NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	185.12
Volume:	214.106
LogP:	4.41
LogD:	3.76
LogS:	-4.105
# Rotatable Bonds:	2
TPSA:	15.79
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	2.105
Fsp3:	0.231
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.553
MDCK Permeability:	1.9618786609498784e-05
Pgp-inhibitor:	0.153
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.62
30% Bioavailability (F30%):	0.95

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.332
Plasma Protein Binding (PPB):	94.38077545166016%
Volume Distribution (VD):	6.368
Pgp-substrate:	5.76192569732666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.571
CYP2C19-inhibitor:	0.965
CYP2C19-substrate:	0.479
CYP2C9-inhibitor:	0.584
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.812
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.53
CYP3A4-substrate:	0.195

ADMET: Excretion

Clearance (CL):	13.47
Half-life (T1/2):	0.617

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.704
Drug-inuced Liver Injury (DILI):	0.341
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.78
Skin Sensitization:	0.843
Carcinogencity:	0.088
Eye Corrosion:	0.102
Eye Irritation:	0.972
Respiratory Toxicity:	0.391

Download Data

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

Natural Product: NPC29886

Natural Product ID:	NPC29886
*Common Name:**	3-Dimethylallylindole
IUPAC Name:	3-(3-methylbut-2-enyl)-1H-indole
Synonyms:	3-Dimethylallylindole
Standard InCHIKey:	ASADUZQNSFEIFO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H15N/c1-10(2)7-8-11-9-14-13-6-4-3-5-12(11)13/h3-7,9,14H,8H2,1-2H3
SMILES:	CC(=CCc1c[nH]c2c1cccc2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508951
PubChem CID:	10867041
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
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3509958]
NPO2697	Monodora tenuifolia	Species	Annonaceae	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
MIC	11

Activity Type	# Activity
Organism	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	12.5	ug.mL-1	PMID[541637]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	3.12	ug.mL-1	PMID[541637]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[541637]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	25.0	ug.mL-1	PMID[541637]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	12.5	ug.mL-1	PMID[541637]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	12.5	ug.mL-1	PMID[541637]
NPT1815	Organism	Helminthosporium	Helminthosporium	MIC	=	0.78	ug.mL-1	PMID[541637]
NPT1816	Organism	Pycnoporus sanguineus	Pycnoporus sanguineus	MIC	=	12.5	ug.mL-1	PMID[541637]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	1.56	ug.mL-1	PMID[541637]

☑ 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 NPC29886 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	1051
0.1-0.2	14185
0.2-0.3	17458
0.3-0.4	4662
0.4-0.5	2087
0.5-0.6	1605
0.6-0.7	978
0.7-0.8	488
0.8-0.85	82
0.85-0.9	51
0.9-0.95	33
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC261195
0.9922	High Similarity	NPC84911
0.9845	High Similarity	NPC96102
0.9771	High Similarity	NPC110126
0.9771	High Similarity	NPC73767
0.9769	High Similarity	NPC105127
0.9697	High Similarity	NPC469780
0.9697	High Similarity	NPC469784
0.9697	High Similarity	NPC469768
0.9697	High Similarity	NPC469783
0.9697	High Similarity	NPC469761
0.9697	High Similarity	NPC469767
0.9697	High Similarity	NPC469779
0.9688	High Similarity	NPC82295
0.9624	High Similarity	NPC469766
0.9552	High Similarity	NPC190296
0.9549	High Similarity	NPC279081
0.9412	High Similarity	NPC314372
0.9403	High Similarity	NPC230002
0.9275	High Similarity	NPC471957
0.927	High Similarity	NPC159856
0.9209	High Similarity	NPC321911
0.9203	High Similarity	NPC288838
0.9203	High Similarity	NPC143872
0.9143	High Similarity	NPC53947
0.9143	High Similarity	NPC24678
0.9143	High Similarity	NPC105818
0.9137	High Similarity	NPC179787
0.9137	High Similarity	NPC469811
0.9137	High Similarity	NPC201380
0.9078	High Similarity	NPC470823
0.9065	High Similarity	NPC63545
0.9015	High Similarity	NPC22079
0.9014	High Similarity	NPC469765
0.9014	High Similarity	NPC25008
0.9014	High Similarity	NPC141926
0.9014	High Similarity	NPC200214
0.9014	High Similarity	NPC259644
0.9014	High Similarity	NPC469786
0.9014	High Similarity	NPC469763
0.9014	High Similarity	NPC73952
0.9014	High Similarity	NPC469760
0.8984	High Similarity	NPC41174
0.8963	High Similarity	NPC325252
0.8951	High Similarity	NPC212376
0.8951	High Similarity	NPC70922
0.8951	High Similarity	NPC75540
0.8951	High Similarity	NPC211572
0.8951	High Similarity	NPC80597
0.8951	High Similarity	NPC34844
0.8944	High Similarity	NPC216713
0.8889	High Similarity	NPC198988
0.8881	High Similarity	NPC325903
0.8855	High Similarity	NPC250361
0.8828	High Similarity	NPC286427
0.8824	High Similarity	NPC218268
0.8797	High Similarity	NPC473587
0.8794	High Similarity	NPC316069
0.8767	High Similarity	NPC56765
0.8767	High Similarity	NPC41257
0.8767	High Similarity	NPC206819
0.8767	High Similarity	NPC318065
0.8759	High Similarity	NPC150259
0.8759	High Similarity	NPC469785
0.8731	High Similarity	NPC475428
0.8722	High Similarity	NPC473762
0.8699	High Similarity	NPC216643
0.8699	High Similarity	NPC236711
0.8699	High Similarity	NPC469762
0.8681	High Similarity	NPC470233
0.8667	High Similarity	NPC475450
0.8667	High Similarity	NPC179365
0.8649	High Similarity	NPC282231
0.8639	High Similarity	NPC135141
0.8639	High Similarity	NPC92796
0.8639	High Similarity	NPC230869
0.8626	High Similarity	NPC46358
0.8623	High Similarity	NPC125746
0.8591	High Similarity	NPC311276
0.8591	High Similarity	NPC90723
0.8591	High Similarity	NPC40779
0.8581	High Similarity	NPC122141
0.8581	High Similarity	NPC131718
0.8581	High Similarity	NPC215584
0.8581	High Similarity	NPC470204
0.8581	High Similarity	NPC279918
0.8581	High Similarity	NPC44773
0.8571	High Similarity	NPC2949
0.8571	High Similarity	NPC115611
0.8571	High Similarity	NPC59084
0.8523	High Similarity	NPC470203
0.8511	High Similarity	NPC63157
0.8511	High Similarity	NPC473868
0.85	High Similarity	NPC88097
0.8477	Intermediate Similarity	NPC474561
0.8477	Intermediate Similarity	NPC49954
0.8477	Intermediate Similarity	NPC160105
0.8477	Intermediate Similarity	NPC49217
0.8467	Intermediate Similarity	NPC102423
0.8467	Intermediate Similarity	NPC317105
0.8467	Intermediate Similarity	NPC149265
0.8467	Intermediate Similarity	NPC473930
0.8421	Intermediate Similarity	NPC201700
0.8421	Intermediate Similarity	NPC27740
0.8411	Intermediate Similarity	NPC17751
0.8411	Intermediate Similarity	NPC280864
0.8366	Intermediate Similarity	NPC194411
0.8357	Intermediate Similarity	NPC251722
0.8357	Intermediate Similarity	NPC314102
0.8355	Intermediate Similarity	NPC54988
0.8333	Intermediate Similarity	NPC285731
0.8333	Intermediate Similarity	NPC470440
0.8333	Intermediate Similarity	NPC204141
0.8312	Intermediate Similarity	NPC470498
0.8301	Intermediate Similarity	NPC78020
0.8301	Intermediate Similarity	NPC63751
0.8289	Intermediate Similarity	NPC274229
0.8289	Intermediate Similarity	NPC42372
0.8288	Intermediate Similarity	NPC2272
0.8258	Intermediate Similarity	NPC314603
0.8258	Intermediate Similarity	NPC313791
0.8244	Intermediate Similarity	NPC91958
0.8224	Intermediate Similarity	NPC194640
0.8219	Intermediate Similarity	NPC470111
0.8219	Intermediate Similarity	NPC21605
0.8205	Intermediate Similarity	NPC275305
0.8205	Intermediate Similarity	NPC37423
0.8205	Intermediate Similarity	NPC293216
0.8194	Intermediate Similarity	NPC82331
0.8188	Intermediate Similarity	NPC282398
0.8169	Intermediate Similarity	NPC169433
0.8153	Intermediate Similarity	NPC474958
0.8153	Intermediate Similarity	NPC267885
0.8141	Intermediate Similarity	NPC477611
0.8129	Intermediate Similarity	NPC97343
0.8112	Intermediate Similarity	NPC312092
0.8108	Intermediate Similarity	NPC40070
0.8108	Intermediate Similarity	NPC33421
0.8101	Intermediate Similarity	NPC248454
0.8101	Intermediate Similarity	NPC151939
0.8101	Intermediate Similarity	NPC14113
0.8101	Intermediate Similarity	NPC240088
0.8101	Intermediate Similarity	NPC68354
0.8101	Intermediate Similarity	NPC473380
0.8101	Intermediate Similarity	NPC145885
0.8101	Intermediate Similarity	NPC84827
0.8092	Intermediate Similarity	NPC148140
0.8089	Intermediate Similarity	NPC149155
0.8089	Intermediate Similarity	NPC110500
0.8089	Intermediate Similarity	NPC203468
0.8088	Intermediate Similarity	NPC146373
0.8088	Intermediate Similarity	NPC245244
0.8088	Intermediate Similarity	NPC166424
0.806	Intermediate Similarity	NPC182570
0.806	Intermediate Similarity	NPC265605
0.806	Intermediate Similarity	NPC48564
0.805	Intermediate Similarity	NPC126709
0.805	Intermediate Similarity	NPC11126
0.805	Intermediate Similarity	NPC213468
0.805	Intermediate Similarity	NPC248041
0.805	Intermediate Similarity	NPC265710
0.805	Intermediate Similarity	NPC233050
0.805	Intermediate Similarity	NPC215795
0.805	Intermediate Similarity	NPC176199
0.805	Intermediate Similarity	NPC276540
0.8041	Intermediate Similarity	NPC37548
0.8039	Intermediate Similarity	NPC225018
0.8038	Intermediate Similarity	NPC280852
0.803	Intermediate Similarity	NPC81561
0.8014	Intermediate Similarity	NPC242556
0.8	Intermediate Similarity	NPC16659
0.8	Intermediate Similarity	NPC314919
0.8	Intermediate Similarity	NPC300688
0.7987	Intermediate Similarity	NPC284775
0.7987	Intermediate Similarity	NPC148592
0.7987	Intermediate Similarity	NPC111275
0.7987	Intermediate Similarity	NPC59269
0.7975	Intermediate Similarity	NPC280297
0.797	Intermediate Similarity	NPC143603
0.795	Intermediate Similarity	NPC233936
0.795	Intermediate Similarity	NPC275292
0.795	Intermediate Similarity	NPC470677
0.795	Intermediate Similarity	NPC243381
0.7937	Intermediate Similarity	NPC283219
0.7937	Intermediate Similarity	NPC55772
0.7931	Intermediate Similarity	NPC284635
0.7908	Intermediate Similarity	NPC474880
0.7908	Intermediate Similarity	NPC221786
0.7908	Intermediate Similarity	NPC475990
0.7901	Intermediate Similarity	NPC163055
0.7901	Intermediate Similarity	NPC469358
0.7895	Intermediate Similarity	NPC51054
0.7895	Intermediate Similarity	NPC476464
0.7888	Intermediate Similarity	NPC164228
0.7881	Intermediate Similarity	NPC232798
0.7877	Intermediate Similarity	NPC476454
0.7872	Intermediate Similarity	NPC101165
0.7862	Intermediate Similarity	NPC104483
0.7853	Intermediate Similarity	NPC228835
0.7853	Intermediate Similarity	NPC204717

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 NPC29886 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	438
0.1-0.2	956
0.2-0.3	919
0.3-0.4	2085
0.4-0.5	2228
0.5-0.6	1599
0.6-0.7	701
0.7-0.8	177
0.8-0.85	37
0.85-0.9	5
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9845	High Similarity	NPD198	Clinical (unspecified phase)
0.9771	High Similarity	NPD786	Approved
0.9478	High Similarity	NPD1722	Approved
0.9209	High Similarity	NPD3100	Discontinued
0.9143	High Similarity	NPD2172	Phase 1
0.9071	High Similarity	NPD4374	Clinical (unspecified phase)
0.875	High Similarity	NPD2837	Discontinued
0.8707	High Similarity	NPD1403	Approved
0.8707	High Similarity	NPD1404	Approved
0.8591	High Similarity	NPD3323	Discontinued
0.8571	High Similarity	NPD3943	Clinical (unspecified phase)
0.8507	High Similarity	NPD992	Clinical (unspecified phase)
0.8507	High Similarity	NPD991	Phase 2
0.8477	Intermediate Similarity	NPD2642	Approved
0.8477	Intermediate Similarity	NPD2639	Approved
0.8421	Intermediate Similarity	NPD2641	Approved
0.8421	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD2640	Approved
0.84	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD5254	Discontinued
0.8382	Intermediate Similarity	NPD3654	Approved
0.8366	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD3476	Approved
0.8321	Intermediate Similarity	NPD3475	Approved
0.8312	Intermediate Similarity	NPD3609	Approved
0.8312	Intermediate Similarity	NPD3610	Approved
0.8301	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD2119	Approved
0.8235	Intermediate Similarity	NPD2118	Approved
0.8231	Intermediate Similarity	NPD4462	Approved
0.8231	Intermediate Similarity	NPD4463	Approved
0.8227	Intermediate Similarity	NPD1262	Discovery
0.8219	Intermediate Similarity	NPD4547	Phase 3
0.8205	Intermediate Similarity	NPD4128	Approved
0.8194	Intermediate Similarity	NPD2006	Phase 2
0.8163	Intermediate Similarity	NPD2430	Phase 2
0.8162	Intermediate Similarity	NPD9583	Approved
0.8153	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD4075	Phase 2
0.8151	Intermediate Similarity	NPD1683	Approved
0.8143	Intermediate Similarity	NPD3385	Approved
0.8133	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD2580	Discontinued
0.8117	Intermediate Similarity	NPD1248	Discontinued
0.8101	Intermediate Similarity	NPD2144	Approved
0.8101	Intermediate Similarity	NPD3506	Approved
0.8101	Intermediate Similarity	NPD4181	Approved
0.8101	Intermediate Similarity	NPD3505	Approved
0.8089	Intermediate Similarity	NPD5065	Approved
0.8089	Intermediate Similarity	NPD482	Approved
0.8079	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD271	Approved
0.806	Intermediate Similarity	NPD268	Approved
0.806	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD4079	Approved
0.805	Intermediate Similarity	NPD4076	Approved
0.803	Intermediate Similarity	NPD9392	Approved
0.803	Intermediate Similarity	NPD9396	Approved
0.8015	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD9357	Approved
0.8014	Intermediate Similarity	NPD4029	Approved
0.8014	Intermediate Similarity	NPD4030	Approved
0.8014	Intermediate Similarity	NPD4028	Approved
0.8	Intermediate Similarity	NPD6595	Phase 3
0.7987	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD3038	Discontinued
0.795	Intermediate Similarity	NPD1708	Approved
0.795	Intermediate Similarity	NPD1707	Approved
0.7949	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD2165	Phase 1
0.7929	Intermediate Similarity	NPD715	Phase 3
0.7901	Intermediate Similarity	NPD5105	Approved
0.7901	Intermediate Similarity	NPD5106	Approved
0.7901	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3113	Approved
0.7895	Intermediate Similarity	NPD3115	Approved
0.7895	Intermediate Similarity	NPD3114	Approved
0.7895	Intermediate Similarity	NPD3112	Approved
0.7888	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD3944	Approved
0.7887	Intermediate Similarity	NPD3942	Approved
0.7862	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1895	Discontinued
0.7829	Intermediate Similarity	NPD977	Approved
0.7829	Intermediate Similarity	NPD976	Approved
0.7829	Intermediate Similarity	NPD975	Approved
0.7806	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD750	Phase 2
0.7791	Intermediate Similarity	NPD2092	Phase 2
0.7791	Intermediate Similarity	NPD2094	Phase 2
0.7791	Intermediate Similarity	NPD2095	Phase 2
0.7791	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD5436	Phase 1
0.7785	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1255	Approved
0.7778	Intermediate Similarity	NPD1254	Approved
0.7778	Intermediate Similarity	NPD1253	Approved
0.7778	Intermediate Similarity	NPD1256	Approved
0.7758	Intermediate Similarity	NPD6217	Discontinued
0.7758	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD803	Phase 1
0.7744	Intermediate Similarity	NPD2091	Phase 2
0.7744	Intermediate Similarity	NPD2096	Phase 2
0.7714	Intermediate Similarity	NPD1598	Discontinued
0.7711	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD3961	Discontinued
0.7711	Intermediate Similarity	NPD8431	Approved
0.7692	Intermediate Similarity	NPD5315	Discontinued
0.7665	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1592	Phase 3
0.7619	Intermediate Similarity	NPD2069	Approved
0.7619	Intermediate Similarity	NPD2068	Approved
0.7619	Intermediate Similarity	NPD2070	Approved
0.7619	Intermediate Similarity	NPD2074	Approved
0.7619	Intermediate Similarity	NPD2075	Approved
0.7619	Intermediate Similarity	NPD2073	Approved
0.7619	Intermediate Similarity	NPD2071	Approved
0.7619	Intermediate Similarity	NPD2072	Approved
0.7609	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD947	Approved
0.7605	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD6554	Approved
0.7603	Intermediate Similarity	NPD45	Approved
0.7595	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4880	Discontinued
0.7562	Intermediate Similarity	NPD1325	Approved
0.7562	Intermediate Similarity	NPD1326	Approved
0.7548	Intermediate Similarity	NPD2150	Discontinued
0.7538	Intermediate Similarity	NPD9098	Phase 3
0.7538	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD9598	Discontinued
0.7532	Intermediate Similarity	NPD3339	Approved
0.7516	Intermediate Similarity	NPD3833	Phase 3
0.7516	Intermediate Similarity	NPD3835	Phase 3
0.7516	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1661	Suspended
0.75	Intermediate Similarity	NPD4640	Approved
0.75	Intermediate Similarity	NPD680	Discontinued
0.75	Intermediate Similarity	NPD4639	Approved
0.75	Intermediate Similarity	NPD4638	Approved
0.75	Intermediate Similarity	NPD4702	Approved
0.75	Intermediate Similarity	NPD4703	Approved
0.7485	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD802	Phase 2
0.7485	Intermediate Similarity	NPD1038	Approved
0.7471	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4047	Discontinued
0.7442	Intermediate Similarity	NPD7618	Phase 3
0.7442	Intermediate Similarity	NPD7619	Phase 3
0.7436	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3117	Approved
0.7407	Intermediate Similarity	NPD3116	Approved
0.7399	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5021	Discontinued
0.7391	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1227	Phase 2
0.7379	Intermediate Similarity	NPD1251	Discontinued
0.7362	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6664	Approved
0.7338	Intermediate Similarity	NPD1183	Approved
0.7329	Intermediate Similarity	NPD1993	Approved
0.7329	Intermediate Similarity	NPD1995	Approved
0.7329	Intermediate Similarity	NPD1994	Approved
0.7308	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6828	Phase 2
0.7299	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1030	Approved
0.729	Intermediate Similarity	NPD1029	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1027	Approved
0.7289	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2720	Phase 1
0.7267	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1313	Approved
0.7259	Intermediate Similarity	NPD4824	Approved
0.7259	Intermediate Similarity	NPD4823	Approved
0.7257	Intermediate Similarity	NPD7948	Phase 1
0.725	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD200	Phase 2
0.7248	Intermediate Similarity	NPD201	Phase 2
0.7229	Intermediate Similarity	NPD7111	Discontinued
0.7225	Intermediate Similarity	NPD4615	Phase 2
0.7219	Intermediate Similarity	NPD7564	Discontinued
0.7208	Intermediate Similarity	NPD7469	Discontinued
0.7205	Intermediate Similarity	NPD5140	Approved
0.7205	Intermediate Similarity	NPD3583	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data