NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	187.06
Volume:	194.458
LogP:	2.467
LogD:	1.597
LogS:	-3.004
# Rotatable Bonds:	2
TPSA:	39.07
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.641
Synthetic Accessibility Score:	2.191
Fsp3:	0.091
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.407
MDCK Permeability:	2.176661837438587e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.995
Plasma Protein Binding (PPB):	61.78280258178711%
Volume Distribution (VD):	0.953
Pgp-substrate:	32.39950180053711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.72
CYP2C19-inhibitor:	0.546
CYP2C19-substrate:	0.369
CYP2C9-inhibitor:	0.227
CYP2C9-substrate:	0.606
CYP2D6-inhibitor:	0.078
CYP2D6-substrate:	0.169
CYP3A4-inhibitor:	0.146
CYP3A4-substrate:	0.341

ADMET: Excretion

Clearance (CL):	2.418
Half-life (T1/2):	0.659

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.767
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.557
Skin Sensitization:	0.212
Carcinogencity:	0.652
Eye Corrosion:	0.018
Eye Irritation:	0.271
Respiratory Toxicity:	0.601

Download Data

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

Natural Product: NPC114637

Natural Product ID:	NPC114637
*Common Name:**	1-Acetylindole-3-Carbaldehyde
IUPAC Name:	1-acetylindole-3-carbaldehyde
Synonyms:
Standard InCHIKey:	LCJLFGSKHBDOAY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H9NO2/c1-8(14)12-6-9(7-13)10-4-2-3-5-11(10)12/h2-7H,1H3
SMILES:	O=Cc1cn(c2c1cccc2)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1650260
PubChem CID:	89915
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s11306-014-0728-9]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1038/sdata.2014.29]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11171227]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12576668]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	seed	n.a.	PMID[25891114]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987503]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	Database[MetaboLights]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21080	Solanum lycopersicum	Species	Solanaceae	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
Potency	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[536279]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[536279]

☑ 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 NPC114637 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	525
0.1-0.2	5391
0.2-0.3	15713
0.3-0.4	14696
0.4-0.5	2503
0.5-0.6	2051
0.6-0.7	1424
0.7-0.8	359
0.8-0.85	29
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9416	High Similarity	NPC242116
0.8931	High Similarity	NPC42372
0.8834	High Similarity	NPC293216
0.8606	High Similarity	NPC469529
0.8571	High Similarity	NPC470677
0.8471	Intermediate Similarity	NPC477003
0.8293	Intermediate Similarity	NPC265100
0.8256	Intermediate Similarity	NPC110158
0.8208	Intermediate Similarity	NPC282103
0.8198	Intermediate Similarity	NPC102755
0.8182	Intermediate Similarity	NPC476460
0.8084	Intermediate Similarity	NPC56233
0.807	Intermediate Similarity	NPC284775
0.8023	Intermediate Similarity	NPC154339
0.8	Intermediate Similarity	NPC293487
0.7989	Intermediate Similarity	NPC267343
0.7978	Intermediate Similarity	NPC138370
0.7977	Intermediate Similarity	NPC73994
0.7965	Intermediate Similarity	NPC64436
0.7964	Intermediate Similarity	NPC478182
0.7949	Intermediate Similarity	NPC65408
0.7931	Intermediate Similarity	NPC191415
0.7911	Intermediate Similarity	NPC238499
0.7869	Intermediate Similarity	NPC477004
0.7866	Intermediate Similarity	NPC281094
0.7857	Intermediate Similarity	NPC478184
0.7824	Intermediate Similarity	NPC70949
0.7816	Intermediate Similarity	NPC248462
0.7816	Intermediate Similarity	NPC11126
0.7809	Intermediate Similarity	NPC278434
0.7805	Intermediate Similarity	NPC217021
0.7805	Intermediate Similarity	NPC472260
0.7805	Intermediate Similarity	NPC470679
0.7798	Intermediate Similarity	NPC478185
0.7797	Intermediate Similarity	NPC133003
0.7784	Intermediate Similarity	NPC80681
0.7778	Intermediate Similarity	NPC32534
0.7772	Intermediate Similarity	NPC81535
0.7771	Intermediate Similarity	NPC88110
0.7771	Intermediate Similarity	NPC24864
0.7765	Intermediate Similarity	NPC478183
0.7759	Intermediate Similarity	NPC83774
0.7725	Intermediate Similarity	NPC76982
0.7722	Intermediate Similarity	NPC150259
0.7714	Intermediate Similarity	NPC12649
0.7706	Intermediate Similarity	NPC115232
0.7701	Intermediate Similarity	NPC317701
0.7697	Intermediate Similarity	NPC70406
0.7692	Intermediate Similarity	NPC214106
0.7684	Intermediate Similarity	NPC159125
0.7674	Intermediate Similarity	NPC91895
0.767	Intermediate Similarity	NPC61011
0.7662	Intermediate Similarity	NPC471589
0.7657	Intermediate Similarity	NPC234987
0.7657	Intermediate Similarity	NPC157583
0.7654	Intermediate Similarity	NPC141612
0.7654	Intermediate Similarity	NPC135601
0.7654	Intermediate Similarity	NPC17273
0.7651	Intermediate Similarity	NPC200214
0.764	Intermediate Similarity	NPC277157
0.764	Intermediate Similarity	NPC228835
0.764	Intermediate Similarity	NPC21429
0.7622	Intermediate Similarity	NPC474916
0.7613	Intermediate Similarity	NPC71236
0.761	Intermediate Similarity	NPC472288
0.7596	Intermediate Similarity	NPC304203
0.7596	Intermediate Similarity	NPC326422
0.7593	Intermediate Similarity	NPC190296
0.7588	Intermediate Similarity	NPC194881
0.7584	Intermediate Similarity	NPC470205
0.7572	Intermediate Similarity	NPC471943
0.7547	Intermediate Similarity	NPC29886
0.7547	Intermediate Similarity	NPC261195
0.7545	Intermediate Similarity	NPC251391
0.7542	Intermediate Similarity	NPC46895
0.753	Intermediate Similarity	NPC313889
0.753	Intermediate Similarity	NPC473878
0.7528	Intermediate Similarity	NPC113626
0.7527	Intermediate Similarity	NPC324091
0.7516	Intermediate Similarity	NPC73767
0.7516	Intermediate Similarity	NPC110126
0.7514	Intermediate Similarity	NPC78020
0.75	Intermediate Similarity	NPC285731
0.75	Intermediate Similarity	NPC233380
0.75	Intermediate Similarity	NPC151635
0.75	Intermediate Similarity	NPC314372
0.75	Intermediate Similarity	NPC308931
0.75	Intermediate Similarity	NPC84911
0.75	Intermediate Similarity	NPC99939
0.75	Intermediate Similarity	NPC470440
0.7487	Intermediate Similarity	NPC183777
0.7486	Intermediate Similarity	NPC117244
0.7486	Intermediate Similarity	NPC473763
0.7474	Intermediate Similarity	NPC153980
0.7474	Intermediate Similarity	NPC6865
0.7471	Intermediate Similarity	NPC65080
0.7459	Intermediate Similarity	NPC294693
0.7458	Intermediate Similarity	NPC111275
0.7458	Intermediate Similarity	NPC473380
0.7458	Intermediate Similarity	NPC145885
0.7458	Intermediate Similarity	NPC14113
0.7458	Intermediate Similarity	NPC237188
0.7458	Intermediate Similarity	NPC84827
0.7458	Intermediate Similarity	NPC240088
0.7455	Intermediate Similarity	NPC478186
0.7449	Intermediate Similarity	NPC471192
0.7448	Intermediate Similarity	NPC171787
0.7438	Intermediate Similarity	NPC96102
0.7436	Intermediate Similarity	NPC313823
0.7435	Intermediate Similarity	NPC82053
0.7427	Intermediate Similarity	NPC470680
0.7427	Intermediate Similarity	NPC100104
0.7423	Intermediate Similarity	NPC72956
0.7419	Intermediate Similarity	NPC79356
0.7419	Intermediate Similarity	NPC102592
0.7418	Intermediate Similarity	NPC17059
0.7416	Intermediate Similarity	NPC55772
0.7416	Intermediate Similarity	NPC265710
0.741	Intermediate Similarity	NPC105811
0.741	Intermediate Similarity	NPC100726
0.7407	Intermediate Similarity	NPC300183
0.7401	Intermediate Similarity	NPC267885
0.7396	Intermediate Similarity	NPC209362
0.7394	Intermediate Similarity	NPC467188
0.7394	Intermediate Similarity	NPC159856
0.7391	Intermediate Similarity	NPC105127
0.7385	Intermediate Similarity	NPC471194
0.7385	Intermediate Similarity	NPC471193
0.738	Intermediate Similarity	NPC167710
0.7374	Intermediate Similarity	NPC16659
0.7365	Intermediate Similarity	NPC123906
0.7363	Intermediate Similarity	NPC94752
0.7362	Intermediate Similarity	NPC469768
0.7362	Intermediate Similarity	NPC469779
0.7362	Intermediate Similarity	NPC469761
0.7362	Intermediate Similarity	NPC469783
0.7362	Intermediate Similarity	NPC469780
0.7362	Intermediate Similarity	NPC469784
0.7362	Intermediate Similarity	NPC469767
0.7345	Intermediate Similarity	NPC149155
0.7345	Intermediate Similarity	NPC110500
0.7345	Intermediate Similarity	NPC203468
0.7338	Intermediate Similarity	NPC46358
0.7326	Intermediate Similarity	NPC472116
0.7321	Intermediate Similarity	NPC105818
0.7321	Intermediate Similarity	NPC24678
0.7318	Intermediate Similarity	NPC213468
0.7318	Intermediate Similarity	NPC248041
0.7318	Intermediate Similarity	NPC126709
0.7317	Intermediate Similarity	NPC469766
0.731	Intermediate Similarity	NPC469762
0.7305	Intermediate Similarity	NPC471957
0.7302	Intermediate Similarity	NPC237414
0.7302	Intermediate Similarity	NPC472296
0.7302	Intermediate Similarity	NPC472297
0.7301	Intermediate Similarity	NPC104483
0.7296	Intermediate Similarity	NPC82295
0.7288	Intermediate Similarity	NPC161861
0.7284	Intermediate Similarity	NPC314102
0.7284	Intermediate Similarity	NPC251722
0.7283	Intermediate Similarity	NPC473666
0.7283	Intermediate Similarity	NPC255909
0.7277	Intermediate Similarity	NPC57398
0.7268	Intermediate Similarity	NPC66210
0.7267	Intermediate Similarity	NPC474492
0.7258	Intermediate Similarity	NPC47190
0.7258	Intermediate Similarity	NPC216550
0.7256	Intermediate Similarity	NPC279081
0.7251	Intermediate Similarity	NPC469785
0.7251	Intermediate Similarity	NPC51054
0.7249	Intermediate Similarity	NPC149708
0.7247	Intermediate Similarity	NPC469938
0.7243	Intermediate Similarity	NPC83111
0.7241	Intermediate Similarity	NPC311276
0.7241	Intermediate Similarity	NPC40779
0.7238	Intermediate Similarity	NPC243381
0.7238	Intermediate Similarity	NPC275292
0.7235	Intermediate Similarity	NPC259644
0.7235	Intermediate Similarity	NPC469786
0.7235	Intermediate Similarity	NPC469760
0.7235	Intermediate Similarity	NPC469763
0.7235	Intermediate Similarity	NPC469765
0.7235	Intermediate Similarity	NPC25008
0.7235	Intermediate Similarity	NPC73952
0.7234	Intermediate Similarity	NPC128244
0.7225	Intermediate Similarity	NPC471944
0.7222	Intermediate Similarity	NPC276540
0.7222	Intermediate Similarity	NPC233050
0.7222	Intermediate Similarity	NPC283219
0.7219	Intermediate Similarity	NPC40070
0.7209	Intermediate Similarity	NPC129721
0.7209	Intermediate Similarity	NPC213914
0.7208	Intermediate Similarity	NPC219087
0.7202	Intermediate Similarity	NPC470111
0.7194	Intermediate Similarity	NPC123839
0.7193	Intermediate Similarity	NPC211572
0.7193	Intermediate Similarity	NPC80597
0.7193	Intermediate Similarity	NPC75540
0.7193	Intermediate Similarity	NPC70922
0.7193	Intermediate Similarity	NPC212376

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 NPC114637 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	737
0.2-0.3	912
0.3-0.4	2184
0.4-0.5	2238
0.5-0.6	1888
0.6-0.7	778
0.7-0.8	125
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD4848	Phase 1
0.7978	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD201	Phase 2
0.7949	Intermediate Similarity	NPD200	Phase 2
0.7844	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7564	Discontinued
0.7824	Intermediate Similarity	NPD1343	Approved
0.7821	Intermediate Similarity	NPD272	Approved
0.7809	Intermediate Similarity	NPD4988	Discontinued
0.774	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD4922	Phase 2
0.773	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1270	Approved
0.7727	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5400	Approved
0.7688	Intermediate Similarity	NPD750	Phase 2
0.768	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD7944	Discontinued
0.7617	Intermediate Similarity	NPD6787	Phase 2
0.7609	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1952	Discontinued
0.7566	Intermediate Similarity	NPD6987	Phase 1
0.7566	Intermediate Similarity	NPD3947	Discontinued
0.7556	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD5809	Phase 3
0.7539	Intermediate Similarity	NPD2509	Approved
0.7539	Intermediate Similarity	NPD2510	Approved
0.75	Intermediate Similarity	NPD4075	Phase 2
0.75	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD3320	Approved
0.7486	Intermediate Similarity	NPD3319	Phase 1
0.7486	Intermediate Similarity	NPD3318	Approved
0.7486	Intermediate Similarity	NPD1658	Discontinued
0.7471	Intermediate Similarity	NPD1630	Approved
0.7468	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD2881	Approved
0.746	Intermediate Similarity	NPD2879	Approved
0.7459	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD2008	Discontinued
0.7432	Intermediate Similarity	NPD1905	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD2511	Approved
0.7407	Intermediate Similarity	NPD786	Approved
0.7401	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6999	Discontinued
0.7394	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3654	Approved
0.7374	Intermediate Similarity	NPD2479	Phase 3
0.7374	Intermediate Similarity	NPD2481	Approved
0.7371	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7619	Phase 3
0.7366	Intermediate Similarity	NPD7618	Phase 3
0.7358	Intermediate Similarity	NPD2443	Approved
0.7358	Intermediate Similarity	NPD2442	Approved
0.7351	Intermediate Similarity	NPD7098	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5505	Discontinued
0.7345	Intermediate Similarity	NPD482	Approved
0.7344	Intermediate Similarity	NPD7001	Phase 3
0.7341	Intermediate Similarity	NPD1631	Approved
0.7333	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6176	Phase 1
0.7314	Intermediate Similarity	NPD4640	Approved
0.7314	Intermediate Similarity	NPD4638	Approved
0.7314	Intermediate Similarity	NPD4639	Approved
0.7306	Intermediate Similarity	NPD3905	Phase 3
0.7305	Intermediate Similarity	NPD4547	Phase 3
0.7297	Intermediate Similarity	NPD2336	Approved
0.7296	Intermediate Similarity	NPD7195	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4524	Discontinued
0.7287	Intermediate Similarity	NPD6664	Approved
0.7282	Intermediate Similarity	NPD4051	Discontinued
0.7282	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7661	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1573	Approved
0.7273	Intermediate Similarity	NPD1575	Approved
0.7258	Intermediate Similarity	NPD3431	Approved
0.7258	Intermediate Similarity	NPD3430	Approved
0.7254	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD3476	Approved
0.7233	Intermediate Similarity	NPD3475	Approved
0.7228	Intermediate Similarity	NPD4948	Discontinued
0.7225	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4348	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1031	Discontinued
0.7213	Intermediate Similarity	NPD5555	Phase 1
0.7213	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1722	Approved
0.7208	Intermediate Similarity	NPD2411	Approved
0.7207	Intermediate Similarity	NPD4385	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD3238	Discontinued
0.7205	Intermediate Similarity	NPD3385	Approved
0.7188	Intermediate Similarity	NPD4924	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD3389	Approved
0.7186	Intermediate Similarity	NPD3393	Approved
0.7186	Intermediate Similarity	NPD3394	Approved
0.7182	Intermediate Similarity	NPD3927	Phase 2
0.7182	Intermediate Similarity	NPD5473	Discontinued
0.7167	Intermediate Similarity	NPD2753	Discontinued
0.716	Intermediate Similarity	NPD3100	Discontinued
0.7158	Intermediate Similarity	NPD2096	Phase 2
0.7158	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD2091	Phase 2
0.7157	Intermediate Similarity	NPD5475	Discontinued
0.7152	Intermediate Similarity	NPD2118	Approved
0.7152	Intermediate Similarity	NPD2119	Approved
0.7151	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2307	Discontinued
0.7143	Intermediate Similarity	NPD2408	Discontinued
0.7136	Intermediate Similarity	NPD5293	Phase 2
0.7135	Intermediate Similarity	NPD5017	Discontinued
0.7135	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD2095	Phase 2
0.7104	Intermediate Similarity	NPD2094	Phase 2
0.7104	Intermediate Similarity	NPD2092	Phase 2
0.7104	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD2915	Discontinued
0.71	Intermediate Similarity	NPD4851	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7666	Phase 3
0.7092	Intermediate Similarity	NPD7665	Phase 2
0.7088	Intermediate Similarity	NPD1618	Phase 2
0.7066	Intermediate Similarity	NPD2006	Phase 2
0.7065	Intermediate Similarity	NPD1591	Approved
0.7059	Intermediate Similarity	NPD2430	Phase 2
0.7056	Intermediate Similarity	NPD4883	Approved
0.7056	Intermediate Similarity	NPD1586	Approved
0.7053	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD9599	Approved
0.7045	Intermediate Similarity	NPD3583	Phase 2
0.7033	Intermediate Similarity	NPD3076	Approved
0.7033	Intermediate Similarity	NPD3077	Approved
0.7033	Intermediate Similarity	NPD2590	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3079	Approved
0.7033	Intermediate Similarity	NPD3078	Approved
0.7031	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2896	Discontinued
0.7029	Intermediate Similarity	NPD1404	Approved
0.7029	Intermediate Similarity	NPD1403	Approved
0.7026	Intermediate Similarity	NPD5901	Discontinued
0.7021	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2172	Phase 1
0.7011	Intermediate Similarity	NPD4326	Phase 2
0.701	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5020	Approved
0.7005	Intermediate Similarity	NPD5421	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5888	Phase 2
0.6995	Remote Similarity	NPD5898	Approved
0.6995	Remote Similarity	NPD5899	Approved
0.6995	Remote Similarity	NPD5897	Approved
0.6994	Remote Similarity	NPD4029	Approved
0.6994	Remote Similarity	NPD2061	Approved
0.6994	Remote Similarity	NPD4030	Approved
0.6994	Remote Similarity	NPD4028	Approved
0.6989	Remote Similarity	NPD6217	Discontinued
0.6987	Remote Similarity	NPD268	Approved
0.6987	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD271	Approved
0.6978	Remote Similarity	NPD2144	Approved
0.6978	Remote Similarity	NPD3506	Approved
0.6978	Remote Similarity	NPD3505	Approved
0.697	Remote Similarity	NPD1600	Suspended
0.6966	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6226	Phase 3
0.6963	Remote Similarity	NPD2290	Phase 3
0.6963	Remote Similarity	NPD2289	Phase 3
0.6959	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4852	Phase 2
0.6947	Remote Similarity	NPD460	Discontinued
0.6943	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.694	Remote Similarity	NPD4079	Approved
0.694	Remote Similarity	NPD1587	Approved
0.694	Remote Similarity	NPD4076	Approved
0.6939	Remote Similarity	NPD4299	Phase 1
0.6939	Remote Similarity	NPD5426	Phase 3
0.6936	Remote Similarity	NPD2837	Discontinued
0.6933	Remote Similarity	NPD9100	Approved
0.6927	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4845	Discontinued
0.6923	Remote Similarity	NPD5104	Approved
0.6915	Remote Similarity	NPD2363	Discontinued
0.6915	Remote Similarity	NPD4334	Discontinued
0.6911	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.691	Remote Similarity	NPD2720	Phase 1
0.691	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD5491	Phase 3

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