NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	449.33
Volume:	500.049
LogP:	6.486
LogD:	4.99
LogS:	-6.225
# Rotatable Bonds:	3
TPSA:	49.93
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.384
Synthetic Accessibility Score:	4.662
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.024
MDCK Permeability:	8.916626029531471e-06
Pgp-inhibitor:	0.913
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.947
30% Bioavailability (F30%):	0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	99.38369750976562%
Volume Distribution (VD):	1.086
Pgp-substrate:	2.849665880203247%

ADMET: Metabolism

CYP1A2-inhibitor:	0.112
CYP1A2-substrate:	0.873
CYP2C19-inhibitor:	0.595
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.516
CYP2C9-substrate:	0.677
CYP2D6-inhibitor:	0.664
CYP2D6-substrate:	0.26
CYP3A4-inhibitor:	0.907
CYP3A4-substrate:	0.815

ADMET: Excretion

Clearance (CL):	7.279
Half-life (T1/2):	0.059

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.22
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.855
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.031
Carcinogencity:	0.132
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC477042

Natural Product ID:	NPC477042
*Common Name:**	Laxiracemosin B
IUPAC Name:	(9R,10R,13S,14S,17R)-4,4,10,13,14-pentamethyl-17-[5-(2-methylpropanoyl)-1H-pyrrol-3-yl]-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	NGBICDGUHNVMPO-UCRHFLBXSA-N
Standard InCHI:	InChI=1S/C30H43NO2/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/h8,16-18,20-21,24,31H,9-15H2,1-7H3/t20-,21-,24?,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(CCC(=O)C5(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49864193
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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	=	12800	nM	PMID[20669932]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	19000	nM	PMID[20669932]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	13400	nM	PMID[20669932]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20000	nM	PMID[20669932]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	20000	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 NPC477042 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	505
0.1-0.2	2310
0.2-0.3	13281
0.3-0.4	19357
0.4-0.5	3482
0.5-0.6	2117
0.6-0.7	1433
0.7-0.8	203
0.8-0.85	4
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9143	High Similarity	NPC477044
0.9143	High Similarity	NPC477041
0.8983	High Similarity	NPC477045
0.884	High Similarity	NPC477043
0.8436	Intermediate Similarity	NPC47190
0.8363	Intermediate Similarity	NPC262338
0.8214	Intermediate Similarity	NPC474492
0.8182	Intermediate Similarity	NPC471655
0.8171	Intermediate Similarity	NPC284775
0.8166	Intermediate Similarity	NPC100104
0.8166	Intermediate Similarity	NPC470680
0.8129	Intermediate Similarity	NPC71132
0.8107	Intermediate Similarity	NPC80681
0.8079	Intermediate Similarity	NPC79777
0.8079	Intermediate Similarity	NPC234403
0.8043	Intermediate Similarity	NPC157828
0.8043	Intermediate Similarity	NPC195239
0.8	Intermediate Similarity	NPC11445
0.7978	Intermediate Similarity	NPC476460
0.7944	Intermediate Similarity	NPC477003
0.7931	Intermediate Similarity	NPC70949
0.7912	Intermediate Similarity	NPC477415
0.7912	Intermediate Similarity	NPC474259
0.7912	Intermediate Similarity	NPC23476
0.7892	Intermediate Similarity	NPC304203
0.7877	Intermediate Similarity	NPC182940
0.7857	Intermediate Similarity	NPC473878
0.7844	Intermediate Similarity	NPC100726
0.7826	Intermediate Similarity	NPC291517
0.7821	Intermediate Similarity	NPC213468
0.7801	Intermediate Similarity	NPC317701
0.7796	Intermediate Similarity	NPC326422
0.7766	Intermediate Similarity	NPC167710
0.7765	Intermediate Similarity	NPC251391
0.7759	Intermediate Similarity	NPC274981
0.7735	Intermediate Similarity	NPC191415
0.7714	Intermediate Similarity	NPC115232
0.7708	Intermediate Similarity	NPC98715
0.7706	Intermediate Similarity	NPC70406
0.7706	Intermediate Similarity	NPC217021
0.7706	Intermediate Similarity	NPC470679
0.7701	Intermediate Similarity	NPC477414
0.7701	Intermediate Similarity	NPC225622
0.7701	Intermediate Similarity	NPC221726
0.7676	Intermediate Similarity	NPC473628
0.7657	Intermediate Similarity	NPC265100
0.7654	Intermediate Similarity	NPC293216
0.7651	Intermediate Similarity	NPC58268
0.7651	Intermediate Similarity	NPC114033
0.7651	Intermediate Similarity	NPC129412
0.7651	Intermediate Similarity	NPC101130
0.7644	Intermediate Similarity	NPC252338
0.7634	Intermediate Similarity	NPC268966
0.7634	Intermediate Similarity	NPC475874
0.763	Intermediate Similarity	NPC286427
0.7619	Intermediate Similarity	NPC467188
0.7614	Intermediate Similarity	NPC42372
0.7614	Intermediate Similarity	NPC233380
0.7604	Intermediate Similarity	NPC300183
0.76	Intermediate Similarity	NPC214106
0.759	Intermediate Similarity	NPC46225
0.759	Intermediate Similarity	NPC225821
0.7588	Intermediate Similarity	NPC123906
0.7579	Intermediate Similarity	NPC227582
0.7577	Intermediate Similarity	NPC88115
0.7565	Intermediate Similarity	NPC260900
0.7551	Intermediate Similarity	NPC258062
0.7551	Intermediate Similarity	NPC127677
0.754	Intermediate Similarity	NPC324091
0.7539	Intermediate Similarity	NPC34837
0.7529	Intermediate Similarity	NPC105811
0.7514	Intermediate Similarity	NPC133003
0.7513	Intermediate Similarity	NPC271862
0.75	Intermediate Similarity	NPC74413
0.7487	Intermediate Similarity	NPC477413
0.7487	Intermediate Similarity	NPC209917
0.7487	Intermediate Similarity	NPC74153
0.7486	Intermediate Similarity	NPC41257
0.7474	Intermediate Similarity	NPC106757
0.7473	Intermediate Similarity	NPC151939
0.7446	Intermediate Similarity	NPC470677
0.7442	Intermediate Similarity	NPC313889
0.743	Intermediate Similarity	NPC201700
0.7419	Intermediate Similarity	NPC280290
0.7414	Intermediate Similarity	NPC209362
0.7409	Intermediate Similarity	NPC477004
0.7405	Intermediate Similarity	NPC102755
0.74	Intermediate Similarity	NPC151976
0.74	Intermediate Similarity	NPC87856
0.7394	Intermediate Similarity	NPC23215
0.7391	Intermediate Similarity	NPC300688
0.7384	Intermediate Similarity	NPC102664
0.7377	Intermediate Similarity	NPC145885
0.7377	Intermediate Similarity	NPC14113
0.7377	Intermediate Similarity	NPC84827
0.7377	Intermediate Similarity	NPC237188
0.7377	Intermediate Similarity	NPC157583
0.7368	Intermediate Similarity	NPC216550
0.7366	Intermediate Similarity	NPC228835
0.7363	Intermediate Similarity	NPC186068
0.7363	Intermediate Similarity	NPC267965
0.7349	Intermediate Similarity	NPC138596
0.7349	Intermediate Similarity	NPC200397
0.7349	Intermediate Similarity	NPC195704
0.7349	Intermediate Similarity	NPC292434
0.7349	Intermediate Similarity	NPC167200
0.7349	Intermediate Similarity	NPC98156
0.7349	Intermediate Similarity	NPC14448
0.7349	Intermediate Similarity	NPC64661
0.7346	Intermediate Similarity	NPC70155
0.7337	Intermediate Similarity	NPC11126
0.733	Intermediate Similarity	NPC473821
0.733	Intermediate Similarity	NPC267343
0.7326	Intermediate Similarity	NPC99939
0.7326	Intermediate Similarity	NPC308931
0.732	Intermediate Similarity	NPC237414
0.7312	Intermediate Similarity	NPC470205
0.7308	Intermediate Similarity	NPC477976
0.7306	Intermediate Similarity	NPC473814
0.7306	Intermediate Similarity	NPC78767
0.7302	Intermediate Similarity	NPC103119
0.7297	Intermediate Similarity	NPC73994
0.7297	Intermediate Similarity	NPC471997
0.7293	Intermediate Similarity	NPC471943
0.7291	Intermediate Similarity	NPC132211
0.7291	Intermediate Similarity	NPC203614
0.7291	Intermediate Similarity	NPC204491
0.7288	Intermediate Similarity	NPC56765
0.7288	Intermediate Similarity	NPC318065
0.7288	Intermediate Similarity	NPC206819
0.7287	Intermediate Similarity	NPC94752
0.7287	Intermediate Similarity	NPC99428
0.7283	Intermediate Similarity	NPC83774
0.7278	Intermediate Similarity	NPC469780
0.7278	Intermediate Similarity	NPC469783
0.7278	Intermediate Similarity	NPC469768
0.7278	Intermediate Similarity	NPC469767
0.7278	Intermediate Similarity	NPC469779
0.7278	Intermediate Similarity	NPC469784
0.7278	Intermediate Similarity	NPC469761
0.7277	Intermediate Similarity	NPC472292
0.7263	Intermediate Similarity	NPC21174
0.7263	Intermediate Similarity	NPC271797
0.7263	Intermediate Similarity	NPC154339
0.7254	Intermediate Similarity	NPC472293
0.7253	Intermediate Similarity	NPC6982
0.7243	Intermediate Similarity	NPC55772
0.7243	Intermediate Similarity	NPC248041
0.7243	Intermediate Similarity	NPC126709
0.7241	Intermediate Similarity	NPC53947
0.7241	Intermediate Similarity	NPC24678
0.7241	Intermediate Similarity	NPC105818
0.7238	Intermediate Similarity	NPC78020
0.7235	Intermediate Similarity	NPC469766
0.7232	Intermediate Similarity	NPC76982
0.7232	Intermediate Similarity	NPC213914
0.7228	Intermediate Similarity	NPC267885
0.7228	Intermediate Similarity	NPC151635
0.7225	Intermediate Similarity	NPC477974
0.7219	Intermediate Similarity	NPC117027
0.7216	Intermediate Similarity	NPC229055
0.7213	Intermediate Similarity	NPC252572
0.7211	Intermediate Similarity	NPC321708
0.7209	Intermediate Similarity	NPC314372
0.7207	Intermediate Similarity	NPC242116
0.7204	Intermediate Similarity	NPC61011
0.7202	Intermediate Similarity	NPC93390
0.72	Intermediate Similarity	NPC143075
0.7198	Intermediate Similarity	NPC194411
0.7196	Intermediate Similarity	NPC469359
0.7196	Intermediate Similarity	NPC235684
0.7194	Intermediate Similarity	NPC470279
0.7193	Intermediate Similarity	NPC190296
0.7175	Intermediate Similarity	NPC74357
0.7174	Intermediate Similarity	NPC110500
0.7174	Intermediate Similarity	NPC203468
0.7174	Intermediate Similarity	NPC149155
0.7174	Intermediate Similarity	NPC469529
0.7165	Intermediate Similarity	NPC102592
0.7165	Intermediate Similarity	NPC79356
0.7159	Intermediate Similarity	NPC469765
0.7159	Intermediate Similarity	NPC200743
0.7159	Intermediate Similarity	NPC469763
0.7159	Intermediate Similarity	NPC73952
0.7159	Intermediate Similarity	NPC469760
0.7159	Intermediate Similarity	NPC469786
0.7159	Intermediate Similarity	NPC25008
0.7159	Intermediate Similarity	NPC259644
0.7158	Intermediate Similarity	NPC17059
0.7151	Intermediate Similarity	NPC283219
0.715	Intermediate Similarity	NPC81802
0.715	Intermediate Similarity	NPC472295
0.715	Intermediate Similarity	NPC247735
0.715	Intermediate Similarity	NPC269886
0.715	Intermediate Similarity	NPC472210
0.7143	Intermediate Similarity	NPC472297
0.7143	Intermediate Similarity	NPC261195
0.7143	Intermediate Similarity	NPC472296
0.7143	Intermediate Similarity	NPC29886
0.7135	Intermediate Similarity	NPC138370

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 NPC477042 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	579
0.2-0.3	811
0.3-0.4	2555
0.4-0.5	2553
0.5-0.6	1773
0.6-0.7	574
0.7-0.8	36
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
0.8146	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD3178	Discontinued
0.7709	Intermediate Similarity	NPD3238	Discontinued
0.7688	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2753	Discontinued
0.7582	Intermediate Similarity	NPD2479	Phase 3
0.7582	Intermediate Similarity	NPD2481	Approved
0.7461	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6664	Approved
0.7391	Intermediate Similarity	NPD5473	Discontinued
0.7387	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7619	Phase 3
0.7382	Intermediate Similarity	NPD7618	Phase 3
0.7378	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6446	Discontinued
0.7366	Intermediate Similarity	NPD7564	Discontinued
0.7344	Intermediate Similarity	NPD4848	Phase 1
0.7322	Intermediate Similarity	NPD4075	Phase 2
0.7312	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3320	Approved
0.7312	Intermediate Similarity	NPD3319	Phase 1
0.7312	Intermediate Similarity	NPD3318	Approved
0.7297	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD3583	Phase 2
0.7241	Intermediate Similarity	NPD2172	Phase 1
0.7228	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD1270	Approved
0.7222	Intermediate Similarity	NPD5901	Discontinued
0.7222	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7187	Phase 2
0.7196	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD2214	Approved
0.7191	Intermediate Similarity	NPD1630	Approved
0.7191	Intermediate Similarity	NPD2213	Approved
0.7175	Intermediate Similarity	NPD2580	Discontinued
0.7174	Intermediate Similarity	NPD482	Approved
0.7167	Intermediate Similarity	NPD3323	Discontinued
0.7158	Intermediate Similarity	NPD3961	Discontinued
0.7158	Intermediate Similarity	NPD4988	Discontinued
0.7143	Intermediate Similarity	NPD2411	Approved
0.7135	Intermediate Similarity	NPD1722	Approved
0.7128	Intermediate Similarity	NPD2094	Phase 2
0.7128	Intermediate Similarity	NPD2092	Phase 2
0.7128	Intermediate Similarity	NPD2095	Phase 2
0.7127	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD786	Approved
0.7113	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD2008	Discontinued
0.7098	Intermediate Similarity	NPD4922	Phase 2
0.7097	Intermediate Similarity	NPD3506	Approved
0.7097	Intermediate Similarity	NPD3505	Approved
0.709	Intermediate Similarity	NPD2096	Phase 2
0.709	Intermediate Similarity	NPD2091	Phase 2
0.7088	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3100	Discontinued
0.7086	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD1631	Approved
0.7072	Intermediate Similarity	NPD6635	Approved
0.7068	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4076	Approved
0.7059	Intermediate Similarity	NPD4079	Approved
0.7056	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6987	Phase 1
0.7049	Intermediate Similarity	NPD1343	Approved
0.7044	Intermediate Similarity	NPD4051	Discontinued
0.7041	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3393	Approved
0.7039	Intermediate Similarity	NPD3389	Approved
0.7039	Intermediate Similarity	NPD3394	Approved
0.703	Intermediate Similarity	NPD7191	Phase 2
0.703	Intermediate Similarity	NPD2509	Approved
0.703	Intermediate Similarity	NPD6376	Discontinued
0.703	Intermediate Similarity	NPD2510	Approved
0.7026	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD1573	Approved
0.7011	Intermediate Similarity	NPD1575	Approved
0.701	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4181	Approved
0.6989	Remote Similarity	NPD4883	Approved
0.6976	Remote Similarity	NPD7454	Approved
0.6976	Remote Similarity	NPD7455	Approved
0.6974	Remote Similarity	NPD460	Discontinued
0.6973	Remote Similarity	NPD3610	Approved
0.6973	Remote Similarity	NPD3609	Approved
0.6965	Remote Similarity	NPD5426	Phase 3
0.6961	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4524	Discontinued
0.6935	Remote Similarity	NPD750	Phase 2
0.6927	Remote Similarity	NPD6152	Phase 1
0.6923	Remote Similarity	NPD5400	Approved
0.6923	Remote Similarity	NPD4029	Approved
0.6923	Remote Similarity	NPD4030	Approved
0.6923	Remote Similarity	NPD4028	Approved
0.6919	Remote Similarity	NPD1982	Phase 1
0.6915	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD1600	Suspended
0.691	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD6226	Phase 3
0.6898	Remote Similarity	NPD4128	Approved
0.6891	Remote Similarity	NPD8431	Approved
0.6889	Remote Similarity	NPD6026	Approved
0.6865	Remote Similarity	NPD2641	Approved
0.6865	Remote Similarity	NPD2640	Approved
0.6862	Remote Similarity	NPD6044	Discontinued
0.686	Remote Similarity	NPD8094	Discontinued
0.6856	Remote Similarity	NPD7233	Approved
0.6856	Remote Similarity	NPD7175	Phase 1
0.6856	Remote Similarity	NPD7234	Approved
0.6854	Remote Similarity	NPD4462	Approved
0.6854	Remote Similarity	NPD4463	Approved
0.6847	Remote Similarity	NPD7010	Phase 3
0.6845	Remote Similarity	NPD3475	Approved
0.6845	Remote Similarity	NPD3476	Approved
0.6842	Remote Similarity	NPD3927	Phase 2
0.6839	Remote Similarity	NPD6217	Discontinued
0.6828	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6242	Discontinued
0.6821	Remote Similarity	NPD4499	Approved
0.6814	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD8093	Discontinued
0.6811	Remote Similarity	NPD2642	Approved
0.6811	Remote Similarity	NPD2639	Approved
0.68	Remote Similarity	NPD2405	Phase 3
0.6798	Remote Similarity	NPD3947	Discontinued
0.6796	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD2881	Approved
0.6782	Remote Similarity	NPD2879	Approved
0.678	Remote Similarity	NPD6459	Phase 2
0.6778	Remote Similarity	NPD2837	Discontinued
0.6778	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5199	Approved
0.6777	Remote Similarity	NPD5198	Approved
0.6776	Remote Similarity	NPD1403	Approved
0.6776	Remote Similarity	NPD1404	Approved
0.6774	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6068	Discontinued
0.6768	Remote Similarity	NPD5855	Phase 3
0.6768	Remote Similarity	NPD5853	Phase 3
0.6766	Remote Similarity	NPD2119	Approved
0.6766	Remote Similarity	NPD2118	Approved
0.6765	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7470	Discontinued
0.6761	Remote Similarity	NPD5254	Discontinued
0.6754	Remote Similarity	NPD6595	Phase 3
0.6753	Remote Similarity	NPD5809	Phase 3
0.6753	Remote Similarity	NPD7026	Phase 2
0.6749	Remote Similarity	NPD6176	Phase 1
0.6749	Remote Similarity	NPD4304	Discovery
0.6748	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.674	Remote Similarity	NPD2061	Approved
0.6739	Remote Similarity	NPD6771	Discontinued
0.6737	Remote Similarity	NPD2144	Approved
0.6736	Remote Similarity	NPD6178	Phase 3
0.6735	Remote Similarity	NPD5685	Approved
0.6735	Remote Similarity	NPD5686	Approved
0.6735	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5017	Discontinued
0.6732	Remote Similarity	NPD3905	Phase 3
0.672	Remote Similarity	NPD5065	Approved
0.672	Remote Similarity	NPD1586	Approved
0.6719	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD3038	Discontinued
0.6716	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD201	Phase 2
0.6705	Remote Similarity	NPD200	Phase 2
0.6705	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6787	Phase 2
0.6699	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5888	Phase 2
0.6686	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7957	Phase 1
0.6683	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD991	Phase 2
0.6667	Remote Similarity	NPD2896	Discontinued
0.6667	Remote Similarity	NPD6277	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