NPASS Compound

Structure

CID235294 OpenBabel06191716032D 42 45 0 0 1 0 0 0 0 0999 V2000 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -4.5000 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 -6.0622 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 -6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -2.5000 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 3.5000 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 -4.0000 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 -8.6603 -3.0000 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 -3.4641 -1.0000 0.0000 C 0 0 2 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 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 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 -1.7321 -0.0000 0.0000 C 0 0 2 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 -2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5263 -2.5000 0.0000 O 0 0 0 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 -6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 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 -3.4641 -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 2 7 1 0 0 0 0 2 16 2 0 0 0 0 3 8 2 0 0 0 0 3 16 1 0 0 0 0 4 9 1 0 0 0 0 4 17 2 0 0 0 0 5 10 2 0 0 0 0 5 17 1 0 0 0 0 6 11 2 0 0 0 0 6 16 1 0 0 0 0 7 18 2 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 38 1 0 0 0 0 14 39 1 0 0 0 0 15 1 1 1 0 0 0 15 22 1 0 0 0 0 15 40 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 14 1 1 0 0 0 20 23 1 0 0 0 0 20 41 1 0 0 0 0 21 32 2 0 0 0 0 21 39 1 0 0 0 0 22 24 1 0 0 0 0 22 33 1 6 0 0 0 23 27 1 0 0 0 0 23 34 1 6 0 0 0 24 25 1 0 0 0 0 24 35 1 1 0 0 0 25 29 1 0 0 0 0 25 36 1 1 0 0 0 26 27 1 0 0 0 0 26 28 1 0 0 0 0 26 37 1 6 0 0 0 27 42 1 1 0 0 0 28 38 1 1 0 0 0 28 41 1 0 0 0 0 29 40 1 0 0 0 0 29 42 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	592.22
Volume:	569.095
LogP:	1.651
LogD:	0.733
LogS:	-2.896
# Rotatable Bonds:	11
TPSA:	204.83
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.138
Synthetic Accessibility Score:	4.515
Fsp3:	0.483
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.381
MDCK Permeability:	3.21312400046736e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.953
20% Bioavailability (F20%):	0.776
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	93.2682113647461%
Volume Distribution (VD):	0.287
Pgp-substrate:	5.786600589752197%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	0.167
CYP2C19-substrate:	0.078
CYP2C9-inhibitor:	0.233
CYP2C9-substrate:	0.838
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.213
CYP3A4-inhibitor:	0.056
CYP3A4-substrate:	0.044

ADMET: Excretion

Clearance (CL):	0.807
Half-life (T1/2):	0.71

ADMET: Toxicity

hERG Blockers:	0.416
Human Hepatotoxicity (H-HT):	0.082
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.309
Rat Oral Acute Toxicity:	0.283
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.963
Carcinogencity:	0.115
Eye Corrosion:	0.003
Eye Irritation:	0.062
Respiratory Toxicity:	0.034

Download Data

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

Natural Product: NPC235294

Natural Product ID:	NPC235294
*Common Name:**	Osmanthuside B6
IUPAC Name:	[(2R,3R,4S,5R,6R)-3,5-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:	Osmanthuside B6
Standard InCHIKey:	NACKALNITXFLJE-KWZXHGFLSA-N
Standard InCHI:	InChI=1S/C29H36O13/c1-15-22(33)24(35)25(36)29(40-15)42-27-23(34)20(14-39-21(32)11-6-16-2-7-18(30)8-3-16)41-28(26(27)37)38-13-12-17-4-9-19(31)10-5-17/h2-11,15,20,22-31,33-37H,12-14H2,1H3/b11-6+/t15-,20+,22-,23+,24+,25+,26+,27-,28+,29-/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1[C@@H]([C@@H](COC(=O)/C=C/c2ccc(cc2)O)O[C@H]([C@@H]1O)OCCc1ccc(cc1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449440
PubChem CID:	10054173
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

*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
NPO2726	Ligustrum robustum	Species	Oleaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828473]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25900014]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2726	Ligustrum robustum	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	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	1

Activity Type	# Activity
NON-MOLECULAR	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	=	91700.0	nM	PMID[473160]

☑ 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 NPC235294 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	261
0.1-0.2	1157
0.2-0.3	2898
0.3-0.4	7210
0.4-0.5	10490
0.5-0.6	8633
0.6-0.7	9299
0.7-0.8	2404
0.8-0.85	203
0.85-0.9	93
0.9-0.95	44
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC46137
0.984	High Similarity	NPC246869
0.984	High Similarity	NPC225384
0.984	High Similarity	NPC138777
0.9688	High Similarity	NPC263829
0.9677	High Similarity	NPC288416
0.9528	High Similarity	NPC478255
0.952	High Similarity	NPC106677
0.9466	High Similarity	NPC472350
0.9466	High Similarity	NPC64141
0.9466	High Similarity	NPC81515
0.9466	High Similarity	NPC68092
0.9466	High Similarity	NPC476383
0.9466	High Similarity	NPC89105
0.9466	High Similarity	NPC197316
0.9444	High Similarity	NPC225307
0.944	High Similarity	NPC471157
0.9389	High Similarity	NPC260425
0.936	High Similarity	NPC83218
0.936	High Similarity	NPC126991
0.9323	High Similarity	NPC47471
0.9323	High Similarity	NPC134405
0.9323	High Similarity	NPC476377
0.9323	High Similarity	NPC476385
0.9318	High Similarity	NPC205195
0.9274	High Similarity	NPC52097
0.9254	High Similarity	NPC222433
0.9254	High Similarity	NPC265648
0.9248	High Similarity	NPC475530
0.9248	High Similarity	NPC473799
0.9242	High Similarity	NPC78363
0.9231	High Similarity	NPC28637
0.9213	High Similarity	NPC471882
0.9213	High Similarity	NPC156692
0.9213	High Similarity	NPC173150
0.9213	High Similarity	NPC35288
0.9213	High Similarity	NPC45224
0.9213	High Similarity	NPC471881
0.9194	High Similarity	NPC11724
0.9185	High Similarity	NPC96795
0.9185	High Similarity	NPC476378
0.9185	High Similarity	NPC264632
0.9185	High Similarity	NPC476397
0.9185	High Similarity	NPC269141
0.9185	High Similarity	NPC476375
0.9185	High Similarity	NPC76406
0.9185	High Similarity	NPC112
0.9185	High Similarity	NPC476381
0.9185	High Similarity	NPC298257
0.9185	High Similarity	NPC175214
0.9185	High Similarity	NPC119537
0.9185	High Similarity	NPC247032
0.9185	High Similarity	NPC476380
0.9185	High Similarity	NPC476384
0.9185	High Similarity	NPC205864
0.916	High Similarity	NPC886
0.916	High Similarity	NPC34293
0.916	High Similarity	NPC287597
0.9134	High Similarity	NPC61181
0.9134	High Similarity	NPC252114
0.9118	High Similarity	NPC196063
0.9118	High Similarity	NPC64195
0.9118	High Similarity	NPC296954
0.9118	High Similarity	NPC300894
0.9118	High Similarity	NPC141455
0.9113	High Similarity	NPC476872
0.9098	High Similarity	NPC65262
0.9098	High Similarity	NPC101686
0.9098	High Similarity	NPC476376
0.9098	High Similarity	NPC469364
0.9062	High Similarity	NPC103533
0.9051	High Similarity	NPC100998
0.9051	High Similarity	NPC34587
0.9051	High Similarity	NPC34927
0.9051	High Similarity	NPC476382
0.9051	High Similarity	NPC252292
0.9044	High Similarity	NPC105005
0.904	High Similarity	NPC55608
0.903	High Similarity	NPC328273
0.903	High Similarity	NPC171134
0.903	High Similarity	NPC321638
0.903	High Similarity	NPC321184
0.9023	High Similarity	NPC471345
0.9015	High Similarity	NPC169398
0.9008	High Similarity	NPC473285
0.8986	High Similarity	NPC229505
0.896	High Similarity	NPC201402
0.896	High Similarity	NPC469703
0.896	High Similarity	NPC160854
0.896	High Similarity	NPC469704
0.8947	High Similarity	NPC476870
0.8923	High Similarity	NPC253595
0.8921	High Similarity	NPC232992
0.8905	High Similarity	NPC204644
0.8889	High Similarity	NPC469686
0.8881	High Similarity	NPC166180
0.8832	High Similarity	NPC140502
0.8819	High Similarity	NPC471067
0.8794	High Similarity	NPC473427
0.8794	High Similarity	NPC259347
0.8794	High Similarity	NPC306890
0.8794	High Similarity	NPC476386
0.8794	High Similarity	NPC94871
0.8794	High Similarity	NPC471062
0.8794	High Similarity	NPC470933
0.8794	High Similarity	NPC476398
0.8788	High Similarity	NPC281798
0.8788	High Similarity	NPC254819
0.8779	High Similarity	NPC229784
0.8779	High Similarity	NPC477294
0.8779	High Similarity	NPC477293
0.8768	High Similarity	NPC478250
0.8768	High Similarity	NPC40305
0.875	High Similarity	NPC232454
0.875	High Similarity	NPC470907
0.875	High Similarity	NPC178449
0.8741	High Similarity	NPC472132
0.8732	High Similarity	NPC470934
0.8732	High Similarity	NPC257970
0.8732	High Similarity	NPC470927
0.8732	High Similarity	NPC188393
0.8731	High Similarity	NPC471883
0.873	High Similarity	NPC469702
0.873	High Similarity	NPC282409
0.8722	High Similarity	NPC254275
0.8714	High Similarity	NPC476865
0.871	High Similarity	NPC148055
0.8705	High Similarity	NPC471028
0.8705	High Similarity	NPC476867
0.8702	High Similarity	NPC232880
0.8696	High Similarity	NPC148080
0.8696	High Similarity	NPC469623
0.8661	High Similarity	NPC476445
0.8661	High Similarity	NPC469548
0.8661	High Similarity	NPC476448
0.8657	High Similarity	NPC254398
0.8652	High Similarity	NPC97240
0.8647	High Similarity	NPC219677
0.8643	High Similarity	NPC476864
0.8643	High Similarity	NPC476869
0.8643	High Similarity	NPC476866
0.8643	High Similarity	NPC226722
0.8643	High Similarity	NPC476868
0.8636	High Similarity	NPC469549
0.8636	High Similarity	NPC184092
0.8636	High Similarity	NPC295970
0.8633	High Similarity	NPC478239
0.8633	High Similarity	NPC293154
0.8626	High Similarity	NPC476873
0.8623	High Similarity	NPC186406
0.8613	High Similarity	NPC49597
0.8611	High Similarity	NPC106818
0.8601	High Similarity	NPC182350
0.8582	High Similarity	NPC473924
0.8582	High Similarity	NPC212808
0.8571	High Similarity	NPC184464
0.8571	High Similarity	NPC251062
0.8571	High Similarity	NPC469705
0.8571	High Similarity	NPC470122
0.8571	High Similarity	NPC110063
0.8571	High Similarity	NPC296659
0.8571	High Similarity	NPC17968
0.8571	High Similarity	NPC202391
0.8561	High Similarity	NPC145319
0.8561	High Similarity	NPC296643
0.8561	High Similarity	NPC157816
0.856	High Similarity	NPC175771
0.8552	High Similarity	NPC87403
0.8548	High Similarity	NPC157338
0.8548	High Similarity	NPC313193
0.8531	High Similarity	NPC106138
0.8527	High Similarity	NPC476142
0.8521	High Similarity	NPC175275
0.8519	High Similarity	NPC114116
0.8516	High Similarity	NPC229600
0.8511	High Similarity	NPC287615
0.8511	High Similarity	NPC83743
0.8511	High Similarity	NPC216819
0.8511	High Similarity	NPC138915
0.8511	High Similarity	NPC262182
0.85	High Similarity	NPC469367
0.8485	Intermediate Similarity	NPC469687
0.8485	Intermediate Similarity	NPC108659
0.8485	Intermediate Similarity	NPC79715
0.8485	Intermediate Similarity	NPC264900
0.8485	Intermediate Similarity	NPC231607
0.8483	Intermediate Similarity	NPC478268
0.8478	Intermediate Similarity	NPC31745
0.8478	Intermediate Similarity	NPC220936
0.8467	Intermediate Similarity	NPC157554
0.8462	Intermediate Similarity	NPC473138
0.8462	Intermediate Similarity	NPC3460
0.8462	Intermediate Similarity	NPC300262
0.8462	Intermediate Similarity	NPC28776
0.8462	Intermediate Similarity	NPC210611
0.8462	Intermediate Similarity	NPC28651
0.8462	Intermediate Similarity	NPC192763
0.8462	Intermediate Similarity	NPC261122
0.8462	Intermediate Similarity	NPC23677
0.8462	Intermediate Similarity	NPC220282

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 NPC235294 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	747
0.2-0.3	1478
0.3-0.4	2849
0.4-0.5	2154
0.5-0.6	1307
0.6-0.7	359
0.7-0.8	29
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9466	High Similarity	NPD7266	Discontinued
0.7785	Intermediate Similarity	NPD1653	Approved
0.7763	Intermediate Similarity	NPD8455	Phase 2
0.7761	Intermediate Similarity	NPD1091	Approved
0.774	Intermediate Similarity	NPD6190	Approved
0.7727	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD7097	Phase 1
0.7485	Intermediate Similarity	NPD7685	Pre-registration
0.7469	Intermediate Similarity	NPD7472	Approved
0.7469	Intermediate Similarity	NPD7074	Phase 3
0.7453	Intermediate Similarity	NPD7228	Approved
0.7432	Intermediate Similarity	NPD4628	Phase 3
0.7378	Intermediate Similarity	NPD7251	Discontinued
0.7365	Intermediate Similarity	NPD1652	Phase 2
0.7361	Intermediate Similarity	NPD4340	Discontinued
0.7353	Intermediate Similarity	NPD5126	Approved
0.7353	Intermediate Similarity	NPD5125	Phase 3
0.7343	Intermediate Similarity	NPD6233	Phase 2
0.7338	Intermediate Similarity	NPD4380	Phase 2
0.7333	Intermediate Similarity	NPD7808	Phase 3
0.7333	Intermediate Similarity	NPD9545	Approved
0.7328	Intermediate Similarity	NPD969	Suspended
0.7324	Intermediate Similarity	NPD3027	Phase 3
0.7317	Intermediate Similarity	NPD6797	Phase 2
0.7289	Intermediate Similarity	NPD8312	Approved
0.7289	Intermediate Similarity	NPD8313	Approved
0.7287	Intermediate Similarity	NPD1358	Approved
0.7285	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7075	Discontinued
0.7273	Intermediate Similarity	NPD6559	Discontinued
0.7241	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5124	Phase 1
0.7229	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5058	Phase 3
0.7215	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1613	Approved
0.7153	Intermediate Similarity	NPD3764	Approved
0.7153	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6798	Discontinued
0.7143	Intermediate Similarity	NPD5403	Approved
0.7143	Intermediate Similarity	NPD7843	Approved
0.7134	Intermediate Similarity	NPD3818	Discontinued
0.7134	Intermediate Similarity	NPD37	Approved
0.7133	Intermediate Similarity	NPD6674	Discontinued
0.7133	Intermediate Similarity	NPD4908	Phase 1
0.7125	Intermediate Similarity	NPD6234	Discontinued
0.7122	Intermediate Similarity	NPD422	Phase 1
0.7107	Intermediate Similarity	NPD4965	Approved
0.7107	Intermediate Similarity	NPD4966	Approved
0.7107	Intermediate Similarity	NPD4967	Phase 2
0.7101	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2933	Approved
0.7097	Intermediate Similarity	NPD2934	Approved
0.7093	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD8166	Discontinued
0.7077	Intermediate Similarity	NPD3134	Approved
0.7066	Intermediate Similarity	NPD7240	Approved
0.7055	Intermediate Similarity	NPD4060	Phase 1
0.7051	Intermediate Similarity	NPD7458	Discontinued
0.704	Intermediate Similarity	NPD2859	Approved
0.704	Intermediate Similarity	NPD2860	Approved
0.7034	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4536	Approved
0.7027	Intermediate Similarity	NPD4538	Approved
0.7027	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6801	Discontinued
0.7021	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5535	Approved
0.7013	Intermediate Similarity	NPD5401	Approved
0.7007	Intermediate Similarity	NPD230	Phase 1
0.7007	Intermediate Similarity	NPD6355	Discontinued
0.6986	Remote Similarity	NPD4062	Phase 3
0.6985	Remote Similarity	NPD7157	Approved
0.698	Remote Similarity	NPD7033	Discontinued
0.6972	Remote Similarity	NPD3225	Approved
0.697	Remote Similarity	NPD2684	Approved
0.6966	Remote Similarity	NPD7095	Approved
0.6962	Remote Similarity	NPD7411	Suspended
0.6957	Remote Similarity	NPD1548	Phase 1
0.6948	Remote Similarity	NPD6799	Approved
0.6944	Remote Similarity	NPD2861	Phase 2
0.6939	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5402	Approved
0.6923	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6166	Phase 2
0.6909	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3536	Discontinued
0.6903	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1610	Phase 2
0.6879	Remote Similarity	NPD3705	Approved
0.6875	Remote Similarity	NPD3020	Approved
0.6867	Remote Similarity	NPD5960	Phase 3
0.6867	Remote Similarity	NPD5588	Approved
0.6863	Remote Similarity	NPD3750	Approved
0.6863	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6653	Approved
0.6842	Remote Similarity	NPD1549	Phase 2
0.6829	Remote Similarity	NPD7199	Phase 2
0.6828	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5736	Approved
0.6821	Remote Similarity	NPD2935	Discontinued
0.6813	Remote Similarity	NPD1934	Approved
0.6812	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3496	Discontinued
0.6809	Remote Similarity	NPD3847	Discontinued
0.6806	Remote Similarity	NPD2797	Approved
0.6806	Remote Similarity	NPD3094	Phase 2
0.6797	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD3021	Approved
0.6791	Remote Similarity	NPD3022	Approved
0.679	Remote Similarity	NPD7768	Phase 2
0.6786	Remote Similarity	NPD1357	Approved
0.6786	Remote Similarity	NPD5844	Phase 1
0.6782	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD6832	Phase 2
0.6779	Remote Similarity	NPD1933	Approved
0.6776	Remote Similarity	NPD5763	Approved
0.6776	Remote Similarity	NPD5762	Approved
0.6776	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7819	Suspended
0.6767	Remote Similarity	NPD290	Approved
0.6761	Remote Similarity	NPD1535	Discovery
0.6758	Remote Similarity	NPD8320	Phase 1
0.6758	Remote Similarity	NPD8319	Approved
0.6752	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4198	Discontinued
0.6738	Remote Similarity	NPD5846	Approved
0.6738	Remote Similarity	NPD6516	Phase 2
0.6736	Remote Similarity	NPD8651	Approved
0.6735	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD2424	Discontinued
0.673	Remote Similarity	NPD3455	Phase 2
0.6728	Remote Similarity	NPD3817	Phase 2
0.6728	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8127	Discontinued
0.6726	Remote Similarity	NPD3751	Discontinued
0.6714	Remote Similarity	NPD1894	Discontinued
0.6713	Remote Similarity	NPD1481	Phase 2
0.6704	Remote Similarity	NPD7700	Phase 2
0.6704	Remote Similarity	NPD7699	Phase 2
0.6703	Remote Similarity	NPD7435	Discontinued
0.6692	Remote Similarity	NPD968	Approved
0.6691	Remote Similarity	NPD9493	Approved
0.6689	Remote Similarity	NPD3268	Approved
0.6688	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6599	Discontinued
0.6667	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4659	Approved
0.6667	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD1465	Phase 2
0.6667	Remote Similarity	NPD7440	Discontinued
0.6649	Remote Similarity	NPD7585	Approved
0.6647	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1510	Phase 2
0.6645	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4108	Discontinued
0.6644	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6663	Approved
0.6643	Remote Similarity	NPD5536	Phase 2
0.6643	Remote Similarity	NPD3092	Approved
0.6642	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD940	Approved
0.6641	Remote Similarity	NPD846	Approved
0.6629	Remote Similarity	NPD6534	Approved
0.6629	Remote Similarity	NPD6535	Approved
0.662	Remote Similarity	NPD4626	Approved
0.6617	Remote Similarity	NPD5048	Discontinued
0.6613	Remote Similarity	NPD8151	Discontinued
0.6612	Remote Similarity	NPD7680	Approved
0.6607	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD1551	Phase 2
0.66	Remote Similarity	NPD4140	Approved
0.66	Remote Similarity	NPD1240	Approved
0.6595	Remote Similarity	NPD7583	Approved
0.6591	Remote Similarity	NPD6647	Phase 2
0.6588	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD3787	Discontinued
0.6582	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4103	Phase 2
0.6575	Remote Similarity	NPD1203	Approved
0.6575	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6362	Approved
0.6569	Remote Similarity	NPD228	Approved
0.6565	Remote Similarity	NPD3028	Approved
0.6565	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