NPASS Compound

Structure

NPC475183 OpenBabel07101719522D 47 51 0 0 1 0 0 0 0 0999 V2000 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3960 -2.4824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6888 -1.7753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1371 -3.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7229 -2.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1712 -3.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9124 -4.6730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3336 -3.9914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 16 2 0 0 0 0 9 20 2 0 0 0 0 10 20 1 0 0 0 0 11 21 2 0 0 0 0 12 21 1 0 0 0 0 13 26 1 0 0 0 0 14 15 1 0 0 0 0 14 23 2 0 0 0 0 15 24 2 0 0 0 0 16 34 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 18 44 1 0 0 0 0 19 43 1 0 0 0 0 20 30 1 0 0 0 0 21 31 1 0 0 0 0 22 24 1 0 0 0 0 23 35 1 0 0 0 0 24 45 1 0 0 0 0 25 19 1 6 0 0 0 25 27 1 0 0 0 0 25 46 1 0 0 0 0 26 34 1 0 0 0 0 26 36 2 0 0 0 0 27 28 1 0 0 0 0 27 37 1 1 0 0 0 28 29 1 0 0 0 0 28 38 1 6 0 0 0 29 32 1 0 0 0 0 29 47 1 1 0 0 0 30 39 2 0 0 0 0 30 43 1 0 0 0 0 31 40 2 0 0 0 0 31 47 1 0 0 0 0 32 45 1 6 0 0 0 32 46 1 0 0 0 0 33 34 1 0 0 0 0 33 41 2 0 0 0 0 33 44 1 0 0 0 0 34 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	648.18
Volume:	631.2
LogP:	3.552
LogD:	2.531
LogS:	-4.021
# Rotatable Bonds:	13
TPSA:	195.35
# H-Bond Aceptor:	13
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.108
Synthetic Accessibility Score:	4.394
Fsp3:	0.294
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.819
MDCK Permeability:	3.834786548395641e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.779
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.232
Plasma Protein Binding (PPB):	100.80176544189453%
Volume Distribution (VD):	0.855
Pgp-substrate:	2.498060941696167%

ADMET: Metabolism

CYP1A2-inhibitor:	0.085
CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.714
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.834
CYP2C9-substrate:	0.585
CYP2D6-inhibitor:	0.957
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.819
CYP3A4-substrate:	0.25

ADMET: Excretion

Clearance (CL):	7.352
Half-life (T1/2):	0.913

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.053
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.283
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.067
Carcinogencity:	0.339
Eye Corrosion:	0.003
Eye Irritation:	0.778
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: NPC475183

Natural Product ID:	NPC475183
*Common Name:**	Itoside B
IUPAC Name:	[(2R,3S,4S,5R,6S)-5-benzoyloxy-3,4-dihydroxy-6-[4-hydroxy-2-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyl)oxymethyl]phenoxy]oxan-2-yl]methyl benzoate
Synonyms:
Standard InCHIKey:	QGZFGXHSODHGAW-PBWCLQEQSA-N
Standard InCHI:	InChI=1S/C34H32O13/c35-23-14-15-24(22(17-23)18-44-33(41)34(42)16-8-7-13-26(34)36)45-32-29(47-31(40)21-11-5-2-6-12-21)28(38)27(37)25(46-32)19-43-30(39)20-9-3-1-4-10-20/h1-6,8-12,14-17,25,27-29,32,35,37-38,42H,7,13,18-19H2/t25-,27-,28+,29-,32-,34?/m1/s1
SMILES:	C1CC(=O)C(C=C1)(C(=O)OCC2=C(C=CC(=C2)O)OC3C(C(C(C(O3)COC(=O)C4=CC=CC=C4)O)O)OC(=O)C5=CC=CC=C5)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500459
PubChem CID:	44577044
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	=	61.0	%	PMID[450888]

☑ 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 NPC475183 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	385
0.1-0.2	1566
0.2-0.3	3770
0.3-0.4	8233
0.4-0.5	9866
0.5-0.6	5023
0.6-0.7	7040
0.7-0.8	5800
0.8-0.85	923
0.85-0.9	67
0.9-0.95	14
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9872	High Similarity	NPC475174
0.9808	High Similarity	NPC280923
0.9675	High Similarity	NPC474441
0.9675	High Similarity	NPC476026
0.9675	High Similarity	NPC474401
0.9675	High Similarity	NPC474398
0.9563	High Similarity	NPC280385
0.9487	High Similarity	NPC231475
0.9487	High Similarity	NPC57072
0.9355	High Similarity	NPC299761
0.9355	High Similarity	NPC279281
0.9355	High Similarity	NPC92153
0.9355	High Similarity	NPC230439
0.9325	High Similarity	NPC470438
0.9286	High Similarity	NPC93619
0.9286	High Similarity	NPC131874
0.9245	High Similarity	NPC71780
0.9245	High Similarity	NPC132737
0.9156	High Similarity	NPC22137
0.9091	High Similarity	NPC140722
0.9091	High Similarity	NPC4958
0.9091	High Similarity	NPC92054
0.9026	High Similarity	NPC474422
0.8924	High Similarity	NPC215811
0.8868	High Similarity	NPC260604
0.8868	High Similarity	NPC299435
0.8846	High Similarity	NPC83975
0.8805	High Similarity	NPC183536
0.8805	High Similarity	NPC34965
0.8797	High Similarity	NPC475890
0.878	High Similarity	NPC80068
0.8774	High Similarity	NPC138915
0.8743	High Similarity	NPC188815
0.8743	High Similarity	NPC96605
0.8743	High Similarity	NPC218161
0.8743	High Similarity	NPC164704
0.8743	High Similarity	NPC469344
0.8743	High Similarity	NPC280642
0.8743	High Similarity	NPC470712
0.8727	High Similarity	NPC205824
0.8727	High Similarity	NPC139060
0.8727	High Similarity	NPC19240
0.8727	High Similarity	NPC85751
0.8727	High Similarity	NPC129264
0.8721	High Similarity	NPC470416
0.8706	High Similarity	NPC477895
0.8701	High Similarity	NPC65833
0.8701	High Similarity	NPC245219
0.8701	High Similarity	NPC31081
0.8698	High Similarity	NPC214621
0.8698	High Similarity	NPC34267
0.8698	High Similarity	NPC81042
0.8698	High Similarity	NPC223426
0.869	High Similarity	NPC101399
0.869	High Similarity	NPC221288
0.869	High Similarity	NPC257011
0.869	High Similarity	NPC217822
0.869	High Similarity	NPC470715
0.869	High Similarity	NPC11847
0.869	High Similarity	NPC474522
0.869	High Similarity	NPC470716
0.869	High Similarity	NPC470714
0.869	High Similarity	NPC137871
0.869	High Similarity	NPC288152
0.869	High Similarity	NPC9002
0.8675	High Similarity	NPC473278
0.8675	High Similarity	NPC260504
0.8675	High Similarity	NPC89809
0.8663	High Similarity	NPC162394
0.8663	High Similarity	NPC470718
0.8663	High Similarity	NPC156785
0.8663	High Similarity	NPC241781
0.8663	High Similarity	NPC36138
0.8659	High Similarity	NPC472994
0.8659	High Similarity	NPC210961
0.8659	High Similarity	NPC270675
0.8659	High Similarity	NPC195685
0.8659	High Similarity	NPC477628
0.8659	High Similarity	NPC477629
0.8647	High Similarity	NPC472992
0.8647	High Similarity	NPC472991
0.8647	High Similarity	NPC61904
0.8647	High Similarity	NPC144097
0.8634	High Similarity	NPC185103
0.8631	High Similarity	NPC76047
0.8631	High Similarity	NPC210808
0.8631	High Similarity	NPC199079
0.8629	High Similarity	NPC314672
0.8623	High Similarity	NPC128403
0.8616	High Similarity	NPC471214
0.8613	High Similarity	NPC275977
0.8613	High Similarity	NPC249560
0.8613	High Similarity	NPC25946
0.8613	High Similarity	NPC470720
0.8613	High Similarity	NPC223860
0.8613	High Similarity	NPC470717
0.8613	High Similarity	NPC460984
0.8613	High Similarity	NPC470713
0.8613	High Similarity	NPC21359
0.8608	High Similarity	NPC302989
0.8606	High Similarity	NPC472876
0.8605	High Similarity	NPC469371
0.8596	High Similarity	NPC139571
0.8596	High Similarity	NPC476619
0.8596	High Similarity	NPC476618
0.8596	High Similarity	NPC476622
0.8596	High Similarity	NPC217520
0.8596	High Similarity	NPC476620
0.8596	High Similarity	NPC476623
0.8596	High Similarity	NPC113836
0.8596	High Similarity	NPC37668
0.8596	High Similarity	NPC472387
0.8596	High Similarity	NPC35167
0.8596	High Similarity	NPC476621
0.8596	High Similarity	NPC253521
0.858	High Similarity	NPC47140
0.858	High Similarity	NPC67134
0.8571	High Similarity	NPC472133
0.8563	High Similarity	NPC104910
0.8563	High Similarity	NPC295625
0.8563	High Similarity	NPC33083
0.8563	High Similarity	NPC474093
0.8563	High Similarity	NPC473554
0.8563	High Similarity	NPC70441
0.8563	High Similarity	NPC470719
0.8555	High Similarity	NPC97119
0.8555	High Similarity	NPC35924
0.8555	High Similarity	NPC199172
0.8555	High Similarity	NPC135831
0.8555	High Similarity	NPC297503
0.8554	High Similarity	NPC121290
0.8554	High Similarity	NPC127415
0.8547	High Similarity	NPC471030
0.8545	High Similarity	NPC470125
0.8545	High Similarity	NPC217950
0.8538	High Similarity	NPC92403
0.8538	High Similarity	NPC170018
0.8538	High Similarity	NPC76112
0.8538	High Similarity	NPC231787
0.8538	High Similarity	NPC66820
0.8529	High Similarity	NPC172033
0.8529	High Similarity	NPC472993
0.8529	High Similarity	NPC88560
0.8529	High Similarity	NPC175230
0.8521	High Similarity	NPC92815
0.8521	High Similarity	NPC277532
0.8521	High Similarity	NPC138990
0.8521	High Similarity	NPC204937
0.8521	High Similarity	NPC175429
0.8521	High Similarity	NPC472129
0.8521	High Similarity	NPC149011
0.8521	High Similarity	NPC209550
0.8521	High Similarity	NPC43434
0.8519	High Similarity	NPC160882
0.8514	High Similarity	NPC475179
0.8514	High Similarity	NPC72554
0.8514	High Similarity	NPC30011
0.8514	High Similarity	NPC97817
0.8506	High Similarity	NPC470455
0.8506	High Similarity	NPC470451
0.8503	High Similarity	NPC178281
0.8503	High Similarity	NPC99216
0.85	High Similarity	NPC182350
0.8494	Intermediate Similarity	NPC90905
0.8494	Intermediate Similarity	NPC4013
0.8488	Intermediate Similarity	NPC258044
0.8488	Intermediate Similarity	NPC293626
0.8488	Intermediate Similarity	NPC267680
0.8488	Intermediate Similarity	NPC196127
0.8488	Intermediate Similarity	NPC217387
0.8485	Intermediate Similarity	NPC328093
0.848	Intermediate Similarity	NPC264735
0.848	Intermediate Similarity	NPC49344
0.848	Intermediate Similarity	NPC101191
0.848	Intermediate Similarity	NPC477848
0.848	Intermediate Similarity	NPC237435
0.848	Intermediate Similarity	NPC135277
0.848	Intermediate Similarity	NPC115760
0.848	Intermediate Similarity	NPC210094
0.848	Intermediate Similarity	NPC470667
0.848	Intermediate Similarity	NPC43211
0.8476	Intermediate Similarity	NPC177742
0.8471	Intermediate Similarity	NPC102851
0.8471	Intermediate Similarity	NPC5786
0.8471	Intermediate Similarity	NPC315619
0.8462	Intermediate Similarity	NPC145319
0.8462	Intermediate Similarity	NPC95421
0.8462	Intermediate Similarity	NPC198125
0.8462	Intermediate Similarity	NPC246274
0.8452	Intermediate Similarity	NPC64425
0.8448	Intermediate Similarity	NPC470447
0.8448	Intermediate Similarity	NPC470445
0.8448	Intermediate Similarity	NPC470449
0.8448	Intermediate Similarity	NPC470446
0.8443	Intermediate Similarity	NPC121703
0.8443	Intermediate Similarity	NPC227297
0.8439	Intermediate Similarity	NPC58538
0.8434	Intermediate Similarity	NPC216496
0.8434	Intermediate Similarity	NPC282169
0.8434	Intermediate Similarity	NPC159579

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 NPC475183 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	880
0.2-0.3	1874
0.3-0.4	2623
0.4-0.5	1956
0.5-0.6	1007
0.6-0.7	330
0.7-0.8	123
0.8-0.85	14
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8538	High Similarity	NPD8312	Approved
0.8538	High Similarity	NPD8313	Approved
0.8514	High Similarity	NPD7879	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD5402	Approved
0.8372	Intermediate Similarity	NPD7808	Phase 3
0.8364	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD7251	Discontinued
0.8256	Intermediate Similarity	NPD6797	Phase 2
0.8246	Intermediate Similarity	NPD7054	Approved
0.8198	Intermediate Similarity	NPD7472	Approved
0.8198	Intermediate Similarity	NPD7074	Phase 3
0.8148	Intermediate Similarity	NPD5403	Approved
0.8103	Intermediate Similarity	NPD6559	Discontinued
0.8081	Intermediate Similarity	NPD3751	Discontinued
0.8072	Intermediate Similarity	NPD8455	Phase 2
0.807	Intermediate Similarity	NPD6166	Phase 2
0.807	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7075	Discontinued
0.8025	Intermediate Similarity	NPD5401	Approved
0.7977	Intermediate Similarity	NPD3818	Discontinued
0.7976	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD7435	Discontinued
0.7889	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD3787	Discontinued
0.7819	Intermediate Similarity	NPD7870	Phase 2
0.7819	Intermediate Similarity	NPD7871	Phase 2
0.7801	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD7874	Approved
0.7796	Intermediate Similarity	NPD6781	Approved
0.7796	Intermediate Similarity	NPD6776	Approved
0.7796	Intermediate Similarity	NPD6777	Approved
0.7796	Intermediate Similarity	NPD6780	Approved
0.7796	Intermediate Similarity	NPD6778	Approved
0.7796	Intermediate Similarity	NPD6782	Approved
0.7796	Intermediate Similarity	NPD6779	Approved
0.7784	Intermediate Similarity	NPD4380	Phase 2
0.7778	Intermediate Similarity	NPD8150	Discontinued
0.7771	Intermediate Similarity	NPD1653	Approved
0.7766	Intermediate Similarity	NPD7698	Approved
0.7766	Intermediate Similarity	NPD7697	Approved
0.7766	Intermediate Similarity	NPD7696	Phase 3
0.7706	Intermediate Similarity	NPD3817	Phase 2
0.7697	Intermediate Similarity	NPD7685	Pre-registration
0.7696	Intermediate Similarity	NPD7701	Phase 2
0.7692	Intermediate Similarity	NPD6801	Discontinued
0.7668	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD7783	Phase 2
0.7647	Intermediate Similarity	NPD7819	Suspended
0.7636	Intermediate Similarity	NPD6799	Approved
0.7633	Intermediate Similarity	NPD7411	Suspended
0.7627	Intermediate Similarity	NPD5844	Phase 1
0.7624	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6823	Phase 2
0.7602	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD7699	Phase 2
0.7594	Intermediate Similarity	NPD7700	Phase 2
0.7588	Intermediate Similarity	NPD1934	Approved
0.7577	Intermediate Similarity	NPD7801	Approved
0.7558	Intermediate Similarity	NPD7768	Phase 2
0.7557	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD2801	Approved
0.7544	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1551	Phase 2
0.7531	Intermediate Similarity	NPD2935	Discontinued
0.7527	Intermediate Similarity	NPD6534	Approved
0.7527	Intermediate Similarity	NPD6535	Approved
0.7515	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1933	Approved
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD7266	Discontinued
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6233	Phase 2
0.7457	Intermediate Similarity	NPD3882	Suspended
0.7455	Intermediate Similarity	NPD3750	Approved
0.7455	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD8320	Phase 1
0.7448	Intermediate Similarity	NPD8319	Approved
0.744	Intermediate Similarity	NPD1512	Approved
0.7439	Intermediate Similarity	NPD1549	Phase 2
0.7436	Intermediate Similarity	NPD1203	Approved
0.7405	Intermediate Similarity	NPD6832	Phase 2
0.7403	Intermediate Similarity	NPD1091	Approved
0.7394	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6959	Discontinued
0.7385	Intermediate Similarity	NPD8151	Discontinued
0.7381	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7228	Approved
0.7368	Intermediate Similarity	NPD6599	Discontinued
0.7349	Intermediate Similarity	NPD4628	Phase 3
0.7321	Intermediate Similarity	NPD1511	Approved
0.7314	Intermediate Similarity	NPD3749	Approved
0.7312	Intermediate Similarity	NPD6798	Discontinued
0.731	Intermediate Similarity	NPD7458	Discontinued
0.731	Intermediate Similarity	NPD3226	Approved
0.7294	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD447	Suspended
0.7284	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6844	Discontinued
0.7263	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5494	Approved
0.7222	Intermediate Similarity	NPD7473	Discontinued
0.7219	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2313	Discontinued
0.7196	Intermediate Similarity	NPD6213	Phase 3
0.7196	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6212	Phase 3
0.7191	Intermediate Similarity	NPD7199	Phase 2
0.7169	Intermediate Similarity	NPD2346	Discontinued
0.7167	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1510	Phase 2
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7152	Intermediate Similarity	NPD3748	Approved
0.7151	Intermediate Similarity	NPD6232	Discontinued
0.7143	Intermediate Similarity	NPD1465	Phase 2
0.7134	Intermediate Similarity	NPD9717	Approved
0.7108	Intermediate Similarity	NPD2796	Approved
0.7107	Intermediate Similarity	NPD7584	Approved
0.7091	Intermediate Similarity	NPD7097	Phase 1
0.7086	Intermediate Similarity	NPD37	Approved
0.7079	Intermediate Similarity	NPD6234	Discontinued
0.7073	Intermediate Similarity	NPD6355	Discontinued
0.707	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4965	Approved
0.7062	Intermediate Similarity	NPD4966	Approved
0.7062	Intermediate Similarity	NPD4967	Phase 2
0.7048	Intermediate Similarity	NPD4308	Phase 3
0.7044	Intermediate Similarity	NPD3225	Approved
0.7027	Intermediate Similarity	NPD7240	Approved
0.6995	Remote Similarity	NPD7799	Discontinued
0.6994	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD411	Approved
0.6985	Remote Similarity	NPD7585	Approved
0.697	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2798	Approved
0.6946	Remote Similarity	NPD2799	Discontinued
0.6935	Remote Similarity	NPD7583	Approved
0.6933	Remote Similarity	NPD7095	Approved
0.6923	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1240	Approved
0.6909	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1613	Approved
0.6906	Remote Similarity	NPD8127	Discontinued
0.6905	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD8059	Phase 3
0.6894	Remote Similarity	NPD2797	Approved
0.689	Remote Similarity	NPD3268	Approved
0.689	Remote Similarity	NPD3764	Approved
0.6865	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7930	Approved
0.686	Remote Similarity	NPD7440	Discontinued
0.6852	Remote Similarity	NPD1019	Discontinued
0.6839	Remote Similarity	NPD6273	Approved
0.6837	Remote Similarity	NPD8285	Discontinued
0.6831	Remote Similarity	NPD3926	Phase 2
0.6826	Remote Similarity	NPD1607	Approved
0.681	Remote Similarity	NPD2861	Phase 2
0.6807	Remote Similarity	NPD4060	Phase 1
0.6807	Remote Similarity	NPD4307	Phase 2
0.6805	Remote Similarity	NPD6099	Approved
0.6805	Remote Similarity	NPD5404	Approved
0.6805	Remote Similarity	NPD6100	Approved
0.6805	Remote Similarity	NPD5406	Approved
0.6805	Remote Similarity	NPD5408	Approved
0.6805	Remote Similarity	NPD5405	Approved
0.6796	Remote Similarity	NPD919	Approved
0.6795	Remote Similarity	NPD9493	Approved
0.6792	Remote Similarity	NPD3496	Discontinued
0.6786	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6674	Discontinued
0.6784	Remote Similarity	NPD7680	Approved
0.6768	Remote Similarity	NPD4908	Phase 1
0.6766	Remote Similarity	NPD230	Phase 1
0.6765	Remote Similarity	NPD5762	Approved
0.6765	Remote Similarity	NPD5763	Approved
0.6765	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD2344	Approved
0.6755	Remote Similarity	NPD7038	Approved
0.6755	Remote Similarity	NPD7039	Approved
0.6747	Remote Similarity	NPD4062	Phase 3
0.6744	Remote Similarity	NPD8166	Discontinued
0.6744	Remote Similarity	NPD7003	Approved
0.6743	Remote Similarity	NPD5049	Phase 3
0.674	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6653	Approved
0.6721	Remote Similarity	NPD1247	Approved
0.672	Remote Similarity	NPD7549	Discontinued
0.672	Remote Similarity	NPD7177	Discontinued
0.6715	Remote Similarity	NPD8404	Phase 2

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