NPASS Compound

Structure

CID78071 OpenBabel06191715412D 33 36 0 0 1 0 0 0 0 0999 V2000 1.8320 0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7355 -0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1603 6.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6603 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 0.8660 1.5000 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 -5.1962 3.0000 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 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 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 -2.5981 1.5000 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 -6.9282 3.0000 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 5.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 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 -8.6603 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 3.5000 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 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 30 1 0 0 0 0 6 7 2 0 0 0 0 6 15 1 0 0 0 0 7 19 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 25 1 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 11 15 2 0 0 0 0 11 22 1 0 0 0 0 12 20 2 0 0 0 0 12 21 1 0 0 0 0 13 18 2 0 0 0 0 13 31 1 0 0 0 0 14 23 1 0 0 0 0 14 32 1 0 0 0 0 15 18 1 0 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 24 1 0 0 0 0 19 22 2 0 0 0 0 19 32 1 0 0 0 0 20 33 1 0 0 0 0 21 31 1 0 0 0 0 22 30 1 0 0 0 0 23 26 1 0 0 0 0 23 27 1 1 0 0 0 24 28 2 0 0 0 0 25 33 1 0 0 0 0 26 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.18
Volume:	461.83
LogP:	4.106
LogD:	2.969
LogS:	-3.189
# Rotatable Bonds:	6
TPSA:	98.36
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.579
Synthetic Accessibility Score:	3.434
Fsp3:	0.346
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.876
MDCK Permeability:	2.1751160602434538e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.213
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	94.7762222290039%
Volume Distribution (VD):	0.557
Pgp-substrate:	4.282192707061768%

ADMET: Metabolism

CYP1A2-inhibitor:	0.352
CYP1A2-substrate:	0.719
CYP2C19-inhibitor:	0.451
CYP2C19-substrate:	0.132
CYP2C9-inhibitor:	0.882
CYP2C9-substrate:	0.876
CYP2D6-inhibitor:	0.856
CYP2D6-substrate:	0.73
CYP3A4-inhibitor:	0.729
CYP3A4-substrate:	0.502

ADMET: Excretion

Clearance (CL):	4.177
Half-life (T1/2):	0.167

ADMET: Toxicity

hERG Blockers:	0.4
Human Hepatotoxicity (H-HT):	0.805
Drug-inuced Liver Injury (DILI):	0.312
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.365
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.14
Carcinogencity:	0.41
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.638

Download Data

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

Natural Product: NPC78071

Natural Product ID:	NPC78071
*Common Name:**	Pierreione B
IUPAC Name:	7-[4-[(2R)-2,3-dihydroxy-3-methylbutoxy]-3-methoxyphenyl]-2,2-dimethylpyrano[3,2-g]chromen-6-one
Synonyms:	Pierreione B
Standard InCHIKey:	RDXLWAJRBPKMPD-HSZRJFAPSA-N
Standard InCHI:	InChI=1S/C26H28O7/c1-25(2)9-8-16-10-17-21(12-20(16)33-25)31-13-18(24(17)28)15-6-7-19(22(11-15)30-5)32-14-23(27)26(3,4)29/h6-13,23,27,29H,14H2,1-5H3/t23-/m1/s1
SMILES:	COc1cc(ccc1OC[C@H](C(O)(C)C)O)c1coc2c(c1=O)cc1c(c2)OC(C=C1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1773673
PubChem CID:	52951514
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003526] 6-prenylated isoflavanones

*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
NPO20249	Antheroporum pierrei	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21452840]
NPO20249	Antheroporum pierrei	Species	Fabaceae	Eukaryota	n.a.	twig	n.a.	PMID[21452840]
NPO20249	Antheroporum pierrei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT730	Cell Line	MC-38	Mus musculus	Activity	=	300.0	Zone units	PMID[507503]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	18.0	ug	PMID[507503]

☑ 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 NPC78071 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	423
0.1-0.2	1627
0.2-0.3	3738
0.3-0.4	9714
0.4-0.5	8903
0.5-0.6	3600
0.6-0.7	5279
0.7-0.8	5110
0.8-0.85	2657
0.85-0.9	1406
0.9-0.95	225
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC187792
0.9671	High Similarity	NPC74178
0.9671	High Similarity	NPC184755
0.9608	High Similarity	NPC475784
0.9597	High Similarity	NPC189270
0.9597	High Similarity	NPC5840
0.9545	High Similarity	NPC474038
0.9539	High Similarity	NPC282307
0.9539	High Similarity	NPC170026
0.9484	High Similarity	NPC474034
0.9484	High Similarity	NPC474033
0.9481	High Similarity	NPC118256
0.9481	High Similarity	NPC192686
0.9481	High Similarity	NPC119209
0.9477	High Similarity	NPC473272
0.9477	High Similarity	NPC52889
0.9477	High Similarity	NPC284820
0.9474	High Similarity	NPC234255
0.947	High Similarity	NPC40033
0.9423	High Similarity	NPC472625
0.9419	High Similarity	NPC472632
0.9419	High Similarity	NPC26326
0.9416	High Similarity	NPC204879
0.9416	High Similarity	NPC473990
0.9412	High Similarity	NPC472455
0.9412	High Similarity	NPC471985
0.9363	High Similarity	NPC303174
0.9363	High Similarity	NPC50960
0.9359	High Similarity	NPC261470
0.9359	High Similarity	NPC476247
0.9355	High Similarity	NPC174953
0.9355	High Similarity	NPC328102
0.9355	High Similarity	NPC28241
0.9351	High Similarity	NPC218313
0.9351	High Similarity	NPC291508
0.9351	High Similarity	NPC474681
0.9351	High Similarity	NPC474055
0.9351	High Similarity	NPC27337
0.9351	High Similarity	NPC472598
0.9346	High Similarity	NPC472280
0.9346	High Similarity	NPC470681
0.9346	High Similarity	NPC477530
0.9342	High Similarity	NPC237994
0.9299	High Similarity	NPC124038
0.9299	High Similarity	NPC186686
0.9295	High Similarity	NPC472634
0.9295	High Similarity	NPC471210
0.9295	High Similarity	NPC198829
0.9295	High Similarity	NPC259456
0.9295	High Similarity	NPC134783
0.929	High Similarity	NPC117418
0.929	High Similarity	NPC53545
0.9286	High Similarity	NPC35038
0.9286	High Similarity	NPC278778
0.9286	High Similarity	NPC133970
0.9286	High Similarity	NPC195796
0.9286	High Similarity	NPC6633
0.9286	High Similarity	NPC5322
0.9286	High Similarity	NPC291878
0.9281	High Similarity	NPC128961
0.9281	High Similarity	NPC7989
0.9281	High Similarity	NPC472408
0.9281	High Similarity	NPC170492
0.9281	High Similarity	NPC223701
0.9281	High Similarity	NPC472583
0.9276	High Similarity	NPC256406
0.9276	High Similarity	NPC154345
0.9262	High Similarity	NPC471590
0.9236	High Similarity	NPC83922
0.9236	High Similarity	NPC474150
0.9236	High Similarity	NPC472635
0.9236	High Similarity	NPC194427
0.9236	High Similarity	NPC472448
0.9236	High Similarity	NPC474162
0.9231	High Similarity	NPC472624
0.9231	High Similarity	NPC472631
0.9231	High Similarity	NPC287328
0.9231	High Similarity	NPC472630
0.9231	High Similarity	NPC474960
0.9231	High Similarity	NPC282009
0.9231	High Similarity	NPC476980
0.9226	High Similarity	NPC471209
0.9226	High Similarity	NPC476981
0.9226	High Similarity	NPC19097
0.9226	High Similarity	NPC183851
0.9226	High Similarity	NPC63454
0.9221	High Similarity	NPC117992
0.9221	High Similarity	NPC226025
0.9221	High Similarity	NPC470327
0.9221	High Similarity	NPC321779
0.9221	High Similarity	NPC477503
0.9221	High Similarity	NPC57674
0.9221	High Similarity	NPC230149
0.9221	High Similarity	NPC168247
0.9221	High Similarity	NPC45849
0.9221	High Similarity	NPC200761
0.9221	High Similarity	NPC256925
0.9221	High Similarity	NPC200246
0.9221	High Similarity	NPC152951
0.9216	High Similarity	NPC285623
0.9216	High Similarity	NPC471982
0.9216	High Similarity	NPC324233
0.9216	High Similarity	NPC323626
0.9205	High Similarity	NPC476342
0.9205	High Similarity	NPC6511
0.9187	High Similarity	NPC288813
0.9187	High Similarity	NPC165456
0.9182	High Similarity	NPC119589
0.9182	High Similarity	NPC173292
0.9182	High Similarity	NPC43319
0.9182	High Similarity	NPC471213
0.9182	High Similarity	NPC272502
0.9177	High Similarity	NPC470772
0.9172	High Similarity	NPC167678
0.9172	High Similarity	NPC142252
0.9172	High Similarity	NPC29876
0.9172	High Similarity	NPC57715
0.9172	High Similarity	NPC471211
0.9172	High Similarity	NPC471499
0.9172	High Similarity	NPC234644
0.9172	High Similarity	NPC289771
0.9172	High Similarity	NPC40037
0.9172	High Similarity	NPC471212
0.9167	High Similarity	NPC113055
0.9167	High Similarity	NPC284127
0.9167	High Similarity	NPC469658
0.9167	High Similarity	NPC22192
0.9167	High Similarity	NPC476410
0.9167	High Similarity	NPC172202
0.9161	High Similarity	NPC209614
0.9161	High Similarity	NPC472626
0.9161	High Similarity	NPC470328
0.9161	High Similarity	NPC208152
0.9161	High Similarity	NPC78492
0.9161	High Similarity	NPC180340
0.9161	High Similarity	NPC470600
0.9161	High Similarity	NPC276444
0.9156	High Similarity	NPC33051
0.9156	High Similarity	NPC192083
0.9156	High Similarity	NPC469405
0.9156	High Similarity	NPC213896
0.9156	High Similarity	NPC18727
0.9156	High Similarity	NPC227337
0.9156	High Similarity	NPC74924
0.9156	High Similarity	NPC273462
0.9156	High Similarity	NPC49402
0.9156	High Similarity	NPC88983
0.9156	High Similarity	NPC70433
0.915	High Similarity	NPC263384
0.915	High Similarity	NPC472420
0.915	High Similarity	NPC244577
0.915	High Similarity	NPC472422
0.915	High Similarity	NPC471676
0.9145	High Similarity	NPC5173
0.9145	High Similarity	NPC171916
0.9145	High Similarity	NPC38545
0.9139	High Similarity	NPC97716
0.9139	High Similarity	NPC237635
0.9139	High Similarity	NPC104406
0.9139	High Similarity	NPC24673
0.9139	High Similarity	NPC201731
0.9139	High Similarity	NPC79469
0.913	High Similarity	NPC103307
0.9128	High Similarity	NPC476054
0.9125	High Similarity	NPC150131
0.9125	High Similarity	NPC218226
0.9125	High Similarity	NPC8965
0.9119	High Similarity	NPC293319
0.9119	High Similarity	NPC470773
0.9119	High Similarity	NPC300053
0.9119	High Similarity	NPC108433
0.9119	High Similarity	NPC62261
0.9114	High Similarity	NPC472964
0.9114	High Similarity	NPC81679
0.9114	High Similarity	NPC78332
0.9108	High Similarity	NPC471976
0.9108	High Similarity	NPC188433
0.9108	High Similarity	NPC36217
0.9108	High Similarity	NPC472902
0.9108	High Similarity	NPC470326
0.9108	High Similarity	NPC204290
0.9108	High Similarity	NPC471973
0.9103	High Similarity	NPC67876
0.9103	High Similarity	NPC237418
0.9103	High Similarity	NPC218871
0.9103	High Similarity	NPC223787
0.9103	High Similarity	NPC52530
0.9103	High Similarity	NPC476630
0.9103	High Similarity	NPC470402
0.9097	High Similarity	NPC477958
0.9097	High Similarity	NPC217706
0.9097	High Similarity	NPC48579
0.9097	High Similarity	NPC259710
0.9097	High Similarity	NPC304207
0.9097	High Similarity	NPC207809
0.9091	High Similarity	NPC161881
0.9091	High Similarity	NPC10807
0.9091	High Similarity	NPC475790
0.9091	High Similarity	NPC236637
0.9091	High Similarity	NPC257648

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 NPC78071 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	940
0.2-0.3	1710
0.3-0.4	2619
0.4-0.5	1890
0.5-0.6	1006
0.6-0.7	431
0.7-0.8	125
0.8-0.85	34
0.85-0.9	21
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9156	High Similarity	NPD2393	Clinical (unspecified phase)
0.9091	High Similarity	NPD1934	Approved
0.8961	High Similarity	NPD4380	Phase 2
0.891	High Similarity	NPD2801	Approved
0.8882	High Similarity	NPD6167	Clinical (unspecified phase)
0.8882	High Similarity	NPD6168	Clinical (unspecified phase)
0.8882	High Similarity	NPD6166	Phase 2
0.8868	High Similarity	NPD5494	Approved
0.8854	High Similarity	NPD3817	Phase 2
0.8797	High Similarity	NPD3882	Suspended
0.879	High Similarity	NPD7096	Clinical (unspecified phase)
0.8773	High Similarity	NPD3818	Discontinued
0.8726	High Similarity	NPD6801	Discontinued
0.8725	High Similarity	NPD2796	Approved
0.872	High Similarity	NPD7054	Approved
0.8693	High Similarity	NPD1511	Approved
0.8667	High Similarity	NPD7472	Approved
0.8667	High Similarity	NPD7074	Phase 3
0.8636	High Similarity	NPD7410	Clinical (unspecified phase)
0.8636	High Similarity	NPD4378	Clinical (unspecified phase)
0.8625	High Similarity	NPD4381	Clinical (unspecified phase)
0.8625	High Similarity	NPD7075	Discontinued
0.8581	High Similarity	NPD1512	Approved
0.8553	High Similarity	NPD7819	Suspended
0.8512	High Similarity	NPD7808	Phase 3
0.8503	High Similarity	NPD6797	Phase 2
0.8494	Intermediate Similarity	NPD5844	Phase 1
0.8487	Intermediate Similarity	NPD1549	Phase 2
0.8452	Intermediate Similarity	NPD7251	Discontinued
0.8452	Intermediate Similarity	NPD6799	Approved
0.8447	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD7411	Suspended
0.8421	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1510	Phase 2
0.8408	Intermediate Similarity	NPD5403	Approved
0.8402	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD5401	Approved
0.8385	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD5402	Approved
0.8383	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD919	Approved
0.825	Intermediate Similarity	NPD6599	Discontinued
0.8242	Intermediate Similarity	NPD1247	Approved
0.8193	Intermediate Similarity	NPD6232	Discontinued
0.8155	Intermediate Similarity	NPD7473	Discontinued
0.8146	Intermediate Similarity	NPD1240	Approved
0.8133	Intermediate Similarity	NPD6959	Discontinued
0.8129	Intermediate Similarity	NPD6559	Discontinued
0.807	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1607	Approved
0.8036	Intermediate Similarity	NPD3926	Phase 2
0.8	Intermediate Similarity	NPD7768	Phase 2
0.7988	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD4628	Phase 3
0.7911	Intermediate Similarity	NPD3750	Approved
0.7908	Intermediate Similarity	NPD943	Approved
0.7879	Intermediate Similarity	NPD1465	Phase 2
0.7848	Intermediate Similarity	NPD1243	Approved
0.784	Intermediate Similarity	NPD920	Approved
0.7821	Intermediate Similarity	NPD3748	Approved
0.7812	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7199	Phase 2
0.7792	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1613	Approved
0.7785	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2935	Discontinued
0.7738	Intermediate Similarity	NPD3749	Approved
0.7716	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD3027	Phase 3
0.7707	Intermediate Similarity	NPD2799	Discontinued
0.7688	Intermediate Similarity	NPD3751	Discontinued
0.767	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2313	Discontinued
0.7661	Intermediate Similarity	NPD3787	Discontinued
0.7658	Intermediate Similarity	NPD1551	Phase 2
0.765	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD5124	Phase 1
0.7628	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1933	Approved
0.7628	Intermediate Similarity	NPD447	Suspended
0.7625	Intermediate Similarity	NPD2800	Approved
0.7624	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2532	Approved
0.7607	Intermediate Similarity	NPD2534	Approved
0.7607	Intermediate Similarity	NPD2533	Approved
0.7595	Intermediate Similarity	NPD7033	Discontinued
0.7578	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD5953	Discontinued
0.7546	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD3226	Approved
0.7516	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD37	Approved
0.7484	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7584	Approved
0.7471	Intermediate Similarity	NPD4965	Approved
0.7471	Intermediate Similarity	NPD4967	Phase 2
0.7471	Intermediate Similarity	NPD4966	Approved
0.747	Intermediate Similarity	NPD1653	Approved
0.7468	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6651	Approved
0.7446	Intermediate Similarity	NPD4363	Phase 3
0.7446	Intermediate Similarity	NPD4360	Phase 2
0.7444	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7286	Phase 2
0.7438	Intermediate Similarity	NPD6100	Approved
0.7438	Intermediate Similarity	NPD6099	Approved
0.7436	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8312	Approved
0.743	Intermediate Similarity	NPD8313	Approved
0.7425	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6190	Approved
0.7419	Intermediate Similarity	NPD6832	Phase 2
0.7416	Intermediate Similarity	NPD7685	Pre-registration
0.7403	Intermediate Similarity	NPD2798	Approved
0.7403	Intermediate Similarity	NPD8434	Phase 2
0.7396	Intermediate Similarity	NPD6844	Discontinued
0.7394	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2344	Approved
0.7384	Intermediate Similarity	NPD6234	Discontinued
0.7371	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD9494	Approved
0.7346	Intermediate Similarity	NPD2424	Discontinued
0.734	Intermediate Similarity	NPD6780	Approved
0.734	Intermediate Similarity	NPD6781	Approved
0.734	Intermediate Similarity	NPD6776	Approved
0.734	Intermediate Similarity	NPD6779	Approved
0.734	Intermediate Similarity	NPD6778	Approved
0.734	Intermediate Similarity	NPD6782	Approved
0.734	Intermediate Similarity	NPD6777	Approved
0.7333	Intermediate Similarity	NPD7390	Discontinued
0.7325	Intermediate Similarity	NPD6798	Discontinued
0.7321	Intermediate Similarity	NPD7458	Discontinued
0.732	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD5242	Approved
0.7308	Intermediate Similarity	NPD8150	Discontinued
0.7308	Intermediate Similarity	NPD4908	Phase 1
0.7299	Intermediate Similarity	NPD8127	Discontinued
0.7296	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4661	Approved
0.7289	Intermediate Similarity	NPD4662	Approved
0.7288	Intermediate Similarity	NPD7228	Approved
0.7267	Intermediate Similarity	NPD4308	Phase 3
0.7267	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD8455	Phase 2
0.7246	Intermediate Similarity	NPD6273	Approved
0.7226	Intermediate Similarity	NPD1203	Approved
0.7225	Intermediate Similarity	NPD7435	Discontinued
0.7219	Intermediate Similarity	NPD4361	Phase 2
0.7219	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8151	Discontinued
0.7215	Intermediate Similarity	NPD3268	Approved
0.7212	Intermediate Similarity	NPD2309	Approved
0.7209	Intermediate Similarity	NPD5353	Approved
0.72	Intermediate Similarity	NPD5536	Phase 2
0.7195	Intermediate Similarity	NPD1652	Phase 2
0.7191	Intermediate Similarity	NPD2163	Approved
0.7188	Intermediate Similarity	NPD6355	Discontinued
0.7167	Intermediate Similarity	NPD3823	Discontinued
0.7161	Intermediate Similarity	NPD3225	Approved
0.7159	Intermediate Similarity	NPD7229	Phase 3
0.7152	Intermediate Similarity	NPD1548	Phase 1
0.7152	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD5049	Phase 3
0.7143	Intermediate Similarity	NPD9717	Approved
0.7135	Intermediate Similarity	NPD6386	Approved
0.7135	Intermediate Similarity	NPD5889	Approved
0.7135	Intermediate Similarity	NPD5890	Approved
0.7135	Intermediate Similarity	NPD7696	Phase 3
0.7135	Intermediate Similarity	NPD7698	Approved
0.7135	Intermediate Similarity	NPD7697	Approved
0.7135	Intermediate Similarity	NPD6385	Approved
0.7135	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3018	Phase 2
0.7127	Intermediate Similarity	NPD7240	Approved
0.7125	Intermediate Similarity	NPD4307	Phase 2
0.7115	Intermediate Similarity	NPD2797	Approved
0.7113	Intermediate Similarity	NPD7583	Approved
0.711	Intermediate Similarity	NPD4288	Approved
0.7108	Intermediate Similarity	NPD3887	Approved
0.7108	Intermediate Similarity	NPD2354	Approved
0.7098	Intermediate Similarity	NPD7870	Phase 2
0.7098	Intermediate Similarity	NPD7871	Phase 2
0.7091	Intermediate Similarity	NPD2654	Approved
0.7091	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6674	Discontinued
0.7088	Intermediate Similarity	NPD7549	Discontinued
0.7083	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6823	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