NPASS Compound

Structure

CID265154 OpenBabel06191716062D 27 31 0 0 1 0 0 0 0 0999 V2000 1.9169 1.2564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0444 -4.5143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5399 -0.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8305 -1.3809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4534 -1.3496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9169 -1.9084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8354 -2.5252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0161 0.7677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7919 -0.9548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3471 -0.7797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9169 0.2015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7309 -1.5307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8305 -0.3260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6094 -0.1458 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3851 -0.0413 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5579 -2.3442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0033 -1.3809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7489 -2.9320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0033 -0.3260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8173 -1.1240 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5930 0.9369 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4715 -2.7509 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8535 -3.9265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0487 -1.6240 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2730 1.4369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1545 -1.4702 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 11 1 0 0 0 0 2 23 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 12 2 0 0 0 0 7 18 1 0 0 0 0 8 25 1 0 0 0 0 9 24 1 0 0 0 0 10 26 1 0 0 0 0 10 27 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 14 8 1 1 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 9 1 1 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 19 2 0 0 0 0 17 26 1 0 0 0 0 18 23 1 0 0 0 0 19 27 1 0 0 0 0 20 12 1 6 0 0 0 20 24 1 0 0 0 0 21 13 1 6 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.14
Volume:	365.912
LogP:	4.002
LogD:	3.445
LogS:	-4.883
# Rotatable Bonds:	3
TPSA:	66.38
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.892
Synthetic Accessibility Score:	3.983
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.747
MDCK Permeability:	4.02654695790261e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.219
Plasma Protein Binding (PPB):	96.2932357788086%
Volume Distribution (VD):	0.621
Pgp-substrate:	4.956503391265869%

ADMET: Metabolism

CYP1A2-inhibitor:	0.181
CYP1A2-substrate:	0.879
CYP2C19-inhibitor:	0.657
CYP2C19-substrate:	0.799
CYP2C9-inhibitor:	0.5
CYP2C9-substrate:	0.636
CYP2D6-inhibitor:	0.916
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.853
CYP3A4-substrate:	0.696

ADMET: Excretion

Clearance (CL):	15.379
Half-life (T1/2):	0.184

ADMET: Toxicity

hERG Blockers:	0.269
Human Hepatotoxicity (H-HT):	0.204
Drug-inuced Liver Injury (DILI):	0.878
AMES Toxicity:	0.334
Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.827
Skin Sensitization:	0.947
Carcinogencity:	0.741
Eye Corrosion:	0.005
Eye Irritation:	0.891
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC265154

Natural Product ID:	NPC265154
*Common Name:**	Kobusin
IUPAC Name:	4-[(3S,3aR,6S,6aR)-6-(4-methyl-1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
Synonyms:	Kobusin
Standard InCHIKey:	OFCHTGCBFRTISG-VUEDXXQZSA-N
Standard InCHI:	InChI=1S/C21H22O6/c1-11-13(4-6-17-19(11)27-10-26-17)21-15-9-24-20(14(15)8-25-21)12-3-5-16(22)18(7-12)23-2/h3-7,14-15,20-22H,8-10H2,1-2H3/t14-,15-,20+,21+/m0/s1
SMILES:	Cc1c(ccc2c1OCO2)[C@@H]1[C@H]2CO[C@H](c3ccc(c(c3)OC)O)[C@H]2CO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462823
PubChem CID:	44559453
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]
NPO10821	Magnolia praecocissima	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10821	Magnolia praecocissima	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10821	Magnolia praecocissima	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	=	7400.0	nM	PMID[512636]

☑ 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 NPC265154 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	423
0.1-0.2	1399
0.2-0.3	3662
0.3-0.4	9560
0.4-0.5	9454
0.5-0.6	5267
0.6-0.7	9088
0.7-0.8	2943
0.8-0.85	643
0.85-0.9	210
0.9-0.95	44
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9704	High Similarity	NPC88640
0.9704	High Similarity	NPC123526
0.9704	High Similarity	NPC193666
0.9481	High Similarity	NPC474139
0.9481	High Similarity	NPC135777
0.9481	High Similarity	NPC142547
0.9424	High Similarity	NPC255566
0.9424	High Similarity	NPC298317
0.9338	High Similarity	NPC18576
0.9286	High Similarity	NPC12728
0.9286	High Similarity	NPC185071
0.9265	High Similarity	NPC47181
0.9259	High Similarity	NPC471505
0.9225	High Similarity	NPC154971
0.9225	High Similarity	NPC252286
0.9209	High Similarity	NPC177868
0.9203	High Similarity	NPC101807
0.9197	High Similarity	NPC184938
0.9197	High Similarity	NPC101624
0.9185	High Similarity	NPC158079
0.9185	High Similarity	NPC82111
0.9185	High Similarity	NPC7171
0.9185	High Similarity	NPC115207
0.9185	High Similarity	NPC161557
0.9185	High Similarity	NPC228346
0.9185	High Similarity	NPC40432
0.9185	High Similarity	NPC27843
0.9185	High Similarity	NPC227160
0.9149	High Similarity	NPC477898
0.9118	High Similarity	NPC181049
0.9118	High Similarity	NPC259742
0.9118	High Similarity	NPC104077
0.9118	High Similarity	NPC219671
0.9118	High Similarity	NPC147616
0.9118	High Similarity	NPC7744
0.9118	High Similarity	NPC207400
0.9118	High Similarity	NPC106739
0.9111	High Similarity	NPC233224
0.9111	High Similarity	NPC271208
0.9085	High Similarity	NPC73467
0.9085	High Similarity	NPC84181
0.9085	High Similarity	NPC121661
0.9078	High Similarity	NPC253878
0.9065	High Similarity	NPC469981
0.9058	High Similarity	NPC174191
0.9051	High Similarity	NPC169973
0.9021	High Similarity	NPC197352
0.9021	High Similarity	NPC22150
0.9021	High Similarity	NPC469586
0.9021	High Similarity	NPC189239
0.9021	High Similarity	NPC38041
0.9021	High Similarity	NPC279298
0.9021	High Similarity	NPC166506
0.9021	High Similarity	NPC110763
0.9021	High Similarity	NPC180953
0.9014	High Similarity	NPC474808
0.9007	High Similarity	NPC471908
0.9007	High Similarity	NPC471414
0.9007	High Similarity	NPC472711
0.8978	High Similarity	NPC100223
0.8978	High Similarity	NPC158526
0.8978	High Similarity	NPC4940
0.8978	High Similarity	NPC171928
0.8978	High Similarity	NPC16830
0.8978	High Similarity	NPC33611
0.8978	High Similarity	NPC129687
0.8973	High Similarity	NPC98624
0.8971	High Similarity	NPC64201
0.8971	High Similarity	NPC187998
0.8971	High Similarity	NPC77040
0.8971	High Similarity	NPC275950
0.8971	High Similarity	NPC257582
0.8971	High Similarity	NPC153739
0.8971	High Similarity	NPC42300
0.8971	High Similarity	NPC145305
0.8971	High Similarity	NPC174495
0.8971	High Similarity	NPC92164
0.8971	High Similarity	NPC241522
0.8971	High Similarity	NPC242807
0.8966	High Similarity	NPC301961
0.8966	High Similarity	NPC166584
0.8963	High Similarity	NPC57119
0.8963	High Similarity	NPC45774
0.8963	High Similarity	NPC11258
0.8963	High Similarity	NPC226862
0.8963	High Similarity	NPC21867
0.8963	High Similarity	NPC184733
0.8963	High Similarity	NPC158471
0.8963	High Similarity	NPC282703
0.8963	High Similarity	NPC165128
0.8963	High Similarity	NPC128208
0.8963	High Similarity	NPC129570
0.8958	High Similarity	NPC112861
0.8951	High Similarity	NPC239254
0.8951	High Similarity	NPC179521
0.8951	High Similarity	NPC172171
0.8944	High Similarity	NPC184641
0.8944	High Similarity	NPC133934
0.8944	High Similarity	NPC184684
0.8944	High Similarity	NPC41782
0.8944	High Similarity	NPC474295
0.8936	High Similarity	NPC46591
0.8936	High Similarity	NPC284464
0.8929	High Similarity	NPC474039
0.8921	High Similarity	NPC126409
0.8921	High Similarity	NPC189474
0.8921	High Similarity	NPC99572
0.8905	High Similarity	NPC277804
0.8905	High Similarity	NPC476345
0.8897	High Similarity	NPC475875
0.8897	High Similarity	NPC114505
0.8897	High Similarity	NPC116019
0.8897	High Similarity	NPC213074
0.8897	High Similarity	NPC15956
0.8897	High Similarity	NPC224674
0.8897	High Similarity	NPC193473
0.8897	High Similarity	NPC275284
0.8897	High Similarity	NPC31325
0.8889	High Similarity	NPC18979
0.8889	High Similarity	NPC477702
0.8889	High Similarity	NPC475868
0.8881	High Similarity	NPC470950
0.8881	High Similarity	NPC185307
0.8873	High Similarity	NPC312199
0.8865	High Similarity	NPC9068
0.8865	High Similarity	NPC6369
0.8865	High Similarity	NPC30951
0.8865	High Similarity	NPC156376
0.8857	High Similarity	NPC177160
0.8857	High Similarity	NPC10737
0.8857	High Similarity	NPC477939
0.8857	High Similarity	NPC54743
0.8857	High Similarity	NPC29799
0.8857	High Similarity	NPC209985
0.8857	High Similarity	NPC263367
0.8857	High Similarity	NPC156502
0.8849	High Similarity	NPC170779
0.8849	High Similarity	NPC49603
0.8849	High Similarity	NPC471942
0.8849	High Similarity	NPC90083
0.8849	High Similarity	NPC31530
0.8849	High Similarity	NPC193026
0.8849	High Similarity	NPC67247
0.8849	High Similarity	NPC187616
0.8832	High Similarity	NPC171550
0.8832	High Similarity	NPC134764
0.8832	High Similarity	NPC181079
0.8832	High Similarity	NPC173308
0.8828	High Similarity	NPC226540
0.8828	High Similarity	NPC212890
0.8828	High Similarity	NPC33832
0.8824	High Similarity	NPC470084
0.8819	High Similarity	NPC283995
0.8819	High Similarity	NPC470235
0.8819	High Similarity	NPC129417
0.8815	High Similarity	NPC274356
0.8811	High Similarity	NPC246947
0.8811	High Similarity	NPC230538
0.8811	High Similarity	NPC36531
0.8811	High Similarity	NPC476356
0.8811	High Similarity	NPC103637
0.8811	High Similarity	NPC48309
0.8811	High Similarity	NPC191231
0.8811	High Similarity	NPC229172
0.8811	High Similarity	NPC302506
0.8803	High Similarity	NPC216434
0.8803	High Similarity	NPC56091
0.8803	High Similarity	NPC103448
0.8794	High Similarity	NPC185908
0.8786	High Similarity	NPC49235
0.8786	High Similarity	NPC24490
0.8786	High Similarity	NPC34103
0.8786	High Similarity	NPC148893
0.8786	High Similarity	NPC165155
0.8786	High Similarity	NPC25333
0.8786	High Similarity	NPC141765
0.8784	High Similarity	NPC475756
0.8777	High Similarity	NPC158331
0.8777	High Similarity	NPC266848
0.8777	High Similarity	NPC471391
0.8777	High Similarity	NPC136750
0.8777	High Similarity	NPC471390
0.8776	High Similarity	NPC286235
0.8776	High Similarity	NPC55158
0.8776	High Similarity	NPC51328
0.8759	High Similarity	NPC307466
0.8759	High Similarity	NPC474749
0.8759	High Similarity	NPC272619
0.8759	High Similarity	NPC11422
0.8759	High Similarity	NPC42716
0.8759	High Similarity	NPC476301
0.8759	High Similarity	NPC43508
0.8759	High Similarity	NPC178014
0.8759	High Similarity	NPC286245
0.875	High Similarity	NPC158737
0.875	High Similarity	NPC81638
0.875	High Similarity	NPC46092
0.875	High Similarity	NPC118533
0.875	High Similarity	NPC324962
0.875	High Similarity	NPC165045

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 NPC265154 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	816
0.2-0.3	1851
0.3-0.4	2796
0.4-0.5	1735
0.5-0.6	1041
0.6-0.7	516
0.7-0.8	58
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8506	High Similarity	NPD6234	Discontinued
0.8444	Intermediate Similarity	NPD3705	Approved
0.8357	Intermediate Similarity	NPD3027	Phase 3
0.8258	Intermediate Similarity	NPD4965	Approved
0.8258	Intermediate Similarity	NPD4966	Approved
0.8258	Intermediate Similarity	NPD4967	Phase 2
0.8137	Intermediate Similarity	NPD7228	Approved
0.8108	Intermediate Similarity	NPD6674	Discontinued
0.8065	Intermediate Similarity	NPD37	Approved
0.8056	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD1613	Approved
0.7937	Intermediate Similarity	NPD7199	Phase 2
0.7902	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD2861	Phase 2
0.7832	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1357	Approved
0.7808	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD4060	Phase 1
0.7808	Intermediate Similarity	NPD3620	Phase 2
0.7778	Intermediate Similarity	NPD5283	Phase 1
0.7778	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7266	Discontinued
0.766	Intermediate Similarity	NPD1091	Approved
0.763	Intermediate Similarity	NPD228	Approved
0.7619	Intermediate Similarity	NPD7240	Approved
0.759	Intermediate Similarity	NPD3818	Discontinued
0.758	Intermediate Similarity	NPD1653	Approved
0.7562	Intermediate Similarity	NPD2978	Approved
0.7562	Intermediate Similarity	NPD2977	Approved
0.7552	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD4908	Phase 1
0.7532	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3021	Approved
0.7481	Intermediate Similarity	NPD3022	Approved
0.7432	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1610	Phase 2
0.7403	Intermediate Similarity	NPD7680	Approved
0.7396	Intermediate Similarity	NPD7074	Phase 3
0.7394	Intermediate Similarity	NPD5126	Approved
0.7394	Intermediate Similarity	NPD5125	Phase 3
0.7391	Intermediate Similarity	NPD1934	Approved
0.7386	Intermediate Similarity	NPD5763	Approved
0.7386	Intermediate Similarity	NPD5762	Approved
0.7372	Intermediate Similarity	NPD5058	Phase 3
0.7347	Intermediate Similarity	NPD3018	Phase 2
0.7337	Intermediate Similarity	NPD7054	Approved
0.7294	Intermediate Similarity	NPD7472	Approved
0.7285	Intermediate Similarity	NPD6355	Discontinued
0.7285	Intermediate Similarity	NPD5735	Approved
0.7278	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1375	Discontinued
0.7256	Intermediate Similarity	NPD3882	Suspended
0.7255	Intermediate Similarity	NPD4108	Discontinued
0.7248	Intermediate Similarity	NPD4625	Phase 3
0.7239	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1558	Phase 1
0.7212	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7685	Pre-registration
0.7197	Intermediate Similarity	NPD2677	Approved
0.7195	Intermediate Similarity	NPD2560	Approved
0.7195	Intermediate Similarity	NPD2563	Approved
0.7192	Intermediate Similarity	NPD2983	Phase 2
0.7192	Intermediate Similarity	NPD2982	Phase 2
0.7179	Intermediate Similarity	NPD4236	Phase 3
0.7179	Intermediate Similarity	NPD4237	Approved
0.717	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD27	Approved
0.716	Intermediate Similarity	NPD2489	Approved
0.716	Intermediate Similarity	NPD7028	Phase 2
0.7152	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD6696	Suspended
0.7134	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2801	Approved
0.7134	Intermediate Similarity	NPD4110	Phase 3
0.7133	Intermediate Similarity	NPD1548	Phase 1
0.7126	Intermediate Similarity	NPD7312	Approved
0.7126	Intermediate Similarity	NPD7313	Approved
0.7126	Intermediate Similarity	NPD7310	Approved
0.7126	Intermediate Similarity	NPD7311	Approved
0.7123	Intermediate Similarity	NPD2981	Phase 2
0.7119	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7251	Discontinued
0.7105	Intermediate Similarity	NPD2238	Phase 2
0.7101	Intermediate Similarity	NPD2970	Approved
0.7101	Intermediate Similarity	NPD2969	Approved
0.7095	Intermediate Similarity	NPD3094	Phase 2
0.7086	Intermediate Similarity	NPD5109	Approved
0.7086	Intermediate Similarity	NPD5111	Phase 2
0.7086	Intermediate Similarity	NPD5110	Phase 2
0.7086	Intermediate Similarity	NPD7309	Approved
0.7081	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4749	Approved
0.707	Intermediate Similarity	NPD3060	Approved
0.707	Intermediate Similarity	NPD5177	Phase 3
0.7069	Intermediate Similarity	NPD7808	Phase 3
0.7069	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6166	Phase 2
0.7059	Intermediate Similarity	NPD3657	Discovery
0.7059	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD709	Approved
0.7042	Intermediate Similarity	NPD6671	Approved
0.7042	Intermediate Similarity	NPD7157	Approved
0.7041	Intermediate Similarity	NPD3051	Approved
0.7041	Intermediate Similarity	NPD6232	Discontinued
0.7035	Intermediate Similarity	NPD5844	Phase 1
0.7034	Intermediate Similarity	NPD4626	Approved
0.7032	Intermediate Similarity	NPD5588	Approved
0.703	Intermediate Similarity	NPD8455	Phase 2
0.703	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4577	Approved
0.7029	Intermediate Similarity	NPD4578	Approved
0.7029	Intermediate Similarity	NPD2684	Approved
0.7027	Intermediate Similarity	NPD8651	Approved
0.7025	Intermediate Similarity	NPD6331	Phase 2
0.7019	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7473	Discontinued
0.7011	Intermediate Similarity	NPD6559	Discontinued
0.7006	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4663	Approved
0.6993	Remote Similarity	NPD4140	Approved
0.6987	Remote Similarity	NPD2161	Phase 2
0.6981	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6798	Discontinued
0.6968	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4536	Approved
0.6968	Remote Similarity	NPD4538	Approved
0.6966	Remote Similarity	NPD5691	Approved
0.6966	Remote Similarity	NPD7906	Approved
0.6966	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5327	Phase 3
0.6957	Remote Similarity	NPD290	Approved
0.695	Remote Similarity	NPD7843	Approved
0.6944	Remote Similarity	NPD5536	Phase 2
0.6944	Remote Similarity	NPD7296	Approved
0.6943	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6004	Phase 3
0.6943	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6002	Phase 3
0.6943	Remote Similarity	NPD6005	Phase 3
0.6941	Remote Similarity	NPD6071	Discontinued
0.6941	Remote Similarity	NPD3787	Discontinued
0.6939	Remote Similarity	NPD3092	Approved
0.6937	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1465	Phase 2
0.6923	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5494	Approved
0.6918	Remote Similarity	NPD3892	Phase 2
0.6918	Remote Similarity	NPD4628	Phase 3
0.6914	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7095	Approved
0.6903	Remote Similarity	NPD6353	Approved
0.6903	Remote Similarity	NPD4097	Suspended
0.6903	Remote Similarity	NPD2157	Approved
0.6903	Remote Similarity	NPD6653	Approved
0.6894	Remote Similarity	NPD7041	Phase 2
0.6894	Remote Similarity	NPD1511	Approved
0.6894	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2232	Approved
0.6892	Remote Similarity	NPD2233	Approved
0.6892	Remote Similarity	NPD2230	Approved
0.689	Remote Similarity	NPD4005	Discontinued
0.6886	Remote Similarity	NPD3817	Phase 2
0.6882	Remote Similarity	NPD8127	Discontinued
0.6879	Remote Similarity	NPD2438	Suspended
0.6875	Remote Similarity	NPD6190	Approved
0.6875	Remote Similarity	NPD5241	Discontinued
0.6863	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7097	Phase 1
0.6852	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4123	Phase 3
0.6836	Remote Similarity	NPD8313	Approved
0.6836	Remote Similarity	NPD8312	Approved
0.6835	Remote Similarity	NPD3540	Phase 1
0.6829	Remote Similarity	NPD4210	Discontinued
0.6824	Remote Similarity	NPD4666	Phase 3
0.6821	Remote Similarity	NPD6584	Phase 3
0.6821	Remote Similarity	NPD4624	Approved
0.6818	Remote Similarity	NPD2674	Phase 3
0.6818	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6233	Phase 2
0.6815	Remote Similarity	NPD5960	Phase 3
0.6815	Remote Similarity	NPD3020	Approved
0.6815	Remote Similarity	NPD7033	Discontinued
0.6813	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1512	Approved
0.681	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5604	Discontinued
0.68	Remote Similarity	NPD1283	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