NPASS Compound

Structure

NPC208507 OpenBabel07101718322D 27 29 0 0 1 0 0 0 0 0999 V2000 -1.9274 2.1736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2567 -1.1919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4051 1.2636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4705 -0.2861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5082 1.1540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8421 1.7733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1939 1.7733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2323 2.1635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6390 -0.8417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6767 0.5985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6310 0.7118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2939 2.3747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4051 0.7118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6310 1.2636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8037 2.1635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7421 2.3747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7421 -0.3994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8421 0.2020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5960 0.6283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3498 1.4586 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 3.3593 2.9950 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5470 3.3555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5684 0.3951 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9322 2.2716 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2843 -0.9587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2323 -0.1882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 7 1 0 0 0 0 3 13 1 0 0 0 0 4 9 1 0 0 0 0 4 13 2 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 0 0 0 0 14 20 1 0 0 0 0 15 22 2 0 0 0 0 16 23 1 6 0 0 0 17 27 1 0 0 0 0 18 21 2 0 0 0 0 18 27 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.16
Volume:	440.987
LogP:	4.964
LogD:	3.681
LogS:	-6.938
# Rotatable Bonds:	6
TPSA:	80.68
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.405
Synthetic Accessibility Score:	2.6
Fsp3:	0.154
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.045
MDCK Permeability:	1.0222469427390024e-05
Pgp-inhibitor:	0.078
Pgp-substrate:	0.044
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	98.8857192993164%
Volume Distribution (VD):	0.593
Pgp-substrate:	1.2535748481750488%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.898
CYP2C19-inhibitor:	0.953
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.896
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.91
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.793
CYP3A4-substrate:	0.202

ADMET: Excretion

Clearance (CL):	8.615
Half-life (T1/2):	0.247

ADMET: Toxicity

hERG Blockers:	0.688
Human Hepatotoxicity (H-HT):	0.717
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.917
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.385
Carcinogencity:	0.889
Eye Corrosion:	0.003
Eye Irritation:	0.038
Respiratory Toxicity:	0.79

Download Data

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

Natural Product: NPC208507

Natural Product ID:	NPC208507
*Common Name:**	ZTWSXGFXLQEXJQ-IOBAAEILSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZTWSXGFXLQEXJQ-IOBAAEILSA-N
Standard InCHI:	InChI=1S/C21H22O6/c1-25-20-14-6-8-16(23)12-15(22)7-3-13-4-9-17(10-5-13)27-18(11-14)21(26-2)19(20)24/h4-6,8-11,16,23-24H,3,7,12H2,1-2H3/b8-6-/t16-/m0/s1
SMILES:	COc1c2/C=C[C@H](O)CC(=O)CCc3ccc(Oc(c2)c(c1O)OC)cc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3359255
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002652] Cyclic diarylheptanoids [CHEMONTID:0003523] Meta,para-diphenylether diarylheptanoids

*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
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Shells; Leaves	n.a.	n.a.	PMID[18163585]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25420236]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26606246]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Green Leafy Covers	n.a.	n.a.	PMID[28520428]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO12631	Corylus avellana	Species	Betulaceae	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
Others	2

Activity Type	# Activity
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT621	Tissue	Plasma	Homo sapiens	Inhibition	=	12.1	%	PMID[523844]
NPT621	Tissue	Plasma	Homo sapiens	Inhibition	=	12.0	%	PMID[523844]

☑ 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 NPC208507 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	370
0.1-0.2	1437
0.2-0.3	3990
0.3-0.4	10307
0.4-0.5	8134
0.5-0.6	3708
0.6-0.7	5090
0.7-0.8	6824
0.8-0.85	2302
0.85-0.9	513
0.9-0.95	18
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472333
0.964	High Similarity	NPC472332
0.964	High Similarity	NPC472335
0.9281	High Similarity	NPC472336
0.9281	High Similarity	NPC472334
0.9209	High Similarity	NPC472337
0.92	High Similarity	NPC48208
0.92	High Similarity	NPC156057
0.92	High Similarity	NPC162869
0.92	High Similarity	NPC475267
0.92	High Similarity	NPC470402
0.92	High Similarity	NPC474208
0.92	High Similarity	NPC474836
0.9133	High Similarity	NPC235165
0.9133	High Similarity	NPC255106
0.9128	High Similarity	NPC18727
0.9103	High Similarity	NPC474799
0.9079	High Similarity	NPC263449
0.9078	High Similarity	NPC107551
0.9078	High Similarity	NPC474282
0.9078	High Similarity	NPC326797
0.9078	High Similarity	NPC102904
0.9078	High Similarity	NPC176051
0.9078	High Similarity	NPC103976
0.9073	High Similarity	NPC472911
0.9073	High Similarity	NPC210084
0.9073	High Similarity	NPC474055
0.9073	High Similarity	NPC472914
0.9073	High Similarity	NPC223787
0.9073	High Similarity	NPC222814
0.9073	High Similarity	NPC245758
0.9073	High Similarity	NPC96167
0.9073	High Similarity	NPC472913
0.9073	High Similarity	NPC99597
0.9073	High Similarity	NPC472910
0.9073	High Similarity	NPC472598
0.9067	High Similarity	NPC213622
0.9067	High Similarity	NPC37392
0.9065	High Similarity	NPC475840
0.906	High Similarity	NPC302950
0.906	High Similarity	NPC236637
0.906	High Similarity	NPC219582
0.9021	High Similarity	NPC19158
0.9021	High Similarity	NPC471389
0.902	High Similarity	NPC308992
0.9013	High Similarity	NPC250214
0.9013	High Similarity	NPC95936
0.9007	High Similarity	NPC35038
0.9007	High Similarity	NPC317383
0.9007	High Similarity	NPC320825
0.9007	High Similarity	NPC472916
0.9007	High Similarity	NPC13858
0.9007	High Similarity	NPC306441
0.9007	High Similarity	NPC278778
0.9007	High Similarity	NPC16435
0.9007	High Similarity	NPC291878
0.9007	High Similarity	NPC326037
0.9007	High Similarity	NPC195796
0.9	High Similarity	NPC22519
0.9	High Similarity	NPC69394
0.9	High Similarity	NPC310854
0.9	High Similarity	NPC231018
0.9	High Similarity	NPC176775
0.9	High Similarity	NPC145379
0.9	High Similarity	NPC274327
0.9	High Similarity	NPC255350
0.9	High Similarity	NPC47781
0.9	High Similarity	NPC183878
0.9	High Similarity	NPC160951
0.8961	High Similarity	NPC55121
0.8954	High Similarity	NPC282009
0.8954	High Similarity	NPC287328
0.8951	High Similarity	NPC160283
0.8951	High Similarity	NPC254759
0.8947	High Similarity	NPC78225
0.8947	High Similarity	NPC471479
0.8947	High Similarity	NPC469584
0.8947	High Similarity	NPC291508
0.8947	High Similarity	NPC52530
0.8947	High Similarity	NPC471515
0.8947	High Similarity	NPC27337
0.8944	High Similarity	NPC276490
0.894	High Similarity	NPC201136
0.894	High Similarity	NPC227325
0.894	High Similarity	NPC321779
0.894	High Similarity	NPC183597
0.894	High Similarity	NPC167815
0.894	High Similarity	NPC2476
0.894	High Similarity	NPC92659
0.894	High Similarity	NPC200761
0.894	High Similarity	NPC50715
0.894	High Similarity	NPC138360
0.894	High Similarity	NPC2928
0.894	High Similarity	NPC128863
0.894	High Similarity	NPC142479
0.894	High Similarity	NPC163780
0.894	High Similarity	NPC196439
0.894	High Similarity	NPC256612
0.894	High Similarity	NPC155015
0.894	High Similarity	NPC20830
0.894	High Similarity	NPC476642
0.894	High Similarity	NPC45849
0.894	High Similarity	NPC146165
0.894	High Similarity	NPC477503
0.894	High Similarity	NPC280339
0.894	High Similarity	NPC4455
0.894	High Similarity	NPC472909
0.894	High Similarity	NPC470327
0.8936	High Similarity	NPC234333
0.8936	High Similarity	NPC112939
0.8936	High Similarity	NPC61946
0.8936	High Similarity	NPC121812
0.8936	High Similarity	NPC134968
0.8936	High Similarity	NPC94750
0.8936	High Similarity	NPC112246
0.8936	High Similarity	NPC260898
0.8936	High Similarity	NPC47398
0.8936	High Similarity	NPC470356
0.8936	High Similarity	NPC474206
0.8933	High Similarity	NPC83508
0.8933	High Similarity	NPC212678
0.8933	High Similarity	NPC57030
0.8933	High Similarity	NPC120163
0.8933	High Similarity	NPC100887
0.8933	High Similarity	NPC301323
0.8933	High Similarity	NPC120537
0.8933	High Similarity	NPC275722
0.8933	High Similarity	NPC25270
0.8933	High Similarity	NPC162313
0.8933	High Similarity	NPC180234
0.8933	High Similarity	NPC199100
0.8933	High Similarity	NPC222830
0.8933	High Similarity	NPC293183
0.8933	High Similarity	NPC473236
0.8933	High Similarity	NPC131624
0.8933	High Similarity	NPC256283
0.8933	High Similarity	NPC239128
0.8933	High Similarity	NPC187498
0.8933	High Similarity	NPC199773
0.8933	High Similarity	NPC472912
0.8933	High Similarity	NPC188203
0.8933	High Similarity	NPC241498
0.8933	High Similarity	NPC71334
0.8933	High Similarity	NPC156222
0.8933	High Similarity	NPC275836
0.8933	High Similarity	NPC198826
0.8926	High Similarity	NPC338131
0.8921	High Similarity	NPC472597
0.8904	High Similarity	NPC474982
0.8897	High Similarity	NPC477616
0.8896	High Similarity	NPC474038
0.8896	High Similarity	NPC158188
0.8896	High Similarity	NPC266314
0.8896	High Similarity	NPC472634
0.8896	High Similarity	NPC26326
0.8896	High Similarity	NPC471499
0.8896	High Similarity	NPC472632
0.8889	High Similarity	NPC476410
0.8889	High Similarity	NPC311530
0.8889	High Similarity	NPC172202
0.8889	High Similarity	NPC284127
0.8889	High Similarity	NPC329091
0.8889	High Similarity	NPC22192
0.8889	High Similarity	NPC152904
0.8882	High Similarity	NPC49824
0.8882	High Similarity	NPC191146
0.8882	High Similarity	NPC470328
0.8882	High Similarity	NPC209614
0.8882	High Similarity	NPC472626
0.8882	High Similarity	NPC250922
0.8882	High Similarity	NPC471500
0.8882	High Similarity	NPC68093
0.8882	High Similarity	NPC201837
0.8881	High Similarity	NPC245207
0.8881	High Similarity	NPC127218
0.8881	High Similarity	NPC319647
0.8881	High Similarity	NPC292882
0.8881	High Similarity	NPC471388
0.8881	High Similarity	NPC25966
0.8874	High Similarity	NPC7178
0.8874	High Similarity	NPC167091
0.8874	High Similarity	NPC62903
0.8874	High Similarity	NPC88645
0.8874	High Similarity	NPC276409
0.8874	High Similarity	NPC292214
0.8874	High Similarity	NPC280937
0.8874	High Similarity	NPC472915
0.8874	High Similarity	NPC75279
0.8874	High Similarity	NPC206238
0.8874	High Similarity	NPC250822
0.8874	High Similarity	NPC192083
0.8874	High Similarity	NPC124714
0.8874	High Similarity	NPC213896
0.8874	High Similarity	NPC271779
0.8873	High Similarity	NPC474639
0.8873	High Similarity	NPC302701
0.8873	High Similarity	NPC230734
0.8873	High Similarity	NPC227503
0.8873	High Similarity	NPC269091
0.8867	High Similarity	NPC208043

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 NPC208507 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	848
0.2-0.3	1845
0.3-0.4	2686
0.4-0.5	1703
0.5-0.6	970
0.6-0.7	614
0.7-0.8	135
0.8-0.85	12
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.906	High Similarity	NPD1934	Approved
0.9	High Similarity	NPD2801	Approved
0.8874	High Similarity	NPD2393	Clinical (unspecified phase)
0.8777	High Similarity	NPD3027	Phase 3
0.8726	High Similarity	NPD6166	Phase 2
0.8726	High Similarity	NPD6168	Clinical (unspecified phase)
0.8726	High Similarity	NPD6167	Clinical (unspecified phase)
0.8723	High Similarity	NPD1612	Clinical (unspecified phase)
0.8723	High Similarity	NPD1613	Approved
0.8636	High Similarity	NPD3882	Suspended
0.8523	High Similarity	NPD1511	Approved
0.8509	High Similarity	NPD7074	Phase 3
0.85	High Similarity	NPD3818	Discontinued
0.8447	Intermediate Similarity	NPD7054	Approved
0.844	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1512	Approved
0.8395	Intermediate Similarity	NPD7472	Approved
0.8369	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3817	Phase 2
0.828	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD5494	Approved
0.8232	Intermediate Similarity	NPD6797	Phase 2
0.8194	Intermediate Similarity	NPD4380	Phase 2
0.8182	Intermediate Similarity	NPD7251	Discontinued
0.8133	Intermediate Similarity	NPD7808	Phase 3
0.8121	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD5844	Phase 1
0.8105	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD5402	Approved
0.8069	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD1549	Phase 2
0.8065	Intermediate Similarity	NPD1653	Approved
0.8063	Intermediate Similarity	NPD6234	Discontinued
0.8	Intermediate Similarity	NPD7075	Discontinued
0.7975	Intermediate Similarity	NPD37	Approved
0.7963	Intermediate Similarity	NPD7199	Phase 2
0.7937	Intermediate Similarity	NPD4965	Approved
0.7937	Intermediate Similarity	NPD4967	Phase 2
0.7937	Intermediate Similarity	NPD4966	Approved
0.7933	Intermediate Similarity	NPD2796	Approved
0.7925	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD6799	Approved
0.7904	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1510	Phase 2
0.7862	Intermediate Similarity	NPD6801	Discontinued
0.7857	Intermediate Similarity	NPD6559	Discontinued
0.7838	Intermediate Similarity	NPD1240	Approved
0.7832	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7228	Approved
0.7815	Intermediate Similarity	NPD2935	Discontinued
0.7808	Intermediate Similarity	NPD4908	Phase 1
0.7805	Intermediate Similarity	NPD6232	Discontinued
0.7805	Intermediate Similarity	NPD3787	Discontinued
0.7784	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7473	Discontinued
0.7771	Intermediate Similarity	NPD5403	Approved
0.777	Intermediate Similarity	NPD6233	Phase 2
0.7764	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1247	Approved
0.774	Intermediate Similarity	NPD2861	Phase 2
0.7736	Intermediate Similarity	NPD6599	Discontinued
0.7733	Intermediate Similarity	NPD1607	Approved
0.7718	Intermediate Similarity	NPD943	Approved
0.7703	Intermediate Similarity	NPD6798	Discontinued
0.7703	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD7819	Suspended
0.7702	Intermediate Similarity	NPD1465	Phase 2
0.7697	Intermediate Similarity	NPD6099	Approved
0.7697	Intermediate Similarity	NPD6100	Approved
0.7692	Intermediate Similarity	NPD1610	Phase 2
0.7677	Intermediate Similarity	NPD6190	Approved
0.7667	Intermediate Similarity	NPD6355	Discontinued
0.766	Intermediate Similarity	NPD1548	Phase 1
0.7643	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD5401	Approved
0.7636	Intermediate Similarity	NPD6959	Discontinued
0.7632	Intermediate Similarity	NPD7033	Discontinued
0.7619	Intermediate Similarity	NPD3018	Phase 2
0.7619	Intermediate Similarity	NPD3751	Discontinued
0.7613	Intermediate Similarity	NPD3750	Approved
0.7613	Intermediate Similarity	NPD4628	Phase 3
0.7582	Intermediate Similarity	NPD1551	Phase 2
0.7578	Intermediate Similarity	NPD7411	Suspended
0.755	Intermediate Similarity	NPD230	Phase 1
0.755	Intermediate Similarity	NPD447	Suspended
0.7545	Intermediate Similarity	NPD3926	Phase 2
0.7515	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4110	Phase 3
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7484	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4060	Phase 1
0.7469	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2982	Phase 2
0.7466	Intermediate Similarity	NPD2983	Phase 2
0.7443	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD228	Approved
0.74	Intermediate Similarity	NPD4625	Phase 3
0.7397	Intermediate Similarity	NPD2981	Phase 2
0.7389	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2424	Discontinued
0.7371	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4749	Approved
0.7343	Intermediate Similarity	NPD5536	Phase 2
0.7341	Intermediate Similarity	NPD7240	Approved
0.7329	Intermediate Similarity	NPD1091	Approved
0.7329	Intermediate Similarity	NPD1535	Discovery
0.7329	Intermediate Similarity	NPD422	Phase 1
0.7325	Intermediate Similarity	NPD1652	Phase 2
0.7325	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2800	Approved
0.7324	Intermediate Similarity	NPD6671	Approved
0.7312	Intermediate Similarity	NPD2534	Approved
0.7312	Intermediate Similarity	NPD2533	Approved
0.7312	Intermediate Similarity	NPD2532	Approved
0.7308	Intermediate Similarity	NPD7266	Discontinued
0.7305	Intermediate Similarity	NPD5283	Phase 1
0.7303	Intermediate Similarity	NPD4062	Phase 3
0.7294	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD3748	Approved
0.7279	Intermediate Similarity	NPD1481	Phase 2
0.7279	Intermediate Similarity	NPD1608	Approved
0.7273	Intermediate Similarity	NPD8455	Phase 2
0.7267	Intermediate Similarity	NPD9494	Approved
0.7255	Intermediate Similarity	NPD1558	Phase 1
0.725	Intermediate Similarity	NPD4357	Discontinued
0.7248	Intermediate Similarity	NPD2797	Approved
0.7237	Intermediate Similarity	NPD3268	Approved
0.7237	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8127	Discontinued
0.7215	Intermediate Similarity	NPD6674	Discontinued
0.7208	Intermediate Similarity	NPD5124	Phase 1
0.7208	Intermediate Similarity	NPD1933	Approved
0.7208	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7549	Discontinued
0.72	Intermediate Similarity	NPD5647	Approved
0.7197	Intermediate Similarity	NPD6004	Phase 3
0.7197	Intermediate Similarity	NPD6002	Phase 3
0.7197	Intermediate Similarity	NPD6005	Phase 3
0.7197	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4675	Approved
0.7195	Intermediate Similarity	NPD4678	Approved
0.7194	Intermediate Similarity	NPD2684	Approved
0.7179	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2799	Discontinued
0.7176	Intermediate Similarity	NPD7229	Phase 3
0.7171	Intermediate Similarity	NPD7095	Approved
0.7167	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6653	Approved
0.7143	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3620	Phase 2
0.7143	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3496	Discontinued
0.7134	Intermediate Similarity	NPD6032	Approved
0.7133	Intermediate Similarity	NPD1203	Approved
0.7126	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD290	Approved
0.7119	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD920	Approved
0.7115	Intermediate Similarity	NPD4538	Approved
0.7115	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4536	Approved
0.7113	Intermediate Similarity	NPD7843	Approved
0.7108	Intermediate Similarity	NPD6844	Discontinued
0.7105	Intermediate Similarity	NPD6832	Phase 2
0.7102	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5762	Approved
0.7089	Intermediate Similarity	NPD2344	Approved
0.7089	Intermediate Similarity	NPD5763	Approved
0.7089	Intermediate Similarity	NPD3540	Phase 1
0.7086	Intermediate Similarity	NPD5953	Discontinued
0.7086	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7157	Approved
0.7081	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD17	Approved
0.7075	Intermediate Similarity	NPD1778	Approved
0.7073	Intermediate Similarity	NPD3686	Approved
0.7073	Intermediate Similarity	NPD3687	Approved
0.7073	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7286	Phase 2
0.7067	Intermediate Similarity	NPD8651	Approved
0.7062	Intermediate Similarity	NPD8312	Approved
0.7062	Intermediate Similarity	NPD8313	Approved
0.7055	Intermediate Similarity	NPD1894	Discontinued

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