NPASS Compound

Structure

NPC265391 OpenBabel07101719252D 31 36 0 0 1 0 0 0 0 0999 V2000 -1.5476 -2.3458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7498 -2.0693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7941 -3.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3673 -1.8556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9905 0.3599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1676 -1.4589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9076 -0.0823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4374 -0.1904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6864 -1.4236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1388 -1.6060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4518 -0.2090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3269 1.4509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1388 -0.3725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4388 -1.0598 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7475 -0.5902 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2853 -0.3825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0555 0.4530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0021 -1.6060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9093 -1.1664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0705 -2.2228 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2287 -0.6254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0021 -0.3725 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4764 -0.9892 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0705 0.2443 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3958 0.1545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2621 0.1965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0662 -2.2228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5537 1.5799 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2860 -0.8650 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 20 1 0 0 0 0 2 20 1 0 0 0 0 5 23 1 0 0 0 0 6 9 1 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 17 1 0 0 0 0 8 22 1 0 0 0 0 10 14 2 0 0 0 0 10 21 1 0 0 0 0 11 16 1 0 0 0 0 11 23 1 0 0 0 0 12 21 1 0 0 0 0 12 24 1 0 0 0 0 13 29 1 0 0 0 0 14 18 1 0 0 0 0 14 25 1 0 0 0 0 15 20 1 0 0 0 0 15 22 1 1 0 0 0 16 22 1 6 0 0 0 16 24 1 0 0 0 0 17 26 2 0 0 0 0 17 30 1 0 0 0 0 18 27 2 0 0 0 0 18 29 1 0 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 19 28 2 0 0 0 0 20 30 1 0 0 0 0 21 3 1 1 0 0 0 22 4 1 1 0 0 0 23 25 1 6 0 0 0 24 9 1 6 0 0 0 24 31 1 0 0 0 0 25 13 1 1 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.2
Volume:	429.176
LogP:	4.028
LogD:	2.845
LogS:	-4.559
# Rotatable Bonds:	0
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	8
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.553
Synthetic Accessibility Score:	7.27
Fsp3:	0.72
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:	-5.371
MDCK Permeability:	2.366579974477645e-05
Pgp-inhibitor:	0.474
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.952

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.909
Plasma Protein Binding (PPB):	79.0651626586914%
Volume Distribution (VD):	0.905
Pgp-substrate:	21.96548080444336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.344
CYP2C19-substrate:	0.68
CYP2C9-inhibitor:	0.222
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.166
CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.937
CYP3A4-substrate:	0.942

ADMET: Excretion

Clearance (CL):	10.044
Half-life (T1/2):	0.214

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.81
Drug-inuced Liver Injury (DILI):	0.106
AMES Toxicity:	0.728
Rat Oral Acute Toxicity:	0.233
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.537
Carcinogencity:	0.907
Eye Corrosion:	0.087
Eye Irritation:	0.027
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC265391

Natural Product ID:	NPC265391
*Common Name:**	Insuetolide C
IUPAC Name:	n.a.
Synonyms:	Insuetolide C
Standard InCHIKey:	FJUKORDKRQJGNE-ZLRFBPIASA-N
Standard InCHI:	InChI=1S/C25H30O6/c1-20(2)15-6-9-24-12-21(3)10-14-18(27)29-13-25(14,31-24)23(5,19(21)28)11-16(24)22(15,4)8-7-17(26)30-20/h7-8,10,15-16H,6,9,11-13H2,1-5H3/t15-,16-,21+,22-,23-,24-,25+/m0/s1
SMILES:	CC1(C)[C@@H]2CC[C@]34C[C@@]5(C)C=C6C(=O)OC[C@@]6([C@@](C)(C[C@H]3[C@@]2(C)C=CC(=O)O1)C5=O)O4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1915266
PubChem CID:	57397405
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
NPO20001	Aspergillus insuetus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19719247]
NPO20001	Aspergillus insuetus	Species	Aspergillaceae	Eukaryota	Mediterranean sponge Psammocinia sp.	coast of Israel	n.a.	PMID[21676619]
NPO20001	Aspergillus insuetus	Species	Aspergillaceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT112	Cell Line	MOLT-4	Homo sapiens	Inhibition	=	51.0	%	PMID[477618]

☑ 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 NPC265391 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	297
0.1-0.2	1750
0.2-0.3	5086
0.3-0.4	8654
0.4-0.5	13418
0.5-0.6	8018
0.6-0.7	4747
0.7-0.8	723
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.934	High Similarity	NPC470246
0.844	Intermediate Similarity	NPC133422
0.8393	Intermediate Similarity	NPC269530
0.8378	Intermediate Similarity	NPC253906
0.8348	Intermediate Similarity	NPC473720
0.8288	Intermediate Similarity	NPC469370
0.8276	Intermediate Similarity	NPC475520
0.8174	Intermediate Similarity	NPC270478
0.8108	Intermediate Similarity	NPC180744
0.8103	Intermediate Similarity	NPC469684
0.8091	Intermediate Similarity	NPC146731
0.8083	Intermediate Similarity	NPC24651
0.807	Intermediate Similarity	NPC277769
0.8037	Intermediate Similarity	NPC38530
0.8037	Intermediate Similarity	NPC84335
0.8	Intermediate Similarity	NPC25909
0.8	Intermediate Similarity	NPC254202
0.7966	Intermediate Similarity	NPC268958
0.7966	Intermediate Similarity	NPC473636
0.7966	Intermediate Similarity	NPC77689
0.7965	Intermediate Similarity	NPC474242
0.7949	Intermediate Similarity	NPC134430
0.7949	Intermediate Similarity	NPC476959
0.7934	Intermediate Similarity	NPC8369
0.7928	Intermediate Similarity	NPC470297
0.7928	Intermediate Similarity	NPC296950
0.7925	Intermediate Similarity	NPC470697
0.7917	Intermediate Similarity	NPC312833
0.7917	Intermediate Similarity	NPC170538
0.7913	Intermediate Similarity	NPC4573
0.7913	Intermediate Similarity	NPC90952
0.7903	Intermediate Similarity	NPC476862
0.7903	Intermediate Similarity	NPC476863
0.7899	Intermediate Similarity	NPC476961
0.7895	Intermediate Similarity	NPC5103
0.7881	Intermediate Similarity	NPC284707
0.7881	Intermediate Similarity	NPC470420
0.7863	Intermediate Similarity	NPC477509
0.7851	Intermediate Similarity	NPC11895
0.7851	Intermediate Similarity	NPC265557
0.7851	Intermediate Similarity	NPC18945
0.7851	Intermediate Similarity	NPC105926
0.7851	Intermediate Similarity	NPC67251
0.7851	Intermediate Similarity	NPC469789
0.7851	Intermediate Similarity	NPC91693
0.7845	Intermediate Similarity	NPC470120
0.7826	Intermediate Similarity	NPC304180
0.7826	Intermediate Similarity	NPC179798
0.7826	Intermediate Similarity	NPC470960
0.7826	Intermediate Similarity	NPC469656
0.7826	Intermediate Similarity	NPC474846
0.7826	Intermediate Similarity	NPC469655
0.7815	Intermediate Similarity	NPC470777
0.7815	Intermediate Similarity	NPC476960
0.7815	Intermediate Similarity	NPC211093
0.7815	Intermediate Similarity	NPC473839
0.781	Intermediate Similarity	NPC152467
0.7805	Intermediate Similarity	NPC287423
0.7797	Intermediate Similarity	NPC58662
0.7797	Intermediate Similarity	NPC53396
0.7797	Intermediate Similarity	NPC98249
0.7797	Intermediate Similarity	NPC475809
0.7788	Intermediate Similarity	NPC476958
0.7787	Intermediate Similarity	NPC476729
0.7787	Intermediate Similarity	NPC470922
0.7787	Intermediate Similarity	NPC81736
0.7787	Intermediate Similarity	NPC172154
0.7778	Intermediate Similarity	NPC168879
0.7778	Intermediate Similarity	NPC470953
0.7759	Intermediate Similarity	NPC476801
0.7759	Intermediate Similarity	NPC222834
0.7759	Intermediate Similarity	NPC472002
0.7757	Intermediate Similarity	NPC471446
0.7757	Intermediate Similarity	NPC473434
0.7757	Intermediate Similarity	NPC474841
0.775	Intermediate Similarity	NPC476962
0.7742	Intermediate Similarity	NPC473620
0.7739	Intermediate Similarity	NPC286880
0.7739	Intermediate Similarity	NPC235014
0.7731	Intermediate Similarity	NPC17772
0.7727	Intermediate Similarity	NPC470761
0.7727	Intermediate Similarity	NPC473219
0.7727	Intermediate Similarity	NPC476933
0.7724	Intermediate Similarity	NPC473635
0.7724	Intermediate Similarity	NPC293112
0.7719	Intermediate Similarity	NPC275539
0.7719	Intermediate Similarity	NPC476802
0.7719	Intermediate Similarity	NPC189075
0.7719	Intermediate Similarity	NPC89171
0.7714	Intermediate Similarity	NPC471222
0.7714	Intermediate Similarity	NPC73995
0.7705	Intermediate Similarity	NPC204812
0.7705	Intermediate Similarity	NPC120724
0.7699	Intermediate Similarity	NPC469607
0.7692	Intermediate Similarity	NPC33360
0.7692	Intermediate Similarity	NPC469496
0.7692	Intermediate Similarity	NPC469454
0.7692	Intermediate Similarity	NPC56448
0.7692	Intermediate Similarity	NPC473535
0.7692	Intermediate Similarity	NPC471204
0.7692	Intermediate Similarity	NPC469463
0.7686	Intermediate Similarity	NPC46570
0.7686	Intermediate Similarity	NPC204731
0.7686	Intermediate Similarity	NPC67569
0.7686	Intermediate Similarity	NPC310511
0.7686	Intermediate Similarity	NPC470779
0.7685	Intermediate Similarity	NPC217329
0.7679	Intermediate Similarity	NPC159533
0.7667	Intermediate Similarity	NPC475775
0.7667	Intermediate Similarity	NPC476529
0.7667	Intermediate Similarity	NPC472933
0.7664	Intermediate Similarity	NPC475657
0.7652	Intermediate Similarity	NPC220705
0.7652	Intermediate Similarity	NPC112457
0.7647	Intermediate Similarity	NPC474654
0.7647	Intermediate Similarity	NPC476965
0.7647	Intermediate Similarity	NPC287343
0.7647	Intermediate Similarity	NPC284068
0.7647	Intermediate Similarity	NPC473968
0.7647	Intermediate Similarity	NPC122033
0.7647	Intermediate Similarity	NPC470854
0.7647	Intermediate Similarity	NPC470959
0.7647	Intermediate Similarity	NPC473656
0.7647	Intermediate Similarity	NPC97908
0.7642	Intermediate Similarity	NPC241456
0.7642	Intermediate Similarity	NPC32868
0.7636	Intermediate Similarity	NPC471932
0.7632	Intermediate Similarity	NPC110496
0.7627	Intermediate Similarity	NPC299849
0.7627	Intermediate Similarity	NPC117712
0.7627	Intermediate Similarity	NPC474181
0.7623	Intermediate Similarity	NPC23786
0.7623	Intermediate Similarity	NPC107493
0.7623	Intermediate Similarity	NPC470265
0.7619	Intermediate Similarity	NPC215831
0.7619	Intermediate Similarity	NPC476852
0.7619	Intermediate Similarity	NPC476855
0.7611	Intermediate Similarity	NPC474898
0.7611	Intermediate Similarity	NPC189616
0.7607	Intermediate Similarity	NPC152117
0.7607	Intermediate Similarity	NPC234042
0.7603	Intermediate Similarity	NPC109607
0.7603	Intermediate Similarity	NPC143755
0.7603	Intermediate Similarity	NPC474585
0.7603	Intermediate Similarity	NPC107338
0.7603	Intermediate Similarity	NPC4548
0.7603	Intermediate Similarity	NPC48692
0.76	Intermediate Similarity	NPC476859
0.7593	Intermediate Similarity	NPC84893
0.7593	Intermediate Similarity	NPC477130
0.7593	Intermediate Similarity	NPC477129
0.7589	Intermediate Similarity	NPC164551
0.7589	Intermediate Similarity	NPC80781
0.7589	Intermediate Similarity	NPC295791
0.7586	Intermediate Similarity	NPC478209
0.7586	Intermediate Similarity	NPC474567
0.7586	Intermediate Similarity	NPC5284
0.7586	Intermediate Similarity	NPC472666
0.7583	Intermediate Similarity	NPC251310
0.7583	Intermediate Similarity	NPC153440
0.7583	Intermediate Similarity	NPC475372
0.7583	Intermediate Similarity	NPC470776
0.7581	Intermediate Similarity	NPC477745
0.7581	Intermediate Similarity	NPC181999
0.757	Intermediate Similarity	NPC473944
0.7568	Intermediate Similarity	NPC476299
0.7568	Intermediate Similarity	NPC471413
0.7568	Intermediate Similarity	NPC474012
0.7568	Intermediate Similarity	NPC198880
0.7563	Intermediate Similarity	NPC190185
0.7563	Intermediate Similarity	NPC270929
0.7563	Intermediate Similarity	NPC476963
0.7563	Intermediate Similarity	NPC176840
0.7563	Intermediate Similarity	NPC213084
0.7563	Intermediate Similarity	NPC207217
0.7563	Intermediate Similarity	NPC190286
0.7559	Intermediate Similarity	NPC102316
0.7547	Intermediate Similarity	NPC173042
0.7545	Intermediate Similarity	NPC292133
0.7545	Intermediate Similarity	NPC2049
0.7545	Intermediate Similarity	NPC70145
0.7545	Intermediate Similarity	NPC91695
0.7545	Intermediate Similarity	NPC226986
0.7544	Intermediate Similarity	NPC470975
0.7544	Intermediate Similarity	NPC477125
0.7544	Intermediate Similarity	NPC103088
0.7544	Intermediate Similarity	NPC470979
0.7544	Intermediate Similarity	NPC181357
0.7544	Intermediate Similarity	NPC102352
0.7542	Intermediate Similarity	NPC159333
0.7542	Intermediate Similarity	NPC194273
0.7542	Intermediate Similarity	NPC478212
0.7542	Intermediate Similarity	NPC49451
0.7541	Intermediate Similarity	NPC472000
0.7541	Intermediate Similarity	NPC471999
0.754	Intermediate Similarity	NPC472770
0.754	Intermediate Similarity	NPC476851
0.754	Intermediate Similarity	NPC476854
0.754	Intermediate Similarity	NPC231529
0.754	Intermediate Similarity	NPC264192

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 NPC265391 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	1940
0.2-0.3	3925
0.3-0.4	1987
0.4-0.5	665
0.5-0.6	204
0.6-0.7	169
0.7-0.8	4
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
0.75	Intermediate Similarity	NPD1694	Approved
0.75	Intermediate Similarity	NPD7115	Discovery
0.7391	Intermediate Similarity	NPD6008	Approved
0.7358	Intermediate Similarity	NPD3573	Approved
0.7328	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4225	Approved
0.7265	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7492	Approved
0.7059	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6054	Approved
0.7031	Intermediate Similarity	NPD6616	Approved
0.6984	Remote Similarity	NPD6016	Approved
0.6984	Remote Similarity	NPD6015	Approved
0.6977	Remote Similarity	NPD7078	Approved
0.6967	Remote Similarity	NPD4632	Approved
0.6929	Remote Similarity	NPD5988	Approved
0.6929	Remote Similarity	NPD6370	Approved
0.6923	Remote Similarity	NPD7736	Approved
0.6903	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7260	Phase 2
0.6891	Remote Similarity	NPD5697	Approved
0.6887	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8297	Approved
0.687	Remote Similarity	NPD7319	Approved
0.687	Remote Similarity	NPD7638	Approved
0.686	Remote Similarity	NPD6371	Approved
0.685	Remote Similarity	NPD8516	Approved
0.685	Remote Similarity	NPD8517	Approved
0.685	Remote Similarity	NPD8515	Approved
0.685	Remote Similarity	NPD8513	Phase 3
0.6833	Remote Similarity	NPD6686	Approved
0.6833	Remote Similarity	NPD6899	Approved
0.6833	Remote Similarity	NPD6881	Approved
0.681	Remote Similarity	NPD7639	Approved
0.681	Remote Similarity	NPD7640	Approved
0.6803	Remote Similarity	NPD6649	Approved
0.6803	Remote Similarity	NPD6650	Approved
0.68	Remote Similarity	NPD6009	Approved
0.6777	Remote Similarity	NPD6013	Approved
0.6777	Remote Similarity	NPD6014	Approved
0.6777	Remote Similarity	NPD6012	Approved
0.6772	Remote Similarity	NPD6059	Approved
0.6769	Remote Similarity	NPD7507	Approved
0.6754	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD8328	Phase 3
0.6724	Remote Similarity	NPD5696	Approved
0.6721	Remote Similarity	NPD7102	Approved
0.6721	Remote Similarity	NPD4634	Approved
0.6721	Remote Similarity	NPD7290	Approved
0.6721	Remote Similarity	NPD6883	Approved
0.6719	Remote Similarity	NPD5983	Phase 2
0.6718	Remote Similarity	NPD8293	Discontinued
0.6716	Remote Similarity	NPD6845	Suspended
0.6697	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6639	Remote Similarity	NPD6372	Approved
0.6639	Remote Similarity	NPD6373	Approved
0.6637	Remote Similarity	NPD5693	Phase 1
0.6637	Remote Similarity	NPD6411	Approved
0.6636	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7604	Phase 2
0.6613	Remote Similarity	NPD6053	Discontinued
0.6613	Remote Similarity	NPD6882	Approved
0.6612	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5701	Approved
0.6591	Remote Similarity	NPD8074	Phase 3
0.6589	Remote Similarity	NPD6921	Approved
0.6579	Remote Similarity	NPD5779	Approved
0.6579	Remote Similarity	NPD5778	Approved
0.6557	Remote Similarity	NPD7320	Approved
0.6555	Remote Similarity	NPD5211	Phase 2
0.6549	Remote Similarity	NPD5207	Approved
0.6535	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD4696	Approved
0.6525	Remote Similarity	NPD5286	Approved
0.6525	Remote Similarity	NPD5285	Approved
0.6522	Remote Similarity	NPD7748	Approved
0.6522	Remote Similarity	NPD5282	Discontinued
0.6522	Remote Similarity	NPD6001	Approved
0.6518	Remote Similarity	NPD6672	Approved
0.6518	Remote Similarity	NPD5737	Approved
0.6515	Remote Similarity	NPD6336	Discontinued
0.6496	Remote Similarity	NPD7902	Approved
0.6491	Remote Similarity	NPD6079	Approved
0.6486	Remote Similarity	NPD7521	Approved
0.6486	Remote Similarity	NPD7334	Approved
0.6486	Remote Similarity	NPD5330	Approved
0.6486	Remote Similarity	NPD6684	Approved
0.6486	Remote Similarity	NPD6409	Approved
0.6486	Remote Similarity	NPD7146	Approved
0.6466	Remote Similarity	NPD5695	Phase 3
0.6466	Remote Similarity	NPD4629	Approved
0.6466	Remote Similarity	NPD5210	Approved
0.646	Remote Similarity	NPD6101	Approved
0.646	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD5141	Approved
0.6435	Remote Similarity	NPD6399	Phase 3
0.6417	Remote Similarity	NPD5226	Approved
0.6417	Remote Similarity	NPD7632	Discontinued
0.6417	Remote Similarity	NPD4633	Approved
0.6417	Remote Similarity	NPD5224	Approved
0.6417	Remote Similarity	NPD5225	Approved
0.641	Remote Similarity	NPD5222	Approved
0.641	Remote Similarity	NPD5221	Approved
0.641	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6648	Approved
0.6372	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6903	Approved
0.6371	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5175	Approved
0.6364	Remote Similarity	NPD5174	Approved
0.6356	Remote Similarity	NPD6084	Phase 2
0.6356	Remote Similarity	NPD5173	Approved
0.6356	Remote Similarity	NPD4755	Approved
0.6356	Remote Similarity	NPD6083	Phase 2
0.6348	Remote Similarity	NPD5694	Approved
0.6348	Remote Similarity	NPD7515	Phase 2
0.6341	Remote Similarity	NPD6412	Phase 2
0.6339	Remote Similarity	NPD3618	Phase 1
0.6336	Remote Similarity	NPD7503	Approved
0.6336	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5344	Discontinued
0.6333	Remote Similarity	NPD5223	Approved
0.6328	Remote Similarity	NPD6274	Approved
0.6316	Remote Similarity	NPD6673	Approved
0.6316	Remote Similarity	NPD1695	Approved
0.6316	Remote Similarity	NPD5328	Approved
0.6316	Remote Similarity	NPD6904	Approved
0.6316	Remote Similarity	NPD6080	Approved
0.6308	Remote Similarity	NPD7101	Approved
0.6308	Remote Similarity	NPD7100	Approved
0.6296	Remote Similarity	NPD6033	Approved
0.6279	Remote Similarity	NPD6317	Approved
0.6271	Remote Similarity	NPD7732	Phase 3
0.6271	Remote Similarity	NPD4697	Phase 3
0.627	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6698	Approved
0.6261	Remote Similarity	NPD46	Approved
0.6261	Remote Similarity	NPD5692	Phase 3
0.6261	Remote Similarity	NPD5785	Approved
0.625	Remote Similarity	NPD4700	Approved
0.6231	Remote Similarity	NPD7327	Approved
0.6231	Remote Similarity	NPD6313	Approved
0.6231	Remote Similarity	NPD6314	Approved
0.6231	Remote Similarity	NPD6335	Approved
0.6231	Remote Similarity	NPD7328	Approved
0.6228	Remote Similarity	NPD5208	Approved
0.6212	Remote Similarity	NPD8033	Approved
0.621	Remote Similarity	NPD6614	Approved
0.6207	Remote Similarity	NPD6050	Approved
0.6207	Remote Similarity	NPD5281	Approved
0.6207	Remote Similarity	NPD5284	Approved
0.6202	Remote Similarity	NPD6868	Approved
0.6183	Remote Similarity	NPD7516	Approved
0.616	Remote Similarity	NPD4729	Approved
0.616	Remote Similarity	NPD4730	Approved
0.6142	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD8377	Approved
0.6136	Remote Similarity	NPD8294	Approved
0.6126	Remote Similarity	NPD5209	Approved
0.6115	Remote Similarity	NPD8338	Approved
0.609	Remote Similarity	NPD8379	Approved
0.609	Remote Similarity	NPD8335	Approved
0.609	Remote Similarity	NPD8378	Approved
0.609	Remote Similarity	NPD8380	Approved
0.609	Remote Similarity	NPD8296	Approved
0.6068	Remote Similarity	NPD7983	Approved
0.6063	Remote Similarity	NPD5247	Approved
0.6063	Remote Similarity	NPD5248	Approved
0.6063	Remote Similarity	NPD5251	Approved
0.6063	Remote Similarity	NPD5250	Approved
0.6063	Remote Similarity	NPD5249	Phase 3
0.6058	Remote Similarity	NPD8336	Approved
0.6058	Remote Similarity	NPD8337	Approved
0.6056	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD4623	Approved
0.6053	Remote Similarity	NPD6098	Approved
0.6053	Remote Similarity	NPD4519	Discontinued
0.605	Remote Similarity	NPD5654	Approved
0.6047	Remote Similarity	NPD8133	Approved
0.6034	Remote Similarity	NPD6051	Approved
0.6034	Remote Similarity	NPD4753	Phase 2
0.6033	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD5128	Approved
0.6018	Remote Similarity	NPD3668	Phase 3
0.6017	Remote Similarity	NPD4202	Approved
0.6016	Remote Similarity	NPD5217	Approved
0.6016	Remote Similarity	NPD5216	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