NPASS Compound

Structure

NPC469549 OpenBabel07101718222D 33 34 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 5.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 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 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 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 3.4641 -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 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 4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 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 4.3301 -0.5000 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 4.8301 0.6340 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 -1.7321 -0.0000 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 3 4 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 7 1 0 0 0 0 5 13 2 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 9 22 1 0 0 0 0 10 17 1 0 0 0 0 10 22 1 0 0 0 0 11 31 1 0 0 0 0 12 1 1 1 0 0 0 12 32 1 0 0 0 0 14 23 1 0 0 0 0 15 11 1 6 0 0 0 15 18 1 0 0 0 0 15 33 1 0 0 0 0 16 24 2 0 0 0 0 16 25 1 0 0 0 0 17 26 2 0 0 0 0 17 31 1 0 0 0 0 18 19 1 0 0 0 0 18 27 1 1 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 21 1 0 0 0 0 20 29 1 1 0 0 0 21 32 1 1 0 0 0 21 33 1 0 0 0 0 22 2 1 1 0 0 0 22 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.19
Volume:	455.465
LogP:	0.297
LogD:	-0.271
LogS:	-1.746
# Rotatable Bonds:	12
TPSA:	183.21
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.232
Synthetic Accessibility Score:	4.198
Fsp3:	0.636
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.141
MDCK Permeability:	0.00010849368118215352
Pgp-inhibitor:	0.001
Pgp-substrate:	0.936
Human Intestinal Absorption (HIA):	0.864
20% Bioavailability (F20%):	0.127
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.145
Plasma Protein Binding (PPB):	54.25536346435547%
Volume Distribution (VD):	0.284
Pgp-substrate:	34.292118072509766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.039

ADMET: Excretion

Clearance (CL):	1.611
Half-life (T1/2):	0.913

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.152
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.133
Skin Sensitization:	0.092
Carcinogencity:	0.201
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.017

Download Data

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

Natural Product: NPC469549

Natural Product ID:	NPC469549
*Common Name:**	1-[(2R)-4-(4-Hydroxyphenyl)-2-Butanol-2-O-B-Dglucopyranosyl]-3-Hydroxyl-3-Methylglutaric Acid
IUPAC Name:	(3S)-3-hydroxy-3-methyl-5-oxo-5-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]oxyoxan-2-yl]methoxy]pentanoic acid
Synonyms:
Standard InCHIKey:	SBAYJWHOFRCVDL-LBQWKFMXSA-N
Standard InCHI:	InChI=1S/C22H32O11/c1-12(3-4-13-5-7-14(23)8-6-13)32-21-20(29)19(28)18(27)15(33-21)11-31-17(26)10-22(2,30)9-16(24)25/h5-8,12,15,18-21,23,27-30H,3-4,9-11H2,1-2H3,(H,24,25)/t12-,15-,18-,19+,20-,21+,22+/m1/s1
SMILES:	C[C@@H](O[C@H]1O[C@H](COC(=O)C[C@](CC(=O)O)(O)C)[C@H]([C@@H]([C@H]1O)O)O)CCc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1086949
PubChem CID:	46889079
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
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[20363129]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4138	Betula platyphylla	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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	26.6	%	PMID[521328]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	20.0	%	PMID[521328]

☑ 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 NPC469549 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	247
0.1-0.2	1006
0.2-0.3	2705
0.3-0.4	6952
0.4-0.5	11132
0.5-0.6	7469
0.6-0.7	11282
0.7-0.8	1724
0.8-0.85	139
0.85-0.9	38
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9154	High Similarity	NPC169398
0.9008	High Similarity	NPC471029
0.8992	High Similarity	NPC470122
0.8992	High Similarity	NPC17968
0.8992	High Similarity	NPC469705
0.8952	High Similarity	NPC476448
0.8952	High Similarity	NPC476445
0.8952	High Similarity	NPC469548
0.8947	High Similarity	NPC101686
0.8947	High Similarity	NPC469364
0.8947	High Similarity	NPC65262
0.8931	High Similarity	NPC164172
0.8923	High Similarity	NPC281798
0.8898	High Similarity	NPC123704
0.8871	High Similarity	NPC282409
0.8871	High Similarity	NPC469702
0.8855	High Similarity	NPC471066
0.8855	High Similarity	NPC471095
0.8852	High Similarity	NPC148055
0.8837	High Similarity	NPC158673
0.876	High Similarity	NPC106677
0.8731	High Similarity	NPC472132
0.873	High Similarity	NPC55608
0.8705	High Similarity	NPC212808
0.8689	High Similarity	NPC157338
0.8686	High Similarity	NPC469623
0.8686	High Similarity	NPC296643
0.8686	High Similarity	NPC148080
0.8667	High Similarity	NPC469696
0.8661	High Similarity	NPC52097
0.8651	High Similarity	NPC469704
0.8651	High Similarity	NPC160854
0.8651	High Similarity	NPC201402
0.8651	High Similarity	NPC469703
0.8636	High Similarity	NPC478255
0.8636	High Similarity	NPC476407
0.8636	High Similarity	NPC235294
0.8636	High Similarity	NPC46137
0.8615	High Similarity	NPC173150
0.8615	High Similarity	NPC45224
0.8615	High Similarity	NPC288416
0.8615	High Similarity	NPC35288
0.8615	High Similarity	NPC471881
0.8615	High Similarity	NPC156692
0.8615	High Similarity	NPC471882
0.8594	High Similarity	NPC178449
0.8594	High Similarity	NPC470907
0.8594	High Similarity	NPC232454
0.8583	High Similarity	NPC469686
0.8583	High Similarity	NPC11724
0.8571	High Similarity	NPC143246
0.8571	High Similarity	NPC475539
0.8571	High Similarity	NPC119773
0.8571	High Similarity	NPC474268
0.8561	High Similarity	NPC63304
0.8538	High Similarity	NPC252114
0.8538	High Similarity	NPC61181
0.8538	High Similarity	NPC471157
0.8529	High Similarity	NPC310252
0.8529	High Similarity	NPC84789
0.8529	High Similarity	NPC302583
0.8529	High Similarity	NPC100558
0.8519	High Similarity	NPC123988
0.8516	High Similarity	NPC469927
0.8516	High Similarity	NPC471067
0.8507	High Similarity	NPC114116
0.8504	High Similarity	NPC476872
0.85	High Similarity	NPC475528
0.8496	Intermediate Similarity	NPC138777
0.8496	Intermediate Similarity	NPC225384
0.8496	Intermediate Similarity	NPC246869
0.8489	Intermediate Similarity	NPC478250
0.8473	Intermediate Similarity	NPC103533
0.8467	Intermediate Similarity	NPC220942
0.8462	Intermediate Similarity	NPC126991
0.8462	Intermediate Similarity	NPC83218
0.8456	Intermediate Similarity	NPC471345
0.845	Intermediate Similarity	NPC236981
0.8429	Intermediate Similarity	NPC296659
0.8429	Intermediate Similarity	NPC202391
0.8409	Intermediate Similarity	NPC225307
0.84	Intermediate Similarity	NPC175771
0.8387	Intermediate Similarity	NPC29607
0.8387	Intermediate Similarity	NPC313193
0.8382	Intermediate Similarity	NPC263829
0.8382	Intermediate Similarity	NPC180171
0.8382	Intermediate Similarity	NPC158325
0.8382	Intermediate Similarity	NPC103398
0.8357	Intermediate Similarity	NPC469367
0.8357	Intermediate Similarity	NPC186296
0.8333	Intermediate Similarity	NPC469687
0.8333	Intermediate Similarity	NPC324262
0.8333	Intermediate Similarity	NPC31745
0.8333	Intermediate Similarity	NPC220936
0.8333	Intermediate Similarity	NPC62800
0.8322	Intermediate Similarity	NPC23677
0.8321	Intermediate Similarity	NPC90318
0.8321	Intermediate Similarity	NPC470572
0.8309	Intermediate Similarity	NPC34456
0.8298	Intermediate Similarity	NPC184464
0.8298	Intermediate Similarity	NPC251062
0.8295	Intermediate Similarity	NPC266045
0.8276	Intermediate Similarity	NPC474620
0.8235	Intermediate Similarity	NPC215484
0.8235	Intermediate Similarity	NPC254398
0.8227	Intermediate Similarity	NPC293154
0.8219	Intermediate Similarity	NPC106818
0.8214	Intermediate Similarity	NPC159387
0.8214	Intermediate Similarity	NPC7518
0.8214	Intermediate Similarity	NPC137501
0.8214	Intermediate Similarity	NPC154262
0.8209	Intermediate Similarity	NPC229784
0.8209	Intermediate Similarity	NPC253595
0.8209	Intermediate Similarity	NPC477294
0.8209	Intermediate Similarity	NPC477293
0.8207	Intermediate Similarity	NPC117346
0.8207	Intermediate Similarity	NPC240592
0.8201	Intermediate Similarity	NPC328273
0.8201	Intermediate Similarity	NPC81515
0.8201	Intermediate Similarity	NPC321184
0.8201	Intermediate Similarity	NPC476383
0.8201	Intermediate Similarity	NPC64141
0.8201	Intermediate Similarity	NPC171134
0.8201	Intermediate Similarity	NPC68092
0.8201	Intermediate Similarity	NPC472350
0.8201	Intermediate Similarity	NPC321638
0.8201	Intermediate Similarity	NPC197316
0.8201	Intermediate Similarity	NPC89105
0.8195	Intermediate Similarity	NPC264900
0.8195	Intermediate Similarity	NPC79715
0.8195	Intermediate Similarity	NPC108659
0.8195	Intermediate Similarity	NPC231607
0.8182	Intermediate Similarity	NPC473147
0.8175	Intermediate Similarity	NPC287597
0.8175	Intermediate Similarity	NPC34293
0.8175	Intermediate Similarity	NPC886
0.8175	Intermediate Similarity	NPC471883
0.8169	Intermediate Similarity	NPC194938
0.8163	Intermediate Similarity	NPC87403
0.8162	Intermediate Similarity	NPC269421
0.8162	Intermediate Similarity	NPC473924
0.8162	Intermediate Similarity	NPC473285
0.8138	Intermediate Similarity	NPC478242
0.8138	Intermediate Similarity	NPC96599
0.8134	Intermediate Similarity	NPC232880
0.8129	Intermediate Similarity	NPC476376
0.8129	Intermediate Similarity	NPC260425
0.8125	Intermediate Similarity	NPC470330
0.812	Intermediate Similarity	NPC94179
0.8112	Intermediate Similarity	NPC210330
0.8102	Intermediate Similarity	NPC28637
0.8099	Intermediate Similarity	NPC475213
0.8099	Intermediate Similarity	NPC152796
0.8092	Intermediate Similarity	NPC476142
0.8088	Intermediate Similarity	NPC254819
0.8088	Intermediate Similarity	NPC219677
0.8085	Intermediate Similarity	NPC476385
0.8085	Intermediate Similarity	NPC476377
0.8085	Intermediate Similarity	NPC134405
0.8085	Intermediate Similarity	NPC47471
0.8082	Intermediate Similarity	NPC35097
0.8074	Intermediate Similarity	NPC295970
0.8074	Intermediate Similarity	NPC184092
0.8071	Intermediate Similarity	NPC205195
0.8071	Intermediate Similarity	NPC49597
0.8069	Intermediate Similarity	NPC28776
0.8069	Intermediate Similarity	NPC473138
0.806	Intermediate Similarity	NPC476873
0.8056	Intermediate Similarity	NPC473867
0.8056	Intermediate Similarity	NPC291153
0.8042	Intermediate Similarity	NPC141455
0.8042	Intermediate Similarity	NPC473281
0.8042	Intermediate Similarity	NPC296954
0.8042	Intermediate Similarity	NPC77922
0.8042	Intermediate Similarity	NPC196063
0.8042	Intermediate Similarity	NPC300894
0.803	Intermediate Similarity	NPC212176
0.803	Intermediate Similarity	NPC138798
0.8028	Intermediate Similarity	NPC222433
0.8028	Intermediate Similarity	NPC265648
0.8027	Intermediate Similarity	NPC475407
0.8027	Intermediate Similarity	NPC158546
0.8027	Intermediate Similarity	NPC289021
0.8014	Intermediate Similarity	NPC478234
0.8014	Intermediate Similarity	NPC473799
0.8014	Intermediate Similarity	NPC475530
0.8013	Intermediate Similarity	NPC469384
0.8	Intermediate Similarity	NPC148982
0.8	Intermediate Similarity	NPC10945
0.8	Intermediate Similarity	NPC475378
0.8	Intermediate Similarity	NPC78363
0.7987	Intermediate Similarity	NPC160882
0.7986	Intermediate Similarity	NPC233350
0.7986	Intermediate Similarity	NPC182217
0.7986	Intermediate Similarity	NPC70680
0.7972	Intermediate Similarity	NPC96795
0.7972	Intermediate Similarity	NPC476384
0.7972	Intermediate Similarity	NPC76406
0.7972	Intermediate Similarity	NPC269141
0.7972	Intermediate Similarity	NPC105005

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 NPC469549 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	677
0.2-0.3	1581
0.3-0.4	2907
0.4-0.5	2076
0.5-0.6	1226
0.6-0.7	446
0.7-0.8	19
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8201	Intermediate Similarity	NPD7266	Discontinued
0.7612	Intermediate Similarity	NPD1091	Approved
0.7484	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6190	Approved
0.7403	Intermediate Similarity	NPD8455	Phase 2
0.7394	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD7097	Phase 1
0.7333	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD9545	Approved
0.731	Intermediate Similarity	NPD7033	Discontinued
0.7284	Intermediate Similarity	NPD7054	Approved
0.7284	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5048	Discontinued
0.7239	Intermediate Similarity	NPD7074	Phase 3
0.7239	Intermediate Similarity	NPD7472	Approved
0.7203	Intermediate Similarity	NPD6233	Phase 2
0.719	Intermediate Similarity	NPD1653	Approved
0.7181	Intermediate Similarity	NPD4628	Phase 3
0.7152	Intermediate Similarity	NPD7251	Discontinued
0.7152	Intermediate Similarity	NPD7685	Pre-registration
0.7152	Intermediate Similarity	NPD7075	Discontinued
0.7117	Intermediate Similarity	NPD7228	Approved
0.7108	Intermediate Similarity	NPD7808	Phase 3
0.7108	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4380	Phase 2
0.7091	Intermediate Similarity	NPD6797	Phase 2
0.7055	Intermediate Similarity	NPD6653	Approved
0.7048	Intermediate Similarity	NPD6559	Discontinued
0.7042	Intermediate Similarity	NPD5736	Approved
0.7039	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6798	Discontinued
0.7012	Intermediate Similarity	NPD3818	Discontinued
0.7006	Intermediate Similarity	NPD37	Approved
0.7	Intermediate Similarity	NPD6234	Discontinued
0.6992	Remote Similarity	NPD7843	Approved
0.6986	Remote Similarity	NPD230	Phase 1
0.6986	Remote Similarity	NPD6355	Discontinued
0.6981	Remote Similarity	NPD4967	Phase 2
0.6981	Remote Similarity	NPD4966	Approved
0.6981	Remote Similarity	NPD4965	Approved
0.6977	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5647	Approved
0.6966	Remote Similarity	NPD4062	Phase 3
0.6962	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3400	Discontinued
0.6954	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3027	Phase 3
0.6935	Remote Similarity	NPD2933	Approved
0.6935	Remote Similarity	NPD2934	Approved
0.6928	Remote Similarity	NPD6799	Approved
0.6917	Remote Similarity	NPD969	Suspended
0.6913	Remote Similarity	NPD9570	Approved
0.6899	Remote Similarity	NPD6801	Discontinued
0.6889	Remote Similarity	NPD2629	Approved
0.6887	Remote Similarity	NPD1652	Phase 2
0.688	Remote Similarity	NPD2859	Approved
0.688	Remote Similarity	NPD2860	Approved
0.687	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7978	Discontinued
0.6864	Remote Similarity	NPD8312	Approved
0.6864	Remote Similarity	NPD8313	Approved
0.6863	Remote Similarity	NPD5058	Phase 3
0.6849	Remote Similarity	NPD6663	Approved
0.6838	Remote Similarity	NPD7157	Approved
0.6835	Remote Similarity	NPD5125	Phase 3
0.6835	Remote Similarity	NPD5126	Approved
0.6835	Remote Similarity	NPD7411	Suspended
0.6828	Remote Similarity	NPD7095	Approved
0.6818	Remote Similarity	NPD2684	Approved
0.681	Remote Similarity	NPD7199	Phase 2
0.6795	Remote Similarity	NPD5403	Approved
0.6792	Remote Similarity	NPD1934	Approved
0.6788	Remote Similarity	NPD9493	Approved
0.6786	Remote Similarity	NPD3847	Discontinued
0.6784	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6362	Approved
0.6781	Remote Similarity	NPD3764	Approved
0.6776	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD9495	Approved
0.677	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3787	Discontinued
0.6757	Remote Similarity	NPD5124	Phase 1
0.6757	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.675	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7240	Approved
0.6744	Remote Similarity	NPD846	Approved
0.6744	Remote Similarity	NPD940	Approved
0.6742	Remote Similarity	NPD1358	Approved
0.6738	Remote Similarity	NPD1535	Discovery
0.6738	Remote Similarity	NPD3705	Approved
0.6738	Remote Similarity	NPD422	Phase 1
0.6732	Remote Similarity	NPD2575	Approved
0.6719	Remote Similarity	NPD3020	Approved
0.6714	Remote Similarity	NPD1778	Approved
0.6713	Remote Similarity	NPD3225	Approved
0.6712	Remote Similarity	NPD3136	Phase 2
0.6711	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2424	Discontinued
0.6711	Remote Similarity	NPD1549	Phase 2
0.6708	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD3817	Phase 2
0.6692	Remote Similarity	NPD6647	Phase 2
0.6692	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD1894	Discontinued
0.669	Remote Similarity	NPD1481	Phase 2
0.6689	Remote Similarity	NPD826	Approved
0.6689	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD4060	Phase 1
0.6689	Remote Similarity	NPD1613	Approved
0.6689	Remote Similarity	NPD825	Approved
0.6689	Remote Similarity	NPD2935	Discontinued
0.6687	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6166	Phase 2
0.6687	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6674	Discontinued
0.6667	Remote Similarity	NPD3094	Phase 2
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD6685	Approved
0.6667	Remote Similarity	NPD6599	Discontinued
0.6646	Remote Similarity	NPD7972	Discontinued
0.6646	Remote Similarity	NPD7819	Suspended
0.6645	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6004	Phase 3
0.6645	Remote Similarity	NPD6005	Phase 3
0.6645	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6002	Phase 3
0.6644	Remote Similarity	NPD4340	Discontinued
0.6644	Remote Similarity	NPD6832	Phase 2
0.6643	Remote Similarity	NPD1357	Approved
0.6642	Remote Similarity	NPD3022	Approved
0.6642	Remote Similarity	NPD3021	Approved
0.6627	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD8166	Discontinued
0.6621	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD290	Approved
0.6607	Remote Similarity	NPD3751	Discontinued
0.6605	Remote Similarity	NPD5402	Approved
0.6604	Remote Similarity	NPD7458	Discontinued
0.6596	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD255	Approved
0.6594	Remote Similarity	NPD256	Approved
0.6594	Remote Similarity	NPD4198	Discontinued
0.6593	Remote Similarity	NPD7435	Discontinued
0.6582	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD2240	Approved
0.6579	Remote Similarity	NPD2239	Approved
0.6577	Remote Similarity	NPD1240	Approved
0.6573	Remote Similarity	NPD1608	Approved
0.6573	Remote Similarity	NPD9269	Phase 2
0.6571	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD9266	Approved
0.6567	Remote Similarity	NPD74	Approved
0.6561	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3536	Discontinued
0.6557	Remote Similarity	NPD8319	Approved
0.6557	Remote Similarity	NPD8320	Phase 1
0.6556	Remote Similarity	NPD4536	Approved
0.6556	Remote Similarity	NPD4538	Approved
0.6556	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD3268	Approved
0.6552	Remote Similarity	NPD8150	Discontinued
0.6543	Remote Similarity	NPD2801	Approved
0.6541	Remote Similarity	NPD3134	Approved
0.6536	Remote Similarity	NPD5763	Approved
0.6536	Remote Similarity	NPD5762	Approved
0.6535	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD555	Phase 2
0.6533	Remote Similarity	NPD1933	Approved
0.6531	Remote Similarity	NPD4908	Phase 1
0.6528	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6534	Approved
0.6517	Remote Similarity	NPD6535	Approved
0.6516	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD1510	Phase 2
0.651	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.651	Remote Similarity	NPD520	Approved
0.6503	Remote Similarity	NPD3092	Approved
0.6503	Remote Similarity	NPD4806	Approved
0.6503	Remote Similarity	NPD4807	Approved
0.65	Remote Similarity	NPD7700	Phase 2
0.65	Remote Similarity	NPD7699	Phase 2
0.6496	Remote Similarity	NPD5535	Approved
0.6494	Remote Similarity	NPD4534	Discontinued
0.6493	Remote Similarity	NPD9267	Approved
0.6493	Remote Similarity	NPD9264	Approved
0.6493	Remote Similarity	NPD9263	Approved
0.649	Remote Similarity	NPD1607	Approved
0.6488	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD8651	Approved
0.6479	Remote Similarity	NPD5305	Approved
0.6479	Remote Similarity	NPD5306	Approved
0.6475	Remote Similarity	NPD6671	Approved
0.6475	Remote Similarity	NPD111	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