NPASS Compound

Structure

NPC215612 OpenBabel07101719152D 22 24 0 0 1 0 0 0 0 0999 V2000 0.9659 -0.7412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 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 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1305 -1.9914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 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 2 21 1 0 0 0 0 3 8 2 0 0 0 0 3 9 1 0 0 0 0 4 15 1 0 0 0 0 5 22 1 0 0 0 0 6 4 1 1 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 5 1 1 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 14 2 0 0 0 0 9 21 1 0 0 0 0 10 11 2 0 0 0 0 10 13 1 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 12 17 1 1 0 0 0 13 18 2 0 0 0 0 14 19 1 0 0 0 0 15 1 1 6 0 0 0 15 20 1 0 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.11
Volume:	293.313
LogP:	0.675
LogD:	0.526
LogS:	-2.017
# Rotatable Bonds:	1
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.558
Synthetic Accessibility Score:	4.547
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.656
MDCK Permeability:	5.634562512568664e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.813
Human Intestinal Absorption (HIA):	0.923
20% Bioavailability (F20%):	0.789
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	51.17028045654297%
Volume Distribution (VD):	1.391
Pgp-substrate:	39.386268615722656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.213
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.678
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.415
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	9.081
Half-life (T1/2):	0.484

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.782
AMES Toxicity:	0.519
Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.779
Carcinogencity:	0.084
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.161

Download Data

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

Natural Product: NPC215612

Natural Product ID:	NPC215612
*Common Name:**	UHLYLCLJRKLDOP-UWTYKGBHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UHLYLCLJRKLDOP-UWTYKGBHSA-N
Standard InCHI:	InChI=1S/C15H18O7/c1-15(20)4-6-7(5-22-15)13(18)10-8(16)3-9(21-2)14(19)11(10)12(6)17/h3,6-7,12,16-17,19-20H,4-5H2,1-2H3/t6-,7+,12-,15-/m1/s1
SMILES:	C[C@@]1(C[C@@H]2[C@H](CO1)C(=O)c1c(cc(c(c1[C@@H]2O)O)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3334768
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO7122	Fusarium solani	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21348469]
NPO7122	Fusarium solani	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25163667]
NPO7122	Fusarium solani	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28257197]
NPO7122	Fusarium solani	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO7122	Fusarium solani	Species	Nectriaceae	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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	30000.0	nM	PMID[450637]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	13100.0	nM	PMID[450637]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	27000.0	nM	PMID[450637]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	30000.0	nM	PMID[450637]

☑ 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 NPC215612 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	398
0.1-0.2	1609
0.2-0.3	3479
0.3-0.4	8127
0.4-0.5	9992
0.5-0.6	4208
0.6-0.7	5083
0.7-0.8	6693
0.8-0.85	2458
0.85-0.9	622
0.9-0.95	24
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9487	High Similarity	NPC155302
0.9487	High Similarity	NPC161947
0.9484	High Similarity	NPC179732
0.9427	High Similarity	NPC87431
0.9231	High Similarity	NPC472048
0.9187	High Similarity	NPC7483
0.9177	High Similarity	NPC329091
0.9167	High Similarity	NPC281477
0.9136	High Similarity	NPC117854
0.9136	High Similarity	NPC477154
0.9136	High Similarity	NPC6588
0.913	High Similarity	NPC326520
0.913	High Similarity	NPC25361
0.9119	High Similarity	NPC14353
0.9119	High Similarity	NPC228785
0.9119	High Similarity	NPC56085
0.9114	High Similarity	NPC241904
0.9114	High Similarity	NPC300727
0.9114	High Similarity	NPC469584
0.9108	High Similarity	NPC16082
0.9108	High Similarity	NPC82592
0.9085	High Similarity	NPC260263
0.9074	High Similarity	NPC472452
0.9074	High Similarity	NPC170245
0.9068	High Similarity	NPC475985
0.9068	High Similarity	NPC236132
0.9068	High Similarity	NPC197168
0.9062	High Similarity	NPC278052
0.9062	High Similarity	NPC474186
0.9062	High Similarity	NPC40491
0.9062	High Similarity	NPC61010
0.9057	High Similarity	NPC476242
0.9057	High Similarity	NPC470339
0.9057	High Similarity	NPC100123
0.9051	High Similarity	NPC164427
0.9051	High Similarity	NPC274730
0.9	High Similarity	NPC320359
0.9	High Similarity	NPC36217
0.9	High Similarity	NPC474287
0.9	High Similarity	NPC472055
0.9	High Similarity	NPC475886
0.8994	High Similarity	NPC217677
0.8994	High Similarity	NPC162869
0.8994	High Similarity	NPC472913
0.8994	High Similarity	NPC48208
0.8994	High Similarity	NPC84935
0.8994	High Similarity	NPC165977
0.8994	High Similarity	NPC472914
0.8994	High Similarity	NPC474836
0.8994	High Similarity	NPC245758
0.8994	High Similarity	NPC222814
0.8994	High Similarity	NPC77679
0.8994	High Similarity	NPC474208
0.8994	High Similarity	NPC472911
0.8994	High Similarity	NPC190020
0.8994	High Similarity	NPC96167
0.8994	High Similarity	NPC475267
0.8994	High Similarity	NPC156057
0.8994	High Similarity	NPC223787
0.8994	High Similarity	NPC472910
0.8987	High Similarity	NPC68727
0.8987	High Similarity	NPC175192
0.8987	High Similarity	NPC199926
0.8981	High Similarity	NPC268992
0.8981	High Similarity	NPC51824
0.8981	High Similarity	NPC167903
0.8981	High Similarity	NPC470338
0.8981	High Similarity	NPC470337
0.8981	High Similarity	NPC113608
0.8963	High Similarity	NPC95855
0.8963	High Similarity	NPC210042
0.8963	High Similarity	NPC183036
0.8951	High Similarity	NPC236521
0.8951	High Similarity	NPC220313
0.8951	High Similarity	NPC94777
0.8951	High Similarity	NPC152659
0.8951	High Similarity	NPC270837
0.8951	High Similarity	NPC248638
0.8944	High Similarity	NPC474351
0.8944	High Similarity	NPC266314
0.8944	High Similarity	NPC474187
0.8944	High Similarity	NPC65746
0.8944	High Similarity	NPC475883
0.8938	High Similarity	NPC250214
0.8938	High Similarity	NPC95936
0.8938	High Similarity	NPC45846
0.8938	High Similarity	NPC85121
0.8931	High Similarity	NPC142339
0.8931	High Similarity	NPC474167
0.8931	High Similarity	NPC470762
0.8931	High Similarity	NPC235165
0.8931	High Similarity	NPC227062
0.8931	High Similarity	NPC255106
0.8931	High Similarity	NPC150227
0.8929	High Similarity	NPC212290
0.8924	High Similarity	NPC291510
0.8924	High Similarity	NPC197188
0.8924	High Similarity	NPC116850
0.8924	High Similarity	NPC144801
0.8924	High Similarity	NPC43872
0.8924	High Similarity	NPC89474
0.8924	High Similarity	NPC238672
0.8917	High Similarity	NPC171010
0.8917	High Similarity	NPC202157
0.8909	High Similarity	NPC21190
0.8909	High Similarity	NPC224462
0.8909	High Similarity	NPC183357
0.8909	High Similarity	NPC22195
0.8909	High Similarity	NPC474434
0.8902	High Similarity	NPC93099
0.8902	High Similarity	NPC474024
0.8896	High Similarity	NPC475888
0.8896	High Similarity	NPC275780
0.8896	High Similarity	NPC473286
0.8896	High Similarity	NPC472450
0.8896	High Similarity	NPC239752
0.8889	High Similarity	NPC25152
0.8889	High Similarity	NPC294965
0.8889	High Similarity	NPC220912
0.8889	High Similarity	NPC211107
0.8889	High Similarity	NPC201800
0.8889	High Similarity	NPC472964
0.8889	High Similarity	NPC469575
0.8882	High Similarity	NPC263449
0.8882	High Similarity	NPC200746
0.8882	High Similarity	NPC119224
0.8882	High Similarity	NPC472902
0.8882	High Similarity	NPC84571
0.8882	High Similarity	NPC321399
0.8875	High Similarity	NPC262286
0.8875	High Similarity	NPC78103
0.8875	High Similarity	NPC210084
0.8875	High Similarity	NPC78225
0.8875	High Similarity	NPC181960
0.8875	High Similarity	NPC472598
0.8875	High Similarity	NPC236796
0.8875	High Similarity	NPC36852
0.8875	High Similarity	NPC470402
0.8875	High Similarity	NPC99597
0.8875	High Similarity	NPC129684
0.8875	High Similarity	NPC474055
0.8875	High Similarity	NPC299520
0.8868	High Similarity	NPC472909
0.8868	High Similarity	NPC45849
0.8868	High Similarity	NPC200761
0.8868	High Similarity	NPC130589
0.8868	High Similarity	NPC134287
0.8868	High Similarity	NPC37392
0.8868	High Similarity	NPC477503
0.8868	High Similarity	NPC470327
0.8868	High Similarity	NPC67396
0.8868	High Similarity	NPC79998
0.8861	High Similarity	NPC470340
0.8861	High Similarity	NPC101996
0.8861	High Similarity	NPC180234
0.8861	High Similarity	NPC180944
0.8861	High Similarity	NPC199100
0.8861	High Similarity	NPC120537
0.8861	High Similarity	NPC39007
0.8861	High Similarity	NPC161277
0.8855	High Similarity	NPC48773
0.8855	High Similarity	NPC205076
0.8855	High Similarity	NPC307518
0.8854	High Similarity	NPC151473
0.8854	High Similarity	NPC216917
0.8848	High Similarity	NPC58053
0.8848	High Similarity	NPC93337
0.8848	High Similarity	NPC469931
0.8848	High Similarity	NPC45638
0.8848	High Similarity	NPC105025
0.8848	High Similarity	NPC170675
0.8848	High Similarity	NPC112755
0.8848	High Similarity	NPC475942
0.8848	High Similarity	NPC186807
0.8848	High Similarity	NPC201292
0.8848	High Similarity	NPC471457
0.8848	High Similarity	NPC472381
0.8848	High Similarity	NPC472383
0.8848	High Similarity	NPC226294
0.8841	High Similarity	NPC43319
0.8841	High Similarity	NPC20237
0.8841	High Similarity	NPC37870
0.8841	High Similarity	NPC99957
0.8841	High Similarity	NPC181616
0.8841	High Similarity	NPC39091
0.8834	High Similarity	NPC470178
0.8834	High Similarity	NPC147596
0.8834	High Similarity	NPC146134
0.8834	High Similarity	NPC186686
0.8834	High Similarity	NPC273959
0.8834	High Similarity	NPC249181
0.8834	High Similarity	NPC474350
0.8834	High Similarity	NPC189473
0.8834	High Similarity	NPC41301
0.8834	High Similarity	NPC23298
0.8834	High Similarity	NPC474240
0.8827	High Similarity	NPC311740
0.8827	High Similarity	NPC32694
0.8827	High Similarity	NPC308992
0.8827	High Similarity	NPC228383

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 NPC215612 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	944
0.2-0.3	1940
0.3-0.4	2621
0.4-0.5	1823
0.5-0.6	906
0.6-0.7	407
0.7-0.8	129
0.8-0.85	32
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8742	High Similarity	NPD1934	Approved
0.8688	High Similarity	NPD2801	Approved
0.8688	High Similarity	NPD2393	Clinical (unspecified phase)
0.8571	High Similarity	NPD7074	Phase 3
0.8563	High Similarity	NPD3818	Discontinued
0.8529	High Similarity	NPD4338	Clinical (unspecified phase)
0.8512	High Similarity	NPD7054	Approved
0.8503	High Similarity	NPD7473	Discontinued
0.8462	Intermediate Similarity	NPD7472	Approved
0.8443	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6166	Phase 2
0.8443	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD6232	Discontinued
0.8424	Intermediate Similarity	NPD5494	Approved
0.8402	Intermediate Similarity	NPD5844	Phase 1
0.8304	Intermediate Similarity	NPD6797	Phase 2
0.8272	Intermediate Similarity	NPD4380	Phase 2
0.8256	Intermediate Similarity	NPD7251	Discontinued
0.8253	Intermediate Similarity	NPD6234	Discontinued
0.8242	Intermediate Similarity	NPD3882	Suspended
0.8242	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1511	Approved
0.8232	Intermediate Similarity	NPD1465	Phase 2
0.8208	Intermediate Similarity	NPD7808	Phase 3
0.8193	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD37	Approved
0.8155	Intermediate Similarity	NPD6959	Discontinued
0.8153	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD1512	Approved
0.8136	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD4967	Phase 2
0.8133	Intermediate Similarity	NPD4965	Approved
0.8133	Intermediate Similarity	NPD4966	Approved
0.8129	Intermediate Similarity	NPD7228	Approved
0.8075	Intermediate Similarity	NPD2534	Approved
0.8075	Intermediate Similarity	NPD2533	Approved
0.8075	Intermediate Similarity	NPD2532	Approved
0.8072	Intermediate Similarity	NPD3817	Phase 2
0.8045	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7819	Suspended
0.7977	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7075	Discontinued
0.7975	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6559	Discontinued
0.7925	Intermediate Similarity	NPD1549	Phase 2
0.7904	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1510	Phase 2
0.7844	Intermediate Similarity	NPD6801	Discontinued
0.7771	Intermediate Similarity	NPD230	Phase 1
0.7751	Intermediate Similarity	NPD5402	Approved
0.7742	Intermediate Similarity	NPD6780	Approved
0.7742	Intermediate Similarity	NPD6782	Approved
0.7742	Intermediate Similarity	NPD6776	Approved
0.7742	Intermediate Similarity	NPD6778	Approved
0.7742	Intermediate Similarity	NPD6781	Approved
0.7742	Intermediate Similarity	NPD6777	Approved
0.7742	Intermediate Similarity	NPD6779	Approved
0.7733	Intermediate Similarity	NPD7199	Phase 2
0.7722	Intermediate Similarity	NPD1607	Approved
0.7714	Intermediate Similarity	NPD3751	Discontinued
0.7711	Intermediate Similarity	NPD1653	Approved
0.7707	Intermediate Similarity	NPD943	Approved
0.7707	Intermediate Similarity	NPD1240	Approved
0.7688	Intermediate Similarity	NPD3787	Discontinued
0.7654	Intermediate Similarity	NPD8313	Approved
0.7654	Intermediate Similarity	NPD8312	Approved
0.764	Intermediate Similarity	NPD7240	Approved
0.763	Intermediate Similarity	NPD1247	Approved
0.7625	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7435	Discontinued
0.7619	Intermediate Similarity	NPD6599	Discontinued
0.7604	Intermediate Similarity	NPD8151	Discontinued
0.7595	Intermediate Similarity	NPD1613	Approved
0.7595	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5711	Approved
0.7586	Intermediate Similarity	NPD5710	Approved
0.7578	Intermediate Similarity	NPD2796	Approved
0.7578	Intermediate Similarity	NPD2935	Discontinued
0.7576	Intermediate Similarity	NPD6799	Approved
0.7574	Intermediate Similarity	NPD7411	Suspended
0.7546	Intermediate Similarity	NPD2800	Approved
0.7545	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7685	Pre-registration
0.7527	Intermediate Similarity	NPD8150	Discontinued
0.7526	Intermediate Similarity	NPD7696	Phase 3
0.7526	Intermediate Similarity	NPD7697	Approved
0.7526	Intermediate Similarity	NPD7698	Approved
0.7516	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7870	Phase 2
0.7487	Intermediate Similarity	NPD7871	Phase 2
0.7474	Intermediate Similarity	NPD6823	Phase 2
0.7473	Intermediate Similarity	NPD6535	Approved
0.7473	Intermediate Similarity	NPD6534	Approved
0.7469	Intermediate Similarity	NPD6099	Approved
0.7469	Intermediate Similarity	NPD6100	Approved
0.7461	Intermediate Similarity	NPD7701	Phase 2
0.7457	Intermediate Similarity	NPD3749	Approved
0.7436	Intermediate Similarity	NPD7801	Approved
0.7425	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD919	Approved
0.7401	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3750	Approved
0.7394	Intermediate Similarity	NPD4628	Phase 3
0.7391	Intermediate Similarity	NPD6651	Approved
0.7389	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7874	Approved
0.7368	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7390	Discontinued
0.7354	Intermediate Similarity	NPD7700	Phase 2
0.7354	Intermediate Similarity	NPD7699	Phase 2
0.7353	Intermediate Similarity	NPD3226	Approved
0.7349	Intermediate Similarity	NPD6190	Approved
0.7347	Intermediate Similarity	NPD7783	Phase 2
0.7347	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD3926	Phase 2
0.7342	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD8434	Phase 2
0.7337	Intermediate Similarity	NPD5403	Approved
0.7333	Intermediate Similarity	NPD6674	Discontinued
0.7329	Intermediate Similarity	NPD447	Suspended
0.7322	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2346	Discontinued
0.7316	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7768	Phase 2
0.7289	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD9494	Approved
0.7256	Intermediate Similarity	NPD1551	Phase 2
0.7241	Intermediate Similarity	NPD5353	Approved
0.7235	Intermediate Similarity	NPD920	Approved
0.7234	Intermediate Similarity	NPD6212	Phase 3
0.7234	Intermediate Similarity	NPD6213	Phase 3
0.7234	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5401	Approved
0.7165	Intermediate Similarity	NPD7680	Approved
0.7151	Intermediate Similarity	NPD7458	Discontinued
0.7151	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD8320	Phase 1
0.7128	Intermediate Similarity	NPD8319	Approved
0.7126	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1933	Approved
0.7107	Intermediate Similarity	NPD2798	Approved
0.7091	Intermediate Similarity	NPD2799	Discontinued
0.7091	Intermediate Similarity	NPD3748	Approved
0.7088	Intermediate Similarity	NPD7286	Phase 2
0.707	Intermediate Similarity	NPD9269	Phase 2
0.7056	Intermediate Similarity	NPD5242	Approved
0.7055	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3620	Phase 2
0.7044	Intermediate Similarity	NPD1470	Approved
0.7039	Intermediate Similarity	NPD8127	Discontinued
0.7037	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD5005	Approved
0.7026	Intermediate Similarity	NPD5006	Approved
0.7024	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD1243	Approved
0.7018	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4363	Phase 3
0.7016	Intermediate Similarity	NPD4360	Phase 2
0.7011	Intermediate Similarity	NPD5953	Discontinued
0.701	Intermediate Similarity	NPD4111	Phase 1
0.701	Intermediate Similarity	NPD4665	Approved
0.7006	Intermediate Similarity	NPD7266	Discontinued
0.7006	Intermediate Similarity	NPD1201	Approved
0.7	Intermediate Similarity	NPD7229	Phase 3
0.6982	Remote Similarity	NPD8166	Discontinued
0.697	Remote Similarity	NPD7584	Approved
0.6933	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2403	Approved
0.6919	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4908	Phase 1
0.6914	Remote Similarity	NPD7028	Phase 2
0.6907	Remote Similarity	NPD4420	Approved
0.6905	Remote Similarity	NPD2344	Approved
0.6901	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3300	Phase 2
0.6899	Remote Similarity	NPD1610	Phase 2
0.6897	Remote Similarity	NPD7930	Approved
0.6893	Remote Similarity	NPD8455	Phase 2
0.6893	Remote Similarity	NPD5761	Phase 2
0.6893	Remote Similarity	NPD5760	Phase 2
0.6888	Remote Similarity	NPD2493	Approved
0.6888	Remote Similarity	NPD2494	Approved
0.6879	Remote Similarity	NPD6273	Approved
0.6875	Remote Similarity	NPD7615	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