NPASS Compound

Structure

CID284127 OpenBabel06191716092D 38 41 0 0 1 0 0 0 0 0999 V2000 -6.0622 -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 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 34 1 0 0 0 0 2 35 1 0 0 0 0 3 36 1 0 0 0 0 4 5 2 0 0 0 0 4 13 1 0 0 0 0 5 16 1 0 0 0 0 6 13 2 0 0 0 0 6 20 1 0 0 0 0 7 14 2 0 0 0 0 7 22 1 0 0 0 0 8 14 1 0 0 0 0 8 23 2 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 15 1 0 0 0 0 10 21 2 0 0 0 0 11 18 1 0 0 0 0 11 19 2 0 0 0 0 12 28 1 0 0 0 0 13 26 1 0 0 0 0 14 19 1 0 0 0 0 15 29 1 0 0 0 0 16 20 2 0 0 0 0 16 30 1 0 0 0 0 17 25 2 0 0 0 0 17 31 1 0 0 0 0 18 25 1 0 0 0 0 18 32 2 0 0 0 0 19 37 1 0 0 0 0 20 34 1 0 0 0 0 21 25 1 0 0 0 0 21 37 1 0 0 0 0 22 27 2 0 0 0 0 22 35 1 0 0 0 0 23 27 1 0 0 0 0 23 36 1 0 0 0 0 24 12 1 6 0 0 0 24 26 1 0 0 0 0 24 38 1 0 0 0 0 26 33 1 6 0 0 0 27 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	526.15
Volume:	509.014
LogP:	2.792
LogD:	2.35
LogS:	-4.18
# Rotatable Bonds:	9
TPSA:	168.28
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.217
Synthetic Accessibility Score:	3.611
Fsp3:	0.222
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.24
MDCK Permeability:	2.1515397747862153e-05
Pgp-inhibitor:	0.633
Pgp-substrate:	0.96
Human Intestinal Absorption (HIA):	0.456
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.918

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	86.71361541748047%
Volume Distribution (VD):	0.847
Pgp-substrate:	21.518770217895508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.321
CYP1A2-substrate:	0.765
CYP2C19-inhibitor:	0.078
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.639
CYP2C9-substrate:	0.884
CYP2D6-inhibitor:	0.205
CYP2D6-substrate:	0.754
CYP3A4-inhibitor:	0.591
CYP3A4-substrate:	0.28

ADMET: Excretion

Clearance (CL):	6.41
Half-life (T1/2):	0.827

ADMET: Toxicity

hERG Blockers:	0.275
Human Hepatotoxicity (H-HT):	0.193
Drug-inuced Liver Injury (DILI):	0.746
AMES Toxicity:	0.234
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.807
Skin Sensitization:	0.777
Carcinogencity:	0.015
Eye Corrosion:	0.003
Eye Irritation:	0.088
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC284127

Natural Product ID:	NPC284127
*Common Name:**	(-)-(7''r,8''s)-4'',5,7-Trihydroxy-3',3'',5'-Trimethoxy-4',8''-Oxyflavonolignan-7'',9''-Diol
IUPAC Name:	2-[4-[(1R,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3,5-dimethoxyphenyl]-5,7-dihydroxychromen-4-one
Synonyms:
Standard InCHIKey:	WXNJNHFYIWEHIL-AZGAKELHSA-N
Standard InCHI:	InChI=1S/C27H26O11/c1-34-20-6-13(4-5-16(20)30)26(33)24(12-28)38-27-22(35-2)7-14(8-23(27)36-3)19-11-18(32)25-17(31)9-15(29)10-21(25)37-19/h4-11,24,26,28-31,33H,12H2,1-3H3/t24-,26+/m0/s1
SMILES:	OC[C@@H]([C@@H](c1ccc(c(c1)OC)O)O)Oc1c(OC)cc(cc1OC)c1cc(=O)c2c(o1)cc(cc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1797782
PubChem CID:	5323535
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002595] 3'-O-methylated flavonoids

*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
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	stem	n.a.	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	skin-removed stems	Pingle Town, Sichuang Province, China	2008-AUG	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22690646]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	<	30.0	%	PMID[529963]

☑ 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 NPC284127 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	430
0.1-0.2	1740
0.2-0.3	4300
0.3-0.4	10173
0.4-0.5	7853
0.5-0.6	3724
0.6-0.7	4845
0.7-0.8	4992
0.8-0.85	2233
0.85-0.9	1555
0.9-0.95	831
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC172202
1.0	High Similarity	NPC476410
0.9933	High Similarity	NPC183851
0.9933	High Similarity	NPC63454
0.9868	High Similarity	NPC66618
0.9868	High Similarity	NPC165970
0.9868	High Similarity	NPC84324
0.9868	High Similarity	NPC288131
0.9868	High Similarity	NPC305987
0.9868	High Similarity	NPC113163
0.9803	High Similarity	NPC101731
0.9739	High Similarity	NPC158188
0.961	High Similarity	NPC142252
0.961	High Similarity	NPC26326
0.9554	High Similarity	NPC295082
0.9554	High Similarity	NPC243877
0.9551	High Similarity	NPC36
0.9551	High Similarity	NPC7688
0.9551	High Similarity	NPC58223
0.9551	High Similarity	NPC125039
0.9551	High Similarity	NPC72787
0.9551	High Similarity	NPC36916
0.9551	High Similarity	NPC7154
0.9548	High Similarity	NPC476247
0.9548	High Similarity	NPC219927
0.9542	High Similarity	NPC470402
0.9494	High Similarity	NPC475212
0.9484	High Similarity	NPC474038
0.9481	High Similarity	NPC53545
0.9481	High Similarity	NPC117418
0.9474	High Similarity	NPC18727
0.9467	High Similarity	NPC52005
0.9467	High Similarity	NPC287101
0.9467	High Similarity	NPC183950
0.9467	High Similarity	NPC48479
0.9467	High Similarity	NPC177298
0.9467	High Similarity	NPC137062
0.9467	High Similarity	NPC223579
0.943	High Similarity	NPC14662
0.9427	High Similarity	NPC311830
0.9427	High Similarity	NPC22832
0.9427	High Similarity	NPC477840
0.9423	High Similarity	NPC477841
0.9419	High Similarity	NPC475784
0.9419	High Similarity	NPC192686
0.9419	High Similarity	NPC119209
0.9419	High Similarity	NPC118256
0.9416	High Similarity	NPC474055
0.9416	High Similarity	NPC112954
0.9416	High Similarity	NPC472598
0.9416	High Similarity	NPC183
0.9412	High Similarity	NPC163780
0.9412	High Similarity	NPC227325
0.9412	High Similarity	NPC196439
0.9412	High Similarity	NPC167815
0.9412	High Similarity	NPC50715
0.9412	High Similarity	NPC201136
0.9412	High Similarity	NPC146165
0.9412	High Similarity	NPC4455
0.9412	High Similarity	NPC92659
0.9412	High Similarity	NPC213622
0.9412	High Similarity	NPC183597
0.9412	High Similarity	NPC2476
0.9412	High Similarity	NPC138360
0.9412	High Similarity	NPC280339
0.9412	High Similarity	NPC128863
0.9408	High Similarity	NPC60972
0.9408	High Similarity	NPC302950
0.9408	High Similarity	NPC236637
0.9408	High Similarity	NPC219582
0.9408	High Similarity	NPC39732
0.94	High Similarity	NPC195202
0.94	High Similarity	NPC120464
0.94	High Similarity	NPC119059
0.9371	High Similarity	NPC188079
0.9363	High Similarity	NPC88023
0.9363	High Similarity	NPC191306
0.9363	High Similarity	NPC19709
0.9363	High Similarity	NPC284960
0.9363	High Similarity	NPC270335
0.9363	High Similarity	NPC309025
0.9363	High Similarity	NPC222936
0.9363	High Similarity	NPC243930
0.9363	High Similarity	NPC472625
0.9363	High Similarity	NPC272064
0.9359	High Similarity	NPC472632
0.9359	High Similarity	NPC471499
0.9359	High Similarity	NPC289771
0.9359	High Similarity	NPC472634
0.9351	High Similarity	NPC278778
0.9351	High Similarity	NPC326037
0.9351	High Similarity	NPC291878
0.9351	High Similarity	NPC195796
0.9351	High Similarity	NPC320825
0.9351	High Similarity	NPC13858
0.9351	High Similarity	NPC35038
0.9351	High Similarity	NPC250922
0.9346	High Similarity	NPC78326
0.9346	High Similarity	NPC176775
0.9346	High Similarity	NPC58382
0.9346	High Similarity	NPC69394
0.9346	High Similarity	NPC47781
0.9346	High Similarity	NPC75279
0.9346	High Similarity	NPC160951
0.9346	High Similarity	NPC255350
0.9346	High Similarity	NPC145379
0.9346	High Similarity	NPC162351
0.9346	High Similarity	NPC274327
0.9346	High Similarity	NPC270620
0.9346	High Similarity	NPC22519
0.9346	High Similarity	NPC183878
0.9346	High Similarity	NPC276409
0.9346	High Similarity	NPC250822
0.9346	High Similarity	NPC231018
0.9346	High Similarity	NPC236223
0.9346	High Similarity	NPC179126
0.9342	High Similarity	NPC54394
0.9342	High Similarity	NPC252933
0.9342	High Similarity	NPC28274
0.9342	High Similarity	NPC200740
0.9342	High Similarity	NPC50403
0.9342	High Similarity	NPC125062
0.9342	High Similarity	NPC133953
0.9333	High Similarity	NPC33265
0.9333	High Similarity	NPC62536
0.9333	High Similarity	NPC12200
0.9333	High Similarity	NPC108406
0.9317	High Similarity	NPC472993
0.9313	High Similarity	NPC102277
0.9313	High Similarity	NPC279209
0.9308	High Similarity	NPC229729
0.9308	High Similarity	NPC260266
0.9299	High Similarity	NPC472635
0.9299	High Similarity	NPC474034
0.9299	High Similarity	NPC189142
0.9299	High Similarity	NPC473043
0.9299	High Similarity	NPC77660
0.9299	High Similarity	NPC474033
0.9295	High Similarity	NPC472631
0.9295	High Similarity	NPC470326
0.9295	High Similarity	NPC472630
0.9295	High Similarity	NPC174953
0.9295	High Similarity	NPC287328
0.9295	High Similarity	NPC282009
0.929	High Similarity	NPC291508
0.929	High Similarity	NPC474208
0.929	High Similarity	NPC75215
0.929	High Similarity	NPC471479
0.929	High Similarity	NPC475267
0.929	High Similarity	NPC27337
0.929	High Similarity	NPC156057
0.929	High Similarity	NPC284820
0.929	High Similarity	NPC48208
0.929	High Similarity	NPC474836
0.929	High Similarity	NPC189179
0.929	High Similarity	NPC227192
0.929	High Similarity	NPC473272
0.929	High Similarity	NPC162869
0.929	High Similarity	NPC52530
0.929	High Similarity	NPC224137
0.929	High Similarity	NPC471515
0.929	High Similarity	NPC93376
0.9286	High Similarity	NPC208197
0.9286	High Similarity	NPC477503
0.9286	High Similarity	NPC256612
0.9286	High Similarity	NPC45849
0.9286	High Similarity	NPC200761
0.9286	High Similarity	NPC321779
0.9286	High Similarity	NPC470327
0.9286	High Similarity	NPC20830
0.9281	High Similarity	NPC55205
0.9281	High Similarity	NPC293183
0.9281	High Similarity	NPC241498
0.9281	High Similarity	NPC222830
0.9281	High Similarity	NPC131624
0.9281	High Similarity	NPC198826
0.9281	High Similarity	NPC142540
0.9281	High Similarity	NPC212678
0.9281	High Similarity	NPC83508
0.9281	High Similarity	NPC275722
0.9281	High Similarity	NPC301323
0.9281	High Similarity	NPC25270
0.9281	High Similarity	NPC279989
0.9281	High Similarity	NPC257648
0.9281	High Similarity	NPC120163
0.9281	High Similarity	NPC275836
0.9281	High Similarity	NPC100887
0.9281	High Similarity	NPC256283
0.9281	High Similarity	NPC57030
0.9281	High Similarity	NPC123886
0.9281	High Similarity	NPC471982
0.9281	High Similarity	NPC71334
0.9281	High Similarity	NPC156222
0.9281	High Similarity	NPC187498
0.9281	High Similarity	NPC239128
0.9281	High Similarity	NPC188203
0.9281	High Similarity	NPC82325
0.9281	High Similarity	NPC472912
0.9281	High Similarity	NPC477231
0.9281	High Similarity	NPC162313

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 NPC284127 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	924
0.2-0.3	1827
0.3-0.4	2659
0.4-0.5	1783
0.5-0.6	981
0.6-0.7	403
0.7-0.8	117
0.8-0.85	28
0.85-0.9	20
0.9-0.95	10
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9551	High Similarity	NPD6167	Clinical (unspecified phase)
0.9551	High Similarity	NPD6166	Phase 2
0.9551	High Similarity	NPD6168	Clinical (unspecified phase)
0.9408	High Similarity	NPD1934	Approved
0.9346	High Similarity	NPD2801	Approved
0.925	High Similarity	NPD7054	Approved
0.9221	High Similarity	NPD2393	Clinical (unspecified phase)
0.9193	High Similarity	NPD7472	Approved
0.9133	High Similarity	NPD1511	Approved
0.9074	High Similarity	NPD7074	Phase 3
0.9068	High Similarity	NPD3818	Discontinued
0.9038	High Similarity	NPD3817	Phase 2
0.9018	High Similarity	NPD6797	Phase 2
0.9013	High Similarity	NPD1512	Approved
0.8981	High Similarity	NPD3882	Suspended
0.8981	High Similarity	NPD4868	Clinical (unspecified phase)
0.8963	High Similarity	NPD7251	Discontinued
0.8909	High Similarity	NPD4338	Clinical (unspecified phase)
0.8909	High Similarity	NPD7808	Phase 3
0.8903	High Similarity	NPD4380	Phase 2
0.8805	High Similarity	NPD4381	Clinical (unspecified phase)
0.8581	High Similarity	NPD7410	Clinical (unspecified phase)
0.8581	High Similarity	NPD4378	Clinical (unspecified phase)
0.8563	High Similarity	NPD7993	Clinical (unspecified phase)
0.8562	High Similarity	NPD8443	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD6232	Discontinued
0.8466	Intermediate Similarity	NPD5494	Approved
0.8457	Intermediate Similarity	NPD7075	Discontinued
0.8447	Intermediate Similarity	NPD5402	Approved
0.8443	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD5844	Phase 1
0.8438	Intermediate Similarity	NPD6801	Discontinued
0.8434	Intermediate Similarity	NPD7473	Discontinued
0.8431	Intermediate Similarity	NPD1549	Phase 2
0.8421	Intermediate Similarity	NPD2796	Approved
0.8415	Intermediate Similarity	NPD6959	Discontinued
0.8375	Intermediate Similarity	NPD7411	Suspended
0.8355	Intermediate Similarity	NPD1510	Phase 2
0.8354	Intermediate Similarity	NPD5403	Approved
0.828	Intermediate Similarity	NPD6799	Approved
0.8272	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD5401	Approved
0.8187	Intermediate Similarity	NPD6559	Discontinued
0.816	Intermediate Similarity	NPD7819	Suspended
0.816	Intermediate Similarity	NPD1465	Phase 2
0.8092	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1240	Approved
0.8092	Intermediate Similarity	NPD1613	Approved
0.8047	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD3027	Phase 3
0.8012	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD3926	Phase 2
0.7987	Intermediate Similarity	NPD1607	Approved
0.7976	Intermediate Similarity	NPD7199	Phase 2
0.7975	Intermediate Similarity	NPD6599	Discontinued
0.7974	Intermediate Similarity	NPD943	Approved
0.7962	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7768	Phase 2
0.787	Intermediate Similarity	NPD1247	Approved
0.7865	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD3750	Approved
0.7857	Intermediate Similarity	NPD919	Approved
0.7853	Intermediate Similarity	NPD1653	Approved
0.7829	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6190	Approved
0.7806	Intermediate Similarity	NPD230	Phase 1
0.7799	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD3749	Approved
0.7778	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6234	Discontinued
0.775	Intermediate Similarity	NPD4628	Phase 3
0.7746	Intermediate Similarity	NPD3751	Discontinued
0.7727	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD1551	Phase 2
0.7719	Intermediate Similarity	NPD3787	Discontinued
0.7716	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD447	Suspended
0.767	Intermediate Similarity	NPD7685	Pre-registration
0.7665	Intermediate Similarity	NPD37	Approved
0.7644	Intermediate Similarity	NPD7228	Approved
0.764	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4965	Approved
0.7633	Intermediate Similarity	NPD4966	Approved
0.7633	Intermediate Similarity	NPD4967	Phase 2
0.761	Intermediate Similarity	NPD2935	Discontinued
0.7607	Intermediate Similarity	NPD7390	Discontinued
0.7598	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD4908	Phase 1
0.7584	Intermediate Similarity	NPD8312	Approved
0.7584	Intermediate Similarity	NPD8313	Approved
0.7582	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2800	Approved
0.7561	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD2534	Approved
0.7561	Intermediate Similarity	NPD2532	Approved
0.7561	Intermediate Similarity	NPD2533	Approved
0.7547	Intermediate Similarity	NPD3748	Approved
0.7547	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD9494	Approved
0.7528	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3226	Approved
0.747	Intermediate Similarity	NPD920	Approved
0.7468	Intermediate Similarity	NPD1933	Approved
0.7455	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2344	Approved
0.7438	Intermediate Similarity	NPD7033	Discontinued
0.7421	Intermediate Similarity	NPD6651	Approved
0.7416	Intermediate Similarity	NPD5953	Discontinued
0.7405	Intermediate Similarity	NPD4360	Phase 2
0.7405	Intermediate Similarity	NPD4363	Phase 3
0.7391	Intermediate Similarity	NPD6100	Approved
0.7391	Intermediate Similarity	NPD6099	Approved
0.7389	Intermediate Similarity	NPD6798	Discontinued
0.7372	Intermediate Similarity	NPD6832	Phase 2
0.7362	Intermediate Similarity	NPD1243	Approved
0.7358	Intermediate Similarity	NPD8151	Discontinued
0.7353	Intermediate Similarity	NPD6844	Discontinued
0.7349	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7266	Discontinued
0.7344	Intermediate Similarity	NPD7584	Approved
0.7342	Intermediate Similarity	NPD6233	Phase 2
0.7333	Intermediate Similarity	NPD1548	Phase 1
0.7333	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD8455	Phase 2
0.7303	Intermediate Similarity	NPD7286	Phase 2
0.7302	Intermediate Similarity	NPD6779	Approved
0.7302	Intermediate Similarity	NPD6782	Approved
0.7302	Intermediate Similarity	NPD6777	Approved
0.7302	Intermediate Similarity	NPD6776	Approved
0.7302	Intermediate Similarity	NPD6780	Approved
0.7302	Intermediate Similarity	NPD6778	Approved
0.7302	Intermediate Similarity	NPD6781	Approved
0.729	Intermediate Similarity	NPD1203	Approved
0.7278	Intermediate Similarity	NPD7038	Approved
0.7278	Intermediate Similarity	NPD2313	Discontinued
0.7278	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7039	Approved
0.7273	Intermediate Similarity	NPD2309	Approved
0.7268	Intermediate Similarity	NPD8434	Phase 2
0.7268	Intermediate Similarity	NPD8150	Discontinued
0.7257	Intermediate Similarity	NPD8127	Discontinued
0.7256	Intermediate Similarity	NPD1652	Phase 2
0.7255	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2799	Discontinued
0.7197	Intermediate Similarity	NPD3018	Phase 2
0.7194	Intermediate Similarity	NPD7783	Phase 2
0.7194	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7435	Discontinued
0.7182	Intermediate Similarity	NPD7240	Approved
0.7175	Intermediate Similarity	NPD5242	Approved
0.717	Intermediate Similarity	NPD3268	Approved
0.7168	Intermediate Similarity	NPD5353	Approved
0.715	Intermediate Similarity	NPD7871	Phase 2
0.715	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD7549	Discontinued
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD5124	Phase 1
0.7143	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1610	Phase 2
0.7134	Intermediate Similarity	NPD2346	Discontinued
0.7134	Intermediate Similarity	NPD2798	Approved
0.7119	Intermediate Similarity	NPD7229	Phase 3
0.7115	Intermediate Similarity	NPD3225	Approved
0.7108	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD7698	Approved
0.7098	Intermediate Similarity	NPD7697	Approved
0.7098	Intermediate Similarity	NPD7696	Phase 3
0.7097	Intermediate Similarity	NPD9717	Approved
0.7097	Intermediate Similarity	NPD9269	Phase 2
0.7093	Intermediate Similarity	NPD6385	Approved
0.7093	Intermediate Similarity	NPD6386	Approved
0.709	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD4361	Phase 2
0.7076	Intermediate Similarity	NPD7458	Discontinued
0.707	Intermediate Similarity	NPD2797	Approved
0.7056	Intermediate Similarity	NPD2163	Approved
0.7051	Intermediate Similarity	NPD2982	Phase 2
0.7051	Intermediate Similarity	NPD2983	Phase 2
0.7048	Intermediate Similarity	NPD2654	Approved
0.7047	Intermediate Similarity	NPD6823	Phase 2
0.7041	Intermediate Similarity	NPD4661	Approved
0.7041	Intermediate Similarity	NPD4662	Approved
0.7041	Intermediate Similarity	NPD7701	Phase 2
0.7039	Intermediate Similarity	NPD5536	Phase 2
0.7037	Intermediate Similarity	NPD6355	Discontinued
0.7037	Intermediate Similarity	NPD6534	Approved
0.7037	Intermediate Similarity	NPD6535	Approved
0.7022	Intermediate Similarity	NPD5710	Approved
0.7022	Intermediate Similarity	NPD5711	Approved
0.7012	Intermediate Similarity	NPD4308	Phase 3

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