NPASS Compound

Structure

NPC474128 OpenBabel07101718182D 26 27 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 2.5000 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 0.0000 1.0000 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 -5.1962 3.0000 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 -1.7321 0.0000 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 -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 -7.7942 4.5000 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 -3.4641 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 5.5000 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 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 26 1 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 21 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 12 1 0 0 0 0 10 15 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 17 2 0 0 0 0 14 20 1 0 0 0 0 15 18 1 0 0 0 0 15 22 2 0 0 0 0 16 23 1 0 0 0 0 17 26 1 0 0 0 0 18 21 2 3 0 0 0 18 24 1 0 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	483.96
Volume:	377.401
LogP:	3.542
LogD:	3.138
LogS:	-4.086
# Rotatable Bonds:	8
TPSA:	91.15
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.317
Synthetic Accessibility Score:	2.497
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.74
MDCK Permeability:	1.71563387993956e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.062
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.611
Plasma Protein Binding (PPB):	98.8470687866211%
Volume Distribution (VD):	0.347
Pgp-substrate:	1.1048680543899536%

ADMET: Metabolism

CYP1A2-inhibitor:	0.915
CYP1A2-substrate:	0.148
CYP2C19-inhibitor:	0.972
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.944
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.933
CYP2D6-substrate:	0.865
CYP3A4-inhibitor:	0.902
CYP3A4-substrate:	0.379

ADMET: Excretion

Clearance (CL):	1.249
Half-life (T1/2):	0.595

ADMET: Toxicity

hERG Blockers:	0.105
Human Hepatotoxicity (H-HT):	0.32
Drug-inuced Liver Injury (DILI):	0.653
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.276
Maximum Recommended Daily Dose:	0.567
Skin Sensitization:	0.341
Carcinogencity:	0.328
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC474128

Natural Product ID:	NPC474128
*Common Name:**	1'-Methoxyhemibastadin 1
IUPAC Name:	(2Z)-N-[2-(3-bromo-4-hydroxyphenyl)ethyl]-3-(3-bromo-4-methoxyphenyl)-2-hydroxyiminopropanamide
Synonyms:	1'-Methoxyhemibastadin 1
Standard InCHIKey:	KOXDPWRJBODQLS-JCMHNJIXSA-N
Standard InCHI:	InChI=1S/C18H18Br2N2O4/c1-26-17-5-3-12(9-14(17)20)10-15(22-25)18(24)21-7-6-11-2-4-16(23)13(19)8-11/h2-5,8-9,23,25H,6-7,10H2,1H3,(H,21,24)/b22-15-
SMILES:	COC1=C(C=C(C=C1)CC(=NO)C(=O)NCCC2=CC(=C(C=C2)O)Br)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462676
PubChem CID:	15338210
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
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[2089117]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23249297]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Bismarck archipelago	n.a.	PMID[7623047]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[8904842]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8988595]
NPO16920	Ianthella basta	Species	Ianthellidae	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1522	Organism	Neisseria gonorrhoeae	Neisseria gonorrhoeae	MIC	=	6.25	ug	PMID[565724]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug	PMID[565724]

☑ 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 NPC474128 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	226
0.1-0.2	2772
0.2-0.3	12262
0.3-0.4	5856
0.4-0.5	10328
0.5-0.6	9469
0.6-0.7	1581
0.7-0.8	164
0.8-0.85	27
0.85-0.9	6
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9242	High Similarity	NPC474091
0.9155	High Similarity	NPC258222
0.903	High Similarity	NPC475735
0.8904	High Similarity	NPC156311
0.863	High Similarity	NPC109968
0.8613	High Similarity	NPC473724
0.8561	High Similarity	NPC303993
0.8561	High Similarity	NPC71888
0.8561	High Similarity	NPC120114
0.8511	High Similarity	NPC213471
0.8472	Intermediate Similarity	NPC78530
0.8446	Intermediate Similarity	NPC47672
0.844	Intermediate Similarity	NPC309667
0.8357	Intermediate Similarity	NPC163810
0.8345	Intermediate Similarity	NPC135349
0.8286	Intermediate Similarity	NPC474753
0.8278	Intermediate Similarity	NPC233926
0.8182	Intermediate Similarity	NPC475132
0.8182	Intermediate Similarity	NPC474587
0.8176	Intermediate Similarity	NPC225130
0.8134	Intermediate Similarity	NPC43275
0.8125	Intermediate Similarity	NPC469979
0.8125	Intermediate Similarity	NPC475293
0.8095	Intermediate Similarity	NPC470472
0.8079	Intermediate Similarity	NPC475432
0.8075	Intermediate Similarity	NPC126128
0.8075	Intermediate Similarity	NPC473462
0.8075	Intermediate Similarity	NPC207819
0.8075	Intermediate Similarity	NPC110454
0.8075	Intermediate Similarity	NPC298981
0.8067	Intermediate Similarity	NPC76412
0.8025	Intermediate Similarity	NPC290534
0.8014	Intermediate Similarity	NPC99280
0.8012	Intermediate Similarity	NPC226001
0.8	Intermediate Similarity	NPC202776
0.7986	Intermediate Similarity	NPC470471
0.7975	Intermediate Similarity	NPC475396
0.7972	Intermediate Similarity	NPC184465
0.7927	Intermediate Similarity	NPC301941
0.7927	Intermediate Similarity	NPC214188
0.7927	Intermediate Similarity	NPC74618
0.7902	Intermediate Similarity	NPC166624
0.7892	Intermediate Similarity	NPC49172
0.7877	Intermediate Similarity	NPC470470
0.7871	Intermediate Similarity	NPC473738
0.7844	Intermediate Similarity	NPC473892
0.7844	Intermediate Similarity	NPC475658
0.7832	Intermediate Similarity	NPC114102
0.781	Intermediate Similarity	NPC263835
0.7798	Intermediate Similarity	NPC141405
0.7798	Intermediate Similarity	NPC82741
0.7798	Intermediate Similarity	NPC473409
0.7786	Intermediate Similarity	NPC95733
0.7786	Intermediate Similarity	NPC62101
0.7755	Intermediate Similarity	NPC197045
0.7746	Intermediate Similarity	NPC122359
0.7746	Intermediate Similarity	NPC251571
0.7746	Intermediate Similarity	NPC78061
0.7746	Intermediate Similarity	NPC159987
0.7738	Intermediate Similarity	NPC471591
0.7738	Intermediate Similarity	NPC144823
0.773	Intermediate Similarity	NPC29477
0.7714	Intermediate Similarity	NPC211218
0.7708	Intermediate Similarity	NPC11449
0.7692	Intermediate Similarity	NPC470951
0.7655	Intermediate Similarity	NPC214869
0.7643	Intermediate Similarity	NPC471315
0.7643	Intermediate Similarity	NPC471314
0.7639	Intermediate Similarity	NPC195749
0.7639	Intermediate Similarity	NPC52029
0.7639	Intermediate Similarity	NPC35961
0.7636	Intermediate Similarity	NPC475615
0.7626	Intermediate Similarity	NPC83279
0.7606	Intermediate Similarity	NPC110131
0.7605	Intermediate Similarity	NPC152205
0.7605	Intermediate Similarity	NPC475283
0.7591	Intermediate Similarity	NPC311737
0.7591	Intermediate Similarity	NPC38458
0.7574	Intermediate Similarity	NPC303370
0.7572	Intermediate Similarity	NPC469721
0.7569	Intermediate Similarity	NPC155838
0.7554	Intermediate Similarity	NPC41801
0.7552	Intermediate Similarity	NPC301713
0.7537	Intermediate Similarity	NPC166837
0.7518	Intermediate Similarity	NPC82963
0.7517	Intermediate Similarity	NPC474673
0.75	Intermediate Similarity	NPC186898
0.7486	Intermediate Similarity	NPC469731
0.7468	Intermediate Similarity	NPC296085
0.7445	Intermediate Similarity	NPC317254
0.7444	Intermediate Similarity	NPC96224
0.7444	Intermediate Similarity	NPC24101
0.7444	Intermediate Similarity	NPC471495
0.7438	Intermediate Similarity	NPC123848
0.7429	Intermediate Similarity	NPC53596
0.7429	Intermediate Similarity	NPC17388
0.7429	Intermediate Similarity	NPC289330
0.7429	Intermediate Similarity	NPC471308
0.7429	Intermediate Similarity	NPC160120
0.7426	Intermediate Similarity	NPC59387
0.7424	Intermediate Similarity	NPC231705
0.7417	Intermediate Similarity	NPC83289
0.7417	Intermediate Similarity	NPC212850
0.7417	Intermediate Similarity	NPC189724
0.7415	Intermediate Similarity	NPC471953
0.7413	Intermediate Similarity	NPC272463
0.74	Intermediate Similarity	NPC160607
0.74	Intermediate Similarity	NPC204848
0.74	Intermediate Similarity	NPC41473
0.74	Intermediate Similarity	NPC312770
0.74	Intermediate Similarity	NPC14600
0.7394	Intermediate Similarity	NPC296202
0.7388	Intermediate Similarity	NPC258056
0.7379	Intermediate Similarity	NPC153990
0.7372	Intermediate Similarity	NPC118202
0.7357	Intermediate Similarity	NPC256369
0.7355	Intermediate Similarity	NPC71629
0.7351	Intermediate Similarity	NPC299583
0.7338	Intermediate Similarity	NPC323948
0.7333	Intermediate Similarity	NPC473358
0.7333	Intermediate Similarity	NPC474149
0.7324	Intermediate Similarity	NPC7830
0.7313	Intermediate Similarity	NPC153690
0.7308	Intermediate Similarity	NPC20755
0.7305	Intermediate Similarity	NPC321133
0.7297	Intermediate Similarity	NPC93882
0.7297	Intermediate Similarity	NPC130595
0.7293	Intermediate Similarity	NPC113457
0.7292	Intermediate Similarity	NPC213414
0.729	Intermediate Similarity	NPC5462
0.7248	Intermediate Similarity	NPC313737
0.7248	Intermediate Similarity	NPC6854
0.7248	Intermediate Similarity	NPC285078
0.7246	Intermediate Similarity	NPC115803
0.7244	Intermediate Similarity	NPC245974
0.7244	Intermediate Similarity	NPC132771
0.7239	Intermediate Similarity	NPC142297
0.7237	Intermediate Similarity	NPC296898
0.7234	Intermediate Similarity	NPC268572
0.7234	Intermediate Similarity	NPC283760
0.7226	Intermediate Similarity	NPC247298
0.7208	Intermediate Similarity	NPC222039
0.7208	Intermediate Similarity	NPC100478
0.72	Intermediate Similarity	NPC218530
0.7197	Intermediate Similarity	NPC178902
0.7194	Intermediate Similarity	NPC37302
0.7192	Intermediate Similarity	NPC218323
0.7181	Intermediate Similarity	NPC158078
0.7181	Intermediate Similarity	NPC470392
0.7168	Intermediate Similarity	NPC259071
0.7168	Intermediate Similarity	NPC77435
0.7143	Intermediate Similarity	NPC258992
0.7143	Intermediate Similarity	NPC56635
0.7132	Intermediate Similarity	NPC54543
0.7127	Intermediate Similarity	NPC156055
0.7126	Intermediate Similarity	NPC477255
0.7124	Intermediate Similarity	NPC40321
0.7119	Intermediate Similarity	NPC227953
0.7114	Intermediate Similarity	NPC45191
0.7114	Intermediate Similarity	NPC308885
0.7114	Intermediate Similarity	NPC255550
0.7105	Intermediate Similarity	NPC470249
0.7103	Intermediate Similarity	NPC105999
0.7089	Intermediate Similarity	NPC277857
0.7089	Intermediate Similarity	NPC115144
0.7078	Intermediate Similarity	NPC477837
0.7078	Intermediate Similarity	NPC477838
0.7069	Intermediate Similarity	NPC8093
0.7069	Intermediate Similarity	NPC121571
0.7059	Intermediate Similarity	NPC75440
0.7059	Intermediate Similarity	NPC309982
0.7059	Intermediate Similarity	NPC201959
0.7051	Intermediate Similarity	NPC63628
0.7051	Intermediate Similarity	NPC178466
0.7047	Intermediate Similarity	NPC478071
0.7042	Intermediate Similarity	NPC122009
0.7039	Intermediate Similarity	NPC237227
0.7034	Intermediate Similarity	NPC116562
0.7022	Intermediate Similarity	NPC474678
0.7022	Intermediate Similarity	NPC471338
0.7019	Intermediate Similarity	NPC127402
0.7007	Intermediate Similarity	NPC474272
0.7	Intermediate Similarity	NPC326966
0.6983	Remote Similarity	NPC475843
0.698	Remote Similarity	NPC325651
0.6975	Remote Similarity	NPC275027
0.6972	Remote Similarity	NPC283468
0.6966	Remote Similarity	NPC474862
0.6962	Remote Similarity	NPC313414
0.6957	Remote Similarity	NPC469711
0.6954	Remote Similarity	NPC244866
0.6954	Remote Similarity	NPC477254
0.6954	Remote Similarity	NPC274732
0.6948	Remote Similarity	NPC254610
0.6948	Remote Similarity	NPC471316
0.6948	Remote Similarity	NPC193528
0.6937	Remote Similarity	NPC470935
0.6937	Remote Similarity	NPC471032
0.6934	Remote Similarity	NPC146530
0.6934	Remote Similarity	NPC97811

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 NPC474128 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	826
0.2-0.3	1139
0.3-0.4	2175
0.4-0.5	2859
0.5-0.6	1574
0.6-0.7	405
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
0.8102	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2183	Approved
0.7484	Intermediate Similarity	NPD2184	Approved
0.7465	Intermediate Similarity	NPD1669	Approved
0.7383	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD821	Approved
0.7305	Intermediate Similarity	NPD2668	Approved
0.7305	Intermediate Similarity	NPD2667	Approved
0.7297	Intermediate Similarity	NPD2674	Phase 3
0.7297	Intermediate Similarity	NPD7477	Discontinued
0.7254	Intermediate Similarity	NPD3421	Phase 3
0.7192	Intermediate Similarity	NPD7451	Discontinued
0.7143	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3145	Approved
0.7114	Intermediate Similarity	NPD3144	Approved
0.7103	Intermediate Similarity	NPD6583	Phase 3
0.7103	Intermediate Similarity	NPD6582	Phase 2
0.7039	Intermediate Similarity	NPD3052	Approved
0.7039	Intermediate Similarity	NPD3054	Approved
0.7027	Intermediate Similarity	NPD4993	Discontinued
0.702	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2459	Approved
0.6987	Remote Similarity	NPD2460	Phase 3
0.6987	Remote Similarity	NPD2458	Approved
0.6959	Remote Similarity	NPD6584	Phase 3
0.6954	Remote Similarity	NPD839	Approved
0.6954	Remote Similarity	NPD840	Approved
0.6948	Remote Similarity	NPD1169	Approved
0.6943	Remote Similarity	NPD6331	Phase 2
0.6943	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1024	Discontinued
0.6918	Remote Similarity	NPD2230	Approved
0.6918	Remote Similarity	NPD2233	Approved
0.6918	Remote Similarity	NPD2232	Approved
0.6897	Remote Similarity	NPD2802	Phase 3
0.6894	Remote Similarity	NPD7131	Phase 3
0.6892	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4123	Phase 3
0.6871	Remote Similarity	NPD3685	Discontinued
0.6864	Remote Similarity	NPD4010	Discontinued
0.6839	Remote Similarity	NPD4108	Discontinued
0.6829	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7438	Suspended
0.6829	Remote Similarity	NPD6072	Discontinued
0.6824	Remote Similarity	NPD2922	Phase 1
0.6821	Remote Similarity	NPD3136	Phase 2
0.6821	Remote Similarity	NPD9718	Approved
0.6818	Remote Similarity	NPD2157	Approved
0.6815	Remote Similarity	NPD7153	Discontinued
0.6809	Remote Similarity	NPD2228	Approved
0.6809	Remote Similarity	NPD2234	Approved
0.6809	Remote Similarity	NPD2229	Approved
0.68	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1712	Approved
0.6795	Remote Similarity	NPD2161	Phase 2
0.6795	Remote Similarity	NPD1725	Approved
0.6783	Remote Similarity	NPD3596	Phase 2
0.6781	Remote Similarity	NPD3847	Discontinued
0.6776	Remote Similarity	NPD5109	Approved
0.6776	Remote Similarity	NPD5110	Phase 2
0.6776	Remote Similarity	NPD1039	Discontinued
0.6776	Remote Similarity	NPD5111	Phase 2
0.6772	Remote Similarity	NPD3060	Approved
0.677	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.677	Remote Similarity	NPD3985	Discontinued
0.677	Remote Similarity	NPD4739	Approved
0.677	Remote Similarity	NPD2874	Phase 2
0.6732	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD1423	Approved
0.6732	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD5745	Approved
0.6731	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6390	Discontinued
0.6711	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD6087	Phase 1
0.6707	Remote Similarity	NPD4005	Discontinued
0.669	Remote Similarity	NPD6581	Approved
0.669	Remote Similarity	NPD2486	Discontinued
0.669	Remote Similarity	NPD6580	Approved
0.6689	Remote Similarity	NPD2231	Phase 2
0.6689	Remote Similarity	NPD2561	Approved
0.6689	Remote Similarity	NPD2562	Approved
0.6689	Remote Similarity	NPD2235	Phase 2
0.6688	Remote Similarity	NPD7450	Phase 2
0.6687	Remote Similarity	NPD3692	Discontinued
0.6687	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4675	Approved
0.6667	Remote Similarity	NPD5718	Phase 2
0.6667	Remote Similarity	NPD2933	Approved
0.6667	Remote Similarity	NPD6502	Phase 2
0.6667	Remote Similarity	NPD3536	Discontinued
0.6667	Remote Similarity	NPD2934	Approved
0.6667	Remote Similarity	NPD4678	Approved
0.6647	Remote Similarity	NPD1411	Approved
0.6647	Remote Similarity	NPD5772	Approved
0.6647	Remote Similarity	NPD5773	Approved
0.6645	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4129	Approved
0.6644	Remote Similarity	NPD4659	Approved
0.6644	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2429	Approved
0.6644	Remote Similarity	NPD2428	Approved
0.6643	Remote Similarity	NPD595	Approved
0.6643	Remote Similarity	NPD593	Approved
0.6642	Remote Similarity	NPD9608	Approved
0.6642	Remote Similarity	NPD9610	Approved
0.6627	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD52	Approved
0.6626	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7526	Approved
0.6623	Remote Similarity	NPD7905	Discontinued
0.6617	Remote Similarity	NPD2859	Approved
0.6617	Remote Similarity	NPD2860	Approved
0.6607	Remote Similarity	NPD3560	Approved
0.6607	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3557	Approved
0.6607	Remote Similarity	NPD3556	Approved
0.6607	Remote Similarity	NPD3558	Approved
0.6606	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD5746	Approved
0.6601	Remote Similarity	NPD5163	Phase 2
0.6599	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD2556	Approved
0.6599	Remote Similarity	NPD2554	Approved
0.6597	Remote Similarity	NPD2557	Approved
0.6597	Remote Similarity	NPD709	Approved
0.6584	Remote Similarity	NPD5241	Discontinued
0.6581	Remote Similarity	NPD2238	Phase 2
0.6579	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD5303	Approved
0.6575	Remote Similarity	NPD5304	Approved
0.657	Remote Similarity	NPD7608	Discontinued
0.6566	Remote Similarity	NPD5617	Suspended
0.6564	Remote Similarity	NPD7020	Approved
0.6564	Remote Similarity	NPD7019	Approved
0.6562	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6364	Approved
0.6562	Remote Similarity	NPD44	Approved
0.6561	Remote Similarity	NPD3553	Approved
0.6561	Remote Similarity	NPD3555	Approved
0.6561	Remote Similarity	NPD6895	Approved
0.6561	Remote Similarity	NPD3554	Approved
0.6561	Remote Similarity	NPD3552	Approved
0.6561	Remote Similarity	NPD6896	Approved
0.6556	Remote Similarity	NPD3567	Approved
0.6556	Remote Similarity	NPD4103	Phase 2
0.6556	Remote Similarity	NPD3568	Approved
0.6556	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD3294	Phase 2
0.6547	Remote Similarity	NPD968	Approved
0.6545	Remote Similarity	NPD4003	Phase 3
0.6541	Remote Similarity	NPD3656	Approved
0.6536	Remote Similarity	NPD2614	Approved
0.6533	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD4083	Discontinued
0.6531	Remote Similarity	NPD6382	Discontinued
0.6531	Remote Similarity	NPD2595	Approved
0.6531	Remote Similarity	NPD4093	Discontinued
0.6531	Remote Similarity	NPD2594	Approved
0.6531	Remote Similarity	NPD3049	Approved
0.6525	Remote Similarity	NPD5451	Approved
0.6524	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5481	Discontinued
0.6519	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2497	Approved
0.6503	Remote Similarity	NPD7212	Phase 2
0.6503	Remote Similarity	NPD7213	Phase 3
0.6503	Remote Similarity	NPD2496	Approved
0.6497	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD2372	Approved
0.649	Remote Similarity	NPD196	Phase 1
0.6488	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.648	Remote Similarity	NPD3337	Discontinued
0.6478	Remote Similarity	NPD1519	Approved
0.6478	Remote Similarity	NPD1538	Phase 1
0.6478	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD1537	Approved
0.6474	Remote Similarity	NPD6346	Approved
0.6471	Remote Similarity	NPD7773	Phase 2
0.6471	Remote Similarity	NPD3020	Approved
0.6467	Remote Similarity	NPD1009	Approved
0.6463	Remote Similarity	NPD7447	Phase 1
0.646	Remote Similarity	NPD4236	Phase 3
0.646	Remote Similarity	NPD4162	Approved
0.646	Remote Similarity	NPD4237	Approved
0.6458	Remote Similarity	NPD5283	Phase 1
0.6456	Remote Similarity	NPD696	Discontinued
0.6454	Remote Similarity	NPD2684	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