NPASS Compound

Structure

NPC290094 OpenBabel07101718332D 22 22 0 0 0 0 0 0 0 0999 V2000 -10.3923 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 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 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -2.0000 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 -9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -2.0000 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 -11.2583 -1.5000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 -11.2583 -0.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 1 0 0 0 0 2 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 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 14 1 0 0 0 0 12 17 1 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 14 19 1 0 0 0 0 15 19 1 0 0 0 0 16 20 2 0 0 0 0 17 21 1 0 0 0 0 18 19 2 0 0 0 0 18 20 1 0 0 0 0 21 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.27
Volume:	351.498
LogP:	5.254
LogD:	3.61
LogS:	-2.801
# Rotatable Bonds:	14
TPSA:	36.36
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.377
Synthetic Accessibility Score:	2.198
Fsp3:	0.737
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:	-4.748
MDCK Permeability:	1.303646968153771e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.405
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.095
30% Bioavailability (F30%):	0.84

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.928
Plasma Protein Binding (PPB):	87.4931411743164%
Volume Distribution (VD):	1.294
Pgp-substrate:	7.4471869468688965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.917
CYP1A2-substrate:	0.523
CYP2C19-inhibitor:	0.849
CYP2C19-substrate:	0.903
CYP2C9-inhibitor:	0.438
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.726
CYP2D6-substrate:	0.6
CYP3A4-inhibitor:	0.899
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	9.007
Half-life (T1/2):	0.203

ADMET: Toxicity

hERG Blockers:	0.721
Human Hepatotoxicity (H-HT):	0.039
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.262
Maximum Recommended Daily Dose:	0.077
Skin Sensitization:	0.965
Carcinogencity:	0.078
Eye Corrosion:	0.97
Eye Irritation:	0.928
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC290094

Natural Product ID:	NPC290094
*Common Name:**	Hachijodine E
IUPAC Name:	N-methyl-N-(13-pyridin-3-yltridecyl)hydroxylamine
Synonyms:	Hachijodine E
Standard InCHIKey:	BIWXINAQTYJZGO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H34N2O/c1-21(22)17-12-10-8-6-4-2-3-5-7-9-11-14-19-15-13-16-20-18-19/h13,15-16,18,22H,2-12,14,17H2,1H3
SMILES:	CN(CCCCCCCCCCCCCc1cccnc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496434
PubChem CID:	10244668
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines 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
NPO32714	xestospongia	Genus	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843588]
NPO32954	amphimedon	Genus	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843588]
NPO32714	xestospongia	Genus	Petrosiidae	Eukaryota	n.a.	South Pacific	n.a.	PMID[20634081]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	Activity	=	2.3	ug ml-1	PMID[481403]

☑ 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 NPC290094 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	664
0.1-0.2	10497
0.2-0.3	18724
0.3-0.4	7172
0.4-0.5	3020
0.5-0.6	1767
0.6-0.7	640
0.7-0.8	168
0.8-0.85	25
0.85-0.9	8
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9748	High Similarity	NPC202957
0.9748	High Similarity	NPC169625
0.9426	High Similarity	NPC89490
0.935	High Similarity	NPC475090
0.935	High Similarity	NPC329896
0.935	High Similarity	NPC475105
0.9153	High Similarity	NPC297486
0.9153	High Similarity	NPC471402
0.9153	High Similarity	NPC240136
0.888	High Similarity	NPC471313
0.888	High Similarity	NPC471311
0.8879	High Similarity	NPC27802
0.879	High Similarity	NPC476322
0.876	High Similarity	NPC91958
0.8699	High Similarity	NPC182570
0.8699	High Similarity	NPC265605
0.8699	High Similarity	NPC48564
0.8629	High Similarity	NPC329825
0.8621	High Similarity	NPC76540
0.8605	High Similarity	NPC471322
0.8527	High Similarity	NPC69914
0.8455	Intermediate Similarity	NPC143603
0.845	Intermediate Similarity	NPC476131
0.8425	Intermediate Similarity	NPC146373
0.8425	Intermediate Similarity	NPC166424
0.8425	Intermediate Similarity	NPC245244
0.8346	Intermediate Similarity	NPC27740
0.8284	Intermediate Similarity	NPC471312
0.8264	Intermediate Similarity	NPC235843
0.8182	Intermediate Similarity	NPC324611
0.8182	Intermediate Similarity	NPC256893
0.8148	Intermediate Similarity	NPC251722
0.8148	Intermediate Similarity	NPC314102
0.8143	Intermediate Similarity	NPC470111
0.8125	Intermediate Similarity	NPC46358
0.8103	Intermediate Similarity	NPC83987
0.8045	Intermediate Similarity	NPC101165
0.8029	Intermediate Similarity	NPC316811
0.8029	Intermediate Similarity	NPC315348
0.8029	Intermediate Similarity	NPC32002
0.8	Intermediate Similarity	NPC231655
0.797	Intermediate Similarity	NPC282398
0.7929	Intermediate Similarity	NPC471323
0.7883	Intermediate Similarity	NPC65408
0.7883	Intermediate Similarity	NPC150259
0.7879	Intermediate Similarity	NPC212125
0.7857	Intermediate Similarity	NPC476566
0.7842	Intermediate Similarity	NPC469767
0.7842	Intermediate Similarity	NPC469768
0.7842	Intermediate Similarity	NPC469779
0.7842	Intermediate Similarity	NPC469784
0.7842	Intermediate Similarity	NPC469783
0.7842	Intermediate Similarity	NPC469780
0.7842	Intermediate Similarity	NPC469761
0.7838	Intermediate Similarity	NPC71079
0.7786	Intermediate Similarity	NPC469766
0.7785	Intermediate Similarity	NPC474217
0.7762	Intermediate Similarity	NPC477974
0.7746	Intermediate Similarity	NPC285731
0.7704	Intermediate Similarity	NPC315320
0.7682	Intermediate Similarity	NPC127730
0.7682	Intermediate Similarity	NPC278366
0.7656	Intermediate Similarity	NPC81561
0.7655	Intermediate Similarity	NPC105818
0.7655	Intermediate Similarity	NPC24678
0.7643	Intermediate Similarity	NPC73767
0.7626	Intermediate Similarity	NPC84911
0.7622	Intermediate Similarity	NPC314372
0.7616	Intermediate Similarity	NPC85918
0.7612	Intermediate Similarity	NPC306397
0.7606	Intermediate Similarity	NPC190296
0.7578	Intermediate Similarity	NPC148140
0.7571	Intermediate Similarity	NPC169433
0.7568	Intermediate Similarity	NPC51054
0.7554	Intermediate Similarity	NPC261195
0.7554	Intermediate Similarity	NPC29886
0.7554	Intermediate Similarity	NPC96102
0.7551	Intermediate Similarity	NPC469760
0.7551	Intermediate Similarity	NPC469763
0.7551	Intermediate Similarity	NPC73952
0.7551	Intermediate Similarity	NPC469786
0.7551	Intermediate Similarity	NPC25008
0.7551	Intermediate Similarity	NPC469765
0.7551	Intermediate Similarity	NPC259644
0.7538	Intermediate Similarity	NPC11863
0.7535	Intermediate Similarity	NPC476454
0.7534	Intermediate Similarity	NPC40070
0.7518	Intermediate Similarity	NPC110126
0.7517	Intermediate Similarity	NPC129721
0.75	Intermediate Similarity	NPC75540
0.75	Intermediate Similarity	NPC105127
0.75	Intermediate Similarity	NPC212376
0.75	Intermediate Similarity	NPC70922
0.75	Intermediate Similarity	NPC80597
0.75	Intermediate Similarity	NPC211572
0.75	Intermediate Similarity	NPC56856
0.7483	Intermediate Similarity	NPC477977
0.7483	Intermediate Similarity	NPC470233
0.7481	Intermediate Similarity	NPC165370
0.748	Intermediate Similarity	NPC473901
0.7464	Intermediate Similarity	NPC322488
0.7432	Intermediate Similarity	NPC138842
0.7429	Intermediate Similarity	NPC29702
0.7407	Intermediate Similarity	NPC135488
0.74	Intermediate Similarity	NPC236711
0.7397	Intermediate Similarity	NPC201380
0.7397	Intermediate Similarity	NPC179787
0.7397	Intermediate Similarity	NPC471957
0.7394	Intermediate Similarity	NPC104483
0.7391	Intermediate Similarity	NPC82295
0.7379	Intermediate Similarity	NPC159856
0.7379	Intermediate Similarity	NPC86288
0.7368	Intermediate Similarity	NPC225018
0.7364	Intermediate Similarity	NPC84268
0.7353	Intermediate Similarity	NPC278451
0.7348	Intermediate Similarity	NPC215519
0.7347	Intermediate Similarity	NPC321911
0.7343	Intermediate Similarity	NPC279081
0.7338	Intermediate Similarity	NPC98187
0.7333	Intermediate Similarity	NPC213774
0.7333	Intermediate Similarity	NPC469785
0.7329	Intermediate Similarity	NPC63545
0.7328	Intermediate Similarity	NPC54102
0.7328	Intermediate Similarity	NPC162689
0.7299	Intermediate Similarity	NPC471589
0.7297	Intermediate Similarity	NPC53947
0.7285	Intermediate Similarity	NPC469762
0.7279	Intermediate Similarity	NPC469811
0.7273	Intermediate Similarity	NPC477975
0.726	Intermediate Similarity	NPC469525
0.7259	Intermediate Similarity	NPC122718
0.7255	Intermediate Similarity	NPC59779
0.7255	Intermediate Similarity	NPC471177
0.7255	Intermediate Similarity	NPC124542
0.7241	Intermediate Similarity	NPC20144
0.7237	Intermediate Similarity	NPC56765
0.7222	Intermediate Similarity	NPC230002
0.7219	Intermediate Similarity	NPC476464
0.7214	Intermediate Similarity	NPC330326
0.7211	Intermediate Similarity	NPC288838
0.7208	Intermediate Similarity	NPC311276
0.7208	Intermediate Similarity	NPC478182
0.72	Intermediate Similarity	NPC325903
0.72	Intermediate Similarity	NPC200214
0.7171	Intermediate Similarity	NPC469897
0.7161	Intermediate Similarity	NPC471178
0.7143	Intermediate Similarity	NPC467188
0.7133	Intermediate Similarity	NPC216713
0.7124	Intermediate Similarity	NPC92796
0.7124	Intermediate Similarity	NPC135141
0.7115	Intermediate Similarity	NPC160105
0.7113	Intermediate Similarity	NPC198988
0.7103	Intermediate Similarity	NPC2949
0.7103	Intermediate Similarity	NPC59084
0.7097	Intermediate Similarity	NPC90723
0.7097	Intermediate Similarity	NPC78375
0.7097	Intermediate Similarity	NPC40779
0.7097	Intermediate Similarity	NPC473057
0.7097	Intermediate Similarity	NPC469813
0.7097	Intermediate Similarity	NPC476446
0.7095	Intermediate Similarity	NPC143872
0.7078	Intermediate Similarity	NPC44773
0.7078	Intermediate Similarity	NPC215584
0.7063	Intermediate Similarity	NPC325252
0.7059	Intermediate Similarity	NPC286427
0.7059	Intermediate Similarity	NPC193740
0.7059	Intermediate Similarity	NPC167635
0.7055	Intermediate Similarity	NPC63157
0.7055	Intermediate Similarity	NPC473868
0.7047	Intermediate Similarity	NPC105811
0.7039	Intermediate Similarity	NPC477815
0.7032	Intermediate Similarity	NPC242116
0.7032	Intermediate Similarity	NPC470203
0.7025	Intermediate Similarity	NPC116961
0.702	Intermediate Similarity	NPC70406
0.702	Intermediate Similarity	NPC470823
0.7014	Intermediate Similarity	NPC114310
0.7013	Intermediate Similarity	NPC80681
0.7013	Intermediate Similarity	NPC41257
0.7013	Intermediate Similarity	NPC293487
0.7013	Intermediate Similarity	NPC206819
0.7013	Intermediate Similarity	NPC477591
0.7013	Intermediate Similarity	NPC318065
0.7006	Intermediate Similarity	NPC108469
0.7006	Intermediate Similarity	NPC49954
0.7006	Intermediate Similarity	NPC474561
0.7	Intermediate Similarity	NPC317054
0.6987	Remote Similarity	NPC97367
0.6981	Remote Similarity	NPC201634
0.6974	Remote Similarity	NPC141926
0.6968	Remote Similarity	NPC470204
0.6962	Remote Similarity	NPC201700
0.6957	Remote Similarity	NPC151489
0.695	Remote Similarity	NPC22079
0.6948	Remote Similarity	NPC216643
0.6944	Remote Similarity	NPC328029
0.6937	Remote Similarity	NPC314603
0.6928	Remote Similarity	NPC34844
0.6928	Remote Similarity	NPC209362
0.6923	Remote Similarity	NPC282231

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 NPC290094 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	884
0.2-0.3	992
0.3-0.4	1905
0.4-0.5	2812
0.5-0.6	1607
0.6-0.7	474
0.7-0.8	126
0.8-0.85	18
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.873	High Similarity	NPD2118	Approved
0.873	High Similarity	NPD2119	Approved
0.8729	High Similarity	NPD4823	Approved
0.8729	High Similarity	NPD4824	Approved
0.8699	High Similarity	NPD268	Approved
0.8699	High Similarity	NPD270	Clinical (unspecified phase)
0.8699	High Similarity	NPD271	Approved
0.8527	High Similarity	NPD3475	Approved
0.8527	High Similarity	NPD3476	Approved
0.8512	High Similarity	NPD269	Clinical (unspecified phase)
0.8504	High Similarity	NPD9583	Approved
0.8397	Intermediate Similarity	NPD1995	Approved
0.8397	Intermediate Similarity	NPD1994	Approved
0.8397	Intermediate Similarity	NPD1993	Approved
0.8346	Intermediate Similarity	NPD9357	Approved
0.8333	Intermediate Similarity	NPD4028	Approved
0.8333	Intermediate Similarity	NPD4030	Approved
0.8333	Intermediate Similarity	NPD3944	Approved
0.8333	Intermediate Similarity	NPD4029	Approved
0.8333	Intermediate Similarity	NPD3942	Approved
0.8295	Intermediate Similarity	NPD991	Phase 2
0.8295	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD792	Discontinued
0.8189	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD1598	Discontinued
0.812	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD715	Phase 3
0.8088	Intermediate Similarity	NPD2896	Discontinued
0.8071	Intermediate Similarity	NPD7469	Discontinued
0.8042	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD2068	Approved
0.8029	Intermediate Similarity	NPD2071	Approved
0.8029	Intermediate Similarity	NPD2069	Approved
0.8029	Intermediate Similarity	NPD2073	Approved
0.8029	Intermediate Similarity	NPD2075	Approved
0.8029	Intermediate Similarity	NPD2070	Approved
0.8029	Intermediate Similarity	NPD2074	Approved
0.8029	Intermediate Similarity	NPD2072	Approved
0.8	Intermediate Similarity	NPD2140	Approved
0.8	Intermediate Similarity	NPD2141	Approved
0.8	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD9098	Phase 3
0.8	Intermediate Similarity	NPD2142	Approved
0.7986	Intermediate Similarity	NPD3717	Discontinued
0.7955	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD9396	Approved
0.7937	Intermediate Similarity	NPD9392	Approved
0.7929	Intermediate Similarity	NPD3813	Approved
0.7887	Intermediate Similarity	NPD4702	Approved
0.7887	Intermediate Similarity	NPD4703	Approved
0.7883	Intermediate Similarity	NPD200	Phase 2
0.7883	Intermediate Similarity	NPD201	Phase 2
0.7879	Intermediate Similarity	NPD9284	Approved
0.7857	Intermediate Similarity	NPD4510	Discontinued
0.7817	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD2809	Approved
0.774	Intermediate Similarity	NPD5358	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2006	Phase 2
0.7704	Intermediate Similarity	NPD9206	Approved
0.7704	Intermediate Similarity	NPD9207	Approved
0.7698	Intermediate Similarity	NPD1380	Discovery
0.7676	Intermediate Similarity	NPD1352	Discontinued
0.766	Intermediate Similarity	NPD1722	Approved
0.7647	Intermediate Similarity	NPD9726	Discontinued
0.7643	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD786	Approved
0.7639	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD4547	Phase 3
0.7638	Intermediate Similarity	NPD60	Approved
0.7612	Intermediate Similarity	NPD9080	Approved
0.7606	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4641	Discontinued
0.7603	Intermediate Similarity	NPD3262	Approved
0.7589	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD2430	Phase 2
0.7554	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD3385	Approved
0.7535	Intermediate Similarity	NPD1383	Phase 3
0.7535	Intermediate Similarity	NPD1382	Phase 2
0.7534	Intermediate Similarity	NPD2466	Phase 3
0.7534	Intermediate Similarity	NPD2465	Approved
0.7534	Intermediate Similarity	NPD2462	Phase 3
0.7519	Intermediate Similarity	NPD8840	Approved
0.7518	Intermediate Similarity	NPD803	Phase 1
0.7517	Intermediate Similarity	NPD1270	Approved
0.7517	Intermediate Similarity	NPD1661	Suspended
0.75	Intermediate Similarity	NPD3654	Approved
0.75	Intermediate Similarity	NPD9506	Approved
0.7482	Intermediate Similarity	NPD272	Approved
0.7467	Intermediate Similarity	NPD5255	Approved
0.7466	Intermediate Similarity	NPD1183	Approved
0.7465	Intermediate Similarity	NPD1649	Discontinued
0.745	Intermediate Similarity	NPD6026	Approved
0.7429	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD2511	Approved
0.7413	Intermediate Similarity	NPD4805	Approved
0.7403	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2581	Approved
0.74	Intermediate Similarity	NPD2582	Approved
0.74	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2110	Approved
0.7394	Intermediate Similarity	NPD4804	Approved
0.7368	Intermediate Similarity	NPD8026	Phase 1
0.7365	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3100	Discontinued
0.7324	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3339	Approved
0.7315	Intermediate Similarity	NPD2837	Discontinued
0.7297	Intermediate Similarity	NPD2172	Phase 1
0.7293	Intermediate Similarity	NPD9598	Discontinued
0.7292	Intermediate Similarity	NPD5020	Approved
0.729	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6497	Approved
0.7267	Intermediate Similarity	NPD2061	Approved
0.7267	Intermediate Similarity	NPD2165	Phase 1
0.7266	Intermediate Similarity	NPD809	Discontinued
0.7255	Intermediate Similarity	NPD5315	Discontinued
0.7255	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6771	Discontinued
0.7239	Intermediate Similarity	NPD5787	Discontinued
0.723	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5611	Phase 2
0.7222	Intermediate Similarity	NPD9599	Approved
0.7219	Intermediate Similarity	NPD3115	Approved
0.7219	Intermediate Similarity	NPD3112	Approved
0.7219	Intermediate Similarity	NPD3113	Approved
0.7219	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3114	Approved
0.7214	Intermediate Similarity	NPD9100	Approved
0.7208	Intermediate Similarity	NPD5088	Discontinued
0.7208	Intermediate Similarity	NPD6635	Approved
0.719	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1328	Approved
0.7143	Intermediate Similarity	NPD4239	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD45	Approved
0.7133	Intermediate Similarity	NPD6554	Approved
0.7124	Intermediate Similarity	NPD5418	Discontinued
0.7124	Intermediate Similarity	NPD3433	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2580	Discontinued
0.7097	Intermediate Similarity	NPD3323	Discontinued
0.7097	Intermediate Similarity	NPD3583	Phase 2
0.7097	Intermediate Similarity	NPD8129	Discovery
0.709	Intermediate Similarity	NPD4811	Discontinued
0.7089	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5862	Discovery
0.707	Intermediate Similarity	NPD2640	Approved
0.707	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2641	Approved
0.7067	Intermediate Similarity	NPD7913	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1255	Approved
0.7063	Intermediate Similarity	NPD1256	Approved
0.7063	Intermediate Similarity	NPD1253	Approved
0.7063	Intermediate Similarity	NPD1254	Approved
0.7059	Intermediate Similarity	NPD2145	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2720	Phase 1
0.7039	Intermediate Similarity	NPD976	Approved
0.7039	Intermediate Similarity	NPD975	Approved
0.7039	Intermediate Similarity	NPD977	Approved
0.7027	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4973	Approved
0.7019	Intermediate Similarity	NPD8123	Approved
0.7019	Intermediate Similarity	NPD8122	Approved
0.7006	Intermediate Similarity	NPD5636	Discontinued
0.7006	Intermediate Similarity	NPD6446	Discontinued
0.6994	Remote Similarity	NPD4891	Phase 2
0.6985	Remote Similarity	NPD1561	Phase 2
0.6981	Remote Similarity	NPD3116	Approved
0.6981	Remote Similarity	NPD3117	Approved
0.6974	Remote Similarity	NPD1917	Discontinued
0.6968	Remote Similarity	NPD1403	Approved
0.6968	Remote Similarity	NPD1404	Approved
0.6962	Remote Similarity	NPD4640	Approved
0.6962	Remote Similarity	NPD1343	Approved
0.6962	Remote Similarity	NPD4639	Approved
0.6962	Remote Similarity	NPD4638	Approved
0.6959	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1988	Phase 1
0.6959	Remote Similarity	NPD649	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5100	Phase 3
0.6957	Remote Similarity	NPD6044	Discontinued
0.6954	Remote Similarity	NPD4463	Approved
0.6954	Remote Similarity	NPD4462	Approved
0.6948	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD490	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD925	Approved
0.6943	Remote Similarity	NPD926	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