NPASS Compound

Structure

NPC470098 OpenBabel07101719512D 58 63 0 0 1 0 0 0 0 0999 V2000 -10.1859 2.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 -0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8558 2.0649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9898 -2.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3199 -0.9351 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 -10.1859 -0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4539 0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1237 1.0649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2577 -0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 0.9945 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 -6.7218 0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 1.4945 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 -1.3090 2.2673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4539 -0.4351 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 -3.2577 0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 0.6581 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -10.1859 0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3199 1.0649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9898 0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1237 -0.9351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7218 -0.4351 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.4347 2.4945 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.5878 -0.9351 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.3007 2.9945 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.3917 1.0649 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.9898 -0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5878 1.0649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0519 1.0649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5878 -1.9351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 3.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3199 2.0649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 -0.0055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8558 1.0649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1237 -1.9351 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 1.8366 3.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2872 2.0594 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 -5.8558 -0.9351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 2.9945 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 54 1 0 0 0 0 7 9 2 0 0 0 0 7 21 1 0 0 0 0 8 10 2 0 0 0 0 8 22 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 21 2 0 0 0 0 11 29 1 0 0 0 0 12 22 2 0 0 0 0 12 30 1 0 0 0 0 13 23 2 0 0 0 0 13 31 1 0 0 0 0 14 23 1 0 0 0 0 14 32 2 0 0 0 0 15 24 2 0 0 0 0 15 33 1 0 0 0 0 16 24 1 0 0 0 0 16 34 2 0 0 0 0 17 35 1 0 0 0 0 17 43 1 0 0 0 0 18 36 1 0 0 0 0 18 44 1 0 0 0 0 19 25 1 0 0 0 0 19 56 1 0 0 0 0 20 26 1 0 0 0 0 20 55 1 0 0 0 0 21 37 1 0 0 0 0 22 38 1 0 0 0 0 23 39 1 0 0 0 0 24 40 1 0 0 0 0 25 26 1 0 0 0 0 25 39 1 0 0 0 0 26 40 1 0 0 0 0 27 29 2 0 0 0 0 27 45 1 0 0 0 0 28 30 2 0 0 0 0 28 46 1 0 0 0 0 29 49 1 0 0 0 0 30 50 1 0 0 0 0 31 41 2 0 0 0 0 31 51 1 0 0 0 0 32 41 1 0 0 0 0 32 52 1 0 0 0 0 33 42 2 0 0 0 0 33 53 1 0 0 0 0 34 42 1 0 0 0 0 34 54 1 0 0 0 0 35 37 1 0 0 0 0 35 57 1 0 0 0 0 36 38 1 0 0 0 0 36 58 1 0 0 0 0 37 47 1 0 0 0 0 38 48 1 0 0 0 0 39 55 1 0 0 0 0 40 56 1 0 0 0 0 41 57 1 0 0 0 0 42 58 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	810.31
Volume:	792.655
LogP:	1.905
LogD:	2.425
LogS:	-4.365
# Rotatable Bonds:	18
TPSA:	213.68
# H-Bond Aceptor:	16
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.083
Synthetic Accessibility Score:	4.979
Fsp3:	0.429
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.705
MDCK Permeability:	2.2186066416907124e-05
Pgp-inhibitor:	0.894
Pgp-substrate:	0.936
Human Intestinal Absorption (HIA):	0.652
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118
Plasma Protein Binding (PPB):	60.65259552001953%
Volume Distribution (VD):	0.476
Pgp-substrate:	39.98397445678711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.231
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.903
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.679
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.835
CYP3A4-inhibitor:	0.519
CYP3A4-substrate:	0.933

ADMET: Excretion

Clearance (CL):	6.734
Half-life (T1/2):	0.376

ADMET: Toxicity

hERG Blockers:	0.164
Human Hepatotoxicity (H-HT):	0.088
Drug-inuced Liver Injury (DILI):	0.168
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.462
Maximum Recommended Daily Dose:	0.586
Skin Sensitization:	0.237
Carcinogencity:	0.017
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.004

Download Data

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

Natural Product: NPC470098

Natural Product ID:	NPC470098
*Common Name:**	Hedyotisol B
IUPAC Name:	2-[4-[6-[4-[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3,5-dimethoxyphenyl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenoxy]-1-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol
Synonyms:	Hedyotisol B; Hedyotisol C
Standard InCHIKey:	LSWNERGQFCAXLI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C42H50O16/c1-49-29-11-21(7-9-27(29)45)37(47)35(17-43)57-41-31(51-3)13-23(14-32(41)52-4)39-25-19-56-40(26(25)20-55-39)24-15-33(53-5)42(34(16-24)54-6)58-36(18-44)38(48)22-8-10-28(46)30(12-22)50-2/h7-16,25-26,35-40,43-48H,17-20H2,1-6H3
SMILES:	OCC(C(c1ccc(c(c1)OC)O)O)Oc1c(OC)cc(cc1OC)C1OCC2C1COC2c1cc(OC)c(c(c1)OC)OC(C(c1ccc(c(c1)OC)O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1761832
PubChem CID:	15628159
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans

*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
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[21435874]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29118	Euonymus alatus	Species	Celastraceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[490553]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[490554]

☑ 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 NPC470098 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	486
0.1-0.2	1373
0.2-0.3	3967
0.3-0.4	10567
0.4-0.5	8563
0.5-0.6	5337
0.6-0.7	8035
0.7-0.8	3428
0.8-0.85	674
0.85-0.9	226
0.9-0.95	26
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470826
1.0	High Similarity	NPC473266
0.986	High Similarity	NPC329343
0.986	High Similarity	NPC324517
0.986	High Similarity	NPC321972
0.9645	High Similarity	NPC471415
0.9645	High Similarity	NPC114119
0.9645	High Similarity	NPC470097
0.958	High Similarity	NPC328567
0.958	High Similarity	NPC320970
0.958	High Similarity	NPC320671
0.958	High Similarity	NPC327412
0.951	High Similarity	NPC317053
0.951	High Similarity	NPC324492
0.9433	High Similarity	NPC470372
0.9362	High Similarity	NPC291101
0.9362	High Similarity	NPC266197
0.9291	High Similarity	NPC260842
0.9262	High Similarity	NPC157333
0.9252	High Similarity	NPC477612
0.9247	High Similarity	NPC304048
0.9247	High Similarity	NPC226153
0.9241	High Similarity	NPC260397
0.9225	High Similarity	NPC55793
0.922	High Similarity	NPC474390
0.9172	High Similarity	NPC181615
0.9155	High Similarity	NPC22517
0.9149	High Similarity	NPC77861
0.9145	High Similarity	NPC470828
0.9116	High Similarity	NPC20757
0.9116	High Similarity	NPC227516
0.9116	High Similarity	NPC329836
0.911	High Similarity	NPC241846
0.911	High Similarity	NPC93610
0.9103	High Similarity	NPC304894
0.9103	High Similarity	NPC15659
0.9091	High Similarity	NPC262189
0.9091	High Similarity	NPC22317
0.9079	High Similarity	NPC470827
0.9078	High Similarity	NPC93783
0.9078	High Similarity	NPC34103
0.9078	High Similarity	NPC165155
0.9078	High Similarity	NPC99572
0.9078	High Similarity	NPC126409
0.9078	High Similarity	NPC141765
0.9078	High Similarity	NPC24490
0.9073	High Similarity	NPC202104
0.9054	High Similarity	NPC286235
0.9054	High Similarity	NPC51328
0.9054	High Similarity	NPC55158
0.9054	High Similarity	NPC211561
0.9038	High Similarity	NPC59516
0.9034	High Similarity	NPC173203
0.9034	High Similarity	NPC163508
0.9028	High Similarity	NPC178054
0.9007	High Similarity	NPC244983
0.9007	High Similarity	NPC287745
0.9007	High Similarity	NPC326095
0.9	High Similarity	NPC226809
0.9	High Similarity	NPC279406
0.8986	High Similarity	NPC248132
0.8986	High Similarity	NPC281549
0.8986	High Similarity	NPC130449
0.8973	High Similarity	NPC28440
0.8973	High Similarity	NPC171932
0.8958	High Similarity	NPC184797
0.8958	High Similarity	NPC309124
0.8954	High Similarity	NPC125495
0.894	High Similarity	NPC224161
0.8936	High Similarity	NPC158331
0.8926	High Similarity	NPC321657
0.8926	High Similarity	NPC95392
0.8926	High Similarity	NPC55715
0.8926	High Similarity	NPC476969
0.8926	High Similarity	NPC475250
0.8926	High Similarity	NPC35877
0.8926	High Similarity	NPC318373
0.8919	High Similarity	NPC170103
0.8919	High Similarity	NPC108811
0.8919	High Similarity	NPC99183
0.8919	High Similarity	NPC204770
0.8919	High Similarity	NPC236202
0.8919	High Similarity	NPC263940
0.8919	High Similarity	NPC82917
0.8919	High Similarity	NPC70409
0.8919	High Similarity	NPC58190
0.8919	High Similarity	NPC202742
0.8919	High Similarity	NPC18185
0.8919	High Similarity	NPC262911
0.8919	High Similarity	NPC294558
0.8919	High Similarity	NPC39657
0.8897	High Similarity	NPC87725
0.8897	High Similarity	NPC263261
0.8897	High Similarity	NPC311530
0.8889	High Similarity	NPC232164
0.8889	High Similarity	NPC473739
0.8889	High Similarity	NPC236306
0.8889	High Similarity	NPC55947
0.8882	High Similarity	NPC46335
0.8873	High Similarity	NPC170694
0.8867	High Similarity	NPC475224
0.8865	High Similarity	NPC470752
0.8865	High Similarity	NPC204215
0.8865	High Similarity	NPC35932
0.8865	High Similarity	NPC184447
0.8865	High Similarity	NPC16208
0.8865	High Similarity	NPC160991
0.8865	High Similarity	NPC131128
0.8865	High Similarity	NPC474134
0.8865	High Similarity	NPC175067
0.8865	High Similarity	NPC7903
0.8859	High Similarity	NPC102934
0.8859	High Similarity	NPC252402
0.8851	High Similarity	NPC96576
0.8836	High Similarity	NPC107161
0.8836	High Similarity	NPC302506
0.8828	High Similarity	NPC472090
0.8828	High Similarity	NPC472092
0.8828	High Similarity	NPC254759
0.8828	High Similarity	NPC160283
0.8828	High Similarity	NPC472091
0.8816	High Similarity	NPC470769
0.8794	High Similarity	NPC158079
0.8794	High Similarity	NPC30043
0.8794	High Similarity	NPC40432
0.8794	High Similarity	NPC309787
0.8794	High Similarity	NPC470096
0.8794	High Similarity	NPC474017
0.8794	High Similarity	NPC115207
0.8794	High Similarity	NPC469625
0.8794	High Similarity	NPC27843
0.8794	High Similarity	NPC469613
0.8794	High Similarity	NPC470095
0.8794	High Similarity	NPC228346
0.8794	High Similarity	NPC7171
0.8794	High Similarity	NPC472597
0.8794	High Similarity	NPC161557
0.8784	High Similarity	NPC38041
0.8784	High Similarity	NPC22150
0.8784	High Similarity	NPC279298
0.8782	High Similarity	NPC149873
0.8782	High Similarity	NPC7191
0.8776	High Similarity	NPC477616
0.8767	High Similarity	NPC247291
0.8767	High Similarity	NPC471389
0.8759	High Similarity	NPC292882
0.875	High Similarity	NPC16435
0.875	High Similarity	NPC162659
0.875	High Similarity	NPC476391
0.875	High Similarity	NPC265433
0.875	High Similarity	NPC306441
0.875	High Similarity	NPC248727
0.875	High Similarity	NPC270456
0.8741	High Similarity	NPC66840
0.8741	High Similarity	NPC310854
0.8741	High Similarity	NPC256307
0.8732	High Similarity	NPC4940
0.8732	High Similarity	NPC181049
0.8732	High Similarity	NPC253105
0.8732	High Similarity	NPC201587
0.8732	High Similarity	NPC207400
0.8725	High Similarity	NPC276753
0.8725	High Similarity	NPC205796
0.8725	High Similarity	NPC14468
0.8725	High Similarity	NPC112861
0.8723	High Similarity	NPC42300
0.8723	High Similarity	NPC472338
0.8723	High Similarity	NPC469612
0.8723	High Similarity	NPC92164
0.8723	High Similarity	NPC145305
0.8723	High Similarity	NPC257582
0.8723	High Similarity	NPC77040
0.8723	High Similarity	NPC187998
0.8723	High Similarity	NPC64201
0.8723	High Similarity	NPC153739
0.8723	High Similarity	NPC174495
0.8723	High Similarity	NPC241522
0.8723	High Similarity	NPC469614
0.8723	High Similarity	NPC242807
0.8718	High Similarity	NPC1253
0.8718	High Similarity	NPC100936
0.8716	High Similarity	NPC45257
0.8716	High Similarity	NPC12641
0.8716	High Similarity	NPC187774
0.8716	High Similarity	NPC84684
0.8716	High Similarity	NPC280092
0.8716	High Similarity	NPC208994
0.8716	High Similarity	NPC473046
0.8716	High Similarity	NPC185388
0.8716	High Similarity	NPC179521
0.8716	High Similarity	NPC63879
0.8716	High Similarity	NPC238216
0.8716	High Similarity	NPC472712
0.8716	High Similarity	NPC118385
0.8716	High Similarity	NPC93323
0.8716	High Similarity	NPC472713
0.871	High Similarity	NPC147743
0.871	High Similarity	NPC73517
0.871	High Similarity	NPC4809
0.8707	High Similarity	NPC476356

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 NPC470098 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	823
0.2-0.3	1897
0.3-0.4	2837
0.4-0.5	1701
0.5-0.6	1022
0.6-0.7	430
0.7-0.8	67
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8652	High Similarity	NPD3027	Phase 3
0.8472	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD1613	Approved
0.8194	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD4908	Phase 1
0.8125	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6234	Discontinued
0.8061	Intermediate Similarity	NPD7228	Approved
0.795	Intermediate Similarity	NPD4965	Approved
0.795	Intermediate Similarity	NPD4966	Approved
0.795	Intermediate Similarity	NPD4967	Phase 2
0.7866	Intermediate Similarity	NPD7199	Phase 2
0.7831	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6166	Phase 2
0.7764	Intermediate Similarity	NPD37	Approved
0.773	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1610	Phase 2
0.7706	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7240	Approved
0.7654	Intermediate Similarity	NPD1934	Approved
0.7635	Intermediate Similarity	NPD2861	Phase 2
0.7616	Intermediate Similarity	NPD3620	Phase 2
0.7616	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6674	Discontinued
0.7544	Intermediate Similarity	NPD7074	Phase 3
0.7544	Intermediate Similarity	NPD7472	Approved
0.7529	Intermediate Similarity	NPD3818	Discontinued
0.7516	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7054	Approved
0.7483	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2982	Phase 2
0.7483	Intermediate Similarity	NPD2983	Phase 2
0.7455	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5735	Approved
0.7447	Intermediate Similarity	NPD5283	Phase 1
0.7436	Intermediate Similarity	NPD7266	Discontinued
0.7431	Intermediate Similarity	NPD1548	Phase 1
0.7429	Intermediate Similarity	NPD8054	Approved
0.7429	Intermediate Similarity	NPD8053	Approved
0.7415	Intermediate Similarity	NPD2981	Phase 2
0.7414	Intermediate Similarity	NPD7808	Phase 3
0.741	Intermediate Similarity	NPD3882	Suspended
0.74	Intermediate Similarity	NPD3018	Phase 2
0.7394	Intermediate Similarity	NPD2801	Approved
0.7394	Intermediate Similarity	NPD8455	Phase 2
0.7386	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5844	Phase 1
0.7376	Intermediate Similarity	NPD7843	Approved
0.7365	Intermediate Similarity	NPD4749	Approved
0.7362	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7251	Discontinued
0.7351	Intermediate Similarity	NPD7680	Approved
0.7349	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD7157	Approved
0.7337	Intermediate Similarity	NPD8127	Discontinued
0.7305	Intermediate Similarity	NPD228	Approved
0.7303	Intermediate Similarity	NPD4625	Phase 3
0.7299	Intermediate Similarity	NPD6797	Phase 2
0.7278	Intermediate Similarity	NPD5494	Approved
0.7267	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD3705	Approved
0.7228	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7447	Phase 1
0.7207	Intermediate Similarity	NPD7906	Approved
0.7202	Intermediate Similarity	NPD7768	Phase 2
0.72	Intermediate Similarity	NPD8651	Approved
0.7197	Intermediate Similarity	NPD5588	Approved
0.7188	Intermediate Similarity	NPD7466	Approved
0.7168	Intermediate Similarity	NPD7473	Discontinued
0.7163	Intermediate Similarity	NPD3021	Approved
0.7163	Intermediate Similarity	NPD3022	Approved
0.7161	Intermediate Similarity	NPD1558	Phase 1
0.7161	Intermediate Similarity	NPD4060	Phase 1
0.716	Intermediate Similarity	NPD7213	Phase 3
0.716	Intermediate Similarity	NPD7212	Phase 2
0.716	Intermediate Similarity	NPD1511	Approved
0.7143	Intermediate Similarity	NPD3817	Phase 2
0.7143	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6959	Discontinued
0.7134	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4536	Approved
0.7134	Intermediate Similarity	NPD4538	Approved
0.7134	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7549	Discontinued
0.7119	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4380	Phase 2
0.7108	Intermediate Similarity	NPD4675	Approved
0.7108	Intermediate Similarity	NPD4678	Approved
0.7105	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6584	Phase 3
0.7099	Intermediate Similarity	NPD5058	Phase 3
0.7095	Intermediate Similarity	NPD5846	Approved
0.7095	Intermediate Similarity	NPD6516	Phase 2
0.7093	Intermediate Similarity	NPD6232	Discontinued
0.7092	Intermediate Similarity	NPD2684	Approved
0.7086	Intermediate Similarity	NPD8156	Discontinued
0.7083	Intermediate Similarity	NPD1465	Phase 2
0.7081	Intermediate Similarity	NPD6331	Phase 2
0.7078	Intermediate Similarity	NPD7095	Approved
0.7073	Intermediate Similarity	NPD1512	Approved
0.7063	Intermediate Similarity	NPD7037	Approved
0.7062	Intermediate Similarity	NPD7685	Pre-registration
0.7062	Intermediate Similarity	NPD6559	Discontinued
0.7059	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7831	Phase 2
0.7059	Intermediate Similarity	NPD7833	Phase 2
0.7059	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4663	Approved
0.7048	Intermediate Similarity	NPD4005	Discontinued
0.7037	Intermediate Similarity	NPD6190	Approved
0.7032	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD8251	Approved
0.7029	Intermediate Similarity	NPD8099	Discontinued
0.7029	Intermediate Similarity	NPD8252	Approved
0.7027	Intermediate Similarity	NPD1357	Approved
0.7025	Intermediate Similarity	NPD7097	Phase 1
0.702	Intermediate Similarity	NPD5327	Phase 3
0.7019	Intermediate Similarity	NPD4237	Approved
0.7019	Intermediate Similarity	NPD4236	Phase 3
0.7011	Intermediate Similarity	NPD2489	Approved
0.7011	Intermediate Similarity	NPD27	Approved
0.7006	Intermediate Similarity	NPD6355	Discontinued
0.7006	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5124	Phase 1
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD5763	Approved
0.7	Intermediate Similarity	NPD1091	Approved
0.6994	Remote Similarity	NPD7229	Phase 3
0.6994	Remote Similarity	NPD7124	Phase 2
0.6994	Remote Similarity	NPD3051	Approved
0.6989	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6233	Phase 2
0.6983	Remote Similarity	NPD7310	Approved
0.6983	Remote Similarity	NPD7312	Approved
0.6983	Remote Similarity	NPD8312	Approved
0.6983	Remote Similarity	NPD8313	Approved
0.6983	Remote Similarity	NPD4577	Approved
0.6983	Remote Similarity	NPD4578	Approved
0.6983	Remote Similarity	NPD7313	Approved
0.6983	Remote Similarity	NPD7311	Approved
0.6982	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5960	Phase 3
0.6978	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3892	Phase 2
0.6975	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4110	Phase 3
0.6962	Remote Similarity	NPD6353	Approved
0.6962	Remote Similarity	NPD6653	Approved
0.6959	Remote Similarity	NPD7075	Discontinued
0.6954	Remote Similarity	NPD2970	Approved
0.6954	Remote Similarity	NPD2969	Approved
0.6944	Remote Similarity	NPD7309	Approved
0.6943	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4140	Approved
0.6937	Remote Similarity	NPD2161	Phase 2
0.6937	Remote Similarity	NPD6099	Approved
0.6937	Remote Similarity	NPD6100	Approved
0.6928	Remote Similarity	NPD3094	Phase 2
0.6923	Remote Similarity	NPD6798	Discontinued
0.6914	Remote Similarity	NPD5177	Phase 3
0.6914	Remote Similarity	NPD1652	Phase 2
0.6914	Remote Similarity	NPD3060	Approved
0.6914	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6582	Phase 2
0.6908	Remote Similarity	NPD6583	Phase 3
0.6897	Remote Similarity	NPD3787	Discontinued
0.6894	Remote Similarity	NPD3540	Phase 1
0.6894	Remote Similarity	NPD1375	Discontinued
0.6894	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7819	Suspended
0.6882	Remote Similarity	NPD2977	Approved
0.6882	Remote Similarity	NPD5773	Approved
0.6882	Remote Similarity	NPD5772	Approved
0.6882	Remote Similarity	NPD2978	Approved
0.6875	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD8166	Discontinued
0.6871	Remote Similarity	NPD4628	Phase 3
0.6871	Remote Similarity	NPD6671	Approved
0.6867	Remote Similarity	NPD7526	Approved
0.6867	Remote Similarity	NPD52	Approved
0.6867	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4357	Discontinued
0.6845	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2560	Approved
0.6842	Remote Similarity	NPD2563	Approved
0.6842	Remote Similarity	NPD5402	Approved
0.6835	Remote Similarity	NPD2238	Phase 2
0.6832	Remote Similarity	NPD3539	Phase 1
0.6829	Remote Similarity	NPD2677	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