NPASS Compound

Structure

NPC295970 OpenBabel07101719242D 29 31 0 0 1 0 0 0 0 0999 V2000 -9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 -6.0622 -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 -8.6603 -3.0000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7942 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 26 1 0 0 0 0 2 5 1 0 0 0 0 2 11 2 0 0 0 0 3 6 2 0 0 0 0 3 11 1 0 0 0 0 4 7 2 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 21 1 0 0 0 0 12 28 1 0 0 0 0 13 27 1 0 0 0 0 14 26 1 0 0 0 0 15 10 1 6 0 0 0 15 17 1 0 0 0 0 15 29 1 0 0 0 0 16 22 2 0 0 0 0 16 27 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 1 0 0 0 18 19 1 0 0 0 0 18 24 1 6 0 0 0 19 20 1 0 0 0 0 19 25 1 1 0 0 0 20 28 1 6 0 0 0 20 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.13
Volume:	389.464
LogP:	0.82
LogD:	1.069
LogS:	-3.381
# Rotatable Bonds:	6
TPSA:	138.82
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.522
Synthetic Accessibility Score:	3.784
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.286
MDCK Permeability:	1.9891516785719432e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.593
Human Intestinal Absorption (HIA):	0.58
20% Bioavailability (F20%):	0.047
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.188
Plasma Protein Binding (PPB):	79.74321746826172%
Volume Distribution (VD):	0.742
Pgp-substrate:	11.244857788085938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.243
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.708
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.78
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.092

ADMET: Excretion

Clearance (CL):	5.729
Half-life (T1/2):	0.506

ADMET: Toxicity

hERG Blockers:	0.499
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.802
AMES Toxicity:	0.165
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.303
Carcinogencity:	0.723
Eye Corrosion:	0.003
Eye Irritation:	0.2
Respiratory Toxicity:	0.025

Download Data

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

Natural Product: NPC295970

Natural Product ID:	NPC295970
*Common Name:**	Desmethylyangonine-4'-O-Beta-D-Glucopyranoside
IUPAC Name:	4-methoxy-6-[(E)-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethenyl]pyran-2-one
Synonyms:
Standard InCHIKey:	KXEASOROAFAOHX-ZAHKZPOQSA-N
Standard InCHI:	InChI=1S/C20H22O9/c1-26-14-8-13(27-16(22)9-14)7-4-11-2-5-12(6-3-11)28-20-19(25)18(24)17(23)15(10-21)29-20/h2-9,15,17-21,23-25H,10H2,1H3/b7-4+/t15-,17-,18+,19-,20-/m1/s1
SMILES:	COc1cc(/C=C/c2ccc(cc2)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)oc(=O)c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2442455
PubChem CID:	73348073
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001761] Kavalactones

*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
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678669]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24094434]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25148	Helichrysum italicum	Species	Asteraceae	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	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	1.045	log10CFU/ml	PMID[503682]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	1.055	log10CFU/ml	PMID[503682]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	1.103	log10CFU/ml	PMID[503682]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	1.157	log10CFU/ml	PMID[503682]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	GI	=	53.0	%	PMID[503682]

☑ 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 NPC295970 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	333
0.1-0.2	1496
0.2-0.3	4066
0.3-0.4	9427
0.4-0.5	9382
0.5-0.6	4688
0.6-0.7	6426
0.7-0.8	6084
0.8-0.85	688
0.85-0.9	103
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.916	High Similarity	NPC166180
0.916	High Similarity	NPC103409
0.916	High Similarity	NPC37468
0.9134	High Similarity	NPC146540
0.9106	High Similarity	NPC469412
0.9106	High Similarity	NPC198734
0.903	High Similarity	NPC476442
0.903	High Similarity	NPC215512
0.9024	High Similarity	NPC60589
0.9024	High Similarity	NPC469708
0.9023	High Similarity	NPC100389
0.9008	High Similarity	NPC471029
0.8976	High Similarity	NPC471157
0.8968	High Similarity	NPC287429
0.8963	High Similarity	NPC157816
0.896	High Similarity	NPC52097
0.896	High Similarity	NPC476142
0.8955	High Similarity	NPC202700
0.8952	High Similarity	NPC269242
0.8947	High Similarity	NPC124149
0.8939	High Similarity	NPC55040
0.8939	High Similarity	NPC185778
0.8915	High Similarity	NPC253595
0.8906	High Similarity	NPC106677
0.8905	High Similarity	NPC85624
0.8905	High Similarity	NPC226722
0.8898	High Similarity	NPC126991
0.8898	High Similarity	NPC83218
0.8897	High Similarity	NPC478239
0.8897	High Similarity	NPC469367
0.8889	High Similarity	NPC186406
0.8889	High Similarity	NPC80098
0.888	High Similarity	NPC11724
0.8872	High Similarity	NPC157554
0.8872	High Similarity	NPC186418
0.8837	High Similarity	NPC302378
0.8832	High Similarity	NPC471028
0.8828	High Similarity	NPC252114
0.8824	High Similarity	NPC145319
0.88	High Similarity	NPC476872
0.8779	High Similarity	NPC246869
0.8779	High Similarity	NPC138777
0.8779	High Similarity	NPC225384
0.8779	High Similarity	NPC254819
0.8777	High Similarity	NPC97240
0.8777	High Similarity	NPC296377
0.8777	High Similarity	NPC87950
0.8777	High Similarity	NPC471764
0.8777	High Similarity	NPC175275
0.8769	High Similarity	NPC248355
0.876	High Similarity	NPC45224
0.876	High Similarity	NPC35288
0.876	High Similarity	NPC173150
0.876	High Similarity	NPC156692
0.876	High Similarity	NPC288416
0.876	High Similarity	NPC471882
0.876	High Similarity	NPC471881
0.8759	High Similarity	NPC302286
0.8759	High Similarity	NPC88754
0.8759	High Similarity	NPC116104
0.8759	High Similarity	NPC263397
0.8759	High Similarity	NPC475213
0.8759	High Similarity	NPC237872
0.8759	High Similarity	NPC152796
0.875	High Similarity	NPC79908
0.8741	High Similarity	NPC226005
0.8722	High Similarity	NPC34456
0.8714	High Similarity	NPC96294
0.8714	High Similarity	NPC220282
0.8714	High Similarity	NPC169510
0.8705	High Similarity	NPC199928
0.8705	High Similarity	NPC476865
0.8705	High Similarity	NPC291153
0.8702	High Similarity	NPC472024
0.8702	High Similarity	NPC80600
0.8696	High Similarity	NPC476867
0.8696	High Similarity	NPC292443
0.8696	High Similarity	NPC478240
0.8696	High Similarity	NPC232228
0.8692	High Similarity	NPC225307
0.8686	High Similarity	NPC140502
0.8676	High Similarity	NPC210478
0.8647	High Similarity	NPC294166
0.8647	High Similarity	NPC115022
0.8643	High Similarity	NPC52740
0.8636	High Similarity	NPC9912
0.8636	High Similarity	NPC235294
0.8636	High Similarity	NPC46137
0.8633	High Similarity	NPC476868
0.8633	High Similarity	NPC476864
0.8633	High Similarity	NPC476869
0.8633	High Similarity	NPC476866
0.8626	High Similarity	NPC26653
0.8626	High Similarity	NPC166040
0.8626	High Similarity	NPC270849
0.8615	High Similarity	NPC198798
0.8615	High Similarity	NPC140750
0.8605	High Similarity	NPC470510
0.8593	High Similarity	NPC294470
0.8592	High Similarity	NPC114740
0.8583	High Similarity	NPC226712
0.8582	High Similarity	NPC187194
0.8582	High Similarity	NPC169398
0.8582	High Similarity	NPC93924
0.8582	High Similarity	NPC478237
0.8571	High Similarity	NPC165686
0.8571	High Similarity	NPC26080
0.8571	High Similarity	NPC85799
0.8571	High Similarity	NPC269421
0.8571	High Similarity	NPC37838
0.8571	High Similarity	NPC473285
0.8571	High Similarity	NPC162093
0.8571	High Similarity	NPC303422
0.8561	High Similarity	NPC470079
0.8561	High Similarity	NPC474491
0.8561	High Similarity	NPC110063
0.8551	High Similarity	NPC65833
0.8551	High Similarity	NPC245219
0.8551	High Similarity	NPC31081
0.8538	High Similarity	NPC233559
0.8538	High Similarity	NPC61181
0.8531	High Similarity	NPC213197
0.8521	High Similarity	NPC106138
0.8521	High Similarity	NPC111785
0.8519	High Similarity	NPC238243
0.8519	High Similarity	NPC476870
0.8519	High Similarity	NPC470236
0.8519	High Similarity	NPC212729
0.8511	High Similarity	NPC41844
0.8511	High Similarity	NPC473149
0.8507	High Similarity	NPC469449
0.8507	High Similarity	NPC49074
0.8507	High Similarity	NPC25821
0.85	High Similarity	NPC252292
0.85	High Similarity	NPC34927
0.85	High Similarity	NPC476382
0.85	High Similarity	NPC262182
0.85	High Similarity	NPC287615
0.85	High Similarity	NPC100998
0.85	High Similarity	NPC216819
0.85	High Similarity	NPC34587
0.85	High Similarity	NPC138915
0.85	High Similarity	NPC83743
0.8496	Intermediate Similarity	NPC478255
0.8496	Intermediate Similarity	NPC29734
0.8496	Intermediate Similarity	NPC281798
0.8496	Intermediate Similarity	NPC121376
0.8489	Intermediate Similarity	NPC242756
0.8485	Intermediate Similarity	NPC477293
0.8485	Intermediate Similarity	NPC307110
0.8485	Intermediate Similarity	NPC477294
0.8485	Intermediate Similarity	NPC229784
0.8473	Intermediate Similarity	NPC103533
0.8472	Intermediate Similarity	NPC215060
0.8472	Intermediate Similarity	NPC53587
0.8472	Intermediate Similarity	NPC176186
0.8472	Intermediate Similarity	NPC476352
0.8472	Intermediate Similarity	NPC169404
0.8467	Intermediate Similarity	NPC220936
0.8467	Intermediate Similarity	NPC49597
0.8467	Intermediate Similarity	NPC31745
0.8462	Intermediate Similarity	NPC182350
0.8462	Intermediate Similarity	NPC100818
0.8462	Intermediate Similarity	NPC476871
0.8456	Intermediate Similarity	NPC165482
0.8456	Intermediate Similarity	NPC197723
0.8456	Intermediate Similarity	NPC164857
0.8456	Intermediate Similarity	NPC3293
0.8456	Intermediate Similarity	NPC40664
0.8456	Intermediate Similarity	NPC138350
0.8456	Intermediate Similarity	NPC472132
0.8451	Intermediate Similarity	NPC308178
0.8444	Intermediate Similarity	NPC130496
0.8444	Intermediate Similarity	NPC476411
0.8444	Intermediate Similarity	NPC188555
0.844	Intermediate Similarity	NPC107120
0.844	Intermediate Similarity	NPC74320
0.8429	Intermediate Similarity	NPC297342
0.8421	Intermediate Similarity	NPC113098
0.8414	Intermediate Similarity	NPC150442
0.8414	Intermediate Similarity	NPC469699
0.8409	Intermediate Similarity	NPC232880
0.8409	Intermediate Similarity	NPC198487
0.8406	Intermediate Similarity	NPC312881
0.84	Intermediate Similarity	NPC175771
0.8394	Intermediate Similarity	NPC87777
0.8394	Intermediate Similarity	NPC262328
0.8394	Intermediate Similarity	NPC469364
0.8394	Intermediate Similarity	NPC232246
0.8394	Intermediate Similarity	NPC470413
0.8394	Intermediate Similarity	NPC153818
0.8394	Intermediate Similarity	NPC138738
0.8394	Intermediate Similarity	NPC65262
0.8394	Intermediate Similarity	NPC126206
0.8394	Intermediate Similarity	NPC101686
0.8392	Intermediate Similarity	NPC313334
0.8392	Intermediate Similarity	NPC212670
0.8392	Intermediate Similarity	NPC206264
0.8387	Intermediate Similarity	NPC313193
0.8382	Intermediate Similarity	NPC79957

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 NPC295970 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	841
0.2-0.3	1789
0.3-0.4	2782
0.4-0.5	1988
0.5-0.6	1024
0.6-0.7	331
0.7-0.8	110
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8583	High Similarity	NPD1091	Approved
0.8392	Intermediate Similarity	NPD1653	Approved
0.8214	Intermediate Similarity	NPD1652	Phase 2
0.8201	Intermediate Similarity	NPD7266	Discontinued
0.7967	Intermediate Similarity	NPD1358	Approved
0.7867	Intermediate Similarity	NPD8455	Phase 2
0.7857	Intermediate Similarity	NPD7097	Phase 1
0.7842	Intermediate Similarity	NPD4340	Discontinued
0.7842	Intermediate Similarity	NPD5124	Phase 1
0.7842	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6233	Phase 2
0.7795	Intermediate Similarity	NPD7843	Approved
0.776	Intermediate Similarity	NPD2684	Approved
0.7744	Intermediate Similarity	NPD422	Phase 1
0.7742	Intermediate Similarity	NPD3134	Approved
0.768	Intermediate Similarity	NPD290	Approved
0.7671	Intermediate Similarity	NPD5058	Phase 3
0.7655	Intermediate Similarity	NPD4628	Phase 3
0.7626	Intermediate Similarity	NPD6798	Discontinued
0.7615	Intermediate Similarity	NPD7157	Approved
0.7519	Intermediate Similarity	NPD5535	Approved
0.75	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4536	Approved
0.7483	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4538	Approved
0.7466	Intermediate Similarity	NPD6674	Discontinued
0.7453	Intermediate Similarity	NPD7472	Approved
0.7447	Intermediate Similarity	NPD4062	Phase 3
0.7445	Intermediate Similarity	NPD3225	Approved
0.7442	Intermediate Similarity	NPD969	Suspended
0.7431	Intermediate Similarity	NPD7033	Discontinued
0.7423	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6797	Phase 2
0.7407	Intermediate Similarity	NPD3496	Discontinued
0.7397	Intermediate Similarity	NPD2424	Discontinued
0.7394	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1613	Approved
0.7388	Intermediate Similarity	NPD1357	Approved
0.7383	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7251	Discontinued
0.7362	Intermediate Similarity	NPD6559	Discontinued
0.7362	Intermediate Similarity	NPD7685	Pre-registration
0.7353	Intermediate Similarity	NPD3705	Approved
0.7351	Intermediate Similarity	NPD5403	Approved
0.7346	Intermediate Similarity	NPD7074	Phase 3
0.7343	Intermediate Similarity	NPD6355	Discontinued
0.7338	Intermediate Similarity	NPD6801	Discontinued
0.7333	Intermediate Similarity	NPD5401	Approved
0.7329	Intermediate Similarity	NPD3818	Discontinued
0.7319	Intermediate Similarity	NPD8651	Approved
0.7317	Intermediate Similarity	NPD7808	Phase 3
0.7313	Intermediate Similarity	NPD1548	Phase 1
0.731	Intermediate Similarity	NPD5960	Phase 3
0.731	Intermediate Similarity	NPD5588	Approved
0.7305	Intermediate Similarity	NPD3027	Phase 3
0.7305	Intermediate Similarity	NPD7095	Approved
0.7292	Intermediate Similarity	NPD6653	Approved
0.729	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4060	Phase 1
0.7267	Intermediate Similarity	NPD6799	Approved
0.7266	Intermediate Similarity	NPD2797	Approved
0.7261	Intermediate Similarity	NPD7075	Discontinued
0.7246	Intermediate Similarity	NPD3685	Discontinued
0.7244	Intermediate Similarity	NPD3817	Phase 2
0.7244	Intermediate Similarity	NPD9697	Approved
0.7234	Intermediate Similarity	NPD4908	Phase 1
0.7233	Intermediate Similarity	NPD7199	Phase 2
0.723	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD37	Approved
0.7222	Intermediate Similarity	NPD1933	Approved
0.7214	Intermediate Similarity	NPD5647	Approved
0.7211	Intermediate Similarity	NPD5762	Approved
0.7211	Intermediate Similarity	NPD5763	Approved
0.7208	Intermediate Similarity	NPD4380	Phase 2
0.7206	Intermediate Similarity	NPD1778	Approved
0.7206	Intermediate Similarity	NPD6516	Phase 2
0.7206	Intermediate Similarity	NPD5846	Approved
0.7197	Intermediate Similarity	NPD4966	Approved
0.7197	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4965	Approved
0.7197	Intermediate Similarity	NPD4967	Phase 2
0.7185	Intermediate Similarity	NPD1894	Discontinued
0.7183	Intermediate Similarity	NPD3180	Approved
0.7183	Intermediate Similarity	NPD3179	Approved
0.7163	Intermediate Similarity	NPD2861	Phase 2
0.7153	Intermediate Similarity	NPD4140	Approved
0.7143	Intermediate Similarity	NPD6362	Approved
0.7143	Intermediate Similarity	NPD291	Approved
0.7134	Intermediate Similarity	NPD5402	Approved
0.7133	Intermediate Similarity	NPD3268	Approved
0.7133	Intermediate Similarity	NPD6190	Approved
0.7133	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7228	Approved
0.7113	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6234	Discontinued
0.7105	Intermediate Similarity	NPD3536	Discontinued
0.7101	Intermediate Similarity	NPD1610	Phase 2
0.708	Intermediate Similarity	NPD5125	Phase 3
0.708	Intermediate Similarity	NPD5126	Approved
0.7068	Intermediate Similarity	NPD1241	Discontinued
0.7067	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD8312	Approved
0.7066	Intermediate Similarity	NPD8313	Approved
0.7059	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD9545	Approved
0.7054	Intermediate Similarity	NPD968	Approved
0.7051	Intermediate Similarity	NPD7411	Suspended
0.7042	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3847	Discontinued
0.7027	Intermediate Similarity	NPD2240	Approved
0.7027	Intermediate Similarity	NPD2239	Approved
0.7023	Intermediate Similarity	NPD556	Approved
0.7014	Intermediate Similarity	NPD1048	Approved
0.7013	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5585	Approved
0.7007	Intermediate Similarity	NPD5691	Approved
0.7006	Intermediate Similarity	NPD1934	Approved
0.6993	Remote Similarity	NPD6832	Phase 2
0.6992	Remote Similarity	NPD821	Approved
0.6987	Remote Similarity	NPD6599	Discontinued
0.6985	Remote Similarity	NPD5536	Phase 2
0.698	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6004	Phase 3
0.698	Remote Similarity	NPD6005	Phase 3
0.698	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6002	Phase 3
0.6978	Remote Similarity	NPD1535	Discovery
0.6968	Remote Similarity	NPD3686	Approved
0.6968	Remote Similarity	NPD3687	Approved
0.6967	Remote Similarity	NPD9365	Approved
0.6962	Remote Similarity	NPD7819	Suspended
0.6962	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4626	Approved
0.6954	Remote Similarity	NPD4535	Phase 3
0.6954	Remote Similarity	NPD3750	Approved
0.6946	Remote Similarity	NPD7240	Approved
0.6944	Remote Similarity	NPD5163	Phase 2
0.6943	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1549	Phase 2
0.6933	Remote Similarity	NPD4534	Discontinued
0.6929	Remote Similarity	NPD1481	Phase 2
0.6929	Remote Similarity	NPD9717	Approved
0.6929	Remote Similarity	NPD1608	Approved
0.6918	Remote Similarity	NPD2415	Discontinued
0.6914	Remote Similarity	NPD8127	Discontinued
0.6913	Remote Similarity	NPD6032	Approved
0.6913	Remote Similarity	NPD2796	Approved
0.6901	Remote Similarity	NPD987	Approved
0.6901	Remote Similarity	NPD3266	Approved
0.6901	Remote Similarity	NPD3267	Approved
0.6899	Remote Similarity	NPD4433	Discontinued
0.6897	Remote Similarity	NPD1296	Phase 2
0.689	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6166	Phase 2
0.6883	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2982	Phase 2
0.6879	Remote Similarity	NPD2983	Phase 2
0.6871	Remote Similarity	NPD3787	Discontinued
0.6871	Remote Similarity	NPD5735	Approved
0.6867	Remote Similarity	NPD5844	Phase 1
0.6863	Remote Similarity	NPD5295	Discontinued
0.6863	Remote Similarity	NPD5756	Phase 2
0.6855	Remote Similarity	NPD2801	Approved
0.6849	Remote Similarity	NPD5745	Approved
0.6846	Remote Similarity	NPD3748	Approved
0.6846	Remote Similarity	NPD4108	Discontinued
0.6842	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4110	Phase 3
0.6842	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6671	Approved
0.6821	Remote Similarity	NPD5958	Discontinued
0.6815	Remote Similarity	NPD7458	Discontinued
0.6809	Remote Similarity	NPD2981	Phase 2
0.6807	Remote Similarity	NPD3751	Discontinued
0.6803	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6841	Approved
0.6802	Remote Similarity	NPD6843	Phase 3
0.6802	Remote Similarity	NPD6842	Approved
0.68	Remote Similarity	NPD1551	Phase 2
0.6797	Remote Similarity	NPD2677	Approved
0.6791	Remote Similarity	NPD228	Approved
0.6786	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1818	Approved
0.6783	Remote Similarity	NPD1819	Approved
0.6783	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1820	Approved
0.6783	Remote Similarity	NPD1817	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