NPASS Compound

Structure

NPC469687 OpenBabel07101719512D 51 55 0 0 1 0 0 0 0 0999 V2000 -6.1667 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 -2.9945 0.0000 C 0 0 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 -4.4347 -2.4945 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 -4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -5.9945 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 -4.4347 -4.4945 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 -7.8988 -5.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -6.9945 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 -3.5686 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1449 2.7024 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 -7.7494 0.8419 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 -7.0327 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -5.4945 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 -4.4347 -7.4945 0.0000 C 0 0 0 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 -3.5686 0.0055 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7026 0.5055 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8366 0.0055 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8366 -0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2712 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7026 -1.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1667 0.5055 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 -7.2494 1.7079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.9539 3.2902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1826 -2.2404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 -6.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -8.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 1.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5281 2.1691 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 -8.0584 2.2957 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 -5.3007 0.0055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0803 0.0987 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 -2.7026 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -0.9945 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 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 20 1 0 0 0 0 5 10 1 0 0 0 0 5 20 2 0 0 0 0 6 11 2 0 0 0 0 6 20 1 0 0 0 0 7 12 1 0 0 0 0 7 21 2 0 0 0 0 8 13 2 0 0 0 0 8 21 1 0 0 0 0 9 14 1 0 0 0 0 9 21 1 0 0 0 0 10 22 2 0 0 0 0 11 22 1 0 0 0 0 12 23 2 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 15 46 1 0 0 0 0 16 34 1 0 0 0 0 16 36 1 0 0 0 0 17 35 1 0 0 0 0 17 37 1 0 0 0 0 18 34 1 0 0 0 0 18 47 1 0 0 0 0 19 35 1 0 0 0 0 19 48 1 0 0 0 0 22 38 1 0 0 0 0 23 39 1 0 0 0 0 24 4 1 1 0 0 0 24 49 1 0 0 0 0 25 15 1 6 0 0 0 25 26 1 0 0 0 0 25 50 1 0 0 0 0 26 27 1 0 0 0 0 26 40 1 1 0 0 0 27 28 1 0 0 0 0 27 41 1 6 0 0 0 28 31 1 0 0 0 0 28 51 1 1 0 0 0 29 32 1 0 0 0 0 29 34 1 6 0 0 0 29 42 1 0 0 0 0 30 33 1 0 0 0 0 30 35 1 6 0 0 0 30 43 1 0 0 0 0 31 49 1 6 0 0 0 31 50 1 0 0 0 0 32 46 1 6 0 0 0 32 47 1 0 0 0 0 33 48 1 0 0 0 0 33 51 1 1 0 0 0 34 44 1 6 0 0 0 35 45 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	726.31
Volume:	695.959
LogP:	1.314
LogD:	1.214
LogS:	-3.099
# Rotatable Bonds:	17
TPSA:	257.68
# H-Bond Aceptor:	16
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.084
Synthetic Accessibility Score:	5.276
Fsp3:	0.657
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:	-6.382
MDCK Permeability:	9.732661965244915e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.993
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.146
Plasma Protein Binding (PPB):	91.38668060302734%
Volume Distribution (VD):	0.111
Pgp-substrate:	5.663139343261719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.029
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.071
CYP3A4-substrate:	0.131

ADMET: Excretion

Clearance (CL):	0.752
Half-life (T1/2):	0.807

ADMET: Toxicity

hERG Blockers:	0.336
Human Hepatotoxicity (H-HT):	0.101
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.251
Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.865
Carcinogencity:	0.365
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.007

Download Data

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

Natural Product: NPC469687

Natural Product ID:	NPC469687
*Common Name:**	(3R)-1,7-Bis-(4-Hydroxyphenyl)-3-Heptanol-3-O-[2,6-Bis-O-(B-D-Apiofuranosyl)-B-D-Glucopyranoside
IUPAC Name:	(2R,3S,4S,5R,6R)-6-[(3R)-1,7-bis(4-hydroxyphenyl)heptan-3-yl]oxy-5-[(2R,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-2-[[(2R,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]oxane-3,4-diol
Synonyms:
Standard InCHIKey:	ZYZHMHXSPPAVCD-RACJMKAXSA-N
Standard InCHI:	InChI=1S/C35H50O16/c36-16-34(44)18-47-32(29(34)42)46-15-25-26(40)27(41)28(51-33-30(43)35(45,17-37)19-48-33)31(50-25)49-24(14-9-21-7-12-23(39)13-8-21)4-2-1-3-20-5-10-22(38)11-6-20/h5-8,10-13,24-33,36-45H,1-4,9,14-19H2/t24-,25-,26-,27+,28-,29-,30-,31-,32-,33-,34+,35+/m1/s1
SMILES:	C1C(C(C(O1)OCC2C(C(C(C(O2)OC(CCCCC3=CC=C(C=C3)O)CCC4=CC=C(C=C4)O)OC5C(C(CO5)(CO)O)O)O)O)O)(CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1098688
PubChem CID:	46889082
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	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	=	22.1	%	PMID[514819]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	23.2	%	PMID[514819]

☑ 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 NPC469687 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	353
0.1-0.2	1131
0.2-0.3	2947
0.3-0.4	8506
0.4-0.5	11037
0.5-0.6	11390
0.6-0.7	6163
0.7-0.8	1051
0.8-0.85	86
0.85-0.9	17
0.9-0.95	15
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC232454
0.9667	High Similarity	NPC178449
0.9667	High Similarity	NPC470907
0.9583	High Similarity	NPC471067
0.9417	High Similarity	NPC469703
0.9417	High Similarity	NPC469704
0.9417	High Similarity	NPC201402
0.9417	High Similarity	NPC160854
0.9339	High Similarity	NPC469686
0.9256	High Similarity	NPC476448
0.9256	High Similarity	NPC476445
0.9256	High Similarity	NPC469548
0.9231	High Similarity	NPC469696
0.9174	High Similarity	NPC282409
0.9174	High Similarity	NPC469702
0.8923	High Similarity	NPC164172
0.8915	High Similarity	NPC478255
0.8898	High Similarity	NPC264900
0.8898	High Similarity	NPC79715
0.8898	High Similarity	NPC231607
0.8898	High Similarity	NPC108659
0.8871	High Similarity	NPC55608
0.8846	High Similarity	NPC471066
0.8846	High Similarity	NPC471095
0.8843	High Similarity	NPC148055
0.8833	High Similarity	NPC157338
0.8819	High Similarity	NPC94179
0.876	High Similarity	NPC184092
0.875	High Similarity	NPC40305
0.874	High Similarity	NPC90318
0.8692	High Similarity	NPC469705
0.8692	High Similarity	NPC470122
0.8692	High Similarity	NPC17968
0.8682	High Similarity	NPC225307
0.8636	High Similarity	NPC28637
0.8605	High Similarity	NPC288416
0.8561	High Similarity	NPC254275
0.8551	High Similarity	NPC84181
0.8538	High Similarity	NPC158673
0.8538	High Similarity	NPC148982
0.8537	High Similarity	NPC473556
0.8537	High Similarity	NPC175771
0.8537	High Similarity	NPC301651
0.8525	High Similarity	NPC313193
0.8507	High Similarity	NPC263829
0.8489	Intermediate Similarity	NPC18979
0.8485	Intermediate Similarity	NPC235294
0.8485	Intermediate Similarity	NPC46137
0.8478	Intermediate Similarity	NPC105005
0.8478	Intermediate Similarity	NPC477898
0.8462	Intermediate Similarity	NPC35288
0.8462	Intermediate Similarity	NPC103533
0.8462	Intermediate Similarity	NPC173150
0.8462	Intermediate Similarity	NPC471882
0.8462	Intermediate Similarity	NPC45224
0.8462	Intermediate Similarity	NPC471881
0.8462	Intermediate Similarity	NPC156692
0.8456	Intermediate Similarity	NPC321638
0.8456	Intermediate Similarity	NPC321184
0.8456	Intermediate Similarity	NPC171134
0.8456	Intermediate Similarity	NPC328273
0.8456	Intermediate Similarity	NPC156376
0.8451	Intermediate Similarity	NPC475224
0.8429	Intermediate Similarity	NPC112861
0.8425	Intermediate Similarity	NPC266045
0.8417	Intermediate Similarity	NPC300894
0.8417	Intermediate Similarity	NPC141455
0.8417	Intermediate Similarity	NPC296954
0.8417	Intermediate Similarity	NPC196063
0.8385	Intermediate Similarity	NPC61181
0.8372	Intermediate Similarity	NPC287429
0.8357	Intermediate Similarity	NPC22150
0.8357	Intermediate Similarity	NPC469586
0.8357	Intermediate Similarity	NPC38041
0.8357	Intermediate Similarity	NPC279298
0.8346	Intermediate Similarity	NPC476407
0.8346	Intermediate Similarity	NPC246869
0.8346	Intermediate Similarity	NPC138777
0.8346	Intermediate Similarity	NPC225384
0.8345	Intermediate Similarity	NPC46092
0.8333	Intermediate Similarity	NPC469549
0.8333	Intermediate Similarity	NPC471908
0.8333	Intermediate Similarity	NPC472711
0.8321	Intermediate Similarity	NPC106677
0.8309	Intermediate Similarity	NPC177035
0.8309	Intermediate Similarity	NPC199459
0.8309	Intermediate Similarity	NPC469383
0.8309	Intermediate Similarity	NPC52277
0.8308	Intermediate Similarity	NPC126991
0.8308	Intermediate Similarity	NPC83218
0.8298	Intermediate Similarity	NPC229505
0.8298	Intermediate Similarity	NPC276753
0.8298	Intermediate Similarity	NPC205796
0.8286	Intermediate Similarity	NPC470235
0.8286	Intermediate Similarity	NPC283995
0.8286	Intermediate Similarity	NPC129417
0.8273	Intermediate Similarity	NPC472353
0.8273	Intermediate Similarity	NPC246947
0.8244	Intermediate Similarity	NPC471157
0.8244	Intermediate Similarity	NPC252114
0.8235	Intermediate Similarity	NPC79957
0.8217	Intermediate Similarity	NPC52097
0.8217	Intermediate Similarity	NPC476142
0.8214	Intermediate Similarity	NPC278961
0.8214	Intermediate Similarity	NPC185307
0.8214	Intermediate Similarity	NPC478250
0.8214	Intermediate Similarity	NPC113680
0.8214	Intermediate Similarity	NPC470950
0.8211	Intermediate Similarity	NPC42911
0.8211	Intermediate Similarity	NPC153795
0.8211	Intermediate Similarity	NPC290353
0.8209	Intermediate Similarity	NPC475824
0.8201	Intermediate Similarity	NPC476377
0.8201	Intermediate Similarity	NPC47471
0.8194	Intermediate Similarity	NPC98624
0.8194	Intermediate Similarity	NPC35097
0.8188	Intermediate Similarity	NPC205195
0.8182	Intermediate Similarity	NPC120728
0.8168	Intermediate Similarity	NPC470510
0.8162	Intermediate Similarity	NPC34293
0.8162	Intermediate Similarity	NPC886
0.8162	Intermediate Similarity	NPC287597
0.8162	Intermediate Similarity	NPC470881
0.8162	Intermediate Similarity	NPC476411
0.8156	Intermediate Similarity	NPC471063
0.8154	Intermediate Similarity	NPC212176
0.8143	Intermediate Similarity	NPC476356
0.8143	Intermediate Similarity	NPC469623
0.8143	Intermediate Similarity	NPC148080
0.814	Intermediate Similarity	NPC11724
0.8129	Intermediate Similarity	NPC475530
0.8129	Intermediate Similarity	NPC473799
0.8129	Intermediate Similarity	NPC106944
0.8125	Intermediate Similarity	NPC286235
0.8125	Intermediate Similarity	NPC55158
0.8125	Intermediate Similarity	NPC51328
0.8116	Intermediate Similarity	NPC262328
0.8116	Intermediate Similarity	NPC87777
0.8116	Intermediate Similarity	NPC304152
0.8116	Intermediate Similarity	NPC470413
0.8116	Intermediate Similarity	NPC260425
0.8116	Intermediate Similarity	NPC138738
0.8102	Intermediate Similarity	NPC103398
0.8102	Intermediate Similarity	NPC158325
0.8102	Intermediate Similarity	NPC123988
0.8102	Intermediate Similarity	NPC180171
0.8088	Intermediate Similarity	NPC6836
0.8088	Intermediate Similarity	NPC215037
0.8085	Intermediate Similarity	NPC175214
0.8085	Intermediate Similarity	NPC119537
0.8085	Intermediate Similarity	NPC112
0.8085	Intermediate Similarity	NPC476380
0.8085	Intermediate Similarity	NPC205864
0.8085	Intermediate Similarity	NPC76406
0.8085	Intermediate Similarity	NPC476378
0.8085	Intermediate Similarity	NPC264632
0.8085	Intermediate Similarity	NPC298257
0.8085	Intermediate Similarity	NPC476375
0.8085	Intermediate Similarity	NPC476384
0.8085	Intermediate Similarity	NPC96795
0.8085	Intermediate Similarity	NPC476381
0.8085	Intermediate Similarity	NPC476397
0.8085	Intermediate Similarity	NPC247032
0.8085	Intermediate Similarity	NPC269141
0.8074	Intermediate Similarity	NPC475067
0.8071	Intermediate Similarity	NPC476385
0.8071	Intermediate Similarity	NPC134405
0.8069	Intermediate Similarity	NPC470934
0.8069	Intermediate Similarity	NPC188393
0.8062	Intermediate Similarity	NPC469412
0.8062	Intermediate Similarity	NPC198734
0.8062	Intermediate Similarity	NPC269242
0.8062	Intermediate Similarity	NPC476872
0.8058	Intermediate Similarity	NPC183781
0.8058	Intermediate Similarity	NPC64141
0.8058	Intermediate Similarity	NPC476383
0.8058	Intermediate Similarity	NPC472350
0.8058	Intermediate Similarity	NPC81515
0.8058	Intermediate Similarity	NPC68092
0.8058	Intermediate Similarity	NPC197316
0.8058	Intermediate Similarity	NPC89105
0.8056	Intermediate Similarity	NPC130449
0.8056	Intermediate Similarity	NPC248132
0.8049	Intermediate Similarity	NPC264784
0.8043	Intermediate Similarity	NPC471345
0.8031	Intermediate Similarity	NPC476266
0.8029	Intermediate Similarity	NPC187194
0.8029	Intermediate Similarity	NPC471883
0.8029	Intermediate Similarity	NPC35731
0.8029	Intermediate Similarity	NPC169398
0.8028	Intermediate Similarity	NPC187774
0.8028	Intermediate Similarity	NPC118385
0.8028	Intermediate Similarity	NPC473046
0.8028	Intermediate Similarity	NPC472712
0.8028	Intermediate Similarity	NPC225445
0.8028	Intermediate Similarity	NPC472713
0.8028	Intermediate Similarity	NPC64195
0.8015	Intermediate Similarity	NPC252833
0.8015	Intermediate Similarity	NPC165686
0.8015	Intermediate Similarity	NPC85799

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 NPC469687 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	268
0.1-0.2	696
0.2-0.3	1513
0.3-0.4	3173
0.4-0.5	2074
0.5-0.6	1204
0.6-0.7	211
0.7-0.8	11
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
0.8058	Intermediate Similarity	NPD7266	Discontinued
0.7727	Intermediate Similarity	NPD1091	Approved
0.7576	Intermediate Similarity	NPD5125	Phase 3
0.7576	Intermediate Similarity	NPD5126	Approved
0.7534	Intermediate Similarity	NPD5058	Phase 3
0.7386	Intermediate Similarity	NPD8455	Phase 2
0.7286	Intermediate Similarity	NPD3027	Phase 3
0.7273	Intermediate Similarity	NPD2860	Approved
0.7273	Intermediate Similarity	NPD2859	Approved
0.7254	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1613	Approved
0.7231	Intermediate Similarity	NPD7843	Approved
0.7222	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7228	Approved
0.719	Intermediate Similarity	NPD2933	Approved
0.719	Intermediate Similarity	NPD2934	Approved
0.7172	Intermediate Similarity	NPD5588	Approved
0.7143	Intermediate Similarity	NPD2861	Phase 2
0.7134	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3094	Phase 2
0.7097	Intermediate Similarity	NPD3020	Approved
0.7089	Intermediate Similarity	NPD6234	Discontinued
0.707	Intermediate Similarity	NPD4965	Approved
0.707	Intermediate Similarity	NPD4966	Approved
0.707	Intermediate Similarity	NPD4967	Phase 2
0.7059	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6190	Approved
0.7	Intermediate Similarity	NPD3021	Approved
0.7	Intermediate Similarity	NPD3022	Approved
0.6986	Remote Similarity	NPD4538	Approved
0.6986	Remote Similarity	NPD7097	Phase 1
0.6986	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4536	Approved
0.698	Remote Similarity	NPD6674	Discontinued
0.6972	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4908	Phase 1
0.6957	Remote Similarity	NPD1610	Phase 2
0.6957	Remote Similarity	NPD3705	Approved
0.6957	Remote Similarity	NPD3092	Approved
0.6951	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1653	Approved
0.694	Remote Similarity	NPD7157	Approved
0.6939	Remote Similarity	NPD5960	Phase 3
0.6928	Remote Similarity	NPD7240	Approved
0.6923	Remote Similarity	NPD2684	Approved
0.6912	Remote Similarity	NPD1548	Phase 1
0.6908	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD969	Suspended
0.689	Remote Similarity	NPD3818	Discontinued
0.6879	Remote Similarity	NPD37	Approved
0.6879	Remote Similarity	NPD4103	Phase 2
0.6879	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD1357	Approved
0.6857	Remote Similarity	NPD4659	Approved
0.685	Remote Similarity	NPD846	Approved
0.685	Remote Similarity	NPD940	Approved
0.6828	Remote Similarity	NPD6407	Approved
0.6828	Remote Similarity	NPD6405	Approved
0.6826	Remote Similarity	NPD7685	Pre-registration
0.6826	Remote Similarity	NPD6559	Discontinued
0.6812	Remote Similarity	NPD6516	Phase 2
0.6812	Remote Similarity	NPD5846	Approved
0.6809	Remote Similarity	NPD8651	Approved
0.6807	Remote Similarity	NPD7472	Approved
0.6807	Remote Similarity	NPD7074	Phase 3
0.6788	Remote Similarity	NPD7741	Discontinued
0.6788	Remote Similarity	NPD3091	Approved
0.6786	Remote Similarity	NPD7808	Phase 3
0.6772	Remote Similarity	NPD1242	Phase 1
0.6765	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3764	Approved
0.6755	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD4380	Phase 2
0.6747	Remote Similarity	NPD7054	Approved
0.6733	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7251	Discontinued
0.6712	Remote Similarity	NPD6233	Phase 2
0.6711	Remote Similarity	NPD7033	Discontinued
0.6687	Remote Similarity	NPD7199	Phase 2
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD6797	Phase 2
0.6647	Remote Similarity	NPD8313	Approved
0.6647	Remote Similarity	NPD8312	Approved
0.6644	Remote Similarity	NPD6798	Discontinued
0.6643	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD968	Approved
0.6641	Remote Similarity	NPD3028	Approved
0.664	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD2978	Approved
0.6625	Remote Similarity	NPD2977	Approved
0.6622	Remote Similarity	NPD4340	Discontinued
0.6622	Remote Similarity	NPD6355	Discontinued
0.6622	Remote Similarity	NPD5735	Approved
0.6617	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD4628	Phase 3
0.66	Remote Similarity	NPD4108	Discontinued
0.6599	Remote Similarity	NPD6663	Approved
0.6591	Remote Similarity	NPD290	Approved
0.6577	Remote Similarity	NPD5314	Approved
0.6575	Remote Similarity	NPD7095	Approved
0.6571	Remote Similarity	NPD3095	Discontinued
0.6569	Remote Similarity	NPD6671	Approved
0.6554	Remote Similarity	NPD3061	Approved
0.6554	Remote Similarity	NPD3059	Approved
0.6554	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD4060	Phase 1
0.6554	Remote Similarity	NPD3062	Approved
0.6549	Remote Similarity	NPD2562	Approved
0.6549	Remote Similarity	NPD2561	Approved
0.6538	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD1652	Phase 2
0.6531	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5124	Phase 1
0.6506	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6583	Phase 3
0.6503	Remote Similarity	NPD3685	Discontinued
0.6503	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7075	Discontinued
0.6503	Remote Similarity	NPD6582	Phase 2
0.6494	Remote Similarity	NPD4535	Phase 3
0.6491	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7680	Approved
0.6483	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5535	Approved
0.6471	Remote Similarity	NPD2424	Discontinued
0.6463	Remote Similarity	NPD4625	Phase 3
0.6454	Remote Similarity	NPD9384	Approved
0.6454	Remote Similarity	NPD9381	Approved
0.6446	Remote Similarity	NPD111	Approved
0.6444	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD3620	Phase 2
0.6442	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD5283	Phase 1
0.6423	Remote Similarity	NPD2234	Approved
0.6423	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD2229	Approved
0.6423	Remote Similarity	NPD2228	Approved
0.6405	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD5762	Approved
0.6405	Remote Similarity	NPD5763	Approved
0.6397	Remote Similarity	NPD228	Approved
0.6397	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4749	Approved
0.6389	Remote Similarity	NPD7876	Discontinued
0.6387	Remote Similarity	NPD3400	Discontinued
0.6376	Remote Similarity	NPD4062	Phase 3
0.6376	Remote Similarity	NPD4404	Approved
0.6374	Remote Similarity	NPD7007	Discovery
0.637	Remote Similarity	NPD5451	Approved
0.637	Remote Similarity	NPD6584	Phase 3
0.637	Remote Similarity	NPD4750	Phase 3
0.6369	Remote Similarity	NPD7213	Phase 3
0.6369	Remote Similarity	NPD7212	Phase 2
0.6364	Remote Similarity	NPD1549	Phase 2
0.6358	Remote Similarity	NPD2568	Approved
0.6358	Remote Similarity	NPD6653	Approved
0.6358	Remote Similarity	NPD1934	Approved
0.6357	Remote Similarity	NPD16	Approved
0.6357	Remote Similarity	NPD856	Approved
0.6352	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.635	Remote Similarity	NPD7635	Approved
0.6347	Remote Similarity	NPD3787	Discontinued
0.6338	Remote Similarity	NPD4059	Approved
0.6333	Remote Similarity	NPD2238	Phase 2
0.6333	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD4198	Discontinued
0.6329	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD3536	Discontinued
0.6329	Remote Similarity	NPD7447	Phase 1
0.6329	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD1809	Phase 2
0.6328	Remote Similarity	NPD844	Approved
0.6323	Remote Similarity	NPD4236	Phase 3
0.6323	Remote Similarity	NPD4237	Approved
0.6322	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5048	Discontinued
0.6312	Remote Similarity	NPD9545	Approved
0.6307	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD845	Approved
0.6299	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6005	Phase 3
0.6299	Remote Similarity	NPD1375	Discontinued
0.6299	Remote Similarity	NPD6004	Phase 3
0.6299	Remote Similarity	NPD6002	Phase 3
0.6296	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD3847	Discontinued

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