NPASS Compound

Structure

CID321363 OpenBabel06191716152D 22 24 0 0 1 0 0 0 0 0999 V2000 0.0999 0.7588 0.0000 C 0 0 0 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 -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 3.4641 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 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 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 1.5000 0.0000 C 0 0 0 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 -0.8660 0.5000 0.0000 C 0 0 2 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 3.4641 -1.0000 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 -1.7321 -1.0000 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 -0.8660 2.5000 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 14 1 0 0 0 0 2 3 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 7 1 0 0 0 0 5 9 2 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 9 22 1 0 0 0 0 10 14 1 1 0 0 0 10 18 1 0 0 0 0 11 15 1 6 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 13 15 1 0 0 0 0 13 20 2 0 0 0 0 14 15 1 1 0 0 0 14 22 1 0 0 0 0 15 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.11
Volume:	293.313
LogP:	-0.047
LogD:	-0.3
LogS:	-3.661
# Rotatable Bonds:	1
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	4.538
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.59
MDCK Permeability:	5.656282155541703e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.965
Human Intestinal Absorption (HIA):	0.149
20% Bioavailability (F20%):	0.148
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.596
Plasma Protein Binding (PPB):	62.71978759765625%
Volume Distribution (VD):	0.951
Pgp-substrate:	47.593017578125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.175
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.08

ADMET: Excretion

Clearance (CL):	3.749
Half-life (T1/2):	0.591

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.143
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.741
Skin Sensitization:	0.144
Carcinogencity:	0.033
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC321363

Natural Product ID:	NPC321363
*Common Name:**	Microdiplodiasol
IUPAC Name:	(1S,4S,4aS,9aR)-1,4,8,9a-tetrahydroxy-6-(hydroxymethyl)-4a-methyl-1,2,3,4-tetrahydroxanthen-9-one
Synonyms:	Microdiplodiasol
Standard InCHIKey:	SCOQIJBVVKZZHE-GVARAGBVSA-N
Standard InCHI:	InChI=1S/C15H18O7/c1-14-10(18)2-3-11(19)15(14,21)13(20)12-8(17)4-7(6-16)5-9(12)22-14/h4-5,10-11,16-19,21H,2-3,6H2,1H3/t10-,11-,14-,15-/m0/s1
SMILES:	OCc1cc2O[C@@]3(C)[C@@H](O)CC[C@@H]([C@@]3(C(=O)c2c(c1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1765409
PubChem CID:	52937070
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
NPO33247	microdiplodia sp.	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21244021]
NPO30809	Microdiplodia	Genus	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21244021]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1465	Organism	Legionella pneumophila	Legionella pneumophila	MIC	=	125.0	ug.mL-1	PMID[487821]

☑ 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 NPC321363 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	384
0.1-0.2	1410
0.2-0.3	3255
0.3-0.4	8135
0.4-0.5	10486
0.5-0.6	4038
0.6-0.7	5460
0.7-0.8	6891
0.8-0.85	2371
0.85-0.9	253
0.9-0.95	8
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC253904
0.9597	High Similarity	NPC175192
0.9597	High Similarity	NPC326910
0.9527	High Similarity	NPC46564
0.9527	High Similarity	NPC207346
0.9324	High Similarity	NPC191634
0.9276	High Similarity	NPC164427
0.9145	High Similarity	NPC301233
0.9	High Similarity	NPC71055
0.9	High Similarity	NPC21835
0.8981	High Similarity	NPC473961
0.8974	High Similarity	NPC470183
0.8973	High Similarity	NPC268691
0.8961	High Similarity	NPC237560
0.894	High Similarity	NPC218569
0.891	High Similarity	NPC329091
0.891	High Similarity	NPC152904
0.8904	High Similarity	NPC287068
0.8903	High Similarity	NPC201837
0.8896	High Similarity	NPC135522
0.8889	High Similarity	NPC471229
0.8882	High Similarity	NPC277032
0.8868	High Similarity	NPC472049
0.8868	High Similarity	NPC224280
0.8868	High Similarity	NPC234052
0.8861	High Similarity	NPC211107
0.8854	High Similarity	NPC470810
0.8854	High Similarity	NPC263449
0.8846	High Similarity	NPC477833
0.8839	High Similarity	NPC68727
0.8831	High Similarity	NPC36835
0.8831	High Similarity	NPC61506
0.8831	High Similarity	NPC281272
0.8831	High Similarity	NPC9743
0.8831	High Similarity	NPC113608
0.8831	High Similarity	NPC19721
0.8831	High Similarity	NPC260491
0.8831	High Similarity	NPC210597
0.8831	High Similarity	NPC240476
0.8831	High Similarity	NPC474843
0.8831	High Similarity	NPC470338
0.8831	High Similarity	NPC470337
0.8831	High Similarity	NPC167903
0.8831	High Similarity	NPC268992
0.8831	High Similarity	NPC51824
0.8831	High Similarity	NPC75069
0.8831	High Similarity	NPC246162
0.8824	High Similarity	NPC267117
0.8824	High Similarity	NPC202595
0.8812	High Similarity	NPC178173
0.8808	High Similarity	NPC469758
0.8805	High Similarity	NPC197168
0.8805	High Similarity	NPC475985
0.8805	High Similarity	NPC474240
0.8805	High Similarity	NPC41301
0.8797	High Similarity	NPC173137
0.8797	High Similarity	NPC308992
0.879	High Similarity	NPC476242
0.879	High Similarity	NPC85121
0.879	High Similarity	NPC22192
0.879	High Similarity	NPC186113
0.879	High Similarity	NPC470339
0.879	High Similarity	NPC55738
0.8782	High Similarity	NPC13858
0.8782	High Similarity	NPC24640
0.8782	High Similarity	NPC471500
0.8782	High Similarity	NPC154341
0.8782	High Similarity	NPC326037
0.8782	High Similarity	NPC320825
0.8782	High Similarity	NPC250922
0.8782	High Similarity	NPC303255
0.8774	High Similarity	NPC209760
0.8774	High Similarity	NPC27532
0.8774	High Similarity	NPC256346
0.8774	High Similarity	NPC325028
0.8774	High Similarity	NPC203080
0.8774	High Similarity	NPC246328
0.8774	High Similarity	NPC100134
0.8773	High Similarity	NPC154986
0.8766	High Similarity	NPC254412
0.8766	High Similarity	NPC475076
0.8766	High Similarity	NPC278476
0.8766	High Similarity	NPC262039
0.8766	High Similarity	NPC39819
0.8766	High Similarity	NPC262038
0.8766	High Similarity	NPC319910
0.8765	High Similarity	NPC241874
0.8758	High Similarity	NPC117854
0.8758	High Similarity	NPC294502
0.8758	High Similarity	NPC200221
0.8758	High Similarity	NPC6588
0.8758	High Similarity	NPC477154
0.8758	High Similarity	NPC225419
0.8758	High Similarity	NPC474024
0.875	High Similarity	NPC3779
0.875	High Similarity	NPC176869
0.875	High Similarity	NPC46941
0.875	High Similarity	NPC122828
0.875	High Similarity	NPC475888
0.875	High Similarity	NPC472918
0.875	High Similarity	NPC44721
0.875	High Similarity	NPC211466
0.875	High Similarity	NPC476182
0.875	High Similarity	NPC25361
0.875	High Similarity	NPC40086
0.875	High Similarity	NPC62261
0.875	High Similarity	NPC85773
0.8742	High Similarity	NPC49130
0.8742	High Similarity	NPC4152
0.8742	High Similarity	NPC279417
0.8742	High Similarity	NPC472964
0.8742	High Similarity	NPC142731
0.8742	High Similarity	NPC469764
0.8742	High Similarity	NPC306607
0.8742	High Similarity	NPC208176
0.8742	High Similarity	NPC326506
0.8742	High Similarity	NPC62290
0.8735	High Similarity	NPC208069
0.8734	High Similarity	NPC472902
0.8734	High Similarity	NPC471976
0.8734	High Similarity	NPC282009
0.8734	High Similarity	NPC472055
0.8734	High Similarity	NPC470326
0.8734	High Similarity	NPC287328
0.8727	High Similarity	NPC477682
0.8727	High Similarity	NPC477683
0.8726	High Similarity	NPC475267
0.8726	High Similarity	NPC52530
0.8726	High Similarity	NPC471515
0.8726	High Similarity	NPC48208
0.8726	High Similarity	NPC282390
0.8726	High Similarity	NPC162869
0.8726	High Similarity	NPC474836
0.8726	High Similarity	NPC474208
0.8726	High Similarity	NPC241904
0.8726	High Similarity	NPC469584
0.8726	High Similarity	NPC471479
0.8726	High Similarity	NPC156057
0.8726	High Similarity	NPC300727
0.8726	High Similarity	NPC281137
0.8726	High Similarity	NPC67876
0.8725	High Similarity	NPC145673
0.8718	High Similarity	NPC259710
0.8718	High Similarity	NPC67396
0.8718	High Similarity	NPC304207
0.8718	High Similarity	NPC207809
0.8718	High Similarity	NPC476169
0.8718	High Similarity	NPC48579
0.8718	High Similarity	NPC37392
0.8718	High Similarity	NPC471116
0.8718	High Similarity	NPC217706
0.871	High Similarity	NPC35567
0.871	High Similarity	NPC275878
0.871	High Similarity	NPC180944
0.871	High Similarity	NPC216035
0.871	High Similarity	NPC171651
0.871	High Similarity	NPC138288
0.871	High Similarity	NPC470340
0.871	High Similarity	NPC243171
0.871	High Similarity	NPC217149
0.8704	High Similarity	NPC326877
0.8701	High Similarity	NPC105136
0.8701	High Similarity	NPC338131
0.8696	High Similarity	NPC43319
0.8696	High Similarity	NPC170245
0.8696	High Similarity	NPC477517
0.8693	High Similarity	NPC5537
0.8688	High Similarity	NPC472625
0.8688	High Similarity	NPC236132
0.8688	High Similarity	NPC7483
0.8684	High Similarity	NPC1940
0.8684	High Similarity	NPC148011
0.8684	High Similarity	NPC209278
0.8679	High Similarity	NPC471499
0.8679	High Similarity	NPC476929
0.8679	High Similarity	NPC61010
0.8679	High Similarity	NPC3629
0.8679	High Similarity	NPC474186
0.8679	High Similarity	NPC474239
0.8679	High Similarity	NPC117985
0.8675	High Similarity	NPC95751
0.8671	High Similarity	NPC473990
0.8671	High Similarity	NPC474290
0.8662	High Similarity	NPC215917
0.8662	High Similarity	NPC235165
0.8662	High Similarity	NPC274730
0.8662	High Similarity	NPC10754
0.8662	High Similarity	NPC255106
0.8662	High Similarity	NPC474638
0.8662	High Similarity	NPC20530
0.8654	High Similarity	NPC74924
0.8654	High Similarity	NPC180301
0.8654	High Similarity	NPC193200
0.8654	High Similarity	NPC18727
0.8654	High Similarity	NPC141212
0.8654	High Similarity	NPC469405
0.8654	High Similarity	NPC89474
0.8654	High Similarity	NPC293286
0.8654	High Similarity	NPC248793
0.865	High Similarity	NPC313717

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 NPC321363 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	872
0.2-0.3	1724
0.3-0.4	2611
0.4-0.5	1945
0.5-0.6	1043
0.6-0.7	456
0.7-0.8	145
0.8-0.85	26
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.859	High Similarity	NPD1934	Approved
0.8535	High Similarity	NPD2393	Clinical (unspecified phase)
0.8519	High Similarity	NPD6166	Phase 2
0.8519	High Similarity	NPD6167	Clinical (unspecified phase)
0.8519	High Similarity	NPD6168	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD5402	Approved
0.8418	Intermediate Similarity	NPD2801	Approved
0.8323	Intermediate Similarity	NPD1512	Approved
0.8313	Intermediate Similarity	NPD3882	Suspended
0.8278	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD7075	Discontinued
0.8258	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD4380	Phase 2
0.8224	Intermediate Similarity	NPD1549	Phase 2
0.8221	Intermediate Similarity	NPD6959	Discontinued
0.8194	Intermediate Similarity	NPD1511	Approved
0.8187	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD6797	Phase 2
0.8153	Intermediate Similarity	NPD5403	Approved
0.8148	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD3817	Phase 2
0.8113	Intermediate Similarity	NPD6599	Discontinued
0.8107	Intermediate Similarity	NPD6559	Discontinued
0.8107	Intermediate Similarity	NPD7251	Discontinued
0.8095	Intermediate Similarity	NPD7074	Phase 3
0.8092	Intermediate Similarity	NPD6100	Approved
0.8092	Intermediate Similarity	NPD6099	Approved
0.8086	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD3818	Discontinued
0.8059	Intermediate Similarity	NPD7808	Phase 3
0.8049	Intermediate Similarity	NPD5494	Approved
0.8036	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD5844	Phase 1
0.8036	Intermediate Similarity	NPD7054	Approved
0.8025	Intermediate Similarity	NPD5401	Approved
0.8012	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7472	Approved
0.7976	Intermediate Similarity	NPD3751	Discontinued
0.7974	Intermediate Similarity	NPD1551	Phase 2
0.7963	Intermediate Similarity	NPD7819	Suspended
0.7962	Intermediate Similarity	NPD6799	Approved
0.7952	Intermediate Similarity	NPD6232	Discontinued
0.7952	Intermediate Similarity	NPD3787	Discontinued
0.7941	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7473	Discontinued
0.7914	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD2533	Approved
0.7911	Intermediate Similarity	NPD2534	Approved
0.7911	Intermediate Similarity	NPD2532	Approved
0.7908	Intermediate Similarity	NPD1510	Phase 2
0.7895	Intermediate Similarity	NPD1607	Approved
0.7885	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2796	Approved
0.7806	Intermediate Similarity	NPD2346	Discontinued
0.7803	Intermediate Similarity	NPD8313	Approved
0.7803	Intermediate Similarity	NPD8312	Approved
0.7771	Intermediate Similarity	NPD8150	Discontinued
0.7763	Intermediate Similarity	NPD1240	Approved
0.7763	Intermediate Similarity	NPD1613	Approved
0.7763	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1465	Phase 2
0.7716	Intermediate Similarity	NPD3226	Approved
0.7692	Intermediate Similarity	NPD6782	Approved
0.7692	Intermediate Similarity	NPD6778	Approved
0.7692	Intermediate Similarity	NPD6779	Approved
0.7692	Intermediate Similarity	NPD6776	Approved
0.7692	Intermediate Similarity	NPD6777	Approved
0.7692	Intermediate Similarity	NPD6780	Approved
0.7692	Intermediate Similarity	NPD6781	Approved
0.7688	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8434	Phase 2
0.7658	Intermediate Similarity	NPD3750	Approved
0.7658	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4628	Phase 3
0.7635	Intermediate Similarity	NPD4749	Approved
0.7632	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7411	Suspended
0.7605	Intermediate Similarity	NPD3749	Approved
0.7597	Intermediate Similarity	NPD447	Suspended
0.7595	Intermediate Similarity	NPD2800	Approved
0.7574	Intermediate Similarity	NPD1247	Approved
0.7568	Intermediate Similarity	NPD7435	Discontinued
0.7566	Intermediate Similarity	NPD4625	Phase 3
0.7564	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7768	Phase 2
0.7516	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3926	Phase 2
0.7473	Intermediate Similarity	NPD7697	Approved
0.7473	Intermediate Similarity	NPD7698	Approved
0.7473	Intermediate Similarity	NPD7696	Phase 3
0.747	Intermediate Similarity	NPD37	Approved
0.7469	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6234	Discontinued
0.7452	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4967	Phase 2
0.744	Intermediate Similarity	NPD4966	Approved
0.744	Intermediate Similarity	NPD4965	Approved
0.7433	Intermediate Similarity	NPD7871	Phase 2
0.7433	Intermediate Similarity	NPD7870	Phase 2
0.7427	Intermediate Similarity	NPD5710	Approved
0.7427	Intermediate Similarity	NPD5711	Approved
0.7419	Intermediate Similarity	NPD943	Approved
0.7419	Intermediate Similarity	NPD6823	Phase 2
0.7418	Intermediate Similarity	NPD6535	Approved
0.7418	Intermediate Similarity	NPD6534	Approved
0.7416	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7701	Phase 2
0.7389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD230	Phase 1
0.7365	Intermediate Similarity	NPD6844	Discontinued
0.7356	Intermediate Similarity	NPD7228	Approved
0.7353	Intermediate Similarity	NPD919	Approved
0.7342	Intermediate Similarity	NPD3748	Approved
0.7338	Intermediate Similarity	NPD3027	Phase 3
0.7333	Intermediate Similarity	NPD1653	Approved
0.733	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7874	Approved
0.7303	Intermediate Similarity	NPD1203	Approved
0.7303	Intermediate Similarity	NPD1470	Approved
0.7301	Intermediate Similarity	NPD7390	Discontinued
0.7297	Intermediate Similarity	NPD7700	Phase 2
0.7297	Intermediate Similarity	NPD7699	Phase 2
0.7292	Intermediate Similarity	NPD7801	Approved
0.729	Intermediate Similarity	NPD411	Approved
0.729	Intermediate Similarity	NPD2313	Discontinued
0.729	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6190	Approved
0.7277	Intermediate Similarity	NPD8151	Discontinued
0.7273	Intermediate Similarity	NPD4908	Phase 1
0.7267	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD1201	Approved
0.7241	Intermediate Similarity	NPD2403	Approved
0.7239	Intermediate Similarity	NPD3300	Phase 2
0.7233	Intermediate Similarity	NPD2799	Discontinued
0.7233	Intermediate Similarity	NPD7033	Discontinued
0.7233	Intermediate Similarity	NPD4308	Phase 3
0.7219	Intermediate Similarity	NPD9717	Approved
0.7205	Intermediate Similarity	NPD2424	Discontinued
0.7202	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7783	Phase 2
0.7184	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6798	Discontinued
0.7179	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD920	Approved
0.7168	Intermediate Similarity	NPD7199	Phase 2
0.7161	Intermediate Similarity	NPD6832	Phase 2
0.716	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1652	Phase 2
0.716	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1933	Approved
0.7152	Intermediate Similarity	NPD6355	Discontinued
0.7151	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD2798	Approved
0.7143	Intermediate Similarity	NPD2344	Approved
0.7143	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7128	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5761	Phase 2
0.7118	Intermediate Similarity	NPD5760	Phase 2
0.7107	Intermediate Similarity	NPD6651	Approved
0.7097	Intermediate Similarity	NPD2861	Phase 2
0.7089	Intermediate Similarity	NPD4060	Phase 1
0.7083	Intermediate Similarity	NPD2651	Approved
0.7083	Intermediate Similarity	NPD2649	Approved
0.7078	Intermediate Similarity	NPD2797	Approved
0.707	Intermediate Similarity	NPD3268	Approved
0.7068	Intermediate Similarity	NPD8320	Phase 1
0.7068	Intermediate Similarity	NPD8319	Approved
0.7059	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1243	Approved
0.7048	Intermediate Similarity	NPD4661	Approved
0.7048	Intermediate Similarity	NPD4662	Approved
0.7048	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5124	Phase 1
0.7043	Intermediate Similarity	NPD4363	Phase 3
0.7043	Intermediate Similarity	NPD4360	Phase 2
0.7039	Intermediate Similarity	NPD1091	Approved
0.7039	Intermediate Similarity	NPD5953	Discontinued
0.7037	Intermediate Similarity	NPD1471	Phase 3
0.7022	Intermediate Similarity	NPD7286	Phase 2
0.7	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7240	Approved
0.7	Intermediate Similarity	NPD1548	Phase 1
0.6993	Remote Similarity	NPD1608	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