NPASS Compound

Structure

CID156635 OpenBabel06191715522D 30 34 0 0 1 0 0 0 0 0999 V2000 -5.1962 -0.0000 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 -4.3301 -2.5000 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 -3.4641 -1.0000 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 -1.7321 -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 1.7321 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 4.1369 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 -2.5981 -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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 2.5981 0.5000 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 -0.8660 0.5000 0.0000 C 0 0 2 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 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 -0.5000 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 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 26 1 0 0 0 0 4 5 1 0 0 0 0 4 12 2 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 15 2 0 0 0 0 8 18 1 0 0 0 0 9 17 2 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 10 27 1 0 0 0 0 11 28 1 0 0 0 0 11 29 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 14 21 2 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 19 2 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 23 1 6 0 0 0 20 30 1 0 0 0 0 21 30 1 0 0 0 0 22 23 1 0 0 0 0 22 24 2 0 0 0 0 23 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.14
Volume:	404.022
LogP:	4.667
LogD:	3.648
LogS:	-5.416
# Rotatable Bonds:	3
TPSA:	83.45
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.778
Synthetic Accessibility Score:	3.819
Fsp3:	0.348
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:	-4.757
MDCK Permeability:	1.9809958757832646e-05
Pgp-inhibitor:	0.08
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.097
Plasma Protein Binding (PPB):	86.87236785888672%
Volume Distribution (VD):	1.081
Pgp-substrate:	6.999334812164307%

ADMET: Metabolism

CYP1A2-inhibitor:	0.532
CYP1A2-substrate:	0.588
CYP2C19-inhibitor:	0.966
CYP2C19-substrate:	0.524
CYP2C9-inhibitor:	0.899
CYP2C9-substrate:	0.854
CYP2D6-inhibitor:	0.862
CYP2D6-substrate:	0.633
CYP3A4-inhibitor:	0.92
CYP3A4-substrate:	0.663

ADMET: Excretion

Clearance (CL):	11.735
Half-life (T1/2):	0.085

ADMET: Toxicity

hERG Blockers:	0.095
Human Hepatotoxicity (H-HT):	0.621
Drug-inuced Liver Injury (DILI):	0.288
AMES Toxicity:	0.516
Rat Oral Acute Toxicity:	0.137
Maximum Recommended Daily Dose:	0.71
Skin Sensitization:	0.414
Carcinogencity:	0.824
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.085

Download Data

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

Natural Product: NPC156635

Natural Product ID:	NPC156635
*Common Name:**	ZFSLOJRJABHMTL-OFNKIYASSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZFSLOJRJABHMTL-OFNKIYASSA-N
Standard InCHI:	InChI=1S/C23H22O7/c1-12(2)4-5-13-16(26-3)7-6-14-21(13)30-20-10-27-17-9-19-18(28-11-29-19)8-15(17)23(20,25)22(14)24/h4,6-9,20,25H,5,10-11H2,1-3H3/t20-,23+/m1/s1
SMILES:	COc1ccc2c(c1CC=C(C)C)O[C@H]1[C@@](C2=O)(O)c2cc3OCOc3cc2OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3758287
PubChem CID:	641748
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001607] Rotenoids [CHEMONTID:0003528] Rotenones

*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
NPO448	Millettia usaramensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26651537]
NPO448	Millettia usaramensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO448	Millettia usaramensis	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	25700.0	nM	PMID[470844]

☑ 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 NPC156635 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	418
0.1-0.2	1658
0.2-0.3	3724
0.3-0.4	9016
0.4-0.5	9230
0.5-0.6	3832
0.6-0.7	4901
0.7-0.8	5665
0.8-0.85	2888
0.85-0.9	1299
0.9-0.95	57
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9818	High Similarity	NPC67302
0.9693	High Similarity	NPC152477
0.9576	High Similarity	NPC121333
0.9573	High Similarity	NPC242395
0.9461	High Similarity	NPC108202
0.9458	High Similarity	NPC475825
0.9458	High Similarity	NPC223375
0.9451	High Similarity	NPC173292
0.9451	High Similarity	NPC113093
0.9412	High Similarity	NPC473883
0.9394	High Similarity	NPC8965
0.939	High Similarity	NPC234052
0.9333	High Similarity	NPC128293
0.9281	High Similarity	NPC44558
0.9281	High Similarity	NPC74559
0.9277	High Similarity	NPC42892
0.9277	High Similarity	NPC150131
0.9273	High Similarity	NPC224280
0.9273	High Similarity	NPC62261
0.9268	High Similarity	NPC478199
0.9268	High Similarity	NPC125991
0.9235	High Similarity	NPC168584
0.9231	High Similarity	NPC472607
0.9222	High Similarity	NPC472383
0.9222	High Similarity	NPC177480
0.9222	High Similarity	NPC472381
0.9212	High Similarity	NPC273959
0.9212	High Similarity	NPC470178
0.9207	High Similarity	NPC34376
0.9176	High Similarity	NPC472384
0.9176	High Similarity	NPC472382
0.9176	High Similarity	NPC472380
0.9167	High Similarity	NPC103307
0.9167	High Similarity	NPC21190
0.9167	High Similarity	NPC34287
0.9167	High Similarity	NPC22195
0.9167	High Similarity	NPC183357
0.9167	High Similarity	NPC474434
0.9167	High Similarity	NPC105511
0.9167	High Similarity	NPC472276
0.9167	High Similarity	NPC471416
0.9167	High Similarity	NPC212748
0.9162	High Similarity	NPC93099
0.9162	High Similarity	NPC135345
0.9152	High Similarity	NPC469575
0.9152	High Similarity	NPC18284
0.9152	High Similarity	NPC273021
0.9146	High Similarity	NPC298093
0.9133	High Similarity	NPC148710
0.9128	High Similarity	NPC473071
0.9128	High Similarity	NPC473073
0.9112	High Similarity	NPC267254
0.9112	High Similarity	NPC205076
0.9112	High Similarity	NPC475155
0.9112	High Similarity	NPC117260
0.9112	High Similarity	NPC235575
0.9112	High Similarity	NPC472386
0.9112	High Similarity	NPC261254
0.9112	High Similarity	NPC307518
0.9112	High Similarity	NPC48773
0.9112	High Similarity	NPC476405
0.9107	High Similarity	NPC95855
0.9107	High Similarity	NPC471287
0.9107	High Similarity	NPC183036
0.9107	High Similarity	NPC288813
0.9107	High Similarity	NPC326877
0.9107	High Similarity	NPC210042
0.9107	High Similarity	NPC229687
0.9107	High Similarity	NPC112755
0.9107	High Similarity	NPC471457
0.9107	High Similarity	NPC170675
0.9102	High Similarity	NPC120593
0.9102	High Similarity	NPC170245
0.9096	High Similarity	NPC41301
0.9096	High Similarity	NPC124038
0.9091	High Similarity	NPC173137
0.9091	High Similarity	NPC94155
0.9091	High Similarity	NPC162668
0.9091	High Similarity	NPC134783
0.9085	High Similarity	NPC152904
0.908	High Similarity	NPC303255
0.908	High Similarity	NPC155063
0.9075	High Similarity	NPC473072
0.9064	High Similarity	NPC169733
0.9064	High Similarity	NPC268533
0.9064	High Similarity	NPC257714
0.9059	High Similarity	NPC239549
0.9059	High Similarity	NPC51774
0.9059	High Similarity	NPC21666
0.9059	High Similarity	NPC42773
0.9059	High Similarity	NPC169977
0.9059	High Similarity	NPC236191
0.9059	High Similarity	NPC101026
0.9059	High Similarity	NPC24043
0.9059	High Similarity	NPC310794
0.9059	High Similarity	NPC45522
0.9053	High Similarity	NPC293004
0.9053	High Similarity	NPC72249
0.9053	High Similarity	NPC224462
0.9053	High Similarity	NPC245014
0.9053	High Similarity	NPC282987
0.9053	High Similarity	NPC84265
0.9048	High Similarity	NPC117854
0.9048	High Similarity	NPC6588
0.9048	High Similarity	NPC76482
0.9048	High Similarity	NPC477502
0.9048	High Similarity	NPC477154
0.9048	High Similarity	NPC45400
0.9042	High Similarity	NPC472277
0.9042	High Similarity	NPC300053
0.9042	High Similarity	NPC108433
0.9042	High Similarity	NPC326520
0.9036	High Similarity	NPC81679
0.9036	High Similarity	NPC472448
0.9036	High Similarity	NPC474033
0.9036	High Similarity	NPC302741
0.9036	High Similarity	NPC83922
0.9036	High Similarity	NPC474034
0.903	High Similarity	NPC472624
0.903	High Similarity	NPC471976
0.9024	High Similarity	NPC258644
0.9012	High Similarity	NPC472387
0.9012	High Similarity	NPC469600
0.9006	High Similarity	NPC469601
0.9006	High Similarity	NPC102028
0.9006	High Similarity	NPC264735
0.9006	High Similarity	NPC294629
0.9006	High Similarity	NPC477848
0.9	High Similarity	NPC256760
0.9	High Similarity	NPC260263
0.9	High Similarity	NPC156977
0.9	High Similarity	NPC301683
0.9	High Similarity	NPC245452
0.8994	High Similarity	NPC105025
0.8994	High Similarity	NPC469931
0.8994	High Similarity	NPC165456
0.8994	High Similarity	NPC226294
0.8994	High Similarity	NPC61791
0.8994	High Similarity	NPC45638
0.8994	High Similarity	NPC52382
0.8994	High Similarity	NPC93337
0.8994	High Similarity	NPC201292
0.8994	High Similarity	NPC270578
0.8994	High Similarity	NPC58053
0.8994	High Similarity	NPC186807
0.8994	High Similarity	NPC475942
0.8988	High Similarity	NPC119589
0.8988	High Similarity	NPC236934
0.8988	High Similarity	NPC477517
0.8988	High Similarity	NPC471213
0.8988	High Similarity	NPC235610
0.8988	High Similarity	NPC5778
0.8982	High Similarity	NPC472281
0.8982	High Similarity	NPC205265
0.8982	High Similarity	NPC329669
0.8982	High Similarity	NPC472625
0.8982	High Similarity	NPC473313
0.8982	High Similarity	NPC18100
0.8982	High Similarity	NPC248638
0.8982	High Similarity	NPC127415
0.8982	High Similarity	NPC236521
0.8982	High Similarity	NPC472278
0.8982	High Similarity	NPC152659
0.8982	High Similarity	NPC475985
0.8976	High Similarity	NPC29876
0.8976	High Similarity	NPC472632
0.8976	High Similarity	NPC3629
0.8976	High Similarity	NPC165549
0.8976	High Similarity	NPC471210
0.8976	High Similarity	NPC308992
0.8976	High Similarity	NPC167678
0.8976	High Similarity	NPC260640
0.8976	High Similarity	NPC295009
0.897	High Similarity	NPC113055
0.897	High Similarity	NPC55738
0.897	High Similarity	NPC473990
0.897	High Similarity	NPC215375
0.897	High Similarity	NPC95936
0.897	High Similarity	NPC62518
0.897	High Similarity	NPC250214
0.896	High Similarity	NPC470444
0.896	High Similarity	NPC473571
0.896	High Similarity	NPC473682
0.896	High Similarity	NPC241423
0.896	High Similarity	NPC126784
0.896	High Similarity	NPC110941
0.896	High Similarity	NPC470443
0.8957	High Similarity	NPC244371
0.8953	High Similarity	NPC198324
0.8953	High Similarity	NPC65563
0.8953	High Similarity	NPC233994
0.8953	High Similarity	NPC8573
0.8953	High Similarity	NPC472385
0.8953	High Similarity	NPC470949
0.8953	High Similarity	NPC211532
0.8947	High Similarity	NPC208668
0.8947	High Similarity	NPC204693
0.8941	High Similarity	NPC102277
0.8941	High Similarity	NPC287884
0.8941	High Similarity	NPC150767

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 NPC156635 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	936
0.2-0.3	1858
0.3-0.4	2629
0.4-0.5	1820
0.5-0.6	943
0.6-0.7	400
0.7-0.8	143
0.8-0.85	36
0.85-0.9	13
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9146	High Similarity	NPD5494	Approved
0.8935	High Similarity	NPD3818	Discontinued
0.8895	High Similarity	NPD4338	Clinical (unspecified phase)
0.883	High Similarity	NPD7074	Phase 3
0.8786	High Similarity	NPD7808	Phase 3
0.8779	High Similarity	NPD6797	Phase 2
0.8772	High Similarity	NPD7054	Approved
0.8735	High Similarity	NPD3882	Suspended
0.8728	High Similarity	NPD7251	Discontinued
0.8727	High Similarity	NPD2393	Clinical (unspecified phase)
0.8721	High Similarity	NPD7472	Approved
0.8706	High Similarity	NPD6166	Phase 2
0.8706	High Similarity	NPD6167	Clinical (unspecified phase)
0.8706	High Similarity	NPD6168	Clinical (unspecified phase)
0.8667	High Similarity	NPD1934	Approved
0.8663	High Similarity	NPD7804	Clinical (unspecified phase)
0.8614	High Similarity	NPD2801	Approved
0.8571	High Similarity	NPD4381	Clinical (unspecified phase)
0.8503	High Similarity	NPD7096	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7075	Discontinued
0.8452	Intermediate Similarity	NPD3817	Phase 2
0.8448	Intermediate Similarity	NPD5844	Phase 1
0.8409	Intermediate Similarity	NPD6559	Discontinued
0.8323	Intermediate Similarity	NPD4380	Phase 2
0.8314	Intermediate Similarity	NPD1247	Approved
0.8297	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD5402	Approved
0.8225	Intermediate Similarity	NPD6801	Discontinued
0.8222	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD1512	Approved
0.8182	Intermediate Similarity	NPD3751	Discontinued
0.8176	Intermediate Similarity	NPD7819	Suspended
0.8146	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD919	Approved
0.8072	Intermediate Similarity	NPD6799	Approved
0.8072	Intermediate Similarity	NPD1511	Approved
0.8059	Intermediate Similarity	NPD7411	Suspended
0.8057	Intermediate Similarity	NPD3787	Discontinued
0.8057	Intermediate Similarity	NPD6232	Discontinued
0.8036	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7473	Discontinued
0.8011	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD3926	Phase 2
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD6959	Discontinued
0.7989	Intermediate Similarity	NPD6782	Approved
0.7989	Intermediate Similarity	NPD6778	Approved
0.7989	Intermediate Similarity	NPD6780	Approved
0.7989	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD6781	Approved
0.7989	Intermediate Similarity	NPD6779	Approved
0.7989	Intermediate Similarity	NPD6777	Approved
0.7989	Intermediate Similarity	NPD6776	Approved
0.7988	Intermediate Similarity	NPD1549	Phase 2
0.7965	Intermediate Similarity	NPD1465	Phase 2
0.7927	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD37	Approved
0.7898	Intermediate Similarity	NPD7199	Phase 2
0.7886	Intermediate Similarity	NPD6234	Discontinued
0.7877	Intermediate Similarity	NPD7228	Approved
0.7874	Intermediate Similarity	NPD4967	Phase 2
0.7874	Intermediate Similarity	NPD4966	Approved
0.7874	Intermediate Similarity	NPD4965	Approved
0.7866	Intermediate Similarity	NPD2796	Approved
0.7865	Intermediate Similarity	NPD7435	Discontinued
0.7865	Intermediate Similarity	NPD7696	Phase 3
0.7865	Intermediate Similarity	NPD7697	Approved
0.7865	Intermediate Similarity	NPD7698	Approved
0.7829	Intermediate Similarity	NPD3749	Approved
0.7824	Intermediate Similarity	NPD5403	Approved
0.7814	Intermediate Similarity	NPD8312	Approved
0.7814	Intermediate Similarity	NPD8313	Approved
0.7795	Intermediate Similarity	NPD7701	Phase 2
0.7765	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD7870	Phase 2
0.7732	Intermediate Similarity	NPD7871	Phase 2
0.7725	Intermediate Similarity	NPD6534	Approved
0.7725	Intermediate Similarity	NPD6535	Approved
0.7706	Intermediate Similarity	NPD5401	Approved
0.7706	Intermediate Similarity	NPD2533	Approved
0.7706	Intermediate Similarity	NPD2534	Approved
0.7706	Intermediate Similarity	NPD2532	Approved
0.7705	Intermediate Similarity	NPD7685	Pre-registration
0.7697	Intermediate Similarity	NPD1510	Phase 2
0.7696	Intermediate Similarity	NPD7699	Phase 2
0.7696	Intermediate Similarity	NPD7700	Phase 2
0.7688	Intermediate Similarity	NPD8434	Phase 2
0.7674	Intermediate Similarity	NPD1653	Approved
0.767	Intermediate Similarity	NPD7768	Phase 2
0.7651	Intermediate Similarity	NPD2935	Discontinued
0.7626	Intermediate Similarity	NPD7874	Approved
0.7626	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2800	Approved
0.7616	Intermediate Similarity	NPD920	Approved
0.7609	Intermediate Similarity	NPD7240	Approved
0.7588	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7801	Approved
0.7588	Intermediate Similarity	NPD7783	Phase 2
0.7576	Intermediate Similarity	NPD8151	Discontinued
0.7561	Intermediate Similarity	NPD1240	Approved
0.7538	Intermediate Similarity	NPD6823	Phase 2
0.7515	Intermediate Similarity	NPD1933	Approved
0.7515	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8150	Discontinued
0.7475	Intermediate Similarity	NPD7584	Approved
0.7471	Intermediate Similarity	NPD4628	Phase 3
0.7471	Intermediate Similarity	NPD3750	Approved
0.747	Intermediate Similarity	NPD1607	Approved
0.7458	Intermediate Similarity	NPD8455	Phase 2
0.7455	Intermediate Similarity	NPD943	Approved
0.7436	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7458	Discontinued
0.7429	Intermediate Similarity	NPD3226	Approved
0.7427	Intermediate Similarity	NPD6190	Approved
0.7412	Intermediate Similarity	NPD1243	Approved
0.741	Intermediate Similarity	NPD447	Suspended
0.7396	Intermediate Similarity	NPD2346	Discontinued
0.7384	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2799	Discontinued
0.7374	Intermediate Similarity	NPD8320	Phase 1
0.7374	Intermediate Similarity	NPD8319	Approved
0.7368	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD1613	Approved
0.7349	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD230	Phase 1
0.7294	Intermediate Similarity	NPD2344	Approved
0.7287	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3748	Approved
0.7273	Intermediate Similarity	NPD5953	Discontinued
0.7268	Intermediate Similarity	NPD5710	Approved
0.7268	Intermediate Similarity	NPD5711	Approved
0.726	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7286	Phase 2
0.725	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1551	Phase 2
0.7229	Intermediate Similarity	NPD2313	Discontinued
0.7229	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6213	Phase 3
0.7216	Intermediate Similarity	NPD6212	Phase 3
0.7212	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6674	Discontinued
0.72	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7266	Discontinued
0.7189	Intermediate Similarity	NPD2403	Approved
0.7186	Intermediate Similarity	NPD5005	Approved
0.7186	Intermediate Similarity	NPD5006	Approved
0.7176	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7229	Phase 3
0.7169	Intermediate Similarity	NPD3027	Phase 3
0.7168	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5242	Approved
0.7135	Intermediate Similarity	NPD6099	Approved
0.7135	Intermediate Similarity	NPD6100	Approved
0.7135	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7583	Approved
0.7126	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2309	Approved
0.7121	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6844	Discontinued
0.7109	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7549	Discontinued
0.7101	Intermediate Similarity	NPD6355	Discontinued
0.7095	Intermediate Similarity	NPD7028	Phase 2
0.7095	Intermediate Similarity	NPD7907	Approved
0.7094	Intermediate Similarity	NPD7585	Approved
0.7092	Intermediate Similarity	NPD4360	Phase 2
0.7092	Intermediate Similarity	NPD4363	Phase 3
0.7091	Intermediate Similarity	NPD2798	Approved
0.7083	Intermediate Similarity	NPD6233	Phase 2
0.7081	Intermediate Similarity	NPD4665	Approved
0.7081	Intermediate Similarity	NPD4111	Phase 1
0.7076	Intermediate Similarity	NPD7033	Discontinued
0.7071	Intermediate Similarity	NPD4420	Approved
0.7065	Intermediate Similarity	NPD7680	Approved
0.7056	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD2424	Discontinued
0.705	Intermediate Similarity	NPD2493	Approved
0.705	Intermediate Similarity	NPD2494	Approved
0.7045	Intermediate Similarity	NPD7390	Discontinued
0.7033	Intermediate Similarity	NPD5353	Approved
0.7031	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8127	Discontinued
0.7024	Intermediate Similarity	NPD6798	Discontinued
0.702	Intermediate Similarity	NPD2973	Approved
0.702	Intermediate Similarity	NPD2974	Approved
0.702	Intermediate Similarity	NPD2975	Approved
0.7009	Intermediate Similarity	NPD8059	Phase 3
0.7009	Intermediate Similarity	NPD8058	Clinical (unspecified phase)

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