NPASS Compound

Structure

NPC471910 OpenBabel07101718182D 28 30 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 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 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 -1.8660 -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 3.4641 -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 -3.0000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 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 -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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 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 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 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 0.0000 -3.0000 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 -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 11 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 8 2 0 0 0 0 6 13 1 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 11 2 0 0 0 0 10 16 1 0 0 0 0 12 22 2 0 0 0 0 12 25 1 0 0 0 0 13 18 2 0 0 0 0 14 17 2 0 0 0 0 14 28 1 0 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 16 24 2 0 0 0 0 16 27 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 25 1 6 0 0 0 20 21 1 0 0 0 0 20 27 1 6 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.14
Volume:	386.543
LogP:	3.62
LogD:	3.039
LogS:	-3.767
# Rotatable Bonds:	5
TPSA:	92.04
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.453
Synthetic Accessibility Score:	3.684
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.701
MDCK Permeability:	4.0387054468737915e-05
Pgp-inhibitor:	0.977
Pgp-substrate:	0.036
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.036
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.106
Plasma Protein Binding (PPB):	80.6321029663086%
Volume Distribution (VD):	1.722
Pgp-substrate:	16.055049896240234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.224
CYP1A2-substrate:	0.185
CYP2C19-inhibitor:	0.865
CYP2C19-substrate:	0.293
CYP2C9-inhibitor:	0.862
CYP2C9-substrate:	0.158
CYP2D6-inhibitor:	0.63
CYP2D6-substrate:	0.278
CYP3A4-inhibitor:	0.814
CYP3A4-substrate:	0.456

ADMET: Excretion

Clearance (CL):	7.192
Half-life (T1/2):	0.523

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.965
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.234
Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.458
Skin Sensitization:	0.419
Carcinogencity:	0.661
Eye Corrosion:	0.014
Eye Irritation:	0.033
Respiratory Toxicity:	0.591

Download Data

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

Natural Product: NPC471910

Natural Product ID:	NPC471910
*Common Name:**	3'-Senecioyl-4'-Acetylkhellactone
IUPAC Name:	[(9S,10S)-10-acetyloxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-9-yl] 3-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	FNVCLGWRMXTDSM-PMACEKPBSA-N
Standard InCHI:	InChI=1S/C21H22O7/c1-11(2)10-16(24)27-20-19(25-12(3)22)17-14(28-21(20,4)5)8-6-13-7-9-15(23)26-18(13)17/h6-10,19-20H,1-5H3/t19-,20-/m0/s1
SMILES:	CC(=CC(=O)OC1C(C2=C(C=CC3=C2OC(=O)C=C3)OC1(C)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3290963
PubChem CID:	12315234
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003485] Angular pyranocoumarins

*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
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24813739]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8874	Glehnia littoralis	Species	Apiaceae	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	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	44300.0	nM	PMID[551995]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	90.0	%	PMID[551995]

☑ 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 NPC471910 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	416
0.1-0.2	1699
0.2-0.3	4257
0.3-0.4	9547
0.4-0.5	8881
0.5-0.6	4023
0.6-0.7	5952
0.7-0.8	5353
0.8-0.85	1900
0.85-0.9	463
0.9-0.95	148
0.95-1	58

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC207002
1.0	High Similarity	NPC296624
1.0	High Similarity	NPC167111
1.0	High Similarity	NPC318400
1.0	High Similarity	NPC133956
0.9921	High Similarity	NPC166672
0.9921	High Similarity	NPC195343
0.9921	High Similarity	NPC74655
0.9921	High Similarity	NPC287182
0.9921	High Similarity	NPC198381
0.9921	High Similarity	NPC319859
0.9921	High Similarity	NPC127888
0.9921	High Similarity	NPC100986
0.9921	High Similarity	NPC84894
0.9921	High Similarity	NPC267412
0.9921	High Similarity	NPC18804
0.9921	High Similarity	NPC164269
0.9921	High Similarity	NPC260265
0.9921	High Similarity	NPC47163
0.9844	High Similarity	NPC86892
0.9844	High Similarity	NPC281241
0.9844	High Similarity	NPC471625
0.9844	High Similarity	NPC472424
0.9844	High Similarity	NPC471909
0.9767	High Similarity	NPC471630
0.9767	High Similarity	NPC149320
0.9767	High Similarity	NPC177281
0.9767	High Similarity	NPC128529
0.9767	High Similarity	NPC160727
0.9767	High Similarity	NPC476455
0.9767	High Similarity	NPC55615
0.9767	High Similarity	NPC283019
0.9618	High Similarity	NPC211110
0.9618	High Similarity	NPC279573
0.9612	High Similarity	NPC307412
0.9612	High Similarity	NPC55149
0.9609	High Similarity	NPC14248
0.9545	High Similarity	NPC312881
0.9542	High Similarity	NPC153818
0.9542	High Similarity	NPC232246
0.9538	High Similarity	NPC469675
0.9535	High Similarity	NPC222036
0.9535	High Similarity	NPC7526
0.9474	High Similarity	NPC152771
0.9474	High Similarity	NPC287286
0.9474	High Similarity	NPC195357
0.9466	High Similarity	NPC224543
0.9466	High Similarity	NPC78746
0.9466	High Similarity	NPC188380
0.9453	High Similarity	NPC80170
0.9444	High Similarity	NPC471826
0.9394	High Similarity	NPC155963
0.9394	High Similarity	NPC225106
0.9394	High Similarity	NPC281014
0.9394	High Similarity	NPC184861
0.9394	High Similarity	NPC294456
0.9394	High Similarity	NPC212124
0.9389	High Similarity	NPC472525
0.9375	High Similarity	NPC168710
0.9333	High Similarity	NPC119640
0.9333	High Similarity	NPC183646
0.9323	High Similarity	NPC151946
0.9318	High Similarity	NPC26954
0.9318	High Similarity	NPC38099
0.9318	High Similarity	NPC283331
0.9313	High Similarity	NPC62366
0.9313	High Similarity	NPC213173
0.9313	High Similarity	NPC180716
0.9313	High Similarity	NPC224475
0.9297	High Similarity	NPC199204
0.9286	High Similarity	NPC111347
0.9286	High Similarity	NPC201667
0.9286	High Similarity	NPC73413
0.9265	High Similarity	NPC476457
0.9242	High Similarity	NPC33986
0.9237	High Similarity	NPC31849
0.9213	High Similarity	NPC471828
0.9213	High Similarity	NPC471827
0.9206	High Similarity	NPC472518
0.9206	High Similarity	NPC273772
0.9206	High Similarity	NPC109675
0.9197	High Similarity	NPC85624
0.9197	High Similarity	NPC469701
0.9179	High Similarity	NPC270256
0.9167	High Similarity	NPC253574
0.9167	High Similarity	NPC98179
0.9167	High Similarity	NPC326600
0.9167	High Similarity	NPC50896
0.9167	High Similarity	NPC204353
0.9147	High Similarity	NPC293642
0.9147	High Similarity	NPC60704
0.9147	High Similarity	NPC472519
0.9147	High Similarity	NPC185066
0.9147	High Similarity	NPC139595
0.9141	High Similarity	NPC188327
0.9141	High Similarity	NPC234109
0.9134	High Similarity	NPC27671
0.9134	High Similarity	NPC291899
0.9127	High Similarity	NPC248429
0.9127	High Similarity	NPC96286
0.9124	High Similarity	NPC471824
0.9091	High Similarity	NPC469955
0.9091	High Similarity	NPC469952
0.9084	High Similarity	NPC29734
0.9065	High Similarity	NPC296377
0.9065	High Similarity	NPC87950
0.9065	High Similarity	NPC471764
0.9055	High Similarity	NPC290605
0.9055	High Similarity	NPC173350
0.9055	High Similarity	NPC154176
0.9055	High Similarity	NPC50720
0.9015	High Similarity	NPC469956
0.9015	High Similarity	NPC19157
0.9015	High Similarity	NPC194277
0.9008	High Similarity	NPC113098
0.9	High Similarity	NPC169510
0.8976	High Similarity	NPC257188
0.8976	High Similarity	NPC150214
0.8976	High Similarity	NPC13007
0.8968	High Similarity	NPC235190
0.8968	High Similarity	NPC163200
0.8968	High Similarity	NPC180006
0.8947	High Similarity	NPC469449
0.8947	High Similarity	NPC163557
0.8939	High Similarity	NPC272650
0.8939	High Similarity	NPC267336
0.8923	High Similarity	NPC289316
0.8906	High Similarity	NPC315807
0.8898	High Similarity	NPC144418
0.8889	High Similarity	NPC167517
0.8881	High Similarity	NPC131950
0.8881	High Similarity	NPC309953
0.8872	High Similarity	NPC123954
0.8864	High Similarity	NPC19242
0.8857	High Similarity	NPC171656
0.8855	High Similarity	NPC157212
0.8846	High Similarity	NPC163248
0.8824	High Similarity	NPC471069
0.8824	High Similarity	NPC306365
0.8824	High Similarity	NPC471068
0.8824	High Similarity	NPC14697
0.8815	High Similarity	NPC311430
0.8815	High Similarity	NPC224941
0.881	High Similarity	NPC281356
0.881	High Similarity	NPC298796
0.8806	High Similarity	NPC469965
0.8806	High Similarity	NPC141822
0.8806	High Similarity	NPC142563
0.8806	High Similarity	NPC205797
0.8806	High Similarity	NPC241165
0.8806	High Similarity	NPC241341
0.8806	High Similarity	NPC1220
0.8806	High Similarity	NPC36437
0.8806	High Similarity	NPC233018
0.8806	High Similarity	NPC291551
0.8806	High Similarity	NPC472522
0.8779	High Similarity	NPC243688
0.8779	High Similarity	NPC121740
0.8779	High Similarity	NPC258567
0.8779	High Similarity	NPC224774
0.8769	High Similarity	NPC232692
0.8769	High Similarity	NPC202594
0.876	High Similarity	NPC143725
0.8759	High Similarity	NPC471072
0.8759	High Similarity	NPC35501
0.8759	High Similarity	NPC278600
0.8759	High Similarity	NPC137262
0.8759	High Similarity	NPC144512
0.8759	High Similarity	NPC37428
0.8759	High Similarity	NPC471071
0.8759	High Similarity	NPC47040
0.8759	High Similarity	NPC471070
0.875	High Similarity	NPC286843
0.8741	High Similarity	NPC147030
0.8741	High Similarity	NPC103116
0.8731	High Similarity	NPC137669
0.8731	High Similarity	NPC319969
0.873	High Similarity	NPC152306
0.873	High Similarity	NPC96705
0.873	High Similarity	NPC265547
0.8723	High Similarity	NPC294365
0.8722	High Similarity	NPC32463
0.8714	High Similarity	NPC471763
0.8712	High Similarity	NPC469453
0.8702	High Similarity	NPC101894
0.8686	High Similarity	NPC131198
0.8676	High Similarity	NPC234865
0.8667	High Similarity	NPC55147
0.8667	High Similarity	NPC54503
0.8652	High Similarity	NPC475719
0.8652	High Similarity	NPC101255
0.8652	High Similarity	NPC43716
0.8652	High Similarity	NPC295696
0.8652	High Similarity	NPC76657
0.8636	High Similarity	NPC473993
0.8633	High Similarity	NPC138149
0.8633	High Similarity	NPC215512
0.8633	High Similarity	NPC476442
0.8633	High Similarity	NPC279851
0.8633	High Similarity	NPC472523

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 NPC471910 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	961
0.2-0.3	1775
0.3-0.4	2636
0.4-0.5	1874
0.5-0.6	1031
0.6-0.7	357
0.7-0.8	114
0.8-0.85	34
0.85-0.9	9
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8806	High Similarity	NPD5123	Clinical (unspecified phase)
0.8806	High Similarity	NPD5124	Phase 1
0.85	High Similarity	NPD1652	Phase 2
0.8321	Intermediate Similarity	NPD422	Phase 1
0.8133	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1653	Approved
0.8029	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD2796	Approved
0.7974	Intermediate Similarity	NPD7075	Discontinued
0.7958	Intermediate Similarity	NPD3748	Approved
0.7947	Intermediate Similarity	NPD6801	Discontinued
0.7914	Intermediate Similarity	NPD1296	Phase 2
0.7914	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD4908	Phase 1
0.7857	Intermediate Similarity	NPD1358	Approved
0.7852	Intermediate Similarity	NPD920	Approved
0.7829	Intermediate Similarity	NPD5535	Approved
0.782	Intermediate Similarity	NPD5691	Approved
0.7815	Intermediate Similarity	NPD4380	Phase 2
0.7808	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1613	Approved
0.7793	Intermediate Similarity	NPD2424	Discontinued
0.7785	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1610	Phase 2
0.7778	Intermediate Similarity	NPD7819	Suspended
0.777	Intermediate Similarity	NPD6799	Approved
0.7763	Intermediate Similarity	NPD7411	Suspended
0.775	Intermediate Similarity	NPD5844	Phase 1
0.7744	Intermediate Similarity	NPD1548	Phase 1
0.774	Intermediate Similarity	NPD1243	Approved
0.7718	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD9697	Approved
0.7687	Intermediate Similarity	NPD3750	Approved
0.7677	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD5494	Approved
0.7639	Intermediate Similarity	NPD7097	Phase 1
0.7638	Intermediate Similarity	NPD3134	Approved
0.7632	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD5403	Approved
0.7613	Intermediate Similarity	NPD3817	Phase 2
0.7609	Intermediate Similarity	NPD8651	Approved
0.76	Intermediate Similarity	NPD5401	Approved
0.7589	Intermediate Similarity	NPD4625	Phase 3
0.7582	Intermediate Similarity	NPD6599	Discontinued
0.758	Intermediate Similarity	NPD919	Approved
0.7574	Intermediate Similarity	NPD3496	Discontinued
0.7571	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD7768	Phase 2
0.7554	Intermediate Similarity	NPD3266	Approved
0.7554	Intermediate Similarity	NPD3267	Approved
0.7554	Intermediate Similarity	NPD2797	Approved
0.7552	Intermediate Similarity	NPD4307	Phase 2
0.7552	Intermediate Similarity	NPD4060	Phase 1
0.7551	Intermediate Similarity	NPD1549	Phase 2
0.7536	Intermediate Similarity	NPD4749	Approved
0.7535	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD6798	Discontinued
0.7518	Intermediate Similarity	NPD1091	Approved
0.7518	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD4340	Discontinued
0.75	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD4626	Approved
0.7484	Intermediate Similarity	NPD1934	Approved
0.7483	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD3225	Approved
0.7466	Intermediate Similarity	NPD7033	Discontinued
0.7465	Intermediate Similarity	NPD3027	Phase 3
0.7455	Intermediate Similarity	NPD7549	Discontinued
0.745	Intermediate Similarity	NPD4628	Phase 3
0.7423	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD3268	Approved
0.7397	Intermediate Similarity	NPD4536	Approved
0.7397	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4538	Approved
0.7394	Intermediate Similarity	NPD6559	Discontinued
0.7391	Intermediate Similarity	NPD1611	Approved
0.7389	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2415	Discontinued
0.7385	Intermediate Similarity	NPD2684	Approved
0.7383	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6355	Discontinued
0.7361	Intermediate Similarity	NPD6233	Phase 2
0.7351	Intermediate Similarity	NPD5058	Phase 3
0.7347	Intermediate Similarity	NPD4308	Phase 3
0.7347	Intermediate Similarity	NPD1510	Phase 2
0.7346	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD8455	Phase 2
0.7324	Intermediate Similarity	NPD2861	Phase 2
0.732	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1551	Phase 2
0.7297	Intermediate Similarity	NPD2935	Discontinued
0.7293	Intermediate Similarity	NPD7843	Approved
0.7292	Intermediate Similarity	NPD2313	Discontinued
0.7273	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1933	Approved
0.7259	Intermediate Similarity	NPD7157	Approved
0.7254	Intermediate Similarity	NPD1019	Discontinued
0.7248	Intermediate Similarity	NPD5762	Approved
0.7248	Intermediate Similarity	NPD6005	Phase 3
0.7248	Intermediate Similarity	NPD5763	Approved
0.7248	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6002	Phase 3
0.7248	Intermediate Similarity	NPD6004	Phase 3
0.7248	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1241	Discontinued
0.723	Intermediate Similarity	NPD5588	Approved
0.723	Intermediate Similarity	NPD2799	Discontinued
0.723	Intermediate Similarity	NPD5960	Phase 3
0.7222	Intermediate Similarity	NPD7095	Approved
0.7219	Intermediate Similarity	NPD7466	Approved
0.7219	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2801	Approved
0.7203	Intermediate Similarity	NPD3018	Phase 2
0.72	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4140	Approved
0.719	Intermediate Similarity	NPD7212	Phase 2
0.719	Intermediate Similarity	NPD7213	Phase 3
0.719	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3749	Approved
0.7176	Intermediate Similarity	NPD290	Approved
0.716	Intermediate Similarity	NPD1247	Approved
0.7153	Intermediate Similarity	NPD7644	Approved
0.7152	Intermediate Similarity	NPD4433	Discontinued
0.7152	Intermediate Similarity	NPD37	Approved
0.7152	Intermediate Similarity	NPD3818	Discontinued
0.7143	Intermediate Similarity	NPD7447	Phase 1
0.7143	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD2534	Approved
0.7143	Intermediate Similarity	NPD2532	Approved
0.7134	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6166	Phase 2
0.7133	Intermediate Similarity	NPD7266	Discontinued
0.7132	Intermediate Similarity	NPD6671	Approved
0.7126	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4965	Approved
0.7125	Intermediate Similarity	NPD4967	Phase 2
0.7125	Intermediate Similarity	NPD4966	Approved
0.7124	Intermediate Similarity	NPD6667	Approved
0.7124	Intermediate Similarity	NPD6666	Approved
0.7122	Intermediate Similarity	NPD1778	Approved
0.7117	Intermediate Similarity	NPD6232	Discontinued
0.7117	Intermediate Similarity	NPD7229	Phase 3
0.7108	Intermediate Similarity	NPD7054	Approved
0.7107	Intermediate Similarity	NPD1465	Phase 2
0.7092	Intermediate Similarity	NPD2981	Phase 2
0.7092	Intermediate Similarity	NPD9717	Approved
0.7078	Intermediate Similarity	NPD1511	Approved
0.7075	Intermediate Similarity	NPD1240	Approved
0.707	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6100	Approved
0.7067	Intermediate Similarity	NPD2438	Suspended
0.7067	Intermediate Similarity	NPD6032	Approved
0.7067	Intermediate Similarity	NPD6099	Approved
0.7066	Intermediate Similarity	NPD7472	Approved
0.7066	Intermediate Similarity	NPD7074	Phase 3
0.7063	Intermediate Similarity	NPD5353	Approved
0.7063	Intermediate Similarity	NPD4288	Approved
0.7059	Intermediate Similarity	NPD3887	Approved
0.7055	Intermediate Similarity	NPD7199	Phase 2
0.7055	Intermediate Similarity	NPD7985	Registered
0.7055	Intermediate Similarity	NPD8127	Discontinued
0.7055	Intermediate Similarity	NPD6959	Discontinued
0.705	Intermediate Similarity	NPD5585	Approved
0.7047	Intermediate Similarity	NPD2200	Suspended
0.7042	Intermediate Similarity	NPD2983	Phase 2
0.7042	Intermediate Similarity	NPD2982	Phase 2
0.7041	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6674	Discontinued
0.7037	Intermediate Similarity	NPD6234	Discontinued
0.7032	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5536	Phase 2
0.7027	Intermediate Similarity	NPD447	Suspended
0.7024	Intermediate Similarity	NPD6797	Phase 2
0.7021	Intermediate Similarity	NPD3705	Approved
0.702	Intermediate Similarity	NPD2346	Discontinued
0.7019	Intermediate Similarity	NPD3882	Suspended
0.7014	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4062	Phase 3
0.7	Intermediate Similarity	NPD17	Approved
0.6988	Remote Similarity	NPD7473	Discontinued
0.6987	Remote Similarity	NPD1512	Approved
0.6985	Remote Similarity	NPD5283	Phase 1
0.6982	Remote Similarity	NPD7251	Discontinued
0.698	Remote Similarity	NPD1607	Approved
0.6974	Remote Similarity	NPD2897	Discontinued

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