NPASS Compound

Structure

NPC472132 OpenBabel07101718292D 37 40 0 0 1 0 0 0 0 0999 V2000 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 -6.9282 0.0000 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 -6.9282 -2.0000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 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 -3.4641 -2.0000 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 -1.7321 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 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 -0.8660 1.5000 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 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 1 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 -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 -0.8660 2.5000 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 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 0.0000 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 2 15 1 0 0 0 0 3 6 1 0 0 0 0 3 13 2 0 0 0 0 4 7 2 0 0 0 0 4 13 1 0 0 0 0 5 8 2 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 7 14 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 25 1 0 0 0 0 10 33 1 0 0 0 0 11 26 1 0 0 0 0 12 16 2 0 0 0 0 12 34 1 0 0 0 0 14 27 1 0 0 0 0 15 23 1 0 0 0 0 15 25 1 6 0 0 0 16 22 1 0 0 0 0 16 25 1 0 0 0 0 17 11 1 1 0 0 0 17 19 1 0 0 0 0 17 35 1 0 0 0 0 18 28 2 0 0 0 0 18 36 1 0 0 0 0 19 20 1 0 0 0 0 19 29 1 6 0 0 0 20 21 1 0 0 0 0 20 30 1 1 0 0 0 21 24 1 0 0 0 0 21 36 1 6 0 0 0 22 31 2 0 0 0 0 22 33 1 0 0 0 0 23 34 1 0 0 0 0 23 37 1 1 0 0 0 24 35 1 0 0 0 0 24 37 1 1 0 0 0 25 32 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	520.16
Volume:	491.121
LogP:	1.065
LogD:	0.665
LogS:	-3.074
# Rotatable Bonds:	8
TPSA:	181.44
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.177
Synthetic Accessibility Score:	4.963
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:	-6.069
MDCK Permeability:	4.835300205741078e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.075
Human Intestinal Absorption (HIA):	0.942
20% Bioavailability (F20%):	0.978
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.136
Plasma Protein Binding (PPB):	79.5102310180664%
Volume Distribution (VD):	0.521
Pgp-substrate:	19.267528533935547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.045
CYP2C19-inhibitor:	0.084
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.103
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.106
CYP3A4-substrate:	0.195

ADMET: Excretion

Clearance (CL):	1.28
Half-life (T1/2):	0.877

ADMET: Toxicity

hERG Blockers:	0.193
Human Hepatotoxicity (H-HT):	0.106
Drug-inuced Liver Injury (DILI):	0.13
AMES Toxicity:	0.087
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.698
Carcinogencity:	0.507
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.066

Download Data

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

Natural Product: NPC472132

Natural Product ID:	NPC472132
*Common Name:**	CKSVOUSTYOPWFX-DOIYPIOUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CKSVOUSTYOPWFX-DOIYPIOUSA-N
Standard InCHI:	InChI=1S/C25H28O12/c1-2-15-23(34-12-16-22(31)33-10-9-25(15,16)32)37-24-21(20(30)19(29)17(11-26)35-24)36-18(28)8-5-13-3-6-14(27)7-4-13/h2-8,12,15,17,19-21,23-24,26-27,29-30,32H,1,9-11H2/b8-5+/t15-,17+,19+,20-,21+,23-,24-,25+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C3[C@@]([C@H]2C=C)(O)CCOC3=O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338644
PubChem CID:	n.a.
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
NPO32460	Gentianella azurea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24806310]
NPO32460	Gentianella azurea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25442320]

☑ 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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	200000.0	nM	PMID[468043]

☑ 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 NPC472132 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	312
0.1-0.2	1175
0.2-0.3	2907
0.3-0.4	6799
0.4-0.5	10286
0.5-0.6	8130
0.6-0.7	10397
0.7-0.8	2447
0.8-0.85	174
0.85-0.9	56
0.9-0.95	13
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9203	High Similarity	NPC63304
0.9185	High Similarity	NPC469364
0.9185	High Similarity	NPC65262
0.9185	High Similarity	NPC101686
0.9137	High Similarity	NPC475528
0.913	High Similarity	NPC293154
0.9118	High Similarity	NPC220936
0.9118	High Similarity	NPC31745
0.9104	High Similarity	NPC169398
0.9071	High Similarity	NPC475539
0.9071	High Similarity	NPC474268
0.9071	High Similarity	NPC143246
0.9071	High Similarity	NPC212808
0.9071	High Similarity	NPC119773
0.9023	High Similarity	NPC254819
0.9023	High Similarity	NPC281798
0.9008	High Similarity	NPC106677
0.8931	High Similarity	NPC252114
0.8915	High Similarity	NPC52097
0.8872	High Similarity	NPC253595
0.8855	High Similarity	NPC126991
0.8855	High Similarity	NPC83218
0.8837	High Similarity	NPC11724
0.8794	High Similarity	NPC202391
0.8794	High Similarity	NPC296659
0.8794	High Similarity	NPC77922
0.8794	High Similarity	NPC473281
0.8788	High Similarity	NPC471157
0.876	High Similarity	NPC476872
0.8759	High Similarity	NPC474620
0.8741	High Similarity	NPC225384
0.8741	High Similarity	NPC138777
0.8741	High Similarity	NPC46137
0.8741	High Similarity	NPC246869
0.8741	High Similarity	NPC235294
0.8731	High Similarity	NPC469549
0.8723	High Similarity	NPC475213
0.8723	High Similarity	NPC152796
0.8722	High Similarity	NPC288416
0.8705	High Similarity	NPC49597
0.869	High Similarity	NPC69367
0.8662	High Similarity	NPC184464
0.8662	High Similarity	NPC251062
0.8657	High Similarity	NPC225307
0.8652	High Similarity	NPC296643
0.8623	High Similarity	NPC476870
0.8621	High Similarity	NPC478234
0.8621	High Similarity	NPC478236
0.8603	High Similarity	NPC478255
0.8592	High Similarity	NPC186296
0.8592	High Similarity	NPC469367
0.8582	High Similarity	NPC137501
0.8582	High Similarity	NPC7518
0.8582	High Similarity	NPC35288
0.8582	High Similarity	NPC156692
0.8582	High Similarity	NPC173150
0.8582	High Similarity	NPC471882
0.8582	High Similarity	NPC45224
0.8582	High Similarity	NPC159387
0.8582	High Similarity	NPC471881
0.8582	High Similarity	NPC46644
0.8582	High Similarity	NPC154262
0.8571	High Similarity	NPC220942
0.8562	High Similarity	NPC117346
0.8562	High Similarity	NPC240592
0.8561	High Similarity	NPC470572
0.8561	High Similarity	NPC471345
0.8552	High Similarity	NPC23677
0.8551	High Similarity	NPC471029
0.854	High Similarity	NPC473285
0.8521	High Similarity	NPC469623
0.8521	High Similarity	NPC148080
0.8503	High Similarity	NPC158546
0.8503	High Similarity	NPC289021
0.8493	Intermediate Similarity	NPC96599
0.8489	Intermediate Similarity	NPC263829
0.8483	Intermediate Similarity	NPC473149
0.8478	Intermediate Similarity	NPC114116
0.8478	Intermediate Similarity	NPC28637
0.8472	Intermediate Similarity	NPC210330
0.8467	Intermediate Similarity	NPC475378
0.8462	Intermediate Similarity	NPC478250
0.8456	Intermediate Similarity	NPC229784
0.8456	Intermediate Similarity	NPC472128
0.8456	Intermediate Similarity	NPC477294
0.8456	Intermediate Similarity	NPC472127
0.8456	Intermediate Similarity	NPC477293
0.8456	Intermediate Similarity	NPC295970
0.8451	Intermediate Similarity	NPC80098
0.8446	Intermediate Similarity	NPC194705
0.8414	Intermediate Similarity	NPC37838
0.8411	Intermediate Similarity	NPC286919
0.8411	Intermediate Similarity	NPC475663
0.8406	Intermediate Similarity	NPC473924
0.8394	Intermediate Similarity	NPC289415
0.8394	Intermediate Similarity	NPC319995
0.8382	Intermediate Similarity	NPC232880
0.837	Intermediate Similarity	NPC61181
0.8369	Intermediate Similarity	NPC476376
0.8369	Intermediate Similarity	NPC260425
0.8369	Intermediate Similarity	NPC78363
0.8355	Intermediate Similarity	NPC469384
0.8345	Intermediate Similarity	NPC254398
0.8345	Intermediate Similarity	NPC215484
0.8333	Intermediate Similarity	NPC116104
0.8333	Intermediate Similarity	NPC237872
0.8333	Intermediate Similarity	NPC302286
0.8333	Intermediate Similarity	NPC263397
0.8333	Intermediate Similarity	NPC88754
0.8333	Intermediate Similarity	NPC219677
0.8322	Intermediate Similarity	NPC203664
0.8322	Intermediate Similarity	NPC478235
0.8322	Intermediate Similarity	NPC106818
0.8311	Intermediate Similarity	NPC182350
0.8311	Intermediate Similarity	NPC12006
0.831	Intermediate Similarity	NPC205195
0.831	Intermediate Similarity	NPC197316
0.831	Intermediate Similarity	NPC64141
0.831	Intermediate Similarity	NPC89105
0.831	Intermediate Similarity	NPC476383
0.831	Intermediate Similarity	NPC81515
0.831	Intermediate Similarity	NPC472350
0.831	Intermediate Similarity	NPC68092
0.8309	Intermediate Similarity	NPC103533
0.8309	Intermediate Similarity	NPC476873
0.8298	Intermediate Similarity	NPC166180
0.8288	Intermediate Similarity	NPC291153
0.8286	Intermediate Similarity	NPC34293
0.8286	Intermediate Similarity	NPC287597
0.8286	Intermediate Similarity	NPC886
0.8276	Intermediate Similarity	NPC471028
0.8267	Intermediate Similarity	NPC229354
0.8267	Intermediate Similarity	NPC87403
0.8261	Intermediate Similarity	NPC470122
0.8261	Intermediate Similarity	NPC17968
0.8261	Intermediate Similarity	NPC469705
0.8252	Intermediate Similarity	NPC202700
0.8248	Intermediate Similarity	NPC158673
0.8231	Intermediate Similarity	NPC18789
0.8227	Intermediate Similarity	NPC320259
0.8217	Intermediate Similarity	NPC313193
0.8214	Intermediate Similarity	NPC164172
0.8207	Intermediate Similarity	NPC204644
0.8207	Intermediate Similarity	NPC105005
0.8194	Intermediate Similarity	NPC79908
0.8194	Intermediate Similarity	NPC47471
0.8194	Intermediate Similarity	NPC476385
0.8194	Intermediate Similarity	NPC476377
0.8194	Intermediate Similarity	NPC134405
0.8182	Intermediate Similarity	NPC321638
0.8182	Intermediate Similarity	NPC321184
0.8182	Intermediate Similarity	NPC171134
0.8182	Intermediate Similarity	NPC328273
0.8176	Intermediate Similarity	NPC189631
0.8176	Intermediate Similarity	NPC473138
0.8176	Intermediate Similarity	NPC28776
0.817	Intermediate Similarity	NPC187205
0.8169	Intermediate Similarity	NPC157554
0.8163	Intermediate Similarity	NPC473867
0.8163	Intermediate Similarity	NPC473147
0.8162	Intermediate Similarity	NPC123704
0.8158	Intermediate Similarity	NPC475484
0.8156	Intermediate Similarity	NPC471883
0.8151	Intermediate Similarity	NPC296954
0.8151	Intermediate Similarity	NPC141455
0.8151	Intermediate Similarity	NPC300894
0.8151	Intermediate Similarity	NPC476867
0.8151	Intermediate Similarity	NPC196063
0.8151	Intermediate Similarity	NPC194938
0.8151	Intermediate Similarity	NPC478240
0.8146	Intermediate Similarity	NPC246893
0.8143	Intermediate Similarity	NPC471066
0.8143	Intermediate Similarity	NPC471095
0.8138	Intermediate Similarity	NPC65833
0.8138	Intermediate Similarity	NPC222433
0.8138	Intermediate Similarity	NPC265648
0.8134	Intermediate Similarity	NPC55608
0.8133	Intermediate Similarity	NPC475379
0.8129	Intermediate Similarity	NPC17567
0.8125	Intermediate Similarity	NPC475530
0.8125	Intermediate Similarity	NPC473799
0.8121	Intermediate Similarity	NPC22137
0.8121	Intermediate Similarity	NPC478242
0.8116	Intermediate Similarity	NPC146540
0.8116	Intermediate Similarity	NPC198487
0.8108	Intermediate Similarity	NPC97240
0.8108	Intermediate Similarity	NPC470330
0.8095	Intermediate Similarity	NPC100998
0.8095	Intermediate Similarity	NPC476869
0.8095	Intermediate Similarity	NPC476868
0.8095	Intermediate Similarity	NPC476866
0.8095	Intermediate Similarity	NPC34927
0.8095	Intermediate Similarity	NPC34587
0.8095	Intermediate Similarity	NPC252292
0.8095	Intermediate Similarity	NPC476864
0.8095	Intermediate Similarity	NPC476382
0.8092	Intermediate Similarity	NPC175771
0.8092	Intermediate Similarity	NPC478232
0.8089	Intermediate Similarity	NPC294722
0.8089	Intermediate Similarity	NPC475979

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 NPC472132 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	733
0.2-0.3	1620
0.3-0.4	2910
0.4-0.5	2100
0.5-0.6	1163
0.6-0.7	335
0.7-0.8	27
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
0.831	Intermediate Similarity	NPD7266	Discontinued
0.7935	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD6190	Approved
0.7683	Intermediate Similarity	NPD7685	Pre-registration
0.7647	Intermediate Similarity	NPD1653	Approved
0.7548	Intermediate Similarity	NPD4380	Phase 2
0.7516	Intermediate Similarity	NPD8455	Phase 2
0.75	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD1091	Approved
0.7455	Intermediate Similarity	NPD7472	Approved
0.7425	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6797	Phase 2
0.7381	Intermediate Similarity	NPD8313	Approved
0.7381	Intermediate Similarity	NPD8312	Approved
0.7365	Intermediate Similarity	NPD7251	Discontinued
0.7349	Intermediate Similarity	NPD7074	Phase 3
0.7333	Intermediate Similarity	NPD3818	Discontinued
0.7321	Intermediate Similarity	NPD7808	Phase 3
0.7319	Intermediate Similarity	NPD9545	Approved
0.7303	Intermediate Similarity	NPD4628	Phase 3
0.7279	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7097	Phase 1
0.7244	Intermediate Similarity	NPD5403	Approved
0.7229	Intermediate Similarity	NPD7228	Approved
0.72	Intermediate Similarity	NPD7033	Discontinued
0.7184	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6559	Discontinued
0.716	Intermediate Similarity	NPD7075	Discontinued
0.7125	Intermediate Similarity	NPD6801	Discontinued
0.7115	Intermediate Similarity	NPD5401	Approved
0.7115	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5124	Phase 1
0.7114	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3225	Approved
0.7078	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5402	Approved
0.7027	Intermediate Similarity	NPD3764	Approved
0.7024	Intermediate Similarity	NPD3751	Discontinued
0.7019	Intermediate Similarity	NPD37	Approved
0.7015	Intermediate Similarity	NPD1358	Approved
0.7013	Intermediate Similarity	NPD1652	Phase 2
0.7012	Intermediate Similarity	NPD6234	Discontinued
0.7	Intermediate Similarity	NPD230	Phase 1
0.6994	Remote Similarity	NPD4966	Approved
0.6994	Remote Similarity	NPD4967	Phase 2
0.6994	Remote Similarity	NPD4965	Approved
0.6986	Remote Similarity	NPD5647	Approved
0.698	Remote Similarity	NPD6233	Phase 2
0.6975	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7411	Suspended
0.6948	Remote Similarity	NPD1549	Phase 2
0.6948	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6799	Approved
0.694	Remote Similarity	NPD3134	Approved
0.6937	Remote Similarity	NPD7458	Discontinued
0.6934	Remote Similarity	NPD969	Suspended
0.6905	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6166	Phase 2
0.6905	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4340	Discontinued
0.6886	Remote Similarity	NPD3787	Discontinued
0.6883	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1510	Phase 2
0.686	Remote Similarity	NPD7240	Approved
0.6859	Remote Similarity	NPD3750	Approved
0.6859	Remote Similarity	NPD8166	Discontinued
0.6848	Remote Similarity	NPD8320	Phase 1
0.6848	Remote Similarity	NPD8319	Approved
0.6842	Remote Similarity	NPD6653	Approved
0.6829	Remote Similarity	NPD3817	Phase 2
0.6829	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7199	Phase 2
0.681	Remote Similarity	NPD1934	Approved
0.6809	Remote Similarity	NPD9493	Approved
0.6803	Remote Similarity	NPD2797	Approved
0.6802	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3268	Approved
0.68	Remote Similarity	NPD6798	Discontinued
0.68	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7435	Discontinued
0.6792	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6599	Discontinued
0.6781	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6355	Discontinued
0.6776	Remote Similarity	NPD1933	Approved
0.6768	Remote Similarity	NPD7819	Suspended
0.6768	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD8150	Discontinued
0.6759	Remote Similarity	NPD422	Phase 1
0.6757	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD6535	Approved
0.6722	Remote Similarity	NPD6534	Approved
0.6721	Remote Similarity	NPD6778	Approved
0.6721	Remote Similarity	NPD6782	Approved
0.6721	Remote Similarity	NPD6776	Approved
0.6721	Remote Similarity	NPD6777	Approved
0.6721	Remote Similarity	NPD6781	Approved
0.6721	Remote Similarity	NPD6780	Approved
0.6721	Remote Similarity	NPD6779	Approved
0.671	Remote Similarity	NPD1551	Phase 2
0.671	Remote Similarity	NPD2935	Discontinued
0.6708	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7700	Phase 2
0.6703	Remote Similarity	NPD7699	Phase 2
0.6689	Remote Similarity	NPD1203	Approved
0.6688	Remote Similarity	NPD6674	Discontinued
0.6687	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7768	Phase 2
0.6686	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD4908	Phase 1
0.6667	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD5058	Phase 3
0.6667	Remote Similarity	NPD1465	Phase 2
0.6647	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3749	Approved
0.6645	Remote Similarity	NPD4062	Phase 3
0.6644	Remote Similarity	NPD2798	Approved
0.6632	Remote Similarity	NPD7783	Phase 2
0.6632	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD7799	Discontinued
0.6627	Remote Similarity	NPD8127	Discontinued
0.6625	Remote Similarity	NPD1511	Approved
0.6624	Remote Similarity	NPD2424	Discontinued
0.6623	Remote Similarity	NPD7095	Approved
0.6623	Remote Similarity	NPD3027	Phase 3
0.6621	Remote Similarity	NPD5125	Phase 3
0.6621	Remote Similarity	NPD5126	Approved
0.6618	Remote Similarity	NPD5048	Discontinued
0.6614	Remote Similarity	NPD8151	Discontinued
0.6613	Remote Similarity	NPD7698	Approved
0.6613	Remote Similarity	NPD7696	Phase 3
0.6613	Remote Similarity	NPD7697	Approved
0.6603	Remote Similarity	NPD2796	Approved
0.6601	Remote Similarity	NPD4060	Phase 1
0.6601	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD1240	Approved
0.6601	Remote Similarity	NPD1613	Approved
0.66	Remote Similarity	NPD2861	Phase 2
0.66	Remote Similarity	NPD5736	Approved
0.6599	Remote Similarity	NPD9717	Approved
0.6596	Remote Similarity	NPD7584	Approved
0.6588	Remote Similarity	NPD6232	Discontinued
0.6579	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7874	Approved
0.6579	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6362	Approved
0.6573	Remote Similarity	NPD8434	Phase 2
0.657	Remote Similarity	NPD7473	Discontinued
0.6568	Remote Similarity	NPD5494	Approved
0.6561	Remote Similarity	NPD7701	Phase 2
0.6561	Remote Similarity	NPD6005	Phase 3
0.6561	Remote Similarity	NPD7585	Approved
0.6561	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6002	Phase 3
0.6561	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6004	Phase 3
0.6559	Remote Similarity	NPD6823	Phase 2
0.6556	Remote Similarity	NPD6832	Phase 2
0.6552	Remote Similarity	NPD1357	Approved
0.6543	Remote Similarity	NPD1512	Approved
0.6541	Remote Similarity	NPD3400	Discontinued
0.6538	Remote Similarity	NPD2799	Discontinued
0.6538	Remote Similarity	NPD3748	Approved
0.6531	Remote Similarity	NPD1535	Discovery
0.6531	Remote Similarity	NPD3705	Approved
0.6531	Remote Similarity	NPD1610	Phase 2
0.6529	Remote Similarity	NPD6959	Discontinued
0.6525	Remote Similarity	NPD7843	Approved
0.6524	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD1607	Approved
0.6508	Remote Similarity	NPD7583	Approved
0.6507	Remote Similarity	NPD1778	Approved
0.6503	Remote Similarity	NPD7157	Approved
0.6497	Remote Similarity	NPD5404	Approved
0.6497	Remote Similarity	NPD5405	Approved
0.6497	Remote Similarity	NPD5408	Approved
0.6497	Remote Similarity	NPD5406	Approved
0.6494	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.649	Remote Similarity	NPD9494	Approved
0.6489	Remote Similarity	NPD7871	Phase 2
0.6489	Remote Similarity	NPD7870	Phase 2
0.6488	Remote Similarity	NPD3882	Suspended
0.6486	Remote Similarity	NPD1481	Phase 2
0.6486	Remote Similarity	NPD1608	Approved
0.6486	Remote Similarity	NPD9269	Phase 2
0.6486	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6212	Phase 3
0.6484	Remote Similarity	NPD6213	Phase 3

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