NPASS Compound

Structure

CID138915 OpenBabel06191715492D 45 48 0 0 1 0 0 0 0 0999 V2000 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 0.5000 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 5.1962 -0.0000 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 2.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 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 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 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 1.5000 0.0000 C 0 0 0 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 -1.7321 0.0000 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 0.8660 -1.5000 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 1.7321 -0.0000 0.0000 C 0 0 2 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 4.3301 3.5000 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 5.1962 2.0000 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 -1.0000 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 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 0.0000 0.0000 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 1 40 1 0 0 0 0 2 41 1 0 0 0 0 3 13 2 0 0 0 0 3 18 1 0 0 0 0 4 14 2 0 0 0 0 4 19 1 0 0 0 0 5 7 1 0 0 0 0 5 20 2 0 0 0 0 6 8 2 0 0 0 0 6 20 1 0 0 0 0 7 21 2 0 0 0 0 8 21 1 0 0 0 0 9 11 1 0 0 0 0 9 22 2 0 0 0 0 10 12 1 0 0 0 0 10 23 2 0 0 0 0 11 24 2 0 0 0 0 12 25 2 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 18 2 0 0 0 0 15 22 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 42 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 33 1 0 0 0 0 21 43 1 0 0 0 0 22 40 1 0 0 0 0 23 41 1 0 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 26 17 1 1 0 0 0 26 29 1 0 0 0 0 26 44 1 0 0 0 0 27 36 2 0 0 0 0 27 42 1 0 0 0 0 28 37 2 0 0 0 0 28 45 1 0 0 0 0 29 30 1 0 0 0 0 29 38 1 6 0 0 0 30 31 1 0 0 0 0 30 39 1 1 0 0 0 31 32 1 0 0 0 0 31 45 1 6 0 0 0 32 43 1 1 0 0 0 32 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.07
Volume:	436.881
LogP:	0.551
LogD:	0.193
LogS:	-4.122
# Rotatable Bonds:	4
TPSA:	247.81
# H-Bond Aceptor:	14
# H-Bond Donor:	9
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.203
Synthetic Accessibility Score:	4.209
Fsp3:	0.238
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.613
MDCK Permeability:	8.703471394255757e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.364
20% Bioavailability (F20%):	0.131
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	87.6646499633789%
Volume Distribution (VD):	0.788
Pgp-substrate:	17.608938217163086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.033
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.108
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	2.284
Half-life (T1/2):	0.961

ADMET: Toxicity

hERG Blockers:	0.104
Human Hepatotoxicity (H-HT):	0.163
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.344
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.83
Carcinogencity:	0.023
Eye Corrosion:	0.003
Eye Irritation:	0.67
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC138915

Natural Product ID:	NPC138915
*Common Name:**	Robustaside F
IUPAC Name:	[(2R,3S,4S,5R,6S)-3,4-dihydroxy-5-[(Z)-3-(2-hydroxy-5-methoxyphenyl)prop-2-enoyl]oxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl (Z)-3-(2-hydroxy-5-methoxyphenyl)prop-2-enoate
Synonyms:	Robustaside F
Standard InCHIKey:	VZMAYTGBKKDAOI-KNPJAZBNSA-N
Standard InCHI:	InChI=1S/C32H32O13/c1-40-22-9-11-24(34)18(15-22)3-13-27(36)42-17-26-29(38)30(39)31(32(44-26)43-21-7-5-20(33)6-8-21)45-28(37)14-4-19-16-23(41-2)10-12-25(19)35/h3-16,26,29-35,38-39H,17H2,1-2H3/b13-3-,14-4-/t26-,29-,30+,31-,32-/m1/s1
SMILES:	COc1ccc(c(/C=CC(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](Oc3ccc(cc3)O)O2)OC(=O)/C=Cc2cc(ccc2O)OC)O)O)c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669713
PubChem CID:	50994837
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
NPO32611	grevillea "poorinda queen"	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21155593]
NPO29927	Grevillea	Genus	Proteaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21155593]
NPO29927	Grevillea	Genus	Proteaceae	Eukaryota	n.a.	twig	n.a.	PMID[21155593]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	14700.0	nM	PMID[520160]

☑ 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 NPC138915 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	315
0.1-0.2	1447
0.2-0.3	3804
0.3-0.4	8944
0.4-0.5	9336
0.5-0.6	5099
0.6-0.7	8829
0.7-0.8	4394
0.8-0.85	435
0.85-0.9	77
0.9-0.95	16
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9357	High Similarity	NPC145319
0.9178	High Similarity	NPC93619
0.9	High Similarity	NPC166180
0.8993	High Similarity	NPC299761
0.8993	High Similarity	NPC230439
0.8993	High Similarity	NPC279281
0.8993	High Similarity	NPC92153
0.8973	High Similarity	NPC92054
0.8973	High Similarity	NPC140722
0.8973	High Similarity	NPC4958
0.8966	High Similarity	NPC199928
0.8958	High Similarity	NPC292443
0.8958	High Similarity	NPC232228
0.8889	High Similarity	NPC132737
0.8889	High Similarity	NPC478239
0.8882	High Similarity	NPC478269
0.8881	High Similarity	NPC186406
0.8851	High Similarity	NPC476871
0.8844	High Similarity	NPC261122
0.8844	High Similarity	NPC80732
0.8844	High Similarity	NPC192763
0.8844	High Similarity	NPC201148
0.8844	High Similarity	NPC28651
0.8844	High Similarity	NPC3460
0.8844	High Similarity	NPC210611
0.8844	High Similarity	NPC215095
0.8844	High Similarity	NPC199311
0.8844	High Similarity	NPC300262
0.8836	High Similarity	NPC476865
0.8832	High Similarity	NPC146540
0.8828	High Similarity	NPC476867
0.8819	High Similarity	NPC157816
0.8794	High Similarity	NPC185778
0.8774	High Similarity	NPC475183
0.8768	High Similarity	NPC97326
0.8767	High Similarity	NPC476864
0.8767	High Similarity	NPC34927
0.8767	High Similarity	NPC476869
0.8767	High Similarity	NPC476382
0.8767	High Similarity	NPC252292
0.8767	High Similarity	NPC476866
0.8767	High Similarity	NPC34587
0.8767	High Similarity	NPC100998
0.8767	High Similarity	NPC476868
0.8766	High Similarity	NPC478267
0.875	High Similarity	NPC11411
0.8733	High Similarity	NPC478268
0.8718	High Similarity	NPC280923
0.8716	High Similarity	NPC478237
0.8696	High Similarity	NPC40377
0.869	High Similarity	NPC140502
0.869	High Similarity	NPC65833
0.8675	High Similarity	NPC215811
0.8671	High Similarity	NPC124149
0.8667	High Similarity	NPC143480
0.8667	High Similarity	NPC7145
0.8667	High Similarity	NPC85192
0.8667	High Similarity	NPC125823
0.8667	High Similarity	NPC213197
0.8662	High Similarity	NPC475174
0.8658	High Similarity	NPC94871
0.8658	High Similarity	NPC470933
0.8658	High Similarity	NPC471062
0.8658	High Similarity	NPC473427
0.8658	High Similarity	NPC106138
0.8658	High Similarity	NPC259347
0.8658	High Similarity	NPC476386
0.8658	High Similarity	NPC306890
0.8658	High Similarity	NPC476398
0.8649	High Similarity	NPC232992
0.8649	High Similarity	NPC97240
0.8643	High Similarity	NPC225384
0.8643	High Similarity	NPC246869
0.8643	High Similarity	NPC138777
0.8639	High Similarity	NPC226722
0.8639	High Similarity	NPC287615
0.8639	High Similarity	NPC216819
0.8639	High Similarity	NPC143120
0.8639	High Similarity	NPC274960
0.8639	High Similarity	NPC473909
0.8639	High Similarity	NPC262182
0.8639	High Similarity	NPC83743
0.8618	High Similarity	NPC260604
0.8618	High Similarity	NPC299435
0.8611	High Similarity	NPC100389
0.8609	High Similarity	NPC176186
0.8609	High Similarity	NPC169404
0.8609	High Similarity	NPC289967
0.8609	High Similarity	NPC472611
0.8609	High Similarity	NPC53587
0.8609	High Similarity	NPC472612
0.8601	High Similarity	NPC37468
0.86	High Similarity	NPC470934
0.86	High Similarity	NPC470927
0.86	High Similarity	NPC257970
0.86	High Similarity	NPC188393
0.86	High Similarity	NPC114740
0.86	High Similarity	NPC182350
0.8591	High Similarity	NPC93924
0.8591	High Similarity	NPC96294
0.8571	High Similarity	NPC474398
0.8571	High Similarity	NPC110063
0.8571	High Similarity	NPC474441
0.8571	High Similarity	NPC476026
0.8571	High Similarity	NPC474401
0.8562	High Similarity	NPC245219
0.8562	High Similarity	NPC31081
0.8553	High Similarity	NPC150442
0.8552	High Similarity	NPC202700
0.8533	High Similarity	NPC313334
0.8533	High Similarity	NPC206264
0.8533	High Similarity	NPC212670
0.8526	High Similarity	NPC149873
0.8526	High Similarity	NPC7191
0.8521	High Similarity	NPC28637
0.8516	High Similarity	NPC57072
0.8516	High Similarity	NPC231475
0.8511	High Similarity	NPC235294
0.8511	High Similarity	NPC46137
0.8506	High Similarity	NPC284810
0.85	High Similarity	NPC295970
0.85	High Similarity	NPC280385
0.8493	Intermediate Similarity	NPC476385
0.8493	Intermediate Similarity	NPC476377
0.8493	Intermediate Similarity	NPC47471
0.8493	Intermediate Similarity	NPC134405
0.8487	Intermediate Similarity	NPC120774
0.8487	Intermediate Similarity	NPC264875
0.8487	Intermediate Similarity	NPC215060
0.8487	Intermediate Similarity	NPC163598
0.8487	Intermediate Similarity	NPC476352
0.8483	Intermediate Similarity	NPC476383
0.8483	Intermediate Similarity	NPC472350
0.8483	Intermediate Similarity	NPC64141
0.8483	Intermediate Similarity	NPC81515
0.8483	Intermediate Similarity	NPC68092
0.8483	Intermediate Similarity	NPC197316
0.8483	Intermediate Similarity	NPC89105
0.8477	Intermediate Similarity	NPC120426
0.8477	Intermediate Similarity	NPC205727
0.8477	Intermediate Similarity	NPC21184
0.8477	Intermediate Similarity	NPC294522
0.8472	Intermediate Similarity	NPC197723
0.8472	Intermediate Similarity	NPC186418
0.8472	Intermediate Similarity	NPC138350
0.8472	Intermediate Similarity	NPC3293
0.8472	Intermediate Similarity	NPC40664
0.8472	Intermediate Similarity	NPC157554
0.8472	Intermediate Similarity	NPC469383
0.8472	Intermediate Similarity	NPC165482
0.8467	Intermediate Similarity	NPC83975
0.8456	Intermediate Similarity	NPC268515
0.8456	Intermediate Similarity	NPC40222
0.8452	Intermediate Similarity	NPC133984
0.8446	Intermediate Similarity	NPC471028
0.8442	Intermediate Similarity	NPC131532
0.844	Intermediate Similarity	NPC470079
0.8435	Intermediate Similarity	NPC222433
0.8435	Intermediate Similarity	NPC164599
0.8435	Intermediate Similarity	NPC473792
0.8435	Intermediate Similarity	NPC473873
0.8435	Intermediate Similarity	NPC265648
0.8431	Intermediate Similarity	NPC34965
0.8431	Intermediate Similarity	NPC183536
0.8425	Intermediate Similarity	NPC475530
0.8425	Intermediate Similarity	NPC473799
0.8421	Intermediate Similarity	NPC475890
0.8414	Intermediate Similarity	NPC78363
0.8414	Intermediate Similarity	NPC138738
0.8414	Intermediate Similarity	NPC134260
0.8414	Intermediate Similarity	NPC470413
0.8414	Intermediate Similarity	NPC126206
0.8414	Intermediate Similarity	NPC260425
0.8411	Intermediate Similarity	NPC475250
0.8411	Intermediate Similarity	NPC30688
0.8411	Intermediate Similarity	NPC283839
0.8411	Intermediate Similarity	NPC111785
0.8411	Intermediate Similarity	NPC176903
0.8411	Intermediate Similarity	NPC90896
0.8403	Intermediate Similarity	NPC263829
0.8403	Intermediate Similarity	NPC476870
0.8403	Intermediate Similarity	NPC238243
0.84	Intermediate Similarity	NPC175275
0.84	Intermediate Similarity	NPC41844
0.84	Intermediate Similarity	NPC227902
0.84	Intermediate Similarity	NPC15577
0.84	Intermediate Similarity	NPC52740
0.84	Intermediate Similarity	NPC474422
0.8395	Intermediate Similarity	NPC470438
0.8392	Intermediate Similarity	NPC294166
0.8392	Intermediate Similarity	NPC115022
0.8387	Intermediate Similarity	NPC228357
0.8378	Intermediate Similarity	NPC298257
0.8378	Intermediate Similarity	NPC252169
0.8378	Intermediate Similarity	NPC476397
0.8378	Intermediate Similarity	NPC264632
0.8378	Intermediate Similarity	NPC476378
0.8378	Intermediate Similarity	NPC205864
0.8378	Intermediate Similarity	NPC175214
0.8378	Intermediate Similarity	NPC476381

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 NPC138915 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	818
0.2-0.3	1736
0.3-0.4	2747
0.4-0.5	1839
0.5-0.6	1134
0.6-0.7	509
0.7-0.8	101
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8533	High Similarity	NPD1653	Approved
0.8483	Intermediate Similarity	NPD7266	Discontinued
0.8188	Intermediate Similarity	NPD1091	Approved
0.8141	Intermediate Similarity	NPD8455	Phase 2
0.8072	Intermediate Similarity	NPD8313	Approved
0.8072	Intermediate Similarity	NPD8312	Approved
0.7875	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7054	Approved
0.775	Intermediate Similarity	NPD5402	Approved
0.7746	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6559	Discontinued
0.773	Intermediate Similarity	NPD3496	Discontinued
0.7725	Intermediate Similarity	NPD7472	Approved
0.7725	Intermediate Similarity	NPD7074	Phase 3
0.7692	Intermediate Similarity	NPD7808	Phase 3
0.7665	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6674	Discontinued
0.7635	Intermediate Similarity	NPD6233	Phase 2
0.7633	Intermediate Similarity	NPD7685	Pre-registration
0.7633	Intermediate Similarity	NPD7251	Discontinued
0.7603	Intermediate Similarity	NPD2861	Phase 2
0.7584	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1613	Approved
0.7574	Intermediate Similarity	NPD6797	Phase 2
0.756	Intermediate Similarity	NPD5844	Phase 1
0.7551	Intermediate Similarity	NPD4908	Phase 1
0.755	Intermediate Similarity	NPD7097	Phase 1
0.7516	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD3818	Discontinued
0.7471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4060	Phase 1
0.7457	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD6798	Discontinued
0.7439	Intermediate Similarity	NPD7075	Discontinued
0.7436	Intermediate Similarity	NPD6190	Approved
0.7429	Intermediate Similarity	NPD6671	Approved
0.7429	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5403	Approved
0.7419	Intermediate Similarity	NPD1652	Phase 2
0.741	Intermediate Similarity	NPD7199	Phase 2
0.7403	Intermediate Similarity	NPD5762	Approved
0.7403	Intermediate Similarity	NPD5763	Approved
0.7397	Intermediate Similarity	NPD3225	Approved
0.7396	Intermediate Similarity	NPD3751	Discontinued
0.7381	Intermediate Similarity	NPD6166	Phase 2
0.7381	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4628	Phase 3
0.7329	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5124	Phase 1
0.7303	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD37	Approved
0.7296	Intermediate Similarity	NPD5401	Approved
0.7289	Intermediate Similarity	NPD6234	Discontinued
0.7284	Intermediate Similarity	NPD4380	Phase 2
0.7273	Intermediate Similarity	NPD4965	Approved
0.7273	Intermediate Similarity	NPD7033	Discontinued
0.7273	Intermediate Similarity	NPD4967	Phase 2
0.7273	Intermediate Similarity	NPD4966	Approved
0.7273	Intermediate Similarity	NPD7768	Phase 2
0.7267	Intermediate Similarity	NPD3027	Phase 3
0.7267	Intermediate Similarity	NPD7095	Approved
0.7262	Intermediate Similarity	NPD3787	Discontinued
0.7261	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7819	Suspended
0.7256	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6653	Approved
0.7248	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7411	Suspended
0.7234	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7783	Phase 2
0.7228	Intermediate Similarity	NPD7435	Discontinued
0.7226	Intermediate Similarity	NPD2935	Discontinued
0.7226	Intermediate Similarity	NPD290	Approved
0.7219	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8127	Discontinued
0.7197	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD1934	Approved
0.7192	Intermediate Similarity	NPD422	Phase 1
0.719	Intermediate Similarity	NPD1933	Approved
0.719	Intermediate Similarity	NPD4340	Discontinued
0.719	Intermediate Similarity	NPD6355	Discontinued
0.7188	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7549	Discontinued
0.7172	Intermediate Similarity	NPD1778	Approved
0.717	Intermediate Similarity	NPD5058	Phase 3
0.7153	Intermediate Similarity	NPD968	Approved
0.7152	Intermediate Similarity	NPD2801	Approved
0.7152	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7240	Approved
0.7117	Intermediate Similarity	NPD7458	Discontinued
0.7115	Intermediate Similarity	NPD6032	Approved
0.7115	Intermediate Similarity	NPD1551	Phase 2
0.7114	Intermediate Similarity	NPD2797	Approved
0.7108	Intermediate Similarity	NPD3817	Phase 2
0.7105	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7870	Phase 2
0.7097	Intermediate Similarity	NPD7871	Phase 2
0.7095	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7843	Approved
0.7091	Intermediate Similarity	NPD6801	Discontinued
0.709	Intermediate Similarity	NPD7874	Approved
0.709	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6832	Phase 2
0.7081	Intermediate Similarity	NPD6823	Phase 2
0.7076	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1610	Phase 2
0.7065	Intermediate Similarity	NPD6780	Approved
0.7065	Intermediate Similarity	NPD6778	Approved
0.7065	Intermediate Similarity	NPD6782	Approved
0.7065	Intermediate Similarity	NPD6781	Approved
0.7065	Intermediate Similarity	NPD6777	Approved
0.7065	Intermediate Similarity	NPD6776	Approved
0.7065	Intermediate Similarity	NPD6779	Approved
0.7047	Intermediate Similarity	NPD8651	Approved
0.7044	Intermediate Similarity	NPD3750	Approved
0.7044	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7696	Phase 3
0.7043	Intermediate Similarity	NPD7698	Approved
0.7043	Intermediate Similarity	NPD7697	Approved
0.7039	Intermediate Similarity	NPD4625	Phase 3
0.7037	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1548	Phase 1
0.7019	Intermediate Similarity	NPD6799	Approved
0.7012	Intermediate Similarity	NPD3226	Approved
0.7	Intermediate Similarity	NPD1203	Approved
0.6993	Remote Similarity	NPD7985	Registered
0.6993	Remote Similarity	NPD3268	Approved
0.6988	Remote Similarity	NPD6844	Discontinued
0.6987	Remote Similarity	NPD4538	Approved
0.6987	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4536	Approved
0.6986	Remote Similarity	NPD5585	Approved
0.6984	Remote Similarity	NPD7701	Phase 2
0.698	Remote Similarity	NPD4749	Approved
0.6978	Remote Similarity	NPD1358	Approved
0.6972	Remote Similarity	NPD5535	Approved
0.6968	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD447	Suspended
0.6959	Remote Similarity	NPD1611	Approved
0.6947	Remote Similarity	NPD8151	Discontinued
0.6946	Remote Similarity	NPD1465	Phase 2
0.6944	Remote Similarity	NPD7157	Approved
0.6927	Remote Similarity	NPD8150	Discontinued
0.6918	Remote Similarity	NPD1549	Phase 2
0.6918	Remote Similarity	NPD2424	Discontinued
0.6913	Remote Similarity	NPD1608	Approved
0.6903	Remote Similarity	NPD4140	Approved
0.6901	Remote Similarity	NPD6959	Discontinued
0.6875	Remote Similarity	NPD6184	Discontinued
0.6875	Remote Similarity	NPD7801	Approved
0.6871	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1357	Approved
0.6871	Remote Similarity	NPD7447	Phase 1
0.6865	Remote Similarity	NPD7699	Phase 2
0.6865	Remote Similarity	NPD7700	Phase 2
0.6864	Remote Similarity	NPD3882	Suspended
0.6862	Remote Similarity	NPD7680	Approved
0.686	Remote Similarity	NPD6232	Discontinued
0.6855	Remote Similarity	NPD6002	Phase 3
0.6855	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6005	Phase 3
0.6855	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2346	Discontinued
0.6855	Remote Similarity	NPD6004	Phase 3
0.6846	Remote Similarity	NPD1535	Discovery
0.6846	Remote Similarity	NPD3705	Approved
0.6842	Remote Similarity	NPD5494	Approved
0.6842	Remote Similarity	NPD6584	Phase 3
0.6839	Remote Similarity	NPD4062	Phase 3
0.6839	Remote Similarity	NPD7473	Discontinued
0.6835	Remote Similarity	NPD4308	Phase 3
0.6835	Remote Similarity	NPD9697	Approved
0.6835	Remote Similarity	NPD5588	Approved
0.6835	Remote Similarity	NPD5960	Phase 3
0.6833	Remote Similarity	NPD8434	Phase 2
0.6829	Remote Similarity	NPD6273	Approved
0.6826	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6516	Phase 2
0.6824	Remote Similarity	NPD4626	Approved
0.6824	Remote Similarity	NPD5126	Approved
0.6824	Remote Similarity	NPD5846	Approved
0.6824	Remote Similarity	NPD5125	Phase 3
0.6821	Remote Similarity	NPD6696	Suspended
0.6818	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1511	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