NPASS Compound

Structure

CID64201 OpenBabel06191715402D 27 29 0 0 1 0 0 0 0 0999 V2000 5.0659 -0.4751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 1.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2579 1.4565 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 -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 -1.9487 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -0.2024 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 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 -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 -1.0827 -1.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 1 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 -3.6808 0.2976 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 0.5000 -0.8660 0.0000 C 0 0 2 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 -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 -3.6808 1.2976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6646 0.5430 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 24 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 7 2 0 0 0 0 5 14 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 13 1 0 0 0 0 9 13 2 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 12 15 1 0 0 0 0 12 27 1 0 0 0 0 15 8 1 1 0 0 0 15 16 1 0 0 0 0 16 11 1 1 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 23 1 0 0 0 0 18 20 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 14 1 6 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.17
Volume:	383.025
LogP:	2.547
LogD:	2.696
LogS:	-3.858
# Rotatable Bonds:	7
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.776
Synthetic Accessibility Score:	3.335
Fsp3:	0.429
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:	-4.725
MDCK Permeability:	1.3994334040035028e-05
Pgp-inhibitor:	0.576
Pgp-substrate:	0.565
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.233
Plasma Protein Binding (PPB):	92.38597869873047%
Volume Distribution (VD):	0.516
Pgp-substrate:	6.545222759246826%

ADMET: Metabolism

CYP1A2-inhibitor:	0.085
CYP1A2-substrate:	0.865
CYP2C19-inhibitor:	0.187
CYP2C19-substrate:	0.87
CYP2C9-inhibitor:	0.396
CYP2C9-substrate:	0.664
CYP2D6-inhibitor:	0.242
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.644
CYP3A4-substrate:	0.873

ADMET: Excretion

Clearance (CL):	11.353
Half-life (T1/2):	0.808

ADMET: Toxicity

hERG Blockers:	0.381
Human Hepatotoxicity (H-HT):	0.202
Drug-inuced Liver Injury (DILI):	0.792
AMES Toxicity:	0.085
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.234
Skin Sensitization:	0.924
Carcinogencity:	0.144
Eye Corrosion:	0.004
Eye Irritation:	0.125
Respiratory Toxicity:	0.549

Download Data

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

Natural Product: NPC64201

Natural Product ID:	NPC64201
*Common Name:**	Lariciresinol-4'-Monomethyl Ether
IUPAC Name:	4-[[(3R,4R,5S)-5-(3,4-dimethoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol
Synonyms:	Lariciresinol-4'-Monomethyl Ether
Standard InCHIKey:	VVKJZDWKHOGKOG-CKJXQJPGSA-N
Standard InCHI:	InChI=1S/C21H26O6/c1-24-18-7-5-14(10-20(18)26-3)21-16(11-22)15(12-27-21)8-13-4-6-17(23)19(9-13)25-2/h4-7,9-10,15-16,21-23H,8,11-12H2,1-3H3/t15-,16-,21+/m0/s1
SMILES:	OC[C@H]1[C@H](CO[C@@H]1c1ccc(c(c1)OC)OC)Cc1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483422
PubChem CID:	155977
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003422] 7,9'-epoxylignans

*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
NPO393	Monechma ciliatum	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6512538]
NPO40945	Turrea nilotica	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[6512538]
NPO5087	Daphne oleoides	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5087	Daphne oleoides	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5087	Daphne oleoides	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO393	Monechma ciliatum	Species	Acanthaceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[450011]

☑ 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 NPC64201 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	369
0.1-0.2	1212
0.2-0.3	3318
0.3-0.4	8896
0.4-0.5	10196
0.5-0.6	4605
0.6-0.7	9173
0.7-0.8	3451
0.8-0.85	815
0.85-0.9	487
0.9-0.95	133
0.95-1	42

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC153739
1.0	High Similarity	NPC42300
1.0	High Similarity	NPC257582
1.0	High Similarity	NPC145305
1.0	High Similarity	NPC242807
1.0	High Similarity	NPC241522
1.0	High Similarity	NPC92164
1.0	High Similarity	NPC187998
1.0	High Similarity	NPC77040
1.0	High Similarity	NPC174495
0.9919	High Similarity	NPC475875
0.9919	High Similarity	NPC277804
0.9837	High Similarity	NPC129570
0.9837	High Similarity	NPC11258
0.9837	High Similarity	NPC128208
0.9837	High Similarity	NPC21867
0.9837	High Similarity	NPC45774
0.9837	High Similarity	NPC184733
0.9837	High Similarity	NPC470084
0.9837	High Similarity	NPC282703
0.976	High Similarity	NPC228346
0.976	High Similarity	NPC158079
0.976	High Similarity	NPC115207
0.976	High Similarity	NPC40432
0.976	High Similarity	NPC7171
0.976	High Similarity	NPC27843
0.976	High Similarity	NPC161557
0.9756	High Similarity	NPC118533
0.9756	High Similarity	NPC165045
0.9685	High Similarity	NPC287745
0.9683	High Similarity	NPC207400
0.9683	High Similarity	NPC181049
0.9675	High Similarity	NPC206882
0.9606	High Similarity	NPC158331
0.9597	High Similarity	NPC5428
0.9593	High Similarity	NPC148627
0.9535	High Similarity	NPC263367
0.9535	High Similarity	NPC10737
0.9535	High Similarity	NPC54743
0.9535	High Similarity	NPC209985
0.9535	High Similarity	NPC477939
0.9535	High Similarity	NPC177160
0.9535	High Similarity	NPC29799
0.9535	High Similarity	NPC156502
0.9531	High Similarity	NPC244983
0.9531	High Similarity	NPC67247
0.9531	High Similarity	NPC326095
0.9528	High Similarity	NPC204215
0.9528	High Similarity	NPC175067
0.9528	High Similarity	NPC4940
0.952	High Similarity	NPC245826
0.952	High Similarity	NPC252307
0.952	High Similarity	NPC474178
0.9457	High Similarity	NPC101624
0.9457	High Similarity	NPC184938
0.9457	High Similarity	NPC126409
0.9457	High Similarity	NPC99572
0.9449	High Similarity	NPC474017
0.944	High Similarity	NPC292056
0.944	High Similarity	NPC163332
0.944	High Similarity	NPC41706
0.944	High Similarity	NPC183181
0.944	High Similarity	NPC319625
0.944	High Similarity	NPC111247
0.944	High Similarity	NPC147821
0.944	High Similarity	NPC118787
0.9431	High Similarity	NPC31344
0.9431	High Similarity	NPC473451
0.9431	High Similarity	NPC317769
0.9431	High Similarity	NPC471693
0.9431	High Similarity	NPC280704
0.9385	High Similarity	NPC471988
0.9385	High Similarity	NPC77861
0.938	High Similarity	NPC193026
0.938	High Similarity	NPC471942
0.938	High Similarity	NPC49603
0.938	High Similarity	NPC187616
0.9375	High Similarity	NPC106739
0.9375	High Similarity	NPC471505
0.936	High Similarity	NPC178284
0.936	High Similarity	NPC58607
0.936	High Similarity	NPC191037
0.935	High Similarity	NPC85488
0.9313	High Similarity	NPC281780
0.9308	High Similarity	NPC34103
0.9308	High Similarity	NPC24490
0.9308	High Similarity	NPC135777
0.9308	High Similarity	NPC141765
0.9308	High Similarity	NPC165155
0.9308	High Similarity	NPC142547
0.9302	High Similarity	NPC26394
0.9291	High Similarity	NPC170844
0.9291	High Similarity	NPC476968
0.9291	High Similarity	NPC86030
0.9291	High Similarity	NPC5851
0.928	High Similarity	NPC194519
0.9268	High Similarity	NPC126935
0.9268	High Similarity	NPC312713
0.9268	High Similarity	NPC113865
0.9268	High Similarity	NPC57268
0.9268	High Similarity	NPC172676
0.9268	High Similarity	NPC262156
0.9268	High Similarity	NPC473853
0.9268	High Similarity	NPC54872
0.9268	High Similarity	NPC343720
0.9268	High Similarity	NPC470212
0.9268	High Similarity	NPC312675
0.9268	High Similarity	NPC216929
0.9268	High Similarity	NPC324571
0.9268	High Similarity	NPC184651
0.9268	High Similarity	NPC65933
0.9268	High Similarity	NPC476343
0.9268	High Similarity	NPC470804
0.9248	High Similarity	NPC87725
0.9248	High Similarity	NPC471414
0.9248	High Similarity	NPC472711
0.9248	High Similarity	NPC263261
0.9242	High Similarity	NPC88640
0.9242	High Similarity	NPC193666
0.9242	High Similarity	NPC123526
0.9231	High Similarity	NPC478085
0.9225	High Similarity	NPC253105
0.9225	High Similarity	NPC230219
0.9225	High Similarity	NPC201587
0.9219	High Similarity	NPC143483
0.9219	High Similarity	NPC173308
0.9219	High Similarity	NPC181079
0.9213	High Similarity	NPC186843
0.9213	High Similarity	NPC470213
0.9213	High Similarity	NPC206615
0.9213	High Similarity	NPC72529
0.9213	High Similarity	NPC98631
0.92	High Similarity	NPC257682
0.92	High Similarity	NPC18449
0.92	High Similarity	NPC146355
0.92	High Similarity	NPC131747
0.92	High Similarity	NPC34902
0.92	High Similarity	NPC94276
0.92	High Similarity	NPC109822
0.92	High Similarity	NPC293701
0.92	High Similarity	NPC114901
0.92	High Similarity	NPC121783
0.92	High Similarity	NPC48990
0.9187	High Similarity	NPC207613
0.9179	High Similarity	NPC476356
0.9179	High Similarity	NPC253878
0.9173	High Similarity	NPC184797
0.9173	High Similarity	NPC55793
0.9173	High Similarity	NPC309124
0.9173	High Similarity	NPC254759
0.9173	High Similarity	NPC160283
0.9167	High Similarity	NPC474039
0.916	High Similarity	NPC93783
0.9147	High Similarity	NPC470096
0.9147	High Similarity	NPC472597
0.9147	High Similarity	NPC470095
0.9134	High Similarity	NPC127587
0.9111	High Similarity	NPC477616
0.9111	High Similarity	NPC477898
0.9111	High Similarity	NPC470950
0.9111	High Similarity	NPC185307
0.9106	High Similarity	NPC232316
0.9106	High Similarity	NPC95614
0.9106	High Similarity	NPC165133
0.9106	High Similarity	NPC56214
0.9106	High Similarity	NPC177475
0.9106	High Similarity	NPC117780
0.9106	High Similarity	NPC242885
0.9106	High Similarity	NPC227217
0.9106	High Similarity	NPC148615
0.9106	High Similarity	NPC35071
0.9104	High Similarity	NPC311530
0.9104	High Similarity	NPC470372
0.9104	High Similarity	NPC100675
0.9098	High Similarity	NPC232164
0.9098	High Similarity	NPC236306
0.9098	High Similarity	NPC473739
0.9098	High Similarity	NPC292882
0.9084	High Similarity	NPC311256
0.9077	High Similarity	NPC160991
0.9077	High Similarity	NPC18842
0.9077	High Similarity	NPC219671
0.9077	High Similarity	NPC184447
0.9077	High Similarity	NPC470752
0.9077	High Similarity	NPC259742
0.9077	High Similarity	NPC16208
0.9077	High Similarity	NPC104077
0.9077	High Similarity	NPC147616
0.9077	High Similarity	NPC7903
0.9077	High Similarity	NPC35932
0.907	High Similarity	NPC275950
0.907	High Similarity	NPC472338
0.9062	High Similarity	NPC472968
0.9055	High Similarity	NPC285725
0.9055	High Similarity	NPC112571
0.9055	High Similarity	NPC50683
0.9055	High Similarity	NPC76451
0.9044	High Similarity	NPC264706
0.9044	High Similarity	NPC284881
0.9044	High Similarity	NPC470097

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 NPC64201 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	771
0.2-0.3	1664
0.3-0.4	2658
0.4-0.5	1894
0.5-0.6	1050
0.6-0.7	658
0.7-0.8	158
0.8-0.85	5
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9291	High Similarity	NPD3027	Phase 3
0.8647	High Similarity	NPD1613	Approved
0.8647	High Similarity	NPD1612	Clinical (unspecified phase)
0.8537	High Similarity	NPD5283	Phase 1
0.8374	Intermediate Similarity	NPD228	Approved
0.837	Intermediate Similarity	NPD3620	Phase 2
0.837	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD2861	Phase 2
0.8271	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD3705	Approved
0.8211	Intermediate Similarity	NPD3021	Approved
0.8211	Intermediate Similarity	NPD3022	Approved
0.8106	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1357	Approved
0.7961	Intermediate Similarity	NPD6234	Discontinued
0.7941	Intermediate Similarity	NPD4908	Phase 1
0.7902	Intermediate Similarity	NPD4237	Approved
0.7902	Intermediate Similarity	NPD4236	Phase 3
0.7887	Intermediate Similarity	NPD7266	Discontinued
0.7867	Intermediate Similarity	NPD37	Approved
0.7842	Intermediate Similarity	NPD1558	Phase 1
0.7842	Intermediate Similarity	NPD4060	Phase 1
0.784	Intermediate Similarity	NPD2684	Approved
0.7836	Intermediate Similarity	NPD2983	Phase 2
0.7836	Intermediate Similarity	NPD2982	Phase 2
0.7829	Intermediate Similarity	NPD4967	Phase 2
0.7829	Intermediate Similarity	NPD4965	Approved
0.7829	Intermediate Similarity	NPD7157	Approved
0.7829	Intermediate Similarity	NPD4966	Approved
0.7826	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1610	Phase 2
0.7778	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3060	Approved
0.7778	Intermediate Similarity	NPD6674	Discontinued
0.7761	Intermediate Similarity	NPD2981	Phase 2
0.7748	Intermediate Similarity	NPD1934	Approved
0.7746	Intermediate Similarity	NPD5588	Approved
0.7737	Intermediate Similarity	NPD3018	Phase 2
0.7734	Intermediate Similarity	NPD7843	Approved
0.7722	Intermediate Similarity	NPD7228	Approved
0.7704	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2977	Approved
0.7697	Intermediate Similarity	NPD2978	Approved
0.7687	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD4536	Approved
0.7676	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD4538	Approved
0.766	Intermediate Similarity	NPD5735	Approved
0.7639	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5058	Phase 3
0.7603	Intermediate Similarity	NPD6331	Phase 2
0.7603	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4110	Phase 3
0.7597	Intermediate Similarity	NPD3882	Suspended
0.7591	Intermediate Similarity	NPD3094	Phase 2
0.7589	Intermediate Similarity	NPD2238	Phase 2
0.7582	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5536	Phase 2
0.7556	Intermediate Similarity	NPD1091	Approved
0.7551	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD6355	Discontinued
0.7534	Intermediate Similarity	NPD5177	Phase 3
0.7519	Intermediate Similarity	NPD1548	Phase 1
0.7518	Intermediate Similarity	NPD8651	Approved
0.7517	Intermediate Similarity	NPD5762	Approved
0.7517	Intermediate Similarity	NPD5763	Approved
0.7517	Intermediate Similarity	NPD1375	Discontinued
0.7516	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD5960	Phase 3
0.75	Intermediate Similarity	NPD3818	Discontinued
0.7484	Intermediate Similarity	NPD6166	Phase 2
0.7484	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.7483	Intermediate Similarity	NPD1653	Approved
0.7483	Intermediate Similarity	NPD6653	Approved
0.748	Intermediate Similarity	NPD290	Approved
0.748	Intermediate Similarity	NPD3020	Approved
0.7468	Intermediate Similarity	NPD2801	Approved
0.7448	Intermediate Similarity	NPD2161	Phase 2
0.7447	Intermediate Similarity	NPD5111	Phase 2
0.7447	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5109	Approved
0.7447	Intermediate Similarity	NPD5110	Phase 2
0.7445	Intermediate Similarity	NPD4749	Approved
0.7432	Intermediate Similarity	NPD2677	Approved
0.7432	Intermediate Similarity	NPD6190	Approved
0.7426	Intermediate Similarity	NPD3092	Approved
0.7424	Intermediate Similarity	NPD6671	Approved
0.7419	Intermediate Similarity	NPD2560	Approved
0.7419	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2563	Approved
0.7415	Intermediate Similarity	NPD4162	Approved
0.7413	Intermediate Similarity	NPD3657	Discovery
0.741	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6584	Phase 3
0.7407	Intermediate Similarity	NPD5846	Approved
0.7407	Intermediate Similarity	NPD5125	Phase 3
0.7407	Intermediate Similarity	NPD6516	Phase 2
0.7407	Intermediate Similarity	NPD5126	Approved
0.7402	Intermediate Similarity	NPD968	Approved
0.74	Intermediate Similarity	NPD4123	Phase 3
0.7394	Intermediate Similarity	NPD2674	Phase 3
0.7376	Intermediate Similarity	NPD7095	Approved
0.7376	Intermediate Similarity	NPD4625	Phase 3
0.7375	Intermediate Similarity	NPD2489	Approved
0.7375	Intermediate Similarity	NPD27	Approved
0.7372	Intermediate Similarity	NPD2231	Phase 2
0.7372	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2235	Phase 2
0.736	Intermediate Similarity	NPD291	Approved
0.7355	Intermediate Similarity	NPD5773	Approved
0.7355	Intermediate Similarity	NPD5772	Approved
0.7351	Intermediate Similarity	NPD7526	Approved
0.7351	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD52	Approved
0.7349	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4140	Approved
0.7325	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD3144	Approved
0.7324	Intermediate Similarity	NPD3145	Approved
0.732	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4005	Discontinued
0.7319	Intermediate Similarity	NPD5327	Phase 3
0.7317	Intermediate Similarity	NPD7685	Pre-registration
0.7315	Intermediate Similarity	NPD5241	Discontinued
0.7312	Intermediate Similarity	NPD2970	Approved
0.7312	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2969	Approved
0.7305	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7074	Phase 3
0.7285	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD4678	Approved
0.7273	Intermediate Similarity	NPD4675	Approved
0.7273	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7124	Phase 2
0.7266	Intermediate Similarity	NPD6696	Suspended
0.726	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD3091	Approved
0.7255	Intermediate Similarity	NPD3687	Approved
0.7255	Intermediate Similarity	NPD3686	Approved
0.725	Intermediate Similarity	NPD3051	Approved
0.7246	Intermediate Similarity	NPD2232	Approved
0.7246	Intermediate Similarity	NPD2233	Approved
0.7246	Intermediate Similarity	NPD2230	Approved
0.7246	Intermediate Similarity	NPD1608	Approved
0.7244	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7054	Approved
0.7236	Intermediate Similarity	NPD2859	Approved
0.7236	Intermediate Similarity	NPD2860	Approved
0.7234	Intermediate Similarity	NPD9494	Approved
0.7233	Intermediate Similarity	NPD5494	Approved
0.7229	Intermediate Similarity	NPD7313	Approved
0.7229	Intermediate Similarity	NPD7312	Approved
0.7229	Intermediate Similarity	NPD7311	Approved
0.7229	Intermediate Similarity	NPD7310	Approved
0.7222	Intermediate Similarity	NPD3062	Approved
0.7222	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3059	Approved
0.7222	Intermediate Similarity	NPD3061	Approved
0.7219	Intermediate Similarity	NPD4357	Discontinued
0.7219	Intermediate Similarity	NPD1511	Approved
0.7212	Intermediate Similarity	NPD7240	Approved
0.7203	Intermediate Similarity	NPD6798	Discontinued
0.7202	Intermediate Similarity	NPD4663	Approved
0.7195	Intermediate Similarity	NPD7472	Approved
0.7194	Intermediate Similarity	NPD6583	Phase 3
0.7194	Intermediate Similarity	NPD6582	Phase 2
0.7192	Intermediate Similarity	NPD6895	Approved
0.7192	Intermediate Similarity	NPD6896	Approved
0.7188	Intermediate Similarity	NPD8127	Discontinued
0.7186	Intermediate Similarity	NPD7309	Approved
0.7171	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4624	Approved
0.7162	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6004	Phase 3
0.7162	Intermediate Similarity	NPD3540	Phase 1
0.7162	Intermediate Similarity	NPD6005	Phase 3
0.7162	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6002	Phase 3
0.7161	Intermediate Similarity	NPD4380	Phase 2
0.7154	Intermediate Similarity	NPD2934	Approved
0.7154	Intermediate Similarity	NPD9296	Approved
0.7154	Intermediate Similarity	NPD2933	Approved
0.7153	Intermediate Similarity	NPD2667	Approved
0.7153	Intermediate Similarity	NPD9381	Approved
0.7153	Intermediate Similarity	NPD9384	Approved
0.7153	Intermediate Similarity	NPD2668	Approved
0.7143	Intermediate Similarity	NPD4210	Discontinued
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD6071	Discontinued
0.7134	Intermediate Similarity	NPD5844	Phase 1
0.7133	Intermediate Similarity	NPD3892	Phase 2
0.7133	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4535	Phase 3
0.7132	Intermediate Similarity	NPD1182	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