NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	187.07
Volume:	184.445
LogP:	0.874
LogD:	0.831
LogS:	-2.597
# Rotatable Bonds:	0
TPSA:	74.4
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	3.708
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.946
MDCK Permeability:	5.06059632243705e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.8
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.107
Plasma Protein Binding (PPB):	69.47067260742188%
Volume Distribution (VD):	1.175
Pgp-substrate:	35.69049072265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.958
CYP1A2-substrate:	0.676
CYP2C19-inhibitor:	0.136
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.166
CYP2C9-substrate:	0.771
CYP2D6-inhibitor:	0.72
CYP2D6-substrate:	0.87
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.148

ADMET: Excretion

Clearance (CL):	7.715
Half-life (T1/2):	0.814

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.391
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.9
Rat Oral Acute Toxicity:	0.917
Maximum Recommended Daily Dose:	0.68
Skin Sensitization:	0.928
Carcinogencity:	0.877
Eye Corrosion:	0.013
Eye Irritation:	0.527
Respiratory Toxicity:	0.906

Download Data

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

Natural Product: NPC471655

Natural Product ID:	NPC471655
*Common Name:**	Makaluvamine I
IUPAC Name:	n.a.
Synonyms:	Makaluvamine I
Standard InCHIKey:	FNVJTPOBDKESTQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H9N3O.C2HF3O2/c11-6-3-7-8-5(1-2-12-7)4-13-9(8)10(6)14;3-2(4,5)1(6)7/h3-4,13H,1-2,11H2;(H,6,7)
SMILES:	OC(=O)C(F)(F)F.NC1=CC2=NCCc3c2c(C1=O)[nH]c3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL308770
PubChem CID:	n.a.
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
NPO32549	zyzzya fuliginosa	Species	n.a.	Eukaryota	n.a.	indopacific	n.a.	PMID[12027767]
NPO32549	zyzzya fuliginosa	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[16180829]
NPO32549	zyzzya fuliginosa	Species	n.a.	Eukaryota	n.a.	pohnpeian	n.a.	PMID[8691207]
NPO32549	zyzzya fuliginosa	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[9134749]

☑ 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
NPT137	Cell Line	L1210	Mus musculus	IC50	=	250.0	nM	PMID[529831]

☑ 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 NPC471655 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	325
0.1-0.2	4187
0.2-0.3	19182
0.3-0.4	12904
0.4-0.5	2823
0.5-0.6	2152
0.6-0.7	965
0.7-0.8	137
0.8-0.85	14
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9441	High Similarity	NPC100726
0.9067	High Similarity	NPC474492
0.9007	High Similarity	NPC470680
0.9007	High Similarity	NPC100104
0.8919	High Similarity	NPC473878
0.8851	High Similarity	NPC102664
0.8846	High Similarity	NPC262338
0.8526	High Similarity	NPC274981
0.8519	High Similarity	NPC234403
0.8519	High Similarity	NPC79777
0.8487	Intermediate Similarity	NPC470679
0.8487	Intermediate Similarity	NPC217021
0.8477	Intermediate Similarity	NPC123906
0.8431	Intermediate Similarity	NPC251391
0.8288	Intermediate Similarity	NPC291517
0.8278	Intermediate Similarity	NPC467188
0.8214	Intermediate Similarity	NPC23476
0.8214	Intermediate Similarity	NPC474259
0.8214	Intermediate Similarity	NPC477415
0.8187	Intermediate Similarity	NPC473821
0.8182	Intermediate Similarity	NPC182940
0.8182	Intermediate Similarity	NPC477042
0.8125	Intermediate Similarity	NPC233380
0.8118	Intermediate Similarity	NPC475874
0.8065	Intermediate Similarity	NPC313889
0.8061	Intermediate Similarity	NPC284775
0.8059	Intermediate Similarity	NPC473628
0.8052	Intermediate Similarity	NPC105811
0.8046	Intermediate Similarity	NPC74153
0.8013	Intermediate Similarity	NPC70406
0.7977	Intermediate Similarity	NPC225622
0.7977	Intermediate Similarity	NPC477414
0.7977	Intermediate Similarity	NPC221726
0.7929	Intermediate Similarity	NPC477003
0.7919	Intermediate Similarity	NPC23215
0.7911	Intermediate Similarity	NPC209362
0.7907	Intermediate Similarity	NPC268966
0.7841	Intermediate Similarity	NPC167710
0.7829	Intermediate Similarity	NPC93390
0.7818	Intermediate Similarity	NPC302647
0.7811	Intermediate Similarity	NPC191415
0.7764	Intermediate Similarity	NPC80681
0.774	Intermediate Similarity	NPC78767
0.774	Intermediate Similarity	NPC473814
0.7725	Intermediate Similarity	NPC186068
0.7702	Intermediate Similarity	NPC213914
0.7688	Intermediate Similarity	NPC229055
0.7683	Intermediate Similarity	NPC42372
0.767	Intermediate Similarity	NPC304203
0.7657	Intermediate Similarity	NPC476460
0.764	Intermediate Similarity	NPC74357
0.7571	Intermediate Similarity	NPC326422
0.7558	Intermediate Similarity	NPC102755
0.7529	Intermediate Similarity	NPC469359
0.7527	Intermediate Similarity	NPC106757
0.7515	Intermediate Similarity	NPC293216
0.7514	Intermediate Similarity	NPC216550
0.75	Intermediate Similarity	NPC477044
0.75	Intermediate Similarity	NPC477041
0.7486	Intermediate Similarity	NPC473946
0.747	Intermediate Similarity	NPC115232
0.7453	Intermediate Similarity	NPC472260
0.7447	Intermediate Similarity	NPC477413
0.7446	Intermediate Similarity	NPC88115
0.743	Intermediate Similarity	NPC202812
0.7412	Intermediate Similarity	NPC469529
0.7389	Intermediate Similarity	NPC292361
0.7384	Intermediate Similarity	NPC11126
0.7381	Intermediate Similarity	NPC70949
0.7371	Intermediate Similarity	NPC474258
0.7363	Intermediate Similarity	NPC477004
0.7363	Intermediate Similarity	NPC477045
0.7355	Intermediate Similarity	NPC472288
0.7355	Intermediate Similarity	NPC105127
0.7351	Intermediate Similarity	NPC71236
0.7342	Intermediate Similarity	NPC190296
0.7341	Intermediate Similarity	NPC73994
0.7326	Intermediate Similarity	NPC237188
0.7326	Intermediate Similarity	NPC83774
0.7326	Intermediate Similarity	NPC143075
0.7318	Intermediate Similarity	NPC47190
0.7312	Intermediate Similarity	NPC175602
0.7305	Intermediate Similarity	NPC265100
0.7299	Intermediate Similarity	NPC470677
0.7297	Intermediate Similarity	NPC317701
0.7292	Intermediate Similarity	NPC291389
0.729	Intermediate Similarity	NPC96102
0.7285	Intermediate Similarity	NPC313823
0.7278	Intermediate Similarity	NPC129412
0.7278	Intermediate Similarity	NPC58268
0.7278	Intermediate Similarity	NPC114033
0.7278	Intermediate Similarity	NPC101130
0.7273	Intermediate Similarity	NPC308931
0.7273	Intermediate Similarity	NPC99939
0.7273	Intermediate Similarity	NPC311282
0.7268	Intermediate Similarity	NPC474767
0.7262	Intermediate Similarity	NPC2414
0.7262	Intermediate Similarity	NPC71132
0.7261	Intermediate Similarity	NPC110126
0.7258	Intermediate Similarity	NPC477043
0.7251	Intermediate Similarity	NPC252572
0.725	Intermediate Similarity	NPC314372
0.725	Intermediate Similarity	NPC159856
0.7247	Intermediate Similarity	NPC209917
0.7244	Intermediate Similarity	NPC84911
0.7241	Intermediate Similarity	NPC61011
0.7235	Intermediate Similarity	NPC471943
0.7225	Intermediate Similarity	NPC145885
0.7225	Intermediate Similarity	NPC14113
0.7225	Intermediate Similarity	NPC157583
0.7225	Intermediate Similarity	NPC84827
0.7216	Intermediate Similarity	NPC228835
0.7209	Intermediate Similarity	NPC203468
0.7209	Intermediate Similarity	NPC110500
0.7209	Intermediate Similarity	NPC149155
0.7207	Intermediate Similarity	NPC154339
0.7205	Intermediate Similarity	NPC143872
0.7196	Intermediate Similarity	NPC61038
0.7184	Intermediate Similarity	NPC55772
0.7184	Intermediate Similarity	NPC283219
0.7184	Intermediate Similarity	NPC126709
0.7184	Intermediate Similarity	NPC248041
0.7179	Intermediate Similarity	NPC14448
0.7179	Intermediate Similarity	NPC98156
0.7179	Intermediate Similarity	NPC138596
0.7179	Intermediate Similarity	NPC29886
0.7179	Intermediate Similarity	NPC261195
0.7179	Intermediate Similarity	NPC195704
0.7179	Intermediate Similarity	NPC167200
0.7179	Intermediate Similarity	NPC292434
0.7179	Intermediate Similarity	NPC200397
0.7179	Intermediate Similarity	NPC64661
0.7176	Intermediate Similarity	NPC78020
0.7175	Intermediate Similarity	NPC133003
0.7174	Intermediate Similarity	NPC237414
0.7168	Intermediate Similarity	NPC151635
0.7168	Intermediate Similarity	NPC267885
0.7152	Intermediate Similarity	NPC73767
0.7152	Intermediate Similarity	NPC33229
0.7151	Intermediate Similarity	NPC103119
0.7143	Intermediate Similarity	NPC242116
0.7143	Intermediate Similarity	NPC82295
0.7143	Intermediate Similarity	NPC116555
0.7135	Intermediate Similarity	NPC476527
0.7134	Intermediate Similarity	NPC65408
0.7133	Intermediate Similarity	NPC27740
0.7127	Intermediate Similarity	NPC472292
0.712	Intermediate Similarity	NPC476143
0.7119	Intermediate Similarity	NPC110158
0.7119	Intermediate Similarity	NPC46895
0.7111	Intermediate Similarity	NPC324091
0.7107	Intermediate Similarity	NPC205604
0.7107	Intermediate Similarity	NPC74928
0.7107	Intermediate Similarity	NPC3698
0.7107	Intermediate Similarity	NPC469783
0.7107	Intermediate Similarity	NPC279081
0.7107	Intermediate Similarity	NPC12831
0.7107	Intermediate Similarity	NPC48171
0.7107	Intermediate Similarity	NPC286529
0.7107	Intermediate Similarity	NPC209281
0.7107	Intermediate Similarity	NPC469761
0.7107	Intermediate Similarity	NPC169308
0.7107	Intermediate Similarity	NPC77582
0.7107	Intermediate Similarity	NPC302717
0.7107	Intermediate Similarity	NPC129753
0.7107	Intermediate Similarity	NPC469784
0.7107	Intermediate Similarity	NPC469779
0.7107	Intermediate Similarity	NPC469768
0.7107	Intermediate Similarity	NPC469780
0.7107	Intermediate Similarity	NPC97230
0.7107	Intermediate Similarity	NPC244087
0.7107	Intermediate Similarity	NPC469767
0.7107	Intermediate Similarity	NPC59839
0.7104	Intermediate Similarity	NPC472293
0.7095	Intermediate Similarity	NPC17059
0.7088	Intermediate Similarity	NPC267343
0.7083	Intermediate Similarity	NPC279918
0.7081	Intermediate Similarity	NPC284338
0.7073	Intermediate Similarity	NPC24678
0.7073	Intermediate Similarity	NPC105818
0.7066	Intermediate Similarity	NPC76982
0.7065	Intermediate Similarity	NPC227582
0.7065	Intermediate Similarity	NPC174281
0.7065	Intermediate Similarity	NPC475286
0.7063	Intermediate Similarity	NPC469766
0.7055	Intermediate Similarity	NPC471957
0.7049	Intermediate Similarity	NPC157828
0.7049	Intermediate Similarity	NPC195239
0.7047	Intermediate Similarity	NPC207866
0.7041	Intermediate Similarity	NPC282231
0.7039	Intermediate Similarity	NPC118084
0.7029	Intermediate Similarity	NPC111275
0.7029	Intermediate Similarity	NPC473380
0.7029	Intermediate Similarity	NPC240088
0.7022	Intermediate Similarity	NPC467063
0.7018	Intermediate Similarity	NPC114637
0.7017	Intermediate Similarity	NPC469489
0.7011	Intermediate Similarity	NPC102592
0.7011	Intermediate Similarity	NPC79356
0.7011	Intermediate Similarity	NPC11445

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 NPC471655 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	584
0.2-0.3	1170
0.3-0.4	2192
0.4-0.5	2719
0.5-0.6	1774
0.6-0.7	502
0.7-0.8	28
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
0.7751	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3178	Discontinued
0.7434	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1270	Approved
0.736	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4848	Phase 1
0.729	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD482	Approved
0.7182	Intermediate Similarity	NPD460	Discontinued
0.7176	Intermediate Similarity	NPD1343	Approved
0.717	Intermediate Similarity	NPD1722	Approved
0.7168	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD786	Approved
0.7143	Intermediate Similarity	NPD5473	Discontinued
0.7134	Intermediate Similarity	NPD9343	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD200	Phase 2
0.7134	Intermediate Similarity	NPD201	Phase 2
0.7117	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD3100	Discontinued
0.7115	Intermediate Similarity	NPD272	Approved
0.7095	Intermediate Similarity	NPD4988	Discontinued
0.7093	Intermediate Similarity	NPD3347	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD4075	Phase 2
0.7041	Intermediate Similarity	NPD5400	Approved
0.7033	Intermediate Similarity	NPD4922	Phase 2
0.7029	Intermediate Similarity	NPD2753	Discontinued
0.7024	Intermediate Similarity	NPD2214	Approved
0.7024	Intermediate Similarity	NPD2213	Approved
0.7024	Intermediate Similarity	NPD1630	Approved
0.7006	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9599	Approved
0.6993	Remote Similarity	NPD991	Phase 2
0.6993	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5901	Discontinued
0.6971	Remote Similarity	NPD3238	Discontinued
0.6966	Remote Similarity	NPD2094	Phase 2
0.6966	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2095	Phase 2
0.6966	Remote Similarity	NPD2092	Phase 2
0.6954	Remote Similarity	NPD4524	Discontinued
0.6949	Remote Similarity	NPD2481	Approved
0.6949	Remote Similarity	NPD2479	Phase 3
0.6937	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7564	Discontinued
0.6927	Remote Similarity	NPD2091	Phase 2
0.6927	Remote Similarity	NPD2096	Phase 2
0.6914	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD1506	Discontinued
0.691	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1631	Approved
0.6886	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD9100	Approved
0.6879	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3319	Phase 1
0.6872	Remote Similarity	NPD3318	Approved
0.6872	Remote Similarity	NPD3320	Approved
0.6871	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2008	Discontinued
0.6857	Remote Similarity	NPD750	Phase 2
0.6854	Remote Similarity	NPD3927	Phase 2
0.6851	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2061	Approved
0.6839	Remote Similarity	NPD1573	Approved
0.6839	Remote Similarity	NPD1575	Approved
0.6839	Remote Similarity	NPD1600	Suspended
0.6833	Remote Similarity	NPD1096	Discontinued
0.6831	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD5685	Approved
0.6831	Remote Similarity	NPD5686	Approved
0.6826	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5017	Discontinued
0.6821	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD271	Approved
0.6821	Remote Similarity	NPD268	Approved
0.6813	Remote Similarity	NPD3961	Discontinued
0.6806	Remote Similarity	NPD4299	Phase 1
0.6802	Remote Similarity	NPD3583	Phase 2
0.6797	Remote Similarity	NPD9357	Approved
0.6786	Remote Similarity	NPD2837	Discontinued
0.6779	Remote Similarity	NPD9392	Approved
0.6779	Remote Similarity	NPD9396	Approved
0.6778	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7619	Phase 3
0.6774	Remote Similarity	NPD7618	Phase 3
0.6772	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2172	Phase 1
0.676	Remote Similarity	NPD1643	Phase 3
0.6755	Remote Similarity	NPD1982	Phase 1
0.6754	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD3475	Approved
0.6752	Remote Similarity	NPD3476	Approved
0.6735	Remote Similarity	NPD2411	Approved
0.6724	Remote Similarity	NPD6446	Discontinued
0.6724	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD4883	Approved
0.6718	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD3394	Approved
0.6717	Remote Similarity	NPD3389	Approved
0.6717	Remote Similarity	NPD3393	Approved
0.671	Remote Similarity	NPD9583	Approved
0.6705	Remote Similarity	NPD1545	Discontinued
0.6701	Remote Similarity	NPD6459	Phase 2
0.6701	Remote Similarity	NPD2509	Approved
0.6701	Remote Similarity	NPD2510	Approved
0.6686	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2119	Approved
0.6667	Remote Similarity	NPD2118	Approved
0.6649	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD2289	Phase 3
0.6649	Remote Similarity	NPD2290	Phase 3
0.6648	Remote Similarity	NPD3506	Approved
0.6648	Remote Similarity	NPD3505	Approved
0.6647	Remote Similarity	NPD6771	Discontinued
0.6644	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3947	Discontinued
0.663	Remote Similarity	NPD2770	Discontinued
0.6629	Remote Similarity	NPD4128	Approved
0.6629	Remote Similarity	NPD1586	Approved
0.6629	Remote Similarity	NPD5065	Approved
0.6626	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD6664	Approved
0.6611	Remote Similarity	NPD4079	Approved
0.6611	Remote Similarity	NPD4076	Approved
0.661	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD803	Phase 1
0.659	Remote Similarity	NPD1403	Approved
0.659	Remote Similarity	NPD1404	Approved
0.6584	Remote Similarity	NPD6242	Discontinued
0.6582	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD6217	Discontinued
0.657	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD2896	Discontinued
0.6561	Remote Similarity	NPD1598	Discontinued
0.6558	Remote Similarity	NPD748	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD1005	Phase 2
0.6548	Remote Similarity	NPD1004	Phase 2
0.6545	Remote Similarity	NPD2405	Phase 3
0.6541	Remote Similarity	NPD3246	Discontinued
0.6536	Remote Similarity	NPD2928	Phase 2
0.6535	Remote Similarity	NPD5198	Approved
0.6535	Remote Similarity	NPD5199	Approved
0.6534	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2336	Approved
0.6522	Remote Similarity	NPD4030	Approved
0.6522	Remote Similarity	NPD4028	Approved
0.6522	Remote Similarity	NPD4029	Approved
0.6519	Remote Similarity	NPD1587	Approved
0.6519	Remote Similarity	NPD1031	Discontinued
0.6515	Remote Similarity	NPD6152	Phase 1
0.6514	Remote Similarity	NPD3323	Discontinued
0.6513	Remote Similarity	NPD3967	Approved
0.6513	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.651	Remote Similarity	NPD484	Approved
0.6508	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD5853	Phase 3
0.6508	Remote Similarity	NPD5855	Phase 3
0.65	Remote Similarity	NPD6044	Discontinued
0.6497	Remote Similarity	NPD2641	Approved
0.6497	Remote Similarity	NPD2640	Approved
0.6495	Remote Similarity	NPD4304	Discovery
0.6485	Remote Similarity	NPD107	Approved
0.6484	Remote Similarity	NPD1618	Phase 2
0.648	Remote Similarity	NPD3410	Approved
0.648	Remote Similarity	NPD3411	Phase 2
0.6477	Remote Similarity	NPD3890	Phase 2
0.6477	Remote Similarity	NPD3891	Phase 2
0.6471	Remote Similarity	NPD4462	Approved
0.6471	Remote Similarity	NPD4463	Approved
0.6468	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4051	Discontinued
0.6462	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.645	Remote Similarity	NPD4703	Approved
0.645	Remote Similarity	NPD4702	Approved
0.6447	Remote Similarity	NPD2443	Approved
0.6447	Remote Similarity	NPD2442	Approved
0.6446	Remote Similarity	NPD5020	Approved
0.6442	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD2639	Approved
0.6441	Remote Similarity	NPD2642	Approved
0.644	Remote Similarity	NPD1952	Discontinued
0.644	Remote Similarity	NPD5446	Phase 2
0.6436	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4336	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD3915	Approved
0.6432	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD1996	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