NPASS Compound

Structure

NPC470203 OpenBabel07101719242D 21 23 0 0 0 0 0 0 0 0999 V2000 -1.4013 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -4.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -4.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -5.6910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -4.1910 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 2 2 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 3 4 1 0 0 0 0 3 7 1 0 0 0 0 4 9 1 0 0 0 0 5 11 2 0 0 0 0 6 13 2 0 0 0 0 7 14 1 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 20 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 15 2 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 19 2 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	281.16
Volume:	296.151
LogP:	1.747
LogD:	1.294
LogS:	-3.122
# Rotatable Bonds:	6
TPSA:	90.58
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.329
Synthetic Accessibility Score:	2.414
Fsp3:	0.25
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:	-5.246
MDCK Permeability:	5.337358743418008e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.926
Human Intestinal Absorption (HIA):	0.358
20% Bioavailability (F20%):	0.952
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.589
Plasma Protein Binding (PPB):	71.82404327392578%
Volume Distribution (VD):	2.092
Pgp-substrate:	23.64244842529297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.514
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.154
CYP2D6-inhibitor:	0.703
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.05
CYP3A4-substrate:	0.121

ADMET: Excretion

Clearance (CL):	9.185
Half-life (T1/2):	0.632

ADMET: Toxicity

hERG Blockers:	0.589
Human Hepatotoxicity (H-HT):	0.825
Drug-inuced Liver Injury (DILI):	0.755
AMES Toxicity:	0.577
Rat Oral Acute Toxicity:	0.959
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.405
Carcinogencity:	0.18
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC470203

Natural Product ID:	NPC470203
*Common Name:**	2-[4-(9H-Pyrido[3,4-B]Indol-1-Yl)Butyl]Guanidine
IUPAC Name:	2-[4-(9H-pyrido[3,4-b]indol-1-yl)butyl]guanidine
Synonyms:
Standard InCHIKey:	DJUXGCPKJDHXCP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H19N5/c17-16(18)20-9-4-3-7-14-15-12(8-10-19-14)11-5-1-2-6-13(11)21-15/h1-2,5-6,8,10,21H,3-4,7,9H2,(H4,17,18,20)
SMILES:	C1=CC=C2C(=C1)C3=C(N2)C(=NC=C3)CCCCN=C(N)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1821997
PubChem CID:	54669866
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO5690	Pseudodistoma opacum	Species	Pseudoceratinidae	Eukaryota	n.a.	New Zealand	n.a.	PMID[21846091]
NPO5690	Pseudodistoma opacum	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21846091]
NPO5690	Pseudodistoma opacum	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26670413]
NPO5690	Pseudodistoma opacum	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	5

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	84000.0	nM	PMID[489688]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	12000.0	nM	PMID[489688]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	110000.0	nM	PMID[489688]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	200000.0	nM	PMID[489688]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	6400.0	nM	PMID[489688]

☑ 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 NPC470203 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	1211
0.1-0.2	14881
0.2-0.3	17772
0.3-0.4	3743
0.4-0.5	1990
0.5-0.6	1597
0.6-0.7	994
0.7-0.8	391
0.8-0.85	73
0.85-0.9	34
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC470204
0.9536	High Similarity	NPC122141
0.9324	High Similarity	NPC469811
0.9262	High Similarity	NPC321911
0.9257	High Similarity	NPC63545
0.9205	High Similarity	NPC325903
0.9195	High Similarity	NPC179787
0.9195	High Similarity	NPC201380
0.9193	High Similarity	NPC307191
0.906	High Similarity	NPC204141
0.9	High Similarity	NPC143872
0.8974	High Similarity	NPC225018
0.8797	High Similarity	NPC317105
0.8782	High Similarity	NPC236711
0.8735	High Similarity	NPC108011
0.8667	High Similarity	NPC115611
0.8667	High Similarity	NPC469784
0.8667	High Similarity	NPC469779
0.8667	High Similarity	NPC469768
0.8667	High Similarity	NPC469767
0.8667	High Similarity	NPC469780
0.8667	High Similarity	NPC469761
0.8667	High Similarity	NPC469783
0.8649	High Similarity	NPC96102
0.8627	High Similarity	NPC288838
0.8609	High Similarity	NPC469766
0.86	High Similarity	NPC73767
0.8591	High Similarity	NPC105127
0.8591	High Similarity	NPC84911
0.8581	High Similarity	NPC53947
0.8535	High Similarity	NPC476219
0.8535	High Similarity	NPC476297
0.8523	High Similarity	NPC261195
0.8523	High Similarity	NPC29886
0.8509	High Similarity	NPC274229
0.8485	Intermediate Similarity	NPC280852
0.8485	Intermediate Similarity	NPC474958
0.8477	Intermediate Similarity	NPC110126
0.8467	Intermediate Similarity	NPC125746
0.8452	Intermediate Similarity	NPC470111
0.8421	Intermediate Similarity	NPC279081
0.8415	Intermediate Similarity	NPC82331
0.8408	Intermediate Similarity	NPC470233
0.84	Intermediate Similarity	NPC325252
0.8378	Intermediate Similarity	NPC82295
0.8354	Intermediate Similarity	NPC97343
0.8333	Intermediate Similarity	NPC198988
0.8333	Intermediate Similarity	NPC247987
0.8323	Intermediate Similarity	NPC314372
0.8313	Intermediate Similarity	NPC216643
0.8312	Intermediate Similarity	NPC190296
0.8301	Intermediate Similarity	NPC230002
0.8282	Intermediate Similarity	NPC17751
0.8282	Intermediate Similarity	NPC280864
0.8261	Intermediate Similarity	NPC135141
0.8261	Intermediate Similarity	NPC56765
0.8261	Intermediate Similarity	NPC92796
0.8235	Intermediate Similarity	NPC88097
0.8232	Intermediate Similarity	NPC49217
0.8228	Intermediate Similarity	NPC24678
0.8228	Intermediate Similarity	NPC105818
0.8225	Intermediate Similarity	NPC16659
0.8214	Intermediate Similarity	NPC473380
0.8214	Intermediate Similarity	NPC240088
0.821	Intermediate Similarity	NPC44773
0.821	Intermediate Similarity	NPC215584
0.8205	Intermediate Similarity	NPC159856
0.8204	Intermediate Similarity	NPC317054
0.8204	Intermediate Similarity	NPC471579
0.8182	Intermediate Similarity	NPC284635
0.8166	Intermediate Similarity	NPC265710
0.8158	Intermediate Similarity	NPC218268
0.8125	Intermediate Similarity	NPC25008
0.8125	Intermediate Similarity	NPC469763
0.8125	Intermediate Similarity	NPC469760
0.8125	Intermediate Similarity	NPC73952
0.8125	Intermediate Similarity	NPC259644
0.8125	Intermediate Similarity	NPC469765
0.8125	Intermediate Similarity	NPC469786
0.8113	Intermediate Similarity	NPC40070
0.811	Intermediate Similarity	NPC90723
0.8101	Intermediate Similarity	NPC471957
0.8086	Intermediate Similarity	NPC286427
0.8075	Intermediate Similarity	NPC212376
0.8075	Intermediate Similarity	NPC70922
0.8075	Intermediate Similarity	NPC211572
0.8075	Intermediate Similarity	NPC75540
0.8075	Intermediate Similarity	NPC80597
0.8065	Intermediate Similarity	NPC2949
0.8065	Intermediate Similarity	NPC59084
0.8037	Intermediate Similarity	NPC41257
0.8037	Intermediate Similarity	NPC318065
0.8037	Intermediate Similarity	NPC206819
0.8025	Intermediate Similarity	NPC469785
0.8013	Intermediate Similarity	NPC63157
0.8013	Intermediate Similarity	NPC473868
0.8012	Intermediate Similarity	NPC200214
0.8	Intermediate Similarity	NPC478182
0.8	Intermediate Similarity	NPC478184
0.7987	Intermediate Similarity	NPC251722
0.7987	Intermediate Similarity	NPC314102
0.7975	Intermediate Similarity	NPC469762
0.7965	Intermediate Similarity	NPC191415
0.7955	Intermediate Similarity	NPC231536
0.795	Intermediate Similarity	NPC216713
0.795	Intermediate Similarity	NPC470823
0.7947	Intermediate Similarity	NPC22079
0.7929	Intermediate Similarity	NPC477611
0.7927	Intermediate Similarity	NPC475990
0.7927	Intermediate Similarity	NPC293487
0.7927	Intermediate Similarity	NPC474880
0.7927	Intermediate Similarity	NPC477591
0.7927	Intermediate Similarity	NPC221786
0.7919	Intermediate Similarity	NPC250361
0.7919	Intermediate Similarity	NPC48938
0.7919	Intermediate Similarity	NPC102755
0.7901	Intermediate Similarity	NPC141926
0.7895	Intermediate Similarity	NPC475450
0.7882	Intermediate Similarity	NPC280297
0.7879	Intermediate Similarity	NPC229173
0.7874	Intermediate Similarity	NPC284678
0.7871	Intermediate Similarity	NPC150259
0.7862	Intermediate Similarity	NPC470440
0.7857	Intermediate Similarity	NPC63751
0.7853	Intermediate Similarity	NPC34844
0.7849	Intermediate Similarity	NPC116555
0.7838	Intermediate Similarity	NPC46358
0.7818	Intermediate Similarity	NPC300238
0.7815	Intermediate Similarity	NPC473762
0.7798	Intermediate Similarity	NPC160105
0.7798	Intermediate Similarity	NPC474561
0.7798	Intermediate Similarity	NPC49954
0.7798	Intermediate Similarity	NPC478183
0.7791	Intermediate Similarity	NPC59269
0.7791	Intermediate Similarity	NPC232798
0.7784	Intermediate Similarity	NPC62749
0.7784	Intermediate Similarity	NPC311276
0.7778	Intermediate Similarity	NPC101165
0.7771	Intermediate Similarity	NPC279918
0.7765	Intermediate Similarity	NPC477166
0.7765	Intermediate Similarity	NPC477167
0.7765	Intermediate Similarity	NPC473342
0.7765	Intermediate Similarity	NPC304187
0.7765	Intermediate Similarity	NPC324149
0.7764	Intermediate Similarity	NPC21605
0.7764	Intermediate Similarity	NPC114209
0.7763	Intermediate Similarity	NPC473587
0.7747	Intermediate Similarity	NPC265576
0.7727	Intermediate Similarity	NPC473930
0.7727	Intermediate Similarity	NPC308931
0.7727	Intermediate Similarity	NPC15102
0.7727	Intermediate Similarity	NPC99939
0.7725	Intermediate Similarity	NPC282231
0.7725	Intermediate Similarity	NPC478185
0.7725	Intermediate Similarity	NPC253687
0.7722	Intermediate Similarity	NPC326422
0.7717	Intermediate Similarity	NPC469308
0.7712	Intermediate Similarity	NPC475428
0.7706	Intermediate Similarity	NPC194411
0.7702	Intermediate Similarity	NPC316069
0.7692	Intermediate Similarity	NPC56233
0.7679	Intermediate Similarity	NPC40779
0.7669	Intermediate Similarity	NPC33421
0.7667	Intermediate Similarity	NPC27740
0.7665	Intermediate Similarity	NPC131718
0.7662	Intermediate Similarity	NPC179365
0.7651	Intermediate Similarity	NPC41174
0.7647	Intermediate Similarity	NPC201700
0.7625	Intermediate Similarity	NPC20144
0.7624	Intermediate Similarity	NPC188821
0.7624	Intermediate Similarity	NPC474180
0.7616	Intermediate Similarity	NPC314603
0.7605	Intermediate Similarity	NPC230869
0.7602	Intermediate Similarity	NPC91895
0.7602	Intermediate Similarity	NPC474897
0.7602	Intermediate Similarity	NPC32534
0.76	Intermediate Similarity	NPC314919
0.7597	Intermediate Similarity	NPC282398
0.7595	Intermediate Similarity	NPC169433
0.7588	Intermediate Similarity	NPC54988
0.7584	Intermediate Similarity	NPC94752
0.7574	Intermediate Similarity	NPC194640
0.7572	Intermediate Similarity	NPC37423
0.7572	Intermediate Similarity	NPC275305
0.7543	Intermediate Similarity	NPC11126
0.754	Intermediate Similarity	NPC317701
0.75	Intermediate Similarity	NPC2272
0.75	Intermediate Similarity	NPC146373
0.75	Intermediate Similarity	NPC166424
0.75	Intermediate Similarity	NPC91958
0.75	Intermediate Similarity	NPC245244
0.7486	Intermediate Similarity	NPC248454
0.7486	Intermediate Similarity	NPC284775
0.7486	Intermediate Similarity	NPC68354
0.7485	Intermediate Similarity	NPC476464
0.7472	Intermediate Similarity	NPC228835
0.7471	Intermediate Similarity	NPC102423
0.7471	Intermediate Similarity	NPC149265
0.7471	Intermediate Similarity	NPC21174
0.7471	Intermediate Similarity	NPC271797

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 NPC470203 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	436
0.1-0.2	918
0.2-0.3	1045
0.3-0.4	2050
0.4-0.5	1908
0.5-0.6	1659
0.6-0.7	850
0.7-0.8	264
0.8-0.85	14
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8859	High Similarity	NPD1722	Approved
0.8727	High Similarity	NPD4649	Clinical (unspecified phase)
0.8727	High Similarity	NPD1895	Discontinued
0.8649	High Similarity	NPD198	Clinical (unspecified phase)
0.8636	High Similarity	NPD4374	Clinical (unspecified phase)
0.86	High Similarity	NPD786	Approved
0.859	High Similarity	NPD2837	Discontinued
0.8494	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD4181	Approved
0.8431	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD3100	Discontinued
0.8383	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD4128	Approved
0.8228	Intermediate Similarity	NPD2172	Phase 1
0.8221	Intermediate Similarity	NPD3323	Discontinued
0.8194	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD1313	Approved
0.816	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD2478	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD2793	Discontinued
0.8092	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD6828	Phase 2
0.8084	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD2333	Discontinued
0.807	Intermediate Similarity	NPD1707	Approved
0.807	Intermediate Similarity	NPD1708	Approved
0.8057	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD2150	Discontinued
0.8025	Intermediate Similarity	NPD2927	Phase 3
0.8023	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5962	Phase 2
0.8	Intermediate Similarity	NPD7111	Discontinued
0.7989	Intermediate Similarity	NPD2880	Discontinued
0.7987	Intermediate Similarity	NPD1262	Discovery
0.7987	Intermediate Similarity	NPD4547	Phase 3
0.7964	Intermediate Similarity	NPD2641	Approved
0.7964	Intermediate Similarity	NPD2640	Approved
0.7962	Intermediate Similarity	NPD2006	Phase 2
0.7949	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD715	Phase 3
0.7937	Intermediate Similarity	NPD2430	Phase 2
0.7933	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD3419	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD1248	Discontinued
0.7882	Intermediate Similarity	NPD5065	Approved
0.787	Intermediate Similarity	NPD3609	Approved
0.787	Intermediate Similarity	NPD3610	Approved
0.7867	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD991	Phase 2
0.7857	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD975	Approved
0.7853	Intermediate Similarity	NPD976	Approved
0.7853	Intermediate Similarity	NPD977	Approved
0.7844	Intermediate Similarity	NPD1333	Phase 3
0.7831	Intermediate Similarity	NPD1016	Phase 2
0.7831	Intermediate Similarity	NPD1015	Phase 2
0.7829	Intermediate Similarity	NPD3476	Approved
0.7829	Intermediate Similarity	NPD3475	Approved
0.7812	Intermediate Similarity	NPD1683	Approved
0.7803	Intermediate Similarity	NPD6595	Phase 3
0.7799	Intermediate Similarity	NPD5254	Discontinued
0.7799	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3385	Approved
0.7784	Intermediate Similarity	NPD4902	Discontinued
0.7784	Intermediate Similarity	NPD706	Phase 1
0.7778	Intermediate Similarity	NPD1029	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1030	Approved
0.7778	Intermediate Similarity	NPD1027	Approved
0.7771	Intermediate Similarity	NPD1403	Approved
0.7771	Intermediate Similarity	NPD1404	Approved
0.7765	Intermediate Similarity	NPD4615	Phase 2
0.7758	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD2443	Approved
0.7754	Intermediate Similarity	NPD2442	Approved
0.7748	Intermediate Similarity	NPD2119	Approved
0.7748	Intermediate Similarity	NPD2118	Approved
0.7746	Intermediate Similarity	NPD5730	Phase 2
0.7746	Intermediate Similarity	NPD1327	Discontinued
0.7746	Intermediate Similarity	NPD40	Phase 2
0.7742	Intermediate Similarity	NPD2008	Discontinued
0.7742	Intermediate Similarity	NPD4023	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD2316	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2868	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD4318	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD5436	Phase 1
0.7706	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5462	Discontinued
0.7692	Intermediate Similarity	NPD2639	Approved
0.7692	Intermediate Similarity	NPD2642	Approved
0.7684	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD3015	Discontinued
0.7669	Intermediate Similarity	NPD4463	Approved
0.7669	Intermediate Similarity	NPD4462	Approved
0.7662	Intermediate Similarity	NPD809	Discontinued
0.7662	Intermediate Similarity	NPD803	Phase 1
0.7657	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD509	Phase 3
0.7632	Intermediate Similarity	NPD1598	Discontinued
0.7625	Intermediate Similarity	NPD4047	Discontinued
0.7619	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD5418	Discontinued
0.76	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD3830	Phase 1
0.7592	Intermediate Similarity	NPD2411	Approved
0.759	Intermediate Similarity	NPD2580	Discontinued
0.759	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6721	Phase 1
0.7576	Intermediate Similarity	NPD1303	Phase 1
0.7576	Intermediate Similarity	NPD1917	Discontinued
0.7564	Intermediate Similarity	NPD4029	Approved
0.7564	Intermediate Similarity	NPD4030	Approved
0.7564	Intermediate Similarity	NPD4028	Approved
0.7558	Intermediate Similarity	NPD3347	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1661	Suspended
0.7545	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7394	Phase 2
0.7542	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD2364	Suspended
0.7532	Intermediate Similarity	NPD3654	Approved
0.753	Intermediate Similarity	NPD2165	Phase 1
0.7529	Intermediate Similarity	NPD4075	Phase 2
0.7528	Intermediate Similarity	NPD4298	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD2408	Discontinued
0.7516	Intermediate Similarity	NPD2140	Approved
0.7516	Intermediate Similarity	NPD2141	Approved
0.7516	Intermediate Similarity	NPD2142	Approved
0.7513	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6664	Approved
0.7486	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7618	Phase 3
0.7486	Intermediate Similarity	NPD7619	Phase 3
0.7486	Intermediate Similarity	NPD3506	Approved
0.7486	Intermediate Similarity	NPD3505	Approved
0.7485	Intermediate Similarity	NPD3114	Approved
0.7485	Intermediate Similarity	NPD3112	Approved
0.7485	Intermediate Similarity	NPD3113	Approved
0.7485	Intermediate Similarity	NPD3115	Approved
0.7485	Intermediate Similarity	NPD2392	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6816	Phase 3
0.7472	Intermediate Similarity	NPD5892	Approved
0.7471	Intermediate Similarity	NPD3799	Suspended
0.747	Intermediate Similarity	NPD695	Discontinued
0.7459	Intermediate Similarity	NPD2818	Discontinued
0.7459	Intermediate Similarity	NPD6468	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6469	Phase 3
0.7452	Intermediate Similarity	NPD3942	Approved
0.7452	Intermediate Similarity	NPD3944	Approved
0.7444	Intermediate Similarity	NPD3961	Discontinued
0.7444	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD1893	Phase 2
0.7443	Intermediate Similarity	NPD1892	Phase 2
0.7443	Intermediate Similarity	NPD8386	Phase 2
0.7443	Intermediate Similarity	NPD4076	Approved
0.7443	Intermediate Similarity	NPD4079	Approved
0.744	Intermediate Similarity	NPD5300	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2445	Approved
0.7432	Intermediate Similarity	NPD2446	Approved
0.7427	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD45	Approved
0.7421	Intermediate Similarity	NPD6554	Approved
0.7416	Intermediate Similarity	NPD5106	Approved
0.7416	Intermediate Similarity	NPD5105	Approved
0.7416	Intermediate Similarity	NPD4441	Phase 2
0.7412	Intermediate Similarity	NPD8026	Phase 1
0.741	Intermediate Similarity	NPD1257	Approved
0.7403	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4024	Phase 3
0.7396	Intermediate Similarity	NPD1042	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7026	Phase 2
0.7389	Intermediate Similarity	NPD5642	Approved
0.7389	Intermediate Similarity	NPD2591	Phase 2
0.7386	Intermediate Similarity	NPD2144	Approved
0.7384	Intermediate Similarity	NPD6794	Approved
0.7384	Intermediate Similarity	NPD1215	Discontinued
0.7381	Intermediate Similarity	NPD1290	Phase 2
0.7381	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD3431	Approved
0.7377	Intermediate Similarity	NPD3430	Approved
0.7366	Intermediate Similarity	NPD1982	Phase 1
0.7351	Intermediate Similarity	NPD9598	Discontinued
0.7351	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2466	Phase 3
0.7349	Intermediate Similarity	NPD2462	Phase 3
0.7349	Intermediate Similarity	NPD2465	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