NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.11
Volume:	246.776
LogP:	3.431
LogD:	3.57
LogS:	-3.832
# Rotatable Bonds:	1
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.768
Synthetic Accessibility Score:	2.602
Fsp3:	0.357
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:	-4.727
MDCK Permeability:	2.039665196207352e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.074
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.624

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	97.81096649169922%
Volume Distribution (VD):	0.418
Pgp-substrate:	2.0853183269500732%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.71
CYP2C19-substrate:	0.545
CYP2C9-inhibitor:	0.672
CYP2C9-substrate:	0.828
CYP2D6-inhibitor:	0.53
CYP2D6-substrate:	0.611
CYP3A4-inhibitor:	0.481
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	1.899
Half-life (T1/2):	0.336

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.833
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.218
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.336
Carcinogencity:	0.368
Eye Corrosion:	0.011
Eye Irritation:	0.617
Respiratory Toxicity:	0.754

Download Data

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

Natural Product: NPC81261

Natural Product ID:	NPC81261
*Common Name:**	Mansonrin B
IUPAC Name:	6-hydroxy-3,8-dimethyl-5-propan-2-ylchromen-2-one
Synonyms:
Standard InCHIKey:	VAOZKYYIOZFKKZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H16O3/c1-7(2)12-10-5-9(4)14(16)17-13(10)8(3)6-11(12)15/h5-7,15H,1-4H3
SMILES:	CC(C)c1c2cc(C)c(=O)oc2c(C)cc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3409091
PubChem CID:	636576
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0002908] Hydroxycoumarins

*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
NPO1662	Mansonia gagei	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	0.61	ug.mL-1	PMID[523547]

☑ 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 NPC81261 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	364
0.1-0.2	1709
0.2-0.3	4150
0.3-0.4	10304
0.4-0.5	8393
0.5-0.6	4622
0.6-0.7	7585
0.7-0.8	5311
0.8-0.85	242
0.85-0.9	12
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9098	High Similarity	NPC14177
0.9084	High Similarity	NPC115861
0.8828	High Similarity	NPC142087
0.8828	High Similarity	NPC95034
0.881	High Similarity	NPC248786
0.88	High Similarity	NPC168707
0.88	High Similarity	NPC48623
0.877	High Similarity	NPC163398
0.876	High Similarity	NPC176590
0.874	High Similarity	NPC474237
0.873	High Similarity	NPC302211
0.872	High Similarity	NPC45663
0.8647	High Similarity	NPC27394
0.8594	High Similarity	NPC147896
0.8583	High Similarity	NPC473464
0.8583	High Similarity	NPC476332
0.8571	High Similarity	NPC322569
0.8496	Intermediate Similarity	NPC317601
0.8496	Intermediate Similarity	NPC329427
0.8485	Intermediate Similarity	NPC196621
0.848	Intermediate Similarity	NPC139047
0.8455	Intermediate Similarity	NPC87563
0.845	Intermediate Similarity	NPC276962
0.845	Intermediate Similarity	NPC61685
0.845	Intermediate Similarity	NPC190086
0.8443	Intermediate Similarity	NPC280760
0.8413	Intermediate Similarity	NPC98748
0.8413	Intermediate Similarity	NPC471449
0.84	Intermediate Similarity	NPC238075
0.84	Intermediate Similarity	NPC187993
0.84	Intermediate Similarity	NPC238176
0.8397	Intermediate Similarity	NPC156298
0.8387	Intermediate Similarity	NPC473718
0.8385	Intermediate Similarity	NPC279118
0.8385	Intermediate Similarity	NPC320847
0.8359	Intermediate Similarity	NPC476165
0.8346	Intermediate Similarity	NPC249425
0.832	Intermediate Similarity	NPC126759
0.832	Intermediate Similarity	NPC242580
0.832	Intermediate Similarity	NPC236070
0.832	Intermediate Similarity	NPC69539
0.8309	Intermediate Similarity	NPC51087
0.8309	Intermediate Similarity	NPC291119
0.8309	Intermediate Similarity	NPC281169
0.8309	Intermediate Similarity	NPC161856
0.8306	Intermediate Similarity	NPC41851
0.8284	Intermediate Similarity	NPC258073
0.8281	Intermediate Similarity	NPC129176
0.8271	Intermediate Similarity	NPC271832
0.8271	Intermediate Similarity	NPC206028
0.8268	Intermediate Similarity	NPC51341
0.8254	Intermediate Similarity	NPC183154
0.8254	Intermediate Similarity	NPC263754
0.8227	Intermediate Similarity	NPC36732
0.8203	Intermediate Similarity	NPC474131
0.8182	Intermediate Similarity	NPC128321
0.8182	Intermediate Similarity	NPC60389
0.8175	Intermediate Similarity	NPC33717
0.8168	Intermediate Similarity	NPC248557
0.8154	Intermediate Similarity	NPC46634
0.8145	Intermediate Similarity	NPC474920
0.8145	Intermediate Similarity	NPC26615
0.8145	Intermediate Similarity	NPC98372
0.814	Intermediate Similarity	NPC277798
0.814	Intermediate Similarity	NPC212559
0.814	Intermediate Similarity	NPC100108
0.8134	Intermediate Similarity	NPC59654
0.8125	Intermediate Similarity	NPC32152
0.812	Intermediate Similarity	NPC243688
0.8106	Intermediate Similarity	NPC93219
0.8106	Intermediate Similarity	NPC244495
0.8092	Intermediate Similarity	NPC275145
0.8088	Intermediate Similarity	NPC118253
0.808	Intermediate Similarity	NPC190212
0.8074	Intermediate Similarity	NPC325003
0.8071	Intermediate Similarity	NPC476191
0.8071	Intermediate Similarity	NPC79372
0.8062	Intermediate Similarity	NPC474874
0.8062	Intermediate Similarity	NPC232295
0.8056	Intermediate Similarity	NPC211565
0.8045	Intermediate Similarity	NPC329272
0.8042	Intermediate Similarity	NPC86069
0.8041	Intermediate Similarity	NPC477691
0.803	Intermediate Similarity	NPC89630
0.8029	Intermediate Similarity	NPC472524
0.8028	Intermediate Similarity	NPC329493
0.8016	Intermediate Similarity	NPC114918
0.8015	Intermediate Similarity	NPC49441
0.8015	Intermediate Similarity	NPC191395
0.8015	Intermediate Similarity	NPC325301
0.8014	Intermediate Similarity	NPC472523
0.8	Intermediate Similarity	NPC199462
0.8	Intermediate Similarity	NPC96423
0.8	Intermediate Similarity	NPC307253
0.7984	Intermediate Similarity	NPC141068
0.7973	Intermediate Similarity	NPC477690
0.7971	Intermediate Similarity	NPC211164
0.797	Intermediate Similarity	NPC252962
0.7958	Intermediate Similarity	NPC469564
0.7956	Intermediate Similarity	NPC194277
0.7956	Intermediate Similarity	NPC312560
0.7953	Intermediate Similarity	NPC283169
0.7951	Intermediate Similarity	NPC30416
0.7941	Intermediate Similarity	NPC475880
0.7941	Intermediate Similarity	NPC475102
0.7934	Intermediate Similarity	NPC272029
0.7929	Intermediate Similarity	NPC476171
0.7926	Intermediate Similarity	NPC185066
0.7926	Intermediate Similarity	NPC47288
0.7923	Intermediate Similarity	NPC328485
0.7923	Intermediate Similarity	NPC478121
0.7923	Intermediate Similarity	NPC31314
0.7923	Intermediate Similarity	NPC193193
0.792	Intermediate Similarity	NPC275627
0.7917	Intermediate Similarity	NPC89664
0.7917	Intermediate Similarity	NPC274085
0.7914	Intermediate Similarity	NPC281513
0.7914	Intermediate Similarity	NPC22222
0.7907	Intermediate Similarity	NPC63010
0.7899	Intermediate Similarity	NPC277021
0.7899	Intermediate Similarity	NPC163557
0.7899	Intermediate Similarity	NPC31849
0.7895	Intermediate Similarity	NPC111088
0.7886	Intermediate Similarity	NPC233320
0.7883	Intermediate Similarity	NPC474246
0.7883	Intermediate Similarity	NPC474143
0.7879	Intermediate Similarity	NPC327070
0.7879	Intermediate Similarity	NPC204535
0.7879	Intermediate Similarity	NPC46586
0.7877	Intermediate Similarity	NPC142863
0.7872	Intermediate Similarity	NPC265335
0.7869	Intermediate Similarity	NPC139891
0.7868	Intermediate Similarity	NPC131684
0.7857	Intermediate Similarity	NPC474610
0.7857	Intermediate Similarity	NPC265515
0.7857	Intermediate Similarity	NPC21797
0.7857	Intermediate Similarity	NPC194847
0.7852	Intermediate Similarity	NPC477212
0.7852	Intermediate Similarity	NPC319422
0.7852	Intermediate Similarity	NPC473993
0.7852	Intermediate Similarity	NPC477214
0.7852	Intermediate Similarity	NPC477211
0.7847	Intermediate Similarity	NPC474599
0.7842	Intermediate Similarity	NPC71372
0.7842	Intermediate Similarity	NPC473054
0.7842	Intermediate Similarity	NPC50896
0.7842	Intermediate Similarity	NPC204353
0.7842	Intermediate Similarity	NPC477210
0.7842	Intermediate Similarity	NPC326600
0.7842	Intermediate Similarity	NPC265793
0.7838	Intermediate Similarity	NPC158866
0.7836	Intermediate Similarity	NPC170749
0.7826	Intermediate Similarity	NPC27578
0.7826	Intermediate Similarity	NPC251549
0.7826	Intermediate Similarity	NPC289624
0.7823	Intermediate Similarity	NPC105415
0.7823	Intermediate Similarity	NPC37139
0.7823	Intermediate Similarity	NPC68260
0.7823	Intermediate Similarity	NPC279887
0.782	Intermediate Similarity	NPC261992
0.782	Intermediate Similarity	NPC474130
0.7817	Intermediate Similarity	NPC475012
0.781	Intermediate Similarity	NPC2989
0.781	Intermediate Similarity	NPC196193
0.781	Intermediate Similarity	NPC32463
0.781	Intermediate Similarity	NPC470725
0.7803	Intermediate Similarity	NPC52247
0.7803	Intermediate Similarity	NPC187868
0.7801	Intermediate Similarity	NPC130976
0.7801	Intermediate Similarity	NPC105493
0.7801	Intermediate Similarity	NPC471542
0.7794	Intermediate Similarity	NPC201419
0.7793	Intermediate Similarity	NPC471600
0.7793	Intermediate Similarity	NPC292256
0.7786	Intermediate Similarity	NPC252095
0.7778	Intermediate Similarity	NPC469912
0.7778	Intermediate Similarity	NPC230157
0.7778	Intermediate Similarity	NPC236419
0.7778	Intermediate Similarity	NPC228609
0.7778	Intermediate Similarity	NPC474737
0.7778	Intermediate Similarity	NPC470723
0.7778	Intermediate Similarity	NPC101894
0.777	Intermediate Similarity	NPC70764
0.777	Intermediate Similarity	NPC233267
0.777	Intermediate Similarity	NPC185777
0.777	Intermediate Similarity	NPC291049
0.7769	Intermediate Similarity	NPC283616
0.7761	Intermediate Similarity	NPC91475
0.7761	Intermediate Similarity	NPC265910
0.776	Intermediate Similarity	NPC282855
0.776	Intermediate Similarity	NPC471954
0.776	Intermediate Similarity	NPC26013
0.776	Intermediate Similarity	NPC75272
0.7754	Intermediate Similarity	NPC279596
0.7754	Intermediate Similarity	NPC160623
0.7754	Intermediate Similarity	NPC153019
0.7752	Intermediate Similarity	NPC290470
0.7752	Intermediate Similarity	NPC154256
0.7746	Intermediate Similarity	NPC151946
0.7744	Intermediate Similarity	NPC96286

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 NPC81261 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	349
0.1-0.2	999
0.2-0.3	1544
0.3-0.4	2641
0.4-0.5	1957
0.5-0.6	1124
0.6-0.7	397
0.7-0.8	124
0.8-0.85	13
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8651	High Similarity	NPD1611	Approved
0.8492	Intermediate Similarity	NPD4626	Approved
0.84	Intermediate Similarity	NPD7644	Approved
0.8374	Intermediate Similarity	NPD1398	Phase 1
0.832	Intermediate Similarity	NPD7340	Approved
0.8268	Intermediate Similarity	NPD5691	Approved
0.8168	Intermediate Similarity	NPD6696	Suspended
0.814	Intermediate Similarity	NPD3496	Discontinued
0.8106	Intermediate Similarity	NPD2797	Approved
0.8095	Intermediate Similarity	NPD6671	Approved
0.8088	Intermediate Similarity	NPD4060	Phase 1
0.8	Intermediate Similarity	NPD2346	Discontinued
0.7958	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7985	Registered
0.7895	Intermediate Similarity	NPD1283	Approved
0.7869	Intermediate Similarity	NPD9697	Approved
0.7852	Intermediate Similarity	NPD2237	Approved
0.781	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD3268	Approved
0.7803	Intermediate Similarity	NPD422	Phase 1
0.7801	Intermediate Similarity	NPD2935	Discontinued
0.7786	Intermediate Similarity	NPD1778	Approved
0.777	Intermediate Similarity	NPD3226	Approved
0.7737	Intermediate Similarity	NPD4625	Phase 3
0.7717	Intermediate Similarity	NPD7635	Approved
0.7698	Intermediate Similarity	NPD4140	Approved
0.7687	Intermediate Similarity	NPD4749	Approved
0.7669	Intermediate Similarity	NPD1281	Approved
0.7651	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD1608	Approved
0.7606	Intermediate Similarity	NPD4308	Phase 3
0.7606	Intermediate Similarity	NPD2799	Discontinued
0.7586	Intermediate Similarity	NPD7003	Approved
0.7556	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD2313	Discontinued
0.7554	Intermediate Similarity	NPD411	Approved
0.75	Intermediate Similarity	NPD5762	Approved
0.75	Intermediate Similarity	NPD8032	Phase 2
0.75	Intermediate Similarity	NPD5763	Approved
0.7481	Intermediate Similarity	NPD9717	Approved
0.7466	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD2861	Phase 2
0.745	Intermediate Similarity	NPD2676	Approved
0.745	Intermediate Similarity	NPD2675	Approved
0.745	Intermediate Similarity	NPD6273	Approved
0.7448	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD2979	Phase 3
0.7445	Intermediate Similarity	NPD3267	Approved
0.7445	Intermediate Similarity	NPD1203	Approved
0.7445	Intermediate Similarity	NPD3266	Approved
0.7444	Intermediate Similarity	NPD1651	Approved
0.7444	Intermediate Similarity	NPD5585	Approved
0.7431	Intermediate Similarity	NPD6100	Approved
0.7431	Intermediate Similarity	NPD6099	Approved
0.7429	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1535	Discovery
0.7394	Intermediate Similarity	NPD447	Suspended
0.7388	Intermediate Similarity	NPD17	Approved
0.7383	Intermediate Similarity	NPD1578	Phase 2
0.7381	Intermediate Similarity	NPD968	Approved
0.7379	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3225	Approved
0.7353	Intermediate Similarity	NPD1481	Phase 2
0.7347	Intermediate Similarity	NPD3750	Approved
0.7333	Intermediate Similarity	NPD6090	Discontinued
0.7329	Intermediate Similarity	NPD5844	Phase 1
0.7324	Intermediate Similarity	NPD4307	Phase 2
0.731	Intermediate Similarity	NPD4477	Approved
0.731	Intermediate Similarity	NPD4476	Approved
0.7308	Intermediate Similarity	NPD5535	Approved
0.7295	Intermediate Similarity	NPD288	Approved
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2534	Approved
0.7267	Intermediate Similarity	NPD2532	Approved
0.7267	Intermediate Similarity	NPD2533	Approved
0.7266	Intermediate Similarity	NPD2798	Approved
0.7266	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3134	Approved
0.7237	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7095	Approved
0.7213	Intermediate Similarity	NPD844	Approved
0.7174	Intermediate Similarity	NPD4359	Approved
0.7162	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD709	Approved
0.7143	Intermediate Similarity	NPD6005	Phase 3
0.7143	Intermediate Similarity	NPD6002	Phase 3
0.7143	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6666	Approved
0.7133	Intermediate Similarity	NPD6667	Approved
0.7124	Intermediate Similarity	NPD1653	Approved
0.7115	Intermediate Similarity	NPD7819	Suspended
0.7114	Intermediate Similarity	NPD4628	Phase 3
0.7103	Intermediate Similarity	NPD4097	Suspended
0.7103	Intermediate Similarity	NPD6653	Approved
0.7101	Intermediate Similarity	NPD2233	Approved
0.7101	Intermediate Similarity	NPD2230	Approved
0.7101	Intermediate Similarity	NPD2232	Approved
0.7092	Intermediate Similarity	NPD1712	Approved
0.7092	Intermediate Similarity	NPD5736	Approved
0.7077	Intermediate Similarity	NPD4750	Phase 3
0.7075	Intermediate Similarity	NPD6032	Approved
0.7075	Intermediate Similarity	NPD1551	Phase 2
0.7075	Intermediate Similarity	NPD2531	Phase 2
0.7075	Intermediate Similarity	NPD2438	Suspended
0.7071	Intermediate Similarity	NPD987	Approved
0.7063	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1358	Approved
0.7054	Intermediate Similarity	NPD2342	Discontinued
0.705	Intermediate Similarity	NPD5327	Phase 3
0.7049	Intermediate Similarity	NPD845	Approved
0.7047	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD2614	Approved
0.7042	Intermediate Similarity	NPD6832	Phase 2
0.7039	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1610	Phase 2
0.7007	Intermediate Similarity	NPD3748	Approved
0.7006	Intermediate Similarity	NPD5929	Approved
0.7	Intermediate Similarity	NPD7976	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1241	Discontinued
0.6986	Remote Similarity	NPD2157	Approved
0.6986	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3453	Discontinued
0.698	Remote Similarity	NPD7974	Phase 3
0.6974	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7458	Discontinued
0.6963	Remote Similarity	NPD9493	Approved
0.6957	Remote Similarity	NPD8127	Discontinued
0.6951	Remote Similarity	NPD7177	Discontinued
0.6944	Remote Similarity	NPD6798	Discontinued
0.694	Remote Similarity	NPD497	Approved
0.6939	Remote Similarity	NPD7097	Phase 1
0.6937	Remote Similarity	NPD5709	Phase 3
0.6933	Remote Similarity	NPD1243	Approved
0.6933	Remote Similarity	NPD6674	Discontinued
0.6929	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD290	Approved
0.6923	Remote Similarity	NPD4908	Phase 1
0.6923	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5735	Approved
0.6917	Remote Similarity	NPD1138	Approved
0.6914	Remote Similarity	NPD6232	Discontinued
0.6913	Remote Similarity	NPD2344	Approved
0.6913	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1201	Approved
0.6905	Remote Similarity	NPD8312	Approved
0.6905	Remote Similarity	NPD8313	Approved
0.6901	Remote Similarity	NPD1019	Discontinued
0.6901	Remote Similarity	NPD4624	Approved
0.6899	Remote Similarity	NPD1465	Phase 2
0.6897	Remote Similarity	NPD6663	Approved
0.6897	Remote Similarity	NPD6233	Phase 2
0.6897	Remote Similarity	NPD4870	Approved
0.6894	Remote Similarity	NPD4666	Phase 3
0.6892	Remote Similarity	NPD7033	Discontinued
0.689	Remote Similarity	NPD7473	Discontinued
0.6887	Remote Similarity	NPD8166	Discontinued
0.6887	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4110	Phase 3
0.6884	Remote Similarity	NPD3019	Approved
0.6884	Remote Similarity	NPD2932	Approved
0.6871	Remote Similarity	NPD6353	Approved
0.687	Remote Similarity	NPD2684	Approved
0.6867	Remote Similarity	NPD2424	Discontinued
0.6866	Remote Similarity	NPD496	Approved
0.6866	Remote Similarity	NPD495	Approved
0.6866	Remote Similarity	NPD498	Approved
0.6861	Remote Similarity	NPD1894	Discontinued
0.6861	Remote Similarity	NPD1548	Phase 1
0.6857	Remote Similarity	NPD2231	Phase 2
0.6857	Remote Similarity	NPD2235	Phase 2
0.6853	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6959	Discontinued
0.6849	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD2203	Discontinued
0.6849	Remote Similarity	NPD3620	Phase 2
0.6846	Remote Similarity	NPD5406	Approved
0.6846	Remote Similarity	NPD5404	Approved
0.6846	Remote Similarity	NPD5408	Approved
0.6846	Remote Similarity	NPD5405	Approved
0.6842	Remote Similarity	NPD1139	Approved
0.6842	Remote Similarity	NPD1137	Approved
0.6842	Remote Similarity	NPD228	Approved
0.6839	Remote Similarity	NPD7427	Discontinued
0.6838	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3847	Discontinued
0.6831	Remote Similarity	NPD1470	Approved
0.6831	Remote Similarity	NPD6362	Approved
0.6828	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3764	Approved
0.6828	Remote Similarity	NPD1296	Phase 2
0.6821	Remote Similarity	NPD1652	Phase 2
0.6813	Remote Similarity	NPD7768	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