NPASS Compound

Structure

CID100697 OpenBabel06191715442D 26 27 0 0 1 0 0 0 0 0999 V2000 1.1340 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1340 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2679 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1340 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2679 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0000 -1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5981 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 1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 10 1 0 0 0 0 8 14 2 0 0 0 0 9 11 1 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 16 1 0 0 0 0 12 21 1 0 0 0 0 15 4 1 1 0 0 0 15 17 1 0 0 0 0 15 25 1 0 0 0 0 16 21 1 6 0 0 0 17 18 1 0 0 0 0 17 22 1 1 0 0 0 18 19 1 0 0 0 0 18 23 1 1 0 0 0 19 20 1 0 0 0 0 19 24 1 6 0 0 0 20 25 1 0 0 0 0 20 26 1 1 0 0 0 21 5 1 6 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.26
Volume:	393.337
LogP:	4.908
LogD:	3.662
LogS:	-3.943
# Rotatable Bonds:	6
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.628
Synthetic Accessibility Score:	4.537
Fsp3:	0.81
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.712
MDCK Permeability:	1.0937366823782213e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.7
Human Intestinal Absorption (HIA):	0.114
20% Bioavailability (F20%):	0.518
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	89.6941909790039%
Volume Distribution (VD):	1.708
Pgp-substrate:	8.019783020019531%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.177
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.755
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.084
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.091

ADMET: Excretion

Clearance (CL):	6.096
Half-life (T1/2):	0.379

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.401
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.917
Carcinogencity:	0.17
Eye Corrosion:	0.01
Eye Irritation:	0.151
Respiratory Toxicity:	0.628

Download Data

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

Natural Product: NPC100697

Natural Product ID:	NPC100697
*Common Name:**	Rel-Alpha-Bisabolol Beta-D-Fucopyranoside
IUPAC Name:	(2R,3R,4S,5R,6S)-2-methyl-6-[(2S)-6-methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-yl]oxyoxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	QZHVNXNQIQXHJI-XITMGRHOSA-N
Standard InCHI:	InChI=1S/C21H36O5/c1-13(2)7-6-12-21(5,16-10-8-14(3)9-11-16)26-20-19(24)18(23)17(22)15(4)25-20/h7-8,15-20,22-24H,6,9-12H2,1-5H3/t15-,16-,17+,18+,19-,20+,21+/m1/s1
SMILES:	CC(=CCC[C@@]([C@H]1CCC(=CC1)C)(O[C@@H]1O[C@H](C)[C@@H]([C@@H]([C@H]1O)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2023564
PubChem CID:	57384017
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO32613	carthamus glaucus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22309250]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20757	Litsea guatemalensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22338	Centaurea jacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23013	Barleria buxifolia	Species	Acanthaceae	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	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT38	Individual Protein	Signal transducer and activator of transcription 3	Homo sapiens	IC50	=	6300.0	nM	PMID[575432]
NPT2	Others	Unspecified		IC50	=	110000.0	nM	PMID[575432]

☑ 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 NPC100697 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	184
0.1-0.2	1540
0.2-0.3	5969
0.3-0.4	14975
0.4-0.5	9169
0.5-0.6	7870
0.6-0.7	2684
0.7-0.8	279
0.8-0.85	15
0.85-0.9	8
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9481	High Similarity	NPC20072
0.9125	High Similarity	NPC477746
0.9125	High Similarity	NPC477747
0.9012	High Similarity	NPC470836
0.881	High Similarity	NPC202886
0.8795	High Similarity	NPC248312
0.8765	High Similarity	NPC166279
0.8706	High Similarity	NPC302584
0.869	High Similarity	NPC477748
0.8605	High Similarity	NPC474792
0.8605	High Similarity	NPC91654
0.8605	High Similarity	NPC67398
0.8506	High Similarity	NPC178949
0.8506	High Similarity	NPC96736
0.8488	Intermediate Similarity	NPC477749
0.8295	Intermediate Similarity	NPC305160
0.8256	Intermediate Similarity	NPC473058
0.8256	Intermediate Similarity	NPC309310
0.8222	Intermediate Similarity	NPC155319
0.8222	Intermediate Similarity	NPC91197
0.8222	Intermediate Similarity	NPC96597
0.8222	Intermediate Similarity	NPC239547
0.8222	Intermediate Similarity	NPC309503
0.8222	Intermediate Similarity	NPC125551
0.8171	Intermediate Similarity	NPC16090
0.8161	Intermediate Similarity	NPC159876
0.8111	Intermediate Similarity	NPC90583
0.809	Intermediate Similarity	NPC477927
0.809	Intermediate Similarity	NPC72817
0.8022	Intermediate Similarity	NPC473890
0.8022	Intermediate Similarity	NPC243728
0.8	Intermediate Similarity	NPC229655
0.8	Intermediate Similarity	NPC108141
0.7935	Intermediate Similarity	NPC158088
0.7935	Intermediate Similarity	NPC5358
0.7935	Intermediate Similarity	NPC216260
0.7912	Intermediate Similarity	NPC207617
0.7889	Intermediate Similarity	NPC211238
0.7849	Intermediate Similarity	NPC64348
0.7849	Intermediate Similarity	NPC282669
0.7849	Intermediate Similarity	NPC469942
0.7848	Intermediate Similarity	NPC55652
0.7826	Intermediate Similarity	NPC240372
0.7805	Intermediate Similarity	NPC477089
0.7802	Intermediate Similarity	NPC286612
0.7802	Intermediate Similarity	NPC230347
0.7802	Intermediate Similarity	NPC275310
0.7791	Intermediate Similarity	NPC470658
0.7766	Intermediate Similarity	NPC280991
0.7766	Intermediate Similarity	NPC263756
0.7766	Intermediate Similarity	NPC309425
0.7766	Intermediate Similarity	NPC88000
0.7766	Intermediate Similarity	NPC4831
0.7766	Intermediate Similarity	NPC129372
0.7766	Intermediate Similarity	NPC117714
0.7766	Intermediate Similarity	NPC21568
0.7766	Intermediate Similarity	NPC470434
0.7766	Intermediate Similarity	NPC47566
0.7766	Intermediate Similarity	NPC285231
0.7766	Intermediate Similarity	NPC160734
0.7766	Intermediate Similarity	NPC267510
0.7766	Intermediate Similarity	NPC472023
0.7742	Intermediate Similarity	NPC477928
0.7742	Intermediate Similarity	NPC70733
0.7742	Intermediate Similarity	NPC280825
0.7742	Intermediate Similarity	NPC234287
0.7742	Intermediate Similarity	NPC56071
0.7717	Intermediate Similarity	NPC256230
0.7708	Intermediate Similarity	NPC221562
0.7708	Intermediate Similarity	NPC187400
0.7708	Intermediate Similarity	NPC470885
0.7684	Intermediate Similarity	NPC256133
0.7684	Intermediate Similarity	NPC154452
0.7684	Intermediate Similarity	NPC136816
0.7684	Intermediate Similarity	NPC213674
0.7684	Intermediate Similarity	NPC76497
0.7684	Intermediate Similarity	NPC272015
0.7684	Intermediate Similarity	NPC30289
0.7674	Intermediate Similarity	NPC266718
0.7667	Intermediate Similarity	NPC472199
0.7667	Intermediate Similarity	NPC472197
0.766	Intermediate Similarity	NPC324598
0.766	Intermediate Similarity	NPC7341
0.766	Intermediate Similarity	NPC473200
0.764	Intermediate Similarity	NPC249408
0.764	Intermediate Similarity	NPC104129
0.7634	Intermediate Similarity	NPC278506
0.7632	Intermediate Similarity	NPC471200
0.7629	Intermediate Similarity	NPC470767
0.7629	Intermediate Similarity	NPC309448
0.7629	Intermediate Similarity	NPC26798
0.7629	Intermediate Similarity	NPC470763
0.7629	Intermediate Similarity	NPC474569
0.7625	Intermediate Similarity	NPC476709
0.7604	Intermediate Similarity	NPC120123
0.7604	Intermediate Similarity	NPC189852
0.7604	Intermediate Similarity	NPC473129
0.7604	Intermediate Similarity	NPC211879
0.7604	Intermediate Similarity	NPC99627
0.7604	Intermediate Similarity	NPC155010
0.7604	Intermediate Similarity	NPC8039
0.7604	Intermediate Similarity	NPC157659
0.7604	Intermediate Similarity	NPC123796
0.7604	Intermediate Similarity	NPC31907
0.7604	Intermediate Similarity	NPC472252
0.7604	Intermediate Similarity	NPC213190
0.7604	Intermediate Similarity	NPC114874
0.7604	Intermediate Similarity	NPC286969
0.7604	Intermediate Similarity	NPC473124
0.7604	Intermediate Similarity	NPC16520
0.7604	Intermediate Similarity	NPC131479
0.7604	Intermediate Similarity	NPC162354
0.7604	Intermediate Similarity	NPC473123
0.7604	Intermediate Similarity	NPC473020
0.7604	Intermediate Similarity	NPC245280
0.7582	Intermediate Similarity	NPC472196
0.7582	Intermediate Similarity	NPC320089
0.7582	Intermediate Similarity	NPC238090
0.7582	Intermediate Similarity	NPC472195
0.7582	Intermediate Similarity	NPC474835
0.7579	Intermediate Similarity	NPC121072
0.7579	Intermediate Similarity	NPC21064
0.7556	Intermediate Similarity	NPC261990
0.7556	Intermediate Similarity	NPC474249
0.7551	Intermediate Similarity	NPC33053
0.7551	Intermediate Similarity	NPC226642
0.7551	Intermediate Similarity	NPC190395
0.7528	Intermediate Similarity	NPC471756
0.7528	Intermediate Similarity	NPC471755
0.7528	Intermediate Similarity	NPC309656
0.7526	Intermediate Similarity	NPC173583
0.7526	Intermediate Similarity	NPC273879
0.7526	Intermediate Similarity	NPC110656
0.7526	Intermediate Similarity	NPC54521
0.7526	Intermediate Similarity	NPC165033
0.7526	Intermediate Similarity	NPC230948
0.7526	Intermediate Similarity	NPC473734
0.7526	Intermediate Similarity	NPC470768
0.7526	Intermediate Similarity	NPC93352
0.7526	Intermediate Similarity	NPC85593
0.7526	Intermediate Similarity	NPC75608
0.7526	Intermediate Similarity	NPC109792
0.7526	Intermediate Similarity	NPC100955
0.7526	Intermediate Similarity	NPC148603
0.7526	Intermediate Similarity	NPC203354
0.7526	Intermediate Similarity	NPC471435
0.7526	Intermediate Similarity	NPC473127
0.7526	Intermediate Similarity	NPC31430
0.7526	Intermediate Similarity	NPC57065
0.7526	Intermediate Similarity	NPC121566
0.7526	Intermediate Similarity	NPC471434
0.75	Intermediate Similarity	NPC159698
0.75	Intermediate Similarity	NPC223834
0.75	Intermediate Similarity	NPC312553
0.75	Intermediate Similarity	NPC159036
0.75	Intermediate Similarity	NPC13143
0.75	Intermediate Similarity	NPC294813
0.75	Intermediate Similarity	NPC472198
0.75	Intermediate Similarity	NPC288694
0.75	Intermediate Similarity	NPC2003
0.75	Intermediate Similarity	NPC470571
0.75	Intermediate Similarity	NPC25701
0.7475	Intermediate Similarity	NPC473288
0.7474	Intermediate Similarity	NPC473790
0.7471	Intermediate Similarity	NPC136699
0.7471	Intermediate Similarity	NPC220167
0.747	Intermediate Similarity	NPC476703
0.747	Intermediate Similarity	NPC40049
0.7449	Intermediate Similarity	NPC181845
0.7449	Intermediate Similarity	NPC69737
0.7449	Intermediate Similarity	NPC160816
0.7449	Intermediate Similarity	NPC208477
0.7449	Intermediate Similarity	NPC208594
0.7449	Intermediate Similarity	NPC242748
0.7449	Intermediate Similarity	NPC473199
0.7449	Intermediate Similarity	NPC210178
0.7449	Intermediate Similarity	NPC472899
0.7449	Intermediate Similarity	NPC138057
0.7449	Intermediate Similarity	NPC95243
0.7449	Intermediate Similarity	NPC473923
0.7449	Intermediate Similarity	NPC470512
0.7449	Intermediate Similarity	NPC269627
0.7449	Intermediate Similarity	NPC472898
0.7449	Intermediate Similarity	NPC173859
0.7449	Intermediate Similarity	NPC152584
0.7449	Intermediate Similarity	NPC472900
0.7449	Intermediate Similarity	NPC473476
0.7449	Intermediate Similarity	NPC127801
0.7449	Intermediate Similarity	NPC194842
0.7449	Intermediate Similarity	NPC63023
0.7444	Intermediate Similarity	NPC470819
0.7436	Intermediate Similarity	NPC477761
0.7436	Intermediate Similarity	NPC477760
0.7436	Intermediate Similarity	NPC477758
0.7436	Intermediate Similarity	NPC477754
0.7436	Intermediate Similarity	NPC477759
0.7423	Intermediate Similarity	NPC475701
0.7423	Intermediate Similarity	NPC16573
0.7423	Intermediate Similarity	NPC151516
0.7423	Intermediate Similarity	NPC473198

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 NPC100697 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	2029
0.2-0.3	4097
0.3-0.4	2009
0.4-0.5	522
0.5-0.6	278
0.6-0.7	56
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
0.7374	Intermediate Similarity	NPD6412	Phase 2
0.6961	Remote Similarity	NPD6686	Approved
0.6848	Remote Similarity	NPD7524	Approved
0.6837	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD46	Approved
0.6809	Remote Similarity	NPD6698	Approved
0.6795	Remote Similarity	NPD368	Approved
0.6731	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7328	Approved
0.6697	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6636	Remote Similarity	NPD7516	Approved
0.6632	Remote Similarity	NPD3168	Discontinued
0.6593	Remote Similarity	NPD6695	Phase 3
0.6577	Remote Similarity	NPD8294	Approved
0.6577	Remote Similarity	NPD8377	Approved
0.6522	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD8033	Approved
0.6518	Remote Similarity	NPD8380	Approved
0.6518	Remote Similarity	NPD8379	Approved
0.6518	Remote Similarity	NPD8296	Approved
0.6518	Remote Similarity	NPD8335	Approved
0.6518	Remote Similarity	NPD8378	Approved
0.6512	Remote Similarity	NPD1810	Approved
0.6512	Remote Similarity	NPD1811	Approved
0.6477	Remote Similarity	NPD6932	Approved
0.6458	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7838	Discovery
0.6449	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD8328	Phase 3
0.6392	Remote Similarity	NPD7983	Approved
0.6373	Remote Similarity	NPD5344	Discontinued
0.6364	Remote Similarity	NPD6933	Approved
0.6333	Remote Similarity	NPD7645	Phase 2
0.6333	Remote Similarity	NPD6683	Phase 2
0.633	Remote Similarity	NPD8133	Approved
0.6316	Remote Similarity	NPD7750	Discontinued
0.6316	Remote Similarity	NPD6370	Approved
0.6306	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7507	Approved
0.6292	Remote Similarity	NPD5776	Phase 2
0.6292	Remote Similarity	NPD6925	Approved
0.6267	Remote Similarity	NPD2269	Approved
0.6264	Remote Similarity	NPD6930	Phase 2
0.6264	Remote Similarity	NPD7332	Phase 2
0.6264	Remote Similarity	NPD7525	Registered
0.6264	Remote Similarity	NPD6931	Approved
0.6264	Remote Similarity	NPD7514	Phase 3
0.625	Remote Similarity	NPD1145	Discontinued
0.6237	Remote Similarity	NPD6110	Phase 1
0.6222	Remote Similarity	NPD7145	Approved
0.622	Remote Similarity	NPD371	Approved
0.6196	Remote Similarity	NPD6898	Phase 1
0.6186	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6101	Approved
0.6184	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD888	Phase 3
0.6184	Remote Similarity	NPD892	Phase 3
0.6184	Remote Similarity	NPD891	Phase 3
0.6184	Remote Similarity	NPD893	Approved
0.6163	Remote Similarity	NPD2686	Approved
0.6163	Remote Similarity	NPD2687	Approved
0.6163	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD2254	Approved
0.6162	Remote Similarity	NPD5779	Approved
0.6162	Remote Similarity	NPD5778	Approved
0.6154	Remote Similarity	NPD6929	Approved
0.614	Remote Similarity	NPD6059	Approved
0.614	Remote Similarity	NPD6054	Approved
0.6136	Remote Similarity	NPD6924	Approved
0.6136	Remote Similarity	NPD6926	Approved
0.6134	Remote Similarity	NPD7319	Approved
0.6133	Remote Similarity	NPD904	Phase 3
0.6133	Remote Similarity	NPD905	Approved
0.6132	Remote Similarity	NPD5357	Phase 1
0.6106	Remote Similarity	NPD7641	Discontinued
0.6102	Remote Similarity	NPD8074	Phase 3
0.6102	Remote Similarity	NPD8293	Discontinued
0.6067	Remote Similarity	NPD7339	Approved
0.6067	Remote Similarity	NPD8264	Approved
0.6067	Remote Similarity	NPD6942	Approved
0.6061	Remote Similarity	NPD7087	Discontinued
0.6061	Remote Similarity	NPD6411	Approved
0.6061	Remote Similarity	NPD7637	Suspended
0.605	Remote Similarity	NPD7736	Approved
0.6049	Remote Similarity	NPD6123	Approved
0.6047	Remote Similarity	NPD6923	Approved
0.6047	Remote Similarity	NPD6922	Approved
0.6022	Remote Similarity	NPD6902	Approved
0.6018	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8171	Discontinued
0.5984	Remote Similarity	NPD8449	Approved
0.5983	Remote Similarity	NPD6067	Discontinued
0.598	Remote Similarity	NPD7839	Suspended
0.5979	Remote Similarity	NPD4251	Approved
0.5979	Remote Similarity	NPD4250	Approved
0.5977	Remote Similarity	NPD7143	Approved
0.5977	Remote Similarity	NPD7144	Approved
0.5974	Remote Similarity	NPD895	Approved
0.5974	Remote Similarity	NPD894	Approved
0.5974	Remote Similarity	NPD887	Approved
0.5974	Remote Similarity	NPD889	Approved
0.5962	Remote Similarity	NPD6648	Approved
0.5957	Remote Similarity	NPD6435	Approved
0.5949	Remote Similarity	NPD2267	Suspended
0.5948	Remote Similarity	NPD6016	Approved
0.5948	Remote Similarity	NPD6015	Approved
0.5941	Remote Similarity	NPD5282	Discontinued
0.5938	Remote Similarity	NPD6893	Approved
0.5935	Remote Similarity	NPD8450	Suspended
0.5932	Remote Similarity	NPD8342	Approved
0.5932	Remote Similarity	NPD8340	Approved
0.5932	Remote Similarity	NPD8341	Approved
0.5932	Remote Similarity	NPD7492	Approved
0.5932	Remote Similarity	NPD8299	Approved
0.5914	Remote Similarity	NPD4821	Approved
0.5914	Remote Similarity	NPD4820	Approved
0.5914	Remote Similarity	NPD7509	Discontinued
0.5914	Remote Similarity	NPD4819	Approved
0.5914	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD4822	Approved
0.5909	Remote Similarity	NPD7151	Approved
0.5909	Remote Similarity	NPD7152	Approved
0.5909	Remote Similarity	NPD7150	Approved
0.5897	Remote Similarity	NPD5988	Approved
0.5895	Remote Similarity	NPD3669	Approved
0.5895	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8451	Approved
0.5882	Remote Similarity	NPD6616	Approved
0.5877	Remote Similarity	NPD6009	Approved
0.5876	Remote Similarity	NPD4249	Approved
0.587	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD7638	Approved
0.5847	Remote Similarity	NPD7830	Approved
0.5847	Remote Similarity	NPD7829	Approved
0.5842	Remote Similarity	NPD6399	Phase 3
0.5833	Remote Similarity	NPD8448	Approved
0.5833	Remote Similarity	NPD7078	Approved
0.5823	Remote Similarity	NPD342	Phase 1
0.5818	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD8444	Approved
0.5812	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.581	Remote Similarity	NPD7640	Approved
0.581	Remote Similarity	NPD7639	Approved
0.5804	Remote Similarity	NPD6430	Approved
0.5804	Remote Similarity	NPD6053	Discontinued
0.5804	Remote Similarity	NPD6882	Approved
0.5804	Remote Similarity	NPD6429	Approved
0.578	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6083	Phase 2
0.5769	Remote Similarity	NPD6084	Phase 2
0.5766	Remote Similarity	NPD6371	Approved
0.5763	Remote Similarity	NPD8080	Discontinued
0.5763	Remote Similarity	NPD5126	Approved
0.5763	Remote Similarity	NPD5125	Phase 3
0.5752	Remote Similarity	NPD4632	Approved
0.5752	Remote Similarity	NPD3731	Phase 3
0.5745	Remote Similarity	NPD5368	Approved
0.573	Remote Similarity	NPD4243	Approved
0.5729	Remote Similarity	NPD7154	Phase 3
0.5727	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6319	Approved
0.5714	Remote Similarity	NPD7642	Approved
0.5714	Remote Similarity	NPD4225	Approved
0.5701	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD4271	Approved
0.5699	Remote Similarity	NPD4268	Approved
0.5696	Remote Similarity	NPD7346	Approved
0.5691	Remote Similarity	NPD8391	Approved
0.5691	Remote Similarity	NPD8390	Approved
0.5691	Remote Similarity	NPD8392	Approved
0.5688	Remote Similarity	NPD6640	Phase 3
0.5688	Remote Similarity	NPD5739	Approved
0.5688	Remote Similarity	NPD6402	Approved
0.5688	Remote Similarity	NPD6675	Approved
0.5688	Remote Similarity	NPD7128	Approved
0.5684	Remote Similarity	NPD5369	Approved
0.5676	Remote Similarity	NPD8998	Phase 2
0.5676	Remote Similarity	NPD8997	Approved
0.5676	Remote Similarity	NPD8993	Phase 1
0.5676	Remote Similarity	NPD8999	Phase 3
0.5676	Remote Similarity	NPD9000	Phase 3
0.567	Remote Similarity	NPD4786	Approved
0.5667	Remote Similarity	NPD4732	Discontinued
0.5664	Remote Similarity	NPD8297	Approved
0.5656	Remote Similarity	NPD6033	Approved
0.5652	Remote Similarity	NPD4832	Approved
0.5652	Remote Similarity	NPD4831	Approved
0.5652	Remote Similarity	NPD4830	Approved
0.5644	Remote Similarity	NPD7136	Phase 2
0.5631	Remote Similarity	NPD7748	Approved
0.5625	Remote Similarity	NPD3667	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