NPASS Compound

Structure

NPC191360 OpenBabel07101719142D 23 26 0 0 1 0 0 0 0 0999 V2000 -0.9747 -2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7408 -0.7377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7461 -1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7957 -1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7957 -2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0140 -2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6942 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2820 -1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1480 -3.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0140 -1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2820 -2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1480 -1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6942 -3.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -3.9052 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2079 -3.5962 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 -0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1480 -4.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1480 -0.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2820 -4.4052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8801 -1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.5743 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 21 1 0 0 0 0 4 5 1 0 0 0 0 4 11 1 0 0 0 0 5 16 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 21 1 0 0 0 0 11 17 1 1 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 15 16 1 1 0 0 0 15 23 1 0 0 0 0 16 1 1 1 0 0 0 16 23 1 0 0 0 0 17 2 1 6 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.13
Volume:	310.558
LogP:	2.626
LogD:	1.697
LogS:	-3.928
# Rotatable Bonds:	1
TPSA:	91.82
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.607
Synthetic Accessibility Score:	4.78
Fsp3:	0.588
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.889
MDCK Permeability:	1.1459432244009804e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.229
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.184
Plasma Protein Binding (PPB):	94.02982330322266%
Volume Distribution (VD):	0.59
Pgp-substrate:	4.6145920753479%

ADMET: Metabolism

CYP1A2-inhibitor:	0.156
CYP1A2-substrate:	0.961
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.762
CYP2C9-inhibitor:	0.127
CYP2C9-substrate:	0.492
CYP2D6-inhibitor:	0.127
CYP2D6-substrate:	0.333
CYP3A4-inhibitor:	0.433
CYP3A4-substrate:	0.337

ADMET: Excretion

Clearance (CL):	10.141
Half-life (T1/2):	0.386

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.222
Drug-inuced Liver Injury (DILI):	0.26
AMES Toxicity:	0.307
Rat Oral Acute Toxicity:	0.354
Maximum Recommended Daily Dose:	0.117
Skin Sensitization:	0.896
Carcinogencity:	0.164
Eye Corrosion:	0.006
Eye Irritation:	0.466
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC191360

Natural Product ID:	NPC191360
*Common Name:**	KLHZTHGOEWAZJD-AHBIMHKDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KLHZTHGOEWAZJD-AHBIMHKDSA-N
Standard InCHI:	InChI=1S/C17H20O6/c1-16-5-4-11-17(2,22-11)7-8-12(14(20)15(16)23-16)9(18)6-10(21-3)13(8)19/h6,11,15,18-19H,4-5,7H2,1-3H3/t11-,15-,16-,17+/m1/s1
SMILES:	COc1cc(O)c2c(c1O)C[C@]1(C)O[C@@H]1CC[C@@]1([C@@H](C2=O)O1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409095
PubChem CID:	71746814
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO33125	tricholoma terreum	Species	Tricholomataceae	Eukaryota	Fruiting Bodies	n.a.	n.a.	PMID[23837944]
NPO33125	tricholoma terreum	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28956915]

☑ 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	9
Others	1

Activity Type	# Activity
Cell Line	8
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	14200.0	nM	PMID[543248]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	16100.0	nM	PMID[543248]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	4200.0	nM	PMID[543248]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	11300.0	nM	PMID[543248]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	4000.0	nM	PMID[543248]
NPT1460	Cell Line	L929	Mus musculus	IC50	=	9900.0	nM	PMID[543249]
NPT1178	Cell Line	KB 3-1	Homo sapiens	IC50	=	9000.0	nM	PMID[543249]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	17000.0	nM	PMID[543249]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	>	25.0	%	PMID[543249]
NPT2	Others	Unspecified		IC50	=	29000.0	nM	PMID[543249]

☑ 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 NPC191360 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	456
0.1-0.2	1941
0.2-0.3	5224
0.3-0.4	11223
0.4-0.5	6433
0.5-0.6	4783
0.6-0.7	6050
0.7-0.8	5704
0.8-0.85	847
0.85-0.9	28
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9677	High Similarity	NPC201560
0.9615	High Similarity	NPC48860
0.8974	High Similarity	NPC103509
0.8882	High Similarity	NPC161947
0.8882	High Similarity	NPC155302
0.8868	High Similarity	NPC79998
0.8834	High Similarity	NPC475985
0.8834	High Similarity	NPC476822
0.8827	High Similarity	NPC87431
0.882	High Similarity	NPC476242
0.882	High Similarity	NPC477410
0.878	High Similarity	NPC472049
0.878	High Similarity	NPC224280
0.8758	High Similarity	NPC179732
0.8758	High Similarity	NPC300727
0.8758	High Similarity	NPC241904
0.875	High Similarity	NPC82592
0.875	High Similarity	NPC16082
0.8727	High Similarity	NPC170245
0.8727	High Similarity	NPC20237
0.8727	High Similarity	NPC477517
0.872	High Similarity	NPC249181
0.872	High Similarity	NPC41301
0.8712	High Similarity	NPC61010
0.8704	High Similarity	NPC152904
0.8704	High Similarity	NPC329091
0.8696	High Similarity	NPC268161
0.8696	High Similarity	NPC274730
0.8696	High Similarity	NPC317383
0.8696	High Similarity	NPC150227
0.8688	High Similarity	NPC281477
0.8675	High Similarity	NPC158761
0.8675	High Similarity	NPC283041
0.8675	High Similarity	NPC477154
0.8675	High Similarity	NPC117854
0.8675	High Similarity	NPC6588
0.8667	High Similarity	NPC470457
0.8667	High Similarity	NPC191930
0.8667	High Similarity	NPC234052
0.8667	High Similarity	NPC326520
0.8659	High Similarity	NPC215612
0.865	High Similarity	NPC14353
0.865	High Similarity	NPC263449
0.865	High Similarity	NPC56085
0.865	High Similarity	NPC228785
0.865	High Similarity	NPC246478
0.865	High Similarity	NPC200746
0.8642	High Similarity	NPC235215
0.8642	High Similarity	NPC156057
0.8642	High Similarity	NPC203891
0.8642	High Similarity	NPC7973
0.8642	High Similarity	NPC101830
0.8642	High Similarity	NPC84935
0.8642	High Similarity	NPC48208
0.8642	High Similarity	NPC469584
0.8642	High Similarity	NPC474208
0.8642	High Similarity	NPC162869
0.8642	High Similarity	NPC78302
0.8642	High Similarity	NPC77679
0.8642	High Similarity	NPC472438
0.8642	High Similarity	NPC29841
0.8642	High Similarity	NPC190020
0.8642	High Similarity	NPC474836
0.8642	High Similarity	NPC471479
0.8642	High Similarity	NPC475267
0.8642	High Similarity	NPC471515
0.8642	High Similarity	NPC110070
0.8634	High Similarity	NPC99381
0.8634	High Similarity	NPC234485
0.8634	High Similarity	NPC199926
0.8634	High Similarity	NPC472048
0.8623	High Similarity	NPC247136
0.8616	High Similarity	NPC96501
0.8606	High Similarity	NPC236521
0.8606	High Similarity	NPC248638
0.8606	High Similarity	NPC470459
0.8606	High Similarity	NPC152659
0.8606	High Similarity	NPC7483
0.8599	High Similarity	NPC226987
0.8599	High Similarity	NPC107625
0.8599	High Similarity	NPC143903
0.8598	High Similarity	NPC278052
0.8598	High Similarity	NPC173137
0.8598	High Similarity	NPC308992
0.8598	High Similarity	NPC40491
0.8598	High Similarity	NPC474186
0.8589	High Similarity	NPC193842
0.8589	High Similarity	NPC253634
0.8589	High Similarity	NPC18607
0.8589	High Similarity	NPC152166
0.8589	High Similarity	NPC55738
0.8589	High Similarity	NPC7846
0.8589	High Similarity	NPC100123
0.8589	High Similarity	NPC18772
0.8589	High Similarity	NPC4481
0.8589	High Similarity	NPC288669
0.8589	High Similarity	NPC130894
0.8589	High Similarity	NPC25495
0.8589	High Similarity	NPC300943
0.8589	High Similarity	NPC176300
0.8589	High Similarity	NPC261004
0.8589	High Similarity	NPC195832
0.8589	High Similarity	NPC204854
0.8589	High Similarity	NPC9609
0.8589	High Similarity	NPC191459
0.8589	High Similarity	NPC19687
0.8589	High Similarity	NPC22472
0.8589	High Similarity	NPC115798
0.8589	High Similarity	NPC143828
0.8589	High Similarity	NPC105242
0.858	High Similarity	NPC474520
0.858	High Similarity	NPC255106
0.858	High Similarity	NPC100916
0.858	High Similarity	NPC55619
0.858	High Similarity	NPC24640
0.858	High Similarity	NPC245546
0.858	High Similarity	NPC471500
0.858	High Similarity	NPC266960
0.858	High Similarity	NPC200388
0.858	High Similarity	NPC303255
0.858	High Similarity	NPC292107
0.858	High Similarity	NPC49824
0.858	High Similarity	NPC235165
0.858	High Similarity	NPC43243
0.8571	High Similarity	NPC127172
0.8571	High Similarity	NPC250557
0.8571	High Similarity	NPC124714
0.8571	High Similarity	NPC477048
0.8571	High Similarity	NPC89474
0.8571	High Similarity	NPC477047
0.8563	High Similarity	NPC470456
0.8562	High Similarity	NPC45291
0.8562	High Similarity	NPC19980
0.8554	High Similarity	NPC275780
0.8554	High Similarity	NPC62261
0.8554	High Similarity	NPC475888
0.8554	High Similarity	NPC45449
0.8554	High Similarity	NPC472450
0.8554	High Similarity	NPC239752
0.8553	High Similarity	NPC102003
0.8553	High Similarity	NPC92722
0.8545	High Similarity	NPC25152
0.8545	High Similarity	NPC472964
0.8545	High Similarity	NPC211107
0.8544	High Similarity	NPC61871
0.8544	High Similarity	NPC30647
0.8544	High Similarity	NPC55557
0.8537	High Similarity	NPC36217
0.8537	High Similarity	NPC474287
0.8537	High Similarity	NPC470183
0.8537	High Similarity	NPC472902
0.8537	High Similarity	NPC139036
0.8537	High Similarity	NPC475886
0.8537	High Similarity	NPC320359
0.8535	High Similarity	NPC472917
0.8528	High Similarity	NPC472911
0.8528	High Similarity	NPC96167
0.8528	High Similarity	NPC75215
0.8528	High Similarity	NPC472914
0.8528	High Similarity	NPC99597
0.8528	High Similarity	NPC217677
0.8528	High Similarity	NPC227192
0.8528	High Similarity	NPC287979
0.8528	High Similarity	NPC472913
0.8528	High Similarity	NPC470402
0.8528	High Similarity	NPC67876
0.8528	High Similarity	NPC223787
0.8528	High Similarity	NPC472910
0.8528	High Similarity	NPC210084
0.8528	High Similarity	NPC305663
0.8528	High Similarity	NPC222814
0.8528	High Similarity	NPC93376
0.8528	High Similarity	NPC245758
0.8528	High Similarity	NPC189179
0.8528	High Similarity	NPC165977
0.8528	High Similarity	NPC176665
0.8528	High Similarity	NPC163524
0.8528	High Similarity	NPC224137
0.8519	High Similarity	NPC189960
0.8519	High Similarity	NPC213622
0.8519	High Similarity	NPC130589
0.8519	High Similarity	NPC56786
0.8519	High Similarity	NPC201451
0.8519	High Similarity	NPC26227
0.8519	High Similarity	NPC37392
0.8519	High Similarity	NPC44079
0.8519	High Similarity	NPC80534
0.8519	High Similarity	NPC67396
0.8519	High Similarity	NPC32557
0.8519	High Similarity	NPC134287
0.8512	High Similarity	NPC177480
0.8512	High Similarity	NPC326877
0.8509	High Similarity	NPC269451
0.8509	High Similarity	NPC327225
0.8509	High Similarity	NPC181209
0.8509	High Similarity	NPC131266
0.8509	High Similarity	NPC216769
0.8509	High Similarity	NPC209487
0.8509	High Similarity	NPC35763
0.8509	High Similarity	NPC100263

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 NPC191360 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	403
0.1-0.2	1189
0.2-0.3	2297
0.3-0.4	2654
0.4-0.5	1476
0.5-0.6	789
0.6-0.7	268
0.7-0.8	68
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8466	Intermediate Similarity	NPD3882	Suspended
0.8457	Intermediate Similarity	NPD2801	Approved
0.8395	Intermediate Similarity	NPD1934	Approved
0.8232	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD6166	Phase 2
0.8103	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD3817	Phase 2
0.8025	Intermediate Similarity	NPD1512	Approved
0.7919	Intermediate Similarity	NPD3818	Discontinued
0.7901	Intermediate Similarity	NPD1511	Approved
0.7895	Intermediate Similarity	NPD6232	Discontinued
0.7886	Intermediate Similarity	NPD6797	Phase 2
0.7882	Intermediate Similarity	NPD5494	Approved
0.7861	Intermediate Similarity	NPD7473	Discontinued
0.7853	Intermediate Similarity	NPD2533	Approved
0.7853	Intermediate Similarity	NPD2534	Approved
0.7853	Intermediate Similarity	NPD2532	Approved
0.7848	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7251	Discontinued
0.7829	Intermediate Similarity	NPD7074	Phase 3
0.7816	Intermediate Similarity	NPD3751	Discontinued
0.7812	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7808	Phase 3
0.7791	Intermediate Similarity	NPD3787	Discontinued
0.7771	Intermediate Similarity	NPD7054	Approved
0.7765	Intermediate Similarity	NPD7075	Discontinued
0.7744	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1247	Approved
0.7727	Intermediate Similarity	NPD7472	Approved
0.7725	Intermediate Similarity	NPD4380	Phase 2
0.7692	Intermediate Similarity	NPD1465	Phase 2
0.7692	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6799	Approved
0.767	Intermediate Similarity	NPD5844	Phase 1
0.7658	Intermediate Similarity	NPD230	Phase 1
0.7647	Intermediate Similarity	NPD5402	Approved
0.7633	Intermediate Similarity	NPD6801	Discontinued
0.763	Intermediate Similarity	NPD6959	Discontinued
0.7619	Intermediate Similarity	NPD6599	Discontinued
0.7584	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1510	Phase 2
0.7485	Intermediate Similarity	NPD7819	Suspended
0.7485	Intermediate Similarity	NPD1549	Phase 2
0.7484	Intermediate Similarity	NPD943	Approved
0.7484	Intermediate Similarity	NPD1240	Approved
0.7472	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD3926	Phase 2
0.7439	Intermediate Similarity	NPD2800	Approved
0.7414	Intermediate Similarity	NPD6234	Discontinued
0.7414	Intermediate Similarity	NPD919	Approved
0.7391	Intermediate Similarity	NPD1607	Approved
0.7377	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2796	Approved
0.7349	Intermediate Similarity	NPD6190	Approved
0.7341	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3027	Phase 3
0.7278	Intermediate Similarity	NPD9494	Approved
0.7256	Intermediate Similarity	NPD2935	Discontinued
0.7247	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5403	Approved
0.7225	Intermediate Similarity	NPD37	Approved
0.7222	Intermediate Similarity	NPD447	Suspended
0.7219	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD2403	Approved
0.72	Intermediate Similarity	NPD4966	Approved
0.72	Intermediate Similarity	NPD4967	Phase 2
0.72	Intermediate Similarity	NPD4965	Approved
0.7191	Intermediate Similarity	NPD5710	Approved
0.7191	Intermediate Similarity	NPD5711	Approved
0.7188	Intermediate Similarity	NPD6776	Approved
0.7188	Intermediate Similarity	NPD6781	Approved
0.7188	Intermediate Similarity	NPD6778	Approved
0.7188	Intermediate Similarity	NPD6782	Approved
0.7188	Intermediate Similarity	NPD6777	Approved
0.7188	Intermediate Similarity	NPD6780	Approved
0.7188	Intermediate Similarity	NPD6779	Approved
0.7178	Intermediate Similarity	NPD6651	Approved
0.7165	Intermediate Similarity	NPD7435	Discontinued
0.7159	Intermediate Similarity	NPD3749	Approved
0.7127	Intermediate Similarity	NPD7228	Approved
0.7118	Intermediate Similarity	NPD5401	Approved
0.7091	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3750	Approved
0.7083	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7411	Suspended
0.7065	Intermediate Similarity	NPD7685	Pre-registration
0.7065	Intermediate Similarity	NPD6559	Discontinued
0.7059	Intermediate Similarity	NPD8150	Discontinued
0.7055	Intermediate Similarity	NPD1613	Approved
0.7055	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6099	Approved
0.7048	Intermediate Similarity	NPD6100	Approved
0.7039	Intermediate Similarity	NPD7199	Phase 2
0.7035	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1653	Approved
0.699	Remote Similarity	NPD7698	Approved
0.699	Remote Similarity	NPD7697	Approved
0.699	Remote Similarity	NPD7696	Phase 3
0.6982	Remote Similarity	NPD4628	Phase 3
0.6968	Remote Similarity	NPD8434	Phase 2
0.6962	Remote Similarity	NPD9269	Phase 2
0.6959	Remote Similarity	NPD7390	Discontinued
0.6957	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7870	Phase 2
0.6954	Remote Similarity	NPD7871	Phase 2
0.695	Remote Similarity	NPD7874	Approved
0.695	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5353	Approved
0.6936	Remote Similarity	NPD920	Approved
0.6935	Remote Similarity	NPD7701	Phase 2
0.6927	Remote Similarity	NPD6535	Approved
0.6927	Remote Similarity	NPD6534	Approved
0.6923	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7768	Phase 2
0.6875	Remote Similarity	NPD5090	Approved
0.6875	Remote Similarity	NPD5089	Approved
0.6868	Remote Similarity	NPD5242	Approved
0.686	Remote Similarity	NPD7907	Approved
0.686	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3226	Approved
0.6845	Remote Similarity	NPD4111	Phase 1
0.6845	Remote Similarity	NPD1551	Phase 2
0.6832	Remote Similarity	NPD7801	Approved
0.6829	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2654	Approved
0.6821	Remote Similarity	NPD7699	Phase 2
0.6821	Remote Similarity	NPD7700	Phase 2
0.6816	Remote Similarity	NPD8151	Discontinued
0.6813	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD7286	Phase 2
0.6805	Remote Similarity	NPD2344	Approved
0.6802	Remote Similarity	NPD2493	Approved
0.6802	Remote Similarity	NPD2494	Approved
0.6786	Remote Similarity	NPD3748	Approved
0.6784	Remote Similarity	NPD4582	Approved
0.6784	Remote Similarity	NPD4583	Approved
0.6784	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6823	Phase 2
0.6763	Remote Similarity	NPD4665	Approved
0.6747	Remote Similarity	NPD4060	Phase 1
0.6738	Remote Similarity	NPD5953	Discontinued
0.6734	Remote Similarity	NPD4004	Approved
0.6734	Remote Similarity	NPD4002	Approved
0.6727	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD1243	Approved
0.6725	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD642	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8313	Approved
0.672	Remote Similarity	NPD8312	Approved
0.6717	Remote Similarity	NPD3452	Approved
0.6717	Remote Similarity	NPD3450	Approved
0.6709	Remote Similarity	NPD9268	Approved
0.6707	Remote Similarity	NPD6355	Discontinued
0.6706	Remote Similarity	NPD2346	Discontinued
0.6705	Remote Similarity	NPD3300	Phase 2
0.6702	Remote Similarity	NPD7240	Approved
0.6687	Remote Similarity	NPD6233	Phase 2
0.6686	Remote Similarity	NPD2799	Discontinued
0.6684	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7783	Phase 2
0.6667	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2163	Approved
0.6647	Remote Similarity	NPD2309	Approved
0.6627	Remote Similarity	NPD6798	Discontinued
0.6619	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD8320	Phase 1
0.6617	Remote Similarity	NPD8319	Approved
0.6614	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD4585	Approved
0.6609	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD1471	Phase 3
0.6599	Remote Similarity	NPD2974	Approved
0.6599	Remote Similarity	NPD2973	Approved
0.6599	Remote Similarity	NPD2975	Approved
0.6597	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6386	Approved
0.6592	Remote Similarity	NPD6385	Approved
0.6591	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD3705	Approved
0.6583	Remote Similarity	NPD4580	Approved
0.657	Remote Similarity	NPD2424	Discontinued
0.6557	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD9717	Approved
0.6541	Remote Similarity	NPD9545	Approved
0.6541	Remote Similarity	NPD7229	Phase 3
0.6534	Remote Similarity	NPD3146	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