NPASS Compound

Structure

NPC470907 OpenBabel07101718282D 42 45 0 0 1 0 0 0 0 0999 V2000 -7.8988 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7648 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8988 -4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6308 -4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 -5.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 -5.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8988 -5.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6308 -5.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 -6.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 -6.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2872 -1.2459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7648 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -5.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7648 -5.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -7.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 -2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8366 -2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8366 -3.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7026 -4.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5686 -3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5686 -2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2007 -0.8392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7648 -6.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -8.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -4.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0169 -2.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3917 -0.2514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -1.4945 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 -4.4347 -2.4945 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 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 18 1 0 0 0 0 5 10 1 0 0 0 0 5 18 2 0 0 0 0 6 11 2 0 0 0 0 6 18 1 0 0 0 0 7 12 1 0 0 0 0 7 19 2 0 0 0 0 8 13 2 0 0 0 0 8 19 1 0 0 0 0 9 14 1 0 0 0 0 9 19 1 0 0 0 0 10 20 2 0 0 0 0 11 20 1 0 0 0 0 12 21 2 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 39 1 0 0 0 0 16 30 1 0 0 0 0 16 31 1 0 0 0 0 17 30 1 0 0 0 0 17 40 1 0 0 0 0 20 32 1 0 0 0 0 21 33 1 0 0 0 0 22 4 1 1 0 0 0 22 41 1 0 0 0 0 23 15 1 6 0 0 0 23 24 1 0 0 0 0 23 42 1 0 0 0 0 24 25 1 0 0 0 0 24 34 1 6 0 0 0 25 26 1 0 0 0 0 25 35 1 1 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 30 1 1 0 0 0 27 37 1 0 0 0 0 28 41 1 6 0 0 0 28 42 1 0 0 0 0 29 39 1 6 0 0 0 29 40 1 0 0 0 0 30 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.27
Volume:	582.874
LogP:	1.975
LogD:	1.627
LogS:	-2.851
# 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:	4.612
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:	-6.184
MDCK Permeability:	6.957114692340838e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.405
Human Intestinal Absorption (HIA):	0.981
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	94.55787658691406%
Volume Distribution (VD):	0.191
Pgp-substrate:	2.742542028427124%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.096
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.208
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.034
CYP3A4-substrate:	0.116

ADMET: Excretion

Clearance (CL):	1.734
Half-life (T1/2):	0.703

ADMET: Toxicity

hERG Blockers:	0.391
Human Hepatotoxicity (H-HT):	0.088
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.62
Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.365
Skin Sensitization:	0.963
Carcinogencity:	0.065
Eye Corrosion:	0.003
Eye Irritation:	0.026
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC470907

Natural Product ID:	NPC470907
*Common Name:**	(2R,3R,4R,5R,6R)-2-[(3R)-1,7-Bis(4-Hydroxyphenyl)Heptan-3-Yl]Oxy-6-[[(2R,3R,4R)-3,4-Dihydroxy-4-(Hydroxymethyl)Oxolan-2-Yl]Oxymethyl]Oxane-3,4,5-Triol
IUPAC Name:	(2R,3R,4R,5R,6R)-2-[(3R)-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	JLMGCBFIPZDHLZ-XVRIUCGVSA-N
Standard InCHI:	InChI=1S/C30H42O12/c31-16-30(38)17-40-29(27(30)37)39-15-23-24(34)25(35)26(36)28(42-23)41-22(14-9-19-7-12-21(33)13-8-19)4-2-1-3-18-5-10-20(32)11-6-18/h5-8,10-13,22-29,31-38H,1-4,9,14-17H2/t22-,23-,24+,25-,26-,27+,28-,29-,30-/m1/s1
SMILES:	OC[C@@]1(O)CO[C@H]([C@@H]1O)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:	CHEMBL2311205
PubChem CID:	71717299
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
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	floral spikes	n.a.	n.a.	PMID[17346076]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[9873651]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	28.3	%	PMID[558816]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	38.4	%	PMID[558816]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	43.9	%	PMID[558816]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	55.3	%	PMID[558816]

☑ 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 NPC470907 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	312
0.1-0.2	1158
0.2-0.3	2872
0.3-0.4	8281
0.4-0.5	10944
0.5-0.6	10476
0.6-0.7	7016
0.7-0.8	1434
0.8-0.85	156
0.85-0.9	30
0.9-0.95	14
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC178449
1.0	High Similarity	NPC232454
0.9914	High Similarity	NPC471067
0.9741	High Similarity	NPC469703
0.9741	High Similarity	NPC201402
0.9741	High Similarity	NPC469704
0.9741	High Similarity	NPC160854
0.9667	High Similarity	NPC469687
0.9658	High Similarity	NPC469686
0.9573	High Similarity	NPC476445
0.9573	High Similarity	NPC476448
0.9573	High Similarity	NPC469548
0.9487	High Similarity	NPC282409
0.9487	High Similarity	NPC469702
0.9206	High Similarity	NPC164172
0.92	High Similarity	NPC478255
0.9187	High Similarity	NPC264900
0.9187	High Similarity	NPC79715
0.9187	High Similarity	NPC108659
0.9187	High Similarity	NPC231607
0.9167	High Similarity	NPC55608
0.9145	High Similarity	NPC148055
0.9138	High Similarity	NPC157338
0.9127	High Similarity	NPC471095
0.9127	High Similarity	NPC471066
0.9106	High Similarity	NPC94179
0.904	High Similarity	NPC184092
0.9024	High Similarity	NPC90318
0.8968	High Similarity	NPC469705
0.8968	High Similarity	NPC17968
0.8968	High Similarity	NPC470122
0.896	High Similarity	NPC225307
0.8923	High Similarity	NPC469696
0.888	High Similarity	NPC288416
0.8828	High Similarity	NPC254275
0.8824	High Similarity	NPC175771
0.8824	High Similarity	NPC301651
0.8824	High Similarity	NPC473556
0.8814	High Similarity	NPC313193
0.881	High Similarity	NPC158673
0.881	High Similarity	NPC148982
0.875	High Similarity	NPC235294
0.875	High Similarity	NPC46137
0.8712	High Similarity	NPC171134
0.8712	High Similarity	NPC321638
0.8712	High Similarity	NPC328273
0.8712	High Similarity	NPC321184
0.8699	High Similarity	NPC266045
0.864	High Similarity	NPC287429
0.8615	High Similarity	NPC28637
0.8605	High Similarity	NPC138777
0.8605	High Similarity	NPC476407
0.8605	High Similarity	NPC225384
0.8605	High Similarity	NPC246869
0.8594	High Similarity	NPC469549
0.8593	High Similarity	NPC46092
0.8583	High Similarity	NPC173150
0.8583	High Similarity	NPC106677
0.8583	High Similarity	NPC471882
0.8583	High Similarity	NPC45224
0.8583	High Similarity	NPC471881
0.8583	High Similarity	NPC35288
0.8583	High Similarity	NPC156692
0.8582	High Similarity	NPC472711
0.8571	High Similarity	NPC83218
0.8571	High Similarity	NPC126991
0.8561	High Similarity	NPC199459
0.8561	High Similarity	NPC177035
0.8561	High Similarity	NPC52277
0.8529	High Similarity	NPC129417
0.8529	High Similarity	NPC283995
0.8529	High Similarity	NPC470235
0.8529	High Similarity	NPC84181
0.8519	High Similarity	NPC472353
0.8504	High Similarity	NPC61181
0.8504	High Similarity	NPC471157
0.8504	High Similarity	NPC252114
0.8487	Intermediate Similarity	NPC153795
0.8487	Intermediate Similarity	NPC290353
0.8487	Intermediate Similarity	NPC42911
0.8485	Intermediate Similarity	NPC79957
0.8485	Intermediate Similarity	NPC263829
0.848	Intermediate Similarity	NPC476142
0.848	Intermediate Similarity	NPC52097
0.8467	Intermediate Similarity	NPC18979
0.8462	Intermediate Similarity	NPC475824
0.8456	Intermediate Similarity	NPC477898
0.8456	Intermediate Similarity	NPC105005
0.8456	Intermediate Similarity	NPC185307
0.8456	Intermediate Similarity	NPC470950
0.8456	Intermediate Similarity	NPC478250
0.8456	Intermediate Similarity	NPC40305
0.8438	Intermediate Similarity	NPC103533
0.8433	Intermediate Similarity	NPC156376
0.8425	Intermediate Similarity	NPC470510
0.8413	Intermediate Similarity	NPC212176
0.8409	Intermediate Similarity	NPC470881
0.8409	Intermediate Similarity	NPC476411
0.8409	Intermediate Similarity	NPC287597
0.8409	Intermediate Similarity	NPC886
0.8409	Intermediate Similarity	NPC34293
0.8406	Intermediate Similarity	NPC112861
0.84	Intermediate Similarity	NPC11724
0.8394	Intermediate Similarity	NPC300894
0.8394	Intermediate Similarity	NPC141455
0.8394	Intermediate Similarity	NPC196063
0.8394	Intermediate Similarity	NPC296954
0.8382	Intermediate Similarity	NPC476356
0.837	Intermediate Similarity	NPC106944
0.8358	Intermediate Similarity	NPC87777
0.8358	Intermediate Similarity	NPC470413
0.8358	Intermediate Similarity	NPC138738
0.8358	Intermediate Similarity	NPC260425
0.8358	Intermediate Similarity	NPC304152
0.8358	Intermediate Similarity	NPC262328
0.8346	Intermediate Similarity	NPC158325
0.8346	Intermediate Similarity	NPC103398
0.8346	Intermediate Similarity	NPC123988
0.8346	Intermediate Similarity	NPC180171
0.8333	Intermediate Similarity	NPC22150
0.8333	Intermediate Similarity	NPC469586
0.8333	Intermediate Similarity	NPC38041
0.8333	Intermediate Similarity	NPC279298
0.8333	Intermediate Similarity	NPC6836
0.8333	Intermediate Similarity	NPC215037
0.8321	Intermediate Similarity	NPC475067
0.832	Intermediate Similarity	NPC269242
0.832	Intermediate Similarity	NPC476872
0.832	Intermediate Similarity	NPC198734
0.832	Intermediate Similarity	NPC469412
0.8319	Intermediate Similarity	NPC264784
0.8309	Intermediate Similarity	NPC471908
0.8296	Intermediate Similarity	NPC89105
0.8296	Intermediate Similarity	NPC205195
0.8296	Intermediate Similarity	NPC197316
0.8296	Intermediate Similarity	NPC81515
0.8296	Intermediate Similarity	NPC64141
0.8296	Intermediate Similarity	NPC476383
0.8296	Intermediate Similarity	NPC472350
0.8296	Intermediate Similarity	NPC68092
0.8293	Intermediate Similarity	NPC476266
0.8284	Intermediate Similarity	NPC471345
0.8284	Intermediate Similarity	NPC469383
0.8276	Intermediate Similarity	NPC47286
0.8273	Intermediate Similarity	NPC229505
0.8271	Intermediate Similarity	NPC35731
0.8271	Intermediate Similarity	NPC169398
0.8271	Intermediate Similarity	NPC187194
0.8261	Intermediate Similarity	NPC473046
0.8261	Intermediate Similarity	NPC187774
0.8261	Intermediate Similarity	NPC118385
0.8261	Intermediate Similarity	NPC472713
0.8261	Intermediate Similarity	NPC472712
0.8258	Intermediate Similarity	NPC473924
0.8258	Intermediate Similarity	NPC26080
0.8258	Intermediate Similarity	NPC165686
0.8258	Intermediate Similarity	NPC303422
0.8258	Intermediate Similarity	NPC252833
0.8258	Intermediate Similarity	NPC85799
0.8248	Intermediate Similarity	NPC148080
0.8248	Intermediate Similarity	NPC469623
0.8248	Intermediate Similarity	NPC246947
0.824	Intermediate Similarity	NPC60589
0.824	Intermediate Similarity	NPC469708
0.8222	Intermediate Similarity	NPC100558
0.8222	Intermediate Similarity	NPC302583
0.8222	Intermediate Similarity	NPC84789
0.8222	Intermediate Similarity	NPC310252
0.8222	Intermediate Similarity	NPC78363
0.8214	Intermediate Similarity	NPC224674
0.8214	Intermediate Similarity	NPC114505
0.8214	Intermediate Similarity	NPC193473
0.8214	Intermediate Similarity	NPC31325
0.8214	Intermediate Similarity	NPC15956
0.8214	Intermediate Similarity	NPC275284
0.8214	Intermediate Similarity	NPC213074
0.8214	Intermediate Similarity	NPC39657
0.8209	Intermediate Similarity	NPC184938
0.8209	Intermediate Similarity	NPC101624
0.8201	Intermediate Similarity	NPC43508
0.8201	Intermediate Similarity	NPC476301
0.8195	Intermediate Similarity	NPC115022
0.8195	Intermediate Similarity	NPC254398
0.8195	Intermediate Similarity	NPC294166
0.8195	Intermediate Similarity	NPC25821
0.8188	Intermediate Similarity	NPC278961
0.8188	Intermediate Similarity	NPC113680
0.8182	Intermediate Similarity	NPC65942
0.8182	Intermediate Similarity	NPC281798
0.8182	Intermediate Similarity	NPC121376
0.8182	Intermediate Similarity	NPC248307
0.8182	Intermediate Similarity	NPC254819
0.8182	Intermediate Similarity	NPC219677
0.8175	Intermediate Similarity	NPC476385
0.8175	Intermediate Similarity	NPC134405
0.8175	Intermediate Similarity	NPC469661
0.8175	Intermediate Similarity	NPC229600
0.8175	Intermediate Similarity	NPC476377
0.8175	Intermediate Similarity	NPC210192
0.8175	Intermediate Similarity	NPC108674

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 NPC470907 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	711
0.2-0.3	1398
0.3-0.4	3090
0.4-0.5	2129
0.5-0.6	1245
0.6-0.7	304
0.7-0.8	22
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
0.8296	Intermediate Similarity	NPD7266	Discontinued
0.7969	Intermediate Similarity	NPD1091	Approved
0.7812	Intermediate Similarity	NPD5125	Phase 3
0.7812	Intermediate Similarity	NPD5126	Approved
0.7746	Intermediate Similarity	NPD5058	Phase 3
0.7521	Intermediate Similarity	NPD2859	Approved
0.7521	Intermediate Similarity	NPD2860	Approved
0.75	Intermediate Similarity	NPD3027	Phase 3
0.7464	Intermediate Similarity	NPD1613	Approved
0.7464	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2934	Approved
0.7436	Intermediate Similarity	NPD2933	Approved
0.7429	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5588	Approved
0.7353	Intermediate Similarity	NPD2861	Phase 2
0.7351	Intermediate Similarity	NPD8455	Phase 2
0.7333	Intermediate Similarity	NPD3094	Phase 2
0.7333	Intermediate Similarity	NPD3020	Approved
0.7323	Intermediate Similarity	NPD7843	Approved
0.732	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3021	Approved
0.7222	Intermediate Similarity	NPD3022	Approved
0.7192	Intermediate Similarity	NPD6190	Approved
0.7183	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4538	Approved
0.7183	Intermediate Similarity	NPD4536	Approved
0.7183	Intermediate Similarity	NPD7097	Phase 1
0.7174	Intermediate Similarity	NPD4908	Phase 1
0.7174	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6674	Discontinued
0.717	Intermediate Similarity	NPD7228	Approved
0.7164	Intermediate Similarity	NPD1610	Phase 2
0.7164	Intermediate Similarity	NPD3092	Approved
0.7164	Intermediate Similarity	NPD3705	Approved
0.7154	Intermediate Similarity	NPD7157	Approved
0.7143	Intermediate Similarity	NPD2684	Approved
0.7133	Intermediate Similarity	NPD5960	Phase 3
0.7133	Intermediate Similarity	NPD1653	Approved
0.7121	Intermediate Similarity	NPD1548	Phase 1
0.7101	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4103	Phase 2
0.708	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD940	Approved
0.7073	Intermediate Similarity	NPD846	Approved
0.7071	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1357	Approved
0.7063	Intermediate Similarity	NPD3818	Discontinued
0.7059	Intermediate Similarity	NPD37	Approved
0.7059	Intermediate Similarity	NPD4659	Approved
0.7051	Intermediate Similarity	NPD6234	Discontinued
0.7032	Intermediate Similarity	NPD4966	Approved
0.7032	Intermediate Similarity	NPD4965	Approved
0.7032	Intermediate Similarity	NPD4967	Phase 2
0.7021	Intermediate Similarity	NPD6405	Approved
0.7021	Intermediate Similarity	NPD6407	Approved
0.7019	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5846	Approved
0.7015	Intermediate Similarity	NPD6516	Phase 2
0.6994	Remote Similarity	NPD6559	Discontinued
0.6992	Remote Similarity	NPD1242	Phase 1
0.6992	Remote Similarity	NPD3091	Approved
0.698	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD969	Suspended
0.6975	Remote Similarity	NPD7074	Phase 3
0.695	Remote Similarity	NPD3764	Approved
0.6939	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4380	Phase 2
0.6918	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7054	Approved
0.6901	Remote Similarity	NPD6233	Phase 2
0.6897	Remote Similarity	NPD7033	Discontinued
0.689	Remote Similarity	NPD7685	Pre-registration
0.6884	Remote Similarity	NPD8651	Approved
0.6871	Remote Similarity	NPD7472	Approved
0.6866	Remote Similarity	NPD7741	Discontinued
0.686	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5736	Approved
0.6855	Remote Similarity	NPD3028	Approved
0.685	Remote Similarity	NPD968	Approved
0.6835	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6798	Discontinued
0.6822	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4340	Discontinued
0.6806	Remote Similarity	NPD6355	Discontinued
0.6797	Remote Similarity	NPD290	Approved
0.6795	Remote Similarity	NPD2978	Approved
0.6795	Remote Similarity	NPD2977	Approved
0.6788	Remote Similarity	NPD7251	Discontinued
0.6788	Remote Similarity	NPD7240	Approved
0.6781	Remote Similarity	NPD4108	Discontinued
0.6779	Remote Similarity	NPD4628	Phase 3
0.6767	Remote Similarity	NPD6671	Approved
0.6765	Remote Similarity	NPD3095	Discontinued
0.6761	Remote Similarity	NPD7095	Approved
0.6759	Remote Similarity	NPD5314	Approved
0.675	Remote Similarity	NPD7199	Phase 2
0.6747	Remote Similarity	NPD7808	Phase 3
0.6739	Remote Similarity	NPD2561	Approved
0.6739	Remote Similarity	NPD2562	Approved
0.6736	Remote Similarity	NPD4060	Phase 1
0.6736	Remote Similarity	NPD3059	Approved
0.6736	Remote Similarity	NPD3062	Approved
0.6736	Remote Similarity	NPD3061	Approved
0.6727	Remote Similarity	NPD6797	Phase 2
0.6726	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1652	Phase 2
0.6691	Remote Similarity	NPD6582	Phase 2
0.6691	Remote Similarity	NPD6583	Phase 3
0.6691	Remote Similarity	NPD3685	Discontinued
0.669	Remote Similarity	NPD5124	Phase 1
0.669	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.669	Remote Similarity	NPD5735	Approved
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD111	Approved
0.6667	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7075	Discontinued
0.6667	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4535	Phase 3
0.6667	Remote Similarity	NPD5535	Approved
0.6647	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2424	Discontinued
0.6643	Remote Similarity	NPD4625	Phase 3
0.6642	Remote Similarity	NPD9381	Approved
0.6642	Remote Similarity	NPD9384	Approved
0.6621	Remote Similarity	NPD3620	Phase 2
0.6621	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD2228	Approved
0.6617	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD2234	Approved
0.6617	Remote Similarity	NPD2229	Approved
0.6617	Remote Similarity	NPD5283	Phase 1
0.6607	Remote Similarity	NPD8313	Approved
0.6607	Remote Similarity	NPD8312	Approved
0.6604	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD228	Approved
0.6577	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5763	Approved
0.6577	Remote Similarity	NPD5762	Approved
0.6577	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4749	Approved
0.6565	Remote Similarity	NPD5451	Approved
0.6565	Remote Similarity	NPD4750	Phase 3
0.6564	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3400	Discontinued
0.6552	Remote Similarity	NPD4404	Approved
0.6552	Remote Similarity	NPD4062	Phase 3
0.6549	Remote Similarity	NPD6584	Phase 3
0.6549	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD856	Approved
0.6544	Remote Similarity	NPD16	Approved
0.6541	Remote Similarity	NPD7635	Approved
0.6536	Remote Similarity	NPD7212	Phase 2
0.6536	Remote Similarity	NPD7213	Phase 3
0.6533	Remote Similarity	NPD1549	Phase 2
0.6532	Remote Similarity	NPD1809	Phase 2
0.6532	Remote Similarity	NPD844	Approved
0.6532	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD2568	Approved
0.6531	Remote Similarity	NPD6653	Approved
0.6527	Remote Similarity	NPD7007	Discovery
0.6522	Remote Similarity	NPD4059	Approved
0.6519	Remote Similarity	NPD4198	Discontinued
0.6519	Remote Similarity	NPD1934	Approved
0.6516	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD5048	Discontinued
0.6507	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD2238	Phase 2
0.6504	Remote Similarity	NPD845	Approved
0.6503	Remote Similarity	NPD3787	Discontinued
0.6496	Remote Similarity	NPD9545	Approved
0.6494	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7447	Phase 1
0.6494	Remote Similarity	NPD3536	Discontinued
0.6494	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.649	Remote Similarity	NPD4236	Phase 3
0.649	Remote Similarity	NPD4237	Approved
0.6478	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD3847	Discontinued
0.6471	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1375	Discontinued
0.6457	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD2982	Phase 2
0.6454	Remote Similarity	NPD9622	Approved
0.6454	Remote Similarity	NPD7876	Discontinued
0.6454	Remote Similarity	NPD2983	Phase 2
0.6454	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD2629	Approved
0.6433	Remote Similarity	NPD6056	Approved
0.6433	Remote Similarity	NPD6057	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