NPASS Compound

Structure

NPC472963 OpenBabel07101719132D 32 34 0 0 1 0 0 0 0 0999 V2000 1.6037 5.0532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1895 5.0532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3449 2.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4483 2.6730 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1895 3.6390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 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 5.1962 -2.0000 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 0.8660 -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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8966 4.3461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.7942 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6037 3.6390 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 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 31 1 0 0 0 0 5 13 1 0 0 0 0 5 14 1 0 0 0 0 6 10 1 0 0 0 0 6 17 1 0 0 0 0 7 11 2 0 0 0 0 7 17 1 0 0 0 0 8 9 2 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 26 1 0 0 0 0 16 18 2 0 0 0 0 16 23 1 0 0 0 0 17 19 2 0 0 0 0 18 27 1 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 23 2 0 0 0 0 21 28 2 0 0 0 0 22 24 2 0 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 24 32 1 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.24
Volume:	466.869
LogP:	4.898
LogD:	3.852
LogS:	-4.049
# Rotatable Bonds:	9
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.456
Synthetic Accessibility Score:	3.49
Fsp3:	0.5
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:	-4.813
MDCK Permeability:	1.680978311924264e-05
Pgp-inhibitor:	0.656
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	98.13550567626953%
Volume Distribution (VD):	0.604
Pgp-substrate:	1.0853300094604492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.704
CYP1A2-substrate:	0.895
CYP2C19-inhibitor:	0.676
CYP2C19-substrate:	0.097
CYP2C9-inhibitor:	0.547
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.877
CYP2D6-substrate:	0.897
CYP3A4-inhibitor:	0.756
CYP3A4-substrate:	0.286

ADMET: Excretion

Clearance (CL):	9.226
Half-life (T1/2):	0.82

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.354
Skin Sensitization:	0.919
Carcinogencity:	0.137
Eye Corrosion:	0.003
Eye Irritation:	0.042
Respiratory Toxicity:	0.063

Download Data

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

Natural Product: NPC472963

Natural Product ID:	NPC472963
*Common Name:**	KMZMDRKKQBTDEX-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KMZMDRKKQBTDEX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H34O6/c1-25(2,31-4)13-5-14-26(3)15-12-19-17(7-11-22(29)24(19)32-26)6-10-21(28)20-9-8-18(27)16-23(20)30/h7-9,11,16,27,29-30H,5-6,10,12-15H2,1-4H3
SMILES:	CC1(CCC2=C(C=CC(=C2O1)O)CCC(=O)C3=C(C=C(C=C3)O)O)CCCC(C)(C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594223
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	=	48300.0	nM	PMID[489568]
NPT610	Others	Molecular identity unknown		IC50	=	39900.0	nM	PMID[489568]

☑ 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 NPC472963 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	414
0.1-0.2	1657
0.2-0.3	4118
0.3-0.4	10415
0.4-0.5	7611
0.5-0.6	3164
0.6-0.7	4813
0.7-0.8	5700
0.8-0.85	2696
0.85-0.9	1655
0.9-0.95	441
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC472907
0.9799	High Similarity	NPC472905
0.9739	High Similarity	NPC472964
0.9737	High Similarity	NPC474960
0.9608	High Similarity	NPC472902
0.9605	High Similarity	NPC136674
0.9542	High Similarity	NPC476242
0.9539	High Similarity	NPC24640
0.9536	High Similarity	NPC469550
0.9487	High Similarity	NPC293319
0.9484	High Similarity	NPC201800
0.9481	High Similarity	NPC36217
0.9481	High Similarity	NPC471973
0.9477	High Similarity	NPC129684
0.9477	High Similarity	NPC241904
0.9477	High Similarity	NPC67876
0.9477	High Similarity	NPC299520
0.9477	High Similarity	NPC300727
0.9474	High Similarity	NPC152951
0.9474	High Similarity	NPC117992
0.9474	High Similarity	NPC230149
0.9474	High Similarity	NPC57674
0.9474	High Similarity	NPC256925
0.9474	High Similarity	NPC67396
0.9474	High Similarity	NPC168247
0.9474	High Similarity	NPC234255
0.947	High Similarity	NPC260979
0.947	High Similarity	NPC472912
0.947	High Similarity	NPC477231
0.947	High Similarity	NPC257648
0.9467	High Similarity	NPC151473
0.9467	High Similarity	NPC29231
0.9427	High Similarity	NPC39091
0.9423	High Similarity	NPC186686
0.9419	High Similarity	NPC278052
0.9419	High Similarity	NPC61010
0.9419	High Similarity	NPC40491
0.9419	High Similarity	NPC472906
0.9416	High Similarity	NPC204879
0.9416	High Similarity	NPC210459
0.9416	High Similarity	NPC55738
0.9416	High Similarity	NPC235448
0.9412	High Similarity	NPC274730
0.9412	High Similarity	NPC472455
0.9408	High Similarity	NPC49402
0.9408	High Similarity	NPC70433
0.9408	High Similarity	NPC227337
0.9408	High Similarity	NPC273462
0.9408	High Similarity	NPC33051
0.9408	High Similarity	NPC18727
0.9404	High Similarity	NPC31363
0.9367	High Similarity	NPC218226
0.9363	High Similarity	NPC303174
0.9363	High Similarity	NPC239752
0.9363	High Similarity	NPC275780
0.9363	High Similarity	NPC472450
0.9355	High Similarity	NPC200746
0.9355	High Similarity	NPC228785
0.9355	High Similarity	NPC14353
0.9355	High Similarity	NPC56085
0.9355	High Similarity	NPC139036
0.9355	High Similarity	NPC470183
0.9355	High Similarity	NPC299436
0.9355	High Similarity	NPC321399
0.9355	High Similarity	NPC320359
0.9351	High Similarity	NPC218313
0.9351	High Similarity	NPC291508
0.9351	High Similarity	NPC474681
0.9351	High Similarity	NPC52889
0.9351	High Similarity	NPC180011
0.9351	High Similarity	NPC27337
0.9351	High Similarity	NPC161960
0.9351	High Similarity	NPC304008
0.9351	High Similarity	NPC187745
0.9351	High Similarity	NPC219867
0.9351	High Similarity	NPC111969
0.9346	High Similarity	NPC472280
0.9346	High Similarity	NPC31018
0.9346	High Similarity	NPC255807
0.9342	High Similarity	NPC39732
0.9342	High Similarity	NPC302950
0.9342	High Similarity	NPC237994
0.9342	High Similarity	NPC219582
0.9342	High Similarity	NPC236637
0.9342	High Similarity	NPC60972
0.9338	High Similarity	NPC85131
0.9333	High Similarity	NPC196277
0.9333	High Similarity	NPC272721
0.9333	High Similarity	NPC43669
0.9304	High Similarity	NPC43319
0.9304	High Similarity	NPC477517
0.9299	High Similarity	NPC236521
0.9299	High Similarity	NPC7483
0.9299	High Similarity	NPC189473
0.9299	High Similarity	NPC248638
0.9299	High Similarity	NPC23298
0.9299	High Similarity	NPC152659
0.9299	High Similarity	NPC475985
0.9299	High Similarity	NPC236132
0.9299	High Similarity	NPC220313
0.9295	High Similarity	NPC472634
0.9295	High Similarity	NPC234644
0.9295	High Similarity	NPC57715
0.9295	High Similarity	NPC471210
0.9295	High Similarity	NPC474187
0.929	High Similarity	NPC474290
0.929	High Similarity	NPC100123
0.929	High Similarity	NPC280680
0.929	High Similarity	NPC184755
0.929	High Similarity	NPC74178
0.9286	High Similarity	NPC115853
0.9286	High Similarity	NPC35038
0.9286	High Similarity	NPC278778
0.9286	High Similarity	NPC470600
0.9286	High Similarity	NPC133970
0.9286	High Similarity	NPC474638
0.9286	High Similarity	NPC209614
0.9286	High Similarity	NPC195796
0.9286	High Similarity	NPC6633
0.9286	High Similarity	NPC472916
0.9286	High Similarity	NPC5322
0.9286	High Similarity	NPC472626
0.9286	High Similarity	NPC470328
0.9286	High Similarity	NPC291878
0.9281	High Similarity	NPC88645
0.9281	High Similarity	NPC89474
0.9281	High Similarity	NPC271779
0.9281	High Similarity	NPC206238
0.9281	High Similarity	NPC167091
0.9281	High Similarity	NPC141212
0.9281	High Similarity	NPC292214
0.9276	High Similarity	NPC154345
0.9272	High Similarity	NPC183950
0.9272	High Similarity	NPC177298
0.9272	High Similarity	NPC137062
0.9272	High Similarity	NPC48479
0.9272	High Similarity	NPC52005
0.9272	High Similarity	NPC287101
0.9272	High Similarity	NPC223579
0.9272	High Similarity	NPC105512
0.9267	High Similarity	NPC95864
0.9267	High Similarity	NPC77378
0.9241	High Similarity	NPC475888
0.9236	High Similarity	NPC83922
0.9236	High Similarity	NPC474150
0.9236	High Similarity	NPC329760
0.9236	High Similarity	NPC472448
0.9236	High Similarity	NPC474162
0.9236	High Similarity	NPC25152
0.9236	High Similarity	NPC229632
0.9236	High Similarity	NPC211107
0.9236	High Similarity	NPC474034
0.9236	High Similarity	NPC474033
0.9231	High Similarity	NPC119209
0.9231	High Similarity	NPC474287
0.9231	High Similarity	NPC472624
0.9231	High Similarity	NPC472631
0.9231	High Similarity	NPC472630
0.9231	High Similarity	NPC192686
0.9231	High Similarity	NPC475886
0.9231	High Similarity	NPC118256
0.9231	High Similarity	NPC188433
0.9231	High Similarity	NPC476980
0.9226	High Similarity	NPC472911
0.9226	High Similarity	NPC156057
0.9226	High Similarity	NPC471515
0.9226	High Similarity	NPC474208
0.9226	High Similarity	NPC273843
0.9226	High Similarity	NPC162869
0.9226	High Similarity	NPC236796
0.9226	High Similarity	NPC78225
0.9226	High Similarity	NPC165977
0.9226	High Similarity	NPC217677
0.9226	High Similarity	NPC472914
0.9226	High Similarity	NPC99597
0.9226	High Similarity	NPC471479
0.9226	High Similarity	NPC48208
0.9226	High Similarity	NPC472598
0.9226	High Similarity	NPC262286
0.9226	High Similarity	NPC210084
0.9226	High Similarity	NPC475267
0.9226	High Similarity	NPC36852
0.9226	High Similarity	NPC181960
0.9226	High Similarity	NPC474836
0.9226	High Similarity	NPC472910
0.9226	High Similarity	NPC96167
0.9226	High Similarity	NPC245758
0.9226	High Similarity	NPC474055
0.9226	High Similarity	NPC469584
0.9226	High Similarity	NPC472913
0.9226	High Similarity	NPC222814
0.9226	High Similarity	NPC52530
0.9221	High Similarity	NPC226025
0.9221	High Similarity	NPC470327
0.9221	High Similarity	NPC20541
0.9221	High Similarity	NPC477503
0.9221	High Similarity	NPC2928
0.9221	High Similarity	NPC256612
0.9221	High Similarity	NPC45849
0.9221	High Similarity	NPC200761

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 NPC472963 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	373
0.1-0.2	980
0.2-0.3	1640
0.3-0.4	2644
0.4-0.5	1774
0.5-0.6	1003
0.6-0.7	531
0.7-0.8	150
0.8-0.85	32
0.85-0.9	19
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9342	High Similarity	NPD1934	Approved
0.9156	High Similarity	NPD2801	Approved
0.9156	High Similarity	NPD2393	Clinical (unspecified phase)
0.9038	High Similarity	NPD3882	Suspended
0.894	High Similarity	NPD1511	Approved
0.8882	High Similarity	NPD6166	Phase 2
0.8882	High Similarity	NPD6167	Clinical (unspecified phase)
0.8882	High Similarity	NPD6168	Clinical (unspecified phase)
0.8824	High Similarity	NPD1512	Approved
0.879	High Similarity	NPD7819	Suspended
0.878	High Similarity	NPD7074	Phase 3
0.872	High Similarity	NPD7054	Approved
0.8667	High Similarity	NPD7472	Approved
0.8659	High Similarity	NPD3818	Discontinued
0.8625	High Similarity	NPD7075	Discontinued
0.8616	High Similarity	NPD3817	Phase 2
0.8609	High Similarity	NPD1549	Phase 2
0.8598	High Similarity	NPD7473	Discontinued
0.8562	High Similarity	NPD4868	Clinical (unspecified phase)
0.8553	High Similarity	NPD1465	Phase 2
0.8553	High Similarity	NPD7096	Clinical (unspecified phase)
0.8543	High Similarity	NPD1552	Clinical (unspecified phase)
0.8543	High Similarity	NPD1550	Clinical (unspecified phase)
0.8528	High Similarity	NPD6232	Discontinued
0.8519	High Similarity	NPD5494	Approved
0.8516	High Similarity	NPD4378	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD4380	Phase 2
0.8452	Intermediate Similarity	NPD7251	Discontinued
0.8411	Intermediate Similarity	NPD1510	Phase 2
0.8402	Intermediate Similarity	NPD7808	Phase 3
0.8397	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD6797	Phase 2
0.8389	Intermediate Similarity	NPD1240	Approved
0.8385	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD5844	Phase 1
0.8355	Intermediate Similarity	NPD2796	Approved
0.8333	Intermediate Similarity	NPD6799	Approved
0.8294	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD3749	Approved
0.8278	Intermediate Similarity	NPD1607	Approved
0.8267	Intermediate Similarity	NPD943	Approved
0.8258	Intermediate Similarity	NPD3750	Approved
0.825	Intermediate Similarity	NPD6599	Discontinued
0.8247	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6959	Discontinued
0.8199	Intermediate Similarity	NPD7411	Suspended
0.8148	Intermediate Similarity	NPD6801	Discontinued
0.8144	Intermediate Similarity	NPD3926	Phase 2
0.8117	Intermediate Similarity	NPD6100	Approved
0.8117	Intermediate Similarity	NPD6099	Approved
0.807	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD3748	Approved
0.7935	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6559	Discontinued
0.7917	Intermediate Similarity	NPD7199	Phase 2
0.7908	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD1613	Approved
0.7904	Intermediate Similarity	NPD919	Approved
0.784	Intermediate Similarity	NPD5403	Approved
0.7831	Intermediate Similarity	NPD5402	Approved
0.7826	Intermediate Similarity	NPD2533	Approved
0.7826	Intermediate Similarity	NPD2532	Approved
0.7826	Intermediate Similarity	NPD2534	Approved
0.7824	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD1247	Approved
0.7809	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD4628	Phase 3
0.7799	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3751	Discontinued
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1551	Phase 2
0.7771	Intermediate Similarity	NPD2935	Discontinued
0.7744	Intermediate Similarity	NPD3226	Approved
0.7742	Intermediate Similarity	NPD230	Phase 1
0.7742	Intermediate Similarity	NPD1933	Approved
0.7742	Intermediate Similarity	NPD447	Suspended
0.774	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2800	Approved
0.7736	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD2344	Approved
0.7722	Intermediate Similarity	NPD2346	Discontinued
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD5401	Approved
0.7712	Intermediate Similarity	NPD3027	Phase 3
0.7692	Intermediate Similarity	NPD6234	Discontinued
0.7667	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3787	Discontinued
0.7654	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD4625	Phase 3
0.7595	Intermediate Similarity	NPD2799	Discontinued
0.7586	Intermediate Similarity	NPD7228	Approved
0.7582	Intermediate Similarity	NPD9494	Approved
0.758	Intermediate Similarity	NPD6651	Approved
0.7546	Intermediate Similarity	NPD7390	Discontinued
0.7532	Intermediate Similarity	NPD4908	Phase 1
0.7531	Intermediate Similarity	NPD2309	Approved
0.7528	Intermediate Similarity	NPD8313	Approved
0.7528	Intermediate Similarity	NPD8312	Approved
0.7516	Intermediate Similarity	NPD1243	Approved
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD37	Approved
0.7472	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4965	Approved
0.7471	Intermediate Similarity	NPD4967	Phase 2
0.7471	Intermediate Similarity	NPD4966	Approved
0.747	Intermediate Similarity	NPD1653	Approved
0.7469	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5953	Discontinued
0.7451	Intermediate Similarity	NPD1203	Approved
0.7443	Intermediate Similarity	NPD7286	Phase 2
0.7436	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6190	Approved
0.7419	Intermediate Similarity	NPD6832	Phase 2
0.7417	Intermediate Similarity	NPD1610	Phase 2
0.7417	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD920	Approved
0.7403	Intermediate Similarity	NPD8150	Discontinued
0.7403	Intermediate Similarity	NPD2798	Approved
0.7403	Intermediate Similarity	NPD8434	Phase 2
0.7378	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5711	Approved
0.7356	Intermediate Similarity	NPD5710	Approved
0.734	Intermediate Similarity	NPD6779	Approved
0.734	Intermediate Similarity	NPD6780	Approved
0.734	Intermediate Similarity	NPD6781	Approved
0.734	Intermediate Similarity	NPD6782	Approved
0.734	Intermediate Similarity	NPD6777	Approved
0.734	Intermediate Similarity	NPD6778	Approved
0.734	Intermediate Similarity	NPD6776	Approved
0.7338	Intermediate Similarity	NPD1470	Approved
0.7325	Intermediate Similarity	NPD2313	Discontinued
0.7325	Intermediate Similarity	NPD3764	Approved
0.7325	Intermediate Similarity	NPD3268	Approved
0.7322	Intermediate Similarity	NPD4287	Approved
0.7321	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4749	Approved
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7314	Intermediate Similarity	NPD5242	Approved
0.731	Intermediate Similarity	NPD4288	Approved
0.7306	Intermediate Similarity	NPD8151	Discontinued
0.7303	Intermediate Similarity	NPD1201	Approved
0.7289	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7033	Discontinued
0.7267	Intermediate Similarity	NPD4308	Phase 3
0.7257	Intermediate Similarity	NPD7229	Phase 3
0.7255	Intermediate Similarity	NPD9717	Approved
0.7255	Intermediate Similarity	NPD1608	Approved
0.7233	Intermediate Similarity	NPD4060	Phase 1
0.7226	Intermediate Similarity	NPD2797	Approved
0.7225	Intermediate Similarity	NPD7698	Approved
0.7225	Intermediate Similarity	NPD7696	Phase 3
0.7225	Intermediate Similarity	NPD7697	Approved
0.7222	Intermediate Similarity	NPD5405	Approved
0.7222	Intermediate Similarity	NPD5404	Approved
0.7222	Intermediate Similarity	NPD5406	Approved
0.7222	Intermediate Similarity	NPD5408	Approved
0.7219	Intermediate Similarity	NPD7458	Discontinued
0.7215	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5353	Approved
0.7202	Intermediate Similarity	NPD7584	Approved
0.72	Intermediate Similarity	NPD5536	Phase 2
0.7188	Intermediate Similarity	NPD7871	Phase 2
0.7188	Intermediate Similarity	NPD6355	Discontinued
0.7188	Intermediate Similarity	NPD7870	Phase 2
0.7188	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1471	Phase 3
0.7175	Intermediate Similarity	NPD2403	Approved
0.7173	Intermediate Similarity	NPD6823	Phase 2
0.7166	Intermediate Similarity	NPD4360	Phase 2
0.7166	Intermediate Similarity	NPD4363	Phase 3
0.7165	Intermediate Similarity	NPD7701	Phase 2
0.7152	Intermediate Similarity	NPD8166	Discontinued
0.7152	Intermediate Similarity	NPD1548	Phase 1
0.7152	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD3972	Approved
0.7143	Intermediate Similarity	NPD7783	Phase 2
0.7143	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7135	Intermediate Similarity	NPD6386	Approved
0.7135	Intermediate Similarity	NPD6385	Approved
0.7134	Intermediate Similarity	NPD3018	Phase 2
0.7127	Intermediate Similarity	NPD7240	Approved
0.7126	Intermediate Similarity	NPD4357	Discontinued
0.711	Intermediate Similarity	NPD5978	Approved
0.711	Intermediate Similarity	NPD5977	Approved
0.7108	Intermediate Similarity	NPD2354	Approved
0.7107	Intermediate Similarity	NPD6798	Discontinued
0.7107	Intermediate Similarity	NPD411	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