NPASS Compound

Structure

NPC89490 OpenBabel07101718282D 21 21 0 0 0 0 0 0 0 0999 V2000 -12.9904 -0.5000 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 -6.9282 -2.0000 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 -7.7942 -1.5000 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 -8.6603 -2.0000 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 -9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 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 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 -1.5000 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 -12.1244 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 -1.5000 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 13 1 0 0 0 0 11 16 1 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 16 20 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 20 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.25
Volume:	334.202
LogP:	4.598
LogD:	3.397
LogS:	-2.731
# 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:	0.399
Synthetic Accessibility Score:	2.192
Fsp3:	0.722
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:	-4.595
MDCK Permeability:	2.071741982945241e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.961
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.803
Plasma Protein Binding (PPB):	85.55278778076172%
Volume Distribution (VD):	1.231
Pgp-substrate:	11.006329536437988%

ADMET: Metabolism

CYP1A2-inhibitor:	0.943
CYP1A2-substrate:	0.524
CYP2C19-inhibitor:	0.861
CYP2C19-substrate:	0.758
CYP2C9-inhibitor:	0.487
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.895
CYP2D6-substrate:	0.371
CYP3A4-inhibitor:	0.95
CYP3A4-substrate:	0.289

ADMET: Excretion

Clearance (CL):	8.534
Half-life (T1/2):	0.284

ADMET: Toxicity

hERG Blockers:	0.567
Human Hepatotoxicity (H-HT):	0.4
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.852
Maximum Recommended Daily Dose:	0.153
Skin Sensitization:	0.965
Carcinogencity:	0.036
Eye Corrosion:	0.75
Eye Irritation:	0.765
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC89490

Natural Product ID:	NPC89490
*Common Name:**	Hachijodine A
IUPAC Name:	N-methoxy-12-pyridin-3-yldodecan-1-amine
Synonyms:
Standard InCHIKey:	UHYBQKKGFAMJFK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H32N2O/c1-21-20-16-11-9-7-5-3-2-4-6-8-10-13-18-14-12-15-19-17-18/h12,14-15,17,20H,2-11,13,16H2,1H3
SMILES:	CONCCCCCCCCCCCCc1cccnc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497091
PubChem CID:	10062944
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[458233]

☑ 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 NPC89490 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	501
0.1-0.2	10204
0.2-0.3	19220
0.3-0.4	6931
0.4-0.5	3005
0.5-0.6	1839
0.6-0.7	742
0.7-0.8	226
0.8-0.85	12
0.85-0.9	9
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9918	High Similarity	NPC329896
0.9918	High Similarity	NPC475105
0.9918	High Similarity	NPC475090
0.9426	High Similarity	NPC290094
0.92	High Similarity	NPC202957
0.92	High Similarity	NPC169625
0.878	High Similarity	NPC297486
0.878	High Similarity	NPC471402
0.878	High Similarity	NPC240136
0.8702	High Similarity	NPC471322
0.8672	High Similarity	NPC146373
0.8672	High Similarity	NPC166424
0.8672	High Similarity	NPC245244
0.8594	High Similarity	NPC27740
0.8538	High Similarity	NPC471311
0.8538	High Similarity	NPC471313
0.8512	High Similarity	NPC27802
0.845	Intermediate Similarity	NPC476322
0.8413	Intermediate Similarity	NPC91958
0.8359	Intermediate Similarity	NPC182570
0.8359	Intermediate Similarity	NPC265605
0.8359	Intermediate Similarity	NPC48564
0.8295	Intermediate Similarity	NPC329825
0.8264	Intermediate Similarity	NPC76540
0.8209	Intermediate Similarity	NPC69914
0.8148	Intermediate Similarity	NPC101165
0.8134	Intermediate Similarity	NPC476131
0.8125	Intermediate Similarity	NPC143603
0.8074	Intermediate Similarity	NPC282398
0.8071	Intermediate Similarity	NPC469783
0.8071	Intermediate Similarity	NPC469768
0.8071	Intermediate Similarity	NPC469761
0.8071	Intermediate Similarity	NPC469779
0.8071	Intermediate Similarity	NPC469780
0.8071	Intermediate Similarity	NPC469784
0.8071	Intermediate Similarity	NPC469767
0.8015	Intermediate Similarity	NPC256893
0.8014	Intermediate Similarity	NPC469766
0.7986	Intermediate Similarity	NPC471312
0.7937	Intermediate Similarity	NPC235843
0.7883	Intermediate Similarity	NPC324611
0.7877	Intermediate Similarity	NPC24678
0.7877	Intermediate Similarity	NPC105818
0.7872	Intermediate Similarity	NPC73767
0.7857	Intermediate Similarity	NPC84911
0.7857	Intermediate Similarity	NPC314102
0.7857	Intermediate Similarity	NPC251722
0.7847	Intermediate Similarity	NPC314372
0.7832	Intermediate Similarity	NPC190296
0.782	Intermediate Similarity	NPC46358
0.7786	Intermediate Similarity	NPC261195
0.7786	Intermediate Similarity	NPC96102
0.7786	Intermediate Similarity	NPC29886
0.7778	Intermediate Similarity	NPC471323
0.777	Intermediate Similarity	NPC469760
0.777	Intermediate Similarity	NPC259644
0.777	Intermediate Similarity	NPC469763
0.777	Intermediate Similarity	NPC25008
0.777	Intermediate Similarity	NPC73952
0.777	Intermediate Similarity	NPC469765
0.777	Intermediate Similarity	NPC469786
0.7769	Intermediate Similarity	NPC83987
0.7762	Intermediate Similarity	NPC476454
0.7746	Intermediate Similarity	NPC110126
0.7746	Intermediate Similarity	NPC316811
0.7746	Intermediate Similarity	NPC315348
0.7746	Intermediate Similarity	NPC32002
0.774	Intermediate Similarity	NPC470111
0.773	Intermediate Similarity	NPC65408
0.773	Intermediate Similarity	NPC105127
0.7724	Intermediate Similarity	NPC285731
0.7718	Intermediate Similarity	NPC211572
0.7718	Intermediate Similarity	NPC212376
0.7718	Intermediate Similarity	NPC75540
0.7718	Intermediate Similarity	NPC80597
0.7718	Intermediate Similarity	NPC70922
0.7697	Intermediate Similarity	NPC71079
0.768	Intermediate Similarity	NPC231655
0.7667	Intermediate Similarity	NPC469785
0.7647	Intermediate Similarity	NPC474217
0.7626	Intermediate Similarity	NPC82295
0.7619	Intermediate Similarity	NPC477974
0.7619	Intermediate Similarity	NPC471957
0.7616	Intermediate Similarity	NPC469762
0.7606	Intermediate Similarity	NPC150259
0.7603	Intermediate Similarity	NPC159856
0.7591	Intermediate Similarity	NPC212125
0.7591	Intermediate Similarity	NPC306397
0.7584	Intermediate Similarity	NPC470233
0.7569	Intermediate Similarity	NPC279081
0.7568	Intermediate Similarity	NPC321911
0.7557	Intermediate Similarity	NPC476566
0.755	Intermediate Similarity	NPC51054
0.7548	Intermediate Similarity	NPC127730
0.7548	Intermediate Similarity	NPC278366
0.7533	Intermediate Similarity	NPC200214
0.7532	Intermediate Similarity	NPC311276
0.7517	Intermediate Similarity	NPC53947
0.75	Intermediate Similarity	NPC201380
0.75	Intermediate Similarity	NPC236711
0.75	Intermediate Similarity	NPC469811
0.75	Intermediate Similarity	NPC179787
0.7484	Intermediate Similarity	NPC85918
0.7483	Intermediate Similarity	NPC477815
0.7481	Intermediate Similarity	NPC84268
0.7451	Intermediate Similarity	NPC56765
0.7448	Intermediate Similarity	NPC230002
0.7434	Intermediate Similarity	NPC476464
0.7432	Intermediate Similarity	NPC63545
0.7432	Intermediate Similarity	NPC288838
0.7429	Intermediate Similarity	NPC315320
0.7419	Intermediate Similarity	NPC40779
0.7419	Intermediate Similarity	NPC78375
0.7419	Intermediate Similarity	NPC476446
0.7419	Intermediate Similarity	NPC469813
0.7417	Intermediate Similarity	NPC325903
0.7386	Intermediate Similarity	NPC469897
0.7379	Intermediate Similarity	NPC104483
0.7368	Intermediate Similarity	NPC81561
0.7365	Intermediate Similarity	NPC467188
0.7355	Intermediate Similarity	NPC225018
0.7351	Intermediate Similarity	NPC216713
0.7338	Intermediate Similarity	NPC92796
0.7338	Intermediate Similarity	NPC165370
0.7338	Intermediate Similarity	NPC135141
0.7325	Intermediate Similarity	NPC160105
0.7324	Intermediate Similarity	NPC330326
0.7315	Intermediate Similarity	NPC143872
0.731	Intermediate Similarity	NPC169433
0.7308	Intermediate Similarity	NPC90723
0.7293	Intermediate Similarity	NPC148140
0.7292	Intermediate Similarity	NPC325252
0.7286	Intermediate Similarity	NPC471589
0.7285	Intermediate Similarity	NPC40070
0.7278	Intermediate Similarity	NPC201700
0.7273	Intermediate Similarity	NPC286427
0.7273	Intermediate Similarity	NPC167635
0.7273	Intermediate Similarity	NPC129721
0.7273	Intermediate Similarity	NPC193740
0.7267	Intermediate Similarity	NPC105811
0.7259	Intermediate Similarity	NPC11863
0.7244	Intermediate Similarity	NPC470203
0.7237	Intermediate Similarity	NPC470823
0.723	Intermediate Similarity	NPC477977
0.7226	Intermediate Similarity	NPC318065
0.7226	Intermediate Similarity	NPC56856
0.7226	Intermediate Similarity	NPC41257
0.7226	Intermediate Similarity	NPC206819
0.7222	Intermediate Similarity	NPC198988
0.7215	Intermediate Similarity	NPC474561
0.7215	Intermediate Similarity	NPC49954
0.7211	Intermediate Similarity	NPC59084
0.7211	Intermediate Similarity	NPC2949
0.7203	Intermediate Similarity	NPC322488
0.7197	Intermediate Similarity	NPC473901
0.7192	Intermediate Similarity	NPC104049
0.719	Intermediate Similarity	NPC138842
0.719	Intermediate Similarity	NPC141926
0.7188	Intermediate Similarity	NPC201634
0.7179	Intermediate Similarity	NPC44773
0.7179	Intermediate Similarity	NPC470204
0.7179	Intermediate Similarity	NPC215584
0.7172	Intermediate Similarity	NPC29702
0.7162	Intermediate Similarity	NPC473868
0.7162	Intermediate Similarity	NPC63157
0.7161	Intermediate Similarity	NPC216643
0.7152	Intermediate Similarity	NPC477975
0.7143	Intermediate Similarity	NPC209362
0.7143	Intermediate Similarity	NPC34844
0.7143	Intermediate Similarity	NPC314603
0.7143	Intermediate Similarity	NPC135488
0.7134	Intermediate Similarity	NPC282231
0.7133	Intermediate Similarity	NPC86288
0.7125	Intermediate Similarity	NPC194411
0.7124	Intermediate Similarity	NPC70406
0.7115	Intermediate Similarity	NPC230869
0.7107	Intermediate Similarity	NPC98187
0.7099	Intermediate Similarity	NPC275305
0.7099	Intermediate Similarity	NPC37423
0.7092	Intermediate Similarity	NPC278451
0.7089	Intermediate Similarity	NPC478182
0.7089	Intermediate Similarity	NPC317105
0.708	Intermediate Similarity	NPC215519
0.7078	Intermediate Similarity	NPC251391
0.707	Intermediate Similarity	NPC122141
0.707	Intermediate Similarity	NPC131718
0.707	Intermediate Similarity	NPC279918
0.7063	Intermediate Similarity	NPC63751
0.7063	Intermediate Similarity	NPC22079
0.7059	Intermediate Similarity	NPC54102
0.7059	Intermediate Similarity	NPC162689
0.7055	Intermediate Similarity	NPC218268
0.7051	Intermediate Similarity	NPC213914
0.704	Intermediate Similarity	NPC213774
0.7027	Intermediate Similarity	NPC88097
0.7025	Intermediate Similarity	NPC59779
0.7025	Intermediate Similarity	NPC242116
0.7025	Intermediate Similarity	NPC124542
0.7025	Intermediate Similarity	NPC471177
0.702	Intermediate Similarity	NPC470440

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 NPC89490 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	837
0.2-0.3	1028
0.3-0.4	1726
0.4-0.5	2873
0.5-0.6	1736
0.6-0.7	521
0.7-0.8	132
0.8-0.85	17
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.877	High Similarity	NPD269	Clinical (unspecified phase)
0.8538	High Similarity	NPD991	Phase 2
0.8538	High Similarity	NPD992	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD9583	Approved
0.8397	Intermediate Similarity	NPD2119	Approved
0.8397	Intermediate Similarity	NPD2118	Approved
0.8374	Intermediate Similarity	NPD4823	Approved
0.8374	Intermediate Similarity	NPD4824	Approved
0.8359	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.8359	Intermediate Similarity	NPD271	Approved
0.8359	Intermediate Similarity	NPD268	Approved
0.8308	Intermediate Similarity	NPD9357	Approved
0.8209	Intermediate Similarity	NPD3475	Approved
0.8209	Intermediate Similarity	NPD3476	Approved
0.8189	Intermediate Similarity	NPD9392	Approved
0.8189	Intermediate Similarity	NPD9396	Approved
0.812	Intermediate Similarity	NPD1598	Discontinued
0.8088	Intermediate Similarity	NPD1995	Approved
0.8088	Intermediate Similarity	NPD1994	Approved
0.8088	Intermediate Similarity	NPD1993	Approved
0.8029	Intermediate Similarity	NPD3944	Approved
0.8029	Intermediate Similarity	NPD4030	Approved
0.8029	Intermediate Similarity	NPD4029	Approved
0.8029	Intermediate Similarity	NPD3942	Approved
0.8029	Intermediate Similarity	NPD4028	Approved
0.7958	Intermediate Similarity	NPD3717	Discontinued
0.7958	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD792	Discontinued
0.7887	Intermediate Similarity	NPD1722	Approved
0.7883	Intermediate Similarity	NPD9726	Discontinued
0.7879	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD786	Approved
0.7872	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4702	Approved
0.7862	Intermediate Similarity	NPD4703	Approved
0.7823	Intermediate Similarity	NPD4641	Discontinued
0.7817	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD715	Phase 3
0.7801	Intermediate Similarity	NPD2896	Discontinued
0.7793	Intermediate Similarity	NPD7469	Discontinued
0.7786	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD803	Phase 1
0.7746	Intermediate Similarity	NPD2070	Approved
0.7746	Intermediate Similarity	NPD2072	Approved
0.7746	Intermediate Similarity	NPD2073	Approved
0.7746	Intermediate Similarity	NPD2071	Approved
0.7746	Intermediate Similarity	NPD2069	Approved
0.7746	Intermediate Similarity	NPD2074	Approved
0.7746	Intermediate Similarity	NPD2075	Approved
0.7746	Intermediate Similarity	NPD2068	Approved
0.773	Intermediate Similarity	NPD200	Phase 2
0.773	Intermediate Similarity	NPD201	Phase 2
0.7714	Intermediate Similarity	NPD2141	Approved
0.7714	Intermediate Similarity	NPD2140	Approved
0.7714	Intermediate Similarity	NPD2142	Approved
0.7708	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD9098	Phase 3
0.768	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD3813	Approved
0.76	Intermediate Similarity	NPD5358	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2809	Approved
0.7591	Intermediate Similarity	NPD9080	Approved
0.7591	Intermediate Similarity	NPD9284	Approved
0.7586	Intermediate Similarity	NPD4510	Discontinued
0.7582	Intermediate Similarity	NPD8026	Phase 1
0.7569	Intermediate Similarity	NPD9599	Approved
0.7568	Intermediate Similarity	NPD3100	Discontinued
0.7552	Intermediate Similarity	NPD1380	Discovery
0.7551	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD9598	Discontinued
0.7533	Intermediate Similarity	NPD3339	Approved
0.7517	Intermediate Similarity	NPD2172	Phase 1
0.7483	Intermediate Similarity	NPD2165	Phase 1
0.7483	Intermediate Similarity	NPD2061	Approved
0.7481	Intermediate Similarity	NPD5787	Discontinued
0.7468	Intermediate Similarity	NPD6771	Discontinued
0.7466	Intermediate Similarity	NPD2006	Phase 2
0.745	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD3112	Approved
0.7434	Intermediate Similarity	NPD3115	Approved
0.7434	Intermediate Similarity	NPD3113	Approved
0.7434	Intermediate Similarity	NPD3114	Approved
0.7429	Intermediate Similarity	NPD9206	Approved
0.7429	Intermediate Similarity	NPD9207	Approved
0.7419	Intermediate Similarity	NPD3583	Phase 2
0.7417	Intermediate Similarity	NPD2837	Discontinued
0.7415	Intermediate Similarity	NPD1352	Discontinued
0.7397	Intermediate Similarity	NPD1382	Phase 2
0.7397	Intermediate Similarity	NPD1383	Phase 3
0.7389	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2581	Approved
0.7386	Intermediate Similarity	NPD2582	Approved
0.7386	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4547	Phase 3
0.7383	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1270	Approved
0.7379	Intermediate Similarity	NPD4804	Approved
0.7376	Intermediate Similarity	NPD809	Discontinued
0.7368	Intermediate Similarity	NPD1328	Approved
0.7361	Intermediate Similarity	NPD9506	Approved
0.7355	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3262	Approved
0.7348	Intermediate Similarity	NPD60	Approved
0.7347	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD272	Approved
0.7342	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4811	Discontinued
0.7333	Intermediate Similarity	NPD2430	Phase 2
0.7325	Intermediate Similarity	NPD5611	Phase 2
0.7324	Intermediate Similarity	NPD9100	Approved
0.732	Intermediate Similarity	NPD6026	Approved
0.732	Intermediate Similarity	NPD2580	Discontinued
0.732	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3323	Discontinued
0.7297	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3116	Approved
0.7296	Intermediate Similarity	NPD3117	Approved
0.7292	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2511	Approved
0.7285	Intermediate Similarity	NPD2466	Phase 3
0.7285	Intermediate Similarity	NPD2465	Approved
0.7285	Intermediate Similarity	NPD2462	Phase 3
0.7279	Intermediate Similarity	NPD4805	Approved
0.7278	Intermediate Similarity	NPD2641	Approved
0.7278	Intermediate Similarity	NPD2640	Approved
0.7273	Intermediate Similarity	NPD3385	Approved
0.7273	Intermediate Similarity	NPD2145	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1661	Suspended
0.7267	Intermediate Similarity	NPD6044	Discontinued
0.7255	Intermediate Similarity	NPD976	Approved
0.7255	Intermediate Similarity	NPD977	Approved
0.7255	Intermediate Similarity	NPD975	Approved
0.7239	Intermediate Similarity	NPD8840	Approved
0.7234	Intermediate Similarity	NPD3654	Approved
0.7226	Intermediate Similarity	NPD5255	Approved
0.7219	Intermediate Similarity	NPD1183	Approved
0.7211	Intermediate Similarity	NPD1649	Discontinued
0.7197	Intermediate Similarity	NPD6635	Approved
0.719	Intermediate Similarity	NPD1917	Discontinued
0.7179	Intermediate Similarity	NPD1403	Approved
0.7179	Intermediate Similarity	NPD1404	Approved
0.7172	Intermediate Similarity	NPD1255	Approved
0.7172	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1254	Approved
0.7172	Intermediate Similarity	NPD1253	Approved
0.7172	Intermediate Similarity	NPD1256	Approved
0.7171	Intermediate Similarity	NPD4462	Approved
0.7171	Intermediate Similarity	NPD4463	Approved
0.717	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2110	Approved
0.7134	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2620	Phase 2
0.7125	Intermediate Similarity	NPD5436	Phase 1
0.7125	Intermediate Similarity	NPD4024	Phase 3
0.7125	Intermediate Similarity	NPD2619	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4181	Approved
0.7107	Intermediate Similarity	NPD2642	Approved
0.7107	Intermediate Similarity	NPD2639	Approved
0.7099	Intermediate Similarity	NPD5065	Approved
0.7091	Intermediate Similarity	NPD4891	Phase 2
0.7089	Intermediate Similarity	NPD8129	Discovery
0.7089	Intermediate Similarity	NPD5088	Discontinued
0.7086	Intermediate Similarity	NPD1683	Approved
0.7081	Intermediate Similarity	NPD3610	Approved
0.7081	Intermediate Similarity	NPD3609	Approved
0.7075	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1988	Phase 1
0.7063	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6497	Approved
0.7051	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5020	Approved
0.7025	Intermediate Similarity	NPD5315	Discontinued
0.7025	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4239	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4973	Approved
0.7012	Intermediate Similarity	NPD2144	Approved
0.7012	Intermediate Similarity	NPD4071	Approved
0.7012	Intermediate Similarity	NPD3506	Approved
0.7012	Intermediate Similarity	NPD3505	Approved
0.7012	Intermediate Similarity	NPD4072	Approved
0.7006	Intermediate Similarity	NPD1679	Approved
0.7006	Intermediate Similarity	NPD7564	Discontinued
0.7	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4128	Approved
0.6993	Remote Similarity	NPD9305	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD947	Approved
0.6987	Remote Similarity	NPD473	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1561	Phase 2
0.697	Remote Similarity	NPD4079	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