NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.15
Volume:	257.918
LogP:	4.032
LogD:	3.174
LogS:	-2.908
# Rotatable Bonds:	0
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.363
Synthetic Accessibility Score:	4.23
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.496
MDCK Permeability:	2.41363904933678e-05
Pgp-inhibitor:	0.074
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.772
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	94.29761505126953%
Volume Distribution (VD):	4.1
Pgp-substrate:	3.915311098098755%

ADMET: Metabolism

CYP1A2-inhibitor:	0.738
CYP1A2-substrate:	0.365
CYP2C19-inhibitor:	0.743
CYP2C19-substrate:	0.375
CYP2C9-inhibitor:	0.642
CYP2C9-substrate:	0.666
CYP2D6-inhibitor:	0.057
CYP2D6-substrate:	0.213
CYP3A4-inhibitor:	0.363
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	6.112
Half-life (T1/2):	0.115

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.457
Drug-inuced Liver Injury (DILI):	0.509
AMES Toxicity:	0.376
Rat Oral Acute Toxicity:	0.71
Maximum Recommended Daily Dose:	0.631
Skin Sensitization:	0.487
Carcinogencity:	0.62
Eye Corrosion:	0.026
Eye Irritation:	0.365
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC58956

Natural Product ID:	NPC58956
*Common Name:**	6,10-Dimethyl-3-Methylidene-3A,4,5,8,9,11A-Hexahydrocyclodeca[B]Furan-2-One
IUPAC Name:	6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
Synonyms:
Standard InCHIKey:	HRYLQFBHBWLLLL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3
SMILES:	CC1=CC2OC(=O)C(=C)C2CCC(=CCC1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3193163
PubChem CID:	556919
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
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1080/10412905.2001.9699624]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[10364842]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11912066]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[12392098]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[12419922]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[14510592]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21188975]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24996657]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[25767328]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572418]
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]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	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]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO30115	Aucklandia lappa	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]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29515	Laurus nobilis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10391	Dolomiaea souliei	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
Potency	11

Activity Type	# Activity
Individual Protein	6
NON-MOLECULAR	4
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	12589.3	nM	PMID[536564]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	89125.1	nM	PMID[536564]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PMID[536564]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	39810.7	nM	PMID[536564]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	15848.9	nM	PMID[536564]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[536564]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	2818.4	nM	PMID[536564]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	14950.2	nM	PMID[536564]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	2369.4	nM	PMID[536564]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	9432.9	nM	PMID[536564]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	21117.7	nM	PMID[536564]

☑ 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 NPC58956 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	177
0.1-0.2	1387
0.2-0.3	6871
0.3-0.4	16888
0.4-0.5	9227
0.5-0.6	5589
0.6-0.7	1944
0.7-0.8	459
0.8-0.85	93
0.85-0.9	39
0.9-0.95	17
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC295633
1.0	High Similarity	NPC269206
0.9571	High Similarity	NPC235906
0.9559	High Similarity	NPC163003
0.9437	High Similarity	NPC171204
0.9437	High Similarity	NPC476028
0.9437	High Similarity	NPC141789
0.9429	High Similarity	NPC155587
0.9306	High Similarity	NPC471465
0.9306	High Similarity	NPC196653
0.9286	High Similarity	NPC140287
0.9286	High Similarity	NPC476355
0.9275	High Similarity	NPC129665
0.9178	High Similarity	NPC270126
0.9178	High Similarity	NPC98557
0.9178	High Similarity	NPC167881
0.9054	High Similarity	NPC281132
0.9028	High Similarity	NPC123360
0.8933	High Similarity	NPC24417
0.8904	High Similarity	NPC65603
0.8904	High Similarity	NPC7563
0.8904	High Similarity	NPC187568
0.8904	High Similarity	NPC320630
0.8904	High Similarity	NPC41780
0.8904	High Similarity	NPC97516
0.8904	High Similarity	NPC116177
0.8889	High Similarity	NPC193351
0.8889	High Similarity	NPC226669
0.8889	High Similarity	NPC138408
0.8816	High Similarity	NPC229825
0.8784	High Similarity	NPC267231
0.8784	High Similarity	NPC93763
0.8784	High Similarity	NPC108816
0.8701	High Similarity	NPC59097
0.8701	High Similarity	NPC40746
0.8701	High Similarity	NPC169575
0.8701	High Similarity	NPC473390
0.8701	High Similarity	NPC131669
0.8696	High Similarity	NPC194871
0.8649	High Similarity	NPC474760
0.8649	High Similarity	NPC470240
0.8649	High Similarity	NPC476794
0.859	High Similarity	NPC191476
0.859	High Similarity	NPC114979
0.859	High Similarity	NPC158756
0.859	High Similarity	NPC96259
0.859	High Similarity	NPC141193
0.859	High Similarity	NPC476804
0.8571	High Similarity	NPC470256
0.8481	Intermediate Similarity	NPC255307
0.8481	Intermediate Similarity	NPC470755
0.8442	Intermediate Similarity	NPC25684
0.8442	Intermediate Similarity	NPC301477
0.8442	Intermediate Similarity	NPC52861
0.8442	Intermediate Similarity	NPC281949
0.8442	Intermediate Similarity	NPC141810
0.8421	Intermediate Similarity	NPC89128
0.8421	Intermediate Similarity	NPC264227
0.8421	Intermediate Similarity	NPC178277
0.8421	Intermediate Similarity	NPC617
0.8421	Intermediate Similarity	NPC470239
0.8421	Intermediate Similarity	NPC470244
0.8421	Intermediate Similarity	NPC182550
0.8421	Intermediate Similarity	NPC472965
0.8421	Intermediate Similarity	NPC63649
0.84	Intermediate Similarity	NPC57744
0.8375	Intermediate Similarity	NPC469910
0.8375	Intermediate Similarity	NPC475461
0.8375	Intermediate Similarity	NPC50637
0.8375	Intermediate Similarity	NPC305475
0.8333	Intermediate Similarity	NPC173609
0.8312	Intermediate Similarity	NPC276356
0.8312	Intermediate Similarity	NPC302426
0.8289	Intermediate Similarity	NPC472960
0.8289	Intermediate Similarity	NPC128276
0.8272	Intermediate Similarity	NPC266957
0.8267	Intermediate Similarity	NPC68819
0.825	Intermediate Similarity	NPC50362
0.825	Intermediate Similarity	NPC38468
0.825	Intermediate Similarity	NPC319795
0.8228	Intermediate Similarity	NPC250315
0.8228	Intermediate Similarity	NPC474703
0.8228	Intermediate Similarity	NPC318468
0.8205	Intermediate Similarity	NPC471325
0.8171	Intermediate Similarity	NPC473715
0.8171	Intermediate Similarity	NPC476805
0.8171	Intermediate Similarity	NPC475819
0.8171	Intermediate Similarity	NPC476803
0.8148	Intermediate Similarity	NPC150755
0.8116	Intermediate Similarity	NPC474658
0.8101	Intermediate Similarity	NPC178676
0.8082	Intermediate Similarity	NPC472955
0.8077	Intermediate Similarity	NPC223904
0.8077	Intermediate Similarity	NPC69271
0.8077	Intermediate Similarity	NPC74673
0.8072	Intermediate Similarity	NPC474032
0.8072	Intermediate Similarity	NPC166919
0.8056	Intermediate Similarity	NPC218477
0.8052	Intermediate Similarity	NPC299235
0.8025	Intermediate Similarity	NPC215364
0.8025	Intermediate Similarity	NPC165162
0.8025	Intermediate Similarity	NPC21469
0.8	Intermediate Similarity	NPC215294
0.8	Intermediate Similarity	NPC39588
0.8	Intermediate Similarity	NPC116543
0.8	Intermediate Similarity	NPC475947
0.8	Intermediate Similarity	NPC272814
0.8	Intermediate Similarity	NPC15499
0.8	Intermediate Similarity	NPC294434
0.8	Intermediate Similarity	NPC117746
0.8	Intermediate Similarity	NPC259599
0.7976	Intermediate Similarity	NPC474232
0.7976	Intermediate Similarity	NPC179394
0.7976	Intermediate Similarity	NPC475855
0.7976	Intermediate Similarity	NPC144133
0.7976	Intermediate Similarity	NPC473619
0.7976	Intermediate Similarity	NPC469368
0.7975	Intermediate Similarity	NPC325031
0.7975	Intermediate Similarity	NPC10276
0.7975	Intermediate Similarity	NPC35089
0.7975	Intermediate Similarity	NPC42470
0.7945	Intermediate Similarity	NPC144511
0.7945	Intermediate Similarity	NPC476591
0.7945	Intermediate Similarity	NPC199557
0.7945	Intermediate Similarity	NPC88877
0.7945	Intermediate Similarity	NPC296522
0.7927	Intermediate Similarity	NPC107787
0.7927	Intermediate Similarity	NPC284902
0.7901	Intermediate Similarity	NPC115786
0.7901	Intermediate Similarity	NPC159635
0.7882	Intermediate Similarity	NPC473321
0.7875	Intermediate Similarity	NPC85772
0.7875	Intermediate Similarity	NPC89555
0.7867	Intermediate Similarity	NPC472956
0.7857	Intermediate Similarity	NPC151770
0.7838	Intermediate Similarity	NPC67183
0.7831	Intermediate Similarity	NPC475703
0.7831	Intermediate Similarity	NPC231889
0.7831	Intermediate Similarity	NPC160138
0.7805	Intermediate Similarity	NPC78089
0.7805	Intermediate Similarity	NPC21471
0.7805	Intermediate Similarity	NPC110405
0.7805	Intermediate Similarity	NPC161957
0.7805	Intermediate Similarity	NPC33570
0.7792	Intermediate Similarity	NPC472967
0.7792	Intermediate Similarity	NPC266159
0.7792	Intermediate Similarity	NPC472959
0.7791	Intermediate Similarity	NPC162205
0.7791	Intermediate Similarity	NPC273579
0.7791	Intermediate Similarity	NPC228451
0.7791	Intermediate Similarity	NPC125674
0.7791	Intermediate Similarity	NPC475302
0.7791	Intermediate Similarity	NPC295204
0.7791	Intermediate Similarity	NPC165383
0.7791	Intermediate Similarity	NPC475838
0.7791	Intermediate Similarity	NPC288240
0.7778	Intermediate Similarity	NPC170286
0.7778	Intermediate Similarity	NPC22611
0.7778	Intermediate Similarity	NPC248125
0.7765	Intermediate Similarity	NPC312042
0.7765	Intermediate Similarity	NPC251385
0.7765	Intermediate Similarity	NPC49342
0.7763	Intermediate Similarity	NPC320537
0.7763	Intermediate Similarity	NPC474758
0.7763	Intermediate Similarity	NPC143979
0.7763	Intermediate Similarity	NPC48641
0.7733	Intermediate Similarity	NPC84038
0.7733	Intermediate Similarity	NPC186531
0.7722	Intermediate Similarity	NPC473981
0.7722	Intermediate Similarity	NPC473980
0.7711	Intermediate Similarity	NPC279859
0.7711	Intermediate Similarity	NPC38576
0.7701	Intermediate Similarity	NPC140543
0.7701	Intermediate Similarity	NPC57405
0.7701	Intermediate Similarity	NPC303942
0.7701	Intermediate Similarity	NPC471147
0.7701	Intermediate Similarity	NPC473316
0.7701	Intermediate Similarity	NPC474247
0.7701	Intermediate Similarity	NPC473330
0.7692	Intermediate Similarity	NPC53581
0.7692	Intermediate Similarity	NPC195785
0.7692	Intermediate Similarity	NPC15975
0.7692	Intermediate Similarity	NPC103987
0.7683	Intermediate Similarity	NPC156485
0.7681	Intermediate Similarity	NPC286189
0.7671	Intermediate Similarity	NPC472266
0.7671	Intermediate Similarity	NPC21998
0.7662	Intermediate Similarity	NPC324762
0.7662	Intermediate Similarity	NPC329852
0.7662	Intermediate Similarity	NPC244166
0.7654	Intermediate Similarity	NPC35556
0.7654	Intermediate Similarity	NPC475690
0.7647	Intermediate Similarity	NPC295312
0.7647	Intermediate Similarity	NPC268298
0.7632	Intermediate Similarity	NPC474705
0.7632	Intermediate Similarity	NPC135703
0.7625	Intermediate Similarity	NPC195424
0.7614	Intermediate Similarity	NPC477922
0.7614	Intermediate Similarity	NPC471141
0.7614	Intermediate Similarity	NPC475659

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 NPC58956 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1916
0.2-0.3	4099
0.3-0.4	2072
0.4-0.5	652
0.5-0.6	194
0.6-0.7	42
0.7-0.8	5
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.825	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1694	Approved
0.7442	Intermediate Similarity	NPD1695	Approved
0.7229	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5209	Approved
0.7	Intermediate Similarity	NPD8039	Approved
0.6966	Remote Similarity	NPD5785	Approved
0.6941	Remote Similarity	NPD7154	Phase 3
0.6782	Remote Similarity	NPD5363	Approved
0.6778	Remote Similarity	NPD46	Approved
0.6778	Remote Similarity	NPD6698	Approved
0.6744	Remote Similarity	NPD5362	Discontinued
0.6628	Remote Similarity	NPD4270	Approved
0.6628	Remote Similarity	NPD4269	Approved
0.6591	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4252	Approved
0.6522	Remote Similarity	NPD6927	Phase 3
0.6517	Remote Similarity	NPD5786	Approved
0.6512	Remote Similarity	NPD5369	Approved
0.65	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4225	Approved
0.6353	Remote Similarity	NPD4268	Approved
0.6353	Remote Similarity	NPD4271	Approved
0.6353	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7521	Approved
0.6333	Remote Similarity	NPD4249	Approved
0.6333	Remote Similarity	NPD6684	Approved
0.6333	Remote Similarity	NPD5330	Approved
0.6333	Remote Similarity	NPD7334	Approved
0.6333	Remote Similarity	NPD7146	Approved
0.6333	Remote Similarity	NPD6409	Approved
0.6264	Remote Similarity	NPD4251	Approved
0.6264	Remote Similarity	NPD4250	Approved
0.625	Remote Similarity	NPD6435	Approved
0.6237	Remote Similarity	NPD7838	Discovery
0.6235	Remote Similarity	NPD4756	Discovery
0.6207	Remote Similarity	NPD4820	Approved
0.6207	Remote Similarity	NPD4821	Approved
0.6207	Remote Similarity	NPD4819	Approved
0.6207	Remote Similarity	NPD4822	Approved
0.6196	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6903	Approved
0.618	Remote Similarity	NPD5331	Approved
0.618	Remote Similarity	NPD5332	Approved
0.617	Remote Similarity	NPD7983	Approved
0.6154	Remote Similarity	NPD6371	Approved
0.6154	Remote Similarity	NPD6422	Discontinued
0.6136	Remote Similarity	NPD4790	Discontinued
0.6129	Remote Similarity	NPD5370	Suspended
0.6122	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6399	Phase 3
0.6105	Remote Similarity	NPD5779	Approved
0.6105	Remote Similarity	NPD5778	Approved
0.6095	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD28	Approved
0.6056	Remote Similarity	NPD29	Approved
0.6027	Remote Similarity	NPD9298	Approved
0.6023	Remote Similarity	NPD5368	Approved
0.6022	Remote Similarity	NPD5737	Approved
0.6022	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5693	Phase 1
0.5974	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6686	Approved
0.596	Remote Similarity	NPD7638	Approved
0.5957	Remote Similarity	NPD6101	Approved
0.5957	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD3197	Phase 1
0.5943	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD7839	Suspended
0.59	Remote Similarity	NPD7640	Approved
0.59	Remote Similarity	NPD7639	Approved
0.5895	Remote Similarity	NPD5207	Approved
0.589	Remote Similarity	NPD3172	Approved
0.5876	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD7900	Approved
0.5876	Remote Similarity	NPD5282	Discontinued
0.5857	Remote Similarity	NPD5343	Approved
0.5849	Remote Similarity	NPD2067	Discontinued
0.5833	Remote Similarity	NPD6411	Approved
0.5818	Remote Similarity	NPD7115	Discovery
0.5816	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD3194	Approved
0.5811	Remote Similarity	NPD3196	Approved
0.5811	Remote Similarity	NPD3195	Phase 2
0.5811	Remote Similarity	NPD4266	Approved
0.5802	Remote Similarity	NPD7331	Phase 2
0.5797	Remote Similarity	NPD3174	Discontinued
0.5789	Remote Similarity	NPD6051	Approved
0.5769	Remote Similarity	NPD6008	Approved
0.5758	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD3573	Approved
0.5741	Remote Similarity	NPD6053	Discontinued
0.5732	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7748	Approved
0.5714	Remote Similarity	NPD6001	Approved
0.5714	Remote Similarity	NPD3667	Approved
0.57	Remote Similarity	NPD7902	Approved
0.5684	Remote Similarity	NPD5208	Approved
0.567	Remote Similarity	NPD7637	Suspended
0.5657	Remote Similarity	NPD5695	Phase 3
0.5644	Remote Similarity	NPD5696	Approved
0.5638	Remote Similarity	NPD3618	Phase 1
0.5638	Remote Similarity	NPD6098	Approved
0.5632	Remote Similarity	NPD1452	Discontinued
0.5625	Remote Similarity	NPD6080	Approved
0.5625	Remote Similarity	NPD6904	Approved
0.5625	Remote Similarity	NPD6673	Approved
0.5625	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD2182	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