NPASS Compound

Structure

NPC28765 OpenBabel07101719242D 21 22 0 0 0 0 0 0 0 0999 V2000 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 15 2 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 17 1 0 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.14
Volume:	304.817
LogP:	3.603
LogD:	3.691
LogS:	-3.881
# Rotatable Bonds:	5
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.887
Synthetic Accessibility Score:	2.236
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.979
MDCK Permeability:	1.5237753359542694e-05
Pgp-inhibitor:	0.292
Pgp-substrate:	0.079
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.976
30% Bioavailability (F30%):	0.125

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	97.9621353149414%
Volume Distribution (VD):	1.297
Pgp-substrate:	1.9425779581069946%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.875
CYP2C19-substrate:	0.4
CYP2C9-inhibitor:	0.611
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.937
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.832
CYP3A4-substrate:	0.449

ADMET: Excretion

Clearance (CL):	12.172
Half-life (T1/2):	0.82

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.195
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.845
Skin Sensitization:	0.957
Carcinogencity:	0.029
Eye Corrosion:	0.058
Eye Irritation:	0.938
Respiratory Toxicity:	0.339

Download Data

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

Natural Product: NPC28765

Natural Product ID:	NPC28765
*Common Name:**	3-Methylgigantol
IUPAC Name:	5-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxy-3-methylphenol
Synonyms:	3-Methylgigantol
Standard InCHIKey:	WGIRILCEBXMODS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H20O4/c1-11-6-12(9-16(19)17(11)21-3)4-5-13-7-14(18)10-15(8-13)20-2/h6-10,18-19H,4-5H2,1-3H3
SMILES:	Cc1cc(CCc2cc(cc(c2)OC)O)cc(c1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481834
PubChem CID:	44575341
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO2022	Ephemerantha lonchophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10514302]
NPO2022	Ephemerantha lonchophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9461658]
NPO2022	Ephemerantha lonchophylla	n.a.	n.a.	n.a.	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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.9	%	PMID[480798]

☑ 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 NPC28765 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	421
0.1-0.2	1804
0.2-0.3	5637
0.3-0.4	13341
0.4-0.5	4015
0.5-0.6	3988
0.6-0.7	6988
0.7-0.8	4946
0.8-0.85	844
0.85-0.9	476
0.9-0.95	189
0.95-1	48

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC252131
0.9754	High Similarity	NPC82679
0.9754	High Similarity	NPC236791
0.9754	High Similarity	NPC282000
0.9754	High Similarity	NPC324112
0.9754	High Similarity	NPC124452
0.9754	High Similarity	NPC293054
0.9754	High Similarity	NPC74817
0.9754	High Similarity	NPC246620
0.9754	High Similarity	NPC159968
0.9754	High Similarity	NPC169474
0.9672	High Similarity	NPC44748
0.9672	High Similarity	NPC28730
0.9672	High Similarity	NPC214406
0.9672	High Similarity	NPC78974
0.9672	High Similarity	NPC223136
0.9672	High Similarity	NPC103823
0.9672	High Similarity	NPC18924
0.959	High Similarity	NPC203133
0.959	High Similarity	NPC105925
0.959	High Similarity	NPC208950
0.959	High Similarity	NPC193544
0.959	High Similarity	NPC298757
0.959	High Similarity	NPC233410
0.959	High Similarity	NPC117214
0.959	High Similarity	NPC116907
0.959	High Similarity	NPC251855
0.959	High Similarity	NPC17943
0.959	High Similarity	NPC472093
0.959	High Similarity	NPC82483
0.959	High Similarity	NPC60885
0.959	High Similarity	NPC221077
0.959	High Similarity	NPC475169
0.959	High Similarity	NPC299584
0.959	High Similarity	NPC234400
0.959	High Similarity	NPC57490
0.959	High Similarity	NPC265483
0.952	High Similarity	NPC299221
0.952	High Similarity	NPC234488
0.952	High Similarity	NPC311680
0.952	High Similarity	NPC126836
0.952	High Similarity	NPC51840
0.9516	High Similarity	NPC154866
0.9512	High Similarity	NPC76451
0.9453	High Similarity	NPC256262
0.9444	High Similarity	NPC15543
0.944	High Similarity	NPC10225
0.944	High Similarity	NPC212015
0.944	High Similarity	NPC58164
0.9435	High Similarity	NPC236760
0.9435	High Similarity	NPC266555
0.9435	High Similarity	NPC127587
0.9426	High Similarity	NPC121115
0.9426	High Similarity	NPC95168
0.9426	High Similarity	NPC282496
0.9426	High Similarity	NPC136319
0.9426	High Similarity	NPC228922
0.9426	High Similarity	NPC233526
0.9426	High Similarity	NPC197757
0.9375	High Similarity	NPC209199
0.9375	High Similarity	NPC125649
0.937	High Similarity	NPC127624
0.937	High Similarity	NPC6451
0.936	High Similarity	NPC206615
0.936	High Similarity	NPC266691
0.936	High Similarity	NPC470213
0.936	High Similarity	NPC98631
0.936	High Similarity	NPC186843
0.9355	High Similarity	NPC223953
0.9344	High Similarity	NPC41562
0.9344	High Similarity	NPC262253
0.9344	High Similarity	NPC473411
0.9344	High Similarity	NPC71579
0.9308	High Similarity	NPC22902
0.9308	High Similarity	NPC242715
0.9308	High Similarity	NPC56329
0.9302	High Similarity	NPC294884
0.9302	High Similarity	NPC108198
0.9302	High Similarity	NPC313081
0.9302	High Similarity	NPC241241
0.9302	High Similarity	NPC200557
0.9302	High Similarity	NPC158142
0.9302	High Similarity	NPC69029
0.9302	High Similarity	NPC10314
0.9297	High Similarity	NPC475840
0.9297	High Similarity	NPC32778
0.9291	High Similarity	NPC474356
0.9291	High Similarity	NPC232275
0.9291	High Similarity	NPC45715
0.9291	High Similarity	NPC12275
0.9286	High Similarity	NPC170844
0.9286	High Similarity	NPC476968
0.928	High Similarity	NPC210355
0.928	High Similarity	NPC21563
0.9262	High Similarity	NPC75713
0.9262	High Similarity	NPC476633
0.9237	High Similarity	NPC132804
0.9237	High Similarity	NPC260741
0.9237	High Similarity	NPC220344
0.9237	High Similarity	NPC70682
0.9237	High Similarity	NPC243996
0.9237	High Similarity	NPC275061
0.9231	High Similarity	NPC30632
0.9231	High Similarity	NPC143139
0.9231	High Similarity	NPC470802
0.9231	High Similarity	NPC202846
0.9225	High Similarity	NPC188378
0.9225	High Similarity	NPC317380
0.9225	High Similarity	NPC206737
0.9225	High Similarity	NPC469659
0.9225	High Similarity	NPC289258
0.9225	High Similarity	NPC555
0.9225	High Similarity	NPC56764
0.9225	High Similarity	NPC7515
0.9225	High Similarity	NPC276026
0.9219	High Similarity	NPC14224
0.9219	High Similarity	NPC161958
0.9219	High Similarity	NPC86655
0.9219	High Similarity	NPC202762
0.9213	High Similarity	NPC214860
0.9213	High Similarity	NPC224157
0.9213	High Similarity	NPC192687
0.9206	High Similarity	NPC472968
0.92	High Similarity	NPC181361
0.9194	High Similarity	NPC206487
0.9194	High Similarity	NPC5796
0.918	High Similarity	NPC166759
0.9167	High Similarity	NPC295719
0.9167	High Similarity	NPC12668
0.9167	High Similarity	NPC165026
0.9167	High Similarity	NPC308768
0.9167	High Similarity	NPC266650
0.9167	High Similarity	NPC73505
0.9167	High Similarity	NPC34431
0.9167	High Similarity	NPC259519
0.916	High Similarity	NPC200935
0.916	High Similarity	NPC266453
0.916	High Similarity	NPC230919
0.9154	High Similarity	NPC260898
0.9154	High Similarity	NPC112939
0.9154	High Similarity	NPC55239
0.9154	High Similarity	NPC47398
0.9154	High Similarity	NPC474206
0.9154	High Similarity	NPC94750
0.9154	High Similarity	NPC121812
0.9154	High Similarity	NPC214853
0.9154	High Similarity	NPC240279
0.9154	High Similarity	NPC180602
0.9154	High Similarity	NPC470356
0.9154	High Similarity	NPC473413
0.9154	High Similarity	NPC234333
0.9154	High Similarity	NPC112246
0.9147	High Similarity	NPC229442
0.9147	High Similarity	NPC471391
0.9147	High Similarity	NPC168059
0.9147	High Similarity	NPC471390
0.9141	High Similarity	NPC474017
0.9134	High Similarity	NPC45824
0.9134	High Similarity	NPC469951
0.9134	High Similarity	NPC190144
0.9134	High Similarity	NPC469963
0.9127	High Similarity	NPC470699
0.9127	High Similarity	NPC242032
0.9113	High Similarity	NPC84086
0.9106	High Similarity	NPC49341
0.9098	High Similarity	NPC10932
0.9098	High Similarity	NPC19158
0.9098	High Similarity	NPC87725
0.9098	High Similarity	NPC61516
0.9098	High Similarity	NPC35216
0.9098	High Similarity	NPC232084
0.9098	High Similarity	NPC474565
0.9098	High Similarity	NPC263261
0.9098	High Similarity	NPC247364
0.9091	High Similarity	NPC212942
0.9091	High Similarity	NPC29868
0.9091	High Similarity	NPC243759
0.9091	High Similarity	NPC79622
0.9091	High Similarity	NPC218131
0.9091	High Similarity	NPC6300
0.9091	High Similarity	NPC114171
0.9091	High Similarity	NPC184613
0.9091	High Similarity	NPC105847
0.9091	High Similarity	NPC230124
0.9084	High Similarity	NPC472334
0.9084	High Similarity	NPC133025
0.9084	High Similarity	NPC472336
0.9084	High Similarity	NPC306441
0.9084	High Similarity	NPC16435
0.9084	High Similarity	NPC474639
0.9084	High Similarity	NPC227503
0.9084	High Similarity	NPC162659
0.9084	High Similarity	NPC270456
0.9084	High Similarity	NPC230734
0.9084	High Similarity	NPC265433
0.9084	High Similarity	NPC248727
0.9077	High Similarity	NPC160697
0.907	High Similarity	NPC204215
0.907	High Similarity	NPC253105
0.907	High Similarity	NPC201587

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 NPC28765 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	1002
0.2-0.3	1880
0.3-0.4	2758
0.4-0.5	1570
0.5-0.6	843
0.6-0.7	596
0.7-0.8	120
0.8-0.85	12
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9286	High Similarity	NPD3027	Phase 3
0.8976	High Similarity	NPD1530	Clinical (unspecified phase)
0.8906	High Similarity	NPD1529	Clinical (unspecified phase)
0.8779	High Similarity	NPD1613	Approved
0.8779	High Similarity	NPD1612	Clinical (unspecified phase)
0.8538	High Similarity	NPD3018	Phase 2
0.8372	Intermediate Similarity	NPD2983	Phase 2
0.8372	Intermediate Similarity	NPD2982	Phase 2
0.8361	Intermediate Similarity	NPD228	Approved
0.8346	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD2981	Phase 2
0.8226	Intermediate Similarity	NPD5283	Phase 1
0.8195	Intermediate Similarity	NPD4908	Phase 1
0.8134	Intermediate Similarity	NPD4625	Phase 3
0.8092	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1610	Phase 2
0.8047	Intermediate Similarity	NPD1548	Phase 1
0.8041	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD1934	Approved
0.7955	Intermediate Similarity	NPD4749	Approved
0.7955	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD2801	Approved
0.791	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD3021	Approved
0.7903	Intermediate Similarity	NPD3022	Approved
0.7872	Intermediate Similarity	NPD3540	Phase 1
0.7829	Intermediate Similarity	NPD6234	Discontinued
0.7826	Intermediate Similarity	NPD4060	Phase 1
0.7826	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3620	Phase 2
0.7815	Intermediate Similarity	NPD3882	Suspended
0.781	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD3539	Phase 1
0.7733	Intermediate Similarity	NPD37	Approved
0.7698	Intermediate Similarity	NPD1558	Phase 1
0.7697	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6232	Discontinued
0.7671	Intermediate Similarity	NPD1511	Approved
0.7623	Intermediate Similarity	NPD846	Approved
0.7623	Intermediate Similarity	NPD940	Approved
0.7619	Intermediate Similarity	NPD4750	Phase 3
0.7591	Intermediate Similarity	NPD2861	Phase 2
0.7584	Intermediate Similarity	NPD1653	Approved
0.7582	Intermediate Similarity	NPD4965	Approved
0.7582	Intermediate Similarity	NPD4967	Phase 2
0.7582	Intermediate Similarity	NPD4966	Approved
0.758	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6166	Phase 2
0.7568	Intermediate Similarity	NPD1512	Approved
0.7557	Intermediate Similarity	NPD5536	Phase 2
0.7554	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4357	Discontinued
0.7541	Intermediate Similarity	NPD1242	Phase 1
0.7537	Intermediate Similarity	NPD422	Phase 1
0.7537	Intermediate Similarity	NPD3705	Approved
0.7534	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD4005	Discontinued
0.7532	Intermediate Similarity	NPD7473	Discontinued
0.7517	Intermediate Similarity	NPD6674	Discontinued
0.7517	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8651	Approved
0.7484	Intermediate Similarity	NPD7228	Approved
0.7483	Intermediate Similarity	NPD7124	Phase 2
0.7483	Intermediate Similarity	NPD4380	Phase 2
0.7447	Intermediate Similarity	NPD1240	Approved
0.7431	Intermediate Similarity	NPD2935	Discontinued
0.7419	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD2219	Phase 1
0.7413	Intermediate Similarity	NPD6111	Discontinued
0.7405	Intermediate Similarity	NPD6671	Approved
0.7403	Intermediate Similarity	NPD3817	Phase 2
0.7402	Intermediate Similarity	NPD2684	Approved
0.7397	Intermediate Similarity	NPD3060	Approved
0.7391	Intermediate Similarity	NPD7074	Phase 3
0.7389	Intermediate Similarity	NPD7199	Phase 2
0.7388	Intermediate Similarity	NPD4626	Approved
0.7376	Intermediate Similarity	NPD2674	Phase 3
0.7375	Intermediate Similarity	NPD3818	Discontinued
0.7368	Intermediate Similarity	NPD4675	Approved
0.7368	Intermediate Similarity	NPD4678	Approved
0.7361	Intermediate Similarity	NPD1510	Phase 2
0.7343	Intermediate Similarity	NPD1607	Approved
0.7338	Intermediate Similarity	NPD1465	Phase 2
0.7329	Intermediate Similarity	NPD5844	Phase 1
0.7329	Intermediate Similarity	NPD7054	Approved
0.7324	Intermediate Similarity	NPD943	Approved
0.7315	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD1357	Approved
0.731	Intermediate Similarity	NPD6099	Approved
0.731	Intermediate Similarity	NPD6100	Approved
0.7308	Intermediate Similarity	NPD7843	Approved
0.7308	Intermediate Similarity	NPD7075	Discontinued
0.7308	Intermediate Similarity	NPD4055	Discovery
0.7296	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4536	Approved
0.7292	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4538	Approved
0.7285	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7472	Approved
0.7279	Intermediate Similarity	NPD1091	Approved
0.7279	Intermediate Similarity	NPD5177	Phase 3
0.7273	Intermediate Similarity	NPD230	Phase 1
0.7273	Intermediate Similarity	NPD7157	Approved
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7447	Phase 1
0.726	Intermediate Similarity	NPD7266	Discontinued
0.726	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6696	Suspended
0.7246	Intermediate Similarity	NPD2922	Phase 1
0.723	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4097	Suspended
0.7219	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5494	Approved
0.7213	Intermediate Similarity	NPD2859	Approved
0.7213	Intermediate Similarity	NPD2860	Approved
0.7211	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD5090	Approved
0.7208	Intermediate Similarity	NPD5089	Approved
0.72	Intermediate Similarity	NPD7213	Phase 3
0.72	Intermediate Similarity	NPD7212	Phase 2
0.719	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD290	Approved
0.7183	Intermediate Similarity	NPD5109	Approved
0.7183	Intermediate Similarity	NPD5110	Phase 2
0.7183	Intermediate Similarity	NPD3145	Approved
0.7183	Intermediate Similarity	NPD3144	Approved
0.7183	Intermediate Similarity	NPD5111	Phase 2
0.7179	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD3020	Approved
0.7169	Intermediate Similarity	NPD8053	Approved
0.7169	Intermediate Similarity	NPD8054	Approved
0.7162	Intermediate Similarity	NPD4237	Approved
0.7162	Intermediate Similarity	NPD4236	Phase 3
0.7152	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6584	Phase 3
0.7143	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6797	Phase 2
0.7134	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD9296	Approved
0.7131	Intermediate Similarity	NPD2933	Approved
0.7131	Intermediate Similarity	NPD2934	Approved
0.7123	Intermediate Similarity	NPD5588	Approved
0.7123	Intermediate Similarity	NPD5960	Phase 3
0.7115	Intermediate Similarity	NPD7819	Suspended
0.7114	Intermediate Similarity	NPD6331	Phase 2
0.7114	Intermediate Similarity	NPD3750	Approved
0.7114	Intermediate Similarity	NPD3892	Phase 2
0.7113	Intermediate Similarity	NPD7095	Approved
0.7097	Intermediate Similarity	NPD6072	Discontinued
0.7095	Intermediate Similarity	NPD1549	Phase 2
0.7092	Intermediate Similarity	NPD9494	Approved
0.7091	Intermediate Similarity	NPD7251	Discontinued
0.7086	Intermediate Similarity	NPD6799	Approved
0.7083	Intermediate Similarity	NPD2238	Phase 2
0.7077	Intermediate Similarity	NPD5451	Approved
0.707	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6798	Discontinued
0.7059	Intermediate Similarity	NPD1651	Approved
0.7059	Intermediate Similarity	NPD5691	Approved
0.7051	Intermediate Similarity	NPD6801	Discontinued
0.705	Intermediate Similarity	NPD1669	Approved
0.7048	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7808	Phase 3
0.7047	Intermediate Similarity	NPD1652	Phase 2
0.7042	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2533	Approved
0.7039	Intermediate Similarity	NPD4123	Phase 3
0.7039	Intermediate Similarity	NPD2532	Approved
0.7039	Intermediate Similarity	NPD2534	Approved
0.7034	Intermediate Similarity	NPD3657	Discovery
0.7034	Intermediate Similarity	NPD6355	Discontinued
0.7027	Intermediate Similarity	NPD5762	Approved
0.7027	Intermediate Similarity	NPD5763	Approved
0.7025	Intermediate Similarity	NPD6788	Approved
0.7025	Intermediate Similarity	NPD7768	Phase 2
0.702	Intermediate Similarity	NPD5058	Phase 3
0.7007	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5846	Approved
0.7007	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6516	Phase 2
0.7006	Intermediate Similarity	NPD2977	Approved
0.7006	Intermediate Similarity	NPD2978	Approved
0.7	Intermediate Similarity	NPD1283	Approved
0.6988	Remote Similarity	NPD7240	Approved
0.6988	Remote Similarity	NPD6559	Discontinued
0.6987	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7411	Suspended
0.6986	Remote Similarity	NPD6651	Approved
0.6981	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2424	Discontinued
0.6978	Remote Similarity	NPD2233	Approved
0.6978	Remote Similarity	NPD2232	Approved
0.6978	Remote Similarity	NPD2230	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