NPASS Compound

Structure

CID164427 OpenBabel06191715532D 22 24 0 0 1 0 0 0 0 0999 V2000 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 21 1 0 0 0 0 4 7 1 0 0 0 0 4 10 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 8 1 0 0 0 0 6 11 2 0 0 0 0 7 1 1 6 0 0 0 7 15 1 0 0 0 0 8 21 1 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 1 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 13 14 1 0 0 0 0 13 16 1 1 0 0 0 14 19 2 0 0 0 0 15 16 1 6 0 0 0 15 20 1 0 0 0 0 16 2 1 6 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.13
Volume:	301.818
LogP:	2.134
LogD:	1.932
LogS:	-3.454
# Rotatable Bonds:	1
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.719
Synthetic Accessibility Score:	4.192
Fsp3:	0.562
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:	-5.064
MDCK Permeability:	1.1967525097134057e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.114
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.859

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.699
Plasma Protein Binding (PPB):	80.25438690185547%
Volume Distribution (VD):	0.913
Pgp-substrate:	17.57381820678711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.524
CYP1A2-substrate:	0.758
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.773
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.503
CYP2D6-inhibitor:	0.061
CYP2D6-substrate:	0.298
CYP3A4-inhibitor:	0.539
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	13.816
Half-life (T1/2):	0.183

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.46
Drug-inuced Liver Injury (DILI):	0.767
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.139
Maximum Recommended Daily Dose:	0.136
Skin Sensitization:	0.441
Carcinogencity:	0.385
Eye Corrosion:	0.005
Eye Irritation:	0.034
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC164427

Natural Product ID:	NPC164427
*Common Name:**	Monodictysin C
IUPAC Name:	(1S,3S,4S,4aS,9aS)-1,4,8-trihydroxy-6-methoxy-3,4a-dimethyl-2,3,4,9a-tetrahydro-1H-xanthen-9-one
Synonyms:	monodictysin C
Standard InCHIKey:	PIJNYABFKNAKHE-YZKPXJPOSA-N
Standard InCHI:	InChI=1S/C16H20O6/c1-7-4-10(18)13-14(19)12-9(17)5-8(21-3)6-11(12)22-16(13,2)15(7)20/h5-7,10,13,15,17-18,20H,4H2,1-3H3/t7-,10-,13+,15-,16-/m0/s1
SMILES:	C[C@H]1C[C@@H]([C@@H]2C(=O)c3c(cc(cc3O[C@]2(C)[C@H]1O)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL376473
PubChem CID:	16114920
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	3
Others	2

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[464237]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	<	50.0	%	PMID[464237]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	28300.0	nM	PMID[464237]
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	Activity	=	12.8	uM	PMID[464237]
NPT2	Others	Unspecified		IC50	=	3000.0	nM	PMID[464237]

☑ 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 NPC164427 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	390
0.1-0.2	1417
0.2-0.3	3132
0.3-0.4	7120
0.4-0.5	10589
0.5-0.6	4786
0.6-0.7	4675
0.7-0.8	6313
0.8-0.85	3106
0.85-0.9	1114
0.9-0.95	48
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC175192
0.9597	High Similarity	NPC207346
0.9597	High Similarity	NPC46564
0.9408	High Similarity	NPC68727
0.9404	High Similarity	NPC470337
0.9404	High Similarity	NPC113608
0.9404	High Similarity	NPC470338
0.9404	High Similarity	NPC268992
0.9404	High Similarity	NPC51824
0.9351	High Similarity	NPC470339
0.9338	High Similarity	NPC470675
0.9338	High Similarity	NPC473131
0.9329	High Similarity	NPC47388
0.9329	High Similarity	NPC470670
0.9329	High Similarity	NPC473133
0.929	High Similarity	NPC472055
0.9276	High Similarity	NPC321363
0.9276	High Similarity	NPC180944
0.9276	High Similarity	NPC470340
0.9276	High Similarity	NPC253904
0.9267	High Similarity	NPC191634
0.9226	High Similarity	NPC329091
0.9216	High Similarity	NPC469405
0.9211	High Similarity	NPC471677
0.9211	High Similarity	NPC263384
0.9211	High Similarity	NPC244577
0.9211	High Similarity	NPC474023
0.9211	High Similarity	NPC472422
0.9211	High Similarity	NPC471676
0.9211	High Similarity	NPC474021
0.9211	High Similarity	NPC472420
0.9205	High Similarity	NPC307052
0.9205	High Similarity	NPC139966
0.92	High Similarity	NPC91902
0.92	High Similarity	NPC85773
0.9182	High Similarity	NPC477154
0.9182	High Similarity	NPC6588
0.9182	High Similarity	NPC117854
0.9182	High Similarity	NPC225419
0.9177	High Similarity	NPC25361
0.9172	High Similarity	NPC473961
0.9167	High Similarity	NPC470810
0.9167	High Similarity	NPC471976
0.9167	High Similarity	NPC161947
0.9167	High Similarity	NPC155302
0.9161	High Similarity	NPC469584
0.9156	High Similarity	NPC326910
0.915	High Similarity	NPC474843
0.915	High Similarity	NPC167903
0.915	High Similarity	NPC210597
0.915	High Similarity	NPC475790
0.915	High Similarity	NPC217149
0.915	High Similarity	NPC216035
0.9145	High Similarity	NPC225854
0.9139	High Similarity	NPC10097
0.9133	High Similarity	NPC474302
0.9128	High Similarity	NPC18886
0.9119	High Similarity	NPC469394
0.9119	High Similarity	NPC170245
0.9114	High Similarity	NPC197168
0.9114	High Similarity	NPC7483
0.9114	High Similarity	NPC475985
0.9108	High Similarity	NPC87431
0.9108	High Similarity	NPC3629
0.9108	High Similarity	NPC61010
0.9108	High Similarity	NPC474186
0.9103	High Similarity	NPC473990
0.9103	High Similarity	NPC85121
0.9103	High Similarity	NPC476242
0.9097	High Similarity	NPC215917
0.9097	High Similarity	NPC20530
0.9097	High Similarity	NPC24640
0.9097	High Similarity	NPC10754
0.9091	High Similarity	NPC472583
0.9091	High Similarity	NPC223701
0.9091	High Similarity	NPC7989
0.9091	High Similarity	NPC74924
0.9091	High Similarity	NPC209760
0.9091	High Similarity	NPC100134
0.9085	High Similarity	NPC262038
0.9085	High Similarity	NPC254412
0.9085	High Similarity	NPC278476
0.9085	High Similarity	NPC472636
0.9085	High Similarity	NPC319910
0.9085	High Similarity	NPC471229
0.9085	High Similarity	NPC262039
0.9079	High Similarity	NPC472628
0.9079	High Similarity	NPC277032
0.9073	High Similarity	NPC308200
0.9073	High Similarity	NPC472627
0.9067	High Similarity	NPC470890
0.9067	High Similarity	NPC311144
0.9062	High Similarity	NPC474024
0.9057	High Similarity	NPC472049
0.9057	High Similarity	NPC326520
0.9051	High Similarity	NPC215612
0.9051	High Similarity	NPC472402
0.9051	High Similarity	NPC472964
0.9051	High Similarity	NPC474162
0.9051	High Similarity	NPC474150
0.9051	High Similarity	NPC211107
0.9045	High Similarity	NPC472902
0.9045	High Similarity	NPC56085
0.9045	High Similarity	NPC470183
0.9045	High Similarity	NPC321399
0.9045	High Similarity	NPC36217
0.9045	High Similarity	NPC474287
0.9045	High Similarity	NPC14353
0.9045	High Similarity	NPC472631
0.9045	High Similarity	NPC174953
0.9045	High Similarity	NPC228785
0.9045	High Similarity	NPC472630
0.9045	High Similarity	NPC475784
0.9045	High Similarity	NPC475886
0.9038	High Similarity	NPC162869
0.9038	High Similarity	NPC27337
0.9038	High Similarity	NPC472598
0.9038	High Similarity	NPC48208
0.9038	High Similarity	NPC474055
0.9038	High Similarity	NPC472911
0.9038	High Similarity	NPC223787
0.9038	High Similarity	NPC165977
0.9038	High Similarity	NPC472914
0.9038	High Similarity	NPC245758
0.9038	High Similarity	NPC217677
0.9038	High Similarity	NPC156057
0.9038	High Similarity	NPC96167
0.9038	High Similarity	NPC222814
0.9038	High Similarity	NPC474836
0.9038	High Similarity	NPC299520
0.9038	High Similarity	NPC475267
0.9038	High Similarity	NPC472913
0.9038	High Similarity	NPC300727
0.9038	High Similarity	NPC472910
0.9038	High Similarity	NPC474208
0.9038	High Similarity	NPC129684
0.9038	High Similarity	NPC181960
0.9038	High Similarity	NPC241904
0.9032	High Similarity	NPC470327
0.9032	High Similarity	NPC471116
0.9032	High Similarity	NPC472909
0.9032	High Similarity	NPC48579
0.9032	High Similarity	NPC37392
0.9032	High Similarity	NPC477503
0.9032	High Similarity	NPC67396
0.9032	High Similarity	NPC304207
0.9032	High Similarity	NPC207809
0.9032	High Similarity	NPC321779
0.9032	High Similarity	NPC259710
0.9032	High Similarity	NPC255807
0.9032	High Similarity	NPC45849
0.9032	High Similarity	NPC200761
0.9032	High Similarity	NPC31018
0.9032	High Similarity	NPC476169
0.9032	High Similarity	NPC217706
0.9032	High Similarity	NPC477958
0.9026	High Similarity	NPC243171
0.9026	High Similarity	NPC10807
0.9026	High Similarity	NPC161881
0.9026	High Similarity	NPC87708
0.9026	High Similarity	NPC56232
0.9026	High Similarity	NPC150123
0.9026	High Similarity	NPC256141
0.9026	High Similarity	NPC171651
0.9026	High Similarity	NPC106976
0.9026	High Similarity	NPC244583
0.9026	High Similarity	NPC35567
0.9026	High Similarity	NPC473996
0.9026	High Similarity	NPC138288
0.902	High Similarity	NPC471115
0.902	High Similarity	NPC338131
0.902	High Similarity	NPC105136
0.902	High Similarity	NPC267117
0.902	High Similarity	NPC29777
0.902	High Similarity	NPC202595
0.9013	High Similarity	NPC39195
0.9013	High Similarity	NPC145467
0.9012	High Similarity	NPC118128
0.9012	High Similarity	NPC472620
0.9007	High Similarity	NPC473135
0.9007	High Similarity	NPC299011
0.9007	High Similarity	NPC470676
0.9007	High Similarity	NPC472629
0.9007	High Similarity	NPC24136
0.9007	High Similarity	NPC290133
0.9007	High Similarity	NPC473132
0.9007	High Similarity	NPC187282
0.9	High Similarity	NPC43319
0.9	High Similarity	NPC120593
0.9	High Similarity	NPC113770
0.9	High Similarity	NPC95751
0.8994	High Similarity	NPC236132
0.8994	High Similarity	NPC186686
0.8994	High Similarity	NPC273959
0.8994	High Similarity	NPC236521
0.8994	High Similarity	NPC41301
0.8994	High Similarity	NPC152659
0.8994	High Similarity	NPC474240
0.8994	High Similarity	NPC124038
0.8994	High Similarity	NPC248638

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 NPC164427 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	866
0.2-0.3	1756
0.3-0.4	2565
0.4-0.5	1931
0.5-0.6	1013
0.6-0.7	484
0.7-0.8	152
0.8-0.85	42
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8968	High Similarity	NPD2393	Clinical (unspecified phase)
0.8903	High Similarity	NPD1934	Approved
0.8774	High Similarity	NPD4380	Phase 2
0.8726	High Similarity	NPD2801	Approved
0.86	High Similarity	NPD1550	Clinical (unspecified phase)
0.86	High Similarity	NPD1552	Clinical (unspecified phase)
0.8589	High Similarity	NPD6167	Clinical (unspecified phase)
0.8589	High Similarity	NPD6166	Phase 2
0.8589	High Similarity	NPD6168	Clinical (unspecified phase)
0.8571	High Similarity	NPD5494	Approved
0.8571	High Similarity	NPD4378	Clinical (unspecified phase)
0.8562	High Similarity	NPD7075	Discontinued
0.8562	High Similarity	NPD4381	Clinical (unspecified phase)
0.8553	High Similarity	NPD8443	Clinical (unspecified phase)
0.8543	High Similarity	NPD1549	Phase 2
0.8519	High Similarity	NPD6959	Discontinued
0.8491	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD1511	Approved
0.8385	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD3882	Suspended
0.8383	Intermediate Similarity	NPD7074	Phase 3
0.8375	Intermediate Similarity	NPD7819	Suspended
0.8373	Intermediate Similarity	NPD3818	Discontinued
0.8323	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD5844	Phase 1
0.8323	Intermediate Similarity	NPD7054	Approved
0.8313	Intermediate Similarity	NPD7473	Discontinued
0.8313	Intermediate Similarity	NPD6801	Discontinued
0.8289	Intermediate Similarity	NPD2796	Approved
0.828	Intermediate Similarity	NPD1512	Approved
0.8274	Intermediate Similarity	NPD7472	Approved
0.8242	Intermediate Similarity	NPD6232	Discontinued
0.8235	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD6797	Phase 2
0.8224	Intermediate Similarity	NPD1510	Phase 2
0.8217	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD2533	Approved
0.8217	Intermediate Similarity	NPD2534	Approved
0.8217	Intermediate Similarity	NPD2532	Approved
0.821	Intermediate Similarity	NPD3817	Phase 2
0.8187	Intermediate Similarity	NPD6599	Discontinued
0.8182	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7251	Discontinued
0.8176	Intermediate Similarity	NPD6559	Discontinued
0.817	Intermediate Similarity	NPD6099	Approved
0.817	Intermediate Similarity	NPD6100	Approved
0.8153	Intermediate Similarity	NPD6799	Approved
0.8137	Intermediate Similarity	NPD7411	Suspended
0.8129	Intermediate Similarity	NPD2800	Approved
0.8129	Intermediate Similarity	NPD7808	Phase 3
0.8098	Intermediate Similarity	NPD5402	Approved
0.8092	Intermediate Similarity	NPD1607	Approved
0.8079	Intermediate Similarity	NPD1240	Approved
0.8012	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3749	Approved
0.7966	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD4628	Phase 3
0.7943	Intermediate Similarity	NPD8434	Phase 2
0.7941	Intermediate Similarity	NPD3751	Discontinued
0.7929	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD1465	Phase 2
0.7917	Intermediate Similarity	NPD3787	Discontinued
0.7888	Intermediate Similarity	NPD5403	Approved
0.7848	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3750	Approved
0.7831	Intermediate Similarity	NPD7768	Phase 2
0.7771	Intermediate Similarity	NPD8312	Approved
0.7771	Intermediate Similarity	NPD8313	Approved
0.7764	Intermediate Similarity	NPD5401	Approved
0.7758	Intermediate Similarity	NPD37	Approved
0.7756	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6651	Approved
0.774	Intermediate Similarity	NPD8150	Discontinued
0.7738	Intermediate Similarity	NPD6234	Discontinued
0.7727	Intermediate Similarity	NPD1613	Approved
0.7727	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD4965	Approved
0.7725	Intermediate Similarity	NPD4966	Approved
0.7725	Intermediate Similarity	NPD4967	Phase 2
0.7714	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1551	Phase 2
0.7707	Intermediate Similarity	NPD2935	Discontinued
0.7706	Intermediate Similarity	NPD5711	Approved
0.7706	Intermediate Similarity	NPD5710	Approved
0.7684	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD3226	Approved
0.7673	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD6777	Approved
0.7663	Intermediate Similarity	NPD6776	Approved
0.7663	Intermediate Similarity	NPD6780	Approved
0.7663	Intermediate Similarity	NPD6782	Approved
0.7663	Intermediate Similarity	NPD6779	Approved
0.7663	Intermediate Similarity	NPD6781	Approved
0.7663	Intermediate Similarity	NPD6778	Approved
0.7658	Intermediate Similarity	NPD2346	Discontinued
0.7647	Intermediate Similarity	NPD1247	Approved
0.7643	Intermediate Similarity	NPD2799	Discontinued
0.763	Intermediate Similarity	NPD7228	Approved
0.7625	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD943	Approved
0.7605	Intermediate Similarity	NPD5761	Phase 2
0.7605	Intermediate Similarity	NPD5760	Phase 2
0.7597	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7390	Discontinued
0.7582	Intermediate Similarity	NPD4360	Phase 2
0.7582	Intermediate Similarity	NPD4908	Phase 1
0.7582	Intermediate Similarity	NPD4363	Phase 3
0.7564	Intermediate Similarity	NPD230	Phase 1
0.7561	Intermediate Similarity	NPD920	Approved
0.7558	Intermediate Similarity	NPD3926	Phase 2
0.7556	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2344	Approved
0.7546	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7199	Phase 2
0.754	Intermediate Similarity	NPD7435	Discontinued
0.7532	Intermediate Similarity	NPD3748	Approved
0.7526	Intermediate Similarity	NPD8151	Discontinued
0.7516	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2403	Approved
0.75	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD2424	Discontinued
0.7486	Intermediate Similarity	NPD7286	Phase 2
0.7483	Intermediate Similarity	NPD4749	Approved
0.7473	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1610	Phase 2
0.7453	Intermediate Similarity	NPD1243	Approved
0.7452	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD5124	Phase 1
0.7448	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7783	Phase 2
0.7447	Intermediate Similarity	NPD7696	Phase 3
0.7447	Intermediate Similarity	NPD7697	Approved
0.7447	Intermediate Similarity	NPD7698	Approved
0.7439	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD919	Approved
0.7421	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7033	Discontinued
0.7419	Intermediate Similarity	NPD3027	Phase 3
0.7419	Intermediate Similarity	NPD4625	Phase 3
0.7407	Intermediate Similarity	NPD7871	Phase 2
0.7407	Intermediate Similarity	NPD7870	Phase 2
0.7394	Intermediate Similarity	NPD6823	Phase 2
0.7391	Intermediate Similarity	NPD6535	Approved
0.7391	Intermediate Similarity	NPD6534	Approved
0.7382	Intermediate Similarity	NPD7701	Phase 2
0.7381	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.7362	Intermediate Similarity	NPD6190	Approved
0.7362	Intermediate Similarity	NPD2309	Approved
0.7358	Intermediate Similarity	NPD7801	Approved
0.7356	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD447	Suspended
0.7333	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7584	Approved
0.7317	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7874	Approved
0.7306	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1653	Approved
0.7299	Intermediate Similarity	NPD7229	Phase 3
0.729	Intermediate Similarity	NPD2861	Phase 2
0.7273	Intermediate Similarity	NPD7700	Phase 2
0.7273	Intermediate Similarity	NPD7699	Phase 2
0.7263	Intermediate Similarity	NPD7240	Approved
0.7263	Intermediate Similarity	NPD7685	Pre-registration
0.7262	Intermediate Similarity	NPD7458	Discontinued
0.7261	Intermediate Similarity	NPD3268	Approved
0.7258	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD4361	Phase 2
0.7246	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1652	Phase 2
0.7239	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6844	Discontinued
0.7233	Intermediate Similarity	NPD6355	Discontinued
0.7226	Intermediate Similarity	NPD2798	Approved
0.7225	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3300	Phase 2
0.7193	Intermediate Similarity	NPD8455	Phase 2
0.7186	Intermediate Similarity	NPD6273	Approved
0.717	Intermediate Similarity	NPD4060	Phase 1
0.7161	Intermediate Similarity	NPD1203	Approved
0.7161	Intermediate Similarity	NPD2797	Approved
0.7161	Intermediate Similarity	NPD1470	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7151	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7135	Intermediate Similarity	NPD8319	Approved
0.7135	Intermediate Similarity	NPD8320	Phase 1
0.7134	Intermediate Similarity	NPD2654	Approved
0.7134	Intermediate Similarity	NPD6674	Discontinued
0.7134	Intermediate Similarity	NPD6832	Phase 2
0.7125	Intermediate Similarity	NPD1933	Approved
0.7124	Intermediate Similarity	NPD1201	Approved
0.7117	Intermediate Similarity	NPD1471	Phase 3
0.7115	Intermediate Similarity	NPD6917	Clinical (unspecified phase)

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