NPASS Compound

Structure

NPC471032 OpenBabel07101718322D 35 38 0 0 1 0 0 0 0 0999 V2000 -3.4641 -0.0000 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 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 4.3301 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 5.1962 -1.0000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 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 0.8660 0.5000 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 1.7321 -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 4.3301 0.5000 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 5.1962 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -5.5000 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 3.4641 0.0000 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 1.7321 -1.0000 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 33 1 0 0 0 0 2 7 1 0 0 0 0 2 17 2 0 0 0 0 3 8 2 0 0 0 0 3 17 1 0 0 0 0 4 10 2 0 0 0 0 4 18 1 0 0 0 0 5 11 2 0 0 0 0 5 18 1 0 0 0 0 6 9 2 0 0 0 0 6 19 1 0 0 0 0 7 20 2 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 26 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 28 1 0 0 0 0 14 18 2 0 0 0 0 14 24 1 0 0 0 0 15 19 2 0 0 0 0 15 23 1 0 0 0 0 16 29 1 0 0 0 0 20 30 1 0 0 0 0 21 23 2 0 0 0 0 21 31 1 0 0 0 0 22 24 2 0 0 0 0 22 35 1 0 0 0 0 23 33 1 0 0 0 0 24 34 1 0 0 0 0 25 16 1 6 0 0 0 25 27 1 0 0 0 0 25 34 1 0 0 0 0 26 28 2 3 0 0 0 26 32 1 0 0 0 0 27 19 1 1 0 0 0 27 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	477.18
Volume:	484.85
LogP:	3.166
LogD:	3.084
LogS:	-4.324
# Rotatable Bonds:	9
TPSA:	117.48
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.368
Synthetic Accessibility Score:	3.293
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.558
MDCK Permeability:	4.477693892113166e-06
Pgp-inhibitor:	0.613
Pgp-substrate:	0.088
Human Intestinal Absorption (HIA):	0.039
20% Bioavailability (F20%):	0.752
30% Bioavailability (F30%):	0.203

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	97.9731674194336%
Volume Distribution (VD):	0.574
Pgp-substrate:	1.0874550342559814%

ADMET: Metabolism

CYP1A2-inhibitor:	0.371
CYP1A2-substrate:	0.223
CYP2C19-inhibitor:	0.613
CYP2C19-substrate:	0.095
CYP2C9-inhibitor:	0.876
CYP2C9-substrate:	0.506
CYP2D6-inhibitor:	0.822
CYP2D6-substrate:	0.235
CYP3A4-inhibitor:	0.885
CYP3A4-substrate:	0.52

ADMET: Excretion

Clearance (CL):	9.321
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.426
Human Hepatotoxicity (H-HT):	0.644
Drug-inuced Liver Injury (DILI):	0.658
AMES Toxicity:	0.628
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.127
Skin Sensitization:	0.165
Carcinogencity:	0.784
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.015

Download Data

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

Natural Product: NPC471032

Natural Product ID:	NPC471032
*Common Name:**	(Z)-3-{(2,3-Trans)-2-(4-Hydroxy-3-Methoxyphenyl)-3-Hydroxymethyl-2,3-Dihydrobenzo[B][1,4]Dioxin-6-Yl}-N-(4-Hydroxyphenethyl)Acrylamide
IUPAC Name:	(Z)-3-[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
Synonyms:
Standard InCHIKey:	SUSRJKSSWXDFKP-GCHVKDGMSA-N
Standard InCHI:	InChI=1S/C27H27NO7/c1-33-23-15-19(6-9-21(23)31)27-25(16-29)34-24-14-18(4-10-22(24)35-27)5-11-26(32)28-13-12-17-2-7-20(30)8-3-17/h2-11,14-15,25,27,29-31H,12-13,16H2,1H3,(H,28,32)/b11-5-/t25-,27-/m1/s1
SMILES:	COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC(=C3)C=CC(=O)NCCC4=CC=C(C=C4)O)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337123
PubChem CID:	71524306
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002699] Benzodioxanes [CHEMONTID:0002704] Phenylbenzodioxanes [CHEMONTID:0002707] Phenylbenzo-1,4-dioxanes

*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
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[12467621]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	root	n.a.	PMID[16212233]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	root bark	n.a.	n.a.	PMID[23282106]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[26982999]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[9090870]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17823	Lycium chinense	Species	Solanaceae	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
IC50	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	49900.0	nM	PMID[448441]
NPT1	Others	Radical scavenging activity		IC50	=	54100.0	nM	PMID[448441]

☑ 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 NPC471032 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	228
0.1-0.2	1278
0.2-0.3	5104
0.3-0.4	12837
0.4-0.5	4723
0.5-0.6	7364
0.6-0.7	8111
0.7-0.8	2761
0.8-0.85	238
0.85-0.9	40
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470935
0.9236	High Similarity	NPC115144
0.9236	High Similarity	NPC277857
0.9143	High Similarity	NPC14600
0.9143	High Similarity	NPC41473
0.9143	High Similarity	NPC204848
0.9143	High Similarity	NPC312770
0.9143	High Similarity	NPC160607
0.9078	High Similarity	NPC299583
0.9013	High Similarity	NPC179250
0.9013	High Similarity	NPC50380
0.8839	High Similarity	NPC90984
0.8811	High Similarity	NPC296898
0.8786	High Similarity	NPC214869
0.8777	High Similarity	NPC35961
0.8777	High Similarity	NPC52029
0.8777	High Similarity	NPC86030
0.8777	High Similarity	NPC195749
0.8777	High Similarity	NPC5851
0.8714	High Similarity	NPC114102
0.8707	High Similarity	NPC5462
0.8705	High Similarity	NPC155838
0.8705	High Similarity	NPC72529
0.8633	High Similarity	NPC292056
0.8633	High Similarity	NPC251571
0.8633	High Similarity	NPC118787
0.8633	High Similarity	NPC147821
0.8633	High Similarity	NPC183181
0.8633	High Similarity	NPC319625
0.8633	High Similarity	NPC111247
0.8633	High Similarity	NPC41706
0.8633	High Similarity	NPC163332
0.863	High Similarity	NPC222039
0.863	High Similarity	NPC100478
0.8609	High Similarity	NPC127402
0.86	High Similarity	NPC182119
0.8571	High Similarity	NPC252307
0.8571	High Similarity	NPC245826
0.8571	High Similarity	NPC474178
0.8562	High Similarity	NPC107602
0.8561	High Similarity	NPC191037
0.8561	High Similarity	NPC58607
0.8561	High Similarity	NPC178284
0.85	High Similarity	NPC153990
0.85	High Similarity	NPC186898
0.8489	Intermediate Similarity	NPC194519
0.8472	Intermediate Similarity	NPC170694
0.8446	Intermediate Similarity	NPC178466
0.8446	Intermediate Similarity	NPC63628
0.8435	Intermediate Similarity	NPC55793
0.8429	Intermediate Similarity	NPC301713
0.8425	Intermediate Similarity	NPC474390
0.8417	Intermediate Similarity	NPC114901
0.8417	Intermediate Similarity	NPC94276
0.8417	Intermediate Similarity	NPC48990
0.8417	Intermediate Similarity	NPC293701
0.8417	Intermediate Similarity	NPC109822
0.8392	Intermediate Similarity	NPC472597
0.8367	Intermediate Similarity	NPC22517
0.8356	Intermediate Similarity	NPC77861
0.8356	Intermediate Similarity	NPC306441
0.8356	Intermediate Similarity	NPC16435
0.8355	Intermediate Similarity	NPC139699
0.8355	Intermediate Similarity	NPC114659
0.8345	Intermediate Similarity	NPC478085
0.8333	Intermediate Similarity	NPC35932
0.8333	Intermediate Similarity	NPC253105
0.8333	Intermediate Similarity	NPC16208
0.8333	Intermediate Similarity	NPC7903
0.8333	Intermediate Similarity	NPC160991
0.8333	Intermediate Similarity	NPC201587
0.8333	Intermediate Similarity	NPC184447
0.8322	Intermediate Similarity	NPC472338
0.8311	Intermediate Similarity	NPC266197
0.8311	Intermediate Similarity	NPC291101
0.8311	Intermediate Similarity	NPC22317
0.8311	Intermediate Similarity	NPC262189
0.8299	Intermediate Similarity	NPC470413
0.8299	Intermediate Similarity	NPC211549
0.8299	Intermediate Similarity	NPC138738
0.8299	Intermediate Similarity	NPC126206
0.8288	Intermediate Similarity	NPC260898
0.8288	Intermediate Similarity	NPC94750
0.8288	Intermediate Similarity	NPC214729
0.8288	Intermediate Similarity	NPC61946
0.8288	Intermediate Similarity	NPC112939
0.8288	Intermediate Similarity	NPC112246
0.8288	Intermediate Similarity	NPC474206
0.8288	Intermediate Similarity	NPC234333
0.8288	Intermediate Similarity	NPC47398
0.8288	Intermediate Similarity	NPC470356
0.8288	Intermediate Similarity	NPC121812
0.8286	Intermediate Similarity	NPC62101
0.8286	Intermediate Similarity	NPC95733
0.8273	Intermediate Similarity	NPC71090
0.8255	Intermediate Similarity	NPC178054
0.8255	Intermediate Similarity	NPC470372
0.8252	Intermediate Similarity	NPC226788
0.8252	Intermediate Similarity	NPC210623
0.8252	Intermediate Similarity	NPC218856
0.8252	Intermediate Similarity	NPC285339
0.8252	Intermediate Similarity	NPC222004
0.8252	Intermediate Similarity	NPC190629
0.8252	Intermediate Similarity	NPC273295
0.8252	Intermediate Similarity	NPC470258
0.8252	Intermediate Similarity	NPC202582
0.8252	Intermediate Similarity	NPC3439
0.8243	Intermediate Similarity	NPC477837
0.8243	Intermediate Similarity	NPC477838
0.8239	Intermediate Similarity	NPC118533
0.8239	Intermediate Similarity	NPC165045
0.8231	Intermediate Similarity	NPC302701
0.8231	Intermediate Similarity	NPC474639
0.8231	Intermediate Similarity	NPC471665
0.8231	Intermediate Similarity	NPC471664
0.8231	Intermediate Similarity	NPC227503
0.8231	Intermediate Similarity	NPC230734
0.8231	Intermediate Similarity	NPC269091
0.8219	Intermediate Similarity	NPC237594
0.8219	Intermediate Similarity	NPC249791
0.8219	Intermediate Similarity	NPC310854
0.8219	Intermediate Similarity	NPC476387
0.8219	Intermediate Similarity	NPC119060
0.8214	Intermediate Similarity	NPC471693
0.8212	Intermediate Similarity	NPC313414
0.8212	Intermediate Similarity	NPC171932
0.8212	Intermediate Similarity	NPC28440
0.8207	Intermediate Similarity	NPC470752
0.8201	Intermediate Similarity	NPC470804
0.8194	Intermediate Similarity	NPC92164
0.8194	Intermediate Similarity	NPC174495
0.8194	Intermediate Similarity	NPC187998
0.8194	Intermediate Similarity	NPC42300
0.8194	Intermediate Similarity	NPC77040
0.8194	Intermediate Similarity	NPC153739
0.8194	Intermediate Similarity	NPC257582
0.8194	Intermediate Similarity	NPC242807
0.8194	Intermediate Similarity	NPC64201
0.8194	Intermediate Similarity	NPC145305
0.8194	Intermediate Similarity	NPC241522
0.8188	Intermediate Similarity	NPC106944
0.8176	Intermediate Similarity	NPC176051
0.8176	Intermediate Similarity	NPC326797
0.8176	Intermediate Similarity	NPC102904
0.8176	Intermediate Similarity	NPC107551
0.8176	Intermediate Similarity	NPC103976
0.8176	Intermediate Similarity	NPC474282
0.8169	Intermediate Similarity	NPC17837
0.8169	Intermediate Similarity	NPC304630
0.8163	Intermediate Similarity	NPC472337
0.8163	Intermediate Similarity	NPC164787
0.8163	Intermediate Similarity	NPC151224
0.8163	Intermediate Similarity	NPC93783
0.8158	Intermediate Similarity	NPC274960
0.8158	Intermediate Similarity	NPC143120
0.8158	Intermediate Similarity	NPC473909
0.8151	Intermediate Similarity	NPC263064
0.8151	Intermediate Similarity	NPC168059
0.8151	Intermediate Similarity	NPC475840
0.8151	Intermediate Similarity	NPC229442
0.8151	Intermediate Similarity	NPC11060
0.8141	Intermediate Similarity	NPC197741
0.8141	Intermediate Similarity	NPC140915
0.8141	Intermediate Similarity	NPC18249
0.8141	Intermediate Similarity	NPC10221
0.8141	Intermediate Similarity	NPC305700
0.8141	Intermediate Similarity	NPC187028
0.8138	Intermediate Similarity	NPC469625
0.8138	Intermediate Similarity	NPC130595
0.8138	Intermediate Similarity	NPC470096
0.8138	Intermediate Similarity	NPC470095
0.8138	Intermediate Similarity	NPC30043
0.8138	Intermediate Similarity	NPC309787
0.8138	Intermediate Similarity	NPC277804
0.8138	Intermediate Similarity	NPC93882
0.8138	Intermediate Similarity	NPC469613
0.8133	Intermediate Similarity	NPC83375
0.8133	Intermediate Similarity	NPC471389
0.8133	Intermediate Similarity	NPC224876
0.8125	Intermediate Similarity	NPC475875
0.8125	Intermediate Similarity	NPC170844
0.8125	Intermediate Similarity	NPC476968
0.8121	Intermediate Similarity	NPC260842
0.8112	Intermediate Similarity	NPC210355
0.8112	Intermediate Similarity	NPC5428
0.8112	Intermediate Similarity	NPC474119
0.8108	Intermediate Similarity	NPC254610
0.8108	Intermediate Similarity	NPC248727
0.8108	Intermediate Similarity	NPC477939
0.8108	Intermediate Similarity	NPC162659
0.8108	Intermediate Similarity	NPC156502
0.8108	Intermediate Similarity	NPC472336
0.8108	Intermediate Similarity	NPC54743
0.8108	Intermediate Similarity	NPC10737
0.8108	Intermediate Similarity	NPC270456
0.8108	Intermediate Similarity	NPC265433
0.8108	Intermediate Similarity	NPC199459
0.8108	Intermediate Similarity	NPC209985
0.8108	Intermediate Similarity	NPC52277
0.8108	Intermediate Similarity	NPC470802

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 NPC471032 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	693
0.2-0.3	1106
0.3-0.4	2459
0.4-0.5	2273
0.5-0.6	1442
0.6-0.7	818
0.7-0.8	187
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
0.8344	Intermediate Similarity	NPD4123	Phase 3
0.82	Intermediate Similarity	NPD6331	Phase 2
0.8194	Intermediate Similarity	NPD4675	Approved
0.8194	Intermediate Similarity	NPD4678	Approved
0.8153	Intermediate Similarity	NPD5772	Approved
0.8153	Intermediate Similarity	NPD5773	Approved
0.8138	Intermediate Similarity	NPD2674	Phase 3
0.8125	Intermediate Similarity	NPD3027	Phase 3
0.8082	Intermediate Similarity	NPD1613	Approved
0.8082	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD3060	Approved
0.8	Intermediate Similarity	NPD2122	Discontinued
0.7975	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD1558	Phase 1
0.7945	Intermediate Similarity	NPD3145	Approved
0.7945	Intermediate Similarity	NPD3144	Approved
0.7935	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2161	Phase 2
0.7925	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD4005	Discontinued
0.7895	Intermediate Similarity	NPD4162	Approved
0.7881	Intermediate Similarity	NPD1375	Discontinued
0.7838	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD52	Approved
0.7821	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7526	Approved
0.7808	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6584	Phase 3
0.7778	Intermediate Similarity	NPD4237	Approved
0.7778	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4236	Phase 3
0.7778	Intermediate Similarity	NPD5177	Phase 3
0.7763	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD3686	Approved
0.7722	Intermediate Similarity	NPD3687	Approved
0.7712	Intermediate Similarity	NPD7153	Discontinued
0.7702	Intermediate Similarity	NPD2978	Approved
0.7702	Intermediate Similarity	NPD2977	Approved
0.7692	Intermediate Similarity	NPD7212	Phase 2
0.7692	Intermediate Similarity	NPD7213	Phase 3
0.7677	Intermediate Similarity	NPD5241	Discontinued
0.7651	Intermediate Similarity	NPD7477	Discontinued
0.7643	Intermediate Similarity	NPD7447	Phase 1
0.7632	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD2489	Approved
0.7605	Intermediate Similarity	NPD27	Approved
0.759	Intermediate Similarity	NPD3051	Approved
0.7586	Intermediate Similarity	NPD6582	Phase 2
0.7586	Intermediate Similarity	NPD6583	Phase 3
0.7568	Intermediate Similarity	NPD4908	Phase 1
0.7545	Intermediate Similarity	NPD2970	Approved
0.7545	Intermediate Similarity	NPD2969	Approved
0.7532	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4663	Approved
0.7517	Intermediate Similarity	NPD2231	Phase 2
0.7517	Intermediate Similarity	NPD2235	Phase 2
0.7514	Intermediate Similarity	NPD8054	Approved
0.7514	Intermediate Similarity	NPD8053	Approved
0.75	Intermediate Similarity	NPD3054	Approved
0.75	Intermediate Similarity	NPD3052	Approved
0.7486	Intermediate Similarity	NPD7906	Approved
0.7485	Intermediate Similarity	NPD7089	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3062	Approved
0.7483	Intermediate Similarity	NPD3061	Approved
0.7483	Intermediate Similarity	NPD3059	Approved
0.7469	Intermediate Similarity	NPD6072	Discontinued
0.7467	Intermediate Similarity	NPD5718	Phase 2
0.7467	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1669	Approved
0.7457	Intermediate Similarity	NPD7310	Approved
0.7457	Intermediate Similarity	NPD4578	Approved
0.7457	Intermediate Similarity	NPD7311	Approved
0.7457	Intermediate Similarity	NPD4577	Approved
0.7457	Intermediate Similarity	NPD7312	Approved
0.7457	Intermediate Similarity	NPD7313	Approved
0.7452	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2677	Approved
0.7442	Intermediate Similarity	NPD7039	Approved
0.7442	Intermediate Similarity	NPD7038	Approved
0.7439	Intermediate Similarity	NPD2560	Approved
0.7439	Intermediate Similarity	NPD2563	Approved
0.7421	Intermediate Similarity	NPD3536	Discontinued
0.7421	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7266	Discontinued
0.7417	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD840	Approved
0.7417	Intermediate Similarity	NPD839	Approved
0.7415	Intermediate Similarity	NPD2922	Phase 1
0.7414	Intermediate Similarity	NPD7309	Approved
0.741	Intermediate Similarity	NPD228	Approved
0.7405	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4108	Discontinued
0.7399	Intermediate Similarity	NPD7549	Discontinued
0.7396	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6166	Phase 2
0.7396	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5314	Approved
0.7383	Intermediate Similarity	NPD2861	Phase 2
0.7381	Intermediate Similarity	NPD6071	Discontinued
0.7372	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2238	Phase 2
0.7358	Intermediate Similarity	NPD4357	Discontinued
0.7358	Intermediate Similarity	NPD1774	Approved
0.7349	Intermediate Similarity	NPD5604	Discontinued
0.7349	Intermediate Similarity	NPD7831	Phase 2
0.7349	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7833	Phase 2
0.7347	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD2219	Phase 1
0.7325	Intermediate Similarity	NPD6674	Discontinued
0.7317	Intermediate Similarity	NPD1934	Approved
0.731	Intermediate Similarity	NPD9381	Approved
0.731	Intermediate Similarity	NPD9384	Approved
0.7303	Intermediate Similarity	NPD3532	Approved
0.7303	Intermediate Similarity	NPD3530	Approved
0.7303	Intermediate Similarity	NPD3531	Approved
0.7297	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7007	Discovery
0.7262	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7037	Approved
0.7256	Intermediate Similarity	NPD3778	Approved
0.7255	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3620	Phase 2
0.7246	Intermediate Similarity	NPD4055	Discovery
0.7237	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD9622	Approved
0.723	Intermediate Similarity	NPD3685	Discontinued
0.723	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4538	Approved
0.7226	Intermediate Similarity	NPD4536	Approved
0.7226	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6030	Approved
0.7222	Intermediate Similarity	NPD6031	Approved
0.7215	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5061	Approved
0.7215	Intermediate Similarity	NPD5062	Approved
0.7212	Intermediate Similarity	NPD5722	Discontinued
0.7205	Intermediate Similarity	NPD3985	Discontinued
0.7205	Intermediate Similarity	NPD4739	Approved
0.72	Intermediate Similarity	NPD9619	Approved
0.72	Intermediate Similarity	NPD558	Phase 2
0.72	Intermediate Similarity	NPD9620	Approved
0.72	Intermediate Similarity	NPD9621	Approved
0.7197	Intermediate Similarity	NPD3656	Approved
0.7195	Intermediate Similarity	NPD3296	Phase 1
0.7191	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7124	Phase 2
0.7186	Intermediate Similarity	NPD7773	Phase 2
0.7183	Intermediate Similarity	NPD5283	Phase 1
0.7178	Intermediate Similarity	NPD1653	Approved
0.7176	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6581	Approved
0.7172	Intermediate Similarity	NPD6580	Approved
0.7171	Intermediate Similarity	NPD3180	Approved
0.7171	Intermediate Similarity	NPD3179	Approved
0.7169	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD8156	Discontinued
0.7162	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2157	Approved
0.716	Intermediate Similarity	NPD6746	Phase 2
0.716	Intermediate Similarity	NPD4666	Phase 3
0.7152	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4773	Phase 2
0.7152	Intermediate Similarity	NPD1712	Approved
0.7152	Intermediate Similarity	NPD4772	Phase 2
0.7152	Intermediate Similarity	NPD4993	Discontinued
0.7152	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8070	Approved
0.7126	Intermediate Similarity	NPD6063	Approved
0.7125	Intermediate Similarity	NPD3692	Discontinued
0.7124	Intermediate Similarity	NPD601	Approved
0.7124	Intermediate Similarity	NPD597	Approved
0.7124	Intermediate Similarity	NPD598	Approved
0.7124	Intermediate Similarity	NPD5110	Phase 2
0.7124	Intermediate Similarity	NPD5109	Approved
0.7124	Intermediate Similarity	NPD5111	Phase 2
0.7123	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6896	Approved
0.7115	Intermediate Similarity	NPD6895	Approved
0.7113	Intermediate Similarity	NPD821	Approved
0.711	Intermediate Similarity	NPD8099	Discontinued
0.711	Intermediate Similarity	NPD8252	Approved
0.711	Intermediate Similarity	NPD8251	Approved
0.7102	Intermediate Similarity	NPD3936	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5709	Phase 3
0.7095	Intermediate Similarity	NPD1091	Approved
0.7095	Intermediate Similarity	NPD6842	Approved
0.7095	Intermediate Similarity	NPD6841	Approved
0.7095	Intermediate Similarity	NPD6843	Phase 3
0.7095	Intermediate Similarity	NPD1610	Phase 2
0.7091	Intermediate Similarity	NPD6502	Phase 2
0.7083	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6788	Approved
0.7078	Intermediate Similarity	NPD1136	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