NPASS Compound

Structure

NPC472837 OpenBabel07101719512D 22 26 0 0 0 0 0 0 0 0999 V2000 -2.5981 -1.5000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9025 -1.8718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9703 -2.5921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2395 -0.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 -1.4757 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4494 -3.0942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -0.2728 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 -2.0000 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 2.7622 -4.0440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7517 0.7160 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 11 2 0 0 0 0 4 16 2 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 12 18 2 0 0 0 0 13 14 1 0 0 0 0 13 17 2 0 0 0 0 14 20 2 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.06
Volume:	294.404
LogP:	4.745
LogD:	3.138
LogS:	-6.945
# Rotatable Bonds:	0
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.339
Synthetic Accessibility Score:	2.417
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.941
MDCK Permeability:	2.6039819204015657e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.309
20% Bioavailability (F20%):	0.355
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	93.5953598022461%
Volume Distribution (VD):	0.482
Pgp-substrate:	5.027238368988037%

ADMET: Metabolism

CYP1A2-inhibitor:	0.988
CYP1A2-substrate:	0.211
CYP2C19-inhibitor:	0.519
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.529
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.608
CYP2D6-substrate:	0.895
CYP3A4-inhibitor:	0.245
CYP3A4-substrate:	0.098

ADMET: Excretion

Clearance (CL):	3.308
Half-life (T1/2):	0.218

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.779
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.855
Rat Oral Acute Toxicity:	0.159
Maximum Recommended Daily Dose:	0.883
Skin Sensitization:	0.948
Carcinogencity:	0.949
Eye Corrosion:	0.018
Eye Irritation:	0.95
Respiratory Toxicity:	0.36

Download Data

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

Natural Product: NPC472837

Natural Product ID:	NPC472837
*Common Name:**	YYEKFUYNJPGGCD-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YYEKFUYNJPGGCD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H10O3/c20-14-8-5-10-9-15(21)19-18-12(6-7-13(14)17(10)18)11-3-1-2-4-16(11)22-19/h1-9,21H
SMILES:	Oc1cc2ccc(=O)c3c2c2c1oc1ccccc1c2cc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3589049
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0003483] Benzoxanthenes

*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
NPO32893	haemodorum spicatum	Species	Haemodoraceae	Eukaryota	n.a.	Australian	n.a.	PMID[26090896]

☑ 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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	3.0	mm	PMID[516339]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	IZ	=	1.0	mm	PMID[516339]

☑ 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 NPC472837 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	623
0.1-0.2	2289
0.2-0.3	5728
0.3-0.4	12187
0.4-0.5	4413
0.5-0.6	4924
0.6-0.7	7336
0.7-0.8	4919
0.8-0.85	265
0.85-0.9	9
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9595	High Similarity	NPC288353
0.9375	High Similarity	NPC308006
0.9195	High Similarity	NPC306011
0.9195	High Similarity	NPC472838
0.9122	High Similarity	NPC472839
0.9	High Similarity	NPC295977
0.9	High Similarity	NPC58310
0.8926	High Similarity	NPC58373
0.891	High Similarity	NPC469472
0.8896	High Similarity	NPC167098
0.8896	High Similarity	NPC296044
0.8859	High Similarity	NPC39361
0.8816	High Similarity	NPC144283
0.8725	High Similarity	NPC472836
0.8725	High Similarity	NPC309169
0.8725	High Similarity	NPC196941
0.8725	High Similarity	NPC300603
0.8725	High Similarity	NPC91694
0.8716	High Similarity	NPC141817
0.8716	High Similarity	NPC176030
0.8716	High Similarity	NPC169214
0.8716	High Similarity	NPC229218
0.8716	High Similarity	NPC192597
0.871	High Similarity	NPC213401
0.871	High Similarity	NPC279605
0.8693	High Similarity	NPC302783
0.8693	High Similarity	NPC118427
0.8693	High Similarity	NPC473201
0.8688	High Similarity	NPC469521
0.8667	High Similarity	NPC73416
0.8667	High Similarity	NPC160777
0.8659	High Similarity	NPC47191
0.8636	High Similarity	NPC164912
0.8627	High Similarity	NPC475718
0.8625	High Similarity	NPC263212
0.8571	High Similarity	NPC78505
0.8562	High Similarity	NPC26386
0.8562	High Similarity	NPC261322
0.8553	High Similarity	NPC52692
0.8528	High Similarity	NPC4200
0.8516	High Similarity	NPC3744
0.8516	High Similarity	NPC137125
0.8497	Intermediate Similarity	NPC474556
0.8491	Intermediate Similarity	NPC472906
0.8481	Intermediate Similarity	NPC104876
0.8481	Intermediate Similarity	NPC245891
0.8462	Intermediate Similarity	NPC472905
0.8452	Intermediate Similarity	NPC70320
0.8447	Intermediate Similarity	NPC303174
0.8442	Intermediate Similarity	NPC300983
0.8438	Intermediate Similarity	NPC149389
0.8428	Intermediate Similarity	NPC471973
0.8421	Intermediate Similarity	NPC225351
0.8418	Intermediate Similarity	NPC136674
0.8418	Intermediate Similarity	NPC178976
0.8411	Intermediate Similarity	NPC50954
0.8408	Intermediate Similarity	NPC80489
0.8405	Intermediate Similarity	NPC188079
0.8405	Intermediate Similarity	NPC476637
0.8405	Intermediate Similarity	NPC300307
0.84	Intermediate Similarity	NPC84273
0.8395	Intermediate Similarity	NPC37870
0.8395	Intermediate Similarity	NPC272560
0.8395	Intermediate Similarity	NPC43319
0.8385	Intermediate Similarity	NPC67959
0.8378	Intermediate Similarity	NPC186647
0.8365	Intermediate Similarity	NPC235448
0.8354	Intermediate Similarity	NPC5322
0.8354	Intermediate Similarity	NPC77807
0.8354	Intermediate Similarity	NPC14561
0.8354	Intermediate Similarity	NPC133970
0.8354	Intermediate Similarity	NPC5379
0.8354	Intermediate Similarity	NPC472907
0.8354	Intermediate Similarity	NPC6633
0.8354	Intermediate Similarity	NPC52598
0.8344	Intermediate Similarity	NPC475770
0.8344	Intermediate Similarity	NPC11314
0.8344	Intermediate Similarity	NPC273462
0.8344	Intermediate Similarity	NPC227337
0.8344	Intermediate Similarity	NPC218226
0.8344	Intermediate Similarity	NPC70433
0.8344	Intermediate Similarity	NPC33051
0.8344	Intermediate Similarity	NPC49402
0.8344	Intermediate Similarity	NPC69755
0.8323	Intermediate Similarity	NPC294965
0.8323	Intermediate Similarity	NPC476247
0.8313	Intermediate Similarity	NPC36217
0.8313	Intermediate Similarity	NPC474960
0.8302	Intermediate Similarity	NPC161960
0.8302	Intermediate Similarity	NPC37543
0.8302	Intermediate Similarity	NPC474681
0.8302	Intermediate Similarity	NPC199463
0.8302	Intermediate Similarity	NPC187745
0.8302	Intermediate Similarity	NPC472963
0.8302	Intermediate Similarity	NPC218313
0.8302	Intermediate Similarity	NPC304008
0.8302	Intermediate Similarity	NPC143328
0.8299	Intermediate Similarity	NPC144662
0.8291	Intermediate Similarity	NPC152951
0.8291	Intermediate Similarity	NPC117992
0.8291	Intermediate Similarity	NPC268008
0.8291	Intermediate Similarity	NPC478161
0.8291	Intermediate Similarity	NPC200246
0.8291	Intermediate Similarity	NPC478159
0.8291	Intermediate Similarity	NPC168247
0.8291	Intermediate Similarity	NPC230149
0.8291	Intermediate Similarity	NPC472835
0.8291	Intermediate Similarity	NPC57674
0.8288	Intermediate Similarity	NPC183103
0.8288	Intermediate Similarity	NPC73656
0.8282	Intermediate Similarity	NPC472449
0.8282	Intermediate Similarity	NPC272502
0.828	Intermediate Similarity	NPC237994
0.828	Intermediate Similarity	NPC312338
0.828	Intermediate Similarity	NPC149889
0.8276	Intermediate Similarity	NPC66905
0.8272	Intermediate Similarity	NPC207690
0.8272	Intermediate Similarity	NPC270837
0.8272	Intermediate Similarity	NPC189473
0.8272	Intermediate Similarity	NPC23298
0.8272	Intermediate Similarity	NPC186686
0.8272	Intermediate Similarity	NPC236132
0.8269	Intermediate Similarity	NPC151473
0.8267	Intermediate Similarity	NPC223336
0.8267	Intermediate Similarity	NPC470407
0.8263	Intermediate Similarity	NPC216307
0.8261	Intermediate Similarity	NPC234644
0.8261	Intermediate Similarity	NPC311740
0.8258	Intermediate Similarity	NPC43669
0.8258	Intermediate Similarity	NPC196277
0.8258	Intermediate Similarity	NPC272721
0.8255	Intermediate Similarity	NPC264022
0.8253	Intermediate Similarity	NPC199357
0.825	Intermediate Similarity	NPC204879
0.825	Intermediate Similarity	NPC85121
0.825	Intermediate Similarity	NPC100123
0.8243	Intermediate Similarity	NPC153088
0.8243	Intermediate Similarity	NPC95485
0.8243	Intermediate Similarity	NPC88065
0.8243	Intermediate Similarity	NPC89504
0.8242	Intermediate Similarity	NPC101107
0.8239	Intermediate Similarity	NPC109765
0.8239	Intermediate Similarity	NPC115853
0.8239	Intermediate Similarity	NPC470600
0.8235	Intermediate Similarity	NPC275278
0.8232	Intermediate Similarity	NPC474024
0.8232	Intermediate Similarity	NPC476306
0.8231	Intermediate Similarity	NPC470406
0.8228	Intermediate Similarity	NPC469550
0.8228	Intermediate Similarity	NPC107109
0.8228	Intermediate Similarity	NPC305710
0.8228	Intermediate Similarity	NPC474000
0.8221	Intermediate Similarity	NPC156432
0.8221	Intermediate Similarity	NPC293319
0.8221	Intermediate Similarity	NPC275780
0.8221	Intermediate Similarity	NPC239752
0.8221	Intermediate Similarity	NPC472450
0.8217	Intermediate Similarity	NPC75377
0.8217	Intermediate Similarity	NPC115869
0.821	Intermediate Similarity	NPC470694
0.821	Intermediate Similarity	NPC201800
0.821	Intermediate Similarity	NPC329760
0.821	Intermediate Similarity	NPC25152
0.821	Intermediate Similarity	NPC206605
0.8205	Intermediate Similarity	NPC37220
0.8204	Intermediate Similarity	NPC245975
0.8204	Intermediate Similarity	NPC193377
0.8199	Intermediate Similarity	NPC228785
0.8199	Intermediate Similarity	NPC320359
0.8199	Intermediate Similarity	NPC119224
0.8199	Intermediate Similarity	NPC472902
0.8199	Intermediate Similarity	NPC188433
0.8199	Intermediate Similarity	NPC84571
0.8199	Intermediate Similarity	NPC56085
0.8199	Intermediate Similarity	NPC14353
0.8199	Intermediate Similarity	NPC139036
0.8198	Intermediate Similarity	NPC205721
0.8194	Intermediate Similarity	NPC428300
0.8194	Intermediate Similarity	NPC77378
0.8194	Intermediate Similarity	NPC77598
0.8188	Intermediate Similarity	NPC324929
0.8187	Intermediate Similarity	NPC52889
0.8187	Intermediate Similarity	NPC180011
0.8187	Intermediate Similarity	NPC219867
0.8187	Intermediate Similarity	NPC291508
0.8187	Intermediate Similarity	NPC202495
0.8182	Intermediate Similarity	NPC475805
0.8182	Intermediate Similarity	NPC157133
0.8182	Intermediate Similarity	NPC3221
0.8182	Intermediate Similarity	NPC163130
0.8182	Intermediate Similarity	NPC165979
0.8176	Intermediate Similarity	NPC234255
0.8176	Intermediate Similarity	NPC472280
0.8176	Intermediate Similarity	NPC141023
0.8176	Intermediate Similarity	NPC256925
0.8171	Intermediate Similarity	NPC39091
0.8166	Intermediate Similarity	NPC120102
0.8165	Intermediate Similarity	NPC131121
0.8165	Intermediate Similarity	NPC260979
0.816	Intermediate Similarity	NPC197168

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 NPC472837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	539
0.1-0.2	1060
0.2-0.3	1695
0.3-0.4	2775
0.4-0.5	1640
0.5-0.6	995
0.6-0.7	350
0.7-0.8	91
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8293	Intermediate Similarity	NPD5844	Phase 1
0.8113	Intermediate Similarity	NPD1465	Phase 2
0.805	Intermediate Similarity	NPD1934	Approved
0.8039	Intermediate Similarity	NPD7003	Approved
0.8023	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6166	Phase 2
0.8	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6232	Discontinued
0.7975	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD2346	Discontinued
0.7952	Intermediate Similarity	NPD7473	Discontinued
0.7927	Intermediate Similarity	NPD6959	Discontinued
0.7885	Intermediate Similarity	NPD1511	Approved
0.7843	Intermediate Similarity	NPD2344	Approved
0.7806	Intermediate Similarity	NPD3750	Approved
0.7785	Intermediate Similarity	NPD1512	Approved
0.7778	Intermediate Similarity	NPD2801	Approved
0.775	Intermediate Similarity	NPD3226	Approved
0.775	Intermediate Similarity	NPD7458	Discontinued
0.7742	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD9494	Approved
0.7683	Intermediate Similarity	NPD3882	Suspended
0.7661	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2309	Approved
0.7636	Intermediate Similarity	NPD3749	Approved
0.761	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7074	Phase 3
0.7593	Intermediate Similarity	NPD4380	Phase 2
0.758	Intermediate Similarity	NPD8166	Discontinued
0.758	Intermediate Similarity	NPD4628	Phase 3
0.7561	Intermediate Similarity	NPD7819	Suspended
0.7551	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5494	Approved
0.7544	Intermediate Similarity	NPD7054	Approved
0.7529	Intermediate Similarity	NPD8313	Approved
0.7529	Intermediate Similarity	NPD8312	Approved
0.7515	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD1283	Approved
0.7485	Intermediate Similarity	NPD3818	Discontinued
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7484	Intermediate Similarity	NPD3748	Approved
0.7471	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6273	Approved
0.7452	Intermediate Similarity	NPD1549	Phase 2
0.7448	Intermediate Similarity	NPD1651	Approved
0.7439	Intermediate Similarity	NPD7411	Suspended
0.7438	Intermediate Similarity	NPD7390	Discontinued
0.7438	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5406	Approved
0.7436	Intermediate Similarity	NPD5405	Approved
0.7436	Intermediate Similarity	NPD5408	Approved
0.7436	Intermediate Similarity	NPD5404	Approved
0.7434	Intermediate Similarity	NPD2313	Discontinued
0.7425	Intermediate Similarity	NPD7075	Discontinued
0.7415	Intermediate Similarity	NPD1201	Approved
0.7391	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3751	Discontinued
0.7384	Intermediate Similarity	NPD7177	Discontinued
0.7372	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3972	Approved
0.7356	Intermediate Similarity	NPD6797	Phase 2
0.7355	Intermediate Similarity	NPD1607	Approved
0.7349	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4060	Phase 1
0.7338	Intermediate Similarity	NPD943	Approved
0.7333	Intermediate Similarity	NPD1470	Approved
0.733	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6099	Approved
0.7325	Intermediate Similarity	NPD2935	Discontinued
0.7325	Intermediate Similarity	NPD6100	Approved
0.7321	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3764	Approved
0.7314	Intermediate Similarity	NPD7251	Discontinued
0.7314	Intermediate Similarity	NPD6559	Discontinued
0.7305	Intermediate Similarity	NPD3817	Phase 2
0.7303	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1281	Approved
0.7297	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD447	Suspended
0.7278	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7808	Phase 3
0.7273	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7768	Phase 2
0.7261	Intermediate Similarity	NPD4308	Phase 3
0.7261	Intermediate Similarity	NPD1510	Phase 2
0.7255	Intermediate Similarity	NPD4625	Phase 3
0.7238	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1240	Approved
0.7208	Intermediate Similarity	NPD6798	Discontinued
0.7195	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7199	Phase 2
0.7179	Intermediate Similarity	NPD1933	Approved
0.7171	Intermediate Similarity	NPD2798	Approved
0.717	Intermediate Similarity	NPD1471	Phase 3
0.7169	Intermediate Similarity	NPD6599	Discontinued
0.7162	Intermediate Similarity	NPD4626	Approved
0.7152	Intermediate Similarity	NPD1876	Approved
0.7143	Intermediate Similarity	NPD8455	Phase 2
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1608	Approved
0.7115	Intermediate Similarity	NPD3620	Phase 2
0.7115	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1613	Approved
0.7115	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8150	Discontinued
0.711	Intermediate Similarity	NPD3926	Phase 2
0.711	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2796	Approved
0.7105	Intermediate Similarity	NPD2797	Approved
0.7105	Intermediate Similarity	NPD1203	Approved
0.7101	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5978	Approved
0.7101	Intermediate Similarity	NPD2296	Approved
0.7101	Intermediate Similarity	NPD5977	Approved
0.7099	Intermediate Similarity	NPD2354	Approved
0.7097	Intermediate Similarity	NPD3268	Approved
0.7093	Intermediate Similarity	NPD8127	Discontinued
0.7091	Intermediate Similarity	NPD7427	Discontinued
0.7088	Intermediate Similarity	NPD2490	Approved
0.7088	Intermediate Similarity	NPD2488	Approved
0.7086	Intermediate Similarity	NPD7228	Approved
0.7083	Intermediate Similarity	NPD6801	Discontinued
0.7083	Intermediate Similarity	NPD7577	Discontinued
0.7081	Intermediate Similarity	NPD6674	Discontinued
0.7076	Intermediate Similarity	NPD6234	Discontinued
0.7076	Intermediate Similarity	NPD919	Approved
0.7075	Intermediate Similarity	NPD5536	Phase 2
0.7074	Intermediate Similarity	NPD3448	Approved
0.7074	Intermediate Similarity	NPD2491	Approved
0.7066	Intermediate Similarity	NPD7028	Phase 2
0.7059	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD3787	Discontinued
0.7051	Intermediate Similarity	NPD8032	Phase 2
0.7044	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1241	Discontinued
0.7032	Intermediate Similarity	NPD7095	Approved
0.703	Intermediate Similarity	NPD5049	Phase 3
0.7019	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD228	Approved
0.7012	Intermediate Similarity	NPD6799	Approved
0.7007	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4307	Phase 2
0.7006	Intermediate Similarity	NPD2979	Phase 3
0.7	Intermediate Similarity	NPD4477	Approved
0.7	Intermediate Similarity	NPD2438	Suspended
0.7	Intermediate Similarity	NPD4476	Approved
0.6994	Remote Similarity	NPD1247	Approved
0.6987	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD3057	Approved
0.698	Remote Similarity	NPD5691	Approved
0.6975	Remote Similarity	NPD2800	Approved
0.6972	Remote Similarity	NPD2342	Discontinued
0.697	Remote Similarity	NPD2533	Approved
0.697	Remote Similarity	NPD2532	Approved
0.697	Remote Similarity	NPD2534	Approved
0.6968	Remote Similarity	NPD6777	Approved
0.6968	Remote Similarity	NPD6781	Approved
0.6968	Remote Similarity	NPD6779	Approved
0.6968	Remote Similarity	NPD6778	Approved
0.6968	Remote Similarity	NPD6782	Approved
0.6968	Remote Similarity	NPD6780	Approved
0.6968	Remote Similarity	NPD6776	Approved
0.6962	Remote Similarity	NPD6355	Discontinued
0.6954	Remote Similarity	NPD1611	Approved
0.6951	Remote Similarity	NPD3300	Phase 2
0.6943	Remote Similarity	NPD8151	Discontinued
0.6933	Remote Similarity	NPD17	Approved
0.6933	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3019	Approved
0.6933	Remote Similarity	NPD2932	Approved
0.6933	Remote Similarity	NPD4110	Phase 3
0.6927	Remote Similarity	NPD7685	Pre-registration
0.6905	Remote Similarity	NPD2649	Approved
0.6905	Remote Similarity	NPD2651	Approved
0.6901	Remote Similarity	NPD4288	Approved
0.6895	Remote Similarity	NPD3533	Approved
0.6895	Remote Similarity	NPD2972	Approved
0.6894	Remote Similarity	NPD1551	Phase 2
0.689	Remote Similarity	NPD6190	Approved
0.6883	Remote Similarity	NPD3266	Approved
0.6883	Remote Similarity	NPD3267	Approved
0.6883	Remote Similarity	NPD1164	Approved
0.6882	Remote Similarity	NPD37	Approved
0.6879	Remote Similarity	NPD411	Approved
0.6872	Remote Similarity	NPD3823	Discontinued
0.6872	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7783	Phase 2
0.6871	Remote Similarity	NPD1243	Approved
0.6871	Remote Similarity	NPD5698	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