NPASS Compound

Structure

CID7171 OpenBabel06191715332D 27 30 0 0 1 0 0 0 0 0999 V2000 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0976 -4.5560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5931 -0.9846 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 -3.5066 -1.3914 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 -1.8886 -2.5669 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 -1.0693 0.7260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7387 -0.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7840 -1.5724 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 -0.6626 -0.1875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3319 -0.0830 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6111 -2.3859 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 -2.8021 -2.9737 0.0000 C 0 0 0 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 -0.8705 -1.1657 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5398 0.8952 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5247 -2.7926 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9066 -3.9682 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0045 -1.6657 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3262 1.3952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 12 2 0 0 0 0 8 18 1 0 0 0 0 9 13 2 0 0 0 0 9 19 1 0 0 0 0 10 27 1 0 0 0 0 11 26 1 0 0 0 0 14 10 1 6 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 11 1 6 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 19 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 12 1 1 0 0 0 20 26 1 0 0 0 0 21 13 1 6 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.16
Volume:	374.469
LogP:	2.833
LogD:	3.097
LogS:	-3.683
# Rotatable Bonds:	5
TPSA:	66.38
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.867
Synthetic Accessibility Score:	3.578
Fsp3:	0.429
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:	-4.81
MDCK Permeability:	5.250861795502715e-05
Pgp-inhibitor:	0.31
Pgp-substrate:	0.073
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.378
Plasma Protein Binding (PPB):	84.92599487304688%
Volume Distribution (VD):	0.749
Pgp-substrate:	9.191573143005371%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.945
CYP2C19-inhibitor:	0.25
CYP2C19-substrate:	0.788
CYP2C9-inhibitor:	0.386
CYP2C9-substrate:	0.765
CYP2D6-inhibitor:	0.247
CYP2D6-substrate:	0.903
CYP3A4-inhibitor:	0.735
CYP3A4-substrate:	0.644

ADMET: Excretion

Clearance (CL):	11.168
Half-life (T1/2):	0.449

ADMET: Toxicity

hERG Blockers:	0.387
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.882
AMES Toxicity:	0.464
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.326
Skin Sensitization:	0.913
Carcinogencity:	0.525
Eye Corrosion:	0.004
Eye Irritation:	0.711
Respiratory Toxicity:	0.721

Download Data

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

Natural Product: NPC7171

Natural Product ID:	NPC7171
*Common Name:**	Phylligenin
IUPAC Name:	4-[(3R,3aS,6S,6aS)-6-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
Synonyms:	(-)-Phylligenin
Standard InCHIKey:	CPJKKWDCUOOTEW-SORVUCRQSA-N
Standard InCHI:	InChI=1S/C21H24O6/c1-23-17-7-5-13(9-19(17)25-3)21-15-11-26-20(14(15)10-27-21)12-4-6-16(22)18(8-12)24-2/h4-9,14-15,20-22H,10-11H2,1-3H3/t14-,15-,20+,21-/m1/s1
SMILES:	COc1ccc(cc1OC)[C@@H]1[C@@H]2CO[C@@H](c3ccc(c(c3)OC)O)[C@@H]2CO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457587
PubChem CID:	12314158
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans

*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
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s00217-007-0799-1]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1016/j.foodchem.2011.01.077]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15620261]
NPO11792	Orophea enneandra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868150]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Twig	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11792	Orophea enneandra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	Inhibition	=	24.7	%	PMID[555740]

☑ 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 NPC7171 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	387
0.1-0.2	1267
0.2-0.3	3617
0.3-0.4	10295
0.4-0.5	8894
0.5-0.6	5384
0.6-0.7	9155
0.7-0.8	2710
0.8-0.85	673
0.85-0.9	218
0.9-0.95	79
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC27843
1.0	High Similarity	NPC158079
1.0	High Similarity	NPC40432
1.0	High Similarity	NPC115207
1.0	High Similarity	NPC228346
1.0	High Similarity	NPC161557
0.992	High Similarity	NPC181049
0.992	High Similarity	NPC207400
0.9762	High Similarity	NPC4940
0.976	High Similarity	NPC241522
0.976	High Similarity	NPC42300
0.976	High Similarity	NPC257582
0.976	High Similarity	NPC153739
0.976	High Similarity	NPC242807
0.976	High Similarity	NPC77040
0.976	High Similarity	NPC145305
0.976	High Similarity	NPC174495
0.976	High Similarity	NPC64201
0.976	High Similarity	NPC187998
0.976	High Similarity	NPC92164
0.9758	High Similarity	NPC11258
0.9758	High Similarity	NPC184733
0.9758	High Similarity	NPC128208
0.9758	High Similarity	NPC129570
0.9758	High Similarity	NPC282703
0.9758	High Similarity	NPC45774
0.9758	High Similarity	NPC21867
0.9688	High Similarity	NPC99572
0.9688	High Similarity	NPC126409
0.9683	High Similarity	NPC277804
0.968	High Similarity	NPC475875
0.96	High Similarity	NPC470084
0.9535	High Similarity	NPC142547
0.9535	High Similarity	NPC141765
0.9535	High Similarity	NPC135777
0.9535	High Similarity	NPC165155
0.9535	High Similarity	NPC24490
0.9535	High Similarity	NPC34103
0.9531	High Similarity	NPC158331
0.952	High Similarity	NPC165045
0.952	High Similarity	NPC118533
0.9466	High Similarity	NPC123526
0.9466	High Similarity	NPC88640
0.9466	High Similarity	NPC193666
0.9457	High Similarity	NPC67247
0.9457	High Similarity	NPC287745
0.9453	High Similarity	NPC175067
0.9453	High Similarity	NPC204215
0.944	High Similarity	NPC206882
0.9435	High Similarity	NPC257682
0.9435	High Similarity	NPC121783
0.9435	High Similarity	NPC34902
0.9435	High Similarity	NPC131747
0.9435	High Similarity	NPC18449
0.9435	High Similarity	NPC146355
0.9365	High Similarity	NPC5428
0.936	High Similarity	NPC148627
0.9355	High Similarity	NPC31344
0.9355	High Similarity	NPC317769
0.9313	High Similarity	NPC54743
0.9313	High Similarity	NPC156502
0.9313	High Similarity	NPC471988
0.9313	High Similarity	NPC177160
0.9313	High Similarity	NPC10737
0.9313	High Similarity	NPC209985
0.9313	High Similarity	NPC263367
0.9313	High Similarity	NPC477939
0.9313	High Similarity	NPC29799
0.9308	High Similarity	NPC49603
0.9308	High Similarity	NPC326095
0.9308	High Similarity	NPC471942
0.9308	High Similarity	NPC193026
0.9308	High Similarity	NPC187616
0.9308	High Similarity	NPC244983
0.9302	High Similarity	NPC471505
0.9291	High Similarity	NPC252307
0.9291	High Similarity	NPC245826
0.9291	High Similarity	NPC474178
0.9248	High Similarity	NPC177868
0.9248	High Similarity	NPC55793
0.9242	High Similarity	NPC281780
0.9237	High Similarity	NPC184938
0.9237	High Similarity	NPC101624
0.9225	High Similarity	NPC474017
0.9213	High Similarity	NPC292056
0.9213	High Similarity	NPC118787
0.9213	High Similarity	NPC147821
0.9213	High Similarity	NPC111247
0.9213	High Similarity	NPC163332
0.9213	High Similarity	NPC183181
0.9213	High Similarity	NPC41706
0.9213	High Similarity	NPC319625
0.92	High Similarity	NPC471693
0.92	High Similarity	NPC280704
0.92	High Similarity	NPC473451
0.9194	High Similarity	NPC126935
0.9194	High Similarity	NPC57268
0.9194	High Similarity	NPC312713
0.9194	High Similarity	NPC172676
0.9194	High Similarity	NPC65933
0.9194	High Similarity	NPC216929
0.9185	High Similarity	NPC477898
0.9185	High Similarity	NPC298317
0.9185	High Similarity	NPC255566
0.9185	High Similarity	NPC265154
0.9167	High Similarity	NPC77861
0.9154	High Similarity	NPC259742
0.9154	High Similarity	NPC219671
0.9154	High Similarity	NPC147616
0.9154	High Similarity	NPC106739
0.9154	High Similarity	NPC104077
0.9141	High Similarity	NPC222127
0.9141	High Similarity	NPC82862
0.9134	High Similarity	NPC58607
0.9134	High Similarity	NPC178284
0.9134	High Similarity	NPC191037
0.912	High Similarity	NPC85488
0.9118	High Similarity	NPC470097
0.9118	High Similarity	NPC84181
0.9118	High Similarity	NPC114119
0.9118	High Similarity	NPC471415
0.9104	High Similarity	NPC160283
0.9104	High Similarity	NPC254759
0.9104	High Similarity	NPC184797
0.9104	High Similarity	NPC309124
0.9091	High Similarity	NPC18576
0.9084	High Similarity	NPC26394
0.9084	High Similarity	NPC169973
0.907	High Similarity	NPC170844
0.907	High Similarity	NPC476968
0.907	High Similarity	NPC5851
0.907	High Similarity	NPC86030
0.9062	High Similarity	NPC8050
0.9062	High Similarity	NPC473093
0.9062	High Similarity	NPC473092
0.9062	High Similarity	NPC127587
0.9055	High Similarity	NPC194519
0.9051	High Similarity	NPC279298
0.9051	High Similarity	NPC223185
0.9051	High Similarity	NPC22150
0.9051	High Similarity	NPC38041
0.9044	High Similarity	NPC12728
0.9044	High Similarity	NPC185071
0.904	High Similarity	NPC262156
0.904	High Similarity	NPC470804
0.904	High Similarity	NPC184651
0.904	High Similarity	NPC324571
0.904	High Similarity	NPC343720
0.904	High Similarity	NPC54872
0.904	High Similarity	NPC470212
0.904	High Similarity	NPC473853
0.904	High Similarity	NPC476343
0.904	High Similarity	NPC312675
0.904	High Similarity	NPC113865
0.9037	High Similarity	NPC87725
0.9037	High Similarity	NPC472711
0.9037	High Similarity	NPC471414
0.9037	High Similarity	NPC263261
0.9032	High Similarity	NPC95614
0.9032	High Similarity	NPC227217
0.9032	High Similarity	NPC56214
0.9032	High Similarity	NPC232316
0.9032	High Similarity	NPC242885
0.9032	High Similarity	NPC165133
0.9032	High Similarity	NPC117780
0.903	High Similarity	NPC236306
0.903	High Similarity	NPC292882
0.903	High Similarity	NPC473739
0.903	High Similarity	NPC232164
0.9015	High Similarity	NPC47181
0.9015	High Similarity	NPC478085
0.9008	High Similarity	NPC253105
0.9008	High Similarity	NPC201587
0.9008	High Similarity	NPC230219
0.9	High Similarity	NPC275950
0.9	High Similarity	NPC173308
0.9	High Similarity	NPC143483
0.9	High Similarity	NPC181079
0.8992	High Similarity	NPC165128
0.8992	High Similarity	NPC186843
0.8992	High Similarity	NPC54321
0.8992	High Similarity	NPC98631
0.8992	High Similarity	NPC57119
0.8992	High Similarity	NPC328682
0.8992	High Similarity	NPC158471
0.8992	High Similarity	NPC470213
0.8992	High Similarity	NPC226862
0.8992	High Similarity	NPC206615
0.8992	High Similarity	NPC72529
0.8992	High Similarity	NPC281864
0.8986	High Similarity	NPC317053
0.8986	High Similarity	NPC112861
0.8986	High Similarity	NPC324492
0.8984	High Similarity	NPC50683
0.8984	High Similarity	NPC112571
0.8984	High Similarity	NPC76451
0.8984	High Similarity	NPC285725
0.8976	High Similarity	NPC293701
0.8976	High Similarity	NPC94276
0.8976	High Similarity	NPC48990

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 NPC7171 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	769
0.2-0.3	1728
0.3-0.4	2767
0.4-0.5	1869
0.5-0.6	1060
0.6-0.7	560
0.7-0.8	82
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.907	High Similarity	NPD3027	Phase 3
0.8468	Intermediate Similarity	NPD5283	Phase 1
0.8444	Intermediate Similarity	NPD1613	Approved
0.8444	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8306	Intermediate Similarity	NPD228	Approved
0.8284	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD2861	Phase 2
0.8175	Intermediate Similarity	NPD3620	Phase 2
0.8175	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD3705	Approved
0.8146	Intermediate Similarity	NPD6234	Discontinued
0.8145	Intermediate Similarity	NPD3021	Approved
0.8145	Intermediate Similarity	NPD3022	Approved
0.8045	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4966	Approved
0.7895	Intermediate Similarity	NPD4967	Phase 2
0.7895	Intermediate Similarity	NPD4965	Approved
0.7883	Intermediate Similarity	NPD4908	Phase 1
0.7803	Intermediate Similarity	NPD1357	Approved
0.7786	Intermediate Similarity	NPD1558	Phase 1
0.7786	Intermediate Similarity	NPD4060	Phase 1
0.7785	Intermediate Similarity	NPD7228	Approved
0.7778	Intermediate Similarity	NPD2982	Phase 2
0.7778	Intermediate Similarity	NPD2983	Phase 2
0.777	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD1610	Phase 2
0.7755	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD4236	Phase 3
0.7724	Intermediate Similarity	NPD4237	Approved
0.7708	Intermediate Similarity	NPD7266	Discontinued
0.7704	Intermediate Similarity	NPD2981	Phase 2
0.7697	Intermediate Similarity	NPD1934	Approved
0.7697	Intermediate Similarity	NPD37	Approved
0.7681	Intermediate Similarity	NPD3018	Phase 2
0.7647	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD2684	Approved
0.7634	Intermediate Similarity	NPD7157	Approved
0.7606	Intermediate Similarity	NPD5735	Approved
0.7603	Intermediate Similarity	NPD6674	Discontinued
0.7603	Intermediate Similarity	NPD3060	Approved
0.7603	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD5588	Approved
0.7551	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6331	Phase 2
0.7551	Intermediate Similarity	NPD4110	Phase 3
0.7548	Intermediate Similarity	NPD3882	Suspended
0.7538	Intermediate Similarity	NPD7843	Approved
0.7532	Intermediate Similarity	NPD2977	Approved
0.7532	Intermediate Similarity	NPD2978	Approved
0.7532	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5536	Phase 2
0.7517	Intermediate Similarity	NPD2161	Phase 2
0.75	Intermediate Similarity	NPD4538	Approved
0.75	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4536	Approved
0.75	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6355	Discontinued
0.7468	Intermediate Similarity	NPD7199	Phase 2
0.7466	Intermediate Similarity	NPD1375	Discontinued
0.7463	Intermediate Similarity	NPD1548	Phase 1
0.745	Intermediate Similarity	NPD5058	Phase 3
0.7419	Intermediate Similarity	NPD3020	Approved
0.7419	Intermediate Similarity	NPD2801	Approved
0.7413	Intermediate Similarity	NPD2238	Phase 2
0.741	Intermediate Similarity	NPD3094	Phase 2
0.741	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5111	Phase 2
0.7394	Intermediate Similarity	NPD5109	Approved
0.7394	Intermediate Similarity	NPD5110	Phase 2
0.7391	Intermediate Similarity	NPD4749	Approved
0.7375	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1091	Approved
0.7368	Intermediate Similarity	NPD6671	Approved
0.7365	Intermediate Similarity	NPD5177	Phase 3
0.7361	Intermediate Similarity	NPD3657	Discovery
0.7357	Intermediate Similarity	NPD6584	Phase 3
0.7351	Intermediate Similarity	NPD4123	Phase 3
0.7347	Intermediate Similarity	NPD5762	Approved
0.7347	Intermediate Similarity	NPD5763	Approved
0.7346	Intermediate Similarity	NPD3818	Discontinued
0.7344	Intermediate Similarity	NPD968	Approved
0.7343	Intermediate Similarity	NPD2674	Phase 3
0.7338	Intermediate Similarity	NPD8651	Approved
0.7329	Intermediate Similarity	NPD5960	Phase 3
0.7329	Intermediate Similarity	NPD6166	Phase 2
0.7329	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD7095	Approved
0.7324	Intermediate Similarity	NPD4625	Phase 3
0.732	Intermediate Similarity	NPD1653	Approved
0.7315	Intermediate Similarity	NPD4628	Phase 3
0.731	Intermediate Similarity	NPD6653	Approved
0.7303	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD290	Approved
0.7273	Intermediate Similarity	NPD3145	Approved
0.7273	Intermediate Similarity	NPD3144	Approved
0.7273	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7240	Approved
0.7267	Intermediate Similarity	NPD2677	Approved
0.7267	Intermediate Similarity	NPD6190	Approved
0.7266	Intermediate Similarity	NPD5327	Phase 3
0.7261	Intermediate Similarity	NPD2560	Approved
0.7261	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2563	Approved
0.7254	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4162	Approved
0.7246	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3092	Approved
0.7237	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5846	Approved
0.7226	Intermediate Similarity	NPD4675	Approved
0.7226	Intermediate Similarity	NPD5126	Approved
0.7226	Intermediate Similarity	NPD5125	Phase 3
0.7226	Intermediate Similarity	NPD4678	Approved
0.7226	Intermediate Similarity	NPD6516	Phase 2
0.7222	Intermediate Similarity	NPD27	Approved
0.7222	Intermediate Similarity	NPD6233	Phase 2
0.7222	Intermediate Similarity	NPD2489	Approved
0.7222	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7124	Phase 2
0.7214	Intermediate Similarity	NPD6696	Suspended
0.7211	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4210	Discontinued
0.7197	Intermediate Similarity	NPD5772	Approved
0.7197	Intermediate Similarity	NPD5773	Approved
0.7194	Intermediate Similarity	NPD2230	Approved
0.7194	Intermediate Similarity	NPD2235	Phase 2
0.7194	Intermediate Similarity	NPD1608	Approved
0.7194	Intermediate Similarity	NPD2233	Approved
0.7194	Intermediate Similarity	NPD2231	Phase 2
0.7194	Intermediate Similarity	NPD2232	Approved
0.7192	Intermediate Similarity	NPD6353	Approved
0.719	Intermediate Similarity	NPD52	Approved
0.719	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7526	Approved
0.7188	Intermediate Similarity	NPD5494	Approved
0.7186	Intermediate Similarity	NPD7312	Approved
0.7186	Intermediate Similarity	NPD7313	Approved
0.7186	Intermediate Similarity	NPD7311	Approved
0.7186	Intermediate Similarity	NPD7310	Approved
0.7183	Intermediate Similarity	NPD9494	Approved
0.7177	Intermediate Similarity	NPD2860	Approved
0.7177	Intermediate Similarity	NPD2859	Approved
0.7172	Intermediate Similarity	NPD4140	Approved
0.7172	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1511	Approved
0.7171	Intermediate Similarity	NPD4357	Discontinued
0.717	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7685	Pre-registration
0.7165	Intermediate Similarity	NPD291	Approved
0.7161	Intermediate Similarity	NPD4005	Discontinued
0.716	Intermediate Similarity	NPD2969	Approved
0.716	Intermediate Similarity	NPD2970	Approved
0.7153	Intermediate Similarity	NPD6798	Discontinued
0.7152	Intermediate Similarity	NPD7074	Phase 3
0.7152	Intermediate Similarity	NPD5241	Discontinued
0.7143	Intermediate Similarity	NPD6583	Phase 3
0.7143	Intermediate Similarity	NPD7309	Approved
0.7143	Intermediate Similarity	NPD6582	Phase 2
0.7143	Intermediate Similarity	NPD6895	Approved
0.7143	Intermediate Similarity	NPD6896	Approved
0.7114	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3540	Phase 1
0.7114	Intermediate Similarity	NPD6004	Phase 3
0.7114	Intermediate Similarity	NPD6005	Phase 3
0.7114	Intermediate Similarity	NPD6002	Phase 3
0.7114	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4624	Approved
0.7101	Intermediate Similarity	NPD2667	Approved
0.7101	Intermediate Similarity	NPD2668	Approved
0.7099	Intermediate Similarity	NPD3051	Approved
0.7097	Intermediate Similarity	NPD2933	Approved
0.7097	Intermediate Similarity	NPD9296	Approved
0.7097	Intermediate Similarity	NPD3687	Approved
0.7097	Intermediate Similarity	NPD2934	Approved
0.7097	Intermediate Similarity	NPD3686	Approved
0.7091	Intermediate Similarity	NPD7054	Approved
0.7089	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4578	Approved
0.7083	Intermediate Similarity	NPD4577	Approved
0.708	Intermediate Similarity	NPD3091	Approved
0.708	Intermediate Similarity	NPD1182	Approved
0.7078	Intermediate Similarity	NPD1512	Approved
0.7071	Intermediate Similarity	NPD1840	Phase 2
0.7067	Intermediate Similarity	NPD7037	Approved
0.7059	Intermediate Similarity	NPD4663	Approved
0.7055	Intermediate Similarity	NPD3062	Approved
0.7055	Intermediate Similarity	NPD3059	Approved
0.7055	Intermediate Similarity	NPD3061	Approved
0.7048	Intermediate Similarity	NPD7472	Approved
0.7047	Intermediate Similarity	NPD3539	Phase 1
0.7047	Intermediate Similarity	NPD2438	Suspended
0.7045	Intermediate Similarity	NPD5451	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