NPASS Compound

Structure

CID146014 OpenBabel06191715502D 29 32 0 0 1 0 0 0 0 0999 V2000 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 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 0.0000 -1.0000 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 4.3301 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 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 -0.0000 0.0000 C 0 0 2 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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 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 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 5 7 2 0 0 0 0 5 15 1 0 0 0 0 6 8 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 24 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 28 1 0 0 0 0 14 17 1 0 0 0 0 15 19 2 0 0 0 0 16 28 1 0 0 0 0 17 24 1 1 0 0 0 18 22 1 0 0 0 0 18 25 2 0 0 0 0 19 29 1 0 0 0 0 20 23 1 0 0 0 0 20 26 1 1 0 0 0 21 27 2 0 0 0 0 21 29 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 1 0 0 0 24 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.19
Volume:	414.93
LogP:	3.233
LogD:	1.936
LogS:	-4.247
# Rotatable Bonds:	3
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.619
Synthetic Accessibility Score:	4.026
Fsp3:	0.5
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:	-4.805
MDCK Permeability:	2.5415123673155904e-05
Pgp-inhibitor:	0.958
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.473
30% Bioavailability (F30%):	0.38

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.084
Plasma Protein Binding (PPB):	95.88782501220703%
Volume Distribution (VD):	1.791
Pgp-substrate:	4.5564422607421875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.24
CYP1A2-substrate:	0.785
CYP2C19-inhibitor:	0.582
CYP2C19-substrate:	0.428
CYP2C9-inhibitor:	0.562
CYP2C9-substrate:	0.914
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.74
CYP3A4-inhibitor:	0.24
CYP3A4-substrate:	0.352

ADMET: Excretion

Clearance (CL):	10.886
Half-life (T1/2):	0.282

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.371
Drug-inuced Liver Injury (DILI):	0.743
AMES Toxicity:	0.251
Rat Oral Acute Toxicity:	0.704
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.455
Carcinogencity:	0.112
Eye Corrosion:	0.022
Eye Irritation:	0.357
Respiratory Toxicity:	0.839

Download Data

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

Natural Product: NPC146014

Natural Product ID:	NPC146014
*Common Name:**	Ligupersin A
IUPAC Name:	7-[[(1R,4aS,6R,8aS)-6-hydroxy-2,5,5,8a-tetramethyl-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]methoxy]chromen-2-one
Synonyms:
Standard InCHIKey:	HIQLOIOGTRDMIW-QSOCRCLWSA-N
Standard InCHI:	InChI=1S/C24H28O5/c1-14-11-18(25)22-23(2,3)20(26)9-10-24(22,4)17(14)13-28-16-7-5-15-6-8-21(27)29-19(15)12-16/h5-8,11-12,17,20,22,26H,9-10,13H2,1-4H3/t17-,20-,22-,24+/m1/s1
SMILES:	CC1=CC(=O)[C@H]2[C@@]([C@@H]1COc1ccc3c(c1)oc(=O)cc3)(C)CC[C@H](C2(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077718
PubChem CID:	11876038
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19691312]
NPO30619	Ferula gumosa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20961138]
NPO30619	Ferula gumosa	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[20961138]
NPO10996	Ferula assa-foetida	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
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	0.86	ug.mL-1	PMID[458480]
NPT742	Organism	Influenza A virus	Influenza A virus	IC90	=	1.75	ug.mL-1	PMID[458480]

☑ 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 NPC146014 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	373
0.1-0.2	1476
0.2-0.3	2923
0.3-0.4	6781
0.4-0.5	10778
0.5-0.6	5813
0.6-0.7	5620
0.7-0.8	6287
0.8-0.85	2207
0.85-0.9	407
0.9-0.95	25
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.979	High Similarity	NPC146388
0.9441	High Similarity	NPC251372
0.9437	High Similarity	NPC93640
0.9437	High Similarity	NPC20631
0.9366	High Similarity	NPC155552
0.9231	High Similarity	NPC138149
0.9155	High Similarity	NPC131198
0.9091	High Similarity	NPC307883
0.8889	High Similarity	NPC306365
0.8851	High Similarity	NPC71739
0.8844	High Similarity	NPC229916
0.88	High Similarity	NPC142863
0.875	High Similarity	NPC140133
0.875	High Similarity	NPC61499
0.8733	High Similarity	NPC286038
0.8696	High Similarity	NPC193698
0.8675	High Similarity	NPC66991
0.8671	High Similarity	NPC473022
0.8616	High Similarity	NPC469395
0.8611	High Similarity	NPC55147
0.8611	High Similarity	NPC54503
0.86	High Similarity	NPC295696
0.86	High Similarity	NPC43716
0.86	High Similarity	NPC475719
0.86	High Similarity	NPC101255
0.8599	High Similarity	NPC4950
0.8581	High Similarity	NPC472523
0.8581	High Similarity	NPC310370
0.8581	High Similarity	NPC183642
0.8571	High Similarity	NPC48671
0.8562	High Similarity	NPC103116
0.8544	High Similarity	NPC472618
0.8535	High Similarity	NPC158542
0.8533	High Similarity	NPC3732
0.8528	High Similarity	NPC472620
0.8519	High Similarity	NPC472619
0.8514	High Similarity	NPC71903
0.8509	High Similarity	NPC17274
0.8509	High Similarity	NPC120857
0.8509	High Similarity	NPC85047
0.8506	High Similarity	NPC474735
0.8506	High Similarity	NPC231668
0.8503	High Similarity	NPC471068
0.8503	High Similarity	NPC471069
0.8503	High Similarity	NPC14697
0.8493	Intermediate Similarity	NPC229128
0.8483	Intermediate Similarity	NPC31849
0.8481	Intermediate Similarity	NPC239118
0.8481	Intermediate Similarity	NPC218818
0.8477	Intermediate Similarity	NPC106126
0.8477	Intermediate Similarity	NPC108994
0.8456	Intermediate Similarity	NPC170812
0.8456	Intermediate Similarity	NPC287286
0.8452	Intermediate Similarity	NPC189773
0.8452	Intermediate Similarity	NPC209142
0.8452	Intermediate Similarity	NPC312549
0.8446	Intermediate Similarity	NPC471072
0.8446	Intermediate Similarity	NPC471070
0.8446	Intermediate Similarity	NPC319870
0.8446	Intermediate Similarity	NPC148738
0.8446	Intermediate Similarity	NPC471071
0.8446	Intermediate Similarity	NPC327612
0.8446	Intermediate Similarity	NPC73078
0.8442	Intermediate Similarity	NPC19238
0.8424	Intermediate Similarity	NPC294149
0.8418	Intermediate Similarity	NPC474611
0.8405	Intermediate Similarity	NPC54903
0.8405	Intermediate Similarity	NPC286074
0.8405	Intermediate Similarity	NPC20734
0.8395	Intermediate Similarity	NPC469394
0.8395	Intermediate Similarity	NPC125465
0.8389	Intermediate Similarity	NPC312881
0.8387	Intermediate Similarity	NPC119252
0.8378	Intermediate Similarity	NPC155963
0.8378	Intermediate Similarity	NPC309452
0.8377	Intermediate Similarity	NPC228012
0.8366	Intermediate Similarity	NPC470322
0.8366	Intermediate Similarity	NPC154217
0.8355	Intermediate Similarity	NPC169942
0.8355	Intermediate Similarity	NPC469701
0.8344	Intermediate Similarity	NPC60084
0.8333	Intermediate Similarity	NPC148945
0.8333	Intermediate Similarity	NPC152771
0.8333	Intermediate Similarity	NPC474289
0.8333	Intermediate Similarity	NPC78835
0.8333	Intermediate Similarity	NPC195357
0.8333	Intermediate Similarity	NPC204561
0.8333	Intermediate Similarity	NPC470675
0.8333	Intermediate Similarity	NPC473131
0.8333	Intermediate Similarity	NPC309512
0.8333	Intermediate Similarity	NPC305965
0.8333	Intermediate Similarity	NPC317715
0.8333	Intermediate Similarity	NPC136095
0.8333	Intermediate Similarity	NPC316960
0.8333	Intermediate Similarity	NPC290671
0.8333	Intermediate Similarity	NPC472515
0.8323	Intermediate Similarity	NPC164205
0.8323	Intermediate Similarity	NPC471114
0.8323	Intermediate Similarity	NPC212257
0.8323	Intermediate Similarity	NPC104236
0.8322	Intermediate Similarity	NPC121740
0.8322	Intermediate Similarity	NPC35501
0.8322	Intermediate Similarity	NPC47040
0.8322	Intermediate Similarity	NPC278600
0.8322	Intermediate Similarity	NPC144512
0.8322	Intermediate Similarity	NPC151946
0.8322	Intermediate Similarity	NPC137262
0.8322	Intermediate Similarity	NPC211110
0.8322	Intermediate Similarity	NPC224774
0.8322	Intermediate Similarity	NPC37428
0.8322	Intermediate Similarity	NPC258567
0.8322	Intermediate Similarity	NPC279573
0.8322	Intermediate Similarity	NPC221046
0.8312	Intermediate Similarity	NPC10990
0.8312	Intermediate Similarity	NPC477483
0.8312	Intermediate Similarity	NPC325032
0.8312	Intermediate Similarity	NPC474108
0.8312	Intermediate Similarity	NPC300988
0.8312	Intermediate Similarity	NPC177995
0.8311	Intermediate Similarity	NPC283019
0.8311	Intermediate Similarity	NPC149320
0.8311	Intermediate Similarity	NPC38099
0.8311	Intermediate Similarity	NPC128529
0.8311	Intermediate Similarity	NPC177281
0.8311	Intermediate Similarity	NPC476455
0.8311	Intermediate Similarity	NPC160727
0.8311	Intermediate Similarity	NPC283331
0.8311	Intermediate Similarity	NPC246177
0.8311	Intermediate Similarity	NPC317045
0.8311	Intermediate Similarity	NPC55615
0.8311	Intermediate Similarity	NPC266245
0.8311	Intermediate Similarity	NPC26954
0.8311	Intermediate Similarity	NPC471630
0.8301	Intermediate Similarity	NPC476055
0.8301	Intermediate Similarity	NPC196137
0.8301	Intermediate Similarity	NPC212697
0.8301	Intermediate Similarity	NPC471608
0.8301	Intermediate Similarity	NPC1886
0.8299	Intermediate Similarity	NPC180716
0.8299	Intermediate Similarity	NPC326600
0.8299	Intermediate Similarity	NPC62366
0.8299	Intermediate Similarity	NPC50896
0.8299	Intermediate Similarity	NPC204353
0.8299	Intermediate Similarity	NPC213173
0.8299	Intermediate Similarity	NPC224475
0.8291	Intermediate Similarity	NPC267242
0.8289	Intermediate Similarity	NPC277369
0.8289	Intermediate Similarity	NPC215451
0.8288	Intermediate Similarity	NPC194277
0.8288	Intermediate Similarity	NPC119985
0.8288	Intermediate Similarity	NPC175159
0.8288	Intermediate Similarity	NPC280476
0.828	Intermediate Similarity	NPC470340
0.828	Intermediate Similarity	NPC273483
0.828	Intermediate Similarity	NPC223720
0.8278	Intermediate Similarity	NPC46180
0.8276	Intermediate Similarity	NPC113098
0.8272	Intermediate Similarity	NPC476295
0.8269	Intermediate Similarity	NPC29777
0.8269	Intermediate Similarity	NPC188403
0.8269	Intermediate Similarity	NPC476185
0.8269	Intermediate Similarity	NPC158866
0.8269	Intermediate Similarity	NPC474660
0.8269	Intermediate Similarity	NPC471115
0.8269	Intermediate Similarity	NPC321896
0.8269	Intermediate Similarity	NPC225854
0.8269	Intermediate Similarity	NPC295036
0.8267	Intermediate Similarity	NPC36414
0.8264	Intermediate Similarity	NPC185066
0.8264	Intermediate Similarity	NPC469453
0.8261	Intermediate Similarity	NPC103816
0.8261	Intermediate Similarity	NPC61382
0.8261	Intermediate Similarity	NPC97812
0.8258	Intermediate Similarity	NPC240253
0.8258	Intermediate Similarity	NPC208303
0.8258	Intermediate Similarity	NPC6511
0.8258	Intermediate Similarity	NPC240622
0.8258	Intermediate Similarity	NPC266572
0.8258	Intermediate Similarity	NPC471641
0.8258	Intermediate Similarity	NPC161864
0.8258	Intermediate Similarity	NPC471642
0.8258	Intermediate Similarity	NPC39195
0.8255	Intermediate Similarity	NPC472516
0.8255	Intermediate Similarity	NPC232246
0.8255	Intermediate Similarity	NPC153818
0.8253	Intermediate Similarity	NPC469393
0.8253	Intermediate Similarity	NPC471969
0.825	Intermediate Similarity	NPC470339
0.825	Intermediate Similarity	NPC226287
0.825	Intermediate Similarity	NPC186113
0.825	Intermediate Similarity	NPC472299
0.825	Intermediate Similarity	NPC472617
0.8247	Intermediate Similarity	NPC181388
0.8247	Intermediate Similarity	NPC474161
0.8247	Intermediate Similarity	NPC476088
0.8247	Intermediate Similarity	NPC469758
0.8247	Intermediate Similarity	NPC299011
0.8243	Intermediate Similarity	NPC471625
0.8243	Intermediate Similarity	NPC472424
0.8243	Intermediate Similarity	NPC86892

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 NPC146014 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	919
0.2-0.3	1594
0.3-0.4	2512
0.4-0.5	2101
0.5-0.6	1103
0.6-0.7	404
0.7-0.8	144
0.8-0.85	40
0.85-0.9	5
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8523	High Similarity	NPD6398	Clinical (unspecified phase)
0.8523	High Similarity	NPD3750	Approved
0.8435	Intermediate Similarity	NPD3748	Approved
0.8344	Intermediate Similarity	NPD7819	Suspended
0.8276	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD5124	Phase 1
0.8231	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5844	Phase 1
0.8182	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD4628	Phase 3
0.8153	Intermediate Similarity	NPD6599	Discontinued
0.8151	Intermediate Similarity	NPD3268	Approved
0.8133	Intermediate Similarity	NPD6100	Approved
0.8133	Intermediate Similarity	NPD6099	Approved
0.8133	Intermediate Similarity	NPD2796	Approved
0.8129	Intermediate Similarity	NPD6273	Approved
0.8113	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7411	Suspended
0.8056	Intermediate Similarity	NPD2797	Approved
0.805	Intermediate Similarity	NPD6801	Discontinued
0.7974	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD7075	Discontinued
0.795	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD3267	Approved
0.7931	Intermediate Similarity	NPD3266	Approved
0.7927	Intermediate Similarity	NPD8127	Discontinued
0.7925	Intermediate Similarity	NPD4380	Phase 2
0.7908	Intermediate Similarity	NPD1549	Phase 2
0.7908	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7768	Phase 2
0.7885	Intermediate Similarity	NPD6799	Approved
0.7862	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3749	Approved
0.7853	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD5403	Approved
0.7843	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD5402	Approved
0.7834	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD5401	Approved
0.7829	Intermediate Similarity	NPD2799	Discontinued
0.7829	Intermediate Similarity	NPD1510	Phase 2
0.7826	Intermediate Similarity	NPD37	Approved
0.78	Intermediate Similarity	NPD4140	Approved
0.7791	Intermediate Similarity	NPD4966	Approved
0.7791	Intermediate Similarity	NPD4965	Approved
0.7791	Intermediate Similarity	NPD4967	Phase 2
0.7785	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD422	Phase 1
0.7778	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7229	Phase 3
0.777	Intermediate Similarity	NPD4908	Phase 1
0.7764	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD5494	Approved
0.775	Intermediate Similarity	NPD3226	Approved
0.774	Intermediate Similarity	NPD3225	Approved
0.7736	Intermediate Similarity	NPD920	Approved
0.7733	Intermediate Similarity	NPD8032	Phase 2
0.773	Intermediate Similarity	NPD3817	Phase 2
0.7722	Intermediate Similarity	NPD2534	Approved
0.7722	Intermediate Similarity	NPD2532	Approved
0.7722	Intermediate Similarity	NPD2533	Approved
0.7712	Intermediate Similarity	NPD7033	Discontinued
0.7711	Intermediate Similarity	NPD6959	Discontinued
0.7711	Intermediate Similarity	NPD7199	Phase 2
0.7692	Intermediate Similarity	NPD7003	Approved
0.7692	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1296	Phase 2
0.7662	Intermediate Similarity	NPD1551	Phase 2
0.764	Intermediate Similarity	NPD7458	Discontinued
0.7639	Intermediate Similarity	NPD1778	Approved
0.7635	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7473	Discontinued
0.7632	Intermediate Similarity	NPD6355	Discontinued
0.7628	Intermediate Similarity	NPD1652	Phase 2
0.7628	Intermediate Similarity	NPD2800	Approved
0.7628	Intermediate Similarity	NPD1243	Approved
0.7622	Intermediate Similarity	NPD4288	Approved
0.7613	Intermediate Similarity	NPD2346	Discontinued
0.761	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1934	Approved
0.7603	Intermediate Similarity	NPD1608	Approved
0.76	Intermediate Similarity	NPD8434	Phase 2
0.7597	Intermediate Similarity	NPD4308	Phase 3
0.7595	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6234	Discontinued
0.7588	Intermediate Similarity	NPD3818	Discontinued
0.7582	Intermediate Similarity	NPD1607	Approved
0.758	Intermediate Similarity	NPD8166	Discontinued
0.7566	Intermediate Similarity	NPD1240	Approved
0.7561	Intermediate Similarity	NPD1465	Phase 2
0.7561	Intermediate Similarity	NPD2801	Approved
0.756	Intermediate Similarity	NPD6232	Discontinued
0.7558	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2313	Discontinued
0.755	Intermediate Similarity	NPD6798	Discontinued
0.7544	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1610	Phase 2
0.7515	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD6005	Phase 3
0.75	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6002	Phase 3
0.75	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6004	Phase 3
0.7485	Intermediate Similarity	NPD3751	Discontinued
0.7485	Intermediate Similarity	NPD7228	Approved
0.7471	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6166	Phase 2
0.7471	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3882	Suspended
0.7468	Intermediate Similarity	NPD4110	Phase 3
0.7468	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4307	Phase 2
0.7442	Intermediate Similarity	NPD7054	Approved
0.7438	Intermediate Similarity	NPD1511	Approved
0.7436	Intermediate Similarity	NPD2935	Discontinued
0.7432	Intermediate Similarity	NPD4749	Approved
0.7417	Intermediate Similarity	NPD6832	Phase 2
0.7399	Intermediate Similarity	NPD7472	Approved
0.7399	Intermediate Similarity	NPD7074	Phase 3
0.7397	Intermediate Similarity	NPD17	Approved
0.7389	Intermediate Similarity	NPD5762	Approved
0.7389	Intermediate Similarity	NPD5763	Approved
0.7389	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1283	Approved
0.7381	Intermediate Similarity	NPD919	Approved
0.7379	Intermediate Similarity	NPD1548	Phase 1
0.7368	Intermediate Similarity	NPD4625	Phase 3
0.7362	Intermediate Similarity	NPD1653	Approved
0.7356	Intermediate Similarity	NPD5953	Discontinued
0.7356	Intermediate Similarity	NPD6797	Phase 2
0.7355	Intermediate Similarity	NPD6651	Approved
0.7353	Intermediate Similarity	NPD3787	Discontinued
0.7349	Intermediate Similarity	NPD5760	Phase 2
0.7349	Intermediate Similarity	NPD5761	Phase 2
0.7349	Intermediate Similarity	NPD8455	Phase 2
0.7346	Intermediate Similarity	NPD1512	Approved
0.7345	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4060	Phase 1
0.733	Intermediate Similarity	NPD8313	Approved
0.733	Intermediate Similarity	NPD8312	Approved
0.7329	Intermediate Similarity	NPD5691	Approved
0.7325	Intermediate Similarity	NPD4476	Approved
0.7325	Intermediate Similarity	NPD4477	Approved
0.732	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7240	Approved
0.7314	Intermediate Similarity	NPD7251	Discontinued
0.7308	Intermediate Similarity	NPD7097	Phase 1
0.7303	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2798	Approved
0.7279	Intermediate Similarity	NPD4626	Approved
0.7273	Intermediate Similarity	NPD7808	Phase 3
0.7273	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1241	Discontinued
0.7273	Intermediate Similarity	NPD6233	Phase 2
0.7267	Intermediate Similarity	NPD8651	Approved
0.7267	Intermediate Similarity	NPD7236	Approved
0.7255	Intermediate Similarity	NPD7095	Approved
0.7248	Intermediate Similarity	NPD3972	Approved
0.7248	Intermediate Similarity	NPD9717	Approved
0.7241	Intermediate Similarity	NPD7286	Phase 2
0.7238	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2424	Discontinued
0.7226	Intermediate Similarity	NPD1613	Approved
0.7226	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2979	Phase 3
0.7222	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6971	Discontinued
0.7219	Intermediate Similarity	NPD1203	Approved
0.7216	Intermediate Similarity	NPD6764	Approved
0.7216	Intermediate Similarity	NPD6765	Approved
0.7215	Intermediate Similarity	NPD2438	Suspended
0.7212	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD5585	Approved
0.7208	Intermediate Similarity	NPD3764	Approved
0.719	Intermediate Similarity	NPD2614	Approved
0.7188	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7177	Discontinued
0.7181	Intermediate Similarity	NPD1281	Approved
0.7179	Intermediate Similarity	NPD5735	Approved
0.7179	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD230	Phase 1
0.7169	Intermediate Similarity	NPD7028	Phase 2
0.7161	Intermediate Similarity	NPD6663	Approved
0.716	Intermediate Similarity	NPD6667	Approved
0.716	Intermediate Similarity	NPD6666	Approved
0.7152	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5710	Approved
0.7151	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD1894	Discontinued
0.7134	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4534	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