NPASS Compound

Structure

CID183851 OpenBabel06191715562D 36 39 0 0 1 0 0 0 0 0999 V2000 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 -4.3301 -0.5000 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 -5.1962 -0.0000 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 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 -5.1962 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 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 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 -6.0622 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 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 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 33 1 0 0 0 0 2 34 1 0 0 0 0 3 5 1 0 0 0 0 3 13 2 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 15 2 0 0 0 0 6 15 1 0 0 0 0 7 14 2 0 0 0 0 7 21 1 0 0 0 0 8 14 1 0 0 0 0 8 22 2 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 16 1 0 0 0 0 10 20 2 0 0 0 0 11 18 1 0 0 0 0 11 19 2 0 0 0 0 12 27 1 0 0 0 0 13 25 1 0 0 0 0 14 19 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 24 2 0 0 0 0 17 30 1 0 0 0 0 18 24 1 0 0 0 0 18 31 2 0 0 0 0 19 35 1 0 0 0 0 20 24 1 0 0 0 0 20 35 1 0 0 0 0 21 26 2 0 0 0 0 21 33 1 0 0 0 0 22 26 1 0 0 0 0 22 34 1 0 0 0 0 23 12 1 6 0 0 0 23 25 1 0 0 0 0 23 36 1 0 0 0 0 25 32 1 6 0 0 0 26 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.14
Volume:	482.927
LogP:	2.847
LogD:	2.382
LogS:	-4.164
# Rotatable Bonds:	8
TPSA:	159.05
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.245
Synthetic Accessibility Score:	3.537
Fsp3:	0.192
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:	-5.095
MDCK Permeability:	1.592815897311084e-05
Pgp-inhibitor:	0.17
Pgp-substrate:	0.966
Human Intestinal Absorption (HIA):	0.24
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	91.246826171875%
Volume Distribution (VD):	0.85
Pgp-substrate:	13.732701301574707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.477
CYP1A2-substrate:	0.618
CYP2C19-inhibitor:	0.173
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.727
CYP2C9-substrate:	0.929
CYP2D6-inhibitor:	0.549
CYP2D6-substrate:	0.647
CYP3A4-inhibitor:	0.717
CYP3A4-substrate:	0.183

ADMET: Excretion

Clearance (CL):	5.913
Half-life (T1/2):	0.821

ADMET: Toxicity

hERG Blockers:	0.278
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.814
AMES Toxicity:	0.29
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.778
Skin Sensitization:	0.835
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.059
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC183851

Natural Product ID:	NPC183851
*Common Name:**	(-)-(7''r,8''s)-4'',5,7-Trihydroxy-3',5'-Dimethoxy-4',8''-Oxyflavonolignan-7'',9''-Diol
IUPAC Name:	2-[4-[(1R,2S)-1,3-dihydroxy-1-(4-hydroxyphenyl)propan-2-yl]oxy-3,5-dimethoxyphenyl]-5,7-dihydroxychromen-4-one
Synonyms:
Standard InCHIKey:	XWGDMVNWFZRSNF-UKILVPOCSA-N
Standard InCHI:	InChI=1S/C26H24O10/c1-33-21-7-14(19-11-18(31)24-17(30)9-16(29)10-20(24)35-19)8-22(34-2)26(21)36-23(12-27)25(32)13-3-5-15(28)6-4-13/h3-11,23,25,27-30,32H,12H2,1-2H3/t23-,25+/m0/s1
SMILES:	COc1cc(cc(c1O[C@@H](CO)[C@@H](c1ccc(cc1)O)O)OC)c1cc(=O)c2c(cc(cc2o1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1797780
PubChem CID:	53354811
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	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	80.7	%	PMID[519055]
NPT2	Others	Unspecified		Inhibition	<	30.0	%	PMID[519055]

☑ 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 NPC183851 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	425
0.1-0.2	1711
0.2-0.3	4200
0.3-0.4	10052
0.4-0.5	8066
0.5-0.6	3659
0.6-0.7	4885
0.7-0.8	4994
0.8-0.85	2215
0.85-0.9	1800
0.9-0.95	673
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC63454
0.9933	High Similarity	NPC284127
0.9933	High Similarity	NPC172202
0.9933	High Similarity	NPC476410
0.9803	High Similarity	NPC305987
0.9803	High Similarity	NPC165970
0.9803	High Similarity	NPC66618
0.9803	High Similarity	NPC288131
0.9803	High Similarity	NPC84324
0.9803	High Similarity	NPC113163
0.9737	High Similarity	NPC101731
0.9673	High Similarity	NPC158188
0.9545	High Similarity	NPC142252
0.9545	High Similarity	NPC26326
0.949	High Similarity	NPC295082
0.949	High Similarity	NPC243877
0.9487	High Similarity	NPC36916
0.9487	High Similarity	NPC72787
0.9487	High Similarity	NPC7154
0.9487	High Similarity	NPC125039
0.9487	High Similarity	NPC36
0.9487	High Similarity	NPC58223
0.9487	High Similarity	NPC7688
0.9484	High Similarity	NPC219927
0.9484	High Similarity	NPC476247
0.9481	High Similarity	NPC475784
0.9477	High Similarity	NPC183
0.9477	High Similarity	NPC470402
0.9463	High Similarity	NPC195202
0.943	High Similarity	NPC475212
0.9423	High Similarity	NPC88023
0.9423	High Similarity	NPC309025
0.9423	High Similarity	NPC243930
0.9419	High Similarity	NPC474038
0.9416	High Similarity	NPC117418
0.9416	High Similarity	NPC53545
0.9408	High Similarity	NPC18727
0.94	High Similarity	NPC137062
0.94	High Similarity	NPC183950
0.94	High Similarity	NPC48479
0.94	High Similarity	NPC52005
0.94	High Similarity	NPC177298
0.94	High Similarity	NPC223579
0.94	High Similarity	NPC287101
0.9396	High Similarity	NPC12200
0.9396	High Similarity	NPC33265
0.9396	High Similarity	NPC62536
0.9367	High Similarity	NPC14662
0.9363	High Similarity	NPC311830
0.9363	High Similarity	NPC477840
0.9363	High Similarity	NPC22832
0.9359	High Similarity	NPC477841
0.9355	High Similarity	NPC119209
0.9355	High Similarity	NPC118256
0.9355	High Similarity	NPC192686
0.9351	High Similarity	NPC112954
0.9351	High Similarity	NPC474055
0.9351	High Similarity	NPC473272
0.9351	High Similarity	NPC472598
0.9351	High Similarity	NPC284820
0.9346	High Similarity	NPC201136
0.9346	High Similarity	NPC4455
0.9346	High Similarity	NPC196439
0.9346	High Similarity	NPC138360
0.9346	High Similarity	NPC280339
0.9346	High Similarity	NPC213622
0.9346	High Similarity	NPC146165
0.9346	High Similarity	NPC92659
0.9346	High Similarity	NPC183597
0.9346	High Similarity	NPC227325
0.9346	High Similarity	NPC163780
0.9346	High Similarity	NPC167815
0.9346	High Similarity	NPC50715
0.9346	High Similarity	NPC2476
0.9346	High Similarity	NPC128863
0.9342	High Similarity	NPC302950
0.9342	High Similarity	NPC236637
0.9342	High Similarity	NPC39732
0.9342	High Similarity	NPC60972
0.9342	High Similarity	NPC219582
0.9338	High Similarity	NPC338131
0.9338	High Similarity	NPC219330
0.9338	High Similarity	NPC50728
0.9338	High Similarity	NPC166753
0.9333	High Similarity	NPC119059
0.9333	High Similarity	NPC120464
0.9308	High Similarity	NPC188079
0.9299	High Similarity	NPC222936
0.9299	High Similarity	NPC272064
0.9299	High Similarity	NPC270335
0.9299	High Similarity	NPC472625
0.9299	High Similarity	NPC191306
0.9299	High Similarity	NPC19709
0.9299	High Similarity	NPC284960
0.9295	High Similarity	NPC472634
0.9295	High Similarity	NPC472632
0.9295	High Similarity	NPC471499
0.9295	High Similarity	NPC289771
0.9295	High Similarity	NPC182045
0.929	High Similarity	NPC190487
0.929	High Similarity	NPC473990
0.929	High Similarity	NPC187792
0.929	High Similarity	NPC154304
0.9286	High Similarity	NPC78492
0.9286	High Similarity	NPC35038
0.9286	High Similarity	NPC278778
0.9286	High Similarity	NPC326037
0.9286	High Similarity	NPC208152
0.9286	High Similarity	NPC13858
0.9286	High Similarity	NPC250922
0.9286	High Similarity	NPC195796
0.9286	High Similarity	NPC320825
0.9286	High Similarity	NPC291878
0.9281	High Similarity	NPC162351
0.9281	High Similarity	NPC176775
0.9281	High Similarity	NPC250822
0.9281	High Similarity	NPC75279
0.9281	High Similarity	NPC160951
0.9281	High Similarity	NPC47781
0.9281	High Similarity	NPC69394
0.9281	High Similarity	NPC274327
0.9281	High Similarity	NPC78326
0.9281	High Similarity	NPC270620
0.9281	High Similarity	NPC145379
0.9281	High Similarity	NPC22519
0.9281	High Similarity	NPC58382
0.9281	High Similarity	NPC231018
0.9281	High Similarity	NPC276409
0.9281	High Similarity	NPC179126
0.9281	High Similarity	NPC255350
0.9281	High Similarity	NPC236223
0.9281	High Similarity	NPC183878
0.9276	High Similarity	NPC200740
0.9276	High Similarity	NPC125062
0.9276	High Similarity	NPC133953
0.9276	High Similarity	NPC308451
0.9276	High Similarity	NPC252933
0.9276	High Similarity	NPC208043
0.9276	High Similarity	NPC54394
0.9276	High Similarity	NPC28274
0.9276	High Similarity	NPC226973
0.9276	High Similarity	NPC236769
0.9276	High Similarity	NPC50403
0.9276	High Similarity	NPC76376
0.9272	High Similarity	NPC159103
0.9272	High Similarity	NPC328119
0.9267	High Similarity	NPC108406
0.9255	High Similarity	NPC472993
0.925	High Similarity	NPC102277
0.925	High Similarity	NPC279209
0.9245	High Similarity	NPC229729
0.9245	High Similarity	NPC260266
0.9236	High Similarity	NPC474033
0.9236	High Similarity	NPC474034
0.9236	High Similarity	NPC472635
0.9236	High Similarity	NPC189142
0.9236	High Similarity	NPC473043
0.9236	High Similarity	NPC77660
0.9231	High Similarity	NPC174953
0.9231	High Similarity	NPC470326
0.9231	High Similarity	NPC282009
0.9231	High Similarity	NPC472631
0.9231	High Similarity	NPC287328
0.9231	High Similarity	NPC472630
0.9231	High Similarity	NPC110349
0.9231	High Similarity	NPC188967
0.9226	High Similarity	NPC156057
0.9226	High Similarity	NPC474208
0.9226	High Similarity	NPC291508
0.9226	High Similarity	NPC471515
0.9226	High Similarity	NPC162869
0.9226	High Similarity	NPC93376
0.9226	High Similarity	NPC224137
0.9226	High Similarity	NPC471479
0.9226	High Similarity	NPC475267
0.9226	High Similarity	NPC474836
0.9226	High Similarity	NPC78071
0.9226	High Similarity	NPC75215
0.9226	High Similarity	NPC227192
0.9226	High Similarity	NPC189179
0.9226	High Similarity	NPC52530
0.9226	High Similarity	NPC27337
0.9226	High Similarity	NPC48208
0.9221	High Similarity	NPC226025
0.9221	High Similarity	NPC470327
0.9221	High Similarity	NPC208197
0.9221	High Similarity	NPC321779
0.9221	High Similarity	NPC37392
0.9221	High Similarity	NPC477503
0.9221	High Similarity	NPC256612
0.9221	High Similarity	NPC45849
0.9221	High Similarity	NPC200761
0.9221	High Similarity	NPC20830
0.9216	High Similarity	NPC301323
0.9216	High Similarity	NPC25270
0.9216	High Similarity	NPC156222
0.9216	High Similarity	NPC275836
0.9216	High Similarity	NPC239128
0.9216	High Similarity	NPC123886
0.9216	High Similarity	NPC187498

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 NPC183851 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	918
0.2-0.3	1797
0.3-0.4	2659
0.4-0.5	1788
0.5-0.6	1004
0.6-0.7	409
0.7-0.8	122
0.8-0.85	29
0.85-0.9	21
0.9-0.95	10
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9487	High Similarity	NPD6166	Phase 2
0.9487	High Similarity	NPD6167	Clinical (unspecified phase)
0.9487	High Similarity	NPD6168	Clinical (unspecified phase)
0.9342	High Similarity	NPD1934	Approved
0.9281	High Similarity	NPD2801	Approved
0.9187	High Similarity	NPD7054	Approved
0.9156	High Similarity	NPD2393	Clinical (unspecified phase)
0.913	High Similarity	NPD7472	Approved
0.9097	High Similarity	NPD3817	Phase 2
0.9067	High Similarity	NPD1511	Approved
0.9012	High Similarity	NPD7074	Phase 3
0.9006	High Similarity	NPD3818	Discontinued
0.8963	High Similarity	NPD7808	Phase 3
0.8961	High Similarity	NPD4380	Phase 2
0.8957	High Similarity	NPD6797	Phase 2
0.8947	High Similarity	NPD1512	Approved
0.8917	High Similarity	NPD4868	Clinical (unspecified phase)
0.8917	High Similarity	NPD3882	Suspended
0.8902	High Similarity	NPD7251	Discontinued
0.8861	High Similarity	NPD4381	Clinical (unspecified phase)
0.8848	High Similarity	NPD4338	Clinical (unspecified phase)
0.8636	High Similarity	NPD7410	Clinical (unspecified phase)
0.8636	High Similarity	NPD4378	Clinical (unspecified phase)
0.8616	High Similarity	NPD8443	Clinical (unspecified phase)
0.8543	High Similarity	NPD1552	Clinical (unspecified phase)
0.8543	High Similarity	NPD1550	Clinical (unspecified phase)
0.8528	High Similarity	NPD6232	Discontinued
0.8519	High Similarity	NPD5494	Approved
0.8509	High Similarity	NPD7075	Discontinued
0.8503	High Similarity	NPD7993	Clinical (unspecified phase)
0.85	High Similarity	NPD5402	Approved
0.8494	Intermediate Similarity	NPD5844	Phase 1
0.8494	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD6801	Discontinued
0.8487	Intermediate Similarity	NPD1549	Phase 2
0.8485	Intermediate Similarity	NPD7473	Discontinued
0.8477	Intermediate Similarity	NPD2796	Approved
0.8466	Intermediate Similarity	NPD6959	Discontinued
0.8428	Intermediate Similarity	NPD7411	Suspended
0.8411	Intermediate Similarity	NPD1510	Phase 2
0.8408	Intermediate Similarity	NPD5403	Approved
0.8333	Intermediate Similarity	NPD6799	Approved
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD5401	Approved
0.8235	Intermediate Similarity	NPD6559	Discontinued
0.821	Intermediate Similarity	NPD7819	Suspended
0.8146	Intermediate Similarity	NPD1240	Approved
0.8098	Intermediate Similarity	NPD1465	Phase 2
0.8095	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1607	Approved
0.8036	Intermediate Similarity	NPD3926	Phase 2
0.8026	Intermediate Similarity	NPD1613	Approved
0.8026	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.8024	Intermediate Similarity	NPD7199	Phase 2
0.8013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7768	Phase 2
0.7947	Intermediate Similarity	NPD3027	Phase 3
0.7917	Intermediate Similarity	NPD1247	Approved
0.7911	Intermediate Similarity	NPD3750	Approved
0.7908	Intermediate Similarity	NPD943	Approved
0.7904	Intermediate Similarity	NPD919	Approved
0.7848	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD3749	Approved
0.7824	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD4628	Phase 3
0.7791	Intermediate Similarity	NPD3751	Discontinued
0.7791	Intermediate Similarity	NPD1653	Approved
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1551	Phase 2
0.7765	Intermediate Similarity	NPD3787	Discontinued
0.7764	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6190	Approved
0.7747	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD230	Phase 1
0.7742	Intermediate Similarity	NPD447	Suspended
0.7711	Intermediate Similarity	NPD37	Approved
0.7697	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6234	Discontinued
0.7688	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD4966	Approved
0.7679	Intermediate Similarity	NPD4967	Phase 2
0.7679	Intermediate Similarity	NPD4965	Approved
0.7658	Intermediate Similarity	NPD2935	Discontinued
0.7654	Intermediate Similarity	NPD7390	Discontinued
0.7647	Intermediate Similarity	NPD4908	Phase 1
0.7627	Intermediate Similarity	NPD8312	Approved
0.7627	Intermediate Similarity	NPD8313	Approved
0.7625	Intermediate Similarity	NPD2800	Approved
0.7624	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7685	Pre-registration
0.7607	Intermediate Similarity	NPD2532	Approved
0.7607	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2534	Approved
0.7607	Intermediate Similarity	NPD2533	Approved
0.7595	Intermediate Similarity	NPD3748	Approved
0.7586	Intermediate Similarity	NPD7228	Approved
0.7571	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD3226	Approved
0.7527	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1933	Approved
0.7515	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD2344	Approved
0.7484	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7033	Discontinued
0.7468	Intermediate Similarity	NPD9494	Approved
0.7468	Intermediate Similarity	NPD6651	Approved
0.7458	Intermediate Similarity	NPD5953	Discontinued
0.7446	Intermediate Similarity	NPD4360	Phase 2
0.7446	Intermediate Similarity	NPD4363	Phase 3
0.7438	Intermediate Similarity	NPD6100	Approved
0.7438	Intermediate Similarity	NPD6099	Approved
0.7436	Intermediate Similarity	NPD6798	Discontinued
0.7434	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6832	Phase 2
0.7407	Intermediate Similarity	NPD1243	Approved
0.7396	Intermediate Similarity	NPD6844	Discontinued
0.7396	Intermediate Similarity	NPD8151	Discontinued
0.7394	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6233	Phase 2
0.7383	Intermediate Similarity	NPD1548	Phase 1
0.7382	Intermediate Similarity	NPD7584	Approved
0.7378	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD8455	Phase 2
0.7345	Intermediate Similarity	NPD7286	Phase 2
0.734	Intermediate Similarity	NPD6779	Approved
0.734	Intermediate Similarity	NPD6780	Approved
0.734	Intermediate Similarity	NPD6781	Approved
0.734	Intermediate Similarity	NPD6776	Approved
0.734	Intermediate Similarity	NPD6778	Approved
0.734	Intermediate Similarity	NPD6782	Approved
0.734	Intermediate Similarity	NPD6777	Approved
0.7338	Intermediate Similarity	NPD1203	Approved
0.7325	Intermediate Similarity	NPD2313	Discontinued
0.7321	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7038	Approved
0.7318	Intermediate Similarity	NPD7039	Approved
0.7317	Intermediate Similarity	NPD2309	Approved
0.7308	Intermediate Similarity	NPD8434	Phase 2
0.7308	Intermediate Similarity	NPD8150	Discontinued
0.7303	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1652	Phase 2
0.7299	Intermediate Similarity	NPD8127	Discontinued
0.7296	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7266	Discontinued
0.7273	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2799	Discontinued
0.7244	Intermediate Similarity	NPD3018	Phase 2
0.7231	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7783	Phase 2
0.7225	Intermediate Similarity	NPD7435	Discontinued
0.7222	Intermediate Similarity	NPD7240	Approved
0.7216	Intermediate Similarity	NPD5242	Approved
0.7215	Intermediate Similarity	NPD3268	Approved
0.7209	Intermediate Similarity	NPD5353	Approved
0.719	Intermediate Similarity	NPD422	Phase 1
0.719	Intermediate Similarity	NPD1610	Phase 2
0.7188	Intermediate Similarity	NPD7871	Phase 2
0.7188	Intermediate Similarity	NPD7870	Phase 2
0.7188	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5124	Phase 1
0.7182	Intermediate Similarity	NPD7549	Discontinued
0.7179	Intermediate Similarity	NPD2798	Approved
0.7178	Intermediate Similarity	NPD2346	Discontinued
0.7161	Intermediate Similarity	NPD3225	Approved
0.7159	Intermediate Similarity	NPD7229	Phase 3
0.7152	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9717	Approved
0.7135	Intermediate Similarity	NPD7697	Approved
0.7135	Intermediate Similarity	NPD7698	Approved
0.7135	Intermediate Similarity	NPD7696	Phase 3
0.7135	Intermediate Similarity	NPD6386	Approved
0.7135	Intermediate Similarity	NPD6385	Approved
0.7128	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4361	Phase 2
0.7118	Intermediate Similarity	NPD7458	Discontinued
0.7115	Intermediate Similarity	NPD2797	Approved
0.7097	Intermediate Similarity	NPD2982	Phase 2
0.7097	Intermediate Similarity	NPD2983	Phase 2
0.7095	Intermediate Similarity	NPD2163	Approved
0.7091	Intermediate Similarity	NPD2654	Approved
0.7086	Intermediate Similarity	NPD5536	Phase 2
0.7083	Intermediate Similarity	NPD4661	Approved
0.7083	Intermediate Similarity	NPD6823	Phase 2
0.7083	Intermediate Similarity	NPD4662	Approved
0.7081	Intermediate Similarity	NPD6355	Discontinued
0.7077	Intermediate Similarity	NPD7701	Phase 2
0.7074	Intermediate Similarity	NPD6534	Approved
0.7074	Intermediate Similarity	NPD6535	Approved
0.7062	Intermediate Similarity	NPD5711	Approved
0.7062	Intermediate Similarity	NPD5710	Approved
0.7055	Intermediate Similarity	NPD4308	Phase 3
0.7041	Intermediate Similarity	NPD6273	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