similarity	NPC148627
0.879	High Similarity	NPC317769
0.879	High Similarity	NPC31344
0.8779	High Similarity	NPC471988
0.8779	High Similarity	NPC263367
0.8779	High Similarity	NPC54743
0.8779	High Similarity	NPC209985
0.8779	High Similarity	NPC477939
0.8779	High Similarity	NPC177160
0.8779	High Similarity	NPC29799
0.8779	High Similarity	NPC156502
0.8779	High Similarity	NPC10737
0.8769	High Similarity	NPC244983
0.8769	High Similarity	NPC187616
0.8769	High Similarity	NPC193026
0.8769	High Similarity	NPC471942
0.8769	High Similarity	NPC326095
0.8769	High Similarity	NPC49603
0.876	High Similarity	NPC471505
0.874	High Similarity	NPC474178
0.874	High Similarity	NPC252307
0.874	High Similarity	NPC245826
0.8722	High Similarity	NPC177868
0.8712	High Similarity	NPC281780
0.8702	High Similarity	NPC18576
0.8702	High Similarity	NPC101624
0.8702	High Similarity	NPC184938
0.8682	High Similarity	NPC474017
0.8667	High Similarity	NPC255566
0.8667	High Similarity	NPC477898
0.8667	High Similarity	NPC298317
0.8667	High Similarity	NPC265154
0.8661	High Similarity	NPC292056
0.8661	High Similarity	NPC319625
0.8661	High Similarity	NPC41706
0.8661	High Similarity	NPC163332
0.8661	High Similarity	NPC111247
0.8661	High Similarity	NPC118787
0.8661	High Similarity	NPC147821
0.8661	High Similarity	NPC183181
0.8644	High Similarity	NPC179002
0.8644	High Similarity	NPC187583
0.8644	High Similarity	NPC257430
0.864	High Similarity	NPC471693
0.864	High Similarity	NPC280704
0.8636	High Similarity	NPC77861
0.8629	High Similarity	NPC172676
0.8629	High Similarity	NPC65933
0.8629	High Similarity	NPC216929
0.8629	High Similarity	NPC126935
0.8629	High Similarity	NPC312713
0.8629	High Similarity	NPC57268
0.8626	High Similarity	NPC47181
0.8615	High Similarity	NPC106739
0.8615	High Similarity	NPC104077
0.8615	High Similarity	NPC259742
0.8615	High Similarity	NPC219671
0.8615	High Similarity	NPC147616
0.8603	High Similarity	NPC114119
0.8603	High Similarity	NPC470097
0.8603	High Similarity	NPC471415
0.8603	High Similarity	NPC84181
0.8595	High Similarity	NPC301651
0.8595	High Similarity	NPC473556
0.8594	High Similarity	NPC222127
0.8594	High Similarity	NPC82862
0.8594	High Similarity	NPC72529
0.8583	High Similarity	NPC58607
0.8583	High Similarity	NPC191037
0.8583	High Similarity	NPC178284
0.8582	High Similarity	NPC184797
0.8582	High Similarity	NPC160283
0.8582	High Similarity	NPC309124
0.8582	High Similarity	NPC254759
0.8571	High Similarity	NPC101807
0.856	High Similarity	NPC85488
0.8559	High Similarity	NPC174096
0.8559	High Similarity	NPC226401
0.8559	High Similarity	NPC79793
0.8559	High Similarity	NPC147634
0.8559	High Similarity	NPC120982
0.855	High Similarity	NPC26394
0.855	High Similarity	NPC169973
0.854	High Similarity	NPC22150
0.854	High Similarity	NPC279298
0.854	High Similarity	NPC38041
0.854	High Similarity	NPC223185
0.8529	High Similarity	NPC185071
0.8529	High Similarity	NPC12728
0.8527	High Similarity	NPC86030
0.8527	High Similarity	NPC5851
0.8527	High Similarity	NPC476968
0.8527	High Similarity	NPC170844
0.8519	High Similarity	NPC471414
0.8519	High Similarity	NPC87725
0.8519	High Similarity	NPC263261
0.8519	High Similarity	NPC472711
0.8516	High Similarity	NPC127587
0.8516	High Similarity	NPC473092
0.8516	High Similarity	NPC8050
0.8516	High Similarity	NPC473093
0.8507	High Similarity	NPC156376
0.8507	High Similarity	NPC292882
0.8507	High Similarity	NPC473739
0.8507	High Similarity	NPC232164
0.8507	High Similarity	NPC236306
0.8504	High Similarity	NPC194519
0.85	High Similarity	NPC471485
0.8492	Intermediate Similarity	NPC136319
0.8485	Intermediate Similarity	NPC478085
0.848	Intermediate Similarity	NPC473853
0.848	Intermediate Similarity	NPC113865
0.848	Intermediate Similarity	NPC262156
0.848	Intermediate Similarity	NPC184651
0.848	Intermediate Similarity	NPC147654
0.848	Intermediate Similarity	NPC343720
0.848	Intermediate Similarity	NPC54872
0.848	Intermediate Similarity	NPC324571
0.848	Intermediate Similarity	NPC476343
0.848	Intermediate Similarity	NPC470212
0.848	Intermediate Similarity	NPC312675
0.848	Intermediate Similarity	NPC470804
0.8478	Intermediate Similarity	NPC112861
0.8478	Intermediate Similarity	NPC324492
0.8478	Intermediate Similarity	NPC317053
0.8475	Intermediate Similarity	NPC62258
0.8475	Intermediate Similarity	NPC254833
0.8475	Intermediate Similarity	NPC228343
0.8475	Intermediate Similarity	NPC55617
0.8473	Intermediate Similarity	NPC230219
0.8473	Intermediate Similarity	NPC254275
0.8473	Intermediate Similarity	NPC201587
0.8473	Intermediate Similarity	NPC470752
0.8473	Intermediate Similarity	NPC253105
0.8468	Intermediate Similarity	NPC232316
0.8468	Intermediate Similarity	NPC56214

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 NPC146355 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	779
0.2-0.3	1655
0.3-0.4	2890
0.4-0.5	1882
0.5-0.6	1150
0.6-0.7	448
0.7-0.8	28
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8527	High Similarity	NPD3027	Phase 3
0.8475	Intermediate Similarity	NPD3022	Approved
0.8475	Intermediate Similarity	NPD3021	Approved
0.8195	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8195	Intermediate Similarity	NPD1613	Approved
0.8092	Intermediate Similarity	NPD2861	Phase 2
0.803	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD5283	Phase 1
0.7842	Intermediate Similarity	NPD7266	Discontinued
0.7742	Intermediate Similarity	NPD228	Approved
0.7712	Intermediate Similarity	NPD3020	Approved
0.7682	Intermediate Similarity	NPD6234	Discontinued
0.7669	Intermediate Similarity	NPD3094	Phase 2
0.7664	Intermediate Similarity	NPD3620	Phase 2
0.7664	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD3705	Approved
0.7634	Intermediate Similarity	NPD1610	Phase 2
0.763	Intermediate Similarity	NPD4908	Phase 1
0.7586	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD3092	Approved
0.7458	Intermediate Similarity	NPD2859	Approved
0.7458	Intermediate Similarity	NPD2860	Approved
0.7434	Intermediate Similarity	NPD4965	Approved
0.7434	Intermediate Similarity	NPD4966	Approved
0.7434	Intermediate Similarity	NPD4967	Phase 2
0.741	Intermediate Similarity	NPD3062	Approved
0.741	Intermediate Similarity	NPD4060	Phase 1
0.741	Intermediate Similarity	NPD3059	Approved
0.741	Intermediate Similarity	NPD3061	Approved
0.7388	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD2933	Approved
0.7373	Intermediate Similarity	NPD2934	Approved
0.7361	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD5735	Approved
0.7355	Intermediate Similarity	NPD1242	Phase 1
0.7348	Intermediate Similarity	NPD9384	Approved
0.7348	Intermediate Similarity	NPD5125	Phase 3
0.7348	Intermediate Similarity	NPD5126	Approved
0.7348	Intermediate Similarity	NPD9381	Approved
0.7342	Intermediate Similarity	NPD7228	Approved
0.7328	Intermediate Similarity	NPD3091	Approved
0.7328	Intermediate Similarity	NPD1548	Phase 1
0.7324	Intermediate Similarity	NPD5588	Approved
0.7305	Intermediate Similarity	NPD5314	Approved
0.7303	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1558	Phase 1
0.7279	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1357	Approved
0.7259	Intermediate Similarity	NPD2982	Phase 2
0.7259	Intermediate Similarity	NPD2983	Phase 2
0.7244	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4237	Approved
0.7241	Intermediate Similarity	NPD4236	Phase 3
0.7237	Intermediate Similarity	NPD37	Approved
0.7237	Intermediate Similarity	NPD1934	Approved
0.7234	Intermediate Similarity	NPD230	Phase 1
0.7231	Intermediate Similarity	NPD7157	Approved
0.7222	Intermediate Similarity	NPD2684	Approved
0.72	Intermediate Similarity	NPD968	Approved
0.7192	Intermediate Similarity	NPD8166	Discontinued
0.7185	Intermediate Similarity	NPD2981	Phase 2
0.7174	Intermediate Similarity	NPD3018	Phase 2
0.7165	Intermediate Similarity	NPD4750	Phase 3
0.7163	Intermediate Similarity	NPD2238	Phase 2
0.7143	Intermediate Similarity	NPD3764	Approved
0.7133	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4538	Approved
0.7133	Intermediate Similarity	NPD4536	Approved
0.7132	Intermediate Similarity	NPD4749	Approved
0.7132	Intermediate Similarity	NPD9622	Approved
0.7132	Intermediate Similarity	NPD7843	Approved
0.7123	Intermediate Similarity	NPD3060	Approved
0.7123	Intermediate Similarity	NPD6674	Discontinued
0.7113	Intermediate Similarity	NPD6355	Discontinued
0.7111	Intermediate Similarity	NPD1091	Approved
0.7101	Intermediate Similarity	NPD6584	Phase 3
0.7099	Intermediate Similarity	NPD6671	Approved
0.7097	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3882	Suspended
0.7095	Intermediate Similarity	NPD5058	Phase 3
0.709	Intermediate Similarity	NPD3095	Discontinued
0.7083	Intermediate Similarity	NPD5960	Phase 3
0.7083	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2977	Approved
0.7078	Intermediate Similarity	NPD2978	Approved
0.7075	Intermediate Similarity	NPD4110	Phase 3
0.7075	Intermediate Similarity	NPD6331	Phase 2
0.7075	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4625	Phase 3
0.7068	Intermediate Similarity	NPD7741	Discontinued
0.7059	Intermediate Similarity	NPD2231	Phase 2
0.7059	Intermediate Similarity	NPD2235	Phase 2
0.705	Intermediate Similarity	NPD5736	Approved
0.7047	Intermediate Similarity	NPD1511	Approved
0.7034	Intermediate Similarity	NPD2161	Phase 2
0.7029	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7199	Phase 2
0.7021	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3818	Discontinued
0.7016	Intermediate Similarity	NPD940	Approved
0.7016	Intermediate Similarity	NPD846	Approved
0.7007	Intermediate Similarity	NPD5327	Phase 3
0.7	Intermediate Similarity	NPD9379	Approved
0.7	Intermediate Similarity	NPD9377	Approved
0.7	Intermediate Similarity	NPD7635	Approved
0.6992	Remote Similarity	NPD5536	Phase 2
0.6988	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5762	Approved
0.6986	Remote Similarity	NPD5763	Approved
0.6986	Remote Similarity	NPD1375	Discontinued
0.6978	Remote Similarity	NPD9620	Approved
0.6978	Remote Similarity	NPD9621	Approved
0.6978	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD9619	Approved
0.6974	Remote Similarity	NPD1653	Approved
0.6972	Remote Similarity	NPD6663	Approved
0.6968	Remote Similarity	NPD2801	Approved
0.6967	Remote Similarity	NPD288	Approved
0.6963	Remote Similarity	NPD5846	Approved
0.6963	Remote Similarity	NPD6516	Phase 2
0.6963	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4628	Phase 3
0.6957	Remote Similarity	NPD8651	Approved
0.6957	Remote Similarity	NPD5311	Approved
0.6957	Remote Similarity	NPD5310	Approved
0.6957	Remote Similarity	NPD6696	Suspended
0.6954	Remote Similarity	NPD1512	Approved
0.695	Remote Similarity	NPD7095	Approved
0.6944	Remote Similarity	NPD823	Approved
0.6944	Remote Similarity	NPD6653	Approved
0.6944	Remote Similarity	NPD817	Approved
0.6944	Remote Similarity	NPD6353	Approved
0.694	Remote Similarity	NPD1182	Approved
0.6939	Remote Similarity	NPD7037	Approved
0.6937	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD2233	Approved
0.6934	Remote Similarity	NPD1840	Phase 2
0.6934	Remote Similarity	NPD2232	Approved
0.6934	Remote Similarity	NPD1608	Approved
0.6934	Remote Similarity	NPD2230	Approved
0.6923	Remote Similarity	NPD943	Approved
0.6923	Remote Similarity	NPD4140	Approved
0.6913	Remote Similarity	NPD2677	Approved
0.6906	Remote Similarity	NPD3055	Approved
0.6906	Remote Similarity	NPD3053	Approved
0.6901	Remote Similarity	NPD601	Approved
0.6901	Remote Similarity	NPD5111	Phase 2
0.6901	Remote Similarity	NPD598	Approved
0.6901	Remote Similarity	NPD597	Approved
0.6901	Remote Similarity	NPD5110	Phase 2
0.6901	Remote Similarity	NPD5109	Approved
0.6897	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6166	Phase 2
0.6894	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5177	Phase 3
0.6887	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4123	Phase 3
0.6885	Remote Similarity	NPD844	Approved
0.6884	Remote Similarity	NPD6582	Phase 2
0.6884	Remote Similarity	NPD6583	Phase 3
0.6875	Remote Similarity	NPD290	Approved
0.6875	Remote Similarity	NPD3657	Discovery
0.6871	Remote Similarity	NPD6004	Phase 3
0.6871	Remote Similarity	NPD6005	Phase 3
0.6871	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6002	Phase 3
0.6871	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4624	Approved
0.6853	Remote Similarity	NPD6405	Approved
0.6853	Remote Similarity	NPD1130	Approved
0.6853	Remote Similarity	NPD6233	Phase 2
0.6853	Remote Similarity	NPD2674	Phase 3
0.6853	Remote Similarity	NPD6407	Approved
0.6853	Remote Similarity	NPD1136	Approved
0.6853	Remote Similarity	NPD1132	Approved
0.6848	Remote Similarity	NPD7240	Approved
0.6846	Remote Similarity	NPD3892	Phase 2
0.6842	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD2932	Approved
0.6838	Remote Similarity	NPD3019	Approved
0.6838	Remote Similarity	NPD2668	Approved
0.6838	Remote Similarity	NPD2667	Approved
0.6838	Remote Similarity	NPD4059	Approved
0.6826	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2229	Approved
0.6818	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3455	Phase 2
0.6818	Remote Similarity	NPD2228	Approved
0.6818	Remote Similarity	NPD2234	Approved
0.6815	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2563	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