NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.12
Volume:	283.924
LogP:	4.267
LogD:	3.993
LogS:	-4.798
# Rotatable Bonds:	2
TPSA:	28.68
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.57
Synthetic Accessibility Score:	2.062
Fsp3:	0.056
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:	-4.882
MDCK Permeability:	2.155987749574706e-05
Pgp-inhibitor:	0.341
Pgp-substrate:	0.118
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.909

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.803
Plasma Protein Binding (PPB):	97.55623626708984%
Volume Distribution (VD):	1.513
Pgp-substrate:	1.4594416618347168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.979
CYP1A2-substrate:	0.694
CYP2C19-inhibitor:	0.95
CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.888
CYP2C9-substrate:	0.834
CYP2D6-inhibitor:	0.861
CYP2D6-substrate:	0.673
CYP3A4-inhibitor:	0.838
CYP3A4-substrate:	0.614

ADMET: Excretion

Clearance (CL):	6.267
Half-life (T1/2):	0.495

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.719
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.794
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.542
Carcinogencity:	0.352
Eye Corrosion:	0.004
Eye Irritation:	0.519
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC325903

Natural Product ID:	NPC325903
*Common Name:**	Marinoquinoline C
IUPAC Name:	4-benzyl-3H-pyrrolo[2,3-c]quinoline
Synonyms:	Marinoquinoline C
Standard InCHIKey:	PWTJJPSHOLKBPE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14N2/c1-2-6-13(7-3-1)12-17-18-15(10-11-19-18)14-8-4-5-9-16(14)20-17/h1-11,19H,12H2
SMILES:	c1ccc(cc1)Cc1nc2ccccc2c2c1[nH]cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1773679
PubChem CID:	52952004
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001734] Pyrroloquinolines

*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
NPO30963	Ohtaekwangia kribbensis	Species	Cytophagaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21456549]

☑ 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	10
MIC	2

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	IC50	=	5.4	ug.mL-1	PMID[543279]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2.6	ug.mL-1	PMID[543279]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	0.55	ug.mL-1	PMID[543279]
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	39100.0	nM	PMID[543279]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.0	ug.mL-1	PMID[543279]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	5500.0	nM	PMID[543279]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	58800.0	nM	PMID[543279]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	28300.0	nM	PMID[543279]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	42200.0	nM	PMID[543279]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	MIC	=	33.5	ug.mL-1	PMID[543279]
NPT3628	Organism	Rhodotorula glutinis	Rhodotorula glutinis	MIC	=	33.5	ug.mL-1	PMID[543279]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	10000.0	nM	PMID[543280]

☑ 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 NPC325903 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	1411
0.1-0.2	14725
0.2-0.3	17597
0.3-0.4	4077
0.4-0.5	1741
0.5-0.6	1573
0.6-0.7	1002
0.7-0.8	405
0.8-0.85	111
0.85-0.9	38
0.9-0.95	11
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9718	High Similarity	NPC469811
0.965	High Similarity	NPC321911
0.9648	High Similarity	NPC63545
0.958	High Similarity	NPC201380
0.958	High Similarity	NPC179787
0.953	High Similarity	NPC317105
0.9267	High Similarity	NPC122141
0.9241	High Similarity	NPC288838
0.9205	High Similarity	NPC470203
0.9139	High Similarity	NPC470204
0.9133	High Similarity	NPC236711
0.9054	High Similarity	NPC53947
0.9028	High Similarity	NPC115611
0.9014	High Similarity	NPC96102
0.8951	High Similarity	NPC105127
0.8951	High Similarity	NPC84911
0.8924	High Similarity	NPC280852
0.8897	High Similarity	NPC469767
0.8897	High Similarity	NPC469784
0.8897	High Similarity	NPC284635
0.8897	High Similarity	NPC469780
0.8897	High Similarity	NPC469783
0.8897	High Similarity	NPC469761
0.8897	High Similarity	NPC469768
0.8897	High Similarity	NPC469779
0.8889	High Similarity	NPC215584
0.8889	High Similarity	NPC44773
0.8882	High Similarity	NPC216643
0.8881	High Similarity	NPC261195
0.8881	High Similarity	NPC29886
0.8839	High Similarity	NPC274229
0.8836	High Similarity	NPC469766
0.8828	High Similarity	NPC110126
0.8828	High Similarity	NPC73767
0.8767	High Similarity	NPC279081
0.875	High Similarity	NPC325252
0.8742	High Similarity	NPC470233
0.8732	High Similarity	NPC82295
0.871	High Similarity	NPC225018
0.8701	High Similarity	NPC135141
0.8701	High Similarity	NPC56765
0.8701	High Similarity	NPC92796
0.8688	High Similarity	NPC474958
0.8681	High Similarity	NPC198988
0.8671	High Similarity	NPC97343
0.8667	High Similarity	NPC470111
0.8649	High Similarity	NPC190296
0.8639	High Similarity	NPC230002
0.8625	High Similarity	NPC471579
0.8616	High Similarity	NPC82331
0.86	High Similarity	NPC143872
0.8571	High Similarity	NPC88097
0.8533	High Similarity	NPC159856
0.8533	High Similarity	NPC314372
0.8516	High Similarity	NPC286427
0.8506	High Similarity	NPC476219
0.8476	Intermediate Similarity	NPC307191
0.8462	Intermediate Similarity	NPC206819
0.8462	Intermediate Similarity	NPC318065
0.8462	Intermediate Similarity	NPC41257
0.8435	Intermediate Similarity	NPC314102
0.8435	Intermediate Similarity	NPC251722
0.8431	Intermediate Similarity	NPC24678
0.8431	Intermediate Similarity	NPC105818
0.8431	Intermediate Similarity	NPC40070
0.8421	Intermediate Similarity	NPC471957
0.8418	Intermediate Similarity	NPC478184
0.8414	Intermediate Similarity	NPC473930
0.8387	Intermediate Similarity	NPC476297
0.838	Intermediate Similarity	NPC250361
0.8367	Intermediate Similarity	NPC218268
0.8353	Intermediate Similarity	NPC324149
0.8344	Intermediate Similarity	NPC293487
0.8343	Intermediate Similarity	NPC231536
0.8323	Intermediate Similarity	NPC469763
0.8323	Intermediate Similarity	NPC259644
0.8323	Intermediate Similarity	NPC469786
0.8323	Intermediate Similarity	NPC469760
0.8323	Intermediate Similarity	NPC25008
0.8323	Intermediate Similarity	NPC73952
0.8323	Intermediate Similarity	NPC469765
0.8304	Intermediate Similarity	NPC326422
0.8302	Intermediate Similarity	NPC90723
0.8302	Intermediate Similarity	NPC478182
0.8291	Intermediate Similarity	NPC229173
0.8289	Intermediate Similarity	NPC204141
0.8276	Intermediate Similarity	NPC22079
0.8269	Intermediate Similarity	NPC75540
0.8269	Intermediate Similarity	NPC211572
0.8269	Intermediate Similarity	NPC80597
0.8269	Intermediate Similarity	NPC212376
0.8269	Intermediate Similarity	NPC70922
0.8267	Intermediate Similarity	NPC2949
0.8267	Intermediate Similarity	NPC59084
0.8264	Intermediate Similarity	NPC473762
0.8261	Intermediate Similarity	NPC63751
0.8258	Intermediate Similarity	NPC470823
0.8258	Intermediate Similarity	NPC216713
0.8253	Intermediate Similarity	NPC191415
0.8228	Intermediate Similarity	NPC474880
0.8228	Intermediate Similarity	NPC221786
0.8228	Intermediate Similarity	NPC477591
0.8228	Intermediate Similarity	NPC475990
0.8221	Intermediate Similarity	NPC477611
0.8219	Intermediate Similarity	NPC475450
0.8217	Intermediate Similarity	NPC469785
0.8212	Intermediate Similarity	NPC63157
0.8212	Intermediate Similarity	NPC473868
0.8207	Intermediate Similarity	NPC473587
0.8205	Intermediate Similarity	NPC141926
0.8205	Intermediate Similarity	NPC200214
0.8204	Intermediate Similarity	NPC102755
0.8204	Intermediate Similarity	NPC48938
0.8199	Intermediate Similarity	NPC478183
0.8182	Intermediate Similarity	NPC59269
0.817	Intermediate Similarity	NPC470440
0.8169	Intermediate Similarity	NPC46358
0.8165	Intermediate Similarity	NPC469762
0.8155	Intermediate Similarity	NPC284678
0.8153	Intermediate Similarity	NPC34844
0.8151	Intermediate Similarity	NPC475428
0.8133	Intermediate Similarity	NPC169433
0.8125	Intermediate Similarity	NPC478185
0.8107	Intermediate Similarity	NPC15102
0.8107	Intermediate Similarity	NPC308931
0.8107	Intermediate Similarity	NPC99939
0.8098	Intermediate Similarity	NPC194411
0.8095	Intermediate Similarity	NPC179365
0.8086	Intermediate Similarity	NPC56233
0.8079	Intermediate Similarity	NPC312092
0.8077	Intermediate Similarity	NPC33421
0.8067	Intermediate Similarity	NPC125746
0.8067	Intermediate Similarity	NPC150259
0.8065	Intermediate Similarity	NPC21605
0.8063	Intermediate Similarity	NPC279918
0.8059	Intermediate Similarity	NPC62749
0.8047	Intermediate Similarity	NPC108011
0.8012	Intermediate Similarity	NPC282231
0.8	Intermediate Similarity	NPC316069
0.7988	Intermediate Similarity	NPC91895
0.7988	Intermediate Similarity	NPC32534
0.7988	Intermediate Similarity	NPC474897
0.7986	Intermediate Similarity	NPC27740
0.7976	Intermediate Similarity	NPC314919
0.7975	Intermediate Similarity	NPC474561
0.7975	Intermediate Similarity	NPC49954
0.7972	Intermediate Similarity	NPC41174
0.7963	Intermediate Similarity	NPC311276
0.7952	Intermediate Similarity	NPC275305
0.7952	Intermediate Similarity	NPC37423
0.795	Intermediate Similarity	NPC131718
0.7935	Intermediate Similarity	NPC86288
0.7927	Intermediate Similarity	NPC201700
0.7922	Intermediate Similarity	NPC20144
0.7914	Intermediate Similarity	NPC17751
0.7914	Intermediate Similarity	NPC280864
0.791	Intermediate Similarity	NPC265576
0.7905	Intermediate Similarity	NPC282398
0.7889	Intermediate Similarity	NPC317701
0.7888	Intermediate Similarity	NPC230869
0.7866	Intermediate Similarity	NPC160105
0.7866	Intermediate Similarity	NPC54988
0.7857	Intermediate Similarity	NPC284775
0.7857	Intermediate Similarity	NPC68354
0.7853	Intermediate Similarity	NPC40779
0.7844	Intermediate Similarity	NPC297034
0.7829	Intermediate Similarity	NPC315617
0.7829	Intermediate Similarity	NPC316359
0.7817	Intermediate Similarity	NPC162689
0.7817	Intermediate Similarity	NPC91958
0.7817	Intermediate Similarity	NPC54102
0.7811	Intermediate Similarity	NPC176199
0.7811	Intermediate Similarity	NPC215795
0.7808	Intermediate Similarity	NPC245244
0.7808	Intermediate Similarity	NPC146373
0.7808	Intermediate Similarity	NPC166424
0.7758	Intermediate Similarity	NPC49217
0.7751	Intermediate Similarity	NPC151939
0.7747	Intermediate Similarity	NPC470505
0.7747	Intermediate Similarity	NPC470500
0.7747	Intermediate Similarity	NPC475070
0.7746	Intermediate Similarity	NPC94752
0.7744	Intermediate Similarity	NPC21174
0.7744	Intermediate Similarity	NPC149265
0.7744	Intermediate Similarity	NPC271797
0.7744	Intermediate Similarity	NPC194640
0.7744	Intermediate Similarity	NPC102423
0.7738	Intermediate Similarity	NPC317054
0.7733	Intermediate Similarity	NPC101165
0.7727	Intermediate Similarity	NPC314058
0.7727	Intermediate Similarity	NPC316018
0.7725	Intermediate Similarity	NPC470498
0.7714	Intermediate Similarity	NPC324091
0.7706	Intermediate Similarity	NPC12649
0.7706	Intermediate Similarity	NPC11126
0.7679	Intermediate Similarity	NPC314603
0.7674	Intermediate Similarity	NPC83381
0.7673	Intermediate Similarity	NPC2272
0.7667	Intermediate Similarity	NPC237414
0.7661	Intermediate Similarity	NPC300688

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 NPC325903 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	541
0.1-0.2	895
0.2-0.3	1042
0.3-0.4	2255
0.4-0.5	1971
0.5-0.6	1514
0.6-0.7	731
0.7-0.8	181
0.8-0.85	14
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9097	High Similarity	NPD1722	Approved
0.9014	High Similarity	NPD198	Clinical (unspecified phase)
0.8986	High Similarity	NPD4374	Clinical (unspecified phase)
0.8933	High Similarity	NPD2837	Discontinued
0.8828	High Similarity	NPD786	Approved
0.871	High Similarity	NPD1853	Clinical (unspecified phase)
0.8654	High Similarity	NPD3323	Discontinued
0.8649	High Similarity	NPD4637	Clinical (unspecified phase)
0.8609	High Similarity	NPD3100	Discontinued
0.8476	Intermediate Similarity	NPD1895	Discontinued
0.8431	Intermediate Similarity	NPD2172	Phase 1
0.8415	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD4547	Phase 3
0.8293	Intermediate Similarity	NPD4181	Approved
0.8282	Intermediate Similarity	NPD5065	Approved
0.8276	Intermediate Similarity	NPD715	Phase 3
0.8272	Intermediate Similarity	NPD3610	Approved
0.8272	Intermediate Similarity	NPD3609	Approved
0.8269	Intermediate Similarity	NPD976	Approved
0.8269	Intermediate Similarity	NPD975	Approved
0.8269	Intermediate Similarity	NPD977	Approved
0.8267	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD1683	Approved
0.8231	Intermediate Similarity	NPD3385	Approved
0.8194	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD991	Phase 2
0.8171	Intermediate Similarity	NPD4128	Approved
0.8158	Intermediate Similarity	NPD2006	Phase 2
0.8158	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD2640	Approved
0.8148	Intermediate Similarity	NPD2641	Approved
0.8129	Intermediate Similarity	NPD2430	Phase 2
0.8107	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD5254	Discontinued
0.8072	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD3476	Approved
0.8027	Intermediate Similarity	NPD3475	Approved
0.8024	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6595	Phase 3
0.7962	Intermediate Similarity	NPD4462	Approved
0.7962	Intermediate Similarity	NPD4463	Approved
0.795	Intermediate Similarity	NPD1404	Approved
0.795	Intermediate Similarity	NPD1403	Approved
0.7947	Intermediate Similarity	NPD6554	Approved
0.7947	Intermediate Similarity	NPD1262	Discovery
0.7947	Intermediate Similarity	NPD45	Approved
0.7945	Intermediate Similarity	NPD2118	Approved
0.7945	Intermediate Similarity	NPD2119	Approved
0.7939	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD4075	Phase 2
0.7898	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD5418	Discontinued
0.7879	Intermediate Similarity	NPD5436	Phase 1
0.7866	Intermediate Similarity	NPD2639	Approved
0.7866	Intermediate Similarity	NPD2642	Approved
0.7857	Intermediate Similarity	NPD3505	Approved
0.7857	Intermediate Similarity	NPD3506	Approved
0.7852	Intermediate Similarity	NPD803	Phase 1
0.7849	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD4079	Approved
0.7811	Intermediate Similarity	NPD4076	Approved
0.7805	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2580	Discontinued
0.7763	Intermediate Similarity	NPD1256	Approved
0.7763	Intermediate Similarity	NPD1255	Approved
0.7763	Intermediate Similarity	NPD1254	Approved
0.7763	Intermediate Similarity	NPD1253	Approved
0.7748	Intermediate Similarity	NPD3944	Approved
0.7748	Intermediate Similarity	NPD4029	Approved
0.7748	Intermediate Similarity	NPD3942	Approved
0.7748	Intermediate Similarity	NPD4030	Approved
0.7748	Intermediate Similarity	NPD4028	Approved
0.774	Intermediate Similarity	NPD7618	Phase 3
0.774	Intermediate Similarity	NPD7619	Phase 3
0.7722	Intermediate Similarity	NPD1661	Suspended
0.7718	Intermediate Similarity	NPD947	Approved
0.7718	Intermediate Similarity	NPD3654	Approved
0.7716	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD2333	Discontinued
0.7702	Intermediate Similarity	NPD2165	Phase 1
0.7701	Intermediate Similarity	NPD8431	Approved
0.7701	Intermediate Similarity	NPD3961	Discontinued
0.7701	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3348	Phase 2
0.7683	Intermediate Similarity	NPD5315	Discontinued
0.7674	Intermediate Similarity	NPD5106	Approved
0.7674	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD5105	Approved
0.7658	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD9598	Discontinued
0.7654	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3114	Approved
0.7654	Intermediate Similarity	NPD3115	Approved
0.7654	Intermediate Similarity	NPD3113	Approved
0.7654	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2927	Phase 3
0.7654	Intermediate Similarity	NPD3112	Approved
0.7651	Intermediate Similarity	NPD1248	Discontinued
0.7644	Intermediate Similarity	NPD6217	Discontinued
0.7644	Intermediate Similarity	NPD2793	Discontinued
0.7644	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD9583	Approved
0.7622	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6828	Phase 2
0.7619	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7394	Phase 2
0.7598	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1227	Phase 2
0.7574	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7469	Discontinued
0.7545	Intermediate Similarity	NPD2478	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD2144	Approved
0.7544	Intermediate Similarity	NPD7111	Discontinued
0.7543	Intermediate Similarity	NPD4902	Discontinued
0.7534	Intermediate Similarity	NPD271	Approved
0.7534	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD268	Approved
0.7531	Intermediate Similarity	NPD3339	Approved
0.7529	Intermediate Similarity	NPD482	Approved
0.7529	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6178	Phase 3
0.7514	Intermediate Similarity	NPD1707	Approved
0.7514	Intermediate Similarity	NPD1708	Approved
0.7514	Intermediate Similarity	NPD6133	Discontinued
0.75	Intermediate Similarity	NPD9392	Approved
0.75	Intermediate Similarity	NPD4326	Phase 2
0.75	Intermediate Similarity	NPD9357	Approved
0.75	Intermediate Similarity	NPD9396	Approved
0.7486	Intermediate Similarity	NPD4318	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2720	Phase 1
0.7485	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1313	Approved
0.7483	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6771	Discontinued
0.7468	Intermediate Similarity	NPD4880	Discontinued
0.7467	Intermediate Similarity	NPD1598	Discontinued
0.7459	Intermediate Similarity	NPD2880	Discontinued
0.7459	Intermediate Similarity	NPD5462	Discontinued
0.7443	Intermediate Similarity	NPD6721	Phase 1
0.743	Intermediate Similarity	NPD4922	Phase 2
0.7429	Intermediate Similarity	NPD7564	Discontinued
0.7425	Intermediate Similarity	NPD3583	Phase 2
0.7419	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3038	Discontinued
0.7414	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2316	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5021	Discontinued
0.7389	Intermediate Similarity	NPD2072	Approved
0.7389	Intermediate Similarity	NPD2068	Approved
0.7389	Intermediate Similarity	NPD2069	Approved
0.7389	Intermediate Similarity	NPD2074	Approved
0.7389	Intermediate Similarity	NPD2071	Approved
0.7389	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2075	Approved
0.7389	Intermediate Similarity	NPD2070	Approved
0.7389	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2073	Approved
0.7386	Intermediate Similarity	NPD4298	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1251	Discontinued
0.7374	Intermediate Similarity	NPD3419	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD2095	Phase 2
0.7371	Intermediate Similarity	NPD2094	Phase 2
0.7371	Intermediate Similarity	NPD2092	Phase 2
0.7368	Intermediate Similarity	NPD7216	Approved
0.7368	Intermediate Similarity	NPD7217	Approved
0.7368	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD5426	Phase 3
0.7365	Intermediate Similarity	NPD5787	Discontinued
0.7363	Intermediate Similarity	NPD7948	Phase 1
0.7363	Intermediate Similarity	NPD6664	Approved
0.7358	Intermediate Similarity	NPD4047	Discontinued
0.7356	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5962	Phase 2
0.7351	Intermediate Similarity	NPD3015	Discontinued
0.7349	Intermediate Similarity	NPD3433	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4811	Discontinued
0.7346	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2150	Discontinued
0.7333	Intermediate Similarity	NPD3404	Approved
0.7333	Intermediate Similarity	NPD4615	Phase 2

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