NPASS Compound

Structure

CID253595 OpenBabel06191716052D 32 34 0 0 1 0 0 0 0 0999 V2000 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 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 -7.7942 4.5000 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 -5.1962 3.0000 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 -3.4641 -0.0000 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 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 4.0000 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 0.8660 -0.5000 0.0000 C 0 0 3 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 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 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 -0.0000 1.0000 0.0000 C 0 0 1 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 4.5000 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 -4.3301 1.5000 0.0000 O 0 0 0 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 1 11 2 0 0 0 0 2 5 2 0 0 0 0 2 11 1 0 0 0 0 3 6 2 0 0 0 0 3 11 1 0 0 0 0 4 12 2 0 0 0 0 5 12 1 0 0 0 0 6 16 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 29 1 0 0 0 0 9 14 1 0 0 0 0 9 22 1 0 0 0 0 10 15 1 0 0 0 0 10 30 1 0 0 0 0 12 23 1 0 0 0 0 13 20 1 0 0 0 0 13 24 2 0 0 0 0 14 17 1 0 0 0 0 14 31 1 0 0 0 0 15 20 2 0 0 0 0 15 29 1 0 0 0 0 16 25 2 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 6 0 0 0 18 19 1 0 0 0 0 18 27 1 1 0 0 0 19 21 1 0 0 0 0 19 28 1 1 0 0 0 20 32 1 0 0 0 0 21 31 1 0 0 0 0 21 32 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.12
Volume:	421.704
LogP:	-0.151
LogD:	0.244
LogS:	-2.377
# Rotatable Bonds:	8
TPSA:	176.12
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.266
Synthetic Accessibility Score:	4.039
Fsp3:	0.333
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:	-6.191
MDCK Permeability:	1.5503055692533962e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.055
Human Intestinal Absorption (HIA):	0.08
20% Bioavailability (F20%):	0.345
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.282
Plasma Protein Binding (PPB):	89.41344451904297%
Volume Distribution (VD):	0.466
Pgp-substrate:	15.108354568481445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.044
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.755
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.09

ADMET: Excretion

Clearance (CL):	4.032
Half-life (T1/2):	0.908

ADMET: Toxicity

hERG Blockers:	0.23
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.711
AMES Toxicity:	0.318
Rat Oral Acute Toxicity:	0.291
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.637
Carcinogencity:	0.583
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC253595

Natural Product ID:	NPC253595
*Common Name:**	[4-Oxo-3-[(2S,3S,4S,5S)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxypyran-2-Yl]Methyl (E)-3-(4-Hydroxyphenyl)Prop-2-Enoate
IUPAC Name:	[4-oxo-3-[(2S,3S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypyran-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	DNXJKXABJCBGPY-ANVWEOPZSA-N
Standard InCHI:	InChI=1S/C21H22O11/c22-9-14-17(26)18(27)19(28)21(31-14)32-20-13(24)7-8-29-15(20)10-30-16(25)6-3-11-1-4-12(23)5-2-11/h1-8,14,17-19,21-23,26-28H,9-10H2/b6-3+/t14?,17-,18+,19+,21+/m1/s1
SMILES:	OCC1O[C@@H](Oc2c(occc2=O)COC(=O)/C=C/c2ccc(cc2)O)[C@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1415386
PubChem CID:	15945064
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

*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
NPO15008	Smilax bockii	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15008	Smilax bockii	Species	Staphylinidae	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
Potency	5

Activity Type	# Activity
Individual Protein	4
PROTEIN COMPLEX	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT61	Individual Protein	Beta-glucocerebrosidase	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[533718]
NPT156	Individual Protein	Sphingomyelin phosphodiesterase	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[533718]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	4109.5	nM	PMID[533718]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	31.6	nM	PMID[533718]
NPT20798	PROTEIN COMPLEX	GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[533718]

☑ 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 NPC253595 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	354
0.1-0.2	1659
0.2-0.3	4714
0.3-0.4	9916
0.4-0.5	8482
0.5-0.6	4736
0.6-0.7	6967
0.7-0.8	5100
0.8-0.85	686
0.85-0.9	79
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9435	High Similarity	NPC252114
0.9426	High Similarity	NPC52097
0.9355	High Similarity	NPC83218
0.9355	High Similarity	NPC126991
0.9344	High Similarity	NPC11724
0.928	High Similarity	NPC471157
0.9262	High Similarity	NPC476872
0.9219	High Similarity	NPC254819
0.9206	High Similarity	NPC288416
0.9206	High Similarity	NPC106677
0.9134	High Similarity	NPC225307
0.9055	High Similarity	NPC35288
0.9055	High Similarity	NPC471881
0.9055	High Similarity	NPC45224
0.9055	High Similarity	NPC156692
0.9055	High Similarity	NPC471882
0.9055	High Similarity	NPC173150
0.8939	High Similarity	NPC476870
0.8923	High Similarity	NPC46137
0.8923	High Similarity	NPC478255
0.8923	High Similarity	NPC225384
0.8923	High Similarity	NPC138777
0.8923	High Similarity	NPC246869
0.8923	High Similarity	NPC235294
0.8915	High Similarity	NPC477293
0.8915	High Similarity	NPC295970
0.8915	High Similarity	NPC477294
0.8915	High Similarity	NPC229784
0.8872	High Similarity	NPC472132
0.8864	High Similarity	NPC169398
0.8855	High Similarity	NPC473285
0.8837	High Similarity	NPC232880
0.8828	High Similarity	NPC61181
0.8788	High Similarity	NPC28637
0.8779	High Similarity	NPC219677
0.8779	High Similarity	NPC281798
0.876	High Similarity	NPC476873
0.876	High Similarity	NPC103533
0.8741	High Similarity	NPC49597
0.8741	High Similarity	NPC31745
0.8741	High Similarity	NPC220936
0.8731	High Similarity	NPC166180
0.8722	High Similarity	NPC34293
0.8722	High Similarity	NPC886
0.8722	High Similarity	NPC287597
0.8712	High Similarity	NPC473924
0.8689	High Similarity	NPC313193
0.8667	High Similarity	NPC101686
0.8667	High Similarity	NPC469364
0.8667	High Similarity	NPC65262
0.8657	High Similarity	NPC263829
0.8647	High Similarity	NPC254398
0.8613	High Similarity	NPC46644
0.8593	High Similarity	NPC471345
0.8593	High Similarity	NPC157554
0.8582	High Similarity	NPC471883
0.855	High Similarity	NPC146540
0.8548	High Similarity	NPC175771
0.854	High Similarity	NPC202700
0.8529	High Similarity	NPC78363
0.8529	High Similarity	NPC476376
0.8529	High Similarity	NPC260425
0.8489	Intermediate Similarity	NPC293154
0.8478	Intermediate Similarity	NPC186406
0.8467	Intermediate Similarity	NPC89105
0.8467	Intermediate Similarity	NPC476383
0.8467	Intermediate Similarity	NPC100389
0.8467	Intermediate Similarity	NPC81515
0.8467	Intermediate Similarity	NPC328273
0.8467	Intermediate Similarity	NPC226005
0.8467	Intermediate Similarity	NPC64141
0.8467	Intermediate Similarity	NPC472350
0.8467	Intermediate Similarity	NPC68092
0.8467	Intermediate Similarity	NPC321184
0.8467	Intermediate Similarity	NPC321638
0.8467	Intermediate Similarity	NPC205195
0.8467	Intermediate Similarity	NPC197316
0.8467	Intermediate Similarity	NPC171134
0.8456	Intermediate Similarity	NPC470572
0.8456	Intermediate Similarity	NPC103409
0.8456	Intermediate Similarity	NPC37468
0.8456	Intermediate Similarity	NPC186418
0.8429	Intermediate Similarity	NPC184464
0.8429	Intermediate Similarity	NPC63304
0.8429	Intermediate Similarity	NPC77922
0.8429	Intermediate Similarity	NPC473281
0.8429	Intermediate Similarity	NPC296659
0.8429	Intermediate Similarity	NPC202391
0.8429	Intermediate Similarity	NPC251062
0.8417	Intermediate Similarity	NPC140502
0.8417	Intermediate Similarity	NPC157816
0.8417	Intermediate Similarity	NPC145319
0.8417	Intermediate Similarity	NPC296643
0.84	Intermediate Similarity	NPC148055
0.8387	Intermediate Similarity	NPC157338
0.8382	Intermediate Similarity	NPC320259
0.8382	Intermediate Similarity	NPC185778
0.837	Intermediate Similarity	NPC215484
0.837	Intermediate Similarity	NPC114116
0.8369	Intermediate Similarity	NPC475528
0.8359	Intermediate Similarity	NPC469703
0.8359	Intermediate Similarity	NPC469704
0.8359	Intermediate Similarity	NPC201402
0.8359	Intermediate Similarity	NPC160854
0.8357	Intermediate Similarity	NPC478239
0.8357	Intermediate Similarity	NPC237872
0.8357	Intermediate Similarity	NPC475213
0.8357	Intermediate Similarity	NPC116104
0.8357	Intermediate Similarity	NPC152796
0.8357	Intermediate Similarity	NPC302286
0.8357	Intermediate Similarity	NPC263397
0.8357	Intermediate Similarity	NPC88754
0.8345	Intermediate Similarity	NPC47471
0.8345	Intermediate Similarity	NPC134405
0.8345	Intermediate Similarity	NPC476377
0.8345	Intermediate Similarity	NPC137501
0.8345	Intermediate Similarity	NPC476385
0.8345	Intermediate Similarity	NPC7518
0.8345	Intermediate Similarity	NPC154262
0.8345	Intermediate Similarity	NPC476442
0.8345	Intermediate Similarity	NPC215512
0.8345	Intermediate Similarity	NPC159387
0.8333	Intermediate Similarity	NPC140750
0.8333	Intermediate Similarity	NPC220942
0.831	Intermediate Similarity	NPC143246
0.831	Intermediate Similarity	NPC212808
0.831	Intermediate Similarity	NPC475539
0.831	Intermediate Similarity	NPC474268
0.831	Intermediate Similarity	NPC291153
0.831	Intermediate Similarity	NPC119773
0.8306	Intermediate Similarity	NPC474641
0.8298	Intermediate Similarity	NPC110063
0.8298	Intermediate Similarity	NPC232228
0.8298	Intermediate Similarity	NPC292443
0.8298	Intermediate Similarity	NPC476867
0.8295	Intermediate Similarity	NPC469686
0.8295	Intermediate Similarity	NPC55608
0.8286	Intermediate Similarity	NPC222433
0.8286	Intermediate Similarity	NPC265648
0.8284	Intermediate Similarity	NPC470079
0.8281	Intermediate Similarity	NPC282409
0.8281	Intermediate Similarity	NPC469702
0.8273	Intermediate Similarity	NPC475530
0.8273	Intermediate Similarity	NPC473799
0.8261	Intermediate Similarity	NPC124149
0.8252	Intermediate Similarity	NPC18789
0.8239	Intermediate Similarity	NPC100998
0.8239	Intermediate Similarity	NPC476864
0.8239	Intermediate Similarity	NPC226722
0.8239	Intermediate Similarity	NPC287615
0.8239	Intermediate Similarity	NPC476382
0.8239	Intermediate Similarity	NPC216819
0.8239	Intermediate Similarity	NPC252292
0.8239	Intermediate Similarity	NPC34587
0.8239	Intermediate Similarity	NPC83743
0.8239	Intermediate Similarity	NPC476869
0.8239	Intermediate Similarity	NPC262182
0.8239	Intermediate Similarity	NPC476868
0.8239	Intermediate Similarity	NPC476866
0.8239	Intermediate Similarity	NPC34927
0.8231	Intermediate Similarity	NPC471067
0.8231	Intermediate Similarity	NPC476142
0.8227	Intermediate Similarity	NPC96795
0.8227	Intermediate Similarity	NPC476384
0.8227	Intermediate Similarity	NPC119537
0.8227	Intermediate Similarity	NPC204644
0.8227	Intermediate Similarity	NPC476397
0.8227	Intermediate Similarity	NPC476378
0.8227	Intermediate Similarity	NPC112
0.8227	Intermediate Similarity	NPC478250
0.8227	Intermediate Similarity	NPC205864
0.8227	Intermediate Similarity	NPC264632
0.8227	Intermediate Similarity	NPC76406
0.8227	Intermediate Similarity	NPC105005
0.8227	Intermediate Similarity	NPC476375
0.8227	Intermediate Similarity	NPC186296
0.8227	Intermediate Similarity	NPC476381
0.8227	Intermediate Similarity	NPC269141
0.8227	Intermediate Similarity	NPC247032
0.8227	Intermediate Similarity	NPC40305
0.8227	Intermediate Similarity	NPC476380
0.8227	Intermediate Similarity	NPC298257
0.8227	Intermediate Similarity	NPC175214
0.8217	Intermediate Similarity	NPC469548
0.8217	Intermediate Similarity	NPC269242
0.8217	Intermediate Similarity	NPC476445
0.8217	Intermediate Similarity	NPC476448
0.8217	Intermediate Similarity	NPC469412
0.8217	Intermediate Similarity	NPC198734
0.8214	Intermediate Similarity	NPC80098
0.8209	Intermediate Similarity	NPC469549
0.8197	Intermediate Similarity	NPC184633
0.8182	Intermediate Similarity	NPC476865
0.8182	Intermediate Similarity	NPC37838
0.8182	Intermediate Similarity	NPC199928
0.8169	Intermediate Similarity	NPC64195
0.8169	Intermediate Similarity	NPC296954
0.8169	Intermediate Similarity	NPC196063
0.8169	Intermediate Similarity	NPC297342
0.8169	Intermediate Similarity	NPC478240

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 NPC253595 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	878
0.2-0.3	1925
0.3-0.4	2784
0.4-0.5	1888
0.5-0.6	961
0.6-0.7	317
0.7-0.8	76
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8467	Intermediate Similarity	NPD7266	Discontinued
0.8014	Intermediate Similarity	NPD1653	Approved
0.7879	Intermediate Similarity	NPD1091	Approved
0.7847	Intermediate Similarity	NPD6190	Approved
0.7597	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD4340	Discontinued
0.7578	Intermediate Similarity	NPD969	Suspended
0.7423	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD1358	Approved
0.7391	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5403	Approved
0.7347	Intermediate Similarity	NPD1652	Phase 2
0.7324	Intermediate Similarity	NPD6233	Phase 2
0.7301	Intermediate Similarity	NPD6797	Phase 2
0.7261	Intermediate Similarity	NPD7075	Discontinued
0.7256	Intermediate Similarity	NPD7251	Discontinued
0.7241	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6801	Discontinued
0.7219	Intermediate Similarity	NPD5401	Approved
0.7212	Intermediate Similarity	NPD7808	Phase 3
0.7208	Intermediate Similarity	NPD4380	Phase 2
0.7188	Intermediate Similarity	NPD3134	Approved
0.7185	Intermediate Similarity	NPD9545	Approved
0.7179	Intermediate Similarity	NPD8455	Phase 2
0.7152	Intermediate Similarity	NPD7685	Pre-registration
0.7134	Intermediate Similarity	NPD5402	Approved
0.7133	Intermediate Similarity	NPD6798	Discontinued
0.7117	Intermediate Similarity	NPD3818	Discontinued
0.7103	Intermediate Similarity	NPD5124	Phase 1
0.7103	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD422	Phase 1
0.7073	Intermediate Similarity	NPD7054	Approved
0.707	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4628	Phase 3
0.7048	Intermediate Similarity	NPD6559	Discontinued
0.7039	Intermediate Similarity	NPD6799	Approved
0.7034	Intermediate Similarity	NPD4060	Phase 1
0.703	Intermediate Similarity	NPD7472	Approved
0.7007	Intermediate Similarity	NPD7097	Phase 1
0.7	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4062	Phase 3
0.6954	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3027	Phase 3
0.6928	Remote Similarity	NPD7074	Phase 3
0.6928	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1613	Approved
0.6918	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3817	Phase 2
0.6884	Remote Similarity	NPD1357	Approved
0.6883	Remote Similarity	NPD3536	Discontinued
0.6882	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD230	Phase 1
0.6871	Remote Similarity	NPD6355	Discontinued
0.6866	Remote Similarity	NPD7843	Approved
0.6864	Remote Similarity	NPD8313	Approved
0.6864	Remote Similarity	NPD8312	Approved
0.6863	Remote Similarity	NPD5058	Phase 3
0.6835	Remote Similarity	NPD5125	Phase 3
0.6835	Remote Similarity	NPD5126	Approved
0.6831	Remote Similarity	NPD3225	Approved
0.6828	Remote Similarity	NPD7095	Approved
0.6818	Remote Similarity	NPD2684	Approved
0.6812	Remote Similarity	NPD1548	Phase 1
0.6807	Remote Similarity	NPD7228	Approved
0.6807	Remote Similarity	NPD3751	Discontinued
0.6792	Remote Similarity	NPD37	Approved
0.679	Remote Similarity	NPD6234	Discontinued
0.6786	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3764	Approved
0.6776	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6599	Discontinued
0.677	Remote Similarity	NPD4966	Approved
0.677	Remote Similarity	NPD4967	Phase 2
0.677	Remote Similarity	NPD4965	Approved
0.6755	Remote Similarity	NPD5763	Approved
0.6755	Remote Similarity	NPD5762	Approved
0.6742	Remote Similarity	NPD290	Approved
0.6738	Remote Similarity	NPD3705	Approved
0.6733	Remote Similarity	NPD7033	Discontinued
0.6732	Remote Similarity	NPD3750	Approved
0.6715	Remote Similarity	NPD4198	Discontinued
0.6715	Remote Similarity	NPD7157	Approved
0.6711	Remote Similarity	NPD2424	Discontinued
0.6711	Remote Similarity	NPD1549	Phase 2
0.669	Remote Similarity	NPD2861	Phase 2
0.6688	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6166	Phase 2
0.6687	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3496	Discontinued
0.6667	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3787	Discontinued
0.6667	Remote Similarity	NPD6674	Discontinued
0.6667	Remote Similarity	NPD4536	Approved
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1048	Approved
0.6667	Remote Similarity	NPD4538	Approved
0.6667	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4908	Phase 1
0.6644	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD2067	Discontinued
0.6627	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD7411	Suspended
0.6623	Remote Similarity	NPD5960	Phase 3
0.6623	Remote Similarity	NPD5588	Approved
0.6623	Remote Similarity	NPD1510	Phase 2
0.6623	Remote Similarity	NPD8166	Discontinued
0.6621	Remote Similarity	NPD5647	Approved
0.662	Remote Similarity	NPD1610	Phase 2
0.6619	Remote Similarity	NPD5536	Phase 2
0.6618	Remote Similarity	NPD5535	Approved
0.6617	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7458	Discontinued
0.66	Remote Similarity	NPD6653	Approved
0.6593	Remote Similarity	NPD7435	Discontinued
0.6591	Remote Similarity	NPD9697	Approved
0.6584	Remote Similarity	NPD1934	Approved
0.6575	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD3882	Suspended
0.6554	Remote Similarity	NPD3268	Approved
0.6554	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD2797	Approved
0.6547	Remote Similarity	NPD9493	Approved
0.6543	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD968	Approved
0.6535	Remote Similarity	NPD2934	Approved
0.6535	Remote Similarity	NPD2933	Approved
0.6533	Remote Similarity	NPD1933	Approved
0.6532	Remote Similarity	NPD689	Discontinued
0.6519	Remote Similarity	NPD1512	Approved
0.6507	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD7199	Phase 2
0.6504	Remote Similarity	NPD1282	Approved
0.6503	Remote Similarity	NPD1535	Discovery
0.6494	Remote Similarity	NPD4534	Discontinued
0.6494	Remote Similarity	NPD5958	Discontinued
0.6484	Remote Similarity	NPD2860	Approved
0.6484	Remote Similarity	NPD2859	Approved
0.6483	Remote Similarity	NPD8651	Approved
0.6479	Remote Similarity	NPD4626	Approved
0.6479	Remote Similarity	NPD5846	Approved
0.6479	Remote Similarity	NPD6516	Phase 2
0.6474	Remote Similarity	NPD2354	Approved
0.6474	Remote Similarity	NPD3887	Approved
0.6471	Remote Similarity	NPD1551	Phase 2
0.6471	Remote Similarity	NPD2935	Discontinued
0.6467	Remote Similarity	NPD8319	Approved
0.6467	Remote Similarity	NPD8320	Phase 1
0.6458	Remote Similarity	NPD1481	Phase 2
0.6456	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD1894	Discontinued
0.6453	Remote Similarity	NPD7240	Approved
0.6452	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD1241	Discontinued
0.6442	Remote Similarity	NPD7819	Suspended
0.6442	Remote Similarity	NPD2801	Approved
0.6438	Remote Similarity	NPD987	Approved
0.6438	Remote Similarity	NPD1203	Approved
0.6438	Remote Similarity	NPD3094	Phase 2
0.6434	Remote Similarity	NPD3847	Discontinued
0.6429	Remote Similarity	NPD6777	Approved
0.6429	Remote Similarity	NPD6778	Approved
0.6429	Remote Similarity	NPD6780	Approved
0.6429	Remote Similarity	NPD6776	Approved
0.6429	Remote Similarity	NPD6781	Approved
0.6429	Remote Similarity	NPD6782	Approved
0.6429	Remote Similarity	NPD6779	Approved
0.6425	Remote Similarity	NPD6535	Approved
0.6425	Remote Similarity	NPD6534	Approved
0.6423	Remote Similarity	NPD228	Approved
0.6415	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD3685	Discontinued
0.6412	Remote Similarity	NPD1242	Phase 1
0.641	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5691	Approved
0.6405	Remote Similarity	NPD3748	Approved
0.6403	Remote Similarity	NPD2629	Approved
0.6392	Remote Similarity	NPD1511	Approved
0.6387	Remote Similarity	NPD2030	Discontinued
0.6387	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD9495	Approved
0.6384	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7874	Approved
0.6383	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD3179	Approved
0.6376	Remote Similarity	NPD3180	Approved
0.6374	Remote Similarity	NPD5844	Phase 1
0.6364	Remote Similarity	NPD8150	Discontinued
0.6364	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2796	Approved
0.6364	Remote Similarity	NPD940	Approved
0.6364	Remote Similarity	NPD846	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