NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	202.07
Volume:	199.535
LogP:	1.697
LogD:	1.463
LogS:	-2.877
# Rotatable Bonds:	0
TPSA:	59.49
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.572
Synthetic Accessibility Score:	3.518
Fsp3:	0.091
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.975
MDCK Permeability:	6.0453530750237405e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.96
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.05
30% Bioavailability (F30%):	0.868

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089
Plasma Protein Binding (PPB):	84.1461410522461%
Volume Distribution (VD):	0.924
Pgp-substrate:	14.56174087524414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.852
CYP1A2-substrate:	0.872
CYP2C19-inhibitor:	0.159
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.435
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.619
CYP2D6-substrate:	0.849
CYP3A4-inhibitor:	0.169
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	12.574
Half-life (T1/2):	0.891

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.364
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.636
Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	0.439
Skin Sensitization:	0.934
Carcinogencity:	0.608
Eye Corrosion:	0.075
Eye Irritation:	0.871
Respiratory Toxicity:	0.872

Download Data

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

Natural Product: NPC100104

Natural Product ID:	NPC100104
*Common Name:**	Damirone B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JYLGJUYDUWMFOL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H10N2O2/c1-13-3-2-6-5-12-10-9(6)7(13)4-8(14)11(10)15/h4-5,12H,2-3H2,1H3
SMILES:	CN1CCc2c3C1=CC(=O)C(=O)c3[nH]c2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462951
PubChem CID:	2947
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
NPO32524	latrunculid sponges	Species	n.a.	n.a.	n.a.	South African	n.a.	PMID[15332840]

☑ 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
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	3102.0	nM	PMID[449561]

☑ 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 NPC100104 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	445
0.1-0.2	4577
0.2-0.3	18444
0.3-0.4	13077
0.4-0.5	2711
0.5-0.6	2093
0.6-0.7	1024
0.7-0.8	288
0.8-0.85	24
0.85-0.9	9
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470680
0.9797	High Similarity	NPC474492
0.9459	High Similarity	NPC470679
0.9459	High Similarity	NPC217021
0.9262	High Similarity	NPC473878
0.9221	High Similarity	NPC274981
0.9007	High Similarity	NPC471655
0.875	High Similarity	NPC100726
0.8693	High Similarity	NPC123906
0.8645	High Similarity	NPC251391
0.858	High Similarity	NPC262338
0.8452	Intermediate Similarity	NPC102664
0.828	Intermediate Similarity	NPC313889
0.8274	Intermediate Similarity	NPC79777
0.8274	Intermediate Similarity	NPC234403
0.8269	Intermediate Similarity	NPC105811
0.8258	Intermediate Similarity	NPC467188
0.8228	Intermediate Similarity	NPC70406
0.8225	Intermediate Similarity	NPC191415
0.8166	Intermediate Similarity	NPC477042
0.8166	Intermediate Similarity	NPC182940
0.8136	Intermediate Similarity	NPC167710
0.8129	Intermediate Similarity	NPC477003
0.8079	Intermediate Similarity	NPC292361
0.8047	Intermediate Similarity	NPC284775
0.8012	Intermediate Similarity	NPC209362
0.8	Intermediate Similarity	NPC475874
0.8	Intermediate Similarity	NPC233380
0.7989	Intermediate Similarity	NPC477415
0.7989	Intermediate Similarity	NPC474259
0.7989	Intermediate Similarity	NPC23476
0.7943	Intermediate Similarity	NPC473628
0.7901	Intermediate Similarity	NPC229055
0.7898	Intermediate Similarity	NPC268966
0.7866	Intermediate Similarity	NPC80681
0.7865	Intermediate Similarity	NPC326422
0.7861	Intermediate Similarity	NPC102755
0.7853	Intermediate Similarity	NPC476460
0.7853	Intermediate Similarity	NPC74357
0.7829	Intermediate Similarity	NPC469359
0.7805	Intermediate Similarity	NPC213914
0.7798	Intermediate Similarity	NPC70949
0.7792	Intermediate Similarity	NPC291517
0.7784	Intermediate Similarity	NPC42372
0.7784	Intermediate Similarity	NPC115232
0.7771	Intermediate Similarity	NPC311282
0.7765	Intermediate Similarity	NPC221726
0.7765	Intermediate Similarity	NPC304203
0.7765	Intermediate Similarity	NPC477414
0.7765	Intermediate Similarity	NPC225622
0.7746	Intermediate Similarity	NPC73994
0.7733	Intermediate Similarity	NPC83774
0.7725	Intermediate Similarity	NPC265100
0.7719	Intermediate Similarity	NPC293216
0.7717	Intermediate Similarity	NPC106757
0.7676	Intermediate Similarity	NPC317701
0.767	Intermediate Similarity	NPC133003
0.7644	Intermediate Similarity	NPC61011
0.7634	Intermediate Similarity	NPC88115
0.763	Intermediate Similarity	NPC157583
0.7611	Intermediate Similarity	NPC216550
0.7572	Intermediate Similarity	NPC151635
0.7569	Intermediate Similarity	NPC473821
0.7554	Intermediate Similarity	NPC477004
0.7554	Intermediate Similarity	NPC237414
0.7541	Intermediate Similarity	NPC74153
0.7514	Intermediate Similarity	NPC186068
0.7514	Intermediate Similarity	NPC46895
0.75	Intermediate Similarity	NPC477041
0.75	Intermediate Similarity	NPC477044
0.75	Intermediate Similarity	NPC324091
0.75	Intermediate Similarity	NPC470677
0.7468	Intermediate Similarity	NPC65408
0.7457	Intermediate Similarity	NPC252572
0.7456	Intermediate Similarity	NPC242116
0.7455	Intermediate Similarity	NPC472260
0.7446	Intermediate Similarity	NPC78767
0.7446	Intermediate Similarity	NPC473814
0.7444	Intermediate Similarity	NPC103119
0.7432	Intermediate Similarity	NPC93390
0.7429	Intermediate Similarity	NPC145885
0.7429	Intermediate Similarity	NPC237188
0.7429	Intermediate Similarity	NPC84827
0.7429	Intermediate Similarity	NPC14113
0.7427	Intermediate Similarity	NPC114637
0.7418	Intermediate Similarity	NPC47190
0.7414	Intermediate Similarity	NPC469529
0.7405	Intermediate Similarity	NPC476143
0.7403	Intermediate Similarity	NPC154339
0.7399	Intermediate Similarity	NPC302647
0.7391	Intermediate Similarity	NPC79356
0.7391	Intermediate Similarity	NPC102592
0.7389	Intermediate Similarity	NPC473946
0.7386	Intermediate Similarity	NPC11126
0.7377	Intermediate Similarity	NPC267343
0.7368	Intermediate Similarity	NPC71132
0.7366	Intermediate Similarity	NPC477045
0.7358	Intermediate Similarity	NPC477413
0.7358	Intermediate Similarity	NPC110182
0.7353	Intermediate Similarity	NPC214106
0.7342	Intermediate Similarity	NPC23215
0.733	Intermediate Similarity	NPC116555
0.731	Intermediate Similarity	NPC21174
0.731	Intermediate Similarity	NPC271797
0.7308	Intermediate Similarity	NPC469489
0.7292	Intermediate Similarity	NPC61038
0.7288	Intermediate Similarity	NPC126709
0.7288	Intermediate Similarity	NPC55772
0.7288	Intermediate Similarity	NPC248041
0.7283	Intermediate Similarity	NPC472210
0.7283	Intermediate Similarity	NPC247735
0.7283	Intermediate Similarity	NPC472295
0.7283	Intermediate Similarity	NPC269886
0.7283	Intermediate Similarity	NPC81802
0.7278	Intermediate Similarity	NPC474258
0.7273	Intermediate Similarity	NPC267885
0.7273	Intermediate Similarity	NPC474767
0.7268	Intermediate Similarity	NPC138370
0.7267	Intermediate Similarity	NPC110126
0.7263	Intermediate Similarity	NPC477043
0.7258	Intermediate Similarity	NPC227582
0.7253	Intermediate Similarity	NPC255909
0.7243	Intermediate Similarity	NPC202812
0.724	Intermediate Similarity	NPC143075
0.7239	Intermediate Similarity	NPC190296
0.7228	Intermediate Similarity	NPC472292
0.7225	Intermediate Similarity	NPC175602
0.7222	Intermediate Similarity	NPC467063
0.7222	Intermediate Similarity	NPC110158
0.7222	Intermediate Similarity	NPC228835
0.7222	Intermediate Similarity	NPC269270
0.7219	Intermediate Similarity	NPC34837
0.7216	Intermediate Similarity	NPC203468
0.7216	Intermediate Similarity	NPC110500
0.7216	Intermediate Similarity	NPC149155
0.7211	Intermediate Similarity	NPC476252
0.7204	Intermediate Similarity	NPC472293
0.7198	Intermediate Similarity	NPC278434
0.7191	Intermediate Similarity	NPC283219
0.7188	Intermediate Similarity	NPC475410
0.7188	Intermediate Similarity	NPC469577
0.7186	Intermediate Similarity	NPC14686
0.7184	Intermediate Similarity	NPC78020
0.7181	Intermediate Similarity	NPC81535
0.7181	Intermediate Similarity	NPC74413
0.7178	Intermediate Similarity	NPC101130
0.7178	Intermediate Similarity	NPC114033
0.7178	Intermediate Similarity	NPC129412
0.7178	Intermediate Similarity	NPC58268
0.7173	Intermediate Similarity	NPC469563
0.7168	Intermediate Similarity	NPC2414
0.716	Intermediate Similarity	NPC73767
0.7158	Intermediate Similarity	NPC209917
0.7152	Intermediate Similarity	NPC314372
0.7151	Intermediate Similarity	NPC195239
0.7151	Intermediate Similarity	NPC157828
0.715	Intermediate Similarity	NPC266249
0.7143	Intermediate Similarity	NPC84911
0.7143	Intermediate Similarity	NPC471943
0.7143	Intermediate Similarity	NPC105127
0.7143	Intermediate Similarity	NPC252338
0.7143	Intermediate Similarity	NPC472288
0.7143	Intermediate Similarity	NPC207866
0.7135	Intermediate Similarity	NPC472065
0.7135	Intermediate Similarity	NPC111275
0.7119	Intermediate Similarity	NPC139763
0.7112	Intermediate Similarity	NPC128244
0.7112	Intermediate Similarity	NPC11445
0.709	Intermediate Similarity	NPC103361
0.709	Intermediate Similarity	NPC472297
0.709	Intermediate Similarity	NPC472296
0.709	Intermediate Similarity	NPC284338
0.7088	Intermediate Similarity	NPC308931
0.7088	Intermediate Similarity	NPC99939
0.7081	Intermediate Similarity	NPC29886
0.7081	Intermediate Similarity	NPC261195
0.7081	Intermediate Similarity	NPC96102
0.7077	Intermediate Similarity	NPC123839
0.7072	Intermediate Similarity	NPC470205
0.7068	Intermediate Similarity	NPC260900
0.7062	Intermediate Similarity	NPC469578
0.7062	Intermediate Similarity	NPC161861
0.7049	Intermediate Similarity	NPC17273
0.7049	Intermediate Similarity	NPC135601
0.7049	Intermediate Similarity	NPC118084
0.7049	Intermediate Similarity	NPC141612
0.7049	Intermediate Similarity	NPC62749
0.7049	Intermediate Similarity	NPC235684
0.7048	Intermediate Similarity	NPC159856
0.7033	Intermediate Similarity	NPC21429
0.7032	Intermediate Similarity	NPC27740
0.7029	Intermediate Similarity	NPC56233
0.7029	Intermediate Similarity	NPC41717
0.7025	Intermediate Similarity	NPC71236
0.7024	Intermediate Similarity	NPC321911
0.7012	Intermediate Similarity	NPC469767
0.7012	Intermediate Similarity	NPC469768
0.7012	Intermediate Similarity	NPC469779
0.7012	Intermediate Similarity	NPC469761
0.7012	Intermediate Similarity	NPC469783

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 NPC100104 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	602
0.2-0.3	1096
0.3-0.4	2150
0.4-0.5	2695
0.5-0.6	1785
0.6-0.7	523
0.7-0.8	59
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
0.7849	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2213	Approved
0.7758	Intermediate Similarity	NPD2214	Approved
0.7714	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1270	Approved
0.7588	Intermediate Similarity	NPD1343	Approved
0.7569	Intermediate Similarity	NPD460	Discontinued
0.7558	Intermediate Similarity	NPD4524	Discontinued
0.7528	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3178	Discontinued
0.7468	Intermediate Similarity	NPD200	Phase 2
0.7468	Intermediate Similarity	NPD201	Phase 2
0.7418	Intermediate Similarity	NPD4922	Phase 2
0.7391	Intermediate Similarity	NPD4848	Phase 1
0.7389	Intermediate Similarity	NPD4988	Discontinued
0.7345	Intermediate Similarity	NPD2479	Phase 3
0.7345	Intermediate Similarity	NPD2481	Approved
0.7345	Intermediate Similarity	NPD5473	Discontinued
0.7321	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7618	Phase 3
0.7243	Intermediate Similarity	NPD7619	Phase 3
0.724	Intermediate Similarity	NPD2509	Approved
0.724	Intermediate Similarity	NPD2510	Approved
0.7235	Intermediate Similarity	NPD1630	Approved
0.7233	Intermediate Similarity	NPD272	Approved
0.7232	Intermediate Similarity	NPD2753	Discontinued
0.7216	Intermediate Similarity	NPD482	Approved
0.7211	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1722	Approved
0.7175	Intermediate Similarity	NPD3238	Discontinued
0.7173	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD3393	Approved
0.7157	Intermediate Similarity	NPD3389	Approved
0.7157	Intermediate Similarity	NPD3394	Approved
0.7143	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2008	Discontinued
0.7127	Intermediate Similarity	NPD7564	Discontinued
0.7126	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1600	Suspended
0.711	Intermediate Similarity	NPD1631	Approved
0.7101	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD1506	Discontinued
0.7081	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6664	Approved
0.7068	Intermediate Similarity	NPD4924	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD750	Phase 2
0.7055	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD786	Approved
0.7045	Intermediate Similarity	NPD1573	Approved
0.7045	Intermediate Similarity	NPD1575	Approved
0.7033	Intermediate Similarity	NPD2091	Phase 2
0.7033	Intermediate Similarity	NPD2096	Phase 2
0.7027	Intermediate Similarity	NPD1905	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1996	Discontinued
0.7006	Intermediate Similarity	NPD991	Phase 2
0.7006	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD2411	Approved
0.6994	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4075	Phase 2
0.6981	Remote Similarity	NPD3476	Approved
0.6981	Remote Similarity	NPD3475	Approved
0.6978	Remote Similarity	NPD2094	Phase 2
0.6978	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2095	Phase 2
0.6978	Remote Similarity	NPD2092	Phase 2
0.6974	Remote Similarity	NPD2443	Approved
0.6974	Remote Similarity	NPD2442	Approved
0.6954	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD271	Approved
0.6948	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD268	Approved
0.6946	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3100	Discontinued
0.6914	Remote Similarity	NPD3583	Phase 2
0.6909	Remote Similarity	NPD9599	Approved
0.6907	Remote Similarity	NPD3947	Discontinued
0.6907	Remote Similarity	NPD4299	Phase 1
0.6904	Remote Similarity	NPD4051	Discontinued
0.6903	Remote Similarity	NPD748	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2837	Discontinued
0.6899	Remote Similarity	NPD2119	Approved
0.6899	Remote Similarity	NPD2118	Approved
0.6898	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD3320	Approved
0.6885	Remote Similarity	NPD3319	Phase 1
0.6885	Remote Similarity	NPD3318	Approved
0.6869	Remote Similarity	NPD6152	Phase 1
0.6868	Remote Similarity	NPD3927	Phase 2
0.6868	Remote Similarity	NPD1643	Phase 3
0.6859	Remote Similarity	NPD1982	Phase 1
0.6859	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5400	Approved
0.6857	Remote Similarity	NPD6771	Discontinued
0.6853	Remote Similarity	NPD2408	Discontinued
0.6842	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5017	Discontinued
0.6835	Remote Similarity	NPD9583	Approved
0.6833	Remote Similarity	NPD1586	Approved
0.6831	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5901	Discontinued
0.6818	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1658	Discontinued
0.6809	Remote Similarity	NPD2336	Approved
0.68	Remote Similarity	NPD6787	Phase 2
0.68	Remote Similarity	NPD5888	Phase 2
0.6798	Remote Similarity	NPD2641	Approved
0.6798	Remote Similarity	NPD2640	Approved
0.6763	Remote Similarity	NPD2061	Approved
0.6757	Remote Similarity	NPD1096	Discontinued
0.6751	Remote Similarity	NPD3905	Phase 3
0.6748	Remote Similarity	NPD4028	Approved
0.6748	Remote Similarity	NPD4030	Approved
0.6748	Remote Similarity	NPD4029	Approved
0.6742	Remote Similarity	NPD6446	Discontinued
0.674	Remote Similarity	NPD5065	Approved
0.6738	Remote Similarity	NPD3961	Discontinued
0.6738	Remote Similarity	NPD2770	Discontinued
0.6736	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5426	Phase 3
0.6725	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD3323	Discontinued
0.6721	Remote Similarity	NPD1587	Approved
0.6718	Remote Similarity	NPD2879	Approved
0.6718	Remote Similarity	NPD2881	Approved
0.6717	Remote Similarity	NPD6459	Phase 2
0.6716	Remote Similarity	NPD5199	Approved
0.6716	Remote Similarity	NPD5198	Approved
0.6709	Remote Similarity	NPD9357	Approved
0.6705	Remote Similarity	NPD1403	Approved
0.6705	Remote Similarity	NPD1404	Approved
0.6704	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6044	Discontinued
0.6702	Remote Similarity	NPD6068	Discontinued
0.6702	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD9396	Approved
0.6688	Remote Similarity	NPD9392	Approved
0.6687	Remote Similarity	NPD2896	Discontinued
0.6687	Remote Similarity	NPD9100	Approved
0.6686	Remote Similarity	NPD2172	Phase 1
0.6686	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7026	Phase 2
0.6684	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4703	Approved
0.6667	Remote Similarity	NPD2290	Phase 3
0.6667	Remote Similarity	NPD7454	Approved
0.6667	Remote Similarity	NPD2307	Discontinued
0.6667	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4702	Approved
0.6667	Remote Similarity	NPD7455	Approved
0.6667	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4499	Approved
0.6667	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3840	Phase 2
0.6667	Remote Similarity	NPD5020	Approved
0.6667	Remote Similarity	NPD2289	Phase 3
0.6667	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3839	Phase 2
0.665	Remote Similarity	NPD6987	Phase 1
0.6649	Remote Similarity	NPD3246	Discontinued
0.6649	Remote Similarity	NPD2405	Phase 3
0.6649	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD4883	Approved
0.6648	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3944	Approved
0.6646	Remote Similarity	NPD3942	Approved
0.6632	Remote Similarity	NPD1952	Discontinued
0.663	Remote Similarity	NPD3078	Approved
0.663	Remote Similarity	NPD3076	Approved
0.663	Remote Similarity	NPD3079	Approved
0.663	Remote Similarity	NPD3077	Approved
0.663	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD1545	Discontinued
0.6629	Remote Similarity	NPD5088	Discontinued
0.6627	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5853	Phase 3
0.6615	Remote Similarity	NPD5855	Phase 3
0.6614	Remote Similarity	NPD7175	Phase 1
0.661	Remote Similarity	NPD2511	Approved
0.6602	Remote Similarity	NPD6242	Discontinued
0.66	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD4304	Discovery
0.6596	Remote Similarity	NPD5809	Phase 3
0.6595	Remote Similarity	NPD1618	Phase 2
0.6591	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6578	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data