NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	230.13
Volume:	249.361
LogP:	3.497
LogD:	3.151
LogS:	-3.428
# 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:	4.356
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.566
MDCK Permeability:	2.6639416319085285e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.951
30% Bioavailability (F30%):	0.298

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.131
Plasma Protein Binding (PPB):	81.02906036376953%
Volume Distribution (VD):	1.907
Pgp-substrate:	12.896108627319336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.764
CYP1A2-substrate:	0.225
CYP2C19-inhibitor:	0.27
CYP2C19-substrate:	0.524
CYP2C9-inhibitor:	0.219
CYP2C9-substrate:	0.11
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.279
CYP3A4-inhibitor:	0.479
CYP3A4-substrate:	0.189

ADMET: Excretion

Clearance (CL):	15.036
Half-life (T1/2):	0.34

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.784
Drug-inuced Liver Injury (DILI):	0.373
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.842
Maximum Recommended Daily Dose:	0.859
Skin Sensitization:	0.402
Carcinogencity:	0.389
Eye Corrosion:	0.759
Eye Irritation:	0.869
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC276356

Natural Product ID:	NPC276356
*Common Name:**	Isodehydrocostus Lactone
IUPAC Name:	(3aS,6aR,9aR,9bS)-9-methyl-3,6-dimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
Synonyms:	Isodehydrocostus Lactone
Standard InCHIKey:	HOKNRQOXIXGZDY-XUXIUFHCSA-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/h5,11-14H,1,3-4,6-7H2,2H3/t11-,12-,13-,14-/m0/s1
SMILES:	CC1=CC[C@@H]2[C@H]1[C@H]1OC(=O)C(=C)[C@@H]1CCC2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451971
PubChem CID:	10933292
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
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[14510592]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[15997133]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[16141313]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	callus	n.a.	PMID[22368856]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23611151]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[24931277]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562066]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572418]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25825	Saussurea lappa	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
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	16000.0	nM	PMID[564864]

☑ 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 NPC276356 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	194
0.1-0.2	1340
0.2-0.3	6350
0.3-0.4	16490
0.4-0.5	9224
0.5-0.6	6273
0.6-0.7	2205
0.7-0.8	505
0.8-0.85	76
0.85-0.9	30
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC69271
0.9474	High Similarity	NPC74673
0.9342	High Similarity	NPC182550
0.9221	High Similarity	NPC302426
0.9114	High Similarity	NPC215294
0.9114	High Similarity	NPC39588
0.9024	High Similarity	NPC91248
0.8933	High Similarity	NPC320537
0.8933	High Similarity	NPC143979
0.8916	High Similarity	NPC4986
0.8889	High Similarity	NPC33570
0.8889	High Similarity	NPC161957
0.8889	High Similarity	NPC21471
0.8861	High Similarity	NPC35089
0.8861	High Similarity	NPC10276
0.8831	High Similarity	NPC65603
0.8831	High Similarity	NPC195785
0.8831	High Similarity	NPC476794
0.8831	High Similarity	NPC470240
0.8831	High Similarity	NPC15975
0.8816	High Similarity	NPC226669
0.8816	High Similarity	NPC193351
0.8816	High Similarity	NPC138408
0.878	High Similarity	NPC107787
0.8765	High Similarity	NPC115786
0.8706	High Similarity	NPC131209
0.8706	High Similarity	NPC133698
0.8701	High Similarity	NPC235906
0.8659	High Similarity	NPC78089
0.8608	High Similarity	NPC470239
0.8608	High Similarity	NPC470244
0.859	High Similarity	NPC208223
0.8571	High Similarity	NPC155587
0.8537	High Similarity	NPC156485
0.8506	High Similarity	NPC323008
0.8506	High Similarity	NPC262133
0.8506	High Similarity	NPC470013
0.8506	High Similarity	NPC198853
0.8506	High Similarity	NPC477131
0.8506	High Similarity	NPC470010
0.85	High Similarity	NPC6823
0.85	High Similarity	NPC73052
0.85	High Similarity	NPC293418
0.85	High Similarity	NPC290508
0.8481	Intermediate Similarity	NPC299235
0.8434	Intermediate Similarity	NPC235792
0.8421	Intermediate Similarity	NPC163003
0.8415	Intermediate Similarity	NPC245665
0.84	Intermediate Similarity	NPC5714
0.8395	Intermediate Similarity	NPC281949
0.8395	Intermediate Similarity	NPC39411
0.8395	Intermediate Similarity	NPC255580
0.8395	Intermediate Similarity	NPC25684
0.8395	Intermediate Similarity	NPC301477
0.8375	Intermediate Similarity	NPC264227
0.8375	Intermediate Similarity	NPC472965
0.8375	Intermediate Similarity	NPC617
0.8375	Intermediate Similarity	NPC63649
0.8372	Intermediate Similarity	NPC301969
0.8372	Intermediate Similarity	NPC37607
0.8354	Intermediate Similarity	NPC41780
0.8354	Intermediate Similarity	NPC103987
0.8354	Intermediate Similarity	NPC53581
0.8354	Intermediate Similarity	NPC187568
0.8333	Intermediate Similarity	NPC64153
0.8333	Intermediate Similarity	NPC67493
0.8312	Intermediate Similarity	NPC58956
0.8312	Intermediate Similarity	NPC295633
0.8312	Intermediate Similarity	NPC269206
0.8293	Intermediate Similarity	NPC246076
0.8289	Intermediate Similarity	NPC472955
0.8276	Intermediate Similarity	NPC150978
0.8276	Intermediate Similarity	NPC123177
0.8276	Intermediate Similarity	NPC74103
0.8276	Intermediate Similarity	NPC70595
0.8272	Intermediate Similarity	NPC223904
0.8256	Intermediate Similarity	NPC268298
0.825	Intermediate Similarity	NPC472960
0.8228	Intermediate Similarity	NPC123360
0.8214	Intermediate Similarity	NPC284534
0.8214	Intermediate Similarity	NPC204105
0.8214	Intermediate Similarity	NPC300082
0.8205	Intermediate Similarity	NPC476355
0.8205	Intermediate Similarity	NPC469643
0.8205	Intermediate Similarity	NPC140287
0.8205	Intermediate Similarity	NPC469641
0.8193	Intermediate Similarity	NPC54468
0.8182	Intermediate Similarity	NPC135776
0.8182	Intermediate Similarity	NPC129665
0.8171	Intermediate Similarity	NPC141810
0.8161	Intermediate Similarity	NPC253144
0.8161	Intermediate Similarity	NPC129419
0.8158	Intermediate Similarity	NPC296522
0.8158	Intermediate Similarity	NPC144511
0.814	Intermediate Similarity	NPC224652
0.8118	Intermediate Similarity	NPC236692
0.8118	Intermediate Similarity	NPC309757
0.8095	Intermediate Similarity	NPC165287
0.809	Intermediate Similarity	NPC167219
0.8077	Intermediate Similarity	NPC472956
0.8072	Intermediate Similarity	NPC173609
0.8072	Intermediate Similarity	NPC89555
0.8072	Intermediate Similarity	NPC178676
0.8068	Intermediate Similarity	NPC284185
0.8025	Intermediate Similarity	NPC128276
0.8023	Intermediate Similarity	NPC270270
0.8023	Intermediate Similarity	NPC237540
0.8	Intermediate Similarity	NPC48803
0.8	Intermediate Similarity	NPC52044
0.8	Intermediate Similarity	NPC304886
0.8	Intermediate Similarity	NPC67584
0.8	Intermediate Similarity	NPC165162
0.8	Intermediate Similarity	NPC275960
0.8	Intermediate Similarity	NPC193645
0.8	Intermediate Similarity	NPC266159
0.8	Intermediate Similarity	NPC472967
0.8	Intermediate Similarity	NPC472959
0.8	Intermediate Similarity	NPC90121
0.7976	Intermediate Similarity	NPC272814
0.7976	Intermediate Similarity	NPC318468
0.7975	Intermediate Similarity	NPC472966
0.7955	Intermediate Similarity	NPC62815
0.7952	Intermediate Similarity	NPC471325
0.7952	Intermediate Similarity	NPC47635
0.7931	Intermediate Similarity	NPC178875
0.7931	Intermediate Similarity	NPC79549
0.7927	Intermediate Similarity	NPC89128
0.7927	Intermediate Similarity	NPC178277
0.7922	Intermediate Similarity	NPC199557
0.7912	Intermediate Similarity	NPC213078
0.7907	Intermediate Similarity	NPC284902
0.7907	Intermediate Similarity	NPC238593
0.7907	Intermediate Similarity	NPC304558
0.7907	Intermediate Similarity	NPC56593
0.7901	Intermediate Similarity	NPC97516
0.7901	Intermediate Similarity	NPC57744
0.7901	Intermediate Similarity	NPC122264
0.7901	Intermediate Similarity	NPC476028
0.7901	Intermediate Similarity	NPC141789
0.7901	Intermediate Similarity	NPC320630
0.7901	Intermediate Similarity	NPC116177
0.7901	Intermediate Similarity	NPC171204
0.7901	Intermediate Similarity	NPC7563
0.7882	Intermediate Similarity	NPC475100
0.7882	Intermediate Similarity	NPC224386
0.7882	Intermediate Similarity	NPC114979
0.7882	Intermediate Similarity	NPC194859
0.7882	Intermediate Similarity	NPC191476
0.7872	Intermediate Similarity	NPC86077
0.7865	Intermediate Similarity	NPC300312
0.7865	Intermediate Similarity	NPC111114
0.7865	Intermediate Similarity	NPC261607
0.7841	Intermediate Similarity	NPC32922
0.7841	Intermediate Similarity	NPC472872
0.7841	Intermediate Similarity	NPC288699
0.7841	Intermediate Similarity	NPC215556
0.7826	Intermediate Similarity	NPC161493
0.7826	Intermediate Similarity	NPC169205
0.7816	Intermediate Similarity	NPC475703
0.7816	Intermediate Similarity	NPC24728
0.7816	Intermediate Similarity	NPC201658
0.7816	Intermediate Similarity	NPC118601
0.7805	Intermediate Similarity	NPC108816
0.7805	Intermediate Similarity	NPC267231
0.7805	Intermediate Similarity	NPC196653
0.7805	Intermediate Similarity	NPC93763
0.7805	Intermediate Similarity	NPC471465
0.7791	Intermediate Similarity	NPC215364
0.7791	Intermediate Similarity	NPC110405
0.7791	Intermediate Similarity	NPC255307
0.7778	Intermediate Similarity	NPC473223
0.7765	Intermediate Similarity	NPC475947
0.7765	Intermediate Similarity	NPC22611
0.7765	Intermediate Similarity	NPC474703
0.7765	Intermediate Similarity	NPC250315
0.7753	Intermediate Similarity	NPC216284
0.7742	Intermediate Similarity	NPC141191
0.7742	Intermediate Similarity	NPC54843
0.7742	Intermediate Similarity	NPC221615
0.7738	Intermediate Similarity	NPC38642
0.7738	Intermediate Similarity	NPC42470
0.7738	Intermediate Similarity	NPC325031
0.7727	Intermediate Similarity	NPC215831
0.7727	Intermediate Similarity	NPC217983
0.7727	Intermediate Similarity	NPC226863
0.7727	Intermediate Similarity	NPC471149
0.7727	Intermediate Similarity	NPC207114
0.7717	Intermediate Similarity	NPC307164
0.7717	Intermediate Similarity	NPC185553
0.7711	Intermediate Similarity	NPC469690
0.7711	Intermediate Similarity	NPC167881
0.7711	Intermediate Similarity	NPC98557
0.7711	Intermediate Similarity	NPC270126
0.7701	Intermediate Similarity	NPC70555
0.7701	Intermediate Similarity	NPC305475
0.7701	Intermediate Similarity	NPC70422
0.7701	Intermediate Similarity	NPC187661
0.7701	Intermediate Similarity	NPC104961
0.7701	Intermediate Similarity	NPC475461
0.7701	Intermediate Similarity	NPC50637

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 NPC276356 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	1936
0.2-0.3	4108
0.3-0.4	2027
0.4-0.5	602
0.5-0.6	238
0.6-0.7	47
0.7-0.8	5
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8916	High Similarity	NPD1695	Approved
0.8	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1694	Approved
0.7586	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5362	Discontinued
0.7241	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5785	Approved
0.6966	Remote Similarity	NPD7154	Phase 3
0.6854	Remote Similarity	NPD5209	Approved
0.6827	Remote Similarity	NPD6371	Approved
0.6813	Remote Similarity	NPD5363	Approved
0.6774	Remote Similarity	NPD6903	Approved
0.675	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5369	Approved
0.6739	Remote Similarity	NPD5330	Approved
0.6739	Remote Similarity	NPD7521	Approved
0.6739	Remote Similarity	NPD6409	Approved
0.6739	Remote Similarity	NPD7334	Approved
0.6739	Remote Similarity	NPD6684	Approved
0.6739	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6632	Remote Similarity	NPD5207	Approved
0.6628	Remote Similarity	NPD8039	Approved
0.6596	Remote Similarity	NPD6672	Approved
0.6596	Remote Similarity	NPD5737	Approved
0.6596	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5331	Approved
0.6593	Remote Similarity	NPD5332	Approved
0.6591	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5693	Phase 1
0.6559	Remote Similarity	NPD5786	Approved
0.6556	Remote Similarity	NPD4790	Discontinued
0.6531	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4225	Approved
0.6484	Remote Similarity	NPD6435	Approved
0.6458	Remote Similarity	NPD46	Approved
0.6458	Remote Similarity	NPD6698	Approved
0.6444	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4252	Approved
0.6442	Remote Similarity	NPD6008	Approved
0.6429	Remote Similarity	NPD5282	Discontinued
0.6429	Remote Similarity	NPD6001	Approved
0.6389	Remote Similarity	NPD6053	Discontinued
0.6383	Remote Similarity	NPD4249	Approved
0.6316	Remote Similarity	NPD4250	Approved
0.6316	Remote Similarity	NPD4251	Approved
0.6264	Remote Similarity	NPD4821	Approved
0.6264	Remote Similarity	NPD4819	Approved
0.6264	Remote Similarity	NPD4822	Approved
0.6264	Remote Similarity	NPD4820	Approved
0.6264	Remote Similarity	NPD5368	Approved
0.625	Remote Similarity	NPD5208	Approved
0.6222	Remote Similarity	NPD4268	Approved
0.6222	Remote Similarity	NPD4271	Approved
0.6211	Remote Similarity	NPD6098	Approved
0.62	Remote Similarity	NPD5695	Phase 3
0.6186	Remote Similarity	NPD6904	Approved
0.6186	Remote Similarity	NPD6673	Approved
0.6186	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6051	Approved
0.6186	Remote Similarity	NPD6101	Approved
0.6186	Remote Similarity	NPD6080	Approved
0.6176	Remote Similarity	NPD5696	Approved
0.6176	Remote Similarity	NPD7638	Approved
0.617	Remote Similarity	NPD4786	Approved
0.6162	Remote Similarity	NPD5779	Approved
0.6162	Remote Similarity	NPD5778	Approved
0.6161	Remote Similarity	NPD7115	Discovery
0.6129	Remote Similarity	NPD3667	Approved
0.6122	Remote Similarity	NPD7838	Discovery
0.6122	Remote Similarity	NPD5692	Phase 3
0.6117	Remote Similarity	NPD7639	Approved
0.6117	Remote Similarity	NPD7640	Approved
0.61	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7900	Approved
0.6078	Remote Similarity	NPD6084	Phase 2
0.6078	Remote Similarity	NPD6083	Phase 2
0.6061	Remote Similarity	NPD5694	Approved
0.6061	Remote Similarity	NPD6411	Approved
0.6061	Remote Similarity	NPD6050	Approved
0.6042	Remote Similarity	NPD3618	Phase 1
0.6042	Remote Similarity	NPD5279	Phase 3
0.6022	Remote Similarity	NPD857	Phase 3
0.6019	Remote Similarity	NPD6686	Approved
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD3668	Phase 3
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD3573	Approved
0.5943	Remote Similarity	NPD6052	Approved
0.5941	Remote Similarity	NPD7748	Approved
0.5926	Remote Similarity	NPD5697	Approved
0.5922	Remote Similarity	NPD7902	Approved
0.59	Remote Similarity	NPD5281	Approved
0.59	Remote Similarity	NPD7983	Approved
0.59	Remote Similarity	NPD8034	Phase 2
0.59	Remote Similarity	NPD8035	Phase 2
0.59	Remote Similarity	NPD7637	Suspended
0.59	Remote Similarity	NPD5284	Approved
0.59	Remote Similarity	NPD6079	Approved
0.5876	Remote Similarity	NPD6422	Discontinued
0.5872	Remote Similarity	NPD6899	Approved
0.5872	Remote Similarity	NPD7320	Approved
0.5872	Remote Similarity	NPD6881	Approved
0.5872	Remote Similarity	NPD6011	Approved
0.5865	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD5328	Approved
0.5856	Remote Similarity	NPD6649	Approved
0.5856	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6650	Approved
0.5833	Remote Similarity	NPD6675	Approved
0.5833	Remote Similarity	NPD5739	Approved
0.5833	Remote Similarity	NPD7128	Approved
0.5833	Remote Similarity	NPD6402	Approved
0.5818	Remote Similarity	NPD6013	Approved
0.5818	Remote Similarity	NPD6373	Approved
0.5818	Remote Similarity	NPD6012	Approved
0.5818	Remote Similarity	NPD6014	Approved
0.5818	Remote Similarity	NPD6372	Approved
0.5789	Remote Similarity	NPD4221	Approved
0.5789	Remote Similarity	NPD4223	Phase 3
0.578	Remote Similarity	NPD5701	Approved
0.5773	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7102	Approved
0.5766	Remote Similarity	NPD6883	Approved
0.5766	Remote Similarity	NPD7290	Approved
0.5761	Remote Similarity	NPD4756	Discovery
0.5745	Remote Similarity	NPD4695	Discontinued
0.5743	Remote Similarity	NPD7515	Phase 2
0.5728	Remote Similarity	NPD5654	Approved
0.5728	Remote Similarity	NPD5210	Approved
0.5728	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD5690	Phase 2
0.5714	Remote Similarity	NPD28	Approved
0.5714	Remote Similarity	NPD6869	Approved
0.5714	Remote Similarity	NPD6847	Approved
0.5714	Remote Similarity	NPD8130	Phase 1
0.5714	Remote Similarity	NPD6617	Approved
0.5714	Remote Similarity	NPD29	Approved
0.5714	Remote Similarity	NPD6927	Phase 3
0.57	Remote Similarity	NPD4753	Phase 2
0.57	Remote Similarity	NPD5370	Suspended
0.5698	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD7331	Phase 2
0.5686	Remote Similarity	NPD4202	Approved
0.5686	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD4697	Phase 3
0.5673	Remote Similarity	NPD7839	Suspended
0.5673	Remote Similarity	NPD5221	Approved
0.5673	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD5222	Approved
0.567	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.567	Remote Similarity	NPD4197	Approved
0.5664	Remote Similarity	NPD8297	Approved
0.5664	Remote Similarity	NPD6882	Approved
0.566	Remote Similarity	NPD6648	Approved
0.5647	Remote Similarity	NPD3197	Phase 1
0.5647	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6614	Approved
0.5636	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD2067	Discontinued
0.5619	Remote Similarity	NPD5959	Approved
0.5619	Remote Similarity	NPD5173	Approved
0.5618	Remote Similarity	NPD4691	Approved
0.5618	Remote Similarity	NPD4747	Approved
0.5612	Remote Similarity	NPD5329	Approved
0.5607	Remote Similarity	NPD5344	Discontinued
0.5604	Remote Similarity	NPD6926	Approved
0.5604	Remote Similarity	NPD6924	Approved
0.56	Remote Similarity	NPD4518	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