NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.09
Volume:	261.669
LogP:	3.749
LogD:	2.731
LogS:	-4.458
# Rotatable Bonds:	0
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.73
Synthetic Accessibility Score:	4.074
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.843
MDCK Permeability:	2.133276757376734e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	88.9616928100586%
Volume Distribution (VD):	1.147
Pgp-substrate:	9.434405326843262%

ADMET: Metabolism

CYP1A2-inhibitor:	0.979
CYP1A2-substrate:	0.799
CYP2C19-inhibitor:	0.387
CYP2C19-substrate:	0.527
CYP2C9-inhibitor:	0.654
CYP2C9-substrate:	0.572
CYP2D6-inhibitor:	0.566
CYP2D6-substrate:	0.242
CYP3A4-inhibitor:	0.299
CYP3A4-substrate:	0.246

ADMET: Excretion

Clearance (CL):	11.711
Half-life (T1/2):	0.612

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.955
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.399
Rat Oral Acute Toxicity:	0.461
Maximum Recommended Daily Dose:	0.81
Skin Sensitization:	0.697
Carcinogencity:	0.911
Eye Corrosion:	0.004
Eye Irritation:	0.026
Respiratory Toxicity:	0.776

Download Data

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

Natural Product: NPC471346

Natural Product ID:	NPC471346
*Common Name:**	(7R)-7-Methyl-2-Propan-2-Ylidene-6,7-Dihydrofuro[3,2-H]Isochromene-3,9-Dione
IUPAC Name:	(7R)-7-methyl-2-propan-2-ylidene-6,7-dihydrofuro[3,2-h]isochromene-3,9-dione
Synonyms:
Standard InCHIKey:	JEBVCMMFVQCLIM-MRVPVSSYSA-N
Standard InCHI:	InChI=1S/C15H14O4/c1-7(2)13-12(16)10-5-4-9-6-8(3)18-15(17)11(9)14(10)19-13/h4-5,8H,6H2,1-3H3/t8-/m1/s1
SMILES:	C[C@H]1OC(=O)c2c(C1)ccc1c2OC(=C(C)C)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419842
PubChem CID:	73349181
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19769341]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	Suberites domuncula	n.a.	n.a.	PMID[19778087]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21348461]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25706180]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29286660]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	9800.0	nM	PMID[459973]

☑ 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 NPC471346 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	400
0.1-0.2	1579
0.2-0.3	3715
0.3-0.4	8738
0.4-0.5	9931
0.5-0.6	4724
0.6-0.7	6719
0.7-0.8	6419
0.8-0.85	446
0.85-0.9	18
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9178	High Similarity	NPC219560
0.9116	High Similarity	NPC469416
0.9116	High Similarity	NPC228906
0.9116	High Similarity	NPC471348
0.9071	High Similarity	NPC217914
0.9034	High Similarity	NPC469385
0.8993	High Similarity	NPC175617
0.8933	High Similarity	NPC471347
0.8933	High Similarity	NPC471349
0.8803	High Similarity	NPC470844
0.8725	High Similarity	NPC469425
0.8714	High Similarity	NPC473271
0.8707	High Similarity	NPC471639
0.8707	High Similarity	NPC471643
0.8514	High Similarity	NPC471644
0.8514	High Similarity	NPC471640
0.8446	Intermediate Similarity	NPC470856
0.8442	Intermediate Similarity	NPC271681
0.8418	Intermediate Similarity	NPC24761
0.8411	Intermediate Similarity	NPC473927
0.84	Intermediate Similarity	NPC184702
0.8389	Intermediate Similarity	NPC297985
0.8367	Intermediate Similarity	NPC221104
0.8366	Intermediate Similarity	NPC226578
0.8366	Intermediate Similarity	NPC198927
0.8356	Intermediate Similarity	NPC232996
0.8354	Intermediate Similarity	NPC313368
0.8354	Intermediate Similarity	NPC243701
0.8344	Intermediate Similarity	NPC476930
0.8344	Intermediate Similarity	NPC217602
0.8344	Intermediate Similarity	NPC104380
0.8344	Intermediate Similarity	NPC473282
0.8344	Intermediate Similarity	NPC474630
0.8344	Intermediate Similarity	NPC473692
0.8323	Intermediate Similarity	NPC24232
0.8323	Intermediate Similarity	NPC298071
0.8323	Intermediate Similarity	NPC10429
0.8323	Intermediate Similarity	NPC472895
0.8322	Intermediate Similarity	NPC470842
0.8322	Intermediate Similarity	NPC149533
0.8313	Intermediate Similarity	NPC132054
0.8312	Intermediate Similarity	NPC474660
0.8288	Intermediate Similarity	NPC27407
0.8278	Intermediate Similarity	NPC470932
0.8269	Intermediate Similarity	NPC301233
0.8264	Intermediate Similarity	NPC279596
0.8252	Intermediate Similarity	NPC66246
0.8252	Intermediate Similarity	NPC170546
0.8247	Intermediate Similarity	NPC70764
0.8243	Intermediate Similarity	NPC265181
0.8235	Intermediate Similarity	NPC52106
0.8235	Intermediate Similarity	NPC471285
0.8235	Intermediate Similarity	NPC14098
0.8235	Intermediate Similarity	NPC137296
0.8231	Intermediate Similarity	NPC291454
0.8228	Intermediate Similarity	NPC317900
0.8228	Intermediate Similarity	NPC476404
0.8228	Intermediate Similarity	NPC294300
0.8224	Intermediate Similarity	NPC472034
0.8219	Intermediate Similarity	NPC247743
0.8194	Intermediate Similarity	NPC282230
0.8194	Intermediate Similarity	NPC473466
0.8194	Intermediate Similarity	NPC119929
0.8194	Intermediate Similarity	NPC144010
0.8194	Intermediate Similarity	NPC158866
0.8194	Intermediate Similarity	NPC183348
0.8188	Intermediate Similarity	NPC36414
0.8188	Intermediate Similarity	NPC473988
0.8187	Intermediate Similarity	NPC472780
0.8187	Intermediate Similarity	NPC472783
0.8182	Intermediate Similarity	NPC37139
0.8182	Intermediate Similarity	NPC240622
0.8182	Intermediate Similarity	NPC240253
0.8182	Intermediate Similarity	NPC471642
0.8182	Intermediate Similarity	NPC471641
0.8176	Intermediate Similarity	NPC33320
0.817	Intermediate Similarity	NPC472033
0.817	Intermediate Similarity	NPC470357
0.8163	Intermediate Similarity	NPC142027
0.8158	Intermediate Similarity	NPC151607
0.8158	Intermediate Similarity	NPC42540
0.8158	Intermediate Similarity	NPC189650
0.8153	Intermediate Similarity	NPC75310
0.8153	Intermediate Similarity	NPC472799
0.8148	Intermediate Similarity	NPC279768
0.8148	Intermediate Similarity	NPC316262
0.8148	Intermediate Similarity	NPC314653
0.8146	Intermediate Similarity	NPC469579
0.8146	Intermediate Similarity	NPC24075
0.8141	Intermediate Similarity	NPC98028
0.8141	Intermediate Similarity	NPC39819
0.8141	Intermediate Similarity	NPC232645
0.8141	Intermediate Similarity	NPC133856
0.8141	Intermediate Similarity	NPC72958
0.8141	Intermediate Similarity	NPC473732
0.8141	Intermediate Similarity	NPC471613
0.8141	Intermediate Similarity	NPC189773
0.8138	Intermediate Similarity	NPC477412
0.8138	Intermediate Similarity	NPC470977
0.8138	Intermediate Similarity	NPC214702
0.8138	Intermediate Similarity	NPC470831
0.8138	Intermediate Similarity	NPC15083
0.8138	Intermediate Similarity	NPC470976
0.8138	Intermediate Similarity	NPC196979
0.8133	Intermediate Similarity	NPC477537
0.8133	Intermediate Similarity	NPC165172
0.8129	Intermediate Similarity	NPC291049
0.8129	Intermediate Similarity	NPC77325
0.8129	Intermediate Similarity	NPC4423
0.8129	Intermediate Similarity	NPC233267
0.8125	Intermediate Similarity	NPC472781
0.8125	Intermediate Similarity	NPC243509
0.8125	Intermediate Similarity	NPC472782
0.8121	Intermediate Similarity	NPC253616
0.8117	Intermediate Similarity	NPC8817
0.8117	Intermediate Similarity	NPC252208
0.8117	Intermediate Similarity	NPC472036
0.8117	Intermediate Similarity	NPC71055
0.8113	Intermediate Similarity	NPC201127
0.8112	Intermediate Similarity	NPC293387
0.811	Intermediate Similarity	NPC191653
0.8105	Intermediate Similarity	NPC312789
0.8105	Intermediate Similarity	NPC75694
0.8105	Intermediate Similarity	NPC171656
0.8105	Intermediate Similarity	NPC28632
0.8105	Intermediate Similarity	NPC49282
0.8101	Intermediate Similarity	NPC89625
0.8101	Intermediate Similarity	NPC471456
0.8101	Intermediate Similarity	NPC237560
0.8101	Intermediate Similarity	NPC149618
0.8098	Intermediate Similarity	NPC475109
0.8095	Intermediate Similarity	NPC1249
0.8092	Intermediate Similarity	NPC159721
0.8092	Intermediate Similarity	NPC469542
0.8092	Intermediate Similarity	NPC215451
0.8092	Intermediate Similarity	NPC277369
0.8092	Intermediate Similarity	NPC472840
0.8092	Intermediate Similarity	NPC117674
0.8089	Intermediate Similarity	NPC87708
0.8089	Intermediate Similarity	NPC288534
0.8089	Intermediate Similarity	NPC273483
0.8089	Intermediate Similarity	NPC475116
0.8079	Intermediate Similarity	NPC171094
0.8077	Intermediate Similarity	NPC325983
0.8077	Intermediate Similarity	NPC150928
0.8077	Intermediate Similarity	NPC202595
0.8077	Intermediate Similarity	NPC475717
0.8077	Intermediate Similarity	NPC470107
0.8075	Intermediate Similarity	NPC216092
0.8075	Intermediate Similarity	NPC117985
0.8067	Intermediate Similarity	NPC52358
0.8065	Intermediate Similarity	NPC215711
0.8065	Intermediate Similarity	NPC153417
0.8065	Intermediate Similarity	NPC73411
0.8065	Intermediate Similarity	NPC105415
0.8054	Intermediate Similarity	NPC268081
0.8054	Intermediate Similarity	NPC29638
0.8054	Intermediate Similarity	NPC301341
0.8054	Intermediate Similarity	NPC284184
0.8054	Intermediate Similarity	NPC472516
0.8052	Intermediate Similarity	NPC190572
0.8052	Intermediate Similarity	NPC225173
0.8052	Intermediate Similarity	NPC286038
0.8052	Intermediate Similarity	NPC163846
0.805	Intermediate Similarity	NPC474360
0.805	Intermediate Similarity	NPC477674
0.8042	Intermediate Similarity	NPC237868
0.8041	Intermediate Similarity	NPC298900
0.8039	Intermediate Similarity	NPC89664
0.8039	Intermediate Similarity	NPC27798
0.8039	Intermediate Similarity	NPC475813
0.8039	Intermediate Similarity	NPC93241
0.8039	Intermediate Similarity	NPC274085
0.8038	Intermediate Similarity	NPC41719
0.8038	Intermediate Similarity	NPC290927
0.8038	Intermediate Similarity	NPC477669
0.8037	Intermediate Similarity	NPC473766
0.8037	Intermediate Similarity	NPC473753
0.8037	Intermediate Similarity	NPC179015
0.8037	Intermediate Similarity	NPC173149
0.8037	Intermediate Similarity	NPC472784
0.8027	Intermediate Similarity	NPC287533
0.8027	Intermediate Similarity	NPC43627
0.8027	Intermediate Similarity	NPC254603
0.8026	Intermediate Similarity	NPC22467
0.8026	Intermediate Similarity	NPC254010
0.8025	Intermediate Similarity	NPC475777
0.8025	Intermediate Similarity	NPC258249
0.8025	Intermediate Similarity	NPC473022
0.8024	Intermediate Similarity	NPC470667
0.8024	Intermediate Similarity	NPC186800
0.8014	Intermediate Similarity	NPC324488
0.8013	Intermediate Similarity	NPC472515
0.8013	Intermediate Similarity	NPC477535
0.8013	Intermediate Similarity	NPC262635
0.8013	Intermediate Similarity	NPC37206
0.8013	Intermediate Similarity	NPC137009
0.8013	Intermediate Similarity	NPC88445
0.8013	Intermediate Similarity	NPC109007
0.8013	Intermediate Similarity	NPC136095

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 NPC471346 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	994
0.2-0.3	1639
0.3-0.4	2572
0.4-0.5	1983
0.5-0.6	1079
0.6-0.7	389
0.7-0.8	148
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8269	Intermediate Similarity	NPD7819	Suspended
0.8247	Intermediate Similarity	NPD3226	Approved
0.8243	Intermediate Similarity	NPD2346	Discontinued
0.8243	Intermediate Similarity	NPD1471	Phase 3
0.8176	Intermediate Similarity	NPD919	Approved
0.8153	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD2533	Approved
0.8105	Intermediate Similarity	NPD2532	Approved
0.8105	Intermediate Similarity	NPD2534	Approved
0.8077	Intermediate Similarity	NPD6599	Discontinued
0.8013	Intermediate Similarity	NPD1243	Approved
0.8	Intermediate Similarity	NPD7075	Discontinued
0.8	Intermediate Similarity	NPD920	Approved
0.7974	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD1247	Approved
0.7922	Intermediate Similarity	NPD6799	Approved
0.7911	Intermediate Similarity	NPD7411	Suspended
0.7871	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6801	Discontinued
0.784	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD2796	Approved
0.7791	Intermediate Similarity	NPD5494	Approved
0.7778	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1549	Phase 2
0.7697	Intermediate Similarity	NPD1551	Phase 2
0.7692	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6832	Phase 2
0.7673	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3817	Phase 2
0.7654	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD5401	Approved
0.7643	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6959	Discontinued
0.7632	Intermediate Similarity	NPD3748	Approved
0.7607	Intermediate Similarity	NPD3882	Suspended
0.7605	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5711	Approved
0.759	Intermediate Similarity	NPD5710	Approved
0.7584	Intermediate Similarity	NPD411	Approved
0.7584	Intermediate Similarity	NPD2313	Discontinued
0.7574	Intermediate Similarity	NPD5844	Phase 1
0.7561	Intermediate Similarity	NPD3749	Approved
0.7557	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD17	Approved
0.7551	Intermediate Similarity	NPD1019	Discontinued
0.7547	Intermediate Similarity	NPD5403	Approved
0.7546	Intermediate Similarity	NPD5402	Approved
0.7532	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD9717	Approved
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD1607	Approved
0.7483	Intermediate Similarity	NPD3266	Approved
0.7483	Intermediate Similarity	NPD3267	Approved
0.7469	Intermediate Similarity	NPD5890	Approved
0.7469	Intermediate Similarity	NPD5889	Approved
0.7468	Intermediate Similarity	NPD2935	Discontinued
0.7442	Intermediate Similarity	NPD6559	Discontinued
0.7436	Intermediate Similarity	NPD2800	Approved
0.7423	Intermediate Similarity	NPD1934	Approved
0.7419	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8285	Discontinued
0.7403	Intermediate Similarity	NPD1510	Phase 2
0.7397	Intermediate Similarity	NPD1608	Approved
0.7389	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3750	Approved
0.7381	Intermediate Similarity	NPD6232	Discontinued
0.7368	Intermediate Similarity	NPD4307	Phase 2
0.7368	Intermediate Similarity	NPD1240	Approved
0.7365	Intermediate Similarity	NPD1203	Approved
0.7361	Intermediate Similarity	NPD5691	Approved
0.7356	Intermediate Similarity	NPD8312	Approved
0.7356	Intermediate Similarity	NPD8313	Approved
0.7353	Intermediate Similarity	NPD7473	Discontinued
0.7337	Intermediate Similarity	NPD3926	Phase 2
0.7329	Intermediate Similarity	NPD1281	Approved
0.732	Intermediate Similarity	NPD1933	Approved
0.732	Intermediate Similarity	NPD447	Suspended
0.7312	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD4380	Phase 2
0.7301	Intermediate Similarity	NPD6585	Discontinued
0.7289	Intermediate Similarity	NPD7768	Phase 2
0.7278	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6808	Phase 2
0.7267	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1512	Approved
0.7237	Intermediate Similarity	NPD3268	Approved
0.7232	Intermediate Similarity	NPD8434	Phase 2
0.7232	Intermediate Similarity	NPD8150	Discontinued
0.7211	Intermediate Similarity	NPD1611	Approved
0.7209	Intermediate Similarity	NPD7177	Discontinued
0.7197	Intermediate Similarity	NPD6004	Phase 3
0.7197	Intermediate Similarity	NPD2344	Approved
0.7197	Intermediate Similarity	NPD6002	Phase 3
0.7197	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5762	Approved
0.7197	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6005	Phase 3
0.7197	Intermediate Similarity	NPD5763	Approved
0.7193	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6166	Phase 2
0.7192	Intermediate Similarity	NPD1778	Approved
0.7181	Intermediate Similarity	NPD1283	Approved
0.7179	Intermediate Similarity	NPD4308	Phase 3
0.7179	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7033	Discontinued
0.716	Intermediate Similarity	NPD6273	Approved
0.7151	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD2979	Phase 3
0.7143	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1511	Approved
0.7134	Intermediate Similarity	NPD5408	Approved
0.7134	Intermediate Similarity	NPD2438	Suspended
0.7134	Intermediate Similarity	NPD5406	Approved
0.7134	Intermediate Similarity	NPD5404	Approved
0.7134	Intermediate Similarity	NPD5405	Approved
0.7134	Intermediate Similarity	NPD6099	Approved
0.7134	Intermediate Similarity	NPD6100	Approved
0.7125	Intermediate Similarity	NPD3887	Approved
0.7124	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1651	Approved
0.7117	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3751	Discontinued
0.711	Intermediate Similarity	NPD3818	Discontinued
0.7102	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6355	Discontinued
0.7093	Intermediate Similarity	NPD2403	Approved
0.7086	Intermediate Similarity	NPD6797	Phase 2
0.7086	Intermediate Similarity	NPD2798	Approved
0.7083	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4626	Approved
0.7063	Intermediate Similarity	NPD1241	Discontinued
0.7047	Intermediate Similarity	NPD3972	Approved
0.7045	Intermediate Similarity	NPD7251	Discontinued
0.7044	Intermediate Similarity	NPD2897	Discontinued
0.7035	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD9493	Approved
0.7032	Intermediate Similarity	NPD4060	Phase 1
0.702	Intermediate Similarity	NPD1470	Approved
0.7019	Intermediate Similarity	NPD2309	Approved
0.7006	Intermediate Similarity	NPD7808	Phase 3
0.6994	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6779	Approved
0.6989	Remote Similarity	NPD6782	Approved
0.6989	Remote Similarity	NPD6777	Approved
0.6989	Remote Similarity	NPD5953	Discontinued
0.6989	Remote Similarity	NPD6776	Approved
0.6989	Remote Similarity	NPD6780	Approved
0.6989	Remote Similarity	NPD6781	Approved
0.6989	Remote Similarity	NPD6778	Approved
0.6981	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2353	Approved
0.698	Remote Similarity	NPD1201	Approved
0.6977	Remote Similarity	NPD3787	Discontinued
0.6977	Remote Similarity	NPD7229	Phase 3
0.6972	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD8032	Phase 2
0.6964	Remote Similarity	NPD2801	Approved
0.6964	Remote Similarity	NPD1465	Phase 2
0.6961	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7003	Approved
0.6954	Remote Similarity	NPD1876	Approved
0.6949	Remote Similarity	NPD6764	Approved
0.6949	Remote Similarity	NPD6765	Approved
0.6939	Remote Similarity	NPD9545	Approved
0.6932	Remote Similarity	NPD7074	Phase 3
0.6928	Remote Similarity	NPD7458	Discontinued
0.6927	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7874	Approved
0.6923	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2531	Phase 2
0.6914	Remote Similarity	NPD2163	Approved
0.6908	Remote Similarity	NPD2797	Approved
0.6903	Remote Similarity	NPD1296	Phase 2
0.6903	Remote Similarity	NPD3764	Approved
0.6903	Remote Similarity	NPD6798	Discontinued
0.6898	Remote Similarity	NPD4107	Approved
0.6894	Remote Similarity	NPD2654	Approved
0.6893	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7697	Approved
0.6878	Remote Similarity	NPD7696	Phase 3
0.6878	Remote Similarity	NPD7698	Approved
0.6875	Remote Similarity	NPD7054	Approved
0.6875	Remote Similarity	NPD7286	Phase 2
0.6864	Remote Similarity	NPD5760	Phase 2
0.6864	Remote Similarity	NPD5761	Phase 2
0.6848	Remote Similarity	NPD5049	Phase 3
0.6846	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3225	Approved
0.6842	Remote Similarity	NPD7871	Phase 2
0.6842	Remote Similarity	NPD7870	Phase 2

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