NPASS Compound

Structure

NPC471067 OpenBabel07101719152D 42 45 0 0 1 0 0 0 0 0999 V2000 -4.3301 -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 -5.1962 -1.0000 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 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 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 -4.3301 0.5000 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 -7.7942 -1.5000 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 0.0000 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 4.0875 -3.6160 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 -6.0622 -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 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6808 -2.7024 0.0000 C 0 0 2 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 4.1808 -1.8364 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 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5116 -1.0933 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 2.5981 -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 2 0 0 0 0 0 0 0 0 0 5.0820 -3.7205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1753 -1.7319 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 3.7195 -0.1151 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 1.7321 -1.0000 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 2.7026 -2.4945 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 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 17 1 0 0 0 0 5 10 1 0 0 0 0 5 17 2 0 0 0 0 6 11 2 0 0 0 0 6 17 1 0 0 0 0 7 12 1 0 0 0 0 7 18 2 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 14 1 0 0 0 0 9 18 1 0 0 0 0 10 19 2 0 0 0 0 11 19 1 0 0 0 0 12 20 2 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 31 1 0 0 0 0 16 39 1 0 0 0 0 19 32 1 0 0 0 0 20 33 1 0 0 0 0 21 4 1 6 0 0 0 21 40 1 0 0 0 0 22 15 1 1 0 0 0 22 24 1 0 0 0 0 22 41 1 0 0 0 0 23 16 1 1 0 0 0 23 25 1 0 0 0 0 23 42 1 0 0 0 0 24 27 1 0 0 0 0 24 34 1 6 0 0 0 25 26 1 0 0 0 0 25 35 1 6 0 0 0 26 28 1 0 0 0 0 26 36 1 1 0 0 0 27 29 1 0 0 0 0 27 37 1 6 0 0 0 28 30 1 0 0 0 0 28 38 1 6 0 0 0 29 39 1 1 0 0 0 29 41 1 0 0 0 0 30 40 1 1 0 0 0 30 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.27
Volume:	582.874
LogP:	1.402
LogD:	1.848
LogS:	-2.742
# Rotatable Bonds:	14
TPSA:	198.76
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.137
Synthetic Accessibility Score:	4.482
Fsp3:	0.6
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:	-6.175
MDCK Permeability:	1.0424860192870256e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.616
Human Intestinal Absorption (HIA):	0.995
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	94.63504791259766%
Volume Distribution (VD):	0.175
Pgp-substrate:	2.7518608570098877%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.023
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.68
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.172
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.078

ADMET: Excretion

Clearance (CL):	1.429
Half-life (T1/2):	0.817

ADMET: Toxicity

hERG Blockers:	0.364
Human Hepatotoxicity (H-HT):	0.054
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.298
Rat Oral Acute Toxicity:	0.183
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.956
Carcinogencity:	0.266
Eye Corrosion:	0.003
Eye Irritation:	0.137
Respiratory Toxicity:	0.015

Download Data

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

Natural Product: NPC471067

Natural Product ID:	NPC471067
*Common Name:**	(3R)-1,7-Bis-(4-Hydroxyphenyl)-3-Heptanol-3-O-Beta-D-Apiofuranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[(3R)-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy-6-[[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	GEZFOHOYLWPGPK-DQKXWWCFSA-N
Standard InCHI:	InChI=1S/C30H42O12/c31-15-22-24(34)27(37)29(41-22)39-16-23-25(35)26(36)28(38)30(42-23)40-21(14-9-18-7-12-20(33)13-8-18)4-2-1-3-17-5-10-19(32)11-6-17/h5-8,10-13,21-38H,1-4,9,14-16H2/t21-,22-,23-,24-,25-,26+,27-,28-,29-,30-/m1/s1
SMILES:	OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)OC[C@H]1O[C@@H](O[C@@H](CCc2ccc(cc2)O)CCCCc2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2346811
PubChem CID:	71718346
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
NPO32876	alnus hirsuta f. sibirica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23465614]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	92.9	%	PMID[565960]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	92.1	%	PMID[565960]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	79.6	%	PMID[565960]

☑ 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 NPC471067 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	306
0.1-0.2	1149
0.2-0.3	2864
0.3-0.4	8374
0.4-0.5	10901
0.5-0.6	10371
0.6-0.7	7026
0.7-0.8	1466
0.8-0.85	183
0.85-0.9	37
0.9-0.95	16
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9914	High Similarity	NPC178449
0.9914	High Similarity	NPC232454
0.9914	High Similarity	NPC470907
0.9826	High Similarity	NPC469704
0.9826	High Similarity	NPC469703
0.9826	High Similarity	NPC160854
0.9826	High Similarity	NPC201402
0.9741	High Similarity	NPC469686
0.9583	High Similarity	NPC469687
0.9569	High Similarity	NPC282409
0.9569	High Similarity	NPC469702
0.9487	High Similarity	NPC476448
0.9487	High Similarity	NPC469548
0.9487	High Similarity	NPC476445
0.9262	High Similarity	NPC108659
0.9262	High Similarity	NPC231607
0.9262	High Similarity	NPC79715
0.9262	High Similarity	NPC264900
0.9244	High Similarity	NPC55608
0.9224	High Similarity	NPC148055
0.9217	High Similarity	NPC157338
0.92	High Similarity	NPC471095
0.92	High Similarity	NPC471066
0.918	High Similarity	NPC94179
0.9127	High Similarity	NPC164172
0.912	High Similarity	NPC478255
0.9113	High Similarity	NPC184092
0.904	High Similarity	NPC470122
0.904	High Similarity	NPC469705
0.904	High Similarity	NPC17968
0.9032	High Similarity	NPC225307
0.8952	High Similarity	NPC288416
0.8943	High Similarity	NPC90318
0.8898	High Similarity	NPC473556
0.8898	High Similarity	NPC254275
0.8898	High Similarity	NPC175771
0.8898	High Similarity	NPC301651
0.8889	High Similarity	NPC313193
0.888	High Similarity	NPC158673
0.888	High Similarity	NPC148982
0.8846	High Similarity	NPC469696
0.8819	High Similarity	NPC235294
0.8819	High Similarity	NPC46137
0.877	High Similarity	NPC266045
0.8682	High Similarity	NPC28637
0.8672	High Similarity	NPC225384
0.8672	High Similarity	NPC246869
0.8672	High Similarity	NPC138777
0.8672	High Similarity	NPC476407
0.8651	High Similarity	NPC45224
0.8651	High Similarity	NPC173150
0.8651	High Similarity	NPC471881
0.8651	High Similarity	NPC35288
0.8651	High Similarity	NPC156692
0.8651	High Similarity	NPC471882
0.8647	High Similarity	NPC472711
0.864	High Similarity	NPC83218
0.864	High Similarity	NPC126991
0.8636	High Similarity	NPC328273
0.8636	High Similarity	NPC321638
0.8636	High Similarity	NPC171134
0.8636	High Similarity	NPC321184
0.8626	High Similarity	NPC52277
0.8626	High Similarity	NPC199459
0.8626	High Similarity	NPC177035
0.8571	High Similarity	NPC61181
0.8571	High Similarity	NPC471157
0.856	High Similarity	NPC287429
0.8559	High Similarity	NPC42911
0.8559	High Similarity	NPC153795
0.8559	High Similarity	NPC290353
0.855	High Similarity	NPC79957
0.855	High Similarity	NPC263829
0.8548	High Similarity	NPC476142
0.8548	High Similarity	NPC52097
0.8519	High Similarity	NPC185307
0.8519	High Similarity	NPC46092
0.8519	High Similarity	NPC477898
0.8519	High Similarity	NPC470950
0.8516	High Similarity	NPC469549
0.8504	High Similarity	NPC106677
0.8504	High Similarity	NPC103533
0.8496	Intermediate Similarity	NPC156376
0.848	Intermediate Similarity	NPC212176
0.8473	Intermediate Similarity	NPC287597
0.8473	Intermediate Similarity	NPC476411
0.8473	Intermediate Similarity	NPC34293
0.8473	Intermediate Similarity	NPC886
0.8468	Intermediate Similarity	NPC11724
0.8456	Intermediate Similarity	NPC283995
0.8456	Intermediate Similarity	NPC129417
0.8456	Intermediate Similarity	NPC84181
0.8456	Intermediate Similarity	NPC470235
0.8444	Intermediate Similarity	NPC476356
0.8444	Intermediate Similarity	NPC472353
0.8433	Intermediate Similarity	NPC106944
0.8425	Intermediate Similarity	NPC252114
0.8421	Intermediate Similarity	NPC260425
0.8421	Intermediate Similarity	NPC262328
0.8421	Intermediate Similarity	NPC138738
0.8421	Intermediate Similarity	NPC87777
0.8421	Intermediate Similarity	NPC470413
0.8409	Intermediate Similarity	NPC180171
0.8409	Intermediate Similarity	NPC123988
0.8409	Intermediate Similarity	NPC158325
0.8409	Intermediate Similarity	NPC103398
0.8394	Intermediate Similarity	NPC279298
0.8394	Intermediate Similarity	NPC38041
0.8394	Intermediate Similarity	NPC18979
0.8394	Intermediate Similarity	NPC22150
0.8387	Intermediate Similarity	NPC269242
0.8387	Intermediate Similarity	NPC476872
0.8387	Intermediate Similarity	NPC198734
0.8387	Intermediate Similarity	NPC469412
0.8385	Intermediate Similarity	NPC475824
0.8385	Intermediate Similarity	NPC475067
0.8382	Intermediate Similarity	NPC478250
0.8382	Intermediate Similarity	NPC40305
0.8382	Intermediate Similarity	NPC105005
0.837	Intermediate Similarity	NPC471908
0.8361	Intermediate Similarity	NPC476266
0.8358	Intermediate Similarity	NPC205195
0.8358	Intermediate Similarity	NPC472350
0.8358	Intermediate Similarity	NPC197316
0.8358	Intermediate Similarity	NPC81515
0.8358	Intermediate Similarity	NPC89105
0.8358	Intermediate Similarity	NPC64141
0.8358	Intermediate Similarity	NPC68092
0.8358	Intermediate Similarity	NPC476383
0.8346	Intermediate Similarity	NPC470510
0.8346	Intermediate Similarity	NPC471345
0.8333	Intermediate Similarity	NPC470881
0.8333	Intermediate Similarity	NPC169398
0.8333	Intermediate Similarity	NPC187194
0.8333	Intermediate Similarity	NPC35731
0.8333	Intermediate Similarity	NPC112861
0.8321	Intermediate Similarity	NPC303422
0.8321	Intermediate Similarity	NPC85799
0.8321	Intermediate Similarity	NPC473046
0.8321	Intermediate Similarity	NPC26080
0.8321	Intermediate Similarity	NPC187774
0.8321	Intermediate Similarity	NPC472712
0.8321	Intermediate Similarity	NPC300894
0.8321	Intermediate Similarity	NPC118385
0.8321	Intermediate Similarity	NPC196063
0.8321	Intermediate Similarity	NPC165686
0.8321	Intermediate Similarity	NPC472713
0.8321	Intermediate Similarity	NPC141455
0.8321	Intermediate Similarity	NPC296954
0.8309	Intermediate Similarity	NPC246947
0.8306	Intermediate Similarity	NPC60589
0.8306	Intermediate Similarity	NPC469708
0.8284	Intermediate Similarity	NPC84789
0.8284	Intermediate Similarity	NPC310252
0.8284	Intermediate Similarity	NPC304152
0.8284	Intermediate Similarity	NPC78363
0.8284	Intermediate Similarity	NPC302583
0.8284	Intermediate Similarity	NPC100558
0.8273	Intermediate Similarity	NPC114505
0.8273	Intermediate Similarity	NPC15956
0.8273	Intermediate Similarity	NPC31325
0.8273	Intermediate Similarity	NPC193473
0.8273	Intermediate Similarity	NPC275284
0.8273	Intermediate Similarity	NPC224674
0.8273	Intermediate Similarity	NPC39657
0.8273	Intermediate Similarity	NPC213074
0.8271	Intermediate Similarity	NPC101624
0.8271	Intermediate Similarity	NPC184938
0.8261	Intermediate Similarity	NPC43508
0.8261	Intermediate Similarity	NPC476301
0.8261	Intermediate Similarity	NPC469586
0.8258	Intermediate Similarity	NPC294166
0.8258	Intermediate Similarity	NPC115022
0.8258	Intermediate Similarity	NPC6836
0.8258	Intermediate Similarity	NPC215037
0.8248	Intermediate Similarity	NPC113680
0.8248	Intermediate Similarity	NPC278961
0.8244	Intermediate Similarity	NPC254819
0.8244	Intermediate Similarity	NPC65942
0.8244	Intermediate Similarity	NPC219677
0.8244	Intermediate Similarity	NPC121376
0.8244	Intermediate Similarity	NPC281798
0.8244	Intermediate Similarity	NPC248307
0.8235	Intermediate Similarity	NPC469661
0.8235	Intermediate Similarity	NPC210192
0.8235	Intermediate Similarity	NPC264784
0.8235	Intermediate Similarity	NPC476385
0.8235	Intermediate Similarity	NPC476377
0.8235	Intermediate Similarity	NPC47471
0.8235	Intermediate Similarity	NPC134405
0.8235	Intermediate Similarity	NPC108674
0.8231	Intermediate Similarity	NPC253595
0.8214	Intermediate Similarity	NPC120728
0.8209	Intermediate Similarity	NPC40664
0.8209	Intermediate Similarity	NPC166180
0.8209	Intermediate Similarity	NPC469383
0.8209	Intermediate Similarity	NPC138350
0.8209	Intermediate Similarity	NPC197723
0.8209	Intermediate Similarity	NPC3293
0.8209	Intermediate Similarity	NPC165482

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 NPC471067 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	714
0.2-0.3	1372
0.3-0.4	3088
0.4-0.5	2143
0.5-0.6	1247
0.6-0.7	311
0.7-0.8	27
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
0.8358	Intermediate Similarity	NPD7266	Discontinued
0.8031	Intermediate Similarity	NPD1091	Approved
0.7874	Intermediate Similarity	NPD5125	Phase 3
0.7874	Intermediate Similarity	NPD5126	Approved
0.7676	Intermediate Similarity	NPD5058	Phase 3
0.7586	Intermediate Similarity	NPD2859	Approved
0.7586	Intermediate Similarity	NPD2860	Approved
0.7556	Intermediate Similarity	NPD3027	Phase 3
0.7518	Intermediate Similarity	NPD1613	Approved
0.7518	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2934	Approved
0.75	Intermediate Similarity	NPD2933	Approved
0.7482	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5588	Approved
0.7407	Intermediate Similarity	NPD2861	Phase 2
0.74	Intermediate Similarity	NPD8455	Phase 2
0.7395	Intermediate Similarity	NPD3020	Approved
0.7388	Intermediate Similarity	NPD3094	Phase 2
0.7381	Intermediate Similarity	NPD7843	Approved
0.7368	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD3022	Approved
0.728	Intermediate Similarity	NPD3021	Approved
0.7234	Intermediate Similarity	NPD4536	Approved
0.7234	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4538	Approved
0.7226	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4908	Phase 1
0.7222	Intermediate Similarity	NPD6674	Discontinued
0.7218	Intermediate Similarity	NPD3092	Approved
0.7218	Intermediate Similarity	NPD1610	Phase 2
0.7218	Intermediate Similarity	NPD3705	Approved
0.7215	Intermediate Similarity	NPD7228	Approved
0.7209	Intermediate Similarity	NPD7157	Approved
0.72	Intermediate Similarity	NPD2684	Approved
0.7183	Intermediate Similarity	NPD5960	Phase 3
0.7181	Intermediate Similarity	NPD1653	Approved
0.7176	Intermediate Similarity	NPD1548	Phase 1
0.7153	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD846	Approved
0.7131	Intermediate Similarity	NPD940	Approved
0.7123	Intermediate Similarity	NPD6190	Approved
0.7122	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1357	Approved
0.7113	Intermediate Similarity	NPD7097	Phase 1
0.7111	Intermediate Similarity	NPD4659	Approved
0.7107	Intermediate Similarity	NPD3818	Discontinued
0.7105	Intermediate Similarity	NPD37	Approved
0.7097	Intermediate Similarity	NPD6234	Discontinued
0.7078	Intermediate Similarity	NPD4967	Phase 2
0.7078	Intermediate Similarity	NPD4966	Approved
0.7078	Intermediate Similarity	NPD4965	Approved
0.7071	Intermediate Similarity	NPD6407	Approved
0.7071	Intermediate Similarity	NPD6405	Approved
0.7068	Intermediate Similarity	NPD5846	Approved
0.7068	Intermediate Similarity	NPD6516	Phase 2
0.7063	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD1242	Phase 1
0.7045	Intermediate Similarity	NPD3091	Approved
0.7037	Intermediate Similarity	NPD6559	Discontinued
0.7031	Intermediate Similarity	NPD969	Suspended
0.7027	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7074	Phase 3
0.7007	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4103	Phase 2
0.6986	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4380	Phase 2
0.6966	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7054	Approved
0.695	Remote Similarity	NPD6233	Phase 2
0.6934	Remote Similarity	NPD8651	Approved
0.6917	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7472	Approved
0.6911	Remote Similarity	NPD3028	Approved
0.6906	Remote Similarity	NPD5736	Approved
0.6905	Remote Similarity	NPD968	Approved
0.6879	Remote Similarity	NPD3764	Approved
0.6879	Remote Similarity	NPD6798	Discontinued
0.6875	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6355	Discontinued
0.6853	Remote Similarity	NPD4340	Discontinued
0.685	Remote Similarity	NPD290	Approved
0.6839	Remote Similarity	NPD2977	Approved
0.6839	Remote Similarity	NPD2978	Approved
0.6829	Remote Similarity	NPD7251	Discontinued
0.6829	Remote Similarity	NPD7685	Pre-registration
0.6829	Remote Similarity	NPD7240	Approved
0.6828	Remote Similarity	NPD7033	Discontinued
0.6828	Remote Similarity	NPD4108	Discontinued
0.6824	Remote Similarity	NPD4628	Phase 3
0.6815	Remote Similarity	NPD3095	Discontinued
0.6806	Remote Similarity	NPD5314	Approved
0.6792	Remote Similarity	NPD7199	Phase 2
0.6791	Remote Similarity	NPD7741	Discontinued
0.6788	Remote Similarity	NPD2562	Approved
0.6788	Remote Similarity	NPD7808	Phase 3
0.6788	Remote Similarity	NPD2561	Approved
0.6783	Remote Similarity	NPD3062	Approved
0.6783	Remote Similarity	NPD3061	Approved
0.6783	Remote Similarity	NPD3059	Approved
0.6783	Remote Similarity	NPD4060	Phase 1
0.6768	Remote Similarity	NPD6797	Phase 2
0.6763	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1652	Phase 2
0.6739	Remote Similarity	NPD3685	Discontinued
0.6739	Remote Similarity	NPD6583	Phase 3
0.6739	Remote Similarity	NPD6582	Phase 2
0.6736	Remote Similarity	NPD5735	Approved
0.6724	Remote Similarity	NPD111	Approved
0.6718	Remote Similarity	NPD5535	Approved
0.6715	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6663	Approved
0.6711	Remote Similarity	NPD4535	Phase 3
0.6709	Remote Similarity	NPD7075	Discontinued
0.6692	Remote Similarity	NPD6671	Approved
0.6691	Remote Similarity	NPD9381	Approved
0.6691	Remote Similarity	NPD9384	Approved
0.669	Remote Similarity	NPD7095	Approved
0.6687	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3620	Phase 2
0.6667	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5283	Phase 1
0.6647	Remote Similarity	NPD8313	Approved
0.6647	Remote Similarity	NPD8312	Approved
0.6646	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD228	Approved
0.6622	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5763	Approved
0.6622	Remote Similarity	NPD5762	Approved
0.6622	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD5124	Phase 1
0.6621	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD4750	Phase 3
0.6615	Remote Similarity	NPD5451	Approved
0.6605	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3400	Discontinued
0.6597	Remote Similarity	NPD4404	Approved
0.6597	Remote Similarity	NPD4062	Phase 3
0.6596	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6584	Phase 3
0.6593	Remote Similarity	NPD856	Approved
0.6593	Remote Similarity	NPD16	Approved
0.6591	Remote Similarity	NPD7635	Approved
0.6585	Remote Similarity	NPD844	Approved
0.6585	Remote Similarity	NPD1809	Phase 2
0.6579	Remote Similarity	NPD7212	Phase 2
0.6579	Remote Similarity	NPD7213	Phase 3
0.6577	Remote Similarity	NPD1549	Phase 2
0.6577	Remote Similarity	NPD2424	Discontinued
0.6575	Remote Similarity	NPD2568	Approved
0.6575	Remote Similarity	NPD6653	Approved
0.6573	Remote Similarity	NPD4625	Phase 3
0.6566	Remote Similarity	NPD7007	Discovery
0.6562	Remote Similarity	NPD5048	Discontinued
0.6561	Remote Similarity	NPD1934	Approved
0.6558	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD845	Approved
0.6552	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD9545	Approved
0.6541	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD2234	Approved
0.6541	Remote Similarity	NPD2229	Approved
0.6541	Remote Similarity	NPD2228	Approved
0.6536	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD3536	Discontinued
0.6536	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7447	Phase 1
0.6536	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4236	Phase 3
0.6533	Remote Similarity	NPD4237	Approved
0.6522	Remote Similarity	NPD3847	Discontinued
0.6519	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD289	Clinical (unspecified phase)
0.65	Remote Similarity	NPD9622	Approved
0.65	Remote Similarity	NPD4749	Approved
0.65	Remote Similarity	NPD2982	Phase 2
0.65	Remote Similarity	NPD7876	Discontinued
0.65	Remote Similarity	NPD2983	Phase 2
0.65	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD2629	Approved
0.6475	Remote Similarity	NPD1535	Discovery
0.6475	Remote Similarity	NPD422	Phase 1
0.6474	Remote Similarity	NPD6056	Approved
0.6474	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6057	Approved
0.6471	Remote Similarity	NPD318	Approved
0.6471	Remote Similarity	NPD317	Approved
0.6463	Remote Similarity	NPD3052	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