NPASS Compound

Structure

NPC211572 OpenBabel07101718302D 35 36 0 0 0 0 0 0 0 0999 V2000 2.3651 22.3643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6741 21.4132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0050 20.6701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3140 19.7190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6448 18.9759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9539 18.0248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2847 17.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5937 16.3306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9246 15.5875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2336 14.6364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5645 13.8933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8735 12.9422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2044 12.1991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5134 11.2480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1557 10.5049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1533 9.5538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5158 8.8107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2068 7.8596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8760 7.1165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5669 6.1654 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 2.6831 0.3090 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 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2361 5.4223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 2.7770 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 -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 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 4.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 3.7281 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 0.0511 4.2633 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 25 1 0 0 0 0 21 22 2 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 30 2 0 0 0 0 24 31 2 0 0 0 0 25 32 1 0 0 0 0 26 27 1 0 0 0 0 26 29 1 0 0 0 0 27 33 1 0 0 0 0 28 29 2 0 0 0 0 28 34 1 0 0 0 0 29 30 1 0 0 0 0 30 31 1 0 0 0 0 31 34 1 0 0 0 0 32 33 2 3 0 0 0 32 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.42
Volume:	562.517
LogP:	10.449
LogD:	5.233
LogS:	-3.69
# Rotatable Bonds:	24
TPSA:	44.89
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.152
Synthetic Accessibility Score:	2.239
Fsp3:	0.719
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.333
MDCK Permeability:	5.896070433664136e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.108
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	99.66924285888672%
Volume Distribution (VD):	3.875
Pgp-substrate:	0.6412999033927917%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.282
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.087
CYP2C9-substrate:	0.978
CYP2D6-inhibitor:	0.779
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.52
CYP3A4-substrate:	0.058

ADMET: Excretion

Clearance (CL):	4.468
Half-life (T1/2):	0.135

ADMET: Toxicity

hERG Blockers:	0.924
Human Hepatotoxicity (H-HT):	0.351
Drug-inuced Liver Injury (DILI):	0.295
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.338
Skin Sensitization:	0.973
Carcinogencity:	0.029
Eye Corrosion:	0.004
Eye Irritation:	0.167
Respiratory Toxicity:	0.847

Download Data

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

Natural Product: NPC211572

Natural Product ID:	NPC211572
*Common Name:**	N-Behenoyltryptamine
IUPAC Name:	N-[2-(1H-indol-3-yl)ethyl]docosanamide
Synonyms:	N-Behenoyltryptamine
Standard InCHIKey:	HAWFHRQOMIMGFR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H54N2O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25-32(35)33-27-26-29-28-34-31-24-22-21-23-30(29)31/h21-24,28,34H,2-20,25-27H2,1H3,(H,33,35)
SMILES:	CCCCCCCCCCCCCCCCCCCCCC(=NCCc1c[nH]c2ccccc12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490312
PubChem CID:	10311044
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
NPO32731	rollinia mucosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10479316]

☑ 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	6
Others	1

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[474642]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[474642]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[474642]
NPT306	Cell Line	PC-3	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[474642]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[474642]
NPT176	Organism	Artemia salina	Artemia salina	LC50	>	500.0	ug.mL-1	PMID[474642]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	10.0	ug ml-1	PMID[474642]

☑ 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 NPC211572 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	360
0.1-0.2	3461
0.2-0.3	19625
0.3-0.4	12166
0.4-0.5	2963
0.5-0.6	1995
0.6-0.7	1253
0.7-0.8	654
0.8-0.85	130
0.85-0.9	48
0.9-0.95	26
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC70922
1.0	High Similarity	NPC75540
1.0	High Similarity	NPC80597
1.0	High Similarity	NPC212376
0.993	High Similarity	NPC469763
0.993	High Similarity	NPC259644
0.993	High Similarity	NPC469760
0.993	High Similarity	NPC469786
0.993	High Similarity	NPC73952
0.993	High Similarity	NPC469765
0.993	High Similarity	NPC25008
0.9658	High Similarity	NPC469785
0.9592	High Similarity	NPC469762
0.951	High Similarity	NPC314372
0.9467	High Similarity	NPC311276
0.9384	High Similarity	NPC105818
0.9384	High Similarity	NPC24678
0.9371	High Similarity	NPC190296
0.9342	High Similarity	NPC160105
0.9301	High Similarity	NPC469766
0.9231	High Similarity	NPC469783
0.9231	High Similarity	NPC469784
0.9231	High Similarity	NPC469761
0.9231	High Similarity	NPC469780
0.9231	High Similarity	NPC469768
0.9231	High Similarity	NPC469779
0.9231	High Similarity	NPC469767
0.9226	High Similarity	NPC314603
0.9216	High Similarity	NPC474561
0.9216	High Similarity	NPC49954
0.9211	High Similarity	NPC40779
0.9156	High Similarity	NPC201700
0.9145	High Similarity	NPC282231
0.911	High Similarity	NPC159856
0.9079	High Similarity	NPC279918
0.9079	High Similarity	NPC131718
0.9032	High Similarity	NPC63751
0.9028	High Similarity	NPC73767
0.9021	High Similarity	NPC84911
0.9013	High Similarity	NPC230869
0.8986	High Similarity	NPC471957
0.8961	High Similarity	NPC194640
0.8951	High Similarity	NPC96102
0.8951	High Similarity	NPC261195
0.8951	High Similarity	NPC29886
0.8897	High Similarity	NPC110126
0.8889	High Similarity	NPC105127
0.8846	High Similarity	NPC54988
0.8839	High Similarity	NPC102423
0.8812	High Similarity	NPC248454
0.8766	High Similarity	NPC92796
0.8766	High Similarity	NPC135141
0.8742	High Similarity	NPC313791
0.8707	High Similarity	NPC279081
0.8704	High Similarity	NPC300688
0.8696	High Similarity	NPC59269
0.8696	High Similarity	NPC151939
0.8684	High Similarity	NPC216713
0.8671	High Similarity	NPC78020
0.8671	High Similarity	NPC82295
0.865	High Similarity	NPC233936
0.8642	High Similarity	NPC213468
0.8634	High Similarity	NPC267885
0.8627	High Similarity	NPC200214
0.8618	High Similarity	NPC53947
0.8616	High Similarity	NPC194411
0.8598	High Similarity	NPC163055
0.8581	High Similarity	NPC230002
0.8571	High Similarity	NPC110500
0.8571	High Similarity	NPC203468
0.8571	High Similarity	NPC149155
0.8554	High Similarity	NPC94752
0.8543	High Similarity	NPC288838
0.8528	High Similarity	NPC248041
0.8528	High Similarity	NPC126709
0.8516	High Similarity	NPC285469
0.8494	Intermediate Similarity	NPC280290
0.8462	Intermediate Similarity	NPC129721
0.8457	Intermediate Similarity	NPC275305
0.8457	Intermediate Similarity	NPC37423
0.8452	Intermediate Similarity	NPC213629
0.8443	Intermediate Similarity	NPC474707
0.8443	Intermediate Similarity	NPC235684
0.8431	Intermediate Similarity	NPC321911
0.8421	Intermediate Similarity	NPC143872
0.8415	Intermediate Similarity	NPC283219
0.8393	Intermediate Similarity	NPC317030
0.8383	Intermediate Similarity	NPC15102
0.8375	Intermediate Similarity	NPC49217
0.8366	Intermediate Similarity	NPC201380
0.8366	Intermediate Similarity	NPC469811
0.8366	Intermediate Similarity	NPC179787
0.8354	Intermediate Similarity	NPC111275
0.8354	Intermediate Similarity	NPC14113
0.8354	Intermediate Similarity	NPC68354
0.8354	Intermediate Similarity	NPC84827
0.8354	Intermediate Similarity	NPC145885
0.8344	Intermediate Similarity	NPC286427
0.8343	Intermediate Similarity	NPC173028
0.8343	Intermediate Similarity	NPC65215
0.8333	Intermediate Similarity	NPC470498
0.8333	Intermediate Similarity	NPC171171
0.8323	Intermediate Similarity	NPC228835
0.8323	Intermediate Similarity	NPC204717
0.8323	Intermediate Similarity	NPC470823
0.8314	Intermediate Similarity	NPC157828
0.8314	Intermediate Similarity	NPC195239
0.8313	Intermediate Similarity	NPC71037
0.8312	Intermediate Similarity	NPC37548
0.8303	Intermediate Similarity	NPC176199
0.8303	Intermediate Similarity	NPC215795
0.8303	Intermediate Similarity	NPC55772
0.8302	Intermediate Similarity	NPC16667
0.8301	Intermediate Similarity	NPC63545
0.8294	Intermediate Similarity	NPC95783
0.8291	Intermediate Similarity	NPC206819
0.8291	Intermediate Similarity	NPC56765
0.8291	Intermediate Similarity	NPC318065
0.8291	Intermediate Similarity	NPC41257
0.8284	Intermediate Similarity	NPC204565
0.8274	Intermediate Similarity	NPC188387
0.8274	Intermediate Similarity	NPC163421
0.8274	Intermediate Similarity	NPC314002
0.8269	Intermediate Similarity	NPC325903
0.8269	Intermediate Similarity	NPC141926
0.8266	Intermediate Similarity	NPC11445
0.8263	Intermediate Similarity	NPC220765
0.8255	Intermediate Similarity	NPC150259
0.8235	Intermediate Similarity	NPC321708
0.8228	Intermediate Similarity	NPC216643
0.8219	Intermediate Similarity	NPC22079
0.8217	Intermediate Similarity	NPC207726
0.8217	Intermediate Similarity	NPC34844
0.8214	Intermediate Similarity	NPC165495
0.8205	Intermediate Similarity	NPC470233
0.8193	Intermediate Similarity	NPC11126
0.8188	Intermediate Similarity	NPC325252
0.8188	Intermediate Similarity	NPC218268
0.8176	Intermediate Similarity	NPC67056
0.8171	Intermediate Similarity	NPC171317
0.8171	Intermediate Similarity	NPC473640
0.817	Intermediate Similarity	NPC242556
0.8165	Intermediate Similarity	NPC141353
0.816	Intermediate Similarity	NPC280548
0.8155	Intermediate Similarity	NPC469358
0.8155	Intermediate Similarity	NPC48938
0.815	Intermediate Similarity	NPC474177
0.8148	Intermediate Similarity	NPC109447
0.8137	Intermediate Similarity	NPC90723
0.8125	Intermediate Similarity	NPC100321
0.8121	Intermediate Similarity	NPC198988
0.8113	Intermediate Similarity	NPC236711
0.8103	Intermediate Similarity	NPC133366
0.8101	Intermediate Similarity	NPC38736
0.8101	Intermediate Similarity	NPC470507
0.8098	Intermediate Similarity	NPC317430
0.8092	Intermediate Similarity	NPC477167
0.8092	Intermediate Similarity	NPC473342
0.8092	Intermediate Similarity	NPC59084
0.8092	Intermediate Similarity	NPC99666
0.8092	Intermediate Similarity	NPC2949
0.8077	Intermediate Similarity	NPC187951
0.8075	Intermediate Similarity	NPC470203
0.807	Intermediate Similarity	NPC17059
0.807	Intermediate Similarity	NPC46580
0.8068	Intermediate Similarity	NPC265576
0.8061	Intermediate Similarity	NPC472123
0.8042	Intermediate Similarity	NPC41174
0.8041	Intermediate Similarity	NPC475450
0.8039	Intermediate Similarity	NPC63157
0.8039	Intermediate Similarity	NPC473868
0.8034	Intermediate Similarity	NPC475506
0.8024	Intermediate Similarity	NPC184964
0.8023	Intermediate Similarity	NPC293917
0.8014	Intermediate Similarity	NPC471311
0.8014	Intermediate Similarity	NPC471313
0.8012	Intermediate Similarity	NPC62749
0.8012	Intermediate Similarity	NPC44773
0.8012	Intermediate Similarity	NPC189812
0.8012	Intermediate Similarity	NPC329688
0.8012	Intermediate Similarity	NPC215584
0.8012	Intermediate Similarity	NPC315555
0.8012	Intermediate Similarity	NPC470204
0.8011	Intermediate Similarity	NPC227582
0.8	Intermediate Similarity	NPC470440
0.7989	Intermediate Similarity	NPC324149
0.7989	Intermediate Similarity	NPC476874
0.7989	Intermediate Similarity	NPC193761
0.7989	Intermediate Similarity	NPC155143
0.7978	Intermediate Similarity	NPC252338
0.7975	Intermediate Similarity	NPC470508
0.7966	Intermediate Similarity	NPC470499
0.7962	Intermediate Similarity	NPC124005
0.7952	Intermediate Similarity	NPC34508
0.7949	Intermediate Similarity	NPC316069
0.7945	Intermediate Similarity	NPC250361
0.7944	Intermediate Similarity	NPC98715
0.7943	Intermediate Similarity	NPC307963
0.7933	Intermediate Similarity	NPC300183
0.7929	Intermediate Similarity	NPC16659

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 NPC211572 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	605
0.2-0.3	1019
0.3-0.4	1487
0.4-0.5	2650
0.5-0.6	1966
0.6-0.7	946
0.7-0.8	241
0.8-0.85	29
0.85-0.9	9
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9097	High Similarity	NPD4184	Clinical (unspecified phase)
0.9028	High Similarity	NPD786	Approved
0.8951	High Similarity	NPD198	Clinical (unspecified phase)
0.8805	High Similarity	NPD5065	Approved
0.8776	High Similarity	NPD1722	Approved
0.8704	High Similarity	NPD6595	Phase 3
0.8696	High Similarity	NPD2144	Approved
0.8675	High Similarity	NPD3100	Discontinued
0.8634	High Similarity	NPD749	Clinical (unspecified phase)
0.8618	High Similarity	NPD2172	Phase 1
0.8614	High Similarity	NPD8431	Approved
0.8598	High Similarity	NPD5728	Clinical (unspecified phase)
0.8571	High Similarity	NPD482	Approved
0.8563	High Similarity	NPD8110	Clinical (unspecified phase)
0.8553	High Similarity	NPD4374	Clinical (unspecified phase)
0.8537	High Similarity	NPD3038	Discontinued
0.8494	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD2094	Phase 2
0.8485	Intermediate Similarity	NPD2092	Phase 2
0.8485	Intermediate Similarity	NPD2095	Phase 2
0.8466	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD2091	Phase 2
0.8434	Intermediate Similarity	NPD2096	Phase 2
0.8415	Intermediate Similarity	NPD4079	Approved
0.8415	Intermediate Similarity	NPD4076	Approved
0.8377	Intermediate Similarity	NPD4462	Approved
0.8377	Intermediate Similarity	NPD4463	Approved
0.8354	Intermediate Similarity	NPD3505	Approved
0.8354	Intermediate Similarity	NPD3506	Approved
0.8282	Intermediate Similarity	NPD750	Phase 2
0.8269	Intermediate Similarity	NPD2837	Discontinued
0.8247	Intermediate Similarity	NPD4702	Approved
0.8247	Intermediate Similarity	NPD4703	Approved
0.8239	Intermediate Similarity	NPD1403	Approved
0.8239	Intermediate Similarity	NPD1404	Approved
0.8232	Intermediate Similarity	NPD4128	Approved
0.816	Intermediate Similarity	NPD1325	Approved
0.816	Intermediate Similarity	NPD1326	Approved
0.8158	Intermediate Similarity	NPD1592	Phase 3
0.8148	Intermediate Similarity	NPD2642	Approved
0.8148	Intermediate Similarity	NPD2639	Approved
0.8137	Intermediate Similarity	NPD3323	Discontinued
0.8133	Intermediate Similarity	NPD4181	Approved
0.8114	Intermediate Similarity	NPD7948	Phase 1
0.8098	Intermediate Similarity	NPD2641	Approved
0.8098	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD2640	Approved
0.8092	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD4075	Phase 2
0.8072	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD8073	Approved
0.7987	Intermediate Similarity	NPD3717	Discontinued
0.7976	Intermediate Similarity	NPD8386	Phase 2
0.7944	Intermediate Similarity	NPD8072	Approved
0.7943	Intermediate Similarity	NPD1038	Approved
0.7935	Intermediate Similarity	NPD5254	Discontinued
0.7914	Intermediate Similarity	NPD5138	Approved
0.7914	Intermediate Similarity	NPD5140	Approved
0.7905	Intermediate Similarity	NPD3654	Approved
0.7901	Intermediate Similarity	NPD8272	Phase 2
0.7892	Intermediate Similarity	NPD3610	Approved
0.7892	Intermediate Similarity	NPD3609	Approved
0.7879	Intermediate Similarity	NPD4638	Approved
0.7879	Intermediate Similarity	NPD4640	Approved
0.7879	Intermediate Similarity	NPD4639	Approved
0.7871	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD3961	Discontinued
0.7857	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7957	Phase 1
0.7853	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD3476	Approved
0.7852	Intermediate Similarity	NPD3475	Approved
0.7841	Intermediate Similarity	NPD802	Phase 2
0.7814	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7618	Phase 3
0.7797	Intermediate Similarity	NPD7619	Phase 3
0.7791	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1661	Suspended
0.7785	Intermediate Similarity	NPD4547	Phase 3
0.7784	Intermediate Similarity	NPD3404	Approved
0.7772	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD991	Phase 2
0.777	Intermediate Similarity	NPD2119	Approved
0.777	Intermediate Similarity	NPD2118	Approved
0.7756	Intermediate Similarity	NPD2006	Phase 2
0.7744	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD8026	Phase 1
0.774	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2430	Phase 2
0.7716	Intermediate Similarity	NPD2580	Discontinued
0.7702	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6217	Discontinued
0.7697	Intermediate Similarity	NPD3385	Approved
0.7688	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD5021	Discontinued
0.7657	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD5106	Approved
0.763	Intermediate Similarity	NPD5105	Approved
0.7622	Intermediate Similarity	NPD5255	Approved
0.7622	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD6664	Approved
0.761	Intermediate Similarity	NPD1683	Approved
0.761	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD5901	Discontinued
0.7609	Intermediate Similarity	NPD5426	Phase 3
0.7606	Intermediate Similarity	NPD8093	Discontinued
0.7606	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD8129	Discovery
0.7582	Intermediate Similarity	NPD484	Approved
0.7582	Intermediate Similarity	NPD4029	Approved
0.7582	Intermediate Similarity	NPD4030	Approved
0.7582	Intermediate Similarity	NPD4028	Approved
0.7574	Intermediate Similarity	NPD3117	Approved
0.7574	Intermediate Similarity	NPD3116	Approved
0.7568	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD8094	Discontinued
0.7561	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD7470	Discontinued
0.7548	Intermediate Similarity	NPD1262	Discovery
0.7546	Intermediate Similarity	NPD2165	Phase 1
0.7541	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2882	Phase 1
0.7531	Intermediate Similarity	NPD6158	Phase 2
0.7531	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8122	Approved
0.75	Intermediate Similarity	NPD3113	Approved
0.75	Intermediate Similarity	NPD7469	Discontinued
0.75	Intermediate Similarity	NPD8123	Approved
0.75	Intermediate Similarity	NPD1248	Discontinued
0.75	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2896	Discontinued
0.75	Intermediate Similarity	NPD3115	Approved
0.75	Intermediate Similarity	NPD3112	Approved
0.75	Intermediate Similarity	NPD7944	Discontinued
0.75	Intermediate Similarity	NPD3114	Approved
0.7486	Intermediate Similarity	NPD4615	Phase 2
0.7486	Intermediate Similarity	NPD6178	Phase 3
0.7486	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2928	Phase 2
0.7471	Intermediate Similarity	NPD1707	Approved
0.7471	Intermediate Similarity	NPD1708	Approved
0.7469	Intermediate Similarity	NPD3833	Phase 3
0.7469	Intermediate Similarity	NPD3835	Phase 3
0.7468	Intermediate Similarity	NPD3942	Approved
0.7468	Intermediate Similarity	NPD3944	Approved
0.7467	Intermediate Similarity	NPD9583	Approved
0.7459	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2844	Phase 3
0.7456	Intermediate Similarity	NPD5862	Discovery
0.7456	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5100	Phase 3
0.7432	Intermediate Similarity	NPD3825	Phase 3
0.743	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD5315	Discontinued
0.7423	Intermediate Similarity	NPD3262	Approved
0.7412	Intermediate Similarity	NPD5436	Phase 1
0.7409	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD706	Phase 1
0.7396	Intermediate Similarity	NPD5611	Phase 2
0.7394	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3813	Approved
0.7374	Intermediate Similarity	NPD6281	Approved
0.7371	Intermediate Similarity	NPD1895	Discontinued
0.7371	Intermediate Similarity	NPD3178	Discontinued
0.7368	Intermediate Similarity	NPD5066	Phase 2
0.7368	Intermediate Similarity	NPD5067	Phase 2
0.7368	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD271	Approved
0.7365	Intermediate Similarity	NPD268	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