NPASS Compound

Structure

NPC474139 OpenBabel07101718292D 28 32 0 0 1 0 0 0 0 0999 V2000 -1.8366 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7218 0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8558 -2.0649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2577 0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1237 0.9351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1237 -1.0649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -2.2673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2414 -1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2577 -0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9898 0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9898 -0.5649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3917 -1.0649 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8558 0.9351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8558 -1.0649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2872 -2.0594 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 -3.6537 -2.8035 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6537 -1.1855 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 7 2 0 0 0 0 5 14 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 13 2 0 0 0 0 8 19 1 0 0 0 0 9 26 1 0 0 0 0 10 25 1 0 0 0 0 11 27 1 0 0 0 0 11 28 1 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 15 9 1 6 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 10 1 6 0 0 0 16 22 1 0 0 0 0 17 19 2 0 0 0 0 17 23 1 0 0 0 0 18 20 2 0 0 0 0 18 27 1 0 0 0 0 19 24 1 0 0 0 0 20 28 1 0 0 0 0 21 13 1 1 0 0 0 21 25 1 0 0 0 0 22 14 1 1 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.16
Volume:	383.208
LogP:	4.308
LogD:	3.54
LogS:	-5.452
# Rotatable Bonds:	4
TPSA:	55.38
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.799
Synthetic Accessibility Score:	3.879
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.822
MDCK Permeability:	6.727182335453108e-05
Pgp-inhibitor:	0.85
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.15
Plasma Protein Binding (PPB):	92.92130279541016%
Volume Distribution (VD):	0.787
Pgp-substrate:	3.3976619243621826%

ADMET: Metabolism

CYP1A2-inhibitor:	0.104
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.734
CYP2C19-substrate:	0.91
CYP2C9-inhibitor:	0.486
CYP2C9-substrate:	0.7
CYP2D6-inhibitor:	0.826
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.927
CYP3A4-substrate:	0.864

ADMET: Excretion

Clearance (CL):	13.51
Half-life (T1/2):	0.155

ADMET: Toxicity

hERG Blockers:	0.468
Human Hepatotoxicity (H-HT):	0.153
Drug-inuced Liver Injury (DILI):	0.911
AMES Toxicity:	0.371
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.79
Skin Sensitization:	0.939
Carcinogencity:	0.705
Eye Corrosion:	0.004
Eye Irritation:	0.207
Respiratory Toxicity:	0.81

Download Data

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

Natural Product: NPC474139

Natural Product ID:	NPC474139
*Common Name:**	2'-Methoxykobusin
IUPAC Name:	5-[(3S,3aR,6S,6aR)-3-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-4-methyl-1,3-benzodioxole
Synonyms:	2'-Methoxykobusin
Standard InCHIKey:	MPPQCCFNXBGKFC-RZTYQLBFSA-N
Standard InCHI:	InChI=1S/C22H24O6/c1-12-14(5-7-18-20(12)28-11-27-18)22-16-10-25-21(15(16)9-26-22)13-4-6-17(23-2)19(8-13)24-3/h4-8,15-16,21-22H,9-11H2,1-3H3/t15-,16-,21+,22+/m0/s1
SMILES:	COc1cc(ccc1OC)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1ccc2c(c1C)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462821
PubChem CID:	11025425
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans

*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
NPO11997	Leucophyllum ambiguum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608853]
NPO11997	Leucophyllum ambiguum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32239935]
NPO11997	Leucophyllum ambiguum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	14400.0	nM	PMID[505607]

☑ 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 NPC474139 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	509
0.1-0.2	1491
0.2-0.3	3971
0.3-0.4	10600
0.4-0.5	8397
0.5-0.6	6352
0.6-0.7	8694
0.7-0.8	2179
0.8-0.85	362
0.85-0.9	105
0.9-0.95	28
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC227160
0.9688	High Similarity	NPC82111
0.9612	High Similarity	NPC7744
0.9609	High Similarity	NPC233224
0.9609	High Similarity	NPC271208
0.9481	High Similarity	NPC265154
0.9462	High Similarity	NPC33611
0.9462	High Similarity	NPC158526
0.9462	High Similarity	NPC129687
0.9462	High Similarity	NPC100223
0.9462	High Similarity	NPC171928
0.9462	High Similarity	NPC16830
0.9453	High Similarity	NPC165128
0.9453	High Similarity	NPC57119
0.9453	High Similarity	NPC158471
0.9453	High Similarity	NPC226862
0.9407	High Similarity	NPC474295
0.9394	High Similarity	NPC189474
0.9333	High Similarity	NPC312199
0.9318	High Similarity	NPC31530
0.9318	High Similarity	NPC90083
0.9318	High Similarity	NPC47181
0.9318	High Similarity	NPC170779
0.9259	High Similarity	NPC103448
0.9259	High Similarity	NPC216434
0.9248	High Similarity	NPC18576
0.9248	High Similarity	NPC49235
0.9248	High Similarity	NPC148893
0.9248	High Similarity	NPC25333
0.9242	High Similarity	NPC266848
0.9242	High Similarity	NPC136750
0.9225	High Similarity	NPC158737
0.9185	High Similarity	NPC193666
0.9185	High Similarity	NPC123526
0.9185	High Similarity	NPC88640
0.9167	High Similarity	NPC261812
0.9167	High Similarity	NPC72046
0.9167	High Similarity	NPC65183
0.9141	High Similarity	NPC121783
0.9141	High Similarity	NPC34902
0.9141	High Similarity	NPC18449
0.9111	High Similarity	NPC469981
0.9111	High Similarity	NPC101807
0.9091	High Similarity	NPC192255
0.9044	High Similarity	NPC113550
0.9037	High Similarity	NPC32189
0.9023	High Similarity	NPC147616
0.9023	High Similarity	NPC219671
0.9023	High Similarity	NPC104077
0.9023	High Similarity	NPC259742
0.8986	High Similarity	NPC472562
0.8986	High Similarity	NPC80326
0.8978	High Similarity	NPC46591
0.8971	High Similarity	NPC196420
0.8963	High Similarity	NPC174191
0.8963	High Similarity	NPC135777
0.8963	High Similarity	NPC142547
0.8929	High Similarity	NPC205316
0.8921	High Similarity	NPC255566
0.8921	High Similarity	NPC298317
0.8913	High Similarity	NPC300798
0.8913	High Similarity	NPC471908
0.8913	High Similarity	NPC58137
0.8906	High Similarity	NPC216929
0.8906	High Similarity	NPC57268
0.8906	High Similarity	NPC312713
0.8906	High Similarity	NPC126935
0.8906	High Similarity	NPC301641
0.8906	High Similarity	NPC80241
0.8906	High Similarity	NPC172676
0.8906	High Similarity	NPC65933
0.8897	High Similarity	NPC121651
0.8889	High Similarity	NPC185680
0.8889	High Similarity	NPC145722
0.8889	High Similarity	NPC256776
0.8872	High Similarity	NPC134764
0.8872	High Similarity	NPC171550
0.8864	High Similarity	NPC222127
0.8864	High Similarity	NPC82862
0.8857	High Similarity	NPC172171
0.8857	High Similarity	NPC239254
0.8849	High Similarity	NPC311057
0.8849	High Similarity	NPC174522
0.8841	High Similarity	NPC56091
0.8832	High Similarity	NPC185908
0.8797	High Similarity	NPC476748
0.8794	High Similarity	NPC180953
0.8794	High Similarity	NPC475868
0.8788	High Similarity	NPC8050
0.8788	High Similarity	NPC473093
0.8788	High Similarity	NPC98745
0.8788	High Similarity	NPC473092
0.8788	High Similarity	NPC177167
0.8786	High Similarity	NPC76415
0.8786	High Similarity	NPC218510
0.8786	High Similarity	NPC185071
0.8786	High Similarity	NPC12728
0.8786	High Similarity	NPC474808
0.8768	High Similarity	NPC156376
0.8759	High Similarity	NPC11453
0.875	High Similarity	NPC344161
0.8741	High Similarity	NPC475856
0.8741	High Similarity	NPC471505
0.8732	High Similarity	NPC252286
0.8732	High Similarity	NPC154971
0.8723	High Similarity	NPC166884
0.8723	High Similarity	NPC141569
0.8723	High Similarity	NPC477701
0.8723	High Similarity	NPC179521
0.8723	High Similarity	NPC326144
0.8722	High Similarity	NPC54321
0.8722	High Similarity	NPC281864
0.8722	High Similarity	NPC328682
0.8714	High Similarity	NPC246947
0.8714	High Similarity	NPC229172
0.8714	High Similarity	NPC230538
0.8714	High Similarity	NPC36531
0.8714	High Similarity	NPC103637
0.8712	High Similarity	NPC40352
0.8712	High Similarity	NPC213711
0.8712	High Similarity	NPC50683
0.8712	High Similarity	NPC112571
0.8712	High Similarity	NPC206882
0.8712	High Similarity	NPC285725
0.8705	High Similarity	NPC177868
0.8696	High Similarity	NPC283949
0.8696	High Similarity	NPC166184
0.8686	High Similarity	NPC184938
0.8686	High Similarity	NPC101624
0.8686	High Similarity	NPC150534
0.8681	High Similarity	NPC85141
0.8676	High Similarity	NPC1474
0.8676	High Similarity	NPC196937
0.8671	High Similarity	NPC116019
0.8667	High Similarity	NPC27843
0.8667	High Similarity	NPC161557
0.8667	High Similarity	NPC115207
0.8667	High Similarity	NPC228346
0.8667	High Similarity	NPC40432
0.8667	High Similarity	NPC7171
0.8667	High Similarity	NPC158079
0.8662	High Similarity	NPC318286
0.8662	High Similarity	NPC327651
0.8652	High Similarity	NPC324962
0.8652	High Similarity	NPC477898
0.8636	High Similarity	NPC17348
0.8633	High Similarity	NPC9068
0.8633	High Similarity	NPC53722
0.8633	High Similarity	NPC290714
0.8633	High Similarity	NPC201404
0.8623	High Similarity	NPC78047
0.8623	High Similarity	NPC143895
0.8621	High Similarity	NPC473989
0.8603	High Similarity	NPC230219
0.8603	High Similarity	NPC207400
0.8603	High Similarity	NPC97316
0.8603	High Similarity	NPC106739
0.8603	High Similarity	NPC181049
0.8601	High Similarity	NPC321958
0.8601	High Similarity	NPC321696
0.8601	High Similarity	NPC3982
0.8601	High Similarity	NPC33832
0.8593	High Similarity	NPC237169
0.8593	High Similarity	NPC470624
0.8592	High Similarity	NPC474036
0.8592	High Similarity	NPC177644
0.8592	High Similarity	NPC84181
0.8592	High Similarity	NPC121661
0.8592	High Similarity	NPC73467
0.8592	High Similarity	NPC217635
0.8592	High Similarity	NPC471667
0.8592	High Similarity	NPC79429
0.8592	High Similarity	NPC191158
0.8582	High Similarity	NPC470084
0.8582	High Similarity	NPC253878
0.8582	High Similarity	NPC287124
0.8582	High Similarity	NPC302506
0.8571	High Similarity	NPC186845
0.8571	High Similarity	NPC9891
0.8571	High Similarity	NPC278076
0.8571	High Similarity	NPC226547
0.8571	High Similarity	NPC88297
0.8562	High Similarity	NPC303519
0.8552	High Similarity	NPC240521
0.854	High Similarity	NPC169973
0.854	High Similarity	NPC26394
0.854	High Similarity	NPC58585
0.8531	High Similarity	NPC38041
0.8531	High Similarity	NPC42716
0.8531	High Similarity	NPC197352
0.8531	High Similarity	NPC469586
0.8531	High Similarity	NPC474749
0.8531	High Similarity	NPC166506
0.8531	High Similarity	NPC476301
0.8531	High Similarity	NPC189239
0.8531	High Similarity	NPC43508
0.8531	High Similarity	NPC110763
0.8531	High Similarity	NPC178014
0.8531	High Similarity	NPC11422
0.8531	High Similarity	NPC279298

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 NPC474139 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	858
0.2-0.3	1820
0.3-0.4	2810
0.4-0.5	1742
0.5-0.6	1005
0.6-0.7	474
0.7-0.8	55
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8906	High Similarity	NPD3705	Approved
0.8203	Intermediate Similarity	NPD5283	Phase 1
0.8158	Intermediate Similarity	NPD4965	Approved
0.8158	Intermediate Similarity	NPD4967	Phase 2
0.8158	Intermediate Similarity	NPD4966	Approved
0.8052	Intermediate Similarity	NPD6234	Discontinued
0.8	Intermediate Similarity	NPD6674	Discontinued
0.7961	Intermediate Similarity	NPD37	Approved
0.7891	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3027	Phase 3
0.7834	Intermediate Similarity	NPD7199	Phase 2
0.7736	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD1357	Approved
0.7702	Intermediate Similarity	NPD7228	Approved
0.7667	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD2861	Phase 2
0.7589	Intermediate Similarity	NPD3018	Phase 2
0.7569	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1613	Approved
0.7515	Intermediate Similarity	NPD7240	Approved
0.7482	Intermediate Similarity	NPD2981	Phase 2
0.7448	Intermediate Similarity	NPD4060	Phase 1
0.7431	Intermediate Similarity	NPD5110	Phase 2
0.7431	Intermediate Similarity	NPD5111	Phase 2
0.7431	Intermediate Similarity	NPD5109	Approved
0.7429	Intermediate Similarity	NPD2983	Phase 2
0.7429	Intermediate Similarity	NPD2982	Phase 2
0.7413	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1091	Approved
0.7403	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD3657	Discovery
0.7383	Intermediate Similarity	NPD1375	Discontinued
0.7365	Intermediate Similarity	NPD4108	Discontinued
0.7343	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3620	Phase 2
0.7329	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5691	Approved
0.7305	Intermediate Similarity	NPD5327	Phase 3
0.7305	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5536	Phase 2
0.7292	Intermediate Similarity	NPD4908	Phase 1
0.7267	Intermediate Similarity	NPD7266	Discontinued
0.7267	Intermediate Similarity	NPD5762	Approved
0.7267	Intermediate Similarity	NPD5763	Approved
0.7266	Intermediate Similarity	NPD5126	Approved
0.7266	Intermediate Similarity	NPD5125	Phase 3
0.7255	Intermediate Similarity	NPD5058	Phase 3
0.7255	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5494	Approved
0.7205	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2438	Suspended
0.7192	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4236	Phase 3
0.7171	Intermediate Similarity	NPD4237	Approved
0.7169	Intermediate Similarity	NPD3818	Discontinued
0.7163	Intermediate Similarity	NPD1610	Phase 2
0.7162	Intermediate Similarity	NPD5735	Approved
0.7162	Intermediate Similarity	NPD6355	Discontinued
0.7153	Intermediate Similarity	NPD709	Approved
0.7152	Intermediate Similarity	NPD7028	Phase 2
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1653	Approved
0.7134	Intermediate Similarity	NPD4210	Discontinued
0.7125	Intermediate Similarity	NPD2977	Approved
0.7125	Intermediate Similarity	NPD2978	Approved
0.7124	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4110	Phase 3
0.7115	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD228	Approved
0.7105	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2979	Phase 3
0.7089	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3539	Phase 1
0.7081	Intermediate Similarity	NPD2563	Approved
0.7081	Intermediate Similarity	NPD2560	Approved
0.7078	Intermediate Similarity	NPD2677	Approved
0.7076	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4481	Phase 3
0.7042	Intermediate Similarity	NPD1611	Approved
0.7039	Intermediate Similarity	NPD3540	Phase 1
0.7039	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7124	Phase 2
0.7029	Intermediate Similarity	NPD7157	Approved
0.7029	Intermediate Similarity	NPD6387	Discontinued
0.7022	Intermediate Similarity	NPD4420	Approved
0.7021	Intermediate Similarity	NPD4626	Approved
0.7019	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7680	Approved
0.7015	Intermediate Similarity	NPD2684	Approved
0.7014	Intermediate Similarity	NPD2922	Phase 1
0.7014	Intermediate Similarity	NPD8651	Approved
0.7013	Intermediate Similarity	NPD6331	Phase 2
0.7007	Intermediate Similarity	NPD4625	Phase 3
0.7006	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1840	Phase 2
0.6985	Remote Similarity	NPD1139	Approved
0.6985	Remote Similarity	NPD1137	Approved
0.6982	Remote Similarity	NPD7074	Phase 3
0.698	Remote Similarity	NPD2238	Phase 2
0.698	Remote Similarity	NPD4140	Approved
0.6974	Remote Similarity	NPD2161	Phase 2
0.6963	Remote Similarity	NPD3022	Approved
0.6963	Remote Similarity	NPD3021	Approved
0.6962	Remote Similarity	NPD5976	Discontinued
0.6957	Remote Similarity	NPD3382	Approved
0.6957	Remote Similarity	NPD1934	Approved
0.6957	Remote Similarity	NPD3383	Approved
0.6957	Remote Similarity	NPD3384	Approved
0.6954	Remote Similarity	NPD6896	Approved
0.6954	Remote Similarity	NPD6895	Approved
0.695	Remote Similarity	NPD3444	Approved
0.695	Remote Similarity	NPD5585	Approved
0.695	Remote Similarity	NPD1651	Approved
0.695	Remote Similarity	NPD3445	Approved
0.695	Remote Similarity	NPD3443	Approved
0.6948	Remote Similarity	NPD5177	Phase 3
0.6944	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1138	Approved
0.6934	Remote Similarity	NPD7843	Approved
0.6934	Remote Similarity	NPD5535	Approved
0.6928	Remote Similarity	NPD3051	Approved
0.6923	Remote Similarity	NPD5844	Phase 1
0.6923	Remote Similarity	NPD1281	Approved
0.6923	Remote Similarity	NPD7054	Approved
0.6918	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD8455	Phase 2
0.6913	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5588	Approved
0.6903	Remote Similarity	NPD3892	Phase 2
0.6901	Remote Similarity	NPD17	Approved
0.6897	Remote Similarity	NPD6696	Suspended
0.6889	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2157	Approved
0.6887	Remote Similarity	NPD6353	Approved
0.6886	Remote Similarity	NPD2970	Approved
0.6886	Remote Similarity	NPD2969	Approved
0.6883	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7472	Approved
0.6879	Remote Similarity	NPD1548	Phase 1
0.6875	Remote Similarity	NPD4005	Discontinued
0.6871	Remote Similarity	NPD3817	Phase 2
0.6871	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD5006	Approved
0.6868	Remote Similarity	NPD5005	Approved
0.6867	Remote Similarity	NPD8127	Discontinued
0.6857	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6798	Discontinued
0.6846	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4536	Approved
0.6842	Remote Similarity	NPD6111	Discontinued
0.6842	Remote Similarity	NPD4538	Approved
0.6842	Remote Similarity	NPD7097	Phase 1
0.6839	Remote Similarity	NPD3060	Approved
0.6838	Remote Similarity	NPD5451	Approved
0.6836	Remote Similarity	NPD7296	Approved
0.6835	Remote Similarity	NPD4584	Approved
0.6829	Remote Similarity	NPD3882	Suspended
0.6828	Remote Similarity	NPD4749	Approved
0.6826	Remote Similarity	NPD6232	Discontinued
0.6826	Remote Similarity	NPD6071	Discontinued
0.6826	Remote Similarity	NPD3787	Discontinued
0.6821	Remote Similarity	NPD1933	Approved
0.6818	Remote Similarity	NPD6005	Phase 3
0.6818	Remote Similarity	NPD6004	Phase 3
0.6818	Remote Similarity	NPD6002	Phase 3
0.6818	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1358	Approved
0.6815	Remote Similarity	NPD290	Approved
0.681	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7473	Discontinued
0.6803	Remote Similarity	NPD4624	Approved
0.6802	Remote Similarity	NPD7685	Pre-registration
0.6795	Remote Similarity	NPD7466	Approved
0.6792	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4055	Discovery
0.6786	Remote Similarity	NPD6671	Approved
0.6781	Remote Similarity	NPD1283	Approved
0.6779	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD7095	Approved
0.6776	Remote Similarity	NPD2492	Phase 1
0.6776	Remote Similarity	NPD4097	Suspended
0.6774	Remote Similarity	NPD2808	Discontinued
0.6768	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7808	Phase 3
0.6761	Remote Similarity	NPD1182	Approved
0.6759	Remote Similarity	NPD1608	Approved
0.6759	Remote Similarity	NPD2233	Approved
0.6759	Remote Similarity	NPD2232	Approved
0.6759	Remote Similarity	NPD2230	Approved
0.6757	Remote Similarity	NPD1712	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