NPASS Compound

Structure

NPC473471 OpenBabel07101719512D 24 24 0 0 1 0 0 0 0 0999 V2000 8.3624 10.6593 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 7.3679 10.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7801 9.9548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1869 9.0412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5991 8.2322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0058 7.3187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4180 6.5096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8248 5.5961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2370 4.7871 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 2 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 6 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.25
Volume:	379.041
LogP:	5.414
LogD:	4.065
LogS:	-3.342
# Rotatable Bonds:	13
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.206
Synthetic Accessibility Score:	3.549
Fsp3:	0.667
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:	-4.965
MDCK Permeability:	3.641631337814033e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.124
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.838
Plasma Protein Binding (PPB):	97.92937469482422%
Volume Distribution (VD):	1.061
Pgp-substrate:	1.3056774139404297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.31
CYP1A2-substrate:	0.176
CYP2C19-inhibitor:	0.515
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.336
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.058
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.54
CYP3A4-substrate:	0.116

ADMET: Excretion

Clearance (CL):	5.224
Half-life (T1/2):	0.71

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.064
Drug-inuced Liver Injury (DILI):	0.149
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.179
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.982
Carcinogencity:	0.728
Eye Corrosion:	0.974
Eye Irritation:	0.983
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC473471

Natural Product ID:	NPC473471
*Common Name:**	Isolinderenolide
IUPAC Name:	(3E,4S)-3-[(Z)-hexadec-6-enylidene]-4-hydroxy-5-methylideneoxolan-2-one
Synonyms:	Isolinderenolide
Standard InCHIKey:	YUKXHIIQDGIKHT-CTRYHVSLSA-N
Standard InCHI:	InChI=1S/C21H34O3/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/h11-12,17,20,22H,2-10,13-16H2,1H3/b12-11-,19-17+/t20-/m1/s1
SMILES:	CCCCCCCCCC=CCCCCC=C1C(C(=C)OC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL442676
PubChem CID:	44576046
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	=	3.01	ug ml-1	PMID[484355]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	2.58	ug ml-1	PMID[484355]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	1.9	ug ml-1	PMID[484355]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	0.52	ppm	PMID[484355]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	41.4	%	PMID[484355]
NPT3061	Organism	Diabrotica undecimpunctata	Diabrotica undecimpunctata	Activity	=	0.0	%	PMID[484355]
NPT3062	Organism	Spodoptera eridania	Spodoptera eridania	Activity	=	0.0	%	PMID[484355]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	Activity	=	0.0	%	PMID[484355]
NPT3063	Organism	Aphis gossypii	Aphis gossypii	Activity	=	0.0	%	PMID[484355]

☑ 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 NPC473471 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	1424
0.2-0.3	6812
0.3-0.4	16745
0.4-0.5	10601
0.5-0.6	5048
0.6-0.7	1486
0.7-0.8	399
0.8-0.85	6
0.85-0.9	10
0.9-0.95	0
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9861	High Similarity	NPC125365
0.9861	High Similarity	NPC176329
0.9861	High Similarity	NPC474818
0.9861	High Similarity	NPC51809
0.9861	High Similarity	NPC49302
0.9726	High Similarity	NPC221095
0.9726	High Similarity	NPC279214
0.9722	High Similarity	NPC127118
0.9722	High Similarity	NPC209113
0.9722	High Similarity	NPC301207
0.8861	High Similarity	NPC284472
0.8861	High Similarity	NPC286770
0.8861	High Similarity	NPC229799
0.8846	High Similarity	NPC150502
0.8734	High Similarity	NPC310450
0.8734	High Similarity	NPC474959
0.8734	High Similarity	NPC475046
0.8734	High Similarity	NPC11383
0.8312	Intermediate Similarity	NPC161038
0.8125	Intermediate Similarity	NPC99651
0.8101	Intermediate Similarity	NPC275530
0.8023	Intermediate Similarity	NPC79027
0.8	Intermediate Similarity	NPC279532
0.7975	Intermediate Similarity	NPC205615
0.7975	Intermediate Similarity	NPC16279
0.7975	Intermediate Similarity	NPC203277
0.7975	Intermediate Similarity	NPC256640
0.7952	Intermediate Similarity	NPC161045
0.7895	Intermediate Similarity	NPC475982
0.7882	Intermediate Similarity	NPC69082
0.7882	Intermediate Similarity	NPC279267
0.7848	Intermediate Similarity	NPC260396
0.7816	Intermediate Similarity	NPC14901
0.7816	Intermediate Similarity	NPC130359
0.7791	Intermediate Similarity	NPC178215
0.7765	Intermediate Similarity	NPC110710
0.7765	Intermediate Similarity	NPC286338
0.7765	Intermediate Similarity	NPC231009
0.7765	Intermediate Similarity	NPC132496
0.7765	Intermediate Similarity	NPC103284
0.7765	Intermediate Similarity	NPC1083
0.7765	Intermediate Similarity	NPC473651
0.7765	Intermediate Similarity	NPC11804
0.7765	Intermediate Similarity	NPC82795
0.7765	Intermediate Similarity	NPC473669
0.7765	Intermediate Similarity	NPC223871
0.7765	Intermediate Similarity	NPC473478
0.7765	Intermediate Similarity	NPC107986
0.7765	Intermediate Similarity	NPC283085
0.7765	Intermediate Similarity	NPC66346
0.7753	Intermediate Similarity	NPC469692
0.7753	Intermediate Similarity	NPC469645
0.775	Intermediate Similarity	NPC470705
0.7738	Intermediate Similarity	NPC253801
0.7722	Intermediate Similarity	NPC315843
0.7722	Intermediate Similarity	NPC107654
0.7711	Intermediate Similarity	NPC297440
0.7701	Intermediate Similarity	NPC280621
0.7701	Intermediate Similarity	NPC20339
0.7701	Intermediate Similarity	NPC40376
0.7701	Intermediate Similarity	NPC48338
0.7701	Intermediate Similarity	NPC21208
0.7701	Intermediate Similarity	NPC233551
0.7692	Intermediate Similarity	NPC293114
0.7674	Intermediate Similarity	NPC240695
0.7674	Intermediate Similarity	NPC107717
0.7674	Intermediate Similarity	NPC308412
0.7674	Intermediate Similarity	NPC103523
0.7674	Intermediate Similarity	NPC204686
0.7674	Intermediate Similarity	NPC114694
0.7674	Intermediate Similarity	NPC473687
0.7674	Intermediate Similarity	NPC171174
0.7674	Intermediate Similarity	NPC134885
0.7674	Intermediate Similarity	NPC210218
0.7674	Intermediate Similarity	NPC134807
0.7674	Intermediate Similarity	NPC469910
0.7674	Intermediate Similarity	NPC219498
0.7674	Intermediate Similarity	NPC231096
0.7674	Intermediate Similarity	NPC134865
0.7674	Intermediate Similarity	NPC112685
0.7674	Intermediate Similarity	NPC232555
0.7674	Intermediate Similarity	NPC142117
0.7674	Intermediate Similarity	NPC475581
0.7674	Intermediate Similarity	NPC62118
0.7667	Intermediate Similarity	NPC121825
0.7647	Intermediate Similarity	NPC163093
0.7625	Intermediate Similarity	NPC478195
0.7625	Intermediate Similarity	NPC478191
0.7625	Intermediate Similarity	NPC478194
0.7625	Intermediate Similarity	NPC478192
0.7625	Intermediate Similarity	NPC478196
0.7625	Intermediate Similarity	NPC478193
0.7619	Intermediate Similarity	NPC180363
0.7619	Intermediate Similarity	NPC131002
0.7619	Intermediate Similarity	NPC473780
0.7619	Intermediate Similarity	NPC11332
0.7619	Intermediate Similarity	NPC73310
0.7619	Intermediate Similarity	NPC475159
0.7619	Intermediate Similarity	NPC329829
0.7619	Intermediate Similarity	NPC473712
0.7619	Intermediate Similarity	NPC473529
0.7619	Intermediate Similarity	NPC65930
0.7619	Intermediate Similarity	NPC94875
0.7619	Intermediate Similarity	NPC145914
0.7614	Intermediate Similarity	NPC139418
0.76	Intermediate Similarity	NPC282760
0.76	Intermediate Similarity	NPC273600
0.76	Intermediate Similarity	NPC19769
0.7595	Intermediate Similarity	NPC470435
0.7595	Intermediate Similarity	NPC284006
0.759	Intermediate Similarity	NPC162741
0.759	Intermediate Similarity	NPC91332
0.759	Intermediate Similarity	NPC47653
0.7564	Intermediate Similarity	NPC202011
0.7561	Intermediate Similarity	NPC248775
0.7561	Intermediate Similarity	NPC182292
0.7561	Intermediate Similarity	NPC318481
0.7558	Intermediate Similarity	NPC470755
0.7558	Intermediate Similarity	NPC120398
0.7558	Intermediate Similarity	NPC182383
0.7558	Intermediate Similarity	NPC477014
0.7558	Intermediate Similarity	NPC322529
0.7558	Intermediate Similarity	NPC471567
0.7558	Intermediate Similarity	NPC477013
0.7532	Intermediate Similarity	NPC474823
0.7531	Intermediate Similarity	NPC68819
0.7529	Intermediate Similarity	NPC144415
0.7528	Intermediate Similarity	NPC239517
0.7528	Intermediate Similarity	NPC473904
0.7528	Intermediate Similarity	NPC474232
0.75	Intermediate Similarity	NPC146811
0.75	Intermediate Similarity	NPC81045
0.75	Intermediate Similarity	NPC169511
0.75	Intermediate Similarity	NPC133730
0.75	Intermediate Similarity	NPC234077
0.75	Intermediate Similarity	NPC151403
0.75	Intermediate Similarity	NPC172821
0.75	Intermediate Similarity	NPC201356
0.75	Intermediate Similarity	NPC287089
0.75	Intermediate Similarity	NPC242364
0.75	Intermediate Similarity	NPC276299
0.75	Intermediate Similarity	NPC476590
0.75	Intermediate Similarity	NPC476803
0.75	Intermediate Similarity	NPC114727
0.75	Intermediate Similarity	NPC191929
0.75	Intermediate Similarity	NPC287164
0.75	Intermediate Similarity	NPC61257
0.75	Intermediate Similarity	NPC39754
0.75	Intermediate Similarity	NPC274446
0.75	Intermediate Similarity	NPC171135
0.75	Intermediate Similarity	NPC261952
0.75	Intermediate Similarity	NPC100454
0.75	Intermediate Similarity	NPC320569
0.7471	Intermediate Similarity	NPC47937
0.7471	Intermediate Similarity	NPC477015
0.7471	Intermediate Similarity	NPC469483
0.7471	Intermediate Similarity	NPC309211
0.747	Intermediate Similarity	NPC180725
0.747	Intermediate Similarity	NPC1180
0.747	Intermediate Similarity	NPC470149
0.747	Intermediate Similarity	NPC470148
0.7468	Intermediate Similarity	NPC316185
0.7442	Intermediate Similarity	NPC158756
0.7442	Intermediate Similarity	NPC156804
0.7442	Intermediate Similarity	NPC41856
0.7439	Intermediate Similarity	NPC116177
0.7439	Intermediate Similarity	NPC475711
0.7439	Intermediate Similarity	NPC7563
0.7439	Intermediate Similarity	NPC320630
0.7436	Intermediate Similarity	NPC475004
0.7416	Intermediate Similarity	NPC42598
0.7416	Intermediate Similarity	NPC40066
0.7416	Intermediate Similarity	NPC81778
0.7416	Intermediate Similarity	NPC477011
0.7416	Intermediate Similarity	NPC20621
0.7416	Intermediate Similarity	NPC93794
0.7416	Intermediate Similarity	NPC318963
0.7416	Intermediate Similarity	NPC91067
0.7416	Intermediate Similarity	NPC473504
0.7416	Intermediate Similarity	NPC280612
0.7407	Intermediate Similarity	NPC469414
0.7407	Intermediate Similarity	NPC329826
0.7403	Intermediate Similarity	NPC478100
0.7403	Intermediate Similarity	NPC478097
0.7381	Intermediate Similarity	NPC470147
0.7381	Intermediate Similarity	NPC133226
0.7375	Intermediate Similarity	NPC144419
0.7375	Intermediate Similarity	NPC329890
0.7368	Intermediate Similarity	NPC96414
0.7368	Intermediate Similarity	NPC470123
0.7363	Intermediate Similarity	NPC11456
0.7363	Intermediate Similarity	NPC288240
0.7363	Intermediate Similarity	NPC162205
0.7363	Intermediate Similarity	NPC273579
0.7363	Intermediate Similarity	NPC295204
0.7356	Intermediate Similarity	NPC470400
0.7356	Intermediate Similarity	NPC292809
0.7356	Intermediate Similarity	NPC473156
0.7356	Intermediate Similarity	NPC319036
0.7356	Intermediate Similarity	NPC329615

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 NPC473471 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	2058
0.2-0.3	4306
0.3-0.4	1935
0.4-0.5	566
0.5-0.6	106
0.6-0.7	35
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.734	Intermediate Similarity	NPD4225	Approved
0.6957	Remote Similarity	NPD7838	Discovery
0.6957	Remote Similarity	NPD5785	Approved
0.6778	Remote Similarity	NPD5363	Approved
0.6774	Remote Similarity	NPD46	Approved
0.6774	Remote Similarity	NPD6698	Approved
0.6742	Remote Similarity	NPD7154	Phase 3
0.6702	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6371	Approved
0.6633	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4252	Approved
0.6579	Remote Similarity	NPD6109	Phase 1
0.6528	Remote Similarity	NPD6927	Phase 3
0.6452	Remote Similarity	NPD4251	Approved
0.6452	Remote Similarity	NPD4250	Approved
0.6444	Remote Similarity	NPD4270	Approved
0.6444	Remote Similarity	NPD4269	Approved
0.6444	Remote Similarity	NPD5209	Approved
0.6422	Remote Similarity	NPD7115	Discovery
0.6375	Remote Similarity	NPD3197	Phase 1
0.6364	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4268	Approved
0.6364	Remote Similarity	NPD4271	Approved
0.6354	Remote Similarity	NPD7637	Suspended
0.6344	Remote Similarity	NPD5786	Approved
0.6344	Remote Similarity	NPD4249	Approved
0.6337	Remote Similarity	NPD5344	Discontinued
0.6296	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4756	Discovery
0.6237	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4822	Approved
0.6222	Remote Similarity	NPD4820	Approved
0.6222	Remote Similarity	NPD4821	Approved
0.6222	Remote Similarity	NPD4819	Approved
0.6196	Remote Similarity	NPD5362	Discontinued
0.6154	Remote Similarity	NPD5369	Approved
0.6154	Remote Similarity	NPD9119	Approved
0.6154	Remote Similarity	NPD69	Approved
0.6146	Remote Similarity	NPD5370	Suspended
0.6145	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5778	Approved
0.6122	Remote Similarity	NPD5779	Approved
0.6111	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD9118	Approved
0.6022	Remote Similarity	NPD5331	Approved
0.6022	Remote Similarity	NPD5332	Approved
0.6022	Remote Similarity	NPD6110	Phase 1
0.602	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6686	Approved
0.5978	Remote Similarity	NPD4790	Discontinued
0.5941	Remote Similarity	NPD7839	Suspended
0.5941	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6648	Approved
0.5913	Remote Similarity	NPD8516	Approved
0.5913	Remote Similarity	NPD8517	Approved
0.5913	Remote Similarity	NPD8515	Approved
0.5913	Remote Similarity	NPD8513	Phase 3
0.5895	Remote Similarity	NPD1694	Approved
0.5833	Remote Similarity	NPD39	Approved
0.5816	Remote Similarity	NPD6101	Approved
0.5816	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD4220	Pre-registration
0.5783	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7640	Approved
0.5769	Remote Similarity	NPD7639	Approved
0.5745	Remote Similarity	NPD6435	Approved
0.5743	Remote Similarity	NPD5282	Discontinued
0.57	Remote Similarity	NPD6411	Approved
0.5694	Remote Similarity	NPD6096	Approved
0.5694	Remote Similarity	NPD6097	Approved
0.5676	Remote Similarity	NPD5343	Approved
0.5673	Remote Similarity	NPD7638	Approved
0.5667	Remote Similarity	NPD8074	Phase 3
0.5667	Remote Similarity	NPD8039	Approved
0.5657	Remote Similarity	NPD1695	Approved
0.5647	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD3194	Approved
0.5641	Remote Similarity	NPD3196	Approved
0.5641	Remote Similarity	NPD3195	Phase 2
0.5641	Remote Similarity	NPD4266	Approved
0.5616	Remote Similarity	NPD4265	Approved
0.5607	Remote Similarity	NPD6647	Phase 2
0.5604	Remote Similarity	NPD819	Approved
0.5604	Remote Similarity	NPD818	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