NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	326.15
Volume:	339.592
LogP:	4.757
LogD:	3.289
LogS:	-3.422
# Rotatable Bonds:	0
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.642
Synthetic Accessibility Score:	3.435
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.929
MDCK Permeability:	2.1245206880848855e-05
Pgp-inhibitor:	0.149
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.879
30% Bioavailability (F30%):	0.057

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	99.42493438720703%
Volume Distribution (VD):	0.925
Pgp-substrate:	1.1030359268188477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.201
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.363
CYP2C19-substrate:	0.522
CYP2C9-inhibitor:	0.382
CYP2C9-substrate:	0.943
CYP2D6-inhibitor:	0.463
CYP2D6-substrate:	0.629
CYP3A4-inhibitor:	0.141
CYP3A4-substrate:	0.669

ADMET: Excretion

Clearance (CL):	8.664
Half-life (T1/2):	0.558

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.411
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.066
Rat Oral Acute Toxicity:	0.267
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.918
Carcinogencity:	0.211
Eye Corrosion:	0.003
Eye Irritation:	0.658
Respiratory Toxicity:	0.328

Download Data

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

Natural Product: NPC71037

Natural Product ID:	NPC71037
*Common Name:**	2-(1H-Indol-3-Yl)Ethyl 5-Hydroxypentanoate
IUPAC Name:	2-(1H-indol-3-yl)ethyl 5-hydroxypentanoate
Synonyms:
Standard InCHIKey:	BFTWGRUJKFQXOW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H19NO3/c17-9-4-3-7-15(18)19-10-8-12-11-16-14-6-2-1-5-13(12)14/h1-2,5-6,11,16-17H,3-4,7-10H2
SMILES:	OCCCCC(=O)OCCc1c[nH]c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087748
PubChem CID:	44605902
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
NPO2605	Pichia membranifaciens	Species	Pichiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19943625]
NPO2605	Pichia membranifaciens	Species	Pichiaceae	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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		Activity	=	47.0	%	PMID[493698]

☑ 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 NPC71037 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	243
0.1-0.2	1994
0.2-0.3	13167
0.3-0.4	18573
0.4-0.5	4109
0.5-0.6	2058
0.6-0.7	1808
0.7-0.8	635
0.8-0.85	78
0.85-0.9	27
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9112	High Similarity	NPC469358
0.9102	High Similarity	NPC111275
0.9068	High Similarity	NPC230869
0.9064	High Similarity	NPC315555
0.897	High Similarity	NPC78020
0.8757	High Similarity	NPC110500
0.8757	High Similarity	NPC203468
0.8757	High Similarity	NPC149155
0.8706	High Similarity	NPC267885
0.8659	High Similarity	NPC469762
0.8605	High Similarity	NPC248041
0.8605	High Similarity	NPC55772
0.8605	High Similarity	NPC283219
0.8605	High Similarity	NPC126709
0.8598	High Similarity	NPC469785
0.8588	High Similarity	NPC154339
0.8563	High Similarity	NPC311276
0.8563	High Similarity	NPC102423
0.8523	High Similarity	NPC235684
0.8497	Intermediate Similarity	NPC213468
0.8478	Intermediate Similarity	NPC476874
0.8462	Intermediate Similarity	NPC54988
0.8444	Intermediate Similarity	NPC267343
0.8439	Intermediate Similarity	NPC14113
0.8439	Intermediate Similarity	NPC84827
0.8439	Intermediate Similarity	NPC145885
0.8418	Intermediate Similarity	NPC62749
0.8372	Intermediate Similarity	NPC313791
0.8364	Intermediate Similarity	NPC73952
0.8364	Intermediate Similarity	NPC25008
0.8364	Intermediate Similarity	NPC469763
0.8364	Intermediate Similarity	NPC259644
0.8364	Intermediate Similarity	NPC469760
0.8364	Intermediate Similarity	NPC469765
0.8364	Intermediate Similarity	NPC469786
0.8343	Intermediate Similarity	NPC88315
0.8343	Intermediate Similarity	NPC40779
0.8333	Intermediate Similarity	NPC131718
0.8333	Intermediate Similarity	NPC279918
0.8324	Intermediate Similarity	NPC321708
0.8313	Intermediate Similarity	NPC211572
0.8313	Intermediate Similarity	NPC70922
0.8313	Intermediate Similarity	NPC80597
0.8313	Intermediate Similarity	NPC212376
0.8313	Intermediate Similarity	NPC75540
0.8284	Intermediate Similarity	NPC282231
0.8278	Intermediate Similarity	NPC83111
0.8268	Intermediate Similarity	NPC278434
0.8258	Intermediate Similarity	NPC188387
0.8258	Intermediate Similarity	NPC163421
0.8246	Intermediate Similarity	NPC49954
0.8246	Intermediate Similarity	NPC160105
0.8246	Intermediate Similarity	NPC474561
0.8229	Intermediate Similarity	NPC229348
0.8221	Intermediate Similarity	NPC314372
0.8207	Intermediate Similarity	NPC156704
0.8201	Intermediate Similarity	NPC88008
0.8198	Intermediate Similarity	NPC63751
0.8198	Intermediate Similarity	NPC201700
0.8182	Intermediate Similarity	NPC193761
0.8172	Intermediate Similarity	NPC213308
0.8162	Intermediate Similarity	NPC67288
0.8132	Intermediate Similarity	NPC138370
0.8098	Intermediate Similarity	NPC190296
0.809	Intermediate Similarity	NPC233936
0.8075	Intermediate Similarity	NPC470497
0.8075	Intermediate Similarity	NPC315491
0.8075	Intermediate Similarity	NPC45459
0.8057	Intermediate Similarity	NPC314603
0.8045	Intermediate Similarity	NPC163055
0.8023	Intermediate Similarity	NPC15573
0.8023	Intermediate Similarity	NPC183662
0.8023	Intermediate Similarity	NPC194640
0.8023	Intermediate Similarity	NPC151939
0.8023	Intermediate Similarity	NPC217372
0.8022	Intermediate Similarity	NPC175474
0.8011	Intermediate Similarity	NPC262898
0.8	Intermediate Similarity	NPC159856
0.7989	Intermediate Similarity	NPC317430
0.7978	Intermediate Similarity	NPC95783
0.7978	Intermediate Similarity	NPC219336
0.797	Intermediate Similarity	NPC281049
0.7968	Intermediate Similarity	NPC131887
0.7968	Intermediate Similarity	NPC470499
0.7957	Intermediate Similarity	NPC251090
0.7957	Intermediate Similarity	NPC179701
0.7956	Intermediate Similarity	NPC15102
0.7956	Intermediate Similarity	NPC280290
0.7933	Intermediate Similarity	NPC469896
0.7927	Intermediate Similarity	NPC478158
0.7926	Intermediate Similarity	NPC100321
0.7926	Intermediate Similarity	NPC293917
0.7923	Intermediate Similarity	NPC213629
0.7921	Intermediate Similarity	NPC59269
0.7921	Intermediate Similarity	NPC248454
0.7917	Intermediate Similarity	NPC24678
0.7917	Intermediate Similarity	NPC105818
0.7914	Intermediate Similarity	NPC272483
0.7912	Intermediate Similarity	NPC94752
0.7908	Intermediate Similarity	NPC313640
0.7908	Intermediate Similarity	NPC478157
0.7869	Intermediate Similarity	NPC317030
0.7869	Intermediate Similarity	NPC46580
0.7869	Intermediate Similarity	NPC17059
0.7857	Intermediate Similarity	NPC314002
0.7857	Intermediate Similarity	NPC62510
0.7845	Intermediate Similarity	NPC220765
0.784	Intermediate Similarity	NPC29886
0.784	Intermediate Similarity	NPC261195
0.784	Intermediate Similarity	NPC96102
0.7839	Intermediate Similarity	NPC74360
0.7833	Intermediate Similarity	NPC300688
0.7819	Intermediate Similarity	NPC227582
0.7814	Intermediate Similarity	NPC474707
0.7814	Intermediate Similarity	NPC171171
0.7806	Intermediate Similarity	NPC219087
0.7805	Intermediate Similarity	NPC73767
0.7802	Intermediate Similarity	NPC204717
0.7802	Intermediate Similarity	NPC228835
0.7801	Intermediate Similarity	NPC476073
0.7798	Intermediate Similarity	NPC471957
0.7797	Intermediate Similarity	NPC470498
0.7791	Intermediate Similarity	NPC84911
0.7791	Intermediate Similarity	NPC105127
0.7778	Intermediate Similarity	NPC11126
0.7778	Intermediate Similarity	NPC473640
0.7772	Intermediate Similarity	NPC204565
0.7771	Intermediate Similarity	NPC42372
0.7766	Intermediate Similarity	NPC54744
0.7761	Intermediate Similarity	NPC2395
0.776	Intermediate Similarity	NPC98715
0.7758	Intermediate Similarity	NPC469767
0.7758	Intermediate Similarity	NPC469779
0.7758	Intermediate Similarity	NPC469783
0.7758	Intermediate Similarity	NPC469784
0.7758	Intermediate Similarity	NPC469761
0.7758	Intermediate Similarity	NPC469780
0.7758	Intermediate Similarity	NPC469768
0.7754	Intermediate Similarity	NPC307963
0.7749	Intermediate Similarity	NPC475506
0.7749	Intermediate Similarity	NPC300183
0.7747	Intermediate Similarity	NPC139291
0.7747	Intermediate Similarity	NPC472108
0.7747	Intermediate Similarity	NPC48938
0.7737	Intermediate Similarity	NPC241024
0.7733	Intermediate Similarity	NPC285469
0.7732	Intermediate Similarity	NPC323927
0.773	Intermediate Similarity	NPC173028
0.773	Intermediate Similarity	NPC65215
0.7722	Intermediate Similarity	NPC68354
0.7722	Intermediate Similarity	NPC184964
0.772	Intermediate Similarity	NPC473376
0.7716	Intermediate Similarity	NPC75634
0.7713	Intermediate Similarity	NPC195239
0.7713	Intermediate Similarity	NPC202812
0.7713	Intermediate Similarity	NPC157828
0.7711	Intermediate Similarity	NPC469766
0.7709	Intermediate Similarity	NPC37423
0.7709	Intermediate Similarity	NPC275305
0.7708	Intermediate Similarity	NPC155143
0.7705	Intermediate Similarity	NPC165495
0.7702	Intermediate Similarity	NPC82295
0.7701	Intermediate Similarity	NPC55493
0.7701	Intermediate Similarity	NPC99666
0.7697	Intermediate Similarity	NPC110126
0.7696	Intermediate Similarity	NPC252338
0.7692	Intermediate Similarity	NPC243381
0.7692	Intermediate Similarity	NPC275292
0.7692	Intermediate Similarity	NPC171787
0.7685	Intermediate Similarity	NPC64216
0.7684	Intermediate Similarity	NPC171317
0.7684	Intermediate Similarity	NPC52557
0.7677	Intermediate Similarity	NPC221100
0.7677	Intermediate Similarity	NPC234078
0.7672	Intermediate Similarity	NPC11445
0.7665	Intermediate Similarity	NPC82370
0.7665	Intermediate Similarity	NPC320968
0.7661	Intermediate Similarity	NPC216713
0.7653	Intermediate Similarity	NPC271862
0.7651	Intermediate Similarity	NPC279081
0.765	Intermediate Similarity	NPC472109
0.765	Intermediate Similarity	NPC472285
0.765	Intermediate Similarity	NPC472110
0.7647	Intermediate Similarity	NPC235885
0.7647	Intermediate Similarity	NPC125597
0.7644	Intermediate Similarity	NPC135141
0.7644	Intermediate Similarity	NPC92796
0.7644	Intermediate Similarity	NPC74413
0.7641	Intermediate Similarity	NPC54420
0.7641	Intermediate Similarity	NPC225821
0.7641	Intermediate Similarity	NPC46225
0.7638	Intermediate Similarity	NPC474412
0.7634	Intermediate Similarity	NPC102338
0.7634	Intermediate Similarity	NPC63199
0.7634	Intermediate Similarity	NPC196251
0.7634	Intermediate Similarity	NPC111602
0.763	Intermediate Similarity	NPC141353
0.7626	Intermediate Similarity	NPC151976
0.7626	Intermediate Similarity	NPC207020
0.7626	Intermediate Similarity	NPC87856

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 NPC71037 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	519
0.2-0.3	915
0.3-0.4	1511
0.4-0.5	2773
0.5-0.6	2234
0.6-0.7	850
0.7-0.8	161
0.8-0.85	5
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD2092	Phase 2
0.8889	High Similarity	NPD2095	Phase 2
0.8889	High Similarity	NPD2094	Phase 2
0.8837	High Similarity	NPD2096	Phase 2
0.8837	High Similarity	NPD2091	Phase 2
0.8757	High Similarity	NPD482	Approved
0.8706	High Similarity	NPD749	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD750	Phase 2
0.8352	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD484	Approved
0.8034	Intermediate Similarity	NPD6595	Phase 3
0.8023	Intermediate Similarity	NPD2144	Approved
0.8	Intermediate Similarity	NPD5901	Discontinued
0.7947	Intermediate Similarity	NPD8072	Approved
0.7947	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD7470	Discontinued
0.7926	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD5065	Approved
0.7889	Intermediate Similarity	NPD3038	Discontinued
0.7886	Intermediate Similarity	NPD2844	Phase 3
0.7865	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD7957	Phase 1
0.784	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5426	Phase 3
0.7805	Intermediate Similarity	NPD786	Approved
0.7801	Intermediate Similarity	NPD8073	Approved
0.7784	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD2509	Approved
0.7784	Intermediate Similarity	NPD2510	Approved
0.7778	Intermediate Similarity	NPD4076	Approved
0.7778	Intermediate Similarity	NPD4079	Approved
0.7754	Intermediate Similarity	NPD1038	Approved
0.7725	Intermediate Similarity	NPD5003	Discontinued
0.7722	Intermediate Similarity	NPD3506	Approved
0.7722	Intermediate Similarity	NPD3505	Approved
0.7711	Intermediate Similarity	NPD1722	Approved
0.764	Intermediate Similarity	NPD1326	Approved
0.764	Intermediate Similarity	NPD1325	Approved
0.7638	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD8272	Phase 2
0.7624	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD4600	Approved
0.7604	Intermediate Similarity	NPD4601	Approved
0.7602	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD3178	Discontinued
0.7594	Intermediate Similarity	NPD4499	Approved
0.7594	Intermediate Similarity	NPD2564	Approved
0.7594	Intermediate Similarity	NPD2565	Phase 2
0.7581	Intermediate Similarity	NPD8431	Approved
0.7576	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD802	Phase 2
0.754	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2896	Discontinued
0.7525	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD4501	Approved
0.7513	Intermediate Similarity	NPD4500	Approved
0.7512	Intermediate Similarity	NPD3389	Approved
0.7512	Intermediate Similarity	NPD3393	Approved
0.7512	Intermediate Similarity	NPD3394	Approved
0.75	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD2809	Approved
0.7462	Intermediate Similarity	NPD1392	Approved
0.7448	Intermediate Similarity	NPD7948	Phase 1
0.7447	Intermediate Similarity	NPD1534	Approved
0.7446	Intermediate Similarity	NPD5898	Approved
0.7446	Intermediate Similarity	NPD5897	Approved
0.7446	Intermediate Similarity	NPD5899	Approved
0.7442	Intermediate Similarity	NPD3100	Discontinued
0.7442	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6178	Phase 3
0.7411	Intermediate Similarity	NPD7001	Phase 3
0.7403	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD2172	Phase 1
0.7396	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1592	Phase 3
0.7389	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4703	Approved
0.7384	Intermediate Similarity	NPD4702	Approved
0.7374	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6987	Phase 1
0.7344	Intermediate Similarity	NPD7944	Discontinued
0.7303	Intermediate Similarity	NPD1403	Approved
0.7303	Intermediate Similarity	NPD1404	Approved
0.7299	Intermediate Similarity	NPD4462	Approved
0.7299	Intermediate Similarity	NPD4463	Approved
0.7293	Intermediate Similarity	NPD4638	Approved
0.7293	Intermediate Similarity	NPD4640	Approved
0.7293	Intermediate Similarity	NPD4639	Approved
0.7291	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD7970	Approved
0.7283	Intermediate Similarity	NPD4075	Phase 2
0.7282	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6999	Discontinued
0.7277	Intermediate Similarity	NPD8093	Discontinued
0.7273	Intermediate Similarity	NPD3947	Discontinued
0.7258	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5612	Discontinued
0.7254	Intermediate Similarity	NPD7619	Phase 3
0.7254	Intermediate Similarity	NPD7618	Phase 3
0.7254	Intermediate Similarity	NPD4427	Phase 2
0.7245	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD8094	Discontinued
0.724	Intermediate Similarity	NPD6665	Discontinued
0.724	Intermediate Similarity	NPD3404	Approved
0.7238	Intermediate Similarity	NPD5611	Phase 2
0.7234	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7778	Approved
0.7231	Intermediate Similarity	NPD7777	Approved
0.7231	Intermediate Similarity	NPD53	Approved
0.7222	Intermediate Similarity	NPD5138	Approved
0.7222	Intermediate Similarity	NPD5140	Approved
0.7222	Intermediate Similarity	NPD6176	Phase 1
0.7216	Intermediate Similarity	NPD2837	Discontinued
0.7214	Intermediate Similarity	NPD6529	Discontinued
0.7211	Intermediate Similarity	NPD4948	Discontinued
0.7207	Intermediate Similarity	NPD2511	Approved
0.7198	Intermediate Similarity	NPD5862	Discovery
0.7194	Intermediate Similarity	NPD3825	Phase 3
0.7192	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7711	Discontinued
0.7189	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5596	Phase 2
0.7175	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7233	Approved
0.7173	Intermediate Similarity	NPD7234	Approved
0.7166	Intermediate Similarity	NPD6452	Discontinued
0.7158	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD3794	Approved
0.7157	Intermediate Similarity	NPD6479	Discontinued
0.7157	Intermediate Similarity	NPD3795	Approved
0.7143	Intermediate Similarity	NPD5067	Phase 2
0.7143	Intermediate Similarity	NPD5066	Phase 2
0.7143	Intermediate Similarity	NPD2642	Approved
0.7143	Intermediate Similarity	NPD2639	Approved
0.7143	Intermediate Similarity	NPD5475	Discontinued
0.7136	Intermediate Similarity	NPD2920	Discontinued
0.7135	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4128	Approved
0.7129	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD3961	Discontinued
0.7115	Intermediate Similarity	NPD6242	Discontinued
0.7112	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD8386	Phase 2
0.7112	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3330	Phase 1
0.7107	Intermediate Similarity	NPD1768	Approved
0.7104	Intermediate Similarity	NPD2640	Approved
0.7104	Intermediate Similarity	NPD2641	Approved
0.7104	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5072	Discontinued
0.7092	Intermediate Similarity	NPD6664	Approved
0.709	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1661	Suspended
0.7077	Intermediate Similarity	NPD4602	Approved
0.7075	Intermediate Similarity	NPD7731	Approved
0.7075	Intermediate Similarity	NPD6165	Phase 2
0.7075	Intermediate Similarity	NPD6164	Phase 2
0.7075	Intermediate Similarity	NPD7730	Approved
0.7072	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2305	Discontinued
0.707	Intermediate Similarity	NPD7558	Phase 2
0.7065	Intermediate Similarity	NPD3003	Approved
0.7062	Intermediate Similarity	NPD7271	Approved
0.7059	Intermediate Similarity	NPD4181	Approved
0.7059	Intermediate Similarity	NPD7865	Approved
0.7056	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4397	Phase 1
0.7053	Intermediate Similarity	NPD1096	Discontinued
0.7053	Intermediate Similarity	NPD5818	Discontinued
0.7052	Intermediate Similarity	NPD3717	Discontinued
0.7049	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6281	Approved
0.7044	Intermediate Similarity	NPD4506	Discontinued
0.7033	Intermediate Similarity	NPD3323	Discontinued
0.7031	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3354	Phase 2
0.7018	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5021	Discontinued
0.701	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4699	Discontinued
0.701	Intermediate Similarity	NPD5913	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