NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	203.09
Volume:	214.39
LogP:	2.339
LogD:	2.413
LogS:	-2.32
# Rotatable Bonds:	1
TPSA:	42.35
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.774
Synthetic Accessibility Score:	2.4
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.629
MDCK Permeability:	1.760128725436516e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.818
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.89
30% Bioavailability (F30%):	0.629

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.681
Plasma Protein Binding (PPB):	91.79566192626953%
Volume Distribution (VD):	0.989
Pgp-substrate:	8.704398155212402%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.765
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.791
CYP2D6-inhibitor:	0.167
CYP2D6-substrate:	0.907
CYP3A4-inhibitor:	0.096
CYP3A4-substrate:	0.287

ADMET: Excretion

Clearance (CL):	11.881
Half-life (T1/2):	0.648

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.38
Drug-inuced Liver Injury (DILI):	0.903
AMES Toxicity:	0.499
Rat Oral Acute Toxicity:	0.603
Maximum Recommended Daily Dose:	0.24
Skin Sensitization:	0.658
Carcinogencity:	0.314
Eye Corrosion:	0.052
Eye Irritation:	0.958
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC224928

Natural Product ID:	NPC224928
*Common Name:**	UBELMBVSZFQTKZ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UBELMBVSZFQTKZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H13NO2/c1-7-4-9-8(2)11(14)5-12(15-3)10(9)6-13-7/h4-6,14H,1-3H3
SMILES:	Cc1cc2c(C)c(cc(c2cn1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2385865
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730261]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15973055]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18656987]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21053938]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	Moroccan	n.a.	PMID[23713692]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26295595]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7766039]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	>	10000.0	nM	PMID[462982]

☑ 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 NPC224928 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	574
0.1-0.2	3223
0.2-0.3	13329
0.3-0.4	4077
0.4-0.5	11198
0.5-0.6	8222
0.6-0.7	1724
0.7-0.8	311
0.8-0.85	26
0.85-0.9	12
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.895	High Similarity	NPC469390
0.8939	High Similarity	NPC61350
0.8821	High Similarity	NPC473822
0.8731	High Similarity	NPC174049
0.8643	High Similarity	NPC122463
0.8595	High Similarity	NPC114335
0.8595	High Similarity	NPC280964
0.8595	High Similarity	NPC141915
0.8586	High Similarity	NPC137929
0.8586	High Similarity	NPC164374
0.836	Intermediate Similarity	NPC473053
0.835	Intermediate Similarity	NPC201508
0.8342	Intermediate Similarity	NPC469440
0.8283	Intermediate Similarity	NPC202605
0.8283	Intermediate Similarity	NPC112206
0.8216	Intermediate Similarity	NPC62069
0.8201	Intermediate Similarity	NPC195268
0.8201	Intermediate Similarity	NPC133140
0.8182	Intermediate Similarity	NPC96584
0.8182	Intermediate Similarity	NPC255800
0.8158	Intermediate Similarity	NPC289786
0.8112	Intermediate Similarity	NPC476581
0.8112	Intermediate Similarity	NPC16452
0.8112	Intermediate Similarity	NPC36229
0.8038	Intermediate Similarity	NPC469792
0.7963	Intermediate Similarity	NPC15406
0.7959	Intermediate Similarity	NPC31930
0.7949	Intermediate Similarity	NPC476582
0.7949	Intermediate Similarity	NPC476578
0.7949	Intermediate Similarity	NPC4071
0.7944	Intermediate Similarity	NPC473057
0.7908	Intermediate Similarity	NPC477019
0.786	Intermediate Similarity	NPC11408
0.7857	Intermediate Similarity	NPC287437
0.7837	Intermediate Similarity	NPC118121
0.7833	Intermediate Similarity	NPC296482
0.7833	Intermediate Similarity	NPC251160
0.7833	Intermediate Similarity	NPC53069
0.7833	Intermediate Similarity	NPC202768
0.7817	Intermediate Similarity	NPC234197
0.7816	Intermediate Similarity	NPC173080
0.7801	Intermediate Similarity	NPC66083
0.7793	Intermediate Similarity	NPC233334
0.779	Intermediate Similarity	NPC177404
0.7789	Intermediate Similarity	NPC42591
0.7788	Intermediate Similarity	NPC217554
0.7783	Intermediate Similarity	NPC134637
0.776	Intermediate Similarity	NPC108469
0.7754	Intermediate Similarity	NPC283152
0.775	Intermediate Similarity	NPC165349
0.775	Intermediate Similarity	NPC274291
0.775	Intermediate Similarity	NPC264166
0.775	Intermediate Similarity	NPC118832
0.775	Intermediate Similarity	NPC47059
0.775	Intermediate Similarity	NPC329708
0.7748	Intermediate Similarity	NPC183537
0.7745	Intermediate Similarity	NPC171409
0.7745	Intermediate Similarity	NPC96405
0.774	Intermediate Similarity	NPC469439
0.7734	Intermediate Similarity	NPC470020
0.7734	Intermediate Similarity	NPC11464
0.7727	Intermediate Similarity	NPC107123
0.7721	Intermediate Similarity	NPC90875
0.7711	Intermediate Similarity	NPC470164
0.7711	Intermediate Similarity	NPC323345
0.7707	Intermediate Similarity	NPC474594
0.7704	Intermediate Similarity	NPC251090
0.7701	Intermediate Similarity	NPC288943
0.7682	Intermediate Similarity	NPC284141
0.7673	Intermediate Similarity	NPC193238
0.7673	Intermediate Similarity	NPC313189
0.767	Intermediate Similarity	NPC235076
0.7668	Intermediate Similarity	NPC77878
0.7659	Intermediate Similarity	NPC316981
0.7644	Intermediate Similarity	NPC204446
0.7642	Intermediate Similarity	NPC200888
0.7633	Intermediate Similarity	NPC8022
0.7633	Intermediate Similarity	NPC470799
0.7632	Intermediate Similarity	NPC470474
0.7626	Intermediate Similarity	NPC119134
0.7609	Intermediate Similarity	NPC471178
0.7602	Intermediate Similarity	NPC307963
0.7602	Intermediate Similarity	NPC329541
0.76	Intermediate Similarity	NPC232727
0.7586	Intermediate Similarity	NPC193777
0.7586	Intermediate Similarity	NPC135549
0.7576	Intermediate Similarity	NPC243834
0.7576	Intermediate Similarity	NPC70956
0.7574	Intermediate Similarity	NPC210256
0.757	Intermediate Similarity	NPC476997
0.757	Intermediate Similarity	NPC476994
0.7562	Intermediate Similarity	NPC66815
0.7561	Intermediate Similarity	NPC290689
0.756	Intermediate Similarity	NPC23614
0.756	Intermediate Similarity	NPC100079
0.7554	Intermediate Similarity	NPC263439
0.7545	Intermediate Similarity	NPC210296
0.7537	Intermediate Similarity	NPC304183
0.7536	Intermediate Similarity	NPC162530
0.7535	Intermediate Similarity	NPC476998
0.7535	Intermediate Similarity	NPC24019
0.7535	Intermediate Similarity	NPC476996
0.7524	Intermediate Similarity	NPC193267
0.7524	Intermediate Similarity	NPC213530
0.7524	Intermediate Similarity	NPC46451
0.7524	Intermediate Similarity	NPC148409
0.7523	Intermediate Similarity	NPC124313
0.7513	Intermediate Similarity	NPC279401
0.7513	Intermediate Similarity	NPC79293
0.7511	Intermediate Similarity	NPC207283
0.7511	Intermediate Similarity	NPC84164
0.75	Intermediate Similarity	NPC210434
0.7488	Intermediate Similarity	NPC285558
0.7488	Intermediate Similarity	NPC246381
0.7488	Intermediate Similarity	NPC54066
0.7487	Intermediate Similarity	NPC296527
0.7476	Intermediate Similarity	NPC188420
0.7463	Intermediate Similarity	NPC176538
0.7463	Intermediate Similarity	NPC315957
0.7463	Intermediate Similarity	NPC470931
0.7459	Intermediate Similarity	NPC26872
0.7453	Intermediate Similarity	NPC310118
0.7452	Intermediate Similarity	NPC236668
0.7452	Intermediate Similarity	NPC266931
0.7451	Intermediate Similarity	NPC472111
0.7449	Intermediate Similarity	NPC76748
0.744	Intermediate Similarity	NPC208284
0.7438	Intermediate Similarity	NPC475774
0.7437	Intermediate Similarity	NPC13880
0.7436	Intermediate Similarity	NPC46580
0.7429	Intermediate Similarity	NPC473513
0.7427	Intermediate Similarity	NPC174758
0.7427	Intermediate Similarity	NPC185782
0.7416	Intermediate Similarity	NPC146976
0.7415	Intermediate Similarity	NPC474595
0.7411	Intermediate Similarity	NPC92111
0.7405	Intermediate Similarity	NPC59779
0.7405	Intermediate Similarity	NPC124542
0.7405	Intermediate Similarity	NPC471177
0.7394	Intermediate Similarity	NPC314940
0.7394	Intermediate Similarity	NPC473764
0.7387	Intermediate Similarity	NPC146724
0.7387	Intermediate Similarity	NPC131017
0.7383	Intermediate Similarity	NPC322482
0.7381	Intermediate Similarity	NPC170114
0.7368	Intermediate Similarity	NPC149471
0.7368	Intermediate Similarity	NPC271215
0.7366	Intermediate Similarity	NPC97367
0.7364	Intermediate Similarity	NPC108342
0.7363	Intermediate Similarity	NPC127085
0.7358	Intermediate Similarity	NPC17565
0.7354	Intermediate Similarity	NPC252590
0.7343	Intermediate Similarity	NPC174672
0.7337	Intermediate Similarity	NPC26850
0.7337	Intermediate Similarity	NPC132680
0.7337	Intermediate Similarity	NPC269919
0.7333	Intermediate Similarity	NPC470549
0.7333	Intermediate Similarity	NPC314002
0.733	Intermediate Similarity	NPC189903
0.733	Intermediate Similarity	NPC182907
0.733	Intermediate Similarity	NPC476995
0.7321	Intermediate Similarity	NPC26679
0.7321	Intermediate Similarity	NPC48353
0.7313	Intermediate Similarity	NPC267928
0.7308	Intermediate Similarity	NPC167860
0.7308	Intermediate Similarity	NPC123976
0.7306	Intermediate Similarity	NPC168486
0.7306	Intermediate Similarity	NPC222592
0.7304	Intermediate Similarity	NPC475085
0.7304	Intermediate Similarity	NPC475112
0.7304	Intermediate Similarity	NPC291535
0.7297	Intermediate Similarity	NPC166722
0.7295	Intermediate Similarity	NPC82548
0.7295	Intermediate Similarity	NPC18348
0.729	Intermediate Similarity	NPC60621
0.7286	Intermediate Similarity	NPC99666
0.7282	Intermediate Similarity	NPC204717
0.7282	Intermediate Similarity	NPC320394
0.7282	Intermediate Similarity	NPC84478
0.7281	Intermediate Similarity	NPC110151
0.7278	Intermediate Similarity	NPC161292
0.7277	Intermediate Similarity	NPC312872
0.7273	Intermediate Similarity	NPC119649
0.7273	Intermediate Similarity	NPC271388
0.7273	Intermediate Similarity	NPC235143
0.7273	Intermediate Similarity	NPC230956
0.7273	Intermediate Similarity	NPC205255
0.7268	Intermediate Similarity	NPC219963
0.7268	Intermediate Similarity	NPC161887
0.7268	Intermediate Similarity	NPC245816
0.7268	Intermediate Similarity	NPC476138
0.7268	Intermediate Similarity	NPC266551
0.7264	Intermediate Similarity	NPC194967
0.7263	Intermediate Similarity	NPC14651
0.7263	Intermediate Similarity	NPC121658
0.726	Intermediate Similarity	NPC469589
0.7235	Intermediate Similarity	NPC470018
0.7234	Intermediate Similarity	NPC79402
0.7234	Intermediate Similarity	NPC80759
0.7231	Intermediate Similarity	NPC220765

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 NPC224928 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	685
0.2-0.3	877
0.3-0.4	1487
0.4-0.5	2694
0.5-0.6	2340
0.6-0.7	644
0.7-0.8	94
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.85	High Similarity	NPD1620	Clinical (unspecified phase)
0.8407	Intermediate Similarity	NPD3386	Phase 2
0.8351	Intermediate Similarity	NPD6361	Phase 2
0.8226	Intermediate Similarity	NPD4375	Approved
0.8201	Intermediate Similarity	NPD3923	Approved
0.8201	Intermediate Similarity	NPD3921	Approved
0.8201	Intermediate Similarity	NPD3924	Approved
0.8201	Intermediate Similarity	NPD3922	Approved
0.8158	Intermediate Similarity	NPD4551	Phase 2
0.8142	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.81	Intermediate Similarity	NPD7069	Discontinued
0.8011	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD3816	Phase 1
0.7833	Intermediate Similarity	NPD3815	Phase 1
0.7824	Intermediate Similarity	NPD6569	Phase 2
0.7757	Intermediate Similarity	NPD6494	Phase 2
0.7752	Intermediate Similarity	NPD1483	Discontinued
0.775	Intermediate Similarity	NPD4038	Approved
0.775	Intermediate Similarity	NPD4033	Approved
0.775	Intermediate Similarity	NPD4122	Approved
0.775	Intermediate Similarity	NPD4039	Approved
0.775	Intermediate Similarity	NPD4037	Approved
0.775	Intermediate Similarity	NPD4036	Approved
0.775	Intermediate Similarity	NPD32	Approved
0.775	Intermediate Similarity	NPD4035	Approved
0.775	Intermediate Similarity	NPD31	Approved
0.775	Intermediate Similarity	NPD4034	Approved
0.7713	Intermediate Similarity	NPD3920	Phase 2
0.7685	Intermediate Similarity	NPD4437	Phase 3
0.7634	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD4889	Approved
0.7602	Intermediate Similarity	NPD1038	Approved
0.759	Intermediate Similarity	NPD2334	Discontinued
0.7563	Intermediate Similarity	NPD3395	Approved
0.7563	Intermediate Similarity	NPD3396	Approved
0.755	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD3763	Approved
0.7488	Intermediate Similarity	NPD4795	Phase 2
0.7487	Intermediate Similarity	NPD4021	Phase 2
0.7487	Intermediate Similarity	NPD1229	Phase 2
0.7475	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD1740	Approved
0.7463	Intermediate Similarity	NPD1739	Approved
0.746	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5530	Phase 1
0.7436	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5100	Phase 3
0.7419	Intermediate Similarity	NPD926	Approved
0.7419	Intermediate Similarity	NPD925	Approved
0.7418	Intermediate Similarity	NPD1856	Discontinued
0.7415	Intermediate Similarity	NPD7222	Phase 2
0.74	Intermediate Similarity	NPD2952	Discontinued
0.7389	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4203	Approved
0.7358	Intermediate Similarity	NPD4204	Approved
0.7356	Intermediate Similarity	NPD4502	Phase 2
0.734	Intermediate Similarity	NPD7134	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD2781	Approved
0.7337	Intermediate Similarity	NPD9382	Approved
0.7337	Intermediate Similarity	NPD9383	Approved
0.7327	Intermediate Similarity	NPD4052	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD2780	Approved
0.7326	Intermediate Similarity	NPD2782	Approved
0.7324	Intermediate Similarity	NPD6856	Discontinued
0.7313	Intermediate Similarity	NPD1622	Discontinued
0.7304	Intermediate Similarity	NPD6975	Discontinued
0.7299	Intermediate Similarity	NPD5612	Discontinued
0.7295	Intermediate Similarity	NPD2739	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4350	Approved
0.7289	Intermediate Similarity	NPD4349	Approved
0.7273	Intermediate Similarity	NPD7558	Phase 2
0.7246	Intermediate Similarity	NPD7452	Approved
0.7246	Intermediate Similarity	NPD7453	Approved
0.723	Intermediate Similarity	NPD6568	Discontinued
0.722	Intermediate Similarity	NPD7123	Suspended
0.7213	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6500	Approved
0.7196	Intermediate Similarity	NPD6501	Approved
0.7194	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD9690	Approved
0.7169	Intermediate Similarity	NPD7555	Discontinued
0.7166	Intermediate Similarity	NPD9705	Discontinued
0.7166	Intermediate Similarity	NPD112	Approved
0.7163	Intermediate Similarity	NPD1392	Approved
0.7157	Intermediate Similarity	NPD2177	Approved
0.7157	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD2175	Phase 3
0.7157	Intermediate Similarity	NPD2176	Approved
0.715	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4418	Discontinued
0.7128	Intermediate Similarity	NPD2599	Approved
0.7128	Intermediate Similarity	NPD2601	Approved
0.7128	Intermediate Similarity	NPD2600	Approved
0.7121	Intermediate Similarity	NPD5256	Discontinued
0.7115	Intermediate Similarity	NPD5601	Phase 2
0.7114	Intermediate Similarity	NPD4372	Phase 1
0.7101	Intermediate Similarity	NPD4044	Discontinued
0.7094	Intermediate Similarity	NPD3477	Phase 2
0.7094	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD2482	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7675	Phase 3
0.7078	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7674	Phase 3
0.7074	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3397	Phase 2
0.7059	Intermediate Similarity	NPD2582	Approved
0.7059	Intermediate Similarity	NPD2581	Approved
0.7051	Intermediate Similarity	NPD7169	Suspended
0.7051	Intermediate Similarity	NPD5147	Discontinued
0.7048	Intermediate Similarity	NPD7672	Approved
0.7048	Intermediate Similarity	NPD7671	Approved
0.7048	Intermediate Similarity	NPD5658	Approved
0.7044	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6219	Discontinued
0.7035	Intermediate Similarity	NPD2917	Approved
0.7028	Intermediate Similarity	NPD4131	Phase 3
0.7009	Intermediate Similarity	NPD2757	Phase 2
0.7	Intermediate Similarity	NPD5429	Discontinued
0.7	Intermediate Similarity	NPD1034	Phase 3
0.7	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD3354	Phase 2
0.699	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5999	Phase 2
0.6986	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD7948	Phase 1
0.697	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5945	Phase 1
0.6963	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5944	Phase 1
0.6961	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5066	Phase 2
0.6948	Remote Similarity	NPD5936	Approved
0.6948	Remote Similarity	NPD6220	Phase 3
0.6948	Remote Similarity	NPD5939	Approved
0.6948	Remote Similarity	NPD5067	Phase 2
0.6944	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1954	Phase 1
0.6939	Remote Similarity	NPD1032	Phase 2
0.6939	Remote Similarity	NPD4071	Approved
0.6939	Remote Similarity	NPD4072	Approved
0.6933	Remote Similarity	NPD6963	Approved
0.6933	Remote Similarity	NPD6964	Approved
0.6931	Remote Similarity	NPD5255	Approved
0.6931	Remote Similarity	NPD1213	Phase 3
0.693	Remote Similarity	NPD7417	Discontinued
0.693	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD425	Approved
0.6927	Remote Similarity	NPD5930	Phase 3
0.6927	Remote Similarity	NPD424	Approved
0.6923	Remote Similarity	NPD7426	Phase 1
0.6917	Remote Similarity	NPD7673	Phase 3
0.6913	Remote Similarity	NPD6230	Discontinued
0.6912	Remote Similarity	NPD802	Phase 2
0.6908	Remote Similarity	NPD3825	Phase 3
0.6906	Remote Similarity	NPD7567	Approved
0.6904	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4875	Phase 3
0.69	Remote Similarity	NPD4876	Phase 3
0.6887	Remote Similarity	NPD2189	Approved
0.6887	Remote Similarity	NPD2187	Approved
0.6885	Remote Similarity	NPD3813	Approved
0.6884	Remote Similarity	NPD2894	Phase 2
0.6878	Remote Similarity	NPD6590	Discontinued
0.6875	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3003	Approved
0.6866	Remote Similarity	NPD4921	Phase 3
0.6866	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4919	Phase 3
0.6859	Remote Similarity	NPD1684	Approved
0.6859	Remote Similarity	NPD1685	Approved
0.6857	Remote Similarity	NPD6991	Approved
0.6857	Remote Similarity	NPD5513	Phase 2
0.6856	Remote Similarity	NPD3872	Phase 3
0.6856	Remote Similarity	NPD6790	Phase 1
0.6853	Remote Similarity	NPD6159	Phase 2
0.6847	Remote Similarity	NPD8063	Discontinued
0.684	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.684	Remote Similarity	NPD6290	Phase 2
0.6838	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7395	Discontinued
0.6834	Remote Similarity	NPD3037	Phase 1
0.6833	Remote Similarity	NPD6306	Phase 2
0.683	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD9695	Approved
0.6827	Remote Similarity	NPD4548	Discontinued
0.6827	Remote Similarity	NPD1768	Approved
0.682	Remote Similarity	NPD7112	Discontinued
0.6818	Remote Similarity	NPD6298	Discontinued

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