NPASS Compound

Structure

CID165155 OpenBabel06191715532D 31 34 0 0 1 0 0 0 0 0999 V2000 -2.0763 -4.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2078 -1.1929 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 2.5411 0.5878 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 -1.8672 -2.5495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5717 -0.9672 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0480 0.7435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7600 -0.9791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7627 -1.5550 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 -0.6413 -0.1701 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3533 -0.0655 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7808 -2.9562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4853 -1.3739 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5898 -2.3684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8492 -1.1482 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5612 0.9126 0.0000 C 0 0 1 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 -4.5034 -2.7752 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8853 -3.9507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2943 -0.7861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0169 -1.6482 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3048 1.4126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 12 2 0 0 0 0 6 16 1 0 0 0 0 7 12 1 0 0 0 0 7 17 2 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 13 1 0 0 0 0 9 19 2 0 0 0 0 10 31 1 0 0 0 0 11 30 1 0 0 0 0 14 10 1 6 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 11 1 6 0 0 0 15 22 1 0 0 0 0 16 20 2 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 18 23 2 0 0 0 0 18 27 1 0 0 0 0 19 23 1 0 0 0 0 19 28 1 0 0 0 0 20 24 1 0 0 0 0 21 12 1 1 0 0 0 21 30 1 0 0 0 0 22 13 1 1 0 0 0 22 31 1 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.18
Volume:	426.641
LogP:	2.456
LogD:	2.843
LogS:	-3.5
# Rotatable Bonds:	7
TPSA:	84.84
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.712
Synthetic Accessibility Score:	3.748
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.87
MDCK Permeability:	3.8945130654610693e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.153

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.329
Plasma Protein Binding (PPB):	66.57133483886719%
Volume Distribution (VD):	0.696
Pgp-substrate:	22.614654541015625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.974
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.9
CYP2C9-inhibitor:	0.16
CYP2C9-substrate:	0.688
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.767
CYP3A4-inhibitor:	0.522
CYP3A4-substrate:	0.821

ADMET: Excretion

Clearance (CL):	7.057
Half-life (T1/2):	0.591

ADMET: Toxicity

hERG Blockers:	0.284
Human Hepatotoxicity (H-HT):	0.102
Drug-inuced Liver Injury (DILI):	0.849
AMES Toxicity:	0.118
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.078
Skin Sensitization:	0.932
Carcinogencity:	0.06
Eye Corrosion:	0.004
Eye Irritation:	0.112
Respiratory Toxicity:	0.185

Download Data

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

Natural Product: NPC165155

Natural Product ID:	NPC165155
*Common Name:**	(-)-(7R,7'r,8S,8's)-4'-Hydroxy-3,3',4,5,5'-Pentamethoxy-7,9':7',9-Diepoxylignane
IUPAC Name:	4-[(3R,3aS,6R,6aS)-6-(3,4,5-trimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenol
Synonyms:
Standard InCHIKey:	AJMQKDTUOKAQNT-SDVFQCAASA-N
Standard InCHI:	InChI=1S/C23H28O8/c1-25-16-6-12(7-17(26-2)20(16)24)21-14-10-31-22(15(14)11-30-21)13-8-18(27-3)23(29-5)19(9-13)28-4/h6-9,14-15,21-22,24H,10-11H2,1-5H3/t14-,15-,21+,22+/m1/s1
SMILES:	COc1cc(cc(c1OC)OC)[C@@H]1OC[C@@H]2[C@H]1CO[C@H]2c1cc(OC)c(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1797774
PubChem CID:	53356312
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans

*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[498577]

☑ 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 NPC165155 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	1363
0.2-0.3	4042
0.3-0.4	11085
0.4-0.5	7946
0.5-0.6	5196
0.6-0.7	8729
0.7-0.8	2754
0.8-0.85	777
0.85-0.9	300
0.9-0.95	67
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC24490
1.0	High Similarity	NPC141765
1.0	High Similarity	NPC34103
0.9845	High Similarity	NPC126409
0.9845	High Similarity	NPC99572
0.9767	High Similarity	NPC244983
0.9767	High Similarity	NPC326095
0.9766	High Similarity	NPC204215
0.9766	High Similarity	NPC175067
0.969	High Similarity	NPC158331
0.9615	High Similarity	NPC287745
0.9549	High Similarity	NPC177868
0.9535	High Similarity	NPC27843
0.9535	High Similarity	NPC115207
0.9535	High Similarity	NPC161557
0.9535	High Similarity	NPC40432
0.9535	High Similarity	NPC228346
0.9535	High Similarity	NPC7171
0.9535	High Similarity	NPC158079
0.9481	High Similarity	NPC185071
0.9481	High Similarity	NPC12728
0.9462	High Similarity	NPC181049
0.9462	High Similarity	NPC207400
0.9462	High Similarity	NPC4940
0.9453	High Similarity	NPC54321
0.9453	High Similarity	NPC328682
0.9453	High Similarity	NPC281864
0.9412	High Similarity	NPC471415
0.9412	High Similarity	NPC114119
0.9412	High Similarity	NPC470097
0.9385	High Similarity	NPC474017
0.9375	High Similarity	NPC8050
0.9375	High Similarity	NPC473092
0.9375	High Similarity	NPC473093
0.9343	High Similarity	NPC477702
0.9338	High Similarity	NPC255566
0.9338	High Similarity	NPC298317
0.9333	High Similarity	NPC311530
0.9308	High Similarity	NPC257582
0.9308	High Similarity	NPC145305
0.9308	High Similarity	NPC187998
0.9308	High Similarity	NPC64201
0.9308	High Similarity	NPC242807
0.9308	High Similarity	NPC241522
0.9308	High Similarity	NPC92164
0.9308	High Similarity	NPC77040
0.9308	High Similarity	NPC42300
0.9308	High Similarity	NPC153739
0.9308	High Similarity	NPC174495
0.9302	High Similarity	NPC11258
0.9302	High Similarity	NPC129570
0.9302	High Similarity	NPC82862
0.9302	High Similarity	NPC128208
0.9302	High Similarity	NPC184733
0.9302	High Similarity	NPC282703
0.9302	High Similarity	NPC21867
0.9302	High Similarity	NPC45774
0.9302	High Similarity	NPC222127
0.9297	High Similarity	NPC76451
0.9275	High Similarity	NPC212890
0.9275	High Similarity	NPC324492
0.9275	High Similarity	NPC317053
0.9259	High Similarity	NPC309124
0.9259	High Similarity	NPC184797
0.9259	High Similarity	NPC160283
0.9259	High Similarity	NPC254759
0.9254	High Similarity	NPC474039
0.9237	High Similarity	NPC277804
0.9237	High Similarity	NPC470095
0.9237	High Similarity	NPC470096
0.9231	High Similarity	NPC170844
0.9231	High Similarity	NPC476968
0.9231	High Similarity	NPC475875
0.9225	High Similarity	NPC127587
0.9209	High Similarity	NPC327412
0.9209	High Similarity	NPC320970
0.9209	High Similarity	NPC328567
0.9209	High Similarity	NPC320671
0.9191	High Similarity	NPC87725
0.9191	High Similarity	NPC247291
0.9191	High Similarity	NPC263261
0.9185	High Similarity	NPC236306
0.9185	High Similarity	NPC292882
0.9185	High Similarity	NPC473739
0.9185	High Similarity	NPC232164
0.9167	High Similarity	NPC7903
0.9167	High Similarity	NPC253105
0.9167	High Similarity	NPC35932
0.9167	High Similarity	NPC160991
0.9167	High Similarity	NPC16208
0.9167	High Similarity	NPC184447
0.9167	High Similarity	NPC201587
0.9154	High Similarity	NPC206615
0.9154	High Similarity	NPC470213
0.9154	High Similarity	NPC98631
0.9154	High Similarity	NPC470084
0.9154	High Similarity	NPC186843
0.9147	High Similarity	NPC9891
0.9147	High Similarity	NPC88297
0.9147	High Similarity	NPC285725
0.9147	High Similarity	NPC112571
0.9147	High Similarity	NPC186845
0.9147	High Similarity	NPC50683
0.9143	High Similarity	NPC130449
0.9143	High Similarity	NPC248132
0.913	High Similarity	NPC472713
0.913	High Similarity	NPC118385
0.913	High Similarity	NPC472712
0.913	High Similarity	NPC187774
0.913	High Similarity	NPC473046
0.9124	High Similarity	NPC107161
0.9118	High Similarity	NPC46591
0.9118	High Similarity	NPC291101
0.9118	High Similarity	NPC266197
0.9111	High Similarity	NPC283949
0.9104	High Similarity	NPC150534
0.9104	High Similarity	NPC142547
0.9104	High Similarity	NPC135777
0.9091	High Similarity	NPC472597
0.9091	High Similarity	NPC309787
0.9078	High Similarity	NPC470098
0.9078	High Similarity	NPC286235
0.9078	High Similarity	NPC473266
0.9078	High Similarity	NPC470826
0.9078	High Similarity	NPC55158
0.9078	High Similarity	NPC51328
0.9078	High Similarity	NPC125570
0.9077	High Similarity	NPC165045
0.9077	High Similarity	NPC118533
0.907	High Similarity	NPC57490
0.907	High Similarity	NPC251855
0.907	High Similarity	NPC17943
0.907	High Similarity	NPC221077
0.907	High Similarity	NPC475169
0.907	High Similarity	NPC203133
0.907	High Similarity	NPC472093
0.907	High Similarity	NPC208950
0.907	High Similarity	NPC193544
0.907	High Similarity	NPC298757
0.907	High Similarity	NPC116907
0.907	High Similarity	NPC117214
0.907	High Similarity	NPC233410
0.9058	High Similarity	NPC477616
0.9058	High Similarity	NPC47633
0.9058	High Similarity	NPC85264
0.9058	High Similarity	NPC102044
0.9044	High Similarity	NPC471183
0.9044	High Similarity	NPC123526
0.9044	High Similarity	NPC88640
0.9044	High Similarity	NPC22517
0.9044	High Similarity	NPC193666
0.9037	High Similarity	NPC270456
0.9037	High Similarity	NPC162659
0.9037	High Similarity	NPC265433
0.9037	High Similarity	NPC471988
0.9037	High Similarity	NPC133025
0.9037	High Similarity	NPC248727
0.903	High Similarity	NPC67247
0.903	High Similarity	NPC310854
0.903	High Similarity	NPC170694
0.9023	High Similarity	NPC6451
0.9023	High Similarity	NPC65183
0.9023	High Similarity	NPC72046
0.9023	High Similarity	NPC261812
0.9023	High Similarity	NPC470752
0.9015	High Similarity	NPC472338
0.9015	High Similarity	NPC469612
0.9015	High Similarity	NPC469614
0.9	High Similarity	NPC260397
0.9	High Similarity	NPC252286
0.9	High Similarity	NPC206882
0.9	High Similarity	NPC154971
0.8993	High Similarity	NPC12641
0.8993	High Similarity	NPC280092
0.8993	High Similarity	NPC63879
0.8993	High Similarity	NPC45257
0.8993	High Similarity	NPC93323
0.8992	High Similarity	NPC257682
0.8992	High Similarity	NPC146355
0.8992	High Similarity	NPC34902
0.8992	High Similarity	NPC18449
0.8992	High Similarity	NPC131747
0.8992	High Similarity	NPC121783
0.8986	High Similarity	NPC5262
0.8986	High Similarity	NPC472714
0.8986	High Similarity	NPC41782
0.8986	High Similarity	NPC287124
0.8978	High Similarity	NPC226547
0.8978	High Similarity	NPC27495
0.8978	High Similarity	NPC56091
0.8978	High Similarity	NPC55793
0.8971	High Similarity	NPC3072
0.8971	High Similarity	NPC46277
0.8971	High Similarity	NPC477938
0.8971	High Similarity	NPC185908
0.8971	High Similarity	NPC301765
0.8971	High Similarity	NPC156948
0.8971	High Similarity	NPC86605
0.8963	High Similarity	NPC256262
0.8963	High Similarity	NPC112246

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 NPC165155 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	811
0.2-0.3	1899
0.3-0.4	2884
0.4-0.5	1696
0.5-0.6	1004
0.6-0.7	460
0.7-0.8	61
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD3027	Phase 3
0.8603	High Similarity	NPD1612	Clinical (unspecified phase)
0.8603	High Similarity	NPD1613	Approved
0.8533	High Similarity	NPD6234	Discontinued
0.8507	High Similarity	NPD1530	Clinical (unspecified phase)
0.8444	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD4967	Phase 2
0.8278	Intermediate Similarity	NPD4965	Approved
0.8278	Intermediate Similarity	NPD4966	Approved
0.8153	Intermediate Similarity	NPD7228	Approved
0.8079	Intermediate Similarity	NPD37	Approved
0.8074	Intermediate Similarity	NPD2982	Phase 2
0.8074	Intermediate Similarity	NPD2983	Phase 2
0.8062	Intermediate Similarity	NPD5283	Phase 1
0.8043	Intermediate Similarity	NPD4908	Phase 1
0.8	Intermediate Similarity	NPD2981	Phase 2
0.7971	Intermediate Similarity	NPD3018	Phase 2
0.7943	Intermediate Similarity	NPD3620	Phase 2
0.7943	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD1610	Phase 2
0.7926	Intermediate Similarity	NPD3705	Approved
0.7907	Intermediate Similarity	NPD228	Approved
0.7843	Intermediate Similarity	NPD1934	Approved
0.7842	Intermediate Similarity	NPD2861	Phase 2
0.7752	Intermediate Similarity	NPD3021	Approved
0.7752	Intermediate Similarity	NPD3022	Approved
0.7722	Intermediate Similarity	NPD7199	Phase 2
0.7692	Intermediate Similarity	NPD3882	Suspended
0.7692	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD4749	Approved
0.7681	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1548	Phase 1
0.7628	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7240	Approved
0.7593	Intermediate Similarity	NPD3818	Discontinued
0.7582	Intermediate Similarity	NPD1653	Approved
0.7578	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6166	Phase 2
0.7578	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD2801	Approved
0.7552	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7266	Discontinued
0.7485	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4625	Phase 3
0.7448	Intermediate Similarity	NPD1558	Phase 1
0.7448	Intermediate Similarity	NPD4060	Phase 1
0.7445	Intermediate Similarity	NPD1357	Approved
0.7434	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4005	Discontinued
0.7407	Intermediate Similarity	NPD7157	Approved
0.74	Intermediate Similarity	NPD6674	Discontinued
0.74	Intermediate Similarity	NPD4236	Phase 3
0.74	Intermediate Similarity	NPD4237	Approved
0.7394	Intermediate Similarity	NPD7074	Phase 3
0.7383	Intermediate Similarity	NPD3540	Phase 1
0.7372	Intermediate Similarity	NPD4675	Approved
0.7372	Intermediate Similarity	NPD4678	Approved
0.7368	Intermediate Similarity	NPD7124	Phase 2
0.7337	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7054	Approved
0.7329	Intermediate Similarity	NPD5494	Approved
0.732	Intermediate Similarity	NPD4357	Discontinued
0.732	Intermediate Similarity	NPD1511	Approved
0.7315	Intermediate Similarity	NPD3539	Phase 1
0.7313	Intermediate Similarity	NPD7843	Approved
0.7305	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6111	Discontinued
0.7296	Intermediate Similarity	NPD3817	Phase 2
0.729	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7472	Approved
0.7285	Intermediate Similarity	NPD3060	Approved
0.7285	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD230	Phase 1
0.7279	Intermediate Similarity	NPD5735	Approved
0.7273	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2684	Approved
0.7267	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4380	Phase 2
0.7248	Intermediate Similarity	NPD5588	Approved
0.7239	Intermediate Similarity	NPD6232	Discontinued
0.7237	Intermediate Similarity	NPD6331	Phase 2
0.7237	Intermediate Similarity	NPD4110	Phase 3
0.7237	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2977	Approved
0.7233	Intermediate Similarity	NPD2978	Approved
0.7233	Intermediate Similarity	NPD1465	Phase 2
0.7226	Intermediate Similarity	NPD1512	Approved
0.7218	Intermediate Similarity	NPD4750	Phase 3
0.7212	Intermediate Similarity	NPD7473	Discontinued
0.7211	Intermediate Similarity	NPD2238	Phase 2
0.72	Intermediate Similarity	NPD2161	Phase 2
0.7192	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6190	Approved
0.719	Intermediate Similarity	NPD2219	Phase 1
0.7181	Intermediate Similarity	NPD4538	Approved
0.7181	Intermediate Similarity	NPD4536	Approved
0.7181	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5536	Phase 2
0.7171	Intermediate Similarity	NPD5177	Phase 3
0.7163	Intermediate Similarity	NPD1091	Approved
0.7162	Intermediate Similarity	NPD6355	Discontinued
0.7162	Intermediate Similarity	NPD3657	Discovery
0.7152	Intermediate Similarity	NPD1375	Discontinued
0.7143	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD5058	Phase 3
0.7132	Intermediate Similarity	NPD1242	Phase 1
0.7126	Intermediate Similarity	NPD5844	Phase 1
0.7124	Intermediate Similarity	NPD3892	Phase 2
0.7111	Intermediate Similarity	NPD7680	Approved
0.7101	Intermediate Similarity	NPD7251	Discontinued
0.7086	Intermediate Similarity	NPD6100	Approved
0.7086	Intermediate Similarity	NPD6099	Approved
0.7083	Intermediate Similarity	NPD3094	Phase 2
0.7075	Intermediate Similarity	NPD5111	Phase 2
0.7075	Intermediate Similarity	NPD5110	Phase 2
0.7075	Intermediate Similarity	NPD5109	Approved
0.7059	Intermediate Similarity	NPD7808	Phase 3
0.7059	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD3020	Approved
0.7051	Intermediate Similarity	NPD4123	Phase 3
0.7042	Intermediate Similarity	NPD422	Phase 1
0.7039	Intermediate Similarity	NPD5762	Approved
0.7039	Intermediate Similarity	NPD5763	Approved
0.7034	Intermediate Similarity	NPD6584	Phase 3
0.7029	Intermediate Similarity	NPD6671	Approved
0.7027	Intermediate Similarity	NPD2674	Phase 3
0.702	Intermediate Similarity	NPD5960	Phase 3
0.7014	Intermediate Similarity	NPD6696	Suspended
0.7014	Intermediate Similarity	NPD8651	Approved
0.7013	Intermediate Similarity	NPD4628	Phase 3
0.7007	Intermediate Similarity	NPD7095	Approved
0.7006	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6559	Discontinued
0.7	Intermediate Similarity	NPD7685	Pre-registration
0.7	Intermediate Similarity	NPD6653	Approved
0.6994	Remote Similarity	NPD4055	Discovery
0.6994	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7075	Discontinued
0.6993	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD968	Approved
0.6987	Remote Similarity	NPD7212	Phase 2
0.6987	Remote Similarity	NPD7213	Phase 3
0.6975	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2563	Approved
0.6975	Remote Similarity	NPD2560	Approved
0.6968	Remote Similarity	NPD2677	Approved
0.6959	Remote Similarity	NPD3144	Approved
0.6959	Remote Similarity	NPD3145	Approved
0.6959	Remote Similarity	NPD7549	Discontinued
0.6954	Remote Similarity	NPD7906	Approved
0.6948	Remote Similarity	NPD4162	Approved
0.6948	Remote Similarity	NPD1652	Phase 2
0.6947	Remote Similarity	NPD846	Approved
0.6947	Remote Similarity	NPD940	Approved
0.6946	Remote Similarity	NPD2489	Approved
0.6946	Remote Similarity	NPD27	Approved
0.6944	Remote Similarity	NPD5327	Phase 3
0.6943	Remote Similarity	NPD7447	Phase 1
0.6943	Remote Similarity	NPD2532	Approved
0.6943	Remote Similarity	NPD2533	Approved
0.6943	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2534	Approved
0.6943	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.694	Remote Similarity	NPD290	Approved
0.6939	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5124	Phase 1
0.6928	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3092	Approved
0.6919	Remote Similarity	NPD4578	Approved
0.6919	Remote Similarity	NPD7310	Approved
0.6919	Remote Similarity	NPD7311	Approved
0.6919	Remote Similarity	NPD7312	Approved
0.6919	Remote Similarity	NPD7313	Approved
0.6919	Remote Similarity	NPD4577	Approved
0.6918	Remote Similarity	NPD4210	Discontinued
0.6914	Remote Similarity	NPD5772	Approved
0.6914	Remote Similarity	NPD5773	Approved
0.6913	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6233	Phase 2
0.6908	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1510	Phase 2
0.6903	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7466	Approved
0.6901	Remote Similarity	NPD5126	Approved
0.6901	Remote Similarity	NPD6516	Phase 2
0.6901	Remote Similarity	NPD5846	Approved
0.6901	Remote Similarity	NPD5125	Phase 3
0.6899	Remote Similarity	NPD52	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