NPASS Compound

Structure

CID322903 OpenBabel06191716172D 31 33 0 0 1 0 0 0 0 0999 V2000 -10.9272 0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2461 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5650 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8839 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8406 2.4265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8406 1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0866 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5217 2.4265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3622 1.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4055 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7244 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5217 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6811 -2.9118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2461 0.4853 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.5650 0.4853 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.8839 0.4853 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6811 1.9412 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8406 -2.4265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5217 0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3622 0.9706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6811 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0433 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8406 0.4853 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6811 0.9706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8406 -0.4853 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6811 -3.8824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6811 -1.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0433 1.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2028 0.4853 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 8 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 19 2 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 21 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 13 20 2 0 0 0 0 13 22 1 0 0 0 0 14 19 1 0 0 0 0 14 27 1 0 0 0 0 17 23 1 0 0 0 0 18 25 1 6 0 0 0 20 21 1 0 0 0 0 20 25 1 0 0 0 0 21 30 1 6 0 0 0 22 26 1 0 0 0 0 22 28 2 0 0 0 0 23 29 2 0 0 0 0 23 30 1 0 0 0 0 24 25 1 1 0 0 0 24 26 1 0 0 0 0 24 31 1 0 0 0 0 25 7 1 6 0 0 0 26 19 1 6 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.29
Volume:	465.988
LogP:	4.505
LogD:	4.652
LogS:	-5.203
# Rotatable Bonds:	10
TPSA:	76.13
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.316
Synthetic Accessibility Score:	5.255
Fsp3:	0.769
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.834
MDCK Permeability:	2.4550801754230633e-05
Pgp-inhibitor:	0.868
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.087
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.908
Plasma Protein Binding (PPB):	56.51000213623047%
Volume Distribution (VD):	0.939
Pgp-substrate:	52.986778259277344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.18
CYP2C19-inhibitor:	0.177
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.273
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.878
CYP3A4-substrate:	0.779

ADMET: Excretion

Clearance (CL):	8.639
Half-life (T1/2):	0.888

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.249
Drug-inuced Liver Injury (DILI):	0.63
AMES Toxicity:	0.728
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.772
Skin Sensitization:	0.968
Carcinogencity:	0.533
Eye Corrosion:	0.864
Eye Irritation:	0.879
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC322903

Natural Product ID:	NPC322903
*Common Name:**	Xylarenone C
IUPAC Name:	[(1aR,4R,7S,7aR,7bR)-1a-(3-hydroxyprop-1-en-2-yl)-7,7a-dimethyl-2-oxo-5,6,7,7b-tetrahydro-4H-naphtho[1,2-b]oxiren-4-yl] 2,4,6-trimethyloctanoate
Synonyms:	Xylarenone C
Standard InCHIKey:	CVLZBOJHINAXHY-VAXWEKKDSA-N
Standard InCHI:	InChI=1S/C26H40O5/c1-8-15(2)11-16(3)12-17(4)23(29)30-21-10-9-18(5)25(7)20(21)13-22(28)26(19(6)14-27)24(25)31-26/h13,15-18,21,24,27H,6,8-12,14H2,1-5,7H3/t15?,16?,17?,18-,21+,24+,25+,26-/m0/s1
SMILES:	CCC(C)CC(C)CC(C)C(=O)O[C@@H]1CC[C@H](C)[C@]2(C)C1=CC(=O)[C@@]1(C(=C)CO)[C@@H]2O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813183
PubChem CID:	53344593
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO30643	Endophytic fungi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21510613]
NPO30643	Endophytic fungi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21954864]
NPO30643	Endophytic fungi	n.a.	n.a.	n.a.	n.a.	Costa Rican	n.a.	PMID[22910038]
NPO40058	Camarops sp.	Species	Boliniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24588269]

☑ 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	6
Others	1

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT620	Individual Protein	Subtilisin/kexin type 7	Homo sapiens	IC50	=	462.0	nM	PMID[528744]
NPT1634	Individual Protein	Myeloperoxidase	Homo sapiens	IC50	>	100000.0	nM	PMID[528745]
NPT2	Others	Unspecified		IC50	=	288.0	nM	PMID[528744]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[528745]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	>	98.0	%	PMID[528745]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6130.0	nM	PMID[528745]

☑ 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 NPC322903 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	230
0.1-0.2	1343
0.2-0.3	4057
0.3-0.4	7013
0.4-0.5	13769
0.5-0.6	7986
0.6-0.7	6182
0.7-0.8	1951
0.8-0.85	148
0.85-0.9	13
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC317107
0.9612	High Similarity	NPC317687
0.9394	High Similarity	NPC207885
0.92	High Similarity	NPC112613
0.9	High Similarity	NPC264378
0.8972	High Similarity	NPC159333
0.89	High Similarity	NPC471916
0.88	High Similarity	NPC94337
0.8774	High Similarity	NPC87335
0.8679	High Similarity	NPC151393
0.8654	High Similarity	NPC131366
0.8558	High Similarity	NPC137430
0.8519	High Similarity	NPC115257
0.8519	High Similarity	NPC161816
0.8505	High Similarity	NPC476479
0.8476	Intermediate Similarity	NPC99266
0.8476	Intermediate Similarity	NPC8196
0.8468	Intermediate Similarity	NPC270478
0.8431	Intermediate Similarity	NPC202833
0.8426	Intermediate Similarity	NPC475922
0.8421	Intermediate Similarity	NPC67569
0.8411	Intermediate Similarity	NPC143609
0.8393	Intermediate Similarity	NPC469684
0.8393	Intermediate Similarity	NPC243065
0.8381	Intermediate Similarity	NPC39996
0.8381	Intermediate Similarity	NPC476081
0.8381	Intermediate Similarity	NPC478176
0.8364	Intermediate Similarity	NPC473877
0.835	Intermediate Similarity	NPC287668
0.8348	Intermediate Similarity	NPC470265
0.8348	Intermediate Similarity	NPC23786
0.8333	Intermediate Similarity	NPC14862
0.8333	Intermediate Similarity	NPC233379
0.8333	Intermediate Similarity	NPC472439
0.8333	Intermediate Similarity	NPC474664
0.8333	Intermediate Similarity	NPC469916
0.8318	Intermediate Similarity	NPC1679
0.8318	Intermediate Similarity	NPC284365
0.8318	Intermediate Similarity	NPC123726
0.8318	Intermediate Similarity	NPC475802
0.8318	Intermediate Similarity	NPC111952
0.8302	Intermediate Similarity	NPC95899
0.8302	Intermediate Similarity	NPC159533
0.8302	Intermediate Similarity	NPC478057
0.8288	Intermediate Similarity	NPC477126
0.8288	Intermediate Similarity	NPC122056
0.8288	Intermediate Similarity	NPC71889
0.8286	Intermediate Similarity	NPC97435
0.8276	Intermediate Similarity	NPC67251
0.8276	Intermediate Similarity	NPC469789
0.8269	Intermediate Similarity	NPC316598
0.8257	Intermediate Similarity	NPC15218
0.825	Intermediate Similarity	NPC476193
0.8246	Intermediate Similarity	NPC472933
0.8241	Intermediate Similarity	NPC324327
0.8241	Intermediate Similarity	NPC474421
0.8241	Intermediate Similarity	NPC266514
0.8241	Intermediate Similarity	NPC187435
0.8241	Intermediate Similarity	NPC72813
0.8241	Intermediate Similarity	NPC326994
0.8241	Intermediate Similarity	NPC67321
0.8241	Intermediate Similarity	NPC194620
0.8224	Intermediate Similarity	NPC146731
0.8224	Intermediate Similarity	NPC296950
0.8214	Intermediate Similarity	NPC474872
0.8214	Intermediate Similarity	NPC238667
0.8208	Intermediate Similarity	NPC469606
0.8208	Intermediate Similarity	NPC273005
0.8208	Intermediate Similarity	NPC31058
0.8205	Intermediate Similarity	NPC476729
0.8205	Intermediate Similarity	NPC470922
0.8198	Intermediate Similarity	NPC269530
0.8198	Intermediate Similarity	NPC90952
0.8198	Intermediate Similarity	NPC277769
0.819	Intermediate Similarity	NPC469551
0.819	Intermediate Similarity	NPC472972
0.819	Intermediate Similarity	NPC54705
0.819	Intermediate Similarity	NPC474718
0.8182	Intermediate Similarity	NPC5103
0.8165	Intermediate Similarity	NPC327286
0.8165	Intermediate Similarity	NPC89171
0.8165	Intermediate Similarity	NPC169888
0.8165	Intermediate Similarity	NPC55972
0.8165	Intermediate Similarity	NPC476802
0.8165	Intermediate Similarity	NPC102843
0.8158	Intermediate Similarity	NPC240509
0.8158	Intermediate Similarity	NPC50774
0.8158	Intermediate Similarity	NPC251310
0.8158	Intermediate Similarity	NPC709
0.8158	Intermediate Similarity	NPC186525
0.8155	Intermediate Similarity	NPC471786
0.8155	Intermediate Similarity	NPC37603
0.8151	Intermediate Similarity	NPC476859
0.8148	Intermediate Similarity	NPC16313
0.8148	Intermediate Similarity	NPC9303
0.8148	Intermediate Similarity	NPC472645
0.8142	Intermediate Similarity	NPC476711
0.8142	Intermediate Similarity	NPC476710
0.8142	Intermediate Similarity	NPC474333
0.8137	Intermediate Similarity	NPC99653
0.8136	Intermediate Similarity	NPC293112
0.8131	Intermediate Similarity	NPC120321
0.8131	Intermediate Similarity	NPC474166
0.8131	Intermediate Similarity	NPC19239
0.8125	Intermediate Similarity	NPC469454
0.8125	Intermediate Similarity	NPC469463
0.8125	Intermediate Similarity	NPC469496
0.8125	Intermediate Similarity	NPC472926
0.8125	Intermediate Similarity	NPC25909
0.812	Intermediate Similarity	NPC265557
0.812	Intermediate Similarity	NPC18945
0.812	Intermediate Similarity	NPC472399
0.812	Intermediate Similarity	NPC91693
0.812	Intermediate Similarity	NPC105926
0.812	Intermediate Similarity	NPC120724
0.8119	Intermediate Similarity	NPC232202
0.8113	Intermediate Similarity	NPC472643
0.8108	Intermediate Similarity	NPC158523
0.8108	Intermediate Similarity	NPC96739
0.8108	Intermediate Similarity	NPC474871
0.8108	Intermediate Similarity	NPC475937
0.8108	Intermediate Similarity	NPC324683
0.8108	Intermediate Similarity	NPC174471
0.8108	Intermediate Similarity	NPC260786
0.8095	Intermediate Similarity	NPC222303
0.8095	Intermediate Similarity	NPC216478
0.8091	Intermediate Similarity	NPC42662
0.8087	Intermediate Similarity	NPC476960
0.8083	Intermediate Similarity	NPC476854
0.8083	Intermediate Similarity	NPC476851
0.8081	Intermediate Similarity	NPC202394
0.8073	Intermediate Similarity	NPC475587
0.8073	Intermediate Similarity	NPC474716
0.8073	Intermediate Similarity	NPC475510
0.8073	Intermediate Similarity	NPC112780
0.807	Intermediate Similarity	NPC183580
0.807	Intermediate Similarity	NPC239273
0.807	Intermediate Similarity	NPC20302
0.807	Intermediate Similarity	NPC286528
0.807	Intermediate Similarity	NPC98249
0.807	Intermediate Similarity	NPC312824
0.807	Intermediate Similarity	NPC167606
0.807	Intermediate Similarity	NPC474518
0.807	Intermediate Similarity	NPC470493
0.807	Intermediate Similarity	NPC53396
0.807	Intermediate Similarity	NPC472927
0.807	Intermediate Similarity	NPC470492
0.807	Intermediate Similarity	NPC296822
0.807	Intermediate Similarity	NPC140055
0.807	Intermediate Similarity	NPC476712
0.807	Intermediate Similarity	NPC476713
0.807	Intermediate Similarity	NPC472934
0.8058	Intermediate Similarity	NPC470697
0.8056	Intermediate Similarity	NPC118911
0.8056	Intermediate Similarity	NPC220964
0.8056	Intermediate Similarity	NPC258532
0.8056	Intermediate Similarity	NPC475676
0.8051	Intermediate Similarity	NPC172154
0.8051	Intermediate Similarity	NPC8369
0.8051	Intermediate Similarity	NPC24651
0.8051	Intermediate Similarity	NPC81736
0.8051	Intermediate Similarity	NPC8374
0.8039	Intermediate Similarity	NPC473944
0.8039	Intermediate Similarity	NPC124374
0.8037	Intermediate Similarity	NPC475038
0.8037	Intermediate Similarity	NPC165250
0.8037	Intermediate Similarity	NPC109195
0.8036	Intermediate Similarity	NPC151216
0.8036	Intermediate Similarity	NPC101825
0.8036	Intermediate Similarity	NPC4573
0.8036	Intermediate Similarity	NPC215643
0.8036	Intermediate Similarity	NPC221511
0.8036	Intermediate Similarity	NPC170212
0.8036	Intermediate Similarity	NPC265499
0.8036	Intermediate Similarity	NPC17138
0.8036	Intermediate Similarity	NPC89227
0.8036	Intermediate Similarity	NPC475391
0.8034	Intermediate Similarity	NPC312833
0.8019	Intermediate Similarity	NPC472644
0.8019	Intermediate Similarity	NPC47024
0.8019	Intermediate Similarity	NPC476299
0.8019	Intermediate Similarity	NPC474012
0.8018	Intermediate Similarity	NPC89408
0.8018	Intermediate Similarity	NPC235014
0.8018	Intermediate Similarity	NPC153036
0.8017	Intermediate Similarity	NPC185876
0.8017	Intermediate Similarity	NPC19336
0.8017	Intermediate Similarity	NPC471128
0.8017	Intermediate Similarity	NPC474370
0.8017	Intermediate Similarity	NPC476852
0.8017	Intermediate Similarity	NPC157252
0.8017	Intermediate Similarity	NPC145182
0.8017	Intermediate Similarity	NPC476855
0.8017	Intermediate Similarity	NPC471126
0.8017	Intermediate Similarity	NPC17938
0.8	Intermediate Similarity	NPC21326
0.8	Intermediate Similarity	NPC189075
0.8	Intermediate Similarity	NPC472760
0.8	Intermediate Similarity	NPC473939
0.8	Intermediate Similarity	NPC275539

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 NPC322903 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	1699
0.2-0.3	3533
0.3-0.4	2298
0.4-0.5	932
0.5-0.6	284
0.6-0.7	180
0.7-0.8	28
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.807	Intermediate Similarity	NPD7115	Discovery
0.7699	Intermediate Similarity	NPD6371	Approved
0.7685	Intermediate Similarity	NPD7640	Approved
0.7685	Intermediate Similarity	NPD7639	Approved
0.7658	Intermediate Similarity	NPD7128	Approved
0.7658	Intermediate Similarity	NPD6675	Approved
0.7658	Intermediate Similarity	NPD5739	Approved
0.7658	Intermediate Similarity	NPD6402	Approved
0.7619	Intermediate Similarity	NPD5779	Approved
0.7619	Intermediate Similarity	NPD5778	Approved
0.7611	Intermediate Similarity	NPD6372	Approved
0.7611	Intermediate Similarity	NPD6373	Approved
0.7611	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD46	Approved
0.7596	Intermediate Similarity	NPD6698	Approved
0.7593	Intermediate Similarity	NPD7638	Approved
0.7593	Intermediate Similarity	NPD4225	Approved
0.7544	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD6881	Approved
0.7522	Intermediate Similarity	NPD6899	Approved
0.7522	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD6084	Phase 2
0.7478	Intermediate Similarity	NPD6650	Approved
0.7478	Intermediate Similarity	NPD6649	Approved
0.7455	Intermediate Similarity	NPD5344	Discontinued
0.7434	Intermediate Similarity	NPD5701	Approved
0.7434	Intermediate Similarity	NPD5697	Approved
0.7417	Intermediate Similarity	NPD6319	Approved
0.7391	Intermediate Similarity	NPD6883	Approved
0.7391	Intermediate Similarity	NPD7102	Approved
0.7391	Intermediate Similarity	NPD7290	Approved
0.7383	Intermediate Similarity	NPD5282	Discontinued
0.7377	Intermediate Similarity	NPD8328	Phase 3
0.7345	Intermediate Similarity	NPD6008	Approved
0.7339	Intermediate Similarity	NPD7902	Approved
0.7328	Intermediate Similarity	NPD8130	Phase 1
0.7328	Intermediate Similarity	NPD6617	Approved
0.7328	Intermediate Similarity	NPD6869	Approved
0.7328	Intermediate Similarity	NPD6847	Approved
0.7317	Intermediate Similarity	NPD7492	Approved
0.7315	Intermediate Similarity	NPD5695	Phase 3
0.7304	Intermediate Similarity	NPD6012	Approved
0.7304	Intermediate Similarity	NPD6014	Approved
0.7304	Intermediate Similarity	NPD6013	Approved
0.729	Intermediate Similarity	NPD6399	Phase 3
0.7281	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6059	Approved
0.7273	Intermediate Similarity	NPD6054	Approved
0.7273	Intermediate Similarity	NPD5696	Approved
0.7265	Intermediate Similarity	NPD6882	Approved
0.7265	Intermediate Similarity	NPD8297	Approved
0.7264	Intermediate Similarity	NPD5785	Approved
0.7258	Intermediate Similarity	NPD6616	Approved
0.7222	Intermediate Similarity	NPD7748	Approved
0.7217	Intermediate Similarity	NPD6011	Approved
0.7217	Intermediate Similarity	NPD6686	Approved
0.7207	Intermediate Similarity	NPD6648	Approved
0.72	Intermediate Similarity	NPD7078	Approved
0.72	Intermediate Similarity	NPD8293	Discontinued
0.7196	Intermediate Similarity	NPD6411	Approved
0.7196	Intermediate Similarity	NPD7515	Phase 2
0.7179	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6370	Approved
0.7143	Intermediate Similarity	NPD7736	Approved
0.7119	Intermediate Similarity	NPD6053	Discontinued
0.7115	Intermediate Similarity	NPD1694	Approved
0.7097	Intermediate Similarity	NPD7604	Phase 2
0.708	Intermediate Similarity	NPD5211	Phase 2
0.708	Intermediate Similarity	NPD7632	Discontinued
0.7075	Intermediate Similarity	NPD5737	Approved
0.7075	Intermediate Similarity	NPD6672	Approved
0.7073	Intermediate Similarity	NPD6016	Approved
0.7073	Intermediate Similarity	NPD6015	Approved
0.7064	Intermediate Similarity	NPD7900	Approved
0.7064	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4632	Approved
0.7037	Intermediate Similarity	NPD7637	Suspended
0.7037	Intermediate Similarity	NPD5693	Phase 1
0.7027	Intermediate Similarity	NPD4755	Approved
0.7025	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6009	Approved
0.7016	Intermediate Similarity	NPD5988	Approved
0.7009	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6101	Approved
0.6957	Remote Similarity	NPD5141	Approved
0.6953	Remote Similarity	NPD7319	Approved
0.6949	Remote Similarity	NPD4634	Approved
0.6944	Remote Similarity	NPD7838	Discovery
0.6942	Remote Similarity	NPD6274	Approved
0.6935	Remote Similarity	NPD8517	Approved
0.6935	Remote Similarity	NPD8515	Approved
0.6935	Remote Similarity	NPD8516	Approved
0.6935	Remote Similarity	NPD5983	Phase 2
0.6935	Remote Similarity	NPD8513	Phase 3
0.6911	Remote Similarity	NPD7100	Approved
0.6911	Remote Similarity	NPD7101	Approved
0.6903	Remote Similarity	NPD4696	Approved
0.6903	Remote Similarity	NPD5285	Approved
0.6903	Remote Similarity	NPD5286	Approved
0.6903	Remote Similarity	NPD4700	Approved
0.6891	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3618	Phase 1
0.6881	Remote Similarity	NPD7983	Approved
0.6852	Remote Similarity	NPD6080	Approved
0.6852	Remote Similarity	NPD4753	Phase 2
0.6852	Remote Similarity	NPD6673	Approved
0.6852	Remote Similarity	NPD6904	Approved
0.685	Remote Similarity	NPD7507	Approved
0.685	Remote Similarity	NPD6336	Discontinued
0.6838	Remote Similarity	NPD6412	Phase 2
0.6829	Remote Similarity	NPD6335	Approved
0.6827	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6921	Approved
0.68	Remote Similarity	NPD6909	Approved
0.68	Remote Similarity	NPD6908	Approved
0.6792	Remote Similarity	NPD5363	Approved
0.6786	Remote Similarity	NPD4697	Phase 3
0.6783	Remote Similarity	NPD5224	Approved
0.6783	Remote Similarity	NPD5226	Approved
0.6783	Remote Similarity	NPD4633	Approved
0.6783	Remote Similarity	NPD5225	Approved
0.6748	Remote Similarity	NPD6317	Approved
0.6744	Remote Similarity	NPD6033	Approved
0.6729	Remote Similarity	NPD6684	Approved
0.6729	Remote Similarity	NPD7334	Approved
0.6729	Remote Similarity	NPD6409	Approved
0.6729	Remote Similarity	NPD7521	Approved
0.6729	Remote Similarity	NPD5330	Approved
0.6729	Remote Similarity	NPD7146	Approved
0.6727	Remote Similarity	NPD6050	Approved
0.6724	Remote Similarity	NPD5174	Approved
0.6724	Remote Similarity	NPD5175	Approved
0.6723	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4786	Approved
0.6697	Remote Similarity	NPD5328	Approved
0.6697	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD1695	Approved
0.6696	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5223	Approved
0.6696	Remote Similarity	NPD5210	Approved
0.6696	Remote Similarity	NPD4629	Approved
0.6694	Remote Similarity	NPD6313	Approved
0.6694	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6637	Remote Similarity	NPD5221	Approved
0.6637	Remote Similarity	NPD5222	Approved
0.6637	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1696	Phase 3
0.6636	Remote Similarity	NPD5692	Phase 3
0.6635	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4695	Discontinued
0.661	Remote Similarity	NPD4767	Approved
0.661	Remote Similarity	NPD4768	Approved
0.6606	Remote Similarity	NPD6903	Approved
0.6606	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6110	Phase 1
0.6591	Remote Similarity	NPD7260	Phase 2
0.6581	Remote Similarity	NPD4754	Approved
0.6579	Remote Similarity	NPD5173	Approved
0.6577	Remote Similarity	NPD5281	Approved
0.6577	Remote Similarity	NPD6079	Approved
0.6577	Remote Similarity	NPD5284	Approved
0.6577	Remote Similarity	NPD5694	Approved
0.6574	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6098	Approved
0.6574	Remote Similarity	NPD5786	Approved
0.6574	Remote Similarity	NPD5279	Phase 3
0.6571	Remote Similarity	NPD5369	Approved
0.656	Remote Similarity	NPD7328	Approved
0.656	Remote Similarity	NPD7327	Approved
0.6542	Remote Similarity	NPD3665	Phase 1
0.6542	Remote Similarity	NPD3133	Approved
0.6542	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD3666	Approved
0.6535	Remote Similarity	NPD8033	Approved
0.6535	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD3573	Approved
0.6508	Remote Similarity	NPD7516	Approved
0.6504	Remote Similarity	NPD8133	Approved
0.65	Remote Similarity	NPD4729	Approved
0.65	Remote Similarity	NPD4730	Approved
0.65	Remote Similarity	NPD5128	Approved
0.6491	Remote Similarity	NPD7839	Suspended
0.6481	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5329	Approved
0.6476	Remote Similarity	NPD4252	Approved
0.6457	Remote Similarity	NPD8377	Approved
0.6457	Remote Similarity	NPD8294	Approved
0.6449	Remote Similarity	NPD7154	Phase 3

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