NPASS Compound

Structure

NPC475090 OpenBabel07101719142D 22 22 0 0 1 0 0 0 0 0999 V2000 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -7.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -1.7321 -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 -3.4641 2.0000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 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 -2.5981 1.5000 0.0000 C 0 0 3 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 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 22 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 1 0 0 0 0 9 12 1 0 0 0 0 10 15 1 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 19 2 0 0 0 0 17 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:	4.965
LogD:	3.643
LogS:	-2.939
# Rotatable Bonds:	14
TPSA:	34.15
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.391
Synthetic Accessibility Score:	2.804
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:	-4.479
MDCK Permeability:	2.027300615736749e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.57
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.948

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.832
Plasma Protein Binding (PPB):	85.1478042602539%
Volume Distribution (VD):	1.322
Pgp-substrate:	9.08937931060791%

ADMET: Metabolism

CYP1A2-inhibitor:	0.935
CYP1A2-substrate:	0.497
CYP2C19-inhibitor:	0.879
CYP2C19-substrate:	0.826
CYP2C9-inhibitor:	0.625
CYP2C9-substrate:	0.854
CYP2D6-inhibitor:	0.906
CYP2D6-substrate:	0.313
CYP3A4-inhibitor:	0.956
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	9.139
Half-life (T1/2):	0.243

ADMET: Toxicity

hERG Blockers:	0.579
Human Hepatotoxicity (H-HT):	0.434
Drug-inuced Liver Injury (DILI):	0.07
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.692
Maximum Recommended Daily Dose:	0.142
Skin Sensitization:	0.964
Carcinogencity:	0.036
Eye Corrosion:	0.224
Eye Irritation:	0.406
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC475090

Natural Product ID:	NPC475090
*Common Name:**	Hachijodine D
IUPAC Name:	N-methoxy-11-methyl-12-pyridin-3-yldodecan-1-amine
Synonyms:	Hachijodine D
Standard InCHIKey:	NXHGYPOMNKIEHF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H34N2O/c1-18(16-19-13-11-14-20-17-19)12-9-7-5-3-4-6-8-10-15-21-22-2/h11,13-14,17-18,21H,3-10,12,15-16H2,1-2H3
SMILES:	CC(CCCCCCCCCCNOC)CC1=CN=CC=C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497090
PubChem CID:	10040837
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	=	2.2	ug ml-1	PMID[494900]

☑ 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 NPC475090 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	485
0.1-0.2	9191
0.2-0.3	19861
0.3-0.4	7300
0.4-0.5	2991
0.5-0.6	1874
0.6-0.7	745
0.7-0.8	224
0.8-0.85	11
0.85-0.9	7
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475105
1.0	High Similarity	NPC329896
0.9918	High Similarity	NPC89490
0.935	High Similarity	NPC290094
0.9127	High Similarity	NPC202957
0.9127	High Similarity	NPC169625
0.871	High Similarity	NPC471402
0.871	High Similarity	NPC240136
0.871	High Similarity	NPC297486
0.8636	High Similarity	NPC471322
0.8605	High Similarity	NPC166424
0.8605	High Similarity	NPC146373
0.8605	High Similarity	NPC245244
0.8527	High Similarity	NPC27740
0.8473	Intermediate Similarity	NPC471311
0.8473	Intermediate Similarity	NPC471313
0.8443	Intermediate Similarity	NPC27802
0.8385	Intermediate Similarity	NPC476322
0.8372	Intermediate Similarity	NPC329825
0.8346	Intermediate Similarity	NPC91958
0.8295	Intermediate Similarity	NPC182570
0.8295	Intermediate Similarity	NPC265605
0.8295	Intermediate Similarity	NPC48564
0.8197	Intermediate Similarity	NPC76540
0.8148	Intermediate Similarity	NPC69914
0.8088	Intermediate Similarity	NPC101165
0.8074	Intermediate Similarity	NPC476131
0.8062	Intermediate Similarity	NPC143603
0.8015	Intermediate Similarity	NPC282398
0.8014	Intermediate Similarity	NPC469779
0.8014	Intermediate Similarity	NPC469761
0.8014	Intermediate Similarity	NPC469780
0.8014	Intermediate Similarity	NPC469767
0.8014	Intermediate Similarity	NPC469783
0.8014	Intermediate Similarity	NPC469784
0.8014	Intermediate Similarity	NPC469768
0.7958	Intermediate Similarity	NPC469766
0.7956	Intermediate Similarity	NPC256893
0.7929	Intermediate Similarity	NPC471312
0.7874	Intermediate Similarity	NPC235843
0.7832	Intermediate Similarity	NPC476454
0.7826	Intermediate Similarity	NPC324611
0.7823	Intermediate Similarity	NPC105818
0.7823	Intermediate Similarity	NPC24678
0.7817	Intermediate Similarity	NPC73767
0.7817	Intermediate Similarity	NPC315348
0.7817	Intermediate Similarity	NPC316811
0.7817	Intermediate Similarity	NPC32002
0.7808	Intermediate Similarity	NPC470111
0.7801	Intermediate Similarity	NPC251722
0.7801	Intermediate Similarity	NPC84911
0.7801	Intermediate Similarity	NPC314102
0.7793	Intermediate Similarity	NPC314372
0.7778	Intermediate Similarity	NPC190296
0.7761	Intermediate Similarity	NPC46358
0.773	Intermediate Similarity	NPC96102
0.773	Intermediate Similarity	NPC29886
0.773	Intermediate Similarity	NPC261195
0.7724	Intermediate Similarity	NPC471323
0.7718	Intermediate Similarity	NPC73952
0.7718	Intermediate Similarity	NPC469765
0.7718	Intermediate Similarity	NPC259644
0.7718	Intermediate Similarity	NPC469760
0.7718	Intermediate Similarity	NPC469763
0.7718	Intermediate Similarity	NPC469786
0.7718	Intermediate Similarity	NPC25008
0.7712	Intermediate Similarity	NPC474217
0.7705	Intermediate Similarity	NPC83987
0.7692	Intermediate Similarity	NPC110126
0.7687	Intermediate Similarity	NPC477974
0.7676	Intermediate Similarity	NPC65408
0.7676	Intermediate Similarity	NPC105127
0.7671	Intermediate Similarity	NPC285731
0.7667	Intermediate Similarity	NPC212376
0.7667	Intermediate Similarity	NPC75540
0.7667	Intermediate Similarity	NPC211572
0.7667	Intermediate Similarity	NPC70922
0.7667	Intermediate Similarity	NPC80597
0.7651	Intermediate Similarity	NPC470233
0.7647	Intermediate Similarity	NPC71079
0.7619	Intermediate Similarity	NPC231655
0.7616	Intermediate Similarity	NPC469785
0.7616	Intermediate Similarity	NPC51054
0.7584	Intermediate Similarity	NPC53947
0.7571	Intermediate Similarity	NPC82295
0.7568	Intermediate Similarity	NPC471957
0.7566	Intermediate Similarity	NPC469762
0.7552	Intermediate Similarity	NPC150259
0.7551	Intermediate Similarity	NPC159856
0.7536	Intermediate Similarity	NPC212125
0.7536	Intermediate Similarity	NPC306397
0.7517	Intermediate Similarity	NPC279081
0.7517	Intermediate Similarity	NPC321911
0.7516	Intermediate Similarity	NPC56765
0.75	Intermediate Similarity	NPC127730
0.75	Intermediate Similarity	NPC278366
0.75	Intermediate Similarity	NPC476566
0.7484	Intermediate Similarity	NPC311276
0.7483	Intermediate Similarity	NPC200214
0.7451	Intermediate Similarity	NPC236711
0.745	Intermediate Similarity	NPC201380
0.745	Intermediate Similarity	NPC179787
0.745	Intermediate Similarity	NPC469811
0.7436	Intermediate Similarity	NPC85918
0.7434	Intermediate Similarity	NPC477815
0.7424	Intermediate Similarity	NPC84268
0.7397	Intermediate Similarity	NPC230002
0.7389	Intermediate Similarity	NPC160105
0.7386	Intermediate Similarity	NPC476464
0.7383	Intermediate Similarity	NPC288838
0.7383	Intermediate Similarity	NPC63545
0.7376	Intermediate Similarity	NPC315320
0.7372	Intermediate Similarity	NPC476446
0.7372	Intermediate Similarity	NPC78375
0.7372	Intermediate Similarity	NPC40779
0.7372	Intermediate Similarity	NPC469813
0.7372	Intermediate Similarity	NPC90723
0.7368	Intermediate Similarity	NPC325903
0.7342	Intermediate Similarity	NPC201700
0.7338	Intermediate Similarity	NPC193740
0.7338	Intermediate Similarity	NPC469897
0.7338	Intermediate Similarity	NPC167635
0.7338	Intermediate Similarity	NPC286427
0.7329	Intermediate Similarity	NPC104483
0.7315	Intermediate Similarity	NPC467188
0.7313	Intermediate Similarity	NPC81561
0.7308	Intermediate Similarity	NPC225018
0.7303	Intermediate Similarity	NPC216713
0.7297	Intermediate Similarity	NPC477977
0.729	Intermediate Similarity	NPC92796
0.729	Intermediate Similarity	NPC41257
0.729	Intermediate Similarity	NPC135141
0.729	Intermediate Similarity	NPC318065
0.729	Intermediate Similarity	NPC206819
0.7286	Intermediate Similarity	NPC165370
0.7279	Intermediate Similarity	NPC59084
0.7278	Intermediate Similarity	NPC49954
0.7278	Intermediate Similarity	NPC474561
0.7273	Intermediate Similarity	NPC330326
0.7267	Intermediate Similarity	NPC143872
0.726	Intermediate Similarity	NPC104049
0.726	Intermediate Similarity	NPC169433
0.725	Intermediate Similarity	NPC201634
0.7241	Intermediate Similarity	NPC325252
0.7239	Intermediate Similarity	NPC148140
0.7237	Intermediate Similarity	NPC40070
0.7234	Intermediate Similarity	NPC471589
0.723	Intermediate Similarity	NPC63157
0.723	Intermediate Similarity	NPC473868
0.7226	Intermediate Similarity	NPC216643
0.7226	Intermediate Similarity	NPC129721
0.7219	Intermediate Similarity	NPC105811
0.7215	Intermediate Similarity	NPC477975
0.7206	Intermediate Similarity	NPC11863
0.7205	Intermediate Similarity	NPC314603
0.7197	Intermediate Similarity	NPC470203
0.719	Intermediate Similarity	NPC470823
0.7188	Intermediate Similarity	NPC194411
0.7174	Intermediate Similarity	NPC56856
0.7172	Intermediate Similarity	NPC198988
0.717	Intermediate Similarity	NPC98187
0.7163	Intermediate Similarity	NPC278451
0.7162	Intermediate Similarity	NPC2949
0.716	Intermediate Similarity	NPC275305
0.716	Intermediate Similarity	NPC37423
0.7153	Intermediate Similarity	NPC322488
0.7143	Intermediate Similarity	NPC141926
0.7143	Intermediate Similarity	NPC473901
0.7143	Intermediate Similarity	NPC138842
0.7134	Intermediate Similarity	NPC215584
0.7134	Intermediate Similarity	NPC470204
0.7134	Intermediate Similarity	NPC44773
0.7123	Intermediate Similarity	NPC29702
0.7097	Intermediate Similarity	NPC34844
0.7097	Intermediate Similarity	NPC209362
0.7092	Intermediate Similarity	NPC135488
0.7089	Intermediate Similarity	NPC282231
0.7086	Intermediate Similarity	NPC86288
0.7078	Intermediate Similarity	NPC70406
0.7073	Intermediate Similarity	NPC68354
0.707	Intermediate Similarity	NPC230869
0.7044	Intermediate Similarity	NPC317105
0.7044	Intermediate Similarity	NPC478182
0.7032	Intermediate Similarity	NPC251391
0.703	Intermediate Similarity	NPC215795
0.703	Intermediate Similarity	NPC176199
0.7029	Intermediate Similarity	NPC215519
0.7025	Intermediate Similarity	NPC131718
0.7025	Intermediate Similarity	NPC279918
0.7025	Intermediate Similarity	NPC122141
0.7019	Intermediate Similarity	NPC63751
0.7014	Intermediate Similarity	NPC22079
0.7012	Intermediate Similarity	NPC474958
0.7007	Intermediate Similarity	NPC162689
0.7007	Intermediate Similarity	NPC54102
0.7007	Intermediate Similarity	NPC218268
0.7006	Intermediate Similarity	NPC213914
0.6993	Remote Similarity	NPC21605
0.6988	Remote Similarity	NPC300688
0.6984	Remote Similarity	NPC213774

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 NPC475090 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	768
0.2-0.3	1081
0.3-0.4	1723
0.4-0.5	2885
0.5-0.6	1770
0.6-0.7	490
0.7-0.8	138
0.8-0.85	15
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8699	High Similarity	NPD269	Clinical (unspecified phase)
0.8473	Intermediate Similarity	NPD991	Phase 2
0.8473	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8473	Intermediate Similarity	NPD2119	Approved
0.8473	Intermediate Similarity	NPD2118	Approved
0.8397	Intermediate Similarity	NPD9583	Approved
0.8306	Intermediate Similarity	NPD4824	Approved
0.8306	Intermediate Similarity	NPD4823	Approved
0.8295	Intermediate Similarity	NPD271	Approved
0.8295	Intermediate Similarity	NPD268	Approved
0.8295	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.8244	Intermediate Similarity	NPD9357	Approved
0.8148	Intermediate Similarity	NPD3476	Approved
0.8148	Intermediate Similarity	NPD3475	Approved
0.8125	Intermediate Similarity	NPD9396	Approved
0.8125	Intermediate Similarity	NPD9392	Approved
0.8102	Intermediate Similarity	NPD4029	Approved
0.8102	Intermediate Similarity	NPD4030	Approved
0.8102	Intermediate Similarity	NPD4028	Approved
0.806	Intermediate Similarity	NPD1598	Discontinued
0.8029	Intermediate Similarity	NPD1993	Approved
0.8029	Intermediate Similarity	NPD1995	Approved
0.8029	Intermediate Similarity	NPD1994	Approved
0.8028	Intermediate Similarity	NPD3717	Discontinued
0.8028	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD3944	Approved
0.7971	Intermediate Similarity	NPD3942	Approved
0.7958	Intermediate Similarity	NPD1722	Approved
0.7943	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD4641	Discontinued
0.7857	Intermediate Similarity	NPD792	Discontinued
0.7826	Intermediate Similarity	NPD9726	Discontinued
0.782	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD2072	Approved
0.7817	Intermediate Similarity	NPD2071	Approved
0.7817	Intermediate Similarity	NPD2075	Approved
0.7817	Intermediate Similarity	NPD2070	Approved
0.7817	Intermediate Similarity	NPD2073	Approved
0.7817	Intermediate Similarity	NPD2074	Approved
0.7817	Intermediate Similarity	NPD786	Approved
0.7817	Intermediate Similarity	NPD2069	Approved
0.7817	Intermediate Similarity	NPD2068	Approved
0.7808	Intermediate Similarity	NPD4703	Approved
0.7808	Intermediate Similarity	NPD4702	Approved
0.7762	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD715	Phase 3
0.7746	Intermediate Similarity	NPD2896	Discontinued
0.774	Intermediate Similarity	NPD7469	Discontinued
0.773	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD803	Phase 1
0.7676	Intermediate Similarity	NPD201	Phase 2
0.7676	Intermediate Similarity	NPD200	Phase 2
0.7667	Intermediate Similarity	NPD5358	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD2142	Approved
0.766	Intermediate Similarity	NPD2140	Approved
0.766	Intermediate Similarity	NPD2141	Approved
0.7655	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD9098	Phase 3
0.7619	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD3813	Approved
0.755	Intermediate Similarity	NPD2809	Approved
0.7536	Intermediate Similarity	NPD9080	Approved
0.7536	Intermediate Similarity	NPD9284	Approved
0.7534	Intermediate Similarity	NPD4510	Discontinued
0.7532	Intermediate Similarity	NPD8026	Phase 1
0.7517	Intermediate Similarity	NPD3100	Discontinued
0.7517	Intermediate Similarity	NPD9599	Approved
0.75	Intermediate Similarity	NPD1380	Discovery
0.75	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3583	Phase 2
0.7483	Intermediate Similarity	NPD3339	Approved
0.7481	Intermediate Similarity	NPD9598	Discontinued
0.7467	Intermediate Similarity	NPD2172	Phase 1
0.7452	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2061	Approved
0.7434	Intermediate Similarity	NPD2165	Phase 1
0.7426	Intermediate Similarity	NPD5787	Discontinued
0.7419	Intermediate Similarity	NPD6771	Discontinued
0.7415	Intermediate Similarity	NPD2006	Phase 2
0.7405	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3112	Approved
0.7386	Intermediate Similarity	NPD3115	Approved
0.7386	Intermediate Similarity	NPD6026	Approved
0.7386	Intermediate Similarity	NPD3114	Approved
0.7386	Intermediate Similarity	NPD3113	Approved
0.7376	Intermediate Similarity	NPD9206	Approved
0.7376	Intermediate Similarity	NPD9207	Approved
0.7372	Intermediate Similarity	NPD3323	Discontinued
0.7368	Intermediate Similarity	NPD2837	Discontinued
0.7365	Intermediate Similarity	NPD1352	Discontinued
0.7355	Intermediate Similarity	NPD2511	Approved
0.7347	Intermediate Similarity	NPD1382	Phase 2
0.7347	Intermediate Similarity	NPD1383	Phase 3
0.7342	Intermediate Similarity	NPD2641	Approved
0.7342	Intermediate Similarity	NPD2640	Approved
0.7342	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2581	Approved
0.7338	Intermediate Similarity	NPD2582	Approved
0.7333	Intermediate Similarity	NPD1270	Approved
0.7333	Intermediate Similarity	NPD4547	Phase 3
0.7333	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4804	Approved
0.7324	Intermediate Similarity	NPD809	Discontinued
0.732	Intermediate Similarity	NPD977	Approved
0.732	Intermediate Similarity	NPD975	Approved
0.732	Intermediate Similarity	NPD1328	Approved
0.732	Intermediate Similarity	NPD976	Approved
0.731	Intermediate Similarity	NPD9506	Approved
0.7308	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3262	Approved
0.7297	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD60	Approved
0.7292	Intermediate Similarity	NPD272	Approved
0.7285	Intermediate Similarity	NPD2430	Phase 2
0.7279	Intermediate Similarity	NPD4811	Discontinued
0.7278	Intermediate Similarity	NPD5611	Phase 2
0.7273	Intermediate Similarity	NPD9100	Approved
0.7273	Intermediate Similarity	NPD2580	Discontinued
0.7273	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6635	Approved
0.725	Intermediate Similarity	NPD3117	Approved
0.725	Intermediate Similarity	NPD3116	Approved
0.7248	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2462	Phase 3
0.7237	Intermediate Similarity	NPD2466	Phase 3
0.7237	Intermediate Similarity	NPD2465	Approved
0.723	Intermediate Similarity	NPD4805	Approved
0.7226	Intermediate Similarity	NPD2145	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6044	Discontinued
0.7222	Intermediate Similarity	NPD3385	Approved
0.7219	Intermediate Similarity	NPD1661	Suspended
0.719	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2619	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2620	Phase 2
0.7185	Intermediate Similarity	NPD8840	Approved
0.7183	Intermediate Similarity	NPD3654	Approved
0.7179	Intermediate Similarity	NPD5255	Approved
0.7178	Intermediate Similarity	NPD4181	Approved
0.7171	Intermediate Similarity	NPD1183	Approved
0.7162	Intermediate Similarity	NPD1649	Discontinued
0.7143	Intermediate Similarity	NPD1917	Discontinued
0.7143	Intermediate Similarity	NPD3609	Approved
0.7143	Intermediate Similarity	NPD3610	Approved
0.7134	Intermediate Similarity	NPD1403	Approved
0.7134	Intermediate Similarity	NPD1404	Approved
0.7125	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4463	Approved
0.7124	Intermediate Similarity	NPD4462	Approved
0.7123	Intermediate Similarity	NPD1254	Approved
0.7123	Intermediate Similarity	NPD1256	Approved
0.7123	Intermediate Similarity	NPD1253	Approved
0.7123	Intermediate Similarity	NPD1255	Approved
0.7105	Intermediate Similarity	NPD2110	Approved
0.7089	Intermediate Similarity	NPD4239	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5315	Discontinued
0.7081	Intermediate Similarity	NPD5436	Phase 1
0.7081	Intermediate Similarity	NPD4024	Phase 3
0.7073	Intermediate Similarity	NPD3505	Approved
0.7073	Intermediate Similarity	NPD3506	Approved
0.7063	Intermediate Similarity	NPD2642	Approved
0.7063	Intermediate Similarity	NPD2639	Approved
0.7055	Intermediate Similarity	NPD5065	Approved
0.7055	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4891	Phase 2
0.7044	Intermediate Similarity	NPD5088	Discontinued
0.7044	Intermediate Similarity	NPD8129	Discovery
0.7039	Intermediate Similarity	NPD1683	Approved
0.703	Intermediate Similarity	NPD4076	Approved
0.703	Intermediate Similarity	NPD4079	Approved
0.7027	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1988	Phase 1
0.7019	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4075	Phase 2
0.7006	Intermediate Similarity	NPD5300	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6497	Approved
0.7006	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5020	Approved
0.6981	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4973	Approved
0.697	Remote Similarity	NPD4071	Approved
0.697	Remote Similarity	NPD2144	Approved
0.697	Remote Similarity	NPD4072	Approved
0.6964	Remote Similarity	NPD7564	Discontinued
0.6962	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1679	Approved
0.6957	Remote Similarity	NPD5636	Discontinued
0.6957	Remote Similarity	NPD3929	Clinical (unspecified phase)

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