NPASS Compound

Structure

NPC308931 OpenBabel07101718312D 25 29 0 0 1 0 0 0 0 0999 V2000 -3.2564 -2.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8745 0.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1225 -2.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7405 0.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3904 -2.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0085 0.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1225 -1.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7405 -0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0540 0.3783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6720 -2.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3904 -1.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0085 -0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2653 -1.3669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2564 -0.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8745 -1.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2872 -1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0485 0.2738 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.6666 -2.1759 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6180 -1.9021 0.0000 N 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 1.6473 0.5352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 12 2 0 0 0 0 6 13 2 0 0 0 0 7 16 2 0 0 0 0 8 17 2 0 0 0 0 9 14 2 0 0 0 0 9 21 1 0 0 0 0 10 15 2 0 0 0 0 10 22 1 0 0 0 0 11 18 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 14 1 6 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 23 2 0 0 0 0 20 24 1 0 0 0 0 20 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.13
Volume:	338.107
LogP:	2.801
LogD:	2.891
LogS:	-2.974
# Rotatable Bonds:	2
TPSA:	73.04
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.528
Synthetic Accessibility Score:	3.246
Fsp3:	0.1
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:	-5.186
MDCK Permeability:	5.3244762057147454e-06
Pgp-inhibitor:	0.625
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.102
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.844
Plasma Protein Binding (PPB):	85.8232421875%
Volume Distribution (VD):	2.125
Pgp-substrate:	8.451912879943848%

ADMET: Metabolism

CYP1A2-inhibitor:	0.855
CYP1A2-substrate:	0.641
CYP2C19-inhibitor:	0.922
CYP2C19-substrate:	0.185
CYP2C9-inhibitor:	0.636
CYP2C9-substrate:	0.976
CYP2D6-inhibitor:	0.675
CYP2D6-substrate:	0.898
CYP3A4-inhibitor:	0.943
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	3.828
Half-life (T1/2):	0.833

ADMET: Toxicity

hERG Blockers:	0.188
Human Hepatotoxicity (H-HT):	0.96
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.631
Rat Oral Acute Toxicity:	0.966
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.14
Carcinogencity:	0.023
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC308931

Natural Product ID:	NPC308931
*Common Name:**	(S)-6',6''-Didebromohamacanthin A
IUPAC Name:	(2S)-2,5-bis(1H-indol-3-yl)-2,3-dihydro-1H-pyrazin-6-one
Synonyms:	(S)-6',6'-Didebromohamacanthin A
Standard InCHIKey:	LIRZQQBDXFBNSN-GOSISDBHSA-N
Standard InCHI:	InChI=1S/C20H16N4O/c25-20-19(15-10-22-17-8-4-2-6-13(15)17)23-11-18(24-20)14-9-21-16-7-3-1-5-12(14)16/h1-10,18,21-22H,11H2,(H,24,25)/t18-/m1/s1
SMILES:	c1ccc2c(c1)c(c[nH]2)[C@H]1CN=C(c2c[nH]c3ccccc23)C(=O)N1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL215977
PubChem CID:	16104843
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921415]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16154746]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253840]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	southern australian	n.a.	PMID[9599272]

☑ 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
ED50	5
MIC	20

Activity Type	# Activity
Cell Line	5
Organism	20

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	8.3	ug ml-1	PMID[466553]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	11.5	ug ml-1	PMID[466553]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	5.0	ug ml-1	PMID[466553]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	17.1	ug ml-1	PMID[466553]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	4.1	ug ml-1	PMID[466553]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	25.0	ug.mL-1	PMID[466553]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	25.0	ug.mL-1	PMID[466553]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	25.0	ug.mL-1	PMID[466553]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	25.0	ug.mL-1	PMID[466553]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	25.0	ug.mL-1	PMID[466553]
NPT4997	Organism	Klebsiella oxytoca	Klebsiella oxytoca	MIC	>	25.0	ug.mL-1	PMID[466553]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	25.0	ug.mL-1	PMID[466553]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	25.0	ug.mL-1	PMID[466553]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	>	25.0	ug.mL-1	PMID[466553]
NPT720	Organism	Enterobacter aerogenes	Enterobacter aerogenes	MIC	>	25.0	ug.mL-1	PMID[466553]

☑ 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 NPC308931 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	678
0.1-0.2	9380
0.2-0.3	20187
0.3-0.4	6494
0.4-0.5	2166
0.5-0.6	1883
0.6-0.7	1284
0.7-0.8	555
0.8-0.85	47
0.85-0.9	11
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC99939
0.9209	High Similarity	NPC268744
0.9209	High Similarity	NPC153123
0.9209	High Similarity	NPC475914
0.9209	High Similarity	NPC220797
0.9209	High Similarity	NPC201266
0.9209	High Similarity	NPC474318
0.9157	High Similarity	NPC166209
0.9157	High Similarity	NPC13456
0.9157	High Similarity	NPC269203
0.9157	High Similarity	NPC77241
0.8814	High Similarity	NPC476460
0.875	High Similarity	NPC17059
0.8671	High Similarity	NPC11126
0.8595	High Similarity	NPC317701
0.858	High Similarity	NPC228835
0.8508	High Similarity	NPC304203
0.8475	Intermediate Similarity	NPC477003
0.8439	Intermediate Similarity	NPC161861
0.8418	Intermediate Similarity	NPC470205
0.8389	Intermediate Similarity	NPC321708
0.8354	Intermediate Similarity	NPC288838
0.8343	Intermediate Similarity	NPC135141
0.8343	Intermediate Similarity	NPC92796
0.8324	Intermediate Similarity	NPC15102
0.8313	Intermediate Similarity	NPC53947
0.8306	Intermediate Similarity	NPC326422
0.8305	Intermediate Similarity	NPC91179
0.8295	Intermediate Similarity	NPC284775
0.8295	Intermediate Similarity	NPC59269
0.8278	Intermediate Similarity	NPC94752
0.827	Intermediate Similarity	NPC227582
0.8226	Intermediate Similarity	NPC131887
0.8208	Intermediate Similarity	NPC56233
0.8198	Intermediate Similarity	NPC317105
0.8182	Intermediate Similarity	NPC74413
0.8176	Intermediate Similarity	NPC216643
0.8138	Intermediate Similarity	NPC252338
0.8122	Intermediate Similarity	NPC133003
0.8107	Intermediate Similarity	NPC325903
0.8092	Intermediate Similarity	NPC21174
0.8092	Intermediate Similarity	NPC271797
0.8087	Intermediate Similarity	NPC213629
0.8075	Intermediate Similarity	NPC167710
0.8073	Intermediate Similarity	NPC54420
0.8071	Intermediate Similarity	NPC477715
0.8065	Intermediate Similarity	NPC294693
0.8053	Intermediate Similarity	NPC476073
0.8053	Intermediate Similarity	NPC260900
0.8043	Intermediate Similarity	NPC324091
0.8032	Intermediate Similarity	NPC67288
0.803	Intermediate Similarity	NPC477714
0.8	Intermediate Similarity	NPC16659
0.8	Intermediate Similarity	NPC72956
0.799	Intermediate Similarity	NPC478158
0.799	Intermediate Similarity	NPC162860
0.7989	Intermediate Similarity	NPC478184
0.797	Intermediate Similarity	NPC478157
0.7967	Intermediate Similarity	NPC21429
0.7959	Intermediate Similarity	NPC153980
0.7959	Intermediate Similarity	NPC6865
0.7955	Intermediate Similarity	NPC63751
0.7944	Intermediate Similarity	NPC265710
0.7937	Intermediate Similarity	NPC171317
0.7933	Intermediate Similarity	NPC280852
0.7895	Intermediate Similarity	NPC477004
0.7895	Intermediate Similarity	NPC200214
0.7889	Intermediate Similarity	NPC473380
0.7889	Intermediate Similarity	NPC240088
0.7886	Intermediate Similarity	NPC478182
0.788	Intermediate Similarity	NPC62749
0.7876	Intermediate Similarity	NPC473376
0.7874	Intermediate Similarity	NPC122141
0.787	Intermediate Similarity	NPC469811
0.7869	Intermediate Similarity	NPC467063
0.7868	Intermediate Similarity	NPC471193
0.7868	Intermediate Similarity	NPC75634
0.7868	Intermediate Similarity	NPC471194
0.7866	Intermediate Similarity	NPC105127
0.7857	Intermediate Similarity	NPC314372
0.7857	Intermediate Similarity	NPC470440
0.7857	Intermediate Similarity	NPC191415
0.7844	Intermediate Similarity	NPC190296
0.7842	Intermediate Similarity	NPC474389
0.7841	Intermediate Similarity	NPC42372
0.7839	Intermediate Similarity	NPC471192
0.7831	Intermediate Similarity	NPC469784
0.7831	Intermediate Similarity	NPC469780
0.7831	Intermediate Similarity	NPC469767
0.7831	Intermediate Similarity	NPC469779
0.7831	Intermediate Similarity	NPC469761
0.7831	Intermediate Similarity	NPC469768
0.7831	Intermediate Similarity	NPC469783
0.7824	Intermediate Similarity	NPC321911
0.7821	Intermediate Similarity	NPC477611
0.7816	Intermediate Similarity	NPC475990
0.7816	Intermediate Similarity	NPC206819
0.7816	Intermediate Similarity	NPC293487
0.7816	Intermediate Similarity	NPC318065
0.7814	Intermediate Similarity	NPC102755
0.7811	Intermediate Similarity	NPC143872
0.7811	Intermediate Similarity	NPC63545
0.7809	Intermediate Similarity	NPC194411
0.7809	Intermediate Similarity	NPC471943
0.7805	Intermediate Similarity	NPC96102
0.7801	Intermediate Similarity	NPC293917
0.779	Intermediate Similarity	NPC84827
0.779	Intermediate Similarity	NPC111275
0.779	Intermediate Similarity	NPC145885
0.779	Intermediate Similarity	NPC14113
0.7784	Intermediate Similarity	NPC17273
0.7784	Intermediate Similarity	NPC469766
0.7784	Intermediate Similarity	NPC141612
0.7784	Intermediate Similarity	NPC135601
0.7778	Intermediate Similarity	NPC105818
0.7778	Intermediate Similarity	NPC110500
0.7778	Intermediate Similarity	NPC470702
0.7778	Intermediate Similarity	NPC473218
0.7778	Intermediate Similarity	NPC149155
0.7778	Intermediate Similarity	NPC203468
0.7778	Intermediate Similarity	NPC24678
0.7772	Intermediate Similarity	NPC165495
0.7771	Intermediate Similarity	NPC110126
0.7771	Intermediate Similarity	NPC73767
0.7765	Intermediate Similarity	NPC179787
0.7765	Intermediate Similarity	NPC201380
0.776	Intermediate Similarity	NPC205254
0.776	Intermediate Similarity	NPC23420
0.776	Intermediate Similarity	NPC106771
0.776	Intermediate Similarity	NPC303820
0.7758	Intermediate Similarity	NPC84911
0.7753	Intermediate Similarity	NPC78020
0.7751	Intermediate Similarity	NPC159856
0.775	Intermediate Similarity	NPC470731
0.775	Intermediate Similarity	NPC470732
0.7747	Intermediate Similarity	NPC213468
0.7747	Intermediate Similarity	NPC55772
0.7739	Intermediate Similarity	NPC470703
0.7735	Intermediate Similarity	NPC267885
0.7727	Intermediate Similarity	NPC194881
0.7727	Intermediate Similarity	NPC470203
0.772	Intermediate Similarity	NPC475935
0.772	Intermediate Similarity	NPC52909
0.772	Intermediate Similarity	NPC94211
0.7705	Intermediate Similarity	NPC88110
0.7697	Intermediate Similarity	NPC29886
0.7697	Intermediate Similarity	NPC474561
0.7697	Intermediate Similarity	NPC49954
0.7697	Intermediate Similarity	NPC478183
0.7697	Intermediate Similarity	NPC261195
0.7688	Intermediate Similarity	NPC469760
0.7688	Intermediate Similarity	NPC469763
0.7688	Intermediate Similarity	NPC25008
0.7688	Intermediate Similarity	NPC110602
0.7688	Intermediate Similarity	NPC259644
0.7688	Intermediate Similarity	NPC469786
0.7688	Intermediate Similarity	NPC75726
0.7688	Intermediate Similarity	NPC73952
0.7688	Intermediate Similarity	NPC31385
0.7688	Intermediate Similarity	NPC469765
0.768	Intermediate Similarity	NPC275305
0.768	Intermediate Similarity	NPC293216
0.768	Intermediate Similarity	NPC37423
0.768	Intermediate Similarity	NPC469529
0.767	Intermediate Similarity	NPC470204
0.767	Intermediate Similarity	NPC279918
0.767	Intermediate Similarity	NPC229173
0.7656	Intermediate Similarity	NPC473640
0.765	Intermediate Similarity	NPC126709
0.765	Intermediate Similarity	NPC283219
0.765	Intermediate Similarity	NPC248041
0.7644	Intermediate Similarity	NPC80597
0.7644	Intermediate Similarity	NPC75540
0.7644	Intermediate Similarity	NPC70922
0.7644	Intermediate Similarity	NPC212376
0.7644	Intermediate Similarity	NPC211572
0.7629	Intermediate Similarity	NPC475506
0.7627	Intermediate Similarity	NPC478185
0.7627	Intermediate Similarity	NPC282231
0.7619	Intermediate Similarity	NPC279081
0.7617	Intermediate Similarity	NPC100321
0.7614	Intermediate Similarity	NPC56765
0.7614	Intermediate Similarity	NPC474880
0.7614	Intermediate Similarity	NPC221786
0.7614	Intermediate Similarity	NPC41257
0.76	Intermediate Similarity	NPC469785
0.7596	Intermediate Similarity	NPC64436
0.7596	Intermediate Similarity	NPC68354
0.7594	Intermediate Similarity	NPC235684
0.759	Intermediate Similarity	NPC155143
0.7579	Intermediate Similarity	NPC216550
0.7576	Intermediate Similarity	NPC116555
0.7571	Intermediate Similarity	NPC44773
0.7571	Intermediate Similarity	NPC215584
0.7562	Intermediate Similarity	NPC54744
0.7561	Intermediate Similarity	NPC82295
0.7558	Intermediate Similarity	NPC471957
0.7557	Intermediate Similarity	NPC286427
0.7557	Intermediate Similarity	NPC469762
0.7557	Intermediate Similarity	NPC236711

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 NPC308931 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	691
0.2-0.3	1089
0.3-0.4	1986
0.4-0.5	2097
0.5-0.6	1945
0.6-0.7	828
0.7-0.8	174
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8708	High Similarity	NPD6180	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7618	Phase 3
0.8462	Intermediate Similarity	NPD7619	Phase 3
0.8448	Intermediate Similarity	NPD4075	Phase 2
0.8278	Intermediate Similarity	NPD6217	Discontinued
0.8253	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8177	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.8172	Intermediate Similarity	NPD6664	Approved
0.8158	Intermediate Similarity	NPD5426	Phase 3
0.8081	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.8066	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.8066	Intermediate Similarity	NPD7564	Discontinued
0.8054	Intermediate Similarity	NPD4922	Phase 2
0.8033	Intermediate Similarity	NPD3961	Discontinued
0.7989	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD2880	Discontinued
0.7979	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD2443	Approved
0.7938	Intermediate Similarity	NPD2442	Approved
0.7923	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD3319	Phase 1
0.7912	Intermediate Similarity	NPD3318	Approved
0.7912	Intermediate Similarity	NPD3320	Approved
0.7901	Intermediate Similarity	NPD6595	Phase 3
0.7887	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD786	Approved
0.7877	Intermediate Similarity	NPD4128	Approved
0.7831	Intermediate Similarity	NPD4848	Phase 1
0.7824	Intermediate Similarity	NPD3100	Discontinued
0.7817	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2837	Discontinued
0.7784	Intermediate Similarity	NPD3583	Phase 2
0.7784	Intermediate Similarity	NPD1722	Approved
0.7784	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2172	Phase 1
0.7778	Intermediate Similarity	NPD482	Approved
0.7778	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD2091	Phase 2
0.7772	Intermediate Similarity	NPD2096	Phase 2
0.7755	Intermediate Similarity	NPD6459	Phase 2
0.7755	Intermediate Similarity	NPD7665	Phase 2
0.7755	Intermediate Similarity	NPD7666	Phase 3
0.7744	Intermediate Similarity	NPD2008	Discontinued
0.7742	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD2095	Phase 2
0.7717	Intermediate Similarity	NPD2094	Phase 2
0.7717	Intermediate Similarity	NPD2092	Phase 2
0.7716	Intermediate Similarity	NPD2408	Discontinued
0.7708	Intermediate Similarity	NPD6999	Discontinued
0.7708	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD2411	Approved
0.7688	Intermediate Similarity	NPD8093	Discontinued
0.7684	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD5065	Approved
0.7677	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2009	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD7470	Discontinued
0.7637	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD6771	Discontinued
0.7609	Intermediate Similarity	NPD5473	Discontinued
0.7602	Intermediate Similarity	NPD5901	Discontinued
0.7596	Intermediate Similarity	NPD4181	Approved
0.7596	Intermediate Similarity	NPD3506	Approved
0.7596	Intermediate Similarity	NPD3505	Approved
0.7594	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD7944	Discontinued
0.7584	Intermediate Similarity	NPD3323	Discontinued
0.7562	Intermediate Similarity	NPD8094	Discontinued
0.7556	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD4076	Approved
0.7554	Intermediate Similarity	NPD4079	Approved
0.7554	Intermediate Similarity	NPD2590	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD8047	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD5400	Approved
0.7528	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7970	Approved
0.7513	Intermediate Similarity	NPD7175	Phase 1
0.7512	Intermediate Similarity	NPD7781	Approved
0.7512	Intermediate Similarity	NPD7780	Approved
0.75	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD1895	Discontinued
0.7464	Intermediate Similarity	NPD6165	Phase 2
0.7464	Intermediate Similarity	NPD6164	Phase 2
0.7463	Intermediate Similarity	NPD5198	Approved
0.7463	Intermediate Similarity	NPD5199	Approved
0.7459	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD5017	Discontinued
0.7449	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD201	Phase 2
0.744	Intermediate Similarity	NPD200	Phase 2
0.7432	Intermediate Similarity	NPD750	Phase 2
0.7419	Intermediate Similarity	NPD2479	Phase 3
0.7419	Intermediate Similarity	NPD2481	Approved
0.7418	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7603	Discontinued
0.7403	Intermediate Similarity	NPD2639	Approved
0.7403	Intermediate Similarity	NPD2642	Approved
0.7398	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD7001	Phase 3
0.7385	Intermediate Similarity	NPD1982	Phase 1
0.7371	Intermediate Similarity	NPD4462	Approved
0.7371	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD4463	Approved
0.7368	Intermediate Similarity	NPD8431	Approved
0.7366	Intermediate Similarity	NPD3079	Approved
0.7366	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD3077	Approved
0.7366	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD3078	Approved
0.7366	Intermediate Similarity	NPD3076	Approved
0.7363	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7704	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6044	Discontinued
0.734	Intermediate Similarity	NPD5106	Approved
0.734	Intermediate Similarity	NPD5105	Approved
0.7333	Intermediate Similarity	NPD5446	Phase 2
0.733	Intermediate Similarity	NPD6470	Phase 3
0.7326	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD2881	Approved
0.7323	Intermediate Similarity	NPD2879	Approved
0.7316	Intermediate Similarity	NPD7026	Phase 2
0.7313	Intermediate Similarity	NPD2510	Approved
0.7313	Intermediate Similarity	NPD2509	Approved
0.7313	Intermediate Similarity	NPD5421	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6178	Phase 3
0.73	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4883	Approved
0.7296	Intermediate Similarity	NPD4364	Phase 1
0.7292	Intermediate Similarity	NPD4499	Approved
0.7291	Intermediate Similarity	NPD4863	Approved
0.7283	Intermediate Similarity	NPD3610	Approved
0.7283	Intermediate Similarity	NPD3609	Approved
0.7282	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4348	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD8322	Phase 2
0.7264	Intermediate Similarity	NPD3905	Phase 3
0.7257	Intermediate Similarity	NPD4547	Phase 3
0.7255	Intermediate Similarity	NPD4852	Phase 2
0.725	Intermediate Similarity	NPD8272	Phase 2
0.7241	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4051	Discontinued
0.724	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6986	Phase 1
0.722	Intermediate Similarity	NPD6787	Phase 2
0.7219	Intermediate Similarity	NPD2144	Approved
0.7216	Intermediate Similarity	NPD3431	Approved
0.7216	Intermediate Similarity	NPD3430	Approved
0.7214	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7789	Approved
0.7209	Intermediate Similarity	NPD7951	Approved
0.7209	Intermediate Similarity	NPD7790	Approved
0.7209	Intermediate Similarity	NPD7950	Approved
0.7209	Intermediate Similarity	NPD7953	Approved
0.7209	Intermediate Similarity	NPD7952	Approved
0.7209	Intermediate Similarity	NPD7791	Approved
0.7206	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1683	Approved
0.7198	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7185	Discontinued
0.7198	Intermediate Similarity	NPD8256	Approved
0.7198	Intermediate Similarity	NPD8257	Approved
0.7198	Intermediate Similarity	NPD5818	Discontinued
0.7196	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7394	Phase 2
0.7188	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5254	Discontinued
0.7182	Intermediate Similarity	NPD1404	Approved
0.7182	Intermediate Similarity	NPD1403	Approved
0.7178	Intermediate Similarity	NPD1506	Discontinued
0.7174	Intermediate Similarity	NPD2640	Approved
0.7174	Intermediate Similarity	NPD2641	Approved
0.7174	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7657	Approved
0.7171	Intermediate Similarity	NPD7656	Approved
0.7165	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD7209	Approved
0.7164	Intermediate Similarity	NPD7207	Approved
0.7164	Intermediate Similarity	NPD7208	Approved
0.716	Intermediate Similarity	NPD3385	Approved
0.7158	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3868	Phase 1
0.715	Intermediate Similarity	NPD6268	Phase 1
0.715	Intermediate Similarity	NPD4851	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6269	Clinical (unspecified phase)

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