NPASS Compound

Structure

NPC132737 OpenBabel07101718202D 48 52 0 0 1 0 0 0 0 0999 V2000 6.0622 4.5000 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 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 -3.4641 0.0000 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 -0.8660 -1.5000 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 2 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 5.1962 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 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 -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 1 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 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 2.5981 -1.5000 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 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 20 2 0 0 0 0 12 21 2 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 14 34 2 0 0 0 0 15 43 1 0 0 0 0 16 44 1 0 0 0 0 17 30 1 0 0 0 0 18 31 1 0 0 0 0 19 21 1 0 0 0 0 20 35 1 0 0 0 0 21 45 1 0 0 0 0 22 15 1 6 0 0 0 22 24 1 0 0 0 0 22 46 1 0 0 0 0 23 16 1 1 0 0 0 23 25 1 0 0 0 0 23 47 1 0 0 0 0 24 26 1 0 0 0 0 24 36 1 1 0 0 0 25 29 1 0 0 0 0 25 37 1 6 0 0 0 26 27 1 0 0 0 0 26 38 1 6 0 0 0 27 32 1 0 0 0 0 27 39 1 1 0 0 0 28 29 1 0 0 0 0 28 33 1 0 0 0 0 28 40 1 6 0 0 0 29 48 1 1 0 0 0 30 41 2 0 0 0 0 30 43 1 0 0 0 0 31 42 2 0 0 0 0 31 44 1 0 0 0 0 32 46 1 0 0 0 0 32 48 1 6 0 0 0 33 45 1 1 0 0 0 33 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	670.19
Volume:	636.758
LogP:	2.22
LogD:	1.194
LogS:	-3.43
# Rotatable Bonds:	13
TPSA:	227.97
# H-Bond Aceptor:	15
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.116
Synthetic Accessibility Score:	4.537
Fsp3:	0.364
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:	-6.454
MDCK Permeability:	4.335323683335446e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.042
Human Intestinal Absorption (HIA):	0.937
20% Bioavailability (F20%):	0.06
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	97.61063385009766%
Volume Distribution (VD):	0.601
Pgp-substrate:	2.137986421585083%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.185
CYP2C9-substrate:	0.303
CYP2D6-inhibitor:	0.139
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.031

ADMET: Excretion

Clearance (CL):	1.625
Half-life (T1/2):	0.783

ADMET: Toxicity

hERG Blockers:	0.273
Human Hepatotoxicity (H-HT):	0.02
Drug-inuced Liver Injury (DILI):	0.74
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.567
Carcinogencity:	0.125
Eye Corrosion:	0.003
Eye Irritation:	0.851
Respiratory Toxicity:	0.009

Download Data

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

Natural Product: NPC132737

Natural Product ID:	NPC132737
*Common Name:**	Flacourtoside C
IUPAC Name:	[(2R,3S,4S,5R,6S)-6-[(2R,3R,4S,5R,6S)-2-(benzoyloxymethyl)-6-(2-formyl-4-hydroxyphenoxy)-3,5-dihydroxyoxan-4-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl benzoate
Synonyms:	Flacourtoside C
Standard InCHIKey:	LYHJYLWDBXOFGX-XERWWOBWSA-N
Standard InCHI:	InChI=1S/C33H34O15/c34-14-19-13-20(35)11-12-21(19)45-33-28(40)29(25(37)23(47-33)16-44-31(42)18-9-5-2-6-10-18)48-32-27(39)26(38)24(36)22(46-32)15-43-30(41)17-7-3-1-4-8-17/h1-14,22-29,32-33,35-40H,15-16H2/t22-,23-,24-,25-,26+,27-,28-,29+,32+,33-/m1/s1
SMILES:	c1ccc(cc1)C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]1[C@@H]([C@@H](COC(=O)c2ccccc2)O[C@H]([C@@H]1O)Oc1ccc(cc1C=O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2036485
PubChem CID:	57409245
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
NPO33462	flacourtia ramontchi	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22439591]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	23800.0	nM	PMID[502199]

☑ 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 NPC132737 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	380
0.1-0.2	1605
0.2-0.3	3938
0.3-0.4	8568
0.4-0.5	9379
0.5-0.6	5256
0.6-0.7	7241
0.7-0.8	5336
0.8-0.85	879
0.85-0.9	99
0.9-0.95	14
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9539	High Similarity	NPC215811
0.9477	High Similarity	NPC279281
0.9477	High Similarity	NPC92153
0.9477	High Similarity	NPC230439
0.9477	High Similarity	NPC299761
0.9308	High Similarity	NPC280923
0.9281	High Similarity	NPC93619
0.925	High Similarity	NPC475174
0.9245	High Similarity	NPC475183
0.9085	High Similarity	NPC92054
0.9085	High Similarity	NPC4958
0.9085	High Similarity	NPC140722
0.9085	High Similarity	NPC83975
0.908	High Similarity	NPC280385
0.8994	High Similarity	NPC57072
0.8994	High Similarity	NPC231475
0.8981	High Similarity	NPC260604
0.8981	High Similarity	NPC299435
0.897	High Similarity	NPC470438
0.8931	High Similarity	NPC474401
0.8931	High Similarity	NPC476026
0.8931	High Similarity	NPC474441
0.8931	High Similarity	NPC474398
0.8917	High Similarity	NPC34965
0.8917	High Similarity	NPC183536
0.8902	High Similarity	NPC472133
0.8889	High Similarity	NPC138915
0.8862	High Similarity	NPC66820
0.8862	High Similarity	NPC170018
0.8862	High Similarity	NPC92403
0.8862	High Similarity	NPC76112
0.8848	High Similarity	NPC472129
0.8848	High Similarity	NPC43434
0.8816	High Similarity	NPC65833
0.881	High Similarity	NPC476620
0.881	High Similarity	NPC472387
0.881	High Similarity	NPC476622
0.881	High Similarity	NPC476618
0.881	High Similarity	NPC476623
0.881	High Similarity	NPC476619
0.881	High Similarity	NPC476621
0.8795	High Similarity	NPC257011
0.8795	High Similarity	NPC137871
0.8795	High Similarity	NPC288152
0.8795	High Similarity	NPC9002
0.8773	High Similarity	NPC127415
0.8765	High Similarity	NPC217950
0.8757	High Similarity	NPC58538
0.875	High Similarity	NPC102053
0.875	High Similarity	NPC472991
0.875	High Similarity	NPC472992
0.8742	High Similarity	NPC185103
0.8735	High Similarity	NPC199079
0.8735	High Similarity	NPC210808
0.8726	High Similarity	NPC182350
0.872	High Similarity	NPC472130
0.872	High Similarity	NPC99216
0.872	High Similarity	NPC178281
0.872	High Similarity	NPC472131
0.8718	High Similarity	NPC302989
0.8712	High Similarity	NPC472876
0.8704	High Similarity	NPC328093
0.8696	High Similarity	NPC177742
0.8693	High Similarity	NPC31081
0.8693	High Similarity	NPC245219
0.8683	High Similarity	NPC102851
0.8683	High Similarity	NPC67134
0.8683	High Similarity	NPC315619
0.8683	High Similarity	NPC5786
0.8683	High Similarity	NPC47140
0.8675	High Similarity	NPC246274
0.8671	High Similarity	NPC475890
0.8667	High Similarity	NPC89809
0.8667	High Similarity	NPC473278
0.8667	High Similarity	NPC260504
0.8667	High Similarity	NPC70441
0.8663	High Similarity	NPC241847
0.8662	High Similarity	NPC22137
0.8659	High Similarity	NPC17432
0.8659	High Similarity	NPC121290
0.865	High Similarity	NPC477628
0.865	High Similarity	NPC477629
0.865	High Similarity	NPC472994
0.865	High Similarity	NPC195685
0.865	High Similarity	NPC210961
0.865	High Similarity	NPC270675
0.8639	High Similarity	NPC289876
0.8631	High Similarity	NPC88560
0.8631	High Similarity	NPC175230
0.8631	High Similarity	NPC203751
0.8631	High Similarity	NPC172033
0.8623	High Similarity	NPC470712
0.8623	High Similarity	NPC149011
0.8623	High Similarity	NPC204937
0.8623	High Similarity	NPC164704
0.8623	High Similarity	NPC76047
0.8614	High Similarity	NPC63470
0.8605	High Similarity	NPC292706
0.8605	High Similarity	NPC224557
0.8605	High Similarity	NPC470416
0.8598	High Similarity	NPC146837
0.8598	High Similarity	NPC101116
0.8598	High Similarity	NPC278329
0.8598	High Similarity	NPC4013
0.8598	High Similarity	NPC90905
0.8598	High Similarity	NPC212099
0.8596	High Similarity	NPC469371
0.8581	High Similarity	NPC471028
0.858	High Similarity	NPC133984
0.8571	High Similarity	NPC472386
0.8571	High Similarity	NPC470715
0.8571	High Similarity	NPC470714
0.8571	High Similarity	NPC470716
0.8571	High Similarity	NPC474522
0.8563	High Similarity	NPC197708
0.8563	High Similarity	NPC95421
0.8563	High Similarity	NPC658
0.8563	High Similarity	NPC198125
0.8553	High Similarity	NPC131874
0.8547	High Similarity	NPC156785
0.8547	High Similarity	NPC241781
0.8547	High Similarity	NPC470718
0.8547	High Similarity	NPC36138
0.8547	High Similarity	NPC162394
0.8547	High Similarity	NPC476203
0.8545	High Similarity	NPC80068
0.8538	High Similarity	NPC471030
0.8537	High Similarity	NPC71780
0.8537	High Similarity	NPC101636
0.8529	High Similarity	NPC144097
0.8529	High Similarity	NPC314489
0.8529	High Similarity	NPC232818
0.8529	High Similarity	NPC61904
0.8529	High Similarity	NPC198893
0.8521	High Similarity	NPC472993
0.8521	High Similarity	NPC163165
0.8521	High Similarity	NPC204693
0.8514	High Similarity	NPC31208
0.8514	High Similarity	NPC472720
0.8514	High Similarity	NPC93065
0.8514	High Similarity	NPC472721
0.8514	High Similarity	NPC469652
0.8514	High Similarity	NPC472724
0.8514	High Similarity	NPC160543
0.8512	High Similarity	NPC44558
0.8512	High Similarity	NPC34287
0.8512	High Similarity	NPC471416
0.8512	High Similarity	NPC188815
0.8512	High Similarity	NPC469344
0.8512	High Similarity	NPC280642
0.8512	High Similarity	NPC96605
0.8512	High Similarity	NPC218161
0.8509	High Similarity	NPC160882
0.8509	High Similarity	NPC470331
0.8503	High Similarity	NPC249977
0.8503	High Similarity	NPC103633
0.8497	Intermediate Similarity	NPC223860
0.8497	Intermediate Similarity	NPC21359
0.8497	Intermediate Similarity	NPC470455
0.8497	Intermediate Similarity	NPC249560
0.8497	Intermediate Similarity	NPC470720
0.8497	Intermediate Similarity	NPC25946
0.8497	Intermediate Similarity	NPC470717
0.8497	Intermediate Similarity	NPC470713
0.8497	Intermediate Similarity	NPC275977
0.8497	Intermediate Similarity	NPC470451
0.8497	Intermediate Similarity	NPC460984
0.8494	Intermediate Similarity	NPC129264
0.8494	Intermediate Similarity	NPC11608
0.8494	Intermediate Similarity	NPC139060
0.8494	Intermediate Similarity	NPC205824
0.8494	Intermediate Similarity	NPC85751
0.8494	Intermediate Similarity	NPC297404
0.8494	Intermediate Similarity	NPC19240
0.8488	Intermediate Similarity	NPC477860
0.8488	Intermediate Similarity	NPC85316
0.8488	Intermediate Similarity	NPC197357
0.8488	Intermediate Similarity	NPC475161
0.8485	Intermediate Similarity	NPC56735
0.8485	Intermediate Similarity	NPC61594
0.8485	Intermediate Similarity	NPC298171
0.8485	Intermediate Similarity	NPC22324
0.8485	Intermediate Similarity	NPC246024
0.848	Intermediate Similarity	NPC37668
0.848	Intermediate Similarity	NPC477895
0.848	Intermediate Similarity	NPC253521
0.848	Intermediate Similarity	NPC35167
0.848	Intermediate Similarity	NPC113836
0.8476	Intermediate Similarity	NPC289346
0.8471	Intermediate Similarity	NPC34267
0.8471	Intermediate Similarity	NPC470667
0.8471	Intermediate Similarity	NPC102028
0.8471	Intermediate Similarity	NPC223426
0.8471	Intermediate Similarity	NPC307754
0.8471	Intermediate Similarity	NPC214621
0.8471	Intermediate Similarity	NPC223735
0.8471	Intermediate Similarity	NPC81042
0.8462	Intermediate Similarity	NPC267254
0.8462	Intermediate Similarity	NPC3583
0.8462	Intermediate Similarity	NPC254540

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 NPC132737 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	871
0.2-0.3	1860
0.3-0.4	2664
0.4-0.5	1927
0.5-0.6	1056
0.6-0.7	303
0.7-0.8	117
0.8-0.85	13
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8862	High Similarity	NPD8313	Approved
0.8862	High Similarity	NPD8312	Approved
0.8363	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD5402	Approved
0.8343	Intermediate Similarity	NPD7054	Approved
0.8304	Intermediate Similarity	NPD6559	Discontinued
0.8295	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD7472	Approved
0.8294	Intermediate Similarity	NPD7074	Phase 3
0.8282	Intermediate Similarity	NPD8455	Phase 2
0.8256	Intermediate Similarity	NPD7808	Phase 3
0.8235	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD7251	Discontinued
0.814	Intermediate Similarity	NPD6797	Phase 2
0.8072	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD3818	Discontinued
0.7978	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD6166	Phase 2
0.7931	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD5403	Approved
0.7848	Intermediate Similarity	NPD1551	Phase 2
0.7842	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD7783	Phase 2
0.7811	Intermediate Similarity	NPD7075	Discontinued
0.7791	Intermediate Similarity	NPD5401	Approved
0.7784	Intermediate Similarity	NPD7685	Pre-registration
0.7771	Intermediate Similarity	NPD4380	Phase 2
0.7758	Intermediate Similarity	NPD1653	Approved
0.7754	Intermediate Similarity	NPD7435	Discontinued
0.7688	Intermediate Similarity	NPD7266	Discontinued
0.766	Intermediate Similarity	NPD7698	Approved
0.766	Intermediate Similarity	NPD7696	Phase 3
0.766	Intermediate Similarity	NPD7697	Approved
0.7657	Intermediate Similarity	NPD3751	Discontinued
0.7647	Intermediate Similarity	NPD7768	Phase 2
0.7633	Intermediate Similarity	NPD7819	Suspended
0.7633	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD2801	Approved
0.7625	Intermediate Similarity	NPD2935	Discontinued
0.7619	Intermediate Similarity	NPD7411	Suspended
0.7619	Intermediate Similarity	NPD7871	Phase 2
0.7619	Intermediate Similarity	NPD7870	Phase 2
0.7614	Intermediate Similarity	NPD5844	Phase 1
0.7606	Intermediate Similarity	NPD6823	Phase 2
0.7604	Intermediate Similarity	NPD7874	Approved
0.7604	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1933	Approved
0.7594	Intermediate Similarity	NPD6777	Approved
0.7594	Intermediate Similarity	NPD6781	Approved
0.7594	Intermediate Similarity	NPD6776	Approved
0.7594	Intermediate Similarity	NPD6778	Approved
0.7594	Intermediate Similarity	NPD6779	Approved
0.7594	Intermediate Similarity	NPD6782	Approved
0.7594	Intermediate Similarity	NPD6780	Approved
0.7592	Intermediate Similarity	NPD7701	Phase 2
0.7588	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1934	Approved
0.7557	Intermediate Similarity	NPD7228	Approved
0.7552	Intermediate Similarity	NPD8151	Discontinued
0.7546	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1203	Approved
0.7529	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3787	Discontinued
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7487	Intermediate Similarity	NPD7699	Phase 2
0.7487	Intermediate Similarity	NPD7700	Phase 2
0.7485	Intermediate Similarity	NPD3817	Phase 2
0.7484	Intermediate Similarity	NPD447	Suspended
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.7471	Intermediate Similarity	NPD6959	Discontinued
0.7471	Intermediate Similarity	NPD6844	Discontinued
0.7471	Intermediate Similarity	NPD6801	Discontinued
0.747	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4628	Phase 3
0.7423	Intermediate Similarity	NPD1549	Phase 2
0.7418	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5494	Approved
0.741	Intermediate Similarity	NPD6799	Approved
0.7405	Intermediate Similarity	NPD2313	Discontinued
0.7394	Intermediate Similarity	NPD6190	Approved
0.7386	Intermediate Similarity	NPD1091	Approved
0.7385	Intermediate Similarity	NPD7801	Approved
0.7378	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD8434	Phase 2
0.7375	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2346	Discontinued
0.7362	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6233	Phase 2
0.7344	Intermediate Similarity	NPD8319	Approved
0.7344	Intermediate Similarity	NPD8320	Phase 1
0.7341	Intermediate Similarity	NPD3882	Suspended
0.733	Intermediate Similarity	NPD6232	Discontinued
0.7326	Intermediate Similarity	NPD1465	Phase 2
0.7326	Intermediate Similarity	NPD6534	Approved
0.7326	Intermediate Similarity	NPD6535	Approved
0.7313	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1511	Approved
0.7305	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7473	Discontinued
0.7299	Intermediate Similarity	NPD3749	Approved
0.7294	Intermediate Similarity	NPD7458	Discontinued
0.7273	Intermediate Similarity	NPD6212	Phase 3
0.7273	Intermediate Similarity	NPD6213	Phase 3
0.7273	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3750	Approved
0.7226	Intermediate Similarity	NPD9717	Approved
0.7219	Intermediate Similarity	NPD1512	Approved
0.7198	Intermediate Similarity	NPD7240	Approved
0.7188	Intermediate Similarity	NPD6798	Discontinued
0.7178	Intermediate Similarity	NPD7097	Phase 1
0.7176	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7199	Phase 2
0.7168	Intermediate Similarity	NPD37	Approved
0.7161	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6234	Discontinued
0.7151	Intermediate Similarity	NPD6599	Discontinued
0.7143	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD4965	Approved
0.7143	Intermediate Similarity	NPD4967	Phase 2
0.7134	Intermediate Similarity	NPD7033	Discontinued
0.7134	Intermediate Similarity	NPD2799	Discontinued
0.7134	Intermediate Similarity	NPD1510	Phase 2
0.7091	Intermediate Similarity	NPD2796	Approved
0.7081	Intermediate Similarity	NPD411	Approved
0.7068	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2798	Approved
0.7025	Intermediate Similarity	NPD3225	Approved
0.7024	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7584	Approved
0.7	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8127	Discontinued
0.6975	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3764	Approved
0.6961	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6355	Discontinued
0.6941	Remote Similarity	NPD7440	Discontinued
0.6939	Remote Similarity	NPD7680	Approved
0.6937	Remote Similarity	NPD1019	Discontinued
0.6928	Remote Similarity	NPD4308	Phase 3
0.6928	Remote Similarity	NPD3748	Approved
0.6919	Remote Similarity	NPD6273	Approved
0.6894	Remote Similarity	NPD2861	Phase 2
0.689	Remote Similarity	NPD1240	Approved
0.689	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.689	Remote Similarity	NPD8059	Phase 3
0.689	Remote Similarity	NPD1613	Approved
0.689	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5405	Approved
0.6886	Remote Similarity	NPD5406	Approved
0.6886	Remote Similarity	NPD5408	Approved
0.6886	Remote Similarity	NPD5404	Approved
0.6884	Remote Similarity	NPD7585	Approved
0.6883	Remote Similarity	NPD9493	Approved
0.6879	Remote Similarity	NPD920	Approved
0.6879	Remote Similarity	NPD3496	Discontinued
0.6875	Remote Similarity	NPD2797	Approved
0.6864	Remote Similarity	NPD6674	Discontinued
0.686	Remote Similarity	NPD2533	Approved
0.686	Remote Similarity	NPD2534	Approved
0.686	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.686	Remote Similarity	NPD642	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2532	Approved
0.6848	Remote Similarity	NPD230	Phase 1
0.6847	Remote Similarity	NPD7930	Approved
0.6845	Remote Similarity	NPD2344	Approved
0.6834	Remote Similarity	NPD7583	Approved
0.6828	Remote Similarity	NPD7038	Approved
0.6828	Remote Similarity	NPD7039	Approved
0.6824	Remote Similarity	NPD7003	Approved
0.6821	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD8285	Discontinued
0.6816	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1607	Approved
0.6807	Remote Similarity	NPD6653	Approved
0.6796	Remote Similarity	NPD1247	Approved
0.6793	Remote Similarity	NPD7177	Discontinued
0.6792	Remote Similarity	NPD1481	Phase 2
0.6792	Remote Similarity	NPD1608	Approved
0.679	Remote Similarity	NPD9494	Approved
0.6784	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD919	Approved
0.6774	Remote Similarity	NPD5953	Discontinued
0.677	Remote Similarity	NPD1470	Approved
0.6768	Remote Similarity	NPD3268	Approved
0.6766	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4662	Approved
0.6763	Remote Similarity	NPD4661	Approved
0.6757	Remote Similarity	NPD7286	Phase 2
0.6748	Remote Similarity	NPD4908	Phase 1

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