NPASS Compound

Structure

CID103398 OpenBabel06191715452D 34 36 0 0 1 0 0 0 0 0999 V2000 0.8660 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 2.5981 2.5000 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 -0.0000 3.0000 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 3.4641 3.0000 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 1.7321 4.0000 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 -0.8660 1.5000 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 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 1 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 -5.1962 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 -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 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 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 -6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 1 13 1 0 0 0 0 2 6 1 0 0 0 0 2 14 1 0 0 0 0 3 7 2 0 0 0 0 3 13 1 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 7 17 1 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 14 2 0 0 0 0 10 20 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 21 1 0 0 0 0 12 33 1 0 0 0 0 15 25 2 0 0 0 0 16 6 1 1 0 0 0 16 34 1 0 0 0 0 17 19 2 0 0 0 0 17 26 1 0 0 0 0 18 20 2 0 0 0 0 18 27 1 0 0 0 0 19 28 1 0 0 0 0 20 29 1 0 0 0 0 21 22 1 0 0 0 0 21 30 1 1 0 0 0 22 23 1 0 0 0 0 22 31 1 6 0 0 0 23 24 1 0 0 0 0 23 32 1 1 0 0 0 24 33 1 0 0 0 0 24 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.18
Volume:	467.438
LogP:	0.331
LogD:	0.133
LogS:	-2.109
# Rotatable Bonds:	10
TPSA:	177.14
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.242
Synthetic Accessibility Score:	4.077
Fsp3:	0.458
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.935
MDCK Permeability:	6.347807357087731e-06
Pgp-inhibitor:	0.015
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.95
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	83.99662780761719%
Volume Distribution (VD):	0.551
Pgp-substrate:	11.744085311889648%

ADMET: Metabolism

CYP1A2-inhibitor:	0.069
CYP1A2-substrate:	0.055
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.256
CYP2C9-substrate:	0.483
CYP2D6-inhibitor:	0.281
CYP2D6-substrate:	0.398
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.047

ADMET: Excretion

Clearance (CL):	11.015
Half-life (T1/2):	0.931

ADMET: Toxicity

hERG Blockers:	0.116
Human Hepatotoxicity (H-HT):	0.277
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.758
Rat Oral Acute Toxicity:	0.065
Maximum Recommended Daily Dose:	0.788
Skin Sensitization:	0.958
Carcinogencity:	0.078
Eye Corrosion:	0.003
Eye Irritation:	0.488
Respiratory Toxicity:	0.082

Download Data

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

Natural Product: NPC103398

Natural Product ID:	NPC103398
*Common Name:**	Oregonin
IUPAC Name:	(5S)-1,7-bis(3,4-dihydroxyphenyl)-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyheptan-3-one
Synonyms:	Oregonin
Standard InCHIKey:	AQRNEKDRSXYJIN-IRFILORWSA-N
Standard InCHI:	InChI=1S/C24H30O10/c25-15(5-1-13-3-7-17(26)19(28)9-13)11-16(6-2-14-4-8-18(27)20(29)10-14)34-24-23(32)22(31)21(30)12-33-24/h3-4,7-10,16,21-24,26-32H,1-2,5-6,11-12H2/t16-,21+,22-,23+,24-/m0/s1
SMILES:	C(CC(=O)C[C@H](CCc1ccc(c(c1)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464570
PubChem CID:	14707658
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
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[20045319]
NPO4971	Alnus firma	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21504848]
NPO32876	alnus hirsuta f. sibirica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23465614]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26341132]
NPO23108	Pinus flexilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834165]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23108	Pinus flexilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4971	Alnus firma	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15361	Alnus japonica	Species	Betulaceae	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
EC50	1
IC50	2
Others	6

Activity Type	# Activity
Cell Line	3
Individual Protein	1
NON-MOLECULAR	2
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT182	Individual Protein	Protein kinase C alpha	Homo sapiens	IC50	=	8.6	ug.mL-1	PMID[490386]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	46.2	%	PMID[490389]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	78.2	%	PMID[490389]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	89.7	%	PMID[490389]
NPT742	Organism	Influenza A virus	Influenza A virus	EC50	>	350000.0	nM	PMID[490387]
NPT27	Others	Unspecified		CC50	>	500000.0	nM	PMID[490387]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[490388]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	22.7	%	PMID[490388]
NPT2	Others	Unspecified		Survival	>	50.0	%	PMID[490390]

☑ 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 NPC103398 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	313
0.1-0.2	1200
0.2-0.3	2815
0.3-0.4	7361
0.4-0.5	11184
0.5-0.6	6064
0.6-0.7	9359
0.7-0.8	4083
0.8-0.85	273
0.85-0.9	25
0.9-0.95	16
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC180171
1.0	High Similarity	NPC158325
0.9688	High Similarity	NPC476407
0.9453	High Similarity	NPC158673
0.9394	High Similarity	NPC123988
0.9308	High Similarity	NPC469705
0.9308	High Similarity	NPC470122
0.9308	High Similarity	NPC17968
0.9254	High Similarity	NPC310252
0.9254	High Similarity	NPC84789
0.9254	High Similarity	NPC302583
0.9254	High Similarity	NPC100558
0.9167	High Similarity	NPC471066
0.9167	High Similarity	NPC471095
0.9147	High Similarity	NPC94179
0.9143	High Similarity	NPC473138
0.9143	High Similarity	NPC28776
0.9098	High Similarity	NPC164172
0.9077	High Similarity	NPC264900
0.9077	High Similarity	NPC231607
0.9077	High Similarity	NPC79715
0.9077	High Similarity	NPC108659
0.8939	High Similarity	NPC184092
0.8873	High Similarity	NPC116229
0.8864	High Similarity	NPC148982
0.8832	High Similarity	NPC469696
0.876	High Similarity	NPC266045
0.875	High Similarity	NPC287597
0.875	High Similarity	NPC34634
0.875	High Similarity	NPC34293
0.875	High Similarity	NPC265454
0.875	High Similarity	NPC886
0.8741	High Similarity	NPC254275
0.8707	High Similarity	NPC131532
0.8699	High Similarity	NPC87403
0.8682	High Similarity	NPC98305
0.8636	High Similarity	NPC90318
0.863	High Similarity	NPC106818
0.8621	High Similarity	NPC12006
0.8601	High Similarity	NPC474465
0.8561	High Similarity	NPC78363
0.8561	High Similarity	NPC260425
0.855	High Similarity	NPC86900
0.8538	High Similarity	NPC160854
0.8538	High Similarity	NPC469704
0.8538	High Similarity	NPC201402
0.8538	High Similarity	NPC469703
0.8523	High Similarity	NPC478055
0.85	High Similarity	NPC197316
0.85	High Similarity	NPC321184
0.85	High Similarity	NPC220942
0.85	High Similarity	NPC328273
0.85	High Similarity	NPC476383
0.85	High Similarity	NPC472350
0.85	High Similarity	NPC89105
0.85	High Similarity	NPC68092
0.85	High Similarity	NPC64141
0.85	High Similarity	NPC81515
0.85	High Similarity	NPC205195
0.85	High Similarity	NPC321638
0.85	High Similarity	NPC171134
0.8489	Intermediate Similarity	NPC199459
0.8489	Intermediate Similarity	NPC470572
0.8489	Intermediate Similarity	NPC177035
0.8489	Intermediate Similarity	NPC52277
0.8478	Intermediate Similarity	NPC106406
0.8473	Intermediate Similarity	NPC472271
0.8473	Intermediate Similarity	NPC469686
0.8451	Intermediate Similarity	NPC148080
0.8451	Intermediate Similarity	NPC296643
0.8451	Intermediate Similarity	NPC469623
0.8446	Intermediate Similarity	NPC245615
0.8446	Intermediate Similarity	NPC115466
0.8446	Intermediate Similarity	NPC61604
0.8446	Intermediate Similarity	NPC299706
0.8435	Intermediate Similarity	NPC140151
0.8425	Intermediate Similarity	NPC478242
0.8417	Intermediate Similarity	NPC476870
0.8409	Intermediate Similarity	NPC471067
0.8382	Intermediate Similarity	NPC477294
0.8382	Intermediate Similarity	NPC229784
0.8382	Intermediate Similarity	NPC469549
0.8382	Intermediate Similarity	NPC477293
0.838	Intermediate Similarity	NPC134405
0.838	Intermediate Similarity	NPC47471
0.838	Intermediate Similarity	NPC476385
0.838	Intermediate Similarity	NPC476377
0.8366	Intermediate Similarity	NPC127782
0.8366	Intermediate Similarity	NPC300537
0.8357	Intermediate Similarity	NPC471345
0.8355	Intermediate Similarity	NPC44507
0.8346	Intermediate Similarity	NPC232454
0.8346	Intermediate Similarity	NPC178449
0.8346	Intermediate Similarity	NPC470907
0.8344	Intermediate Similarity	NPC40920
0.8344	Intermediate Similarity	NPC223335
0.8333	Intermediate Similarity	NPC183824
0.8333	Intermediate Similarity	NPC38699
0.8333	Intermediate Similarity	NPC473285
0.8322	Intermediate Similarity	NPC157898
0.8322	Intermediate Similarity	NPC140502
0.8322	Intermediate Similarity	NPC265648
0.8322	Intermediate Similarity	NPC222433
0.8321	Intermediate Similarity	NPC311419
0.8321	Intermediate Similarity	NPC123196
0.8321	Intermediate Similarity	NPC215941
0.8321	Intermediate Similarity	NPC319282
0.8321	Intermediate Similarity	NPC65935
0.8321	Intermediate Similarity	NPC275724
0.8321	Intermediate Similarity	NPC244246
0.8321	Intermediate Similarity	NPC137427
0.8312	Intermediate Similarity	NPC29830
0.8312	Intermediate Similarity	NPC147596
0.831	Intermediate Similarity	NPC156709
0.831	Intermediate Similarity	NPC106944
0.831	Intermediate Similarity	NPC179505
0.831	Intermediate Similarity	NPC475530
0.831	Intermediate Similarity	NPC473799
0.8309	Intermediate Similarity	NPC232880
0.8299	Intermediate Similarity	NPC92117
0.8298	Intermediate Similarity	NPC279676
0.8298	Intermediate Similarity	NPC470413
0.8298	Intermediate Similarity	NPC67349
0.8298	Intermediate Similarity	NPC138738
0.8298	Intermediate Similarity	NPC308976
0.8289	Intermediate Similarity	NPC469654
0.8286	Intermediate Similarity	NPC311742
0.8284	Intermediate Similarity	NPC85565
0.8278	Intermediate Similarity	NPC163635
0.8278	Intermediate Similarity	NPC471405
0.8264	Intermediate Similarity	NPC119537
0.8264	Intermediate Similarity	NPC112
0.8264	Intermediate Similarity	NPC476384
0.8264	Intermediate Similarity	NPC269141
0.8264	Intermediate Similarity	NPC298257
0.8264	Intermediate Similarity	NPC96795
0.8264	Intermediate Similarity	NPC247032
0.8264	Intermediate Similarity	NPC264632
0.8264	Intermediate Similarity	NPC476378
0.8264	Intermediate Similarity	NPC76406
0.8264	Intermediate Similarity	NPC476375
0.8264	Intermediate Similarity	NPC205864
0.8264	Intermediate Similarity	NPC40305
0.8264	Intermediate Similarity	NPC476397
0.8264	Intermediate Similarity	NPC105005
0.8264	Intermediate Similarity	NPC285550
0.8264	Intermediate Similarity	NPC476381
0.8264	Intermediate Similarity	NPC175214
0.8264	Intermediate Similarity	NPC476380
0.8261	Intermediate Similarity	NPC65942
0.8261	Intermediate Similarity	NPC219677
0.8261	Intermediate Similarity	NPC248307
0.8258	Intermediate Similarity	NPC165720
0.8252	Intermediate Similarity	NPC472711
0.8252	Intermediate Similarity	NPC186406
0.8252	Intermediate Similarity	NPC469661
0.8247	Intermediate Similarity	NPC56735
0.8247	Intermediate Similarity	NPC471873
0.8247	Intermediate Similarity	NPC189142
0.8247	Intermediate Similarity	NPC77660
0.8247	Intermediate Similarity	NPC61594
0.8244	Intermediate Similarity	NPC109371
0.8244	Intermediate Similarity	NPC470214
0.8244	Intermediate Similarity	NPC70084
0.8244	Intermediate Similarity	NPC470215
0.8243	Intermediate Similarity	NPC229882
0.8243	Intermediate Similarity	NPC158635
0.8239	Intermediate Similarity	NPC324262
0.8239	Intermediate Similarity	NPC62800
0.8235	Intermediate Similarity	NPC476873
0.8235	Intermediate Similarity	NPC288416
0.8231	Intermediate Similarity	NPC120621
0.8231	Intermediate Similarity	NPC248257
0.8222	Intermediate Similarity	NPC123704
0.8219	Intermediate Similarity	NPC473867
0.8214	Intermediate Similarity	NPC35731
0.8214	Intermediate Similarity	NPC476411
0.8212	Intermediate Similarity	NPC10205
0.8212	Intermediate Similarity	NPC186316
0.8207	Intermediate Similarity	NPC196063
0.8207	Intermediate Similarity	NPC64195
0.8207	Intermediate Similarity	NPC300894
0.8207	Intermediate Similarity	NPC141455
0.8207	Intermediate Similarity	NPC296954
0.8205	Intermediate Similarity	NPC5778
0.8205	Intermediate Similarity	NPC236934
0.8201	Intermediate Similarity	NPC18074
0.8201	Intermediate Similarity	NPC473924
0.8201	Intermediate Similarity	NPC25581
0.8201	Intermediate Similarity	NPC61
0.8201	Intermediate Similarity	NPC5419
0.8194	Intermediate Similarity	NPC48309
0.8194	Intermediate Similarity	NPC52664
0.8194	Intermediate Similarity	NPC191306
0.8194	Intermediate Similarity	NPC168822
0.8194	Intermediate Similarity	NPC189115
0.8194	Intermediate Similarity	NPC88043
0.8194	Intermediate Similarity	NPC19709
0.8194	Intermediate Similarity	NPC270335
0.8182	Intermediate Similarity	NPC471869

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 NPC103398 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	267
0.1-0.2	761
0.2-0.3	1509
0.3-0.4	2841
0.4-0.5	2085
0.5-0.6	1178
0.6-0.7	453
0.7-0.8	54
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.85	High Similarity	NPD7266	Discontinued
0.805	Intermediate Similarity	NPD7074	Phase 3
0.8038	Intermediate Similarity	NPD3818	Discontinued
0.8014	Intermediate Similarity	NPD6190	Approved
0.7987	Intermediate Similarity	NPD7054	Approved
0.7937	Intermediate Similarity	NPD7472	Approved
0.7888	Intermediate Similarity	NPD6797	Phase 2
0.7871	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7251	Discontinued
0.7791	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1934	Approved
0.7707	Intermediate Similarity	NPD6234	Discontinued
0.7702	Intermediate Similarity	NPD7228	Approved
0.7683	Intermediate Similarity	NPD7808	Phase 3
0.7677	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD37	Approved
0.7606	Intermediate Similarity	NPD3027	Phase 3
0.758	Intermediate Similarity	NPD4967	Phase 2
0.758	Intermediate Similarity	NPD4966	Approved
0.758	Intermediate Similarity	NPD4965	Approved
0.7578	Intermediate Similarity	NPD6166	Phase 2
0.7578	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1613	Approved
0.755	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6559	Discontinued
0.7484	Intermediate Similarity	NPD4380	Phase 2
0.7481	Intermediate Similarity	NPD3022	Approved
0.7481	Intermediate Similarity	NPD3021	Approved
0.7468	Intermediate Similarity	NPD1653	Approved
0.7468	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD8455	Phase 2
0.7448	Intermediate Similarity	NPD943	Approved
0.7439	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7685	Pre-registration
0.7351	Intermediate Similarity	NPD8166	Discontinued
0.7342	Intermediate Similarity	NPD2801	Approved
0.732	Intermediate Similarity	NPD1511	Approved
0.7315	Intermediate Similarity	NPD9570	Approved
0.7305	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7199	Phase 2
0.7239	Intermediate Similarity	NPD3787	Discontinued
0.7235	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1512	Approved
0.7222	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8312	Approved
0.7219	Intermediate Similarity	NPD8313	Approved
0.7211	Intermediate Similarity	NPD825	Approved
0.7211	Intermediate Similarity	NPD826	Approved
0.7202	Intermediate Similarity	NPD7240	Approved
0.7188	Intermediate Similarity	NPD3817	Phase 2
0.7181	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6674	Discontinued
0.7163	Intermediate Similarity	NPD1091	Approved
0.7162	Intermediate Similarity	NPD230	Phase 1
0.7161	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD3882	Suspended
0.7143	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7075	Discontinued
0.7091	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6798	Discontinued
0.7066	Intermediate Similarity	NPD3751	Discontinued
0.7039	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6663	Approved
0.7021	Intermediate Similarity	NPD2932	Approved
0.7021	Intermediate Similarity	NPD3019	Approved
0.7013	Intermediate Similarity	NPD4628	Phase 3
0.7013	Intermediate Similarity	NPD3400	Discontinued
0.6993	Remote Similarity	NPD1549	Phase 2
0.6986	Remote Similarity	NPD5736	Approved
0.6981	Remote Similarity	NPD3455	Phase 2
0.6975	Remote Similarity	NPD5402	Approved
0.6974	Remote Similarity	NPD2935	Discontinued
0.6966	Remote Similarity	NPD3094	Phase 2
0.6957	Remote Similarity	NPD2629	Approved
0.695	Remote Similarity	NPD1357	Approved
0.6933	Remote Similarity	NPD6355	Discontinued
0.6933	Remote Similarity	NPD555	Phase 2
0.6928	Remote Similarity	NPD6232	Discontinued
0.6923	Remote Similarity	NPD3705	Approved
0.6923	Remote Similarity	NPD1201	Approved
0.6918	Remote Similarity	NPD257	Approved
0.6918	Remote Similarity	NPD258	Approved
0.6914	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1510	Phase 2
0.6908	Remote Similarity	NPD7033	Discontinued
0.6908	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7473	Discontinued
0.6903	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4110	Phase 3
0.6901	Remote Similarity	NPD5126	Approved
0.6901	Remote Similarity	NPD5125	Phase 3
0.6889	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD9269	Phase 2
0.6871	Remote Similarity	NPD2861	Phase 2
0.6867	Remote Similarity	NPD3062	Approved
0.6867	Remote Similarity	NPD3061	Approved
0.6867	Remote Similarity	NPD3059	Approved
0.6861	Remote Similarity	NPD228	Approved
0.6855	Remote Similarity	NPD5403	Approved
0.6854	Remote Similarity	NPD6534	Approved
0.6854	Remote Similarity	NPD6535	Approved
0.6852	Remote Similarity	NPD6801	Discontinued
0.6849	Remote Similarity	NPD1470	Approved
0.6846	Remote Similarity	NPD3764	Approved
0.6842	Remote Similarity	NPD7097	Phase 1
0.6835	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7028	Phase 2
0.6831	Remote Similarity	NPD7680	Approved
0.6824	Remote Similarity	NPD5844	Phase 1
0.6822	Remote Similarity	NPD2859	Approved
0.6822	Remote Similarity	NPD2860	Approved
0.6821	Remote Similarity	NPD1933	Approved
0.6815	Remote Similarity	NPD5058	Phase 3
0.681	Remote Similarity	NPD7819	Suspended
0.681	Remote Similarity	NPD1465	Phase 2
0.6809	Remote Similarity	NPD5536	Phase 2
0.6807	Remote Similarity	NPD5494	Approved
0.6806	Remote Similarity	NPD3092	Approved
0.68	Remote Similarity	NPD4062	Phase 3
0.68	Remote Similarity	NPD259	Phase 1
0.6798	Remote Similarity	NPD6212	Phase 3
0.6798	Remote Similarity	NPD6213	Phase 3
0.6798	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3020	Approved
0.6791	Remote Similarity	NPD5048	Discontinued
0.6783	Remote Similarity	NPD9381	Approved
0.6783	Remote Similarity	NPD9384	Approved
0.6782	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD7095	Approved
0.6776	Remote Similarity	NPD5314	Approved
0.6768	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5283	Phase 1
0.6758	Remote Similarity	NPD6778	Approved
0.6758	Remote Similarity	NPD6776	Approved
0.6758	Remote Similarity	NPD6781	Approved
0.6758	Remote Similarity	NPD6780	Approved
0.6758	Remote Similarity	NPD6782	Approved
0.6758	Remote Similarity	NPD6777	Approved
0.6758	Remote Similarity	NPD6779	Approved
0.6757	Remote Similarity	NPD9569	Approved
0.6757	Remote Similarity	NPD9494	Approved
0.6755	Remote Similarity	NPD3620	Phase 2
0.6755	Remote Similarity	NPD4060	Phase 1
0.6755	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5408	Approved
0.6753	Remote Similarity	NPD5406	Approved
0.6753	Remote Similarity	NPD2438	Suspended
0.6753	Remote Similarity	NPD5404	Approved
0.6753	Remote Similarity	NPD5405	Approved
0.6744	Remote Similarity	NPD2934	Approved
0.6744	Remote Similarity	NPD2933	Approved
0.674	Remote Similarity	NPD7700	Phase 2
0.674	Remote Similarity	NPD7699	Phase 2
0.6733	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5401	Approved
0.6707	Remote Similarity	NPD2977	Approved
0.6707	Remote Similarity	NPD2978	Approved
0.6705	Remote Similarity	NPD8150	Discontinued
0.669	Remote Similarity	NPD1535	Discovery
0.6689	Remote Similarity	NPD2798	Approved
0.6689	Remote Similarity	NPD5647	Approved
0.6688	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7411	Suspended
0.6685	Remote Similarity	NPD6823	Phase 2
0.6667	Remote Similarity	NPD7390	Discontinued
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD8127	Discontinued
0.6667	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD6799	Approved
0.6667	Remote Similarity	NPD6653	Approved
0.6649	Remote Similarity	NPD7435	Discontinued
0.6645	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1240	Approved
0.6645	Remote Similarity	NPD2796	Approved
0.6644	Remote Similarity	NPD1481	Phase 2
0.6644	Remote Similarity	NPD1608	Approved
0.6643	Remote Similarity	NPD3091	Approved
0.6643	Remote Similarity	NPD9545	Approved
0.6643	Remote Similarity	NPD1894	Discontinued
0.6625	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4536	Approved
0.6623	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4538	Approved
0.6622	Remote Similarity	NPD1164	Approved
0.6621	Remote Similarity	NPD3026	Approved
0.6621	Remote Similarity	NPD3023	Approved
0.6617	Remote Similarity	NPD1242	Phase 1

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