NPASS Compound

Structure

CID67302 OpenBabel06191715402D 29 34 0 0 1 0 0 0 0 0999 V2000 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -0.3660 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6010 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 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 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 2 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 4.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 4 14 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 21 1 0 0 0 0 7 13 2 0 0 0 0 7 16 1 0 0 0 0 8 15 2 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 9 25 1 0 0 0 0 10 26 1 0 0 0 0 10 27 1 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 29 1 0 0 0 0 15 25 1 0 0 0 0 16 17 2 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 22 1 6 0 0 0 18 28 1 0 0 0 0 19 28 1 0 0 0 0 20 22 1 0 0 0 0 20 23 2 0 0 0 0 21 29 1 0 0 0 0 22 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.11
Volume:	378.169
LogP:	4.166
LogD:	3.925
LogS:	-4.941
# Rotatable Bonds:	0
TPSA:	83.45
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.736
Synthetic Accessibility Score:	3.99
Fsp3:	0.318
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:	-4.843
MDCK Permeability:	2.4404893338214606e-05
Pgp-inhibitor:	0.792
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.081
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	97.7721176147461%
Volume Distribution (VD):	0.809
Pgp-substrate:	2.62935733795166%

ADMET: Metabolism

CYP1A2-inhibitor:	0.828
CYP1A2-substrate:	0.368
CYP2C19-inhibitor:	0.96
CYP2C19-substrate:	0.493
CYP2C9-inhibitor:	0.897
CYP2C9-substrate:	0.68
CYP2D6-inhibitor:	0.961
CYP2D6-substrate:	0.265
CYP3A4-inhibitor:	0.942
CYP3A4-substrate:	0.718

ADMET: Excretion

Clearance (CL):	9.51
Half-life (T1/2):	0.096

ADMET: Toxicity

hERG Blockers:	0.27
Human Hepatotoxicity (H-HT):	0.845
Drug-inuced Liver Injury (DILI):	0.306
AMES Toxicity:	0.686
Rat Oral Acute Toxicity:	0.332
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.31
Carcinogencity:	0.947
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.198

Download Data

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

Natural Product: NPC67302

Natural Product ID:	NPC67302
*Common Name:**	UMORYJJPSIXKBM-GCJKJVERSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UMORYJJPSIXKBM-GCJKJVERSA-N
Standard InCHI:	InChI=1S/C22H18O7/c1-21(2)6-5-11-14(29-21)4-3-12-19(11)28-18-9-25-15-8-17-16(26-10-27-17)7-13(15)22(18,24)20(12)23/h3-8,18,24H,9-10H2,1-2H3/t18-,22+/m1/s1
SMILES:	O=C1c2ccc3c(c2O[C@H]2[C@@]1(O)c1cc4OCOc4cc1OC2)C=CC(O3)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3759427
PubChem CID:	7330544
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
Others	2

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	100700.0	nM	PMID[450076]
NPT757	Organism	Plasmodium falciparum 3D7	Plasmodium falciparum 3D7	Inhibition	=	28.0	%	PMID[450076]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Inhibition	=	29.0	%	PMID[450076]

☑ 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 NPC67302 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	420
0.1-0.2	1745
0.2-0.3	3922
0.3-0.4	9325
0.4-0.5	8941
0.5-0.6	3820
0.6-0.7	5112
0.7-0.8	5550
0.8-0.85	2880
0.85-0.9	938
0.9-0.95	37
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9818	High Similarity	NPC156635
0.9573	High Similarity	NPC8965
0.9515	High Similarity	NPC242395
0.9515	High Similarity	NPC152477
0.9401	High Similarity	NPC121333
0.9401	High Similarity	NPC475825
0.9401	High Similarity	NPC223375
0.9398	High Similarity	NPC177480
0.9357	High Similarity	NPC473883
0.9341	High Similarity	NPC74559
0.929	High Similarity	NPC108202
0.9277	High Similarity	NPC173292
0.9277	High Similarity	NPC113093
0.9226	High Similarity	NPC472276
0.9217	High Similarity	NPC234052
0.9212	High Similarity	NPC18284
0.9212	High Similarity	NPC273021
0.9191	High Similarity	NPC148710
0.9186	High Similarity	NPC473071
0.9186	High Similarity	NPC473073
0.9181	High Similarity	NPC168584
0.9176	High Similarity	NPC472607
0.9172	High Similarity	NPC475155
0.9167	High Similarity	NPC326877
0.9162	High Similarity	NPC120593
0.9162	High Similarity	NPC128293
0.9152	High Similarity	NPC34376
0.9133	High Similarity	NPC473072
0.9123	High Similarity	NPC257714
0.9123	High Similarity	NPC169733
0.9112	High Similarity	NPC474434
0.9112	High Similarity	NPC105511
0.9112	High Similarity	NPC103307
0.9112	High Similarity	NPC44558
0.9107	High Similarity	NPC150131
0.9107	High Similarity	NPC42892
0.9107	High Similarity	NPC135345
0.9107	High Similarity	NPC93099
0.9102	High Similarity	NPC224280
0.9102	High Similarity	NPC62261
0.9096	High Similarity	NPC125991
0.9096	High Similarity	NPC478199
0.9064	High Similarity	NPC294629
0.9059	High Similarity	NPC235575
0.9059	High Similarity	NPC205076
0.9059	High Similarity	NPC476405
0.9059	High Similarity	NPC307518
0.9059	High Similarity	NPC256760
0.9059	High Similarity	NPC117260
0.9059	High Similarity	NPC267254
0.9059	High Similarity	NPC48773
0.9059	High Similarity	NPC156977
0.9053	High Similarity	NPC183036
0.9053	High Similarity	NPC210042
0.9053	High Similarity	NPC288813
0.9053	High Similarity	NPC95855
0.9053	High Similarity	NPC472383
0.9053	High Similarity	NPC472381
0.9053	High Similarity	NPC471287
0.9042	High Similarity	NPC273959
0.9042	High Similarity	NPC470178
0.9036	High Similarity	NPC94155
0.9036	High Similarity	NPC165549
0.9017	High Similarity	NPC110941
0.9017	High Similarity	NPC126784
0.9017	High Similarity	NPC473682
0.9017	High Similarity	NPC473571
0.9017	High Similarity	NPC470443
0.9017	High Similarity	NPC241423
0.9017	High Similarity	NPC470444
0.9012	High Similarity	NPC472384
0.9012	High Similarity	NPC8573
0.9012	High Similarity	NPC472380
0.9012	High Similarity	NPC470949
0.9012	High Similarity	NPC65563
0.9012	High Similarity	NPC472382
0.9006	High Similarity	NPC21666
0.9006	High Similarity	NPC51774
0.9006	High Similarity	NPC169977
0.9006	High Similarity	NPC101026
0.9006	High Similarity	NPC42773
0.9006	High Similarity	NPC310794
0.9006	High Similarity	NPC236191
0.9006	High Similarity	NPC24043
0.9006	High Similarity	NPC45522
0.9006	High Similarity	NPC208668
0.9006	High Similarity	NPC239549
0.9006	High Similarity	NPC204693
0.9	High Similarity	NPC84265
0.9	High Similarity	NPC212748
0.9	High Similarity	NPC471416
0.9	High Similarity	NPC78734
0.9	High Similarity	NPC22195
0.9	High Similarity	NPC282987
0.9	High Similarity	NPC231194
0.9	High Similarity	NPC21190
0.9	High Similarity	NPC183357
0.9	High Similarity	NPC194483
0.9	High Similarity	NPC245014
0.9	High Similarity	NPC51326
0.9	High Similarity	NPC293004
0.9	High Similarity	NPC150767
0.9	High Similarity	NPC34287
0.9	High Similarity	NPC224462
0.8994	High Similarity	NPC76482
0.8982	High Similarity	NPC261470
0.8982	High Similarity	NPC472402
0.8982	High Similarity	NPC472448
0.8982	High Similarity	NPC83922
0.8982	High Similarity	NPC302741
0.8982	High Similarity	NPC469575
0.8982	High Similarity	NPC81679
0.8976	High Similarity	NPC298093
0.8966	High Similarity	NPC6709
0.896	High Similarity	NPC472387
0.896	High Similarity	NPC475261
0.8953	High Similarity	NPC477848
0.8953	High Similarity	NPC142996
0.8953	High Similarity	NPC264735
0.8953	High Similarity	NPC102028
0.8947	High Similarity	NPC245452
0.8947	High Similarity	NPC301683
0.8947	High Similarity	NPC472386
0.8947	High Similarity	NPC261254
0.8947	High Similarity	NPC3583
0.8947	High Similarity	NPC259152
0.8941	High Similarity	NPC58053
0.8941	High Similarity	NPC475942
0.8941	High Similarity	NPC165456
0.8941	High Similarity	NPC226294
0.8941	High Similarity	NPC61791
0.8941	High Similarity	NPC471457
0.8941	High Similarity	NPC229687
0.8941	High Similarity	NPC186807
0.8941	High Similarity	NPC170675
0.8941	High Similarity	NPC201292
0.8941	High Similarity	NPC93337
0.8941	High Similarity	NPC112755
0.8941	High Similarity	NPC105025
0.8941	High Similarity	NPC469931
0.8941	High Similarity	NPC45638
0.8935	High Similarity	NPC472449
0.8935	High Similarity	NPC170245
0.8929	High Similarity	NPC41301
0.8929	High Similarity	NPC303460
0.8929	High Similarity	NPC472281
0.8929	High Similarity	NPC205265
0.8929	High Similarity	NPC124038
0.8929	High Similarity	NPC306321
0.8929	High Similarity	NPC472625
0.8922	High Similarity	NPC173137
0.8922	High Similarity	NPC134783
0.8922	High Similarity	NPC260640
0.8922	High Similarity	NPC162668
0.8922	High Similarity	NPC167678
0.8922	High Similarity	NPC295009
0.8922	High Similarity	NPC40037
0.8922	High Similarity	NPC29876
0.8916	High Similarity	NPC62518
0.8916	High Similarity	NPC113055
0.8916	High Similarity	NPC152904
0.8916	High Similarity	NPC215375
0.8914	High Similarity	NPC36138
0.8914	High Similarity	NPC470447
0.8914	High Similarity	NPC470445
0.8914	High Similarity	NPC470449
0.8914	High Similarity	NPC470446
0.8909	High Similarity	NPC303255
0.8909	High Similarity	NPC155063
0.8908	High Similarity	NPC473895
0.8902	High Similarity	NPC233994
0.8902	High Similarity	NPC211532
0.8902	High Similarity	NPC472385
0.8902	High Similarity	NPC198324
0.8902	High Similarity	NPC268533
0.8889	High Similarity	NPC287884
0.8889	High Similarity	NPC218488
0.8889	High Similarity	NPC285197
0.8889	High Similarity	NPC67105
0.8889	High Similarity	NPC72249
0.8889	High Similarity	NPC52353
0.8889	High Similarity	NPC206123
0.8889	High Similarity	NPC95866
0.8889	High Similarity	NPC8704
0.8882	High Similarity	NPC146792
0.8882	High Similarity	NPC45618
0.8882	High Similarity	NPC229729
0.8882	High Similarity	NPC6588
0.8882	High Similarity	NPC58716
0.8882	High Similarity	NPC45400
0.8882	High Similarity	NPC471288
0.8882	High Similarity	NPC477502
0.8882	High Similarity	NPC117854
0.8882	High Similarity	NPC477154
0.8876	High Similarity	NPC275780
0.8876	High Similarity	NPC300053
0.8876	High Similarity	NPC50960
0.8876	High Similarity	NPC326520
0.8876	High Similarity	NPC475366
0.8876	High Similarity	NPC108433

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 NPC67302 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	373
0.1-0.2	963
0.2-0.3	1973
0.3-0.4	2598
0.4-0.5	1803
0.5-0.6	897
0.6-0.7	371
0.7-0.8	129
0.8-0.85	33
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8976	High Similarity	NPD5494	Approved
0.8882	High Similarity	NPD3818	Discontinued
0.8844	High Similarity	NPD7808	Phase 3
0.8844	High Similarity	NPD4338	Clinical (unspecified phase)
0.8837	High Similarity	NPD6797	Phase 2
0.883	High Similarity	NPD7054	Approved
0.8786	High Similarity	NPD7251	Discontinued
0.8779	High Similarity	NPD7074	Phase 3
0.8779	High Similarity	NPD7472	Approved
0.8721	High Similarity	NPD7804	Clinical (unspecified phase)
0.8655	High Similarity	NPD6166	Phase 2
0.8655	High Similarity	NPD6168	Clinical (unspecified phase)
0.8655	High Similarity	NPD6167	Clinical (unspecified phase)
0.8571	High Similarity	NPD3882	Suspended
0.8563	High Similarity	NPD2801	Approved
0.8563	High Similarity	NPD2393	Clinical (unspecified phase)
0.8521	High Similarity	NPD4381	Clinical (unspecified phase)
0.8503	High Similarity	NPD1934	Approved
0.8402	Intermediate Similarity	NPD3817	Phase 2
0.8343	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD7075	Discontinued
0.8295	Intermediate Similarity	NPD5844	Phase 1
0.8284	Intermediate Similarity	NPD6801	Discontinued
0.8274	Intermediate Similarity	NPD4380	Phase 2
0.8266	Intermediate Similarity	NPD1247	Approved
0.8258	Intermediate Similarity	NPD6559	Discontinued
0.8251	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD5402	Approved
0.8144	Intermediate Similarity	NPD1512	Approved
0.814	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD3751	Discontinued
0.8101	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD6959	Discontinued
0.8046	Intermediate Similarity	NPD919	Approved
0.8024	Intermediate Similarity	NPD1511	Approved
0.8023	Intermediate Similarity	NPD7819	Suspended
0.8011	Intermediate Similarity	NPD3787	Discontinued
0.7947	Intermediate Similarity	NPD6781	Approved
0.7947	Intermediate Similarity	NPD6780	Approved
0.7947	Intermediate Similarity	NPD6782	Approved
0.7947	Intermediate Similarity	NPD6776	Approved
0.7947	Intermediate Similarity	NPD6779	Approved
0.7947	Intermediate Similarity	NPD6778	Approved
0.7947	Intermediate Similarity	NPD6777	Approved
0.7946	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1465	Phase 2
0.7917	Intermediate Similarity	NPD6799	Approved
0.791	Intermediate Similarity	NPD6232	Discontinued
0.7907	Intermediate Similarity	NPD7411	Suspended
0.7882	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD7473	Discontinued
0.7874	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD3926	Phase 2
0.7849	Intermediate Similarity	NPD6599	Discontinued
0.7833	Intermediate Similarity	NPD7228	Approved
0.7831	Intermediate Similarity	NPD1549	Phase 2
0.7824	Intermediate Similarity	NPD7697	Approved
0.7824	Intermediate Similarity	NPD7435	Discontinued
0.7824	Intermediate Similarity	NPD7696	Phase 3
0.7824	Intermediate Similarity	NPD7698	Approved
0.7818	Intermediate Similarity	NPD2796	Approved
0.7778	Intermediate Similarity	NPD5403	Approved
0.7772	Intermediate Similarity	NPD8312	Approved
0.7772	Intermediate Similarity	NPD8313	Approved
0.7771	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD37	Approved
0.7755	Intermediate Similarity	NPD7701	Phase 2
0.7753	Intermediate Similarity	NPD7199	Phase 2
0.774	Intermediate Similarity	NPD6234	Discontinued
0.7727	Intermediate Similarity	NPD4965	Approved
0.7727	Intermediate Similarity	NPD4967	Phase 2
0.7727	Intermediate Similarity	NPD4966	Approved
0.7722	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7871	Phase 2
0.7692	Intermediate Similarity	NPD7870	Phase 2
0.7684	Intermediate Similarity	NPD3749	Approved
0.7684	Intermediate Similarity	NPD6534	Approved
0.7684	Intermediate Similarity	NPD6535	Approved
0.7674	Intermediate Similarity	NPD920	Approved
0.7663	Intermediate Similarity	NPD7685	Pre-registration
0.7661	Intermediate Similarity	NPD5401	Approved
0.7656	Intermediate Similarity	NPD7699	Phase 2
0.7656	Intermediate Similarity	NPD7700	Phase 2
0.7651	Intermediate Similarity	NPD1510	Phase 2
0.763	Intermediate Similarity	NPD1653	Approved
0.7602	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7874	Approved
0.7574	Intermediate Similarity	NPD2800	Approved
0.7568	Intermediate Similarity	NPD7240	Approved
0.7558	Intermediate Similarity	NPD2532	Approved
0.7558	Intermediate Similarity	NPD2533	Approved
0.7558	Intermediate Similarity	NPD2534	Approved
0.7553	Intermediate Similarity	NPD8434	Phase 2
0.755	Intermediate Similarity	NPD7801	Approved
0.755	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7783	Phase 2
0.7538	Intermediate Similarity	NPD8151	Discontinued
0.7528	Intermediate Similarity	NPD7768	Phase 2
0.75	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD6823	Phase 2
0.746	Intermediate Similarity	NPD8150	Discontinued
0.7457	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD7584	Approved
0.7427	Intermediate Similarity	NPD3750	Approved
0.7416	Intermediate Similarity	NPD8455	Phase 2
0.741	Intermediate Similarity	NPD1240	Approved
0.7386	Intermediate Similarity	NPD7458	Discontinued
0.7368	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1243	Approved
0.7365	Intermediate Similarity	NPD1933	Approved
0.7341	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD8320	Phase 1
0.7337	Intermediate Similarity	NPD8319	Approved
0.7326	Intermediate Similarity	NPD4628	Phase 3
0.7326	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1607	Approved
0.731	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD943	Approved
0.7288	Intermediate Similarity	NPD3226	Approved
0.7283	Intermediate Similarity	NPD6190	Approved
0.7262	Intermediate Similarity	NPD447	Suspended
0.7251	Intermediate Similarity	NPD2346	Discontinued
0.7249	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2799	Discontinued
0.7235	Intermediate Similarity	NPD3748	Approved
0.7225	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7286	Phase 2
0.7214	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1613	Approved
0.7186	Intermediate Similarity	NPD2313	Discontinued
0.7179	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6212	Phase 3
0.7179	Intermediate Similarity	NPD6213	Phase 3
0.716	Intermediate Similarity	NPD230	Phase 1
0.7158	Intermediate Similarity	NPD7549	Discontinued
0.7151	Intermediate Similarity	NPD2344	Approved
0.7151	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD5953	Discontinued
0.7135	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5711	Approved
0.7135	Intermediate Similarity	NPD5710	Approved
0.7094	Intermediate Similarity	NPD7583	Approved
0.7093	Intermediate Similarity	NPD1551	Phase 2
0.7085	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6844	Discontinued
0.7069	Intermediate Similarity	NPD6674	Discontinued
0.7066	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5005	Approved
0.7065	Intermediate Similarity	NPD5006	Approved
0.7062	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7585	Approved
0.7056	Intermediate Similarity	NPD4363	Phase 3
0.7056	Intermediate Similarity	NPD4360	Phase 2
0.7052	Intermediate Similarity	NPD7266	Discontinued
0.7048	Intermediate Similarity	NPD2798	Approved
0.7043	Intermediate Similarity	NPD7229	Phase 3
0.7035	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7033	Discontinued
0.703	Intermediate Similarity	NPD7680	Approved
0.7029	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3027	Phase 3
0.7006	Intermediate Similarity	NPD7390	Discontinued
0.7006	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5242	Approved
0.7	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6100	Approved
0.6994	Remote Similarity	NPD6099	Approved
0.6989	Remote Similarity	NPD2309	Approved
0.6982	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7907	Approved
0.6977	Remote Similarity	NPD8059	Phase 3
0.6977	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD4665	Approved
0.6967	Remote Similarity	NPD4111	Phase 1
0.6961	Remote Similarity	NPD7028	Phase 2
0.6959	Remote Similarity	NPD6355	Discontinued
0.6959	Remote Similarity	NPD5124	Phase 1
0.6959	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4420	Approved
0.6941	Remote Similarity	NPD6233	Phase 2
0.6931	Remote Similarity	NPD2493	Approved
0.6931	Remote Similarity	NPD2494	Approved
0.6923	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6651	Approved
0.6914	Remote Similarity	NPD2424	Discontinued
0.6907	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD5353	Approved
0.69	Remote Similarity	NPD2973	Approved
0.69	Remote Similarity	NPD2975	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