NPASS Compound

Structure

NPC475712 OpenBabel07101718192D 22 23 0 0 1 0 0 0 0 0999 V2000 -1.5462 0.7669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5462 -0.2331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2117 -2.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -3.7131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5065 -2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6007 -4.0784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3574 -1.0356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6035 -4.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7941 -0.2094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2626 -3.5037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9281 0.2906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9614 -1.5248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8259 -2.6775 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9749 -1.6886 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4221 -2.4124 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6802 -0.7331 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9309 0.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7203 -3.1248 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4109 -2.5614 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 1.3542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8841 -4.1113 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 2 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 11 1 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 13 10 1 6 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 12 1 1 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 6 0 0 0 16 2 1 6 0 0 0 16 22 1 0 0 0 0 17 20 2 0 0 0 0 17 22 1 0 0 0 0 18 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.18
Volume:	339.08
LogP:	4.5
LogD:	4.258
LogS:	-4.298
# Rotatable Bonds:	1
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.445
Synthetic Accessibility Score:	4.679
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.703
MDCK Permeability:	5.138116830494255e-05
Pgp-inhibitor:	0.94
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.172
20% Bioavailability (F20%):	0.856
30% Bioavailability (F30%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.417
Plasma Protein Binding (PPB):	96.22552490234375%
Volume Distribution (VD):	1.311
Pgp-substrate:	3.060748815536499%

ADMET: Metabolism

CYP1A2-inhibitor:	0.24
CYP1A2-substrate:	0.312
CYP2C19-inhibitor:	0.104
CYP2C19-substrate:	0.793
CYP2C9-inhibitor:	0.266
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.847
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	6.633
Half-life (T1/2):	0.932

ADMET: Toxicity

hERG Blockers:	0.121
Human Hepatotoxicity (H-HT):	0.353
Drug-inuced Liver Injury (DILI):	0.617
AMES Toxicity:	0.126
Rat Oral Acute Toxicity:	0.361
Maximum Recommended Daily Dose:	0.41
Skin Sensitization:	0.728
Carcinogencity:	0.129
Eye Corrosion:	0.12
Eye Irritation:	0.086
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC475712

Natural Product ID:	NPC475712
*Common Name:**	Eiseniachloride B
IUPAC Name:	(1R,2S,12Z,14S,15R,16R)-16-chloro-2-ethyl-15-hydroxy-3-oxabicyclo[12.3.0]heptadec-12-en-4-one
Synonyms:
Standard InCHIKey:	HXFOJGYVWJVNOO-RAETWKFMSA-N
Standard InCHI:	InChI=1S/C18H29ClO3/c1-2-16-14-12-15(19)18(21)13(14)10-8-6-4-3-5-7-9-11-17(20)22-16/h8,10,13-16,18,21H,2-7,9,11-12H2,1H3/b10-8-/t13-,14+,15+,16-,18+/m0/s1
SMILES:	CCC1C2CC(C(C2C=CCCCCCCCC(=O)O1)O)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512421
PubChem CID:	11163290
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO27567	Eisenia bicyclis	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14575430]
NPO27567	Eisenia bicyclis	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738398]
NPO27567	Eisenia bicyclis	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20462757]
NPO27567	Eisenia bicyclis	Species	Lessoniaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	Activity	=	0.31	n.a.	PMID[564197]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	0.53	n.a.	PMID[564197]

☑ 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 NPC475712 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	186
0.1-0.2	1489
0.2-0.3	7045
0.3-0.4	16926
0.4-0.5	9121
0.5-0.6	6720
0.6-0.7	1166
0.7-0.8	39
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC475405
0.9756	High Similarity	NPC184461
0.9048	High Similarity	NPC475732
0.8471	Intermediate Similarity	NPC191711
0.7527	Intermediate Similarity	NPC316629
0.7444	Intermediate Similarity	NPC88735
0.7379	Intermediate Similarity	NPC166115
0.7303	Intermediate Similarity	NPC260814
0.7303	Intermediate Similarity	NPC39547
0.7303	Intermediate Similarity	NPC27949
0.7303	Intermediate Similarity	NPC323249
0.7222	Intermediate Similarity	NPC477088
0.7222	Intermediate Similarity	NPC164308
0.7174	Intermediate Similarity	NPC7414
0.7143	Intermediate Similarity	NPC115418
0.713	Intermediate Similarity	NPC258711
0.713	Intermediate Similarity	NPC35069
0.7097	Intermediate Similarity	NPC111409
0.7079	Intermediate Similarity	NPC279537
0.7075	Intermediate Similarity	NPC68248
0.7065	Intermediate Similarity	NPC47031
0.7065	Intermediate Similarity	NPC316844
0.7065	Intermediate Similarity	NPC126248
0.7064	Intermediate Similarity	NPC273242
0.7033	Intermediate Similarity	NPC226226
0.7033	Intermediate Similarity	NPC55304
0.7033	Intermediate Similarity	NPC201225
0.703	Intermediate Similarity	NPC161493
0.703	Intermediate Similarity	NPC472290
0.7009	Intermediate Similarity	NPC115352
0.7	Intermediate Similarity	NPC67584
0.7	Intermediate Similarity	NPC52044
0.7	Intermediate Similarity	NPC213698
0.7	Intermediate Similarity	NPC121816
0.6972	Remote Similarity	NPC189338
0.6972	Remote Similarity	NPC95290
0.6966	Remote Similarity	NPC217725
0.6957	Remote Similarity	NPC156658
0.6957	Remote Similarity	NPC258965
0.6939	Remote Similarity	NPC37607
0.6939	Remote Similarity	NPC301969
0.6937	Remote Similarity	NPC170692
0.6937	Remote Similarity	NPC255450
0.6931	Remote Similarity	NPC213078
0.6915	Remote Similarity	NPC477667
0.6915	Remote Similarity	NPC128246
0.69	Remote Similarity	NPC127019
0.6875	Remote Similarity	NPC67493
0.6869	Remote Similarity	NPC475925
0.6854	Remote Similarity	NPC472966
0.6832	Remote Similarity	NPC170120
0.6827	Remote Similarity	NPC150923
0.6796	Remote Similarity	NPC152480
0.6782	Remote Similarity	NPC317583
0.6782	Remote Similarity	NPC199557
0.6778	Remote Similarity	NPC113639
0.6774	Remote Similarity	NPC200446
0.6768	Remote Similarity	NPC297474
0.6768	Remote Similarity	NPC54065
0.6765	Remote Similarity	NPC24956
0.6765	Remote Similarity	NPC18019
0.6747	Remote Similarity	NPC201939
0.6744	Remote Similarity	NPC60120
0.6739	Remote Similarity	NPC11796
0.6739	Remote Similarity	NPC218817
0.6739	Remote Similarity	NPC469495
0.6737	Remote Similarity	NPC250315
0.6735	Remote Similarity	NPC217983
0.6735	Remote Similarity	NPC207114
0.6735	Remote Similarity	NPC202672
0.6735	Remote Similarity	NPC91248
0.6735	Remote Similarity	NPC294480
0.6733	Remote Similarity	NPC90453
0.6733	Remote Similarity	NPC198853
0.6701	Remote Similarity	NPC477668
0.6701	Remote Similarity	NPC56593
0.67	Remote Similarity	NPC293001
0.67	Remote Similarity	NPC133698
0.67	Remote Similarity	NPC133888
0.67	Remote Similarity	NPC57304
0.67	Remote Similarity	NPC131209
0.67	Remote Similarity	NPC35959
0.67	Remote Similarity	NPC29821
0.67	Remote Similarity	NPC63193
0.67	Remote Similarity	NPC221282
0.67	Remote Similarity	NPC171360
0.6699	Remote Similarity	NPC477949
0.6698	Remote Similarity	NPC474775
0.6667	Remote Similarity	NPC209995
0.6667	Remote Similarity	NPC82297
0.6667	Remote Similarity	NPC155935
0.6667	Remote Similarity	NPC215556
0.6667	Remote Similarity	NPC304886
0.6667	Remote Similarity	NPC474776
0.6667	Remote Similarity	NPC165287
0.6667	Remote Similarity	NPC224386
0.6667	Remote Similarity	NPC194859
0.6636	Remote Similarity	NPC29705
0.6635	Remote Similarity	NPC477854
0.6635	Remote Similarity	NPC221615
0.6634	Remote Similarity	NPC109414
0.6633	Remote Similarity	NPC477959
0.6633	Remote Similarity	NPC312215
0.6632	Remote Similarity	NPC474252
0.6632	Remote Similarity	NPC89555
0.663	Remote Similarity	NPC276769
0.663	Remote Similarity	NPC7563
0.663	Remote Similarity	NPC320630
0.663	Remote Similarity	NPC186109
0.663	Remote Similarity	NPC116177
0.6628	Remote Similarity	NPC126899
0.6628	Remote Similarity	NPC304665
0.6628	Remote Similarity	NPC154728
0.6627	Remote Similarity	NPC243532
0.6602	Remote Similarity	NPC477853
0.6602	Remote Similarity	NPC42042
0.66	Remote Similarity	NPC478003
0.66	Remote Similarity	NPC35809
0.66	Remote Similarity	NPC216284
0.66	Remote Similarity	NPC46281
0.66	Remote Similarity	NPC158388
0.66	Remote Similarity	NPC19087
0.66	Remote Similarity	NPC123854
0.66	Remote Similarity	NPC478004
0.66	Remote Similarity	NPC475855
0.66	Remote Similarity	NPC473448
0.6598	Remote Similarity	NPC284534
0.6598	Remote Similarity	NPC235792
0.6598	Remote Similarity	NPC204105
0.6598	Remote Similarity	NPC475206
0.6598	Remote Similarity	NPC300082
0.6588	Remote Similarity	NPC328089
0.6588	Remote Similarity	NPC68343
0.6574	Remote Similarity	NPC278628
0.6574	Remote Similarity	NPC231530
0.6571	Remote Similarity	NPC218383
0.6569	Remote Similarity	NPC470010
0.6569	Remote Similarity	NPC323008
0.6569	Remote Similarity	NPC262133
0.6569	Remote Similarity	NPC477131
0.6569	Remote Similarity	NPC470013
0.6566	Remote Similarity	NPC79549
0.6566	Remote Similarity	NPC183546
0.6566	Remote Similarity	NPC247406
0.6566	Remote Similarity	NPC48866
0.6566	Remote Similarity	NPC224652
0.6562	Remote Similarity	NPC52609
0.6562	Remote Similarity	NPC1761
0.6562	Remote Similarity	NPC69469
0.6559	Remote Similarity	NPC267231
0.6559	Remote Similarity	NPC192006
0.6556	Remote Similarity	NPC477085
0.6555	Remote Similarity	NPC470973
0.6542	Remote Similarity	NPC140723
0.6538	Remote Similarity	NPC245521
0.6538	Remote Similarity	NPC87090
0.6538	Remote Similarity	NPC475438
0.6535	Remote Similarity	NPC184063
0.6535	Remote Similarity	NPC208886
0.6535	Remote Similarity	NPC472468
0.6535	Remote Similarity	NPC184463
0.6535	Remote Similarity	NPC12172
0.6535	Remote Similarity	NPC30515
0.6535	Remote Similarity	NPC154101
0.6531	Remote Similarity	NPC477993
0.6531	Remote Similarity	NPC64153
0.6531	Remote Similarity	NPC475753
0.6531	Remote Similarity	NPC187661
0.6531	Remote Similarity	NPC477994
0.6531	Remote Similarity	NPC212843
0.6526	Remote Similarity	NPC52861
0.6526	Remote Similarity	NPC470241
0.6526	Remote Similarity	NPC325031
0.6522	Remote Similarity	NPC61863
0.6522	Remote Similarity	NPC12740
0.6522	Remote Similarity	NPC110461
0.6522	Remote Similarity	NPC93688
0.6522	Remote Similarity	NPC109603
0.6517	Remote Similarity	NPC318766
0.6517	Remote Similarity	NPC472955
0.6509	Remote Similarity	NPC171759
0.6505	Remote Similarity	NPC54905
0.6505	Remote Similarity	NPC469599
0.6505	Remote Similarity	NPC314009
0.6505	Remote Similarity	NPC107476
0.6505	Remote Similarity	NPC472873
0.65	Remote Similarity	NPC38392
0.65	Remote Similarity	NPC256902
0.65	Remote Similarity	NPC118193
0.65	Remote Similarity	NPC232747
0.65	Remote Similarity	NPC295312
0.65	Remote Similarity	NPC307411
0.65	Remote Similarity	NPC474032
0.6495	Remote Similarity	NPC472958
0.6495	Remote Similarity	NPC476804
0.6495	Remote Similarity	NPC156485
0.6495	Remote Similarity	NPC472957
0.6491	Remote Similarity	NPC329869
0.6489	Remote Similarity	NPC167881
0.6489	Remote Similarity	NPC470239

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 NPC475712 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	2036
0.2-0.3	4225
0.3-0.4	1959
0.4-0.5	453
0.5-0.6	263
0.6-0.7	39
0.7-0.8	17
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
0.7778	Intermediate Similarity	NPD5766	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4249	Approved
0.7556	Intermediate Similarity	NPD6435	Approved
0.7528	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4250	Approved
0.7527	Intermediate Similarity	NPD4251	Approved
0.7444	Intermediate Similarity	NPD5369	Approved
0.7333	Intermediate Similarity	NPD5368	Approved
0.7303	Intermediate Similarity	NPD4271	Approved
0.7303	Intermediate Similarity	NPD4268	Approved
0.7283	Intermediate Similarity	NPD5362	Discontinued
0.7174	Intermediate Similarity	NPD4270	Approved
0.7174	Intermediate Similarity	NPD4269	Approved
0.7143	Intermediate Similarity	NPD4252	Approved
0.7143	Intermediate Similarity	NPD4822	Approved
0.7143	Intermediate Similarity	NPD4819	Approved
0.7143	Intermediate Similarity	NPD4820	Approved
0.7143	Intermediate Similarity	NPD4821	Approved
0.71	Intermediate Similarity	NPD4792	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5786	Approved
0.6947	Remote Similarity	NPD5363	Approved
0.6915	Remote Similarity	NPD7154	Phase 3
0.6768	Remote Similarity	NPD5785	Approved
0.6739	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5332	Approved
0.6737	Remote Similarity	NPD5331	Approved
0.6702	Remote Similarity	NPD4790	Discontinued
0.6638	Remote Similarity	NPD5983	Phase 2
0.6598	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7983	Approved
0.6522	Remote Similarity	NPD6314	Approved
0.6522	Remote Similarity	NPD6313	Approved
0.6522	Remote Similarity	NPD6335	Approved
0.6466	Remote Similarity	NPD7100	Approved
0.646	Remote Similarity	NPD4632	Approved
0.6436	Remote Similarity	NPD46	Approved
0.6436	Remote Similarity	NPD6698	Approved
0.6429	Remote Similarity	NPD1719	Phase 1
0.6417	Remote Similarity	NPD6336	Discontinued
0.6337	Remote Similarity	NPD1695	Approved
0.6325	Remote Similarity	NPD7101	Approved
0.6311	Remote Similarity	NPD6399	Phase 3
0.6311	Remote Similarity	NPD5778	Approved
0.6311	Remote Similarity	NPD5779	Approved
0.631	Remote Similarity	NPD3198	Approved
0.6293	Remote Similarity	NPD6009	Approved
0.6228	Remote Similarity	NPD6053	Discontinued
0.6216	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7637	Suspended
0.6207	Remote Similarity	NPD3197	Phase 1
0.62	Remote Similarity	NPD7146	Approved
0.62	Remote Similarity	NPD6409	Approved
0.62	Remote Similarity	NPD7334	Approved
0.62	Remote Similarity	NPD7521	Approved
0.62	Remote Similarity	NPD5330	Approved
0.62	Remote Similarity	NPD6684	Approved
0.6195	Remote Similarity	NPD5169	Approved
0.6176	Remote Similarity	NPD5370	Suspended
0.6176	Remote Similarity	NPD6101	Approved
0.6176	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7638	Approved
0.6162	Remote Similarity	NPD3133	Approved
0.6162	Remote Similarity	NPD3666	Approved
0.6162	Remote Similarity	NPD3665	Phase 1
0.614	Remote Similarity	NPD5215	Approved
0.614	Remote Similarity	NPD5127	Approved
0.6122	Remote Similarity	NPD3667	Approved
0.6121	Remote Similarity	NPD5167	Approved
0.6111	Remote Similarity	NPD7639	Approved
0.6111	Remote Similarity	NPD7640	Approved
0.6095	Remote Similarity	NPD5282	Discontinued
0.608	Remote Similarity	NPD5956	Approved
0.6078	Remote Similarity	NPD6903	Approved
0.6078	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6084	Phase 2
0.6075	Remote Similarity	NPD6083	Phase 2
0.6071	Remote Similarity	NPD6685	Approved
0.6071	Remote Similarity	NPD5697	Approved
0.6071	Remote Similarity	NPD6412	Phase 2
0.6068	Remote Similarity	NPD6868	Approved
0.6058	Remote Similarity	NPD6411	Approved
0.6058	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6371	Approved
0.605	Remote Similarity	NPD4522	Approved
0.6048	Remote Similarity	NPD6033	Approved
0.6038	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5695	Phase 3
0.6018	Remote Similarity	NPD6899	Approved
0.6018	Remote Similarity	NPD6881	Approved
0.6018	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD5216	Approved
0.6	Remote Similarity	NPD5217	Approved
0.6	Remote Similarity	NPD4786	Approved
0.5982	Remote Similarity	NPD6675	Approved
0.5982	Remote Similarity	NPD7128	Approved
0.5982	Remote Similarity	NPD5739	Approved
0.5982	Remote Similarity	NPD6402	Approved
0.5982	Remote Similarity	NPD6008	Approved
0.5981	Remote Similarity	NPD7839	Suspended
0.5976	Remote Similarity	NPD3172	Approved
0.5965	Remote Similarity	NPD6013	Approved
0.5965	Remote Similarity	NPD6012	Approved
0.5965	Remote Similarity	NPD6014	Approved
0.5962	Remote Similarity	NPD7838	Discovery
0.5941	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6614	Approved
0.5929	Remote Similarity	NPD5701	Approved
0.5913	Remote Similarity	NPD6883	Approved
0.5913	Remote Similarity	NPD7102	Approved
0.5913	Remote Similarity	NPD7290	Approved
0.5905	Remote Similarity	NPD5284	Approved
0.5905	Remote Similarity	NPD5281	Approved
0.5904	Remote Similarity	NPD3195	Phase 2
0.5904	Remote Similarity	NPD4266	Approved
0.5904	Remote Similarity	NPD3194	Approved
0.5904	Remote Similarity	NPD3196	Approved
0.5888	Remote Similarity	NPD5654	Approved
0.5877	Remote Similarity	NPD7320	Approved
0.5872	Remote Similarity	NPD5696	Approved
0.5868	Remote Similarity	NPD6319	Approved
0.5862	Remote Similarity	NPD6650	Approved
0.5862	Remote Similarity	NPD8130	Phase 1
0.5862	Remote Similarity	NPD6617	Approved
0.5862	Remote Similarity	NPD6847	Approved
0.5862	Remote Similarity	NPD6649	Approved
0.5862	Remote Similarity	NPD6869	Approved
0.5856	Remote Similarity	NPD5091	Approved
0.5849	Remote Similarity	NPD4202	Approved
0.5826	Remote Similarity	NPD6373	Approved
0.5826	Remote Similarity	NPD6372	Approved
0.5824	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD6882	Approved
0.5812	Remote Similarity	NPD8297	Approved
0.5804	Remote Similarity	NPD5765	Approved
0.578	Remote Similarity	NPD5959	Approved
0.5776	Remote Similarity	NPD6420	Discontinued
0.5739	Remote Similarity	NPD6686	Approved
0.5739	Remote Similarity	NPD5128	Approved
0.5739	Remote Similarity	NPD5168	Approved
0.5728	Remote Similarity	NPD3618	Phase 1
0.5728	Remote Similarity	NPD6422	Discontinued
0.5728	Remote Similarity	NPD5279	Phase 3
0.5728	Remote Similarity	NPD6098	Approved
0.5727	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD7604	Phase 2
0.5726	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4802	Phase 2
0.5714	Remote Similarity	NPD4753	Phase 2
0.5714	Remote Similarity	NPD4238	Approved
0.5701	Remote Similarity	NPD5133	Approved
0.5686	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.568	Remote Similarity	NPD7492	Approved
0.5678	Remote Similarity	NPD6912	Phase 3
0.5676	Remote Similarity	NPD5285	Approved
0.5676	Remote Similarity	NPD5286	Approved
0.5676	Remote Similarity	NPD4696	Approved
0.567	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.566	Remote Similarity	NPD5207	Approved
0.5644	Remote Similarity	NPD4223	Phase 3
0.5644	Remote Similarity	NPD5209	Approved
0.5644	Remote Similarity	NPD4221	Approved
0.5636	Remote Similarity	NPD4755	Approved
0.5635	Remote Similarity	NPD6616	Approved
0.5631	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5223	Approved
0.562	Remote Similarity	NPD6317	Approved
0.5619	Remote Similarity	NPD6672	Approved
0.5619	Remote Similarity	NPD4518	Approved
0.5619	Remote Similarity	NPD5737	Approved
0.5619	Remote Similarity	NPD5208	Approved
0.5612	Remote Similarity	NPD6932	Approved
0.561	Remote Similarity	NPD6054	Approved
0.5607	Remote Similarity	NPD6079	Approved
0.5607	Remote Similarity	NPD5694	Approved
0.5607	Remote Similarity	NPD8034	Phase 2
0.5607	Remote Similarity	NPD8035	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