NPASS Compound

Structure

NPC176329 OpenBabel07101719152D 24 24 0 0 1 0 0 0 0 0999 V2000 12.5662 -7.6050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9730 -6.6915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3852 -5.8825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3906 -5.9870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8029 -5.1780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8083 -5.2825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2206 -4.4735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2260 -4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6382 -3.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6437 -3.8735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0559 -3.0645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0614 -3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4736 -2.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4791 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8913 -1.6555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8968 -1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5691 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -1.7601 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 3 1 0 0 0 0 2 18 2 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 19 2 0 0 0 0 18 20 1 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 1 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.27
Volume:	381.677
LogP:	6.899
LogD:	4.114
LogS:	-4.877
# Rotatable Bonds:	14
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.247
Synthetic Accessibility Score:	3.309
Fsp3:	0.762
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.037
MDCK Permeability:	2.187969039368909e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.697
Plasma Protein Binding (PPB):	98.09117889404297%
Volume Distribution (VD):	0.978
Pgp-substrate:	1.3196430206298828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.237
CYP1A2-substrate:	0.163
CYP2C19-inhibitor:	0.486
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.197
CYP2C9-substrate:	0.884
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.333
CYP3A4-substrate:	0.085

ADMET: Excretion

Clearance (CL):	4.851
Half-life (T1/2):	0.104

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.261
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.243
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.982
Carcinogencity:	0.53
Eye Corrosion:	0.987
Eye Irritation:	0.963
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC176329

Natural Product ID:	NPC176329
*Common Name:**	Isolinderanolide
IUPAC Name:	(3E,4S)-3-hexadecylidene-4-hydroxy-5-methylideneoxolan-2-one
Synonyms:	Isolinderanolide
Standard InCHIKey:	HFEZVKMFKXUREP-LFNFIXQYSA-N
Standard InCHI:	InChI=1S/C21H36O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19-20(22)18(2)24-21(19)23/h17,20,22H,2-16H2,1H3/b19-17+/t20-/m1/s1
SMILES:	CCCCCCCCCCCCCCC/C=C/1[C@@H](C(=C)OC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450686
PubChem CID:	44576045
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001967] Oxolanes

*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
NPO5141	Lindera benzoin	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1602301]
NPO5141	Lindera benzoin	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5141	Lindera benzoin	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
ED50	3
Others	6

Activity Type	# Activity
Cell Line	3
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	4.57	ug ml-1	PMID[549478]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	3.12	ug ml-1	PMID[549478]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	3.07	ug ml-1	PMID[549478]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	0.96	ppm	PMID[549478]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	44.9	%	PMID[549478]
NPT3061	Organism	Diabrotica undecimpunctata	Diabrotica undecimpunctata	Activity	=	20.0	%	PMID[549478]
NPT3062	Organism	Spodoptera eridania	Spodoptera eridania	Activity	=	0.0	%	PMID[549478]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	Activity	=	0.0	%	PMID[549478]
NPT3063	Organism	Aphis gossypii	Aphis gossypii	Activity	=	0.0	%	PMID[549478]

☑ 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 NPC176329 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	1575
0.2-0.3	6902
0.3-0.4	16902
0.4-0.5	10247
0.5-0.6	5016
0.6-0.7	1469
0.7-0.8	404
0.8-0.85	7
0.85-0.9	8
0.9-0.95	1
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC49302
1.0	High Similarity	NPC125365
1.0	High Similarity	NPC474818
1.0	High Similarity	NPC51809
0.9861	High Similarity	NPC279214
0.9861	High Similarity	NPC473471
0.9861	High Similarity	NPC221095
0.9859	High Similarity	NPC301207
0.9583	High Similarity	NPC127118
0.9583	High Similarity	NPC209113
0.8974	High Similarity	NPC229799
0.8974	High Similarity	NPC286770
0.8974	High Similarity	NPC284472
0.8961	High Similarity	NPC150502
0.8846	High Similarity	NPC11383
0.8846	High Similarity	NPC310450
0.8846	High Similarity	NPC475046
0.8846	High Similarity	NPC474959
0.8182	Intermediate Similarity	NPC161038
0.8118	Intermediate Similarity	NPC79027
0.8077	Intermediate Similarity	NPC256640
0.8077	Intermediate Similarity	NPC16279
0.8077	Intermediate Similarity	NPC205615
0.8	Intermediate Similarity	NPC99651
0.7975	Intermediate Similarity	NPC275530
0.7907	Intermediate Similarity	NPC14901
0.7907	Intermediate Similarity	NPC130359
0.7882	Intermediate Similarity	NPC178215
0.7875	Intermediate Similarity	NPC279532
0.7857	Intermediate Similarity	NPC132496
0.7857	Intermediate Similarity	NPC107986
0.7857	Intermediate Similarity	NPC82795
0.7857	Intermediate Similarity	NPC283085
0.7857	Intermediate Similarity	NPC473478
0.7857	Intermediate Similarity	NPC473669
0.7857	Intermediate Similarity	NPC103284
0.7857	Intermediate Similarity	NPC1083
0.7857	Intermediate Similarity	NPC66346
0.7857	Intermediate Similarity	NPC110710
0.7857	Intermediate Similarity	NPC231009
0.7857	Intermediate Similarity	NPC223871
0.7857	Intermediate Similarity	NPC473651
0.7857	Intermediate Similarity	NPC286338
0.7848	Intermediate Similarity	NPC203277
0.7848	Intermediate Similarity	NPC470705
0.7841	Intermediate Similarity	NPC469692
0.7841	Intermediate Similarity	NPC469645
0.7831	Intermediate Similarity	NPC161045
0.7791	Intermediate Similarity	NPC20339
0.7791	Intermediate Similarity	NPC48338
0.7791	Intermediate Similarity	NPC233551
0.7791	Intermediate Similarity	NPC21208
0.7791	Intermediate Similarity	NPC280621
0.7791	Intermediate Similarity	NPC40376
0.7765	Intermediate Similarity	NPC62118
0.7765	Intermediate Similarity	NPC134865
0.7765	Intermediate Similarity	NPC232555
0.7765	Intermediate Similarity	NPC231096
0.7765	Intermediate Similarity	NPC469910
0.7765	Intermediate Similarity	NPC112685
0.7765	Intermediate Similarity	NPC134807
0.7765	Intermediate Similarity	NPC134885
0.7765	Intermediate Similarity	NPC219498
0.7765	Intermediate Similarity	NPC171174
0.7765	Intermediate Similarity	NPC107717
0.7765	Intermediate Similarity	NPC240695
0.7765	Intermediate Similarity	NPC142117
0.7765	Intermediate Similarity	NPC279267
0.7765	Intermediate Similarity	NPC103523
0.7765	Intermediate Similarity	NPC69082
0.7765	Intermediate Similarity	NPC308412
0.7765	Intermediate Similarity	NPC210218
0.7765	Intermediate Similarity	NPC204686
0.7765	Intermediate Similarity	NPC114694
0.7765	Intermediate Similarity	NPC473687
0.7765	Intermediate Similarity	NPC475581
0.7763	Intermediate Similarity	NPC475982
0.7753	Intermediate Similarity	NPC121825
0.7738	Intermediate Similarity	NPC163093
0.7722	Intermediate Similarity	NPC478192
0.7722	Intermediate Similarity	NPC260396
0.7722	Intermediate Similarity	NPC478195
0.7722	Intermediate Similarity	NPC478194
0.7722	Intermediate Similarity	NPC478193
0.7722	Intermediate Similarity	NPC478191
0.7722	Intermediate Similarity	NPC478196
0.7711	Intermediate Similarity	NPC94875
0.7711	Intermediate Similarity	NPC11332
0.7711	Intermediate Similarity	NPC73310
0.7711	Intermediate Similarity	NPC180363
0.7711	Intermediate Similarity	NPC473712
0.7711	Intermediate Similarity	NPC131002
0.7711	Intermediate Similarity	NPC473780
0.7711	Intermediate Similarity	NPC473529
0.7711	Intermediate Similarity	NPC475159
0.7711	Intermediate Similarity	NPC145914
0.7711	Intermediate Similarity	NPC329829
0.7711	Intermediate Similarity	NPC65930
0.7703	Intermediate Similarity	NPC282760
0.7701	Intermediate Similarity	NPC139418
0.7683	Intermediate Similarity	NPC47653
0.7662	Intermediate Similarity	NPC202011
0.7647	Intermediate Similarity	NPC471567
0.7647	Intermediate Similarity	NPC182383
0.7647	Intermediate Similarity	NPC477014
0.7647	Intermediate Similarity	NPC477013
0.7647	Intermediate Similarity	NPC470755
0.7647	Intermediate Similarity	NPC11804
0.7647	Intermediate Similarity	NPC120398
0.7625	Intermediate Similarity	NPC68819
0.7619	Intermediate Similarity	NPC144415
0.7619	Intermediate Similarity	NPC253801
0.7614	Intermediate Similarity	NPC239517
0.7614	Intermediate Similarity	NPC474232
0.7614	Intermediate Similarity	NPC473904
0.7595	Intermediate Similarity	NPC114727
0.7595	Intermediate Similarity	NPC315843
0.7595	Intermediate Similarity	NPC107654
0.7595	Intermediate Similarity	NPC476590
0.759	Intermediate Similarity	NPC297440
0.7586	Intermediate Similarity	NPC81045
0.7586	Intermediate Similarity	NPC476803
0.7586	Intermediate Similarity	NPC172821
0.7586	Intermediate Similarity	NPC242364
0.7586	Intermediate Similarity	NPC320569
0.7586	Intermediate Similarity	NPC274446
0.7586	Intermediate Similarity	NPC169511
0.7586	Intermediate Similarity	NPC287164
0.7586	Intermediate Similarity	NPC191929
0.7586	Intermediate Similarity	NPC151403
0.7586	Intermediate Similarity	NPC171135
0.7586	Intermediate Similarity	NPC133730
0.7586	Intermediate Similarity	NPC39754
0.7586	Intermediate Similarity	NPC100454
0.7586	Intermediate Similarity	NPC234077
0.7586	Intermediate Similarity	NPC61257
0.7586	Intermediate Similarity	NPC261952
0.7586	Intermediate Similarity	NPC287089
0.7564	Intermediate Similarity	NPC293114
0.7558	Intermediate Similarity	NPC469483
0.7558	Intermediate Similarity	NPC47937
0.7558	Intermediate Similarity	NPC477015
0.7531	Intermediate Similarity	NPC7563
0.7531	Intermediate Similarity	NPC116177
0.7531	Intermediate Similarity	NPC320630
0.7529	Intermediate Similarity	NPC158756
0.7529	Intermediate Similarity	NPC156804
0.7529	Intermediate Similarity	NPC41856
0.75	Intermediate Similarity	NPC91067
0.75	Intermediate Similarity	NPC318963
0.75	Intermediate Similarity	NPC473504
0.75	Intermediate Similarity	NPC280612
0.75	Intermediate Similarity	NPC20621
0.75	Intermediate Similarity	NPC329826
0.75	Intermediate Similarity	NPC40066
0.75	Intermediate Similarity	NPC469414
0.75	Intermediate Similarity	NPC81778
0.75	Intermediate Similarity	NPC477011
0.75	Intermediate Similarity	NPC42598
0.75	Intermediate Similarity	NPC93794
0.747	Intermediate Similarity	NPC162741
0.747	Intermediate Similarity	NPC91332
0.7468	Intermediate Similarity	NPC470435
0.7468	Intermediate Similarity	NPC284006
0.7468	Intermediate Similarity	NPC144419
0.7467	Intermediate Similarity	NPC273600
0.7467	Intermediate Similarity	NPC470123
0.7467	Intermediate Similarity	NPC19769
0.7444	Intermediate Similarity	NPC162205
0.7444	Intermediate Similarity	NPC295204
0.7444	Intermediate Similarity	NPC11456
0.7444	Intermediate Similarity	NPC288240
0.7444	Intermediate Similarity	NPC273579
0.7442	Intermediate Similarity	NPC9678
0.7442	Intermediate Similarity	NPC473671
0.7442	Intermediate Similarity	NPC475268
0.7442	Intermediate Similarity	NPC100921
0.7442	Intermediate Similarity	NPC473156
0.7442	Intermediate Similarity	NPC202055
0.7442	Intermediate Similarity	NPC39279
0.7442	Intermediate Similarity	NPC329838
0.7442	Intermediate Similarity	NPC322529
0.7442	Intermediate Similarity	NPC470400
0.7442	Intermediate Similarity	NPC235809
0.7442	Intermediate Similarity	NPC292809
0.7442	Intermediate Similarity	NPC319036
0.7442	Intermediate Similarity	NPC25764
0.7442	Intermediate Similarity	NPC329615
0.7442	Intermediate Similarity	NPC77871
0.7442	Intermediate Similarity	NPC21469
0.7442	Intermediate Similarity	NPC39167
0.7442	Intermediate Similarity	NPC477018
0.7439	Intermediate Similarity	NPC108816
0.7439	Intermediate Similarity	NPC248775
0.7439	Intermediate Similarity	NPC182292
0.7439	Intermediate Similarity	NPC318481
0.7439	Intermediate Similarity	NPC93763
0.7419	Intermediate Similarity	NPC124512
0.7419	Intermediate Similarity	NPC159763
0.7419	Intermediate Similarity	NPC278386

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 NPC176329 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	2238
0.2-0.3	4295
0.3-0.4	1810
0.4-0.5	536
0.5-0.6	93
0.6-0.7	36
0.7-0.8	1
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
0.7419	Intermediate Similarity	NPD4225	Approved
0.6848	Remote Similarity	NPD6698	Approved
0.6848	Remote Similarity	NPD5785	Approved
0.6848	Remote Similarity	NPD46	Approved
0.6848	Remote Similarity	NPD7838	Discovery
0.6742	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6371	Approved
0.6667	Remote Similarity	NPD5363	Approved
0.6629	Remote Similarity	NPD7154	Phase 3
0.662	Remote Similarity	NPD6927	Phase 3
0.6596	Remote Similarity	NPD7983	Approved
0.6562	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4252	Approved
0.6447	Remote Similarity	NPD6109	Phase 1
0.6375	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD4251	Approved
0.6344	Remote Similarity	NPD4250	Approved
0.6333	Remote Similarity	NPD5209	Approved
0.6333	Remote Similarity	NPD4269	Approved
0.6333	Remote Similarity	NPD4270	Approved
0.633	Remote Similarity	NPD7115	Discovery
0.6322	Remote Similarity	NPD4756	Discovery
0.6304	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3197	Phase 1
0.625	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD4268	Approved
0.625	Remote Similarity	NPD4271	Approved
0.6238	Remote Similarity	NPD5344	Discontinued
0.6237	Remote Similarity	NPD4249	Approved
0.6237	Remote Similarity	NPD5786	Approved
0.6234	Remote Similarity	NPD69	Approved
0.6234	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD9119	Approved
0.6111	Remote Similarity	NPD4820	Approved
0.6111	Remote Similarity	NPD4822	Approved
0.6111	Remote Similarity	NPD4819	Approved
0.6111	Remote Similarity	NPD4821	Approved
0.6104	Remote Similarity	NPD9118	Approved
0.6087	Remote Similarity	NPD6110	Phase 1
0.6087	Remote Similarity	NPD5362	Discontinued
0.6044	Remote Similarity	NPD5369	Approved
0.6042	Remote Similarity	NPD5370	Suspended
0.6038	Remote Similarity	NPD6686	Approved
0.6024	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5779	Approved
0.602	Remote Similarity	NPD5778	Approved
0.6019	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5332	Approved
0.5914	Remote Similarity	NPD5331	Approved
0.5889	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4790	Discontinued
0.5842	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD7839	Suspended
0.5826	Remote Similarity	NPD8517	Approved
0.5826	Remote Similarity	NPD8515	Approved
0.5826	Remote Similarity	NPD8513	Phase 3
0.5826	Remote Similarity	NPD8516	Approved
0.5825	Remote Similarity	NPD6648	Approved
0.5825	Remote Similarity	NPD7640	Approved
0.5825	Remote Similarity	NPD7639	Approved
0.5789	Remote Similarity	NPD1694	Approved
0.5728	Remote Similarity	NPD7638	Approved
0.5714	Remote Similarity	NPD1695	Approved
0.5714	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6101	Approved
0.5694	Remote Similarity	NPD4265	Approved
0.5694	Remote Similarity	NPD39	Approved
0.5676	Remote Similarity	NPD4220	Pre-registration
0.5663	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD5282	Discontinued
0.5638	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD6435	Approved
0.56	Remote Similarity	NPD6411	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