NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	230.13
Volume:	249.361
LogP:	2.639
LogD:	2.537
LogS:	-3.506
# Rotatable Bonds:	0
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.363
Synthetic Accessibility Score:	4.402
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:	-4.578
MDCK Permeability:	5.551331560127437e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.781
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.977
Plasma Protein Binding (PPB):	78.04639434814453%
Volume Distribution (VD):	1.245
Pgp-substrate:	15.919839859008789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.399
CYP1A2-substrate:	0.499
CYP2C19-inhibitor:	0.126
CYP2C19-substrate:	0.229
CYP2C9-inhibitor:	0.208
CYP2C9-substrate:	0.109
CYP2D6-inhibitor:	0.056
CYP2D6-substrate:	0.75
CYP3A4-inhibitor:	0.095
CYP3A4-substrate:	0.203

ADMET: Excretion

Clearance (CL):	12.016
Half-life (T1/2):	0.051

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.502
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.839
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.064
Carcinogencity:	0.663
Eye Corrosion:	0.005
Eye Irritation:	0.118
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC320537

Natural Product ID:	NPC320537
*Common Name:**	Dehydro-Alpha-Curcumene
IUPAC Name:	3,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
Synonyms:	Dehydro-Alpha-Curcumene
Standard InCHIKey:	NETSQGRTUNRXEO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H18O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h11-14H,1-7H2
SMILES:	C=C1C(=O)OC2C1CCC(=C)C1C2C(=C)CC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1939730
PubChem CID:	4426320
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
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1080/10412905.2001.9699624]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11912066]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[12419922]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21188975]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3531	Vladimiria denticulata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO30004	Vladimiria souliei	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO3531	Vladimiria denticulata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3531	Vladimiria denticulata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30004	Vladimiria souliei	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30115	Aucklandia lappa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29515	Laurus nobilis	Species	Lauraceae	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
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	41.95	%	PMID[474954]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	42.54	%	PMID[474954]

☑ 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 NPC320537 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	244
0.1-0.2	2010
0.2-0.3	10399
0.3-0.4	15499
0.4-0.5	8746
0.5-0.6	4438
0.6-0.7	1063
0.7-0.8	224
0.8-0.85	46
0.85-0.9	20
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC143979
0.9577	High Similarity	NPC208223
0.9189	High Similarity	NPC6823
0.9189	High Similarity	NPC290508
0.9189	High Similarity	NPC293418
0.9189	High Similarity	NPC73052
0.913	High Similarity	NPC5714
0.9054	High Similarity	NPC182550
0.8947	High Similarity	NPC246076
0.8933	High Similarity	NPC276356
0.8933	High Similarity	NPC74673
0.8933	High Similarity	NPC69271
0.8831	High Similarity	NPC54468
0.8831	High Similarity	NPC245665
0.8718	High Similarity	NPC194859
0.8718	High Similarity	NPC224386
0.8608	High Similarity	NPC284534
0.8608	High Similarity	NPC204105
0.8608	High Similarity	NPC300082
0.85	High Similarity	NPC64153
0.85	High Similarity	NPC238593
0.85	High Similarity	NPC187661
0.85	High Similarity	NPC309757
0.85	High Similarity	NPC56593
0.85	High Similarity	NPC304558
0.85	High Similarity	NPC236692
0.8481	Intermediate Similarity	NPC156485
0.8442	Intermediate Similarity	NPC302426
0.8395	Intermediate Similarity	NPC270270
0.8395	Intermediate Similarity	NPC24728
0.8395	Intermediate Similarity	NPC201658
0.8395	Intermediate Similarity	NPC118601
0.8375	Intermediate Similarity	NPC235792
0.8354	Intermediate Similarity	NPC215294
0.8354	Intermediate Similarity	NPC39588
0.8333	Intermediate Similarity	NPC35089
0.8333	Intermediate Similarity	NPC10276
0.8333	Intermediate Similarity	NPC47635
0.8293	Intermediate Similarity	NPC217983
0.8293	Intermediate Similarity	NPC471149
0.8293	Intermediate Similarity	NPC79549
0.8293	Intermediate Similarity	NPC207114
0.8293	Intermediate Similarity	NPC178875
0.8289	Intermediate Similarity	NPC470240
0.8289	Intermediate Similarity	NPC65603
0.8289	Intermediate Similarity	NPC476794
0.8272	Intermediate Similarity	NPC67493
0.8267	Intermediate Similarity	NPC226669
0.8267	Intermediate Similarity	NPC138408
0.8267	Intermediate Similarity	NPC193351
0.8193	Intermediate Similarity	NPC168679
0.8193	Intermediate Similarity	NPC472872
0.8193	Intermediate Similarity	NPC38392
0.8193	Intermediate Similarity	NPC215556
0.8193	Intermediate Similarity	NPC12872
0.8193	Intermediate Similarity	NPC155935
0.8193	Intermediate Similarity	NPC283409
0.8158	Intermediate Similarity	NPC235906
0.8148	Intermediate Similarity	NPC33570
0.8148	Intermediate Similarity	NPC21471
0.8148	Intermediate Similarity	NPC161957
0.8133	Intermediate Similarity	NPC469641
0.8133	Intermediate Similarity	NPC469643
0.8101	Intermediate Similarity	NPC126248
0.8095	Intermediate Similarity	NPC297474
0.8095	Intermediate Similarity	NPC19087
0.8095	Intermediate Similarity	NPC35809
0.8095	Intermediate Similarity	NPC216284
0.8095	Intermediate Similarity	NPC54065
0.8077	Intermediate Similarity	NPC470239
0.8077	Intermediate Similarity	NPC470244
0.8072	Intermediate Similarity	NPC224652
0.8072	Intermediate Similarity	NPC91248
0.8052	Intermediate Similarity	NPC15975
0.8052	Intermediate Similarity	NPC53581
0.8052	Intermediate Similarity	NPC195785
0.8052	Intermediate Similarity	NPC103987
0.8049	Intermediate Similarity	NPC107787
0.8026	Intermediate Similarity	NPC155587
0.8025	Intermediate Similarity	NPC115786
0.8	Intermediate Similarity	NPC133888
0.8	Intermediate Similarity	NPC286341
0.8	Intermediate Similarity	NPC29821
0.8	Intermediate Similarity	NPC191339
0.8	Intermediate Similarity	NPC293001
0.8	Intermediate Similarity	NPC35959
0.8	Intermediate Similarity	NPC184063
0.8	Intermediate Similarity	NPC155215
0.8	Intermediate Similarity	NPC57304
0.8	Intermediate Similarity	NPC171360
0.8	Intermediate Similarity	NPC63193
0.7976	Intermediate Similarity	NPC4986
0.7975	Intermediate Similarity	NPC258965
0.7975	Intermediate Similarity	NPC156658
0.7975	Intermediate Similarity	NPC51507
0.7952	Intermediate Similarity	NPC190753
0.7927	Intermediate Similarity	NPC78089
0.7907	Intermediate Similarity	NPC473273
0.7907	Intermediate Similarity	NPC473234
0.7907	Intermediate Similarity	NPC60386
0.7907	Intermediate Similarity	NPC308656
0.7907	Intermediate Similarity	NPC153590
0.7907	Intermediate Similarity	NPC200237
0.7907	Intermediate Similarity	NPC473263
0.7907	Intermediate Similarity	NPC258216
0.7901	Intermediate Similarity	NPC128246
0.7882	Intermediate Similarity	NPC301969
0.7882	Intermediate Similarity	NPC37607
0.7875	Intermediate Similarity	NPC301477
0.7875	Intermediate Similarity	NPC25684
0.7875	Intermediate Similarity	NPC38642
0.7875	Intermediate Similarity	NPC281949
0.7867	Intermediate Similarity	NPC163003
0.7848	Intermediate Similarity	NPC472965
0.7848	Intermediate Similarity	NPC63649
0.7848	Intermediate Similarity	NPC264227
0.7848	Intermediate Similarity	NPC617
0.7831	Intermediate Similarity	NPC470242
0.7821	Intermediate Similarity	NPC187568
0.7821	Intermediate Similarity	NPC41780
0.7816	Intermediate Similarity	NPC473331
0.7791	Intermediate Similarity	NPC475925
0.7791	Intermediate Similarity	NPC131209
0.7791	Intermediate Similarity	NPC133698
0.7778	Intermediate Similarity	NPC226988
0.7765	Intermediate Similarity	NPC288699
0.7763	Intermediate Similarity	NPC58956
0.7763	Intermediate Similarity	NPC269206
0.7763	Intermediate Similarity	NPC295633
0.775	Intermediate Similarity	NPC223904
0.7733	Intermediate Similarity	NPC472955
0.7727	Intermediate Similarity	NPC163228
0.7727	Intermediate Similarity	NPC167893
0.7727	Intermediate Similarity	NPC472873
0.7727	Intermediate Similarity	NPC476053
0.7722	Intermediate Similarity	NPC472960
0.7722	Intermediate Similarity	NPC299235
0.7701	Intermediate Similarity	NPC472874
0.7701	Intermediate Similarity	NPC135776
0.7692	Intermediate Similarity	NPC123360
0.7683	Intermediate Similarity	NPC111409
0.7683	Intermediate Similarity	NPC194637
0.7662	Intermediate Similarity	NPC140287
0.7662	Intermediate Similarity	NPC476355
0.7654	Intermediate Similarity	NPC255580
0.7654	Intermediate Similarity	NPC39411
0.7654	Intermediate Similarity	NPC141810
0.764	Intermediate Similarity	NPC142529
0.764	Intermediate Similarity	NPC18019
0.764	Intermediate Similarity	NPC91771
0.764	Intermediate Similarity	NPC24956
0.7632	Intermediate Similarity	NPC129665
0.7625	Intermediate Similarity	NPC19841
0.7614	Intermediate Similarity	NPC470013
0.7614	Intermediate Similarity	NPC198853
0.7614	Intermediate Similarity	NPC477131
0.7614	Intermediate Similarity	NPC127019
0.7614	Intermediate Similarity	NPC262133
0.7614	Intermediate Similarity	NPC323008
0.7614	Intermediate Similarity	NPC470010
0.76	Intermediate Similarity	NPC144511
0.76	Intermediate Similarity	NPC296522
0.759	Intermediate Similarity	NPC470011
0.759	Intermediate Similarity	NPC219011
0.7586	Intermediate Similarity	NPC150978
0.7586	Intermediate Similarity	NPC123177
0.7586	Intermediate Similarity	NPC70595
0.7586	Intermediate Similarity	NPC74103
0.7564	Intermediate Similarity	NPC471491
0.7561	Intermediate Similarity	NPC173609
0.7561	Intermediate Similarity	NPC178676
0.7561	Intermediate Similarity	NPC89555
0.7558	Intermediate Similarity	NPC268298
0.7556	Intermediate Similarity	NPC170143
0.7556	Intermediate Similarity	NPC311904
0.7556	Intermediate Similarity	NPC108475
0.7556	Intermediate Similarity	NPC474313
0.7556	Intermediate Similarity	NPC471150
0.7556	Intermediate Similarity	NPC213947
0.7532	Intermediate Similarity	NPC472956
0.7531	Intermediate Similarity	NPC474981
0.7528	Intermediate Similarity	NPC67584
0.7528	Intermediate Similarity	NPC170120
0.7528	Intermediate Similarity	NPC52044
0.7528	Intermediate Similarity	NPC213698
0.75	Intermediate Similarity	NPC128276
0.75	Intermediate Similarity	NPC475700
0.75	Intermediate Similarity	NPC18543
0.75	Intermediate Similarity	NPC165162
0.7473	Intermediate Similarity	NPC249171
0.7473	Intermediate Similarity	NPC45125
0.7473	Intermediate Similarity	NPC49833
0.7471	Intermediate Similarity	NPC129419
0.7471	Intermediate Similarity	NPC62815
0.7471	Intermediate Similarity	NPC253144
0.747	Intermediate Similarity	NPC272814
0.747	Intermediate Similarity	NPC128429
0.747	Intermediate Similarity	NPC318468
0.7468	Intermediate Similarity	NPC266159
0.7468	Intermediate Similarity	NPC472959

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 NPC320537 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	2814
0.2-0.3	4069
0.3-0.4	1386
0.4-0.5	452
0.5-0.6	112
0.6-0.7	20
0.7-0.8	2
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
0.7976	Intermediate Similarity	NPD1695	Approved
0.7333	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1694	Approved
0.6768	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD5362	Discontinued
0.6517	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5363	Approved
0.6484	Remote Similarity	NPD6903	Approved
0.6444	Remote Similarity	NPD7334	Approved
0.6444	Remote Similarity	NPD6409	Approved
0.6444	Remote Similarity	NPD6684	Approved
0.6444	Remote Similarity	NPD7146	Approved
0.6444	Remote Similarity	NPD7521	Approved
0.6444	Remote Similarity	NPD5330	Approved
0.6437	Remote Similarity	NPD5369	Approved
0.6364	Remote Similarity	NPD4270	Approved
0.6364	Remote Similarity	NPD4269	Approved
0.6304	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7154	Phase 3
0.6264	Remote Similarity	NPD5786	Approved
0.625	Remote Similarity	NPD4790	Discontinued
0.6211	Remote Similarity	NPD6399	Phase 3
0.6203	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.618	Remote Similarity	NPD6435	Approved
0.618	Remote Similarity	NPD5209	Approved
0.617	Remote Similarity	NPD5207	Approved
0.6164	Remote Similarity	NPD9298	Approved
0.6136	Remote Similarity	NPD4252	Approved
0.6136	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6672	Approved
0.6129	Remote Similarity	NPD5737	Approved
0.6118	Remote Similarity	NPD8039	Approved
0.6111	Remote Similarity	NPD5332	Approved
0.6111	Remote Similarity	NPD5331	Approved
0.6105	Remote Similarity	NPD8034	Phase 2
0.6105	Remote Similarity	NPD8035	Phase 2
0.6105	Remote Similarity	NPD5693	Phase 1
0.6095	Remote Similarity	NPD6371	Approved
0.6092	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4249	Approved
0.6082	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4225	Approved
0.6022	Remote Similarity	NPD4251	Approved
0.6022	Remote Similarity	NPD4250	Approved
0.6019	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6698	Approved
0.6	Remote Similarity	NPD46	Approved
0.5981	Remote Similarity	NPD6053	Discontinued
0.5979	Remote Similarity	NPD6001	Approved
0.5978	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD3198	Approved
0.5955	Remote Similarity	NPD4822	Approved
0.5955	Remote Similarity	NPD5368	Approved
0.5955	Remote Similarity	NPD4820	Approved
0.5955	Remote Similarity	NPD4821	Approved
0.5955	Remote Similarity	NPD4819	Approved
0.5909	Remote Similarity	NPD4271	Approved
0.5909	Remote Similarity	NPD4268	Approved
0.59	Remote Similarity	NPD7638	Approved
0.5842	Remote Similarity	NPD7639	Approved
0.5842	Remote Similarity	NPD7640	Approved
0.5824	Remote Similarity	NPD3667	Approved
0.5816	Remote Similarity	NPD5282	Discontinued
0.5789	Remote Similarity	NPD5208	Approved
0.5783	Remote Similarity	NPD229	Approved
0.5766	Remote Similarity	NPD7115	Discovery
0.5765	Remote Similarity	NPD5777	Approved
0.5761	Remote Similarity	NPD4788	Approved
0.5758	Remote Similarity	NPD5695	Phase 3
0.5745	Remote Similarity	NPD3618	Phase 1
0.5745	Remote Similarity	NPD6098	Approved
0.5743	Remote Similarity	NPD5696	Approved
0.5729	Remote Similarity	NPD6051	Approved
0.5729	Remote Similarity	NPD6673	Approved
0.5729	Remote Similarity	NPD6080	Approved
0.5729	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6101	Approved
0.5729	Remote Similarity	NPD6904	Approved
0.5714	Remote Similarity	NPD5779	Approved
0.5714	Remote Similarity	NPD5778	Approved
0.5699	Remote Similarity	NPD3668	Phase 3
0.5699	Remote Similarity	NPD3665	Phase 1
0.5699	Remote Similarity	NPD3666	Approved
0.5699	Remote Similarity	NPD3133	Approved
0.5699	Remote Similarity	NPD4786	Approved
0.5696	Remote Similarity	NPD1145	Discontinued
0.567	Remote Similarity	NPD7838	Discovery
0.567	Remote Similarity	NPD5692	Phase 3
0.5657	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD7900	Approved
0.5644	Remote Similarity	NPD6083	Phase 2
0.5644	Remote Similarity	NPD6084	Phase 2
0.5612	Remote Similarity	NPD5694	Approved
0.5612	Remote Similarity	NPD6411	Approved
0.5612	Remote Similarity	NPD6050	Approved
0.5607	Remote Similarity	NPD6686	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