NPASS Compound

Structure

NPC475174 OpenBabel07101718272D 59 64 0 0 1 0 0 0 0 0999 V2000 3.6177 3.6177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3629 2.6666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9215 4.3139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4118 -1.5290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4118 2.4118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9704 4.0591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4118 -0.5444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1172 2.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3435 1.1376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1172 1.4248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 0.4414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5591 -2.0213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5591 0.9325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4118 2.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5494 -0.0683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6753 -0.0521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1080 -1.7156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2059 1.2059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7156 3.1080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5591 -0.0521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4118 1.4248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8532 -0.7645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2645 2.9017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2946 0.8828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2645 0.9325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9021 -0.5097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8226 -0.5444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.2548 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.8226 -1.5290 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6473 -0.4414 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.9699 -2.0213 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3925 -1.3925 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1172 -1.5290 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4414 -1.6473 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7064 -0.5444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7645 2.8532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1172 -0.5444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2548 -0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7553 -1.2742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7064 -1.5290 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -11.6753 0.9325 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2645 3.8864 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9908 1.5790 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.6753 -2.0213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5984 -0.1866 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9699 -3.0059 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0887 -2.0887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2645 -2.0213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1866 -2.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0010 0.4402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0683 3.5494 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5005 -0.3231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8349 -2.5052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5097 1.9021 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0591 -1.9704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2645 -0.0521 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2059 -1.2059 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9699 -0.0521 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 4 7 1 0 0 0 0 4 12 2 0 0 0 0 5 19 2 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 8 23 2 0 0 0 0 9 11 1 0 0 0 0 9 24 2 0 0 0 0 10 25 2 0 0 0 0 11 26 2 0 0 0 0 12 40 1 0 0 0 0 13 20 2 0 0 0 0 13 21 1 0 0 0 0 14 21 2 0 0 0 0 14 23 1 0 0 0 0 15 22 2 0 0 0 0 15 24 1 0 0 0 0 16 41 1 0 0 0 0 17 22 1 0 0 0 0 17 55 1 0 0 0 0 18 54 1 0 0 0 0 19 36 1 0 0 0 0 20 35 1 0 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 23 42 1 0 0 0 0 24 43 1 0 0 0 0 25 56 1 0 0 0 0 26 57 1 0 0 0 0 27 16 1 1 0 0 0 27 29 1 0 0 0 0 27 58 1 0 0 0 0 28 18 1 6 0 0 0 28 30 1 0 0 0 0 28 59 1 0 0 0 0 29 31 1 0 0 0 0 29 44 1 6 0 0 0 30 32 1 0 0 0 0 30 45 1 1 0 0 0 31 33 1 0 0 0 0 31 46 1 1 0 0 0 32 34 1 0 0 0 0 32 47 1 6 0 0 0 33 37 1 0 0 0 0 33 48 1 6 0 0 0 34 38 1 0 0 0 0 34 49 1 1 0 0 0 35 40 1 0 0 0 0 35 50 2 0 0 0 0 36 51 2 0 0 0 0 36 54 1 0 0 0 0 37 56 1 1 0 0 0 37 58 1 0 0 0 0 38 57 1 6 0 0 0 38 59 1 0 0 0 0 39 40 1 0 0 0 0 39 52 2 0 0 0 0 39 55 1 0 0 0 0 40 53 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	826.23
Volume:	779.161
LogP:	1.257
LogD:	0.89
LogS:	-2.783
# Rotatable Bonds:	14
TPSA:	308.89
# H-Bond Aceptor:	19
# H-Bond Donor:	10
# Rings:	6
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.044
Synthetic Accessibility Score:	5.386
Fsp3:	0.375
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:	-6.79
MDCK Permeability:	1.9183906260877848e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.341
Human Intestinal Absorption (HIA):	0.868
20% Bioavailability (F20%):	0.472
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.121
Plasma Protein Binding (PPB):	98.01806640625%
Volume Distribution (VD):	0.577
Pgp-substrate:	4.183319091796875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.022
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.115
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.361
CYP3A4-substrate:	0.068

ADMET: Excretion

Clearance (CL):	1.03
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.17
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.157
Carcinogencity:	0.362
Eye Corrosion:	0.003
Eye Irritation:	0.057
Respiratory Toxicity:	0.001

Download Data

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

Natural Product: NPC475174

Natural Product ID:	NPC475174
*Common Name:**	Itoside J
IUPAC Name:	[2-[(2S,3R,4S,5S,6R)-6-(benzoyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxyphenyl]methyl (5E)-1-hydroxy-5-[[5-hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methylidene]-6-oxocyclohex-2-ene-1-carboxylate
Synonyms:	Itoside J
Standard InCHIKey:	VJDJBHKKFHYOAP-BQQHIGENSA-N
Standard InCHI:	InChI=1S/C40H42O19/c41-16-27-29(44)31(46)33(48)37(58-27)56-25-10-8-23(42)14-21(25)13-20-7-4-12-40(53,35(20)50)39(52)55-17-22-15-24(43)9-11-26(22)57-38-34(49)32(47)30(45)28(59-38)18-54-36(51)19-5-2-1-3-6-19/h1-6,8-15,27-34,37-38,41-49,53H,7,16-18H2/b20-13+/t27-,28-,29-,30-,31+,32+,33-,34-,37-,38-,40?/m1/s1
SMILES:	C1C=CC(C(=O)C1=CC2=C(C=CC(=C2)O)OC3C(C(C(C(O3)CO)O)O)O)(C(=O)OCC4=C(C=CC(=C4)O)OC5C(C(C(C(O5)COC(=O)C6=CC=CC=C6)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500077
PubChem CID:	24879103
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO9317	Itoa orientalis	Species	Salicaceae	Eukaryota	bark, twigs, and leaves	n.a.	n.a.	PMID[18412396]
NPO9317	Itoa orientalis	Species	Salicaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	3.3	%	PMID[517670]

☑ 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 NPC475174 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	395
0.1-0.2	1620
0.2-0.3	3807
0.3-0.4	8394
0.4-0.5	9535
0.5-0.6	5711
0.6-0.7	7408
0.7-0.8	4843
0.8-0.85	906
0.85-0.9	59
0.9-0.95	15
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9872	High Similarity	NPC475183
0.9684	High Similarity	NPC280923
0.9565	High Similarity	NPC280385
0.9551	High Similarity	NPC474441
0.9551	High Similarity	NPC476026
0.9551	High Similarity	NPC474398
0.9551	High Similarity	NPC474401
0.9367	High Similarity	NPC57072
0.9367	High Similarity	NPC231475
0.9329	High Similarity	NPC470438
0.925	High Similarity	NPC132737
0.9236	High Similarity	NPC279281
0.9236	High Similarity	NPC92153
0.9236	High Similarity	NPC230439
0.9236	High Similarity	NPC299761
0.9167	High Similarity	NPC131874
0.9167	High Similarity	NPC93619
0.913	High Similarity	NPC71780
0.9038	High Similarity	NPC22137
0.8974	High Similarity	NPC92054
0.8974	High Similarity	NPC140722
0.8974	High Similarity	NPC4958
0.891	High Similarity	NPC474422
0.8862	High Similarity	NPC164704
0.8862	High Similarity	NPC470712
0.8812	High Similarity	NPC215811
0.881	High Similarity	NPC470716
0.881	High Similarity	NPC257011
0.881	High Similarity	NPC474522
0.881	High Similarity	NPC9002
0.881	High Similarity	NPC137871
0.881	High Similarity	NPC470714
0.881	High Similarity	NPC470715
0.881	High Similarity	NPC288152
0.8779	High Similarity	NPC470718
0.8779	High Similarity	NPC156785
0.8779	High Similarity	NPC241781
0.8779	High Similarity	NPC162394
0.8758	High Similarity	NPC260604
0.8758	High Similarity	NPC299435
0.875	High Similarity	NPC199079
0.875	High Similarity	NPC210808
0.8734	High Similarity	NPC83975
0.8728	High Similarity	NPC223860
0.8728	High Similarity	NPC249560
0.8728	High Similarity	NPC25946
0.8728	High Similarity	NPC470720
0.8728	High Similarity	NPC21359
0.8728	High Similarity	NPC275977
0.8728	High Similarity	NPC460984
0.8728	High Similarity	NPC470713
0.8728	High Similarity	NPC470717
0.8721	High Similarity	NPC469371
0.8696	High Similarity	NPC183536
0.8696	High Similarity	NPC34965
0.869	High Similarity	NPC472133
0.8688	High Similarity	NPC475890
0.8678	High Similarity	NPC33083
0.8678	High Similarity	NPC295625
0.8678	High Similarity	NPC470719
0.8678	High Similarity	NPC473554
0.8675	High Similarity	NPC80068
0.8662	High Similarity	NPC138915
0.8655	High Similarity	NPC76112
0.8655	High Similarity	NPC170018
0.8655	High Similarity	NPC231787
0.8655	High Similarity	NPC66820
0.8655	High Similarity	NPC92403
0.8642	High Similarity	NPC160882
0.8639	High Similarity	NPC209550
0.8639	High Similarity	NPC175429
0.8639	High Similarity	NPC469344
0.8639	High Similarity	NPC472129
0.8639	High Similarity	NPC280642
0.8639	High Similarity	NPC188815
0.8639	High Similarity	NPC277532
0.8639	High Similarity	NPC43434
0.8639	High Similarity	NPC218161
0.8639	High Similarity	NPC96605
0.8639	High Similarity	NPC138990
0.8631	High Similarity	NPC128403
0.8629	High Similarity	NPC97817
0.8629	High Similarity	NPC30011
0.8629	High Similarity	NPC72554
0.8623	High Similarity	NPC139060
0.8623	High Similarity	NPC129264
0.8623	High Similarity	NPC19240
0.8623	High Similarity	NPC85751
0.8623	High Similarity	NPC205824
0.8621	High Similarity	NPC470455
0.8621	High Similarity	NPC470416
0.8621	High Similarity	NPC470451
0.8614	High Similarity	NPC472876
0.8605	High Similarity	NPC253521
0.8605	High Similarity	NPC113836
0.8605	High Similarity	NPC37668
0.8605	High Similarity	NPC476619
0.8605	High Similarity	NPC476618
0.8605	High Similarity	NPC476620
0.8605	High Similarity	NPC476622
0.8605	High Similarity	NPC472387
0.8605	High Similarity	NPC477895
0.8605	High Similarity	NPC476621
0.8605	High Similarity	NPC476623
0.8596	High Similarity	NPC34267
0.8596	High Similarity	NPC223426
0.8596	High Similarity	NPC214621
0.8596	High Similarity	NPC81042
0.859	High Similarity	NPC245219
0.859	High Similarity	NPC65833
0.859	High Similarity	NPC31081
0.8588	High Similarity	NPC11847
0.8588	High Similarity	NPC102851
0.8588	High Similarity	NPC217822
0.8588	High Similarity	NPC101399
0.8588	High Similarity	NPC47140
0.8588	High Similarity	NPC67134
0.8588	High Similarity	NPC5786
0.8588	High Similarity	NPC221288
0.8571	High Similarity	NPC473278
0.8571	High Similarity	NPC70441
0.8571	High Similarity	NPC260504
0.8571	High Similarity	NPC64425
0.8571	High Similarity	NPC89809
0.8571	High Similarity	NPC104910
0.8571	High Similarity	NPC474093
0.8563	High Similarity	NPC121290
0.8563	High Similarity	NPC36138
0.8563	High Similarity	NPC199172
0.8563	High Similarity	NPC297503
0.8563	High Similarity	NPC97119
0.8563	High Similarity	NPC470446
0.8563	High Similarity	NPC470449
0.8563	High Similarity	NPC135831
0.8563	High Similarity	NPC470445
0.8563	High Similarity	NPC470447
0.8563	High Similarity	NPC35924
0.8563	High Similarity	NPC127415
0.8554	High Similarity	NPC477629
0.8554	High Similarity	NPC270675
0.8554	High Similarity	NPC472994
0.8554	High Similarity	NPC195685
0.8554	High Similarity	NPC210961
0.8554	High Similarity	NPC477628
0.8547	High Similarity	NPC61904
0.8547	High Similarity	NPC471669
0.8547	High Similarity	NPC472992
0.8547	High Similarity	NPC144097
0.8547	High Similarity	NPC473862
0.8547	High Similarity	NPC472991
0.8547	High Similarity	NPC89127
0.8531	High Similarity	NPC314672
0.8529	High Similarity	NPC76047
0.8529	High Similarity	NPC92815
0.8528	High Similarity	NPC185103
0.8523	High Similarity	NPC475179
0.8512	High Similarity	NPC287889
0.8512	High Similarity	NPC99216
0.8512	High Similarity	NPC135358
0.8512	High Similarity	NPC292929
0.8512	High Similarity	NPC472130
0.8512	High Similarity	NPC289667
0.8512	High Similarity	NPC472131
0.8512	High Similarity	NPC76831
0.8509	High Similarity	NPC182350
0.8509	High Similarity	NPC471214
0.8508	High Similarity	NPC131405
0.8503	High Similarity	NPC298171
0.85	High Similarity	NPC302989
0.8497	Intermediate Similarity	NPC293626
0.8497	Intermediate Similarity	NPC139571
0.8497	Intermediate Similarity	NPC196127
0.8497	Intermediate Similarity	NPC217520
0.8497	Intermediate Similarity	NPC217387
0.8497	Intermediate Similarity	NPC173837
0.8497	Intermediate Similarity	NPC258044
0.8497	Intermediate Similarity	NPC267680
0.8497	Intermediate Similarity	NPC35167
0.8494	Intermediate Similarity	NPC328093
0.8494	Intermediate Similarity	NPC136761
0.8488	Intermediate Similarity	NPC253685
0.848	Intermediate Similarity	NPC315619
0.8471	Intermediate Similarity	NPC658
0.8471	Intermediate Similarity	NPC246274
0.8471	Intermediate Similarity	NPC95421
0.8471	Intermediate Similarity	NPC198125
0.8471	Intermediate Similarity	NPC197708
0.8462	Intermediate Similarity	NPC203145
0.8462	Intermediate Similarity	NPC12013
0.8462	Intermediate Similarity	NPC477613
0.8462	Intermediate Similarity	NPC262222
0.8462	Intermediate Similarity	NPC68592
0.8462	Intermediate Similarity	NPC186816
0.8462	Intermediate Similarity	NPC32641
0.8462	Intermediate Similarity	NPC11432
0.8462	Intermediate Similarity	NPC476470
0.8462	Intermediate Similarity	NPC221342
0.8462	Intermediate Similarity	NPC142142
0.8462	Intermediate Similarity	NPC189564
0.8462	Intermediate Similarity	NPC256188

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 NPC475174 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	904
0.2-0.3	1918
0.3-0.4	2644
0.4-0.5	1977
0.5-0.6	954
0.6-0.7	282
0.7-0.8	106
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8655	High Similarity	NPD8313	Approved
0.8655	High Similarity	NPD8312	Approved
0.8488	Intermediate Similarity	NPD7808	Phase 3
0.843	Intermediate Similarity	NPD7251	Discontinued
0.8418	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD6797	Phase 2
0.8364	Intermediate Similarity	NPD5402	Approved
0.8363	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD7472	Approved
0.8263	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD7054	Approved
0.8208	Intermediate Similarity	NPD7074	Phase 3
0.8193	Intermediate Similarity	NPD8455	Phase 2
0.8161	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD6166	Phase 2
0.8081	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD5403	Approved
0.8011	Intermediate Similarity	NPD6559	Discontinued
0.7989	Intermediate Similarity	NPD3751	Discontinued
0.7941	Intermediate Similarity	NPD7075	Discontinued
0.7927	Intermediate Similarity	NPD5401	Approved
0.7886	Intermediate Similarity	NPD3818	Discontinued
0.7882	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD7435	Discontinued
0.7802	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7698	Approved
0.7778	Intermediate Similarity	NPD7696	Phase 3
0.7778	Intermediate Similarity	NPD7697	Approved
0.7765	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD3787	Discontinued
0.7737	Intermediate Similarity	NPD7871	Phase 2
0.7737	Intermediate Similarity	NPD7870	Phase 2
0.772	Intermediate Similarity	NPD7874	Approved
0.772	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD6779	Approved
0.7713	Intermediate Similarity	NPD6776	Approved
0.7713	Intermediate Similarity	NPD6780	Approved
0.7713	Intermediate Similarity	NPD6781	Approved
0.7713	Intermediate Similarity	NPD6777	Approved
0.7713	Intermediate Similarity	NPD6782	Approved
0.7713	Intermediate Similarity	NPD6778	Approved
0.7708	Intermediate Similarity	NPD7701	Phase 2
0.7692	Intermediate Similarity	NPD8150	Discontinued
0.7692	Intermediate Similarity	NPD4380	Phase 2
0.768	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7783	Phase 2
0.7679	Intermediate Similarity	NPD1653	Approved
0.7616	Intermediate Similarity	NPD3817	Phase 2
0.7611	Intermediate Similarity	NPD7685	Pre-registration
0.7606	Intermediate Similarity	NPD7699	Phase 2
0.7606	Intermediate Similarity	NPD7700	Phase 2
0.7602	Intermediate Similarity	NPD6801	Discontinued
0.7558	Intermediate Similarity	NPD7819	Suspended
0.7545	Intermediate Similarity	NPD6799	Approved
0.7544	Intermediate Similarity	NPD7411	Suspended
0.7542	Intermediate Similarity	NPD5844	Phase 1
0.7541	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD6823	Phase 2
0.7514	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7266	Discontinued
0.75	Intermediate Similarity	NPD7801	Approved
0.75	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD1934	Approved
0.7487	Intermediate Similarity	NPD8151	Discontinued
0.7472	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7768	Phase 2
0.7461	Intermediate Similarity	NPD8320	Phase 1
0.7461	Intermediate Similarity	NPD8319	Approved
0.7457	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD2801	Approved
0.7447	Intermediate Similarity	NPD6534	Approved
0.7447	Intermediate Similarity	NPD6535	Approved
0.7439	Intermediate Similarity	NPD1551	Phase 2
0.7439	Intermediate Similarity	NPD2935	Discontinued
0.7427	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6190	Approved
0.7407	Intermediate Similarity	NPD1933	Approved
0.7401	Intermediate Similarity	NPD6959	Discontinued
0.7396	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6233	Phase 2
0.7389	Intermediate Similarity	NPD7228	Approved
0.7371	Intermediate Similarity	NPD3882	Suspended
0.7365	Intermediate Similarity	NPD3750	Approved
0.7365	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1512	Approved
0.7349	Intermediate Similarity	NPD1549	Phase 2
0.7342	Intermediate Similarity	NPD1203	Approved
0.7312	Intermediate Similarity	NPD6832	Phase 2
0.7308	Intermediate Similarity	NPD1091	Approved
0.7305	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6599	Discontinued
0.7262	Intermediate Similarity	NPD4628	Phase 3
0.7247	Intermediate Similarity	NPD5494	Approved
0.7235	Intermediate Similarity	NPD1511	Approved
0.7232	Intermediate Similarity	NPD3749	Approved
0.7225	Intermediate Similarity	NPD7458	Discontinued
0.7225	Intermediate Similarity	NPD3226	Approved
0.7222	Intermediate Similarity	NPD6798	Discontinued
0.7209	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6844	Discontinued
0.7195	Intermediate Similarity	NPD447	Suspended
0.7195	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD1465	Phase 2
0.7143	Intermediate Similarity	NPD7473	Discontinued
0.7135	Intermediate Similarity	NPD7240	Approved
0.7135	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6213	Phase 3
0.712	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6212	Phase 3
0.7117	Intermediate Similarity	NPD2313	Discontinued
0.7111	Intermediate Similarity	NPD7199	Phase 2
0.7088	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2346	Discontinued
0.7072	Intermediate Similarity	NPD6232	Discontinued
0.7066	Intermediate Similarity	NPD1510	Phase 2
0.7066	Intermediate Similarity	NPD7033	Discontinued
0.7066	Intermediate Similarity	NPD3748	Approved
0.7044	Intermediate Similarity	NPD9717	Approved
0.7035	Intermediate Similarity	NPD7584	Approved
0.7024	Intermediate Similarity	NPD2796	Approved
0.7006	Intermediate Similarity	NPD7097	Phase 1
0.7006	Intermediate Similarity	NPD37	Approved
0.7	Intermediate Similarity	NPD6234	Discontinued
0.6988	Remote Similarity	NPD6355	Discontinued
0.6983	Remote Similarity	NPD4965	Approved
0.6983	Remote Similarity	NPD4966	Approved
0.6983	Remote Similarity	NPD4967	Phase 2
0.6981	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4308	Phase 3
0.6957	Remote Similarity	NPD3225	Approved
0.6919	Remote Similarity	NPD7799	Discontinued
0.6915	Remote Similarity	NPD7585	Approved
0.6909	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD411	Approved
0.69	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2798	Approved
0.6866	Remote Similarity	NPD7583	Approved
0.6864	Remote Similarity	NPD2799	Discontinued
0.6848	Remote Similarity	NPD7095	Approved
0.6842	Remote Similarity	NPD970	Clinical (unspecified phase)
0.684	Remote Similarity	NPD8059	Phase 3
0.684	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD8127	Discontinued
0.6826	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1613	Approved
0.6826	Remote Similarity	NPD1240	Approved
0.681	Remote Similarity	NPD2797	Approved
0.6807	Remote Similarity	NPD3268	Approved
0.6807	Remote Similarity	NPD3764	Approved
0.68	Remote Similarity	NPD7680	Approved
0.6796	Remote Similarity	NPD7930	Approved
0.6791	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7440	Discontinued
0.6768	Remote Similarity	NPD8285	Discontinued
0.6768	Remote Similarity	NPD1019	Discontinued
0.6761	Remote Similarity	NPD6273	Approved
0.6757	Remote Similarity	NPD3926	Phase 2
0.6746	Remote Similarity	NPD1607	Approved
0.6731	Remote Similarity	NPD8404	Phase 2
0.6727	Remote Similarity	NPD2861	Phase 2
0.6726	Remote Similarity	NPD4060	Phase 1
0.6726	Remote Similarity	NPD4307	Phase 2
0.6725	Remote Similarity	NPD5404	Approved
0.6725	Remote Similarity	NPD5406	Approved
0.6725	Remote Similarity	NPD6100	Approved
0.6725	Remote Similarity	NPD6099	Approved
0.6725	Remote Similarity	NPD5405	Approved
0.6725	Remote Similarity	NPD5408	Approved
0.6721	Remote Similarity	NPD919	Approved
0.6709	Remote Similarity	NPD9493	Approved
0.6708	Remote Similarity	NPD3496	Discontinued
0.6706	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6674	Discontinued
0.6698	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4908	Phase 1
0.6686	Remote Similarity	NPD230	Phase 1
0.6686	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2344	Approved
0.6686	Remote Similarity	NPD5763	Approved
0.6686	Remote Similarity	NPD5762	Approved
0.6684	Remote Similarity	NPD7039	Approved
0.6684	Remote Similarity	NPD8368	Discontinued
0.6684	Remote Similarity	NPD7038	Approved
0.6683	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5049	Phase 3
0.6667	Remote Similarity	NPD4062	Phase 3
0.6667	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD1247	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