NPASS Compound

Structure

NPC476455 OpenBabel07101718192D 28 30 0 0 1 0 0 0 0 0999 V2000 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 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 -1.3660 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 -0.0000 -5.0000 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 -0.8660 -4.5000 0.0000 C 0 0 3 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 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 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 2 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 -0.8660 -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 -3.4641 -2.0000 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 -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 1.7321 -3.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 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 11 1 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 20 1 0 0 0 0 12 22 2 0 0 0 0 12 25 1 0 0 0 0 13 17 2 0 0 0 0 14 16 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 17 1 0 0 0 0 16 18 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 27 1 1 0 0 0 19 21 1 0 0 0 0 19 25 1 1 0 0 0 20 24 2 0 0 0 0 20 27 1 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.15
Volume:	389.179
LogP:	3.637
LogD:	2.961
LogS:	-3.891
# Rotatable Bonds:	6
TPSA:	92.04
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.584
Synthetic Accessibility Score:	3.768
Fsp3:	0.476
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:	-4.748
MDCK Permeability:	3.593677683966234e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113
Plasma Protein Binding (PPB):	88.65940856933594%
Volume Distribution (VD):	1.422
Pgp-substrate:	14.722015380859375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.663
CYP1A2-substrate:	0.391
CYP2C19-inhibitor:	0.645
CYP2C19-substrate:	0.17
CYP2C9-inhibitor:	0.678
CYP2C9-substrate:	0.126
CYP2D6-inhibitor:	0.535
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.74
CYP3A4-substrate:	0.388

ADMET: Excretion

Clearance (CL):	2.577
Half-life (T1/2):	0.291

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.982
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.162
Rat Oral Acute Toxicity:	0.074
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.102
Carcinogencity:	0.496
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.241

Download Data

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

Natural Product: NPC476455

Natural Product ID:	NPC476455
*Common Name:**	[(9R,10R)-9-Acetyloxy-8,8-Dimethyl-2-Oxo-9,10-Dihydropyrano[2,3-F]Chromen-10-Yl] 2-Methylbutanoate
IUPAC Name:	[(9R,10R)-9-acetyloxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] 2-methylbutanoate
Synonyms:
Standard InCHIKey:	CVCGZZMJIGSWHX-CDDDFZJFSA-N
Standard InCHI:	InChI=1S/C21H24O7/c1-6-11(2)20(24)27-18-16-14(28-21(4,5)19(18)25-12(3)22)9-7-13-8-10-15(23)26-17(13)16/h7-11,18-19H,6H2,1-5H3/t11?,18-,19-/m1/s1
SMILES:	CCC(C(=O)O[C@@H]1c2c(ccc3c2oc(=O)cc3)OC([C@@H]1OC(=O)C)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL68513
PubChem CID:	10068841
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
NPO3509	Angelica furcijuga	Species	Apiaceae	Eukaryota	roots	Miyazaki prefecture, Japan	n.a.	PMID[9873511]
NPO3509	Angelica furcijuga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3509	Angelica furcijuga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3509	Angelica furcijuga	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	2
Others	1

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	IC50	>	100000.0	nM	PMID[559289]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	-2.5	%	PMID[559289]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	8200.0	nM	PMID[559289]

☑ 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 NPC476455 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	1646
0.2-0.3	4074
0.3-0.4	9180
0.4-0.5	9424
0.5-0.6	4062
0.6-0.7	5920
0.7-0.8	5532
0.8-0.85	1848
0.85-0.9	392
0.9-0.95	154
0.95-1	49

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC55615
1.0	High Similarity	NPC149320
1.0	High Similarity	NPC160727
1.0	High Similarity	NPC128529
1.0	High Similarity	NPC177281
1.0	High Similarity	NPC471630
1.0	High Similarity	NPC283019
0.9922	High Similarity	NPC86892
0.9922	High Similarity	NPC471909
0.9922	High Similarity	NPC472424
0.9922	High Similarity	NPC471625
0.9922	High Similarity	NPC281241
0.9845	High Similarity	NPC18804
0.9845	High Similarity	NPC260265
0.9845	High Similarity	NPC198381
0.9845	High Similarity	NPC287182
0.9845	High Similarity	NPC164269
0.9845	High Similarity	NPC127888
0.9845	High Similarity	NPC74655
0.9845	High Similarity	NPC195343
0.9845	High Similarity	NPC84894
0.9845	High Similarity	NPC319859
0.9845	High Similarity	NPC166672
0.9845	High Similarity	NPC100986
0.9845	High Similarity	NPC47163
0.9845	High Similarity	NPC267412
0.9767	High Similarity	NPC167111
0.9767	High Similarity	NPC296624
0.9767	High Similarity	NPC471910
0.9767	High Similarity	NPC133956
0.9767	High Similarity	NPC207002
0.9767	High Similarity	NPC318400
0.9552	High Similarity	NPC287286
0.9549	High Similarity	NPC211110
0.9542	High Similarity	NPC307412
0.9542	High Similarity	NPC55149
0.9478	High Similarity	NPC312881
0.9466	High Similarity	NPC222036
0.9466	High Similarity	NPC7526
0.9412	High Similarity	NPC119640
0.9412	High Similarity	NPC183646
0.9407	High Similarity	NPC195357
0.9407	High Similarity	NPC152771
0.9403	High Similarity	NPC279573
0.9398	High Similarity	NPC283331
0.9389	High Similarity	NPC14248
0.9343	High Similarity	NPC476457
0.9328	High Similarity	NPC153818
0.9328	High Similarity	NPC155963
0.9328	High Similarity	NPC232246
0.9323	High Similarity	NPC469675
0.9259	High Similarity	NPC151946
0.9254	High Similarity	NPC224543
0.9254	High Similarity	NPC78746
0.9254	High Similarity	NPC188380
0.9237	High Similarity	NPC80170
0.9225	High Similarity	NPC471826
0.9185	High Similarity	NPC225106
0.9185	High Similarity	NPC294456
0.9185	High Similarity	NPC212124
0.9185	High Similarity	NPC184861
0.9185	High Similarity	NPC281014
0.9179	High Similarity	NPC472525
0.916	High Similarity	NPC168710
0.9147	High Similarity	NPC471828
0.9147	High Similarity	NPC471827
0.9137	High Similarity	NPC469701
0.9111	High Similarity	NPC38099
0.9111	High Similarity	NPC26954
0.9104	High Similarity	NPC224475
0.9104	High Similarity	NPC213173
0.9104	High Similarity	NPC62366
0.9104	High Similarity	NPC180716
0.9084	High Similarity	NPC60704
0.9084	High Similarity	NPC139595
0.9084	High Similarity	NPC293642
0.9084	High Similarity	NPC199204
0.9084	High Similarity	NPC472519
0.907	High Similarity	NPC201667
0.907	High Similarity	NPC73413
0.907	High Similarity	NPC111347
0.907	High Similarity	NPC27671
0.9037	High Similarity	NPC33986
0.903	High Similarity	NPC31849
0.903	High Similarity	NPC469955
0.903	High Similarity	NPC469952
0.9	High Similarity	NPC85624
0.8992	High Similarity	NPC273772
0.8992	High Similarity	NPC472518
0.8992	High Similarity	NPC109675
0.8978	High Similarity	NPC270256
0.8963	High Similarity	NPC326600
0.8963	High Similarity	NPC50896
0.8963	High Similarity	NPC204353
0.8963	High Similarity	NPC98179
0.8963	High Similarity	NPC253574
0.8939	High Similarity	NPC185066
0.8939	High Similarity	NPC157212
0.8936	High Similarity	NPC294365
0.8936	High Similarity	NPC171656
0.8931	High Similarity	NPC188327
0.8931	High Similarity	NPC234109
0.8929	High Similarity	NPC471824
0.8923	High Similarity	NPC291899
0.8915	High Similarity	NPC96286
0.8915	High Similarity	NPC248429
0.8905	High Similarity	NPC471069
0.8905	High Similarity	NPC471068
0.8889	High Similarity	NPC55147
0.8889	High Similarity	NPC54503
0.8881	High Similarity	NPC29734
0.8873	High Similarity	NPC87950
0.8873	High Similarity	NPC296377
0.8873	High Similarity	NPC471764
0.8849	High Similarity	NPC472523
0.8846	High Similarity	NPC50720
0.8846	High Similarity	NPC173350
0.8846	High Similarity	NPC290605
0.8846	High Similarity	NPC154176
0.8841	High Similarity	NPC307883
0.8841	High Similarity	NPC471071
0.8841	High Similarity	NPC471072
0.8841	High Similarity	NPC471070
0.8819	High Similarity	NPC103116
0.8815	High Similarity	NPC194277
0.8815	High Similarity	NPC469956
0.8815	High Similarity	NPC19157
0.8811	High Similarity	NPC169510
0.8806	High Similarity	NPC113098
0.8769	High Similarity	NPC13007
0.8769	High Similarity	NPC257188
0.8769	High Similarity	NPC150214
0.8768	High Similarity	NPC306365
0.8768	High Similarity	NPC14697
0.876	High Similarity	NPC180006
0.876	High Similarity	NPC163200
0.876	High Similarity	NPC235190
0.875	High Similarity	NPC205797
0.875	High Similarity	NPC1220
0.875	High Similarity	NPC141822
0.875	High Similarity	NPC163557
0.875	High Similarity	NPC469449
0.875	High Similarity	NPC142563
0.875	High Similarity	NPC241165
0.875	High Similarity	NPC469965
0.875	High Similarity	NPC291551
0.8741	High Similarity	NPC272650
0.8741	High Similarity	NPC267336
0.8732	High Similarity	NPC76657
0.8732	High Similarity	NPC295696
0.8722	High Similarity	NPC289316
0.8714	High Similarity	NPC155552
0.8705	High Similarity	NPC37428
0.8705	High Similarity	NPC144512
0.8705	High Similarity	NPC47040
0.8705	High Similarity	NPC35501
0.8705	High Similarity	NPC278600
0.8705	High Similarity	NPC137262
0.8702	High Similarity	NPC315807
0.8696	High Similarity	NPC104796
0.8696	High Similarity	NPC167517
0.8692	High Similarity	NPC144418
0.869	High Similarity	NPC164299
0.8686	High Similarity	NPC309953
0.8686	High Similarity	NPC131950
0.8676	High Similarity	NPC175159
0.8676	High Similarity	NPC123954
0.8667	High Similarity	NPC19242
0.8647	High Similarity	NPC163248
0.8633	High Similarity	NPC131198
0.863	High Similarity	NPC180351
0.8623	High Similarity	NPC311430
0.8623	High Similarity	NPC229128
0.8623	High Similarity	NPC224941
0.8613	High Similarity	NPC36437
0.8613	High Similarity	NPC241341
0.8613	High Similarity	NPC472522
0.8613	High Similarity	NPC233018
0.8605	High Similarity	NPC281356
0.8605	High Similarity	NPC298796
0.8603	High Similarity	NPC472517
0.8601	High Similarity	NPC475719
0.8601	High Similarity	NPC101255
0.8601	High Similarity	NPC43716
0.8592	High Similarity	NPC229916
0.8582	High Similarity	NPC258567
0.8582	High Similarity	NPC243688
0.8582	High Similarity	NPC138149
0.8582	High Similarity	NPC183642
0.8582	High Similarity	NPC121740
0.8582	High Similarity	NPC310370
0.8582	High Similarity	NPC224774
0.8571	High Similarity	NPC232692
0.8571	High Similarity	NPC202594
0.8561	High Similarity	NPC143725
0.8561	High Similarity	NPC286843
0.8551	High Similarity	NPC147030
0.854	High Similarity	NPC137669
0.854	High Similarity	NPC319969
0.8531	High Similarity	NPC471763

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 NPC476455 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	951
0.2-0.3	1755
0.3-0.4	2640
0.4-0.5	1889
0.5-0.6	1034
0.6-0.7	361
0.7-0.8	116
0.8-0.85	34
0.85-0.9	8
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD5123	Clinical (unspecified phase)
0.875	High Similarity	NPD5124	Phase 1
0.8322	Intermediate Similarity	NPD1652	Phase 2
0.8212	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD422	Phase 1
0.8112	Intermediate Similarity	NPD2796	Approved
0.8052	Intermediate Similarity	NPD7075	Discontinued
0.8042	Intermediate Similarity	NPD3748	Approved
0.8026	Intermediate Similarity	NPD6801	Discontinued
0.8014	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1296	Phase 2
0.8	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD920	Approved
0.7895	Intermediate Similarity	NPD4380	Phase 2
0.7881	Intermediate Similarity	NPD1653	Approved
0.7877	Intermediate Similarity	NPD2424	Discontinued
0.7857	Intermediate Similarity	NPD4908	Phase 1
0.7857	Intermediate Similarity	NPD7819	Suspended
0.7852	Intermediate Similarity	NPD6799	Approved
0.7847	Intermediate Similarity	NPD7097	Phase 1
0.7843	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD7411	Suspended
0.7834	Intermediate Similarity	NPD5494	Approved
0.7826	Intermediate Similarity	NPD5844	Phase 1
0.7823	Intermediate Similarity	NPD1243	Approved
0.78	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD3266	Approved
0.777	Intermediate Similarity	NPD3267	Approved
0.777	Intermediate Similarity	NPD3750	Approved
0.777	Intermediate Similarity	NPD2797	Approved
0.7756	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD1610	Phase 2
0.7707	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5403	Approved
0.7692	Intermediate Similarity	NPD3817	Phase 2
0.7682	Intermediate Similarity	NPD5401	Approved
0.7674	Intermediate Similarity	NPD1358	Approved
0.7662	Intermediate Similarity	NPD6599	Discontinued
0.7658	Intermediate Similarity	NPD919	Approved
0.7652	Intermediate Similarity	NPD5535	Approved
0.7647	Intermediate Similarity	NPD5691	Approved
0.7643	Intermediate Similarity	NPD7768	Phase 2
0.7639	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1613	Approved
0.7639	Intermediate Similarity	NPD4307	Phase 2
0.7635	Intermediate Similarity	NPD1549	Phase 2
0.7622	Intermediate Similarity	NPD3268	Approved
0.7622	Intermediate Similarity	NPD6798	Discontinued
0.7606	Intermediate Similarity	NPD6832	Phase 2
0.7597	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD3134	Approved
0.7586	Intermediate Similarity	NPD6355	Discontinued
0.758	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD5402	Approved
0.7574	Intermediate Similarity	NPD1548	Phase 1
0.7571	Intermediate Similarity	NPD3225	Approved
0.7568	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1934	Approved
0.7551	Intermediate Similarity	NPD7033	Discontinued
0.7533	Intermediate Similarity	NPD4628	Phase 3
0.7519	Intermediate Similarity	NPD9697	Approved
0.7517	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6559	Discontinued
0.745	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD6002	Phase 3
0.745	Intermediate Similarity	NPD6005	Phase 3
0.745	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD6004	Phase 3
0.7448	Intermediate Similarity	NPD6233	Phase 2
0.7447	Intermediate Similarity	NPD8651	Approved
0.7432	Intermediate Similarity	NPD2799	Discontinued
0.7432	Intermediate Similarity	NPD1510	Phase 2
0.7432	Intermediate Similarity	NPD4308	Phase 3
0.7431	Intermediate Similarity	NPD4625	Phase 3
0.7425	Intermediate Similarity	NPD7549	Discontinued
0.7423	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3496	Discontinued
0.7405	Intermediate Similarity	NPD8455	Phase 2
0.74	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2935	Discontinued
0.7383	Intermediate Similarity	NPD1551	Phase 2
0.7379	Intermediate Similarity	NPD2313	Discontinued
0.7357	Intermediate Similarity	NPD1091	Approved
0.7355	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4340	Discontinued
0.7347	Intermediate Similarity	NPD1933	Approved
0.7347	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1019	Discontinued
0.7342	Intermediate Similarity	NPD37	Approved
0.7338	Intermediate Similarity	NPD4626	Approved
0.7333	Intermediate Similarity	NPD1241	Discontinued
0.7312	Intermediate Similarity	NPD4966	Approved
0.7312	Intermediate Similarity	NPD4967	Phase 2
0.7312	Intermediate Similarity	NPD4965	Approved
0.731	Intermediate Similarity	NPD7095	Approved
0.731	Intermediate Similarity	NPD3027	Phase 3
0.7303	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7229	Phase 3
0.7296	Intermediate Similarity	NPD2801	Approved
0.7292	Intermediate Similarity	NPD2861	Phase 2
0.7267	Intermediate Similarity	NPD3749	Approved
0.7267	Intermediate Similarity	NPD2438	Suspended
0.7267	Intermediate Similarity	NPD6100	Approved
0.7267	Intermediate Similarity	NPD6099	Approved
0.7266	Intermediate Similarity	NPD5585	Approved
0.7261	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7985	Registered
0.725	Intermediate Similarity	NPD5353	Approved
0.725	Intermediate Similarity	NPD2415	Discontinued
0.7248	Intermediate Similarity	NPD4536	Approved
0.7248	Intermediate Similarity	NPD4538	Approved
0.7248	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD8127	Discontinued
0.7239	Intermediate Similarity	NPD7199	Phase 2
0.7239	Intermediate Similarity	NPD1247	Approved
0.7237	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1611	Approved
0.7229	Intermediate Similarity	NPD3818	Discontinued
0.7226	Intermediate Similarity	NPD2533	Approved
0.7226	Intermediate Similarity	NPD2534	Approved
0.7226	Intermediate Similarity	NPD2532	Approved
0.7226	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6234	Discontinued
0.7219	Intermediate Similarity	NPD5763	Approved
0.7219	Intermediate Similarity	NPD5762	Approved
0.7218	Intermediate Similarity	NPD2684	Approved
0.7214	Intermediate Similarity	NPD1778	Approved
0.7214	Intermediate Similarity	NPD17	Approved
0.7212	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6166	Phase 2
0.7212	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6667	Approved
0.7208	Intermediate Similarity	NPD5058	Phase 3
0.7208	Intermediate Similarity	NPD6666	Approved
0.7202	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6232	Discontinued
0.719	Intermediate Similarity	NPD7466	Approved
0.7188	Intermediate Similarity	NPD1465	Phase 2
0.7186	Intermediate Similarity	NPD7054	Approved
0.7183	Intermediate Similarity	NPD9717	Approved
0.7179	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7473	Discontinued
0.7162	Intermediate Similarity	NPD4140	Approved
0.7162	Intermediate Similarity	NPD1240	Approved
0.7162	Intermediate Similarity	NPD2979	Phase 3
0.7161	Intermediate Similarity	NPD1511	Approved
0.7152	Intermediate Similarity	NPD6032	Approved
0.7152	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD3887	Approved
0.7143	Intermediate Similarity	NPD7074	Phase 3
0.7143	Intermediate Similarity	NPD7472	Approved
0.7134	Intermediate Similarity	NPD6959	Discontinued
0.7132	Intermediate Similarity	NPD7843	Approved
0.7122	Intermediate Similarity	NPD5536	Phase 2
0.7122	Intermediate Similarity	NPD7644	Approved
0.7118	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4618	Approved
0.7114	Intermediate Similarity	NPD4622	Approved
0.7114	Intermediate Similarity	NPD447	Suspended
0.7108	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2346	Discontinued
0.7101	Intermediate Similarity	NPD7157	Approved
0.7101	Intermediate Similarity	NPD6797	Phase 2
0.7099	Intermediate Similarity	NPD3882	Suspended
0.7097	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD8032	Phase 2
0.7095	Intermediate Similarity	NPD4062	Phase 3
0.7086	Intermediate Similarity	NPD5588	Approved
0.7086	Intermediate Similarity	NPD5960	Phase 3
0.707	Intermediate Similarity	NPD1512	Approved
0.707	Intermediate Similarity	NPD6273	Approved
0.7067	Intermediate Similarity	NPD6653	Approved
0.7067	Intermediate Similarity	NPD1607	Approved
0.7063	Intermediate Similarity	NPD1608	Approved
0.7059	Intermediate Similarity	NPD2897	Discontinued
0.7059	Intermediate Similarity	NPD7251	Discontinued
0.7055	Intermediate Similarity	NPD3018	Phase 2
0.7051	Intermediate Similarity	NPD7213	Phase 3
0.7051	Intermediate Similarity	NPD7212	Phase 2
0.7044	Intermediate Similarity	NPD7458	Discontinued
0.7044	Intermediate Similarity	NPD3226	Approved
0.7039	Intermediate Similarity	NPD4477	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