NPASS Compound

Structure

NPC280385 OpenBabel07101718322D 57 62 0 0 1 0 0 0 0 0999 V2000 5.1137 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2614 -4.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8885 -0.5270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2614 -0.4921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1137 0.9841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2614 -3.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4091 -4.9206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1432 0.4236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9379 -0.7817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4091 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2614 1.4762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4091 -2.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5568 -4.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4474 1.1194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2421 -0.0859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4091 -1.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9185 4.8536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5568 -1.4762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9679 4.5989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2614 -0.4921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4091 0.9841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7046 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4091 0.9841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5568 -3.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4968 0.8647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4091 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2614 -1.4762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6144 4.1577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5568 -0.4921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8523 -0.4921 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7132 3.6483 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8523 -1.4762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.9683 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8523 -1.4762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3597 3.2071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5568 1.4762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7046 -2.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8009 1.5606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8523 -0.4921 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5568 2.4603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4091 2.9524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1137 -1.9683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5650 4.4124 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8120 3.1388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7046 -1.9683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5568 2.4603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8523 -3.4444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8503 1.3059 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7046 2.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1899 2.3533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7046 0.9841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5568 1.4762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7046 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 -1.7046 -1.9683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0556 2.5112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 5 1 0 0 0 0 2 6 2 0 0 0 0 2 7 1 0 0 0 0 3 8 2 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 10 23 2 0 0 0 0 11 23 1 0 0 0 0 12 24 2 0 0 0 0 13 24 1 0 0 0 0 14 25 2 0 0 0 0 15 25 1 0 0 0 0 16 18 1 0 0 0 0 16 27 2 0 0 0 0 17 19 2 0 0 0 0 17 28 1 0 0 0 0 18 29 2 0 0 0 0 19 31 1 0 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 21 26 1 0 0 0 0 21 53 1 0 0 0 0 22 52 1 0 0 0 0 23 36 1 0 0 0 0 24 37 1 0 0 0 0 25 38 1 0 0 0 0 26 29 1 0 0 0 0 27 42 1 0 0 0 0 28 35 1 0 0 0 0 28 43 2 0 0 0 0 29 54 1 0 0 0 0 30 22 1 6 0 0 0 30 32 1 0 0 0 0 30 55 1 0 0 0 0 31 41 1 1 0 0 0 31 44 1 0 0 0 0 32 33 1 0 0 0 0 32 45 1 1 0 0 0 33 34 1 0 0 0 0 33 46 1 6 0 0 0 34 39 1 0 0 0 0 34 56 1 1 0 0 0 35 41 1 1 0 0 0 35 57 1 0 0 0 0 36 47 2 0 0 0 0 36 52 1 0 0 0 0 37 48 2 0 0 0 0 37 56 1 0 0 0 0 38 49 2 0 0 0 0 38 57 1 0 0 0 0 39 54 1 6 0 0 0 39 55 1 0 0 0 0 40 41 1 0 0 0 0 40 50 2 0 0 0 0 40 53 1 0 0 0 0 41 51 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	784.2
Volume:	759.54
LogP:	3.712
LogD:	2.122
LogS:	-4.026
# Rotatable Bonds:	16
TPSA:	238.72
# H-Bond Aceptor:	16
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.092
Synthetic Accessibility Score:	4.721
Fsp3:	0.268
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:	-5.979
MDCK Permeability:	4.125744817429222e-05
Pgp-inhibitor:	0.343
Pgp-substrate:	0.052
Human Intestinal Absorption (HIA):	0.838
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.235
Plasma Protein Binding (PPB):	104.75381469726562%
Volume Distribution (VD):	0.872
Pgp-substrate:	1.5446408987045288%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.026
CYP2C19-inhibitor:	0.776
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.924
CYP2C9-substrate:	0.399
CYP2D6-inhibitor:	0.854
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.334
CYP3A4-substrate:	0.153

ADMET: Excretion

Clearance (CL):	10.891
Half-life (T1/2):	0.891

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.289
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.175
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.051
Carcinogencity:	0.302
Eye Corrosion:	0.003
Eye Irritation:	0.623
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: NPC280385

Natural Product ID:	NPC280385
*Common Name:**	Flacourtoside F
IUPAC Name:	[2-[(2S,3R,4S,5S,6R)-3-benzoyloxy-6-(benzoyloxymethyl)-4,5-dihydroxyoxan-2-yl]oxy-5-hydroxyphenyl]methyl (1R,2R,6R)-6-benzoyloxy-1,2-dihydroxy-5-oxocyclohex-3-ene-1-carboxylate
Synonyms:	Flacourtoside F
Standard InCHIKey:	OCONHFDQQLUZPI-KWSNQTRASA-N
Standard InCHI:	InChI=1S/C41H36O16/c42-27-16-18-29(26(20-27)21-53-40(50)41(51)31(44)19-17-28(43)35(41)57-38(49)25-14-8-3-9-15-25)54-39-34(56-37(48)24-12-6-2-7-13-24)33(46)32(45)30(55-39)22-52-36(47)23-10-4-1-5-11-23/h1-20,30-35,39,42,44-46,51H,21-22H2/t30-,31-,32-,33+,34-,35+,39-,41-/m1/s1
SMILES:	Oc1ccc(c(c1)COC(=O)[C@@]1(O)[C@H](O)C=CC(=O)[C@@H]1OC(=O)c1ccccc1)O[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@H]([C@@H]([C@H]1OC(=O)c1ccccc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2036488
PubChem CID:	57409350
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	=	39800.0	nM	PMID[550603]

☑ 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 NPC280385 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	397
0.1-0.2	1660
0.2-0.3	4076
0.3-0.4	8561
0.4-0.5	9667
0.5-0.6	5171
0.6-0.7	7522
0.7-0.8	4780
0.8-0.85	802
0.85-0.9	44
0.9-0.95	13
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9748	High Similarity	NPC280923
0.9565	High Similarity	NPC475174
0.9563	High Similarity	NPC475183
0.9512	High Similarity	NPC470438
0.9434	High Similarity	NPC57072
0.9434	High Similarity	NPC231475
0.925	High Similarity	NPC474401
0.925	High Similarity	NPC476026
0.925	High Similarity	NPC474398
0.925	High Similarity	NPC474441
0.908	High Similarity	NPC132737
0.9062	High Similarity	NPC92153
0.9062	High Similarity	NPC230439
0.9062	High Similarity	NPC279281
0.9062	High Similarity	NPC299761
0.8994	High Similarity	NPC93619
0.8875	High Similarity	NPC131874
0.8868	High Similarity	NPC22137
0.8848	High Similarity	NPC71780
0.8844	High Similarity	NPC97119
0.8844	High Similarity	NPC297503
0.8844	High Similarity	NPC135831
0.8817	High Similarity	NPC218161
0.8817	High Similarity	NPC96605
0.8817	High Similarity	NPC280642
0.8817	High Similarity	NPC469344
0.8805	High Similarity	NPC140722
0.8805	High Similarity	NPC4958
0.8805	High Similarity	NPC92054
0.8765	High Similarity	NPC11847
0.8765	High Similarity	NPC221288
0.8765	High Similarity	NPC215811
0.8765	High Similarity	NPC217822
0.8765	High Similarity	NPC101399
0.8743	High Similarity	NPC104910
0.8743	High Similarity	NPC474093
0.8721	High Similarity	NPC231787
0.8721	High Similarity	NPC66820
0.8721	High Similarity	NPC92403
0.8721	High Similarity	NPC170018
0.8721	High Similarity	NPC76112
0.8706	High Similarity	NPC188815
0.8706	High Similarity	NPC164704
0.8706	High Similarity	NPC470712
0.8706	High Similarity	NPC92815
0.8693	High Similarity	NPC30011
0.8693	High Similarity	NPC97817
0.8693	High Similarity	NPC72554
0.8693	High Similarity	NPC475179
0.8688	High Similarity	NPC83975
0.8686	High Similarity	NPC470416
0.8671	High Similarity	NPC253521
0.8671	High Similarity	NPC37668
0.8671	High Similarity	NPC113836
0.8655	High Similarity	NPC470716
0.8655	High Similarity	NPC474522
0.8655	High Similarity	NPC470715
0.8655	High Similarity	NPC470714
0.865	High Similarity	NPC183536
0.865	High Similarity	NPC34965
0.8647	High Similarity	NPC95421
0.8647	High Similarity	NPC198125
0.8639	High Similarity	NPC473278
0.8639	High Similarity	NPC260504
0.8639	High Similarity	NPC89809
0.8629	High Similarity	NPC162394
0.8629	High Similarity	NPC470718
0.8629	High Similarity	NPC156785
0.8629	High Similarity	NPC241781
0.8629	High Similarity	NPC36138
0.8625	High Similarity	NPC474422
0.8613	High Similarity	NPC144097
0.8613	High Similarity	NPC61904
0.8598	High Similarity	NPC260604
0.8598	High Similarity	NPC160882
0.8598	High Similarity	NPC299435
0.8596	High Similarity	NPC314672
0.8588	High Similarity	NPC128403
0.858	High Similarity	NPC470451
0.858	High Similarity	NPC25946
0.858	High Similarity	NPC470713
0.858	High Similarity	NPC205824
0.858	High Similarity	NPC129264
0.858	High Similarity	NPC249560
0.858	High Similarity	NPC470717
0.858	High Similarity	NPC470720
0.858	High Similarity	NPC223860
0.858	High Similarity	NPC19240
0.858	High Similarity	NPC21359
0.858	High Similarity	NPC275977
0.858	High Similarity	NPC460984
0.858	High Similarity	NPC470455
0.858	High Similarity	NPC85751
0.8564	High Similarity	NPC3474
0.8563	High Similarity	NPC217387
0.8563	High Similarity	NPC477895
0.8563	High Similarity	NPC258044
0.8563	High Similarity	NPC267680
0.8563	High Similarity	NPC196127
0.8563	High Similarity	NPC293626
0.8563	High Similarity	NPC35167
0.8555	High Similarity	NPC470667
0.8555	High Similarity	NPC34267
0.8555	High Similarity	NPC223426
0.8555	High Similarity	NPC186800
0.8555	High Similarity	NPC214621
0.8555	High Similarity	NPC81042
0.8547	High Similarity	NPC257011
0.8547	High Similarity	NPC137871
0.8547	High Similarity	NPC9002
0.8547	High Similarity	NPC288152
0.8538	High Similarity	NPC472133
0.8531	High Similarity	NPC295625
0.8531	High Similarity	NPC473554
0.8531	High Similarity	NPC470719
0.8531	High Similarity	NPC33083
0.8528	High Similarity	NPC475890
0.8523	High Similarity	NPC470449
0.8523	High Similarity	NPC470445
0.8523	High Similarity	NPC470447
0.8523	High Similarity	NPC470446
0.8521	High Similarity	NPC80068
0.8521	High Similarity	NPC227297
0.8514	High Similarity	NPC471030
0.8514	High Similarity	NPC58538
0.8506	High Similarity	NPC472992
0.8506	High Similarity	NPC102053
0.8506	High Similarity	NPC472991
0.85	High Similarity	NPC138915
0.8492	Intermediate Similarity	NPC201814
0.8488	Intermediate Similarity	NPC43434
0.8488	Intermediate Similarity	NPC209550
0.8488	Intermediate Similarity	NPC199079
0.8488	Intermediate Similarity	NPC138990
0.8488	Intermediate Similarity	NPC175429
0.8488	Intermediate Similarity	NPC210808
0.8488	Intermediate Similarity	NPC277532
0.8488	Intermediate Similarity	NPC472129
0.8483	Intermediate Similarity	NPC65489
0.8475	Intermediate Similarity	NPC292706
0.8475	Intermediate Similarity	NPC231254
0.8475	Intermediate Similarity	NPC75574
0.8475	Intermediate Similarity	NPC224557
0.8471	Intermediate Similarity	NPC139060
0.8471	Intermediate Similarity	NPC178281
0.847	Intermediate Similarity	NPC131405
0.8466	Intermediate Similarity	NPC469371
0.8457	Intermediate Similarity	NPC476622
0.8457	Intermediate Similarity	NPC476618
0.8457	Intermediate Similarity	NPC476619
0.8457	Intermediate Similarity	NPC139571
0.8457	Intermediate Similarity	NPC476623
0.8457	Intermediate Similarity	NPC217520
0.8457	Intermediate Similarity	NPC476620
0.8457	Intermediate Similarity	NPC472387
0.8457	Intermediate Similarity	NPC476621
0.8448	Intermediate Similarity	NPC115760
0.8448	Intermediate Similarity	NPC264735
0.8448	Intermediate Similarity	NPC101191
0.8448	Intermediate Similarity	NPC253685
0.8448	Intermediate Similarity	NPC473630
0.8448	Intermediate Similarity	NPC237435
0.8448	Intermediate Similarity	NPC210094
0.8448	Intermediate Similarity	NPC135277
0.8448	Intermediate Similarity	NPC49344
0.8448	Intermediate Similarity	NPC43211
0.8444	Intermediate Similarity	NPC48474
0.8439	Intermediate Similarity	NPC102851
0.8439	Intermediate Similarity	NPC5786
0.8439	Intermediate Similarity	NPC315619
0.843	Intermediate Similarity	NPC246274
0.843	Intermediate Similarity	NPC137460
0.8428	Intermediate Similarity	NPC245219
0.8428	Intermediate Similarity	NPC65833
0.8428	Intermediate Similarity	NPC31081
0.8427	Intermediate Similarity	NPC261623
0.8427	Intermediate Similarity	NPC111490
0.8424	Intermediate Similarity	NPC470450
0.8421	Intermediate Similarity	NPC64425
0.8418	Intermediate Similarity	NPC35924
0.8418	Intermediate Similarity	NPC199172
0.8418	Intermediate Similarity	NPC476203
0.8412	Intermediate Similarity	NPC127415
0.8409	Intermediate Similarity	NPC241423
0.8409	Intermediate Similarity	NPC126784
0.8409	Intermediate Similarity	NPC470443
0.8409	Intermediate Similarity	NPC179862
0.8409	Intermediate Similarity	NPC110941
0.8409	Intermediate Similarity	NPC473571
0.8409	Intermediate Similarity	NPC470444
0.8409	Intermediate Similarity	NPC473682
0.8402	Intermediate Similarity	NPC477628
0.8402	Intermediate Similarity	NPC210961
0.8402	Intermediate Similarity	NPC270675
0.8402	Intermediate Similarity	NPC477629
0.8402	Intermediate Similarity	NPC470125
0.8402	Intermediate Similarity	NPC217950
0.8402	Intermediate Similarity	NPC472994
0.8402	Intermediate Similarity	NPC282169
0.8402	Intermediate Similarity	NPC195685

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 NPC280385 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	924
0.2-0.3	1959
0.3-0.4	2672
0.4-0.5	1917
0.5-0.6	915
0.6-0.7	283
0.7-0.8	109
0.8-0.85	11
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8721	High Similarity	NPD8313	Approved
0.8721	High Similarity	NPD8312	Approved
0.8693	High Similarity	NPD7879	Clinical (unspecified phase)
0.8448	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD5402	Approved
0.8343	Intermediate Similarity	NPD7808	Phase 3
0.8286	Intermediate Similarity	NPD7251	Discontinued
0.8229	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8229	Intermediate Similarity	NPD6797	Phase 2
0.8218	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD3751	Discontinued
0.8155	Intermediate Similarity	NPD8455	Phase 2
0.8128	Intermediate Similarity	NPD7435	Discontinued
0.8118	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD7472	Approved
0.8012	Intermediate Similarity	NPD5403	Approved
0.8011	Intermediate Similarity	NPD7054	Approved
0.7969	Intermediate Similarity	NPD7874	Approved
0.7969	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD7074	Phase 3
0.7931	Intermediate Similarity	NPD3787	Discontinued
0.7907	Intermediate Similarity	NPD7075	Discontinued
0.7895	Intermediate Similarity	NPD7871	Phase 2
0.7895	Intermediate Similarity	NPD7870	Phase 2
0.7892	Intermediate Similarity	NPD5401	Approved
0.7877	Intermediate Similarity	NPD6559	Discontinued
0.7872	Intermediate Similarity	NPD6778	Approved
0.7872	Intermediate Similarity	NPD6776	Approved
0.7872	Intermediate Similarity	NPD6781	Approved
0.7872	Intermediate Similarity	NPD6782	Approved
0.7872	Intermediate Similarity	NPD6779	Approved
0.7872	Intermediate Similarity	NPD6780	Approved
0.7872	Intermediate Similarity	NPD6777	Approved
0.7853	Intermediate Similarity	NPD3818	Discontinued
0.7849	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD7697	Approved
0.7842	Intermediate Similarity	NPD7698	Approved
0.7842	Intermediate Similarity	NPD7696	Phase 3
0.7841	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6166	Phase 2
0.7841	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD7701	Phase 2
0.7733	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD7700	Phase 2
0.7672	Intermediate Similarity	NPD7699	Phase 2
0.7663	Intermediate Similarity	NPD8150	Discontinued
0.7662	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD7801	Approved
0.7617	Intermediate Similarity	NPD8319	Approved
0.7617	Intermediate Similarity	NPD8320	Phase 1
0.7606	Intermediate Similarity	NPD6534	Approved
0.7606	Intermediate Similarity	NPD6535	Approved
0.7604	Intermediate Similarity	NPD6823	Phase 2
0.7586	Intermediate Similarity	NPD3817	Phase 2
0.7582	Intermediate Similarity	NPD7685	Pre-registration
0.7572	Intermediate Similarity	NPD6801	Discontinued
0.7568	Intermediate Similarity	NPD8434	Phase 2
0.7563	Intermediate Similarity	NPD7783	Phase 2
0.7563	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD4380	Phase 2
0.7551	Intermediate Similarity	NPD8151	Discontinued
0.7544	Intermediate Similarity	NPD1653	Approved
0.7543	Intermediate Similarity	NPD7768	Phase 2
0.7542	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6799	Approved
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6190	Approved
0.7443	Intermediate Similarity	NPD3882	Suspended
0.744	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7819	Suspended
0.7429	Intermediate Similarity	NPD2801	Approved
0.7418	Intermediate Similarity	NPD5844	Phase 1
0.7414	Intermediate Similarity	NPD7411	Suspended
0.7386	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6959	Discontinued
0.7371	Intermediate Similarity	NPD1934	Approved
0.7362	Intermediate Similarity	NPD6233	Phase 2
0.733	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2935	Discontinued
0.7305	Intermediate Similarity	NPD1551	Phase 2
0.7303	Intermediate Similarity	NPD3749	Approved
0.7299	Intermediate Similarity	NPD3226	Approved
0.7299	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6212	Phase 3
0.7277	Intermediate Similarity	NPD6213	Phase 3
0.7277	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1933	Approved
0.7268	Intermediate Similarity	NPD7228	Approved
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7266	Discontinued
0.7257	Intermediate Similarity	NPD6599	Discontinued
0.7235	Intermediate Similarity	NPD3750	Approved
0.7225	Intermediate Similarity	NPD1512	Approved
0.7219	Intermediate Similarity	NPD1549	Phase 2
0.7213	Intermediate Similarity	NPD7473	Discontinued
0.7205	Intermediate Similarity	NPD1203	Approved
0.72	Intermediate Similarity	NPD7458	Discontinued
0.7195	Intermediate Similarity	NPD6798	Discontinued
0.7186	Intermediate Similarity	NPD7097	Phase 1
0.7178	Intermediate Similarity	NPD6832	Phase 2
0.7176	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD6844	Discontinued
0.717	Intermediate Similarity	NPD1091	Approved
0.7169	Intermediate Similarity	NPD447	Suspended
0.7168	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6232	Discontinued
0.7135	Intermediate Similarity	NPD4628	Phase 3
0.7127	Intermediate Similarity	NPD5494	Approved
0.711	Intermediate Similarity	NPD1511	Approved
0.7104	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2313	Discontinued
0.7086	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2346	Discontinued
0.705	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1465	Phase 2
0.7035	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7240	Approved
0.7011	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7199	Phase 2
0.6983	Remote Similarity	NPD37	Approved
0.6981	Remote Similarity	NPD8059	Phase 3
0.6981	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6234	Discontinued
0.6964	Remote Similarity	NPD6355	Discontinued
0.6961	Remote Similarity	NPD4967	Phase 2
0.6961	Remote Similarity	NPD4965	Approved
0.6961	Remote Similarity	NPD4966	Approved
0.6941	Remote Similarity	NPD7033	Discontinued
0.6941	Remote Similarity	NPD1510	Phase 2
0.6941	Remote Similarity	NPD3748	Approved
0.6931	Remote Similarity	NPD7584	Approved
0.6914	Remote Similarity	NPD9717	Approved
0.6901	Remote Similarity	NPD2796	Approved
0.6898	Remote Similarity	NPD7799	Discontinued
0.6852	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4308	Phase 3
0.6842	Remote Similarity	NPD2799	Discontinued
0.6834	Remote Similarity	NPD8285	Discontinued
0.6829	Remote Similarity	NPD3225	Approved
0.6826	Remote Similarity	NPD7095	Approved
0.6814	Remote Similarity	NPD7585	Approved
0.6811	Remote Similarity	NPD8127	Discontinued
0.6805	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5404	Approved
0.6802	Remote Similarity	NPD5406	Approved
0.6802	Remote Similarity	NPD5408	Approved
0.6802	Remote Similarity	NPD5405	Approved
0.6794	Remote Similarity	NPD8404	Phase 2
0.6786	Remote Similarity	NPD3764	Approved
0.6786	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD411	Approved
0.6765	Remote Similarity	NPD7583	Approved
0.6763	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD8368	Discontinued
0.6747	Remote Similarity	NPD2798	Approved
0.6742	Remote Similarity	NPD6273	Approved
0.6739	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD3926	Phase 2
0.6724	Remote Similarity	NPD970	Clinical (unspecified phase)
0.672	Remote Similarity	NPD1247	Approved
0.672	Remote Similarity	NPD7177	Discontinued
0.6716	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD1240	Approved
0.6706	Remote Similarity	NPD1613	Approved
0.6706	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4060	Phase 1
0.6703	Remote Similarity	NPD919	Approved
0.6702	Remote Similarity	NPD5953	Discontinued
0.67	Remote Similarity	NPD7680	Approved
0.6699	Remote Similarity	NPD7930	Approved
0.6687	Remote Similarity	NPD2797	Approved
0.6686	Remote Similarity	NPD3268	Approved
0.6684	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD230	Phase 1
0.6667	Remote Similarity	NPD2344	Approved
0.6667	Remote Similarity	NPD5763	Approved
0.6667	Remote Similarity	NPD5762	Approved
0.6667	Remote Similarity	NPD7440	Discontinued
0.6649	Remote Similarity	NPD8407	Phase 2
0.6648	Remote Similarity	NPD8166	Discontinued
0.6648	Remote Similarity	NPD5049	Phase 3
0.6648	Remote Similarity	NPD7003	Approved
0.6647	Remote Similarity	NPD1019	Discontinued
0.6647	Remote Similarity	NPD4062	Phase 3
0.6628	Remote Similarity	NPD1607	Approved
0.6613	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.661	Remote Similarity	NPD2354	Approved
0.661	Remote Similarity	NPD3887	Approved
0.6609	Remote Similarity	NPD6100	Approved
0.6609	Remote Similarity	NPD6099	Approved
0.6608	Remote Similarity	NPD4307	Phase 2
0.6607	Remote Similarity	NPD2861	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