NPASS Compound

Structure

NPC253105 OpenBabel07101718182D 27 29 0 0 1 0 0 0 0 0999 V2000 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 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 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 -3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 4 1 0 0 0 0 2 11 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 5 15 1 0 0 0 0 6 11 2 0 0 0 0 6 16 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 12 1 0 0 0 0 8 19 2 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 0 0 0 0 13 21 1 6 0 0 0 14 4 1 1 0 0 0 14 27 1 0 0 0 0 15 16 2 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 20 2 0 0 0 0 17 24 1 0 0 0 0 18 12 1 1 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.15
Volume:	374.52
LogP:	1.998
LogD:	2.35
LogS:	-2.792
# Rotatable Bonds:	5
TPSA:	119.61
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.509
Synthetic Accessibility Score:	3.569
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.91
MDCK Permeability:	1.193166826851666e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.596
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	93.31478118896484%
Volume Distribution (VD):	0.497
Pgp-substrate:	8.548065185546875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.265
CYP1A2-substrate:	0.688
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.074
CYP2C9-inhibitor:	0.545
CYP2C9-substrate:	0.705
CYP2D6-inhibitor:	0.178
CYP2D6-substrate:	0.47
CYP3A4-inhibitor:	0.211
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	16.35
Half-life (T1/2):	0.902

ADMET: Toxicity

hERG Blockers:	0.14
Human Hepatotoxicity (H-HT):	0.349
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.564
Rat Oral Acute Toxicity:	0.188
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.974
Carcinogencity:	0.765
Eye Corrosion:	0.032
Eye Irritation:	0.922
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC253105

Natural Product ID:	NPC253105
*Common Name:**	1,5-Epoxy-3-Hydroxy-1-(4,5-Dihydroxy-3-Methoxyphenyl)-7-(3,4-Dihydroxyphenyl)Heptane
IUPAC Name:	5-[(2S,4S,6S)-6-[2-(3,4-dihydroxyphenyl)ethyl]-4-hydroxyoxan-2-yl]-3-methoxybenzene-1,2-diol
Synonyms:
Standard InCHIKey:	CDLANTQZSUXRAX-DEYYWGMASA-N
Standard InCHI:	InChI=1S/C20H24O7/c1-26-19-8-12(7-17(24)20(19)25)18-10-13(21)9-14(27-18)4-2-11-3-5-15(22)16(23)6-11/h3,5-8,13-14,18,21-25H,2,4,9-10H2,1H3/t13-,14-,18-/m0/s1
SMILES:	COc1cc(cc(c1O)O)[C@@H]1C[C@H](C[C@H](CCc2ccc(c(c2)O)O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL257556
PubChem CID:	44448125
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[18177011]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271742]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20590154]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
Tissue	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	=	39890.0	nM	PMID[477560]
NPT625	Tissue	Liver	Mus musculus	IC50	=	21860.0	nM	PMID[477560]

☑ 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 NPC253105 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	392
0.1-0.2	1412
0.2-0.3	3870
0.3-0.4	10858
0.4-0.5	7930
0.5-0.6	4145
0.6-0.7	6897
0.7-0.8	5351
0.8-0.85	1006
0.85-0.9	618
0.9-0.95	203
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC201587
0.976	High Similarity	NPC476968
0.976	High Similarity	NPC170844
0.969	High Similarity	NPC306441
0.969	High Similarity	NPC16435
0.9688	High Similarity	NPC170694
0.968	High Similarity	NPC98631
0.968	High Similarity	NPC474178
0.968	High Similarity	NPC186843
0.968	High Similarity	NPC206615
0.968	High Similarity	NPC245826
0.968	High Similarity	NPC252307
0.968	High Similarity	NPC470213
0.9612	High Similarity	NPC61946
0.9612	High Similarity	NPC112246
0.9612	High Similarity	NPC47398
0.9612	High Similarity	NPC474206
0.9612	High Similarity	NPC121812
0.9612	High Similarity	NPC234333
0.9612	High Similarity	NPC260898
0.9612	High Similarity	NPC470356
0.9612	High Similarity	NPC94750
0.9612	High Similarity	NPC112939
0.9606	High Similarity	NPC474017
0.9606	High Similarity	NPC472597
0.9606	High Similarity	NPC470096
0.9606	High Similarity	NPC470095
0.9538	High Similarity	NPC302701
0.9538	High Similarity	NPC227503
0.9538	High Similarity	NPC230734
0.9538	High Similarity	NPC474639
0.9538	High Similarity	NPC269091
0.9535	High Similarity	NPC287745
0.9531	High Similarity	NPC16208
0.9531	High Similarity	NPC7903
0.9531	High Similarity	NPC160991
0.9531	High Similarity	NPC470752
0.9531	High Similarity	NPC184447
0.9531	High Similarity	NPC35932
0.9528	High Similarity	NPC472338
0.9466	High Similarity	NPC326797
0.9466	High Similarity	NPC211549
0.9466	High Similarity	NPC474282
0.9466	High Similarity	NPC176051
0.9466	High Similarity	NPC103976
0.9466	High Similarity	NPC102904
0.9466	High Similarity	NPC107551
0.9462	High Similarity	NPC164787
0.9462	High Similarity	NPC151224
0.9457	High Similarity	NPC11060
0.9457	High Similarity	NPC475840
0.9457	High Similarity	NPC158331
0.9457	High Similarity	NPC263064
0.9453	High Similarity	NPC309787
0.9449	High Similarity	NPC3439
0.9449	High Similarity	NPC190629
0.9449	High Similarity	NPC222004
0.9449	High Similarity	NPC226788
0.9449	High Similarity	NPC86030
0.9449	High Similarity	NPC210623
0.9449	High Similarity	NPC212015
0.9449	High Similarity	NPC5851
0.9449	High Similarity	NPC470258
0.9449	High Similarity	NPC285339
0.9449	High Similarity	NPC273295
0.9449	High Similarity	NPC218856
0.9449	High Similarity	NPC202582
0.944	High Similarity	NPC116907
0.944	High Similarity	NPC251855
0.944	High Similarity	NPC17943
0.944	High Similarity	NPC472093
0.944	High Similarity	NPC221077
0.944	High Similarity	NPC475169
0.944	High Similarity	NPC57490
0.944	High Similarity	NPC203133
0.944	High Similarity	NPC208950
0.944	High Similarity	NPC193544
0.944	High Similarity	NPC233410
0.944	High Similarity	NPC298757
0.944	High Similarity	NPC117214
0.9398	High Similarity	NPC471389
0.9394	High Similarity	NPC22517
0.9389	High Similarity	NPC248727
0.9389	High Similarity	NPC472336
0.9389	High Similarity	NPC162659
0.9389	High Similarity	NPC472334
0.9389	High Similarity	NPC265433
0.9389	High Similarity	NPC270456
0.9389	High Similarity	NPC470802
0.9385	High Similarity	NPC326095
0.9385	High Similarity	NPC317380
0.9385	High Similarity	NPC310854
0.9385	High Similarity	NPC244983
0.938	High Similarity	NPC185604
0.938	High Similarity	NPC61477
0.938	High Similarity	NPC219876
0.938	High Similarity	NPC86655
0.938	High Similarity	NPC127624
0.938	High Similarity	NPC261619
0.938	High Similarity	NPC204215
0.938	High Similarity	NPC78770
0.938	High Similarity	NPC126029
0.938	High Similarity	NPC175067
0.938	High Similarity	NPC15658
0.938	High Similarity	NPC202762
0.937	High Similarity	NPC72529
0.9328	High Similarity	NPC189115
0.9323	High Similarity	NPC184797
0.9323	High Similarity	NPC309124
0.9323	High Similarity	NPC291101
0.9323	High Similarity	NPC266197
0.9318	High Similarity	NPC474390
0.9318	High Similarity	NPC276490
0.9313	High Similarity	NPC99572
0.9313	High Similarity	NPC256262
0.9313	High Similarity	NPC472337
0.9313	High Similarity	NPC126409
0.9313	High Similarity	NPC473413
0.9308	High Similarity	NPC168059
0.9308	High Similarity	NPC229442
0.9302	High Similarity	NPC469613
0.9302	High Similarity	NPC268266
0.9302	High Similarity	NPC469625
0.9302	High Similarity	NPC220825
0.9302	High Similarity	NPC30043
0.9302	High Similarity	NPC268342
0.9302	High Similarity	NPC42760
0.9297	High Similarity	NPC469951
0.9297	High Similarity	NPC469963
0.9291	High Similarity	NPC292056
0.9291	High Similarity	NPC74817
0.9291	High Similarity	NPC82679
0.9291	High Similarity	NPC474119
0.9291	High Similarity	NPC118533
0.9291	High Similarity	NPC236791
0.9291	High Similarity	NPC41706
0.9291	High Similarity	NPC159968
0.9291	High Similarity	NPC282000
0.9291	High Similarity	NPC118787
0.9291	High Similarity	NPC165045
0.9291	High Similarity	NPC210355
0.9291	High Similarity	NPC169474
0.9291	High Similarity	NPC242032
0.9291	High Similarity	NPC246620
0.9291	High Similarity	NPC163332
0.9291	High Similarity	NPC183181
0.9291	High Similarity	NPC293054
0.9291	High Similarity	NPC319625
0.9291	High Similarity	NPC147821
0.9291	High Similarity	NPC324112
0.9291	High Similarity	NPC111247
0.9291	High Similarity	NPC124452
0.9291	High Similarity	NPC127587
0.928	High Similarity	NPC165375
0.928	High Similarity	NPC136319
0.928	High Similarity	NPC197757
0.928	High Similarity	NPC233526
0.928	High Similarity	NPC220598
0.928	High Similarity	NPC228922
0.928	High Similarity	NPC282496
0.928	High Similarity	NPC471693
0.9254	High Similarity	NPC224876
0.9254	High Similarity	NPC469661
0.9254	High Similarity	NPC83375
0.9248	High Similarity	NPC260741
0.9248	High Similarity	NPC473739
0.9248	High Similarity	NPC232164
0.9248	High Similarity	NPC70682
0.9248	High Similarity	NPC25966
0.9248	High Similarity	NPC319647
0.9248	High Similarity	NPC471388
0.9248	High Similarity	NPC127218
0.9248	High Similarity	NPC236306
0.9248	High Similarity	NPC245207
0.9242	High Similarity	NPC234952
0.9237	High Similarity	NPC478085
0.9225	High Similarity	NPC51840
0.9225	High Similarity	NPC469614
0.9225	High Similarity	NPC187998
0.9225	High Similarity	NPC241522
0.9225	High Similarity	NPC257582
0.9225	High Similarity	NPC77040
0.9225	High Similarity	NPC469612
0.9225	High Similarity	NPC92164
0.9225	High Similarity	NPC64201
0.9225	High Similarity	NPC234488
0.9225	High Similarity	NPC174495
0.9225	High Similarity	NPC299221
0.9225	High Similarity	NPC242807
0.9225	High Similarity	NPC153739
0.9225	High Similarity	NPC145305
0.9225	High Similarity	NPC311680
0.9225	High Similarity	NPC42300
0.9213	High Similarity	NPC103823
0.9213	High Similarity	NPC178284
0.9213	High Similarity	NPC76451
0.9213	High Similarity	NPC44748
0.9213	High Similarity	NPC18924
0.9213	High Similarity	NPC58607
0.9213	High Similarity	NPC78974

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 NPC253105 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	817
0.2-0.3	1732
0.3-0.4	2731
0.4-0.5	1747
0.5-0.6	995
0.6-0.7	629
0.7-0.8	164
0.8-0.85	5
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.976	High Similarity	NPD3027	Phase 3
0.938	High Similarity	NPD1613	Approved
0.938	High Similarity	NPD1612	Clinical (unspecified phase)
0.907	High Similarity	NPD1529	Clinical (unspecified phase)
0.8992	High Similarity	NPD1530	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1934	Approved
0.8358	Intermediate Similarity	NPD4908	Phase 1
0.8258	Intermediate Similarity	NPD2982	Phase 2
0.8258	Intermediate Similarity	NPD2983	Phase 2
0.8244	Intermediate Similarity	NPD1610	Phase 2
0.824	Intermediate Similarity	NPD228	Approved
0.8235	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2981	Phase 2
0.8148	Intermediate Similarity	NPD3018	Phase 2
0.811	Intermediate Similarity	NPD5283	Phase 1
0.8095	Intermediate Similarity	NPD1653	Approved
0.8077	Intermediate Similarity	NPD1548	Phase 1
0.8065	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6166	Phase 2
0.8028	Intermediate Similarity	NPD7266	Discontinued
0.8015	Intermediate Similarity	NPD2861	Phase 2
0.7986	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD3620	Phase 2
0.7985	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD6234	Discontinued
0.7961	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD2801	Approved
0.7899	Intermediate Similarity	NPD4625	Phase 3
0.7881	Intermediate Similarity	NPD37	Approved
0.7862	Intermediate Similarity	NPD7074	Phase 3
0.7852	Intermediate Similarity	NPD4749	Approved
0.7848	Intermediate Similarity	NPD7228	Approved
0.7843	Intermediate Similarity	NPD4966	Approved
0.7843	Intermediate Similarity	NPD4965	Approved
0.7843	Intermediate Similarity	NPD4967	Phase 2
0.7842	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD4536	Approved
0.7817	Intermediate Similarity	NPD4538	Approved
0.7808	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7054	Approved
0.7795	Intermediate Similarity	NPD3022	Approved
0.7795	Intermediate Similarity	NPD3021	Approved
0.7793	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7472	Approved
0.7748	Intermediate Similarity	NPD4380	Phase 2
0.7736	Intermediate Similarity	NPD3818	Discontinued
0.773	Intermediate Similarity	NPD1558	Phase 1
0.7727	Intermediate Similarity	NPD3882	Suspended
0.7717	Intermediate Similarity	NPD2684	Approved
0.7704	Intermediate Similarity	NPD3705	Approved
0.7704	Intermediate Similarity	NPD1091	Approved
0.7703	Intermediate Similarity	NPD1511	Approved
0.7682	Intermediate Similarity	NPD4005	Discontinued
0.7671	Intermediate Similarity	NPD6674	Discontinued
0.7671	Intermediate Similarity	NPD5177	Phase 3
0.7671	Intermediate Similarity	NPD3060	Approved
0.7655	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD5960	Phase 3
0.7639	Intermediate Similarity	NPD5588	Approved
0.7632	Intermediate Similarity	NPD4678	Approved
0.7632	Intermediate Similarity	NPD4675	Approved
0.7615	Intermediate Similarity	NPD7843	Approved
0.7612	Intermediate Similarity	NPD1357	Approved
0.76	Intermediate Similarity	NPD1512	Approved
0.7593	Intermediate Similarity	NPD6797	Phase 2
0.7578	Intermediate Similarity	NPD5844	Phase 1
0.7576	Intermediate Similarity	NPD7157	Approved
0.7568	Intermediate Similarity	NPD6190	Approved
0.7564	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4237	Approved
0.7551	Intermediate Similarity	NPD4236	Phase 3
0.7551	Intermediate Similarity	NPD1652	Phase 2
0.7548	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD3817	Phase 2
0.7546	Intermediate Similarity	NPD7251	Discontinued
0.7534	Intermediate Similarity	NPD3540	Phase 1
0.7532	Intermediate Similarity	NPD7199	Phase 2
0.7517	Intermediate Similarity	NPD5058	Phase 3
0.75	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4060	Phase 1
0.7467	Intermediate Similarity	NPD7213	Phase 3
0.7467	Intermediate Similarity	NPD4357	Discontinued
0.7467	Intermediate Similarity	NPD7212	Phase 2
0.7467	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD3539	Phase 1
0.7465	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD5536	Phase 2
0.7452	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6671	Approved
0.744	Intermediate Similarity	NPD1242	Phase 1
0.7431	Intermediate Similarity	NPD5124	Phase 1
0.7431	Intermediate Similarity	NPD230	Phase 1
0.7431	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6584	Phase 3
0.7426	Intermediate Similarity	NPD6516	Phase 2
0.7426	Intermediate Similarity	NPD5846	Approved
0.7417	Intermediate Similarity	NPD7447	Phase 1
0.7415	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD8651	Approved
0.74	Intermediate Similarity	NPD7124	Phase 2
0.7375	Intermediate Similarity	NPD6232	Discontinued
0.7372	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2977	Approved
0.7372	Intermediate Similarity	NPD1465	Phase 2
0.7372	Intermediate Similarity	NPD2978	Approved
0.7365	Intermediate Similarity	NPD1549	Phase 2
0.7364	Intermediate Similarity	NPD290	Approved
0.7361	Intermediate Similarity	NPD2238	Phase 2
0.7358	Intermediate Similarity	NPD5494	Approved
0.7342	Intermediate Similarity	NPD7075	Discontinued
0.7338	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2219	Phase 1
0.7333	Intermediate Similarity	NPD7240	Approved
0.7329	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD422	Phase 1
0.7315	Intermediate Similarity	NPD4162	Approved
0.731	Intermediate Similarity	NPD5735	Approved
0.7303	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4123	Phase 3
0.7292	Intermediate Similarity	NPD2674	Phase 3
0.7292	Intermediate Similarity	NPD6233	Phase 2
0.7287	Intermediate Similarity	NPD968	Approved
0.7279	Intermediate Similarity	NPD1510	Phase 2
0.7273	Intermediate Similarity	NPD7095	Approved
0.7267	Intermediate Similarity	NPD4535	Phase 3
0.7267	Intermediate Similarity	NPD6331	Phase 2
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.7261	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD940	Approved
0.7244	Intermediate Similarity	NPD846	Approved
0.7244	Intermediate Similarity	NPD291	Approved
0.7239	Intermediate Similarity	NPD7473	Discontinued
0.7234	Intermediate Similarity	NPD3094	Phase 2
0.723	Intermediate Similarity	NPD6100	Approved
0.723	Intermediate Similarity	NPD6099	Approved
0.7229	Intermediate Similarity	NPD6559	Discontinued
0.7222	Intermediate Similarity	NPD6798	Discontinued
0.7219	Intermediate Similarity	NPD2677	Approved
0.7219	Intermediate Similarity	NPD5241	Discontinued
0.7214	Intermediate Similarity	NPD6583	Phase 3
0.7214	Intermediate Similarity	NPD6582	Phase 2
0.7211	Intermediate Similarity	NPD6111	Discontinued
0.7203	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8054	Approved
0.7202	Intermediate Similarity	NPD8053	Approved
0.719	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7549	Discontinued
0.7181	Intermediate Similarity	NPD1375	Discontinued
0.7174	Intermediate Similarity	NPD5125	Phase 3
0.7174	Intermediate Similarity	NPD5126	Approved
0.7162	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3686	Approved
0.7161	Intermediate Similarity	NPD3687	Approved
0.716	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3892	Phase 2
0.7152	Intermediate Similarity	NPD5772	Approved
0.7152	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4110	Phase 3
0.7152	Intermediate Similarity	NPD5773	Approved
0.7143	Intermediate Similarity	NPD2231	Phase 2
0.7143	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2235	Phase 2
0.7143	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2424	Discontinued
0.7133	Intermediate Similarity	NPD9494	Approved
0.7126	Intermediate Similarity	NPD7685	Pre-registration
0.7124	Intermediate Similarity	NPD1774	Approved
0.7123	Intermediate Similarity	NPD3062	Approved
0.7123	Intermediate Similarity	NPD1240	Approved
0.7123	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3059	Approved
0.7123	Intermediate Similarity	NPD3061	Approved
0.7121	Intermediate Similarity	NPD5451	Approved
0.7121	Intermediate Similarity	NPD4750	Phase 3
0.712	Intermediate Similarity	NPD2859	Approved
0.712	Intermediate Similarity	NPD2860	Approved
0.7114	Intermediate Similarity	NPD2796	Approved
0.7107	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5402	Approved
0.7103	Intermediate Similarity	NPD3144	Approved
0.7103	Intermediate Similarity	NPD5111	Phase 2
0.7103	Intermediate Similarity	NPD5718	Phase 2
0.7103	Intermediate Similarity	NPD3145	Approved
0.7103	Intermediate Similarity	NPD5110	Phase 2
0.7103	Intermediate Similarity	NPD5109	Approved
0.7101	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5535	Approved
0.7089	Intermediate Similarity	NPD6801	Discontinued

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