NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	221.1
Volume:	236.929
LogP:	2.35
LogD:	2.078
LogS:	-3.012
# Rotatable Bonds:	1
TPSA:	52.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.652
Synthetic Accessibility Score:	2.491
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.584
MDCK Permeability:	1.9902876374544576e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.052
Human Intestinal Absorption (HIA):	0.058
20% Bioavailability (F20%):	0.899
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.857
Plasma Protein Binding (PPB):	65.71788787841797%
Volume Distribution (VD):	1.782
Pgp-substrate:	27.701292037963867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.516
CYP2C19-inhibitor:	0.626
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.362
CYP2C9-substrate:	0.659
CYP2D6-inhibitor:	0.978
CYP2D6-substrate:	0.879
CYP3A4-inhibitor:	0.866
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	7.63
Half-life (T1/2):	0.757

ADMET: Toxicity

hERG Blockers:	0.68
Human Hepatotoxicity (H-HT):	0.943
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.417
Rat Oral Acute Toxicity:	0.944
Maximum Recommended Daily Dose:	0.892
Skin Sensitization:	0.868
Carcinogencity:	0.053
Eye Corrosion:	0.004
Eye Irritation:	0.137
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC101165

Natural Product ID:	NPC101165
*Common Name:**	Lophocladine B
IUPAC Name:	4-phenyl-2,7-naphthyridin-1-amine
Synonyms:
Standard InCHIKey:	UGLZUYWXOHMUSU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H11N3/c15-14-13-8-16-7-6-11(13)12(9-17-14)10-4-2-1-3-5-10/h1-9H,(H2,15,17)
SMILES:	N=c1[nH]cc(c2c1cncc2)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480873
PubChem CID:	11665726
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0002317] Phenylpyridines

*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
NPO32709	lophocladia sp.	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643042]

☑ 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	2
Others	5

Activity Type	# Activity
Cell Line	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	3100.0	nM	PMID[528739]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	64600.0	nM	PMID[528739]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	80.0	%	PMID[528739]
NPT2657	Cell Line	A10	Rattus norvegicus	Inhibition	=	85.0	%	PMID[528739]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	Activity	=	19.8	%	PMID[528739]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	Activity	=	8.0	%	PMID[528739]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	Activity	=	72.2	%	PMID[528739]

☑ 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 NPC101165 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	1488
0.1-0.2	14718
0.2-0.3	17683
0.3-0.4	4266
0.4-0.5	2164
0.5-0.6	1614
0.6-0.7	587
0.7-0.8	166
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.88	High Similarity	NPC91958
0.876	High Similarity	NPC245244
0.876	High Similarity	NPC146373
0.876	High Similarity	NPC166424
0.8538	High Similarity	NPC27740
0.8504	High Similarity	NPC143603
0.838	Intermediate Similarity	NPC143872
0.837	Intermediate Similarity	NPC471322
0.8296	Intermediate Similarity	NPC282398
0.8281	Intermediate Similarity	NPC240136
0.8281	Intermediate Similarity	NPC471402
0.8281	Intermediate Similarity	NPC297486
0.8188	Intermediate Similarity	NPC122141
0.8168	Intermediate Similarity	NPC182570
0.8168	Intermediate Similarity	NPC48564
0.8168	Intermediate Similarity	NPC265605
0.816	Intermediate Similarity	NPC27802
0.8148	Intermediate Similarity	NPC89490
0.8133	Intermediate Similarity	NPC225018
0.812	Intermediate Similarity	NPC476322
0.8088	Intermediate Similarity	NPC329896
0.8088	Intermediate Similarity	NPC475105
0.8088	Intermediate Similarity	NPC475090
0.8071	Intermediate Similarity	NPC105127
0.8045	Intermediate Similarity	NPC46358
0.8045	Intermediate Similarity	NPC290094
0.8029	Intermediate Similarity	NPC69914
0.8	Intermediate Similarity	NPC96102
0.797	Intermediate Similarity	NPC329825
0.7958	Intermediate Similarity	NPC110126
0.7956	Intermediate Similarity	NPC476131
0.7943	Intermediate Similarity	NPC84911
0.7943	Intermediate Similarity	NPC314102
0.7943	Intermediate Similarity	NPC251722
0.792	Intermediate Similarity	NPC76540
0.7872	Intermediate Similarity	NPC29886
0.7872	Intermediate Similarity	NPC261195
0.7868	Intermediate Similarity	NPC202957
0.7868	Intermediate Similarity	NPC169625
0.7842	Intermediate Similarity	NPC256893
0.7832	Intermediate Similarity	NPC73767
0.7829	Intermediate Similarity	NPC470204
0.7823	Intermediate Similarity	NPC469811
0.7817	Intermediate Similarity	NPC125746
0.7778	Intermediate Similarity	NPC279081
0.7778	Intermediate Similarity	NPC469783
0.7778	Intermediate Similarity	NPC469784
0.7778	Intermediate Similarity	NPC469761
0.7778	Intermediate Similarity	NPC470203
0.7778	Intermediate Similarity	NPC469768
0.7778	Intermediate Similarity	NPC469767
0.7778	Intermediate Similarity	NPC469780
0.7778	Intermediate Similarity	NPC469779
0.777	Intermediate Similarity	NPC321911
0.7762	Intermediate Similarity	NPC169433
0.7755	Intermediate Similarity	NPC63545
0.7752	Intermediate Similarity	NPC235843
0.7733	Intermediate Similarity	NPC325903
0.7724	Intermediate Similarity	NPC469766
0.7724	Intermediate Similarity	NPC476454
0.7714	Intermediate Similarity	NPC82295
0.7708	Intermediate Similarity	NPC315348
0.7708	Intermediate Similarity	NPC32002
0.7708	Intermediate Similarity	NPC316811
0.7703	Intermediate Similarity	NPC201380
0.7703	Intermediate Similarity	NPC179787
0.7687	Intermediate Similarity	NPC86288
0.7681	Intermediate Similarity	NPC471311
0.7681	Intermediate Similarity	NPC471313
0.7677	Intermediate Similarity	NPC280864
0.7677	Intermediate Similarity	NPC17751
0.7671	Intermediate Similarity	NPC190296
0.7667	Intermediate Similarity	NPC470233
0.7655	Intermediate Similarity	NPC230002
0.7635	Intermediate Similarity	NPC288838
0.7589	Intermediate Similarity	NPC324611
0.7581	Intermediate Similarity	NPC83987
0.7576	Intermediate Similarity	NPC84268
0.7568	Intermediate Similarity	NPC314372
0.7568	Intermediate Similarity	NPC204141
0.7568	Intermediate Similarity	NPC159856
0.7532	Intermediate Similarity	NPC318065
0.7532	Intermediate Similarity	NPC56765
0.7532	Intermediate Similarity	NPC206819
0.7518	Intermediate Similarity	NPC22079
0.75	Intermediate Similarity	NPC478184
0.75	Intermediate Similarity	NPC317105
0.75	Intermediate Similarity	NPC325252
0.7483	Intermediate Similarity	NPC53947
0.7483	Intermediate Similarity	NPC40070
0.7468	Intermediate Similarity	NPC193740
0.7468	Intermediate Similarity	NPC469897
0.7467	Intermediate Similarity	NPC471957
0.7448	Intermediate Similarity	NPC150259
0.7431	Intermediate Similarity	NPC198988
0.7407	Intermediate Similarity	NPC54102
0.7407	Intermediate Similarity	NPC162689
0.7403	Intermediate Similarity	NPC476464
0.7388	Intermediate Similarity	NPC148140
0.7386	Intermediate Similarity	NPC138842
0.7372	Intermediate Similarity	NPC279918
0.7372	Intermediate Similarity	NPC44773
0.7372	Intermediate Similarity	NPC215584
0.7368	Intermediate Similarity	NPC105818
0.7368	Intermediate Similarity	NPC24678
0.7364	Intermediate Similarity	NPC231655
0.7355	Intermediate Similarity	NPC216643
0.7355	Intermediate Similarity	NPC286427
0.7355	Intermediate Similarity	NPC236711
0.7351	Intermediate Similarity	NPC470111
0.7347	Intermediate Similarity	NPC88097
0.7333	Intermediate Similarity	NPC81561
0.7329	Intermediate Similarity	NPC65408
0.7325	Intermediate Similarity	NPC282231
0.732	Intermediate Similarity	NPC216713
0.732	Intermediate Similarity	NPC470823
0.7315	Intermediate Similarity	NPC20144
0.7308	Intermediate Similarity	NPC41257
0.7308	Intermediate Similarity	NPC293487
0.7297	Intermediate Similarity	NPC115611
0.7297	Intermediate Similarity	NPC59084
0.7284	Intermediate Similarity	NPC280297
0.7278	Intermediate Similarity	NPC90723
0.7273	Intermediate Similarity	NPC259644
0.7273	Intermediate Similarity	NPC469765
0.7273	Intermediate Similarity	NPC469786
0.7273	Intermediate Similarity	NPC200214
0.7273	Intermediate Similarity	NPC141926
0.7273	Intermediate Similarity	NPC25008
0.7273	Intermediate Similarity	NPC469760
0.7273	Intermediate Similarity	NPC73952
0.7273	Intermediate Similarity	NPC469763
0.7267	Intermediate Similarity	NPC201634
0.725	Intermediate Similarity	NPC63751
0.7248	Intermediate Similarity	NPC63157
0.7248	Intermediate Similarity	NPC473868
0.7244	Intermediate Similarity	NPC167635
0.7237	Intermediate Similarity	NPC477974
0.7226	Intermediate Similarity	NPC211572
0.7226	Intermediate Similarity	NPC70922
0.7226	Intermediate Similarity	NPC212376
0.7226	Intermediate Similarity	NPC80597
0.7226	Intermediate Similarity	NPC34844
0.7226	Intermediate Similarity	NPC75540
0.7226	Intermediate Similarity	NPC476219
0.7219	Intermediate Similarity	NPC285731
0.7219	Intermediate Similarity	NPC467188
0.7211	Intermediate Similarity	NPC471312
0.7205	Intermediate Similarity	NPC194411
0.72	Intermediate Similarity	NPC477977
0.7197	Intermediate Similarity	NPC92796
0.7197	Intermediate Similarity	NPC135141
0.7188	Intermediate Similarity	NPC49217
0.7188	Intermediate Similarity	NPC54988
0.7188	Intermediate Similarity	NPC474561
0.7188	Intermediate Similarity	NPC49954
0.7183	Intermediate Similarity	NPC306397
0.7181	Intermediate Similarity	NPC2949
0.7179	Intermediate Similarity	NPC51054
0.7179	Intermediate Similarity	NPC469785
0.7178	Intermediate Similarity	NPC317054
0.7174	Intermediate Similarity	NPC215519
0.717	Intermediate Similarity	NPC478182
0.7169	Intermediate Similarity	NPC307191
0.7161	Intermediate Similarity	NPC232798
0.7143	Intermediate Similarity	NPC218268
0.7134	Intermediate Similarity	NPC469762
0.7125	Intermediate Similarity	NPC274229
0.7124	Intermediate Similarity	NPC105811
0.7124	Intermediate Similarity	NPC21605
0.7115	Intermediate Similarity	NPC476297
0.7113	Intermediate Similarity	NPC250361
0.7107	Intermediate Similarity	NPC478185
0.7092	Intermediate Similarity	NPC122718
0.7083	Intermediate Similarity	NPC467063
0.7083	Intermediate Similarity	NPC108011
0.7081	Intermediate Similarity	NPC478183
0.7073	Intermediate Similarity	NPC37423
0.7073	Intermediate Similarity	NPC275305
0.7073	Intermediate Similarity	NPC471579
0.7063	Intermediate Similarity	NPC212125
0.7063	Intermediate Similarity	NPC97367
0.7063	Intermediate Similarity	NPC194640
0.7059	Intermediate Similarity	NPC316069
0.7055	Intermediate Similarity	NPC82331
0.7055	Intermediate Similarity	NPC470498
0.7044	Intermediate Similarity	NPC131718
0.7034	Intermediate Similarity	NPC315320
0.703	Intermediate Similarity	NPC474958
0.7025	Intermediate Similarity	NPC129721
0.7014	Intermediate Similarity	NPC473762
0.7007	Intermediate Similarity	NPC476566
0.7	Intermediate Similarity	NPC59779
0.7	Intermediate Similarity	NPC471177
0.7	Intermediate Similarity	NPC124542
0.7	Intermediate Similarity	NPC104483
0.6994	Remote Similarity	NPC32534
0.6994	Remote Similarity	NPC97343
0.6994	Remote Similarity	NPC91895
0.6993	Remote 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 NPC101165 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	532
0.1-0.2	944
0.2-0.3	1039
0.3-0.4	2326
0.4-0.5	2097
0.5-0.6	1501
0.6-0.7	585
0.7-0.8	124
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9213	High Similarity	NPD1598	Discontinued
0.8769	High Similarity	NPD992	Clinical (unspecified phase)
0.8769	High Similarity	NPD991	Phase 2
0.8561	High Similarity	NPD2007	Clinical (unspecified phase)
0.8413	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD2118	Approved
0.8346	Intermediate Similarity	NPD2119	Approved
0.8168	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD268	Approved
0.8168	Intermediate Similarity	NPD271	Approved
0.8134	Intermediate Similarity	NPD9583	Approved
0.8116	Intermediate Similarity	NPD3944	Approved
0.8116	Intermediate Similarity	NPD3942	Approved
0.8099	Intermediate Similarity	NPD1722	Approved
0.8058	Intermediate Similarity	NPD2142	Approved
0.8058	Intermediate Similarity	NPD2140	Approved
0.8058	Intermediate Similarity	NPD2141	Approved
0.8029	Intermediate Similarity	NPD3476	Approved
0.8029	Intermediate Similarity	NPD3475	Approved
0.8	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD9392	Approved
0.8	Intermediate Similarity	NPD9396	Approved
0.7986	Intermediate Similarity	NPD4030	Approved
0.7986	Intermediate Similarity	NPD4029	Approved
0.7986	Intermediate Similarity	NPD4028	Approved
0.7985	Intermediate Similarity	NPD9357	Approved
0.7973	Intermediate Similarity	NPD1917	Discontinued
0.7971	Intermediate Similarity	NPD9726	Discontinued
0.7958	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1994	Approved
0.7914	Intermediate Similarity	NPD1995	Approved
0.7914	Intermediate Similarity	NPD1993	Approved
0.7891	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD2466	Phase 3
0.7838	Intermediate Similarity	NPD2462	Phase 3
0.7838	Intermediate Similarity	NPD2465	Approved
0.7832	Intermediate Similarity	NPD786	Approved
0.7778	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD3100	Discontinued
0.777	Intermediate Similarity	NPD715	Phase 3
0.7748	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1988	Phase 1
0.7733	Intermediate Similarity	NPD3339	Approved
0.7733	Intermediate Similarity	NPD2837	Discontinued
0.7708	Intermediate Similarity	NPD2072	Approved
0.7708	Intermediate Similarity	NPD2068	Approved
0.7708	Intermediate Similarity	NPD2069	Approved
0.7708	Intermediate Similarity	NPD2074	Approved
0.7708	Intermediate Similarity	NPD2075	Approved
0.7708	Intermediate Similarity	NPD2073	Approved
0.7708	Intermediate Similarity	NPD2071	Approved
0.7708	Intermediate Similarity	NPD2070	Approved
0.7704	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD975	Approved
0.7682	Intermediate Similarity	NPD976	Approved
0.7682	Intermediate Similarity	NPD977	Approved
0.7671	Intermediate Similarity	NPD4510	Discontinued
0.7667	Intermediate Similarity	NPD4641	Discontinued
0.7667	Intermediate Similarity	NPD3262	Approved
0.7662	Intermediate Similarity	NPD8026	Phase 1
0.7622	Intermediate Similarity	NPD792	Discontinued
0.7615	Intermediate Similarity	NPD4824	Approved
0.7615	Intermediate Similarity	NPD4823	Approved
0.7589	Intermediate Similarity	NPD803	Phase 1
0.7584	Intermediate Similarity	NPD4702	Approved
0.7584	Intermediate Similarity	NPD4547	Phase 3
0.7584	Intermediate Similarity	NPD4703	Approved
0.7566	Intermediate Similarity	NPD1328	Approved
0.7551	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2896	Discontinued
0.75	Intermediate Similarity	NPD3813	Approved
0.75	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4891	Phase 2
0.7483	Intermediate Similarity	NPD3385	Approved
0.7468	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5300	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD2110	Approved
0.7451	Intermediate Similarity	NPD2165	Phase 1
0.7436	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6771	Discontinued
0.7432	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2006	Phase 2
0.7421	Intermediate Similarity	NPD5436	Phase 1
0.7417	Intermediate Similarity	NPD2430	Phase 2
0.7403	Intermediate Similarity	NPD3113	Approved
0.7403	Intermediate Similarity	NPD3115	Approved
0.7403	Intermediate Similarity	NPD3114	Approved
0.7403	Intermediate Similarity	NPD3112	Approved
0.74	Intermediate Similarity	NPD7469	Discontinued
0.74	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4128	Approved
0.7391	Intermediate Similarity	NPD2928	Phase 2
0.7389	Intermediate Similarity	NPD3323	Discontinued
0.7379	Intermediate Similarity	NPD1256	Approved
0.7379	Intermediate Similarity	NPD1255	Approved
0.7379	Intermediate Similarity	NPD1254	Approved
0.7379	Intermediate Similarity	NPD1253	Approved
0.7372	Intermediate Similarity	NPD9598	Discontinued
0.7368	Intermediate Similarity	NPD2172	Phase 1
0.7364	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD9098	Phase 3
0.7355	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7402	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD809	Discontinued
0.7329	Intermediate Similarity	NPD200	Phase 2
0.7329	Intermediate Similarity	NPD201	Phase 2
0.7325	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD947	Approved
0.7312	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4371	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD4181	Approved
0.7296	Intermediate Similarity	NPD5611	Phase 2
0.729	Intermediate Similarity	NPD2150	Discontinued
0.7285	Intermediate Similarity	NPD1683	Approved
0.7278	Intermediate Similarity	NPD3583	Phase 2
0.7273	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6828	Phase 2
0.7267	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6497	Approved
0.7244	Intermediate Similarity	NPD2145	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1270	Approved
0.7222	Intermediate Similarity	NPD1251	Discontinued
0.7211	Intermediate Similarity	NPD1262	Discovery
0.7203	Intermediate Similarity	NPD3654	Approved
0.72	Intermediate Similarity	NPD4047	Discontinued
0.7194	Intermediate Similarity	NPD5787	Discontinued
0.719	Intermediate Similarity	NPD1183	Approved
0.7188	Intermediate Similarity	NPD1248	Discontinued
0.7183	Intermediate Similarity	NPD9080	Approved
0.7178	Intermediate Similarity	NPD3799	Suspended
0.7178	Intermediate Similarity	NPD5065	Approved
0.7174	Intermediate Similarity	NPD4811	Discontinued
0.7169	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3610	Approved
0.716	Intermediate Similarity	NPD3609	Approved
0.7152	Intermediate Similarity	NPD5671	Approved
0.7152	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4298	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2640	Approved
0.7143	Intermediate Similarity	NPD2641	Approved
0.7134	Intermediate Similarity	NPD4075	Phase 2
0.7134	Intermediate Similarity	NPD6044	Discontinued
0.7134	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1661	Suspended
0.7118	Intermediate Similarity	NPD7175	Phase 1
0.7115	Intermediate Similarity	NPD2061	Approved
0.7114	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2480	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5400	Approved
0.7101	Intermediate Similarity	NPD706	Phase 1
0.7099	Intermediate Similarity	NPD4024	Phase 3
0.7089	Intermediate Similarity	NPD1679	Approved
0.7089	Intermediate Similarity	NPD5255	Approved
0.7086	Intermediate Similarity	NPD3717	Discontinued
0.7083	Intermediate Similarity	NPD9305	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1589	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1561	Phase 2
0.707	Intermediate Similarity	NPD2580	Discontinued
0.7063	Intermediate Similarity	NPD9284	Approved
0.7044	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1404	Approved
0.7044	Intermediate Similarity	NPD1403	Approved
0.7041	Intermediate Similarity	NPD3771	Phase 3
0.7041	Intermediate Similarity	NPD2868	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2333	Discontinued
0.7034	Intermediate Similarity	NPD9207	Approved
0.7034	Intermediate Similarity	NPD9206	Approved
0.7032	Intermediate Similarity	NPD971	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2581	Approved
0.7025	Intermediate Similarity	NPD2582	Approved
0.702	Intermediate Similarity	NPD461	Approved
0.7019	Intermediate Similarity	NPD1313	Approved
0.7006	Intermediate Similarity	NPD2809	Approved
0.7	Intermediate Similarity	NPD1016	Phase 2
0.7	Intermediate Similarity	NPD7026	Phase 2
0.7	Intermediate Similarity	NPD1015	Phase 2
0.7	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5315	Discontinued
0.6988	Remote Similarity	NPD7111	Discontinued
0.6988	Remote Similarity	NPD3506	Approved
0.6988	Remote Similarity	NPD3505	Approved
0.6987	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5418	Discontinued
0.6977	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5636	Discontinued
0.6964	Remote Similarity	NPD1895	Discontinued
0.6962	Remote Similarity	NPD6026	Approved
0.6959	Remote Similarity	NPD272	Approved
0.6954	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD9599	Approved
0.6951	Remote Similarity	NPD3117	Approved
0.6951	Remote Similarity	NPD3116	Approved
0.6946	Remote Similarity	NPD4076	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