NPASS Compound

Structure

NPC76047 OpenBabel07101718312D 47 51 0 0 1 0 0 0 0 0999 V2000 -10.3923 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 6.5000 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 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 5.0000 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 -6.9282 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 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 -7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 6.0000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 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 0.8660 0.5000 0.0000 C 0 0 2 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 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 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 0.5000 0.0000 C 0 0 2 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 -6.0622 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 -8.6603 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 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 20 1 0 0 0 0 2 20 1 0 0 0 0 3 43 1 0 0 0 0 4 8 1 0 0 0 0 4 20 2 0 0 0 0 5 10 1 0 0 0 0 5 21 2 0 0 0 0 6 11 2 0 0 0 0 6 21 1 0 0 0 0 7 15 2 0 0 0 0 7 21 1 0 0 0 0 8 23 1 0 0 0 0 9 14 2 0 0 0 0 9 22 1 0 0 0 0 10 24 2 0 0 0 0 11 24 1 0 0 0 0 12 13 2 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 28 1 0 0 0 0 15 31 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 25 2 0 0 0 0 17 29 1 0 0 0 0 18 37 1 0 0 0 0 19 27 2 0 0 0 0 19 44 1 0 0 0 0 22 27 1 0 0 0 0 23 28 2 0 0 0 0 24 38 1 0 0 0 0 25 45 1 0 0 0 0 26 29 2 0 0 0 0 26 32 1 0 0 0 0 27 32 1 0 0 0 0 28 43 1 0 0 0 0 29 44 1 0 0 0 0 30 18 1 1 0 0 0 30 33 1 0 0 0 0 30 46 1 0 0 0 0 31 39 2 0 0 0 0 31 47 1 0 0 0 0 32 40 2 0 0 0 0 33 34 1 0 0 0 0 33 41 1 6 0 0 0 34 35 1 0 0 0 0 34 42 1 1 0 0 0 35 36 1 0 0 0 0 35 47 1 6 0 0 0 36 45 1 1 0 0 0 36 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	644.23
Volume:	648.212
LogP:	4.923
LogD:	3.136
LogS:	-3.758
# Rotatable Bonds:	11
TPSA:	165.12
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.111
Synthetic Accessibility Score:	4.285
Fsp3:	0.278
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:	-5.788
MDCK Permeability:	2.3628801500308327e-05
Pgp-inhibitor:	0.386
Pgp-substrate:	0.878
Human Intestinal Absorption (HIA):	0.321
20% Bioavailability (F20%):	0.144
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	96.9109878540039%
Volume Distribution (VD):	0.58
Pgp-substrate:	7.430647373199463%

ADMET: Metabolism

CYP1A2-inhibitor:	0.231
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.705
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.632
CYP2C9-substrate:	0.866
CYP2D6-inhibitor:	0.906
CYP2D6-substrate:	0.868
CYP3A4-inhibitor:	0.566
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	7.08
Half-life (T1/2):	0.352

ADMET: Toxicity

hERG Blockers:	0.713
Human Hepatotoxicity (H-HT):	0.841
Drug-inuced Liver Injury (DILI):	0.57
AMES Toxicity:	0.21
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.368
Skin Sensitization:	0.907
Carcinogencity:	0.099
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.047

Download Data

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

Natural Product: NPC76047

Natural Product ID:	NPC76047
*Common Name:**	3'-Prenyl-4'-Methoxy-Isoflavone-7-O-Beta-D-(2''-O-P-Coumaroyl)Glucopyranoside
IUPAC Name:	[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[3-[4-methoxy-3-(3-methylbut-2-enyl)phenyl]-4-oxochromen-7-yl]oxyoxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	ZJTGUFCATXASHE-XLTJWZCXSA-N
Standard InCHI:	InChI=1S/C36H36O11/c1-20(2)4-8-23-16-22(9-14-28(23)43-3)27-19-44-29-17-25(12-13-26(29)32(27)40)45-36-35(34(42)33(41)30(18-37)46-36)47-31(39)15-7-21-5-10-24(38)11-6-21/h4-7,9-17,19,30,33-38,41-42H,8,18H2,1-3H3/b15-7+/t30-,33-,34+,35-,36-/m1/s1
SMILES:	CC(=CCc1cc(ccc1OC)c1coc2cc(ccc2c1=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)OC(=O)/C=C/c1ccc(cc1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453212
PubChem CID:	6439258
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0000507] Isoflavonoid O-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
NPO1231	Sopubia delphinifolia	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2348204]
NPO1231	Sopubia delphinifolia	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	100.0	%	PMID[488256]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	18.0	%	PMID[488256]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	27.79	%	PMID[488256]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	33.21	%	PMID[488256]

☑ 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 NPC76047 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	1637
0.2-0.3	3486
0.3-0.4	8410
0.4-0.5	9863
0.5-0.6	4886
0.6-0.7	5628
0.7-0.8	5361
0.8-0.85	1939
0.85-0.9	875
0.9-0.95	201
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC473278
0.9565	High Similarity	NPC260504
0.9565	High Similarity	NPC89809
0.9563	High Similarity	NPC124155
0.9563	High Similarity	NPC257566
0.956	High Similarity	NPC477628
0.956	High Similarity	NPC477629
0.956	High Similarity	NPC195685
0.956	High Similarity	NPC270675
0.956	High Similarity	NPC472994
0.956	High Similarity	NPC210961
0.9509	High Similarity	NPC188815
0.9503	High Similarity	NPC139060
0.95	High Similarity	NPC44947
0.95	High Similarity	NPC472876
0.9451	High Similarity	NPC217822
0.9451	High Similarity	NPC11847
0.9451	High Similarity	NPC101399
0.9451	High Similarity	NPC221288
0.9451	High Similarity	NPC474522
0.9448	High Similarity	NPC5319
0.9441	High Similarity	NPC80068
0.9437	High Similarity	NPC47923
0.9437	High Similarity	NPC303913
0.9437	High Similarity	NPC101636
0.9434	High Similarity	NPC43761
0.9434	High Similarity	NPC73511
0.939	High Similarity	NPC280642
0.939	High Similarity	NPC218161
0.939	High Similarity	NPC164704
0.939	High Similarity	NPC469344
0.939	High Similarity	NPC470712
0.939	High Similarity	NPC96605
0.9383	High Similarity	NPC205824
0.9383	High Similarity	NPC85751
0.9383	High Similarity	NPC129264
0.9383	High Similarity	NPC19240
0.9379	High Similarity	NPC190450
0.9379	High Similarity	NPC131745
0.9379	High Similarity	NPC298171
0.9375	High Similarity	NPC472320
0.9371	High Similarity	NPC23817
0.9371	High Similarity	NPC43638
0.9371	High Similarity	NPC161749
0.9371	High Similarity	NPC197896
0.9371	High Similarity	NPC313163
0.9371	High Similarity	NPC156457
0.9371	High Similarity	NPC258035
0.9349	High Similarity	NPC75574
0.9333	High Similarity	NPC470716
0.9333	High Similarity	NPC470714
0.9333	High Similarity	NPC470715
0.9325	High Similarity	NPC68592
0.9325	High Similarity	NPC298666
0.9325	High Similarity	NPC262222
0.9321	High Similarity	NPC278419
0.9321	High Similarity	NPC183672
0.9321	High Similarity	NPC66087
0.9321	High Similarity	NPC179198
0.9317	High Similarity	NPC97812
0.9313	High Similarity	NPC22062
0.9313	High Similarity	NPC473634
0.9313	High Similarity	NPC138811
0.9308	High Similarity	NPC45165
0.9308	High Similarity	NPC471787
0.9308	High Similarity	NPC127406
0.9286	High Similarity	NPC471030
0.9281	High Similarity	NPC231787
0.9277	High Similarity	NPC472993
0.9277	High Similarity	NPC168789
0.9273	High Similarity	NPC92815
0.9259	High Similarity	NPC259834
0.9259	High Similarity	NPC475382
0.9255	High Similarity	NPC271270
0.9255	High Similarity	NPC473623
0.9255	High Similarity	NPC97285
0.9255	High Similarity	NPC142860
0.9255	High Similarity	NPC246469
0.925	High Similarity	NPC129827
0.925	High Similarity	NPC65003
0.925	High Similarity	NPC473512
0.925	High Similarity	NPC44931
0.9245	High Similarity	NPC470605
0.9245	High Similarity	NPC99233
0.9245	High Similarity	NPC27408
0.9245	High Similarity	NPC95090
0.9245	High Similarity	NPC470604
0.9245	High Similarity	NPC470603
0.9231	High Similarity	NPC477860
0.9231	High Similarity	NPC475161
0.9226	High Similarity	NPC477895
0.9217	High Similarity	NPC137871
0.9217	High Similarity	NPC257011
0.9217	High Similarity	NPC288152
0.9217	High Similarity	NPC47140
0.9217	High Similarity	NPC9002
0.9217	High Similarity	NPC67134
0.9207	High Similarity	NPC64425
0.9202	High Similarity	NPC473644
0.9202	High Similarity	NPC311850
0.9198	High Similarity	NPC216496
0.9198	High Similarity	NPC175513
0.9198	High Similarity	NPC48093
0.9198	High Similarity	NPC85707
0.9198	High Similarity	NPC470125
0.9198	High Similarity	NPC224530
0.9198	High Similarity	NPC129217
0.9198	High Similarity	NPC159579
0.9198	High Similarity	NPC259957
0.9187	High Similarity	NPC206378
0.9187	High Similarity	NPC170475
0.9187	High Similarity	NPC473657
0.9187	High Similarity	NPC295613
0.9182	High Similarity	NPC106625
0.9182	High Similarity	NPC83283
0.9182	High Similarity	NPC29763
0.9182	High Similarity	NPC78021
0.9182	High Similarity	NPC143851
0.9182	High Similarity	NPC268950
0.9182	High Similarity	NPC211158
0.9182	High Similarity	NPC108706
0.9182	High Similarity	NPC87304
0.9182	High Similarity	NPC39360
0.9182	High Similarity	NPC210003
0.9176	High Similarity	NPC199172
0.9176	High Similarity	NPC293227
0.9176	High Similarity	NPC35924
0.9176	High Similarity	NPC473717
0.9176	High Similarity	NPC475662
0.9176	High Similarity	NPC473631
0.9176	High Similarity	NPC162394
0.9176	High Similarity	NPC156785
0.9176	High Similarity	NPC241781
0.9172	High Similarity	NPC179862
0.9162	High Similarity	NPC172033
0.9162	High Similarity	NPC88560
0.9162	High Similarity	NPC25724
0.9162	High Similarity	NPC208668
0.9162	High Similarity	NPC175230
0.9157	High Similarity	NPC175429
0.9157	High Similarity	NPC209550
0.9157	High Similarity	NPC298778
0.9157	High Similarity	NPC199079
0.9157	High Similarity	NPC78734
0.9157	High Similarity	NPC277532
0.9157	High Similarity	NPC210808
0.9157	High Similarity	NPC138990
0.9157	High Similarity	NPC150767
0.9146	High Similarity	NPC294722
0.9146	High Similarity	NPC135358
0.9146	High Similarity	NPC287889
0.9141	High Similarity	NPC27942
0.9141	High Similarity	NPC240306
0.9136	High Similarity	NPC271479
0.9136	High Similarity	NPC187379
0.913	High Similarity	NPC60966
0.913	High Similarity	NPC108831
0.913	High Similarity	NPC470606
0.913	High Similarity	NPC182634
0.9125	High Similarity	NPC26195
0.9125	High Similarity	NPC97052
0.9125	High Similarity	NPC169248
0.9125	High Similarity	NPC72649
0.9125	High Similarity	NPC39351
0.9123	High Similarity	NPC21359
0.9123	High Similarity	NPC249560
0.9123	High Similarity	NPC106700
0.9123	High Similarity	NPC223860
0.9123	High Similarity	NPC25946
0.9123	High Similarity	NPC470720
0.9123	High Similarity	NPC275977
0.9123	High Similarity	NPC470717
0.9123	High Similarity	NPC470713
0.9123	High Similarity	NPC460984
0.9119	High Similarity	NPC88484
0.9119	High Similarity	NPC259767
0.9119	High Similarity	NPC10807
0.9119	High Similarity	NPC150123
0.9119	High Similarity	NPC56232
0.9119	High Similarity	NPC259182
0.9119	High Similarity	NPC121001
0.9119	High Similarity	NPC244583
0.9119	High Similarity	NPC161881
0.9118	High Similarity	NPC469371
0.9112	High Similarity	NPC139571
0.9112	High Similarity	NPC267549
0.9112	High Similarity	NPC217520
0.9112	High Similarity	NPC35167
0.9112	High Similarity	NPC472387
0.9107	High Similarity	NPC214621
0.9107	High Similarity	NPC34267
0.9107	High Similarity	NPC68381
0.9107	High Similarity	NPC223426
0.9107	High Similarity	NPC63105
0.9107	High Similarity	NPC81042
0.9102	High Similarity	NPC256760
0.9091	High Similarity	NPC477613
0.9091	High Similarity	NPC70441
0.9091	High Similarity	NPC12013
0.9091	High Similarity	NPC11432

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 NPC76047 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	922
0.2-0.3	1776
0.3-0.4	2651
0.4-0.5	1966
0.5-0.6	1004
0.6-0.7	284
0.7-0.8	140
0.8-0.85	29
0.85-0.9	13
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9448	High Similarity	NPD7804	Clinical (unspecified phase)
0.9371	High Similarity	NPD4381	Clinical (unspecified phase)
0.9012	High Similarity	NPD7075	Discontinued
0.8994	High Similarity	NPD4380	Phase 2
0.8982	High Similarity	NPD7054	Approved
0.8929	High Similarity	NPD7074	Phase 3
0.8929	High Similarity	NPD7472	Approved
0.8882	High Similarity	NPD7808	Phase 3
0.8827	High Similarity	NPD7096	Clinical (unspecified phase)
0.8824	High Similarity	NPD6559	Discontinued
0.8824	High Similarity	NPD7251	Discontinued
0.882	High Similarity	NPD7411	Suspended
0.8773	High Similarity	NPD8443	Clinical (unspecified phase)
0.8765	High Similarity	NPD6801	Discontinued
0.8765	High Similarity	NPD6797	Phase 2
0.8698	High Similarity	NPD3818	Discontinued
0.869	High Similarity	NPD7852	Clinical (unspecified phase)
0.8663	High Similarity	NPD4338	Clinical (unspecified phase)
0.8613	High Similarity	NPD8313	Approved
0.8613	High Similarity	NPD8312	Approved
0.8598	High Similarity	NPD7819	Suspended
0.8588	High Similarity	NPD7879	Clinical (unspecified phase)
0.858	High Similarity	NPD6168	Clinical (unspecified phase)
0.858	High Similarity	NPD6166	Phase 2
0.858	High Similarity	NPD6167	Clinical (unspecified phase)
0.8562	High Similarity	NPD7410	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD7768	Phase 2
0.8485	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD8455	Phase 2
0.8447	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD5403	Approved
0.8333	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD1934	Approved
0.8302	Intermediate Similarity	NPD1549	Phase 2
0.8294	Intermediate Similarity	NPD6959	Discontinued
0.8272	Intermediate Similarity	NPD6799	Approved
0.8239	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD5401	Approved
0.8218	Intermediate Similarity	NPD5844	Phase 1
0.8214	Intermediate Similarity	NPD5402	Approved
0.8214	Intermediate Similarity	NPD3817	Phase 2
0.8201	Intermediate Similarity	NPD8151	Discontinued
0.8197	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD2796	Approved
0.8137	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD1510	Phase 2
0.8103	Intermediate Similarity	NPD7473	Discontinued
0.8095	Intermediate Similarity	NPD7584	Approved
0.8084	Intermediate Similarity	NPD6599	Discontinued
0.8066	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD2801	Approved
0.8035	Intermediate Similarity	NPD6232	Discontinued
0.8032	Intermediate Similarity	NPD7435	Discontinued
0.8024	Intermediate Similarity	NPD7458	Discontinued
0.8021	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD7783	Phase 2
0.8012	Intermediate Similarity	NPD3749	Approved
0.7975	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3750	Approved
0.7939	Intermediate Similarity	NPD1511	Approved
0.7919	Intermediate Similarity	NPD5494	Approved
0.7904	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7871	Phase 2
0.7895	Intermediate Similarity	NPD7870	Phase 2
0.7876	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD7874	Approved
0.7872	Intermediate Similarity	NPD6778	Approved
0.7872	Intermediate Similarity	NPD6779	Approved
0.7872	Intermediate Similarity	NPD6777	Approved
0.7872	Intermediate Similarity	NPD6781	Approved
0.7872	Intermediate Similarity	NPD6782	Approved
0.7872	Intermediate Similarity	NPD6780	Approved
0.7872	Intermediate Similarity	NPD6776	Approved
0.7866	Intermediate Similarity	NPD4628	Phase 3
0.7865	Intermediate Similarity	NPD7585	Approved
0.7862	Intermediate Similarity	NPD1240	Approved
0.7853	Intermediate Similarity	NPD7228	Approved
0.7849	Intermediate Similarity	NPD3882	Suspended
0.7844	Intermediate Similarity	NPD1512	Approved
0.7842	Intermediate Similarity	NPD7697	Approved
0.7842	Intermediate Similarity	NPD7698	Approved
0.7842	Intermediate Similarity	NPD7696	Phase 3
0.7812	Intermediate Similarity	NPD7583	Approved
0.7798	Intermediate Similarity	NPD920	Approved
0.7778	Intermediate Similarity	NPD7685	Pre-registration
0.7772	Intermediate Similarity	NPD7701	Phase 2
0.7771	Intermediate Similarity	NPD7199	Phase 2
0.7764	Intermediate Similarity	NPD1607	Approved
0.7753	Intermediate Similarity	NPD3751	Discontinued
0.7751	Intermediate Similarity	NPD1653	Approved
0.7736	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2935	Discontinued
0.773	Intermediate Similarity	NPD1551	Phase 2
0.7722	Intermediate Similarity	NPD5953	Discontinued
0.7709	Intermediate Similarity	NPD7286	Phase 2
0.7708	Intermediate Similarity	NPD8319	Approved
0.7708	Intermediate Similarity	NPD8320	Phase 1
0.7705	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1243	Approved
0.7696	Intermediate Similarity	NPD6823	Phase 2
0.7679	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD7699	Phase 2
0.7672	Intermediate Similarity	NPD7700	Phase 2
0.7669	Intermediate Similarity	NPD3748	Approved
0.7665	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD8150	Discontinued
0.7653	Intermediate Similarity	NPD7801	Approved
0.7636	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1465	Phase 2
0.7627	Intermediate Similarity	NPD3787	Discontinued
0.7625	Intermediate Similarity	NPD2313	Discontinued
0.7606	Intermediate Similarity	NPD6534	Approved
0.7606	Intermediate Similarity	NPD6535	Approved
0.7602	Intermediate Similarity	NPD3226	Approved
0.7584	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD2533	Approved
0.7574	Intermediate Similarity	NPD2534	Approved
0.7574	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD2532	Approved
0.7572	Intermediate Similarity	NPD37	Approved
0.7561	Intermediate Similarity	NPD2799	Discontinued
0.7557	Intermediate Similarity	NPD919	Approved
0.7557	Intermediate Similarity	NPD6234	Discontinued
0.7543	Intermediate Similarity	NPD4965	Approved
0.7543	Intermediate Similarity	NPD4966	Approved
0.7543	Intermediate Similarity	NPD4967	Phase 2
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7486	Intermediate Similarity	NPD7240	Approved
0.7485	Intermediate Similarity	NPD5124	Phase 1
0.7485	Intermediate Similarity	NPD2800	Approved
0.7485	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1933	Approved
0.7473	Intermediate Similarity	NPD8434	Phase 2
0.7471	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7266	Discontinued
0.7455	Intermediate Similarity	NPD7033	Discontinued
0.7446	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6651	Approved
0.7421	Intermediate Similarity	NPD4363	Phase 3
0.7421	Intermediate Similarity	NPD4360	Phase 2
0.7414	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7390	Discontinued
0.7407	Intermediate Similarity	NPD6798	Discontinued
0.7394	Intermediate Similarity	NPD7097	Phase 1
0.7391	Intermediate Similarity	NPD4908	Phase 1
0.7368	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6212	Phase 3
0.7368	Intermediate Similarity	NPD6213	Phase 3
0.7365	Intermediate Similarity	NPD2346	Discontinued
0.7337	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1203	Approved
0.7278	Intermediate Similarity	NPD1652	Phase 2
0.7278	Intermediate Similarity	NPD1247	Approved
0.7277	Intermediate Similarity	NPD7930	Approved
0.7267	Intermediate Similarity	NPD2798	Approved
0.7262	Intermediate Similarity	NPD2344	Approved
0.7256	Intermediate Similarity	NPD6233	Phase 2
0.7238	Intermediate Similarity	NPD7229	Phase 3
0.7235	Intermediate Similarity	NPD7003	Approved
0.7212	Intermediate Similarity	NPD1613	Approved
0.7212	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7680	Approved
0.7198	Intermediate Similarity	NPD3926	Phase 2
0.7195	Intermediate Similarity	NPD3268	Approved
0.7193	Intermediate Similarity	NPD6190	Approved
0.7179	Intermediate Similarity	NPD8285	Discontinued
0.7174	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1091	Approved
0.717	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD230	Phase 1
0.7169	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8059	Phase 3
0.7143	Intermediate Similarity	NPD5710	Approved
0.7125	Intermediate Similarity	NPD9717	Approved
0.712	Intermediate Similarity	NPD4287	Approved
0.7119	Intermediate Similarity	NPD5889	Approved
0.7119	Intermediate Similarity	NPD5890	Approved
0.7108	Intermediate Similarity	NPD943	Approved
0.7101	Intermediate Similarity	NPD6100	Approved
0.7101	Intermediate Similarity	NPD5408	Approved
0.7101	Intermediate Similarity	NPD5405	Approved
0.7101	Intermediate Similarity	NPD5404	Approved
0.7101	Intermediate Similarity	NPD6099	Approved
0.7101	Intermediate Similarity	NPD5406	Approved
0.7099	Intermediate Similarity	NPD2797	Approved
0.7095	Intermediate Similarity	NPD4288	Approved
0.7093	Intermediate Similarity	NPD2309	Approved
0.7092	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD8127	Discontinued

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