NPASS Compound

Structure

NPC349525 OpenBabel07101718192D 28 30 0 0 1 0 0 0 0 0999 V2000 4.3052 0.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5367 2.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8296 1.7765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3461 1.5176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2247 3.6390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 3.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5731 0.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4392 1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6049 2.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4392 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9319 2.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5731 2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8978 3.1907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 2.4142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5708 2.7424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5731 3.2071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1566 4.1566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6310 0.3244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8296 3.7083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3801 1.2588 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 1.0000 2.4142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 4 26 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 11 1 0 0 0 0 8 14 2 0 0 0 0 9 15 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 27 1 0 0 0 0 12 18 2 0 0 0 0 13 15 1 0 0 0 0 13 19 2 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 6 0 0 0 16 17 2 0 0 0 0 16 28 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 28 1 0 0 0 0 19 26 1 0 0 0 0 20 24 2 0 0 0 0 20 27 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.15
Volume:	389.179
LogP:	2.594
LogD:	2.199
LogS:	-3.551
# Rotatable Bonds:	4
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	3.453
Fsp3:	0.381
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:	-4.933
MDCK Permeability:	1.6830910681164823e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.312
Plasma Protein Binding (PPB):	91.82875061035156%
Volume Distribution (VD):	0.961
Pgp-substrate:	10.271036148071289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.771
CYP1A2-substrate:	0.726
CYP2C19-inhibitor:	0.374
CYP2C19-substrate:	0.511
CYP2C9-inhibitor:	0.229
CYP2C9-substrate:	0.709
CYP2D6-inhibitor:	0.362
CYP2D6-substrate:	0.291
CYP3A4-inhibitor:	0.265
CYP3A4-substrate:	0.417

ADMET: Excretion

Clearance (CL):	13.091
Half-life (T1/2):	0.734

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.015
Drug-inuced Liver Injury (DILI):	0.127
AMES Toxicity:	0.326
Rat Oral Acute Toxicity:	0.692
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.123
Carcinogencity:	0.862
Eye Corrosion:	0.003
Eye Irritation:	0.284
Respiratory Toxicity:	0.06

Download Data

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

Natural Product: NPC349525

Natural Product ID:	NPC349525
*Common Name:**	VEFXEQGGTGFPCA-HNNXBMFYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VEFXEQGGTGFPCA-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C21H24O7/c1-11-7-12-10-27-20(24)17-16(28-18(12)14(22)8-11)6-5-13(19(17)26-4)15(23)9-21(2,3)25/h5-8,15,22-23,25H,9-10H2,1-4H3/t15-/m0/s1
SMILES:	COc1c(ccc2c1C(=O)OCc1c(O2)c(O)cc(c1)C)[C@H](CC(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3609762
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0002463] Diarylethers

*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
NPO33444	penicillium pinophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22264170]
NPO33444	penicillium pinophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26291474]

☑ 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
EC50	1
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2540	Organism	Balanus amphitrite	Balanus amphitrite	EC50	=	20.0	ug.mL-1	PMID[490250]
NPT2540	Organism	Balanus amphitrite	Balanus amphitrite	Ratio CC50/EC50	>	50.0	n.a.	PMID[490250]

☑ 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 NPC349525 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	363
0.1-0.2	1524
0.2-0.3	3821
0.3-0.4	8823
0.4-0.5	9419
0.5-0.6	3520
0.6-0.7	4738
0.7-0.8	5803
0.8-0.85	3219
0.85-0.9	1242
0.9-0.95	208
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9869	High Similarity	NPC473106
0.9869	High Similarity	NPC103201
0.9804	High Similarity	NPC292415
0.9671	High Similarity	NPC286052
0.9605	High Similarity	NPC298802
0.9539	High Similarity	NPC199773
0.9419	High Similarity	NPC474055
0.9419	High Similarity	NPC472598
0.9419	High Similarity	NPC27337
0.9363	High Similarity	NPC474038
0.9363	High Similarity	NPC472632
0.9363	High Similarity	NPC472634
0.9355	High Similarity	NPC278778
0.9355	High Similarity	NPC291878
0.9355	High Similarity	NPC195796
0.9355	High Similarity	NPC35038
0.9304	High Similarity	NPC474034
0.9304	High Similarity	NPC474033
0.9304	High Similarity	NPC472635
0.9299	High Similarity	NPC472631
0.9299	High Similarity	NPC472624
0.9299	High Similarity	NPC119209
0.9299	High Similarity	NPC192686
0.9299	High Similarity	NPC475784
0.9299	High Similarity	NPC472630
0.9299	High Similarity	NPC118256
0.9299	High Similarity	NPC174953
0.9299	High Similarity	NPC282009
0.9299	High Similarity	NPC287328
0.9295	High Similarity	NPC291508
0.929	High Similarity	NPC200761
0.929	High Similarity	NPC470327
0.929	High Similarity	NPC321779
0.929	High Similarity	NPC45849
0.929	High Similarity	NPC477503
0.9245	High Similarity	NPC234004
0.9245	High Similarity	NPC124038
0.9245	High Similarity	NPC472625
0.9241	High Similarity	NPC471499
0.9241	High Similarity	NPC26326
0.9241	High Similarity	NPC471210
0.9236	High Similarity	NPC83763
0.9236	High Similarity	NPC473990
0.9236	High Similarity	NPC168616
0.9236	High Similarity	NPC22192
0.9231	High Similarity	NPC470328
0.9231	High Similarity	NPC472626
0.9231	High Similarity	NPC209614
0.9226	High Similarity	NPC74924
0.9226	High Similarity	NPC18727
0.9226	High Similarity	NPC213896
0.9226	High Similarity	NPC192083
0.9182	High Similarity	NPC476247
0.9182	High Similarity	NPC8300
0.9177	High Similarity	NPC470326
0.9177	High Similarity	NPC328102
0.9177	High Similarity	NPC36217
0.9172	High Similarity	NPC284820
0.9172	High Similarity	NPC223787
0.9172	High Similarity	NPC108456
0.9172	High Similarity	NPC473272
0.9172	High Similarity	NPC471209
0.9167	High Similarity	NPC226025
0.9167	High Similarity	NPC234255
0.9161	High Similarity	NPC289968
0.9161	High Similarity	NPC106976
0.9161	High Similarity	NPC219582
0.9161	High Similarity	NPC236637
0.9161	High Similarity	NPC302950
0.9161	High Similarity	NPC471982
0.913	High Similarity	NPC13481
0.913	High Similarity	NPC207575
0.913	High Similarity	NPC471213
0.9125	High Similarity	NPC186686
0.9119	High Similarity	NPC112418
0.9119	High Similarity	NPC471211
0.9119	High Similarity	NPC142252
0.9119	High Similarity	NPC134783
0.9119	High Similarity	NPC471212
0.9114	High Similarity	NPC184755
0.9114	High Similarity	NPC95936
0.9114	High Similarity	NPC53545
0.9114	High Similarity	NPC250214
0.9114	High Similarity	NPC117418
0.9114	High Similarity	NPC74178
0.9108	High Similarity	NPC13858
0.9108	High Similarity	NPC320825
0.9108	High Similarity	NPC326037
0.9108	High Similarity	NPC227062
0.9108	High Similarity	NPC471985
0.9108	High Similarity	NPC472455
0.9108	High Similarity	NPC472456
0.9103	High Similarity	NPC475895
0.9103	High Similarity	NPC298692
0.9097	High Similarity	NPC75695
0.9068	High Similarity	NPC471788
0.9068	High Similarity	NPC85057
0.9068	High Similarity	NPC130920
0.9068	High Similarity	NPC62261
0.9068	High Similarity	NPC293319
0.9068	High Similarity	NPC300053
0.9068	High Similarity	NPC108433
0.9062	High Similarity	NPC474150
0.9062	High Similarity	NPC472964
0.9062	High Similarity	NPC201800
0.9062	High Similarity	NPC474162
0.9062	High Similarity	NPC471745
0.9057	High Similarity	NPC476980
0.9057	High Similarity	NPC321399
0.9057	High Similarity	NPC470183
0.9057	High Similarity	NPC472902
0.9057	High Similarity	NPC471744
0.9051	High Similarity	NPC474208
0.9051	High Similarity	NPC48208
0.9051	High Similarity	NPC222689
0.9051	High Similarity	NPC162869
0.9051	High Similarity	NPC156057
0.9051	High Similarity	NPC78225
0.9051	High Similarity	NPC52530
0.9051	High Similarity	NPC475267
0.9051	High Similarity	NPC471479
0.9051	High Similarity	NPC474836
0.9051	High Similarity	NPC67876
0.9051	High Similarity	NPC471515
0.9051	High Similarity	NPC78071
0.9051	High Similarity	NPC470402
0.9051	High Similarity	NPC52889
0.9051	High Similarity	NPC35598
0.9045	High Similarity	NPC472280
0.9045	High Similarity	NPC117992
0.9045	High Similarity	NPC16082
0.9045	High Similarity	NPC230149
0.9045	High Similarity	NPC152951
0.9045	High Similarity	NPC82592
0.9045	High Similarity	NPC256925
0.9045	High Similarity	NPC168247
0.9045	High Similarity	NPC57674
0.9038	High Similarity	NPC472912
0.9038	High Similarity	NPC237994
0.9038	High Similarity	NPC324233
0.9038	High Similarity	NPC323626
0.9032	High Similarity	NPC338131
0.9032	High Similarity	NPC88804
0.9032	High Similarity	NPC3825
0.9012	High Similarity	NPC43319
0.9012	High Similarity	NPC119589
0.9012	High Similarity	NPC472452
0.9006	High Similarity	NPC472582
0.9	High Similarity	NPC266314
0.9	High Similarity	NPC158188
0.9	High Similarity	NPC289771
0.9	High Similarity	NPC198829
0.8994	High Similarity	NPC187792
0.8994	High Similarity	NPC204879
0.8994	High Similarity	NPC210459
0.8994	High Similarity	NPC284127
0.8994	High Similarity	NPC172202
0.8994	High Similarity	NPC476410
0.8987	High Similarity	NPC235165
0.8987	High Similarity	NPC24640
0.8987	High Similarity	NPC471500
0.8987	High Similarity	NPC54928
0.8987	High Similarity	NPC191146
0.8987	High Similarity	NPC68093
0.8987	High Similarity	NPC250922
0.8987	High Similarity	NPC170026
0.8987	High Similarity	NPC255106
0.8987	High Similarity	NPC282307
0.8981	High Similarity	NPC33051
0.8981	High Similarity	NPC70433
0.8981	High Similarity	NPC227337
0.8981	High Similarity	NPC281477
0.8981	High Similarity	NPC49402
0.8981	High Similarity	NPC170492
0.8981	High Similarity	NPC273462
0.8974	High Similarity	NPC472423
0.8974	High Similarity	NPC471676
0.8974	High Similarity	NPC244577
0.8974	High Similarity	NPC474772
0.8974	High Similarity	NPC474744
0.8974	High Similarity	NPC472422
0.8974	High Similarity	NPC472420
0.8974	High Similarity	NPC256406
0.8974	High Similarity	NPC154345
0.8974	High Similarity	NPC263384
0.8974	High Similarity	NPC471677
0.8968	High Similarity	NPC223579
0.8968	High Similarity	NPC287101
0.8968	High Similarity	NPC177298
0.8968	High Similarity	NPC48479
0.8968	High Similarity	NPC473091
0.8968	High Similarity	NPC52005
0.8968	High Similarity	NPC137062
0.8968	High Similarity	NPC183950
0.8957	High Similarity	NPC116745
0.8957	High Similarity	NPC477154
0.8957	High Similarity	NPC218226
0.8957	High Similarity	NPC477502
0.8957	High Similarity	NPC6588
0.8957	High Similarity	NPC474024

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 NPC349525 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	893
0.2-0.3	1880
0.3-0.4	2534
0.4-0.5	1792
0.5-0.6	1012
0.6-0.7	509
0.7-0.8	145
0.8-0.85	40
0.85-0.9	14
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9226	High Similarity	NPD2393	Clinical (unspecified phase)
0.9161	High Similarity	NPD1934	Approved
0.8861	High Similarity	NPD2801	Approved
0.8834	High Similarity	NPD6168	Clinical (unspecified phase)
0.8834	High Similarity	NPD6167	Clinical (unspecified phase)
0.8834	High Similarity	NPD6166	Phase 2
0.8805	High Similarity	NPD3817	Phase 2
0.875	High Similarity	NPD4868	Clinical (unspecified phase)
0.875	High Similarity	NPD3882	Suspended
0.8735	High Similarity	NPD7074	Phase 3
0.8727	High Similarity	NPD3818	Discontinued
0.8696	High Similarity	NPD7075	Discontinued
0.8675	High Similarity	NPD7054	Approved
0.8645	High Similarity	NPD1511	Approved
0.8625	High Similarity	NPD7096	Clinical (unspecified phase)
0.8623	High Similarity	NPD7472	Approved
0.8598	High Similarity	NPD6232	Discontinued
0.858	High Similarity	NPD4338	Clinical (unspecified phase)
0.8563	High Similarity	NPD5844	Phase 1
0.8562	High Similarity	NPD6801	Discontinued
0.8553	High Similarity	NPD4380	Phase 2
0.8535	High Similarity	NPD1512	Approved
0.8471	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD6797	Phase 2
0.8443	Intermediate Similarity	NPD7473	Discontinued
0.8412	Intermediate Similarity	NPD7251	Discontinued
0.8408	Intermediate Similarity	NPD6799	Approved
0.8395	Intermediate Similarity	NPD7819	Suspended
0.8364	Intermediate Similarity	NPD5494	Approved
0.8363	Intermediate Similarity	NPD7808	Phase 3
0.8354	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD7411	Suspended
0.8258	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD6599	Discontinued
0.8205	Intermediate Similarity	NPD1549	Phase 2
0.8198	Intermediate Similarity	NPD6559	Discontinued
0.8194	Intermediate Similarity	NPD2935	Discontinued
0.8193	Intermediate Similarity	NPD919	Approved
0.8171	Intermediate Similarity	NPD1465	Phase 2
0.8125	Intermediate Similarity	NPD2532	Approved
0.8125	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD2533	Approved
0.8125	Intermediate Similarity	NPD2534	Approved
0.8121	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD5402	Approved
0.8101	Intermediate Similarity	NPD4628	Phase 3
0.8089	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD2796	Approved
0.8072	Intermediate Similarity	NPD7768	Phase 2
0.8052	Intermediate Similarity	NPD230	Phase 1
0.8026	Intermediate Similarity	NPD3027	Phase 3
0.8025	Intermediate Similarity	NPD5403	Approved
0.8013	Intermediate Similarity	NPD1510	Phase 2
0.7988	Intermediate Similarity	NPD6959	Discontinued
0.7987	Intermediate Similarity	NPD1240	Approved
0.7987	Intermediate Similarity	NPD1613	Approved
0.7987	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1551	Phase 2
0.7953	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD447	Suspended
0.7925	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD5401	Approved
0.7885	Intermediate Similarity	NPD1607	Approved
0.7882	Intermediate Similarity	NPD1247	Approved
0.7882	Intermediate Similarity	NPD7199	Phase 2
0.7871	Intermediate Similarity	NPD943	Approved
0.787	Intermediate Similarity	NPD6234	Discontinued
0.7826	Intermediate Similarity	NPD6190	Approved
0.7805	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD920	Approved
0.7784	Intermediate Similarity	NPD37	Approved
0.7778	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD3750	Approved
0.7758	Intermediate Similarity	NPD1653	Approved
0.7751	Intermediate Similarity	NPD4967	Phase 2
0.7751	Intermediate Similarity	NPD4965	Approved
0.7751	Intermediate Similarity	NPD4966	Approved
0.773	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5953	Discontinued
0.7714	Intermediate Similarity	NPD7286	Phase 2
0.7706	Intermediate Similarity	NPD3749	Approved
0.7702	Intermediate Similarity	NPD2800	Approved
0.7702	Intermediate Similarity	NPD1243	Approved
0.7692	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3926	Phase 2
0.7683	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD7033	Discontinued
0.7673	Intermediate Similarity	NPD2799	Discontinued
0.7669	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD7228	Approved
0.7654	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD3226	Approved
0.7595	Intermediate Similarity	NPD1933	Approved
0.7584	Intermediate Similarity	NPD7685	Pre-registration
0.7569	Intermediate Similarity	NPD8434	Phase 2
0.7546	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1203	Approved
0.7529	Intermediate Similarity	NPD5711	Approved
0.7529	Intermediate Similarity	NPD5710	Approved
0.7527	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD8313	Approved
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7486	Intermediate Similarity	NPD5242	Approved
0.7484	Intermediate Similarity	NPD5124	Phase 1
0.7484	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2346	Discontinued
0.7458	Intermediate Similarity	NPD3751	Discontinued
0.7453	Intermediate Similarity	NPD3748	Approved
0.7444	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6651	Approved
0.7436	Intermediate Similarity	NPD9494	Approved
0.7429	Intermediate Similarity	NPD3787	Discontinued
0.7421	Intermediate Similarity	NPD4060	Phase 1
0.7412	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6798	Discontinued
0.7396	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5353	Approved
0.7377	Intermediate Similarity	NPD8150	Discontinued
0.7375	Intermediate Similarity	NPD6355	Discontinued
0.7346	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD9269	Phase 2
0.7338	Intermediate Similarity	NPD9717	Approved
0.7338	Intermediate Similarity	NPD1608	Approved
0.733	Intermediate Similarity	NPD7229	Phase 3
0.7326	Intermediate Similarity	NPD8455	Phase 2
0.731	Intermediate Similarity	NPD6385	Approved
0.731	Intermediate Similarity	NPD6386	Approved
0.7301	Intermediate Similarity	NPD6100	Approved
0.7301	Intermediate Similarity	NPD6099	Approved
0.7296	Intermediate Similarity	NPD7783	Phase 2
0.7296	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7435	Discontinued
0.729	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8151	Discontinued
0.7273	Intermediate Similarity	NPD1652	Phase 2
0.7273	Intermediate Similarity	NPD8127	Discontinued
0.7273	Intermediate Similarity	NPD422	Phase 1
0.7268	Intermediate Similarity	NPD7584	Approved
0.7256	Intermediate Similarity	NPD7266	Discontinued
0.7256	Intermediate Similarity	NPD2344	Approved
0.725	Intermediate Similarity	NPD6233	Phase 2
0.7239	Intermediate Similarity	NPD4308	Phase 3
0.7239	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4360	Phase 2
0.7234	Intermediate Similarity	NPD4363	Phase 3
0.7229	Intermediate Similarity	NPD4110	Phase 3
0.7229	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6781	Approved
0.7225	Intermediate Similarity	NPD6776	Approved
0.7225	Intermediate Similarity	NPD6778	Approved
0.7225	Intermediate Similarity	NPD6779	Approved
0.7225	Intermediate Similarity	NPD6777	Approved
0.7225	Intermediate Similarity	NPD6780	Approved
0.7225	Intermediate Similarity	NPD6782	Approved
0.7212	Intermediate Similarity	NPD2424	Discontinued
0.7202	Intermediate Similarity	NPD7390	Discontinued
0.7198	Intermediate Similarity	NPD7038	Approved
0.7198	Intermediate Similarity	NPD7039	Approved
0.7198	Intermediate Similarity	NPD7240	Approved
0.7197	Intermediate Similarity	NPD2797	Approved
0.7193	Intermediate Similarity	NPD7458	Discontinued
0.7188	Intermediate Similarity	NPD411	Approved
0.7188	Intermediate Similarity	NPD3268	Approved
0.717	Intermediate Similarity	NPD4908	Phase 1
0.716	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6005	Phase 3
0.7152	Intermediate Similarity	NPD6002	Phase 3
0.7152	Intermediate Similarity	NPD6004	Phase 3
0.7152	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD7585	Approved
0.7125	Intermediate Similarity	NPD4625	Phase 3
0.7124	Intermediate Similarity	NPD9545	Approved
0.7118	Intermediate Similarity	NPD6273	Approved
0.7118	Intermediate Similarity	NPD5049	Phase 3
0.7093	Intermediate Similarity	NPD3455	Phase 2
0.7092	Intermediate Similarity	NPD7583	Approved
0.7091	Intermediate Similarity	NPD5405	Approved
0.7091	Intermediate Similarity	NPD5404	Approved
0.7091	Intermediate Similarity	NPD5408	Approved
0.7091	Intermediate Similarity	NPD5406	Approved
0.7083	Intermediate Similarity	NPD2354	Approved
0.7083	Intermediate Similarity	NPD3887	Approved
0.7083	Intermediate Similarity	NPD2309	Approved
0.7078	Intermediate Similarity	NPD9268	Approved

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