NPASS Compound

Structure

NPC181361 OpenBabel07101718322D 30 32 0 0 0 0 0 0 0 0999 V2000 2.9605 3.1699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5013 3.5435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3019 2.6863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9583 3.7793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5001 2.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3718 3.8600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5405 1.5379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7854 3.7793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4201 0.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2424 3.5435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1477 0.4326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2168 3.1699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7437 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5582 2.6863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2379 0.6924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3718 -0.8076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7969 1.5379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4027 1.5519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5058 0.6924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2379 -0.3076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7565 2.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3718 1.1924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5058 -0.3076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6764 0.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2265 0.7040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4041 0.4326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3718 2.1924 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6187 0.6234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9727 0.0383 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 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 20 2 0 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 16 23 2 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 21 1 0 0 0 0 18 25 2 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 22 27 1 0 0 0 0 23 30 1 0 0 0 0 24 26 2 0 0 0 0 24 28 1 0 0 0 0 25 26 1 0 0 0 0 25 29 1 0 0 0 0 26 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.26
Volume:	451.925
LogP:	8.265
LogD:	4.583
LogS:	-3.198
# Rotatable Bonds:	0
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.422
Synthetic Accessibility Score:	4.273
Fsp3:	0.538
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.364
MDCK Permeability:	1.13601154225762e-05
Pgp-inhibitor:	0.791
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	99.75835418701172%
Volume Distribution (VD):	2.474
Pgp-substrate:	0.48408061265945435%

ADMET: Metabolism

CYP1A2-inhibitor:	0.582
CYP1A2-substrate:	0.181
CYP2C19-inhibitor:	0.862
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.182
CYP2C9-substrate:	0.971
CYP2D6-inhibitor:	0.835
CYP2D6-substrate:	0.48
CYP3A4-inhibitor:	0.212
CYP3A4-substrate:	0.072

ADMET: Excretion

Clearance (CL):	6.402
Half-life (T1/2):	0.582

ADMET: Toxicity

hERG Blockers:	0.391
Human Hepatotoxicity (H-HT):	0.058
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.146
Rat Oral Acute Toxicity:	0.082
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.981
Carcinogencity:	0.032
Eye Corrosion:	0.083
Eye Irritation:	0.948
Respiratory Toxicity:	0.835

Download Data

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

Natural Product: NPC181361

Natural Product ID:	NPC181361
*Common Name:**	Robustol
IUPAC Name:	n.a.
Synonyms:	Robustol
Standard InCHIKey:	ORJQIEGXRFXFHY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H36O4/c27-22-15-20-13-11-9-7-5-3-1-2-4-6-8-10-12-14-21-17-24(28)26(25(29)18-21)30-23(16-20)19-22/h15-19,27-29H,1-14H2
SMILES:	C1CCCCCCCc2cc(c(c(c2)O)Oc2cc(CCCCCC1)cc(c2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL218660
PubChem CID:	634353
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17243726]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8945	Grevillea robusta	Species	Proteaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	32400.0	nM	PMID[502961]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	24000.0	nM	PMID[502961]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	32700.0	nM	PMID[502961]

☑ 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 NPC181361 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	467
0.1-0.2	1821
0.2-0.3	6287
0.3-0.4	13390
0.4-0.5	3463
0.5-0.6	4368
0.6-0.7	7296
0.7-0.8	4295
0.8-0.85	823
0.85-0.9	377
0.9-0.95	106
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC470699
0.9667	High Similarity	NPC228972
0.9667	High Similarity	NPC122792
0.9597	High Similarity	NPC309787
0.959	High Similarity	NPC210355
0.952	High Similarity	NPC470752
0.9426	High Similarity	NPC298757
0.9426	High Similarity	NPC203133
0.9426	High Similarity	NPC233410
0.9426	High Similarity	NPC57490
0.9426	High Similarity	NPC117214
0.9426	High Similarity	NPC475169
0.9426	High Similarity	NPC472093
0.9426	High Similarity	NPC208950
0.9426	High Similarity	NPC17943
0.9426	High Similarity	NPC251855
0.9426	High Similarity	NPC116907
0.9426	High Similarity	NPC221077
0.9426	High Similarity	NPC193544
0.9417	High Similarity	NPC145780
0.9365	High Similarity	NPC131128
0.9365	High Similarity	NPC127624
0.9365	High Similarity	NPC474134
0.936	High Similarity	NPC472338
0.935	High Similarity	NPC76451
0.9291	High Similarity	NPC475840
0.9286	High Similarity	NPC472597
0.9274	High Similarity	NPC127587
0.9274	High Similarity	NPC74817
0.9274	High Similarity	NPC82679
0.9274	High Similarity	NPC124452
0.9274	High Similarity	NPC5447
0.9274	High Similarity	NPC282000
0.9274	High Similarity	NPC159968
0.9274	High Similarity	NPC236791
0.9274	High Similarity	NPC250432
0.9274	High Similarity	NPC293054
0.9274	High Similarity	NPC324112
0.9274	High Similarity	NPC246620
0.9274	High Similarity	NPC169474
0.9262	High Similarity	NPC197757
0.9262	High Similarity	NPC282496
0.9262	High Similarity	NPC228922
0.9262	High Similarity	NPC233526
0.9262	High Similarity	NPC136319
0.9219	High Similarity	NPC66840
0.9219	High Similarity	NPC317380
0.9219	High Similarity	NPC256307
0.9213	High Similarity	NPC7903
0.9213	High Similarity	NPC35932
0.9213	High Similarity	NPC16208
0.9213	High Similarity	NPC160991
0.9213	High Similarity	NPC184447
0.9213	High Similarity	NPC202762
0.9213	High Similarity	NPC86655
0.9206	High Similarity	NPC91291
0.9206	High Similarity	NPC214860
0.9206	High Similarity	NPC469612
0.9206	High Similarity	NPC469614
0.92	High Similarity	NPC470213
0.92	High Similarity	NPC46274
0.92	High Similarity	NPC226331
0.92	High Similarity	NPC98631
0.92	High Similarity	NPC28765
0.92	High Similarity	NPC206615
0.92	High Similarity	NPC186843
0.9194	High Similarity	NPC28730
0.9194	High Similarity	NPC78974
0.9194	High Similarity	NPC223136
0.9194	High Similarity	NPC214406
0.9194	High Similarity	NPC103823
0.9194	High Similarity	NPC18924
0.9194	High Similarity	NPC44748
0.918	High Similarity	NPC262253
0.918	High Similarity	NPC71579
0.918	High Similarity	NPC41562
0.918	High Similarity	NPC473411
0.9147	High Similarity	NPC121812
0.9147	High Similarity	NPC112246
0.9147	High Similarity	NPC260898
0.9147	High Similarity	NPC234333
0.9147	High Similarity	NPC470356
0.9147	High Similarity	NPC47398
0.9147	High Similarity	NPC474206
0.9147	High Similarity	NPC112939
0.9147	High Similarity	NPC94750
0.9141	High Similarity	NPC168059
0.9141	High Similarity	NPC229442
0.9134	High Similarity	NPC469625
0.9134	High Similarity	NPC469907
0.9134	High Similarity	NPC470096
0.9134	High Similarity	NPC469613
0.9134	High Similarity	NPC470095
0.9134	High Similarity	NPC30043
0.9127	High Similarity	NPC202582
0.9127	High Similarity	NPC3439
0.9127	High Similarity	NPC218856
0.9127	High Similarity	NPC170844
0.9127	High Similarity	NPC476968
0.9127	High Similarity	NPC222004
0.9127	High Similarity	NPC226788
0.9127	High Similarity	NPC210623
0.9127	High Similarity	NPC190629
0.9127	High Similarity	NPC285339
0.9127	High Similarity	NPC273295
0.9127	High Similarity	NPC45824
0.9127	High Similarity	NPC470258
0.912	High Similarity	NPC252131
0.912	High Similarity	NPC474119
0.9113	High Similarity	NPC234400
0.9113	High Similarity	NPC105925
0.9113	High Similarity	NPC60885
0.9113	High Similarity	NPC299584
0.9113	High Similarity	NPC82483
0.9113	High Similarity	NPC265483
0.9077	High Similarity	NPC248727
0.9077	High Similarity	NPC306441
0.9077	High Similarity	NPC270456
0.9077	High Similarity	NPC230734
0.9077	High Similarity	NPC162659
0.9077	High Similarity	NPC227503
0.9077	High Similarity	NPC474639
0.9077	High Similarity	NPC302701
0.9077	High Similarity	NPC472336
0.9077	High Similarity	NPC269091
0.9077	High Similarity	NPC472334
0.9077	High Similarity	NPC16435
0.9077	High Similarity	NPC265433
0.907	High Similarity	NPC310854
0.907	High Similarity	NPC170694
0.9062	High Similarity	NPC204215
0.9062	High Similarity	NPC201587
0.9062	High Similarity	NPC253105
0.9062	High Similarity	NPC175067
0.9055	High Similarity	NPC311680
0.9055	High Similarity	NPC299221
0.9055	High Similarity	NPC51840
0.9055	High Similarity	NPC234488
0.9055	High Similarity	NPC126836
0.9048	High Similarity	NPC154866
0.9032	High Similarity	NPC206487
0.9032	High Similarity	NPC5796
0.9016	High Similarity	NPC166759
0.9016	High Similarity	NPC472596
0.9015	High Similarity	NPC291101
0.9015	High Similarity	NPC266197
0.9008	High Similarity	NPC103976
0.9008	High Similarity	NPC102904
0.9008	High Similarity	NPC176051
0.9008	High Similarity	NPC276490
0.9008	High Similarity	NPC474390
0.9008	High Similarity	NPC107551
0.9008	High Similarity	NPC474282
0.9008	High Similarity	NPC211549
0.9008	High Similarity	NPC326797
0.9	High Similarity	NPC151224
0.9	High Similarity	NPC86947
0.9	High Similarity	NPC472337
0.9	High Similarity	NPC61946
0.9	High Similarity	NPC164787
0.8992	High Similarity	NPC158331
0.8992	High Similarity	NPC11060
0.8992	High Similarity	NPC36490
0.8992	High Similarity	NPC36661
0.8984	High Similarity	NPC268342
0.8984	High Similarity	NPC42760
0.8984	High Similarity	NPC268266
0.8984	High Similarity	NPC220825
0.8984	High Similarity	NPC474017
0.8976	High Similarity	NPC58164
0.8976	High Similarity	NPC212015
0.8976	High Similarity	NPC10225
0.8968	High Similarity	NPC319625
0.8968	High Similarity	NPC216836
0.8968	High Similarity	NPC118787
0.8968	High Similarity	NPC236760
0.8968	High Similarity	NPC147821
0.8968	High Similarity	NPC183181
0.8968	High Similarity	NPC111247
0.8968	High Similarity	NPC266555
0.8968	High Similarity	NPC292056
0.8968	High Similarity	NPC163332
0.8968	High Similarity	NPC41706
0.896	High Similarity	NPC194519
0.8952	High Similarity	NPC95168
0.8952	High Similarity	NPC121115
0.8952	High Similarity	NPC84086
0.8943	High Similarity	NPC49341
0.8939	High Similarity	NPC55947
0.8939	High Similarity	NPC25966
0.8939	High Similarity	NPC70682
0.8939	High Similarity	NPC245207
0.8939	High Similarity	NPC260741
0.8939	High Similarity	NPC127218
0.8939	High Similarity	NPC22517
0.8939	High Similarity	NPC319647
0.8934	High Similarity	NPC10932
0.8934	High Similarity	NPC232084
0.8934	High Similarity	NPC61516
0.8934	High Similarity	NPC474565

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 NPC181361 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	976
0.2-0.3	1953
0.3-0.4	2736
0.4-0.5	1543
0.5-0.6	874
0.6-0.7	562
0.7-0.8	107
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9274	High Similarity	NPD1530	Clinical (unspecified phase)
0.92	High Similarity	NPD1529	Clinical (unspecified phase)
0.9127	High Similarity	NPD3027	Phase 3
0.8915	High Similarity	NPD1612	Clinical (unspecified phase)
0.8915	High Similarity	NPD1613	Approved
0.8217	Intermediate Similarity	NPD2982	Phase 2
0.8217	Intermediate Similarity	NPD2983	Phase 2
0.8203	Intermediate Similarity	NPD1610	Phase 2
0.8197	Intermediate Similarity	NPD228	Approved
0.8182	Intermediate Similarity	NPD4908	Phase 1
0.8175	Intermediate Similarity	NPD1548	Phase 1
0.814	Intermediate Similarity	NPD2981	Phase 2
0.8106	Intermediate Similarity	NPD3018	Phase 2
0.8077	Intermediate Similarity	NPD4749	Approved
0.8074	Intermediate Similarity	NPD1558	Phase 1
0.8065	Intermediate Similarity	NPD5283	Phase 1
0.806	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD4625	Phase 3
0.7959	Intermediate Similarity	NPD1934	Approved
0.7939	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD2801	Approved
0.7902	Intermediate Similarity	NPD1511	Approved
0.7886	Intermediate Similarity	NPD3022	Approved
0.7886	Intermediate Similarity	NPD3021	Approved
0.78	Intermediate Similarity	NPD3882	Suspended
0.78	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD1512	Approved
0.7785	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD2861	Phase 2
0.7698	Intermediate Similarity	NPD7843	Approved
0.7687	Intermediate Similarity	NPD1653	Approved
0.7667	Intermediate Similarity	NPD1242	Phase 1
0.7664	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD2684	Approved
0.7656	Intermediate Similarity	NPD7157	Approved
0.7656	Intermediate Similarity	NPD6671	Approved
0.7652	Intermediate Similarity	NPD422	Phase 1
0.7591	Intermediate Similarity	NPD7095	Approved
0.7584	Intermediate Similarity	NPD4675	Approved
0.7584	Intermediate Similarity	NPD4678	Approved
0.7582	Intermediate Similarity	NPD6234	Discontinued
0.7564	Intermediate Similarity	NPD6166	Phase 2
0.7564	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD4060	Phase 1
0.7554	Intermediate Similarity	NPD3620	Phase 2
0.755	Intermediate Similarity	NPD1465	Phase 2
0.7535	Intermediate Similarity	NPD6100	Approved
0.7535	Intermediate Similarity	NPD6099	Approved
0.7519	Intermediate Similarity	NPD3705	Approved
0.7517	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7074	Phase 3
0.7483	Intermediate Similarity	NPD3540	Phase 1
0.7468	Intermediate Similarity	NPD3818	Discontinued
0.7466	Intermediate Similarity	NPD7124	Phase 2
0.7421	Intermediate Similarity	NPD7054	Approved
0.7415	Intermediate Similarity	NPD4357	Discontinued
0.7413	Intermediate Similarity	NPD3539	Phase 1
0.7405	Intermediate Similarity	NPD5536	Phase 2
0.74	Intermediate Similarity	NPD4005	Discontinued
0.7394	Intermediate Similarity	NPD6111	Discontinued
0.7391	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD1091	Approved
0.7386	Intermediate Similarity	NPD3817	Phase 2
0.7379	Intermediate Similarity	NPD6674	Discontinued
0.7375	Intermediate Similarity	NPD7472	Approved
0.7372	Intermediate Similarity	NPD7199	Phase 2
0.7372	Intermediate Similarity	NPD6584	Phase 3
0.7368	Intermediate Similarity	NPD6516	Phase 2
0.7368	Intermediate Similarity	NPD5846	Approved
0.7368	Intermediate Similarity	NPD37	Approved
0.7365	Intermediate Similarity	NPD7447	Phase 1
0.7361	Intermediate Similarity	NPD7266	Discontinued
0.736	Intermediate Similarity	NPD968	Approved
0.7358	Intermediate Similarity	NPD7228	Approved
0.7353	Intermediate Similarity	NPD8651	Approved
0.7338	Intermediate Similarity	NPD4967	Phase 2
0.7338	Intermediate Similarity	NPD4966	Approved
0.7338	Intermediate Similarity	NPD4965	Approved
0.7329	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3750	Approved
0.7323	Intermediate Similarity	NPD4750	Phase 3
0.7317	Intermediate Similarity	NPD846	Approved
0.7317	Intermediate Similarity	NPD940	Approved
0.7297	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD5535	Approved
0.7279	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2219	Phase 1
0.7278	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4538	Approved
0.7273	Intermediate Similarity	NPD4536	Approved
0.7273	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3060	Approved
0.7256	Intermediate Similarity	NPD8054	Approved
0.7256	Intermediate Similarity	NPD8053	Approved
0.7254	Intermediate Similarity	NPD230	Phase 1
0.7248	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4123	Phase 3
0.7241	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2674	Phase 3
0.7226	Intermediate Similarity	NPD6696	Suspended
0.7222	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5960	Phase 3
0.7222	Intermediate Similarity	NPD5588	Approved
0.7211	Intermediate Similarity	NPD3892	Phase 2
0.7206	Intermediate Similarity	NPD1608	Approved
0.72	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1549	Phase 2
0.719	Intermediate Similarity	NPD2859	Approved
0.719	Intermediate Similarity	NPD2860	Approved
0.7183	Intermediate Similarity	NPD943	Approved
0.7181	Intermediate Similarity	NPD7213	Phase 3
0.7181	Intermediate Similarity	NPD7212	Phase 2
0.7179	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7075	Discontinued
0.7178	Intermediate Similarity	NPD7251	Discontinued
0.7165	Intermediate Similarity	NPD290	Approved
0.7164	Intermediate Similarity	NPD1357	Approved
0.7154	Intermediate Similarity	NPD3020	Approved
0.7153	Intermediate Similarity	NPD6582	Phase 2
0.7153	Intermediate Similarity	NPD6583	Phase 3
0.7152	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4237	Approved
0.7143	Intermediate Similarity	NPD4162	Approved
0.7143	Intermediate Similarity	NPD4236	Phase 3
0.7134	Intermediate Similarity	NPD7808	Phase 3
0.7134	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5735	Approved
0.7133	Intermediate Similarity	NPD6355	Discontinued
0.7133	Intermediate Similarity	NPD4340	Discontinued
0.7124	Intermediate Similarity	NPD4380	Phase 2
0.7123	Intermediate Similarity	NPD1375	Discontinued
0.7123	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6797	Phase 2
0.7107	Intermediate Similarity	NPD6232	Discontinued
0.7107	Intermediate Similarity	NPD2933	Approved
0.7107	Intermediate Similarity	NPD2934	Approved
0.7103	Intermediate Similarity	NPD1510	Phase 2
0.7099	Intermediate Similarity	NPD5844	Phase 1
0.7097	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4628	Phase 3
0.7095	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4110	Phase 3
0.7095	Intermediate Similarity	NPD6331	Phase 2
0.7081	Intermediate Similarity	NPD7473	Discontinued
0.707	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6799	Approved
0.7063	Intermediate Similarity	NPD1240	Approved
0.7048	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6190	Approved
0.7042	Intermediate Similarity	NPD5110	Phase 2
0.7042	Intermediate Similarity	NPD3145	Approved
0.7042	Intermediate Similarity	NPD3144	Approved
0.7042	Intermediate Similarity	NPD5111	Phase 2
0.7042	Intermediate Similarity	NPD6798	Discontinued
0.7042	Intermediate Similarity	NPD5109	Approved
0.704	Intermediate Similarity	NPD291	Approved
0.7027	Intermediate Similarity	NPD1652	Phase 2
0.702	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5124	Phase 1
0.7007	Intermediate Similarity	NPD1535	Discovery
0.7007	Intermediate Similarity	NPD5763	Approved
0.7007	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD5058	Phase 3
0.6993	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6233	Phase 2
0.6987	Remote Similarity	NPD7819	Suspended
0.6986	Remote Similarity	NPD3748	Approved
0.6986	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD17	Approved
0.6981	Remote Similarity	NPD5494	Approved
0.698	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3225	Approved
0.6968	Remote Similarity	NPD6072	Discontinued
0.6967	Remote Similarity	NPD9296	Approved
0.6966	Remote Similarity	NPD1607	Approved
0.6962	Remote Similarity	NPD4055	Discovery
0.6959	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1481	Phase 2
0.6957	Remote Similarity	NPD2235	Phase 2
0.6957	Remote Similarity	NPD2231	Phase 2
0.695	Remote Similarity	NPD9494	Approved
0.6948	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2796	Approved
0.6939	Remote Similarity	NPD2161	Phase 2
0.6939	Remote Similarity	NPD1551	Phase 2
0.6933	Remote Similarity	NPD2677	Approved
0.6929	Remote Similarity	NPD2797	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