NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	275.498
LogP:	0.512
LogD:	1.199
LogS:	-2.108
# Rotatable Bonds:	1
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.428
Synthetic Accessibility Score:	4.69
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.755
MDCK Permeability:	2.6767689632833935e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.631
20% Bioavailability (F20%):	0.892
30% Bioavailability (F30%):	0.571

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	70.69512939453125%
Volume Distribution (VD):	0.703
Pgp-substrate:	38.03526306152344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.14
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.391
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.215
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.124
CYP3A4-substrate:	0.232

ADMET: Excretion

Clearance (CL):	5.29
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.203
AMES Toxicity:	0.29
Rat Oral Acute Toxicity:	0.654
Maximum Recommended Daily Dose:	0.499
Skin Sensitization:	0.529
Carcinogencity:	0.066
Eye Corrosion:	0.009
Eye Irritation:	0.075
Respiratory Toxicity:	0.798

Download Data

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

Natural Product: NPC229825

Natural Product ID:	NPC229825
*Common Name:**	Deacetylovatifolin
IUPAC Name:	(3aR,4R,6Z,10E,11aR)-4-hydroxy-6-(hydroxymethyl)-10-methyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
Synonyms:
Standard InCHIKey:	IAYQFYAFBVYKJZ-ROFUYRKGSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-9-4-3-5-11(8-16)7-12(17)14-10(2)15(18)19-13(14)6-9/h5-6,12-14,16-17H,2-4,7-8H2,1H3/b9-6+,11-5-/t12-,13-,14-/m1/s1
SMILES:	OC/C/1=CCC/C(=C/[C@@H]2[C@@H]([C@@H](C1)O)C(=C)C(=O)O2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2426504
PubChem CID:	11108215
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO19629	Laurencia scoparia	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754610]
NPO11074	Mycale izuensis	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088446]
NPO18159	Crypteronia paniculata	Species	Crypteroniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502343]
NPO18159	Crypteronia paniculata	Species	Crypteroniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787463]
NPO19629	Laurencia scoparia	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872159]
NPO32526	lineariifolia turcz	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24044895]
NPO15112	Premna oligotricha	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8450316]
NPO17110	Barleria prionitis	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9784173]
NPO17989	Astragalus falcatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17989	Astragalus falcatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11074	Mycale izuensis	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19081	Iris halophila	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18159	Crypteronia paniculata	Species	Crypteroniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19007	Lycopodium fastigiatum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17486	Alpinia javanica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18837	Ulva rigida	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23391	Nidula niveotomentosa	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17989	Astragalus falcatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15112	Premna oligotricha	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19433	Trichocline caulescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9841	Picramnia hirsuta	Species	Picramniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16972	Penicillium spiculisporum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19629	Laurencia scoparia	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17110	Barleria prionitis	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2257	Cell Line	MCF-10A	Homo sapiens	IC50	=	45700.0	nM	PMID[455083]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	13800.0	nM	PMID[455083]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	6900.0	nM	PMID[455083]

☑ 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 NPC229825 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	165
0.1-0.2	1147
0.2-0.3	4954
0.3-0.4	12695
0.4-0.5	12519
0.5-0.6	6778
0.6-0.7	3370
0.7-0.8	860
0.8-0.85	87
0.85-0.9	56
0.9-0.95	50
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.987	High Similarity	NPC473390
0.987	High Similarity	NPC131669
0.9868	High Similarity	NPC24417
0.9744	High Similarity	NPC114979
0.9744	High Similarity	NPC191476
0.962	High Similarity	NPC255307
0.9615	High Similarity	NPC169575
0.9615	High Similarity	NPC40746
0.9605	High Similarity	NPC98557
0.9605	High Similarity	NPC167881
0.95	High Similarity	NPC305475
0.95	High Similarity	NPC475461
0.9494	High Similarity	NPC96259
0.9494	High Similarity	NPC141193
0.9494	High Similarity	NPC476804
0.9494	High Similarity	NPC158756
0.9474	High Similarity	NPC471465
0.9474	High Similarity	NPC196653
0.9375	High Similarity	NPC470755
0.9367	High Similarity	NPC59097
0.9359	High Similarity	NPC52861
0.9259	High Similarity	NPC469910
0.9211	High Similarity	NPC68819
0.9136	High Similarity	NPC165162
0.9091	High Similarity	NPC7563
0.9091	High Similarity	NPC116177
0.9091	High Similarity	NPC476028
0.9091	High Similarity	NPC141789
0.9091	High Similarity	NPC171204
0.9091	High Similarity	NPC320630
0.9048	High Similarity	NPC469368
0.9048	High Similarity	NPC475855
0.9036	High Similarity	NPC473715
0.9036	High Similarity	NPC475819
0.9036	High Similarity	NPC476805
0.9036	High Similarity	NPC476803
0.9024	High Similarity	NPC150755
0.8974	High Similarity	NPC108816
0.8974	High Similarity	NPC93763
0.8889	High Similarity	NPC116543
0.8861	High Similarity	NPC89128
0.8861	High Similarity	NPC270126
0.8837	High Similarity	NPC228451
0.8837	High Similarity	NPC125674
0.8837	High Similarity	NPC475838
0.8824	High Similarity	NPC179394
0.8824	High Similarity	NPC474232
0.8824	High Similarity	NPC144133
0.8816	High Similarity	NPC295633
0.8816	High Similarity	NPC58956
0.8816	High Similarity	NPC269206
0.8765	High Similarity	NPC89555
0.875	High Similarity	NPC281132
0.8736	High Similarity	NPC474247
0.8734	High Similarity	NPC267231
0.8721	High Similarity	NPC473321
0.8718	High Similarity	NPC235906
0.8636	High Similarity	NPC471142
0.8625	High Similarity	NPC470239
0.8625	High Similarity	NPC470244
0.8621	High Similarity	NPC475302
0.8621	High Similarity	NPC162205
0.8621	High Similarity	NPC273579
0.8621	High Similarity	NPC295204
0.8621	High Similarity	NPC288240
0.8608	High Similarity	NPC97516
0.8605	High Similarity	NPC473619
0.8605	High Similarity	NPC129419
0.8588	High Similarity	NPC136879
0.8539	High Similarity	NPC230800
0.8539	High Similarity	NPC279621
0.8523	High Similarity	NPC57405
0.8523	High Similarity	NPC303942
0.8488	Intermediate Similarity	NPC218927
0.8488	Intermediate Similarity	NPC206001
0.8488	Intermediate Similarity	NPC474032
0.8488	Intermediate Similarity	NPC268298
0.8462	Intermediate Similarity	NPC114727
0.8462	Intermediate Similarity	NPC476590
0.8462	Intermediate Similarity	NPC476355
0.8462	Intermediate Similarity	NPC140287
0.8452	Intermediate Similarity	NPC21469
0.8442	Intermediate Similarity	NPC163003
0.8434	Intermediate Similarity	NPC250315
0.8427	Intermediate Similarity	NPC477922
0.8415	Intermediate Similarity	NPC301477
0.8415	Intermediate Similarity	NPC281949
0.8415	Intermediate Similarity	NPC141810
0.8415	Intermediate Similarity	NPC25684
0.8415	Intermediate Similarity	NPC470241
0.8409	Intermediate Similarity	NPC475912
0.8372	Intermediate Similarity	NPC477302
0.8354	Intermediate Similarity	NPC155587
0.8353	Intermediate Similarity	NPC50637
0.8333	Intermediate Similarity	NPC477921
0.8276	Intermediate Similarity	NPC295312
0.8261	Intermediate Similarity	NPC288876
0.8256	Intermediate Similarity	NPC160138
0.825	Intermediate Similarity	NPC123360
0.8235	Intermediate Similarity	NPC261380
0.8228	Intermediate Similarity	NPC48641
0.8222	Intermediate Similarity	NPC36954
0.8222	Intermediate Similarity	NPC471141
0.8222	Intermediate Similarity	NPC14961
0.8222	Intermediate Similarity	NPC270013
0.8222	Intermediate Similarity	NPC304886
0.8214	Intermediate Similarity	NPC474703
0.8205	Intermediate Similarity	NPC129665
0.8202	Intermediate Similarity	NPC469645
0.8202	Intermediate Similarity	NPC469692
0.8193	Intermediate Similarity	NPC325031
0.8171	Intermediate Similarity	NPC475210
0.8171	Intermediate Similarity	NPC617
0.8161	Intermediate Similarity	NPC202672
0.8152	Intermediate Similarity	NPC471144
0.8152	Intermediate Similarity	NPC473326
0.8148	Intermediate Similarity	NPC65603
0.8148	Intermediate Similarity	NPC470240
0.8148	Intermediate Similarity	NPC474760
0.8148	Intermediate Similarity	NPC476794
0.8132	Intermediate Similarity	NPC306041
0.8132	Intermediate Similarity	NPC473859
0.8132	Intermediate Similarity	NPC476315
0.8111	Intermediate Similarity	NPC81386
0.8111	Intermediate Similarity	NPC470010
0.8111	Intermediate Similarity	NPC323008
0.8111	Intermediate Similarity	NPC474035
0.8111	Intermediate Similarity	NPC470013
0.8111	Intermediate Similarity	NPC121825
0.8111	Intermediate Similarity	NPC262133
0.8111	Intermediate Similarity	NPC474338
0.8095	Intermediate Similarity	NPC474252
0.809	Intermediate Similarity	NPC131209
0.809	Intermediate Similarity	NPC184463
0.809	Intermediate Similarity	NPC30515
0.809	Intermediate Similarity	NPC300312
0.809	Intermediate Similarity	NPC261607
0.809	Intermediate Similarity	NPC111114
0.8068	Intermediate Similarity	NPC166919
0.8046	Intermediate Similarity	NPC237540
0.8046	Intermediate Similarity	NPC266957
0.8022	Intermediate Similarity	NPC170120
0.8022	Intermediate Similarity	NPC475659
0.8022	Intermediate Similarity	NPC52044
0.8	Intermediate Similarity	NPC179746
0.8	Intermediate Similarity	NPC212486
0.8	Intermediate Similarity	NPC476300
0.8	Intermediate Similarity	NPC81419
0.7978	Intermediate Similarity	NPC476004
0.7978	Intermediate Similarity	NPC474761
0.7978	Intermediate Similarity	NPC51004
0.7978	Intermediate Similarity	NPC473448
0.7957	Intermediate Similarity	NPC187268
0.7957	Intermediate Similarity	NPC141191
0.7955	Intermediate Similarity	NPC287089
0.7952	Intermediate Similarity	NPC19841
0.7952	Intermediate Similarity	NPC178277
0.7931	Intermediate Similarity	NPC469483
0.7931	Intermediate Similarity	NPC107787
0.7931	Intermediate Similarity	NPC261721
0.7927	Intermediate Similarity	NPC187568
0.7927	Intermediate Similarity	NPC474278
0.7927	Intermediate Similarity	NPC41780
0.7922	Intermediate Similarity	NPC194871
0.7912	Intermediate Similarity	NPC167219
0.7912	Intermediate Similarity	NPC198853
0.7912	Intermediate Similarity	NPC477131
0.7907	Intermediate Similarity	NPC295799
0.7907	Intermediate Similarity	NPC165287
0.7907	Intermediate Similarity	NPC159635
0.7907	Intermediate Similarity	NPC82297
0.7907	Intermediate Similarity	NPC115786
0.7907	Intermediate Similarity	NPC156485
0.7901	Intermediate Similarity	NPC138408
0.7901	Intermediate Similarity	NPC226669
0.7901	Intermediate Similarity	NPC193351
0.7895	Intermediate Similarity	NPC471148
0.7889	Intermediate Similarity	NPC475925
0.7889	Intermediate Similarity	NPC133698
0.7889	Intermediate Similarity	NPC12172
0.7889	Intermediate Similarity	NPC208886
0.7882	Intermediate Similarity	NPC85772
0.7872	Intermediate Similarity	NPC475949
0.7865	Intermediate Similarity	NPC307411
0.7865	Intermediate Similarity	NPC151770
0.7849	Intermediate Similarity	NPC169205
0.7849	Intermediate Similarity	NPC161493
0.7849	Intermediate Similarity	NPC471462
0.7848	Intermediate Similarity	NPC67183
0.7826	Intermediate Similarity	NPC90121
0.7826	Intermediate Similarity	NPC275960
0.7826	Intermediate Similarity	NPC67584
0.7826	Intermediate Similarity	NPC213698
0.7826	Intermediate Similarity	NPC48803
0.7826	Intermediate Similarity	NPC193645
0.7816	Intermediate Similarity	NPC78089
0.7816	Intermediate Similarity	NPC215364
0.7789	Intermediate Similarity	NPC46998
0.7789	Intermediate Similarity	NPC150923
0.7789	Intermediate Similarity	NPC473332

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 NPC229825 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1703
0.2-0.3	3747
0.3-0.4	2443
0.4-0.5	720
0.5-0.6	321
0.6-0.7	48
0.7-0.8	20
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
0.7826	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7154	Phase 3
0.7442	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6698	Approved
0.7391	Intermediate Similarity	NPD46	Approved
0.7391	Intermediate Similarity	NPD5785	Approved
0.7283	Intermediate Similarity	NPD1695	Approved
0.7222	Intermediate Similarity	NPD5363	Approved
0.7216	Intermediate Similarity	NPD4225	Approved
0.7209	Intermediate Similarity	NPD4268	Approved
0.7209	Intermediate Similarity	NPD4271	Approved
0.7191	Intermediate Similarity	NPD5362	Discontinued
0.7143	Intermediate Similarity	NPD4249	Approved
0.7079	Intermediate Similarity	NPD4269	Approved
0.7079	Intermediate Similarity	NPD4270	Approved
0.7065	Intermediate Similarity	NPD4251	Approved
0.7065	Intermediate Similarity	NPD4250	Approved
0.7059	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4819	Approved
0.7045	Intermediate Similarity	NPD4252	Approved
0.7045	Intermediate Similarity	NPD4821	Approved
0.7045	Intermediate Similarity	NPD4820	Approved
0.7045	Intermediate Similarity	NPD4822	Approved
0.7033	Intermediate Similarity	NPD1694	Approved
0.7033	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7838	Discovery
0.7019	Intermediate Similarity	NPD6371	Approved
0.6957	Remote Similarity	NPD5786	Approved
0.6947	Remote Similarity	NPD7983	Approved
0.6889	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6435	Approved
0.6875	Remote Similarity	NPD5778	Approved
0.6875	Remote Similarity	NPD5779	Approved
0.6818	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5369	Approved
0.67	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD5368	Approved
0.663	Remote Similarity	NPD5331	Approved
0.663	Remote Similarity	NPD5332	Approved
0.6593	Remote Similarity	NPD4790	Discontinued
0.6562	Remote Similarity	NPD6101	Approved
0.6562	Remote Similarity	NPD5370	Suspended
0.6562	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6399	Phase 3
0.6522	Remote Similarity	NPD5209	Approved
0.6517	Remote Similarity	NPD4756	Discovery
0.65	Remote Similarity	NPD7839	Suspended
0.6486	Remote Similarity	NPD7115	Discovery
0.6471	Remote Similarity	NPD7639	Approved
0.6471	Remote Similarity	NPD7640	Approved
0.6465	Remote Similarity	NPD5282	Discontinued
0.6429	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6411	Approved
0.6422	Remote Similarity	NPD6053	Discontinued
0.6408	Remote Similarity	NPD5344	Discontinued
0.6386	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7638	Approved
0.6296	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD8039	Approved
0.6263	Remote Similarity	NPD7637	Suspended
0.6235	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6648	Approved
0.6121	Remote Similarity	NPD8516	Approved
0.6121	Remote Similarity	NPD8513	Phase 3
0.6121	Remote Similarity	NPD8517	Approved
0.6121	Remote Similarity	NPD8515	Approved
0.6117	Remote Similarity	NPD6083	Phase 2
0.6117	Remote Similarity	NPD6084	Phase 2
0.6117	Remote Similarity	NPD7902	Approved
0.6111	Remote Similarity	NPD5697	Approved
0.6082	Remote Similarity	NPD6422	Discontinued
0.6078	Remote Similarity	NPD5695	Phase 3
0.6076	Remote Similarity	NPD342	Phase 1
0.6071	Remote Similarity	NPD3197	Phase 1
0.6058	Remote Similarity	NPD5696	Approved
0.6055	Remote Similarity	NPD6881	Approved
0.6055	Remote Similarity	NPD6899	Approved
0.6036	Remote Similarity	NPD6650	Approved
0.6036	Remote Similarity	NPD6649	Approved
0.6024	Remote Similarity	NPD368	Approved
0.6019	Remote Similarity	NPD5739	Approved
0.6019	Remote Similarity	NPD6675	Approved
0.6019	Remote Similarity	NPD7128	Approved
0.6019	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6014	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD3667	Approved
0.6	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD6012	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5981	Remote Similarity	NPD6647	Phase 2
0.598	Remote Similarity	NPD7748	Approved
0.5963	Remote Similarity	NPD5701	Approved
0.5946	Remote Similarity	NPD7102	Approved
0.5946	Remote Similarity	NPD6883	Approved
0.5946	Remote Similarity	NPD7290	Approved
0.5946	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD7515	Phase 2
0.5938	Remote Similarity	NPD6110	Phase 1
0.5918	Remote Similarity	NPD6684	Approved
0.5918	Remote Similarity	NPD5330	Approved
0.5918	Remote Similarity	NPD3618	Phase 1
0.5918	Remote Similarity	NPD7521	Approved
0.5918	Remote Similarity	NPD7146	Approved
0.5918	Remote Similarity	NPD6409	Approved
0.5918	Remote Similarity	NPD7334	Approved
0.5909	Remote Similarity	NPD6011	Approved
0.5909	Remote Similarity	NPD7320	Approved
0.5893	Remote Similarity	NPD8130	Phase 1
0.5893	Remote Similarity	NPD6847	Approved
0.5893	Remote Similarity	NPD6869	Approved
0.5893	Remote Similarity	NPD6617	Approved
0.5888	Remote Similarity	NPD7632	Discontinued
0.5888	Remote Similarity	NPD5211	Phase 2
0.5876	Remote Similarity	NPD4786	Approved
0.5876	Remote Similarity	NPD3133	Approved
0.5876	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD3665	Phase 1
0.5876	Remote Similarity	NPD3666	Approved
0.5868	Remote Similarity	NPD8074	Phase 3
0.5865	Remote Similarity	NPD4228	Discovery
0.5865	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6882	Approved
0.5841	Remote Similarity	NPD8297	Approved
0.5825	Remote Similarity	NPD7900	Approved
0.5825	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD3172	Approved
0.5804	Remote Similarity	NPD6421	Discontinued
0.58	Remote Similarity	NPD5737	Approved
0.58	Remote Similarity	NPD6672	Approved
0.58	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6903	Approved
0.5789	Remote Similarity	NPD4695	Discontinued
0.5784	Remote Similarity	NPD8034	Phase 2
0.5784	Remote Similarity	NPD8035	Phase 2
0.5784	Remote Similarity	NPD5281	Approved
0.5784	Remote Similarity	NPD5284	Approved
0.5784	Remote Similarity	NPD5693	Phase 1
0.578	Remote Similarity	NPD5141	Approved
0.5773	Remote Similarity	NPD6695	Phase 3
0.5769	Remote Similarity	NPD5210	Approved
0.5769	Remote Similarity	NPD4629	Approved
0.5769	Remote Similarity	NPD6927	Phase 3
0.5765	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD5279	Phase 3
0.5752	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD2204	Approved
0.575	Remote Similarity	NPD4266	Approved
0.575	Remote Similarity	NPD3196	Approved
0.575	Remote Similarity	NPD3195	Phase 2
0.575	Remote Similarity	NPD3194	Approved
0.5747	Remote Similarity	NPD3704	Approved
0.5747	Remote Similarity	NPD7331	Phase 2
0.5743	Remote Similarity	NPD4753	Phase 2
0.5728	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6008	Approved
0.5701	Remote Similarity	NPD5286	Approved
0.5701	Remote Similarity	NPD5285	Approved
0.5701	Remote Similarity	NPD4696	Approved
0.569	Remote Similarity	NPD6274	Approved
0.5688	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6412	Phase 2
0.5676	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD6420	Discontinued
0.5664	Remote Similarity	NPD2067	Discontinued
0.566	Remote Similarity	NPD4755	Approved
0.5657	Remote Similarity	NPD1696	Phase 3
0.5656	Remote Similarity	NPD8273	Phase 1
0.5656	Remote Similarity	NPD7507	Approved
0.5641	Remote Similarity	NPD7505	Discontinued
0.5632	Remote Similarity	NPD7341	Phase 2
0.5631	Remote Similarity	NPD6079	Approved
0.562	Remote Similarity	NPD7829	Approved
0.562	Remote Similarity	NPD7830	Approved
0.562	Remote Similarity	NPD7642	Approved
0.5619	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.56	Remote Similarity	NPD4519	Discontinued
0.56	Remote Similarity	NPD4623	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