NPASS Compound

Structure

NPC281798 OpenBabel07101718182D 36 38 0 0 1 0 0 0 0 0999 V2000 3.1506 -4.3659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7329 -5.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 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 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 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 -4.3301 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5519 -3.3479 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 4.1452 -4.2614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.5388 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2731 -1.5878 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 -0.0000 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 2.6551 -1.5878 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 -8.6603 2.0000 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 5.2242 -1.2788 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 1.7040 -1.2788 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 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -2.5388 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 6 1 0 0 0 0 3 14 2 0 0 0 0 4 7 2 0 0 0 0 4 14 1 0 0 0 0 5 8 2 0 0 0 0 5 14 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 16 2 0 0 0 0 10 33 1 0 0 0 0 11 13 2 0 0 0 0 12 34 1 0 0 0 0 15 26 1 0 0 0 0 16 20 1 0 0 0 0 16 24 1 0 0 0 0 17 11 1 1 0 0 0 17 20 1 0 0 0 0 17 35 1 0 0 0 0 18 12 1 6 0 0 0 18 21 1 0 0 0 0 18 36 1 0 0 0 0 19 27 2 0 0 0 0 19 34 1 0 0 0 0 20 28 1 6 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 23 1 0 0 0 0 22 30 1 6 0 0 0 23 25 1 0 0 0 0 23 31 1 1 0 0 0 24 32 2 0 0 0 0 24 35 1 0 0 0 0 25 33 1 6 0 0 0 25 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.18
Volume:	490.888
LogP:	1.768
LogD:	1.192
LogS:	-2.622
# Rotatable Bonds:	9
TPSA:	172.21
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.182
Synthetic Accessibility Score:	4.654
Fsp3:	0.44
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.021
MDCK Permeability:	3.650739017757587e-05
Pgp-inhibitor:	0.107
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.977
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.12
Plasma Protein Binding (PPB):	85.0304183959961%
Volume Distribution (VD):	0.556
Pgp-substrate:	11.823121070861816%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.142
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.219
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.142
CYP3A4-substrate:	0.186

ADMET: Excretion

Clearance (CL):	1.521
Half-life (T1/2):	0.911

ADMET: Toxicity

hERG Blockers:	0.105
Human Hepatotoxicity (H-HT):	0.692
Drug-inuced Liver Injury (DILI):	0.334
AMES Toxicity:	0.218
Rat Oral Acute Toxicity:	0.413
Maximum Recommended Daily Dose:	0.893
Skin Sensitization:	0.864
Carcinogencity:	0.093
Eye Corrosion:	0.003
Eye Irritation:	0.039
Respiratory Toxicity:	0.18

Download Data

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

Natural Product: NPC281798

Natural Product ID:	NPC281798
*Common Name:**	Kodemariosides A
IUPAC Name:	[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2Z)-2-[(4S,5R)-4-hydroxy-5-(2-methylprop-1-enyl)-2-oxooxolan-3-ylidene]ethoxy]oxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	KRHXGSVJPFGCQY-PBPOHICXSA-N
Standard InCHI:	InChI=1S/C25H30O11/c1-13(2)11-17-20(28)16(24(32)35-17)9-10-33-25-23(31)22(30)21(29)18(36-25)12-34-19(27)8-5-14-3-6-15(26)7-4-14/h3-9,11,17-18,20-23,25-26,28-31H,10,12H2,1-2H3/b8-5+,16-9-/t17-,18-,20+,21-,22+,23-,25-/m1/s1
SMILES:	CC(=C[C@@H]1[C@H](/C(=C/CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](COC(=O)/C=C/c3ccc(cc3)O)O2)O)O)O)/C(=O)O1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1088521
PubChem CID:	46833712
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
NPO8538	Spiraea cantoniensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20329740]
NPO8538	Spiraea cantoniensis	Species	Rosaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT671	Individual Protein	Acidic alpha-glucosidase	Rattus norvegicus	Inhibition	=	15.0	%	PMID[481444]

☑ 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 NPC281798 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	257
0.1-0.2	1000
0.2-0.3	2658
0.3-0.4	6619
0.4-0.5	10454
0.5-0.6	8213
0.6-0.7	11187
0.7-0.8	2056
0.8-0.85	170
0.85-0.9	69
0.9-0.95	13
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9466	High Similarity	NPC220942
0.9365	High Similarity	NPC45224
0.9365	High Similarity	NPC471881
0.9365	High Similarity	NPC173150
0.9365	High Similarity	NPC156692
0.9365	High Similarity	NPC471882
0.9365	High Similarity	NPC35288
0.9313	High Similarity	NPC470572
0.9274	High Similarity	NPC52097
0.9194	High Similarity	NPC11724
0.9141	High Similarity	NPC225307
0.9134	High Similarity	NPC61181
0.9134	High Similarity	NPC471157
0.9113	High Similarity	NPC476872
0.9062	High Similarity	NPC106677
0.9062	High Similarity	NPC103533
0.9055	High Similarity	NPC83218
0.9055	High Similarity	NPC126991
0.903	High Similarity	NPC220936
0.903	High Similarity	NPC31745
0.9023	High Similarity	NPC472132
0.8984	High Similarity	NPC252114
0.8939	High Similarity	NPC254398
0.8931	High Similarity	NPC219677
0.8931	High Similarity	NPC478255
0.8923	High Similarity	NPC469549
0.8915	High Similarity	NPC288416
0.8872	High Similarity	NPC471883
0.8872	High Similarity	NPC169398
0.8864	High Similarity	NPC473924
0.8841	High Similarity	NPC63304
0.8797	High Similarity	NPC28637
0.8797	High Similarity	NPC114116
0.8788	High Similarity	NPC138777
0.8788	High Similarity	NPC225384
0.8788	High Similarity	NPC46137
0.8788	High Similarity	NPC254819
0.8788	High Similarity	NPC235294
0.8788	High Similarity	NPC246869
0.8779	High Similarity	NPC229784
0.8779	High Similarity	NPC477293
0.8779	High Similarity	NPC477294
0.8779	High Similarity	NPC253595
0.8741	High Similarity	NPC471345
0.8722	High Similarity	NPC473285
0.8714	High Similarity	NPC143246
0.8714	High Similarity	NPC475539
0.8714	High Similarity	NPC119773
0.8714	High Similarity	NPC474268
0.8702	High Similarity	NPC232880
0.8676	High Similarity	NPC469364
0.8676	High Similarity	NPC65262
0.8676	High Similarity	NPC101686
0.8643	High Similarity	NPC475528
0.8633	High Similarity	NPC478250
0.8633	High Similarity	NPC152796
0.8633	High Similarity	NPC475213
0.8633	High Similarity	NPC293154
0.8626	High Similarity	NPC476873
0.8613	High Similarity	NPC226005
0.8593	High Similarity	NPC471029
0.8583	High Similarity	NPC282409
0.8583	High Similarity	NPC469702
0.8582	High Similarity	NPC471095
0.8582	High Similarity	NPC471066
0.8582	High Similarity	NPC473867
0.8582	High Similarity	NPC473147
0.8571	High Similarity	NPC296659
0.8571	High Similarity	NPC202391
0.8571	High Similarity	NPC194938
0.8548	High Similarity	NPC313193
0.8529	High Similarity	NPC263829
0.8519	High Similarity	NPC215484
0.8519	High Similarity	NPC164172
0.8516	High Similarity	NPC476445
0.8516	High Similarity	NPC469548
0.8516	High Similarity	NPC476448
0.8511	High Similarity	NPC210330
0.85	High Similarity	NPC186296
0.8496	Intermediate Similarity	NPC295970
0.8489	Intermediate Similarity	NPC154262
0.8489	Intermediate Similarity	NPC159387
0.8489	Intermediate Similarity	NPC137501
0.8489	Intermediate Similarity	NPC7518
0.8478	Intermediate Similarity	NPC321184
0.8478	Intermediate Similarity	NPC321638
0.8478	Intermediate Similarity	NPC171134
0.8478	Intermediate Similarity	NPC49597
0.8478	Intermediate Similarity	NPC328273
0.8467	Intermediate Similarity	NPC157554
0.8456	Intermediate Similarity	NPC34293
0.8456	Intermediate Similarity	NPC886
0.8456	Intermediate Similarity	NPC474895
0.8456	Intermediate Similarity	NPC287597
0.8451	Intermediate Similarity	NPC212808
0.844	Intermediate Similarity	NPC77922
0.844	Intermediate Similarity	NPC251062
0.844	Intermediate Similarity	NPC184464
0.844	Intermediate Similarity	NPC473281
0.8433	Intermediate Similarity	NPC469705
0.8433	Intermediate Similarity	NPC470122
0.8433	Intermediate Similarity	NPC17968
0.8429	Intermediate Similarity	NPC469623
0.8429	Intermediate Similarity	NPC296643
0.8429	Intermediate Similarity	NPC148080
0.8421	Intermediate Similarity	NPC158673
0.8421	Intermediate Similarity	NPC198487
0.8414	Intermediate Similarity	NPC474620
0.8413	Intermediate Similarity	NPC148055
0.8413	Intermediate Similarity	NPC175771
0.8406	Intermediate Similarity	NPC476376
0.8403	Intermediate Similarity	NPC96599
0.8394	Intermediate Similarity	NPC476870
0.8369	Intermediate Similarity	NPC242756
0.8345	Intermediate Similarity	NPC89105
0.8345	Intermediate Similarity	NPC100389
0.8345	Intermediate Similarity	NPC64141
0.8345	Intermediate Similarity	NPC68092
0.8345	Intermediate Similarity	NPC476383
0.8345	Intermediate Similarity	NPC35097
0.8345	Intermediate Similarity	NPC240592
0.8345	Intermediate Similarity	NPC117346
0.8345	Intermediate Similarity	NPC472350
0.8345	Intermediate Similarity	NPC81515
0.8345	Intermediate Similarity	NPC197316
0.8333	Intermediate Similarity	NPC166180
0.8333	Intermediate Similarity	NPC123704
0.8333	Intermediate Similarity	NPC120728
0.8333	Intermediate Similarity	NPC37468
0.8322	Intermediate Similarity	NPC291153
0.8322	Intermediate Similarity	NPC320734
0.831	Intermediate Similarity	NPC196063
0.831	Intermediate Similarity	NPC110063
0.831	Intermediate Similarity	NPC300894
0.831	Intermediate Similarity	NPC297342
0.831	Intermediate Similarity	NPC296954
0.831	Intermediate Similarity	NPC141455
0.8299	Intermediate Similarity	NPC183536
0.8299	Intermediate Similarity	NPC87403
0.8299	Intermediate Similarity	NPC34965
0.8284	Intermediate Similarity	NPC146540
0.8276	Intermediate Similarity	NPC478242
0.8276	Intermediate Similarity	NPC478234
0.8273	Intermediate Similarity	NPC78363
0.8273	Intermediate Similarity	NPC260425
0.8273	Intermediate Similarity	NPC469696
0.8271	Intermediate Similarity	NPC233559
0.8271	Intermediate Similarity	NPC147192
0.8264	Intermediate Similarity	NPC473149
0.8261	Intermediate Similarity	NPC70680
0.8261	Intermediate Similarity	NPC233350
0.8261	Intermediate Similarity	NPC182217
0.8261	Intermediate Similarity	NPC185778
0.8255	Intermediate Similarity	NPC475378
0.8254	Intermediate Similarity	NPC157338
0.8252	Intermediate Similarity	NPC83743
0.8252	Intermediate Similarity	NPC262182
0.8252	Intermediate Similarity	NPC287615
0.8252	Intermediate Similarity	NPC216819
0.8244	Intermediate Similarity	NPC471067
0.8244	Intermediate Similarity	NPC469927
0.8239	Intermediate Similarity	NPC105005
0.8239	Intermediate Similarity	NPC40305
0.8235	Intermediate Similarity	NPC476407
0.8231	Intermediate Similarity	NPC106818
0.8231	Intermediate Similarity	NPC203664
0.8227	Intermediate Similarity	NPC46644
0.8227	Intermediate Similarity	NPC80098
0.8227	Intermediate Similarity	NPC476385
0.8227	Intermediate Similarity	NPC476377
0.8227	Intermediate Similarity	NPC47471
0.8227	Intermediate Similarity	NPC134405
0.8222	Intermediate Similarity	NPC214246
0.8219	Intermediate Similarity	NPC12006
0.8219	Intermediate Similarity	NPC69367
0.8214	Intermediate Similarity	NPC62800
0.8214	Intermediate Similarity	NPC205195
0.8214	Intermediate Similarity	NPC324262
0.8207	Intermediate Similarity	NPC473138
0.8207	Intermediate Similarity	NPC28776
0.8201	Intermediate Similarity	NPC186418
0.8194	Intermediate Similarity	NPC229505
0.8188	Intermediate Similarity	NPC68517
0.8188	Intermediate Similarity	NPC106406
0.8182	Intermediate Similarity	NPC471028
0.8182	Intermediate Similarity	NPC236981
0.8182	Intermediate Similarity	NPC178449
0.8182	Intermediate Similarity	NPC470907
0.8182	Intermediate Similarity	NPC232454
0.8169	Intermediate Similarity	NPC222433
0.8169	Intermediate Similarity	NPC265648
0.8169	Intermediate Similarity	NPC157816
0.8169	Intermediate Similarity	NPC65833
0.8169	Intermediate Similarity	NPC140502
0.8168	Intermediate Similarity	NPC55608
0.8163	Intermediate Similarity	NPC158546
0.8163	Intermediate Similarity	NPC289021
0.8158	Intermediate Similarity	NPC477627
0.8156	Intermediate Similarity	NPC202700
0.8156	Intermediate Similarity	NPC475530

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 NPC281798 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	642
0.2-0.3	1552
0.3-0.4	2845
0.4-0.5	2285
0.5-0.6	1190
0.6-0.7	399
0.7-0.8	29
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8345	Intermediate Similarity	NPD7266	Discontinued
0.774	Intermediate Similarity	NPD6190	Approved
0.763	Intermediate Similarity	NPD1091	Approved
0.7613	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD9545	Approved
0.755	Intermediate Similarity	NPD1653	Approved
0.7535	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6559	Discontinued
0.7462	Intermediate Similarity	NPD969	Suspended
0.7453	Intermediate Similarity	NPD3818	Discontinued
0.7378	Intermediate Similarity	NPD7685	Pre-registration
0.7361	Intermediate Similarity	NPD230	Phase 1
0.7315	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4628	Phase 3
0.7287	Intermediate Similarity	NPD1358	Approved
0.7285	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3764	Approved
0.726	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD37	Approved
0.7239	Intermediate Similarity	NPD7228	Approved
0.7234	Intermediate Similarity	NPD5647	Approved
0.7233	Intermediate Similarity	NPD6234	Discontinued
0.7229	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4380	Phase 2
0.7215	Intermediate Similarity	NPD4966	Approved
0.7215	Intermediate Similarity	NPD4967	Phase 2
0.7215	Intermediate Similarity	NPD4965	Approved
0.7197	Intermediate Similarity	NPD8455	Phase 2
0.7195	Intermediate Similarity	NPD7054	Approved
0.7195	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD9493	Approved
0.717	Intermediate Similarity	NPD7075	Discontinued
0.7152	Intermediate Similarity	NPD7074	Phase 3
0.7152	Intermediate Similarity	NPD7472	Approved
0.7143	Intermediate Similarity	NPD7097	Phase 1
0.7108	Intermediate Similarity	NPD6797	Phase 2
0.7103	Intermediate Similarity	NPD6233	Phase 2
0.7095	Intermediate Similarity	NPD7033	Discontinued
0.7083	Intermediate Similarity	NPD8312	Approved
0.7083	Intermediate Similarity	NPD8313	Approved
0.7077	Intermediate Similarity	NPD3134	Approved
0.7066	Intermediate Similarity	NPD7251	Discontinued
0.7059	Intermediate Similarity	NPD6799	Approved
0.7032	Intermediate Similarity	NPD5403	Approved
0.7029	Intermediate Similarity	NPD1357	Approved
0.7025	Intermediate Similarity	NPD6801	Discontinued
0.7024	Intermediate Similarity	NPD7808	Phase 3
0.7021	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1652	Phase 2
0.7	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5126	Approved
0.6978	Remote Similarity	NPD5125	Phase 3
0.6959	Remote Similarity	NPD6653	Approved
0.6954	Remote Similarity	NPD2424	Discontinued
0.6937	Remote Similarity	NPD5402	Approved
0.6933	Remote Similarity	NPD2935	Discontinued
0.6923	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6798	Discontinued
0.6918	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5401	Approved
0.6894	Remote Similarity	NPD3882	Suspended
0.6894	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1933	Approved
0.6892	Remote Similarity	NPD6355	Discontinued
0.6883	Remote Similarity	NPD5058	Phase 3
0.6879	Remote Similarity	NPD3705	Approved
0.6879	Remote Similarity	NPD422	Phase 1
0.6875	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4062	Phase 3
0.687	Remote Similarity	NPD5048	Discontinued
0.6864	Remote Similarity	NPD7240	Approved
0.6855	Remote Similarity	NPD7411	Suspended
0.6849	Remote Similarity	NPD3027	Phase 3
0.6842	Remote Similarity	NPD1549	Phase 2
0.6831	Remote Similarity	NPD9717	Approved
0.6829	Remote Similarity	NPD7199	Phase 2
0.6821	Remote Similarity	NPD1551	Phase 2
0.6813	Remote Similarity	NPD1934	Approved
0.6806	Remote Similarity	NPD1203	Approved
0.6797	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD2534	Approved
0.6795	Remote Similarity	NPD2532	Approved
0.6795	Remote Similarity	NPD2533	Approved
0.6792	Remote Similarity	NPD6599	Discontinued
0.6791	Remote Similarity	NPD2067	Discontinued
0.6781	Remote Similarity	NPD6832	Phase 2
0.6779	Remote Similarity	NPD447	Suspended
0.6779	Remote Similarity	NPD4340	Discontinued
0.6779	Remote Similarity	NPD5124	Phase 1
0.6779	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6002	Phase 3
0.6776	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6004	Phase 3
0.6776	Remote Similarity	NPD6005	Phase 3
0.6776	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7843	Approved
0.6753	Remote Similarity	NPD8166	Discontinued
0.6736	Remote Similarity	NPD3225	Approved
0.6735	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD3817	Phase 2
0.6726	Remote Similarity	NPD3751	Discontinued
0.6718	Remote Similarity	NPD6647	Phase 2
0.6716	Remote Similarity	NPD2684	Approved
0.6716	Remote Similarity	NPD74	Approved
0.6716	Remote Similarity	NPD9266	Approved
0.6713	Remote Similarity	NPD9269	Phase 2
0.6712	Remote Similarity	NPD5736	Approved
0.6712	Remote Similarity	NPD9494	Approved
0.6711	Remote Similarity	NPD1240	Approved
0.6707	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6166	Phase 2
0.6707	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD694	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6362	Approved
0.669	Remote Similarity	NPD3847	Discontinued
0.6686	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD7819	Suspended
0.6647	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3400	Discontinued
0.6645	Remote Similarity	NPD2799	Discontinued
0.6645	Remote Similarity	NPD1510	Phase 2
0.6644	Remote Similarity	NPD520	Approved
0.6643	Remote Similarity	NPD5536	Phase 2
0.6643	Remote Similarity	NPD1535	Discovery
0.6642	Remote Similarity	NPD9264	Approved
0.6642	Remote Similarity	NPD9267	Approved
0.6642	Remote Similarity	NPD290	Approved
0.6642	Remote Similarity	NPD9263	Approved
0.6629	Remote Similarity	NPD6535	Approved
0.6629	Remote Similarity	NPD6534	Approved
0.6625	Remote Similarity	NPD7458	Discontinued
0.6625	Remote Similarity	NPD3455	Phase 2
0.6623	Remote Similarity	NPD1607	Approved
0.662	Remote Similarity	NPD1778	Approved
0.6619	Remote Similarity	NPD7157	Approved
0.6618	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7435	Discontinued
0.6608	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD9570	Approved
0.66	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4060	Phase 1
0.66	Remote Similarity	NPD1613	Approved
0.6597	Remote Similarity	NPD1481	Phase 2
0.6596	Remote Similarity	NPD1894	Discontinued
0.6594	Remote Similarity	NPD1241	Discontinued
0.6587	Remote Similarity	NPD6232	Discontinued
0.6587	Remote Similarity	NPD3787	Discontinued
0.6585	Remote Similarity	NPD7768	Phase 2
0.6582	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD8320	Phase 1
0.6576	Remote Similarity	NPD8319	Approved
0.6575	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD2797	Approved
0.6573	Remote Similarity	NPD3496	Discontinued
0.6571	Remote Similarity	NPD8434	Phase 2
0.6571	Remote Similarity	NPD8150	Discontinued
0.6562	Remote Similarity	NPD2934	Approved
0.6562	Remote Similarity	NPD2933	Approved
0.656	Remote Similarity	NPD689	Discontinued
0.6549	Remote Similarity	NPD9268	Approved
0.6547	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD2629	Approved
0.6545	Remote Similarity	NPD3749	Approved
0.6543	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6779	Approved
0.6538	Remote Similarity	NPD6781	Approved
0.6538	Remote Similarity	NPD6780	Approved
0.6538	Remote Similarity	NPD6782	Approved
0.6538	Remote Similarity	NPD6776	Approved
0.6538	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6778	Approved
0.6538	Remote Similarity	NPD3750	Approved
0.6538	Remote Similarity	NPD2575	Approved
0.6538	Remote Similarity	NPD6777	Approved
0.6536	Remote Similarity	NPD5588	Approved
0.6533	Remote Similarity	NPD6663	Approved
0.6531	Remote Similarity	NPD1019	Discontinued
0.6529	Remote Similarity	NPD7799	Discontinued
0.6527	Remote Similarity	NPD8127	Discontinued
0.6524	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7699	Phase 2
0.6519	Remote Similarity	NPD7700	Phase 2
0.6519	Remote Similarity	NPD4357	Discontinued
0.6512	Remote Similarity	NPD2860	Approved
0.6512	Remote Similarity	NPD2859	Approved
0.651	Remote Similarity	NPD7095	Approved
0.6509	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.65	Remote Similarity	NPD920	Approved
0.6494	Remote Similarity	NPD2240	Approved
0.6494	Remote Similarity	NPD2239	Approved
0.6494	Remote Similarity	NPD2796	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