NPASS Compound

Structure

NPC476382 OpenBabel07101718182D 45 48 0 0 1 0 0 0 0 0999 V2000 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 -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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 1 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 -5.1962 2.0000 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 3.0000 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 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 1 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 -5.1962 -4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 -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 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 -0.0000 2.0000 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 3.5000 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 -6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -5.5000 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 -7.7942 1.5000 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 -2.5981 -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 -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 2 40 1 0 0 0 0 3 7 1 0 0 0 0 3 17 2 0 0 0 0 4 8 2 0 0 0 0 4 17 1 0 0 0 0 5 9 2 0 0 0 0 5 18 1 0 0 0 0 6 10 2 0 0 0 0 6 18 1 0 0 0 0 7 19 2 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 24 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 41 1 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 32 1 0 0 0 0 15 42 1 0 0 0 0 16 1 1 6 0 0 0 16 25 1 0 0 0 0 16 43 1 0 0 0 0 19 33 1 0 0 0 0 20 21 2 0 0 0 0 20 34 1 0 0 0 0 21 40 1 0 0 0 0 22 14 1 1 0 0 0 22 29 1 0 0 0 0 22 44 1 0 0 0 0 23 15 1 1 0 0 0 23 26 1 0 0 0 0 23 43 1 0 0 0 0 24 35 2 0 0 0 0 24 45 1 0 0 0 0 25 27 1 0 0 0 0 25 36 1 1 0 0 0 26 27 1 0 0 0 0 26 37 1 6 0 0 0 27 38 1 6 0 0 0 28 30 1 0 0 0 0 28 31 1 0 0 0 0 28 39 1 6 0 0 0 29 30 1 0 0 0 0 29 45 1 6 0 0 0 30 42 1 1 0 0 0 31 41 1 1 0 0 0 31 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	636.24
Volume:	612.478
LogP:	1.236
LogD:	0.684
LogS:	-2.801
# Rotatable Bonds:	13
TPSA:	214.06
# H-Bond Aceptor:	14
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.117
Synthetic Accessibility Score:	4.675
Fsp3:	0.516
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.426
MDCK Permeability:	3.415613537072204e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.912
20% Bioavailability (F20%):	0.871
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	92.87682342529297%
Volume Distribution (VD):	0.275
Pgp-substrate:	5.761707782745361%

ADMET: Metabolism

CYP1A2-inhibitor:	0.079
CYP1A2-substrate:	0.042
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.112
CYP2C9-inhibitor:	0.068
CYP2C9-substrate:	0.231
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.185
CYP3A4-inhibitor:	0.067
CYP3A4-substrate:	0.072

ADMET: Excretion

Clearance (CL):	1.958
Half-life (T1/2):	0.745

ADMET: Toxicity

hERG Blockers:	0.803
Human Hepatotoxicity (H-HT):	0.861
Drug-inuced Liver Injury (DILI):	0.112
AMES Toxicity:	0.395
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.952
Carcinogencity:	0.029
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.149

Download Data

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

Natural Product: NPC476382

Natural Product ID:	NPC476382
*Common Name:**	[(2R,3R,4R,5R,6R)-5-Hydroxy-2-(Hydroxymethyl)-6-[2-(4-Hydroxyphenyl)Ethoxy]-4-[[(2S,3R,4R,5R,6S)-3,4,5-Trihydroxy-6-Methyloxan-2-Yl]Methoxy]Oxan-3-Yl] (E)-3-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoate
IUPAC Name:	[(2R,3R,4R,5R,6R)-5-hydroxy-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]-4-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]methoxy]oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:	Syringalide A 3'-O-Rha
Standard InCHIKey:	VCVDCGNCACPEQN-MXIJRSCASA-N
Standard InCHI:	InChI=1S/C31H40O14/c1-16-25(36)27(38)26(37)23(43-16)15-42-30-28(39)31(41-12-11-17-3-7-19(33)8-4-17)44-22(14-32)29(30)45-24(35)10-6-18-5-9-20(34)21(13-18)40-2/h3-10,13,16,22-23,25-34,36-39H,11-12,14-15H2,1-2H3/b10-6+/t16-,22+,23-,25-,26-,27+,28+,29+,30+,31+/m0/s1
SMILES:	CC1C(C(C(C(O1)COC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)OC)CO)OCCC4=CC=C(C=C4)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL590396
PubChem CID:	46228755
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
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	fresh stems	n.a.	n.a.	PMID[20159656]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	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
IC50	1
Others	8

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	9.7	%	PMID[523097]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	21.4	%	PMID[523097]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	35.7	%	PMID[523097]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	55.7	%	PMID[523097]
NPT993	Cell Line	Hepatocyte	Mus musculus	IC50	=	71200.0	nM	PMID[523097]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	4.5	%	PMID[523097]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	4.6	%	PMID[523097]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	13.3	%	PMID[523097]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	22.2	%	PMID[523097]

☑ 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 NPC476382 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	330
0.1-0.2	1431
0.2-0.3	3471
0.3-0.4	8381
0.4-0.5	9436
0.5-0.6	6043
0.6-0.7	8432
0.7-0.8	4345
0.8-0.85	558
0.85-0.9	167
0.9-0.95	72
0.95-1	31

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC34927
1.0	High Similarity	NPC252292
1.0	High Similarity	NPC34587
1.0	High Similarity	NPC100998
0.9856	High Similarity	NPC232992
0.9781	High Similarity	NPC140502
0.9716	High Similarity	NPC473427
0.9716	High Similarity	NPC94871
0.9716	High Similarity	NPC470933
0.9716	High Similarity	NPC259347
0.9716	High Similarity	NPC476386
0.9716	High Similarity	NPC306890
0.9716	High Similarity	NPC471062
0.9716	High Similarity	NPC476398
0.9648	High Similarity	NPC470934
0.9648	High Similarity	NPC470927
0.9648	High Similarity	NPC188393
0.9648	High Similarity	NPC257970
0.9643	High Similarity	NPC476865
0.9571	High Similarity	NPC476864
0.9571	High Similarity	NPC476866
0.9571	High Similarity	NPC476869
0.9571	High Similarity	NPC476868
0.9568	High Similarity	NPC478239
0.9565	High Similarity	NPC134405
0.9565	High Similarity	NPC476385
0.9562	High Similarity	NPC472350
0.9562	High Similarity	NPC68092
0.9562	High Similarity	NPC81515
0.9562	High Similarity	NPC476383
0.9562	High Similarity	NPC197316
0.9562	High Similarity	NPC89105
0.9562	High Similarity	NPC64141
0.95	High Similarity	NPC476867
0.95	High Similarity	NPC110063
0.9496	High Similarity	NPC222433
0.9496	High Similarity	NPC157816
0.9496	High Similarity	NPC265648
0.9489	High Similarity	NPC78363
0.9489	High Similarity	NPC260425
0.9441	High Similarity	NPC106138
0.9433	High Similarity	NPC287615
0.9433	High Similarity	NPC216819
0.9433	High Similarity	NPC83743
0.9433	High Similarity	NPC262182
0.9424	High Similarity	NPC47471
0.9424	High Similarity	NPC186406
0.9424	High Similarity	NPC476377
0.942	High Similarity	NPC205195
0.9416	High Similarity	NPC157554
0.9379	High Similarity	NPC478268
0.9371	High Similarity	NPC215095
0.9371	High Similarity	NPC3460
0.9371	High Similarity	NPC192763
0.9371	High Similarity	NPC80732
0.9371	High Similarity	NPC199311
0.9371	High Similarity	NPC300262
0.9371	High Similarity	NPC261122
0.9371	High Similarity	NPC28651
0.9371	High Similarity	NPC201148
0.9371	High Similarity	NPC210611
0.9366	High Similarity	NPC199928
0.9362	High Similarity	NPC232228
0.9353	High Similarity	NPC473799
0.9353	High Similarity	NPC475530
0.9353	High Similarity	NPC202700
0.9306	High Similarity	NPC478242
0.9291	High Similarity	NPC264632
0.9291	High Similarity	NPC298257
0.9291	High Similarity	NPC476378
0.9291	High Similarity	NPC476380
0.9291	High Similarity	NPC205864
0.9291	High Similarity	NPC247032
0.9291	High Similarity	NPC112
0.9291	High Similarity	NPC76406
0.9291	High Similarity	NPC476384
0.9291	High Similarity	NPC476375
0.9291	High Similarity	NPC96795
0.9291	High Similarity	NPC119537
0.9291	High Similarity	NPC476381
0.9291	High Similarity	NPC269141
0.9291	High Similarity	NPC476397
0.9291	High Similarity	NPC175214
0.9281	High Similarity	NPC100389
0.9281	High Similarity	NPC226005
0.9275	High Similarity	NPC199459
0.9275	High Similarity	NPC177035
0.9275	High Similarity	NPC52277
0.927	High Similarity	NPC886
0.927	High Similarity	NPC135127
0.927	High Similarity	NPC287597
0.927	High Similarity	NPC34293
0.927	High Similarity	NPC35731
0.9241	High Similarity	NPC476871
0.9225	High Similarity	NPC64195
0.9225	High Similarity	NPC300894
0.9225	High Similarity	NPC141455
0.9225	High Similarity	NPC292443
0.9225	High Similarity	NPC296954
0.9225	High Similarity	NPC196063
0.9214	High Similarity	NPC106944
0.9209	High Similarity	NPC138738
0.9209	High Similarity	NPC126206
0.9209	High Similarity	NPC470413
0.9209	High Similarity	NPC476376
0.9203	High Similarity	NPC476870
0.9178	High Similarity	NPC143480
0.9178	High Similarity	NPC85192
0.9178	High Similarity	NPC125823
0.9178	High Similarity	NPC7145
0.9172	High Similarity	NPC90896
0.9172	High Similarity	NPC283839
0.9155	High Similarity	NPC278961
0.9155	High Similarity	NPC105005
0.9155	High Similarity	NPC113680
0.9143	High Similarity	NPC171134
0.9143	High Similarity	NPC321638
0.9143	High Similarity	NPC328273
0.9143	High Similarity	NPC321184
0.9137	High Similarity	NPC471664
0.9137	High Similarity	NPC471665
0.9137	High Similarity	NPC186418
0.9137	High Similarity	NPC37468
0.9128	High Similarity	NPC11411
0.9124	High Similarity	NPC473285
0.9116	High Similarity	NPC472612
0.9116	High Similarity	NPC289967
0.9116	High Similarity	NPC472611
0.9103	High Similarity	NPC478237
0.9097	High Similarity	NPC229505
0.9091	High Similarity	NPC297342
0.9085	High Similarity	NPC473873
0.9085	High Similarity	NPC473792
0.9071	High Similarity	NPC304152
0.906	High Similarity	NPC131532
0.9054	High Similarity	NPC150442
0.9051	High Similarity	NPC138777
0.9051	High Similarity	NPC235294
0.9051	High Similarity	NPC246869
0.9051	High Similarity	NPC225384
0.9051	High Similarity	NPC248307
0.9051	High Similarity	NPC46137
0.9051	High Similarity	NPC65942
0.9028	High Similarity	NPC473909
0.9028	High Similarity	NPC143120
0.9028	High Similarity	NPC274960
0.9014	High Similarity	NPC472711
0.9007	High Similarity	NPC478269
0.8993	High Similarity	NPC187194
0.8986	High Similarity	NPC53587
0.8986	High Similarity	NPC215060
0.8986	High Similarity	NPC254275
0.8986	High Similarity	NPC169404
0.8986	High Similarity	NPC476352
0.8986	High Similarity	NPC176186
0.8973	High Similarity	NPC116229
0.8973	High Similarity	NPC93924
0.8951	High Similarity	NPC469559
0.894	High Similarity	NPC226759
0.8919	High Similarity	NPC269914
0.8919	High Similarity	NPC478249
0.8912	High Similarity	NPC111785
0.8905	High Similarity	NPC229784
0.8905	High Similarity	NPC307110
0.8905	High Similarity	NPC477293
0.8905	High Similarity	NPC477294
0.8897	High Similarity	NPC286245
0.8897	High Similarity	NPC272619
0.8889	High Similarity	NPC7191
0.8889	High Similarity	NPC40305
0.8889	High Similarity	NPC149873
0.8889	High Similarity	NPC46092
0.8889	High Similarity	NPC185307
0.8889	High Similarity	NPC477898
0.8889	High Similarity	NPC478267
0.8889	High Similarity	NPC470950
0.8874	High Similarity	NPC471405
0.8874	High Similarity	NPC478248
0.8874	High Similarity	NPC228357
0.8867	High Similarity	NPC191046
0.8867	High Similarity	NPC194095
0.8867	High Similarity	NPC327032
0.8857	High Similarity	NPC476411
0.8857	High Similarity	NPC471883
0.8857	High Similarity	NPC470881
0.8844	High Similarity	NPC476348
0.8844	High Similarity	NPC187398
0.8836	High Similarity	NPC125755
0.8832	High Similarity	NPC232880
0.8831	High Similarity	NPC246024
0.8828	High Similarity	NPC253015
0.8828	High Similarity	NPC129417
0.8828	High Similarity	NPC471065
0.8828	High Similarity	NPC470235
0.8828	High Similarity	NPC84181
0.8828	High Similarity	NPC283995
0.8824	High Similarity	NPC478265
0.8819	High Similarity	NPC476356
0.8819	High Similarity	NPC145319
0.8819	High Similarity	NPC296643

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 NPC476382 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	827
0.2-0.3	1698
0.3-0.4	2805
0.4-0.5	1932
0.5-0.6	1048
0.6-0.7	507
0.7-0.8	55
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9562	High Similarity	NPD7266	Discontinued
0.8658	High Similarity	NPD1653	Approved
0.8323	Intermediate Similarity	NPD7054	Approved
0.8282	Intermediate Similarity	NPD7685	Pre-registration
0.8272	Intermediate Similarity	NPD7074	Phase 3
0.8272	Intermediate Similarity	NPD7472	Approved
0.8261	Intermediate Similarity	NPD7228	Approved
0.8239	Intermediate Similarity	NPD3027	Phase 3
0.8061	Intermediate Similarity	NPD7251	Discontinued
0.8026	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD6797	Phase 2
0.7945	Intermediate Similarity	NPD1613	Approved
0.7945	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6234	Discontinued
0.7927	Intermediate Similarity	NPD3818	Discontinued
0.7925	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6190	Approved
0.7881	Intermediate Similarity	NPD6674	Discontinued
0.787	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD37	Approved
0.7812	Intermediate Similarity	NPD4966	Approved
0.7812	Intermediate Similarity	NPD4965	Approved
0.7812	Intermediate Similarity	NPD4967	Phase 2
0.7799	Intermediate Similarity	NPD8455	Phase 2
0.7764	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7240	Approved
0.7697	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6166	Phase 2
0.7697	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1091	Approved
0.7676	Intermediate Similarity	NPD3705	Approved
0.7671	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1934	Approved
0.7603	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1357	Approved
0.7574	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD8313	Approved
0.7544	Intermediate Similarity	NPD8312	Approved
0.7529	Intermediate Similarity	NPD6559	Discontinued
0.7529	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD228	Approved
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.7469	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1465	Phase 2
0.7456	Intermediate Similarity	NPD5844	Phase 1
0.7447	Intermediate Similarity	NPD5536	Phase 2
0.7434	Intermediate Similarity	NPD7097	Phase 1
0.7423	Intermediate Similarity	NPD3817	Phase 2
0.741	Intermediate Similarity	NPD8127	Discontinued
0.7391	Intermediate Similarity	NPD4380	Phase 2
0.7389	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2978	Approved
0.7362	Intermediate Similarity	NPD2801	Approved
0.7362	Intermediate Similarity	NPD2977	Approved
0.7351	Intermediate Similarity	NPD4060	Phase 1
0.7345	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7075	Discontinued
0.7322	Intermediate Similarity	NPD7680	Approved
0.7321	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1652	Phase 2
0.7303	Intermediate Similarity	NPD230	Phase 1
0.7303	Intermediate Similarity	NPD4340	Discontinued
0.7286	Intermediate Similarity	NPD5283	Phase 1
0.7285	Intermediate Similarity	NPD6233	Phase 2
0.7278	Intermediate Similarity	NPD5058	Phase 3
0.7273	Intermediate Similarity	NPD3882	Suspended
0.7267	Intermediate Similarity	NPD7095	Approved
0.7261	Intermediate Similarity	NPD8166	Discontinued
0.7248	Intermediate Similarity	NPD2861	Phase 2
0.7237	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3620	Phase 2
0.7226	Intermediate Similarity	NPD1358	Approved
0.7212	Intermediate Similarity	NPD5402	Approved
0.7211	Intermediate Similarity	NPD2983	Phase 2
0.7211	Intermediate Similarity	NPD2982	Phase 2
0.72	Intermediate Similarity	NPD4908	Phase 1
0.7195	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5124	Phase 1
0.719	Intermediate Similarity	NPD1933	Approved
0.716	Intermediate Similarity	NPD3686	Approved
0.716	Intermediate Similarity	NPD3687	Approved
0.716	Intermediate Similarity	NPD6232	Discontinued
0.7152	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2981	Phase 2
0.7143	Intermediate Similarity	NPD6653	Approved
0.7135	Intermediate Similarity	NPD7473	Discontinued
0.7134	Intermediate Similarity	NPD6386	Approved
0.7134	Intermediate Similarity	NPD6385	Approved
0.7133	Intermediate Similarity	NPD9494	Approved
0.7133	Intermediate Similarity	NPD3018	Phase 2
0.7125	Intermediate Similarity	NPD1511	Approved
0.7124	Intermediate Similarity	NPD1558	Phase 1
0.7123	Intermediate Similarity	NPD3496	Discontinued
0.7117	Intermediate Similarity	NPD7458	Discontinued
0.7115	Intermediate Similarity	NPD2935	Discontinued
0.7105	Intermediate Similarity	NPD6798	Discontinued
0.7105	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5403	Approved
0.7097	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4536	Approved
0.7097	Intermediate Similarity	NPD4538	Approved
0.7093	Intermediate Similarity	NPD3751	Discontinued
0.7092	Intermediate Similarity	NPD7843	Approved
0.7089	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3060	Approved
0.7086	Intermediate Similarity	NPD7549	Discontinued
0.7079	Intermediate Similarity	NPD6841	Approved
0.7079	Intermediate Similarity	NPD6843	Phase 3
0.7079	Intermediate Similarity	NPD6842	Approved
0.7078	Intermediate Similarity	NPD6355	Discontinued
0.7075	Intermediate Similarity	NPD422	Phase 1
0.707	Intermediate Similarity	NPD5762	Approved
0.707	Intermediate Similarity	NPD5763	Approved
0.7063	Intermediate Similarity	NPD7157	Approved
0.7048	Intermediate Similarity	NPD7819	Suspended
0.7044	Intermediate Similarity	NPD4110	Phase 3
0.7044	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5494	Approved
0.7037	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1512	Approved
0.7029	Intermediate Similarity	NPD3134	Approved
0.7029	Intermediate Similarity	NPD7039	Approved
0.7029	Intermediate Similarity	NPD7038	Approved
0.7024	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4357	Discontinued
0.7012	Intermediate Similarity	NPD3455	Phase 2
0.7	Intermediate Similarity	NPD3021	Approved
0.7	Intermediate Similarity	NPD3022	Approved
0.6988	Remote Similarity	NPD6801	Discontinued
0.6981	Remote Similarity	NPD4236	Phase 3
0.6981	Remote Similarity	NPD4237	Approved
0.6981	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5401	Approved
0.6972	Remote Similarity	NPD5535	Approved
0.697	Remote Similarity	NPD7028	Phase 2
0.6968	Remote Similarity	NPD447	Suspended
0.6962	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1610	Phase 2
0.6959	Remote Similarity	NPD3787	Discontinued
0.6952	Remote Similarity	NPD7435	Discontinued
0.6948	Remote Similarity	NPD4062	Phase 3
0.6947	Remote Similarity	NPD8151	Discontinued
0.6946	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7033	Discontinued
0.6943	Remote Similarity	NPD4108	Discontinued
0.6943	Remote Similarity	NPD5588	Approved
0.6943	Remote Similarity	NPD5960	Phase 3
0.6939	Remote Similarity	NPD5125	Phase 3
0.6939	Remote Similarity	NPD5126	Approved
0.6939	Remote Similarity	NPD4626	Approved
0.6937	Remote Similarity	NPD3750	Approved
0.6937	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3225	Approved
0.6929	Remote Similarity	NPD2684	Approved
0.6928	Remote Similarity	NPD7411	Suspended
0.6918	Remote Similarity	NPD1548	Phase 1
0.6914	Remote Similarity	NPD6799	Approved
0.6905	Remote Similarity	NPD5353	Approved
0.6903	Remote Similarity	NPD4140	Approved
0.6875	Remote Similarity	NPD5177	Phase 3
0.6871	Remote Similarity	NPD3536	Discontinued
0.6871	Remote Similarity	NPD5691	Approved
0.6864	Remote Similarity	NPD7768	Phase 2
0.6855	Remote Similarity	NPD1375	Discontinued
0.6852	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6273	Approved
0.6828	Remote Similarity	NPD6671	Approved
0.6821	Remote Similarity	NPD8651	Approved
0.6815	Remote Similarity	NPD2492	Phase 1
0.6813	Remote Similarity	NPD1549	Phase 2
0.6813	Remote Similarity	NPD2424	Discontinued
0.6809	Remote Similarity	NPD6823	Phase 2
0.6807	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD9545	Approved
0.68	Remote Similarity	NPD1608	Approved
0.6792	Remote Similarity	NPD6032	Approved
0.6792	Remote Similarity	NPD2438	Suspended
0.6791	Remote Similarity	NPD6779	Approved
0.6791	Remote Similarity	NPD6776	Approved
0.6791	Remote Similarity	NPD6782	Approved
0.6791	Remote Similarity	NPD6781	Approved
0.6791	Remote Similarity	NPD6777	Approved
0.6791	Remote Similarity	NPD6778	Approved
0.6791	Remote Similarity	NPD6780	Approved
0.6788	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7783	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