NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	224.07
Volume:	215.105
LogP:	0.212
LogD:	-0.287
LogS:	-2.248
# Rotatable Bonds:	0
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.355
Synthetic Accessibility Score:	4.939
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.891
MDCK Permeability:	5.453475387184881e-05
Pgp-inhibitor:	0.141
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.685
30% Bioavailability (F30%):	0.067

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.844
Plasma Protein Binding (PPB):	50.47014617919922%
Volume Distribution (VD):	0.422
Pgp-substrate:	67.123291015625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.137
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.353
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.186
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.223
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	3.7
Half-life (T1/2):	0.734

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.103
AMES Toxicity:	0.617
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.941
Carcinogencity:	0.541
Eye Corrosion:	0.636
Eye Irritation:	0.937
Respiratory Toxicity:	0.858

Download Data

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

Natural Product: NPC119740

Natural Product ID:	NPC119740
*Common Name:**	Massarigenin C
IUPAC Name:	(4R,5R,6R,10R)-4,6-dihydroxy-10-methyl-3-methylidene-2-oxaspiro[4.5]dec-8-ene-1,7-dione
Synonyms:	Massarigenin C
Standard InCHIKey:	MWZYYACVPIJBPD-SIWOTSRUSA-N
Standard InCHI:	InChI=1S/C11H12O5/c1-5-3-4-7(12)9(14)11(5)8(13)6(2)16-10(11)15/h3-5,8-9,13-14H,2H2,1H3/t5-,8+,9+,11-/m1/s1
SMILES:	C[C@@H]1C=CC(=O)[C@@H]([C@@]21[C@H](C(=C)OC2=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506572
PubChem CID:	10398700
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO32853	massarina tunicata	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096869]
NPO32853	massarina tunicata	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542349]
NPO40412	Malbranchea flavorosea	Species	Myxotrichaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28060505]

☑ 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
Others	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	9.0	mm	PMID[504763]
NPT2	Others	Unspecified		IC50	=	1250000.0	nM	PMID[504764]

☑ 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 NPC119740 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	180
0.1-0.2	1291
0.2-0.3	5793
0.3-0.4	13602
0.4-0.5	11545
0.5-0.6	7283
0.6-0.7	2753
0.7-0.8	244
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC150063
0.8605	High Similarity	NPC32676
0.8409	Intermediate Similarity	NPC278283
0.8	Intermediate Similarity	NPC478112
0.7935	Intermediate Similarity	NPC478110
0.7841	Intermediate Similarity	NPC474980
0.7742	Intermediate Similarity	NPC87306
0.7684	Intermediate Similarity	NPC469692
0.7684	Intermediate Similarity	NPC469645
0.766	Intermediate Similarity	NPC473455
0.7604	Intermediate Similarity	NPC121825
0.7582	Intermediate Similarity	NPC219966
0.7527	Intermediate Similarity	NPC473248
0.75	Intermediate Similarity	NPC128733
0.75	Intermediate Similarity	NPC185141
0.75	Intermediate Similarity	NPC133907
0.75	Intermediate Similarity	NPC110443
0.75	Intermediate Similarity	NPC46998
0.7471	Intermediate Similarity	NPC474197
0.7447	Intermediate Similarity	NPC153570
0.7426	Intermediate Similarity	NPC474747
0.7374	Intermediate Similarity	NPC169205
0.7368	Intermediate Similarity	NPC52198
0.7368	Intermediate Similarity	NPC117405
0.7353	Intermediate Similarity	NPC472755
0.7353	Intermediate Similarity	NPC475945
0.7353	Intermediate Similarity	NPC475871
0.7347	Intermediate Similarity	NPC214694
0.7347	Intermediate Similarity	NPC48803
0.7347	Intermediate Similarity	NPC275960
0.7347	Intermediate Similarity	NPC193645
0.7347	Intermediate Similarity	NPC90121
0.734	Intermediate Similarity	NPC472007
0.7327	Intermediate Similarity	NPC472753
0.7303	Intermediate Similarity	NPC469510
0.7303	Intermediate Similarity	NPC475699
0.73	Intermediate Similarity	NPC141191
0.7282	Intermediate Similarity	NPC475676
0.7282	Intermediate Similarity	NPC203659
0.7282	Intermediate Similarity	NPC472756
0.7282	Intermediate Similarity	NPC220964
0.7273	Intermediate Similarity	NPC185553
0.7264	Intermediate Similarity	NPC5103
0.7263	Intermediate Similarity	NPC472008
0.7263	Intermediate Similarity	NPC476803
0.7255	Intermediate Similarity	NPC472754
0.7255	Intermediate Similarity	NPC225353
0.7253	Intermediate Similarity	NPC275507
0.7253	Intermediate Similarity	NPC297440
0.7241	Intermediate Similarity	NPC476590
0.7241	Intermediate Similarity	NPC114727
0.7238	Intermediate Similarity	NPC264819
0.7234	Intermediate Similarity	NPC469910
0.7234	Intermediate Similarity	NPC472009
0.7222	Intermediate Similarity	NPC473981
0.7222	Intermediate Similarity	NPC291260
0.7222	Intermediate Similarity	NPC99651
0.7222	Intermediate Similarity	NPC473980
0.7222	Intermediate Similarity	NPC475210
0.7212	Intermediate Similarity	NPC469852
0.7204	Intermediate Similarity	NPC163615
0.7204	Intermediate Similarity	NPC38569
0.7204	Intermediate Similarity	NPC469884
0.7191	Intermediate Similarity	NPC474278
0.7188	Intermediate Similarity	NPC79027
0.7184	Intermediate Similarity	NPC110989
0.7184	Intermediate Similarity	NPC475873
0.7184	Intermediate Similarity	NPC4620
0.7159	Intermediate Similarity	NPC161038
0.7158	Intermediate Similarity	NPC23622
0.7157	Intermediate Similarity	NPC474742
0.7157	Intermediate Similarity	NPC47880
0.7143	Intermediate Similarity	NPC288240
0.7143	Intermediate Similarity	NPC162205
0.7143	Intermediate Similarity	NPC273579
0.7143	Intermediate Similarity	NPC295204
0.713	Intermediate Similarity	NPC66108
0.7129	Intermediate Similarity	NPC278386
0.7129	Intermediate Similarity	NPC124512
0.7129	Intermediate Similarity	NPC475284
0.7129	Intermediate Similarity	NPC159763
0.7129	Intermediate Similarity	NPC278008
0.7129	Intermediate Similarity	NPC281608
0.7129	Intermediate Similarity	NPC471144
0.7129	Intermediate Similarity	NPC300584
0.7128	Intermediate Similarity	NPC125290
0.7128	Intermediate Similarity	NPC470755
0.7128	Intermediate Similarity	NPC28887
0.7128	Intermediate Similarity	NPC155873
0.7115	Intermediate Similarity	NPC474741
0.7115	Intermediate Similarity	NPC296950
0.7113	Intermediate Similarity	NPC166554
0.7113	Intermediate Similarity	NPC474232
0.7113	Intermediate Similarity	NPC15059
0.7111	Intermediate Similarity	NPC279532
0.71	Intermediate Similarity	NPC477921
0.7097	Intermediate Similarity	NPC477785
0.7097	Intermediate Similarity	NPC477786
0.7097	Intermediate Similarity	NPC477784
0.7097	Intermediate Similarity	NPC161045
0.7097	Intermediate Similarity	NPC52923
0.7093	Intermediate Similarity	NPC107848
0.7087	Intermediate Similarity	NPC149371
0.7083	Intermediate Similarity	NPC228415
0.7083	Intermediate Similarity	NPC476805
0.7083	Intermediate Similarity	NPC87189
0.7083	Intermediate Similarity	NPC287089
0.7075	Intermediate Similarity	NPC233379
0.7075	Intermediate Similarity	NPC14862
0.7075	Intermediate Similarity	NPC474664
0.7071	Intermediate Similarity	NPC167219
0.7064	Intermediate Similarity	NPC469463
0.7064	Intermediate Similarity	NPC469454
0.7064	Intermediate Similarity	NPC469496
0.7048	Intermediate Similarity	NPC477125
0.7048	Intermediate Similarity	NPC472751
0.7048	Intermediate Similarity	NPC472749
0.7045	Intermediate Similarity	NPC474280
0.7041	Intermediate Similarity	NPC261607
0.7041	Intermediate Similarity	NPC300312
0.7041	Intermediate Similarity	NPC230623
0.7041	Intermediate Similarity	NPC473321
0.7041	Intermediate Similarity	NPC111114
0.7037	Intermediate Similarity	NPC179798
0.7037	Intermediate Similarity	NPC304180
0.703	Intermediate Similarity	NPC20066
0.7021	Intermediate Similarity	NPC158756
0.7021	Intermediate Similarity	NPC469809
0.7019	Intermediate Similarity	NPC472750
0.7019	Intermediate Similarity	NPC469980
0.7019	Intermediate Similarity	NPC118902
0.7019	Intermediate Similarity	NPC472747
0.7019	Intermediate Similarity	NPC104161
0.7011	Intermediate Similarity	NPC319163
0.7011	Intermediate Similarity	NPC67076
0.7009	Intermediate Similarity	NPC15218
0.7	Intermediate Similarity	NPC272267
0.7	Intermediate Similarity	NPC275530
0.7	Intermediate Similarity	NPC477922
0.7	Intermediate Similarity	NPC471142
0.699	Remote Similarity	NPC469657
0.699	Remote Similarity	NPC244456
0.699	Remote Similarity	NPC101067
0.699	Remote Similarity	NPC476134
0.6989	Remote Similarity	NPC475690
0.6989	Remote Similarity	NPC11383
0.6989	Remote Similarity	NPC310450
0.6989	Remote Similarity	NPC475046
0.6989	Remote Similarity	NPC26624
0.6989	Remote Similarity	NPC474252
0.6989	Remote Similarity	NPC474959
0.6981	Remote Similarity	NPC324327
0.6981	Remote Similarity	NPC474421
0.6981	Remote Similarity	NPC194620
0.6981	Remote Similarity	NPC469853
0.6981	Remote Similarity	NPC72813
0.6981	Remote Similarity	NPC326994
0.6977	Remote Similarity	NPC475982
0.697	Remote Similarity	NPC475302
0.6966	Remote Similarity	NPC473948
0.6952	Remote Similarity	NPC258532
0.6952	Remote Similarity	NPC472748
0.6952	Remote Similarity	NPC146731
0.6947	Remote Similarity	NPC21469
0.6947	Remote Similarity	NPC77971
0.6947	Remote Similarity	NPC11804
0.6939	Remote Similarity	NPC274075
0.6939	Remote Similarity	NPC265856
0.6939	Remote Similarity	NPC471399
0.6939	Remote Similarity	NPC473619
0.6937	Remote Similarity	NPC207217
0.6931	Remote Similarity	NPC469369
0.6931	Remote Similarity	NPC184065
0.6931	Remote Similarity	NPC469528
0.6923	Remote Similarity	NPC11796
0.6923	Remote Similarity	NPC473471
0.6923	Remote Similarity	NPC39996
0.6923	Remote Similarity	NPC218817
0.6923	Remote Similarity	NPC318481
0.6916	Remote Similarity	NPC154608
0.6916	Remote Similarity	NPC192813
0.6916	Remote Similarity	NPC55972
0.6916	Remote Similarity	NPC327286
0.6916	Remote Similarity	NPC277017
0.6916	Remote Similarity	NPC169888
0.6915	Remote Similarity	NPC284472
0.6915	Remote Similarity	NPC229799
0.6915	Remote Similarity	NPC40746
0.6915	Remote Similarity	NPC286770
0.6915	Remote Similarity	NPC169575
0.6909	Remote Similarity	NPC56448
0.6907	Remote Similarity	NPC475819
0.6907	Remote Similarity	NPC473715
0.6903	Remote Similarity	NPC268958
0.69	Remote Similarity	NPC289004
0.69	Remote Similarity	NPC65829
0.69	Remote Similarity	NPC469632
0.6897	Remote Similarity	NPC202011
0.6893	Remote Similarity	NPC475949
0.6889	Remote Similarity	NPC127118

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 NPC119740 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1958
0.2-0.3	4049
0.3-0.4	2067
0.4-0.5	594
0.5-0.6	250
0.6-0.7	72
0.7-0.8	5
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
0.7347	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4225	Approved
0.7097	Intermediate Similarity	NPD6110	Phase 1
0.6939	Remote Similarity	NPD5785	Approved
0.69	Remote Similarity	NPD5282	Discontinued
0.6771	Remote Similarity	NPD5363	Approved
0.6701	Remote Similarity	NPD5786	Approved
0.6636	Remote Similarity	NPD6371	Approved
0.6596	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4252	Approved
0.6579	Remote Similarity	NPD7115	Discovery
0.6535	Remote Similarity	NPD7983	Approved
0.6531	Remote Similarity	NPD4249	Approved
0.6514	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4250	Approved
0.6465	Remote Similarity	NPD4251	Approved
0.6458	Remote Similarity	NPD5209	Approved
0.6458	Remote Similarity	NPD4269	Approved
0.6458	Remote Similarity	NPD4270	Approved
0.6429	Remote Similarity	NPD6650	Approved
0.6429	Remote Similarity	NPD6649	Approved
0.641	Remote Similarity	NPD6319	Approved
0.6383	Remote Similarity	NPD4271	Approved
0.6383	Remote Similarity	NPD4268	Approved
0.6383	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6411	Approved
0.6373	Remote Similarity	NPD7637	Suspended
0.6372	Remote Similarity	NPD8297	Approved
0.6364	Remote Similarity	NPD5697	Approved
0.6354	Remote Similarity	NPD5369	Approved
0.6311	Remote Similarity	NPD5778	Approved
0.6311	Remote Similarity	NPD5779	Approved
0.6306	Remote Similarity	NPD6881	Approved
0.6306	Remote Similarity	NPD6899	Approved
0.6289	Remote Similarity	NPD6435	Approved
0.6275	Remote Similarity	NPD6698	Approved
0.6275	Remote Similarity	NPD46	Approved
0.6263	Remote Similarity	NPD1694	Approved
0.625	Remote Similarity	NPD4822	Approved
0.625	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD4821	Approved
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD6372	Approved
0.625	Remote Similarity	NPD4819	Approved
0.625	Remote Similarity	NPD6013	Approved
0.6224	Remote Similarity	NPD7154	Phase 3
0.6198	Remote Similarity	NPD7492	Approved
0.6195	Remote Similarity	NPD7290	Approved
0.6195	Remote Similarity	NPD6883	Approved
0.6195	Remote Similarity	NPD7102	Approved
0.6176	Remote Similarity	NPD6101	Approved
0.6176	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD4632	Approved
0.6168	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6011	Approved
0.6154	Remote Similarity	NPD6399	Phase 3
0.6148	Remote Similarity	NPD6616	Approved
0.6147	Remote Similarity	NPD5211	Phase 2
0.614	Remote Similarity	NPD6869	Approved
0.614	Remote Similarity	NPD6847	Approved
0.614	Remote Similarity	NPD8130	Phase 1
0.614	Remote Similarity	NPD6617	Approved
0.6134	Remote Similarity	NPD6054	Approved
0.6126	Remote Similarity	NPD7128	Approved
0.6126	Remote Similarity	NPD5739	Approved
0.6126	Remote Similarity	NPD6402	Approved
0.6126	Remote Similarity	NPD6675	Approved
0.6117	Remote Similarity	NPD7838	Discovery
0.6105	Remote Similarity	NPD4756	Discovery
0.61	Remote Similarity	NPD1696	Phase 3
0.6098	Remote Similarity	NPD7078	Approved
0.6087	Remote Similarity	NPD6882	Approved
0.6083	Remote Similarity	NPD6016	Approved
0.6083	Remote Similarity	NPD6015	Approved
0.6082	Remote Similarity	NPD5368	Approved
0.6075	Remote Similarity	NPD6084	Phase 2
0.6075	Remote Similarity	NPD6083	Phase 2
0.6071	Remote Similarity	NPD5701	Approved
0.6058	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD4634	Approved
0.6048	Remote Similarity	NPD7736	Approved
0.6038	Remote Similarity	NPD5695	Phase 3
0.6036	Remote Similarity	NPD5141	Approved
0.6033	Remote Similarity	NPD6370	Approved
0.6033	Remote Similarity	NPD5988	Approved
0.6019	Remote Similarity	NPD5696	Approved
0.6019	Remote Similarity	NPD5370	Suspended
0.6018	Remote Similarity	NPD6686	Approved
0.6018	Remote Similarity	NPD7320	Approved
0.6018	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2204	Approved
0.6	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD8328	Phase 3
0.5963	Remote Similarity	NPD5286	Approved
0.5963	Remote Similarity	NPD4696	Approved
0.5963	Remote Similarity	NPD5285	Approved
0.595	Remote Similarity	NPD8516	Approved
0.595	Remote Similarity	NPD8515	Approved
0.595	Remote Similarity	NPD8517	Approved
0.595	Remote Similarity	NPD8513	Phase 3
0.5941	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7902	Approved
0.5918	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5344	Discontinued
0.59	Remote Similarity	NPD5362	Discontinued
0.5888	Remote Similarity	NPD4629	Approved
0.5888	Remote Similarity	NPD5210	Approved
0.5882	Remote Similarity	NPD6009	Approved
0.5868	Remote Similarity	NPD6059	Approved
0.5862	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5226	Approved
0.5856	Remote Similarity	NPD4633	Approved
0.5856	Remote Similarity	NPD5224	Approved
0.5856	Remote Similarity	NPD5225	Approved
0.584	Remote Similarity	NPD8293	Discontinued
0.5833	Remote Similarity	NPD5222	Approved
0.5833	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4697	Phase 3
0.5833	Remote Similarity	NPD7839	Suspended
0.5833	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5221	Approved
0.582	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.582	Remote Similarity	NPD5983	Phase 2
0.5814	Remote Similarity	NPD6109	Phase 1
0.5804	Remote Similarity	NPD5174	Approved
0.5804	Remote Similarity	NPD5175	Approved
0.5798	Remote Similarity	NPD6274	Approved
0.5789	Remote Similarity	NPD6412	Phase 2
0.5785	Remote Similarity	NPD7100	Approved
0.5785	Remote Similarity	NPD7101	Approved
0.578	Remote Similarity	NPD4755	Approved
0.578	Remote Similarity	NPD5173	Approved
0.5769	Remote Similarity	NPD6672	Approved
0.5769	Remote Similarity	NPD5737	Approved
0.5766	Remote Similarity	NPD5223	Approved
0.5758	Remote Similarity	NPD4695	Discontinued
0.575	Remote Similarity	NPD6317	Approved
0.5743	Remote Similarity	NPD5331	Approved
0.5743	Remote Similarity	NPD5332	Approved
0.5728	Remote Similarity	NPD5279	Phase 3
0.5726	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD7604	Phase 2
0.5714	Remote Similarity	NPD8074	Phase 3
0.5714	Remote Similarity	NPD4753	Phase 2
0.5702	Remote Similarity	NPD6314	Approved
0.5702	Remote Similarity	NPD6313	Approved
0.5702	Remote Similarity	NPD6335	Approved
0.57	Remote Similarity	NPD4790	Discontinued
0.5682	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD9120	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD7639	Approved
0.5676	Remote Similarity	NPD4700	Approved
0.5676	Remote Similarity	NPD7640	Approved
0.5667	Remote Similarity	NPD6868	Approved
0.5667	Remote Similarity	NPD3197	Phase 1
0.5664	Remote Similarity	NPD6647	Phase 2
0.5659	Remote Similarity	NPD7260	Phase 2
0.5652	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD7748	Approved
0.5648	Remote Similarity	NPD7900	Approved
0.5648	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD6336	Discontinued
0.5632	Remote Similarity	NPD69	Approved
0.5632	Remote Similarity	NPD9119	Approved
0.5631	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.562	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD6079	Approved
0.5607	Remote Similarity	NPD5284	Approved
0.5607	Remote Similarity	NPD7515	Phase 2
0.5607	Remote Similarity	NPD5281	Approved
0.5603	Remote Similarity	NPD4730	Approved
0.5603	Remote Similarity	NPD4729	Approved
0.56	Remote Similarity	NPD7642	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data