NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.12
Volume:	266.942
LogP:	2.889
LogD:	3.004
LogS:	-3.68
# Rotatable Bonds:	1
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.828
Synthetic Accessibility Score:	3.916
Fsp3:	0.467
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:	-4.899
MDCK Permeability:	1.7283218767261133e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.23
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.141
Plasma Protein Binding (PPB):	98.2013931274414%
Volume Distribution (VD):	1.397
Pgp-substrate:	4.228013038635254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.797
CYP1A2-substrate:	0.929
CYP2C19-inhibitor:	0.195
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.554
CYP2C9-substrate:	0.626
CYP2D6-inhibitor:	0.128
CYP2D6-substrate:	0.383
CYP3A4-inhibitor:	0.1
CYP3A4-substrate:	0.516

ADMET: Excretion

Clearance (CL):	7.407
Half-life (T1/2):	0.498

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.962
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.603
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.491
Carcinogencity:	0.913
Eye Corrosion:	0.003
Eye Irritation:	0.032
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: NPC471349

Natural Product ID:	NPC471349
*Common Name:**	(2R,7R,9S)-9-Hydroxy-7-Methyl-2-Propan-2-Yl-7,9-Dihydro-6H-Furo[3,2-H]Isochromen-3-One
IUPAC Name:	(2R,7R,9S)-9-hydroxy-7-methyl-2-propan-2-yl-7,9-dihydro-6H-furo[3,2-h]isochromen-3-one
Synonyms:
Standard InCHIKey:	AVYZYONEAKDESK-YVILZHTOSA-N
Standard InCHI:	InChI=1S/C15H18O4/c1-7(2)13-12(16)10-5-4-9-6-8(3)18-15(17)11(9)14(10)19-13/h4-5,7-8,13,15,17H,6H2,1-3H3/t8-,13-,15+/m1/s1
SMILES:	C[C@H]1O[C@H](O)c2c(C1)ccc1c2O[C@@H](C1=O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419846
PubChem CID:	73347663
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	>	100000.0	nM	PMID[564983]

☑ 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 NPC471349 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	365
0.1-0.2	1359
0.2-0.3	3043
0.3-0.4	7431
0.4-0.5	11510
0.5-0.6	4206
0.6-0.7	6929
0.7-0.8	7403
0.8-0.85	433
0.85-0.9	9
0.9-0.95	2
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471347
0.9931	High Similarity	NPC175617
0.9524	High Similarity	NPC228906
0.9524	High Similarity	NPC471348
0.9524	High Similarity	NPC469416
0.9456	High Similarity	NPC219560
0.9448	High Similarity	NPC469385
0.9128	High Similarity	NPC469425
0.8933	High Similarity	NPC471346
0.8784	High Similarity	NPC477537
0.8699	High Similarity	NPC217914
0.8658	High Similarity	NPC477535
0.8625	High Similarity	NPC216752
0.859	High Similarity	NPC473967
0.8535	High Similarity	NPC470331
0.8509	High Similarity	NPC212099
0.8509	High Similarity	NPC101116
0.8509	High Similarity	NPC278329
0.8509	High Similarity	NPC146837
0.85	High Similarity	NPC313368
0.8497	Intermediate Similarity	NPC474630
0.8494	Intermediate Similarity	NPC470667
0.8456	Intermediate Similarity	NPC477534
0.8405	Intermediate Similarity	NPC314653
0.8405	Intermediate Similarity	NPC316262
0.8405	Intermediate Similarity	NPC178281
0.8397	Intermediate Similarity	NPC104172
0.8397	Intermediate Similarity	NPC88886
0.8387	Intermediate Similarity	NPC471734
0.8387	Intermediate Similarity	NPC71055
0.8383	Intermediate Similarity	NPC186800
0.8366	Intermediate Similarity	NPC469885
0.8364	Intermediate Similarity	NPC191653
0.8364	Intermediate Similarity	NPC473202
0.8354	Intermediate Similarity	NPC87708
0.8354	Intermediate Similarity	NPC178851
0.8344	Intermediate Similarity	NPC477408
0.8344	Intermediate Similarity	NPC325983
0.8333	Intermediate Similarity	NPC475233
0.8323	Intermediate Similarity	NPC471735
0.8323	Intermediate Similarity	NPC98776
0.8323	Intermediate Similarity	NPC85368
0.8313	Intermediate Similarity	NPC315306
0.8313	Intermediate Similarity	NPC164244
0.8313	Intermediate Similarity	NPC313717
0.8312	Intermediate Similarity	NPC477409
0.8311	Intermediate Similarity	NPC477536
0.8303	Intermediate Similarity	NPC63470
0.8302	Intermediate Similarity	NPC301233
0.8299	Intermediate Similarity	NPC324488
0.8291	Intermediate Similarity	NPC232645
0.8291	Intermediate Similarity	NPC318424
0.8291	Intermediate Similarity	NPC72958
0.8278	Intermediate Similarity	NPC98395
0.8272	Intermediate Similarity	NPC470358
0.8272	Intermediate Similarity	NPC306978
0.8263	Intermediate Similarity	NPC76128
0.8263	Intermediate Similarity	NPC30432
0.8263	Intermediate Similarity	NPC111536
0.8263	Intermediate Similarity	NPC271385
0.8263	Intermediate Similarity	NPC5029
0.8261	Intermediate Similarity	NPC217602
0.8261	Intermediate Similarity	NPC104380
0.8261	Intermediate Similarity	NPC473282
0.8253	Intermediate Similarity	NPC470207
0.8253	Intermediate Similarity	NPC470206
0.8253	Intermediate Similarity	NPC259905
0.8239	Intermediate Similarity	NPC271681
0.8239	Intermediate Similarity	NPC275878
0.8232	Intermediate Similarity	NPC17432
0.8232	Intermediate Similarity	NPC471286
0.8228	Intermediate Similarity	NPC158866
0.8228	Intermediate Similarity	NPC202595
0.8228	Intermediate Similarity	NPC473966
0.8225	Intermediate Similarity	NPC475246
0.8224	Intermediate Similarity	NPC268691
0.8221	Intermediate Similarity	NPC269117
0.8221	Intermediate Similarity	NPC472783
0.8221	Intermediate Similarity	NPC472780
0.8214	Intermediate Similarity	NPC203751
0.8214	Intermediate Similarity	NPC199357
0.821	Intermediate Similarity	NPC186113
0.8205	Intermediate Similarity	NPC470357
0.8204	Intermediate Similarity	NPC298778
0.82	Intermediate Similarity	NPC27407
0.82	Intermediate Similarity	NPC142027
0.8199	Intermediate Similarity	NPC211482
0.8199	Intermediate Similarity	NPC476652
0.8194	Intermediate Similarity	NPC475813
0.8193	Intermediate Similarity	NPC472660
0.8187	Intermediate Similarity	NPC472799
0.8187	Intermediate Similarity	NPC193200
0.8187	Intermediate Similarity	NPC135522
0.8182	Intermediate Similarity	NPC329493
0.8176	Intermediate Similarity	NPC5671
0.8176	Intermediate Similarity	NPC39819
0.8171	Intermediate Similarity	NPC125991
0.8171	Intermediate Similarity	NPC475106
0.8171	Intermediate Similarity	NPC310603
0.817	Intermediate Similarity	NPC37206
0.8166	Intermediate Similarity	NPC474345
0.8166	Intermediate Similarity	NPC3718
0.8166	Intermediate Similarity	NPC68381
0.8165	Intermediate Similarity	NPC70764
0.8165	Intermediate Similarity	NPC226578
0.816	Intermediate Similarity	NPC472618
0.816	Intermediate Similarity	NPC472782
0.816	Intermediate Similarity	NPC472781
0.8153	Intermediate Similarity	NPC137296
0.8153	Intermediate Similarity	NPC8817
0.8153	Intermediate Similarity	NPC66991
0.8148	Intermediate Similarity	NPC281137
0.8148	Intermediate Similarity	NPC476930
0.8148	Intermediate Similarity	NPC96342
0.8148	Intermediate Similarity	NPC470606
0.8148	Intermediate Similarity	NPC164110
0.8148	Intermediate Similarity	NPC212967
0.8148	Intermediate Similarity	NPC282390
0.8148	Intermediate Similarity	NPC317900
0.8148	Intermediate Similarity	NPC294300
0.8148	Intermediate Similarity	NPC476404
0.8148	Intermediate Similarity	NPC246647
0.8148	Intermediate Similarity	NPC177742
0.8144	Intermediate Similarity	NPC222455
0.8144	Intermediate Similarity	NPC246274
0.8141	Intermediate Similarity	NPC28632
0.8137	Intermediate Similarity	NPC174599
0.8137	Intermediate Similarity	NPC192219
0.8137	Intermediate Similarity	NPC237560
0.8137	Intermediate Similarity	NPC82190
0.8133	Intermediate Similarity	NPC191012
0.8129	Intermediate Similarity	NPC471731
0.8129	Intermediate Similarity	NPC299149
0.8129	Intermediate Similarity	NPC277710
0.8129	Intermediate Similarity	NPC469542
0.8129	Intermediate Similarity	NPC153578
0.8129	Intermediate Similarity	NPC244903
0.8129	Intermediate Similarity	NPC114257
0.8125	Intermediate Similarity	NPC321363
0.8125	Intermediate Similarity	NPC183536
0.8125	Intermediate Similarity	NPC34965
0.8125	Intermediate Similarity	NPC253904
0.8125	Intermediate Similarity	NPC154683
0.8125	Intermediate Similarity	NPC273483
0.8125	Intermediate Similarity	NPC40356
0.8121	Intermediate Similarity	NPC100849
0.8121	Intermediate Similarity	NPC66087
0.8121	Intermediate Similarity	NPC179198
0.8121	Intermediate Similarity	NPC290160
0.8121	Intermediate Similarity	NPC278419
0.8121	Intermediate Similarity	NPC91288
0.8118	Intermediate Similarity	NPC46958
0.8118	Intermediate Similarity	NPC289876
0.8118	Intermediate Similarity	NPC102053
0.8117	Intermediate Similarity	NPC149533
0.8117	Intermediate Similarity	NPC283292
0.8113	Intermediate Similarity	NPC150928
0.811	Intermediate Similarity	NPC476929
0.811	Intermediate Similarity	NPC117985
0.811	Intermediate Similarity	NPC24761
0.8107	Intermediate Similarity	NPC213052
0.8101	Intermediate Similarity	NPC37139
0.8101	Intermediate Similarity	NPC5537
0.8101	Intermediate Similarity	NPC215711
0.8101	Intermediate Similarity	NPC73411
0.8098	Intermediate Similarity	NPC53139
0.8098	Intermediate Similarity	NPC279732
0.8098	Intermediate Similarity	NPC470607
0.8095	Intermediate Similarity	NPC477571
0.8095	Intermediate Similarity	NPC477573
0.8095	Intermediate Similarity	NPC477572
0.8089	Intermediate Similarity	NPC286038
0.8089	Intermediate Similarity	NPC300540
0.8089	Intermediate Similarity	NPC120536
0.8089	Intermediate Similarity	NPC469758
0.8086	Intermediate Similarity	NPC17521
0.8086	Intermediate Similarity	NPC283480
0.8086	Intermediate Similarity	NPC148323
0.8086	Intermediate Similarity	NPC180924
0.8086	Intermediate Similarity	NPC477674
0.8086	Intermediate Similarity	NPC154341
0.8084	Intermediate Similarity	NPC48640
0.8084	Intermediate Similarity	NPC149244
0.8084	Intermediate Similarity	NPC150131
0.8081	Intermediate Similarity	NPC477860
0.8081	Intermediate Similarity	NPC475161
0.8079	Intermediate Similarity	NPC470844
0.8077	Intermediate Similarity	NPC10302
0.8077	Intermediate Similarity	NPC105381
0.8077	Intermediate Similarity	NPC89664
0.8077	Intermediate Similarity	NPC471451
0.8077	Intermediate Similarity	NPC274085
0.8077	Intermediate Similarity	NPC42540
0.8077	Intermediate Similarity	NPC151607
0.8075	Intermediate Similarity	NPC60084
0.8075	Intermediate Similarity	NPC185103
0.8075	Intermediate Similarity	NPC210942
0.8075	Intermediate Similarity	NPC169990
0.8072	Intermediate Similarity	NPC472784
0.807	Intermediate Similarity	NPC47191

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 NPC471349 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	899
0.2-0.3	1640
0.3-0.4	2545
0.4-0.5	2074
0.5-0.6	1087
0.6-0.7	418
0.7-0.8	170
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8107	Intermediate Similarity	NPD6559	Discontinued
0.8075	Intermediate Similarity	NPD7819	Suspended
0.8039	Intermediate Similarity	NPD2346	Discontinued
0.8025	Intermediate Similarity	NPD2532	Approved
0.8025	Intermediate Similarity	NPD2534	Approved
0.8025	Intermediate Similarity	NPD2533	Approved
0.8012	Intermediate Similarity	NPD8313	Approved
0.8012	Intermediate Similarity	NPD8312	Approved
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD3226	Approved
0.7937	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7075	Discontinued
0.7818	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6801	Discontinued
0.7784	Intermediate Similarity	NPD6959	Discontinued
0.7778	Intermediate Similarity	NPD6599	Discontinued
0.7765	Intermediate Similarity	NPD3818	Discontinued
0.7758	Intermediate Similarity	NPD3882	Suspended
0.7756	Intermediate Similarity	NPD1549	Phase 2
0.7756	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6797	Phase 2
0.7697	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7251	Discontinued
0.7644	Intermediate Similarity	NPD7808	Phase 3
0.7628	Intermediate Similarity	NPD1551	Phase 2
0.7625	Intermediate Similarity	NPD6799	Approved
0.7622	Intermediate Similarity	NPD7411	Suspended
0.7619	Intermediate Similarity	NPD5494	Approved
0.7616	Intermediate Similarity	NPD5844	Phase 1
0.7596	Intermediate Similarity	NPD6776	Approved
0.7596	Intermediate Similarity	NPD6777	Approved
0.7596	Intermediate Similarity	NPD6778	Approved
0.7596	Intermediate Similarity	NPD6781	Approved
0.7596	Intermediate Similarity	NPD6779	Approved
0.7596	Intermediate Similarity	NPD6782	Approved
0.7596	Intermediate Similarity	NPD6780	Approved
0.7593	Intermediate Similarity	NPD5403	Approved
0.759	Intermediate Similarity	NPD5402	Approved
0.758	Intermediate Similarity	NPD1471	Phase 3
0.7572	Intermediate Similarity	NPD7074	Phase 3
0.7568	Intermediate Similarity	NPD7435	Discontinued
0.7564	Intermediate Similarity	NPD2799	Discontinued
0.7561	Intermediate Similarity	NPD4380	Phase 2
0.756	Intermediate Similarity	NPD919	Approved
0.7548	Intermediate Similarity	NPD1607	Approved
0.7547	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4628	Phase 3
0.7547	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5711	Approved
0.7529	Intermediate Similarity	NPD5710	Approved
0.7516	Intermediate Similarity	NPD2796	Approved
0.7516	Intermediate Similarity	NPD2935	Discontinued
0.7516	Intermediate Similarity	NPD411	Approved
0.7514	Intermediate Similarity	NPD7054	Approved
0.7484	Intermediate Similarity	NPD2800	Approved
0.7484	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2798	Approved
0.7473	Intermediate Similarity	NPD7697	Approved
0.7473	Intermediate Similarity	NPD7698	Approved
0.7473	Intermediate Similarity	NPD7696	Phase 3
0.7471	Intermediate Similarity	NPD7472	Approved
0.747	Intermediate Similarity	NPD1934	Approved
0.7469	Intermediate Similarity	NPD5401	Approved
0.7469	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6004	Phase 3
0.7468	Intermediate Similarity	NPD6002	Phase 3
0.7468	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6005	Phase 3
0.7468	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD3751	Discontinued
0.7452	Intermediate Similarity	NPD1510	Phase 2
0.745	Intermediate Similarity	NPD9717	Approved
0.7442	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6166	Phase 2
0.7442	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD7871	Phase 2
0.7433	Intermediate Similarity	NPD7870	Phase 2
0.7419	Intermediate Similarity	NPD1240	Approved
0.7418	Intermediate Similarity	NPD6534	Approved
0.7418	Intermediate Similarity	NPD6535	Approved
0.7405	Intermediate Similarity	NPD6099	Approved
0.7405	Intermediate Similarity	NPD6100	Approved
0.7403	Intermediate Similarity	NPD2313	Discontinued
0.7399	Intermediate Similarity	NPD7473	Discontinued
0.7396	Intermediate Similarity	NPD3749	Approved
0.7383	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3817	Phase 2
0.7378	Intermediate Similarity	NPD920	Approved
0.7375	Intermediate Similarity	NPD1243	Approved
0.7374	Intermediate Similarity	NPD8150	Discontinued
0.7368	Intermediate Similarity	NPD1247	Approved
0.7358	Intermediate Similarity	NPD5763	Approved
0.7358	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5762	Approved
0.7346	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7768	Phase 2
0.733	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7874	Approved
0.7329	Intermediate Similarity	NPD3750	Approved
0.7326	Intermediate Similarity	NPD3787	Discontinued
0.7326	Intermediate Similarity	NPD6232	Discontinued
0.7317	Intermediate Similarity	NPD6273	Approved
0.7317	Intermediate Similarity	NPD1512	Approved
0.7316	Intermediate Similarity	NPD7701	Phase 2
0.7303	Intermediate Similarity	NPD1203	Approved
0.7297	Intermediate Similarity	NPD7700	Phase 2
0.7297	Intermediate Similarity	NPD7699	Phase 2
0.7292	Intermediate Similarity	NPD7801	Approved
0.7289	Intermediate Similarity	NPD7458	Discontinued
0.7283	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD6832	Phase 2
0.7262	Intermediate Similarity	NPD37	Approved
0.7261	Intermediate Similarity	NPD447	Suspended
0.7256	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2344	Approved
0.7249	Intermediate Similarity	NPD8320	Phase 1
0.7249	Intermediate Similarity	NPD8319	Approved
0.7235	Intermediate Similarity	NPD4967	Phase 2
0.7235	Intermediate Similarity	NPD4965	Approved
0.7235	Intermediate Similarity	NPD4966	Approved
0.7234	Intermediate Similarity	NPD6823	Phase 2
0.7233	Intermediate Similarity	NPD7033	Discontinued
0.7233	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1608	Approved
0.7219	Intermediate Similarity	NPD5761	Phase 2
0.7219	Intermediate Similarity	NPD5760	Phase 2
0.7198	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4060	Phase 1
0.7195	Intermediate Similarity	NPD1511	Approved
0.719	Intermediate Similarity	NPD1470	Approved
0.7188	Intermediate Similarity	NPD5408	Approved
0.7188	Intermediate Similarity	NPD5404	Approved
0.7188	Intermediate Similarity	NPD5406	Approved
0.7188	Intermediate Similarity	NPD5405	Approved
0.7179	Intermediate Similarity	NPD3268	Approved
0.7174	Intermediate Similarity	NPD6212	Phase 3
0.7174	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6213	Phase 3
0.7168	Intermediate Similarity	NPD7199	Phase 2
0.716	Intermediate Similarity	NPD6674	Discontinued
0.7159	Intermediate Similarity	NPD7177	Discontinued
0.7152	Intermediate Similarity	NPD1091	Approved
0.7152	Intermediate Similarity	NPD1201	Approved
0.7152	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1778	Approved
0.7127	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4308	Phase 3
0.7125	Intermediate Similarity	NPD3748	Approved
0.7124	Intermediate Similarity	NPD1283	Approved
0.7118	Intermediate Similarity	NPD2801	Approved
0.7117	Intermediate Similarity	NPD7003	Approved
0.7115	Intermediate Similarity	NPD4625	Phase 3
0.7107	Intermediate Similarity	NPD6651	Approved
0.7086	Intermediate Similarity	NPD3926	Phase 2
0.7078	Intermediate Similarity	NPD2797	Approved
0.7073	Intermediate Similarity	NPD2309	Approved
0.707	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7799	Discontinued
0.7062	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7228	Approved
0.7052	Intermediate Similarity	NPD6234	Discontinued
0.705	Intermediate Similarity	NPD8366	Approved
0.7044	Intermediate Similarity	NPD1933	Approved
0.7044	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5124	Phase 1
0.7035	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1019	Discontinued
0.7026	Intermediate Similarity	NPD7783	Phase 2
0.7026	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD17	Approved
0.702	Intermediate Similarity	NPD4626	Approved
0.7018	Intermediate Similarity	NPD8455	Phase 2
0.701	Intermediate Similarity	NPD8151	Discontinued
0.7006	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.698	Remote Similarity	NPD9493	Approved
0.6965	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6844	Discontinued
0.6954	Remote Similarity	NPD5691	Approved
0.6954	Remote Similarity	NPD1651	Approved
0.6951	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4749	Approved
0.6944	Remote Similarity	NPD5953	Discontinued
0.6944	Remote Similarity	NPD7993	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