NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	422.19
Volume:	426.458
LogP:	0.71
LogD:	1.078
LogS:	-2.264
# Rotatable Bonds:	8
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.288
Synthetic Accessibility Score:	5.379
Fsp3:	0.591
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.908
MDCK Permeability:	0.00010810977983055636
Pgp-inhibitor:	0.01
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.862
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.691

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.477
Plasma Protein Binding (PPB):	58.27143096923828%
Volume Distribution (VD):	0.592
Pgp-substrate:	64.04486083984375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.124
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.061
CYP3A4-inhibitor:	0.477
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	4.665
Half-life (T1/2):	0.935

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.905
Drug-inuced Liver Injury (DILI):	0.486
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.83
Skin Sensitization:	0.592
Carcinogencity:	0.389
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.102

Download Data

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

Natural Product: NPC476805

Natural Product ID:	NPC476805
*Common Name:**	[(3R,3aR,4S,6E,10Z,11aR)-10-(hydroxymethyl)-3,6-dimethyl-2-oxo-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-4-yl] (Z)-4-acetyloxy-2-(hydroxymethyl)but-2-enoate
IUPAC Name:	[(3R,3aR,4S,6E,10Z,11aR)-10-(hydroxymethyl)-3,6-dimethyl-2-oxo-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-4-yl] (Z)-4-acetyloxy-2-(hydroxymethyl)but-2-enoate
Synonyms:
Standard InCHIKey:	QVMJTYNTCBEZMJ-MKKXVNNWSA-N
Standard InCHI:	InChI=1S/C22H30O8/c1-13-5-4-6-16(11-23)10-19-20(14(2)21(26)29-19)18(9-13)30-22(27)17(12-24)7-8-28-15(3)25/h5,7,10,14,18-20,23-24H,4,6,8-9,11-12H2,1-3H3/b13-5+,16-10-,17-7-/t14-,18+,19-,20-/m1/s1
SMILES:	C[C@@H]1[C@@H]2[C@H](C/C(=C/CC/C(=C/[C@H]2OC1=O)/CO)/C)OC(=O)/C(=C\COC(=O)C)/CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	162989417
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
NPO10212	Centaurea pullata	Species	Asteraceae	Eukaryota	Aerial parts	Chra Mountain in Blida (North Algeria)	2006-APR	PMID[17979247]
NPO10212	Centaurea pullata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18280170]
NPO10212	Centaurea pullata	Species	Asteraceae	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
MIC	14
Others	14

Activity Type	# Activity
Organism	28

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	0.2	ug/ml	PMID[17979247]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MBC	=	0.3	ug/ml	PMID[17979247]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.2	ug/ml	PMID[17979247]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MBC	=	0.3	ug/ml	PMID[17979247]
NPT3729	Organism	Pseudomonas tolaasii	Pseudomonas tolaasii	MIC	=	0.2	ug/ml	PMID[17979247]
NPT3729	Organism	Pseudomonas tolaasii	Pseudomonas tolaasii	MBC	=	0.3	ug/ml	PMID[17979247]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	0.4	ug/ml	PMID[17979247]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MBC	=	0.5	ug/ml	PMID[17979247]
NPT3608	Organism	Salmonella enteritidis	Salmonella enterica subsp. enterica serovar Enteritidis	MIC	=	0.3	ug/ml	PMID[17979247]
NPT3608	Organism	Salmonella enteritidis	Salmonella enterica subsp. enterica serovar Enteritidis	MBC	=	0.3	ug/ml	PMID[17979247]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	0.3	ug/ml	PMID[17979247]
NPT19	Organism	Escherichia coli	Escherichia coli	MBC	=	0.3	ug/ml	PMID[17979247]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	MIC	=	0.2	ug/ml	PMID[17979247]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	MFC	=	0.2	ug/ml	PMID[17979247]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	0.2	ug/ml	PMID[17979247]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MFC	=	0.3	ug/ml	PMID[17979247]
NPT3176	Organism	Aspergillus ochraceus	Aspergillus ochraceus	MIC	=	0.1	ug/ml	PMID[17979247]
NPT3176	Organism	Aspergillus ochraceus	Aspergillus ochraceus	MFC	=	0.2	ug/ml	PMID[17979247]
NPT3695	Organism	Penicillium funiculosum	Penicillium funiculosum	MIC	=	0.2	ug/ml	PMID[17979247]
NPT3695	Organism	Penicillium funiculosum	Penicillium funiculosum	MFC	=	0.3	ug/ml	PMID[17979247]
NPT6344	Organism	Penicillium ochrochloron	Penicillium ochrochloron	MIC	=	0.1	ug/ml	PMID[17979247]
NPT6344	Organism	Penicillium ochrochloron	Penicillium ochrochloron	MFC	=	0.2	ug/ml	PMID[17979247]
NPT2567	Organism	Trichoderma viride	Hypocrea rufa	MIC	=	0.2	ug/ml	PMID[17979247]
NPT2567	Organism	Trichoderma viride	Hypocrea rufa	MFC	=	0.3	ug/ml	PMID[17979247]
NPT4945	Organism	Fusarium tricinctum	Fusarium tricinctum	MIC	=	0.2	ug/ml	PMID[17979247]
NPT4945	Organism	Fusarium tricinctum	Fusarium tricinctum	MFC	=	0.3	ug/ml	PMID[17979247]
NPT962	Organism	Alternaria alternata	Alternaria alternata	MIC	=	0.2	ug/ml	PMID[17979247]
NPT962	Organism	Alternaria alternata	Alternaria alternata	MFC	=	0.3	ug/ml	PMID[17979247]

☑ 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 NPC476805 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	185
0.1-0.2	1149
0.2-0.3	4858
0.3-0.4	10578
0.4-0.5	13463
0.5-0.6	7117
0.6-0.7	4092
0.7-0.8	1040
0.8-0.85	112
0.85-0.9	51
0.9-0.95	34
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9634	High Similarity	NPC470755
0.9524	High Similarity	NPC476803
0.9524	High Similarity	NPC475819
0.9512	High Similarity	NPC158756
0.9512	High Similarity	NPC476804
0.939	High Similarity	NPC169575
0.939	High Similarity	NPC40746
0.9286	High Similarity	NPC469910
0.9286	High Similarity	NPC305475
0.9286	High Similarity	NPC475461
0.9167	High Similarity	NPC255307
0.9157	High Similarity	NPC131669
0.9157	High Similarity	NPC473390
0.9146	High Similarity	NPC24417
0.9146	High Similarity	NPC52861
0.908	High Similarity	NPC474232
0.9048	High Similarity	NPC114979
0.9048	High Similarity	NPC96259
0.9048	High Similarity	NPC141193
0.9048	High Similarity	NPC191476
0.9036	High Similarity	NPC229825
0.9	High Similarity	NPC230800
0.8929	High Similarity	NPC116543
0.8929	High Similarity	NPC59097
0.8902	High Similarity	NPC98557
0.8902	High Similarity	NPC167881
0.8889	High Similarity	NPC471142
0.8864	High Similarity	NPC469368
0.8864	High Similarity	NPC475855
0.8837	High Similarity	NPC150755
0.878	High Similarity	NPC108816
0.878	High Similarity	NPC196653
0.878	High Similarity	NPC93763
0.878	High Similarity	NPC471465
0.8778	High Similarity	NPC474247
0.8681	High Similarity	NPC477922
0.8675	High Similarity	NPC270126
0.8667	High Similarity	NPC228451
0.8667	High Similarity	NPC475838
0.8667	High Similarity	NPC475302
0.8667	High Similarity	NPC125674
0.8659	High Similarity	NPC7563
0.8659	High Similarity	NPC171204
0.8659	High Similarity	NPC474760
0.8659	High Similarity	NPC476028
0.8659	High Similarity	NPC320630
0.8659	High Similarity	NPC116177
0.8659	High Similarity	NPC141789
0.8652	High Similarity	NPC179394
0.8652	High Similarity	NPC144133
0.8621	High Similarity	NPC469483
0.8587	High Similarity	NPC279621
0.8587	High Similarity	NPC477921
0.8571	High Similarity	NPC281132
0.8556	High Similarity	NPC473321
0.8537	High Similarity	NPC68819
0.8511	High Similarity	NPC288876
0.8506	High Similarity	NPC261380
0.8506	High Similarity	NPC165162
0.8462	Intermediate Similarity	NPC469692
0.8462	Intermediate Similarity	NPC162205
0.8462	Intermediate Similarity	NPC288240
0.8462	Intermediate Similarity	NPC273579
0.8462	Intermediate Similarity	NPC469645
0.8462	Intermediate Similarity	NPC295204
0.8452	Intermediate Similarity	NPC89128
0.8444	Intermediate Similarity	NPC473619
0.8434	Intermediate Similarity	NPC97516
0.8427	Intermediate Similarity	NPC473715
0.8404	Intermediate Similarity	NPC471144
0.8404	Intermediate Similarity	NPC141191
0.8387	Intermediate Similarity	NPC473859
0.8372	Intermediate Similarity	NPC85772
0.8372	Intermediate Similarity	NPC89555
0.837	Intermediate Similarity	NPC121825
0.8352	Intermediate Similarity	NPC111114
0.8352	Intermediate Similarity	NPC300312
0.8352	Intermediate Similarity	NPC261607
0.8333	Intermediate Similarity	NPC267231
0.8333	Intermediate Similarity	NPC474032
0.8298	Intermediate Similarity	NPC169205
0.8298	Intermediate Similarity	NPC471462
0.8293	Intermediate Similarity	NPC476355
0.828	Intermediate Similarity	NPC304886
0.828	Intermediate Similarity	NPC471141
0.828	Intermediate Similarity	NPC475659
0.8256	Intermediate Similarity	NPC325031
0.8242	Intermediate Similarity	NPC129419
0.8235	Intermediate Similarity	NPC19841
0.8235	Intermediate Similarity	NPC178277
0.8222	Intermediate Similarity	NPC260343
0.8222	Intermediate Similarity	NPC287089
0.8202	Intermediate Similarity	NPC261721
0.8191	Intermediate Similarity	NPC185553
0.8172	Intermediate Similarity	NPC167219
0.8172	Intermediate Similarity	NPC57405
0.8172	Intermediate Similarity	NPC303942
0.8171	Intermediate Similarity	NPC295633
0.8171	Intermediate Similarity	NPC58956
0.8171	Intermediate Similarity	NPC269206
0.8144	Intermediate Similarity	NPC149371
0.8132	Intermediate Similarity	NPC206001
0.8132	Intermediate Similarity	NPC295312
0.8132	Intermediate Similarity	NPC218927
0.8132	Intermediate Similarity	NPC268298
0.8125	Intermediate Similarity	NPC475949
0.8111	Intermediate Similarity	NPC160138
0.8111	Intermediate Similarity	NPC266957
0.8111	Intermediate Similarity	NPC72513
0.8095	Intermediate Similarity	NPC235906
0.8095	Intermediate Similarity	NPC123360
0.809	Intermediate Similarity	NPC125290
0.809	Intermediate Similarity	NPC21469
0.8085	Intermediate Similarity	NPC36954
0.8085	Intermediate Similarity	NPC48803
0.8085	Intermediate Similarity	NPC90121
0.8085	Intermediate Similarity	NPC193645
0.8085	Intermediate Similarity	NPC275960
0.8072	Intermediate Similarity	NPC48641
0.8072	Intermediate Similarity	NPC476590
0.8072	Intermediate Similarity	NPC114727
0.8072	Intermediate Similarity	NPC140287
0.8068	Intermediate Similarity	NPC475947
0.8068	Intermediate Similarity	NPC250315
0.8068	Intermediate Similarity	NPC474703
0.8065	Intermediate Similarity	NPC475912
0.8049	Intermediate Similarity	NPC129665
0.8049	Intermediate Similarity	NPC163003
0.8046	Intermediate Similarity	NPC25684
0.8046	Intermediate Similarity	NPC301477
0.8046	Intermediate Similarity	NPC470241
0.8046	Intermediate Similarity	NPC141810
0.8046	Intermediate Similarity	NPC471325
0.8046	Intermediate Similarity	NPC281949
0.8043	Intermediate Similarity	NPC473448
0.8043	Intermediate Similarity	NPC71533
0.8043	Intermediate Similarity	NPC106510
0.8041	Intermediate Similarity	NPC47880
0.8041	Intermediate Similarity	NPC133907
0.8041	Intermediate Similarity	NPC185141
0.8041	Intermediate Similarity	NPC469657
0.8041	Intermediate Similarity	NPC164598
0.8041	Intermediate Similarity	NPC128733
0.8041	Intermediate Similarity	NPC244456
0.8041	Intermediate Similarity	NPC110443
0.8041	Intermediate Similarity	NPC474339
0.8041	Intermediate Similarity	NPC46998
0.8023	Intermediate Similarity	NPC470244
0.8023	Intermediate Similarity	NPC470239
0.8022	Intermediate Similarity	NPC136879
0.8022	Intermediate Similarity	NPC477302
0.8	Intermediate Similarity	NPC306041
0.8	Intermediate Similarity	NPC57744
0.8	Intermediate Similarity	NPC477513
0.8	Intermediate Similarity	NPC107787
0.8	Intermediate Similarity	NPC50637
0.8	Intermediate Similarity	NPC476315
0.798	Intermediate Similarity	NPC475676
0.798	Intermediate Similarity	NPC220964
0.7979	Intermediate Similarity	NPC140543
0.7979	Intermediate Similarity	NPC474338
0.7979	Intermediate Similarity	NPC477131
0.7979	Intermediate Similarity	NPC476267
0.7979	Intermediate Similarity	NPC469632
0.7978	Intermediate Similarity	NPC82297
0.7976	Intermediate Similarity	NPC155587
0.7976	Intermediate Similarity	NPC329852
0.7959	Intermediate Similarity	NPC471148
0.7957	Intermediate Similarity	NPC472814
0.7957	Intermediate Similarity	NPC177037
0.7957	Intermediate Similarity	NPC475925
0.7935	Intermediate Similarity	NPC166919
0.7912	Intermediate Similarity	NPC237540
0.7907	Intermediate Similarity	NPC128276
0.7895	Intermediate Similarity	NPC270013
0.7895	Intermediate Similarity	NPC14961
0.7889	Intermediate Similarity	NPC78089
0.7879	Intermediate Similarity	NPC475871
0.7879	Intermediate Similarity	NPC4620
0.7879	Intermediate Similarity	NPC475945
0.7879	Intermediate Similarity	NPC474165
0.7879	Intermediate Similarity	NPC69171
0.7879	Intermediate Similarity	NPC472755
0.7872	Intermediate Similarity	NPC476300
0.7872	Intermediate Similarity	NPC165383
0.7872	Intermediate Similarity	NPC115021
0.7865	Intermediate Similarity	NPC318468
0.7857	Intermediate Similarity	NPC150923
0.7849	Intermediate Similarity	NPC19087
0.7835	Intermediate Similarity	NPC187268
0.7835	Intermediate Similarity	NPC473326
0.7826	Intermediate Similarity	NPC202672
0.7816	Intermediate Similarity	NPC617
0.7812	Intermediate Similarity	NPC242848
0.7812	Intermediate Similarity	NPC17585
0.7812	Intermediate Similarity	NPC54731
0.7802	Intermediate Similarity	NPC316426
0.7802	Intermediate Similarity	NPC315395
0.78	Intermediate Similarity	NPC100487
0.78	Intermediate Similarity	NPC203659

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 NPC476805 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1721
0.2-0.3	3693
0.3-0.4	2400
0.4-0.5	728
0.5-0.6	350
0.6-0.7	65
0.7-0.8	24
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8085	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD5785	Approved
0.7889	Intermediate Similarity	NPD5363	Approved
0.766	Intermediate Similarity	NPD6698	Approved
0.766	Intermediate Similarity	NPD46	Approved
0.7653	Intermediate Similarity	NPD4225	Approved
0.7647	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4269	Approved
0.7556	Intermediate Similarity	NPD4270	Approved
0.7473	Intermediate Similarity	NPD7154	Phase 3
0.7429	Intermediate Similarity	NPD6371	Approved
0.7419	Intermediate Similarity	NPD5786	Approved
0.7396	Intermediate Similarity	NPD7983	Approved
0.7333	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4252	Approved
0.7312	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5362	Discontinued
0.7253	Intermediate Similarity	NPD5369	Approved
0.7143	Intermediate Similarity	NPD4820	Approved
0.7143	Intermediate Similarity	NPD4822	Approved
0.7143	Intermediate Similarity	NPD4819	Approved
0.7143	Intermediate Similarity	NPD5779	Approved
0.7143	Intermediate Similarity	NPD4821	Approved
0.7143	Intermediate Similarity	NPD5778	Approved
0.7128	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7838	Discovery
0.7111	Intermediate Similarity	NPD4268	Approved
0.7111	Intermediate Similarity	NPD4271	Approved
0.7053	Intermediate Similarity	NPD4249	Approved
0.701	Intermediate Similarity	NPD1695	Approved
0.6989	Remote Similarity	NPD5209	Approved
0.6989	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6435	Approved
0.6979	Remote Similarity	NPD4250	Approved
0.6979	Remote Similarity	NPD4251	Approved
0.6961	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1694	Approved
0.6931	Remote Similarity	NPD7839	Suspended
0.6923	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6686	Approved
0.69	Remote Similarity	NPD5282	Discontinued
0.6875	Remote Similarity	NPD7115	Discovery
0.6837	Remote Similarity	NPD6101	Approved
0.6837	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5368	Approved
0.6737	Remote Similarity	NPD5332	Approved
0.6737	Remote Similarity	NPD5331	Approved
0.6727	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4790	Discontinued
0.67	Remote Similarity	NPD7637	Suspended
0.67	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD5370	Suspended
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD8516	Approved
0.6638	Remote Similarity	NPD8517	Approved
0.6638	Remote Similarity	NPD8515	Approved
0.6638	Remote Similarity	NPD8513	Phase 3
0.6571	Remote Similarity	NPD7640	Approved
0.6571	Remote Similarity	NPD7639	Approved
0.6535	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6053	Discontinued
0.6512	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5344	Discontinued
0.6476	Remote Similarity	NPD7638	Approved
0.6471	Remote Similarity	NPD6399	Phase 3
0.6452	Remote Similarity	NPD4756	Discovery
0.6364	Remote Similarity	NPD8074	Phase 3
0.6283	Remote Similarity	NPD6649	Approved
0.6283	Remote Similarity	NPD6650	Approved
0.6262	Remote Similarity	NPD6648	Approved
0.625	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD6372	Approved
0.6237	Remote Similarity	NPD8039	Approved
0.6226	Remote Similarity	NPD7902	Approved
0.6226	Remote Similarity	NPD6083	Phase 2
0.6226	Remote Similarity	NPD6084	Phase 2
0.6216	Remote Similarity	NPD5697	Approved
0.6195	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5695	Phase 3
0.6168	Remote Similarity	NPD5696	Approved
0.6161	Remote Similarity	NPD6899	Approved
0.6161	Remote Similarity	NPD6881	Approved
0.6126	Remote Similarity	NPD5739	Approved
0.6126	Remote Similarity	NPD7128	Approved
0.6126	Remote Similarity	NPD6402	Approved
0.6126	Remote Similarity	NPD6675	Approved
0.6116	Remote Similarity	NPD7642	Approved
0.6116	Remote Similarity	NPD7830	Approved
0.6116	Remote Similarity	NPD7829	Approved
0.6106	Remote Similarity	NPD6012	Approved
0.6106	Remote Similarity	NPD6013	Approved
0.6106	Remote Similarity	NPD6014	Approved
0.6106	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD7748	Approved
0.6091	Remote Similarity	NPD6647	Phase 2
0.6087	Remote Similarity	NPD6882	Approved
0.6087	Remote Similarity	NPD8297	Approved
0.6071	Remote Similarity	NPD5701	Approved
0.6061	Remote Similarity	NPD6110	Phase 1
0.6058	Remote Similarity	NPD7515	Phase 2
0.6053	Remote Similarity	NPD7290	Approved
0.6053	Remote Similarity	NPD6883	Approved
0.6053	Remote Similarity	NPD7102	Approved
0.6047	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5330	Approved
0.604	Remote Similarity	NPD7334	Approved
0.604	Remote Similarity	NPD6409	Approved
0.604	Remote Similarity	NPD7521	Approved
0.604	Remote Similarity	NPD7146	Approved
0.604	Remote Similarity	NPD6684	Approved
0.604	Remote Similarity	NPD3618	Phase 1
0.6018	Remote Similarity	NPD7320	Approved
0.6018	Remote Similarity	NPD6011	Approved
0.6017	Remote Similarity	NPD7500	Approved
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2204	Approved
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD7632	Discontinued
0.6	Remote Similarity	NPD6847	Approved
0.5977	Remote Similarity	NPD368	Approved
0.596	Remote Similarity	NPD3667	Approved
0.596	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7900	Approved
0.5943	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6672	Approved
0.5922	Remote Similarity	NPD5737	Approved
0.5922	Remote Similarity	NPD6903	Approved
0.5922	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4695	Discontinued
0.5905	Remote Similarity	NPD5284	Approved
0.5905	Remote Similarity	NPD5281	Approved
0.5905	Remote Similarity	NPD5693	Phase 1
0.5893	Remote Similarity	NPD5141	Approved
0.5889	Remote Similarity	NPD7331	Phase 2
0.5888	Remote Similarity	NPD4629	Approved
0.5888	Remote Similarity	NPD5210	Approved
0.5887	Remote Similarity	NPD7507	Approved
0.5887	Remote Similarity	NPD8273	Phase 1
0.5882	Remote Similarity	NPD5279	Phase 3
0.5882	Remote Similarity	NPD6422	Discontinued
0.5882	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD3732	Approved
0.5865	Remote Similarity	NPD4753	Phase 2
0.5862	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD3197	Phase 1
0.5842	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD4786	Approved
0.5841	Remote Similarity	NPD6008	Approved
0.5833	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7641	Discontinued
0.5833	Remote Similarity	NPD4228	Discovery
0.5826	Remote Similarity	NPD6413	Approved
0.582	Remote Similarity	NPD8444	Approved
0.5818	Remote Similarity	NPD5285	Approved
0.5818	Remote Similarity	NPD4696	Approved
0.5818	Remote Similarity	NPD5286	Approved
0.5806	Remote Similarity	NPD7492	Approved
0.5798	Remote Similarity	NPD6274	Approved
0.5789	Remote Similarity	NPD6412	Phase 2
0.5784	Remote Similarity	NPD1696	Phase 3
0.5781	Remote Similarity	NPD7260	Phase 2
0.578	Remote Similarity	NPD4755	Approved
0.5776	Remote Similarity	NPD6421	Discontinued
0.5776	Remote Similarity	NPD2067	Discontinued
0.576	Remote Similarity	NPD6616	Approved
0.576	Remote Similarity	NPD8451	Approved
0.5755	Remote Similarity	NPD8035	Phase 2
0.5755	Remote Similarity	NPD6079	Approved
0.5755	Remote Similarity	NPD8034	Phase 2
0.575	Remote Similarity	NPD7505	Discontinued
0.5743	Remote Similarity	NPD6695	Phase 3
0.5741	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD6054	Approved
0.573	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD4623	Approved
0.5728	Remote Similarity	NPD4519	Discontinued
0.5726	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8328	Phase 3
0.5714	Remote Similarity	NPD8448	Approved
0.5714	Remote Similarity	NPD7078	Approved
0.5714	Remote Similarity	NPD4633	Approved
0.5714	Remote Similarity	NPD5225	Approved
0.5714	Remote Similarity	NPD5224	Approved
0.5714	Remote Similarity	NPD3704	Approved
0.5714	Remote Similarity	NPD5226	Approved
0.5714	Remote Similarity	NPD5328	Approved
0.5703	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD4202	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