NPASS Compound

Structure

NPC469696 OpenBabel07101718332D 52 56 0 0 1 0 0 0 0 0999 V2000 -2.5411 7.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6750 9.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4071 6.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2731 4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 7.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5411 4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4071 8.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5411 9.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2731 6.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1391 5.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 6.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6750 5.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 5.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 4.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2226 -1.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6038 6.2902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6750 8.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4071 5.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4071 9.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1391 6.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 6.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 4.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7891 3.0878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7891 2.0878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9230 1.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0570 2.0878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4347 4.6810 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6180 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0570 3.0878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5211 5.0878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1038 5.4242 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3090 -0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8263 5.2431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3271 -2.3523 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2731 9.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0052 6.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 6.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 1.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 0.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6426 3.7029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5691 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0173 5.8309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4135 -1.9456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 4.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6256 6.0823 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 -0.8090 3.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 3.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 19 2 0 0 0 0 2 8 2 0 0 0 0 2 19 1 0 0 0 0 3 9 1 0 0 0 0 3 20 2 0 0 0 0 4 10 2 0 0 0 0 4 20 1 0 0 0 0 5 11 1 0 0 0 0 5 19 1 0 0 0 0 6 12 1 0 0 0 0 6 20 1 0 0 0 0 7 21 2 0 0 0 0 8 21 1 0 0 0 0 9 22 2 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 13 23 1 0 0 0 0 13 24 1 0 0 0 0 14 47 1 0 0 0 0 15 34 1 0 0 0 0 15 36 1 0 0 0 0 16 35 1 0 0 0 0 16 37 1 0 0 0 0 17 34 1 0 0 0 0 17 48 1 0 0 0 0 18 35 1 0 0 0 0 18 49 1 0 0 0 0 21 38 1 0 0 0 0 22 39 1 0 0 0 0 23 40 2 0 0 0 0 24 12 1 6 0 0 0 24 50 1 0 0 0 0 25 14 1 6 0 0 0 25 26 1 0 0 0 0 25 51 1 0 0 0 0 26 27 1 0 0 0 0 26 41 1 1 0 0 0 27 28 1 0 0 0 0 27 42 1 6 0 0 0 28 31 1 0 0 0 0 28 52 1 1 0 0 0 29 32 1 0 0 0 0 29 34 1 1 0 0 0 29 43 1 0 0 0 0 30 33 1 0 0 0 0 30 35 1 6 0 0 0 30 44 1 0 0 0 0 31 50 1 6 0 0 0 31 51 1 0 0 0 0 32 47 1 6 0 0 0 32 48 1 0 0 0 0 33 49 1 0 0 0 0 33 52 1 1 0 0 0 34 45 1 1 0 0 0 35 46 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	740.29
Volume:	702.112
LogP:	-0.201
LogD:	-0.302
LogS:	-2.801
# Rotatable Bonds:	17
TPSA:	274.75
# H-Bond Aceptor:	17
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.082
Synthetic Accessibility Score:	5.362
Fsp3:	0.629
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:	-6.507
MDCK Permeability:	6.951510385988513e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.973
Human Intestinal Absorption (HIA):	0.997
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.152
Plasma Protein Binding (PPB):	64.26029968261719%
Volume Distribution (VD):	0.105
Pgp-substrate:	16.74915885925293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.015
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.115

ADMET: Excretion

Clearance (CL):	0.64
Half-life (T1/2):	0.851

ADMET: Toxicity

hERG Blockers:	0.355
Human Hepatotoxicity (H-HT):	0.226
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.278
Rat Oral Acute Toxicity:	0.09
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.777
Carcinogencity:	0.17
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC469696

Natural Product ID:	NPC469696
*Common Name:**	(5S)-5-Hydroxy-1,7-Bis-(4-Hydroxyphenyl)-3-Heptanone-5-O-[2,6-Bis-O-(B-D-Apiofuranosyl)-B-D-Glucopyranoside]
IUPAC Name:	(5R)-5-[(2R,3R,4S,5S,6R)-3-[(2R,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxy-1,7-bis(4-hydroxyphenyl)heptan-3-one
Synonyms:
Standard InCHIKey:	BTVWDANIMYMMGY-RISIZWLVSA-N
Standard InCHI:	InChI=1S/C35H48O17/c36-15-34(45)17-48-32(29(34)43)47-14-25-26(41)27(42)28(52-33-30(44)35(46,16-37)18-49-33)31(51-25)50-24(12-6-20-3-9-22(39)10-4-20)13-23(40)11-5-19-1-7-21(38)8-2-19/h1-4,7-10,24-33,36-39,41-46H,5-6,11-18H2/t24-,25-,26-,27+,28-,29+,30-,31-,32-,33-,34-,35+/m1/s1
SMILES:	OC[C@]1(O)CO[C@@H]([C@H]1O)O[C@H]1[C@H](O[C@@H](CC(=O)CCc2ccc(cc2)O)CCc2ccc(cc2)O)O[C@@H]([C@H]([C@@H]1O)O)CO[C@@H]1OC[C@]([C@H]1O)(O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1099359
PubChem CID:	46889109
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids [CHEMONTID:0000356] Curcuminoids

*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	=	11.8	%	PMID[573183]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	23.4	%	PMID[573183]

☑ 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 NPC469696 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	1027
0.2-0.3	2588
0.3-0.4	5990
0.4-0.5	11978
0.5-0.6	8914
0.6-0.7	10379
0.7-0.8	1436
0.8-0.85	54
0.85-0.9	10
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9692	High Similarity	NPC164172
0.9615	High Similarity	NPC471095
0.9615	High Similarity	NPC471066
0.9462	High Similarity	NPC469705
0.9462	High Similarity	NPC17968
0.9462	High Similarity	NPC470122
0.9308	High Similarity	NPC158673
0.9231	High Similarity	NPC469687
0.9098	High Similarity	NPC476407
0.8923	High Similarity	NPC470907
0.8923	High Similarity	NPC178449
0.8923	High Similarity	NPC232454
0.8857	High Similarity	NPC469623
0.8857	High Similarity	NPC148080
0.8846	High Similarity	NPC471067
0.8832	High Similarity	NPC180171
0.8832	High Similarity	NPC103398
0.8832	High Similarity	NPC158325
0.8692	High Similarity	NPC201402
0.8692	High Similarity	NPC160854
0.8692	High Similarity	NPC469703
0.8692	High Similarity	NPC469704
0.8667	High Similarity	NPC469549
0.8626	High Similarity	NPC469686
0.855	High Similarity	NPC469548
0.855	High Similarity	NPC476448
0.855	High Similarity	NPC476445
0.854	High Similarity	NPC478255
0.8531	High Similarity	NPC478250
0.8503	High Similarity	NPC35097
0.8493	Intermediate Similarity	NPC120728
0.8473	Intermediate Similarity	NPC469702
0.8473	Intermediate Similarity	NPC282409
0.8429	Intermediate Similarity	NPC123988
0.8403	Intermediate Similarity	NPC40305
0.8369	Intermediate Similarity	NPC471345
0.8367	Intermediate Similarity	NPC473138
0.8367	Intermediate Similarity	NPC28776
0.8333	Intermediate Similarity	NPC87403
0.8321	Intermediate Similarity	NPC225307
0.831	Intermediate Similarity	NPC310252
0.831	Intermediate Similarity	NPC100558
0.831	Intermediate Similarity	NPC84789
0.831	Intermediate Similarity	NPC302583
0.8288	Intermediate Similarity	NPC475528
0.8286	Intermediate Similarity	NPC28637
0.8284	Intermediate Similarity	NPC469927
0.8278	Intermediate Similarity	NPC160882
0.8273	Intermediate Similarity	NPC281798
0.8267	Intermediate Similarity	NPC106818
0.8248	Intermediate Similarity	NPC288416
0.8248	Intermediate Similarity	NPC264900
0.8248	Intermediate Similarity	NPC79715
0.8248	Intermediate Similarity	NPC231607
0.8248	Intermediate Similarity	NPC108659
0.8235	Intermediate Similarity	NPC123704
0.8231	Intermediate Similarity	NPC143246
0.8231	Intermediate Similarity	NPC475539
0.8231	Intermediate Similarity	NPC119773
0.8231	Intermediate Similarity	NPC212808
0.8231	Intermediate Similarity	NPC474268
0.8222	Intermediate Similarity	NPC236981
0.8219	Intermediate Similarity	NPC194938
0.8209	Intermediate Similarity	NPC55608
0.8176	Intermediate Similarity	NPC470330
0.8175	Intermediate Similarity	NPC94179
0.817	Intermediate Similarity	NPC478055
0.8169	Intermediate Similarity	NPC263829
0.8168	Intermediate Similarity	NPC148055
0.8154	Intermediate Similarity	NPC157338
0.8151	Intermediate Similarity	NPC105005
0.8143	Intermediate Similarity	NPC46137
0.8143	Intermediate Similarity	NPC235294
0.8129	Intermediate Similarity	NPC184092
0.8125	Intermediate Similarity	NPC62800
0.8125	Intermediate Similarity	NPC171134
0.8125	Intermediate Similarity	NPC321184
0.8125	Intermediate Similarity	NPC321638
0.8125	Intermediate Similarity	NPC328273
0.8125	Intermediate Similarity	NPC324262
0.8121	Intermediate Similarity	NPC116229
0.8116	Intermediate Similarity	NPC45224
0.8116	Intermediate Similarity	NPC103533
0.8116	Intermediate Similarity	NPC471882
0.8116	Intermediate Similarity	NPC156692
0.8116	Intermediate Similarity	NPC35288
0.8116	Intermediate Similarity	NPC173150
0.8116	Intermediate Similarity	NPC471881
0.8108	Intermediate Similarity	NPC473147
0.8102	Intermediate Similarity	NPC90318
0.8099	Intermediate Similarity	NPC169398
0.8095	Intermediate Similarity	NPC296659
0.8095	Intermediate Similarity	NPC300894
0.8095	Intermediate Similarity	NPC141455
0.8095	Intermediate Similarity	NPC196063
0.8095	Intermediate Similarity	NPC63304
0.8095	Intermediate Similarity	NPC296954
0.8095	Intermediate Similarity	NPC202391
0.8079	Intermediate Similarity	NPC474620
0.8056	Intermediate Similarity	NPC469364
0.8056	Intermediate Similarity	NPC101686
0.8056	Intermediate Similarity	NPC65262
0.8052	Intermediate Similarity	NPC149368
0.8052	Intermediate Similarity	NPC265480
0.8043	Intermediate Similarity	NPC61181
0.8043	Intermediate Similarity	NPC252114
0.8041	Intermediate Similarity	NPC210330
0.8025	Intermediate Similarity	NPC471850
0.8014	Intermediate Similarity	NPC246869
0.8014	Intermediate Similarity	NPC138777
0.8014	Intermediate Similarity	NPC225384
0.8013	Intermediate Similarity	NPC200708
0.8	Intermediate Similarity	NPC122809
0.8	Intermediate Similarity	NPC11025
0.7987	Intermediate Similarity	NPC131532
0.7987	Intermediate Similarity	NPC186316
0.7987	Intermediate Similarity	NPC229505
0.7987	Intermediate Similarity	NPC38699
0.7986	Intermediate Similarity	NPC106677
0.7986	Intermediate Similarity	NPC472132
0.7974	Intermediate Similarity	NPC299706
0.7974	Intermediate Similarity	NPC121001
0.7974	Intermediate Similarity	NPC245615
0.7974	Intermediate Similarity	NPC259182
0.7974	Intermediate Similarity	NPC61604
0.7974	Intermediate Similarity	NPC115466
0.7974	Intermediate Similarity	NPC257847
0.7973	Intermediate Similarity	NPC84181
0.7971	Intermediate Similarity	NPC83218
0.7971	Intermediate Similarity	NPC126991
0.7962	Intermediate Similarity	NPC471858
0.7958	Intermediate Similarity	NPC254275
0.7947	Intermediate Similarity	NPC287294
0.7935	Intermediate Similarity	NPC163635
0.7931	Intermediate Similarity	NPC308976
0.7929	Intermediate Similarity	NPC148982
0.7927	Intermediate Similarity	NPC241196
0.7923	Intermediate Similarity	NPC177576
0.7922	Intermediate Similarity	NPC106625
0.7922	Intermediate Similarity	NPC476194
0.7919	Intermediate Similarity	NPC18979
0.7914	Intermediate Similarity	NPC471157
0.7905	Intermediate Similarity	NPC477898
0.7905	Intermediate Similarity	NPC293154
0.7898	Intermediate Similarity	NPC130489
0.7898	Intermediate Similarity	NPC208676
0.7895	Intermediate Similarity	NPC240592
0.7895	Intermediate Similarity	NPC475224
0.7895	Intermediate Similarity	NPC175771
0.7895	Intermediate Similarity	NPC301651
0.7895	Intermediate Similarity	NPC117346
0.7895	Intermediate Similarity	NPC229882
0.7895	Intermediate Similarity	NPC473556
0.7895	Intermediate Similarity	NPC12006
0.7895	Intermediate Similarity	NPC158635
0.7891	Intermediate Similarity	NPC476377
0.7891	Intermediate Similarity	NPC47471
0.7883	Intermediate Similarity	NPC52097
0.7881	Intermediate Similarity	NPC472339
0.7879	Intermediate Similarity	NPC313193
0.7877	Intermediate Similarity	NPC205195
0.7877	Intermediate Similarity	NPC220942
0.7877	Intermediate Similarity	NPC156376
0.7875	Intermediate Similarity	NPC469419
0.7871	Intermediate Similarity	NPC26195
0.7871	Intermediate Similarity	NPC169248
0.7871	Intermediate Similarity	NPC99233
0.7871	Intermediate Similarity	NPC39351
0.7871	Intermediate Similarity	NPC72649
0.7871	Intermediate Similarity	NPC97052
0.7867	Intermediate Similarity	NPC291153
0.7867	Intermediate Similarity	NPC320734
0.7867	Intermediate Similarity	NPC112861
0.7862	Intermediate Similarity	NPC470572
0.7857	Intermediate Similarity	NPC259767
0.7857	Intermediate Similarity	NPC88484
0.7852	Intermediate Similarity	NPC251062
0.7852	Intermediate Similarity	NPC184464
0.7848	Intermediate Similarity	NPC477627
0.7847	Intermediate Similarity	NPC34293
0.7847	Intermediate Similarity	NPC886
0.7847	Intermediate Similarity	NPC287597
0.7847	Intermediate Similarity	NPC471029
0.7846	Intermediate Similarity	NPC321252
0.7846	Intermediate Similarity	NPC252544
0.7834	Intermediate Similarity	NPC469654
0.7829	Intermediate Similarity	NPC478242
0.7829	Intermediate Similarity	NPC96599
0.7826	Intermediate Similarity	NPC471859
0.7823	Intermediate Similarity	NPC475530
0.7823	Intermediate Similarity	NPC473799
0.7821	Intermediate Similarity	NPC170475
0.7821	Intermediate Similarity	NPC127406
0.7821	Intermediate Similarity	NPC475378
0.7821	Intermediate Similarity	NPC206378
0.781	Intermediate Similarity	NPC266045
0.781	Intermediate Similarity	NPC11724
0.7808	Intermediate Similarity	NPC260425
0.7806	Intermediate Similarity	NPC39360
0.7806	Intermediate Similarity	NPC29763

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 NPC469696 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	656
0.2-0.3	1478
0.3-0.4	2886
0.4-0.5	2366
0.5-0.6	1162
0.6-0.7	326
0.7-0.8	20
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
0.7771	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7266	Discontinued
0.7692	Intermediate Similarity	NPD8455	Phase 2
0.7561	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD7228	Approved
0.7425	Intermediate Similarity	NPD6559	Discontinued
0.741	Intermediate Similarity	NPD7472	Approved
0.741	Intermediate Similarity	NPD7074	Phase 3
0.7391	Intermediate Similarity	NPD6234	Discontinued
0.7389	Intermediate Similarity	NPD4380	Phase 2
0.7381	Intermediate Similarity	NPD7808	Phase 3
0.7375	Intermediate Similarity	NPD4966	Approved
0.7375	Intermediate Similarity	NPD4967	Phase 2
0.7375	Intermediate Similarity	NPD4965	Approved
0.7349	Intermediate Similarity	NPD7054	Approved
0.7321	Intermediate Similarity	NPD7251	Discontinued
0.732	Intermediate Similarity	NPD6190	Approved
0.7262	Intermediate Similarity	NPD6797	Phase 2
0.7235	Intermediate Similarity	NPD8313	Approved
0.7235	Intermediate Similarity	NPD8312	Approved
0.7226	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7240	Approved
0.72	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD37	Approved
0.7183	Intermediate Similarity	NPD1091	Approved
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7151	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7685	Pre-registration
0.7117	Intermediate Similarity	NPD7075	Discontinued
0.7114	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3764	Approved
0.7076	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5058	Phase 3
0.7047	Intermediate Similarity	NPD6233	Phase 2
0.7045	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5125	Phase 3
0.7042	Intermediate Similarity	NPD5126	Approved
0.7013	Intermediate Similarity	NPD1549	Phase 2
0.6988	Remote Similarity	NPD7199	Phase 2
0.698	Remote Similarity	NPD6798	Discontinued
0.6975	Remote Similarity	NPD1934	Approved
0.6974	Remote Similarity	NPD7097	Phase 1
0.6954	Remote Similarity	NPD6355	Discontinued
0.6946	Remote Similarity	NPD3787	Discontinued
0.6933	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6663	Approved
0.6933	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4628	Phase 3
0.6923	Remote Similarity	NPD3400	Discontinued
0.689	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5403	Approved
0.6871	Remote Similarity	NPD6801	Discontinued
0.6867	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6166	Phase 2
0.6864	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1510	Phase 2
0.6815	Remote Similarity	NPD5048	Discontinued
0.6805	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3027	Phase 3
0.6784	Remote Similarity	NPD3751	Discontinued
0.6779	Remote Similarity	NPD5736	Approved
0.6776	Remote Similarity	NPD1613	Approved
0.6776	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7700	Phase 2
0.6758	Remote Similarity	NPD7699	Phase 2
0.6757	Remote Similarity	NPD7680	Approved
0.675	Remote Similarity	NPD5401	Approved
0.675	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1653	Approved
0.6727	Remote Similarity	NPD7819	Suspended
0.6723	Remote Similarity	NPD8434	Phase 2
0.6721	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD2859	Approved
0.6718	Remote Similarity	NPD2860	Approved
0.6714	Remote Similarity	NPD7843	Approved
0.6711	Remote Similarity	NPD5647	Approved
0.6711	Remote Similarity	NPD4062	Phase 3
0.671	Remote Similarity	NPD5588	Approved
0.6709	Remote Similarity	NPD8166	Discontinued
0.6707	Remote Similarity	NPD7411	Suspended
0.669	Remote Similarity	NPD2932	Approved
0.669	Remote Similarity	NPD3019	Approved
0.6687	Remote Similarity	NPD6799	Approved
0.6687	Remote Similarity	NPD5402	Approved
0.6686	Remote Similarity	NPD7799	Discontinued
0.6685	Remote Similarity	NPD6535	Approved
0.6685	Remote Similarity	NPD6534	Approved
0.6667	Remote Similarity	NPD943	Approved
0.6667	Remote Similarity	NPD2861	Phase 2
0.6667	Remote Similarity	NPD1240	Approved
0.6667	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9545	Approved
0.6648	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3882	Suspended
0.6646	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3094	Phase 2
0.6643	Remote Similarity	NPD969	Suspended
0.6641	Remote Similarity	NPD2934	Approved
0.6641	Remote Similarity	NPD2933	Approved
0.6631	Remote Similarity	NPD8320	Phase 1
0.6631	Remote Similarity	NPD8319	Approved
0.6629	Remote Similarity	NPD8150	Discontinued
0.6627	Remote Similarity	NPD2801	Approved
0.6624	Remote Similarity	NPD6002	Phase 3
0.6624	Remote Similarity	NPD6005	Phase 3
0.6624	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6004	Phase 3
0.662	Remote Similarity	NPD2629	Approved
0.6613	Remote Similarity	NPD6823	Phase 2
0.661	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD2575	Approved
0.6604	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD1201	Approved
0.6599	Remote Similarity	NPD1535	Discovery
0.6595	Remote Similarity	NPD6779	Approved
0.6595	Remote Similarity	NPD6782	Approved
0.6595	Remote Similarity	NPD6780	Approved
0.6595	Remote Similarity	NPD6781	Approved
0.6595	Remote Similarity	NPD6778	Approved
0.6595	Remote Similarity	NPD6776	Approved
0.6595	Remote Similarity	NPD6777	Approved
0.6587	Remote Similarity	NPD3817	Phase 2
0.6585	Remote Similarity	NPD7458	Discontinued
0.6584	Remote Similarity	NPD1511	Approved
0.6582	Remote Similarity	NPD2424	Discontinued
0.6581	Remote Similarity	NPD1607	Approved
0.658	Remote Similarity	NPD7930	Approved
0.6579	Remote Similarity	NPD7095	Approved
0.6578	Remote Similarity	NPD7697	Approved
0.6578	Remote Similarity	NPD7698	Approved
0.6578	Remote Similarity	NPD7435	Discontinued
0.6578	Remote Similarity	NPD7696	Phase 3
0.6575	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD3020	Approved
0.6561	Remote Similarity	NPD2935	Discontinued
0.6561	Remote Similarity	NPD2796	Approved
0.6561	Remote Similarity	NPD9570	Approved
0.6561	Remote Similarity	NPD7584	Approved
0.6558	Remote Similarity	NPD6311	Approved
0.6558	Remote Similarity	NPD6310	Approved
0.6558	Remote Similarity	NPD6309	Approved
0.6554	Remote Similarity	NPD1481	Phase 2
0.6552	Remote Similarity	NPD1894	Discontinued
0.6548	Remote Similarity	NPD7768	Phase 2
0.6545	Remote Similarity	NPD6599	Discontinued
0.6545	Remote Similarity	NPD7028	Phase 2
0.6543	Remote Similarity	NPD7871	Phase 2
0.6543	Remote Similarity	NPD7870	Phase 2
0.6541	Remote Similarity	NPD6674	Discontinued
0.6538	Remote Similarity	NPD4536	Approved
0.6538	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4538	Approved
0.6533	Remote Similarity	NPD1470	Approved
0.6526	Remote Similarity	NPD7701	Phase 2
0.6513	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4908	Phase 1
0.6509	Remote Similarity	NPD3749	Approved
0.6508	Remote Similarity	NPD7999	Approved
0.6503	Remote Similarity	NPD1512	Approved
0.65	Remote Similarity	NPD3021	Approved
0.65	Remote Similarity	NPD3022	Approved
0.65	Remote Similarity	NPD3750	Approved
0.6497	Remote Similarity	NPD5960	Phase 3
0.6492	Remote Similarity	NPD8151	Discontinued
0.649	Remote Similarity	NPD2798	Approved
0.6486	Remote Similarity	NPD1610	Phase 2
0.6486	Remote Similarity	NPD3092	Approved
0.6486	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3705	Approved
0.6478	Remote Similarity	NPD5958	Discontinued
0.6474	Remote Similarity	NPD6653	Approved
0.6474	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7874	Approved
0.6458	Remote Similarity	NPD7157	Approved
0.6458	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD6100	Approved
0.6456	Remote Similarity	NPD5404	Approved
0.6456	Remote Similarity	NPD5405	Approved
0.6456	Remote Similarity	NPD5408	Approved
0.6456	Remote Similarity	NPD5406	Approved
0.6456	Remote Similarity	NPD6099	Approved
0.6448	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD6212	Phase 3
0.6448	Remote Similarity	NPD6213	Phase 3
0.6447	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7798	Approved
0.6442	Remote Similarity	NPD7422	Clinical (unspecified phase)

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