NPASS Compound

Structure

NPC171656 OpenBabel07101719512D 27 29 0 0 1 0 0 0 0 0999 V2000 -2.5981 3.5000 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 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 3.5000 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 4.3301 1.5000 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 1.7321 0.0000 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 4.3301 0.5000 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 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 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 1.7321 2.0000 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 0.5000 0.0000 C 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 -2.5981 0.5000 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 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 7 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 21 1 0 0 0 0 5 21 1 0 0 0 0 6 24 1 0 0 0 0 7 11 2 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 20 1 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 19 2 0 0 0 0 14 18 1 0 0 0 0 14 22 2 0 0 0 0 15 27 1 0 0 0 0 16 18 2 0 0 0 0 16 25 1 0 0 0 0 17 21 1 0 0 0 0 17 26 1 6 0 0 0 18 19 1 0 0 0 0 19 24 1 0 0 0 0 20 23 2 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.16
Volume:	380.389
LogP:	4.104
LogD:	2.693
LogS:	-3.511
# Rotatable Bonds:	4
TPSA:	74.97
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.604
Synthetic Accessibility Score:	3.66
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.634
MDCK Permeability:	1.887518919829745e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.11

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	81.18343353271484%
Volume Distribution (VD):	1.01
Pgp-substrate:	11.066015243530273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.459
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.94
CYP2C19-substrate:	0.784
CYP2C9-inhibitor:	0.932
CYP2C9-substrate:	0.876
CYP2D6-inhibitor:	0.441
CYP2D6-substrate:	0.533
CYP3A4-inhibitor:	0.709
CYP3A4-substrate:	0.759

ADMET: Excretion

Clearance (CL):	3.527
Half-life (T1/2):	0.219

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.944
Drug-inuced Liver Injury (DILI):	0.271
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.165
Maximum Recommended Daily Dose:	0.846
Skin Sensitization:	0.372
Carcinogencity:	0.333
Eye Corrosion:	0.003
Eye Irritation:	0.035
Respiratory Toxicity:	0.352

Download Data

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

Natural Product: NPC171656

Natural Product ID:	NPC171656
*Common Name:**	[(3R)-5-Methoxy-2,2,8-Trimethyl-6-Oxo-3,4-Dihydropyrano[3,2-G]Chromen-3-Yl] (Z)-2-Methylbut-2-Enoate
IUPAC Name:	[(3R)-5-methoxy-2,2,8-trimethyl-6-oxo-3,4-dihydropyrano[3,2-g]chromen-3-yl] (Z)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	QNOQNIIIQHXDAV-CGICMKJESA-N
Standard InCHI:	InChI=1S/C21H24O6/c1-7-11(2)20(23)26-17-9-13-15(27-21(17,4)5)10-16-18(19(13)24-6)14(22)8-12(3)25-16/h7-8,10,17H,9H2,1-6H3/b11-7-/t17-/m1/s1
SMILES:	C/C=C(C(=O)O[C@@H]1Cc2c(OC1(C)C)cc1c(c2OC)c(=O)cc(o1)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458524
PubChem CID:	10904780
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003543] Pyranochromenes

*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
NPO32915	prionosciadium watsoni	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088423]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	14300.0	nM	PMID[466527]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	IC50	=	26400.0	nM	PMID[466527]

☑ 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 NPC171656 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	403
0.1-0.2	1651
0.2-0.3	4121
0.3-0.4	9256
0.4-0.5	9306
0.5-0.6	3954
0.6-0.7	6012
0.7-0.8	5079
0.8-0.85	2101
0.85-0.9	704
0.9-0.95	73
0.95-1	37

Similarity Score	Similarity Level	Natural Product ID
0.9856	High Similarity	NPC294365
0.965	High Similarity	NPC180351
0.958	High Similarity	NPC164299
0.9517	High Similarity	NPC256141
0.9371	High Similarity	NPC474302
0.9281	High Similarity	NPC268081
0.922	High Similarity	NPC11566
0.9214	High Similarity	NPC253616
0.9195	High Similarity	NPC470625
0.9172	High Similarity	NPC85773
0.9155	High Similarity	NPC472409
0.9155	High Similarity	NPC470856
0.9149	High Similarity	NPC36414
0.9122	High Similarity	NPC40033
0.911	High Similarity	NPC10097
0.9097	High Similarity	NPC59522
0.9091	High Similarity	NPC201820
0.9085	High Similarity	NPC472515
0.9085	High Similarity	NPC136095
0.9078	High Similarity	NPC259685
0.9078	High Similarity	NPC38153
0.9071	High Similarity	NPC46869
0.906	High Similarity	NPC7989
0.906	High Similarity	NPC472583
0.906	High Similarity	NPC469405
0.906	High Similarity	NPC223701
0.9054	High Similarity	NPC472422
0.9054	High Similarity	NPC263384
0.9054	High Similarity	NPC244577
0.9054	High Similarity	NPC471676
0.9054	High Similarity	NPC472420
0.9048	High Similarity	NPC139966
0.9048	High Similarity	NPC307052
0.9041	High Similarity	NPC470670
0.9041	High Similarity	NPC473133
0.9041	High Similarity	NPC47388
0.9041	High Similarity	NPC282335
0.9041	High Similarity	NPC218300
0.9041	High Similarity	NPC91902
0.9028	High Similarity	NPC147145
0.9013	High Similarity	NPC43971
0.9013	High Similarity	NPC19554
0.9013	High Similarity	NPC74749
0.9007	High Similarity	NPC254741
0.9007	High Similarity	NPC161196
0.9	High Similarity	NPC477530
0.9	High Similarity	NPC108937
0.9	High Similarity	NPC279218
0.8993	High Similarity	NPC476238
0.8993	High Similarity	NPC327269
0.8993	High Similarity	NPC229646
0.8993	High Similarity	NPC473996
0.8993	High Similarity	NPC31627
0.898	High Similarity	NPC476342
0.8958	High Similarity	NPC52576
0.8951	High Similarity	NPC473209
0.8947	High Similarity	NPC50430
0.8944	High Similarity	NPC103001
0.894	High Similarity	NPC474738
0.894	High Similarity	NPC474609
0.894	High Similarity	NPC469936
0.894	High Similarity	NPC321372
0.894	High Similarity	NPC109967
0.894	High Similarity	NPC129053
0.894	High Similarity	NPC78554
0.894	High Similarity	NPC17521
0.894	High Similarity	NPC475797
0.8936	High Similarity	NPC160727
0.8936	High Similarity	NPC55615
0.8936	High Similarity	NPC177281
0.8936	High Similarity	NPC149320
0.8936	High Similarity	NPC476455
0.8936	High Similarity	NPC99854
0.8936	High Similarity	NPC128529
0.8936	High Similarity	NPC283019
0.8936	High Similarity	NPC471630
0.8933	High Similarity	NPC131725
0.8933	High Similarity	NPC236756
0.8933	High Similarity	NPC311579
0.8929	High Similarity	NPC47163
0.8929	High Similarity	NPC84894
0.8929	High Similarity	NPC166672
0.8929	High Similarity	NPC164269
0.8929	High Similarity	NPC195343
0.8929	High Similarity	NPC198381
0.8929	High Similarity	NPC319859
0.8929	High Similarity	NPC287182
0.8929	High Similarity	NPC267412
0.8929	High Similarity	NPC100986
0.8929	High Similarity	NPC74655
0.8929	High Similarity	NPC18804
0.8929	High Similarity	NPC127888
0.8929	High Similarity	NPC260265
0.8929	High Similarity	NPC247743
0.8926	High Similarity	NPC474021
0.8926	High Similarity	NPC472580
0.8926	High Similarity	NPC472636
0.8926	High Similarity	NPC471677
0.8926	High Similarity	NPC474023
0.8926	High Similarity	NPC471675
0.8919	High Similarity	NPC164205
0.8919	High Similarity	NPC104236
0.8912	High Similarity	NPC473077
0.8912	High Similarity	NPC202494
0.8912	High Similarity	NPC110303
0.8912	High Similarity	NPC296998
0.8912	High Similarity	NPC129650
0.8912	High Similarity	NPC23728
0.8912	High Similarity	NPC285748
0.8912	High Similarity	NPC471285
0.8904	High Similarity	NPC87486
0.8904	High Similarity	NPC179970
0.8904	High Similarity	NPC470890
0.8904	High Similarity	NPC124780
0.8904	High Similarity	NPC316535
0.8904	High Similarity	NPC469953
0.8904	High Similarity	NPC224714
0.8904	High Similarity	NPC209040
0.8897	High Similarity	NPC471643
0.8897	High Similarity	NPC276565
0.8897	High Similarity	NPC470556
0.8897	High Similarity	NPC471639
0.8897	High Similarity	NPC294432
0.8897	High Similarity	NPC112829
0.8889	High Similarity	NPC477164
0.8881	High Similarity	NPC17848
0.8881	High Similarity	NPC131130
0.8874	High Similarity	NPC217706
0.8874	High Similarity	NPC470681
0.8874	High Similarity	NPC470603
0.8874	High Similarity	NPC295608
0.8874	High Similarity	NPC207809
0.8874	High Similarity	NPC470604
0.8874	High Similarity	NPC259710
0.8874	High Similarity	NPC470605
0.8874	High Similarity	NPC250769
0.8874	High Similarity	NPC477958
0.8874	High Similarity	NPC278010
0.8874	High Similarity	NPC48579
0.8874	High Similarity	NPC304207
0.8873	High Similarity	NPC472516
0.8867	High Similarity	NPC171651
0.8867	High Similarity	NPC475790
0.8867	High Similarity	NPC285623
0.8867	High Similarity	NPC161881
0.8867	High Similarity	NPC35567
0.8867	High Similarity	NPC150123
0.8867	High Similarity	NPC244583
0.8867	High Similarity	NPC56232
0.8867	High Similarity	NPC10807
0.8867	High Similarity	NPC477957
0.8867	High Similarity	NPC288534
0.8867	High Similarity	NPC243171
0.8865	High Similarity	NPC86892
0.8865	High Similarity	NPC471909
0.8865	High Similarity	NPC125269
0.8865	High Similarity	NPC471625
0.8865	High Similarity	NPC472424
0.8865	High Similarity	NPC281241
0.8859	High Similarity	NPC470908
0.8859	High Similarity	NPC474735
0.8859	High Similarity	NPC5840
0.8859	High Similarity	NPC189270
0.8859	High Similarity	NPC191104
0.8859	High Similarity	NPC61258
0.8859	High Similarity	NPC321387
0.8859	High Similarity	NPC327059
0.8859	High Similarity	NPC472421
0.8859	High Similarity	NPC472633
0.8857	High Similarity	NPC207002
0.8857	High Similarity	NPC471910
0.8857	High Similarity	NPC296624
0.8857	High Similarity	NPC133956
0.8857	High Similarity	NPC318400
0.8857	High Similarity	NPC167111
0.8851	High Similarity	NPC472345
0.8851	High Similarity	NPC160821
0.8851	High Similarity	NPC168085
0.8851	High Similarity	NPC132592
0.8851	High Similarity	NPC211811
0.8844	High Similarity	NPC195621
0.8844	High Similarity	NPC54577
0.8844	High Similarity	NPC472629
0.8844	High Similarity	NPC267375
0.8844	High Similarity	NPC470647
0.8844	High Similarity	NPC301276
0.8844	High Similarity	NPC67805
0.8844	High Similarity	NPC214774
0.8844	High Similarity	NPC246948
0.8844	High Similarity	NPC111786
0.8844	High Similarity	NPC142405
0.8844	High Similarity	NPC20488
0.8844	High Similarity	NPC176229
0.8844	High Similarity	NPC88964
0.8844	High Similarity	NPC24136
0.8844	High Similarity	NPC312973
0.8844	High Similarity	NPC187282
0.8844	High Similarity	NPC290133
0.8844	High Similarity	NPC475052
0.8844	High Similarity	NPC83357

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 NPC171656 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	968
0.2-0.3	1782
0.3-0.4	2597
0.4-0.5	1893
0.5-0.6	1044
0.6-0.7	365
0.7-0.8	117
0.8-0.85	34
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.906	High Similarity	NPD7096	Clinical (unspecified phase)
0.9007	High Similarity	NPD2796	Approved
0.8882	High Similarity	NPD7075	Discontinued
0.8867	High Similarity	NPD6801	Discontinued
0.8733	High Similarity	NPD4380	Phase 2
0.8707	High Similarity	NPD6799	Approved
0.869	High Similarity	NPD1243	Approved
0.8684	High Similarity	NPD7819	Suspended
0.8675	High Similarity	NPD7411	Suspended
0.8658	High Similarity	NPD920	Approved
0.8649	High Similarity	NPD4378	Clinical (unspecified phase)
0.8562	High Similarity	NPD2393	Clinical (unspecified phase)
0.8526	High Similarity	NPD5494	Approved
0.8523	High Similarity	NPD642	Clinical (unspecified phase)
0.8516	High Similarity	NPD4381	Clinical (unspecified phase)
0.8514	High Similarity	NPD643	Clinical (unspecified phase)
0.8506	High Similarity	NPD3817	Phase 2
0.8493	Intermediate Similarity	NPD1549	Phase 2
0.8487	Intermediate Similarity	NPD6599	Discontinued
0.8425	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD1934	Approved
0.8344	Intermediate Similarity	NPD919	Approved
0.8289	Intermediate Similarity	NPD5403	Approved
0.8288	Intermediate Similarity	NPD3748	Approved
0.8288	Intermediate Similarity	NPD1510	Phase 2
0.8278	Intermediate Similarity	NPD5401	Approved
0.8272	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD5402	Approved
0.8121	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7768	Phase 2
0.8089	Intermediate Similarity	NPD2801	Approved
0.8049	Intermediate Similarity	NPD5844	Phase 1
0.8039	Intermediate Similarity	NPD2533	Approved
0.8039	Intermediate Similarity	NPD2534	Approved
0.8039	Intermediate Similarity	NPD2532	Approved
0.8014	Intermediate Similarity	NPD1240	Approved
0.8013	Intermediate Similarity	NPD3750	Approved
0.8012	Intermediate Similarity	NPD6559	Discontinued
0.8012	Intermediate Similarity	NPD1247	Approved
0.8012	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2313	Discontinued
0.7988	Intermediate Similarity	NPD3818	Discontinued
0.7986	Intermediate Similarity	NPD6832	Phase 2
0.7975	Intermediate Similarity	NPD6166	Phase 2
0.7975	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1511	Approved
0.7947	Intermediate Similarity	NPD2800	Approved
0.7939	Intermediate Similarity	NPD7054	Approved
0.7937	Intermediate Similarity	NPD3749	Approved
0.7919	Intermediate Similarity	NPD2799	Discontinued
0.7905	Intermediate Similarity	NPD1607	Approved
0.7895	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4628	Phase 3
0.7892	Intermediate Similarity	NPD7074	Phase 3
0.7892	Intermediate Similarity	NPD7472	Approved
0.7875	Intermediate Similarity	NPD3882	Suspended
0.7872	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1512	Approved
0.7867	Intermediate Similarity	NPD1551	Phase 2
0.7867	Intermediate Similarity	NPD2935	Discontinued
0.7857	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6232	Discontinued
0.7844	Intermediate Similarity	NPD6797	Phase 2
0.7838	Intermediate Similarity	NPD5124	Phase 1
0.7838	Intermediate Similarity	NPD1933	Approved
0.7838	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7473	Discontinued
0.7798	Intermediate Similarity	NPD7251	Discontinued
0.7778	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7808	Phase 3
0.7738	Intermediate Similarity	NPD5953	Discontinued
0.7738	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7286	Phase 2
0.7724	Intermediate Similarity	NPD1019	Discontinued
0.7718	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2346	Discontinued
0.7682	Intermediate Similarity	NPD7033	Discontinued
0.7667	Intermediate Similarity	NPD6651	Approved
0.7651	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4307	Phase 2
0.7635	Intermediate Similarity	NPD1296	Phase 2
0.7625	Intermediate Similarity	NPD5889	Approved
0.7625	Intermediate Similarity	NPD5890	Approved
0.7613	Intermediate Similarity	NPD3887	Approved
0.761	Intermediate Similarity	NPD3226	Approved
0.7597	Intermediate Similarity	NPD1652	Phase 2
0.7597	Intermediate Similarity	NPD2654	Approved
0.7593	Intermediate Similarity	NPD5353	Approved
0.759	Intermediate Similarity	NPD3926	Phase 2
0.7569	Intermediate Similarity	NPD9717	Approved
0.7562	Intermediate Similarity	NPD6585	Discontinued
0.7545	Intermediate Similarity	NPD2403	Approved
0.7534	Intermediate Similarity	NPD3267	Approved
0.7534	Intermediate Similarity	NPD3266	Approved
0.7531	Intermediate Similarity	NPD1465	Phase 2
0.753	Intermediate Similarity	NPD5711	Approved
0.753	Intermediate Similarity	NPD5710	Approved
0.7528	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD447	Suspended
0.7483	Intermediate Similarity	NPD230	Phase 1
0.7483	Intermediate Similarity	NPD2798	Approved
0.7456	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4308	Phase 3
0.7442	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2424	Discontinued
0.7415	Intermediate Similarity	NPD1203	Approved
0.7403	Intermediate Similarity	NPD6099	Approved
0.7403	Intermediate Similarity	NPD6100	Approved
0.74	Intermediate Similarity	NPD6798	Discontinued
0.74	Intermediate Similarity	NPD3268	Approved
0.7391	Intermediate Similarity	NPD7458	Discontinued
0.7379	Intermediate Similarity	NPD422	Phase 1
0.7357	Intermediate Similarity	NPD1241	Discontinued
0.7355	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2353	Approved
0.7351	Intermediate Similarity	NPD7584	Approved
0.7318	Intermediate Similarity	NPD4360	Phase 2
0.7318	Intermediate Similarity	NPD4363	Phase 3
0.7317	Intermediate Similarity	NPD8455	Phase 2
0.7299	Intermediate Similarity	NPD8313	Approved
0.7299	Intermediate Similarity	NPD8312	Approved
0.7297	Intermediate Similarity	NPD2797	Approved
0.7285	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5242	Approved
0.7273	Intermediate Similarity	NPD4288	Approved
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.7267	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6355	Discontinued
0.7253	Intermediate Similarity	NPD8285	Discontinued
0.7251	Intermediate Similarity	NPD3751	Discontinued
0.725	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2344	Approved
0.7241	Intermediate Similarity	NPD17	Approved
0.7237	Intermediate Similarity	NPD6233	Phase 2
0.7226	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD9545	Approved
0.7222	Intermediate Similarity	NPD1653	Approved
0.7219	Intermediate Similarity	NPD7229	Phase 3
0.7219	Intermediate Similarity	NPD6808	Phase 2
0.7219	Intermediate Similarity	NPD3787	Discontinued
0.7211	Intermediate Similarity	NPD3972	Approved
0.7205	Intermediate Similarity	NPD5049	Phase 3
0.719	Intermediate Similarity	NPD3142	Approved
0.719	Intermediate Similarity	NPD3140	Approved
0.7171	Intermediate Similarity	NPD411	Approved
0.717	Intermediate Similarity	NPD2354	Approved
0.7166	Intermediate Similarity	NPD7583	Approved
0.7161	Intermediate Similarity	NPD7097	Phase 1
0.716	Intermediate Similarity	NPD7199	Phase 2
0.7152	Intermediate Similarity	NPD37	Approved
0.7152	Intermediate Similarity	NPD4908	Phase 1
0.7134	Intermediate Similarity	NPD6002	Phase 3
0.7134	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6004	Phase 3
0.7134	Intermediate Similarity	NPD6005	Phase 3
0.7134	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7585	Approved
0.7126	Intermediate Similarity	NPD4967	Phase 2
0.7126	Intermediate Similarity	NPD4965	Approved
0.7126	Intermediate Similarity	NPD4966	Approved
0.7114	Intermediate Similarity	NPD3225	Approved
0.7099	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7435	Discontinued
0.7095	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1608	Approved
0.7091	Intermediate Similarity	NPD6385	Approved
0.7091	Intermediate Similarity	NPD6386	Approved
0.709	Intermediate Similarity	NPD8151	Discontinued
0.7086	Intermediate Similarity	NPD6104	Discontinued
0.7083	Intermediate Similarity	NPD9493	Approved
0.7081	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7390	Discontinued
0.7079	Intermediate Similarity	NPD8150	Discontinued
0.7078	Intermediate Similarity	NPD943	Approved
0.7078	Intermediate Similarity	NPD1613	Approved
0.7078	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2438	Suspended
0.7063	Intermediate Similarity	NPD2309	Approved
0.7059	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5691	Approved
0.705	Intermediate Similarity	NPD1358	Approved
0.7048	Intermediate Similarity	NPD6844	Discontinued
0.7041	Intermediate Similarity	NPD6234	Discontinued
0.7037	Intermediate Similarity	NPD4662	Approved
0.7037	Intermediate Similarity	NPD4661	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