NPASS Compound

Structure

NPC213471 OpenBabel07101719132D 26 27 0 0 0 0 0 0 0 0999 V2000 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 5 1 0 0 0 0 3 12 2 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 14 2 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 22 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 16 2 0 0 0 0 11 12 1 0 0 0 0 11 17 2 0 0 0 0 14 23 1 0 0 0 0 15 18 2 0 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 22 2 3 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.95
Volume:	381.064
LogP:	3.792
LogD:	3.534
LogS:	-4.461
# Rotatable Bonds:	7
TPSA:	68.12
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.366
Synthetic Accessibility Score:	3.013
Fsp3:	0.158
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:	-4.944
MDCK Permeability:	1.4911965081410017e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.168
20% Bioavailability (F20%):	0.069
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.389
Plasma Protein Binding (PPB):	98.37755584716797%
Volume Distribution (VD):	0.394
Pgp-substrate:	1.443583607673645%

ADMET: Metabolism

CYP1A2-inhibitor:	0.9
CYP1A2-substrate:	0.782
CYP2C19-inhibitor:	0.952
CYP2C19-substrate:	0.611
CYP2C9-inhibitor:	0.889
CYP2C9-substrate:	0.865
CYP2D6-inhibitor:	0.551
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.888
CYP3A4-substrate:	0.3

ADMET: Excretion

Clearance (CL):	1.252
Half-life (T1/2):	0.561

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.68
Drug-inuced Liver Injury (DILI):	0.561
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.106
Maximum Recommended Daily Dose:	0.83
Skin Sensitization:	0.886
Carcinogencity:	0.813
Eye Corrosion:	0.003
Eye Irritation:	0.041
Respiratory Toxicity:	0.242

Download Data

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

Natural Product: NPC213471

Natural Product ID:	NPC213471
*Common Name:**	Botryllamide A
IUPAC Name:	(Z)-N-[(E)-2-(3,5-dibromo-4-methoxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide
Synonyms:
Standard InCHIKey:	VIVASROQEPDEJV-HQFFKOPYSA-N
Standard InCHI:	InChI=1S/C19H17Br2NO4/c1-25-17(11-12-3-5-14(23)6-4-12)19(24)22-8-7-13-9-15(20)18(26-2)16(21)10-13/h3-11,23H,1-2H3,(H,22,24)/b8-7+,17-11-
SMILES:	CO/C(=Cc1ccc(cc1)O)/C(=N/C=C/c1cc(c(c(c1)Br)OC)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511679
PubChem CID:	10254699
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO17784	Botrylloides tyreum	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217298]
NPO17784	Botrylloides tyreum	Species	Styelidae	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
IC50	5

Activity Type	# Activity
Cell Line	1
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	33000.0	nM	PMID[479159]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	=	33000.0	nM	PMID[479160]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	=	11200.0	nM	PMID[479160]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	=	11200	nM	PMID[15387656]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	=	33000	nM	PMID[16643052]

☑ 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 NPC213471 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	224
0.1-0.2	3031
0.2-0.3	12434
0.3-0.4	6153
0.4-0.5	9472
0.5-0.6	9559
0.6-0.7	1699
0.7-0.8	111
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC303993
0.9457	High Similarity	NPC99280
0.876	High Similarity	NPC83279
0.8511	High Similarity	NPC474128
0.8295	Intermediate Similarity	NPC37302
0.8264	Intermediate Similarity	NPC78530
0.8264	Intermediate Similarity	NPC470472
0.8156	Intermediate Similarity	NPC470471
0.8154	Intermediate Similarity	NPC303370
0.8138	Intermediate Similarity	NPC135349
0.8129	Intermediate Similarity	NPC473724
0.8054	Intermediate Similarity	NPC258222
0.8042	Intermediate Similarity	NPC470470
0.791	Intermediate Similarity	NPC256369
0.7872	Intermediate Similarity	NPC475735
0.7872	Intermediate Similarity	NPC11449
0.7867	Intermediate Similarity	NPC76412
0.7843	Intermediate Similarity	NPC156311
0.7801	Intermediate Similarity	NPC474091
0.7786	Intermediate Similarity	NPC186898
0.7763	Intermediate Similarity	NPC47672
0.7724	Intermediate Similarity	NPC309667
0.7721	Intermediate Similarity	NPC41801
0.7676	Intermediate Similarity	NPC52029
0.7676	Intermediate Similarity	NPC195749
0.7676	Intermediate Similarity	NPC35961
0.766	Intermediate Similarity	NPC122359
0.766	Intermediate Similarity	NPC251571
0.766	Intermediate Similarity	NPC78061
0.766	Intermediate Similarity	NPC159987
0.7647	Intermediate Similarity	NPC43275
0.7636	Intermediate Similarity	NPC214188
0.7636	Intermediate Similarity	NPC74618
0.7636	Intermediate Similarity	NPC301941
0.7613	Intermediate Similarity	NPC233926
0.7606	Intermediate Similarity	NPC155838
0.7586	Intermediate Similarity	NPC71888
0.7586	Intermediate Similarity	NPC120114
0.7582	Intermediate Similarity	NPC109968
0.7576	Intermediate Similarity	NPC166837
0.7576	Intermediate Similarity	NPC475396
0.7569	Intermediate Similarity	NPC214869
0.7515	Intermediate Similarity	NPC290534
0.75	Intermediate Similarity	NPC323948
0.75	Intermediate Similarity	NPC469979
0.75	Intermediate Similarity	NPC473358
0.75	Intermediate Similarity	NPC114102
0.7481	Intermediate Similarity	NPC146530
0.7464	Intermediate Similarity	NPC263835
0.7456	Intermediate Similarity	NPC144823
0.7455	Intermediate Similarity	NPC298981
0.7455	Intermediate Similarity	NPC207819
0.7455	Intermediate Similarity	NPC473462
0.7455	Intermediate Similarity	NPC126128
0.7455	Intermediate Similarity	NPC110454
0.7448	Intermediate Similarity	NPC471953
0.7447	Intermediate Similarity	NPC213414
0.7426	Intermediate Similarity	NPC258992
0.7397	Intermediate Similarity	NPC163810
0.7394	Intermediate Similarity	NPC226001
0.7394	Intermediate Similarity	NPC110131
0.7348	Intermediate Similarity	NPC471495
0.7343	Intermediate Similarity	NPC301713
0.7333	Intermediate Similarity	NPC225130
0.7329	Intermediate Similarity	NPC474753
0.7324	Intermediate Similarity	NPC62101
0.7324	Intermediate Similarity	NPC95733
0.7315	Intermediate Similarity	NPC312770
0.7315	Intermediate Similarity	NPC14600
0.7315	Intermediate Similarity	NPC204848
0.7315	Intermediate Similarity	NPC160607
0.7315	Intermediate Similarity	NPC41473
0.7305	Intermediate Similarity	NPC296202
0.7293	Intermediate Similarity	NPC54543
0.7292	Intermediate Similarity	NPC153990
0.7273	Intermediate Similarity	NPC29477
0.7273	Intermediate Similarity	NPC296085
0.7267	Intermediate Similarity	NPC299583
0.7267	Intermediate Similarity	NPC296898
0.7254	Intermediate Similarity	NPC211218
0.7254	Intermediate Similarity	NPC105999
0.7248	Intermediate Similarity	NPC474587
0.7248	Intermediate Similarity	NPC475132
0.7234	Intermediate Similarity	NPC7830
0.7216	Intermediate Similarity	NPC469731
0.7209	Intermediate Similarity	NPC141405
0.7209	Intermediate Similarity	NPC473409
0.7209	Intermediate Similarity	NPC82741
0.7203	Intermediate Similarity	NPC272463
0.72	Intermediate Similarity	NPC474673
0.72	Intermediate Similarity	NPC475293
0.7197	Intermediate Similarity	NPC113457
0.7192	Intermediate Similarity	NPC478071
0.7183	Intermediate Similarity	NPC116562
0.7171	Intermediate Similarity	NPC195814
0.7161	Intermediate Similarity	NPC71629
0.7153	Intermediate Similarity	NPC115803
0.7151	Intermediate Similarity	NPC475658
0.7151	Intermediate Similarity	NPC471591
0.7151	Intermediate Similarity	NPC473892
0.7124	Intermediate Similarity	NPC222039
0.7124	Intermediate Similarity	NPC100478
0.7118	Intermediate Similarity	NPC475283
0.7118	Intermediate Similarity	NPC152205
0.7093	Intermediate Similarity	NPC49172
0.709	Intermediate Similarity	NPC96224
0.709	Intermediate Similarity	NPC201959
0.709	Intermediate Similarity	NPC24101
0.708	Intermediate Similarity	NPC59387
0.7071	Intermediate Similarity	NPC470626
0.7055	Intermediate Similarity	NPC202776
0.7047	Intermediate Similarity	NPC184465
0.7045	Intermediate Similarity	NPC12987
0.7045	Intermediate Similarity	NPC474603
0.7044	Intermediate Similarity	NPC73132
0.7044	Intermediate Similarity	NPC471235
0.7044	Intermediate Similarity	NPC235033
0.7042	Intermediate Similarity	NPC170824
0.7041	Intermediate Similarity	NPC475615
0.7034	Intermediate Similarity	NPC170583
0.7034	Intermediate Similarity	NPC207541
0.7034	Intermediate Similarity	NPC246133
0.7034	Intermediate Similarity	NPC182147
0.7034	Intermediate Similarity	NPC71105
0.7034	Intermediate Similarity	NPC152186
0.7027	Intermediate Similarity	NPC308885
0.7027	Intermediate Similarity	NPC255550
0.7027	Intermediate Similarity	NPC45191
0.7021	Intermediate Similarity	NPC38483
0.7006	Intermediate Similarity	NPC469721
0.7	Intermediate Similarity	NPC293619
0.6993	Remote Similarity	NPC477837
0.6993	Remote Similarity	NPC477838
0.6987	Remote Similarity	NPC5462
0.6986	Remote Similarity	NPC156944
0.6986	Remote Similarity	NPC251466
0.698	Remote Similarity	NPC166624
0.698	Remote Similarity	NPC130595
0.698	Remote Similarity	NPC93882
0.6972	Remote Similarity	NPC227217
0.6972	Remote Similarity	NPC232316
0.6972	Remote Similarity	NPC117780
0.6972	Remote Similarity	NPC95614
0.6972	Remote Similarity	NPC56214
0.6972	Remote Similarity	NPC165133
0.6972	Remote Similarity	NPC242885
0.6968	Remote Similarity	NPC178466
0.6968	Remote Similarity	NPC63628
0.6966	Remote Similarity	NPC236265
0.6966	Remote Similarity	NPC300955
0.6963	Remote Similarity	NPC75440
0.6963	Remote Similarity	NPC309982
0.6959	Remote Similarity	NPC470706
0.695	Remote Similarity	NPC122009
0.6944	Remote Similarity	NPC471315
0.6944	Remote Similarity	NPC471314
0.6944	Remote Similarity	NPC229213
0.6939	Remote Similarity	NPC99798
0.6939	Remote Similarity	NPC41331
0.6939	Remote Similarity	NPC291449
0.6939	Remote Similarity	NPC157740
0.6937	Remote Similarity	NPC470710
0.6933	Remote Similarity	NPC6854
0.6933	Remote Similarity	NPC285078
0.6933	Remote Similarity	NPC313737
0.6928	Remote Similarity	NPC197766
0.6928	Remote Similarity	NPC471236
0.6923	Remote Similarity	NPC207613
0.6923	Remote Similarity	NPC109083
0.6923	Remote Similarity	NPC189844
0.6923	Remote Similarity	NPC224814
0.6923	Remote Similarity	NPC60962
0.6923	Remote Similarity	NPC14007
0.6923	Remote Similarity	NPC269843
0.6914	Remote Similarity	NPC470951
0.6912	Remote Similarity	NPC474272
0.6908	Remote Similarity	NPC470249
0.6906	Remote Similarity	NPC94217
0.6901	Remote Similarity	NPC86007
0.6901	Remote Similarity	NPC281298
0.6901	Remote Similarity	NPC44270
0.6901	Remote Similarity	NPC310338
0.6901	Remote Similarity	NPC163036
0.6897	Remote Similarity	NPC474169
0.6897	Remote Similarity	NPC473572
0.6892	Remote Similarity	NPC147247
0.6892	Remote Similarity	NPC246974
0.6889	Remote Similarity	NPC142297
0.6887	Remote Similarity	NPC218530
0.6883	Remote Similarity	NPC83289
0.6883	Remote Similarity	NPC189724
0.6883	Remote Similarity	NPC212850
0.6879	Remote Similarity	NPC313414
0.6879	Remote Similarity	NPC283468
0.6875	Remote Similarity	NPC38996
0.6875	Remote Similarity	NPC113865
0.6875	Remote Similarity	NPC312675
0.6875	Remote Similarity	NPC343720
0.6875	Remote Similarity	NPC54872
0.6875	Remote Similarity	NPC475432

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 NPC213471 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	965
0.2-0.3	1271
0.3-0.4	2745
0.4-0.5	2522
0.5-0.6	1260
0.6-0.7	229
0.7-0.8	0
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
0.7292	Intermediate Similarity	NPD4993	Discontinued
0.707	Intermediate Similarity	NPD2184	Approved
0.707	Intermediate Similarity	NPD2183	Approved
0.7047	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3144	Approved
0.7027	Intermediate Similarity	NPD3145	Approved
0.7014	Intermediate Similarity	NPD6583	Phase 3
0.7014	Intermediate Similarity	NPD6582	Phase 2
0.698	Remote Similarity	NPD2674	Phase 3
0.6974	Remote Similarity	NPD1169	Approved
0.6966	Remote Similarity	NPD2922	Phase 1
0.6897	Remote Similarity	NPD1669	Approved
0.6897	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6584	Phase 3
0.6853	Remote Similarity	NPD2667	Approved
0.6853	Remote Similarity	NPD2668	Approved
0.6781	Remote Similarity	NPD3685	Discontinued
0.6781	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD821	Approved
0.6715	Remote Similarity	NPD2684	Approved
0.6691	Remote Similarity	NPD228	Approved
0.669	Remote Similarity	NPD3596	Phase 2
0.669	Remote Similarity	NPD3847	Discontinued
0.6689	Remote Similarity	NPD1048	Approved
0.6687	Remote Similarity	NPD3985	Discontinued
0.6687	Remote Similarity	NPD4123	Phase 3
0.6686	Remote Similarity	NPD4010	Discontinued
0.6646	Remote Similarity	NPD5481	Discontinued
0.6643	Remote Similarity	NPD7843	Approved
0.6629	Remote Similarity	NPD2802	Phase 3
0.6601	Remote Similarity	NPD1558	Phase 1
0.6599	Remote Similarity	NPD2233	Approved
0.6599	Remote Similarity	NPD2232	Approved
0.6599	Remote Similarity	NPD2230	Approved
0.6597	Remote Similarity	NPD6581	Approved
0.6597	Remote Similarity	NPD6580	Approved
0.6596	Remote Similarity	NPD5283	Phase 1
0.6582	Remote Similarity	NPD3060	Approved
0.6577	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD3421	Phase 3
0.6569	Remote Similarity	NPD968	Approved
0.6565	Remote Similarity	NPD2933	Approved
0.6565	Remote Similarity	NPD2934	Approved
0.6552	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6331	Phase 2
0.6538	Remote Similarity	NPD4108	Discontinued
0.6536	Remote Similarity	NPD7477	Discontinued
0.6536	Remote Similarity	NPD1423	Approved
0.6527	Remote Similarity	NPD2296	Approved
0.6522	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4357	Discontinued
0.6516	Remote Similarity	NPD3054	Approved
0.6516	Remote Similarity	NPD3052	Approved
0.6515	Remote Similarity	NPD2860	Approved
0.6515	Remote Similarity	NPD2859	Approved
0.6513	Remote Similarity	NPD3179	Approved
0.6513	Remote Similarity	NPD3180	Approved
0.6513	Remote Similarity	NPD3027	Phase 3
0.6513	Remote Similarity	NPD5163	Phase 2
0.6513	Remote Similarity	NPD9718	Approved
0.6503	Remote Similarity	NPD7157	Approved
0.6503	Remote Similarity	NPD2557	Approved
0.6503	Remote Similarity	NPD709	Approved
0.6486	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD4678	Approved
0.6485	Remote Similarity	NPD4675	Approved
0.6481	Remote Similarity	NPD3536	Discontinued
0.6471	Remote Similarity	NPD5110	Phase 2
0.6471	Remote Similarity	NPD5111	Phase 2
0.6471	Remote Similarity	NPD5109	Approved
0.6467	Remote Similarity	NPD1820	Approved
0.6467	Remote Similarity	NPD1819	Approved
0.6467	Remote Similarity	NPD1818	Approved
0.6467	Remote Similarity	NPD1817	Approved
0.6456	Remote Similarity	NPD3656	Approved
0.6447	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6072	Discontinued
0.6443	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5451	Approved
0.6415	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD5536	Phase 2
0.6408	Remote Similarity	NPD2497	Approved
0.6408	Remote Similarity	NPD2496	Approved
0.6405	Remote Similarity	NPD3166	Approved
0.6405	Remote Similarity	NPD3167	Approved
0.6405	Remote Similarity	NPD3165	Approved
0.6405	Remote Similarity	NPD3164	Approved
0.6403	Remote Similarity	NPD290	Approved
0.6403	Remote Similarity	NPD1358	Approved
0.6402	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD2219	Phase 1
0.6395	Remote Similarity	NPD6516	Phase 2
0.6395	Remote Similarity	NPD5846	Approved
0.6395	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD2161	Phase 2
0.6387	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4060	Phase 1
0.6382	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD2231	Phase 2
0.6376	Remote Similarity	NPD2235	Phase 2
0.6375	Remote Similarity	NPD4162	Approved
0.6374	Remote Similarity	NPD1411	Approved
0.637	Remote Similarity	NPD3020	Approved
0.6364	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2229	Approved
0.6364	Remote Similarity	NPD2234	Approved
0.6364	Remote Similarity	NPD2228	Approved
0.6364	Remote Similarity	NPD4003	Phase 3
0.6364	Remote Similarity	NPD5718	Phase 2
0.6358	Remote Similarity	NPD1232	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD3778	Approved
0.6341	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6540	Phase 3
0.6333	Remote Similarity	NPD6542	Approved
0.6333	Remote Similarity	NPD2428	Approved
0.6333	Remote Similarity	NPD6543	Approved
0.6333	Remote Similarity	NPD6539	Approved
0.6333	Remote Similarity	NPD4129	Approved
0.6333	Remote Similarity	NPD2429	Approved
0.6327	Remote Similarity	NPD6382	Discontinued
0.6327	Remote Similarity	NPD2595	Approved
0.6327	Remote Similarity	NPD3444	Approved
0.6327	Remote Similarity	NPD2594	Approved
0.6327	Remote Similarity	NPD3049	Approved
0.6327	Remote Similarity	NPD3445	Approved
0.6327	Remote Similarity	NPD3443	Approved
0.6325	Remote Similarity	NPD4005	Discontinued
0.6323	Remote Similarity	NPD840	Approved
0.6323	Remote Similarity	NPD7265	Discontinued
0.6323	Remote Similarity	NPD839	Approved
0.6316	Remote Similarity	NPD7451	Discontinued
0.6312	Remote Similarity	NPD3022	Approved
0.6312	Remote Similarity	NPD7153	Discontinued
0.6312	Remote Similarity	NPD3021	Approved
0.631	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD776	Approved
0.6306	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4097	Suspended
0.6306	Remote Similarity	NPD2157	Approved
0.6304	Remote Similarity	NPD9244	Approved
0.6303	Remote Similarity	NPD7131	Phase 3
0.6299	Remote Similarity	NPD1024	Discontinued
0.6299	Remote Similarity	NPD6179	Discontinued
0.6299	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5241	Discontinued
0.6294	Remote Similarity	NPD5535	Approved
0.6291	Remote Similarity	NPD6541	Approved
0.6291	Remote Similarity	NPD6538	Approved
0.6289	Remote Similarity	NPD6032	Approved
0.6289	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD6502	Phase 2
0.6287	Remote Similarity	NPD1009	Approved
0.6284	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD2554	Approved
0.6284	Remote Similarity	NPD2556	Approved
0.6282	Remote Similarity	NPD2238	Phase 2
0.6275	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD1712	Approved
0.6273	Remote Similarity	NPD2458	Approved
0.6273	Remote Similarity	NPD2459	Approved
0.6273	Remote Similarity	NPD4236	Phase 3
0.6273	Remote Similarity	NPD4237	Approved
0.6273	Remote Similarity	NPD2460	Phase 3
0.6272	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD6895	Approved
0.6266	Remote Similarity	NPD6896	Approved
0.6264	Remote Similarity	NPD4083	Discontinued
0.6259	Remote Similarity	NPD2486	Discontinued
0.6259	Remote Similarity	NPD1548	Phase 1
0.6258	Remote Similarity	NPD6798	Discontinued
0.6258	Remote Similarity	NPD5756	Phase 2
0.625	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3567	Approved
0.625	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3236	Phase 3
0.625	Remote Similarity	NPD1794	Approved
0.625	Remote Similarity	NPD3568	Approved
0.6235	Remote Similarity	NPD3560	Approved
0.6235	Remote Similarity	NPD3558	Approved
0.6235	Remote Similarity	NPD3557	Approved
0.6235	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD3556	Approved
0.6234	Remote Similarity	NPD2614	Approved
0.6234	Remote Similarity	NPD4908	Phase 1
0.6226	Remote Similarity	NPD2154	Approved
0.6226	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD2156	Approved
0.6226	Remote Similarity	NPD2155	Approved
0.6225	Remote Similarity	NPD2983	Phase 2
0.6225	Remote Similarity	NPD2982	Phase 2
0.622	Remote Similarity	NPD7212	Phase 2
0.622	Remote Similarity	NPD7213	Phase 3
0.6218	Remote Similarity	NPD6233	Phase 2
0.6218	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4062	Phase 3
0.6216	Remote Similarity	NPD1357	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