NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.12
Volume:	275.732
LogP:	1.928
LogD:	1.684
LogS:	-3.278
# Rotatable Bonds:	0
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.661
Synthetic Accessibility Score:	4.186
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.013
MDCK Permeability:	1.516749762231484e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.055
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.446

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.672
Plasma Protein Binding (PPB):	79.70451354980469%
Volume Distribution (VD):	0.892
Pgp-substrate:	23.818334579467773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.371
CYP1A2-substrate:	0.647
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.699
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.435
CYP2D6-inhibitor:	0.06
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.333
CYP3A4-substrate:	0.255

ADMET: Excretion

Clearance (CL):	14.425
Half-life (T1/2):	0.194

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.4
Drug-inuced Liver Injury (DILI):	0.803
AMES Toxicity:	0.115
Rat Oral Acute Toxicity:	0.247
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.515
Carcinogencity:	0.617
Eye Corrosion:	0.008
Eye Irritation:	0.058
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC207346

Natural Product ID:	NPC207346
*Common Name:**	Monodictysin B
IUPAC Name:	(1S,3S,4S,4aS,9aS)-1,4,8-trihydroxy-3,4a-dimethyl-2,3,4,9a-tetrahydro-1H-xanthen-9-one
Synonyms:	monodictysin B
Standard InCHIKey:	NFHLHXVIHBGFKO-XHOOZROUSA-N
Standard InCHI:	InChI=1S/C15H18O5/c1-7-6-9(17)12-13(18)11-8(16)4-3-5-10(11)20-15(12,2)14(7)19/h3-5,7,9,12,14,16-17,19H,6H2,1-2H3/t7-,9-,12+,14-,15-/m0/s1
SMILES:	C[C@H]1C[C@@H]([C@@H]2C(=O)c3c(cccc3O[C@]2(C)[C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL223073
PubChem CID:	16114919
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO5623	Monodictys putredinis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[17291041]
NPO5623	Monodictys putredinis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[18939864]
NPO5623	Monodictys putredinis	Species	n.a.	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
Others	3

Activity Type	# Activity
Individual Protein	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	IC50	>	50000.0	nM	PMID[520743]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	<	50.0	%	PMID[520743]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	Inhibition	=	9.0	%	PMID[520743]
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	Activity	=	12.0	uM	PMID[520743]
NPT2	Others	Unspecified		IC50	=	23300.0	nM	PMID[520743]

☑ 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 NPC207346 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	374
0.1-0.2	1323
0.2-0.3	2956
0.3-0.4	6991
0.4-0.5	11114
0.5-0.6	4511
0.6-0.7	4994
0.7-0.8	7476
0.8-0.85	2539
0.85-0.9	394
0.9-0.95	16
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC46564
0.9655	High Similarity	NPC191634
0.9597	High Similarity	NPC164427
0.953	High Similarity	NPC175192
0.9527	High Similarity	NPC321363
0.9527	High Similarity	NPC253904
0.9161	High Similarity	NPC473961
0.9145	High Similarity	NPC326910
0.906	High Similarity	NPC71055
0.902	High Similarity	NPC68727
0.9013	High Similarity	NPC113608
0.9013	High Similarity	NPC268992
0.9013	High Similarity	NPC470338
0.9013	High Similarity	NPC51824
0.9013	High Similarity	NPC470337
0.8968	High Similarity	NPC470339
0.8968	High Similarity	NPC186113
0.8954	High Similarity	NPC135522
0.8947	High Similarity	NPC470675
0.8947	High Similarity	NPC471677
0.8947	High Similarity	NPC263384
0.8947	High Similarity	NPC244577
0.8947	High Similarity	NPC471676
0.8947	High Similarity	NPC473131
0.8947	High Similarity	NPC472420
0.8947	High Similarity	NPC472422
0.8947	High Similarity	NPC475076
0.8938	High Similarity	NPC241874
0.8933	High Similarity	NPC473133
0.8933	High Similarity	NPC47388
0.8933	High Similarity	NPC470670
0.8933	High Similarity	NPC85773
0.8931	High Similarity	NPC225419
0.891	High Similarity	NPC471976
0.891	High Similarity	NPC472055
0.8903	High Similarity	NPC477833
0.8889	High Similarity	NPC470340
0.8889	High Similarity	NPC474843
0.8889	High Similarity	NPC210597
0.8889	High Similarity	NPC475790
0.8889	High Similarity	NPC216035
0.8889	High Similarity	NPC167903
0.8889	High Similarity	NPC180944
0.8889	High Similarity	NPC275878
0.8889	High Similarity	NPC217149
0.8868	High Similarity	NPC178173
0.8854	High Similarity	NPC3629
0.8854	High Similarity	NPC476929
0.8846	High Similarity	NPC329091
0.8839	High Similarity	NPC10754
0.8839	High Similarity	NPC20530
0.8839	High Similarity	NPC24640
0.8839	High Similarity	NPC215917
0.8836	High Similarity	NPC287068
0.8831	High Similarity	NPC100134
0.8831	High Similarity	NPC469405
0.8831	High Similarity	NPC7989
0.8831	High Similarity	NPC223701
0.8831	High Similarity	NPC209760
0.8831	High Similarity	NPC472583
0.8824	High Similarity	NPC262039
0.8824	High Similarity	NPC262038
0.8824	High Similarity	NPC319910
0.8824	High Similarity	NPC471229
0.8824	High Similarity	NPC254412
0.8824	High Similarity	NPC472636
0.8824	High Similarity	NPC474023
0.8824	High Similarity	NPC278476
0.8824	High Similarity	NPC474021
0.882	High Similarity	NPC251144
0.882	High Similarity	NPC241387
0.8816	High Similarity	NPC307052
0.8816	High Similarity	NPC139966
0.8816	High Similarity	NPC277032
0.8816	High Similarity	NPC472628
0.8816	High Similarity	NPC294502
0.8816	High Similarity	NPC200221
0.8812	High Similarity	NPC6588
0.8812	High Similarity	NPC477154
0.8812	High Similarity	NPC117854
0.8808	High Similarity	NPC91902
0.8808	High Similarity	NPC472627
0.8808	High Similarity	NPC46941
0.8808	High Similarity	NPC308200
0.8805	High Similarity	NPC25361
0.88	High Similarity	NPC311144
0.8797	High Similarity	NPC472402
0.8797	High Similarity	NPC474150
0.8797	High Similarity	NPC215612
0.8797	High Similarity	NPC474162
0.8797	High Similarity	NPC472964
0.8792	High Similarity	NPC130206
0.879	High Similarity	NPC155302
0.879	High Similarity	NPC161947
0.879	High Similarity	NPC36217
0.879	High Similarity	NPC470183
0.879	High Similarity	NPC321399
0.879	High Similarity	NPC470810
0.879	High Similarity	NPC475784
0.879	High Similarity	NPC472902
0.8784	High Similarity	NPC145673
0.8782	High Similarity	NPC245758
0.8782	High Similarity	NPC475267
0.8782	High Similarity	NPC181960
0.8782	High Similarity	NPC472910
0.8782	High Similarity	NPC48208
0.8782	High Similarity	NPC299520
0.8782	High Similarity	NPC96167
0.8782	High Similarity	NPC472911
0.8782	High Similarity	NPC474208
0.8782	High Similarity	NPC162869
0.8782	High Similarity	NPC469584
0.8782	High Similarity	NPC472598
0.8782	High Similarity	NPC472914
0.8782	High Similarity	NPC474055
0.8782	High Similarity	NPC222814
0.8782	High Similarity	NPC27337
0.8782	High Similarity	NPC474836
0.8782	High Similarity	NPC472913
0.8782	High Similarity	NPC129684
0.8782	High Similarity	NPC156057
0.8774	High Similarity	NPC259710
0.8774	High Similarity	NPC217706
0.8774	High Similarity	NPC477958
0.8774	High Similarity	NPC207809
0.8774	High Similarity	NPC304207
0.8774	High Similarity	NPC476169
0.8774	High Similarity	NPC31018
0.8774	High Similarity	NPC37392
0.8774	High Similarity	NPC48579
0.8774	High Similarity	NPC472909
0.8774	High Similarity	NPC255807
0.8774	High Similarity	NPC471116
0.8774	High Similarity	NPC67396
0.8774	High Similarity	NPC321779
0.8766	High Similarity	NPC281272
0.8766	High Similarity	NPC56232
0.8766	High Similarity	NPC138288
0.8766	High Similarity	NPC35567
0.8766	High Similarity	NPC473996
0.8766	High Similarity	NPC150123
0.8766	High Similarity	NPC10807
0.8766	High Similarity	NPC243171
0.8766	High Similarity	NPC75069
0.8766	High Similarity	NPC171651
0.8766	High Similarity	NPC161881
0.8766	High Similarity	NPC244583
0.8765	High Similarity	NPC472620
0.8765	High Similarity	NPC118128
0.8758	High Similarity	NPC29777
0.8758	High Similarity	NPC202595
0.8758	High Similarity	NPC267117
0.8758	High Similarity	NPC105136
0.8758	High Similarity	NPC471115
0.8758	High Similarity	NPC225854
0.875	High Similarity	NPC145467
0.875	High Similarity	NPC43319
0.875	High Similarity	NPC5537
0.875	High Similarity	NPC469394
0.875	High Similarity	NPC120593
0.875	High Similarity	NPC10097
0.875	High Similarity	NPC39195
0.875	High Similarity	NPC170245
0.875	High Similarity	NPC218569
0.8742	High Similarity	NPC475985
0.8742	High Similarity	NPC474302
0.8742	High Similarity	NPC124038
0.8742	High Similarity	NPC197168
0.8742	High Similarity	NPC299011
0.8742	High Similarity	NPC476931
0.8742	High Similarity	NPC7483
0.8742	High Similarity	NPC469758
0.8742	High Similarity	NPC186686
0.8742	High Similarity	NPC472629
0.8742	High Similarity	NPC209278
0.8734	High Similarity	NPC87431
0.8734	High Similarity	NPC61010
0.8734	High Similarity	NPC472632
0.8734	High Similarity	NPC474186
0.8734	High Similarity	NPC474038
0.8734	High Similarity	NPC474187
0.8734	High Similarity	NPC266314
0.8734	High Similarity	NPC472634
0.8733	High Similarity	NPC18886
0.8733	High Similarity	NPC113770
0.8733	High Similarity	NPC95751
0.8726	High Similarity	NPC474290
0.8726	High Similarity	NPC152904
0.8726	High Similarity	NPC95936
0.8726	High Similarity	NPC476242
0.8726	High Similarity	NPC22192
0.8726	High Similarity	NPC250214
0.8726	High Similarity	NPC210459
0.8726	High Similarity	NPC473990
0.8726	High Similarity	NPC85121
0.8718	High Similarity	NPC195796
0.8718	High Similarity	NPC255106
0.8718	High Similarity	NPC235165
0.8718	High Similarity	NPC78492
0.8718	High Similarity	NPC278778

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 NPC207346 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	823
0.2-0.3	1623
0.3-0.4	2576
0.4-0.5	2030
0.5-0.6	1082
0.6-0.7	496
0.7-0.8	173
0.8-0.85	27
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.871	High Similarity	NPD2393	Clinical (unspecified phase)
0.8645	High Similarity	NPD1934	Approved
0.8516	High Similarity	NPD4380	Phase 2
0.8471	Intermediate Similarity	NPD2801	Approved
0.8456	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1549	Phase 2
0.8344	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6166	Phase 2
0.8323	Intermediate Similarity	NPD5494	Approved
0.8313	Intermediate Similarity	NPD7075	Discontinued
0.8313	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD5402	Approved
0.8247	Intermediate Similarity	NPD1511	Approved
0.8239	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD6959	Discontinued
0.8155	Intermediate Similarity	NPD6559	Discontinued
0.8144	Intermediate Similarity	NPD7074	Phase 3
0.8141	Intermediate Similarity	NPD1512	Approved
0.8137	Intermediate Similarity	NPD3882	Suspended
0.8133	Intermediate Similarity	NPD3818	Discontinued
0.8125	Intermediate Similarity	NPD7819	Suspended
0.8089	Intermediate Similarity	NPD5403	Approved
0.8084	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD5844	Phase 1
0.8084	Intermediate Similarity	NPD7054	Approved
0.8079	Intermediate Similarity	NPD1510	Phase 2
0.8072	Intermediate Similarity	NPD7473	Discontinued
0.8063	Intermediate Similarity	NPD6801	Discontinued
0.8036	Intermediate Similarity	NPD7472	Approved
0.8026	Intermediate Similarity	NPD6100	Approved
0.8026	Intermediate Similarity	NPD1551	Phase 2
0.8026	Intermediate Similarity	NPD2796	Approved
0.8026	Intermediate Similarity	NPD6099	Approved
0.8025	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6797	Phase 2
0.7963	Intermediate Similarity	NPD3817	Phase 2
0.7962	Intermediate Similarity	NPD5401	Approved
0.7962	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD8312	Approved
0.7953	Intermediate Similarity	NPD8313	Approved
0.7947	Intermediate Similarity	NPD1607	Approved
0.7941	Intermediate Similarity	NPD7251	Discontinued
0.7937	Intermediate Similarity	NPD6599	Discontinued
0.7935	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD1240	Approved
0.7922	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6799	Approved
0.7895	Intermediate Similarity	NPD7808	Phase 3
0.7888	Intermediate Similarity	NPD7411	Suspended
0.7857	Intermediate Similarity	NPD2346	Discontinued
0.7848	Intermediate Similarity	NPD2533	Approved
0.7848	Intermediate Similarity	NPD2532	Approved
0.7848	Intermediate Similarity	NPD2534	Approved
0.7841	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD3750	Approved
0.7821	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD8434	Phase 2
0.7815	Intermediate Similarity	NPD1613	Approved
0.7815	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3751	Discontinued
0.7805	Intermediate Similarity	NPD7768	Phase 2
0.7784	Intermediate Similarity	NPD3787	Discontinued
0.7764	Intermediate Similarity	NPD3226	Approved
0.7758	Intermediate Similarity	NPD3749	Approved
0.7756	Intermediate Similarity	NPD2800	Approved
0.7714	Intermediate Similarity	NPD8150	Discontinued
0.7707	Intermediate Similarity	NPD4628	Phase 3
0.7692	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD1465	Phase 2
0.7682	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2935	Discontinued
0.7674	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD447	Suspended
0.7622	Intermediate Similarity	NPD37	Approved
0.7616	Intermediate Similarity	NPD4625	Phase 3
0.7613	Intermediate Similarity	NPD2799	Discontinued
0.7605	Intermediate Similarity	NPD6234	Discontinued
0.759	Intermediate Similarity	NPD4967	Phase 2
0.759	Intermediate Similarity	NPD4966	Approved
0.759	Intermediate Similarity	NPD4965	Approved
0.7568	Intermediate Similarity	NPD4749	Approved
0.7566	Intermediate Similarity	NPD2313	Discontinued
0.7566	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1610	Phase 2
0.755	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4908	Phase 1
0.7541	Intermediate Similarity	NPD6781	Approved
0.7541	Intermediate Similarity	NPD6780	Approved
0.7541	Intermediate Similarity	NPD6776	Approved
0.7541	Intermediate Similarity	NPD6779	Approved
0.7541	Intermediate Similarity	NPD6778	Approved
0.7541	Intermediate Similarity	NPD6777	Approved
0.7541	Intermediate Similarity	NPD6782	Approved
0.7516	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5760	Phase 2
0.747	Intermediate Similarity	NPD5761	Phase 2
0.7468	Intermediate Similarity	NPD2424	Discontinued
0.7468	Intermediate Similarity	NPD943	Approved
0.7467	Intermediate Similarity	NPD1470	Approved
0.7467	Intermediate Similarity	NPD1203	Approved
0.7459	Intermediate Similarity	NPD6823	Phase 2
0.7458	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1201	Approved
0.743	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD920	Approved
0.7421	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5124	Phase 1
0.7419	Intermediate Similarity	NPD7435	Discontinued
0.7417	Intermediate Similarity	NPD2798	Approved
0.741	Intermediate Similarity	NPD6844	Discontinued
0.7389	Intermediate Similarity	NPD7033	Discontinued
0.7386	Intermediate Similarity	NPD3027	Phase 3
0.7383	Intermediate Similarity	NPD9717	Approved
0.7378	Intermediate Similarity	NPD1653	Approved
0.7372	Intermediate Similarity	NPD6651	Approved
0.7368	Intermediate Similarity	NPD5711	Approved
0.7368	Intermediate Similarity	NPD5710	Approved
0.7363	Intermediate Similarity	NPD4360	Phase 2
0.7363	Intermediate Similarity	NPD4363	Phase 3
0.7351	Intermediate Similarity	NPD2797	Approved
0.7349	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3268	Approved
0.7338	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7696	Phase 3
0.7326	Intermediate Similarity	NPD7698	Approved
0.7326	Intermediate Similarity	NPD7697	Approved
0.7326	Intermediate Similarity	NPD3926	Phase 2
0.732	Intermediate Similarity	NPD6832	Phase 2
0.7312	Intermediate Similarity	NPD1652	Phase 2
0.731	Intermediate Similarity	NPD7199	Phase 2
0.7308	Intermediate Similarity	NPD230	Phase 1
0.7308	Intermediate Similarity	NPD1933	Approved
0.7301	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2344	Approved
0.7294	Intermediate Similarity	NPD919	Approved
0.7287	Intermediate Similarity	NPD7870	Phase 2
0.7287	Intermediate Similarity	NPD7871	Phase 2
0.7284	Intermediate Similarity	NPD3300	Phase 2
0.7278	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4308	Phase 3
0.7273	Intermediate Similarity	NPD5953	Discontinued
0.7268	Intermediate Similarity	NPD6535	Approved
0.7268	Intermediate Similarity	NPD6534	Approved
0.7263	Intermediate Similarity	NPD7701	Phase 2
0.7258	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7286	Phase 2
0.7255	Intermediate Similarity	NPD2861	Phase 2
0.724	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7801	Approved
0.724	Intermediate Similarity	NPD7783	Phase 2
0.7239	Intermediate Similarity	NPD7390	Discontinued
0.7226	Intermediate Similarity	NPD411	Approved
0.7226	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8151	Discontinued
0.7205	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1243	Approved
0.72	Intermediate Similarity	NPD1091	Approved
0.7197	Intermediate Similarity	NPD6355	Discontinued
0.7197	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4662	Approved
0.7195	Intermediate Similarity	NPD4661	Approved
0.7195	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5647	Approved
0.719	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7874	Approved
0.7188	Intermediate Similarity	NPD6004	Phase 3
0.7188	Intermediate Similarity	NPD6005	Phase 3
0.7188	Intermediate Similarity	NPD6002	Phase 3
0.7188	Intermediate Similarity	NPD5762	Approved
0.7188	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5763	Approved
0.7184	Intermediate Similarity	NPD2403	Approved
0.7178	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1548	Phase 1
0.716	Intermediate Similarity	NPD8455	Phase 2
0.7152	Intermediate Similarity	NPD6273	Approved
0.7152	Intermediate Similarity	NPD1608	Approved
0.7151	Intermediate Similarity	NPD7699	Phase 2
0.7151	Intermediate Similarity	NPD7700	Phase 2
0.7135	Intermediate Similarity	NPD7240	Approved
0.7134	Intermediate Similarity	NPD4060	Phase 1
0.7126	Intermediate Similarity	NPD2649	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