NPASS Compound

Structure

CID303993 OpenBabel06191716112D 25 26 0 0 0 0 0 0 0 0999 V2000 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 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 -0.8660 1.5000 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 -0.0000 1.0000 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 -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 -0.8660 -0.5000 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 -6.0622 1.5000 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 -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 0.8660 -0.5000 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 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 6 1 0 0 0 0 3 13 2 0 0 0 0 4 7 2 0 0 0 0 4 13 1 0 0 0 0 5 8 2 0 0 0 0 5 14 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 21 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 18 2 0 0 0 0 15 22 1 0 0 0 0 16 17 2 0 0 0 0 16 20 1 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 25 1 0 0 0 0 19 21 2 3 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	403.04
Volume:	361.78
LogP:	3.124
LogD:	3.32
LogS:	-4.044
# Rotatable Bonds:	7
TPSA:	68.12
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.449
Synthetic Accessibility Score:	2.823
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:	-4.861
MDCK Permeability:	1.599198003532365e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.135
20% Bioavailability (F20%):	0.07
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.421
Plasma Protein Binding (PPB):	97.4367446899414%
Volume Distribution (VD):	0.491
Pgp-substrate:	1.398094892501831%

ADMET: Metabolism

CYP1A2-inhibitor:	0.885
CYP1A2-substrate:	0.908
CYP2C19-inhibitor:	0.952
CYP2C19-substrate:	0.681
CYP2C9-inhibitor:	0.864
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.684
CYP2D6-substrate:	0.906
CYP3A4-inhibitor:	0.861
CYP3A4-substrate:	0.579

ADMET: Excretion

Clearance (CL):	3.171
Half-life (T1/2):	0.755

ADMET: Toxicity

hERG Blockers:	0.103
Human Hepatotoxicity (H-HT):	0.824
Drug-inuced Liver Injury (DILI):	0.742
AMES Toxicity:	0.176
Rat Oral Acute Toxicity:	0.065
Maximum Recommended Daily Dose:	0.586
Skin Sensitization:	0.934
Carcinogencity:	0.896
Eye Corrosion:	0.003
Eye Irritation:	0.096
Respiratory Toxicity:	0.222

Download Data

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

Natural Product: NPC303993

Natural Product ID:	NPC303993
*Common Name:**	Botryllamide C
IUPAC Name:	(Z)-N-[(E)-2-(3-bromo-4-methoxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide
Synonyms:	Botryllamide C
Standard InCHIKey:	UCXFHNQSLPZQNU-IGZKKZBOSA-N
Standard InCHI:	InChI=1S/C19H18BrNO4/c1-24-17-8-5-14(11-16(17)20)9-10-21-19(23)18(25-2)12-13-3-6-15(22)7-4-13/h3-12,22H,1-2H3,(H,21,23)/b10-9+,18-12-
SMILES:	CO/C(=Cc1ccc(cc1)O)/C(=N/C=C/c1ccc(c(c1)Br)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458921
PubChem CID:	9978531
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]
NPO8895	Dictyota pfaffii	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8895	Dictyota pfaffii	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	3

Activity Type	# Activity
Cell Line	1
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	28000.0	nM	PMID[505562]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	=	16400.0	nM	PMID[505563]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	=	16400	nM	Patent: US8470888 B2

☑ 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 NPC303993 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	210
0.1-0.2	2803
0.2-0.3	11912
0.3-0.4	6558
0.4-0.5	8745
0.5-0.6	10149
0.6-0.7	2180
0.7-0.8	130
0.8-0.85	4
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC213471
0.9225	High Similarity	NPC99280
0.8968	High Similarity	NPC83279
0.8561	High Similarity	NPC474128
0.8492	Intermediate Similarity	NPC37302
0.8346	Intermediate Similarity	NPC303370
0.8175	Intermediate Similarity	NPC473724
0.8092	Intermediate Similarity	NPC256369
0.8056	Intermediate Similarity	NPC78530
0.8056	Intermediate Similarity	NPC470472
0.7956	Intermediate Similarity	NPC186898
0.7943	Intermediate Similarity	NPC470471
0.7931	Intermediate Similarity	NPC135349
0.7895	Intermediate Similarity	NPC41801
0.7852	Intermediate Similarity	NPC258222
0.7842	Intermediate Similarity	NPC35961
0.7842	Intermediate Similarity	NPC195749
0.7842	Intermediate Similarity	NPC474091
0.7842	Intermediate Similarity	NPC52029
0.7832	Intermediate Similarity	NPC470470
0.7826	Intermediate Similarity	NPC251571
0.7826	Intermediate Similarity	NPC122359
0.7826	Intermediate Similarity	NPC78061
0.7826	Intermediate Similarity	NPC159987
0.782	Intermediate Similarity	NPC43275
0.777	Intermediate Similarity	NPC155838
0.7752	Intermediate Similarity	NPC166837
0.773	Intermediate Similarity	NPC214869
0.7669	Intermediate Similarity	NPC323948
0.7667	Intermediate Similarity	NPC76412
0.766	Intermediate Similarity	NPC114102
0.766	Intermediate Similarity	NPC475735
0.766	Intermediate Similarity	NPC11449
0.7656	Intermediate Similarity	NPC146530
0.7647	Intermediate Similarity	NPC156311
0.763	Intermediate Similarity	NPC263835
0.7622	Intermediate Similarity	NPC120114
0.7622	Intermediate Similarity	NPC71888
0.7606	Intermediate Similarity	NPC471953
0.7594	Intermediate Similarity	NPC258992
0.7566	Intermediate Similarity	NPC47672
0.7552	Intermediate Similarity	NPC163810
0.7546	Intermediate Similarity	NPC290534
0.7517	Intermediate Similarity	NPC309667
0.75	Intermediate Similarity	NPC301713
0.7483	Intermediate Similarity	NPC474753
0.7482	Intermediate Similarity	NPC95733
0.7482	Intermediate Similarity	NPC62101
0.7466	Intermediate Similarity	NPC41473
0.7466	Intermediate Similarity	NPC160607
0.7466	Intermediate Similarity	NPC204848
0.7466	Intermediate Similarity	NPC14600
0.7466	Intermediate Similarity	NPC312770
0.7455	Intermediate Similarity	NPC301941
0.7455	Intermediate Similarity	NPC74618
0.7455	Intermediate Similarity	NPC214188
0.7447	Intermediate Similarity	NPC153990
0.7429	Intermediate Similarity	NPC29477
0.7419	Intermediate Similarity	NPC233926
0.7415	Intermediate Similarity	NPC296898
0.7415	Intermediate Similarity	NPC299583
0.741	Intermediate Similarity	NPC211218
0.7394	Intermediate Similarity	NPC475396
0.7391	Intermediate Similarity	NPC7830
0.7386	Intermediate Similarity	NPC109968
0.7385	Intermediate Similarity	NPC471495
0.7364	Intermediate Similarity	NPC113457
0.7362	Intermediate Similarity	NPC225130
0.7338	Intermediate Similarity	NPC296202
0.7317	Intermediate Similarity	NPC469979
0.7315	Intermediate Similarity	NPC195814
0.7279	Intermediate Similarity	NPC475132
0.7279	Intermediate Similarity	NPC474587
0.7278	Intermediate Similarity	NPC144823
0.7273	Intermediate Similarity	NPC298981
0.7273	Intermediate Similarity	NPC473462
0.7273	Intermediate Similarity	NPC473358
0.7273	Intermediate Similarity	NPC207819
0.7273	Intermediate Similarity	NPC126128
0.7273	Intermediate Similarity	NPC110454
0.7267	Intermediate Similarity	NPC222039
0.7267	Intermediate Similarity	NPC100478
0.7252	Intermediate Similarity	NPC24101
0.7252	Intermediate Similarity	NPC201959
0.7252	Intermediate Similarity	NPC96224
0.7239	Intermediate Similarity	NPC59387
0.7234	Intermediate Similarity	NPC213414
0.723	Intermediate Similarity	NPC475293
0.7226	Intermediate Similarity	NPC470626
0.7212	Intermediate Similarity	NPC226001
0.7209	Intermediate Similarity	NPC474603
0.7209	Intermediate Similarity	NPC12987
0.7203	Intermediate Similarity	NPC202776
0.7192	Intermediate Similarity	NPC184465
0.7183	Intermediate Similarity	NPC152186
0.7183	Intermediate Similarity	NPC170583
0.7183	Intermediate Similarity	NPC71105
0.7183	Intermediate Similarity	NPC182147
0.7183	Intermediate Similarity	NPC207541
0.7183	Intermediate Similarity	NPC110131
0.7183	Intermediate Similarity	NPC246133
0.7172	Intermediate Similarity	NPC45191
0.7172	Intermediate Similarity	NPC255550
0.7172	Intermediate Similarity	NPC308885
0.7153	Intermediate Similarity	NPC293619
0.7143	Intermediate Similarity	NPC475283
0.7143	Intermediate Similarity	NPC152205
0.7133	Intermediate Similarity	NPC477838
0.7133	Intermediate Similarity	NPC477837
0.7133	Intermediate Similarity	NPC251466
0.7133	Intermediate Similarity	NPC156944
0.7124	Intermediate Similarity	NPC5462
0.7123	Intermediate Similarity	NPC93882
0.7123	Intermediate Similarity	NPC130595
0.7123	Intermediate Similarity	NPC166624
0.7122	Intermediate Similarity	NPC242885
0.7122	Intermediate Similarity	NPC56214
0.7122	Intermediate Similarity	NPC117780
0.7122	Intermediate Similarity	NPC227217
0.7122	Intermediate Similarity	NPC95614
0.7122	Intermediate Similarity	NPC165133
0.7122	Intermediate Similarity	NPC232316
0.7121	Intermediate Similarity	NPC309982
0.7121	Intermediate Similarity	NPC75440
0.7118	Intermediate Similarity	NPC49172
0.7113	Intermediate Similarity	NPC300955
0.7105	Intermediate Similarity	NPC63628
0.7105	Intermediate Similarity	NPC178466
0.7103	Intermediate Similarity	NPC470706
0.7101	Intermediate Similarity	NPC122009
0.7092	Intermediate Similarity	NPC229213
0.7092	Intermediate Similarity	NPC471315
0.7092	Intermediate Similarity	NPC471314
0.7083	Intermediate Similarity	NPC157740
0.7083	Intermediate Similarity	NPC291449
0.7083	Intermediate Similarity	NPC99798
0.7083	Intermediate Similarity	NPC41331
0.7078	Intermediate Similarity	NPC296085
0.7075	Intermediate Similarity	NPC313737
0.7075	Intermediate Similarity	NPC285078
0.7075	Intermediate Similarity	NPC6854
0.7071	Intermediate Similarity	NPC207613
0.7071	Intermediate Similarity	NPC224814
0.7071	Intermediate Similarity	NPC189844
0.7071	Intermediate Similarity	NPC14007
0.7071	Intermediate Similarity	NPC269843
0.7071	Intermediate Similarity	NPC109083
0.7071	Intermediate Similarity	NPC60962
0.7068	Intermediate Similarity	NPC54543
0.7068	Intermediate Similarity	NPC474272
0.7066	Intermediate Similarity	NPC475615
0.705	Intermediate Similarity	NPC281298
0.705	Intermediate Similarity	NPC38483
0.705	Intermediate Similarity	NPC310338
0.705	Intermediate Similarity	NPC163036
0.7045	Intermediate Similarity	NPC142297
0.7045	Intermediate Similarity	NPC469731
0.7042	Intermediate Similarity	NPC105999
0.7042	Intermediate Similarity	NPC474169
0.7042	Intermediate Similarity	NPC473572
0.7035	Intermediate Similarity	NPC82741
0.7035	Intermediate Similarity	NPC473409
0.7035	Intermediate Similarity	NPC141405
0.7034	Intermediate Similarity	NPC147247
0.7034	Intermediate Similarity	NPC246974
0.7029	Intermediate Similarity	NPC283468
0.7027	Intermediate Similarity	NPC218530
0.7021	Intermediate Similarity	NPC470212
0.7021	Intermediate Similarity	NPC184651
0.7021	Intermediate Similarity	NPC262156
0.7021	Intermediate Similarity	NPC473853
0.7021	Intermediate Similarity	NPC38996
0.7021	Intermediate Similarity	NPC343720
0.7021	Intermediate Similarity	NPC113865
0.7021	Intermediate Similarity	NPC324571
0.7021	Intermediate Similarity	NPC160380
0.7021	Intermediate Similarity	NPC312675
0.7021	Intermediate Similarity	NPC54872
0.702	Intermediate Similarity	NPC212850
0.702	Intermediate Similarity	NPC83289
0.702	Intermediate Similarity	NPC189724
0.7015	Intermediate Similarity	NPC46844
0.7014	Intermediate Similarity	NPC218323
0.7013	Intermediate Similarity	NPC313414
0.7007	Intermediate Similarity	NPC158078
0.7007	Intermediate Similarity	NPC274732
0.7	Intermediate Similarity	NPC474673
0.7	Intermediate Similarity	NPC252817
0.7	Intermediate Similarity	NPC321133
0.7	Intermediate Similarity	NPC474565
0.6993	Remote Similarity	NPC272463
0.6992	Remote Similarity	NPC153690
0.6987	Remote Similarity	NPC153644
0.6987	Remote Similarity	NPC470935
0.6987	Remote Similarity	NPC471032
0.6986	Remote Similarity	NPC478071
0.6985	Remote Similarity	NPC35344
0.6985	Remote Similarity	NPC141003
0.6977	Remote Similarity	NPC471591
0.6977	Remote Similarity	NPC475658

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 NPC303993 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	938
0.2-0.3	1228
0.3-0.4	2633
0.4-0.5	2528
0.5-0.6	1356
0.6-0.7	310
0.7-0.8	7
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
0.7447	Intermediate Similarity	NPD4993	Discontinued
0.7208	Intermediate Similarity	NPD2184	Approved
0.7208	Intermediate Similarity	NPD2183	Approved
0.7192	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3145	Approved
0.7172	Intermediate Similarity	NPD3144	Approved
0.7163	Intermediate Similarity	NPD6583	Phase 3
0.7163	Intermediate Similarity	NPD6582	Phase 2
0.7123	Intermediate Similarity	NPD2674	Phase 3
0.7113	Intermediate Similarity	NPD2922	Phase 1
0.7042	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1669	Approved
0.7014	Intermediate Similarity	NPD6584	Phase 3
0.7	Intermediate Similarity	NPD2667	Approved
0.7	Intermediate Similarity	NPD2668	Approved
0.6923	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3685	Discontinued
0.6912	Remote Similarity	NPD821	Approved
0.6866	Remote Similarity	NPD2684	Approved
0.6838	Remote Similarity	NPD228	Approved
0.6835	Remote Similarity	NPD3596	Phase 2
0.6831	Remote Similarity	NPD3847	Discontinued
0.6824	Remote Similarity	NPD1048	Approved
0.6815	Remote Similarity	NPD3985	Discontinued
0.6815	Remote Similarity	NPD4123	Phase 3
0.6807	Remote Similarity	NPD4010	Discontinued
0.6788	Remote Similarity	NPD7843	Approved
0.6776	Remote Similarity	NPD1169	Approved
0.6774	Remote Similarity	NPD5481	Discontinued
0.6739	Remote Similarity	NPD5283	Phase 1
0.6738	Remote Similarity	NPD6580	Approved
0.6738	Remote Similarity	NPD6581	Approved
0.6736	Remote Similarity	NPD2230	Approved
0.6736	Remote Similarity	NPD2233	Approved
0.6736	Remote Similarity	NPD2232	Approved
0.6733	Remote Similarity	NPD1558	Phase 1
0.6719	Remote Similarity	NPD2934	Approved
0.6719	Remote Similarity	NPD2933	Approved
0.6716	Remote Similarity	NPD968	Approved
0.6713	Remote Similarity	NPD3421	Phase 3
0.6712	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.671	Remote Similarity	NPD3060	Approved
0.669	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7477	Discontinued
0.6667	Remote Similarity	NPD1423	Approved
0.6667	Remote Similarity	NPD6331	Phase 2
0.6667	Remote Similarity	NPD2859	Approved
0.6667	Remote Similarity	NPD2860	Approved
0.6667	Remote Similarity	NPD4108	Discontinued
0.6646	Remote Similarity	NPD4357	Discontinued
0.6646	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3052	Approved
0.6645	Remote Similarity	NPD3054	Approved
0.6644	Remote Similarity	NPD3027	Phase 3
0.6644	Remote Similarity	NPD3180	Approved
0.6644	Remote Similarity	NPD3179	Approved
0.6644	Remote Similarity	NPD5163	Phase 2
0.6643	Remote Similarity	NPD709	Approved
0.6643	Remote Similarity	NPD7157	Approved
0.6643	Remote Similarity	NPD2557	Approved
0.6621	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD4675	Approved
0.6605	Remote Similarity	NPD4678	Approved
0.6604	Remote Similarity	NPD3536	Discontinued
0.66	Remote Similarity	NPD5110	Phase 2
0.66	Remote Similarity	NPD5109	Approved
0.66	Remote Similarity	NPD5111	Phase 2
0.6599	Remote Similarity	NPD1817	Approved
0.6599	Remote Similarity	NPD1819	Approved
0.6599	Remote Similarity	NPD1820	Approved
0.6599	Remote Similarity	NPD1818	Approved
0.6581	Remote Similarity	NPD3656	Approved
0.6577	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5451	Approved
0.6564	Remote Similarity	NPD6072	Discontinued
0.6561	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5536	Phase 2
0.6547	Remote Similarity	NPD2497	Approved
0.6547	Remote Similarity	NPD2496	Approved
0.6544	Remote Similarity	NPD1358	Approved
0.6544	Remote Similarity	NPD290	Approved
0.6538	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD3164	Approved
0.6533	Remote Similarity	NPD3166	Approved
0.6533	Remote Similarity	NPD3167	Approved
0.6533	Remote Similarity	NPD3165	Approved
0.6531	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6516	Phase 2
0.6528	Remote Similarity	NPD5846	Approved
0.6522	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD2219	Phase 1
0.6516	Remote Similarity	NPD2161	Phase 2
0.6515	Remote Similarity	NPD3020	Approved
0.6513	Remote Similarity	NPD4060	Phase 1
0.6513	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD2231	Phase 2
0.6507	Remote Similarity	NPD2235	Phase 2
0.65	Remote Similarity	NPD2234	Approved
0.65	Remote Similarity	NPD2228	Approved
0.65	Remote Similarity	NPD2229	Approved
0.6497	Remote Similarity	NPD4162	Approved
0.649	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.649	Remote Similarity	NPD5718	Phase 2
0.6488	Remote Similarity	NPD1411	Approved
0.6486	Remote Similarity	NPD1232	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4003	Phase 3
0.6463	Remote Similarity	NPD4129	Approved
0.6463	Remote Similarity	NPD2429	Approved
0.6463	Remote Similarity	NPD6539	Approved
0.6463	Remote Similarity	NPD6542	Approved
0.6463	Remote Similarity	NPD6540	Phase 3
0.6463	Remote Similarity	NPD6543	Approved
0.6463	Remote Similarity	NPD2428	Approved
0.6463	Remote Similarity	NPD3778	Approved
0.646	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD3445	Approved
0.6458	Remote Similarity	NPD2594	Approved
0.6458	Remote Similarity	NPD3444	Approved
0.6458	Remote Similarity	NPD2595	Approved
0.6458	Remote Similarity	NPD6382	Discontinued
0.6458	Remote Similarity	NPD3443	Approved
0.6458	Remote Similarity	NPD3049	Approved
0.6457	Remote Similarity	NPD2802	Phase 3
0.6449	Remote Similarity	NPD3022	Approved
0.6449	Remote Similarity	NPD3021	Approved
0.6447	Remote Similarity	NPD839	Approved
0.6447	Remote Similarity	NPD7265	Discontinued
0.6447	Remote Similarity	NPD840	Approved
0.6443	Remote Similarity	NPD7451	Discontinued
0.6442	Remote Similarity	NPD4005	Discontinued
0.6438	Remote Similarity	NPD776	Approved
0.6433	Remote Similarity	NPD7153	Discontinued
0.6429	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2157	Approved
0.6429	Remote Similarity	NPD5535	Approved
0.6429	Remote Similarity	NPD4097	Suspended
0.6424	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD6179	Discontinued
0.6424	Remote Similarity	NPD1024	Discontinued
0.642	Remote Similarity	NPD7131	Phase 3
0.6419	Remote Similarity	NPD6541	Approved
0.6419	Remote Similarity	NPD6538	Approved
0.6415	Remote Similarity	NPD5241	Discontinued
0.6414	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD2556	Approved
0.6414	Remote Similarity	NPD2554	Approved
0.641	Remote Similarity	NPD6032	Approved
0.641	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD2238	Phase 2
0.6402	Remote Similarity	NPD1009	Approved
0.6402	Remote Similarity	NPD6502	Phase 2
0.64	Remote Similarity	NPD1712	Approved
0.64	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4237	Approved
0.6392	Remote Similarity	NPD4236	Phase 3
0.6392	Remote Similarity	NPD2458	Approved
0.6392	Remote Similarity	NPD2459	Approved
0.6392	Remote Similarity	NPD2460	Phase 3
0.6389	Remote Similarity	NPD1548	Phase 1
0.6389	Remote Similarity	NPD2486	Discontinued
0.6387	Remote Similarity	NPD6895	Approved
0.6387	Remote Similarity	NPD6896	Approved
0.6386	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD6798	Discontinued
0.6376	Remote Similarity	NPD3567	Approved
0.6376	Remote Similarity	NPD3568	Approved
0.6376	Remote Similarity	NPD1794	Approved
0.6375	Remote Similarity	NPD5756	Phase 2
0.6374	Remote Similarity	NPD4083	Discontinued
0.6364	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3236	Phase 3
0.6364	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2614	Approved
0.6358	Remote Similarity	NPD4908	Phase 1
0.6351	Remote Similarity	NPD2982	Phase 2
0.6351	Remote Similarity	NPD2983	Phase 2
0.635	Remote Similarity	NPD3134	Approved
0.6347	Remote Similarity	NPD3558	Approved
0.6347	Remote Similarity	NPD3560	Approved
0.6347	Remote Similarity	NPD2296	Approved
0.6347	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD3556	Approved
0.6347	Remote Similarity	NPD3557	Approved
0.6346	Remote Similarity	NPD2154	Approved
0.6346	Remote Similarity	NPD2156	Approved
0.6346	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD2155	Approved
0.6345	Remote Similarity	NPD1357	Approved
0.634	Remote Similarity	NPD4062	Phase 3
0.634	Remote Similarity	NPD6233	Phase 2
0.634	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD9296	Approved
0.6335	Remote Similarity	NPD7212	Phase 2
0.6335	Remote Similarity	NPD7213	Phase 3
0.6333	Remote Similarity	NPD7018	Phase 2

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