NPASS Compound

Structure

NPC11449 OpenBabel07101719152D 24 26 0 0 0 0 0 0 0 0999 V2000 4.0862 2.2882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6977 3.0085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2330 1.3612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6488 3.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1840 1.6702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4612 1.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4898 2.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3920 2.6483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5827 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 3.3364 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 0.3364 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.0933 -1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 2.3364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3430 2.9574 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 23 1 0 0 0 0 2 4 1 0 0 0 0 2 10 2 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 12 2 0 0 0 0 5 12 1 0 0 0 0 6 10 1 0 0 0 0 6 16 2 3 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 15 2 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 11 13 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 18 1 0 0 0 0 15 20 1 0 0 0 0 16 24 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	449.91
Volume:	344.215
LogP:	4.486
LogD:	2.69
LogS:	-4.963
# Rotatable Bonds:	3
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.673
Synthetic Accessibility Score:	2.723
Fsp3:	0.056
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.407
MDCK Permeability:	1.570856329635717e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.329
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.131
Plasma Protein Binding (PPB):	99.77244567871094%
Volume Distribution (VD):	0.436
Pgp-substrate:	2.0350100994110107%

ADMET: Metabolism

CYP1A2-inhibitor:	0.926
CYP1A2-substrate:	0.251
CYP2C19-inhibitor:	0.893
CYP2C19-substrate:	0.09
CYP2C9-inhibitor:	0.842
CYP2C9-substrate:	0.841
CYP2D6-inhibitor:	0.184
CYP2D6-substrate:	0.692
CYP3A4-inhibitor:	0.301
CYP3A4-substrate:	0.144

ADMET: Excretion

Clearance (CL):	0.601
Half-life (T1/2):	0.755

ADMET: Toxicity

hERG Blockers:	0.331
Human Hepatotoxicity (H-HT):	0.549
Drug-inuced Liver Injury (DILI):	0.095
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.879
Maximum Recommended Daily Dose:	0.823
Skin Sensitization:	0.933
Carcinogencity:	0.285
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.667

Download Data

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

Natural Product: NPC11449

Natural Product ID:	NPC11449
*Common Name:**	Rubrolide P
IUPAC Name:	4-(3,5-dibromo-4-hydroxyphenyl)-5-[(4-methoxyphenyl)methylidene]furan-2-one
Synonyms:	Rubrolide P
Standard InCHIKey:	KBZLYXAVDMVYSJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12Br2O4/c1-23-12-4-2-10(3-5-12)6-16-13(9-17(21)24-16)11-7-14(19)18(22)15(20)8-11/h2-9,22H,1H3
SMILES:	COc1ccc(cc1)C=C1OC(=O)C=C1c1cc(Br)c(c(c1)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204148
PubChem CID:	73355891
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO33352	pseudodistoma antinboja	Species	Pseudodistomidae	Eukaryota	n.a.	Korean	n.a.	PMID[23145884]

☑ 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
MIC	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	32.0	ug.mL-1	PMID[555947]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	50.0	ug.mL-1	PMID[555947]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	=	6.3	ug.mL-1	PMID[555947]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	50.0	ug.mL-1	PMID[555947]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	50.0	ug.mL-1	PMID[555947]

☑ 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 NPC11449 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	298
0.1-0.2	1848
0.2-0.3	5908
0.3-0.4	13034
0.4-0.5	4833
0.5-0.6	10651
0.6-0.7	5824
0.7-0.8	263
0.8-0.85	17
0.85-0.9	8
0.9-0.95	9
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC159987
0.9756	High Similarity	NPC122359
0.9756	High Similarity	NPC78061
0.9512	High Similarity	NPC213414
0.935	High Similarity	NPC296202
0.9274	High Similarity	NPC105999
0.9268	High Similarity	NPC7830
0.9141	High Similarity	NPC478071
0.8699	High Similarity	NPC296526
0.8662	High Similarity	NPC235033
0.8662	High Similarity	NPC471235
0.8662	High Similarity	NPC470710
0.8662	High Similarity	NPC73132
0.854	High Similarity	NPC81137
0.845	Intermediate Similarity	NPC116562
0.8333	Intermediate Similarity	NPC471236
0.8333	Intermediate Similarity	NPC197766
0.8239	Intermediate Similarity	NPC122599
0.8239	Intermediate Similarity	NPC270848
0.8239	Intermediate Similarity	NPC272868
0.8211	Intermediate Similarity	NPC79543
0.8145	Intermediate Similarity	NPC473358
0.8129	Intermediate Similarity	NPC177967
0.8129	Intermediate Similarity	NPC471237
0.8099	Intermediate Similarity	NPC147137
0.8077	Intermediate Similarity	NPC180207
0.7984	Intermediate Similarity	NPC471495
0.792	Intermediate Similarity	NPC54543
0.7872	Intermediate Similarity	NPC213471
0.7857	Intermediate Similarity	NPC183700
0.784	Intermediate Similarity	NPC206341
0.781	Intermediate Similarity	NPC219923
0.7769	Intermediate Similarity	NPC128249
0.7742	Intermediate Similarity	NPC127676
0.7708	Intermediate Similarity	NPC474128
0.768	Intermediate Similarity	NPC113457
0.7664	Intermediate Similarity	NPC213552
0.7664	Intermediate Similarity	NPC120225
0.7661	Intermediate Similarity	NPC2518
0.7661	Intermediate Similarity	NPC109637
0.766	Intermediate Similarity	NPC303993
0.7652	Intermediate Similarity	NPC311091
0.7652	Intermediate Similarity	NPC471033
0.7634	Intermediate Similarity	NPC19290
0.7619	Intermediate Similarity	NPC260952
0.7594	Intermediate Similarity	NPC264976
0.7591	Intermediate Similarity	NPC289459
0.7574	Intermediate Similarity	NPC473942
0.7557	Intermediate Similarity	NPC51345
0.7554	Intermediate Similarity	NPC2596
0.7518	Intermediate Similarity	NPC236265
0.7518	Intermediate Similarity	NPC246704
0.75	Intermediate Similarity	NPC99280
0.75	Intermediate Similarity	NPC83062
0.7483	Intermediate Similarity	NPC78530
0.7483	Intermediate Similarity	NPC184632
0.7481	Intermediate Similarity	NPC94217
0.7462	Intermediate Similarity	NPC199462
0.7462	Intermediate Similarity	NPC17693
0.746	Intermediate Similarity	NPC227255
0.745	Intermediate Similarity	NPC296085
0.7445	Intermediate Similarity	NPC14141
0.7442	Intermediate Similarity	NPC63345
0.744	Intermediate Similarity	NPC179686
0.744	Intermediate Similarity	NPC304638
0.7426	Intermediate Similarity	NPC251259
0.7422	Intermediate Similarity	NPC75440
0.7422	Intermediate Similarity	NPC201959
0.7419	Intermediate Similarity	NPC253746
0.7419	Intermediate Similarity	NPC474535
0.7417	Intermediate Similarity	NPC258222
0.7413	Intermediate Similarity	NPC471328
0.741	Intermediate Similarity	NPC474476
0.7407	Intermediate Similarity	NPC2058
0.7405	Intermediate Similarity	NPC471488
0.7402	Intermediate Similarity	NPC326447
0.7394	Intermediate Similarity	NPC259017
0.7391	Intermediate Similarity	NPC60517
0.7391	Intermediate Similarity	NPC146886
0.7391	Intermediate Similarity	NPC20443
0.7391	Intermediate Similarity	NPC89630
0.7388	Intermediate Similarity	NPC293424
0.7388	Intermediate Similarity	NPC275519
0.7381	Intermediate Similarity	NPC474603
0.7381	Intermediate Similarity	NPC12987
0.7372	Intermediate Similarity	NPC475697
0.7365	Intermediate Similarity	NPC135349
0.7364	Intermediate Similarity	NPC234639
0.7364	Intermediate Similarity	NPC474272
0.7353	Intermediate Similarity	NPC470848
0.7353	Intermediate Similarity	NPC470849
0.7353	Intermediate Similarity	NPC131868
0.7353	Intermediate Similarity	NPC471486
0.7348	Intermediate Similarity	NPC235250
0.7344	Intermediate Similarity	NPC151530
0.7344	Intermediate Similarity	NPC157473
0.7339	Intermediate Similarity	NPC171843
0.7338	Intermediate Similarity	NPC168259
0.7333	Intermediate Similarity	NPC38483
0.7333	Intermediate Similarity	NPC263386
0.7333	Intermediate Similarity	NPC71629
0.7333	Intermediate Similarity	NPC141791
0.7324	Intermediate Similarity	NPC32463
0.7323	Intermediate Similarity	NPC288760
0.7323	Intermediate Similarity	NPC128730
0.7323	Intermediate Similarity	NPC473855
0.7319	Intermediate Similarity	NPC212541
0.7313	Intermediate Similarity	NPC263754
0.7313	Intermediate Similarity	NPC183154
0.7308	Intermediate Similarity	NPC473809
0.7308	Intermediate Similarity	NPC471487
0.7305	Intermediate Similarity	NPC110313
0.7305	Intermediate Similarity	NPC478215
0.7299	Intermediate Similarity	NPC52247
0.7299	Intermediate Similarity	NPC187868
0.7279	Intermediate Similarity	NPC202474
0.7279	Intermediate Similarity	NPC31314
0.7279	Intermediate Similarity	NPC193193
0.7273	Intermediate Similarity	NPC474753
0.7273	Intermediate Similarity	NPC141003
0.7273	Intermediate Similarity	NPC35344
0.7273	Intermediate Similarity	NPC33244
0.7273	Intermediate Similarity	NPC250727
0.7266	Intermediate Similarity	NPC176971
0.7266	Intermediate Similarity	NPC288945
0.726	Intermediate Similarity	NPC223616
0.726	Intermediate Similarity	NPC90431
0.7259	Intermediate Similarity	NPC277460
0.7259	Intermediate Similarity	NPC107588
0.7259	Intermediate Similarity	NPC137537
0.7259	Intermediate Similarity	NPC70744
0.7259	Intermediate Similarity	NPC164706
0.7259	Intermediate Similarity	NPC272471
0.7255	Intermediate Similarity	NPC47672
0.7252	Intermediate Similarity	NPC139946
0.7248	Intermediate Similarity	NPC470472
0.7244	Intermediate Similarity	NPC283546
0.7241	Intermediate Similarity	NPC135127
0.7239	Intermediate Similarity	NPC33717
0.7237	Intermediate Similarity	NPC178097
0.7231	Intermediate Similarity	NPC75272
0.7231	Intermediate Similarity	NPC473372
0.7231	Intermediate Similarity	NPC471954
0.7226	Intermediate Similarity	NPC156311
0.7226	Intermediate Similarity	NPC224814
0.7226	Intermediate Similarity	NPC14007
0.7226	Intermediate Similarity	NPC189844
0.7226	Intermediate Similarity	NPC204466
0.7226	Intermediate Similarity	NPC109083
0.7226	Intermediate Similarity	NPC269843
0.7226	Intermediate Similarity	NPC60962
0.7222	Intermediate Similarity	NPC307425
0.7218	Intermediate Similarity	NPC294941
0.7214	Intermediate Similarity	NPC4164
0.7214	Intermediate Similarity	NPC88403
0.7206	Intermediate Similarity	NPC117759
0.7203	Intermediate Similarity	NPC475735
0.72	Intermediate Similarity	NPC100870
0.7194	Intermediate Similarity	NPC473572
0.7194	Intermediate Similarity	NPC474169
0.7194	Intermediate Similarity	NPC315807
0.7192	Intermediate Similarity	NPC477301
0.7188	Intermediate Similarity	NPC238115
0.7188	Intermediate Similarity	NPC470393
0.7185	Intermediate Similarity	NPC280001
0.7185	Intermediate Similarity	NPC122117
0.7183	Intermediate Similarity	NPC217431
0.7181	Intermediate Similarity	NPC89341
0.7176	Intermediate Similarity	NPC25067
0.7176	Intermediate Similarity	NPC88868
0.7176	Intermediate Similarity	NPC231251
0.7176	Intermediate Similarity	NPC141068
0.7174	Intermediate Similarity	NPC70752
0.7174	Intermediate Similarity	NPC147654
0.7164	Intermediate Similarity	NPC185541
0.7164	Intermediate Similarity	NPC464
0.7163	Intermediate Similarity	NPC90128
0.7163	Intermediate Similarity	NPC303680
0.7163	Intermediate Similarity	NPC84076
0.7154	Intermediate Similarity	NPC291837
0.7153	Intermediate Similarity	NPC474874
0.7143	Intermediate Similarity	NPC107101
0.7143	Intermediate Similarity	NPC474673
0.7143	Intermediate Similarity	NPC140521
0.7143	Intermediate Similarity	NPC109241
0.7143	Intermediate Similarity	NPC120852
0.7133	Intermediate Similarity	NPC241354
0.7132	Intermediate Similarity	NPC1065
0.7132	Intermediate Similarity	NPC124916
0.7132	Intermediate Similarity	NPC203124
0.7132	Intermediate Similarity	NPC470626
0.7132	Intermediate Similarity	NPC309434
0.7132	Intermediate Similarity	NPC135464
0.7132	Intermediate Similarity	NPC92623
0.7124	Intermediate Similarity	NPC76412
0.7123	Intermediate Similarity	NPC470471
0.7123	Intermediate Similarity	NPC245386
0.7123	Intermediate Similarity	NPC5310
0.7123	Intermediate Similarity	NPC67247
0.7123	Intermediate Similarity	NPC131950

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 NPC11449 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	1091
0.2-0.3	1542
0.3-0.4	2943
0.4-0.5	1835
0.5-0.6	1171
0.6-0.7	300
0.7-0.8	13
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
0.7647	Intermediate Similarity	NPD2296	Approved
0.7462	Intermediate Similarity	NPD5535	Approved
0.7419	Intermediate Similarity	NPD4288	Approved
0.7402	Intermediate Similarity	NPD3134	Approved
0.7353	Intermediate Similarity	NPD3847	Discontinued
0.7344	Intermediate Similarity	NPD1358	Approved
0.7299	Intermediate Similarity	NPD422	Phase 1
0.7299	Intermediate Similarity	NPD1535	Discovery
0.7259	Intermediate Similarity	NPD1894	Discontinued
0.7246	Intermediate Similarity	NPD1481	Phase 2
0.7153	Intermediate Similarity	NPD4626	Approved
0.7132	Intermediate Similarity	NPD968	Approved
0.7103	Intermediate Similarity	NPD4060	Phase 1
0.7101	Intermediate Similarity	NPD3496	Discontinued
0.7092	Intermediate Similarity	NPD2797	Approved
0.7071	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3225	Approved
0.7016	Intermediate Similarity	NPD2933	Approved
0.7016	Intermediate Similarity	NPD2934	Approved
0.7014	Intermediate Similarity	NPD9718	Approved
0.698	Remote Similarity	NPD2935	Discontinued
0.6972	Remote Similarity	NPD1203	Approved
0.6966	Remote Similarity	NPD3268	Approved
0.6966	Remote Similarity	NPD6798	Discontinued
0.6966	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.696	Remote Similarity	NPD2859	Approved
0.696	Remote Similarity	NPD2860	Approved
0.6957	Remote Similarity	NPD5691	Approved
0.6939	Remote Similarity	NPD4340	Discontinued
0.6939	Remote Similarity	NPD6355	Discontinued
0.6923	Remote Similarity	NPD9697	Approved
0.6919	Remote Similarity	NPD4287	Approved
0.6918	Remote Similarity	NPD4062	Phase 3
0.6918	Remote Similarity	NPD6233	Phase 2
0.6901	Remote Similarity	NPD1283	Approved
0.6897	Remote Similarity	NPD7095	Approved
0.6897	Remote Similarity	NPD5163	Phase 2
0.6894	Remote Similarity	NPD2684	Approved
0.6889	Remote Similarity	NPD1241	Discontinued
0.6884	Remote Similarity	NPD1548	Phase 1
0.6884	Remote Similarity	NPD9545	Approved
0.6883	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD228	Approved
0.6849	Remote Similarity	NPD3764	Approved
0.6842	Remote Similarity	NPD5451	Approved
0.6842	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6582	Phase 2
0.6831	Remote Similarity	NPD6583	Phase 3
0.6815	Remote Similarity	NPD7843	Approved
0.6812	Remote Similarity	NPD5536	Phase 2
0.68	Remote Similarity	NPD2799	Discontinued
0.6797	Remote Similarity	NPD3020	Approved
0.6797	Remote Similarity	NPD4628	Phase 3
0.6765	Remote Similarity	NPD5283	Phase 1
0.6761	Remote Similarity	NPD1608	Approved
0.6761	Remote Similarity	NPD9717	Approved
0.6757	Remote Similarity	NPD4140	Approved
0.6743	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3267	Approved
0.6736	Remote Similarity	NPD3266	Approved
0.6714	Remote Similarity	NPD5585	Approved
0.6712	Remote Similarity	NPD2614	Approved
0.6712	Remote Similarity	NPD6832	Phase 2
0.6712	Remote Similarity	NPD4908	Phase 1
0.6691	Remote Similarity	NPD821	Approved
0.669	Remote Similarity	NPD6584	Phase 3
0.669	Remote Similarity	NPD1281	Approved
0.669	Remote Similarity	NPD1610	Phase 2
0.6689	Remote Similarity	NPD4870	Approved
0.6689	Remote Similarity	NPD4308	Phase 3
0.6689	Remote Similarity	NPD7033	Discontinued
0.6688	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD6671	Approved
0.6667	Remote Similarity	NPD2802	Phase 3
0.6667	Remote Similarity	NPD7157	Approved
0.6646	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2861	Phase 2
0.6644	Remote Similarity	NPD1240	Approved
0.6643	Remote Similarity	NPD3972	Approved
0.6623	Remote Similarity	NPD7097	Phase 1
0.6622	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD2313	Discontinued
0.6619	Remote Similarity	NPD9493	Approved
0.6603	Remote Similarity	NPD7440	Discontinued
0.6601	Remote Similarity	NPD2344	Approved
0.66	Remote Similarity	NPD5124	Phase 1
0.66	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD9244	Approved
0.6581	Remote Similarity	NPD7003	Approved
0.6573	Remote Similarity	NPD1611	Approved
0.6567	Remote Similarity	NPD290	Approved
0.6558	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1607	Approved
0.6554	Remote Similarity	NPD3027	Phase 3
0.6549	Remote Similarity	NPD2668	Approved
0.6549	Remote Similarity	NPD6516	Phase 2
0.6549	Remote Similarity	NPD1778	Approved
0.6549	Remote Similarity	NPD17	Approved
0.6549	Remote Similarity	NPD2667	Approved
0.6549	Remote Similarity	NPD5846	Approved
0.6538	Remote Similarity	NPD2354	Approved
0.6536	Remote Similarity	NPD4476	Approved
0.6536	Remote Similarity	NPD4477	Approved
0.6536	Remote Similarity	NPD1538	Phase 1
0.6536	Remote Similarity	NPD1519	Approved
0.6536	Remote Similarity	NPD1537	Approved
0.6536	Remote Similarity	NPD1551	Phase 2
0.6533	Remote Similarity	NPD2979	Phase 3
0.6519	Remote Similarity	NPD3536	Discontinued
0.6516	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.651	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD6362	Approved
0.6507	Remote Similarity	NPD987	Approved
0.65	Remote Similarity	NPD3596	Phase 2
0.6494	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7266	Discontinued
0.6494	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD4359	Approved
0.6483	Remote Similarity	NPD3685	Discontinued
0.6479	Remote Similarity	NPD1651	Approved
0.6478	Remote Similarity	NPD6273	Approved
0.6474	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4110	Phase 3
0.6471	Remote Similarity	NPD1510	Phase 2
0.6471	Remote Similarity	NPD3021	Approved
0.6471	Remote Similarity	NPD3022	Approved
0.6467	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD5745	Approved
0.6463	Remote Similarity	NPD2798	Approved
0.6463	Remote Similarity	NPD5647	Approved
0.6456	Remote Similarity	NPD6799	Approved
0.6452	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5958	Discontinued
0.6452	Remote Similarity	NPD1549	Phase 2
0.6452	Remote Similarity	NPD4534	Discontinued
0.6447	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD6653	Approved
0.6438	Remote Similarity	NPD196	Phase 1
0.6433	Remote Similarity	NPD2309	Approved
0.6429	Remote Similarity	NPD709	Approved
0.6429	Remote Similarity	NPD6032	Approved
0.6429	Remote Similarity	NPD1522	Approved
0.6429	Remote Similarity	NPD1523	Approved
0.6424	Remote Similarity	NPD4307	Phase 2
0.6423	Remote Similarity	NPD111	Approved
0.6419	Remote Similarity	NPD5736	Approved
0.6419	Remote Similarity	NPD454	Approved
0.6415	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.641	Remote Similarity	NPD1652	Phase 2
0.6408	Remote Similarity	NPD6580	Approved
0.6408	Remote Similarity	NPD1182	Approved
0.6408	Remote Similarity	NPD6581	Approved
0.6405	Remote Similarity	NPD1536	Approved
0.6392	Remote Similarity	NPD6667	Approved
0.6392	Remote Similarity	NPD6666	Approved
0.6387	Remote Similarity	NPD5763	Approved
0.6387	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD2346	Discontinued
0.6387	Remote Similarity	NPD5762	Approved
0.6387	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD2353	Approved
0.6383	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD1933	Approved
0.638	Remote Similarity	NPD7411	Suspended
0.6376	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD2183	Approved
0.6375	Remote Similarity	NPD2184	Approved
0.6369	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3028	Approved
0.6364	Remote Similarity	NPD1357	Approved
0.6364	Remote Similarity	NPD3748	Approved
0.6364	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD7458	Discontinued
0.6358	Remote Similarity	NPD8032	Phase 2
0.6357	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD4624	Approved
0.6349	Remote Similarity	NPD9295	Approved
0.6346	Remote Similarity	NPD2424	Discontinued
0.6345	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD5909	Discontinued
0.634	Remote Similarity	NPD3054	Approved
0.634	Remote Similarity	NPD3052	Approved
0.6333	Remote Similarity	NPD5746	Approved
0.6329	Remote Similarity	NPD3887	Approved
0.6325	Remote Similarity	NPD7768	Phase 2
0.6324	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD2531	Phase 2
0.6323	Remote Similarity	NPD2438	Suspended
0.6316	Remote Similarity	NPD1613	Approved
0.6316	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD2557	Approved
0.6312	Remote Similarity	NPD6387	Discontinued
0.6309	Remote Similarity	NPD9494	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