NPASS Compound

Structure

NPC291228 OpenBabel07101718292D 47 48 0 0 1 0 0 0 0 0999 V2000 -0.2782 11.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5160 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6500 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9271 4.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7202 5.0064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -2.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2782 10.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 9.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 8.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 8.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 7.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 6.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 5.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0519 3.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 -0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7839 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 3.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6500 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0511 4.2633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 -0.6910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0519 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0519 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0519 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1859 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3198 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3198 -2.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6736 0.1280 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2782 -0.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9179 2.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9179 -0.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 1.8968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9179 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 -0.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 2.3090 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 1.4538 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 27 1 0 0 0 0 17 35 1 0 0 0 0 18 36 1 0 0 0 0 19 22 1 0 0 0 0 19 41 1 0 0 0 0 20 23 1 0 0 0 0 20 42 1 0 0 0 0 21 43 1 0 0 0 0 24 37 2 0 0 0 0 24 43 1 0 0 0 0 25 17 1 1 0 0 0 25 28 1 0 0 0 0 25 44 1 0 0 0 0 26 18 1 6 0 0 0 26 29 1 0 0 0 0 26 46 1 0 0 0 0 27 38 2 0 0 0 0 27 45 1 0 0 0 0 28 30 1 0 0 0 0 28 39 1 6 0 0 0 29 32 1 0 0 0 0 29 40 1 1 0 0 0 30 31 1 0 0 0 0 30 41 1 1 0 0 0 31 33 1 0 0 0 0 31 45 1 6 0 0 0 32 34 1 6 0 0 0 32 42 1 0 0 0 0 33 44 1 0 0 0 0 33 47 1 6 0 0 0 34 21 1 1 0 0 0 34 46 1 0 0 0 0 34 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	678.42
Volume:	688.507
LogP:	4.671
LogD:	3.549
LogS:	-4.476
# Rotatable Bonds:	25
TPSA:	179.67
# H-Bond Aceptor:	13
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.092
Synthetic Accessibility Score:	4.914
Fsp3:	0.941
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.091
MDCK Permeability:	3.70871857739985e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.977
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.204

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	95.93982696533203%
Volume Distribution (VD):	0.842
Pgp-substrate:	3.8685121536254883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.132
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.022
CYP3A4-inhibitor:	0.091
CYP3A4-substrate:	0.068

ADMET: Excretion

Clearance (CL):	2.91
Half-life (T1/2):	0.673

ADMET: Toxicity

hERG Blockers:	0.702
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.643
AMES Toxicity:	0.444
Rat Oral Acute Toxicity:	0.109
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.921
Carcinogencity:	0.078
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC291228

Natural Product ID:	NPC291228
*Common Name:**	Physordinose A
IUPAC Name:	[(2R,3R,4S,5R,6R)-2-[(2S,3S,4R,5R)-2-(acetyloxymethyl)-4-hydroxy-5-(hydroxymethyl)-3-(2-methylpropoxy)oxolan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-(2-methylpropoxy)oxan-3-yl] dodecanoate
Synonyms:	Physordinose A
Standard InCHIKey:	VCEVJQODZQDDCZ-GJNRDOBYSA-N
Standard InCHI:	InChI=1S/C34H62O13/c1-7-8-9-10-11-12-13-14-15-16-27(38)45-31-30(41-19-22(2)3)28(39)25(17-35)44-33(31)47-34(21-43-24(6)37)32(42-20-23(4)5)29(40)26(18-36)46-34/h22-23,25-26,28-33,35-36,39-40H,7-21H2,1-6H3/t25-,26-,28-,29-,30+,31-,32+,33-,34+/m1/s1
SMILES:	CCCCCCCCCCCC(=O)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@@H]1O[C@@]1(COC(=O)C)[C@H]([C@@H]([C@@H](CO)O1)O)OCC(C)C)O)OCC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1171815
PubChem CID:	46872008
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

*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
NPO23525	Physalis sordida	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20575572]
NPO23525	Physalis sordida	Species	Solanaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	260.0	nM	PMID[449323]

☑ 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 NPC291228 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	513
0.1-0.2	4266
0.2-0.3	13060
0.3-0.4	11056
0.4-0.5	7814
0.5-0.6	5011
0.6-0.7	798
0.7-0.8	164
0.8-0.85	8
0.85-0.9	2
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC308096
0.9851	High Similarity	NPC184550
0.9851	High Similarity	NPC185419
0.9254	High Similarity	NPC206601
0.8986	High Similarity	NPC241265
0.8986	High Similarity	NPC211428
0.8986	High Similarity	NPC285003
0.8873	High Similarity	NPC206823
0.8841	High Similarity	NPC97736
0.8841	High Similarity	NPC50228
0.8667	High Similarity	NPC477346
0.8667	High Similarity	NPC158302
0.8667	High Similarity	NPC22742
0.8667	High Similarity	NPC85759
0.8667	High Similarity	NPC294748
0.8667	High Similarity	NPC146992
0.8667	High Similarity	NPC477344
0.8657	High Similarity	NPC325773
0.8611	High Similarity	NPC163812
0.8611	High Similarity	NPC39266
0.8611	High Similarity	NPC9763
0.8611	High Similarity	NPC225748
0.8611	High Similarity	NPC169085
0.8553	High Similarity	NPC267592
0.8514	High Similarity	NPC477350
0.8442	Intermediate Similarity	NPC119583
0.8442	Intermediate Similarity	NPC475270
0.8442	Intermediate Similarity	NPC115013
0.8442	Intermediate Similarity	NPC477319
0.8442	Intermediate Similarity	NPC472203
0.8442	Intermediate Similarity	NPC477317
0.8442	Intermediate Similarity	NPC224953
0.8442	Intermediate Similarity	NPC143421
0.8442	Intermediate Similarity	NPC184915
0.8442	Intermediate Similarity	NPC44782
0.8442	Intermediate Similarity	NPC307400
0.8442	Intermediate Similarity	NPC126685
0.8442	Intermediate Similarity	NPC475667
0.8442	Intermediate Similarity	NPC472204
0.8442	Intermediate Similarity	NPC27289
0.8442	Intermediate Similarity	NPC477347
0.8442	Intermediate Similarity	NPC123204
0.8442	Intermediate Similarity	NPC183888
0.8442	Intermediate Similarity	NPC472200
0.8442	Intermediate Similarity	NPC238056
0.8442	Intermediate Similarity	NPC477318
0.8442	Intermediate Similarity	NPC259294
0.8442	Intermediate Similarity	NPC475327
0.8442	Intermediate Similarity	NPC89843
0.8442	Intermediate Similarity	NPC169345
0.8442	Intermediate Similarity	NPC297768
0.8442	Intermediate Similarity	NPC472205
0.8442	Intermediate Similarity	NPC472202
0.8442	Intermediate Similarity	NPC173328
0.8442	Intermediate Similarity	NPC186992
0.8442	Intermediate Similarity	NPC269318
0.8442	Intermediate Similarity	NPC476087
0.8442	Intermediate Similarity	NPC290012
0.8442	Intermediate Similarity	NPC477331
0.8442	Intermediate Similarity	NPC472201
0.8406	Intermediate Similarity	NPC76881
0.8406	Intermediate Similarity	NPC471760
0.8406	Intermediate Similarity	NPC12040
0.8406	Intermediate Similarity	NPC471761
0.8406	Intermediate Similarity	NPC190418
0.84	Intermediate Similarity	NPC476781
0.84	Intermediate Similarity	NPC476783
0.84	Intermediate Similarity	NPC216883
0.84	Intermediate Similarity	NPC476782
0.8289	Intermediate Similarity	NPC477326
0.8289	Intermediate Similarity	NPC113745
0.8289	Intermediate Similarity	NPC109887
0.8289	Intermediate Similarity	NPC477330
0.8289	Intermediate Similarity	NPC477325
0.8289	Intermediate Similarity	NPC477323
0.8289	Intermediate Similarity	NPC475425
0.8289	Intermediate Similarity	NPC477329
0.8289	Intermediate Similarity	NPC477328
0.8289	Intermediate Similarity	NPC146380
0.8289	Intermediate Similarity	NPC477320
0.8289	Intermediate Similarity	NPC281563
0.8228	Intermediate Similarity	NPC60849
0.8228	Intermediate Similarity	NPC472352
0.8228	Intermediate Similarity	NPC477332
0.8125	Intermediate Similarity	NPC288471
0.8056	Intermediate Similarity	NPC250619
0.8056	Intermediate Similarity	NPC67099
0.7975	Intermediate Similarity	NPC236649
0.7975	Intermediate Similarity	NPC21693
0.7952	Intermediate Similarity	NPC470009
0.7857	Intermediate Similarity	NPC268243
0.7838	Intermediate Similarity	NPC52268
0.7838	Intermediate Similarity	NPC53760
0.7831	Intermediate Similarity	NPC314364
0.7831	Intermediate Similarity	NPC51662
0.7826	Intermediate Similarity	NPC477753
0.7826	Intermediate Similarity	NPC477762
0.7826	Intermediate Similarity	NPC477763
0.7826	Intermediate Similarity	NPC472026
0.7826	Intermediate Similarity	NPC477755
0.7826	Intermediate Similarity	NPC477757
0.7826	Intermediate Similarity	NPC477750
0.7778	Intermediate Similarity	NPC477751
0.7778	Intermediate Similarity	NPC477752
0.7778	Intermediate Similarity	NPC477764
0.7778	Intermediate Similarity	NPC477756
0.7778	Intermediate Similarity	NPC473500
0.7778	Intermediate Similarity	NPC156089
0.7778	Intermediate Similarity	NPC38295
0.7778	Intermediate Similarity	NPC470313
0.7761	Intermediate Similarity	NPC148424
0.7711	Intermediate Similarity	NPC470657
0.7683	Intermediate Similarity	NPC473791
0.7671	Intermediate Similarity	NPC477761
0.7671	Intermediate Similarity	NPC477759
0.7671	Intermediate Similarity	NPC477754
0.7671	Intermediate Similarity	NPC477758
0.7671	Intermediate Similarity	NPC477760
0.7619	Intermediate Similarity	NPC31349
0.759	Intermediate Similarity	NPC83839
0.7536	Intermediate Similarity	NPC322855
0.7536	Intermediate Similarity	NPC320032
0.7468	Intermediate Similarity	NPC110813
0.7463	Intermediate Similarity	NPC469937
0.7463	Intermediate Similarity	NPC320588
0.7463	Intermediate Similarity	NPC53463
0.7463	Intermediate Similarity	NPC23155
0.7436	Intermediate Similarity	NPC228411
0.7432	Intermediate Similarity	NPC32148
0.7429	Intermediate Similarity	NPC470363
0.7391	Intermediate Similarity	NPC219040
0.7391	Intermediate Similarity	NPC472025
0.7375	Intermediate Similarity	NPC475616
0.7375	Intermediate Similarity	NPC133377
0.7349	Intermediate Similarity	NPC474266
0.7313	Intermediate Similarity	NPC323361
0.7313	Intermediate Similarity	NPC130683
0.7303	Intermediate Similarity	NPC477345
0.7303	Intermediate Similarity	NPC477348
0.7303	Intermediate Similarity	NPC238264
0.7286	Intermediate Similarity	NPC34877
0.7286	Intermediate Similarity	NPC290179
0.7273	Intermediate Similarity	NPC477349
0.7273	Intermediate Similarity	NPC472197
0.7262	Intermediate Similarity	NPC125253
0.7262	Intermediate Similarity	NPC253975
0.7262	Intermediate Similarity	NPC192025
0.7253	Intermediate Similarity	NPC261372
0.7253	Intermediate Similarity	NPC476612
0.7253	Intermediate Similarity	NPC263674
0.7253	Intermediate Similarity	NPC58267
0.7253	Intermediate Similarity	NPC476613
0.725	Intermediate Similarity	NPC70996
0.725	Intermediate Similarity	NPC474003
0.7229	Intermediate Similarity	NPC475849
0.7222	Intermediate Similarity	NPC215570
0.72	Intermediate Similarity	NPC286842
0.72	Intermediate Similarity	NPC469925
0.7191	Intermediate Similarity	NPC320089
0.7179	Intermediate Similarity	NPC475232
0.7179	Intermediate Similarity	NPC473699
0.7179	Intermediate Similarity	NPC475260
0.7179	Intermediate Similarity	NPC473775
0.7179	Intermediate Similarity	NPC51249
0.7179	Intermediate Similarity	NPC474100
0.7143	Intermediate Similarity	NPC475593
0.7143	Intermediate Similarity	NPC54731
0.7143	Intermediate Similarity	NPC475241
0.7143	Intermediate Similarity	NPC475164
0.7143	Intermediate Similarity	NPC473765
0.7143	Intermediate Similarity	NPC473605
0.7143	Intermediate Similarity	NPC475525
0.7143	Intermediate Similarity	NPC321873
0.7143	Intermediate Similarity	NPC476066
0.7143	Intermediate Similarity	NPC474297
0.7143	Intermediate Similarity	NPC475540
0.7143	Intermediate Similarity	NPC475375
0.7111	Intermediate Similarity	NPC44682
0.7111	Intermediate Similarity	NPC163409
0.7108	Intermediate Similarity	NPC216941
0.7105	Intermediate Similarity	NPC82315
0.7089	Intermediate Similarity	NPC138273
0.7079	Intermediate Similarity	NPC472199
0.7065	Intermediate Similarity	NPC236580
0.7065	Intermediate Similarity	NPC304445
0.7065	Intermediate Similarity	NPC472273
0.7024	Intermediate Similarity	NPC248415
0.7021	Intermediate Similarity	NPC476611
0.7015	Intermediate Similarity	NPC23134
0.7015	Intermediate Similarity	NPC124963
0.7015	Intermediate Similarity	NPC326533
0.7015	Intermediate Similarity	NPC233726
0.7013	Intermediate Similarity	NPC28526
0.6977	Remote Similarity	NPC478111
0.6957	Remote Similarity	NPC303727
0.6957	Remote Similarity	NPC475785
0.6957	Remote Similarity	NPC306041
0.6957	Remote Similarity	NPC475765
0.6947	Remote Similarity	NPC94919
0.6923	Remote Similarity	NPC472198

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 NPC291228 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	666
0.1-0.2	4097
0.2-0.3	2901
0.3-0.4	780
0.4-0.5	470
0.5-0.6	179
0.6-0.7	49
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7463	Intermediate Similarity	NPD3728	Approved
0.7463	Intermediate Similarity	NPD3730	Approved
0.7432	Intermediate Similarity	NPD897	Approved
0.7432	Intermediate Similarity	NPD898	Approved
0.7432	Intermediate Similarity	NPD896	Approved
0.7313	Intermediate Similarity	NPD887	Approved
0.7313	Intermediate Similarity	NPD895	Approved
0.7313	Intermediate Similarity	NPD889	Approved
0.7313	Intermediate Similarity	NPD894	Approved
0.7246	Intermediate Similarity	NPD2267	Suspended
0.7164	Intermediate Similarity	NPD2269	Approved
0.7073	Intermediate Similarity	NPD7329	Approved
0.7015	Intermediate Similarity	NPD904	Phase 3
0.7015	Intermediate Similarity	NPD905	Approved
0.6962	Remote Similarity	NPD3181	Approved
0.6923	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD891	Phase 3
0.6812	Remote Similarity	NPD888	Phase 3
0.6812	Remote Similarity	NPD893	Approved
0.6812	Remote Similarity	NPD892	Phase 3
0.68	Remote Similarity	NPD7909	Approved
0.6771	Remote Similarity	NPD8082	Approved
0.6771	Remote Similarity	NPD8086	Approved
0.6771	Remote Similarity	NPD8085	Approved
0.6771	Remote Similarity	NPD8084	Approved
0.6771	Remote Similarity	NPD8083	Approved
0.6771	Remote Similarity	NPD8138	Approved
0.6771	Remote Similarity	NPD8139	Approved
0.6701	Remote Similarity	NPD8275	Approved
0.6701	Remote Similarity	NPD8276	Approved
0.6667	Remote Similarity	NPD8961	Approved
0.6633	Remote Similarity	NPD8081	Approved
0.6633	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6123	Approved
0.6567	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD8393	Approved
0.65	Remote Similarity	NPD8140	Approved
0.65	Remote Similarity	NPD8307	Discontinued
0.6447	Remote Similarity	NPD847	Phase 1
0.6436	Remote Similarity	NPD6686	Approved
0.6413	Remote Similarity	NPD6698	Approved
0.6413	Remote Similarity	NPD46	Approved
0.6373	Remote Similarity	NPD8305	Approved
0.6373	Remote Similarity	NPD8306	Approved
0.6373	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3669	Approved
0.6364	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD4802	Phase 2
0.6353	Remote Similarity	NPD4238	Approved
0.6311	Remote Similarity	NPD8087	Discontinued
0.63	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD8133	Approved
0.6269	Remote Similarity	NPD9000	Phase 3
0.6269	Remote Similarity	NPD8998	Phase 2
0.6269	Remote Similarity	NPD8993	Phase 1
0.6269	Remote Similarity	NPD8997	Approved
0.6269	Remote Similarity	NPD8999	Phase 3
0.625	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7346	Approved
0.6216	Remote Similarity	NPD8959	Approved
0.617	Remote Similarity	NPD7983	Approved
0.6136	Remote Similarity	NPD1780	Approved
0.6136	Remote Similarity	NPD1779	Approved
0.6119	Remote Similarity	NPD2699	Approved
0.6111	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD8171	Discontinued
0.6087	Remote Similarity	NPD8965	Approved
0.6087	Remote Similarity	NPD8966	Approved
0.6081	Remote Similarity	NPD73	Approved
0.6053	Remote Similarity	NPD3198	Approved
0.6036	Remote Similarity	NPD8516	Approved
0.6036	Remote Similarity	NPD8517	Approved
0.6036	Remote Similarity	NPD8515	Approved
0.6036	Remote Similarity	NPD8513	Phase 3
0.6022	Remote Similarity	NPD618	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6412	Phase 2
0.597	Remote Similarity	NPD9006	Approved
0.5963	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD1457	Discontinued
0.5941	Remote Similarity	NPD8301	Approved
0.5941	Remote Similarity	NPD8300	Approved
0.5905	Remote Similarity	NPD6941	Approved
0.5893	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.589	Remote Similarity	NPD9036	Phase 3
0.589	Remote Similarity	NPD9035	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD882	Phase 2
0.5889	Remote Similarity	NPD883	Phase 2
0.5872	Remote Similarity	NPD6940	Discontinued
0.5841	Remote Similarity	NPD8080	Discontinued
0.5833	Remote Similarity	NPD1399	Approved
0.5833	Remote Similarity	NPD1400	Approved
0.5821	Remote Similarity	NPD8788	Approved
0.5814	Remote Similarity	NPD2257	Approved
0.5804	Remote Similarity	NPD8347	Approved
0.5804	Remote Similarity	NPD8345	Approved
0.5804	Remote Similarity	NPD8346	Approved
0.58	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD3716	Discontinued
0.5789	Remote Similarity	NPD369	Approved
0.5783	Remote Similarity	NPD8277	Approved
0.5773	Remote Similarity	NPD1447	Phase 3
0.5773	Remote Similarity	NPD1446	Phase 3
0.5766	Remote Similarity	NPD7641	Discontinued
0.5758	Remote Similarity	NPD6428	Approved
0.5758	Remote Similarity	NPD7839	Suspended
0.5752	Remote Similarity	NPD8444	Approved
0.5733	Remote Similarity	NPD885	Approved
0.5733	Remote Similarity	NPD884	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD1811	Approved
0.5698	Remote Similarity	NPD1810	Approved
0.5672	Remote Similarity	NPD2270	Approved
0.5663	Remote Similarity	NPD8278	Approved
0.5652	Remote Similarity	NPD7830	Approved
0.5652	Remote Similarity	NPD7829	Approved
0.5652	Remote Similarity	NPD8328	Phase 3
0.5644	Remote Similarity	NPD2255	Approved
0.5632	Remote Similarity	NPD376	Approved
0.5632	Remote Similarity	NPD11	Approved
0.5631	Remote Similarity	NPD7139	Approved
0.5631	Remote Similarity	NPD7140	Approved
0.5631	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD6115	Approved
0.5618	Remote Similarity	NPD6118	Approved
0.5618	Remote Similarity	NPD6114	Approved
0.5618	Remote Similarity	NPD6697	Approved
0.5603	Remote Similarity	NPD8340	Approved
0.5603	Remote Similarity	NPD8341	Approved
0.5603	Remote Similarity	NPD8342	Approved
0.5603	Remote Similarity	NPD8299	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