NPASS Compound

Structure

CID260425 OpenBabel06191716062D 43 46 0 0 1 0 0 0 0 0999 V2000 -5.1962 3.0000 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 -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 -1.0000 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 1.7321 -1.0000 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 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 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 -5.1962 2.0000 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 -6.9282 3.0000 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 -6.9282 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 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 -7.7942 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 -7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 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 -1.7321 -3.0000 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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 0.0000 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 4 2 0 0 0 0 1 13 1 0 0 0 0 2 5 2 0 0 0 0 2 14 1 0 0 0 0 3 6 2 0 0 0 0 3 13 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 21 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 39 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 11 40 1 0 0 0 0 12 41 1 0 0 0 0 15 17 2 0 0 0 0 15 29 1 0 0 0 0 16 18 2 0 0 0 0 16 30 1 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 19 22 1 0 0 0 0 19 33 1 1 0 0 0 20 12 1 6 0 0 0 20 26 1 0 0 0 0 20 42 1 0 0 0 0 21 34 2 0 0 0 0 21 43 1 0 0 0 0 22 24 1 0 0 0 0 22 35 1 6 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 23 36 1 6 0 0 0 24 27 1 0 0 0 0 24 37 1 1 0 0 0 25 28 1 0 0 0 0 25 38 1 1 0 0 0 26 43 1 1 0 0 0 27 40 1 0 0 0 0 27 41 1 6 0 0 0 28 39 1 6 0 0 0 28 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	610.19
Volume:	569.38
LogP:	0.187
LogD:	-0.149
LogS:	-2.066
# Rotatable Bonds:	11
TPSA:	245.29
# H-Bond Aceptor:	15
# H-Bond Donor:	9
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.085
Synthetic Accessibility Score:	4.695
Fsp3:	0.464
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.56
MDCK Permeability:	1.641145172470715e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.983
20% Bioavailability (F20%):	0.967
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.103
Plasma Protein Binding (PPB):	95.1359634399414%
Volume Distribution (VD):	0.218
Pgp-substrate:	7.215146064758301%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.017
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.115
CYP2C9-substrate:	0.16
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.016

ADMET: Excretion

Clearance (CL):	1.14
Half-life (T1/2):	0.83

ADMET: Toxicity

hERG Blockers:	0.247
Human Hepatotoxicity (H-HT):	0.119
Drug-inuced Liver Injury (DILI):	0.331
AMES Toxicity:	0.596
Rat Oral Acute Toxicity:	0.135
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.977
Carcinogencity:	0.05
Eye Corrosion:	0.003
Eye Irritation:	0.164
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC260425

Natural Product ID:	NPC260425
*Common Name:**	Calceolarioside C
IUPAC Name:	[(2R,3S,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-2-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	GNDDBOHLMOANGU-TYGLCWKWSA-N
Standard InCHI:	InChI=1S/C28H34O15/c29-15-4-1-13(9-17(15)31)3-6-21(34)43-26-20(12-41-27-24(37)22(35)19(33)11-40-27)42-28(25(38)23(26)36)39-8-7-14-2-5-16(30)18(32)10-14/h1-6,9-10,19-20,22-33,35-38H,7-8,11-12H2/b6-3+/t19-,20-,22+,23-,24-,25-,26-,27+,28-/m1/s1
SMILES:	c1cc(c(cc1/C=C/C(=O)O[C@@H]1[C@@H](CO[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)O[C@H]([C@@H]([C@H]1O)O)OCCc1ccc(c(c1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3632940
PubChem CID:	45360240
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	flower	n.a.	PMID[15481244]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17156960]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26422318]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28218000]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30676026]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21387	Forsythia suspensa	Species	Oleaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	56.2	%	PMID[564180]

☑ 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 NPC260425 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	328
0.1-0.2	1362
0.2-0.3	3262
0.3-0.4	7997
0.4-0.5	9816
0.5-0.6	7884
0.6-0.7	8337
0.7-0.8	3219
0.8-0.85	306
0.85-0.9	88
0.9-0.95	82
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9924	High Similarity	NPC89105
0.9924	High Similarity	NPC476383
0.9924	High Similarity	NPC81515
0.9924	High Similarity	NPC197316
0.9924	High Similarity	NPC68092
0.9924	High Similarity	NPC205195
0.9924	High Similarity	NPC64141
0.9924	High Similarity	NPC472350
0.9847	High Similarity	NPC78363
0.9774	High Similarity	NPC476385
0.9774	High Similarity	NPC476377
0.9774	High Similarity	NPC134405
0.9774	High Similarity	NPC47471
0.9769	High Similarity	NPC287597
0.9769	High Similarity	NPC34293
0.9769	High Similarity	NPC886
0.9701	High Similarity	NPC265648
0.9701	High Similarity	NPC222433
0.9699	High Similarity	NPC475530
0.9699	High Similarity	NPC473799
0.963	High Similarity	NPC476380
0.963	High Similarity	NPC269141
0.963	High Similarity	NPC205864
0.963	High Similarity	NPC76406
0.963	High Similarity	NPC119537
0.963	High Similarity	NPC175214
0.963	High Similarity	NPC476381
0.963	High Similarity	NPC247032
0.963	High Similarity	NPC112
0.963	High Similarity	NPC476397
0.963	High Similarity	NPC476384
0.963	High Similarity	NPC264632
0.963	High Similarity	NPC105005
0.963	High Similarity	NPC96795
0.963	High Similarity	NPC298257
0.963	High Similarity	NPC476378
0.963	High Similarity	NPC476375
0.9624	High Similarity	NPC321638
0.9624	High Similarity	NPC171134
0.9624	High Similarity	NPC328273
0.9624	High Similarity	NPC321184
0.9559	High Similarity	NPC296954
0.9559	High Similarity	NPC300894
0.9559	High Similarity	NPC196063
0.9559	High Similarity	NPC141455
0.9559	High Similarity	NPC64195
0.9549	High Similarity	NPC476376
0.9545	High Similarity	NPC476870
0.9489	High Similarity	NPC34927
0.9489	High Similarity	NPC34587
0.9489	High Similarity	NPC100998
0.9489	High Similarity	NPC252292
0.9489	High Similarity	NPC476382
0.9466	High Similarity	NPC473285
0.942	High Similarity	NPC229505
0.9389	High Similarity	NPC235294
0.9389	High Similarity	NPC46137
0.9385	High Similarity	NPC477293
0.9385	High Similarity	NPC229784
0.9385	High Similarity	NPC477294
0.9353	High Similarity	NPC232992
0.9343	High Similarity	NPC40305
0.9318	High Similarity	NPC254275
0.9308	High Similarity	NPC232880
0.9275	High Similarity	NPC476867
0.927	High Similarity	NPC140502
0.9242	High Similarity	NPC219677
0.9242	High Similarity	NPC246869
0.9242	High Similarity	NPC225384
0.9242	High Similarity	NPC138777
0.9237	High Similarity	NPC184092
0.9231	High Similarity	NPC476873
0.9231	High Similarity	NPC288416
0.922	High Similarity	NPC476398
0.922	High Similarity	NPC259347
0.922	High Similarity	NPC94871
0.922	High Similarity	NPC471062
0.922	High Similarity	NPC306890
0.922	High Similarity	NPC476386
0.922	High Similarity	NPC470933
0.922	High Similarity	NPC473427
0.9209	High Similarity	NPC476866
0.9209	High Similarity	NPC476868
0.9209	High Similarity	NPC476869
0.9209	High Similarity	NPC476864
0.9197	High Similarity	NPC186406
0.9179	High Similarity	NPC471883
0.9173	High Similarity	NPC473924
0.9155	High Similarity	NPC257970
0.9155	High Similarity	NPC188393
0.9155	High Similarity	NPC470927
0.9155	High Similarity	NPC470934
0.9143	High Similarity	NPC476865
0.9111	High Similarity	NPC263829
0.9104	High Similarity	NPC254398
0.9098	High Similarity	NPC478255
0.9084	High Similarity	NPC79715
0.9084	High Similarity	NPC108659
0.9084	High Similarity	NPC264900
0.9084	High Similarity	NPC231607
0.9077	High Similarity	NPC83218
0.9077	High Similarity	NPC126991
0.9065	High Similarity	NPC478239
0.9028	High Similarity	NPC106818
0.9015	High Similarity	NPC225307
0.9014	High Similarity	NPC28776
0.9014	High Similarity	NPC473138
0.9008	High Similarity	NPC471157
0.9008	High Similarity	NPC94179
0.9	High Similarity	NPC110063
0.9	High Similarity	NPC232228
0.9	High Similarity	NPC292443
0.8993	High Similarity	NPC157816
0.8993	High Similarity	NPC296643
0.8986	High Similarity	NPC202700
0.8971	High Similarity	NPC123988
0.8966	High Similarity	NPC471874
0.8966	High Similarity	NPC87403
0.8951	High Similarity	NPC106138
0.8939	High Similarity	NPC106677
0.8936	High Similarity	NPC262182
0.8936	High Similarity	NPC216819
0.8936	High Similarity	NPC83743
0.8936	High Similarity	NPC287615
0.8905	High Similarity	NPC157554
0.8905	High Similarity	NPC470572
0.8897	High Similarity	NPC478268
0.8889	High Similarity	NPC476871
0.8881	High Similarity	NPC80732
0.8881	High Similarity	NPC201148
0.8881	High Similarity	NPC3460
0.8881	High Similarity	NPC199311
0.8881	High Similarity	NPC192763
0.8881	High Similarity	NPC215095
0.8881	High Similarity	NPC261122
0.8881	High Similarity	NPC28651
0.8881	High Similarity	NPC23677
0.8881	High Similarity	NPC210611
0.8881	High Similarity	NPC300262
0.8873	High Similarity	NPC199928
0.8872	High Similarity	NPC148982
0.8849	High Similarity	NPC106944
0.8846	High Similarity	NPC52097
0.8841	High Similarity	NPC302583
0.8841	High Similarity	NPC310252
0.8841	High Similarity	NPC100558
0.8841	High Similarity	NPC84789
0.8824	High Similarity	NPC28637
0.8819	High Similarity	NPC478242
0.8777	High Similarity	NPC220942
0.8777	High Similarity	NPC226005
0.8777	High Similarity	NPC100389
0.8769	High Similarity	NPC266045
0.8769	High Similarity	NPC147654
0.8769	High Similarity	NPC11724
0.8768	High Similarity	NPC177035
0.8768	High Similarity	NPC186418
0.8768	High Similarity	NPC199459
0.8768	High Similarity	NPC471664
0.8768	High Similarity	NPC52277
0.8768	High Similarity	NPC471665
0.8759	High Similarity	NPC35731
0.8759	High Similarity	NPC135127
0.8722	High Similarity	NPC252114
0.8705	High Similarity	NPC126206
0.8705	High Similarity	NPC470413
0.8705	High Similarity	NPC138738
0.8699	High Similarity	NPC125823
0.8699	High Similarity	NPC85192
0.8699	High Similarity	NPC140151
0.8699	High Similarity	NPC143480
0.8699	High Similarity	NPC7145
0.8692	High Similarity	NPC476872
0.869	High Similarity	NPC90896
0.869	High Similarity	NPC283839
0.8662	High Similarity	NPC204644
0.8662	High Similarity	NPC113680
0.8662	High Similarity	NPC278961
0.8658	High Similarity	NPC11411
0.8657	High Similarity	NPC156692
0.8657	High Similarity	NPC45224
0.8657	High Similarity	NPC173150
0.8657	High Similarity	NPC471881
0.8657	High Similarity	NPC35288
0.8657	High Similarity	NPC471882
0.8647	High Similarity	NPC90318
0.8639	High Similarity	NPC289967
0.8639	High Similarity	NPC53587
0.8639	High Similarity	NPC472611
0.8639	High Similarity	NPC472612
0.8639	High Similarity	NPC176186
0.8639	High Similarity	NPC169404
0.8633	High Similarity	NPC37468
0.8633	High Similarity	NPC154485
0.8633	High Similarity	NPC471345
0.8633	High Similarity	NPC471872
0.863	High Similarity	NPC12006
0.863	High Similarity	NPC69367
0.8621	High Similarity	NPC116229
0.8621	High Similarity	NPC478237

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 NPC260425 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	783
0.2-0.3	1649
0.3-0.4	2977
0.4-0.5	1952
0.5-0.6	1140
0.6-0.7	343
0.7-0.8	35
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9924	High Similarity	NPD7266	Discontinued
0.8311	Intermediate Similarity	NPD1653	Approved
0.8276	Intermediate Similarity	NPD6190	Approved
0.7888	Intermediate Similarity	NPD7054	Approved
0.7853	Intermediate Similarity	NPD7685	Pre-registration
0.784	Intermediate Similarity	NPD7074	Phase 3
0.784	Intermediate Similarity	NPD7472	Approved
0.7826	Intermediate Similarity	NPD7228	Approved
0.7746	Intermediate Similarity	NPD3027	Phase 3
0.7744	Intermediate Similarity	NPD7251	Discontinued
0.7708	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1613	Approved
0.7707	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6797	Phase 2
0.7607	Intermediate Similarity	NPD3818	Discontinued
0.759	Intermediate Similarity	NPD7808	Phase 3
0.758	Intermediate Similarity	NPD8455	Phase 2
0.7566	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7483	Intermediate Similarity	NPD8166	Discontinued
0.7456	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1091	Approved
0.7417	Intermediate Similarity	NPD6674	Discontinued
0.7415	Intermediate Similarity	NPD230	Phase 1
0.7405	Intermediate Similarity	NPD37	Approved
0.7375	Intermediate Similarity	NPD4965	Approved
0.7375	Intermediate Similarity	NPD4966	Approved
0.7375	Intermediate Similarity	NPD4967	Phase 2
0.7365	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD8313	Approved
0.7337	Intermediate Similarity	NPD8312	Approved
0.7321	Intermediate Similarity	NPD7240	Approved
0.7315	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6166	Phase 2
0.7273	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3021	Approved
0.7239	Intermediate Similarity	NPD3022	Approved
0.7219	Intermediate Similarity	NPD6559	Discontinued
0.7197	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1934	Approved
0.7183	Intermediate Similarity	NPD3705	Approved
0.7171	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7143	Intermediate Similarity	NPD1465	Phase 2
0.7143	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3455	Phase 2
0.7092	Intermediate Similarity	NPD1357	Approved
0.7091	Intermediate Similarity	NPD7199	Phase 2
0.7086	Intermediate Similarity	NPD7097	Phase 1
0.7067	Intermediate Similarity	NPD4340	Discontinued
0.7045	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5125	Phase 3
0.7042	Intermediate Similarity	NPD5126	Approved
0.7041	Intermediate Similarity	NPD5844	Phase 1
0.7012	Intermediate Similarity	NPD7075	Discontinued
0.7007	Intermediate Similarity	NPD969	Suspended
0.7007	Intermediate Similarity	NPD2861	Phase 2
0.7007	Intermediate Similarity	NPD228	Approved
0.7	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4060	Phase 1
0.6994	Remote Similarity	NPD5402	Approved
0.6994	Remote Similarity	NPD3817	Phase 2
0.6988	Remote Similarity	NPD8127	Discontinued
0.698	Remote Similarity	NPD3764	Approved
0.6968	Remote Similarity	NPD1652	Phase 2
0.695	Remote Similarity	NPD5536	Phase 2
0.6943	Remote Similarity	NPD5058	Phase 3
0.694	Remote Similarity	NPD7680	Approved
0.6933	Remote Similarity	NPD2977	Approved
0.6933	Remote Similarity	NPD2801	Approved
0.6933	Remote Similarity	NPD2978	Approved
0.6933	Remote Similarity	NPD6233	Phase 2
0.6913	Remote Similarity	NPD7095	Approved
0.6908	Remote Similarity	NPD5314	Approved
0.6905	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD9545	Approved
0.6899	Remote Similarity	NPD1511	Approved
0.6897	Remote Similarity	NPD9269	Phase 2
0.6887	Remote Similarity	NPD3062	Approved
0.6887	Remote Similarity	NPD3059	Approved
0.6887	Remote Similarity	NPD3061	Approved
0.6882	Remote Similarity	NPD3751	Discontinued
0.6875	Remote Similarity	NPD5403	Approved
0.6855	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3882	Suspended
0.6846	Remote Similarity	NPD4908	Phase 1
0.6842	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5124	Phase 1
0.6838	Remote Similarity	NPD1358	Approved
0.6829	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1512	Approved
0.6806	Remote Similarity	NPD9381	Approved
0.6806	Remote Similarity	NPD9384	Approved
0.6797	Remote Similarity	NPD6653	Approved
0.679	Remote Similarity	NPD7458	Discontinued
0.6786	Remote Similarity	NPD5283	Phase 1
0.6779	Remote Similarity	NPD5736	Approved
0.6776	Remote Similarity	NPD3620	Phase 2
0.6776	Remote Similarity	NPD943	Approved
0.6776	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD9570	Approved
0.6774	Remote Similarity	NPD2935	Discontinued
0.6768	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3496	Discontinued
0.6757	Remote Similarity	NPD3094	Phase 2
0.6755	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6798	Discontinued
0.6753	Remote Similarity	NPD4538	Approved
0.6753	Remote Similarity	NPD4536	Approved
0.6753	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5401	Approved
0.6746	Remote Similarity	NPD6232	Discontinued
0.6746	Remote Similarity	NPD3787	Discontinued
0.6735	Remote Similarity	NPD2983	Phase 2
0.6735	Remote Similarity	NPD2982	Phase 2
0.6732	Remote Similarity	NPD6355	Discontinued
0.6732	Remote Similarity	NPD1933	Approved
0.6731	Remote Similarity	NPD5763	Approved
0.6731	Remote Similarity	NPD5762	Approved
0.6728	Remote Similarity	NPD3687	Approved
0.6728	Remote Similarity	NPD3686	Approved
0.6727	Remote Similarity	NPD7819	Suspended
0.6725	Remote Similarity	NPD7473	Discontinued
0.6723	Remote Similarity	NPD8150	Discontinued
0.672	Remote Similarity	NPD8319	Approved
0.672	Remote Similarity	NPD8320	Phase 1
0.6714	Remote Similarity	NPD7843	Approved
0.6712	Remote Similarity	NPD1610	Phase 2
0.6712	Remote Similarity	NPD422	Phase 1
0.671	Remote Similarity	NPD5588	Approved
0.671	Remote Similarity	NPD5960	Phase 3
0.6709	Remote Similarity	NPD3750	Approved
0.6708	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6385	Approved
0.6707	Remote Similarity	NPD6386	Approved
0.6705	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.669	Remote Similarity	NPD7157	Approved
0.6689	Remote Similarity	NPD3225	Approved
0.6686	Remote Similarity	NPD7549	Discontinued
0.6685	Remote Similarity	NPD6843	Phase 3
0.6685	Remote Similarity	NPD6842	Approved
0.6685	Remote Similarity	NPD6841	Approved
0.6667	Remote Similarity	NPD2981	Phase 2
0.6667	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD826	Approved
0.6667	Remote Similarity	NPD6801	Discontinued
0.6667	Remote Similarity	NPD1548	Phase 1
0.6667	Remote Similarity	NPD825	Approved
0.6667	Remote Similarity	NPD3018	Phase 2
0.6667	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7699	Phase 2
0.6667	Remote Similarity	NPD9494	Approved
0.6667	Remote Similarity	NPD8151	Discontinued
0.6667	Remote Similarity	NPD7700	Phase 2
0.6667	Remote Similarity	NPD1558	Phase 1
0.6646	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3060	Approved
0.6646	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1242	Phase 1
0.6642	Remote Similarity	NPD3134	Approved
0.6641	Remote Similarity	NPD2934	Approved
0.6641	Remote Similarity	NPD2933	Approved
0.6629	Remote Similarity	NPD7039	Approved
0.6629	Remote Similarity	NPD7038	Approved
0.6627	Remote Similarity	NPD5494	Approved
0.6622	Remote Similarity	NPD9622	Approved
0.6621	Remote Similarity	NPD9268	Approved
0.6607	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7411	Suspended
0.6604	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4110	Phase 3
0.6603	Remote Similarity	NPD7033	Discontinued
0.6603	Remote Similarity	NPD4108	Discontinued
0.6601	Remote Similarity	NPD6663	Approved
0.6601	Remote Similarity	NPD4062	Phase 3
0.6599	Remote Similarity	NPD3092	Approved
0.6596	Remote Similarity	NPD5535	Approved
0.6593	Remote Similarity	NPD6534	Approved
0.6593	Remote Similarity	NPD6535	Approved
0.6591	Remote Similarity	NPD2859	Approved
0.6591	Remote Similarity	NPD2860	Approved
0.6585	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4357	Discontinued
0.6584	Remote Similarity	NPD6799	Approved
0.6582	Remote Similarity	NPD1549	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