NPASS Compound

Structure

NPC472961 OpenBabel07101719132D 28 30 0 0 1 0 0 0 0 0999 V2000 -3.0878 1.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -2.7770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 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 26 1 0 0 0 0 2 27 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 14 1 0 0 0 0 5 11 2 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 11 1 0 0 0 0 7 17 2 0 0 0 0 8 21 1 0 0 0 0 9 15 1 0 0 0 0 9 22 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 20 2 0 0 0 0 13 8 1 6 0 0 0 13 19 1 0 0 0 0 14 16 2 0 0 0 0 14 23 1 0 0 0 0 15 18 1 0 0 0 0 15 24 1 1 0 0 0 16 26 1 0 0 0 0 17 20 1 0 0 0 0 17 27 1 0 0 0 0 18 25 2 0 0 0 0 19 10 1 1 0 0 0 19 28 1 0 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.13
Volume:	380.673
LogP:	0.991
LogD:	0.785
LogS:	-4.002
# Rotatable Bonds:	7
TPSA:	125.68
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.519
Synthetic Accessibility Score:	3.679
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.358
MDCK Permeability:	1.3639816643262748e-05
Pgp-inhibitor:	0.241
Pgp-substrate:	0.089
Human Intestinal Absorption (HIA):	0.113
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.811
Plasma Protein Binding (PPB):	75.6301498413086%
Volume Distribution (VD):	0.849
Pgp-substrate:	17.692596435546875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.335
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.714
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.463
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.211
CYP3A4-inhibitor:	0.238
CYP3A4-substrate:	0.669

ADMET: Excretion

Clearance (CL):	5.987
Half-life (T1/2):	0.775

ADMET: Toxicity

hERG Blockers:	0.239
Human Hepatotoxicity (H-HT):	0.25
Drug-inuced Liver Injury (DILI):	0.692
AMES Toxicity:	0.155
Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.034
Skin Sensitization:	0.141
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.018

Download Data

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

Natural Product: NPC472961

Natural Product ID:	NPC472961
*Common Name:**	MRPSCUONCYIKEY-ZUEVXXBESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MRPSCUONCYIKEY-ZUEVXXBESA-N
Standard InCHI:	InChI=1S/C20H22O8/c1-26-16-6-10(3-4-14(16)23)19-13(8-21)12-5-11(18(25)15(24)9-22)7-17(27-2)20(12)28-19/h3-7,13,15,19,21-24H,8-9H2,1-2H3/t13-,15-,19+/m0/s1
SMILES:	OC[C@@H](C(=O)c1cc2c(c(c1)OC)O[C@@H]([C@H]2CO)c1ccc(c(c1)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594193
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[26110443]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17612	Xanthium sibiricum	Species	Asteraceae	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	3

Activity Type	# Activity
NON-MOLECULAR	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[488181]
NPT3119	Organism	Human coxsackievirus B3	Human coxsackievirus B3	IC50	>	35000.0	nM	PMID[488181]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	35000.0	nM	PMID[488181]

☑ 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 NPC472961 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	394
0.1-0.2	1403
0.2-0.3	3252
0.3-0.4	8068
0.4-0.5	10082
0.5-0.6	3997
0.6-0.7	4880
0.7-0.8	7122
0.8-0.85	2694
0.85-0.9	750
0.9-0.95	53
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472962
0.9477	High Similarity	NPC180901
0.9477	High Similarity	NPC300757
0.9346	High Similarity	NPC131121
0.9255	High Similarity	NPC102277
0.9255	High Similarity	NPC279209
0.9182	High Similarity	NPC124038
0.9177	High Similarity	NPC471499
0.9161	High Similarity	NPC287504
0.9161	High Similarity	NPC25127
0.9139	High Similarity	NPC30890
0.913	High Similarity	NPC186392
0.9125	High Similarity	NPC472277
0.9119	High Similarity	NPC472635
0.9114	High Similarity	NPC287328
0.9114	High Similarity	NPC470326
0.9114	High Similarity	NPC282009
0.9103	High Similarity	NPC268008
0.908	High Similarity	NPC121333
0.9068	High Similarity	NPC119589
0.9068	High Similarity	NPC235610
0.9068	High Similarity	NPC43065
0.9062	High Similarity	NPC223006
0.9062	High Similarity	NPC272750
0.9062	High Similarity	NPC134047
0.9062	High Similarity	NPC472281
0.9062	High Similarity	NPC18100
0.9062	High Similarity	NPC472582
0.9062	High Similarity	NPC173729
0.9062	High Similarity	NPC205265
0.9057	High Similarity	NPC469889
0.9051	High Similarity	NPC22192
0.9032	High Similarity	NPC151425
0.9012	High Similarity	NPC247973
0.9012	High Similarity	NPC470456
0.9007	High Similarity	NPC239608
0.9007	High Similarity	NPC46161
0.9006	High Similarity	NPC470457
0.9006	High Similarity	NPC108433
0.9006	High Similarity	NPC62261
0.9006	High Similarity	NPC300053
0.9	High Similarity	NPC81679
0.9	High Similarity	NPC144557
0.8994	High Similarity	NPC472624
0.8994	High Similarity	NPC328102
0.8987	High Similarity	NPC129684
0.8987	High Similarity	NPC472598
0.8987	High Similarity	NPC299520
0.8987	High Similarity	NPC474055
0.8987	High Similarity	NPC52530
0.8987	High Similarity	NPC291508
0.8974	High Similarity	NPC60211
0.8968	High Similarity	NPC62354
0.8957	High Similarity	NPC152477
0.8957	High Similarity	NPC242395
0.8957	High Similarity	NPC165456
0.8957	High Similarity	NPC288813
0.8951	High Similarity	NPC128293
0.8951	High Similarity	NPC470462
0.8951	High Similarity	NPC471213
0.8944	High Similarity	NPC470459
0.8944	High Similarity	NPC41301
0.8944	High Similarity	NPC45943
0.8944	High Similarity	NPC472625
0.8938	High Similarity	NPC266314
0.8938	High Similarity	NPC308992
0.8938	High Similarity	NPC187354
0.8938	High Similarity	NPC472634
0.8938	High Similarity	NPC289771
0.8938	High Similarity	NPC26326
0.8931	High Similarity	NPC195832
0.8931	High Similarity	NPC55738
0.8924	High Similarity	NPC291878
0.8924	High Similarity	NPC278778
0.8924	High Similarity	NPC195796
0.8924	High Similarity	NPC35038
0.8924	High Similarity	NPC250922
0.8924	High Similarity	NPC13858
0.8924	High Similarity	NPC326037
0.8924	High Similarity	NPC320825
0.8917	High Similarity	NPC189130
0.8902	High Similarity	NPC131866
0.8896	High Similarity	NPC158761
0.8896	High Similarity	NPC150131
0.8896	High Similarity	NPC472969
0.8896	High Similarity	NPC260266
0.8889	High Similarity	NPC475888
0.8889	High Similarity	NPC326520
0.8889	High Similarity	NPC9370
0.8889	High Similarity	NPC287495
0.8882	High Similarity	NPC272722
0.8882	High Similarity	NPC476247
0.8882	High Similarity	NPC50954
0.8882	High Similarity	NPC474033
0.8882	High Similarity	NPC211107
0.8882	High Similarity	NPC474034
0.8882	High Similarity	NPC474150
0.8882	High Similarity	NPC474162
0.8875	High Similarity	NPC36217
0.8875	High Similarity	NPC476283
0.8875	High Similarity	NPC472631
0.8875	High Similarity	NPC472630
0.8875	High Similarity	NPC263449
0.8875	High Similarity	NPC470183
0.8868	High Similarity	NPC471515
0.8868	High Similarity	NPC471479
0.8868	High Similarity	NPC27337
0.8868	High Similarity	NPC67876
0.8861	High Similarity	NPC45849
0.8861	High Similarity	NPC200761
0.8861	High Similarity	NPC168247
0.8861	High Similarity	NPC477503
0.8861	High Similarity	NPC57674
0.8861	High Similarity	NPC255807
0.8861	High Similarity	NPC31018
0.8861	High Similarity	NPC152951
0.8861	High Similarity	NPC117992
0.8861	High Similarity	NPC470327
0.8861	High Similarity	NPC230149
0.8861	High Similarity	NPC321779
0.8854	High Similarity	NPC304954
0.8848	High Similarity	NPC186847
0.8848	High Similarity	NPC257667
0.8848	High Similarity	NPC472454
0.8846	High Similarity	NPC472279
0.8839	High Similarity	NPC474903
0.8834	High Similarity	NPC207575
0.8834	High Similarity	NPC173292
0.8834	High Similarity	NPC13481
0.8834	High Similarity	NPC477517
0.8834	High Similarity	NPC263212
0.8834	High Similarity	NPC170245
0.8827	High Similarity	NPC474240
0.8827	High Similarity	NPC472278
0.8827	High Similarity	NPC273959
0.8827	High Similarity	NPC473313
0.8827	High Similarity	NPC329669
0.882	High Similarity	NPC216916
0.882	High Similarity	NPC103201
0.882	High Similarity	NPC473106
0.882	High Similarity	NPC472632
0.882	High Similarity	NPC134783
0.882	High Similarity	NPC142252
0.882	High Similarity	NPC474038
0.882	High Similarity	NPC173137
0.8812	High Similarity	NPC250214
0.8812	High Similarity	NPC95936
0.8812	High Similarity	NPC117418
0.8812	High Similarity	NPC53545
0.881	High Similarity	NPC244903
0.8805	High Similarity	NPC265511
0.8805	High Similarity	NPC470328
0.8805	High Similarity	NPC472455
0.8805	High Similarity	NPC472626
0.8805	High Similarity	NPC474638
0.8805	High Similarity	NPC209614
0.8805	High Similarity	NPC471500
0.8805	High Similarity	NPC478223
0.8797	High Similarity	NPC256346
0.8797	High Similarity	NPC273462
0.8797	High Similarity	NPC18727
0.8797	High Similarity	NPC469550
0.8797	High Similarity	NPC27532
0.8797	High Similarity	NPC33051
0.8797	High Similarity	NPC227337
0.8797	High Similarity	NPC70433
0.8797	High Similarity	NPC49402
0.8797	High Similarity	NPC325028
0.8797	High Similarity	NPC246328
0.8797	High Similarity	NPC213896
0.8797	High Similarity	NPC474000
0.8797	High Similarity	NPC192083
0.8795	High Similarity	NPC316539
0.879	High Similarity	NPC474744
0.879	High Similarity	NPC474772
0.879	High Similarity	NPC472423
0.879	High Similarity	NPC267091
0.8788	High Similarity	NPC72249
0.8788	High Similarity	NPC74559
0.8788	High Similarity	NPC103307
0.8788	High Similarity	NPC212748
0.8788	High Similarity	NPC472276
0.8773	High Similarity	NPC125039
0.8773	High Similarity	NPC7688
0.8773	High Similarity	NPC36
0.8773	High Similarity	NPC234052
0.8773	High Similarity	NPC72787
0.8773	High Similarity	NPC224280
0.8773	High Similarity	NPC36320
0.8773	High Similarity	NPC50960
0.8773	High Similarity	NPC36916
0.8773	High Similarity	NPC58223
0.8773	High Similarity	NPC7154
0.8773	High Similarity	NPC45449
0.8765	High Similarity	NPC312056
0.8765	High Similarity	NPC472964
0.8765	High Similarity	NPC144843
0.8765	High Similarity	NPC84515
0.8765	High Similarity	NPC220912
0.8765	High Similarity	NPC201800

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 NPC472961 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	855
0.2-0.3	1714
0.3-0.4	2558
0.4-0.5	1901
0.5-0.6	1025
0.6-0.7	543
0.7-0.8	175
0.8-0.85	26
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9045	High Similarity	NPD3882	Suspended
0.8797	High Similarity	NPD2393	Clinical (unspecified phase)
0.878	High Similarity	NPD3818	Discontinued
0.8773	High Similarity	NPD6167	Clinical (unspecified phase)
0.8773	High Similarity	NPD6166	Phase 2
0.8773	High Similarity	NPD6168	Clinical (unspecified phase)
0.8734	High Similarity	NPD1934	Approved
0.8642	High Similarity	NPD5494	Approved
0.8562	High Similarity	NPD2801	Approved
0.8405	Intermediate Similarity	NPD7075	Discontinued
0.8395	Intermediate Similarity	NPD3817	Phase 2
0.8375	Intermediate Similarity	NPD4380	Phase 2
0.8354	Intermediate Similarity	NPD1512	Approved
0.8344	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD7074	Phase 3
0.8304	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD6797	Phase 2
0.8291	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7054	Approved
0.8272	Intermediate Similarity	NPD6801	Discontinued
0.8246	Intermediate Similarity	NPD7251	Discontinued
0.8235	Intermediate Similarity	NPD7472	Approved
0.8228	Intermediate Similarity	NPD1511	Approved
0.8221	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD7808	Phase 3
0.8187	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD7473	Discontinued
0.8161	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD3926	Phase 2
0.8144	Intermediate Similarity	NPD1247	Approved
0.8095	Intermediate Similarity	NPD6232	Discontinued
0.8072	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD5844	Phase 1
0.8061	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD4628	Phase 3
0.8035	Intermediate Similarity	NPD6559	Discontinued
0.8024	Intermediate Similarity	NPD919	Approved
0.8011	Intermediate Similarity	NPD8434	Phase 2
0.8	Intermediate Similarity	NPD6799	Approved
0.8	Intermediate Similarity	NPD7819	Suspended
0.7952	Intermediate Similarity	NPD5402	Approved
0.7927	Intermediate Similarity	NPD6599	Discontinued
0.7921	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD1549	Phase 2
0.7892	Intermediate Similarity	NPD1465	Phase 2
0.7875	Intermediate Similarity	NPD6190	Approved
0.7862	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2344	Approved
0.7848	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD2799	Discontinued
0.7829	Intermediate Similarity	NPD7685	Pre-registration
0.7824	Intermediate Similarity	NPD6959	Discontinued
0.7811	Intermediate Similarity	NPD6234	Discontinued
0.7785	Intermediate Similarity	NPD2935	Discontinued
0.7785	Intermediate Similarity	NPD2796	Approved
0.7771	Intermediate Similarity	NPD7411	Suspended
0.7758	Intermediate Similarity	NPD3226	Approved
0.775	Intermediate Similarity	NPD2800	Approved
0.7744	Intermediate Similarity	NPD5403	Approved
0.774	Intermediate Similarity	NPD8313	Approved
0.774	Intermediate Similarity	NPD8312	Approved
0.7735	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2534	Approved
0.773	Intermediate Similarity	NPD2532	Approved
0.773	Intermediate Similarity	NPD2533	Approved
0.7725	Intermediate Similarity	NPD37	Approved
0.7722	Intermediate Similarity	NPD1510	Phase 2
0.7719	Intermediate Similarity	NPD7199	Phase 2
0.7712	Intermediate Similarity	NPD9494	Approved
0.7692	Intermediate Similarity	NPD1240	Approved
0.7692	Intermediate Similarity	NPD943	Approved
0.7692	Intermediate Similarity	NPD4966	Approved
0.7692	Intermediate Similarity	NPD4965	Approved
0.7692	Intermediate Similarity	NPD4967	Phase 2
0.7669	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2309	Approved
0.7643	Intermediate Similarity	NPD447	Suspended
0.7643	Intermediate Similarity	NPD6355	Discontinued
0.7636	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5401	Approved
0.7613	Intermediate Similarity	NPD3027	Phase 3
0.7611	Intermediate Similarity	NPD8150	Discontinued
0.76	Intermediate Similarity	NPD7228	Approved
0.76	Intermediate Similarity	NPD3751	Discontinued
0.7595	Intermediate Similarity	NPD1607	Approved
0.7586	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1613	Approved
0.758	Intermediate Similarity	NPD4060	Phase 1
0.758	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD230	Phase 1
0.753	Intermediate Similarity	NPD920	Approved
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.7516	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8127	Discontinued
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2163	Approved
0.7486	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7768	Phase 2
0.7471	Intermediate Similarity	NPD3787	Discontinued
0.7469	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2313	Discontinued
0.7447	Intermediate Similarity	NPD6782	Approved
0.7447	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6778	Approved
0.7447	Intermediate Similarity	NPD6780	Approved
0.7447	Intermediate Similarity	NPD6776	Approved
0.7447	Intermediate Similarity	NPD6781	Approved
0.7447	Intermediate Similarity	NPD6777	Approved
0.7447	Intermediate Similarity	NPD6779	Approved
0.7442	Intermediate Similarity	NPD3749	Approved
0.741	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1471	Phase 3
0.7391	Intermediate Similarity	NPD7033	Discontinued
0.7386	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD3750	Approved
0.7374	Intermediate Similarity	NPD5953	Discontinued
0.7368	Intermediate Similarity	NPD5761	Phase 2
0.7368	Intermediate Similarity	NPD5760	Phase 2
0.7362	Intermediate Similarity	NPD2424	Discontinued
0.7342	Intermediate Similarity	NPD6798	Discontinued
0.7337	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7458	Discontinued
0.733	Intermediate Similarity	NPD7435	Discontinued
0.7325	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1243	Approved
0.7301	Intermediate Similarity	NPD6002	Phase 3
0.7301	Intermediate Similarity	NPD6005	Phase 3
0.7301	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6004	Phase 3
0.7301	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1653	Approved
0.7273	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4110	Phase 3
0.7273	Intermediate Similarity	NPD1608	Approved
0.7267	Intermediate Similarity	NPD6651	Approved
0.7267	Intermediate Similarity	NPD8455	Phase 2
0.7263	Intermediate Similarity	NPD7286	Phase 2
0.7262	Intermediate Similarity	NPD6273	Approved
0.7261	Intermediate Similarity	NPD2861	Phase 2
0.7261	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6386	Approved
0.7251	Intermediate Similarity	NPD6385	Approved
0.725	Intermediate Similarity	NPD4111	Phase 1
0.725	Intermediate Similarity	NPD4665	Approved
0.724	Intermediate Similarity	NPD7697	Approved
0.724	Intermediate Similarity	NPD7696	Phase 3
0.724	Intermediate Similarity	NPD7698	Approved
0.7239	Intermediate Similarity	NPD1551	Phase 2
0.7233	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2494	Approved
0.7225	Intermediate Similarity	NPD2493	Approved
0.7215	Intermediate Similarity	NPD6832	Phase 2
0.7208	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1933	Approved
0.7204	Intermediate Similarity	NPD2490	Approved
0.7204	Intermediate Similarity	NPD2488	Approved
0.7202	Intermediate Similarity	NPD7870	Phase 2
0.7202	Intermediate Similarity	NPD4582	Approved
0.7202	Intermediate Similarity	NPD7871	Phase 2
0.7202	Intermediate Similarity	NPD4583	Approved
0.7197	Intermediate Similarity	NPD2798	Approved
0.7195	Intermediate Similarity	NPD5762	Approved
0.7195	Intermediate Similarity	NPD7266	Discontinued
0.7195	Intermediate Similarity	NPD5763	Approved
0.7192	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD2403	Approved
0.7188	Intermediate Similarity	NPD3057	Approved
0.7188	Intermediate Similarity	NPD6233	Phase 2
0.7188	Intermediate Similarity	NPD2491	Approved
0.7181	Intermediate Similarity	NPD6534	Approved
0.7181	Intermediate Similarity	NPD6535	Approved
0.7179	Intermediate Similarity	NPD7701	Phase 2
0.7178	Intermediate Similarity	NPD7907	Approved
0.7178	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5711	Approved
0.7175	Intermediate Similarity	NPD7229	Phase 3
0.7175	Intermediate Similarity	NPD5710	Approved
0.7169	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5049	Phase 3
0.7157	Intermediate Similarity	NPD7801	Approved
0.715	Intermediate Similarity	NPD4004	Approved
0.715	Intermediate Similarity	NPD4002	Approved
0.7143	Intermediate Similarity	NPD7240	Approved
0.7135	Intermediate Similarity	NPD5242	Approved
0.7135	Intermediate Similarity	NPD3452	Approved
0.7135	Intermediate Similarity	NPD3450	Approved
0.7134	Intermediate Similarity	NPD1203	Approved
0.7134	Intermediate Similarity	NPD6100	Approved
0.7134	Intermediate Similarity	NPD6099	Approved
0.7126	Intermediate Similarity	NPD2354	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