NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	146.08
Volume:	158.555
LogP:	1.283
LogD:	0.499
LogS:	0.075
# Rotatable Bonds:	1
TPSA:	41.81
# H-Bond Aceptor:	2
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.63
Synthetic Accessibility Score:	1.841
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.63
MDCK Permeability:	6.869204298709519e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.196

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.541
Plasma Protein Binding (PPB):	10.748327255249023%
Volume Distribution (VD):	1.766
Pgp-substrate:	69.2028579711914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.958
CYP1A2-substrate:	0.783
CYP2C19-inhibitor:	0.334
CYP2C19-substrate:	0.239
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.822
CYP2D6-inhibitor:	0.738
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.167
CYP3A4-substrate:	0.158

ADMET: Excretion

Clearance (CL):	9.42
Half-life (T1/2):	0.895

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.296
Drug-inuced Liver Injury (DILI):	0.093
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.944
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.746
Carcinogencity:	0.059
Eye Corrosion:	0.606
Eye Irritation:	0.56
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC105127

Natural Product ID:	NPC105127
*Common Name:**	1H-Indol-3-Ylmethanamine
IUPAC Name:	1H-indol-3-ylmethanamine
Synonyms:
Standard InCHIKey:	JXYGLMATGAAIBU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10N2/c10-5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5,10H2
SMILES:	NCc1c[nH]c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL6509
PubChem CID:	472107
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
NPO27821	Pochonia chlamydosporia	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.tetlet.2008.10.099]
NPO27821	Pochonia chlamydosporia	Species	Clavicipitaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20000774]
NPO7578	Trichoderma cornu-damae	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30457333]
NPO27408	Stereospermum kunthianum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27408	Stereospermum kunthianum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16238	Lactarius subdulcis	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23289.2	Heracleum sphondylium subsp. sibiricum	Subspecies	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17621	Ammocharis tinneana	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18987.1	Lupinus polyphyllus var. humicola	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28684	Amianthium muscitoxicum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27821	Pochonia chlamydosporia	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17082	Lolium remotum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14032	Gossypium arboreum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7578	Trichoderma cornu-damae	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11781	Amauroascus niger	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27408	Stereospermum kunthianum	Species	Bignoniaceae	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
Ki	2

Activity Type	# Activity
Others	1
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ki	=	3440.0	nM	PMID[504798]
NPT969	Protein Family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	14700.0	nM	PMID[504798]

☑ 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 NPC105127 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	2039
0.1-0.2	14687
0.2-0.3	17011
0.3-0.4	3905
0.4-0.5	2041
0.5-0.6	1489
0.6-0.7	939
0.7-0.8	418
0.8-0.85	81
0.85-0.9	53
0.9-0.95	15
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC96102
0.9847	High Similarity	NPC110126
0.9846	High Similarity	NPC84911
0.9769	High Similarity	NPC261195
0.9769	High Similarity	NPC29886
0.9697	High Similarity	NPC73767
0.9624	High Similarity	NPC279081
0.9624	High Similarity	NPC469779
0.9624	High Similarity	NPC469768
0.9624	High Similarity	NPC469784
0.9624	High Similarity	NPC469767
0.9624	High Similarity	NPC469780
0.9624	High Similarity	NPC469761
0.9624	High Similarity	NPC469783
0.9612	High Similarity	NPC82295
0.9552	High Similarity	NPC469766
0.9481	High Similarity	NPC190296
0.9478	High Similarity	NPC230002
0.9343	High Similarity	NPC314372
0.9343	High Similarity	NPC159856
0.9275	High Similarity	NPC143872
0.9275	High Similarity	NPC288838
0.9209	High Similarity	NPC471957
0.9209	High Similarity	NPC469811
0.9143	High Similarity	NPC321911
0.9137	High Similarity	NPC63545
0.9078	High Similarity	NPC105818
0.9078	High Similarity	NPC24678
0.9078	High Similarity	NPC53947
0.9071	High Similarity	NPC179787
0.9071	High Similarity	NPC201380
0.9014	High Similarity	NPC470823
0.9014	High Similarity	NPC216713
0.8951	High Similarity	NPC25008
0.8951	High Similarity	NPC73952
0.8951	High Similarity	NPC325903
0.8951	High Similarity	NPC141926
0.8951	High Similarity	NPC469760
0.8951	High Similarity	NPC200214
0.8951	High Similarity	NPC469763
0.8951	High Similarity	NPC469765
0.8951	High Similarity	NPC259644
0.8951	High Similarity	NPC469786
0.8947	High Similarity	NPC22079
0.8897	High Similarity	NPC325252
0.8897	High Similarity	NPC218268
0.8889	High Similarity	NPC34844
0.8889	High Similarity	NPC211572
0.8889	High Similarity	NPC70922
0.8889	High Similarity	NPC80597
0.8889	High Similarity	NPC212376
0.8889	High Similarity	NPC75540
0.8828	High Similarity	NPC469785
0.8824	High Similarity	NPC198988
0.8788	High Similarity	NPC250361
0.8769	High Similarity	NPC41174
0.8767	High Similarity	NPC216643
0.8767	High Similarity	NPC469762
0.8767	High Similarity	NPC286427
0.8732	High Similarity	NPC316069
0.8707	High Similarity	NPC135141
0.8707	High Similarity	NPC56765
0.8707	High Similarity	NPC318065
0.8707	High Similarity	NPC206819
0.8707	High Similarity	NPC92796
0.8707	High Similarity	NPC41257
0.8696	High Similarity	NPC125746
0.8696	High Similarity	NPC150259
0.8658	High Similarity	NPC317105
0.8657	High Similarity	NPC473762
0.8649	High Similarity	NPC279918
0.8649	High Similarity	NPC122141
0.8649	High Similarity	NPC131718
0.8649	High Similarity	NPC470204
0.8643	High Similarity	NPC59084
0.8643	High Similarity	NPC115611
0.8639	High Similarity	NPC236711
0.8636	High Similarity	NPC27740
0.8621	High Similarity	NPC470233
0.8593	High Similarity	NPC473587
0.8591	High Similarity	NPC470203
0.8591	High Similarity	NPC282231
0.8582	High Similarity	NPC473868
0.8582	High Similarity	NPC63157
0.8581	High Similarity	NPC230869
0.8571	High Similarity	NPC88097
0.8561	High Similarity	NPC46358
0.8533	High Similarity	NPC311276
0.8533	High Similarity	NPC90723
0.8529	High Similarity	NPC475428
0.8523	High Similarity	NPC44773
0.8523	High Similarity	NPC215584
0.8511	High Similarity	NPC2949
0.8477	Intermediate Similarity	NPC280864
0.8477	Intermediate Similarity	NPC17751
0.8467	Intermediate Similarity	NPC475450
0.8467	Intermediate Similarity	NPC179365
0.8421	Intermediate Similarity	NPC49954
0.8421	Intermediate Similarity	NPC54988
0.8421	Intermediate Similarity	NPC49217
0.8421	Intermediate Similarity	NPC160105
0.8421	Intermediate Similarity	NPC474561
0.8411	Intermediate Similarity	NPC40779
0.8411	Intermediate Similarity	NPC149265
0.8411	Intermediate Similarity	NPC102423
0.8406	Intermediate Similarity	NPC473930
0.8403	Intermediate Similarity	NPC285731
0.8403	Intermediate Similarity	NPC204141
0.8366	Intermediate Similarity	NPC63751
0.8355	Intermediate Similarity	NPC274229
0.8323	Intermediate Similarity	NPC477611
0.8312	Intermediate Similarity	NPC194411
0.8298	Intermediate Similarity	NPC251722
0.8298	Intermediate Similarity	NPC314102
0.8296	Intermediate Similarity	NPC245244
0.8296	Intermediate Similarity	NPC146373
0.8296	Intermediate Similarity	NPC166424
0.8288	Intermediate Similarity	NPC21605
0.8276	Intermediate Similarity	NPC470440
0.8261	Intermediate Similarity	NPC282398
0.8258	Intermediate Similarity	NPC82331
0.8258	Intermediate Similarity	NPC470498
0.8247	Intermediate Similarity	NPC78020
0.8247	Intermediate Similarity	NPC201700
0.8235	Intermediate Similarity	NPC42372
0.8231	Intermediate Similarity	NPC2272
0.8217	Intermediate Similarity	NPC474958
0.8205	Intermediate Similarity	NPC314603
0.8194	Intermediate Similarity	NPC97343
0.8182	Intermediate Similarity	NPC91958
0.8176	Intermediate Similarity	NPC40070
0.817	Intermediate Similarity	NPC194640
0.8163	Intermediate Similarity	NPC470111
0.8153	Intermediate Similarity	NPC37423
0.8153	Intermediate Similarity	NPC149155
0.8153	Intermediate Similarity	NPC203468
0.8153	Intermediate Similarity	NPC110500
0.8153	Intermediate Similarity	NPC275305
0.8134	Intermediate Similarity	NPC48564
0.8134	Intermediate Similarity	NPC182570
0.8134	Intermediate Similarity	NPC265605
0.8125	Intermediate Similarity	NPC284635
0.8112	Intermediate Similarity	NPC169433
0.8105	Intermediate Similarity	NPC225018
0.8101	Intermediate Similarity	NPC267885
0.8089	Intermediate Similarity	NPC313791
0.8071	Intermediate Similarity	NPC101165
0.8063	Intermediate Similarity	NPC164228
0.8056	Intermediate Similarity	NPC312092
0.8054	Intermediate Similarity	NPC33421
0.8054	Intermediate Similarity	NPC148592
0.805	Intermediate Similarity	NPC14113
0.805	Intermediate Similarity	NPC145885
0.805	Intermediate Similarity	NPC248454
0.805	Intermediate Similarity	NPC68354
0.805	Intermediate Similarity	NPC240088
0.805	Intermediate Similarity	NPC284775
0.805	Intermediate Similarity	NPC59269
0.805	Intermediate Similarity	NPC473380
0.805	Intermediate Similarity	NPC84827
0.8038	Intermediate Similarity	NPC293216
0.8038	Intermediate Similarity	NPC280297
0.8012	Intermediate Similarity	NPC233936
0.8	Intermediate Similarity	NPC283219
0.8	Intermediate Similarity	NPC176199
0.8	Intermediate Similarity	NPC248041
0.8	Intermediate Similarity	NPC265710
0.8	Intermediate Similarity	NPC11126
0.8	Intermediate Similarity	NPC215795
0.8	Intermediate Similarity	NPC126709
0.7987	Intermediate Similarity	NPC37548
0.7987	Intermediate Similarity	NPC280852
0.7961	Intermediate Similarity	NPC476464
0.7959	Intermediate Similarity	NPC242556
0.795	Intermediate Similarity	NPC314919
0.795	Intermediate Similarity	NPC16659
0.7947	Intermediate Similarity	NPC232798
0.7945	Intermediate Similarity	NPC476454
0.7937	Intermediate Similarity	NPC111275
0.7937	Intermediate Similarity	NPC151939
0.7935	Intermediate Similarity	NPC478184
0.7925	Intermediate Similarity	NPC471579
0.7914	Intermediate Similarity	NPC477003
0.791	Intermediate Similarity	NPC143603
0.7905	Intermediate Similarity	NPC86288
0.7901	Intermediate Similarity	NPC307191
0.7895	Intermediate Similarity	NPC476219
0.7895	Intermediate Similarity	NPC148140
0.7895	Intermediate Similarity	NPC476297
0.7888	Intermediate Similarity	NPC276540
0.7888	Intermediate Similarity	NPC233050
0.7888	Intermediate Similarity	NPC55772
0.7888	Intermediate Similarity	NPC213468
0.7866	Intermediate Similarity	NPC99939
0.7866	Intermediate Similarity	NPC15102
0.7866	Intermediate Similarity	NPC308931
0.7857	Intermediate Similarity	NPC475990
0.7857	Intermediate Similarity	NPC474880
0.7857	Intermediate Similarity	NPC221786
0.7853	Intermediate Similarity	NPC163055

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 NPC105127 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	504
0.1-0.2	1004
0.2-0.3	966
0.3-0.4	2148
0.4-0.5	2163
0.5-0.6	1531
0.6-0.7	634
0.7-0.8	166
0.8-0.85	22
0.85-0.9	8
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9922	High Similarity	NPD198	Clinical (unspecified phase)
0.9697	High Similarity	NPD786	Approved
0.9552	High Similarity	NPD1722	Approved
0.9143	High Similarity	NPD3100	Discontinued
0.9143	High Similarity	NPD4374	Clinical (unspecified phase)
0.9078	High Similarity	NPD2172	Phase 1
0.8951	High Similarity	NPD2837	Discontinued
0.8722	High Similarity	NPD992	Clinical (unspecified phase)
0.8722	High Similarity	NPD991	Phase 2
0.8649	High Similarity	NPD1404	Approved
0.8649	High Similarity	NPD1403	Approved
0.8591	High Similarity	NPD1853	Clinical (unspecified phase)
0.8533	High Similarity	NPD3323	Discontinued
0.8511	High Similarity	NPD3943	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD3654	Approved
0.8421	Intermediate Similarity	NPD2642	Approved
0.8421	Intermediate Similarity	NPD2639	Approved
0.8392	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD2641	Approved
0.8366	Intermediate Similarity	NPD2640	Approved
0.8333	Intermediate Similarity	NPD5254	Discontinued
0.8312	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD1262	Discovery
0.8288	Intermediate Similarity	NPD4547	Phase 3
0.8269	Intermediate Similarity	NPD5065	Approved
0.8267	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD2006	Phase 2
0.8261	Intermediate Similarity	NPD3476	Approved
0.8261	Intermediate Similarity	NPD3475	Approved
0.8258	Intermediate Similarity	NPD3609	Approved
0.8258	Intermediate Similarity	NPD3610	Approved
0.8231	Intermediate Similarity	NPD2430	Phase 2
0.8217	Intermediate Similarity	NPD4075	Phase 2
0.8214	Intermediate Similarity	NPD3385	Approved
0.8176	Intermediate Similarity	NPD4462	Approved
0.8176	Intermediate Similarity	NPD4463	Approved
0.8175	Intermediate Similarity	NPD2119	Approved
0.8175	Intermediate Similarity	NPD2118	Approved
0.8165	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD482	Approved
0.8153	Intermediate Similarity	NPD4128	Approved
0.8138	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD268	Approved
0.8134	Intermediate Similarity	NPD271	Approved
0.8106	Intermediate Similarity	NPD9392	Approved
0.8106	Intermediate Similarity	NPD9396	Approved
0.8102	Intermediate Similarity	NPD9583	Approved
0.8101	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1683	Approved
0.8079	Intermediate Similarity	NPD2580	Discontinued
0.8079	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD1248	Discontinued
0.805	Intermediate Similarity	NPD4181	Approved
0.805	Intermediate Similarity	NPD3506	Approved
0.805	Intermediate Similarity	NPD3505	Approved
0.805	Intermediate Similarity	NPD2144	Approved
0.8026	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2165	Phase 1
0.8	Intermediate Similarity	NPD4076	Approved
0.8	Intermediate Similarity	NPD4079	Approved
0.7961	Intermediate Similarity	NPD3115	Approved
0.7961	Intermediate Similarity	NPD3112	Approved
0.7961	Intermediate Similarity	NPD3113	Approved
0.7961	Intermediate Similarity	NPD3114	Approved
0.7958	Intermediate Similarity	NPD4030	Approved
0.7958	Intermediate Similarity	NPD4029	Approved
0.7958	Intermediate Similarity	NPD4028	Approved
0.7956	Intermediate Similarity	NPD9357	Approved
0.7955	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6595	Phase 3
0.7943	Intermediate Similarity	NPD803	Phase 1
0.7931	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1598	Discontinued
0.7901	Intermediate Similarity	NPD1707	Approved
0.7901	Intermediate Similarity	NPD3038	Discontinued
0.7901	Intermediate Similarity	NPD1708	Approved
0.7901	Intermediate Similarity	NPD1895	Discontinued
0.7898	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD976	Approved
0.7895	Intermediate Similarity	NPD977	Approved
0.7895	Intermediate Similarity	NPD975	Approved
0.7872	Intermediate Similarity	NPD715	Phase 3
0.7871	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD5106	Approved
0.7853	Intermediate Similarity	NPD2092	Phase 2
0.7853	Intermediate Similarity	NPD2095	Phase 2
0.7853	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD5105	Approved
0.7853	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD2094	Phase 2
0.7848	Intermediate Similarity	NPD5436	Phase 1
0.7847	Intermediate Similarity	NPD1256	Approved
0.7847	Intermediate Similarity	NPD1255	Approved
0.7847	Intermediate Similarity	NPD1253	Approved
0.7847	Intermediate Similarity	NPD1254	Approved
0.7832	Intermediate Similarity	NPD3942	Approved
0.7832	Intermediate Similarity	NPD3944	Approved
0.7805	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD2091	Phase 2
0.7805	Intermediate Similarity	NPD2096	Phase 2
0.7801	Intermediate Similarity	NPD947	Approved
0.7771	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3961	Discontinued
0.775	Intermediate Similarity	NPD750	Phase 2
0.7737	Intermediate Similarity	NPD9598	Discontinued
0.7733	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6217	Discontinued
0.7681	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD8431	Approved
0.7665	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD5315	Discontinued
0.7619	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD2150	Discontinued
0.76	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD3339	Approved
0.7584	Intermediate Similarity	NPD1592	Phase 3
0.7578	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1251	Discontinued
0.7568	Intermediate Similarity	NPD2068	Approved
0.7568	Intermediate Similarity	NPD2070	Approved
0.7568	Intermediate Similarity	NPD2071	Approved
0.7568	Intermediate Similarity	NPD2072	Approved
0.7568	Intermediate Similarity	NPD2074	Approved
0.7568	Intermediate Similarity	NPD2073	Approved
0.7568	Intermediate Similarity	NPD2069	Approved
0.7568	Intermediate Similarity	NPD2075	Approved
0.7566	Intermediate Similarity	NPD1661	Suspended
0.756	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6554	Approved
0.7551	Intermediate Similarity	NPD45	Approved
0.7547	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD4880	Discontinued
0.7529	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1325	Approved
0.7516	Intermediate Similarity	NPD1326	Approved
0.75	Intermediate Similarity	NPD7619	Phase 3
0.75	Intermediate Similarity	NPD7618	Phase 3
0.75	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD3116	Approved
0.7469	Intermediate Similarity	NPD3117	Approved
0.7468	Intermediate Similarity	NPD3833	Phase 3
0.7468	Intermediate Similarity	NPD3835	Phase 3
0.7457	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4639	Approved
0.7453	Intermediate Similarity	NPD4638	Approved
0.7453	Intermediate Similarity	NPD4640	Approved
0.7451	Intermediate Similarity	NPD4702	Approved
0.7451	Intermediate Similarity	NPD4703	Approved
0.745	Intermediate Similarity	NPD680	Discontinued
0.7442	Intermediate Similarity	NPD1038	Approved
0.7442	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD802	Phase 2
0.7442	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1227	Phase 2
0.7417	Intermediate Similarity	NPD4047	Discontinued
0.7414	Intermediate Similarity	NPD6664	Approved
0.7403	Intermediate Similarity	NPD1183	Approved
0.7372	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6828	Phase 2
0.7362	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD9098	Phase 3
0.7346	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5021	Discontinued
0.7329	Intermediate Similarity	NPD2720	Phase 1
0.7329	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1313	Approved
0.7324	Intermediate Similarity	NPD9253	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD200	Phase 2
0.7315	Intermediate Similarity	NPD201	Phase 2
0.7314	Intermediate Similarity	NPD7948	Phase 1
0.7312	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD3404	Approved
0.7283	Intermediate Similarity	NPD4615	Phase 2
0.7279	Intermediate Similarity	NPD1995	Approved
0.7279	Intermediate Similarity	NPD1993	Approved
0.7279	Intermediate Similarity	NPD1994	Approved
0.7278	Intermediate Similarity	NPD7564	Discontinued
0.7267	Intermediate Similarity	NPD6133	Discontinued
0.725	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1030	Approved
0.7244	Intermediate Similarity	NPD1027	Approved
0.7244	Intermediate Similarity	NPD1029	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD3825	Phase 3
0.7232	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6375	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