NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	260.788
LogP:	2.346
LogD:	2.262
LogS:	-3.493
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.406
Synthetic Accessibility Score:	4.508
Fsp3:	0.667
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:	-4.532
MDCK Permeability:	3.204436143278144e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.068
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.758
Plasma Protein Binding (PPB):	61.27916717529297%
Volume Distribution (VD):	1.092
Pgp-substrate:	30.77782440185547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.579
CYP1A2-substrate:	0.414
CYP2C19-inhibitor:	0.112
CYP2C19-substrate:	0.595
CYP2C9-inhibitor:	0.145
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.199
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.236

ADMET: Excretion

Clearance (CL):	8.628
Half-life (T1/2):	0.531

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.34
Drug-inuced Liver Injury (DILI):	0.268
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.838
Maximum Recommended Daily Dose:	0.29
Skin Sensitization:	0.37
Carcinogencity:	0.757
Eye Corrosion:	0.71
Eye Irritation:	0.882
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC245665

Natural Product ID:	NPC245665
*Common Name:**	(3As,6Ar,9R,9As,9Bs)-9-Hydroxy-9-Methyl-3,6-Dimethylenedecahydroazuleno[4,5-B]Furan-2(9Bh)-One
IUPAC Name:	(3aS,6aR,9R,9aS,9bS)-9-hydroxy-9-methyl-3,6-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
Synonyms:
Standard InCHIKey:	QRVGCXGOIPXKQE-MJDBTJCESA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-8-4-5-11-9(2)14(16)18-13(11)12-10(8)6-7-15(12,3)17/h10-13,17H,1-2,4-7H2,3H3/t10-,11-,12-,13-,15+/m0/s1
SMILES:	C=C1CC[C@H]2C(=C)C(=O)O[C@@H]2[C@@H]2[C@H]1CC[C@@]2(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2206435
PubChem CID:	14466196
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:0001770] Guaianolides 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
NPO27465	Sinularia erecta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27142697]
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27742	Mollugo pentaphylla	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27742	Mollugo pentaphylla	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16221	Dolichos kilimandscharicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27130	Tsuga sieboldii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27777	Artemisia phaeolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5146	Tuta absoluta	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26934	Naucleopsis mello-barretoi	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27465	Sinularia erecta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27593	Silene dioica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27742	Mollugo pentaphylla	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27570	Paederia foetida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27635	Laurencia dendroidea	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27339	Lactarius blennius	Species	Russulaceae	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	2
Others	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	9400.0	nM	PMID[463183]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	22.6	%	PMID[463183]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	53.7	%	PMID[463183]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	30.6	%	PMID[463183]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	61.6	%	PMID[463183]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	9900.0	nM	PMID[463183]

☑ 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 NPC245665 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	225
0.1-0.2	1694
0.2-0.3	7485
0.3-0.4	16252
0.4-0.5	8745
0.5-0.6	6121
0.6-0.7	1778
0.7-0.8	282
0.8-0.85	57
0.85-0.9	48
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC300082
0.95	High Similarity	NPC284534
0.95	High Similarity	NPC204105
0.939	High Similarity	NPC79549
0.9277	High Similarity	NPC215556
0.9167	High Similarity	NPC216284
0.9136	High Similarity	NPC156485
0.9059	High Similarity	NPC155215
0.9036	High Similarity	NPC201658
0.8953	High Similarity	NPC258216
0.8916	High Similarity	NPC56593
0.8916	High Similarity	NPC236692
0.8916	High Similarity	NPC309757
0.8875	High Similarity	NPC258965
0.8875	High Similarity	NPC156658
0.8831	High Similarity	NPC143979
0.8831	High Similarity	NPC320537
0.8824	High Similarity	NPC155935
0.875	High Similarity	NPC472873
0.875	High Similarity	NPC163228
0.8721	High Similarity	NPC301969
0.8721	High Similarity	NPC35809
0.8721	High Similarity	NPC37607
0.8721	High Similarity	NPC54065
0.8721	High Similarity	NPC297474
0.8706	High Similarity	NPC217983
0.8706	High Similarity	NPC91248
0.8706	High Similarity	NPC178875
0.8706	High Similarity	NPC207114
0.869	High Similarity	NPC67493
0.869	High Similarity	NPC187661
0.8675	High Similarity	NPC224386
0.8675	High Similarity	NPC194859
0.8621	High Similarity	NPC57304
0.8621	High Similarity	NPC35959
0.8621	High Similarity	NPC184063
0.8621	High Similarity	NPC133888
0.8621	High Similarity	NPC29821
0.8621	High Similarity	NPC293001
0.8621	High Similarity	NPC171360
0.8621	High Similarity	NPC63193
0.8605	High Similarity	NPC472872
0.8588	High Similarity	NPC118601
0.8588	High Similarity	NPC270270
0.8554	High Similarity	NPC111409
0.8539	High Similarity	NPC52044
0.8539	High Similarity	NPC67584
0.8539	High Similarity	NPC476053
0.8523	High Similarity	NPC473263
0.8523	High Similarity	NPC473273
0.8523	High Similarity	NPC60386
0.8523	High Similarity	NPC308656
0.8523	High Similarity	NPC473234
0.8506	High Similarity	NPC19087
0.85	High Similarity	NPC208223
0.8462	Intermediate Similarity	NPC45125
0.8444	Intermediate Similarity	NPC213078
0.8434	Intermediate Similarity	NPC246076
0.8427	Intermediate Similarity	NPC127019
0.8427	Intermediate Similarity	NPC323008
0.8427	Intermediate Similarity	NPC198853
0.8427	Intermediate Similarity	NPC262133
0.8427	Intermediate Similarity	NPC470013
0.8427	Intermediate Similarity	NPC470010
0.8415	Intermediate Similarity	NPC6823
0.8415	Intermediate Similarity	NPC293418
0.8415	Intermediate Similarity	NPC276356
0.8415	Intermediate Similarity	NPC73052
0.8415	Intermediate Similarity	NPC290508
0.8409	Intermediate Similarity	NPC133698
0.8409	Intermediate Similarity	NPC131209
0.8391	Intermediate Similarity	NPC168679
0.8391	Intermediate Similarity	NPC12872
0.8391	Intermediate Similarity	NPC38392
0.8372	Intermediate Similarity	NPC190753
0.8372	Intermediate Similarity	NPC24728
0.837	Intermediate Similarity	NPC471381
0.837	Intermediate Similarity	NPC186861
0.8352	Intermediate Similarity	NPC181151
0.8352	Intermediate Similarity	NPC161493
0.8352	Intermediate Similarity	NPC311904
0.8352	Intermediate Similarity	NPC471150
0.8333	Intermediate Similarity	NPC128246
0.8333	Intermediate Similarity	NPC170120
0.8333	Intermediate Similarity	NPC213698
0.8315	Intermediate Similarity	NPC200237
0.8315	Intermediate Similarity	NPC153590
0.8313	Intermediate Similarity	NPC126248
0.8312	Intermediate Similarity	NPC5714
0.8293	Intermediate Similarity	NPC182550
0.8276	Intermediate Similarity	NPC471149
0.8276	Intermediate Similarity	NPC224652
0.8261	Intermediate Similarity	NPC221615
0.8256	Intermediate Similarity	NPC304558
0.8242	Intermediate Similarity	NPC91771
0.8242	Intermediate Similarity	NPC142529
0.8242	Intermediate Similarity	NPC18019
0.8242	Intermediate Similarity	NPC24956
0.8222	Intermediate Similarity	NPC477131
0.8202	Intermediate Similarity	NPC475925
0.8193	Intermediate Similarity	NPC51507
0.8193	Intermediate Similarity	NPC69271
0.8193	Intermediate Similarity	NPC74673
0.8182	Intermediate Similarity	NPC4986
0.8182	Intermediate Similarity	NPC283409
0.8152	Intermediate Similarity	NPC108475
0.8152	Intermediate Similarity	NPC213947
0.8152	Intermediate Similarity	NPC474313
0.8152	Intermediate Similarity	NPC170143
0.814	Intermediate Similarity	NPC235792
0.8118	Intermediate Similarity	NPC54468
0.8111	Intermediate Similarity	NPC472874
0.8072	Intermediate Similarity	NPC470239
0.8072	Intermediate Similarity	NPC470244
0.8049	Intermediate Similarity	NPC53581
0.8049	Intermediate Similarity	NPC103987
0.8046	Intermediate Similarity	NPC470242
0.8046	Intermediate Similarity	NPC238593
0.8046	Intermediate Similarity	NPC64153
0.8022	Intermediate Similarity	NPC473331
0.8	Intermediate Similarity	NPC191339
0.8	Intermediate Similarity	NPC286341
0.7938	Intermediate Similarity	NPC54737
0.7938	Intermediate Similarity	NPC44004
0.7931	Intermediate Similarity	NPC245434
0.7912	Intermediate Similarity	NPC135776
0.7895	Intermediate Similarity	NPC150923
0.7895	Intermediate Similarity	NPC171759
0.7857	Intermediate Similarity	NPC19841
0.7841	Intermediate Similarity	NPC9231
0.7841	Intermediate Similarity	NPC162071
0.7826	Intermediate Similarity	NPC167219
0.7791	Intermediate Similarity	NPC89555
0.7789	Intermediate Similarity	NPC70865
0.7778	Intermediate Similarity	NPC212664
0.7778	Intermediate Similarity	NPC68248
0.7765	Intermediate Similarity	NPC302426
0.7753	Intermediate Similarity	NPC45957
0.7753	Intermediate Similarity	NPC471657
0.7742	Intermediate Similarity	NPC304886
0.7732	Intermediate Similarity	NPC124881
0.7727	Intermediate Similarity	NPC165162
0.7717	Intermediate Similarity	NPC475788
0.7708	Intermediate Similarity	NPC477950
0.7701	Intermediate Similarity	NPC215294
0.7701	Intermediate Similarity	NPC39588
0.77	Intermediate Similarity	NPC115352
0.77	Intermediate Similarity	NPC59489
0.77	Intermediate Similarity	NPC139838
0.7692	Intermediate Similarity	NPC129419
0.7684	Intermediate Similarity	NPC249171
0.7684	Intermediate Similarity	NPC49833
0.7683	Intermediate Similarity	NPC48641
0.7674	Intermediate Similarity	NPC10276
0.7674	Intermediate Similarity	NPC35089
0.7674	Intermediate Similarity	NPC47635
0.7667	Intermediate Similarity	NPC53158
0.7647	Intermediate Similarity	NPC617
0.764	Intermediate Similarity	NPC107787
0.7629	Intermediate Similarity	NPC86077
0.7619	Intermediate Similarity	NPC470240
0.7619	Intermediate Similarity	NPC65603
0.7619	Intermediate Similarity	NPC476794
0.7614	Intermediate Similarity	NPC154893
0.7614	Intermediate Similarity	NPC114979
0.7614	Intermediate Similarity	NPC191476
0.7614	Intermediate Similarity	NPC115786
0.7614	Intermediate Similarity	NPC53011
0.7614	Intermediate Similarity	NPC37005
0.7614	Intermediate Similarity	NPC165287
0.7614	Intermediate Similarity	NPC16887
0.7609	Intermediate Similarity	NPC300312
0.7609	Intermediate Similarity	NPC261607
0.7609	Intermediate Similarity	NPC111114
0.759	Intermediate Similarity	NPC138408
0.759	Intermediate Similarity	NPC226669
0.759	Intermediate Similarity	NPC193351
0.7582	Intermediate Similarity	NPC32922
0.7582	Intermediate Similarity	NPC268298
0.7579	Intermediate Similarity	NPC236580
0.7579	Intermediate Similarity	NPC304445
0.7579	Intermediate Similarity	NPC477949
0.7576	Intermediate Similarity	NPC243998
0.7576	Intermediate Similarity	NPC223450
0.7558	Intermediate Similarity	NPC80622
0.7558	Intermediate Similarity	NPC476625
0.7556	Intermediate Similarity	NPC186148
0.7553	Intermediate Similarity	NPC193645
0.7553	Intermediate Similarity	NPC469873
0.7553	Intermediate Similarity	NPC90121
0.7553	Intermediate Similarity	NPC167893
0.7553	Intermediate Similarity	NPC475900
0.7553	Intermediate Similarity	NPC48803
0.7553	Intermediate Similarity	NPC224689
0.7553	Intermediate Similarity	NPC275960
0.7551	Intermediate Similarity	NPC473148
0.7531	Intermediate Similarity	NPC18543
0.7529	Intermediate Similarity	NPC267231
0.7528	Intermediate Similarity	NPC78089
0.7528	Intermediate Similarity	NPC33570

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 NPC245665 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	2493
0.2-0.3	4046
0.3-0.4	1631
0.4-0.5	428
0.5-0.6	244
0.6-0.7	33
0.7-0.8	6
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
0.8182	Intermediate Similarity	NPD1695	Approved
0.7553	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5362	Discontinued
0.7143	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5785	Approved
0.7079	Intermediate Similarity	NPD5369	Approved
0.6957	Remote Similarity	NPD5363	Approved
0.6957	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6371	Approved
0.6822	Remote Similarity	NPD6053	Discontinued
0.6813	Remote Similarity	NPD4269	Approved
0.6813	Remote Similarity	NPD4270	Approved
0.6813	Remote Similarity	NPD6435	Approved
0.6778	Remote Similarity	NPD4819	Approved
0.6778	Remote Similarity	NPD4821	Approved
0.6778	Remote Similarity	NPD4820	Approved
0.6778	Remote Similarity	NPD4822	Approved
0.6778	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5332	Approved
0.6739	Remote Similarity	NPD5331	Approved
0.6739	Remote Similarity	NPD7154	Phase 3
0.6703	Remote Similarity	NPD4790	Discontinued
0.6702	Remote Similarity	NPD4249	Approved
0.6702	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6634	Remote Similarity	NPD5696	Approved
0.6632	Remote Similarity	NPD4250	Approved
0.6632	Remote Similarity	NPD4251	Approved
0.6596	Remote Similarity	NPD1694	Approved
0.6593	Remote Similarity	NPD4252	Approved
0.6593	Remote Similarity	NPD5368	Approved
0.6559	Remote Similarity	NPD4788	Approved
0.6556	Remote Similarity	NPD4268	Approved
0.6556	Remote Similarity	NPD4271	Approved
0.6535	Remote Similarity	NPD6083	Phase 2
0.6535	Remote Similarity	NPD6084	Phase 2
0.65	Remote Similarity	NPD3198	Approved
0.6465	Remote Similarity	NPD6399	Phase 3
0.6429	Remote Similarity	NPD5207	Approved
0.6392	Remote Similarity	NPD6903	Approved
0.6374	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8034	Phase 2
0.6364	Remote Similarity	NPD8035	Phase 2
0.6364	Remote Similarity	NPD5693	Phase 1
0.6355	Remote Similarity	NPD5697	Approved
0.6354	Remote Similarity	NPD7334	Approved
0.6354	Remote Similarity	NPD6409	Approved
0.6354	Remote Similarity	NPD5330	Approved
0.6354	Remote Similarity	NPD7146	Approved
0.6354	Remote Similarity	NPD6684	Approved
0.6354	Remote Similarity	NPD7521	Approved
0.6337	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4225	Approved
0.6296	Remote Similarity	NPD7320	Approved
0.6296	Remote Similarity	NPD6899	Approved
0.6296	Remote Similarity	NPD6881	Approved
0.6283	Remote Similarity	NPD7115	Discovery
0.6277	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6650	Approved
0.6273	Remote Similarity	NPD6649	Approved
0.6263	Remote Similarity	NPD46	Approved
0.6263	Remote Similarity	NPD6698	Approved
0.6262	Remote Similarity	NPD5739	Approved
0.6262	Remote Similarity	NPD6402	Approved
0.6262	Remote Similarity	NPD6008	Approved
0.6262	Remote Similarity	NPD6675	Approved
0.6262	Remote Similarity	NPD7128	Approved
0.625	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6012	Approved
0.6239	Remote Similarity	NPD6014	Approved
0.6239	Remote Similarity	NPD6373	Approved
0.6239	Remote Similarity	NPD6372	Approved
0.6239	Remote Similarity	NPD6013	Approved
0.6238	Remote Similarity	NPD5282	Discontinued
0.6238	Remote Similarity	NPD6001	Approved
0.6224	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD3702	Approved
0.6204	Remote Similarity	NPD5701	Approved
0.62	Remote Similarity	NPD5281	Approved
0.62	Remote Similarity	NPD5284	Approved
0.6182	Remote Similarity	NPD7290	Approved
0.6182	Remote Similarity	NPD6883	Approved
0.6182	Remote Similarity	NPD7102	Approved
0.6176	Remote Similarity	NPD4629	Approved
0.6176	Remote Similarity	NPD5210	Approved
0.6162	Remote Similarity	NPD4753	Phase 2
0.6154	Remote Similarity	NPD7638	Approved
0.6147	Remote Similarity	NPD6011	Approved
0.6146	Remote Similarity	NPD3665	Phase 1
0.6146	Remote Similarity	NPD3133	Approved
0.6146	Remote Similarity	NPD3666	Approved
0.6126	Remote Similarity	NPD6847	Approved
0.6126	Remote Similarity	NPD6617	Approved
0.6126	Remote Similarity	NPD6869	Approved
0.6126	Remote Similarity	NPD8130	Phase 1
0.6105	Remote Similarity	NPD4221	Approved
0.6105	Remote Similarity	NPD4223	Phase 3
0.6095	Remote Similarity	NPD7640	Approved
0.6095	Remote Similarity	NPD7639	Approved
0.6071	Remote Similarity	NPD8297	Approved
0.6071	Remote Similarity	NPD6882	Approved
0.6061	Remote Similarity	NPD5208	Approved
0.6022	Remote Similarity	NPD4238	Approved
0.6022	Remote Similarity	NPD4802	Phase 2
0.602	Remote Similarity	NPD5690	Phase 2
0.602	Remote Similarity	NPD6098	Approved
0.6	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD6080	Approved
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD6904	Approved
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6101	Approved
0.5981	Remote Similarity	NPD5211	Phase 2
0.598	Remote Similarity	NPD4202	Approved
0.598	Remote Similarity	NPD5779	Approved
0.598	Remote Similarity	NPD5778	Approved
0.5979	Remote Similarity	NPD4786	Approved
0.5979	Remote Similarity	NPD4197	Approved
0.5943	Remote Similarity	NPD4696	Approved
0.5943	Remote Similarity	NPD5285	Approved
0.5943	Remote Similarity	NPD5286	Approved
0.5941	Remote Similarity	NPD5692	Phase 3
0.5941	Remote Similarity	NPD7838	Discovery
0.5938	Remote Similarity	NPD3667	Approved
0.5938	Remote Similarity	NPD5209	Approved
0.5932	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.593	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5329	Approved
0.5913	Remote Similarity	NPD6274	Approved
0.5905	Remote Similarity	NPD4755	Approved
0.59	Remote Similarity	NPD6672	Approved
0.59	Remote Similarity	NPD4518	Approved
0.59	Remote Similarity	NPD5737	Approved
0.5882	Remote Similarity	NPD5694	Approved
0.5882	Remote Similarity	NPD7637	Suspended
0.5882	Remote Similarity	NPD6050	Approved
0.5882	Remote Similarity	NPD6411	Approved
0.5877	Remote Similarity	NPD8133	Approved
0.5872	Remote Similarity	NPD5141	Approved
0.5868	Remote Similarity	NPD7507	Approved
0.5859	Remote Similarity	NPD4694	Approved
0.5859	Remote Similarity	NPD4693	Phase 3
0.5859	Remote Similarity	NPD3618	Phase 1
0.5859	Remote Similarity	NPD5279	Phase 3
0.5859	Remote Similarity	NPD4689	Approved
0.5859	Remote Similarity	NPD4688	Approved
0.5859	Remote Similarity	NPD5205	Approved
0.5859	Remote Similarity	NPD5280	Approved
0.5859	Remote Similarity	NPD4138	Approved
0.5859	Remote Similarity	NPD4690	Approved
0.5856	Remote Similarity	NPD6686	Approved
0.5841	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5226	Approved
0.5833	Remote Similarity	NPD5225	Approved
0.5833	Remote Similarity	NPD5224	Approved
0.5833	Remote Similarity	NPD4633	Approved
0.5794	Remote Similarity	NPD4700	Approved
0.5785	Remote Similarity	NPD7492	Approved
0.578	Remote Similarity	NPD6052	Approved
0.578	Remote Similarity	NPD5175	Approved
0.578	Remote Similarity	NPD5174	Approved
0.5763	Remote Similarity	NPD7101	Approved
0.5763	Remote Similarity	NPD7100	Approved
0.5741	Remote Similarity	NPD5223	Approved
0.5739	Remote Similarity	NPD4632	Approved
0.5738	Remote Similarity	NPD6616	Approved
0.5728	Remote Similarity	NPD6079	Approved
0.5728	Remote Similarity	NPD7983	Approved
0.5726	Remote Similarity	NPD6317	Approved
0.5726	Remote Similarity	NPD7319	Approved
0.5714	Remote Similarity	NPD5777	Approved
0.5714	Remote Similarity	NPD6695	Phase 3
0.5714	Remote Similarity	NPD6054	Approved
0.5714	Remote Similarity	NPD6319	Approved
0.5701	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.57	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD8039	Approved
0.5691	Remote Similarity	NPD7078	Approved
0.5688	Remote Similarity	NPD7632	Discontinued
0.5686	Remote Similarity	NPD5370	Suspended
0.5686	Remote Similarity	NPD5328	Approved
0.5678	Remote Similarity	NPD6313	Approved
0.5678	Remote Similarity	NPD6335	Approved
0.5678	Remote Similarity	NPD6314	Approved
0.567	Remote Similarity	NPD4139	Approved
0.567	Remote Similarity	NPD4692	Approved
0.5667	Remote Similarity	NPD6015	Approved
0.5667	Remote Similarity	NPD6016	Approved
0.5657	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD7736	Approved
0.5631	Remote Similarity	NPD4096	Approved
0.5625	Remote Similarity	NPD4195	Approved
0.5625	Remote Similarity	NPD6412	Phase 2
0.562	Remote Similarity	NPD5988	Approved
0.562	Remote Similarity	NPD6370	Approved
0.5619	Remote Similarity	NPD7748	Approved
0.5614	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD6420	Discontinued

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