NPASS Compound

Structure

CID14322 OpenBabel06191715342D 37 40 0 0 1 0 0 0 0 0999 V2000 3.5825 5.8323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6421 5.3445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9332 -0.9469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9332 0.0287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4581 -1.9225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6132 -1.4347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5825 4.8567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6421 4.3689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4274 4.3689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2028 3.8811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8926 0.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2723 2.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6421 2.4177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9973 1.2771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3671 0.7893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4274 3.3933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2028 2.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5825 1.9299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0477 1.4421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6005 0.3858 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9703 -0.1020 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5825 2.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0477 2.4177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4274 1.4421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2028 0.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0883 -0.4591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4581 -0.9469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2723 1.9299 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6421 1.4421 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7375 3.3933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8926 2.9055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6005 -1.3040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4337 -0.9469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8457 2.7192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2155 2.2314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6302 0.4878 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 7 2 0 0 0 0 2 8 2 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 27 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 28 1 0 0 0 0 13 17 2 0 0 0 0 13 29 1 0 0 0 0 14 20 1 0 0 0 0 14 28 1 0 0 0 0 15 21 1 0 0 0 0 15 29 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 18 24 2 0 0 0 0 19 23 1 0 0 0 0 19 25 2 0 0 0 0 20 26 1 6 0 0 0 20 36 1 0 0 0 0 21 27 1 1 0 0 0 21 37 1 0 0 0 0 22 30 2 0 0 0 0 23 31 2 0 0 0 0 24 28 1 0 0 0 0 24 36 1 0 0 0 0 25 29 1 0 0 0 0 25 37 1 0 0 0 0 26 32 1 0 0 0 0 27 33 1 0 0 0 0 28 34 1 1 0 0 0 29 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.24
Volume:	525.144
LogP:	3.39
LogD:	2.157
LogS:	-3.749
# Rotatable Bonds:	8
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.365
Synthetic Accessibility Score:	5.618
Fsp3:	0.517
Lipinski Rule-of-5:	Accepted
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:	-4.578
MDCK Permeability:	1.6473610230605118e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.954
Plasma Protein Binding (PPB):	82.29190063476562%
Volume Distribution (VD):	0.673
Pgp-substrate:	6.391549110412598%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.3
CYP2C19-substrate:	0.17
CYP2C9-inhibitor:	0.936
CYP2C9-substrate:	0.225
CYP2D6-inhibitor:	0.832
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.939
CYP3A4-substrate:	0.837

ADMET: Excretion

Clearance (CL):	2.426
Half-life (T1/2):	0.296

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.379
Drug-inuced Liver Injury (DILI):	0.148
AMES Toxicity:	0.972
Rat Oral Acute Toxicity:	0.695
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.844
Carcinogencity:	0.846
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.855

Download Data

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

Natural Product: NPC14322

Natural Product ID:	NPC14322
*Common Name:**	Illicidione B
IUPAC Name:	(2R,3aR)-7-[[(2R,3aR)-3a-hydroxy-2-(2-hydroxypropan-2-yl)-6-oxo-5-prop-2-enyl-2,3-dihydro-1-benzofuran-7-yl]methyl]-3a-hydroxy-2-(2-hydroxypropan-2-yl)-5-prop-2-enyl-2,3-dihydro-1-benzofuran-6-one
Synonyms:	Illicidione B
Standard InCHIKey:	AVMQANMZZMKFSS-SKZNYKRCSA-N
Standard InCHI:	InChI=1S/C29H36O8/c1-7-9-16-12-28(34)14-20(26(3,4)32)36-24(28)18(22(16)30)11-19-23(31)17(10-8-2)13-29(35)15-21(27(5,6)33)37-25(19)29/h7-8,12-13,20-21,32-35H,1-2,9-11,14-15H2,3-6H3/t20-,21-,28+,29+/m1/s1
SMILES:	C=CCC1=C[C@@]2(C[C@H](C(C)(C)O)OC2=C(CC2=C3[C@](C=C(CC=C)C2=O)(C[C@H](C(C)(C)O)O3)O)C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1784752
PubChem CID:	53262722
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO31423	Illicium oligandrum	Species	Schisandraceae	Eukaryota	pericarps	n.a.	n.a.	PMID[19159273]
NPO31423	Illicium oligandrum	Species	Schisandraceae	Eukaryota	stem bark	n.a.	n.a.	PMID[19496609]
NPO31423	Illicium oligandrum	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[21524101]
NPO31423	Illicium oligandrum	Species	Schisandraceae	Eukaryota	n.a.	root	n.a.	PMID[25966312]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	18.6	%	PMID[511250]

☑ 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 NPC14322 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	186
0.1-0.2	1106
0.2-0.3	4968
0.3-0.4	10484
0.4-0.5	16146
0.5-0.6	7539
0.6-0.7	2114
0.7-0.8	151
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8947	High Similarity	NPC9878
0.8391	Intermediate Similarity	NPC291260
0.7979	Intermediate Similarity	NPC87189
0.7979	Intermediate Similarity	NPC228415
0.7629	Intermediate Similarity	NPC478004
0.7629	Intermediate Similarity	NPC158388
0.7629	Intermediate Similarity	NPC478003
0.7551	Intermediate Similarity	NPC476705
0.7426	Intermediate Similarity	NPC135576
0.7426	Intermediate Similarity	NPC93271
0.7423	Intermediate Similarity	NPC476708
0.74	Intermediate Similarity	NPC469819
0.74	Intermediate Similarity	NPC114162
0.7396	Intermediate Similarity	NPC477015
0.7396	Intermediate Similarity	NPC472009
0.7358	Intermediate Similarity	NPC471333
0.7358	Intermediate Similarity	NPC471332
0.7353	Intermediate Similarity	NPC20066
0.7353	Intermediate Similarity	NPC266842
0.7327	Intermediate Similarity	NPC36954
0.732	Intermediate Similarity	NPC178215
0.732	Intermediate Similarity	NPC477012
0.732	Intermediate Similarity	NPC472007
0.7312	Intermediate Similarity	NPC472948
0.7308	Intermediate Similarity	NPC476134
0.7308	Intermediate Similarity	NPC477870
0.7308	Intermediate Similarity	NPC477871
0.7308	Intermediate Similarity	NPC471401
0.7308	Intermediate Similarity	NPC476246
0.7308	Intermediate Similarity	NPC101067
0.7308	Intermediate Similarity	NPC476213
0.73	Intermediate Similarity	NPC61275
0.73	Intermediate Similarity	NPC476300
0.7292	Intermediate Similarity	NPC477014
0.7292	Intermediate Similarity	NPC477013
0.7282	Intermediate Similarity	NPC187268
0.7282	Intermediate Similarity	NPC300584
0.7273	Intermediate Similarity	NPC473448
0.7273	Intermediate Similarity	NPC166554
0.7273	Intermediate Similarity	NPC239517
0.7273	Intermediate Similarity	NPC265856
0.7264	Intermediate Similarity	NPC472756
0.7245	Intermediate Similarity	NPC472008
0.7245	Intermediate Similarity	NPC20339
0.7245	Intermediate Similarity	NPC473905
0.7245	Intermediate Similarity	NPC40376
0.7245	Intermediate Similarity	NPC320458
0.7245	Intermediate Similarity	NPC476707
0.7245	Intermediate Similarity	NPC476706
0.7245	Intermediate Similarity	NPC280621
0.7245	Intermediate Similarity	NPC21208
0.7245	Intermediate Similarity	NPC48338
0.7245	Intermediate Similarity	NPC233551
0.7238	Intermediate Similarity	NPC70369
0.7238	Intermediate Similarity	NPC476235
0.7238	Intermediate Similarity	NPC476126
0.7216	Intermediate Similarity	NPC279267
0.7216	Intermediate Similarity	NPC473687
0.7216	Intermediate Similarity	NPC69082
0.7216	Intermediate Similarity	NPC204686
0.7216	Intermediate Similarity	NPC134885
0.7216	Intermediate Similarity	NPC103523
0.7216	Intermediate Similarity	NPC134865
0.7216	Intermediate Similarity	NPC210218
0.7216	Intermediate Similarity	NPC134807
0.7216	Intermediate Similarity	NPC219498
0.7216	Intermediate Similarity	NPC308412
0.72	Intermediate Similarity	NPC146852
0.7196	Intermediate Similarity	NPC472751
0.7196	Intermediate Similarity	NPC472749
0.7188	Intermediate Similarity	NPC163093
0.7172	Intermediate Similarity	NPC14901
0.7172	Intermediate Similarity	NPC40066
0.7172	Intermediate Similarity	NPC20621
0.7172	Intermediate Similarity	NPC93794
0.7172	Intermediate Similarity	NPC130359
0.7172	Intermediate Similarity	NPC477016
0.7172	Intermediate Similarity	NPC280612
0.7172	Intermediate Similarity	NPC477017
0.7172	Intermediate Similarity	NPC473504
0.7172	Intermediate Similarity	NPC81778
0.7172	Intermediate Similarity	NPC42598
0.7172	Intermediate Similarity	NPC139418
0.7172	Intermediate Similarity	NPC91067
0.7172	Intermediate Similarity	NPC318963
0.717	Intermediate Similarity	NPC472755
0.7158	Intermediate Similarity	NPC474252
0.7156	Intermediate Similarity	NPC471400
0.7143	Intermediate Similarity	NPC476583
0.7143	Intermediate Similarity	NPC20533
0.7143	Intermediate Similarity	NPC258068
0.7143	Intermediate Similarity	NPC15993
0.7129	Intermediate Similarity	NPC288240
0.7129	Intermediate Similarity	NPC179746
0.7129	Intermediate Similarity	NPC81419
0.7129	Intermediate Similarity	NPC162205
0.7129	Intermediate Similarity	NPC475912
0.7129	Intermediate Similarity	NPC295204
0.7129	Intermediate Similarity	NPC11456
0.7129	Intermediate Similarity	NPC273579
0.7117	Intermediate Similarity	NPC66108
0.7113	Intermediate Similarity	NPC473669
0.7113	Intermediate Similarity	NPC473478
0.7113	Intermediate Similarity	NPC223871
0.7113	Intermediate Similarity	NPC231009
0.7113	Intermediate Similarity	NPC329838
0.7113	Intermediate Similarity	NPC471567
0.7113	Intermediate Similarity	NPC283085
0.7113	Intermediate Similarity	NPC132496
0.7113	Intermediate Similarity	NPC329615
0.7113	Intermediate Similarity	NPC110710
0.7113	Intermediate Similarity	NPC107986
0.7113	Intermediate Similarity	NPC286338
0.7113	Intermediate Similarity	NPC66346
0.7113	Intermediate Similarity	NPC1083
0.7113	Intermediate Similarity	NPC103284
0.7113	Intermediate Similarity	NPC82795
0.7113	Intermediate Similarity	NPC120398
0.7113	Intermediate Similarity	NPC473651
0.7113	Intermediate Similarity	NPC322529
0.7103	Intermediate Similarity	NPC472748
0.71	Intermediate Similarity	NPC179394
0.71	Intermediate Similarity	NPC177668
0.71	Intermediate Similarity	NPC476004
0.71	Intermediate Similarity	NPC473904
0.71	Intermediate Similarity	NPC144133
0.71	Intermediate Similarity	NPC51004
0.71	Intermediate Similarity	NPC474761
0.7087	Intermediate Similarity	NPC476315
0.7087	Intermediate Similarity	NPC279621
0.7083	Intermediate Similarity	NPC253801
0.7083	Intermediate Similarity	NPC144415
0.7083	Intermediate Similarity	NPC477786
0.7083	Intermediate Similarity	NPC477784
0.7083	Intermediate Similarity	NPC477785
0.7075	Intermediate Similarity	NPC472754
0.7075	Intermediate Similarity	NPC86077
0.7075	Intermediate Similarity	NPC324017
0.7075	Intermediate Similarity	NPC320019
0.7075	Intermediate Similarity	NPC149371
0.7075	Intermediate Similarity	NPC223834
0.7071	Intermediate Similarity	NPC100454
0.7071	Intermediate Similarity	NPC133730
0.7071	Intermediate Similarity	NPC89001
0.7071	Intermediate Similarity	NPC39754
0.7071	Intermediate Similarity	NPC234077
0.7071	Intermediate Similarity	NPC261952
0.7071	Intermediate Similarity	NPC169511
0.7071	Intermediate Similarity	NPC81045
0.7071	Intermediate Similarity	NPC61257
0.7071	Intermediate Similarity	NPC171135
0.7071	Intermediate Similarity	NPC151403
0.7071	Intermediate Similarity	NPC274446
0.7071	Intermediate Similarity	NPC191929
0.7071	Intermediate Similarity	NPC242364
0.7071	Intermediate Similarity	NPC320569
0.7071	Intermediate Similarity	NPC172821
0.7071	Intermediate Similarity	NPC476704
0.7071	Intermediate Similarity	NPC287164
0.7065	Intermediate Similarity	NPC474197
0.7059	Intermediate Similarity	NPC474338
0.7041	Intermediate Similarity	NPC240695
0.7041	Intermediate Similarity	NPC171174
0.7041	Intermediate Similarity	NPC293136
0.7041	Intermediate Similarity	NPC219652
0.7041	Intermediate Similarity	NPC112685
0.7041	Intermediate Similarity	NPC473840
0.7041	Intermediate Similarity	NPC232555
0.7041	Intermediate Similarity	NPC475581
0.7041	Intermediate Similarity	NPC114694
0.7041	Intermediate Similarity	NPC241360
0.7041	Intermediate Similarity	NPC231096
0.7041	Intermediate Similarity	NPC62118
0.7041	Intermediate Similarity	NPC142117
0.7041	Intermediate Similarity	NPC25703
0.7041	Intermediate Similarity	NPC282815
0.7041	Intermediate Similarity	NPC132940
0.7041	Intermediate Similarity	NPC107717
0.7033	Intermediate Similarity	NPC264178
0.703	Intermediate Similarity	NPC184463
0.703	Intermediate Similarity	NPC30515
0.703	Intermediate Similarity	NPC12172
0.703	Intermediate Similarity	NPC208886
0.7027	Intermediate Similarity	NPC38159
0.7019	Intermediate Similarity	NPC124246
0.7019	Intermediate Similarity	NPC40812
0.7019	Intermediate Similarity	NPC27105
0.7019	Intermediate Similarity	NPC474194
0.7018	Intermediate Similarity	NPC471145
0.7018	Intermediate Similarity	NPC471146
0.701	Intermediate Similarity	NPC156804
0.7009	Intermediate Similarity	NPC472747
0.7009	Intermediate Similarity	NPC472750
0.7	Intermediate Similarity	NPC477011
0.7	Intermediate Similarity	NPC133450
0.7	Intermediate Similarity	NPC307411
0.699	Remote Similarity	NPC304886
0.699	Remote Similarity	NPC270013
0.699	Remote Similarity	NPC14961
0.6989	Remote Similarity	NPC471061

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 NPC14322 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1605
0.2-0.3	4096
0.3-0.4	2396
0.4-0.5	587
0.5-0.6	287
0.6-0.7	22
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7059	Intermediate Similarity	NPD5282	Discontinued
0.6931	Remote Similarity	NPD46	Approved
0.6931	Remote Similarity	NPD6698	Approved
0.6818	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6110	Phase 1
0.6699	Remote Similarity	NPD7983	Approved
0.6635	Remote Similarity	NPD5778	Approved
0.6635	Remote Similarity	NPD5779	Approved
0.6634	Remote Similarity	NPD4250	Approved
0.6634	Remote Similarity	NPD4251	Approved
0.6602	Remote Similarity	NPD7838	Discovery
0.6579	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7154	Phase 3
0.6535	Remote Similarity	NPD4249	Approved
0.6491	Remote Similarity	NPD6371	Approved
0.6481	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6686	Approved
0.6458	Remote Similarity	NPD4756	Discovery
0.6379	Remote Similarity	NPD6053	Discontinued
0.6303	Remote Similarity	NPD7115	Discovery
0.6264	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6412	Phase 2
0.6216	Remote Similarity	NPD5344	Discontinued
0.6204	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD4225	Approved
0.6172	Remote Similarity	NPD7260	Phase 2
0.6148	Remote Similarity	NPD6054	Approved
0.6117	Remote Similarity	NPD5363	Approved
0.6111	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD8297	Approved
0.61	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.61	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD8515	Approved
0.6098	Remote Similarity	NPD8513	Phase 3
0.6098	Remote Similarity	NPD8517	Approved
0.6098	Remote Similarity	NPD8516	Approved
0.6087	Remote Similarity	NPD7331	Phase 2
0.6087	Remote Similarity	NPD3704	Approved
0.6078	Remote Similarity	NPD5362	Discontinued
0.6055	Remote Similarity	NPD5210	Approved
0.6055	Remote Similarity	NPD4629	Approved
0.6048	Remote Similarity	NPD6370	Approved
0.6038	Remote Similarity	NPD6101	Approved
0.6038	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD5211	Phase 2
0.6016	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD6845	Suspended
0.6	Remote Similarity	NPD7839	Suspended
0.6	Remote Similarity	NPD7524	Approved
0.5982	Remote Similarity	NPD6648	Approved
0.5981	Remote Similarity	NPD5785	Approved
0.5968	Remote Similarity	NPD6015	Approved
0.5968	Remote Similarity	NPD6016	Approved
0.5962	Remote Similarity	NPD1694	Approved
0.5962	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD7492	Approved
0.5941	Remote Similarity	NPD4822	Approved
0.5941	Remote Similarity	NPD4695	Discontinued
0.5941	Remote Similarity	NPD4821	Approved
0.5941	Remote Similarity	NPD4252	Approved
0.5941	Remote Similarity	NPD4820	Approved
0.5941	Remote Similarity	NPD4819	Approved
0.5932	Remote Similarity	NPD4634	Approved
0.5926	Remote Similarity	NPD7637	Suspended
0.5926	Remote Similarity	NPD6411	Approved
0.592	Remote Similarity	NPD5988	Approved
0.5917	Remote Similarity	NPD4632	Approved
0.5913	Remote Similarity	NPD5141	Approved
0.5909	Remote Similarity	NPD5695	Phase 3
0.5906	Remote Similarity	NPD6616	Approved
0.5905	Remote Similarity	NPD4519	Discontinued
0.5905	Remote Similarity	NPD4623	Approved
0.5902	Remote Similarity	NPD7500	Approved
0.59	Remote Similarity	NPD4271	Approved
0.59	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4268	Approved
0.5897	Remote Similarity	NPD6881	Approved
0.5897	Remote Similarity	NPD6899	Approved
0.5893	Remote Similarity	NPD5696	Approved
0.5888	Remote Similarity	NPD1695	Approved
0.5887	Remote Similarity	NPD6059	Approved
0.5882	Remote Similarity	NPD6649	Approved
0.5882	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6650	Approved
0.5872	Remote Similarity	NPD6399	Phase 3
0.5865	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7078	Approved
0.5859	Remote Similarity	NPD8074	Phase 3
0.5847	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD4696	Approved
0.5841	Remote Similarity	NPD5286	Approved
0.5841	Remote Similarity	NPD5285	Approved
0.584	Remote Similarity	NPD7503	Approved
0.5833	Remote Similarity	NPD6882	Approved
0.5825	Remote Similarity	NPD6435	Approved
0.5825	Remote Similarity	NPD4270	Approved
0.5825	Remote Similarity	NPD4269	Approved
0.5814	Remote Similarity	NPD7736	Approved
0.5812	Remote Similarity	NPD5697	Approved
0.5806	Remote Similarity	NPD7341	Phase 2
0.5804	Remote Similarity	NPD6084	Phase 2
0.5804	Remote Similarity	NPD6083	Phase 2
0.5798	Remote Similarity	NPD7290	Approved
0.5798	Remote Similarity	NPD6883	Approved
0.5798	Remote Similarity	NPD7102	Approved
0.5798	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD7507	Approved
0.578	Remote Similarity	NPD6079	Approved
0.5769	Remote Similarity	NPD6695	Phase 3
0.5763	Remote Similarity	NPD7320	Approved
0.5755	Remote Similarity	NPD5279	Phase 3
0.5755	Remote Similarity	NPD5690	Phase 2
0.5755	Remote Similarity	NPD5786	Approved
0.575	Remote Similarity	NPD6869	Approved
0.575	Remote Similarity	NPD8130	Phase 1
0.575	Remote Similarity	NPD6847	Approved
0.575	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.575	Remote Similarity	NPD6617	Approved
0.5741	Remote Similarity	NPD4753	Phase 2
0.5739	Remote Similarity	NPD5226	Approved
0.5739	Remote Similarity	NPD5225	Approved
0.5739	Remote Similarity	NPD5224	Approved
0.5739	Remote Similarity	NPD4633	Approved
0.5728	Remote Similarity	NPD5369	Approved
0.5726	Remote Similarity	NPD7641	Discontinued
0.5726	Remote Similarity	NPD6675	Approved
0.5726	Remote Similarity	NPD5739	Approved
0.5726	Remote Similarity	NPD6008	Approved
0.5726	Remote Similarity	NPD7128	Approved
0.5726	Remote Similarity	NPD6402	Approved
0.5714	Remote Similarity	NPD3133	Approved
0.5714	Remote Similarity	NPD4786	Approved
0.5714	Remote Similarity	NPD3665	Phase 1
0.5714	Remote Similarity	NPD6014	Approved
0.5714	Remote Similarity	NPD6012	Approved
0.5714	Remote Similarity	NPD6373	Approved
0.5714	Remote Similarity	NPD3666	Approved
0.5714	Remote Similarity	NPD6372	Approved
0.5714	Remote Similarity	NPD6013	Approved
0.5704	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD7639	Approved
0.5702	Remote Similarity	NPD7640	Approved
0.569	Remote Similarity	NPD5175	Approved
0.569	Remote Similarity	NPD5174	Approved
0.5684	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD7748	Approved
0.5673	Remote Similarity	NPD3667	Approved
0.5673	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD8080	Discontinued
0.5667	Remote Similarity	NPD6421	Discontinued
0.5664	Remote Similarity	NPD4755	Approved
0.5664	Remote Similarity	NPD7902	Approved
0.5652	Remote Similarity	NPD5223	Approved
0.5649	Remote Similarity	NPD7319	Approved
0.5648	Remote Similarity	NPD6903	Approved
0.5648	Remote Similarity	NPD4518	Approved
0.5645	Remote Similarity	NPD6009	Approved
0.5636	Remote Similarity	NPD5284	Approved
0.5636	Remote Similarity	NPD5281	Approved
0.5635	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD7514	Phase 3
0.5631	Remote Similarity	NPD7332	Phase 2
0.5631	Remote Similarity	NPD5368	Approved
0.563	Remote Similarity	NPD4729	Approved
0.563	Remote Similarity	NPD6011	Approved
0.563	Remote Similarity	NPD4730	Approved
0.5625	Remote Similarity	NPD7604	Phase 2
0.5625	Remote Similarity	NPD7642	Approved
0.5625	Remote Similarity	NPD7829	Approved
0.5625	Remote Similarity	NPD7830	Approved
0.5619	Remote Similarity	NPD5332	Approved
0.5619	Remote Similarity	NPD5331	Approved
0.5615	Remote Similarity	NPD8293	Discontinued
0.5614	Remote Similarity	NPD7638	Approved
0.5607	Remote Similarity	NPD5330	Approved
0.5607	Remote Similarity	NPD7146	Approved
0.5607	Remote Similarity	NPD6684	Approved
0.5607	Remote Similarity	NPD7521	Approved
0.5607	Remote Similarity	NPD7334	Approved
0.5607	Remote Similarity	NPD3618	Phase 1
0.5607	Remote Similarity	NPD6409	Approved
0.5606	Remote Similarity	NPD5956	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