NPASS Compound

Structure

NPC470827 OpenBabel07101719162D 56 60 0 0 1 0 0 0 0 0999 V2000 -13.9039 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7078 -1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 0.9889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 -4.2072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 -3.3412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.0379 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.9039 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7078 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 -5.0733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1719 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 -2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4398 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 -2.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1719 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 0 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 -13.9039 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7078 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.0379 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4398 0.0933 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.2437 1.0933 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -11.3059 -0.4067 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.1097 1.5933 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 -5.9393 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5032 -1.7614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3059 1.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.7700 1.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3059 -1.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.0379 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 -1.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 0.1229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5738 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 1.5933 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 49 1 0 0 0 0 2 50 1 0 0 0 0 3 51 1 0 0 0 0 4 52 1 0 0 0 0 5 53 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 22 1 0 0 0 0 8 10 2 0 0 0 0 8 23 1 0 0 0 0 9 11 2 0 0 0 0 9 24 1 0 0 0 0 10 28 1 0 0 0 0 11 29 1 0 0 0 0 12 42 2 0 0 0 0 13 22 2 0 0 0 0 13 26 1 0 0 0 0 14 22 1 0 0 0 0 14 32 2 0 0 0 0 15 23 2 0 0 0 0 15 30 1 0 0 0 0 16 24 2 0 0 0 0 16 31 1 0 0 0 0 17 25 2 0 0 0 0 17 33 1 0 0 0 0 18 25 1 0 0 0 0 18 34 2 0 0 0 0 19 43 1 0 0 0 0 20 35 1 0 0 0 0 20 44 1 0 0 0 0 21 36 1 0 0 0 0 21 45 1 0 0 0 0 23 37 1 0 0 0 0 24 38 1 0 0 0 0 26 27 1 0 0 0 0 26 40 2 0 0 0 0 27 19 1 1 0 0 0 27 39 1 0 0 0 0 28 30 2 0 0 0 0 28 46 1 0 0 0 0 29 31 2 0 0 0 0 29 54 1 0 0 0 0 30 49 1 0 0 0 0 31 50 1 0 0 0 0 32 40 1 0 0 0 0 32 51 1 0 0 0 0 33 41 2 0 0 0 0 33 52 1 0 0 0 0 34 41 1 0 0 0 0 34 53 1 0 0 0 0 35 37 1 0 0 0 0 35 54 1 0 0 0 0 36 38 1 0 0 0 0 36 55 1 0 0 0 0 37 47 1 0 0 0 0 38 48 1 0 0 0 0 39 25 1 6 0 0 0 39 56 1 0 0 0 0 40 56 1 0 0 0 0 41 55 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	778.28
Volume:	769.853
LogP:	1.806
LogD:	2.125
LogS:	-4.579
# Rotatable Bonds:	19
TPSA:	212.29
# H-Bond Aceptor:	15
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.059
Synthetic Accessibility Score:	4.901
Fsp3:	0.341
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.721
MDCK Permeability:	1.3887341992813163e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.672
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.094

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.204
Plasma Protein Binding (PPB):	64.87747955322266%
Volume Distribution (VD):	0.575
Pgp-substrate:	47.3109245300293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.184
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.893
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.806
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.777
CYP3A4-inhibitor:	0.761
CYP3A4-substrate:	0.939

ADMET: Excretion

Clearance (CL):	6.037
Half-life (T1/2):	0.405

ADMET: Toxicity

hERG Blockers:	0.164
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.158
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.484
Maximum Recommended Daily Dose:	0.77
Skin Sensitization:	0.122
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.01

Download Data

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

Natural Product: NPC470827

Natural Product ID:	NPC470827
*Common Name:**	4''-O-(8-Guaiacylglycerol)Buddlenol A
IUPAC Name:	(E)-3-[(2R,3S)-2-[4-[1-[4-[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-methoxyphenyl]-1,3-dihydroxypropan-2-yl]oxy-3,5-dimethoxyphenyl]-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal
Synonyms:
Standard InCHIKey:	HITLEOURIXKLBL-DRATVDAASA-N
Standard InCHI:	InChI=1S/C41H46O15/c1-49-30-15-23(8-10-28(30)46)37(47)35(20-44)54-29-11-9-24(16-31(29)50-2)38(48)36(21-45)55-41-33(52-4)17-25(18-34(41)53-5)39-27(19-43)26-13-22(7-6-12-42)14-32(51-3)40(26)56-39/h6-18,27,35-39,43-48H,19-21H2,1-5H3/b7-6+/t27-,35?,36?,37?,38?,39+/m1/s1
SMILES:	O=C/C=C/c1cc(OC)c2c(c1)[C@@H](CO)[C@@H](O2)c1cc(OC)c(c(c1)OC)OC(C(c1ccc(c(c1)OC)OC(C(c1ccc(c(c1)OC)O)O)CO)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL225531
PubChem CID:	16216400
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792422]
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17343407]
NPO14922	Tarenna attenuata	Species	Rubiaceae	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
IC50	1
Others	4

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	52.8	%	PMID[492355]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	47.9	%	PMID[492355]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	64.4	%	PMID[492355]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	55.9	%	PMID[492355]
NPT1	Others	Radical scavenging activity		IC50	=	201000.0	nM	PMID[492355]

☑ 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 NPC470827 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	432
0.1-0.2	1454
0.2-0.3	3732
0.3-0.4	9890
0.4-0.5	8995
0.5-0.6	3646
0.6-0.7	6192
0.7-0.8	6932
0.8-0.85	1117
0.85-0.9	261
0.9-0.95	39
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC470828
0.9732	High Similarity	NPC470769
0.9605	High Similarity	NPC125495
0.9396	High Similarity	NPC473408
0.9342	High Similarity	NPC115203
0.9272	High Similarity	NPC477612
0.9262	High Similarity	NPC260397
0.9211	High Similarity	NPC324517
0.9211	High Similarity	NPC329343
0.9211	High Similarity	NPC321972
0.9195	High Similarity	NPC181615
0.9139	High Similarity	NPC20757
0.9139	High Similarity	NPC227516
0.9128	High Similarity	NPC284881
0.9128	High Similarity	NPC93433
0.9128	High Similarity	NPC474444
0.9128	High Similarity	NPC264706
0.9079	High Similarity	NPC470098
0.9079	High Similarity	NPC470826
0.9079	High Similarity	NPC475250
0.9079	High Similarity	NPC211561
0.9079	High Similarity	NPC473266
0.9073	High Similarity	NPC320970
0.9073	High Similarity	NPC320671
0.9073	High Similarity	NPC328567
0.9073	High Similarity	NPC327412
0.9062	High Similarity	NPC43065
0.9051	High Similarity	NPC478267
0.9032	High Similarity	NPC157333
0.9013	High Similarity	NPC102934
0.9013	High Similarity	NPC252402
0.9012	High Similarity	NPC180768
0.9007	High Similarity	NPC324492
0.9007	High Similarity	NPC317053
0.8947	High Similarity	NPC18185
0.8947	High Similarity	NPC204770
0.8947	High Similarity	NPC262911
0.8947	High Similarity	NPC294558
0.8947	High Similarity	NPC170103
0.8947	High Similarity	NPC108811
0.8947	High Similarity	NPC263940
0.8947	High Similarity	NPC236202
0.8947	High Similarity	NPC82917
0.8947	High Similarity	NPC58190
0.8947	High Similarity	NPC70409
0.8947	High Similarity	NPC202742
0.8926	High Similarity	NPC87725
0.8926	High Similarity	NPC470372
0.8926	High Similarity	NPC263261
0.8924	High Similarity	NPC478269
0.8903	High Similarity	NPC226809
0.8903	High Similarity	NPC279406
0.8889	High Similarity	NPC329836
0.8882	High Similarity	NPC96576
0.8875	High Similarity	NPC12326
0.8874	High Similarity	NPC304894
0.8874	High Similarity	NPC114119
0.8874	High Similarity	NPC471415
0.8874	High Similarity	NPC470097
0.8874	High Similarity	NPC15659
0.8867	High Similarity	NPC278469
0.8867	High Similarity	NPC193722
0.8859	High Similarity	NPC266197
0.8859	High Similarity	NPC267291
0.8859	High Similarity	NPC22317
0.8859	High Similarity	NPC291101
0.8854	High Similarity	NPC202104
0.8846	High Similarity	NPC224161
0.8827	High Similarity	NPC59516
0.8816	High Similarity	NPC274960
0.8816	High Similarity	NPC163898
0.8816	High Similarity	NPC473909
0.8816	High Similarity	NPC143120
0.8812	High Similarity	NPC216916
0.8808	High Similarity	NPC173203
0.8808	High Similarity	NPC163508
0.88	High Similarity	NPC224876
0.88	High Similarity	NPC83375
0.88	High Similarity	NPC178054
0.8792	High Similarity	NPC260842
0.879	High Similarity	NPC46335
0.8766	High Similarity	NPC281549
0.8766	High Similarity	NPC236166
0.8758	High Similarity	NPC40222
0.8758	High Similarity	NPC268515
0.875	High Similarity	NPC28440
0.875	High Similarity	NPC93323
0.875	High Similarity	NPC45257
0.875	High Similarity	NPC63879
0.875	High Similarity	NPC280092
0.875	High Similarity	NPC12641
0.875	High Similarity	NPC171932
0.8733	High Similarity	NPC309124
0.8733	High Similarity	NPC184797
0.8726	High Similarity	NPC475141
0.8725	High Similarity	NPC477938
0.8725	High Similarity	NPC474390
0.871	High Similarity	NPC321657
0.871	High Similarity	NPC318373
0.871	High Similarity	NPC476969
0.8704	High Similarity	NPC45943
0.8701	High Similarity	NPC16269
0.8701	High Similarity	NPC101376
0.8701	High Similarity	NPC21776
0.8684	High Similarity	NPC85264
0.8684	High Similarity	NPC47633
0.8684	High Similarity	NPC102044
0.8675	High Similarity	NPC311530
0.8671	High Similarity	NPC473736
0.8671	High Similarity	NPC268484
0.8667	High Similarity	NPC473739
0.8667	High Similarity	NPC70682
0.8667	High Similarity	NPC260741
0.8667	High Similarity	NPC22517
0.8667	High Similarity	NPC236306
0.8667	High Similarity	NPC232164
0.8662	High Similarity	NPC59692
0.8662	High Similarity	NPC157783
0.8662	High Similarity	NPC469944
0.8662	High Similarity	NPC134911
0.8662	High Similarity	NPC44192
0.8662	High Similarity	NPC226108
0.8662	High Similarity	NPC272552
0.8662	High Similarity	NPC46283
0.8662	High Similarity	NPC322899
0.8658	High Similarity	NPC54743
0.8658	High Similarity	NPC77861
0.8658	High Similarity	NPC29799
0.8658	High Similarity	NPC209985
0.8658	High Similarity	NPC177160
0.8658	High Similarity	NPC263367
0.8658	High Similarity	NPC10737
0.8658	High Similarity	NPC477939
0.8658	High Similarity	NPC156502
0.8654	High Similarity	NPC472709
0.8654	High Similarity	NPC472710
0.8645	High Similarity	NPC476348
0.8645	High Similarity	NPC187398
0.8642	High Similarity	NPC476371
0.8642	High Similarity	NPC476372
0.8627	High Similarity	NPC473108
0.8625	High Similarity	NPC73517
0.8625	High Similarity	NPC147743
0.8625	High Similarity	NPC4809
0.8618	High Similarity	NPC204347
0.8618	High Similarity	NPC2613
0.8618	High Similarity	NPC131971
0.8618	High Similarity	NPC59841
0.8618	High Similarity	NPC475891
0.8618	High Similarity	NPC107161
0.8618	High Similarity	NPC67467
0.8609	High Similarity	NPC472090
0.8609	High Similarity	NPC472092
0.8609	High Similarity	NPC262189
0.8609	High Similarity	NPC472091
0.8609	High Similarity	NPC160283
0.8609	High Similarity	NPC254759
0.8608	High Similarity	NPC20050
0.8608	High Similarity	NPC306267
0.8608	High Similarity	NPC223720
0.8599	High Similarity	NPC2745
0.8599	High Similarity	NPC302915
0.8591	High Similarity	NPC93783
0.8591	High Similarity	NPC125579
0.8581	High Similarity	NPC476347
0.8581	High Similarity	NPC262297
0.858	High Similarity	NPC7191
0.858	High Similarity	NPC469889
0.858	High Similarity	NPC149873
0.8571	High Similarity	NPC471404
0.8571	High Similarity	NPC241600
0.8571	High Similarity	NPC86630
0.8571	High Similarity	NPC469557
0.8571	High Similarity	NPC230531
0.8571	High Similarity	NPC173726
0.8571	High Similarity	NPC159526
0.8571	High Similarity	NPC185231
0.8571	High Similarity	NPC205613
0.8571	High Similarity	NPC151474
0.8571	High Similarity	NPC215400
0.8571	High Similarity	NPC106601
0.8571	High Similarity	NPC212614
0.8562	High Similarity	NPC11411
0.8562	High Similarity	NPC477616
0.8562	High Similarity	NPC165483
0.8554	High Similarity	NPC102277
0.8554	High Similarity	NPC279209
0.8553	High Similarity	NPC35216
0.8553	High Similarity	NPC247291
0.8553	High Similarity	NPC8712
0.8553	High Similarity	NPC277331
0.8553	High Similarity	NPC100482
0.8553	High Similarity	NPC471389
0.8544	High Similarity	NPC476391
0.8544	High Similarity	NPC264875
0.8544	High Similarity	NPC478268
0.8544	High Similarity	NPC476434
0.8544	High Similarity	NPC302610
0.8544	High Similarity	NPC163598
0.8544	High Similarity	NPC160196

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 NPC470827 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	902
0.2-0.3	1775
0.3-0.4	2754
0.4-0.5	1746
0.5-0.6	955
0.6-0.7	539
0.7-0.8	110
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8267	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1613	Approved
0.8188	Intermediate Similarity	NPD3027	Phase 3
0.8133	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD6166	Phase 2
0.8095	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4908	Phase 1
0.8	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD5844	Phase 1
0.7933	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD1934	Approved
0.7904	Intermediate Similarity	NPD6234	Discontinued
0.7901	Intermediate Similarity	NPD1653	Approved
0.7895	Intermediate Similarity	NPD3818	Discontinued
0.7895	Intermediate Similarity	NPD7228	Approved
0.7857	Intermediate Similarity	NPD5494	Approved
0.7831	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD37	Approved
0.7816	Intermediate Similarity	NPD6559	Discontinued
0.7811	Intermediate Similarity	NPD7199	Phase 2
0.7803	Intermediate Similarity	NPD7074	Phase 3
0.7784	Intermediate Similarity	NPD4967	Phase 2
0.7784	Intermediate Similarity	NPD7768	Phase 2
0.7784	Intermediate Similarity	NPD4965	Approved
0.7784	Intermediate Similarity	NPD3882	Suspended
0.7784	Intermediate Similarity	NPD4966	Approved
0.7746	Intermediate Similarity	NPD7054	Approved
0.7706	Intermediate Similarity	NPD8127	Discontinued
0.7701	Intermediate Similarity	NPD7472	Approved
0.7697	Intermediate Similarity	NPD4380	Phase 2
0.7665	Intermediate Similarity	NPD2801	Approved
0.764	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7473	Discontinued
0.7625	Intermediate Similarity	NPD6674	Discontinued
0.7616	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7266	Discontinued
0.7602	Intermediate Similarity	NPD6959	Discontinued
0.7571	Intermediate Similarity	NPD7808	Phase 3
0.756	Intermediate Similarity	NPD8455	Phase 2
0.7558	Intermediate Similarity	NPD6232	Discontinued
0.7533	Intermediate Similarity	NPD1610	Phase 2
0.7529	Intermediate Similarity	NPD7075	Discontinued
0.7516	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5124	Phase 1
0.7514	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7251	Discontinued
0.7472	Intermediate Similarity	NPD7549	Discontinued
0.7471	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2861	Phase 2
0.7458	Intermediate Similarity	NPD6797	Phase 2
0.7456	Intermediate Similarity	NPD1465	Phase 2
0.7456	Intermediate Similarity	NPD7819	Suspended
0.7452	Intermediate Similarity	NPD4060	Phase 1
0.7443	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1511	Approved
0.7436	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8312	Approved
0.743	Intermediate Similarity	NPD8313	Approved
0.7427	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7240	Approved
0.7412	Intermediate Similarity	NPD3817	Phase 2
0.7394	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4625	Phase 3
0.7353	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD1512	Approved
0.7342	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3620	Phase 2
0.7337	Intermediate Similarity	NPD7411	Suspended
0.732	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6801	Discontinued
0.7293	Intermediate Similarity	NPD8053	Approved
0.7293	Intermediate Similarity	NPD8054	Approved
0.7289	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8651	Approved
0.7267	Intermediate Similarity	NPD1548	Phase 1
0.7257	Intermediate Similarity	NPD7229	Phase 3
0.7256	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3018	Phase 2
0.7229	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7680	Approved
0.7222	Intermediate Similarity	NPD7685	Pre-registration
0.7212	Intermediate Similarity	NPD6190	Approved
0.7209	Intermediate Similarity	NPD5402	Approved
0.7208	Intermediate Similarity	NPD4749	Approved
0.72	Intermediate Similarity	NPD1247	Approved
0.7195	Intermediate Similarity	NPD1652	Phase 2
0.7186	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD919	Approved
0.7178	Intermediate Similarity	NPD5762	Approved
0.7178	Intermediate Similarity	NPD5763	Approved
0.7174	Intermediate Similarity	NPD7906	Approved
0.7152	Intermediate Similarity	NPD8166	Discontinued
0.7152	Intermediate Similarity	NPD3750	Approved
0.7134	Intermediate Similarity	NPD2424	Discontinued
0.7134	Intermediate Similarity	NPD1549	Phase 2
0.7126	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD8434	Phase 2
0.7119	Intermediate Similarity	NPD3926	Phase 2
0.7118	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5403	Approved
0.7099	Intermediate Similarity	NPD7097	Phase 1
0.7097	Intermediate Similarity	NPD2982	Phase 2
0.7097	Intermediate Similarity	NPD2983	Phase 2
0.7091	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7447	Phase 1
0.7081	Intermediate Similarity	NPD6355	Discontinued
0.7081	Intermediate Similarity	NPD5735	Approved
0.7078	Intermediate Similarity	NPD422	Phase 1
0.7073	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5588	Approved
0.7048	Intermediate Similarity	NPD4628	Phase 3
0.7048	Intermediate Similarity	NPD7466	Approved
0.7047	Intermediate Similarity	NPD5283	Phase 1
0.7035	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2981	Phase 2
0.7029	Intermediate Similarity	NPD3749	Approved
0.7027	Intermediate Similarity	NPD4663	Approved
0.7024	Intermediate Similarity	NPD7213	Phase 3
0.7024	Intermediate Similarity	NPD7212	Phase 2
0.7024	Intermediate Similarity	NPD4357	Discontinued
0.7018	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2796	Approved
0.7012	Intermediate Similarity	NPD6099	Approved
0.7012	Intermediate Similarity	NPD6100	Approved
0.7011	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3751	Discontinued
0.7	Intermediate Similarity	NPD6798	Discontinued
0.6994	Remote Similarity	NPD4536	Approved
0.6994	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4538	Approved
0.6983	Remote Similarity	NPD27	Approved
0.6983	Remote Similarity	NPD2489	Approved
0.6982	Remote Similarity	NPD5401	Approved
0.6982	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7843	Approved
0.6966	Remote Similarity	NPD3051	Approved
0.6966	Remote Similarity	NPD3787	Discontinued
0.6964	Remote Similarity	NPD5058	Phase 3
0.6961	Remote Similarity	NPD8156	Discontinued
0.6957	Remote Similarity	NPD4578	Approved
0.6957	Remote Similarity	NPD7310	Approved
0.6957	Remote Similarity	NPD7311	Approved
0.6957	Remote Similarity	NPD7312	Approved
0.6957	Remote Similarity	NPD7313	Approved
0.6957	Remote Similarity	NPD4577	Approved
0.6954	Remote Similarity	NPD7157	Approved
0.6951	Remote Similarity	NPD1510	Phase 2
0.6946	Remote Similarity	NPD6331	Phase 2
0.6941	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6273	Approved
0.6937	Remote Similarity	NPD7095	Approved
0.6927	Remote Similarity	NPD2969	Approved
0.6927	Remote Similarity	NPD2970	Approved
0.6923	Remote Similarity	NPD6799	Approved
0.6919	Remote Similarity	NPD7309	Approved
0.6915	Remote Similarity	NPD7047	Phase 3
0.6914	Remote Similarity	NPD4140	Approved
0.6913	Remote Similarity	NPD228	Approved
0.6911	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD2935	Discontinued
0.6909	Remote Similarity	NPD1551	Phase 2
0.6906	Remote Similarity	NPD8099	Discontinued
0.6906	Remote Similarity	NPD8251	Approved
0.6906	Remote Similarity	NPD8252	Approved
0.6898	Remote Similarity	NPD6841	Approved
0.6898	Remote Similarity	NPD6843	Phase 3
0.6898	Remote Similarity	NPD6842	Approved
0.6882	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2532	Approved
0.6882	Remote Similarity	NPD2534	Approved
0.6882	Remote Similarity	NPD2533	Approved
0.6879	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6599	Discontinued
0.6871	Remote Similarity	NPD230	Phase 1
0.6869	Remote Similarity	NPD8151	Discontinued
0.6867	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6005	Phase 3
0.6867	Remote Similarity	NPD6004	Phase 3
0.6867	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6002	Phase 3
0.6867	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5536	Phase 2
0.6859	Remote Similarity	NPD1091	Approved
0.6859	Remote Similarity	NPD3705	Approved
0.6852	Remote Similarity	NPD6233	Phase 2
0.6848	Remote Similarity	NPD3748	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