NPASS Compound

Structure

NPC471686 OpenBabel07101718202D 34 38 0 0 1 0 0 0 0 0999 V2000 4.2174 -3.4089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2285 -1.1200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2758 -1.3225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4870 1.8175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9740 0.9740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2863 1.8030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5910 -0.1355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8711 0.1850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6870 -2.9219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6870 0.9740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3740 -2.9219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6870 -1.9480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5305 -3.4089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6870 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8435 1.4610 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2285 0.3277 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5305 -1.4610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3740 -1.9480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8435 -1.4610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5305 -0.4870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5767 -0.3962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7888 0.9686 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6870 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8435 -0.4870 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8435 2.4349 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.5305 0.4870 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.5305 -4.3829 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2174 -1.4610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3740 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7415 1.1711 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 12 1 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 7 8 1 0 0 0 0 8 24 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 11 25 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 29 1 0 0 0 0 15 22 1 0 0 0 0 15 24 1 1 0 0 0 16 23 1 0 0 0 0 16 27 1 6 0 0 0 17 7 1 1 0 0 0 17 22 1 0 0 0 0 17 33 1 0 0 0 0 18 19 2 0 0 0 0 18 21 1 0 0 0 0 19 30 1 0 0 0 0 20 26 1 0 0 0 0 20 31 2 0 0 0 0 21 25 1 0 0 0 0 21 32 2 0 0 0 0 23 34 1 0 0 0 0 24 6 1 1 0 0 0 24 33 1 0 0 0 0 25 26 1 1 0 0 0 25 28 1 0 0 0 0 26 10 1 1 0 0 0 26 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	554.11
Volume:	489.524
LogP:	5.83
LogD:	3.818
LogS:	-4.374
# Rotatable Bonds:	2
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.472
Synthetic Accessibility Score:	5.889
Fsp3:	0.692
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.931
MDCK Permeability:	1.6416948710684665e-05
Pgp-inhibitor:	0.557
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.088
20% Bioavailability (F20%):	0.052
30% Bioavailability (F30%):	0.134

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.371
Plasma Protein Binding (PPB):	100.21537017822266%
Volume Distribution (VD):	1.81
Pgp-substrate:	3.4869208335876465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.228
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.503
CYP2C19-substrate:	0.726
CYP2C9-inhibitor:	0.913
CYP2C9-substrate:	0.451
CYP2D6-inhibitor:	0.196
CYP2D6-substrate:	0.265
CYP3A4-inhibitor:	0.79
CYP3A4-substrate:	0.91

ADMET: Excretion

Clearance (CL):	3.681
Half-life (T1/2):	0.035

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.302
Drug-inuced Liver Injury (DILI):	0.4
AMES Toxicity:	0.113
Rat Oral Acute Toxicity:	0.786
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.545
Carcinogencity:	0.466
Eye Corrosion:	0.008
Eye Irritation:	0.791
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC471686

Natural Product ID:	NPC471686
*Common Name:**	Napyradiomycin Cnq525.554
IUPAC Name:	(3R,4aR,10aS)-3-bromo-4a-chloro-6,8-dihydroxy-2,2,7-trimethyl-10a-[[(1R,3S,4S)-2,2,4-trimethyl-7-oxabicyclo[2.2.1]heptan-3-yl]methyl]-3,4-dihydrobenzo[g]chromene-5,10-dione
Synonyms:
Standard InCHIKey:	UGEWFNIBLSXHJU-VCQHOALXSA-N
Standard InCHI:	InChI=1S/C26H32BrClO6/c1-12-14(29)9-13-18(19(12)30)21(32)25(28)11-16(27)23(4,5)34-26(25,20(13)31)10-15-22(2,3)17-7-8-24(15,6)33-17/h9,15-17,29-30H,7-8,10-11H2,1-6H3/t15-,16+,17+,24-,25-,26-/m0/s1
SMILES:	Oc1cc2c(c(c1C)O)C(=O)[C@@]1([C@@](C2=O)(C[C@@H]2[C@]3(C)CC[C@H](C2(C)C)O3)OC([C@@H](C1)Br)(C)C)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3104841
PubChem CID:	76328312
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO32475	actinomycete sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24328269]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	100000.0	nM	PMID[546163]

☑ 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 NPC471686 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	464
0.1-0.2	1780
0.2-0.3	3488
0.3-0.4	9949
0.4-0.5	11350
0.5-0.6	6644
0.6-0.7	8358
0.7-0.8	648
0.8-0.85	10
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9464	High Similarity	NPC471684
0.9277	High Similarity	NPC471685
0.8902	High Similarity	NPC158699
0.8889	High Similarity	NPC108948
0.8772	High Similarity	NPC301846
0.8772	High Similarity	NPC311679
0.8663	High Similarity	NPC131078
0.8563	High Similarity	NPC184518
0.8547	High Similarity	NPC471687
0.8391	Intermediate Similarity	NPC73544
0.8182	Intermediate Similarity	NPC314653
0.8182	Intermediate Similarity	NPC316262
0.8023	Intermediate Similarity	NPC470563
0.8	Intermediate Similarity	NPC470559
0.8	Intermediate Similarity	NPC315306
0.8	Intermediate Similarity	NPC313717
0.7966	Intermediate Similarity	NPC470561
0.7955	Intermediate Similarity	NPC313368
0.787	Intermediate Similarity	NPC471906
0.7865	Intermediate Similarity	NPC475106
0.7849	Intermediate Similarity	NPC475656
0.7849	Intermediate Similarity	NPC475148
0.7821	Intermediate Similarity	NPC100849
0.7814	Intermediate Similarity	NPC475080
0.7802	Intermediate Similarity	NPC470562
0.7784	Intermediate Similarity	NPC470564
0.7778	Intermediate Similarity	NPC470570
0.7765	Intermediate Similarity	NPC245122
0.776	Intermediate Similarity	NPC470560
0.7751	Intermediate Similarity	NPC474961
0.7751	Intermediate Similarity	NPC135524
0.7751	Intermediate Similarity	NPC308572
0.7733	Intermediate Similarity	NPC5568
0.7719	Intermediate Similarity	NPC474630
0.7719	Intermediate Similarity	NPC34482
0.7692	Intermediate Similarity	NPC305845
0.7692	Intermediate Similarity	NPC204045
0.7688	Intermediate Similarity	NPC94781
0.7674	Intermediate Similarity	NPC136878
0.767	Intermediate Similarity	NPC472211
0.7663	Intermediate Similarity	NPC118128
0.7661	Intermediate Similarity	NPC244691
0.7661	Intermediate Similarity	NPC48762
0.7644	Intermediate Similarity	NPC474310
0.7644	Intermediate Similarity	NPC120171
0.764	Intermediate Similarity	NPC196448
0.7637	Intermediate Similarity	NPC125465
0.7633	Intermediate Similarity	NPC169452
0.7633	Intermediate Similarity	NPC181560
0.7609	Intermediate Similarity	NPC470565
0.7609	Intermediate Similarity	NPC474004
0.76	Intermediate Similarity	NPC470568
0.7598	Intermediate Similarity	NPC472617
0.7598	Intermediate Similarity	NPC218818
0.7598	Intermediate Similarity	NPC239118
0.7588	Intermediate Similarity	NPC110810
0.7586	Intermediate Similarity	NPC112816
0.7584	Intermediate Similarity	NPC280497
0.7581	Intermediate Similarity	NPC264922
0.7574	Intermediate Similarity	NPC242994
0.7574	Intermediate Similarity	NPC114620
0.7574	Intermediate Similarity	NPC138099
0.7574	Intermediate Similarity	NPC190457
0.7574	Intermediate Similarity	NPC103337
0.7568	Intermediate Similarity	NPC169018
0.7568	Intermediate Similarity	NPC474857
0.756	Intermediate Similarity	NPC471905
0.7558	Intermediate Similarity	NPC21599
0.7558	Intermediate Similarity	NPC193703
0.7558	Intermediate Similarity	NPC29932
0.7557	Intermediate Similarity	NPC470569
0.7557	Intermediate Similarity	NPC470675
0.7557	Intermediate Similarity	NPC473131
0.7556	Intermediate Similarity	NPC472618
0.7556	Intermediate Similarity	NPC470810
0.7554	Intermediate Similarity	NPC286074
0.7554	Intermediate Similarity	NPC54903
0.7553	Intermediate Similarity	NPC70318
0.7544	Intermediate Similarity	NPC193555
0.7543	Intermediate Similarity	NPC44378
0.7543	Intermediate Similarity	NPC280753
0.7542	Intermediate Similarity	NPC158542
0.7542	Intermediate Similarity	NPC474637
0.7542	Intermediate Similarity	NPC272196
0.7541	Intermediate Similarity	NPC475109
0.7527	Intermediate Similarity	NPC476822
0.7514	Intermediate Similarity	NPC277865
0.7514	Intermediate Similarity	NPC87708
0.7514	Intermediate Similarity	NPC40356
0.7514	Intermediate Similarity	NPC154683
0.7514	Intermediate Similarity	NPC470340
0.7514	Intermediate Similarity	NPC28632
0.7514	Intermediate Similarity	NPC117985
0.75	Intermediate Similarity	NPC147735
0.75	Intermediate Similarity	NPC470566
0.75	Intermediate Similarity	NPC4950
0.75	Intermediate Similarity	NPC191976
0.75	Intermediate Similarity	NPC254847
0.75	Intermediate Similarity	NPC193222
0.75	Intermediate Similarity	NPC159721
0.7486	Intermediate Similarity	NPC142846
0.7486	Intermediate Similarity	NPC477674
0.7486	Intermediate Similarity	NPC472049
0.7485	Intermediate Similarity	NPC472603
0.7474	Intermediate Similarity	NPC470332
0.7473	Intermediate Similarity	NPC473022
0.7472	Intermediate Similarity	NPC312482
0.7472	Intermediate Similarity	NPC218870
0.7472	Intermediate Similarity	NPC470408
0.7472	Intermediate Similarity	NPC477669
0.7472	Intermediate Similarity	NPC182921
0.7472	Intermediate Similarity	NPC474824
0.7471	Intermediate Similarity	NPC51513
0.7471	Intermediate Similarity	NPC143438
0.7471	Intermediate Similarity	NPC202112
0.746	Intermediate Similarity	NPC473729
0.746	Intermediate Similarity	NPC473607
0.7459	Intermediate Similarity	NPC470567
0.7458	Intermediate Similarity	NPC230848
0.7458	Intermediate Similarity	NPC232645
0.7458	Intermediate Similarity	NPC478148
0.7458	Intermediate Similarity	NPC205918
0.7458	Intermediate Similarity	NPC477672
0.7458	Intermediate Similarity	NPC477673
0.7458	Intermediate Similarity	NPC72958
0.7457	Intermediate Similarity	NPC42540
0.7457	Intermediate Similarity	NPC151607
0.7456	Intermediate Similarity	NPC53206
0.7456	Intermediate Similarity	NPC53414
0.7456	Intermediate Similarity	NPC53001
0.7447	Intermediate Similarity	NPC98943
0.7447	Intermediate Similarity	NPC324220
0.7447	Intermediate Similarity	NPC312630
0.7447	Intermediate Similarity	NPC472661
0.7446	Intermediate Similarity	NPC17274
0.7446	Intermediate Similarity	NPC476255
0.7446	Intermediate Similarity	NPC53640
0.7446	Intermediate Similarity	NPC85047
0.7446	Intermediate Similarity	NPC120857
0.7446	Intermediate Similarity	NPC62444
0.7446	Intermediate Similarity	NPC476056
0.7444	Intermediate Similarity	NPC201127
0.7444	Intermediate Similarity	NPC281137
0.7444	Intermediate Similarity	NPC472404
0.7444	Intermediate Similarity	NPC197326
0.7444	Intermediate Similarity	NPC282390
0.7433	Intermediate Similarity	NPC470333
0.7433	Intermediate Similarity	NPC469393
0.7432	Intermediate Similarity	NPC109180
0.743	Intermediate Similarity	NPC477687
0.743	Intermediate Similarity	NPC314257
0.743	Intermediate Similarity	NPC478133
0.743	Intermediate Similarity	NPC478221
0.743	Intermediate Similarity	NPC477671
0.7429	Intermediate Similarity	NPC289042
0.7429	Intermediate Similarity	NPC245584
0.7429	Intermediate Similarity	NPC56433
0.7429	Intermediate Similarity	NPC312929
0.7429	Intermediate Similarity	NPC190648
0.7429	Intermediate Similarity	NPC118027
0.7429	Intermediate Similarity	NPC126767
0.7429	Intermediate Similarity	NPC476821
0.7427	Intermediate Similarity	NPC472601
0.7427	Intermediate Similarity	NPC472600
0.7427	Intermediate Similarity	NPC156872
0.7419	Intermediate Similarity	NPC477573
0.7419	Intermediate Similarity	NPC477571
0.7419	Intermediate Similarity	NPC477572
0.7418	Intermediate Similarity	NPC476929
0.7416	Intermediate Similarity	NPC470337
0.7416	Intermediate Similarity	NPC180944
0.7416	Intermediate Similarity	NPC470338
0.7416	Intermediate Similarity	NPC113608
0.7416	Intermediate Similarity	NPC268992
0.7416	Intermediate Similarity	NPC51824
0.7414	Intermediate Similarity	NPC117716
0.7414	Intermediate Similarity	NPC470674
0.7414	Intermediate Similarity	NPC470673
0.7412	Intermediate Similarity	NPC87723
0.7409	Intermediate Similarity	NPC313386
0.7407	Intermediate Similarity	NPC470334
0.7407	Intermediate Similarity	NPC233978
0.7407	Intermediate Similarity	NPC246877
0.7405	Intermediate Similarity	NPC476459
0.7403	Intermediate Similarity	NPC40583
0.7403	Intermediate Similarity	NPC125969
0.7401	Intermediate Similarity	NPC255641
0.7401	Intermediate Similarity	NPC290954
0.7401	Intermediate Similarity	NPC202595
0.7401	Intermediate Similarity	NPC294646
0.7401	Intermediate Similarity	NPC280295
0.7399	Intermediate Similarity	NPC143898
0.7399	Intermediate Similarity	NPC471731
0.7399	Intermediate Similarity	NPC354984
0.7396	Intermediate Similarity	NPC474311
0.7394	Intermediate Similarity	NPC294149
0.7394	Intermediate Similarity	NPC162248
0.7391	Intermediate Similarity	NPC473286
0.7389	Intermediate Similarity	NPC477675
0.7389	Intermediate Similarity	NPC180924

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 NPC471686 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	961
0.2-0.3	2022
0.3-0.4	3259
0.4-0.5	1799
0.5-0.6	562
0.6-0.7	176
0.7-0.8	1
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	NPD1509	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6959	Discontinued
0.7216	Intermediate Similarity	NPD2533	Approved
0.7216	Intermediate Similarity	NPD2532	Approved
0.7216	Intermediate Similarity	NPD2534	Approved
0.7159	Intermediate Similarity	NPD7390	Discontinued
0.7088	Intermediate Similarity	NPD7819	Suspended
0.7074	Intermediate Similarity	NPD7473	Discontinued
0.7065	Intermediate Similarity	NPD7075	Discontinued
0.7022	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD2800	Approved
0.6931	Remote Similarity	NPD2403	Approved
0.6923	Remote Similarity	NPD4380	Phase 2
0.6919	Remote Similarity	NPD3882	Suspended
0.6915	Remote Similarity	NPD6232	Discontinued
0.6898	Remote Similarity	NPD5494	Approved
0.6888	Remote Similarity	NPD8150	Discontinued
0.6857	Remote Similarity	NPD6100	Approved
0.6857	Remote Similarity	NPD6099	Approved
0.6837	Remote Similarity	NPD6784	Approved
0.6837	Remote Similarity	NPD6785	Approved
0.6831	Remote Similarity	NPD6599	Discontinued
0.6825	Remote Similarity	NPD5711	Approved
0.6825	Remote Similarity	NPD5710	Approved
0.68	Remote Similarity	NPD651	Clinical (unspecified phase)
0.678	Remote Similarity	NPD970	Clinical (unspecified phase)
0.678	Remote Similarity	NPD1549	Phase 2
0.6757	Remote Similarity	NPD1934	Approved
0.6757	Remote Similarity	NPD6801	Discontinued
0.6746	Remote Similarity	NPD1470	Approved
0.6736	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6559	Discontinued
0.6715	Remote Similarity	NPD8319	Approved
0.6715	Remote Similarity	NPD8320	Phase 1
0.6705	Remote Similarity	NPD1510	Phase 2
0.6704	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3749	Approved
0.6686	Remote Similarity	NPD1607	Approved
0.6686	Remote Similarity	NPD6651	Approved
0.6684	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6534	Approved
0.6683	Remote Similarity	NPD6535	Approved
0.6667	Remote Similarity	NPD943	Approved
0.6667	Remote Similarity	NPD5408	Approved
0.6667	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD6166	Phase 2
0.6667	Remote Similarity	NPD5404	Approved
0.6667	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5405	Approved
0.6667	Remote Similarity	NPD7699	Phase 2
0.6667	Remote Similarity	NPD5406	Approved
0.6667	Remote Similarity	NPD7700	Phase 2
0.6649	Remote Similarity	NPD5844	Phase 1
0.6648	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD8434	Phase 2
0.6613	Remote Similarity	NPD7411	Suspended
0.6602	Remote Similarity	NPD6782	Approved
0.6602	Remote Similarity	NPD6779	Approved
0.6602	Remote Similarity	NPD6778	Approved
0.6602	Remote Similarity	NPD6777	Approved
0.6602	Remote Similarity	NPD6776	Approved
0.6602	Remote Similarity	NPD6781	Approved
0.6602	Remote Similarity	NPD6780	Approved
0.6601	Remote Similarity	NPD4360	Phase 2
0.6601	Remote Similarity	NPD4363	Phase 3
0.6598	Remote Similarity	NPD3818	Discontinued
0.6595	Remote Similarity	NPD3226	Approved
0.6587	Remote Similarity	NPD7698	Approved
0.6587	Remote Similarity	NPD7696	Phase 3
0.6587	Remote Similarity	NPD7697	Approved
0.6583	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD2796	Approved
0.6571	Remote Similarity	NPD1240	Approved
0.6555	Remote Similarity	NPD7870	Phase 2
0.6555	Remote Similarity	NPD7871	Phase 2
0.6548	Remote Similarity	NPD7251	Discontinued
0.6543	Remote Similarity	NPD5761	Phase 2
0.6543	Remote Similarity	NPD5760	Phase 2
0.6543	Remote Similarity	NPD2801	Approved
0.6526	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1512	Approved
0.6515	Remote Similarity	NPD7808	Phase 3
0.6509	Remote Similarity	NPD1201	Approved
0.6508	Remote Similarity	NPD3817	Phase 2
0.6503	Remote Similarity	NPD6799	Approved
0.6497	Remote Similarity	NPD6797	Phase 2
0.6495	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD6234	Discontinued
0.6492	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD4361	Phase 2
0.6479	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD7874	Approved
0.6474	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4967	Phase 2
0.6474	Remote Similarity	NPD4966	Approved
0.6474	Remote Similarity	NPD7768	Phase 2
0.6474	Remote Similarity	NPD4965	Approved
0.6462	Remote Similarity	NPD7701	Phase 2
0.6449	Remote Similarity	NPD7801	Approved
0.6448	Remote Similarity	NPD3300	Phase 2
0.6447	Remote Similarity	NPD7074	Phase 3
0.6444	Remote Similarity	NPD2346	Discontinued
0.6432	Remote Similarity	NPD8151	Discontinued
0.6432	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7228	Approved
0.6429	Remote Similarity	NPD3751	Discontinued
0.6425	Remote Similarity	NPD1247	Approved
0.6421	Remote Similarity	NPD5402	Approved
0.642	Remote Similarity	NPD6663	Approved
0.6413	Remote Similarity	NPD1511	Approved
0.6404	Remote Similarity	NPD4287	Approved
0.64	Remote Similarity	NPD8313	Approved
0.64	Remote Similarity	NPD8312	Approved
0.6398	Remote Similarity	NPD920	Approved
0.6396	Remote Similarity	NPD7054	Approved
0.6396	Remote Similarity	NPD6020	Phase 2
0.6389	Remote Similarity	NPD2935	Discontinued
0.6368	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3764	Approved
0.6364	Remote Similarity	NPD7472	Approved
0.6359	Remote Similarity	NPD7236	Approved
0.6359	Remote Similarity	NPD3926	Phase 2
0.635	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD230	Phase 1
0.6345	Remote Similarity	NPD7799	Discontinued
0.6339	Remote Similarity	NPD3750	Approved
0.6332	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD919	Approved
0.6316	Remote Similarity	NPD37	Approved
0.6313	Remote Similarity	NPD7286	Phase 2
0.6308	Remote Similarity	NPD7229	Phase 3
0.6304	Remote Similarity	NPD6190	Approved
0.6294	Remote Similarity	NPD3019	Approved
0.6294	Remote Similarity	NPD2932	Approved
0.629	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5736	Approved
0.6283	Remote Similarity	NPD1465	Phase 2
0.6277	Remote Similarity	NPD7239	Suspended
0.6271	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD2344	Approved
0.6264	Remote Similarity	NPD1471	Phase 3
0.6261	Remote Similarity	NPD8366	Approved
0.625	Remote Similarity	NPD4628	Phase 3
0.625	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5953	Discontinued
0.625	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD7458	Discontinued
0.6243	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD6213	Phase 3
0.6232	Remote Similarity	NPD6212	Phase 3
0.6232	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6823	Phase 2
0.6224	Remote Similarity	NPD3787	Discontinued
0.6223	Remote Similarity	NPD5403	Approved
0.6222	Remote Similarity	NPD8491	Approved
0.6209	Remote Similarity	NPD4914	Approved
0.6209	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD1551	Phase 2
0.6203	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD1243	Approved
0.6196	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6166	Remote Similarity	NPD2296	Approved
0.6162	Remote Similarity	NPD8166	Discontinued
0.6162	Remote Similarity	NPD7003	Approved
0.6154	Remote Similarity	NPD2799	Discontinued
0.615	Remote Similarity	NPD4387	Approved
0.615	Remote Similarity	NPD4386	Approved
0.6139	Remote Similarity	NPD7240	Approved
0.6129	Remote Similarity	NPD2309	Approved
0.6127	Remote Similarity	NPD8407	Phase 2
0.6124	Remote Similarity	NPD4625	Phase 3
0.6117	Remote Similarity	NPD5401	Approved
0.6116	Remote Similarity	NPD7907	Approved
0.6108	Remote Similarity	NPD5028	Approved
0.6108	Remote Similarity	NPD4954	Approved
0.6108	Remote Similarity	NPD4955	Approved
0.6108	Remote Similarity	NPD36	Approved
0.6108	Remote Similarity	NPD5034	Approved
0.6108	Remote Similarity	NPD5026	Approved
0.6105	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD6273	Approved
0.6085	Remote Similarity	NPD5544	Approved
0.6082	Remote Similarity	NPD4288	Approved
0.608	Remote Similarity	NPD1164	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