NPASS Compound

Structure

CID93763 OpenBabel06191715432D 24 25 0 0 1 0 0 0 0 0999 V2000 2.6847 -4.3085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9507 1.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3083 -2.5699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5496 -1.8088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5488 1.1913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5498 -2.8083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.6911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4155 -1.3085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5490 0.1918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8178 -2.8087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8175 -1.8092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8170 0.1913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6844 -3.3085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8168 1.1908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0004 -1.6189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -0.3080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9519 -1.3094 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9516 -0.3089 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2811 0.1922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5879 -0.8096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9392 -0.5607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6040 1.1386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5877 -0.8099 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 2 0 0 0 0 4 6 1 0 0 0 0 4 8 1 0 0 0 0 5 7 1 0 0 0 0 5 9 1 0 0 0 0 6 13 2 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 16 2 0 0 0 0 10 11 1 0 0 0 0 10 13 1 0 0 0 0 12 14 2 0 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 17 11 1 1 0 0 0 17 18 1 0 0 0 0 18 12 1 1 0 0 0 18 24 1 0 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.18
Volume:	356.705
LogP:	3.7
LogD:	2.595
LogS:	-3.714
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.445
Synthetic Accessibility Score:	4.762
Fsp3:	0.5
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:	-5.19
MDCK Permeability:	1.561042336106766e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.963
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	96.96680450439453%
Volume Distribution (VD):	0.212
Pgp-substrate:	1.2515223026275635%

ADMET: Metabolism

CYP1A2-inhibitor:	0.106
CYP1A2-substrate:	0.145
CYP2C19-inhibitor:	0.073
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.299
CYP2C9-substrate:	0.972
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.181
CYP3A4-inhibitor:	0.077
CYP3A4-substrate:	0.135

ADMET: Excretion

Clearance (CL):	2.572
Half-life (T1/2):	0.663

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.484
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.158
Maximum Recommended Daily Dose:	0.349
Skin Sensitization:	0.566
Carcinogencity:	0.13
Eye Corrosion:	0.014
Eye Irritation:	0.029
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC93763

Natural Product ID:	NPC93763
*Common Name:**	(7Z)-Lobohedleolide
IUPAC Name:	(3aS,6E,10Z,14E,15aS)-6,14-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,12,13,15a-octahydrocyclotetradeca[b]furan-10-carboxylic acid
Synonyms:	(7Z)-Lobohedleolide; Lobohedleolide
Standard InCHIKey:	SORYERHBQFTRIK-JMQTVVQQSA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-13-6-4-8-16(19(21)22)9-5-7-14(2)12-18-17(11-10-13)15(3)20(23)24-18/h6,9,12,17-18H,3-5,7-8,10-11H2,1-2H3,(H,21,22)/p-1/b13-6+,14-12+,16-9-/t17-,18-/m0/s1
SMILES:	C/C/1=CCC/C(=C/CC/C(=C/[C@H]2[C@@H](CC1)C(=C)C(=O)O2)/C)/C(=O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524633
PubChem CID:	6475568
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones [CHEMONTID:0002502] Cembranolides

*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
NPO2125	Lobophytum hedleyi	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)82073-6]
NPO29790	Lobophytum	Genus	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10785433]
NPO2125	Lobophytum hedleyi	Species	Alcyoniidae	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
EC50	1
IC50	1
Others	1

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	4.6	ug.mL-1	PMID[575708]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	7.6	ug.mL-1	PMID[575708]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Activity	=	55.0	%	PMID[575708]

☑ 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 NPC93763 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	154
0.1-0.2	1071
0.2-0.3	5066
0.3-0.4	13176
0.4-0.5	12018
0.5-0.6	6218
0.6-0.7	3650
0.7-0.8	1098
0.8-0.85	140
0.85-0.9	78
0.9-0.95	23
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC108816
0.9589	High Similarity	NPC320630
0.9589	High Similarity	NPC116177
0.9589	High Similarity	NPC7563
0.9459	High Similarity	NPC267231
0.9444	High Similarity	NPC476355
0.9351	High Similarity	NPC40746
0.9351	High Similarity	NPC169575
0.92	High Similarity	NPC471465
0.92	High Similarity	NPC196653
0.9189	High Similarity	NPC123360
0.9178	High Similarity	NPC140287
0.9167	High Similarity	NPC163003
0.9114	High Similarity	NPC470755
0.9103	High Similarity	NPC131669
0.9103	High Similarity	NPC473390
0.9091	High Similarity	NPC24417
0.9	High Similarity	NPC305475
0.9	High Similarity	NPC475461
0.8987	High Similarity	NPC476804
0.8987	High Similarity	NPC158756
0.8974	High Similarity	NPC229825
0.8889	High Similarity	NPC160138
0.8875	High Similarity	NPC255307
0.8875	High Similarity	NPC21469
0.8861	High Similarity	NPC250315
0.8861	High Similarity	NPC59097
0.8846	High Similarity	NPC325031
0.8831	High Similarity	NPC270126
0.8831	High Similarity	NPC98557
0.8831	High Similarity	NPC167881
0.8816	High Similarity	NPC171204
0.8816	High Similarity	NPC141789
0.8816	High Similarity	NPC97516
0.8816	High Similarity	NPC476028
0.8784	High Similarity	NPC58956
0.8784	High Similarity	NPC269206
0.8784	High Similarity	NPC295633
0.878	High Similarity	NPC476805
0.878	High Similarity	NPC475819
0.8767	High Similarity	NPC67183
0.8765	High Similarity	NPC469910
0.875	High Similarity	NPC114979
0.875	High Similarity	NPC191476
0.875	High Similarity	NPC141193
0.875	High Similarity	NPC96259
0.8718	High Similarity	NPC281132
0.8675	High Similarity	NPC295312
0.8642	High Similarity	NPC165162
0.8625	High Similarity	NPC116543
0.8611	High Similarity	NPC194871
0.8608	High Similarity	NPC52861
0.859	High Similarity	NPC178277
0.859	High Similarity	NPC470244
0.859	High Similarity	NPC470239
0.8571	High Similarity	NPC470240
0.8571	High Similarity	NPC41780
0.8571	High Similarity	NPC179394
0.8571	High Similarity	NPC475855
0.8571	High Similarity	NPC476794
0.8571	High Similarity	NPC187568
0.8571	High Similarity	NPC144133
0.8571	High Similarity	NPC57744
0.8554	High Similarity	NPC476803
0.8537	High Similarity	NPC150755
0.85	High Similarity	NPC173609
0.8493	Intermediate Similarity	NPC470256
0.8471	Intermediate Similarity	NPC473321
0.8462	Intermediate Similarity	NPC128276
0.8452	Intermediate Similarity	NPC268298
0.8452	Intermediate Similarity	NPC474032
0.8442	Intermediate Similarity	NPC68819
0.8442	Intermediate Similarity	NPC235906
0.8434	Intermediate Similarity	NPC72513
0.8421	Intermediate Similarity	NPC114727
0.8421	Intermediate Similarity	NPC476590
0.8415	Intermediate Similarity	NPC215364
0.8375	Intermediate Similarity	NPC281949
0.8375	Intermediate Similarity	NPC25684
0.8375	Intermediate Similarity	NPC141810
0.8375	Intermediate Similarity	NPC471325
0.8375	Intermediate Similarity	NPC301477
0.8372	Intermediate Similarity	NPC125674
0.8372	Intermediate Similarity	NPC288240
0.8372	Intermediate Similarity	NPC295204
0.8372	Intermediate Similarity	NPC469645
0.8372	Intermediate Similarity	NPC273579
0.8372	Intermediate Similarity	NPC469692
0.8372	Intermediate Similarity	NPC475838
0.8372	Intermediate Similarity	NPC228451
0.8372	Intermediate Similarity	NPC162205
0.8354	Intermediate Similarity	NPC89128
0.8353	Intermediate Similarity	NPC474232
0.8353	Intermediate Similarity	NPC129419
0.8353	Intermediate Similarity	NPC469368
0.8353	Intermediate Similarity	NPC473619
0.8333	Intermediate Similarity	NPC65603
0.8333	Intermediate Similarity	NPC473715
0.8313	Intermediate Similarity	NPC469483
0.8313	Intermediate Similarity	NPC284902
0.8313	Intermediate Similarity	NPC261721
0.8312	Intermediate Similarity	NPC193351
0.8312	Intermediate Similarity	NPC329852
0.8312	Intermediate Similarity	NPC226669
0.8312	Intermediate Similarity	NPC155587
0.8312	Intermediate Similarity	NPC138408
0.8293	Intermediate Similarity	NPC472957
0.8293	Intermediate Similarity	NPC472958
0.8276	Intermediate Similarity	NPC474247
0.8276	Intermediate Similarity	NPC474338
0.8276	Intermediate Similarity	NPC121825
0.8272	Intermediate Similarity	NPC89555
0.8272	Intermediate Similarity	NPC85772
0.8256	Intermediate Similarity	NPC300312
0.8256	Intermediate Similarity	NPC261607
0.8256	Intermediate Similarity	NPC111114
0.8235	Intermediate Similarity	NPC218927
0.8235	Intermediate Similarity	NPC206001
0.8193	Intermediate Similarity	NPC125290
0.8193	Intermediate Similarity	NPC261380
0.8182	Intermediate Similarity	NPC15499
0.8182	Intermediate Similarity	NPC259599
0.8182	Intermediate Similarity	NPC471142
0.8182	Intermediate Similarity	NPC117746
0.8182	Intermediate Similarity	NPC48641
0.8182	Intermediate Similarity	NPC477922
0.8182	Intermediate Similarity	NPC304886
0.8182	Intermediate Similarity	NPC294434
0.8171	Intermediate Similarity	NPC318468
0.8171	Intermediate Similarity	NPC475947
0.8161	Intermediate Similarity	NPC475912
0.8158	Intermediate Similarity	NPC129665
0.8148	Intermediate Similarity	NPC42470
0.814	Intermediate Similarity	NPC476004
0.814	Intermediate Similarity	NPC51004
0.814	Intermediate Similarity	NPC106510
0.814	Intermediate Similarity	NPC474761
0.814	Intermediate Similarity	NPC71533
0.8133	Intermediate Similarity	NPC88877
0.8133	Intermediate Similarity	NPC476591
0.8125	Intermediate Similarity	NPC617
0.8125	Intermediate Similarity	NPC19841
0.8125	Intermediate Similarity	NPC264227
0.8125	Intermediate Similarity	NPC63649
0.8125	Intermediate Similarity	NPC472965
0.8118	Intermediate Similarity	NPC136879
0.8118	Intermediate Similarity	NPC477302
0.8118	Intermediate Similarity	NPC202672
0.8095	Intermediate Similarity	NPC107787
0.8095	Intermediate Similarity	NPC122502
0.809	Intermediate Similarity	NPC477921
0.809	Intermediate Similarity	NPC230800
0.809	Intermediate Similarity	NPC279621
0.8072	Intermediate Similarity	NPC115786
0.8072	Intermediate Similarity	NPC82297
0.8072	Intermediate Similarity	NPC70424
0.8072	Intermediate Similarity	NPC243618
0.8072	Intermediate Similarity	NPC295799
0.8068	Intermediate Similarity	NPC81386
0.8068	Intermediate Similarity	NPC474035
0.8068	Intermediate Similarity	NPC477131
0.8068	Intermediate Similarity	NPC167219
0.8049	Intermediate Similarity	NPC474291
0.8049	Intermediate Similarity	NPC474252
0.8046	Intermediate Similarity	NPC30515
0.8026	Intermediate Similarity	NPC4299
0.8025	Intermediate Similarity	NPC223904
0.8025	Intermediate Similarity	NPC302426
0.8023	Intermediate Similarity	NPC212598
0.8023	Intermediate Similarity	NPC307411
0.8	Intermediate Similarity	NPC312561
0.8	Intermediate Similarity	NPC237540
0.8	Intermediate Similarity	NPC475703
0.8	Intermediate Similarity	NPC474343
0.8	Intermediate Similarity	NPC471462
0.8	Intermediate Similarity	NPC472960
0.8	Intermediate Similarity	NPC218477
0.8	Intermediate Similarity	NPC192006
0.7978	Intermediate Similarity	NPC36954
0.7978	Intermediate Similarity	NPC471141
0.7978	Intermediate Similarity	NPC270013
0.7978	Intermediate Similarity	NPC14961
0.7978	Intermediate Similarity	NPC150041
0.7976	Intermediate Similarity	NPC110710
0.7976	Intermediate Similarity	NPC231009
0.7976	Intermediate Similarity	NPC223871
0.7976	Intermediate Similarity	NPC82795
0.7976	Intermediate Similarity	NPC473478
0.7976	Intermediate Similarity	NPC107986
0.7976	Intermediate Similarity	NPC1083
0.7976	Intermediate Similarity	NPC473651
0.7976	Intermediate Similarity	NPC473669
0.7976	Intermediate Similarity	NPC103284
0.7976	Intermediate Similarity	NPC66346
0.7976	Intermediate Similarity	NPC78089
0.7976	Intermediate Similarity	NPC132496
0.7976	Intermediate Similarity	NPC286338
0.7976	Intermediate Similarity	NPC283085
0.7973	Intermediate Similarity	NPC248125
0.7955	Intermediate Similarity	NPC476300

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 NPC93763 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	137
0.1-0.2	1591
0.2-0.3	3781
0.3-0.4	2473
0.4-0.5	744
0.5-0.6	326
0.6-0.7	73
0.7-0.8	23
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7931	Intermediate Similarity	NPD5785	Approved
0.7765	Intermediate Similarity	NPD5363	Approved
0.7738	Intermediate Similarity	NPD7154	Phase 3
0.7582	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5362	Discontinued
0.7528	Intermediate Similarity	NPD46	Approved
0.7528	Intermediate Similarity	NPD6698	Approved
0.7412	Intermediate Similarity	NPD4269	Approved
0.7412	Intermediate Similarity	NPD4270	Approved
0.7412	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4252	Approved
0.7356	Intermediate Similarity	NPD1694	Approved
0.7356	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4225	Approved
0.7273	Intermediate Similarity	NPD5786	Approved
0.7229	Intermediate Similarity	NPD4756	Discovery
0.7209	Intermediate Similarity	NPD5209	Approved
0.7172	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4271	Approved
0.7143	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4268	Approved
0.7143	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5369	Approved
0.7079	Intermediate Similarity	NPD4249	Approved
0.7033	Intermediate Similarity	NPD1695	Approved
0.7	Intermediate Similarity	NPD4250	Approved
0.7	Intermediate Similarity	NPD4251	Approved
0.6979	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4819	Approved
0.6977	Remote Similarity	NPD4822	Approved
0.6977	Remote Similarity	NPD4821	Approved
0.6977	Remote Similarity	NPD4820	Approved
0.6961	Remote Similarity	NPD6371	Approved
0.6957	Remote Similarity	NPD7838	Discovery
0.6932	Remote Similarity	NPD5332	Approved
0.6932	Remote Similarity	NPD5331	Approved
0.6897	Remote Similarity	NPD4790	Discontinued
0.6882	Remote Similarity	NPD7983	Approved
0.6854	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5370	Suspended
0.6818	Remote Similarity	NPD6435	Approved
0.6809	Remote Similarity	NPD5779	Approved
0.6809	Remote Similarity	NPD5778	Approved
0.6786	Remote Similarity	NPD8039	Approved
0.6735	Remote Similarity	NPD7640	Approved
0.6735	Remote Similarity	NPD7639	Approved
0.6702	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7638	Approved
0.6632	Remote Similarity	NPD6399	Phase 3
0.6623	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6686	Approved
0.6598	Remote Similarity	NPD7839	Suspended
0.6591	Remote Similarity	NPD5368	Approved
0.6574	Remote Similarity	NPD7115	Discovery
0.6571	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5282	Discontinued
0.6543	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6422	Discontinued
0.6489	Remote Similarity	NPD6101	Approved
0.6489	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7331	Phase 2
0.6392	Remote Similarity	NPD7748	Approved
0.6375	Remote Similarity	NPD3197	Phase 1
0.6374	Remote Similarity	NPD6110	Phase 1
0.6373	Remote Similarity	NPD6647	Phase 2
0.6364	Remote Similarity	NPD7902	Approved
0.6355	Remote Similarity	NPD6053	Discontinued
0.6354	Remote Similarity	NPD7637	Suspended
0.6354	Remote Similarity	NPD6411	Approved
0.6351	Remote Similarity	NPD3172	Approved
0.6344	Remote Similarity	NPD7334	Approved
0.6344	Remote Similarity	NPD7146	Approved
0.6344	Remote Similarity	NPD5330	Approved
0.6344	Remote Similarity	NPD6684	Approved
0.6344	Remote Similarity	NPD6409	Approved
0.6344	Remote Similarity	NPD7521	Approved
0.6337	Remote Similarity	NPD5344	Discontinued
0.6327	Remote Similarity	NPD5695	Phase 3
0.6301	Remote Similarity	NPD6927	Phase 3
0.63	Remote Similarity	NPD5696	Approved
0.6267	Remote Similarity	NPD3195	Phase 2
0.6267	Remote Similarity	NPD3194	Approved
0.6267	Remote Similarity	NPD3196	Approved
0.6267	Remote Similarity	NPD4266	Approved
0.6238	Remote Similarity	NPD6648	Approved
0.6222	Remote Similarity	NPD4695	Discontinued
0.622	Remote Similarity	NPD3704	Approved
0.6211	Remote Similarity	NPD5737	Approved
0.6211	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6672	Approved
0.6211	Remote Similarity	NPD6903	Approved
0.62	Remote Similarity	NPD6083	Phase 2
0.62	Remote Similarity	NPD6084	Phase 2
0.6186	Remote Similarity	NPD7515	Phase 2
0.6186	Remote Similarity	NPD5693	Phase 1
0.617	Remote Similarity	NPD3618	Phase 1
0.6129	Remote Similarity	NPD3665	Phase 1
0.6129	Remote Similarity	NPD3133	Approved
0.6129	Remote Similarity	NPD3666	Approved
0.6117	Remote Similarity	NPD7632	Discontinued
0.6111	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD7341	Phase 2
0.6087	Remote Similarity	NPD3667	Approved
0.6061	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7900	Approved
0.6053	Remote Similarity	NPD8515	Approved
0.6053	Remote Similarity	NPD8513	Phase 3
0.6053	Remote Similarity	NPD8517	Approved
0.6053	Remote Similarity	NPD8516	Approved
0.6038	Remote Similarity	NPD5697	Approved
0.6027	Remote Similarity	NPD3173	Approved
0.6024	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5281	Approved
0.602	Remote Similarity	NPD5284	Approved
0.6019	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD2067	Discontinued
0.6	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4519	Discontinued
0.6	Remote Similarity	NPD4623	Approved
0.6	Remote Similarity	NPD5279	Phase 3
0.5981	Remote Similarity	NPD6011	Approved
0.5981	Remote Similarity	NPD6881	Approved
0.5981	Remote Similarity	NPD6899	Approved
0.5974	Remote Similarity	NPD342	Phase 1
0.5963	Remote Similarity	NPD6650	Approved
0.5963	Remote Similarity	NPD6649	Approved
0.596	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD4786	Approved
0.5943	Remote Similarity	NPD6008	Approved
0.5943	Remote Similarity	NPD6675	Approved
0.5943	Remote Similarity	NPD5739	Approved
0.5943	Remote Similarity	NPD7128	Approved
0.5943	Remote Similarity	NPD6402	Approved
0.5926	Remote Similarity	NPD6014	Approved
0.5926	Remote Similarity	NPD6373	Approved
0.5926	Remote Similarity	NPD6372	Approved
0.5926	Remote Similarity	NPD6013	Approved
0.5926	Remote Similarity	NPD6012	Approved
0.5926	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD368	Approved
0.5918	Remote Similarity	NPD5207	Approved
0.5914	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD2259	Approved
0.5905	Remote Similarity	NPD2258	Approved
0.5895	Remote Similarity	NPD1696	Phase 3
0.5888	Remote Similarity	NPD5701	Approved
0.5872	Remote Similarity	NPD7290	Approved
0.5872	Remote Similarity	NPD6883	Approved
0.5872	Remote Similarity	NPD7102	Approved
0.587	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD28	Approved
0.5867	Remote Similarity	NPD29	Approved
0.5859	Remote Similarity	NPD6079	Approved
0.5859	Remote Similarity	NPD8034	Phase 2
0.5859	Remote Similarity	NPD8035	Phase 2
0.5849	Remote Similarity	NPD5909	Discontinued
0.5842	Remote Similarity	NPD4629	Approved
0.5842	Remote Similarity	NPD5210	Approved
0.5841	Remote Similarity	NPD7500	Approved
0.5833	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7320	Approved
0.5818	Remote Similarity	NPD2204	Approved
0.5818	Remote Similarity	NPD6847	Approved
0.5818	Remote Similarity	NPD6617	Approved
0.5818	Remote Similarity	NPD6869	Approved
0.5818	Remote Similarity	NPD8130	Phase 1
0.5816	Remote Similarity	NPD6673	Approved
0.5816	Remote Similarity	NPD6080	Approved
0.5816	Remote Similarity	NPD6051	Approved
0.5816	Remote Similarity	NPD4753	Phase 2
0.5816	Remote Similarity	NPD6904	Approved
0.5816	Remote Similarity	NPD5328	Approved
0.5816	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5211	Phase 2
0.5798	Remote Similarity	NPD8074	Phase 3
0.5789	Remote Similarity	NPD3668	Phase 3
0.5789	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD4228	Discovery
0.5784	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD5222	Approved
0.5784	Remote Similarity	NPD4697	Phase 3
0.5784	Remote Similarity	NPD5221	Approved
0.5783	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.578	Remote Similarity	NPD6413	Approved
0.578	Remote Similarity	NPD2182	Approved
0.5773	Remote Similarity	NPD3573	Approved
0.5769	Remote Similarity	NPD6404	Discontinued
0.5766	Remote Similarity	NPD8297	Approved
0.5766	Remote Similarity	NPD6882	Approved
0.5758	Remote Similarity	NPD5692	Phase 3
0.575	Remote Similarity	NPD6109	Phase 1
0.5745	Remote Similarity	NPD4223	Phase 3
0.5745	Remote Similarity	NPD4221	Approved
0.5743	Remote Similarity	NPD6001	Approved
0.5741	Remote Similarity	NPD5954	Clinical (unspecified phase)

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