NPASS Compound

Structure

NPC202957 OpenBabel07101719512D 23 23 0 0 0 0 0 0 0 0999 V2000 -9.5263 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -10.0000 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 -7.7942 -10.5000 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 -8.6603 -10.0000 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 -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 -8.6603 -9.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 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 3 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 13 1 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 18 22 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 22 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.25
Volume:	363.521
LogP:	4.291
LogD:	3.243
LogS:	-2.76
# Rotatable Bonds:	12
TPSA:	36.36
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.34
Synthetic Accessibility Score:	2.601
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.703
MDCK Permeability:	1.3273307558847591e-05
Pgp-inhibitor:	0.08
Pgp-substrate:	0.879
Human Intestinal Absorption (HIA):	0.045
20% Bioavailability (F20%):	0.968
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	91.1414566040039%
Volume Distribution (VD):	0.837
Pgp-substrate:	2.689081907272339%

ADMET: Metabolism

CYP1A2-inhibitor:	0.958
CYP1A2-substrate:	0.636
CYP2C19-inhibitor:	0.946
CYP2C19-substrate:	0.856
CYP2C9-inhibitor:	0.891
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.847
CYP2D6-substrate:	0.652
CYP3A4-inhibitor:	0.937
CYP3A4-substrate:	0.224

ADMET: Excretion

Clearance (CL):	9.795
Half-life (T1/2):	0.287

ADMET: Toxicity

hERG Blockers:	0.742
Human Hepatotoxicity (H-HT):	0.045
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.184
Maximum Recommended Daily Dose:	0.32
Skin Sensitization:	0.97
Carcinogencity:	0.117
Eye Corrosion:	0.961
Eye Irritation:	0.923
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC202957

Natural Product ID:	NPC202957
*Common Name:**	Hachijodine F
IUPAC Name:	N-methyl-N-(14-pyridin-3-yltetradec-9-ynyl)hydroxylamine
Synonyms:	Hachijodine F
Standard InCHIKey:	USKLJJAATAWJPP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H32N2O/c1-22(23)18-13-11-9-7-5-3-2-4-6-8-10-12-15-20-16-14-17-21-19-20/h14,16-17,19,23H,2-3,5,7-13,15,18H2,1H3
SMILES:	CN(CCCCCCCCC#CCCCCc1cccnc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501067
PubChem CID:	10448484
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	=	1.0	ug ml-1	PMID[507674]

☑ 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 NPC202957 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	713
0.1-0.2	11101
0.2-0.3	18822
0.3-0.4	6677
0.4-0.5	2953
0.5-0.6	1677
0.6-0.7	577
0.7-0.8	148
0.8-0.85	15
0.85-0.9	6
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC169625
0.9748	High Similarity	NPC290094
0.92	High Similarity	NPC89490
0.9127	High Similarity	NPC329896
0.9127	High Similarity	NPC475090
0.9127	High Similarity	NPC475105
0.8926	High Similarity	NPC240136
0.8926	High Similarity	NPC297486
0.8926	High Similarity	NPC471402
0.8672	High Similarity	NPC471311
0.8672	High Similarity	NPC471313
0.8655	High Similarity	NPC27802
0.8583	High Similarity	NPC476322
0.8548	High Similarity	NPC91958
0.8492	Intermediate Similarity	NPC182570
0.8492	Intermediate Similarity	NPC265605
0.8492	Intermediate Similarity	NPC48564
0.8425	Intermediate Similarity	NPC329825
0.8409	Intermediate Similarity	NPC471322
0.8403	Intermediate Similarity	NPC76540
0.8333	Intermediate Similarity	NPC69914
0.8258	Intermediate Similarity	NPC476131
0.8254	Intermediate Similarity	NPC143603
0.8231	Intermediate Similarity	NPC166424
0.8231	Intermediate Similarity	NPC146373
0.8231	Intermediate Similarity	NPC245244
0.8154	Intermediate Similarity	NPC27740
0.8102	Intermediate Similarity	NPC471312
0.8065	Intermediate Similarity	NPC235843
0.8	Intermediate Similarity	NPC324611
0.8	Intermediate Similarity	NPC256893
0.7972	Intermediate Similarity	NPC470111
0.7971	Intermediate Similarity	NPC314102
0.7971	Intermediate Similarity	NPC251722
0.7939	Intermediate Similarity	NPC46358
0.7899	Intermediate Similarity	NPC83987
0.7881	Intermediate Similarity	NPC127730
0.7881	Intermediate Similarity	NPC278366
0.7868	Intermediate Similarity	NPC101165
0.7857	Intermediate Similarity	NPC32002
0.7857	Intermediate Similarity	NPC316811
0.7857	Intermediate Similarity	NPC315348
0.7815	Intermediate Similarity	NPC85918
0.7805	Intermediate Similarity	NPC231655
0.7794	Intermediate Similarity	NPC282398
0.7762	Intermediate Similarity	NPC471323
0.7714	Intermediate Similarity	NPC150259
0.7714	Intermediate Similarity	NPC65408
0.7704	Intermediate Similarity	NPC212125
0.7682	Intermediate Similarity	NPC71079
0.7676	Intermediate Similarity	NPC469768
0.7676	Intermediate Similarity	NPC469783
0.7676	Intermediate Similarity	NPC469784
0.7676	Intermediate Similarity	NPC469779
0.7676	Intermediate Similarity	NPC469767
0.7676	Intermediate Similarity	NPC469780
0.7676	Intermediate Similarity	NPC469761
0.7674	Intermediate Similarity	NPC476566
0.7632	Intermediate Similarity	NPC474217
0.7622	Intermediate Similarity	NPC469766
0.7603	Intermediate Similarity	NPC477974
0.7586	Intermediate Similarity	NPC285731
0.7536	Intermediate Similarity	NPC315320
0.75	Intermediate Similarity	NPC105818
0.75	Intermediate Similarity	NPC24678
0.7483	Intermediate Similarity	NPC73767
0.7481	Intermediate Similarity	NPC81561
0.7466	Intermediate Similarity	NPC314372
0.7465	Intermediate Similarity	NPC84911
0.7448	Intermediate Similarity	NPC190296
0.7445	Intermediate Similarity	NPC306397
0.7417	Intermediate Similarity	NPC51054
0.7413	Intermediate Similarity	NPC169433
0.7405	Intermediate Similarity	NPC148140
0.74	Intermediate Similarity	NPC259644
0.74	Intermediate Similarity	NPC469786
0.74	Intermediate Similarity	NPC25008
0.74	Intermediate Similarity	NPC73952
0.74	Intermediate Similarity	NPC469763
0.74	Intermediate Similarity	NPC469765
0.74	Intermediate Similarity	NPC469760
0.7394	Intermediate Similarity	NPC29886
0.7394	Intermediate Similarity	NPC261195
0.7394	Intermediate Similarity	NPC96102
0.7383	Intermediate Similarity	NPC40070
0.7379	Intermediate Similarity	NPC476454
0.7368	Intermediate Similarity	NPC11863
0.7368	Intermediate Similarity	NPC129721
0.7361	Intermediate Similarity	NPC110126
0.7351	Intermediate Similarity	NPC70922
0.7351	Intermediate Similarity	NPC80597
0.7351	Intermediate Similarity	NPC212376
0.7351	Intermediate Similarity	NPC75540
0.7351	Intermediate Similarity	NPC211572
0.7343	Intermediate Similarity	NPC105127
0.7333	Intermediate Similarity	NPC470233
0.7333	Intermediate Similarity	NPC56856
0.7329	Intermediate Similarity	NPC477977
0.7319	Intermediate Similarity	NPC165370
0.7308	Intermediate Similarity	NPC473901
0.7305	Intermediate Similarity	NPC322488
0.7285	Intermediate Similarity	NPC138842
0.7273	Intermediate Similarity	NPC29702
0.7255	Intermediate Similarity	NPC236711
0.7248	Intermediate Similarity	NPC179787
0.7248	Intermediate Similarity	NPC471957
0.7248	Intermediate Similarity	NPC201380
0.7246	Intermediate Similarity	NPC135488
0.7241	Intermediate Similarity	NPC104483
0.7234	Intermediate Similarity	NPC82295
0.723	Intermediate Similarity	NPC159856
0.723	Intermediate Similarity	NPC86288
0.7226	Intermediate Similarity	NPC225018
0.72	Intermediate Similarity	NPC321911
0.7197	Intermediate Similarity	NPC98187
0.7197	Intermediate Similarity	NPC84268
0.7194	Intermediate Similarity	NPC278451
0.7192	Intermediate Similarity	NPC279081
0.719	Intermediate Similarity	NPC469785
0.7185	Intermediate Similarity	NPC215519
0.7181	Intermediate Similarity	NPC63545
0.7164	Intermediate Similarity	NPC162689
0.7164	Intermediate Similarity	NPC54102
0.7154	Intermediate Similarity	NPC213774
0.7152	Intermediate Similarity	NPC53947
0.7143	Intermediate Similarity	NPC469762
0.7143	Intermediate Similarity	NPC471589
0.7134	Intermediate Similarity	NPC477975
0.7133	Intermediate Similarity	NPC469811
0.7115	Intermediate Similarity	NPC124542
0.7115	Intermediate Similarity	NPC59779
0.7115	Intermediate Similarity	NPC471177
0.7114	Intermediate Similarity	NPC469525
0.7101	Intermediate Similarity	NPC122718
0.7097	Intermediate Similarity	NPC56765
0.7095	Intermediate Similarity	NPC20144
0.7078	Intermediate Similarity	NPC476464
0.7075	Intermediate Similarity	NPC230002
0.707	Intermediate Similarity	NPC478182
0.707	Intermediate Similarity	NPC311276
0.7067	Intermediate Similarity	NPC288838
0.7063	Intermediate Similarity	NPC330326
0.7059	Intermediate Similarity	NPC325903
0.7059	Intermediate Similarity	NPC200214
0.7032	Intermediate Similarity	NPC469897
0.7025	Intermediate Similarity	NPC471178
0.7	Intermediate Similarity	NPC467188
0.6993	Remote Similarity	NPC216713
0.6987	Remote Similarity	NPC92796
0.6987	Remote Similarity	NPC135141
0.6981	Remote Similarity	NPC160105
0.6966	Remote Similarity	NPC198988
0.6962	Remote Similarity	NPC476446
0.6962	Remote Similarity	NPC90723
0.6962	Remote Similarity	NPC40779
0.6962	Remote Similarity	NPC469813
0.6962	Remote Similarity	NPC473057
0.6962	Remote Similarity	NPC78375
0.6959	Remote Similarity	NPC59084
0.6959	Remote Similarity	NPC2949
0.6954	Remote Similarity	NPC143872
0.6943	Remote Similarity	NPC44773
0.6943	Remote Similarity	NPC215584
0.6923	Remote Similarity	NPC286427
0.6923	Remote Similarity	NPC193740
0.6923	Remote Similarity	NPC167635
0.6918	Remote Similarity	NPC325252
0.6913	Remote Similarity	NPC473868
0.6913	Remote Similarity	NPC63157
0.6908	Remote Similarity	NPC105811
0.6903	Remote Similarity	NPC477815
0.6899	Remote Similarity	NPC470203
0.6899	Remote Similarity	NPC242116
0.6894	Remote Similarity	NPC116961
0.6883	Remote Similarity	NPC470823
0.6883	Remote Similarity	NPC70406
0.6879	Remote Similarity	NPC80681
0.6879	Remote Similarity	NPC41257
0.6879	Remote Similarity	NPC206819
0.6879	Remote Similarity	NPC477591
0.6879	Remote Similarity	NPC293487
0.6879	Remote Similarity	NPC318065
0.6875	Remote Similarity	NPC108469
0.6875	Remote Similarity	NPC49954
0.6875	Remote Similarity	NPC474561
0.6871	Remote Similarity	NPC114310
0.6871	Remote Similarity	NPC317054
0.6855	Remote Similarity	NPC97367
0.6852	Remote Similarity	NPC201634
0.6839	Remote Similarity	NPC141926
0.6835	Remote Similarity	NPC470204
0.6832	Remote Similarity	NPC201700
0.6815	Remote Similarity	NPC216643
0.681	Remote Similarity	NPC314603
0.6809	Remote Similarity	NPC151489
0.6806	Remote Similarity	NPC22079
0.6803	Remote Similarity	NPC328029
0.6795	Remote Similarity	NPC34844
0.6795	Remote Similarity	NPC209362
0.6792	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 NPC202957 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	913
0.2-0.3	1015
0.3-0.4	2040
0.4-0.5	2820
0.5-0.6	1496
0.6-0.7	406
0.7-0.8	102
0.8-0.85	20
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8527	High Similarity	NPD2119	Approved
0.8527	High Similarity	NPD2118	Approved
0.8512	High Similarity	NPD4824	Approved
0.8512	High Similarity	NPD4823	Approved
0.8492	Intermediate Similarity	NPD271	Approved
0.8492	Intermediate Similarity	NPD268	Approved
0.8492	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3475	Approved
0.8333	Intermediate Similarity	NPD3476	Approved
0.8308	Intermediate Similarity	NPD9583	Approved
0.8306	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD1993	Approved
0.8209	Intermediate Similarity	NPD1994	Approved
0.8209	Intermediate Similarity	NPD1995	Approved
0.8154	Intermediate Similarity	NPD9357	Approved
0.8148	Intermediate Similarity	NPD3944	Approved
0.8148	Intermediate Similarity	NPD4029	Approved
0.8148	Intermediate Similarity	NPD3942	Approved
0.8148	Intermediate Similarity	NPD4028	Approved
0.8148	Intermediate Similarity	NPD4030	Approved
0.8106	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD991	Phase 2
0.8029	Intermediate Similarity	NPD792	Discontinued
0.797	Intermediate Similarity	NPD1598	Discontinued
0.7941	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD715	Phase 3
0.7914	Intermediate Similarity	NPD2896	Discontinued
0.7902	Intermediate Similarity	NPD7469	Discontinued
0.7877	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2073	Approved
0.7857	Intermediate Similarity	NPD2071	Approved
0.7857	Intermediate Similarity	NPD2072	Approved
0.7857	Intermediate Similarity	NPD2075	Approved
0.7857	Intermediate Similarity	NPD2070	Approved
0.7857	Intermediate Similarity	NPD2069	Approved
0.7857	Intermediate Similarity	NPD2068	Approved
0.7857	Intermediate Similarity	NPD2074	Approved
0.7826	Intermediate Similarity	NPD2142	Approved
0.7826	Intermediate Similarity	NPD2140	Approved
0.7826	Intermediate Similarity	NPD2141	Approved
0.7817	Intermediate Similarity	NPD3717	Discontinued
0.7805	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD9098	Phase 3
0.7778	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD3813	Approved
0.7752	Intermediate Similarity	NPD9392	Approved
0.7752	Intermediate Similarity	NPD9396	Approved
0.7724	Intermediate Similarity	NPD4702	Approved
0.7724	Intermediate Similarity	NPD4703	Approved
0.7714	Intermediate Similarity	NPD200	Phase 2
0.7714	Intermediate Similarity	NPD201	Phase 2
0.7704	Intermediate Similarity	NPD9284	Approved
0.7692	Intermediate Similarity	NPD4510	Discontinued
0.7655	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD5358	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD2809	Approved
0.7569	Intermediate Similarity	NPD2006	Phase 2
0.7569	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD9206	Approved
0.7536	Intermediate Similarity	NPD9207	Approved
0.7535	Intermediate Similarity	NPD1380	Discovery
0.7517	Intermediate Similarity	NPD1352	Discontinued
0.75	Intermediate Similarity	NPD1722	Approved
0.7483	Intermediate Similarity	NPD786	Approved
0.7483	Intermediate Similarity	NPD4547	Phase 3
0.7483	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD9726	Discontinued
0.7462	Intermediate Similarity	NPD60	Approved
0.745	Intermediate Similarity	NPD3262	Approved
0.745	Intermediate Similarity	NPD4641	Discontinued
0.7448	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD9080	Approved
0.7432	Intermediate Similarity	NPD2430	Phase 2
0.7431	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2466	Phase 3
0.7383	Intermediate Similarity	NPD2462	Phase 3
0.7383	Intermediate Similarity	NPD2465	Approved
0.7379	Intermediate Similarity	NPD1382	Phase 2
0.7379	Intermediate Similarity	NPD1383	Phase 3
0.7376	Intermediate Similarity	NPD3385	Approved
0.7365	Intermediate Similarity	NPD1270	Approved
0.7365	Intermediate Similarity	NPD1661	Suspended
0.7357	Intermediate Similarity	NPD803	Phase 1
0.7348	Intermediate Similarity	NPD8840	Approved
0.7343	Intermediate Similarity	NPD9506	Approved
0.7338	Intermediate Similarity	NPD3654	Approved
0.7324	Intermediate Similarity	NPD272	Approved
0.732	Intermediate Similarity	NPD5255	Approved
0.7315	Intermediate Similarity	NPD1183	Approved
0.731	Intermediate Similarity	NPD1649	Discontinued
0.7303	Intermediate Similarity	NPD6026	Approved
0.7273	Intermediate Similarity	NPD2511	Approved
0.7273	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4805	Approved
0.7255	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2581	Approved
0.7255	Intermediate Similarity	NPD2582	Approved
0.7248	Intermediate Similarity	NPD2110	Approved
0.7241	Intermediate Similarity	NPD4804	Approved
0.7226	Intermediate Similarity	NPD8026	Phase 1
0.7219	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD1561	Phase 2
0.72	Intermediate Similarity	NPD3100	Discontinued
0.7172	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3339	Approved
0.7171	Intermediate Similarity	NPD2837	Discontinued
0.7162	Intermediate Similarity	NPD649	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2172	Phase 1
0.7152	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6497	Approved
0.7143	Intermediate Similarity	NPD5020	Approved
0.7132	Intermediate Similarity	NPD9598	Discontinued
0.7124	Intermediate Similarity	NPD2061	Approved
0.7124	Intermediate Similarity	NPD2165	Phase 1
0.7115	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6771	Discontinued
0.7115	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5315	Discontinued
0.7113	Intermediate Similarity	NPD809	Discontinued
0.7089	Intermediate Similarity	NPD5611	Phase 2
0.7086	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5787	Discontinued
0.7078	Intermediate Similarity	NPD3114	Approved
0.7078	Intermediate Similarity	NPD3112	Approved
0.7078	Intermediate Similarity	NPD3113	Approved
0.7078	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3115	Approved
0.7075	Intermediate Similarity	NPD9599	Approved
0.707	Intermediate Similarity	NPD6635	Approved
0.707	Intermediate Similarity	NPD5088	Discontinued
0.7063	Intermediate Similarity	NPD9100	Approved
0.7051	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1328	Approved
0.7007	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4239	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD5418	Discontinued
0.6987	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD45	Approved
0.6986	Remote Similarity	NPD6554	Approved
0.6981	Remote Similarity	NPD3929	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2580	Discontinued
0.6962	Remote Similarity	NPD3323	Discontinued
0.6962	Remote Similarity	NPD3583	Phase 2
0.6962	Remote Similarity	NPD8129	Discovery
0.6957	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2640	Approved
0.6937	Remote Similarity	NPD2641	Approved
0.6937	Remote Similarity	NPD5862	Discovery
0.6937	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4811	Discontinued
0.6933	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2145	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1254	Approved
0.6918	Remote Similarity	NPD2720	Phase 1
0.6918	Remote Similarity	NPD1253	Approved
0.6918	Remote Similarity	NPD1256	Approved
0.6918	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1255	Approved
0.6903	Remote Similarity	NPD976	Approved
0.6903	Remote Similarity	NPD975	Approved
0.6903	Remote Similarity	NPD977	Approved
0.6901	Remote Similarity	NPD1031	Discontinued
0.6894	Remote Similarity	NPD4973	Approved
0.689	Remote Similarity	NPD8122	Approved
0.689	Remote Similarity	NPD8123	Approved
0.6887	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5636	Discontinued
0.6875	Remote Similarity	NPD6446	Discontinued
0.6867	Remote Similarity	NPD4891	Phase 2
0.6852	Remote Similarity	NPD3116	Approved
0.6852	Remote Similarity	NPD3117	Approved
0.6839	Remote Similarity	NPD1917	Discontinued
0.6835	Remote Similarity	NPD1404	Approved
0.6835	Remote Similarity	NPD1403	Approved
0.6832	Remote Similarity	NPD4639	Approved
0.6832	Remote Similarity	NPD1343	Approved
0.6832	Remote Similarity	NPD4640	Approved
0.6832	Remote Similarity	NPD4638	Approved
0.6829	Remote Similarity	NPD5100	Phase 3
0.6829	Remote Similarity	NPD6044	Discontinued
0.6821	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1988	Phase 1
0.6818	Remote Similarity	NPD4463	Approved
0.6818	Remote Similarity	NPD4462	Approved
0.6815	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD925	Approved
0.6813	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