NPASS Compound

Structure

NPC79184 OpenBabel07101719252D 33 34 0 0 1 0 0 0 0 0999 V2000 9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 4.3301 -1.5000 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 0.0000 -2.0000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 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 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 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 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 2 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 6.9282 0.0000 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 5.1962 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 0.8660 -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 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 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 1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 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 -0.8660 1.5000 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 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 3 16 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 30 1 0 0 0 0 8 31 1 0 0 0 0 9 10 2 0 0 0 0 10 17 1 0 0 0 0 11 17 2 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 20 2 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 22 2 0 0 0 0 15 2 1 6 0 0 0 15 23 1 0 0 0 0 15 32 1 0 0 0 0 16 26 2 0 0 0 0 16 33 1 0 0 0 0 18 23 1 0 0 0 0 19 25 2 0 0 0 0 19 27 1 0 0 0 0 20 25 1 0 0 0 0 20 28 1 0 0 0 0 21 24 2 0 0 0 0 21 29 1 0 0 0 0 22 24 1 0 0 0 0 22 30 1 0 0 0 0 23 33 1 1 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.21
Volume:	473.073
LogP:	3.402
LogD:	3.121
LogS:	-4.518
# Rotatable Bonds:	12
TPSA:	81.68
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.441
Synthetic Accessibility Score:	3.409
Fsp3:	0.4
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:	-4.644
MDCK Permeability:	2.5504128643660806e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.162
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.287

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.315
Plasma Protein Binding (PPB):	68.53533172607422%
Volume Distribution (VD):	0.681
Pgp-substrate:	25.848526000976562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.069
CYP1A2-substrate:	0.949
CYP2C19-inhibitor:	0.432
CYP2C19-substrate:	0.927
CYP2C9-inhibitor:	0.401
CYP2C9-substrate:	0.865
CYP2D6-inhibitor:	0.071
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.885
CYP3A4-substrate:	0.929

ADMET: Excretion

Clearance (CL):	3.001
Half-life (T1/2):	0.615

ADMET: Toxicity

hERG Blockers:	0.152
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.901
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.343
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.056
Respiratory Toxicity:	0.017

Download Data

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

Natural Product: NPC79184

Natural Product ID:	NPC79184
*Common Name:**	(-)-(7R,8R)-7-O-Acetylpolysphorin
IUPAC Name:	[(1R,2R)-2-[2,6-dimethoxy-4-[(E)-prop-1-enyl]phenoxy]-1-(3,4,5-trimethoxyphenyl)propyl] acetate
Synonyms:
Standard InCHIKey:	KDVYEAVKWMGOPV-YDORHEMQSA-N
Standard InCHI:	InChI=1S/C25H32O8/c1-9-10-17-11-19(27-4)25(20(12-17)28-5)32-15(2)23(33-16(3)26)18-13-21(29-6)24(31-8)22(14-18)30-7/h9-15,23H,1-8H3/b10-9+/t15-,23+/m1/s1
SMILES:	C/C=C/c1cc(c(c(c1)OC)O[C@H](C)[C@@H](c1cc(c(c(c1)OC)OC)OC)OC(=O)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3105535
PubChem CID:	76317426
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0001097] Benzyloxycarbonyls

*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
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754613]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	root	n.a.	PMID[14750033]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15482936]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	roots	n.a.	n.a.	PMID[18841903]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24359277]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[24387347]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20323	Saururus chinensis	Species	Saururaceae	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
EC50	1
IC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	16900.0	nM	PMID[533716]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	3.0	n.a.	PMID[533715]
NPT27	Others	Unspecified		CC50	=	76800.0	nM	PMID[533715]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	EC50	=	25400.0	nM	PMID[533715]

☑ 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 NPC79184 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	335
0.1-0.2	1528
0.2-0.3	4926
0.3-0.4	11892
0.4-0.5	5994
0.5-0.6	4396
0.6-0.7	7953
0.7-0.8	4679
0.8-0.85	802
0.85-0.9	150
0.9-0.95	32
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC307042
0.9837	High Similarity	NPC210674
0.9685	High Similarity	NPC309744
0.968	High Similarity	NPC476399
0.9535	High Similarity	NPC471719
0.9457	High Similarity	NPC224941
0.9457	High Similarity	NPC311430
0.9431	High Similarity	NPC279379
0.9365	High Similarity	NPC474651
0.9365	High Similarity	NPC474623
0.935	High Similarity	NPC261661
0.9231	High Similarity	NPC474600
0.9187	High Similarity	NPC472596
0.9147	High Similarity	NPC30043
0.9147	High Similarity	NPC469613
0.9147	High Similarity	NPC469625
0.9134	High Similarity	NPC194841
0.9091	High Similarity	NPC143895
0.907	High Similarity	NPC469612
0.907	High Similarity	NPC469614
0.9062	High Similarity	NPC31707
0.9032	High Similarity	NPC267064
0.9023	High Similarity	NPC865
0.9	High Similarity	NPC469698
0.9	High Similarity	NPC473412
0.8992	High Similarity	NPC190629
0.8992	High Similarity	NPC285339
0.8992	High Similarity	NPC226788
0.8992	High Similarity	NPC218856
0.8992	High Similarity	NPC3439
0.8992	High Similarity	NPC202582
0.8992	High Similarity	NPC470258
0.8992	High Similarity	NPC273295
0.8992	High Similarity	NPC222004
0.8992	High Similarity	NPC210623
0.8984	High Similarity	NPC474119
0.8984	High Similarity	NPC474670
0.8947	High Similarity	NPC286843
0.8931	High Similarity	NPC35932
0.8931	High Similarity	NPC160991
0.8931	High Similarity	NPC16208
0.8931	High Similarity	NPC319969
0.8931	High Similarity	NPC7903
0.8931	High Similarity	NPC184447
0.8931	High Similarity	NPC5423
0.8923	High Similarity	NPC19242
0.8906	High Similarity	NPC88297
0.8906	High Similarity	NPC285725
0.8906	High Similarity	NPC50683
0.8906	High Similarity	NPC112571
0.8906	High Similarity	NPC186845
0.8906	High Similarity	NPC9891
0.8906	High Similarity	NPC127604
0.8889	High Similarity	NPC288238
0.8872	High Similarity	NPC234865
0.8871	High Similarity	NPC254625
0.8871	High Similarity	NPC475961
0.8864	High Similarity	NPC36437
0.8864	High Similarity	NPC241341
0.8864	High Similarity	NPC233018
0.8855	High Similarity	NPC470095
0.8855	High Similarity	NPC472597
0.8855	High Similarity	NPC470096
0.8837	High Similarity	NPC474821
0.881	High Similarity	NPC477886
0.8806	High Similarity	NPC11453
0.88	High Similarity	NPC473290
0.88	High Similarity	NPC471504
0.8797	High Similarity	NPC310854
0.8797	High Similarity	NPC170694
0.8788	High Similarity	NPC245120
0.8788	High Similarity	NPC470752
0.8788	High Similarity	NPC137669
0.878	High Similarity	NPC123948
0.8779	High Similarity	NPC472338
0.8769	High Similarity	NPC281864
0.8769	High Similarity	NPC54321
0.8769	High Similarity	NPC222127
0.8769	High Similarity	NPC82862
0.8769	High Similarity	NPC328682
0.8769	High Similarity	NPC474616
0.876	High Similarity	NPC474632
0.875	High Similarity	NPC267291
0.8731	High Similarity	NPC72796
0.8731	High Similarity	NPC44245
0.8731	High Similarity	NPC211386
0.8723	High Similarity	NPC475250
0.8723	High Similarity	NPC106138
0.8722	High Similarity	NPC263064
0.8714	High Similarity	NPC15577
0.8712	High Similarity	NPC309787
0.8692	High Similarity	NPC473092
0.8692	High Similarity	NPC8050
0.8692	High Similarity	NPC210355
0.8692	High Similarity	NPC473093
0.8692	High Similarity	NPC242032
0.8672	High Similarity	NPC108545
0.8667	High Similarity	NPC172818
0.8667	High Similarity	NPC25695
0.8657	High Similarity	NPC135127
0.8657	High Similarity	NPC111635
0.8657	High Similarity	NPC474478
0.8657	High Similarity	NPC309953
0.8652	High Similarity	NPC477879
0.8652	High Similarity	NPC187398
0.8652	High Similarity	NPC93924
0.8652	High Similarity	NPC476348
0.8651	High Similarity	NPC222175
0.8636	High Similarity	NPC474617
0.8636	High Similarity	NPC237169
0.8636	High Similarity	NPC470624
0.8636	High Similarity	NPC244799
0.8636	High Similarity	NPC240722
0.8633	High Similarity	NPC326144
0.8626	High Similarity	NPC474636
0.8623	High Similarity	NPC473873
0.8623	High Similarity	NPC193722
0.8623	High Similarity	NPC473792
0.8623	High Similarity	NPC278469
0.8623	High Similarity	NPC287124
0.8623	High Similarity	NPC469559
0.8615	High Similarity	NPC244364
0.8613	High Similarity	NPC291101
0.8613	High Similarity	NPC266197
0.8605	High Similarity	NPC109822
0.8605	High Similarity	NPC94276
0.8603	High Similarity	NPC474530
0.8603	High Similarity	NPC474521
0.8603	High Similarity	NPC126206
0.8603	High Similarity	NPC474540
0.8594	High Similarity	NPC71090
0.8593	High Similarity	NPC112939
0.8593	High Similarity	NPC474206
0.8593	High Similarity	NPC470356
0.8593	High Similarity	NPC94750
0.8593	High Similarity	NPC61946
0.8593	High Similarity	NPC121812
0.8593	High Similarity	NPC112246
0.8593	High Similarity	NPC472337
0.8592	High Similarity	NPC30688
0.8592	High Similarity	NPC176903
0.8583	High Similarity	NPC199023
0.8582	High Similarity	NPC475840
0.8582	High Similarity	NPC1474
0.8582	High Similarity	NPC266848
0.8582	High Similarity	NPC69513
0.8582	High Similarity	NPC476347
0.8582	High Similarity	NPC136750
0.8582	High Similarity	NPC215833
0.8582	High Similarity	NPC168059
0.8582	High Similarity	NPC229442
0.8571	High Similarity	NPC141493
0.8571	High Similarity	NPC327651
0.8571	High Similarity	NPC474238
0.8571	High Similarity	NPC318286
0.8571	High Similarity	NPC184928
0.8571	High Similarity	NPC15805
0.8561	High Similarity	NPC170844
0.8561	High Similarity	NPC76415
0.8561	High Similarity	NPC218510
0.8561	High Similarity	NPC476968
0.8561	High Similarity	NPC123127
0.8561	High Similarity	NPC474227
0.8561	High Similarity	NPC27239
0.856	High Similarity	NPC471503
0.856	High Similarity	NPC471498
0.8551	High Similarity	NPC224876
0.8551	High Similarity	NPC83375
0.8551	High Similarity	NPC300611
0.855	High Similarity	NPC111247
0.855	High Similarity	NPC118787
0.855	High Similarity	NPC41706
0.855	High Similarity	NPC183181
0.855	High Similarity	NPC319625
0.855	High Similarity	NPC163332
0.855	High Similarity	NPC470699
0.855	High Similarity	NPC292056
0.855	High Similarity	NPC147821
0.8542	High Similarity	NPC302610
0.854	High Similarity	NPC43500
0.854	High Similarity	NPC164148
0.854	High Similarity	NPC22517
0.8538	High Similarity	NPC27352
0.8537	High Similarity	NPC204120
0.8531	High Similarity	NPC477381
0.8531	High Similarity	NPC21184
0.8531	High Similarity	NPC120426
0.8531	High Similarity	NPC294522
0.8531	High Similarity	NPC205727
0.8531	High Similarity	NPC473091
0.8529	High Similarity	NPC78047
0.8529	High Similarity	NPC474639
0.8529	High Similarity	NPC471665
0.8529	High Similarity	NPC471988
0.8529	High Similarity	NPC227503
0.8529	High Similarity	NPC471664
0.8529	High Similarity	NPC16435
0.8529	High Similarity	NPC306441
0.8529	High Similarity	NPC472334
0.8529	High Similarity	NPC472336

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 NPC79184 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	910
0.2-0.3	1876
0.3-0.4	2685
0.4-0.5	1647
0.5-0.6	991
0.6-0.7	590
0.7-0.8	150
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8561	High Similarity	NPD3027	Phase 3
0.845	Intermediate Similarity	NPD2981	Phase 2
0.8385	Intermediate Similarity	NPD2983	Phase 2
0.8385	Intermediate Similarity	NPD2982	Phase 2
0.8271	Intermediate Similarity	NPD3018	Phase 2
0.8235	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD1613	Approved
0.8222	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD3817	Phase 2
0.8095	Intermediate Similarity	NPD5283	Phase 1
0.8074	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD1653	Approved
0.7955	Intermediate Similarity	NPD3705	Approved
0.7905	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD5535	Approved
0.7867	Intermediate Similarity	NPD37	Approved
0.7846	Intermediate Similarity	NPD5536	Phase 2
0.7829	Intermediate Similarity	NPD4966	Approved
0.7829	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD4967	Phase 2
0.7829	Intermediate Similarity	NPD4965	Approved
0.7793	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD7266	Discontinued
0.7748	Intermediate Similarity	NPD1934	Approved
0.7742	Intermediate Similarity	NPD7199	Phase 2
0.7727	Intermediate Similarity	NPD6234	Discontinued
0.7727	Intermediate Similarity	NPD5585	Approved
0.7703	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3539	Phase 1
0.7687	Intermediate Similarity	NPD422	Phase 1
0.7681	Intermediate Similarity	NPD4908	Phase 1
0.7681	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD1652	Phase 2
0.7652	Intermediate Similarity	NPD1548	Phase 1
0.7647	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6233	Phase 2
0.7643	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD3540	Phase 1
0.7626	Intermediate Similarity	NPD7095	Approved
0.7619	Intermediate Similarity	NPD1358	Approved
0.7603	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4110	Phase 3
0.7597	Intermediate Similarity	NPD7843	Approved
0.7589	Intermediate Similarity	NPD4060	Phase 1
0.7582	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD2801	Approved
0.7571	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6799	Approved
0.7564	Intermediate Similarity	NPD5494	Approved
0.7562	Intermediate Similarity	NPD7054	Approved
0.7562	Intermediate Similarity	NPD5844	Phase 1
0.7557	Intermediate Similarity	NPD7157	Approved
0.7556	Intermediate Similarity	NPD1610	Phase 2
0.7537	Intermediate Similarity	NPD17	Approved
0.7535	Intermediate Similarity	NPD6355	Discontinued
0.7532	Intermediate Similarity	NPD5353	Approved
0.7516	Intermediate Similarity	NPD7074	Phase 3
0.7516	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD4678	Approved
0.75	Intermediate Similarity	NPD7124	Phase 2
0.75	Intermediate Similarity	NPD4675	Approved
0.75	Intermediate Similarity	NPD7228	Approved
0.7484	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6166	Phase 2
0.7484	Intermediate Similarity	NPD3882	Suspended
0.7483	Intermediate Similarity	NPD3686	Approved
0.7483	Intermediate Similarity	NPD3687	Approved
0.7481	Intermediate Similarity	NPD3496	Discontinued
0.7468	Intermediate Similarity	NPD7819	Suspended
0.7468	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD5677	Discontinued
0.7451	Intermediate Similarity	NPD6386	Approved
0.7451	Intermediate Similarity	NPD6385	Approved
0.745	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD2796	Approved
0.7448	Intermediate Similarity	NPD2438	Suspended
0.7447	Intermediate Similarity	NPD6798	Discontinued
0.7445	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD4359	Approved
0.7436	Intermediate Similarity	NPD7075	Discontinued
0.7436	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD7097	Phase 1
0.7429	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6832	Phase 2
0.7422	Intermediate Similarity	NPD2684	Approved
0.7421	Intermediate Similarity	NPD5242	Approved
0.7419	Intermediate Similarity	NPD5402	Approved
0.7413	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4340	Discontinued
0.7413	Intermediate Similarity	NPD5124	Phase 1
0.7402	Intermediate Similarity	NPD3134	Approved
0.74	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3146	Approved
0.7397	Intermediate Similarity	NPD5762	Approved
0.7397	Intermediate Similarity	NPD5763	Approved
0.7394	Intermediate Similarity	NPD4062	Phase 3
0.7391	Intermediate Similarity	NPD3818	Discontinued
0.7389	Intermediate Similarity	NPD919	Approved
0.7385	Intermediate Similarity	NPD228	Approved
0.7379	Intermediate Similarity	NPD3748	Approved
0.7378	Intermediate Similarity	NPD7808	Phase 3
0.7378	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1608	Approved
0.7365	Intermediate Similarity	NPD4628	Phase 3
0.7361	Intermediate Similarity	NPD2653	Approved
0.7361	Intermediate Similarity	NPD6653	Approved
0.7358	Intermediate Similarity	NPD6232	Discontinued
0.7357	Intermediate Similarity	NPD2861	Phase 2
0.7338	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4357	Discontinued
0.7333	Intermediate Similarity	NPD1511	Approved
0.7333	Intermediate Similarity	NPD5691	Approved
0.7329	Intermediate Similarity	NPD6032	Approved
0.7329	Intermediate Similarity	NPD7473	Discontinued
0.732	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7240	Approved
0.7317	Intermediate Similarity	NPD7251	Discontinued
0.7315	Intermediate Similarity	NPD6190	Approved
0.731	Intermediate Similarity	NPD6111	Discontinued
0.7303	Intermediate Similarity	NPD5403	Approved
0.7299	Intermediate Similarity	NPD1611	Approved
0.7299	Intermediate Similarity	NPD1091	Approved
0.7297	Intermediate Similarity	NPD6674	Discontinued
0.7296	Intermediate Similarity	NPD8127	Discontinued
0.7292	Intermediate Similarity	NPD1933	Approved
0.7292	Intermediate Similarity	NPD230	Phase 1
0.729	Intermediate Similarity	NPD6801	Discontinued
0.7285	Intermediate Similarity	NPD5401	Approved
0.7279	Intermediate Similarity	NPD1375	Discontinued
0.7279	Intermediate Similarity	NPD1778	Approved
0.7273	Intermediate Similarity	NPD7549	Discontinued
0.7273	Intermediate Similarity	NPD4870	Approved
0.7273	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6599	Discontinued
0.7259	Intermediate Similarity	NPD1894	Discontinued
0.7256	Intermediate Similarity	NPD6797	Phase 2
0.7256	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4625	Phase 3
0.7248	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1465	Phase 2
0.7237	Intermediate Similarity	NPD1512	Approved
0.7222	Intermediate Similarity	NPD4140	Approved
0.7222	Intermediate Similarity	NPD2979	Phase 3
0.7222	Intermediate Similarity	NPD1558	Phase 1
0.7206	Intermediate Similarity	NPD1357	Approved
0.7205	Intermediate Similarity	NPD3926	Phase 2
0.7203	Intermediate Similarity	NPD1296	Phase 2
0.7203	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2219	Phase 1
0.7194	Intermediate Similarity	NPD4749	Approved
0.7194	Intermediate Similarity	NPD5327	Phase 3
0.7192	Intermediate Similarity	NPD4538	Approved
0.7192	Intermediate Similarity	NPD4536	Approved
0.7192	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4236	Phase 3
0.7181	Intermediate Similarity	NPD4237	Approved
0.7181	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4162	Approved
0.7172	Intermediate Similarity	NPD447	Suspended
0.7172	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4123	Phase 3
0.7143	Intermediate Similarity	NPD4210	Discontinued
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD8651	Approved
0.7143	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD8455	Phase 2
0.7133	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3750	Approved
0.7132	Intermediate Similarity	NPD7533	Approved
0.7132	Intermediate Similarity	NPD7534	Approved
0.7115	Intermediate Similarity	NPD7411	Suspended
0.7107	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5297	Approved
0.7101	Intermediate Similarity	NPD3847	Discontinued
0.7097	Intermediate Similarity	NPD4005	Discontinued
0.7095	Intermediate Similarity	NPD1551	Phase 2
0.7083	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5718	Phase 2
0.7083	Intermediate Similarity	NPD5110	Phase 2
0.7083	Intermediate Similarity	NPD5109	Approved
0.7083	Intermediate Similarity	NPD5111	Phase 2
0.7081	Intermediate Similarity	NPD1247	Approved
0.7077	Intermediate Similarity	NPD290	Approved
0.7067	Intermediate Similarity	NPD3060	Approved
0.7063	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4972	Discontinued
0.7051	Intermediate Similarity	NPD4380	Phase 2
0.705	Intermediate Similarity	NPD1281	Approved
0.705	Intermediate Similarity	NPD1535	Discovery
0.7047	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1550	Clinical (unspecified phase)

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