NPASS Compound

Structure

NPC469785 OpenBabel07101719252D 28 29 0 0 0 0 0 0 0 0999 V2000 -3.3967 -4.7429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7276 -3.9998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0877 -5.6940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0366 -3.0487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7569 -6.4371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3675 -2.3056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4478 -7.3882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6765 -1.3545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1170 -8.1314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0074 -0.6114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8080 -9.0824 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 -2.3164 0.3397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4771 -9.8256 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 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 1.0828 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 -4.1681 -10.7766 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 -1.9563 2.0339 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 -4.8372 -11.5198 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 13 2 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 19 1 0 0 0 0 15 21 1 0 0 0 0 16 24 2 0 0 0 0 17 25 2 0 0 0 0 18 20 1 0 0 0 0 18 23 1 0 0 0 0 19 26 1 0 0 0 0 20 26 1 0 0 0 0 21 28 1 0 0 0 0 22 23 2 0 0 0 0 22 27 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 25 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.33
Volume:	444.081
LogP:	6.363
LogD:	4.099
LogS:	-3.719
# Rotatable Bonds:	18
TPSA:	48.05
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.261
Synthetic Accessibility Score:	2.159
Fsp3:	0.68
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.168
MDCK Permeability:	1.3959145690023433e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.954
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.884

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.332
Plasma Protein Binding (PPB):	94.0123062133789%
Volume Distribution (VD):	2.094
Pgp-substrate:	1.885835886001587%

ADMET: Metabolism

CYP1A2-inhibitor:	0.405
CYP1A2-substrate:	0.243
CYP2C19-inhibitor:	0.529
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	0.644
CYP2D6-inhibitor:	0.983
CYP2D6-substrate:	0.814
CYP3A4-inhibitor:	0.84
CYP3A4-substrate:	0.156

ADMET: Excretion

Clearance (CL):	5.421
Half-life (T1/2):	0.179

ADMET: Toxicity

hERG Blockers:	0.83
Human Hepatotoxicity (H-HT):	0.713
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.456
Maximum Recommended Daily Dose:	0.764
Skin Sensitization:	0.971
Carcinogencity:	0.021
Eye Corrosion:	0.029
Eye Irritation:	0.214
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC469785

Natural Product ID:	NPC469785
*Common Name:**	15-[2-(1H-Indol-3-Yl)Ethylamino]Pentadecan-1-Ol
IUPAC Name:	15-[2-(1H-indol-3-yl)ethylamino]pentadecan-1-ol
Synonyms:
Standard InCHIKey:	UVEDAHXNGZHHLW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H42N2O/c28-21-15-11-9-7-5-3-1-2-4-6-8-10-14-19-26-20-18-23-22-27-25-17-13-12-16-24(23)25/h12-13,16-17,22,26-28H,1-11,14-15,18-21H2
SMILES:	OCCCCCCCCCCCCCCCNCCc1c[nH]c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1171492
PubChem CID:	46897304
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000183] Tryptamines and derivatives

*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
NPO31161	Annonaceae	Genus	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20579892]
NPO31161	Annonaceae	Genus	Annonaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23513739]
NPO31161	Annonaceae	Genus	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26920282]

☑ 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	1
Others	3

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4564	Cell Line	Neurons		Activity	=	129.4	%	PMID[558456]
NPT4564	Cell Line	Neurons		Activity	=	160.8	%	PMID[558456]
NPT4564	Cell Line	Neurons		Activity	=	43.7	%	PMID[558456]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	730000.0	nM	PMID[558456]

☑ 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 NPC469785 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	334
0.1-0.2	2949
0.2-0.3	19178
0.3-0.4	13030
0.4-0.5	3058
0.5-0.6	2036
0.6-0.7	1305
0.7-0.8	610
0.8-0.85	116
0.85-0.9	55
0.9-0.95	11
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC469762
0.9724	High Similarity	NPC469760
0.9724	High Similarity	NPC469763
0.9724	High Similarity	NPC469765
0.9724	High Similarity	NPC25008
0.9724	High Similarity	NPC259644
0.9724	High Similarity	NPC469786
0.9724	High Similarity	NPC73952
0.9658	High Similarity	NPC75540
0.9658	High Similarity	NPC70922
0.9658	High Similarity	NPC212376
0.9658	High Similarity	NPC80597
0.9658	High Similarity	NPC211572
0.9533	High Similarity	NPC311276
0.9404	High Similarity	NPC40779
0.9346	High Similarity	NPC201700
0.9333	High Similarity	NPC230869
0.931	High Similarity	NPC314372
0.9189	High Similarity	NPC24678
0.9189	High Similarity	NPC105818
0.9172	High Similarity	NPC190296
0.9156	High Similarity	NPC54988
0.9156	High Similarity	NPC160105
0.915	High Similarity	NPC102423
0.9048	High Similarity	NPC159856
0.9034	High Similarity	NPC469768
0.9034	High Similarity	NPC469761
0.9034	High Similarity	NPC469779
0.9034	High Similarity	NPC469783
0.9034	High Similarity	NPC469784
0.9034	High Similarity	NPC469780
0.9034	High Similarity	NPC469767
0.9032	High Similarity	NPC474561
0.9032	High Similarity	NPC49954
0.902	High Similarity	NPC131718
0.902	High Similarity	NPC279918
0.8974	High Similarity	NPC63751
0.8973	High Similarity	NPC469766
0.8961	High Similarity	NPC282231
0.8924	High Similarity	NPC314603
0.8924	High Similarity	NPC313791
0.8889	High Similarity	NPC96102
0.8882	High Similarity	NPC300688
0.8875	High Similarity	NPC151939
0.8836	High Similarity	NPC73767
0.8828	High Similarity	NPC84911
0.8828	High Similarity	NPC105127
0.8827	High Similarity	NPC233936
0.88	High Similarity	NPC471957
0.8782	High Similarity	NPC194640
0.8773	High Similarity	NPC163055
0.8759	High Similarity	NPC261195
0.8759	High Similarity	NPC29886
0.871	High Similarity	NPC135141
0.871	High Similarity	NPC92796
0.8707	High Similarity	NPC110126
0.8649	High Similarity	NPC279081
0.8642	High Similarity	NPC248454
0.8642	High Similarity	NPC59269
0.8634	High Similarity	NPC275305
0.8634	High Similarity	NPC37423
0.8627	High Similarity	NPC216713
0.8616	High Similarity	NPC78020
0.8614	High Similarity	NPC474707
0.8611	High Similarity	NPC82295
0.8598	High Similarity	NPC71037
0.8563	High Similarity	NPC317030
0.8528	High Similarity	NPC68354
0.8523	High Similarity	NPC230002
0.8519	High Similarity	NPC149155
0.8519	High Similarity	NPC110500
0.8519	High Similarity	NPC203468
0.8512	High Similarity	NPC173028
0.8512	High Similarity	NPC65215
0.8509	High Similarity	NPC470498
0.8487	Intermediate Similarity	NPC288838
0.8476	Intermediate Similarity	NPC176199
0.8476	Intermediate Similarity	NPC213468
0.8476	Intermediate Similarity	NPC215795
0.8466	Intermediate Similarity	NPC267885
0.8462	Intermediate Similarity	NPC95783
0.8452	Intermediate Similarity	NPC204565
0.8452	Intermediate Similarity	NPC200214
0.8447	Intermediate Similarity	NPC194411
0.8442	Intermediate Similarity	NPC53947
0.8434	Intermediate Similarity	NPC48938
0.8393	Intermediate Similarity	NPC94752
0.8385	Intermediate Similarity	NPC317430
0.8366	Intermediate Similarity	NPC143872
0.8364	Intermediate Similarity	NPC126709
0.8364	Intermediate Similarity	NPC248041
0.8364	Intermediate Similarity	NPC283219
0.8344	Intermediate Similarity	NPC285469
0.8333	Intermediate Similarity	NPC15102
0.8333	Intermediate Similarity	NPC188387
0.8333	Intermediate Similarity	NPC280290
0.8333	Intermediate Similarity	NPC163421
0.8323	Intermediate Similarity	NPC469358
0.8314	Intermediate Similarity	NPC474177
0.8312	Intermediate Similarity	NPC469811
0.8303	Intermediate Similarity	NPC111275
0.8294	Intermediate Similarity	NPC213629
0.8291	Intermediate Similarity	NPC129721
0.8284	Intermediate Similarity	NPC315555
0.8284	Intermediate Similarity	NPC235684
0.828	Intermediate Similarity	NPC470507
0.8266	Intermediate Similarity	NPC133366
0.8258	Intermediate Similarity	NPC321911
0.8253	Intermediate Similarity	NPC55772
0.8247	Intermediate Similarity	NPC63545
0.8232	Intermediate Similarity	NPC472123
0.8229	Intermediate Similarity	NPC473640
0.8217	Intermediate Similarity	NPC325903
0.8214	Intermediate Similarity	NPC220765
0.821	Intermediate Similarity	NPC49217
0.8194	Intermediate Similarity	NPC201380
0.8194	Intermediate Similarity	NPC179787
0.8193	Intermediate Similarity	NPC145885
0.8193	Intermediate Similarity	NPC84827
0.8193	Intermediate Similarity	NPC14113
0.8187	Intermediate Similarity	NPC321708
0.8182	Intermediate Similarity	NPC329688
0.8182	Intermediate Similarity	NPC189812
0.8182	Intermediate Similarity	NPC100321
0.8176	Intermediate Similarity	NPC171171
0.8176	Intermediate Similarity	NPC286427
0.8176	Intermediate Similarity	NPC216643
0.8166	Intermediate Similarity	NPC228835
0.8166	Intermediate Similarity	NPC204717
0.8153	Intermediate Similarity	NPC470823
0.8148	Intermediate Similarity	NPC470508
0.8141	Intermediate Similarity	NPC37548
0.814	Intermediate Similarity	NPC154339
0.8137	Intermediate Similarity	NPC16667
0.8133	Intermediate Similarity	NPC218268
0.8125	Intermediate Similarity	NPC318065
0.8125	Intermediate Similarity	NPC41257
0.8125	Intermediate Similarity	NPC206819
0.8125	Intermediate Similarity	NPC56765
0.8121	Intermediate Similarity	NPC34508
0.8118	Intermediate Similarity	NPC314002
0.8113	Intermediate Similarity	NPC141353
0.8101	Intermediate Similarity	NPC141926
0.809	Intermediate Similarity	NPC300183
0.809	Intermediate Similarity	NPC475506
0.8079	Intermediate Similarity	NPC150259
0.8068	Intermediate Similarity	NPC229332
0.8059	Intermediate Similarity	NPC165495
0.8057	Intermediate Similarity	NPC157828
0.8057	Intermediate Similarity	NPC195239
0.805	Intermediate Similarity	NPC207726
0.805	Intermediate Similarity	NPC34844
0.8046	Intermediate Similarity	NPC99666
0.8046	Intermediate Similarity	NPC477167
0.8046	Intermediate Similarity	NPC473342
0.8045	Intermediate Similarity	NPC476874
0.8045	Intermediate Similarity	NPC155143
0.8041	Intermediate Similarity	NPC22079
0.8038	Intermediate Similarity	NPC470233
0.8037	Intermediate Similarity	NPC42372
0.8036	Intermediate Similarity	NPC11126
0.8025	Intermediate Similarity	NPC470203
0.8023	Intermediate Similarity	NPC17059
0.8023	Intermediate Similarity	NPC46580
0.8013	Intermediate Similarity	NPC325252
0.8012	Intermediate Similarity	NPC67056
0.8011	Intermediate Similarity	NPC11445
0.8	Intermediate Similarity	NPC267343
0.8	Intermediate Similarity	NPC98715
0.8	Intermediate Similarity	NPC242556
0.8	Intermediate Similarity	NPC280548
0.7988	Intermediate Similarity	NPC109447
0.7976	Intermediate Similarity	NPC184964
0.7975	Intermediate Similarity	NPC90723
0.7975	Intermediate Similarity	NPC476446
0.7975	Intermediate Similarity	NPC78375
0.7975	Intermediate Similarity	NPC469813
0.7965	Intermediate Similarity	NPC62749
0.7963	Intermediate Similarity	NPC470204
0.7953	Intermediate Similarity	NPC284678
0.795	Intermediate Similarity	NPC236711
0.7947	Intermediate Similarity	NPC198988
0.7944	Intermediate Similarity	NPC193761
0.7943	Intermediate Similarity	NPC324149
0.7939	Intermediate Similarity	NPC154293
0.7937	Intermediate Similarity	NPC38736
0.7933	Intermediate Similarity	NPC470497
0.7929	Intermediate Similarity	NPC270009
0.7922	Intermediate Similarity	NPC59084
0.7922	Intermediate Similarity	NPC2949
0.7921	Intermediate Similarity	NPC171317
0.7921	Intermediate Similarity	NPC470499
0.7921	Intermediate Similarity	NPC265576
0.7911	Intermediate Similarity	NPC187951
0.791	Intermediate Similarity	NPC251090
0.7904	Intermediate Similarity	NPC97525
0.7898	Intermediate Similarity	NPC316069
0.7898	Intermediate Similarity	NPC307963
0.7895	Intermediate Similarity	NPC472108
0.7895	Intermediate Similarity	NPC139291

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 NPC469785 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	584
0.2-0.3	1009
0.3-0.4	1515
0.4-0.5	2690
0.5-0.6	2015
0.6-0.7	886
0.7-0.8	227
0.8-0.85	22
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8917	High Similarity	NPD4184	Clinical (unspecified phase)
0.8889	High Similarity	NPD198	Clinical (unspecified phase)
0.8836	High Similarity	NPD786	Approved
0.8765	High Similarity	NPD6595	Phase 3
0.8758	High Similarity	NPD2144	Approved
0.875	High Similarity	NPD5065	Approved
0.8734	High Similarity	NPD5069	Clinical (unspecified phase)
0.8716	High Similarity	NPD1722	Approved
0.8598	High Similarity	NPD3038	Discontinued
0.8589	High Similarity	NPD4076	Approved
0.8589	High Similarity	NPD4079	Approved
0.8545	High Similarity	NPD5728	Clinical (unspecified phase)
0.8528	High Similarity	NPD3505	Approved
0.8528	High Similarity	NPD3506	Approved
0.8519	High Similarity	NPD482	Approved
0.8497	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD3100	Discontinued
0.8466	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD2172	Phase 1
0.8434	Intermediate Similarity	NPD2095	Phase 2
0.8434	Intermediate Similarity	NPD2092	Phase 2
0.8434	Intermediate Similarity	NPD2094	Phase 2
0.8415	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD2096	Phase 2
0.8383	Intermediate Similarity	NPD2091	Phase 2
0.8343	Intermediate Similarity	NPD8431	Approved
0.8333	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD2837	Discontinued
0.8205	Intermediate Similarity	NPD4463	Approved
0.8205	Intermediate Similarity	NPD4462	Approved
0.8121	Intermediate Similarity	NPD750	Phase 2
0.8077	Intermediate Similarity	NPD4702	Approved
0.8077	Intermediate Similarity	NPD4703	Approved
0.8075	Intermediate Similarity	NPD1404	Approved
0.8075	Intermediate Similarity	NPD1403	Approved
0.8072	Intermediate Similarity	NPD4128	Approved
0.8049	Intermediate Similarity	NPD4639	Approved
0.8049	Intermediate Similarity	NPD4640	Approved
0.8049	Intermediate Similarity	NPD4638	Approved
0.8	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1326	Approved
0.8	Intermediate Similarity	NPD1325	Approved
0.7988	Intermediate Similarity	NPD2642	Approved
0.7988	Intermediate Similarity	NPD2639	Approved
0.7987	Intermediate Similarity	NPD1592	Phase 3
0.7976	Intermediate Similarity	NPD4181	Approved
0.7975	Intermediate Similarity	NPD3323	Discontinued
0.7966	Intermediate Similarity	NPD7948	Phase 1
0.7956	Intermediate Similarity	NPD8272	Phase 2
0.7939	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD2640	Approved
0.7939	Intermediate Similarity	NPD2641	Approved
0.7927	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4075	Phase 2
0.7901	Intermediate Similarity	NPD8072	Approved
0.7898	Intermediate Similarity	NPD1038	Approved
0.7877	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD5021	Discontinued
0.7821	Intermediate Similarity	NPD3717	Discontinued
0.7814	Intermediate Similarity	NPD7957	Phase 1
0.7814	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5254	Discontinued
0.7758	Intermediate Similarity	NPD5138	Approved
0.7758	Intermediate Similarity	NPD5140	Approved
0.7751	Intermediate Similarity	NPD2928	Phase 2
0.7747	Intermediate Similarity	NPD8073	Approved
0.7742	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3404	Approved
0.7738	Intermediate Similarity	NPD3610	Approved
0.7738	Intermediate Similarity	NPD3117	Approved
0.7738	Intermediate Similarity	NPD3116	Approved
0.7738	Intermediate Similarity	NPD3609	Approved
0.7736	Intermediate Similarity	NPD1661	Suspended
0.7733	Intermediate Similarity	NPD3654	Approved
0.773	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD8386	Phase 2
0.7718	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD991	Phase 2
0.7714	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD3961	Discontinued
0.7707	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD802	Phase 2
0.7682	Intermediate Similarity	NPD3476	Approved
0.7682	Intermediate Similarity	NPD3475	Approved
0.7654	Intermediate Similarity	NPD7619	Phase 3
0.7654	Intermediate Similarity	NPD7618	Phase 3
0.7644	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4547	Phase 3
0.7622	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5862	Discovery
0.7619	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD7470	Discontinued
0.7602	Intermediate Similarity	NPD2381	Approved
0.7602	Intermediate Similarity	NPD2380	Approved
0.7602	Intermediate Similarity	NPD2382	Approved
0.76	Intermediate Similarity	NPD2118	Approved
0.76	Intermediate Similarity	NPD2119	Approved
0.7595	Intermediate Similarity	NPD2006	Phase 2
0.7595	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD3825	Phase 3
0.7581	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2430	Phase 2
0.7572	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD5426	Phase 3
0.7568	Intermediate Similarity	NPD5901	Discontinued
0.7561	Intermediate Similarity	NPD2580	Discontinued
0.7558	Intermediate Similarity	NPD8123	Approved
0.7558	Intermediate Similarity	NPD8122	Approved
0.7557	Intermediate Similarity	NPD6217	Discontinued
0.7557	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7944	Discontinued
0.7546	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD8129	Discovery
0.7541	Intermediate Similarity	NPD484	Approved
0.7532	Intermediate Similarity	NPD3385	Approved
0.7514	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD5067	Phase 2
0.7513	Intermediate Similarity	NPD5066	Phase 2
0.75	Intermediate Similarity	NPD1262	Discovery
0.75	Intermediate Similarity	NPD5555	Phase 1
0.7487	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5106	Approved
0.7486	Intermediate Similarity	NPD5105	Approved
0.7486	Intermediate Similarity	NPD5596	Phase 2
0.7485	Intermediate Similarity	NPD8026	Phase 1
0.7485	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6664	Approved
0.747	Intermediate Similarity	NPD5255	Approved
0.746	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1683	Approved
0.7453	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2896	Discontinued
0.7443	Intermediate Similarity	NPD6178	Phase 3
0.743	Intermediate Similarity	NPD6281	Approved
0.7423	Intermediate Similarity	NPD3835	Phase 3
0.7423	Intermediate Similarity	NPD3833	Phase 3
0.7419	Intermediate Similarity	NPD4029	Approved
0.7419	Intermediate Similarity	NPD4030	Approved
0.7419	Intermediate Similarity	NPD4028	Approved
0.7416	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2582	Approved
0.741	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2581	Approved
0.7405	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2165	Phase 1
0.7394	Intermediate Similarity	NPD1392	Approved
0.7389	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD8093	Discontinued
0.7382	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD3330	Phase 1
0.7381	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD3262	Approved
0.7378	Intermediate Similarity	NPD6158	Phase 2
0.7378	Intermediate Similarity	NPD2882	Phase 1
0.7365	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD706	Phase 1
0.7358	Intermediate Similarity	NPD5612	Discontinued
0.7354	Intermediate Similarity	NPD2509	Approved
0.7354	Intermediate Similarity	NPD2510	Approved
0.7353	Intermediate Similarity	NPD1248	Discontinued
0.7349	Intermediate Similarity	NPD3112	Approved
0.7349	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3115	Approved
0.7349	Intermediate Similarity	NPD6026	Approved
0.7349	Intermediate Similarity	NPD3114	Approved
0.7349	Intermediate Similarity	NPD3113	Approved
0.7348	Intermediate Similarity	NPD4615	Phase 2
0.7346	Intermediate Similarity	NPD7469	Discontinued
0.7344	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD8094	Discontinued
0.733	Intermediate Similarity	NPD1895	Discontinued
0.733	Intermediate Similarity	NPD1708	Approved
0.733	Intermediate Similarity	NPD1707	Approved
0.7329	Intermediate Similarity	NPD3813	Approved
0.7321	Intermediate Similarity	NPD2511	Approved
0.732	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2390	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