NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.22
Volume:	304.54
LogP:	4.472
LogD:	4.099
LogS:	-3.279
# Rotatable Bonds:	0
TPSA:	3.88
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.473
Synthetic Accessibility Score:	4.552
Fsp3:	0.611
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:	-4.871
MDCK Permeability:	3.146740345982835e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.534
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.56
Plasma Protein Binding (PPB):	86.94761657714844%
Volume Distribution (VD):	1.624
Pgp-substrate:	8.380825996398926%

ADMET: Metabolism

CYP1A2-inhibitor:	0.087
CYP1A2-substrate:	0.872
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.981
CYP2D6-substrate:	0.295
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.438

ADMET: Excretion

Clearance (CL):	6.362
Half-life (T1/2):	0.891

ADMET: Toxicity

hERG Blockers:	0.203
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.074
Maximum Recommended Daily Dose:	0.495
Skin Sensitization:	0.963
Carcinogencity:	0.268
Eye Corrosion:	0.046
Eye Irritation:	0.457
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC240136

Natural Product ID:	NPC240136
*Common Name:**	Dehydrohaliclocyclin C
IUPAC Name:	(7Z)-1-azoniabicyclo[13.3.1]nonadeca-1(18),7,15(19),16-tetraene
Synonyms:
Standard InCHIKey:	GXMFNZNPCVZZCK-IWQZZHSRSA-N
Standard InCHI:	InChI=1S/C18H28N/c1-2-4-6-8-10-13-18-14-12-16-19(17-18)15-11-9-7-5-3-1/h1,3,12,14,16-17H,2,4-11,13,15H2/q+1/b3-1-
SMILES:	C1C/C=CCCCCC[n+]2cc(CCCC1)ccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431892
PubChem CID:	72705440
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0001764] Pyridinium 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
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575970]
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17848089]
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	Pacific	n.a.	PMID[19133758]
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	Culasian Point, Leyte, Philippines (S 1119.00', E 12435.60')	1991-MAR	PMID[22873824]
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	New Zealand	n.a.	PMID[24128145]

☑ 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
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC50	=	1.5	ug.mL-1	PMID[558796]

☑ 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 NPC240136 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	1130
0.1-0.2	12719
0.2-0.3	17844
0.3-0.4	5805
0.4-0.5	2729
0.5-0.6	1676
0.6-0.7	560
0.7-0.8	178
0.8-0.85	27
0.85-0.9	21
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC297486
1.0	High Similarity	NPC471402
0.9237	High Similarity	NPC476322
0.9217	High Similarity	NPC91958
0.9189	High Similarity	NPC27802
0.9153	High Similarity	NPC290094
0.9068	High Similarity	NPC329825
0.8983	High Similarity	NPC265605
0.8983	High Similarity	NPC48564
0.8983	High Similarity	NPC182570
0.8943	High Similarity	NPC69914
0.8926	High Similarity	NPC169625
0.8926	High Similarity	NPC202957
0.8919	High Similarity	NPC76540
0.8889	High Similarity	NPC143603
0.8862	High Similarity	NPC476131
0.878	High Similarity	NPC89490
0.871	High Similarity	NPC475105
0.871	High Similarity	NPC329896
0.871	High Similarity	NPC475090
0.8689	High Similarity	NPC245244
0.8689	High Similarity	NPC166424
0.8689	High Similarity	NPC146373
0.8607	High Similarity	NPC27740
0.8548	High Similarity	NPC471311
0.8548	High Similarity	NPC471313
0.8545	High Similarity	NPC83987
0.8534	High Similarity	NPC235843
0.8525	High Similarity	NPC46358
0.8385	Intermediate Similarity	NPC251722
0.8385	Intermediate Similarity	NPC314102
0.8281	Intermediate Similarity	NPC101165
0.8281	Intermediate Similarity	NPC256893
0.8281	Intermediate Similarity	NPC471322
0.8261	Intermediate Similarity	NPC231655
0.8258	Intermediate Similarity	NPC315348
0.8258	Intermediate Similarity	NPC32002
0.8258	Intermediate Similarity	NPC316811
0.825	Intermediate Similarity	NPC476566
0.8244	Intermediate Similarity	NPC150259
0.8203	Intermediate Similarity	NPC282398
0.814	Intermediate Similarity	NPC324611
0.7971	Intermediate Similarity	NPC477974
0.797	Intermediate Similarity	NPC65408
0.797	Intermediate Similarity	NPC471312
0.791	Intermediate Similarity	NPC169433
0.7886	Intermediate Similarity	NPC81561
0.7857	Intermediate Similarity	NPC40070
0.7852	Intermediate Similarity	NPC73767
0.7805	Intermediate Similarity	NPC148140
0.7794	Intermediate Similarity	NPC469784
0.7794	Intermediate Similarity	NPC469768
0.7794	Intermediate Similarity	NPC469767
0.7794	Intermediate Similarity	NPC469779
0.7794	Intermediate Similarity	NPC469761
0.7794	Intermediate Similarity	NPC469780
0.7794	Intermediate Similarity	NPC469783
0.7786	Intermediate Similarity	NPC315320
0.7761	Intermediate Similarity	NPC261195
0.7761	Intermediate Similarity	NPC29886
0.7761	Intermediate Similarity	NPC96102
0.7737	Intermediate Similarity	NPC476454
0.7737	Intermediate Similarity	NPC469766
0.7727	Intermediate Similarity	NPC82295
0.7721	Intermediate Similarity	NPC110126
0.7705	Intermediate Similarity	NPC473901
0.7704	Intermediate Similarity	NPC105127
0.7704	Intermediate Similarity	NPC84911
0.7692	Intermediate Similarity	NPC212125
0.7681	Intermediate Similarity	NPC477977
0.768	Intermediate Similarity	NPC162689
0.768	Intermediate Similarity	NPC54102
0.7676	Intermediate Similarity	NPC470233
0.7626	Intermediate Similarity	NPC471323
0.7591	Intermediate Similarity	NPC104483
0.7589	Intermediate Similarity	NPC470111
0.7586	Intermediate Similarity	NPC129721
0.7581	Intermediate Similarity	NPC84268
0.7571	Intermediate Similarity	NPC86288
0.7565	Intermediate Similarity	NPC213774
0.7559	Intermediate Similarity	NPC215519
0.7557	Intermediate Similarity	NPC306397
0.7557	Intermediate Similarity	NPC165370
0.7554	Intermediate Similarity	NPC20144
0.7537	Intermediate Similarity	NPC322488
0.7536	Intermediate Similarity	NPC279081
0.7518	Intermediate Similarity	NPC63545
0.75	Intermediate Similarity	NPC471589
0.7465	Intermediate Similarity	NPC201380
0.7465	Intermediate Similarity	NPC469811
0.7465	Intermediate Similarity	NPC179787
0.7462	Intermediate Similarity	NPC122718
0.7447	Intermediate Similarity	NPC314372
0.7429	Intermediate Similarity	NPC190296
0.7415	Intermediate Similarity	NPC56765
0.7413	Intermediate Similarity	NPC321911
0.741	Intermediate Similarity	NPC230002
0.7397	Intermediate Similarity	NPC476464
0.7394	Intermediate Similarity	NPC288838
0.7383	Intermediate Similarity	NPC478182
0.7379	Intermediate Similarity	NPC325903
0.7372	Intermediate Similarity	NPC29702
0.7361	Intermediate Similarity	NPC105818
0.7361	Intermediate Similarity	NPC53947
0.7361	Intermediate Similarity	NPC24678
0.7344	Intermediate Similarity	NPC11863
0.7333	Intermediate Similarity	NPC477975
0.7324	Intermediate Similarity	NPC285731
0.7324	Intermediate Similarity	NPC159856
0.7315	Intermediate Similarity	NPC471177
0.7315	Intermediate Similarity	NPC124542
0.7315	Intermediate Similarity	NPC59779
0.7308	Intermediate Similarity	NPC56856
0.7299	Intermediate Similarity	NPC198988
0.7297	Intermediate Similarity	NPC477591
0.7297	Intermediate Similarity	NPC293487
0.7293	Intermediate Similarity	NPC278451
0.7286	Intermediate Similarity	NPC59084
0.7286	Intermediate Similarity	NPC2949
0.7279	Intermediate Similarity	NPC51054
0.7279	Intermediate Similarity	NPC330326
0.7273	Intermediate Similarity	NPC143872
0.7267	Intermediate Similarity	NPC90723
0.726	Intermediate Similarity	NPC469786
0.726	Intermediate Similarity	NPC469765
0.726	Intermediate Similarity	NPC200214
0.726	Intermediate Similarity	NPC25008
0.726	Intermediate Similarity	NPC73952
0.726	Intermediate Similarity	NPC469763
0.726	Intermediate Similarity	NPC138842
0.726	Intermediate Similarity	NPC259644
0.726	Intermediate Similarity	NPC469760
0.7234	Intermediate Similarity	NPC473868
0.7234	Intermediate Similarity	NPC63157
0.7222	Intermediate Similarity	NPC471957
0.7219	Intermediate Similarity	NPC471178
0.7218	Intermediate Similarity	NPC135488
0.7214	Intermediate Similarity	NPC88097
0.7211	Intermediate Similarity	NPC70922
0.7211	Intermediate Similarity	NPC212376
0.7211	Intermediate Similarity	NPC211572
0.7211	Intermediate Similarity	NPC80597
0.7211	Intermediate Similarity	NPC75540
0.7203	Intermediate Similarity	NPC469525
0.72	Intermediate Similarity	NPC71079
0.72	Intermediate Similarity	NPC470203
0.7181	Intermediate Similarity	NPC206819
0.7181	Intermediate Similarity	NPC318065
0.7171	Intermediate Similarity	NPC478183
0.7171	Intermediate Similarity	NPC98187
0.7162	Intermediate Similarity	NPC469785
0.7152	Intermediate Similarity	NPC474217
0.7152	Intermediate Similarity	NPC478184
0.7133	Intermediate Similarity	NPC470204
0.7133	Intermediate Similarity	NPC215584
0.7133	Intermediate Similarity	NPC44773
0.7122	Intermediate Similarity	NPC325252
0.7114	Intermediate Similarity	NPC236711
0.7114	Intermediate Similarity	NPC469897
0.7114	Intermediate Similarity	NPC286427
0.7114	Intermediate Similarity	NPC216643
0.7114	Intermediate Similarity	NPC469762
0.7095	Intermediate Similarity	NPC34844
0.709	Intermediate Similarity	NPC476140
0.7086	Intermediate Similarity	NPC478185
0.7083	Intermediate Similarity	NPC467188
0.7078	Intermediate Similarity	NPC116961
0.7075	Intermediate Similarity	NPC470823
0.7075	Intermediate Similarity	NPC216713
0.7071	Intermediate Similarity	NPC114310
0.7067	Intermediate Similarity	NPC135141
0.7067	Intermediate Similarity	NPC41257
0.7067	Intermediate Similarity	NPC92796
0.7067	Intermediate Similarity	NPC80681
0.7059	Intermediate Similarity	NPC278366
0.7059	Intermediate Similarity	NPC56233
0.7059	Intermediate Similarity	NPC127730
0.7045	Intermediate Similarity	NPC41174
0.7039	Intermediate Similarity	NPC473057
0.7039	Intermediate Similarity	NPC469813
0.7039	Intermediate Similarity	NPC476446
0.7039	Intermediate Similarity	NPC317105
0.7039	Intermediate Similarity	NPC78375
0.7034	Intermediate Similarity	NPC316069
0.7027	Intermediate Similarity	NPC141926
0.702	Intermediate Similarity	NPC122141
0.7015	Intermediate Similarity	NPC151489
0.7014	Intermediate Similarity	NPC230085
0.7014	Intermediate Similarity	NPC159630
0.7007	Intermediate Similarity	NPC22079
0.7007	Intermediate Similarity	NPC473878
0.7	Intermediate Similarity	NPC167635
0.7	Intermediate Similarity	NPC193740
0.7	Intermediate Similarity	NPC218268
0.6993	Remote Similarity	NPC85918
0.6986	Remote Similarity	NPC105811
0.6986	Remote Similarity	NPC21605
0.6985	Remote Similarity	NPC313823
0.698	Remote Similarity	NPC476219
0.698	Remote Similarity	NPC477815

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 NPC240136 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	420
0.1-0.2	963
0.2-0.3	971
0.3-0.4	2066
0.4-0.5	2622
0.5-0.6	1507
0.6-0.7	455
0.7-0.8	115
0.8-0.85	19
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9196	High Similarity	NPD4823	Approved
0.9196	High Similarity	NPD4824	Approved
0.9008	High Similarity	NPD2118	Approved
0.9008	High Similarity	NPD2119	Approved
0.8983	High Similarity	NPD268	Approved
0.8983	High Similarity	NPD271	Approved
0.8983	High Similarity	NPD270	Clinical (unspecified phase)
0.879	High Similarity	NPD3475	Approved
0.879	High Similarity	NPD3476	Approved
0.8651	High Similarity	NPD1995	Approved
0.8651	High Similarity	NPD1993	Approved
0.8651	High Similarity	NPD1994	Approved
0.8632	High Similarity	NPD269	Clinical (unspecified phase)
0.8618	High Similarity	NPD9583	Approved
0.8583	High Similarity	NPD4028	Approved
0.8583	High Similarity	NPD3942	Approved
0.8583	High Similarity	NPD3944	Approved
0.8583	High Similarity	NPD4029	Approved
0.8583	High Similarity	NPD4030	Approved
0.8548	High Similarity	NPD991	Phase 2
0.8548	High Similarity	NPD992	Clinical (unspecified phase)
0.8455	Intermediate Similarity	NPD9357	Approved
0.8443	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1598	Discontinued
0.8261	Intermediate Similarity	NPD9098	Phase 3
0.8261	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD2070	Approved
0.8258	Intermediate Similarity	NPD2072	Approved
0.8258	Intermediate Similarity	NPD2075	Approved
0.8258	Intermediate Similarity	NPD2073	Approved
0.8258	Intermediate Similarity	NPD2069	Approved
0.8258	Intermediate Similarity	NPD2068	Approved
0.8258	Intermediate Similarity	NPD2074	Approved
0.8258	Intermediate Similarity	NPD2071	Approved
0.8231	Intermediate Similarity	NPD2141	Approved
0.8231	Intermediate Similarity	NPD2140	Approved
0.8231	Intermediate Similarity	NPD2142	Approved
0.8217	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.8203	Intermediate Similarity	NPD715	Phase 3
0.8182	Intermediate Similarity	NPD2896	Discontinued
0.8168	Intermediate Similarity	NPD792	Discontinued
0.8033	Intermediate Similarity	NPD9396	Approved
0.8033	Intermediate Similarity	NPD9392	Approved
0.7971	Intermediate Similarity	NPD4547	Phase 3
0.797	Intermediate Similarity	NPD201	Phase 2
0.797	Intermediate Similarity	NPD200	Phase 2
0.7941	Intermediate Similarity	NPD4510	Discontinued
0.7941	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD7469	Discontinued
0.7883	Intermediate Similarity	NPD3813	Approved
0.7879	Intermediate Similarity	NPD3385	Approved
0.7868	Intermediate Similarity	NPD1722	Approved
0.7863	Intermediate Similarity	NPD803	Phase 1
0.7852	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD3654	Approved
0.7842	Intermediate Similarity	NPD4702	Approved
0.7842	Intermediate Similarity	NPD4703	Approved
0.781	Intermediate Similarity	NPD2006	Phase 2
0.781	Intermediate Similarity	NPD3717	Discontinued
0.7786	Intermediate Similarity	NPD9206	Approved
0.7786	Intermediate Similarity	NPD9207	Approved
0.7761	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2465	Approved
0.773	Intermediate Similarity	NPD2466	Phase 3
0.773	Intermediate Similarity	NPD2462	Phase 3
0.7721	Intermediate Similarity	NPD786	Approved
0.7692	Intermediate Similarity	NPD9284	Approved
0.766	Intermediate Similarity	NPD2430	Phase 2
0.7643	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD9598	Discontinued
0.7634	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2837	Discontinued
0.7594	Intermediate Similarity	NPD9726	Discontinued
0.7589	Intermediate Similarity	NPD2110	Approved
0.7581	Intermediate Similarity	NPD60	Approved
0.7557	Intermediate Similarity	NPD9080	Approved
0.7556	Intermediate Similarity	NPD272	Approved
0.7552	Intermediate Similarity	NPD4641	Discontinued
0.7552	Intermediate Similarity	NPD3262	Approved
0.7535	Intermediate Similarity	NPD3100	Discontinued
0.7518	Intermediate Similarity	NPD1380	Discovery
0.75	Intermediate Similarity	NPD3339	Approved
0.75	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2581	Approved
0.7466	Intermediate Similarity	NPD6497	Approved
0.7466	Intermediate Similarity	NPD2582	Approved
0.7465	Intermediate Similarity	NPD1270	Approved
0.7465	Intermediate Similarity	NPD1661	Suspended
0.7464	Intermediate Similarity	NPD4804	Approved
0.746	Intermediate Similarity	NPD8840	Approved
0.7448	Intermediate Similarity	NPD2809	Approved
0.7448	Intermediate Similarity	NPD2165	Phase 1
0.7445	Intermediate Similarity	NPD45	Approved
0.7445	Intermediate Similarity	NPD6554	Approved
0.7432	Intermediate Similarity	NPD5315	Discontinued
0.7431	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD5255	Approved
0.7413	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1183	Approved
0.741	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD3115	Approved
0.7397	Intermediate Similarity	NPD3113	Approved
0.7397	Intermediate Similarity	NPD2580	Discontinued
0.7397	Intermediate Similarity	NPD3114	Approved
0.7397	Intermediate Similarity	NPD6026	Approved
0.7397	Intermediate Similarity	NPD3112	Approved
0.7376	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1255	Approved
0.7372	Intermediate Similarity	NPD1256	Approved
0.7372	Intermediate Similarity	NPD1254	Approved
0.7372	Intermediate Similarity	NPD1253	Approved
0.7365	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2511	Approved
0.7361	Intermediate Similarity	NPD2172	Phase 1
0.7357	Intermediate Similarity	NPD1383	Phase 3
0.7357	Intermediate Similarity	NPD1382	Phase 2
0.7357	Intermediate Similarity	NPD4805	Approved
0.7347	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD809	Discontinued
0.7319	Intermediate Similarity	NPD9506	Approved
0.7315	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6771	Discontinued
0.7305	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5418	Discontinued
0.7286	Intermediate Similarity	NPD1649	Discontinued
0.7279	Intermediate Similarity	NPD9100	Approved
0.7267	Intermediate Similarity	NPD3323	Discontinued
0.7266	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5020	Approved
0.7211	Intermediate Similarity	NPD976	Approved
0.7211	Intermediate Similarity	NPD977	Approved
0.7211	Intermediate Similarity	NPD1328	Approved
0.7211	Intermediate Similarity	NPD975	Approved
0.7211	Intermediate Similarity	NPD2061	Approved
0.72	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5787	Discontinued
0.7171	Intermediate Similarity	NPD5636	Discontinued
0.7171	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD9599	Approved
0.7162	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD4811	Discontinued
0.7153	Intermediate Similarity	NPD1683	Approved
0.7152	Intermediate Similarity	NPD6635	Approved
0.7152	Intermediate Similarity	NPD5088	Discontinued
0.7143	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1917	Discontinued
0.7133	Intermediate Similarity	NPD1988	Phase 1
0.7133	Intermediate Similarity	NPD1352	Discontinued
0.7133	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2640	Approved
0.7124	Intermediate Similarity	NPD5862	Discovery
0.7124	Intermediate Similarity	NPD2641	Approved
0.7124	Intermediate Similarity	NPD2333	Discontinued
0.7114	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5358	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5400	Approved
0.7086	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD8026	Phase 1
0.7078	Intermediate Similarity	NPD4973	Approved
0.7067	Intermediate Similarity	NPD3433	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4047	Discontinued
0.7059	Intermediate Similarity	NPD5611	Phase 2
0.7059	Intermediate Similarity	NPD947	Approved
0.7059	Intermediate Similarity	NPD9305	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6446	Discontinued
0.7055	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1561	Phase 2
0.7042	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3583	Phase 2
0.7039	Intermediate Similarity	NPD8129	Discovery
0.7032	Intermediate Similarity	NPD3609	Approved
0.7032	Intermediate Similarity	NPD3610	Approved
0.702	Intermediate Similarity	NPD1403	Approved
0.702	Intermediate Similarity	NPD1404	Approved
0.7014	Intermediate Similarity	NPD4509	Discontinued
0.7014	Intermediate Similarity	NPD649	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5671	Approved
0.7013	Intermediate Similarity	NPD4638	Approved
0.7013	Intermediate Similarity	NPD4639	Approved
0.7013	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4640	Approved
0.7007	Intermediate Similarity	NPD7913	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2145	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5300	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2782	Approved
0.6993	Remote Similarity	NPD2780	Approved
0.6993	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2720	Phase 1

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