NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	188.06
Volume:	182.239
LogP:	1.308
LogD:	1.13
LogS:	-2.346
# Rotatable Bonds:	0
TPSA:	68.61
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.552
Synthetic Accessibility Score:	3.609
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.032
MDCK Permeability:	5.17911257702508e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.137
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	90.53768157958984%
Volume Distribution (VD):	0.548
Pgp-substrate:	12.181151390075684%

ADMET: Metabolism

CYP1A2-inhibitor:	0.968
CYP1A2-substrate:	0.777
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.144
CYP2C9-substrate:	0.746
CYP2D6-inhibitor:	0.698
CYP2D6-substrate:	0.84
CYP3A4-inhibitor:	0.131
CYP3A4-substrate:	0.156

ADMET: Excretion

Clearance (CL):	8.025
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.341
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.73
Rat Oral Acute Toxicity:	0.955
Maximum Recommended Daily Dose:	0.627
Skin Sensitization:	0.94
Carcinogencity:	0.814
Eye Corrosion:	0.066
Eye Irritation:	0.9
Respiratory Toxicity:	0.868

Download Data

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

Natural Product: NPC474492

Natural Product ID:	NPC474492
*Common Name:**	Damirone C
IUPAC Name:	n.a.
Synonyms:	Damirone C
Standard InCHIKey:	KYPUUOLJPNAIDV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H8N2O2/c13-7-3-6-8-5(1-2-11-6)4-12-9(8)10(7)14/h3-4,11-12H,1-2H2
SMILES:	O=C1C=C2NCCc3c2c(C1=O)[nH]c3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469984
PubChem CID:	10465081
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001734] Pyrroloquinolines [CHEMONTID:0002829] Pyrrolo[4,3,2-de]quinolines

*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
NPO9722	Strongylodesma aliwaliensis	n.a.	n.a.	n.a.	n.a.	South African	n.a.	PMID[15844938]
NPO9722	Strongylodesma aliwaliensis	n.a.	n.a.	n.a.	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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	56000.0	nM	PMID[480069]

☑ 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 NPC474492 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	486
0.1-0.2	5165
0.2-0.3	18790
0.3-0.4	12288
0.4-0.5	2645
0.5-0.6	2003
0.6-0.7	980
0.7-0.8	301
0.8-0.85	26
0.85-0.9	8
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9797	High Similarity	NPC100104
0.9797	High Similarity	NPC470680
0.9408	High Similarity	NPC274981
0.9262	High Similarity	NPC217021
0.9262	High Similarity	NPC470679
0.9067	High Similarity	NPC471655
0.9067	High Similarity	NPC473878
0.875	High Similarity	NPC262338
0.8627	High Similarity	NPC123906
0.8581	High Similarity	NPC251391
0.8562	High Similarity	NPC100726
0.8434	Intermediate Similarity	NPC234403
0.8434	Intermediate Similarity	NPC79777
0.8286	Intermediate Similarity	NPC167710
0.8284	Intermediate Similarity	NPC477003
0.8274	Intermediate Similarity	NPC191415
0.8269	Intermediate Similarity	NPC102664
0.8217	Intermediate Similarity	NPC313889
0.8214	Intermediate Similarity	NPC477042
0.8205	Intermediate Similarity	NPC105811
0.8204	Intermediate Similarity	NPC284775
0.8194	Intermediate Similarity	NPC467188
0.8165	Intermediate Similarity	NPC70406
0.816	Intermediate Similarity	NPC233380
0.814	Intermediate Similarity	NPC477415
0.814	Intermediate Similarity	NPC23476
0.814	Intermediate Similarity	NPC474259
0.8125	Intermediate Similarity	NPC292361
0.8107	Intermediate Similarity	NPC182940
0.8092	Intermediate Similarity	NPC473628
0.8046	Intermediate Similarity	NPC475874
0.8012	Intermediate Similarity	NPC102755
0.8011	Intermediate Similarity	NPC326422
0.8	Intermediate Similarity	NPC476460
0.7963	Intermediate Similarity	NPC213914
0.795	Intermediate Similarity	NPC209362
0.7939	Intermediate Similarity	NPC42372
0.791	Intermediate Similarity	NPC304203
0.791	Intermediate Similarity	NPC477414
0.791	Intermediate Similarity	NPC225622
0.791	Intermediate Similarity	NPC221726
0.7874	Intermediate Similarity	NPC469359
0.7843	Intermediate Similarity	NPC291517
0.784	Intermediate Similarity	NPC229055
0.7831	Intermediate Similarity	NPC115232
0.7805	Intermediate Similarity	NPC80681
0.7791	Intermediate Similarity	NPC74357
0.7765	Intermediate Similarity	NPC293216
0.774	Intermediate Similarity	NPC268966
0.7738	Intermediate Similarity	NPC70949
0.7717	Intermediate Similarity	NPC317701
0.7692	Intermediate Similarity	NPC477004
0.768	Intermediate Similarity	NPC74153
0.7665	Intermediate Similarity	NPC265100
0.7661	Intermediate Similarity	NPC186068
0.7654	Intermediate Similarity	NPC216550
0.7616	Intermediate Similarity	NPC151635
0.7614	Intermediate Similarity	NPC133003
0.7614	Intermediate Similarity	NPC311282
0.7611	Intermediate Similarity	NPC473821
0.7602	Intermediate Similarity	NPC252572
0.7596	Intermediate Similarity	NPC237414
0.7586	Intermediate Similarity	NPC73994
0.7581	Intermediate Similarity	NPC88115
0.7572	Intermediate Similarity	NPC83774
0.7572	Intermediate Similarity	NPC157583
0.7568	Intermediate Similarity	NPC106757
0.7543	Intermediate Similarity	NPC470677
0.7542	Intermediate Similarity	NPC324091
0.7542	Intermediate Similarity	NPC154339
0.7541	Intermediate Similarity	NPC477041
0.7541	Intermediate Similarity	NPC477044
0.75	Intermediate Similarity	NPC23215
0.7487	Intermediate Similarity	NPC477413
0.7486	Intermediate Similarity	NPC103119
0.7486	Intermediate Similarity	NPC61011
0.7471	Intermediate Similarity	NPC237188
0.746	Intermediate Similarity	NPC116555
0.7459	Intermediate Similarity	NPC47190
0.7446	Intermediate Similarity	NPC476143
0.7442	Intermediate Similarity	NPC302647
0.7432	Intermediate Similarity	NPC102592
0.7432	Intermediate Similarity	NPC79356
0.743	Intermediate Similarity	NPC473946
0.7429	Intermediate Similarity	NPC55772
0.7418	Intermediate Similarity	NPC267343
0.7416	Intermediate Similarity	NPC474258
0.7405	Intermediate Similarity	NPC477045
0.7396	Intermediate Similarity	NPC242116
0.7396	Intermediate Similarity	NPC214106
0.7396	Intermediate Similarity	NPC110182
0.7391	Intermediate Similarity	NPC78767
0.7391	Intermediate Similarity	NPC473814
0.7377	Intermediate Similarity	NPC202812
0.7371	Intermediate Similarity	NPC145885
0.7371	Intermediate Similarity	NPC14113
0.7371	Intermediate Similarity	NPC84827
0.7368	Intermediate Similarity	NPC143075
0.736	Intermediate Similarity	NPC467063
0.736	Intermediate Similarity	NPC46895
0.736	Intermediate Similarity	NPC110158
0.7356	Intermediate Similarity	NPC110500
0.7356	Intermediate Similarity	NPC149155
0.7356	Intermediate Similarity	NPC203468
0.7333	Intermediate Similarity	NPC278434
0.733	Intermediate Similarity	NPC126709
0.733	Intermediate Similarity	NPC283219
0.733	Intermediate Similarity	NPC11126
0.733	Intermediate Similarity	NPC248041
0.7326	Intermediate Similarity	NPC78020
0.7314	Intermediate Similarity	NPC267885
0.731	Intermediate Similarity	NPC71132
0.731	Intermediate Similarity	NPC2414
0.7308	Intermediate Similarity	NPC138370
0.7302	Intermediate Similarity	NPC477043
0.7297	Intermediate Similarity	NPC227582
0.7296	Intermediate Similarity	NPC105127
0.7296	Intermediate Similarity	NPC65408
0.7289	Intermediate Similarity	NPC472260
0.7284	Intermediate Similarity	NPC190296
0.7283	Intermediate Similarity	NPC93390
0.7273	Intermediate Similarity	NPC111275
0.7267	Intermediate Similarity	NPC114637
0.7263	Intermediate Similarity	NPC175602
0.7258	Intermediate Similarity	NPC34837
0.7257	Intermediate Similarity	NPC469529
0.7253	Intermediate Similarity	NPC469489
0.7251	Intermediate Similarity	NPC21174
0.7251	Intermediate Similarity	NPC271797
0.7249	Intermediate Similarity	NPC476252
0.7233	Intermediate Similarity	NPC96102
0.7228	Intermediate Similarity	NPC247735
0.7228	Intermediate Similarity	NPC472295
0.7228	Intermediate Similarity	NPC269886
0.7228	Intermediate Similarity	NPC81802
0.7228	Intermediate Similarity	NPC472210
0.7222	Intermediate Similarity	NPC114033
0.7222	Intermediate Similarity	NPC308931
0.7222	Intermediate Similarity	NPC101130
0.7222	Intermediate Similarity	NPC129412
0.7222	Intermediate Similarity	NPC99939
0.7222	Intermediate Similarity	NPC58268
0.7219	Intermediate Similarity	NPC474767
0.7219	Intermediate Similarity	NPC74413
0.7211	Intermediate Similarity	NPC469563
0.7205	Intermediate Similarity	NPC110126
0.7198	Intermediate Similarity	NPC209917
0.7198	Intermediate Similarity	NPC255909
0.7195	Intermediate Similarity	NPC159856
0.7195	Intermediate Similarity	NPC314372
0.719	Intermediate Similarity	NPC27740
0.7189	Intermediate Similarity	NPC157828
0.7189	Intermediate Similarity	NPC195239
0.7188	Intermediate Similarity	NPC266249
0.7188	Intermediate Similarity	NPC84911
0.7184	Intermediate Similarity	NPC471943
0.7182	Intermediate Similarity	NPC62749
0.7181	Intermediate Similarity	NPC252338
0.7174	Intermediate Similarity	NPC472292
0.7173	Intermediate Similarity	NPC472065
0.7167	Intermediate Similarity	NPC228835
0.7151	Intermediate Similarity	NPC11445
0.7151	Intermediate Similarity	NPC472293
0.7151	Intermediate Similarity	NPC128244
0.715	Intermediate Similarity	NPC61038
0.7135	Intermediate Similarity	NPC475410
0.7135	Intermediate Similarity	NPC469577
0.7128	Intermediate Similarity	NPC470702
0.7128	Intermediate Similarity	NPC473218
0.7128	Intermediate Similarity	NPC284338
0.7125	Intermediate Similarity	NPC261195
0.7125	Intermediate Similarity	NPC29886
0.7114	Intermediate Similarity	NPC229893
0.7113	Intermediate Similarity	NPC123839
0.7111	Intermediate Similarity	NPC470205
0.7108	Intermediate Similarity	NPC469811
0.7105	Intermediate Similarity	NPC260900
0.7099	Intermediate Similarity	NPC73767
0.7098	Intermediate Similarity	NPC469578
0.7092	Intermediate Similarity	NPC470703
0.7088	Intermediate Similarity	NPC235684
0.7085	Intermediate Similarity	NPC269270
0.7072	Intermediate Similarity	NPC21429
0.7071	Intermediate Similarity	NPC267811
0.7071	Intermediate Similarity	NPC27041
0.7066	Intermediate Similarity	NPC321911
0.7062	Intermediate Similarity	NPC139763
0.7055	Intermediate Similarity	NPC469780
0.7055	Intermediate Similarity	NPC469784
0.7055	Intermediate Similarity	NPC469768
0.7055	Intermediate Similarity	NPC279081
0.7055	Intermediate Similarity	NPC469767
0.7055	Intermediate Similarity	NPC469779
0.7055	Intermediate Similarity	NPC469783
0.7055	Intermediate Similarity	NPC469761
0.705	Intermediate Similarity	NPC14686
0.7049	Intermediate Similarity	NPC17059
0.7048	Intermediate Similarity	NPC63545
0.7039	Intermediate Similarity	NPC213468
0.7037	Intermediate Similarity	NPC472296

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 NPC474492 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	630
0.2-0.3	1115
0.3-0.4	2216
0.4-0.5	2687
0.5-0.6	1699
0.6-0.7	494
0.7-0.8	53
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
0.7895	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2213	Approved
0.7697	Intermediate Similarity	NPD2214	Approved
0.7657	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1270	Approved
0.7543	Intermediate Similarity	NPD3178	Discontinued
0.7529	Intermediate Similarity	NPD1343	Approved
0.7514	Intermediate Similarity	NPD460	Discontinued
0.7486	Intermediate Similarity	NPD2481	Approved
0.7486	Intermediate Similarity	NPD2479	Phase 3
0.7472	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4524	Discontinued
0.7386	Intermediate Similarity	NPD5473	Discontinued
0.7363	Intermediate Similarity	NPD4922	Phase 2
0.7356	Intermediate Similarity	NPD482	Approved
0.7337	Intermediate Similarity	NPD4848	Phase 1
0.7329	Intermediate Similarity	NPD1722	Approved
0.7314	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD201	Phase 2
0.7296	Intermediate Similarity	NPD200	Phase 2
0.7249	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD4988	Discontinued
0.7233	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD3394	Approved
0.7194	Intermediate Similarity	NPD3389	Approved
0.7194	Intermediate Similarity	NPD3393	Approved
0.7189	Intermediate Similarity	NPD7619	Phase 3
0.7189	Intermediate Similarity	NPD7618	Phase 3
0.7188	Intermediate Similarity	NPD2509	Approved
0.7188	Intermediate Similarity	NPD2510	Approved
0.7175	Intermediate Similarity	NPD2753	Discontinued
0.7167	Intermediate Similarity	NPD2091	Phase 2
0.7167	Intermediate Similarity	NPD2096	Phase 2
0.7161	Intermediate Similarity	NPD991	Phase 2
0.7161	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD3238	Discontinued
0.7111	Intermediate Similarity	NPD2092	Phase 2
0.7111	Intermediate Similarity	NPD2094	Phase 2
0.7111	Intermediate Similarity	NPD2095	Phase 2
0.7099	Intermediate Similarity	NPD786	Approved
0.709	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2008	Discontinued
0.7076	Intermediate Similarity	NPD1630	Approved
0.7072	Intermediate Similarity	NPD7564	Discontinued
0.7069	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD1905	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD272	Approved
0.7047	Intermediate Similarity	NPD1506	Discontinued
0.7041	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6664	Approved
0.7011	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD750	Phase 2
0.6995	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD1573	Approved
0.6989	Remote Similarity	NPD1575	Approved
0.6982	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1600	Suspended
0.6966	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3583	Phase 2
0.6954	Remote Similarity	NPD1631	Approved
0.6954	Remote Similarity	NPD2411	Approved
0.6951	Remote Similarity	NPD9599	Approved
0.6941	Remote Similarity	NPD2837	Discontinued
0.6939	Remote Similarity	NPD4051	Discontinued
0.6936	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4075	Phase 2
0.6923	Remote Similarity	NPD3320	Approved
0.6923	Remote Similarity	NPD2442	Approved
0.6923	Remote Similarity	NPD3318	Approved
0.6923	Remote Similarity	NPD2443	Approved
0.6923	Remote Similarity	NPD3319	Phase 1
0.6904	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2061	Approved
0.6895	Remote Similarity	NPD1982	Phase 1
0.689	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD1996	Discontinued
0.6878	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3100	Discontinued
0.6856	Remote Similarity	NPD4299	Phase 1
0.6856	Remote Similarity	NPD3947	Discontinued
0.6856	Remote Similarity	NPD5901	Discontinued
0.6854	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD5888	Phase 2
0.6831	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6152	Phase 1
0.6813	Remote Similarity	NPD3476	Approved
0.6813	Remote Similarity	NPD3475	Approved
0.6802	Remote Similarity	NPD2408	Discontinued
0.68	Remote Similarity	NPD5400	Approved
0.6793	Remote Similarity	NPD1096	Discontinued
0.6788	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6446	Discontinued
0.6778	Remote Similarity	NPD5065	Approved
0.6778	Remote Similarity	NPD4883	Approved
0.6774	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD268	Approved
0.6774	Remote Similarity	NPD271	Approved
0.6772	Remote Similarity	NPD9583	Approved
0.6769	Remote Similarity	NPD5426	Phase 3
0.6768	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD6459	Phase 2
0.6742	Remote Similarity	NPD2641	Approved
0.6742	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD2640	Approved
0.6737	Remote Similarity	NPD5855	Phase 3
0.6737	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5853	Phase 3
0.6735	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD9396	Approved
0.6732	Remote Similarity	NPD9392	Approved
0.6731	Remote Similarity	NPD748	Clinical (unspecified phase)
0.673	Remote Similarity	NPD2118	Approved
0.673	Remote Similarity	NPD2119	Approved
0.6728	Remote Similarity	NPD9100	Approved
0.6727	Remote Similarity	NPD2896	Discontinued
0.6725	Remote Similarity	NPD2172	Phase 1
0.6721	Remote Similarity	NPD3927	Phase 2
0.6721	Remote Similarity	NPD1618	Phase 2
0.6721	Remote Similarity	NPD1643	Phase 3
0.6719	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD4304	Discovery
0.6705	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6771	Discontinued
0.6701	Remote Similarity	NPD5017	Discontinued
0.6685	Remote Similarity	NPD1586	Approved
0.6684	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2770	Discontinued
0.6684	Remote Similarity	NPD2405	Phase 3
0.6684	Remote Similarity	NPD3961	Discontinued
0.6684	Remote Similarity	NPD3246	Discontinued
0.6667	Remote Similarity	NPD2336	Approved
0.6667	Remote Similarity	NPD5198	Approved
0.6667	Remote Similarity	NPD1658	Discontinued
0.6667	Remote Similarity	NPD3323	Discontinued
0.6667	Remote Similarity	NPD5199	Approved
0.6667	Remote Similarity	NPD6787	Phase 2
0.6649	Remote Similarity	NPD6068	Discontinued
0.6649	Remote Similarity	NPD484	Approved
0.6648	Remote Similarity	NPD1404	Approved
0.6648	Remote Similarity	NPD6044	Discontinued
0.6648	Remote Similarity	NPD1403	Approved
0.6646	Remote Similarity	NPD9357	Approved
0.6631	Remote Similarity	NPD7026	Phase 2
0.6629	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7454	Approved
0.6617	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7455	Approved
0.6616	Remote Similarity	NPD3905	Phase 3
0.6616	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD2290	Phase 3
0.6615	Remote Similarity	NPD2289	Phase 3
0.6614	Remote Similarity	NPD4499	Approved
0.6611	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4029	Approved
0.6585	Remote Similarity	NPD4028	Approved
0.6585	Remote Similarity	NPD4030	Approved
0.6582	Remote Similarity	NPD2881	Approved
0.6582	Remote Similarity	NPD2879	Approved
0.6576	Remote Similarity	NPD3078	Approved
0.6576	Remote Similarity	NPD3079	Approved
0.6576	Remote Similarity	NPD3076	Approved
0.6576	Remote Similarity	NPD3077	Approved
0.6576	Remote Similarity	NPD1587	Approved
0.6576	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD1545	Discontinued
0.6573	Remote Similarity	NPD5088	Discontinued
0.6567	Remote Similarity	NPD5475	Discontinued
0.6564	Remote Similarity	NPD803	Phase 1
0.6561	Remote Similarity	NPD7175	Phase 1
0.6553	Remote Similarity	NPD6242	Discontinued
0.655	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2295	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD107	Approved
0.6545	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5809	Phase 3
0.6533	Remote Similarity	NPD3840	Phase 2
0.6533	Remote Similarity	NPD3839	Phase 2
0.6532	Remote Similarity	NPD4463	Approved

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