NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	451.35
Volume:	502.685
LogP:	6.627
LogD:	5.091
LogS:	-6.551
# Rotatable Bonds:	3
TPSA:	53.09
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.374
Synthetic Accessibility Score:	4.709
Fsp3:	0.767
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.972
MDCK Permeability:	1.0102732630912215e-05
Pgp-inhibitor:	0.962
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.745
30% Bioavailability (F30%):	0.597

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	99.53934478759766%
Volume Distribution (VD):	1.123
Pgp-substrate:	2.321641445159912%

ADMET: Metabolism

CYP1A2-inhibitor:	0.089
CYP1A2-substrate:	0.641
CYP2C19-inhibitor:	0.357
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.545
CYP2C9-substrate:	0.502
CYP2D6-inhibitor:	0.637
CYP2D6-substrate:	0.247
CYP3A4-inhibitor:	0.867
CYP3A4-substrate:	0.732

ADMET: Excretion

Clearance (CL):	5.9
Half-life (T1/2):	0.02

ADMET: Toxicity

hERG Blockers:	0.362
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.885
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.048
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC477041

Natural Product ID:	NPC477041
*Common Name:**	Laxiracemosin A
IUPAC Name:	1-[4-[(3R,9R,10R,13S,14S,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-1H-pyrrol-2-yl]-2-methylpropan-1-one
Synonyms:
Standard InCHIKey:	OYZKNOGIJLFQSF-MQKGYZFGSA-N
Standard InCHI:	InChI=1S/C30H45NO2/c1-18(2)26(33)23-16-19(17-31-23)20-10-14-30(7)22-8-9-24-27(3,4)25(32)12-13-28(24,5)21(22)11-15-29(20,30)6/h8,16-18,20-21,24-25,31-32H,9-15H2,1-7H3/t20-,21-,24?,25+,28+,29-,30+/m0/s1
SMILES:	CC(C)C(=O)C1=CC(=CN1)[C@@H]2CC[C@]3([C@]2(CC[C@H]4C3=CCC5[C@@]4(CC[C@H](C5(C)C)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49864192
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003027] 3-hydroxysteroids [CHEMONTID:0003232] 3-alpha-hydroxysteroids

*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
NPO33538	Dysoxylum laxiracemosum	Species	Meliaceae	Eukaryota	bark	Xishuangbanna, Yunnan Province, China	n.a.	PMID[20669932]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	3100	nM	PMID[20669932]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	9500	nM	PMID[20669932]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5400	nM	PMID[20669932]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	16800	nM	PMID[20669932]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	7200	nM	PMID[20669932]

☑ 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 NPC477041 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	297
0.1-0.2	1453
0.2-0.3	5088
0.3-0.4	23310
0.4-0.5	8228
0.5-0.6	2386
0.6-0.7	1679
0.7-0.8	248
0.8-0.85	2
0.85-0.9	1
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477044
0.9831	High Similarity	NPC477045
0.9669	High Similarity	NPC477043
0.9143	High Similarity	NPC477042
0.8207	Intermediate Similarity	NPC300688
0.8125	Intermediate Similarity	NPC11445
0.8112	Intermediate Similarity	NPC98715
0.8098	Intermediate Similarity	NPC151939
0.8073	Intermediate Similarity	NPC157828
0.8073	Intermediate Similarity	NPC195239
0.8063	Intermediate Similarity	NPC47190
0.804	Intermediate Similarity	NPC258062
0.804	Intermediate Similarity	NPC127677
0.803	Intermediate Similarity	NPC204491
0.803	Intermediate Similarity	NPC203614
0.801	Intermediate Similarity	NPC300183
0.8	Intermediate Similarity	NPC209917
0.799	Intermediate Similarity	NPC225821
0.799	Intermediate Similarity	NPC46225
0.7972	Intermediate Similarity	NPC70155
0.7957	Intermediate Similarity	NPC213468
0.791	Intermediate Similarity	NPC271862
0.7882	Intermediate Similarity	NPC151976
0.7882	Intermediate Similarity	NPC87856
0.7869	Intermediate Similarity	NPC201700
0.7865	Intermediate Similarity	NPC206967
0.7854	Intermediate Similarity	NPC132211
0.7847	Intermediate Similarity	NPC147446
0.7843	Intermediate Similarity	NPC267965
0.7778	Intermediate Similarity	NPC252338
0.7744	Intermediate Similarity	NPC267343
0.7742	Intermediate Similarity	NPC97525
0.7725	Intermediate Similarity	NPC471997
0.7725	Intermediate Similarity	NPC235885
0.7725	Intermediate Similarity	NPC141428
0.7716	Intermediate Similarity	NPC227582
0.7708	Intermediate Similarity	NPC99428
0.7689	Intermediate Similarity	NPC267926
0.7688	Intermediate Similarity	NPC262338
0.7678	Intermediate Similarity	NPC266192
0.7653	Intermediate Similarity	NPC57690
0.7632	Intermediate Similarity	NPC198339
0.7629	Intermediate Similarity	NPC473628
0.76	Intermediate Similarity	NPC470279
0.7598	Intermediate Similarity	NPC143075
0.759	Intermediate Similarity	NPC154339
0.759	Intermediate Similarity	NPC475874
0.7588	Intermediate Similarity	NPC473747
0.7583	Intermediate Similarity	NPC2395
0.7546	Intermediate Similarity	NPC290529
0.7541	Intermediate Similarity	NPC474492
0.7538	Intermediate Similarity	NPC74153
0.7526	Intermediate Similarity	NPC284775
0.7525	Intermediate Similarity	NPC260900
0.7512	Intermediate Similarity	NPC475151
0.7511	Intermediate Similarity	NPC37473
0.75	Intermediate Similarity	NPC470680
0.75	Intermediate Similarity	NPC471655
0.75	Intermediate Similarity	NPC100104
0.75	Intermediate Similarity	NPC302191
0.7473	Intermediate Similarity	NPC71132
0.7463	Intermediate Similarity	NPC74413
0.7448	Intermediate Similarity	NPC79777
0.7448	Intermediate Similarity	NPC234403
0.7446	Intermediate Similarity	NPC80681
0.7423	Intermediate Similarity	NPC165201
0.7419	Intermediate Similarity	NPC311276
0.7419	Intermediate Similarity	NPC40779
0.7398	Intermediate Similarity	NPC119700
0.7396	Intermediate Similarity	NPC248041
0.7396	Intermediate Similarity	NPC55772
0.7396	Intermediate Similarity	NPC126709
0.7394	Intermediate Similarity	NPC154293
0.7394	Intermediate Similarity	NPC78020
0.7391	Intermediate Similarity	NPC469762
0.7387	Intermediate Similarity	NPC473821
0.7385	Intermediate Similarity	NPC280290
0.7382	Intermediate Similarity	NPC267885
0.7374	Intermediate Similarity	NPC476460
0.7368	Intermediate Similarity	NPC477976
0.7363	Intermediate Similarity	NPC473814
0.7363	Intermediate Similarity	NPC78767
0.736	Intermediate Similarity	NPC321708
0.7353	Intermediate Similarity	NPC123019
0.7353	Intermediate Similarity	NPC476874
0.735	Intermediate Similarity	NPC181502
0.735	Intermediate Similarity	NPC85066
0.7347	Intermediate Similarity	NPC235684
0.7347	Intermediate Similarity	NPC94752
0.7347	Intermediate Similarity	NPC315555
0.7337	Intermediate Similarity	NPC469785
0.7333	Intermediate Similarity	NPC477003
0.733	Intermediate Similarity	NPC18661
0.733	Intermediate Similarity	NPC149155
0.733	Intermediate Similarity	NPC110500
0.733	Intermediate Similarity	NPC203468
0.733	Intermediate Similarity	NPC175602
0.7323	Intermediate Similarity	NPC95783
0.7311	Intermediate Similarity	NPC472285
0.731	Intermediate Similarity	NPC23476
0.731	Intermediate Similarity	NPC477415
0.731	Intermediate Similarity	NPC474259
0.7308	Intermediate Similarity	NPC162860
0.7308	Intermediate Similarity	NPC61038
0.7306	Intermediate Similarity	NPC283219
0.7302	Intermediate Similarity	NPC70949
0.73	Intermediate Similarity	NPC304203
0.7286	Intermediate Similarity	NPC110182
0.7283	Intermediate Similarity	NPC209362
0.7268	Intermediate Similarity	NPC182940
0.7264	Intermediate Similarity	NPC93390
0.7255	Intermediate Similarity	NPC195461
0.7255	Intermediate Similarity	NPC81654
0.7255	Intermediate Similarity	NPC79129
0.7255	Intermediate Similarity	NPC249150
0.7255	Intermediate Similarity	NPC49196
0.7255	Intermediate Similarity	NPC313985
0.7254	Intermediate Similarity	NPC84827
0.7254	Intermediate Similarity	NPC145885
0.7254	Intermediate Similarity	NPC14113
0.725	Intermediate Similarity	NPC472292
0.7245	Intermediate Similarity	NPC228835
0.7241	Intermediate Similarity	NPC50503
0.724	Intermediate Similarity	NPC293216
0.7235	Intermediate Similarity	NPC473850
0.7235	Intermediate Similarity	NPC475137
0.7235	Intermediate Similarity	NPC475498
0.7233	Intermediate Similarity	NPC317701
0.7228	Intermediate Similarity	NPC259644
0.7228	Intermediate Similarity	NPC472293
0.7228	Intermediate Similarity	NPC469763
0.7228	Intermediate Similarity	NPC469786
0.7228	Intermediate Similarity	NPC469760
0.7228	Intermediate Similarity	NPC292361
0.7228	Intermediate Similarity	NPC73952
0.7228	Intermediate Similarity	NPC469765
0.7228	Intermediate Similarity	NPC25008
0.7225	Intermediate Similarity	NPC478158
0.7216	Intermediate Similarity	NPC6093
0.7214	Intermediate Similarity	NPC326422
0.7213	Intermediate Similarity	NPC473878
0.7212	Intermediate Similarity	NPC54420
0.7207	Intermediate Similarity	NPC114033
0.7207	Intermediate Similarity	NPC129412
0.7207	Intermediate Similarity	NPC101130
0.7207	Intermediate Similarity	NPC58268
0.7206	Intermediate Similarity	NPC472297
0.7206	Intermediate Similarity	NPC472296
0.7202	Intermediate Similarity	NPC472762
0.7198	Intermediate Similarity	NPC100726
0.7196	Intermediate Similarity	NPC42372
0.7196	Intermediate Similarity	NPC281049
0.7194	Intermediate Similarity	NPC159125
0.7192	Intermediate Similarity	NPC167710
0.719	Intermediate Similarity	NPC234999
0.719	Intermediate Similarity	NPC475165
0.7189	Intermediate Similarity	NPC250807
0.7189	Intermediate Similarity	NPC76565
0.7189	Intermediate Similarity	NPC211572
0.7189	Intermediate Similarity	NPC57797
0.7189	Intermediate Similarity	NPC80597
0.7189	Intermediate Similarity	NPC75540
0.7189	Intermediate Similarity	NPC212376
0.7189	Intermediate Similarity	NPC70922
0.7186	Intermediate Similarity	NPC34271
0.7184	Intermediate Similarity	NPC328318
0.7184	Intermediate Similarity	NPC328596
0.7178	Intermediate Similarity	NPC202812
0.717	Intermediate Similarity	NPC207866
0.717	Intermediate Similarity	NPC229348
0.7165	Intermediate Similarity	NPC111275
0.7164	Intermediate Similarity	NPC67551
0.7159	Intermediate Similarity	NPC291517
0.7158	Intermediate Similarity	NPC160105
0.7158	Intermediate Similarity	NPC49954
0.7158	Intermediate Similarity	NPC474561
0.7157	Intermediate Similarity	NPC207851
0.7156	Intermediate Similarity	NPC82370
0.7156	Intermediate Similarity	NPC250129
0.715	Intermediate Similarity	NPC83111
0.7143	Intermediate Similarity	NPC191415
0.7143	Intermediate Similarity	NPC231342
0.7143	Intermediate Similarity	NPC274981
0.7136	Intermediate Similarity	NPC471284
0.7136	Intermediate Similarity	NPC471190
0.7136	Intermediate Similarity	NPC475506
0.7136	Intermediate Similarity	NPC475362
0.7136	Intermediate Similarity	NPC278434
0.7136	Intermediate Similarity	NPC470486
0.7136	Intermediate Similarity	NPC475644
0.7136	Intermediate Similarity	NPC478157
0.7136	Intermediate Similarity	NPC471977
0.7135	Intermediate Similarity	NPC251391
0.7129	Intermediate Similarity	NPC247735
0.7129	Intermediate Similarity	NPC472210
0.7129	Intermediate Similarity	NPC81802
0.7129	Intermediate Similarity	NPC477414
0.7129	Intermediate Similarity	NPC225622
0.7129	Intermediate Similarity	NPC221726
0.7129	Intermediate Similarity	NPC269886

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 NPC477041 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	531
0.2-0.3	610
0.3-0.4	2164
0.4-0.5	3119
0.5-0.6	1958
0.6-0.7	545
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
0.7778	Intermediate Similarity	NPD3178	Discontinued
0.7606	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD6026	Approved
0.7525	Intermediate Similarity	NPD7187	Phase 2
0.7524	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD5901	Discontinued
0.733	Intermediate Similarity	NPD482	Approved
0.7326	Intermediate Similarity	NPD6635	Approved
0.7299	Intermediate Similarity	NPD7707	Approved
0.7282	Intermediate Similarity	NPD2094	Phase 2
0.7282	Intermediate Similarity	NPD2095	Phase 2
0.7282	Intermediate Similarity	NPD2092	Phase 2
0.726	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6376	Discontinued
0.7255	Intermediate Similarity	NPD4600	Approved
0.7255	Intermediate Similarity	NPD4601	Approved
0.7255	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7957	Phase 1
0.7246	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD2096	Phase 2
0.7245	Intermediate Similarity	NPD2091	Phase 2
0.7217	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7234	Approved
0.7186	Intermediate Similarity	NPD7233	Approved
0.7183	Intermediate Similarity	NPD3394	Approved
0.7183	Intermediate Similarity	NPD3389	Approved
0.7183	Intermediate Similarity	NPD3393	Approved
0.7177	Intermediate Similarity	NPD7191	Phase 2
0.7172	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1631	Approved
0.7128	Intermediate Similarity	NPD4076	Approved
0.7128	Intermediate Similarity	NPD4079	Approved
0.7115	Intermediate Similarity	NPD5426	Phase 3
0.7115	Intermediate Similarity	NPD6987	Phase 1
0.7114	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3238	Discontinued
0.7109	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD750	Phase 2
0.7095	Intermediate Similarity	NPD2509	Approved
0.7095	Intermediate Similarity	NPD2510	Approved
0.7094	Intermediate Similarity	NPD7619	Phase 3
0.7094	Intermediate Similarity	NPD7618	Phase 3
0.7094	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6595	Phase 3
0.7083	Intermediate Similarity	NPD1573	Approved
0.7083	Intermediate Similarity	NPD1575	Approved
0.7077	Intermediate Similarity	NPD3506	Approved
0.7077	Intermediate Similarity	NPD3505	Approved
0.7077	Intermediate Similarity	NPD2753	Discontinued
0.7075	Intermediate Similarity	NPD7470	Discontinued
0.705	Intermediate Similarity	NPD8431	Approved
0.7033	Intermediate Similarity	NPD8114	Approved
0.7033	Intermediate Similarity	NPD8115	Approved
0.703	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6664	Approved
0.701	Intermediate Similarity	NPD7944	Discontinued
0.7005	Intermediate Similarity	NPD2481	Approved
0.7005	Intermediate Similarity	NPD2479	Phase 3
0.7	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1630	Approved
0.6968	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4051	Discontinued
0.693	Remote Similarity	NPD8094	Discontinued
0.6919	Remote Similarity	NPD7010	Phase 3
0.6916	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6995	Phase 1
0.6905	Remote Similarity	NPD6176	Phase 1
0.6905	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD2144	Approved
0.6895	Remote Similarity	NPD6242	Discontinued
0.689	Remote Similarity	NPD7817	Phase 1
0.6884	Remote Similarity	NPD8093	Discontinued
0.6884	Remote Similarity	NPD3038	Discontinued
0.6875	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2511	Approved
0.6856	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD5473	Discontinued
0.6825	Remote Similarity	NPD8072	Approved
0.6818	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7564	Discontinued
0.6816	Remote Similarity	NPD6178	Phase 3
0.6814	Remote Similarity	NPD4499	Approved
0.6812	Remote Similarity	NPD4848	Phase 1
0.6812	Remote Similarity	NPD6226	Phase 3
0.681	Remote Similarity	NPD7727	Phase 2
0.681	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2214	Approved
0.6806	Remote Similarity	NPD2213	Approved
0.6804	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6446	Discontinued
0.6802	Remote Similarity	NPD5065	Approved
0.68	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7824	Approved
0.6798	Remote Similarity	NPD3961	Discontinued
0.6794	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3947	Discontinued
0.6792	Remote Similarity	NPD8272	Phase 2
0.6788	Remote Similarity	NPD5088	Discontinued
0.6784	Remote Similarity	NPD1587	Approved
0.6784	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4075	Phase 2
0.6766	Remote Similarity	NPD3320	Approved
0.6766	Remote Similarity	NPD3318	Approved
0.6766	Remote Similarity	NPD3319	Phase 1
0.6765	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD8641	Approved
0.6762	Remote Similarity	NPD484	Approved
0.676	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD8289	Discontinued
0.6738	Remote Similarity	NPD4703	Approved
0.6738	Remote Similarity	NPD4702	Approved
0.6733	Remote Similarity	NPD1096	Discontinued
0.6728	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6849	Phase 2
0.6726	Remote Similarity	NPD6850	Phase 2
0.6716	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD8169	Discontinued
0.6714	Remote Similarity	NPD6999	Discontinued
0.6714	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7950	Approved
0.6711	Remote Similarity	NPD7789	Approved
0.6711	Remote Similarity	NPD7952	Approved
0.6711	Remote Similarity	NPD7791	Approved
0.6711	Remote Similarity	NPD7953	Approved
0.6711	Remote Similarity	NPD7790	Approved
0.6711	Remote Similarity	NPD7730	Approved
0.6711	Remote Similarity	NPD7731	Approved
0.6711	Remote Similarity	NPD7951	Approved
0.6709	Remote Similarity	NPD8468	Phase 2
0.6701	Remote Similarity	NPD3583	Phase 2
0.67	Remote Similarity	NPD6555	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD2336	Approved
0.6698	Remote Similarity	NPD8073	Approved
0.6697	Remote Similarity	NPD3794	Approved
0.6697	Remote Similarity	NPD3795	Approved
0.6696	Remote Similarity	NPD7271	Approved
0.6696	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4639	Approved
0.6684	Remote Similarity	NPD4638	Approved
0.6684	Remote Similarity	NPD4640	Approved
0.6683	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6068	Discontinued
0.6682	Remote Similarity	NPD6479	Discontinued
0.6682	Remote Similarity	NPD7001	Phase 3
0.6682	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2172	Phase 1
0.6667	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2896	Discontinued
0.6667	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD7454	Approved
0.6651	Remote Similarity	NPD7455	Approved
0.6651	Remote Similarity	NPD2411	Approved
0.6651	Remote Similarity	NPD5017	Discontinued
0.665	Remote Similarity	NPD4181	Approved
0.665	Remote Similarity	NPD8123	Approved
0.665	Remote Similarity	NPD8122	Approved
0.6649	Remote Similarity	NPD1270	Approved
0.6649	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD460	Discontinued
0.6635	Remote Similarity	NPD7308	Discontinued
0.6634	Remote Similarity	NPD6791	Phase 2
0.6634	Remote Similarity	NPD4988	Discontinued
0.6633	Remote Similarity	NPD1586	Approved
0.6633	Remote Similarity	NPD2928	Phase 2
0.6633	Remote Similarity	NPD4883	Approved
0.6623	Remote Similarity	NPD7688	Phase 1
0.6619	Remote Similarity	NPD7948	Phase 1
0.6615	Remote Similarity	NPD3323	Discontinued
0.6615	Remote Similarity	NPD2580	Discontinued
0.6613	Remote Similarity	NPD3717	Discontinued
0.6605	Remote Similarity	NPD2008	Discontinued
0.6605	Remote Similarity	NPD7568	Phase 1
0.6605	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD2844	Phase 3
0.6596	Remote Similarity	NPD6148	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