NPASS Compound

Structure

NPC475974 OpenBabel07101718202D 22 23 0 0 1 0 0 0 0 0999 V2000 -1.5731 -0.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 0.8660 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 1.0000 3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.7321 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0981 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 4.6980 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5731 3.9392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2588 -0.9659 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 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 9 1 0 0 0 0 4 11 1 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 10 1 0 0 0 0 6 15 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 1 1 1 0 0 0 9 22 1 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 13 19 2 0 0 0 0 14 16 2 0 0 0 0 14 20 1 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.13
Volume:	307.738
LogP:	2.484
LogD:	1.894
LogS:	-2.912
# Rotatable Bonds:	0
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.63
Synthetic Accessibility Score:	3.946
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:	-4.91
MDCK Permeability:	2.7910056815017015e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.813
Human Intestinal Absorption (HIA):	0.044
20% Bioavailability (F20%):	0.174
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.323
Plasma Protein Binding (PPB):	49.77715301513672%
Volume Distribution (VD):	0.555
Pgp-substrate:	49.00259017944336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.516
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.095
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.138
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.3
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.413
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	16.123
Half-life (T1/2):	0.878

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.709
AMES Toxicity:	0.091
Rat Oral Acute Toxicity:	0.137
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.406
Carcinogencity:	0.239
Eye Corrosion:	0.012
Eye Irritation:	0.066
Respiratory Toxicity:	0.748

Download Data

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

Natural Product: NPC475974

Natural Product ID:	NPC475974
*Common Name:**	11-Hydroxycurvularin
IUPAC Name:	(5S)-9,13,15-trihydroxy-5-methyl-4-oxabicyclo[10.4.0]hexadeca-1(16),12,14-triene-3,11-dione
Synonyms:	11-Hydroxycurvularin
Standard InCHIKey:	QPBNFQKLPIXNFL-FTNKSUMCSA-N
Standard InCHI:	InChI=1S/C16H20O6/c1-9-3-2-4-11(17)7-13(19)16-10(6-15(21)22-9)5-12(18)8-14(16)20/h5,8-9,11,17-18,20H,2-4,6-7H2,1H3/t9-,11?/m0/s1
SMILES:	OC1CCC[C@H](C)OC(=O)Cc2c(C(=O)C1)c(O)cc(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520015
PubChem CID:	11209020
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	rhizosphere	Sonoran desert	n.a.	PMID[15620238]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17542490]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17564467]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053517]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21366228]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	healthy leaf of Ginkgo biloba	campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	isolated from the sponge Xestospongia testudinaria	n.a.	n.a.	PMID[22225637]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	Isolated from a sandy-loam soil sample	50 m inland from Waikiki Beach, Honolulu, Hawaii	2010-JUL	PMID[22400916]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22703109]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23527875]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24050204]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25001296]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25581396]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26273902]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31012585]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33305943]

☑ 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	5

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	2100.0	nM	PMID[474244]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2000.0	nM	PMID[474244]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	4100.0	nM	PMID[474244]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	3300.0	nM	PMID[474244]
NPT27	Others	Unspecified		IC50	=	11600.0	nM	PMID[474244]

☑ 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 NPC475974 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	303
0.1-0.2	1281
0.2-0.3	3255
0.3-0.4	7829
0.4-0.5	11430
0.5-0.6	4312
0.6-0.7	7351
0.7-0.8	5968
0.8-0.85	723
0.85-0.9	177
0.9-0.95	55
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9924	High Similarity	NPC149372
0.9924	High Similarity	NPC178467
0.9924	High Similarity	NPC474771
0.9924	High Similarity	NPC474849
0.9924	High Similarity	NPC65837
0.9774	High Similarity	NPC474655
0.9699	High Similarity	NPC472403
0.9699	High Similarity	NPC177307
0.9699	High Similarity	NPC9121
0.963	High Similarity	NPC478217
0.963	High Similarity	NPC313123
0.9552	High Similarity	NPC212693
0.9552	High Similarity	NPC94248
0.9552	High Similarity	NPC191835
0.9489	High Similarity	NPC354984
0.9489	High Similarity	NPC478202
0.9485	High Similarity	NPC478201
0.9485	High Similarity	NPC472035
0.9478	High Similarity	NPC70380
0.9407	High Similarity	NPC478200
0.9407	High Similarity	NPC33144
0.9353	High Similarity	NPC257558
0.9338	High Similarity	NPC139634
0.9338	High Similarity	NPC105456
0.9333	High Similarity	NPC71256
0.9281	High Similarity	NPC126882
0.9281	High Similarity	NPC478203
0.9281	High Similarity	NPC210966
0.927	High Similarity	NPC158472
0.9265	High Similarity	NPC472602
0.9237	High Similarity	NPC41263
0.922	High Similarity	NPC472036
0.9214	High Similarity	NPC472034
0.9209	High Similarity	NPC51106
0.9209	High Similarity	NPC472006
0.9203	High Similarity	NPC1704
0.9203	High Similarity	NPC472603
0.9203	High Similarity	NPC472604
0.9203	High Similarity	NPC67650
0.9203	High Similarity	NPC472605
0.9203	High Similarity	NPC158634
0.9203	High Similarity	NPC244923
0.9203	High Similarity	NPC53649
0.9197	High Similarity	NPC268052
0.9197	High Similarity	NPC32360
0.9179	High Similarity	NPC153783
0.9155	High Similarity	NPC471642
0.9155	High Similarity	NPC471641
0.9155	High Similarity	NPC240622
0.9155	High Similarity	NPC240253
0.9149	High Similarity	NPC472033
0.9137	High Similarity	NPC474385
0.913	High Similarity	NPC472601
0.913	High Similarity	NPC472600
0.9118	High Similarity	NPC235115
0.9098	High Similarity	NPC17840
0.9098	High Similarity	NPC247477
0.9078	High Similarity	NPC83272
0.9071	High Similarity	NPC159721
0.9071	High Similarity	NPC469542
0.9071	High Similarity	NPC471731
0.9058	High Similarity	NPC92655
0.9051	High Similarity	NPC194579
0.9037	High Similarity	NPC48036
0.9034	High Similarity	NPC213224
0.903	High Similarity	NPC189823
0.903	High Similarity	NPC219892
0.9014	High Similarity	NPC473023
0.9014	High Similarity	NPC107625
0.9008	High Similarity	NPC201728
0.9008	High Similarity	NPC262671
0.9008	High Similarity	NPC477454
0.9007	High Similarity	NPC280404
0.9007	High Similarity	NPC151607
0.9007	High Similarity	NPC210425
0.9007	High Similarity	NPC277426
0.9007	High Similarity	NPC86373
0.9007	High Similarity	NPC42540
0.9	High Similarity	NPC471733
0.9	High Similarity	NPC469579
0.8973	High Similarity	NPC55092
0.8971	High Similarity	NPC474394
0.8971	High Similarity	NPC474097
0.8951	High Similarity	NPC210320
0.8951	High Similarity	NPC14098
0.8944	High Similarity	NPC312789
0.8939	High Similarity	NPC473691
0.8936	High Similarity	NPC472610
0.8929	High Similarity	NPC475730
0.8929	High Similarity	NPC37530
0.8921	High Similarity	NPC88269
0.8921	High Similarity	NPC52358
0.8913	High Similarity	NPC135837
0.8905	High Similarity	NPC142027
0.8905	High Similarity	NPC27407
0.8905	High Similarity	NPC278375
0.8897	High Similarity	NPC37299
0.8897	High Similarity	NPC56204
0.8897	High Similarity	NPC180261
0.8897	High Similarity	NPC43627
0.8889	High Similarity	NPC215711
0.8889	High Similarity	NPC73411
0.8889	High Similarity	NPC221352
0.8889	High Similarity	NPC153417
0.8857	High Similarity	NPC155205
0.8857	High Similarity	NPC99441
0.8844	High Similarity	NPC275837
0.8841	High Similarity	NPC158481
0.8832	High Similarity	NPC474519
0.8832	High Similarity	NPC175943
0.8824	High Similarity	NPC476389
0.8819	High Similarity	NPC471734
0.8815	High Similarity	NPC147757
0.8811	High Similarity	NPC473692
0.8803	High Similarity	NPC471639
0.8803	High Similarity	NPC471643
0.8786	High Similarity	NPC275356
0.8786	High Similarity	NPC247409
0.8786	High Similarity	NPC162939
0.8768	High Similarity	NPC290803
0.8768	High Similarity	NPC182496
0.8768	High Similarity	NPC180905
0.8767	High Similarity	NPC60413
0.8767	High Similarity	NPC469670
0.8767	High Similarity	NPC469619
0.875	High Similarity	NPC471735
0.8741	High Similarity	NPC92624
0.8732	High Similarity	NPC82913
0.8732	High Similarity	NPC471644
0.8732	High Similarity	NPC250755
0.8732	High Similarity	NPC471640
0.8722	High Similarity	NPC167055
0.8722	High Similarity	NPC240744
0.8714	High Similarity	NPC221104
0.8707	High Similarity	NPC200773
0.8707	High Similarity	NPC70016
0.8707	High Similarity	NPC240768
0.8707	High Similarity	NPC215921
0.8705	High Similarity	NPC475955
0.8705	High Similarity	NPC474726
0.8705	High Similarity	NPC50455
0.8705	High Similarity	NPC118919
0.8705	High Similarity	NPC291454
0.8699	High Similarity	NPC237440
0.8699	High Similarity	NPC77325
0.8699	High Similarity	NPC270160
0.8699	High Similarity	NPC6923
0.8699	High Similarity	NPC476684
0.8699	High Similarity	NPC4423
0.869	High Similarity	NPC166583
0.869	High Similarity	NPC53362
0.8686	High Similarity	NPC478190
0.8681	High Similarity	NPC134621
0.8676	High Similarity	NPC259942
0.8662	High Similarity	NPC470842
0.8662	High Similarity	NPC307990
0.8662	High Similarity	NPC16455
0.8662	High Similarity	NPC90411
0.8658	High Similarity	NPC99381
0.8649	High Similarity	NPC478224
0.8643	High Similarity	NPC261292
0.8643	High Similarity	NPC301915
0.8639	High Similarity	NPC472891
0.8626	High Similarity	NPC149246
0.8621	High Similarity	NPC237208
0.8613	High Similarity	NPC470831
0.8613	High Similarity	NPC214702
0.8611	High Similarity	NPC95123
0.8611	High Similarity	NPC66404
0.8601	High Similarity	NPC474961
0.8601	High Similarity	NPC96692
0.8601	High Similarity	NPC135524
0.8593	High Similarity	NPC209959
0.8592	High Similarity	NPC165172
0.8591	High Similarity	NPC470102
0.8581	High Similarity	NPC91809
0.8571	High Similarity	NPC84142
0.8571	High Similarity	NPC472599
0.8562	High Similarity	NPC8817
0.8561	High Similarity	NPC282780
0.8561	High Similarity	NPC166480
0.8552	High Similarity	NPC29577
0.8543	High Similarity	NPC472404
0.854	High Similarity	NPC62219
0.8533	High Similarity	NPC79998
0.8533	High Similarity	NPC170189
0.8533	High Similarity	NPC69043
0.8533	High Similarity	NPC478230
0.8533	High Similarity	NPC16082
0.8533	High Similarity	NPC82592
0.8533	High Similarity	NPC208173
0.8531	High Similarity	NPC305845
0.8531	High Similarity	NPC204045
0.8529	High Similarity	NPC95537
0.8523	High Similarity	NPC167903
0.8523	High Similarity	NPC184284
0.8523	High Similarity	NPC115249
0.8523	High Similarity	NPC273483
0.8523	High Similarity	NPC76041
0.8521	High Similarity	NPC471819

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 NPC475974 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	892
0.2-0.3	1810
0.3-0.4	2654
0.4-0.5	1988
0.5-0.6	1071
0.6-0.7	360
0.7-0.8	112
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8652	High Similarity	NPD970	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD2533	Approved
0.8425	Intermediate Similarity	NPD2532	Approved
0.8425	Intermediate Similarity	NPD2534	Approved
0.8224	Intermediate Similarity	NPD7819	Suspended
0.8182	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7390	Discontinued
0.7974	Intermediate Similarity	NPD7411	Suspended
0.7972	Intermediate Similarity	NPD230	Phase 1
0.7945	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD1510	Phase 2
0.7902	Intermediate Similarity	NPD1240	Approved
0.7902	Intermediate Similarity	NPD943	Approved
0.7891	Intermediate Similarity	NPD1549	Phase 2
0.7871	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD7075	Discontinued
0.7815	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1934	Approved
0.7799	Intermediate Similarity	NPD6959	Discontinued
0.7793	Intermediate Similarity	NPD1607	Approved
0.7792	Intermediate Similarity	NPD4380	Phase 2
0.7785	Intermediate Similarity	NPD3750	Approved
0.7785	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD5408	Approved
0.7755	Intermediate Similarity	NPD5406	Approved
0.7755	Intermediate Similarity	NPD2796	Approved
0.7755	Intermediate Similarity	NPD5404	Approved
0.7755	Intermediate Similarity	NPD5405	Approved
0.775	Intermediate Similarity	NPD6232	Discontinued
0.7748	Intermediate Similarity	NPD6799	Approved
0.7721	Intermediate Similarity	NPD9545	Approved
0.7716	Intermediate Similarity	NPD7473	Discontinued
0.7692	Intermediate Similarity	NPD6801	Discontinued
0.7677	Intermediate Similarity	NPD6599	Discontinued
0.764	Intermediate Similarity	NPD5711	Approved
0.764	Intermediate Similarity	NPD5710	Approved
0.7635	Intermediate Similarity	NPD2935	Discontinued
0.7626	Intermediate Similarity	NPD1201	Approved
0.761	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD3749	Approved
0.76	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD3817	Phase 2
0.7574	Intermediate Similarity	NPD9493	Approved
0.7571	Intermediate Similarity	NPD9269	Phase 2
0.7547	Intermediate Similarity	NPD3882	Suspended
0.7547	Intermediate Similarity	NPD7768	Phase 2
0.7547	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6166	Phase 2
0.7536	Intermediate Similarity	NPD9268	Approved
0.7535	Intermediate Similarity	NPD1470	Approved
0.7532	Intermediate Similarity	NPD2801	Approved
0.7517	Intermediate Similarity	NPD1551	Phase 2
0.7517	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1511	Approved
0.7515	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD3226	Approved
0.7483	Intermediate Similarity	NPD2800	Approved
0.747	Intermediate Similarity	NPD7074	Phase 3
0.7468	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD3818	Discontinued
0.745	Intermediate Similarity	NPD3748	Approved
0.7445	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4628	Phase 3
0.7432	Intermediate Similarity	NPD6651	Approved
0.7419	Intermediate Similarity	NPD1512	Approved
0.7413	Intermediate Similarity	NPD1164	Approved
0.741	Intermediate Similarity	NPD7054	Approved
0.7397	Intermediate Similarity	NPD3764	Approved
0.7375	Intermediate Similarity	NPD5402	Approved
0.7372	Intermediate Similarity	NPD5403	Approved
0.7368	Intermediate Similarity	NPD9266	Approved
0.7368	Intermediate Similarity	NPD74	Approved
0.7368	Intermediate Similarity	NPD1243	Approved
0.7365	Intermediate Similarity	NPD7472	Approved
0.7337	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6797	Phase 2
0.732	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD9267	Approved
0.7293	Intermediate Similarity	NPD9263	Approved
0.7293	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD9264	Approved
0.7286	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6099	Approved
0.7285	Intermediate Similarity	NPD6100	Approved
0.7278	Intermediate Similarity	NPD7251	Discontinued
0.7278	Intermediate Similarity	NPD6559	Discontinued
0.7261	Intermediate Similarity	NPD920	Approved
0.7244	Intermediate Similarity	NPD5401	Approved
0.7235	Intermediate Similarity	NPD7808	Phase 3
0.7226	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5953	Discontinued
0.7219	Intermediate Similarity	NPD2799	Discontinued
0.7205	Intermediate Similarity	NPD1465	Phase 2
0.7203	Intermediate Similarity	NPD9717	Approved
0.72	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5494	Approved
0.7168	Intermediate Similarity	NPD8150	Discontinued
0.7162	Intermediate Similarity	NPD3268	Approved
0.7161	Intermediate Similarity	NPD6190	Approved
0.7143	Intermediate Similarity	NPD2654	Approved
0.7143	Intermediate Similarity	NPD37	Approved
0.7134	Intermediate Similarity	NPD919	Approved
0.7134	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2346	Discontinued
0.7117	Intermediate Similarity	NPD4965	Approved
0.7117	Intermediate Similarity	NPD4967	Phase 2
0.7117	Intermediate Similarity	NPD4966	Approved
0.7114	Intermediate Similarity	NPD6663	Approved
0.7105	Intermediate Similarity	NPD7033	Discontinued
0.7101	Intermediate Similarity	NPD7286	Phase 2
0.7075	Intermediate Similarity	NPD5736	Approved
0.7063	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4750	Phase 3
0.7055	Intermediate Similarity	NPD1203	Approved
0.705	Intermediate Similarity	NPD9281	Approved
0.7048	Intermediate Similarity	NPD7199	Phase 2
0.7047	Intermediate Similarity	NPD411	Approved
0.7045	Intermediate Similarity	NPD940	Approved
0.7045	Intermediate Similarity	NPD846	Approved
0.7044	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6234	Discontinued
0.7027	Intermediate Similarity	NPD6832	Phase 2
0.702	Intermediate Similarity	NPD447	Suspended
0.7014	Intermediate Similarity	NPD422	Phase 1
0.7013	Intermediate Similarity	NPD2344	Approved
0.7	Intermediate Similarity	NPD520	Approved
0.6993	Remote Similarity	NPD4626	Approved
0.6992	Remote Similarity	NPD9261	Approved
0.6966	Remote Similarity	NPD1608	Approved
0.6946	Remote Similarity	NPD1247	Approved
0.6933	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5691	Approved
0.6908	Remote Similarity	NPD5124	Phase 1
0.6908	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7229	Phase 3
0.6899	Remote Similarity	NPD3300	Phase 2
0.6898	Remote Similarity	NPD8151	Discontinued
0.6897	Remote Similarity	NPD8312	Approved
0.6897	Remote Similarity	NPD8313	Approved
0.6893	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2798	Approved
0.6892	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5048	Discontinued
0.6883	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD8166	Discontinued
0.6879	Remote Similarity	NPD3400	Discontinued
0.6875	Remote Similarity	NPD6273	Approved
0.6875	Remote Similarity	NPD3019	Approved
0.6875	Remote Similarity	NPD2932	Approved
0.6864	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3926	Phase 2
0.6855	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4288	Approved
0.6842	Remote Similarity	NPD7228	Approved
0.6842	Remote Similarity	NPD3751	Discontinued
0.6835	Remote Similarity	NPD2309	Approved
0.6833	Remote Similarity	NPD6535	Approved
0.6833	Remote Similarity	NPD6534	Approved
0.6831	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3267	Approved
0.6824	Remote Similarity	NPD3266	Approved
0.6824	Remote Similarity	NPD2797	Approved
0.6821	Remote Similarity	NPD2313	Discontinued
0.6811	Remote Similarity	NPD7435	Discontinued
0.6805	Remote Similarity	NPD3787	Discontinued
0.68	Remote Similarity	NPD4908	Phase 1
0.6795	Remote Similarity	NPD6004	Phase 3
0.6795	Remote Similarity	NPD6005	Phase 3
0.6795	Remote Similarity	NPD6002	Phase 3
0.6795	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8434	Phase 2
0.6779	Remote Similarity	NPD1019	Discontinued
0.6779	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8320	Phase 1
0.6774	Remote Similarity	NPD8319	Approved
0.6772	Remote Similarity	NPD7003	Approved
0.6763	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1778	Approved
0.6759	Remote Similarity	NPD17	Approved
0.6758	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1283	Approved
0.6755	Remote Similarity	NPD3027	Phase 3
0.6748	Remote Similarity	NPD7458	Discontinued
0.6747	Remote Similarity	NPD5353	Approved
0.6744	Remote Similarity	NPD7893	Clinical (unspecified phase)

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