NPASS Compound

Structure

NPC472907 OpenBabel07101718292D 31 33 0 0 1 0 0 0 0 0999 V2000 4.0226 1.2424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0226 -0.6895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0579 -0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 -0.9483 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 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7979 0.0176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5731 -1.2071 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 5.1962 4.0000 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 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 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 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 3.7638 0.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 3 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 2.5981 5.5000 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 4.3301 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7297 0.0176 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 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 12 1 0 0 0 0 4 13 1 0 0 0 0 5 9 1 0 0 0 0 5 16 1 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 8 2 0 0 0 0 7 17 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 25 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 17 26 1 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 22 2 0 0 0 0 20 27 2 0 0 0 0 21 23 2 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 23 31 1 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.22
Volume:	449.573
LogP:	4.222
LogD:	3.399
LogS:	-4.035
# Rotatable Bonds:	8
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.456
Synthetic Accessibility Score:	3.422
Fsp3:	0.48
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:	-4.8
MDCK Permeability:	1.7664924598648213e-05
Pgp-inhibitor:	0.175
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.179
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	97.6697769165039%
Volume Distribution (VD):	0.596
Pgp-substrate:	1.5800890922546387%

ADMET: Metabolism

CYP1A2-inhibitor:	0.596
CYP1A2-substrate:	0.815
CYP2C19-inhibitor:	0.534
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.563
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.836
CYP2D6-substrate:	0.844
CYP3A4-inhibitor:	0.681
CYP3A4-substrate:	0.182

ADMET: Excretion

Clearance (CL):	11.791
Half-life (T1/2):	0.862

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.106
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.385
Skin Sensitization:	0.847
Carcinogencity:	0.101
Eye Corrosion:	0.003
Eye Irritation:	0.167
Respiratory Toxicity:	0.04

Download Data

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

Natural Product: NPC472907

Natural Product ID:	NPC472907
*Common Name:**	XVCXFWODDIZFKK-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XVCXFWODDIZFKK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H32O6/c1-24(2,30)12-4-13-25(3)14-11-18-16(6-10-21(28)23(18)31-25)5-9-20(27)19-8-7-17(26)15-22(19)29/h6-8,10,15,26,28-30H,4-5,9,11-14H2,1-3H3
SMILES:	CC1(CCC2=C(C=CC(=C2O1)O)CCC(=O)C3=C(C=C(C=C3)O)O)CCCC(C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593940
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003473] 2'-Hydroxy-dihydrochalcones

*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
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	heartwood	n.a.	n.a.	PMID[16643064]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	roots	Khon Kaen, Thailand	2009-DEC	PMID[25537111]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26178912]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26178912]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	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	=	36700.0	nM	PMID[456288]
NPT610	Others	Molecular identity unknown		IC50	=	29500.0	nM	PMID[456288]

☑ 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 NPC472907 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	428
0.1-0.2	1737
0.2-0.3	4261
0.3-0.4	10895
0.4-0.5	6996
0.5-0.6	3239
0.6-0.7	4830
0.7-0.8	5811
0.8-0.85	2598
0.85-0.9	1536
0.9-0.95	354
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC472963
0.9865	High Similarity	NPC472905
0.9673	High Similarity	NPC472964
0.9671	High Similarity	NPC474960
0.9669	High Similarity	NPC136674
0.9542	High Similarity	NPC472902
0.9542	High Similarity	NPC471973
0.953	High Similarity	NPC151473
0.9481	High Similarity	NPC472906
0.9477	High Similarity	NPC476242
0.9477	High Similarity	NPC235448
0.9474	High Similarity	NPC274730
0.9474	High Similarity	NPC24640
0.947	High Similarity	NPC49402
0.947	High Similarity	NPC33051
0.947	High Similarity	NPC273462
0.947	High Similarity	NPC469550
0.947	High Similarity	NPC227337
0.947	High Similarity	NPC70433
0.9423	High Similarity	NPC293319
0.9419	High Similarity	NPC201800
0.9416	High Similarity	NPC36217
0.9416	High Similarity	NPC139036
0.9416	High Similarity	NPC200746
0.9416	High Similarity	NPC320359
0.9412	High Similarity	NPC300727
0.9412	High Similarity	NPC129684
0.9412	High Similarity	NPC187745
0.9412	High Similarity	NPC474681
0.9412	High Similarity	NPC241904
0.9412	High Similarity	NPC161960
0.9412	High Similarity	NPC299520
0.9412	High Similarity	NPC304008
0.9412	High Similarity	NPC67876
0.9412	High Similarity	NPC218313
0.9408	High Similarity	NPC472280
0.9408	High Similarity	NPC256925
0.9408	High Similarity	NPC57674
0.9408	High Similarity	NPC67396
0.9408	High Similarity	NPC152951
0.9408	High Similarity	NPC117992
0.9408	High Similarity	NPC230149
0.9408	High Similarity	NPC234255
0.9408	High Similarity	NPC168247
0.9404	High Similarity	NPC257648
0.9404	High Similarity	NPC237994
0.9404	High Similarity	NPC477231
0.9404	High Similarity	NPC260979
0.9404	High Similarity	NPC472912
0.94	High Similarity	NPC29231
0.9396	High Similarity	NPC196277
0.9396	High Similarity	NPC43669
0.9396	High Similarity	NPC272721
0.9363	High Similarity	NPC39091
0.9359	High Similarity	NPC186686
0.9359	High Similarity	NPC189473
0.9359	High Similarity	NPC23298
0.9355	High Similarity	NPC40491
0.9355	High Similarity	NPC61010
0.9355	High Similarity	NPC278052
0.9355	High Similarity	NPC234644
0.9351	High Similarity	NPC474290
0.9351	High Similarity	NPC210459
0.9351	High Similarity	NPC204879
0.9351	High Similarity	NPC55738
0.9351	High Similarity	NPC280680
0.9351	High Similarity	NPC100123
0.9346	High Similarity	NPC115853
0.9346	High Similarity	NPC470600
0.9346	High Similarity	NPC472455
0.9346	High Similarity	NPC133970
0.9346	High Similarity	NPC6633
0.9346	High Similarity	NPC5322
0.9342	High Similarity	NPC89474
0.9342	High Similarity	NPC18727
0.9338	High Similarity	NPC31363
0.9338	High Similarity	NPC154345
0.9329	High Similarity	NPC77378
0.9304	High Similarity	NPC218226
0.9299	High Similarity	NPC303174
0.9299	High Similarity	NPC239752
0.9299	High Similarity	NPC472450
0.9299	High Similarity	NPC275780
0.9295	High Similarity	NPC329760
0.9295	High Similarity	NPC25152
0.929	High Similarity	NPC470183
0.929	High Similarity	NPC56085
0.929	High Similarity	NPC228785
0.929	High Similarity	NPC299436
0.929	High Similarity	NPC188433
0.929	High Similarity	NPC321399
0.929	High Similarity	NPC14353
0.9286	High Similarity	NPC27337
0.9286	High Similarity	NPC291508
0.9286	High Similarity	NPC273843
0.9286	High Similarity	NPC180011
0.9286	High Similarity	NPC219867
0.9286	High Similarity	NPC111969
0.9286	High Similarity	NPC52889
0.9286	High Similarity	NPC236796
0.9281	High Similarity	NPC200246
0.9281	High Similarity	NPC255807
0.9281	High Similarity	NPC31018
0.9276	High Similarity	NPC236637
0.9276	High Similarity	NPC39732
0.9276	High Similarity	NPC60972
0.9276	High Similarity	NPC302950
0.9276	High Similarity	NPC219582
0.9272	High Similarity	NPC85131
0.9241	High Similarity	NPC37870
0.9241	High Similarity	NPC43319
0.9241	High Similarity	NPC477517
0.9241	High Similarity	NPC472449
0.9236	High Similarity	NPC236521
0.9236	High Similarity	NPC7483
0.9236	High Similarity	NPC236132
0.9236	High Similarity	NPC248638
0.9236	High Similarity	NPC152659
0.9236	High Similarity	NPC475985
0.9236	High Similarity	NPC220313
0.9231	High Similarity	NPC471210
0.9231	High Similarity	NPC57715
0.9231	High Similarity	NPC472634
0.9231	High Similarity	NPC167678
0.9231	High Similarity	NPC474187
0.9231	High Similarity	NPC29876
0.9226	High Similarity	NPC74178
0.9226	High Similarity	NPC184755
0.9221	High Similarity	NPC291878
0.9221	High Similarity	NPC142339
0.9221	High Similarity	NPC472626
0.9221	High Similarity	NPC209614
0.9221	High Similarity	NPC195796
0.9221	High Similarity	NPC475799
0.9221	High Similarity	NPC13779
0.9221	High Similarity	NPC138243
0.9221	High Similarity	NPC472916
0.9221	High Similarity	NPC474638
0.9221	High Similarity	NPC470328
0.9221	High Similarity	NPC471985
0.9221	High Similarity	NPC278778
0.9221	High Similarity	NPC191146
0.9221	High Similarity	NPC68093
0.9221	High Similarity	NPC35038
0.9216	High Similarity	NPC141212
0.9216	High Similarity	NPC206238
0.9216	High Similarity	NPC292214
0.9216	High Similarity	NPC167091
0.9216	High Similarity	NPC271779
0.9216	High Similarity	NPC88645
0.9211	High Similarity	NPC202157
0.9211	High Similarity	NPC251110
0.9205	High Similarity	NPC48479
0.9205	High Similarity	NPC223579
0.9205	High Similarity	NPC287101
0.9205	High Similarity	NPC105512
0.9205	High Similarity	NPC183950
0.9205	High Similarity	NPC177298
0.9205	High Similarity	NPC137062
0.9205	High Similarity	NPC52005
0.92	High Similarity	NPC168803
0.92	High Similarity	NPC95864
0.9182	High Similarity	NPC476306
0.9177	High Similarity	NPC475888
0.9172	High Similarity	NPC474034
0.9172	High Similarity	NPC211107
0.9172	High Similarity	NPC474162
0.9172	High Similarity	NPC474033
0.9172	High Similarity	NPC474150
0.9172	High Similarity	NPC83922
0.9172	High Similarity	NPC472448
0.9172	High Similarity	NPC229632
0.9167	High Similarity	NPC472630
0.9167	High Similarity	NPC472624
0.9167	High Similarity	NPC476980
0.9167	High Similarity	NPC192686
0.9167	High Similarity	NPC80375
0.9167	High Similarity	NPC472631
0.9167	High Similarity	NPC119209
0.9167	High Similarity	NPC475886
0.9167	High Similarity	NPC118256
0.9167	High Similarity	NPC235018
0.9167	High Similarity	NPC119224
0.9167	High Similarity	NPC45146
0.9167	High Similarity	NPC204290
0.9167	High Similarity	NPC474287
0.9161	High Similarity	NPC471515
0.9161	High Similarity	NPC469584
0.9161	High Similarity	NPC48208
0.9161	High Similarity	NPC471479
0.9161	High Similarity	NPC181960
0.9161	High Similarity	NPC96167
0.9161	High Similarity	NPC472598
0.9161	High Similarity	NPC474208
0.9161	High Similarity	NPC472913
0.9161	High Similarity	NPC162869
0.9161	High Similarity	NPC474836
0.9161	High Similarity	NPC165977
0.9161	High Similarity	NPC474055
0.9161	High Similarity	NPC472914

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 NPC472907 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	991
0.2-0.3	1640
0.3-0.4	2653
0.4-0.5	1776
0.5-0.6	1012
0.6-0.7	491
0.7-0.8	152
0.8-0.85	29
0.85-0.9	15
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9276	High Similarity	NPD1934	Approved
0.9091	High Similarity	NPD2393	Clinical (unspecified phase)
0.9091	High Similarity	NPD2801	Approved
0.9	High Similarity	NPD1511	Approved
0.8974	High Similarity	NPD3882	Suspended
0.8882	High Similarity	NPD1512	Approved
0.882	High Similarity	NPD6168	Clinical (unspecified phase)
0.882	High Similarity	NPD6167	Clinical (unspecified phase)
0.882	High Similarity	NPD6166	Phase 2
0.8726	High Similarity	NPD7819	Suspended
0.872	High Similarity	NPD7074	Phase 3
0.8659	High Similarity	NPD7054	Approved
0.8608	High Similarity	NPD1465	Phase 2
0.8606	High Similarity	NPD7472	Approved
0.8598	High Similarity	NPD3818	Discontinued
0.8562	High Similarity	NPD7075	Discontinued
0.8553	High Similarity	NPD3817	Phase 2
0.8543	High Similarity	NPD1549	Phase 2
0.8537	High Similarity	NPD7473	Discontinued
0.85	High Similarity	NPD4868	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD6232	Discontinued
0.8457	Intermediate Similarity	NPD5494	Approved
0.8452	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD4380	Phase 2
0.8393	Intermediate Similarity	NPD7251	Discontinued
0.8344	Intermediate Similarity	NPD1510	Phase 2
0.8343	Intermediate Similarity	NPD7808	Phase 3
0.8333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6797	Phase 2
0.8333	Intermediate Similarity	NPD3749	Approved
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD5844	Phase 1
0.8322	Intermediate Similarity	NPD943	Approved
0.8322	Intermediate Similarity	NPD1240	Approved
0.8312	Intermediate Similarity	NPD3750	Approved
0.8289	Intermediate Similarity	NPD2796	Approved
0.8269	Intermediate Similarity	NPD6799	Approved
0.8235	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1607	Approved
0.8187	Intermediate Similarity	NPD6599	Discontinued
0.8182	Intermediate Similarity	NPD6959	Discontinued
0.8182	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD6099	Approved
0.817	Intermediate Similarity	NPD6100	Approved
0.8137	Intermediate Similarity	NPD7411	Suspended
0.8086	Intermediate Similarity	NPD6801	Discontinued
0.8084	Intermediate Similarity	NPD3926	Phase 2
0.8054	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3748	Approved
0.7987	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7768	Phase 2
0.7929	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6559	Discontinued
0.7857	Intermediate Similarity	NPD7199	Phase 2
0.7848	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD919	Approved
0.7843	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1613	Approved
0.7792	Intermediate Similarity	NPD447	Suspended
0.7791	Intermediate Similarity	NPD3226	Approved
0.7785	Intermediate Similarity	NPD2800	Approved
0.7778	Intermediate Similarity	NPD5403	Approved
0.7771	Intermediate Similarity	NPD2346	Discontinued
0.7771	Intermediate Similarity	NPD2344	Approved
0.7771	Intermediate Similarity	NPD5402	Approved
0.7765	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2534	Approved
0.7764	Intermediate Similarity	NPD2532	Approved
0.7764	Intermediate Similarity	NPD2533	Approved
0.7753	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD1247	Approved
0.7736	Intermediate Similarity	NPD4628	Phase 3
0.7733	Intermediate Similarity	NPD3751	Discontinued
0.7712	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1551	Phase 2
0.7707	Intermediate Similarity	NPD2935	Discontinued
0.7684	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD230	Phase 1
0.7677	Intermediate Similarity	NPD1933	Approved
0.7673	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD5401	Approved
0.7647	Intermediate Similarity	NPD4625	Phase 3
0.7647	Intermediate Similarity	NPD3027	Phase 3
0.7643	Intermediate Similarity	NPD2799	Discontinued
0.7633	Intermediate Similarity	NPD6234	Discontinued
0.7602	Intermediate Similarity	NPD3787	Discontinued
0.76	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7390	Discontinued
0.7593	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2309	Approved
0.7562	Intermediate Similarity	NPD1243	Approved
0.7529	Intermediate Similarity	NPD7228	Approved
0.7516	Intermediate Similarity	NPD6651	Approved
0.7516	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD1203	Approved
0.7472	Intermediate Similarity	NPD8312	Approved
0.7472	Intermediate Similarity	NPD8313	Approved
0.7468	Intermediate Similarity	NPD4908	Phase 1
0.7458	Intermediate Similarity	NPD7685	Pre-registration
0.7451	Intermediate Similarity	NPD2798	Approved
0.744	Intermediate Similarity	NPD37	Approved
0.7416	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4967	Phase 2
0.7412	Intermediate Similarity	NPD4966	Approved
0.7412	Intermediate Similarity	NPD4965	Approved
0.741	Intermediate Similarity	NPD1653	Approved
0.7407	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD5953	Discontinued
0.7386	Intermediate Similarity	NPD7286	Phase 2
0.7386	Intermediate Similarity	NPD1470	Approved
0.7372	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3268	Approved
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.7372	Intermediate Similarity	NPD3764	Approved
0.7368	Intermediate Similarity	NPD4749	Approved
0.7363	Intermediate Similarity	NPD4287	Approved
0.7362	Intermediate Similarity	NPD6190	Approved
0.7355	Intermediate Similarity	NPD6832	Phase 2
0.7353	Intermediate Similarity	NPD4288	Approved
0.7351	Intermediate Similarity	NPD1610	Phase 2
0.7351	Intermediate Similarity	NPD1201	Approved
0.7351	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD920	Approved
0.7348	Intermediate Similarity	NPD8150	Discontinued
0.7348	Intermediate Similarity	NPD8434	Phase 2
0.7317	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4308	Phase 3
0.7303	Intermediate Similarity	NPD9717	Approved
0.7303	Intermediate Similarity	NPD1608	Approved
0.7299	Intermediate Similarity	NPD5710	Approved
0.7299	Intermediate Similarity	NPD5711	Approved
0.7287	Intermediate Similarity	NPD6779	Approved
0.7287	Intermediate Similarity	NPD6780	Approved
0.7287	Intermediate Similarity	NPD6778	Approved
0.7287	Intermediate Similarity	NPD6777	Approved
0.7287	Intermediate Similarity	NPD6776	Approved
0.7287	Intermediate Similarity	NPD6781	Approved
0.7287	Intermediate Similarity	NPD6782	Approved
0.7273	Intermediate Similarity	NPD2797	Approved
0.7267	Intermediate Similarity	NPD5405	Approved
0.7267	Intermediate Similarity	NPD5406	Approved
0.7267	Intermediate Similarity	NPD5404	Approved
0.7267	Intermediate Similarity	NPD5408	Approved
0.7263	Intermediate Similarity	NPD7435	Discontinued
0.7262	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5242	Approved
0.7254	Intermediate Similarity	NPD8151	Discontinued
0.7229	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1471	Phase 3
0.7219	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7033	Discontinued
0.72	Intermediate Similarity	NPD7229	Phase 3
0.7197	Intermediate Similarity	NPD7095	Approved
0.719	Intermediate Similarity	NPD9269	Phase 2
0.7173	Intermediate Similarity	NPD7698	Approved
0.7173	Intermediate Similarity	NPD7697	Approved
0.7173	Intermediate Similarity	NPD7696	Phase 3
0.717	Intermediate Similarity	NPD4060	Phase 1
0.716	Intermediate Similarity	NPD7458	Discontinued
0.7152	Intermediate Similarity	NPD2354	Approved
0.7152	Intermediate Similarity	NPD411	Approved
0.7152	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5353	Approved
0.715	Intermediate Similarity	NPD7584	Approved
0.7135	Intermediate Similarity	NPD7870	Phase 2
0.7135	Intermediate Similarity	NPD7871	Phase 2
0.7133	Intermediate Similarity	NPD5536	Phase 2
0.7125	Intermediate Similarity	NPD6355	Discontinued
0.7125	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD422	Phase 1
0.712	Intermediate Similarity	NPD6823	Phase 2
0.7119	Intermediate Similarity	NPD2403	Approved
0.7113	Intermediate Similarity	NPD7701	Phase 2
0.7112	Intermediate Similarity	NPD4360	Phase 2
0.7112	Intermediate Similarity	NPD4363	Phase 3
0.7105	Intermediate Similarity	NPD17	Approved
0.7092	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7783	Phase 2
0.7091	Intermediate Similarity	NPD8166	Discontinued
0.7086	Intermediate Similarity	NPD1548	Phase 1
0.7078	Intermediate Similarity	NPD3972	Approved
0.7076	Intermediate Similarity	NPD6386	Approved
0.7076	Intermediate Similarity	NPD6385	Approved
0.7072	Intermediate Similarity	NPD7240	Approved
0.707	Intermediate Similarity	NPD3018	Phase 2
0.7066	Intermediate Similarity	NPD4357	Discontinued
0.7063	Intermediate Similarity	NPD4307	Phase 2

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