NPASS Compound

Structure

CID303697 OpenBabel06191716112D 23 24 0 0 1 0 0 0 0 0999 V2000 5.5549 2.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1235 0.8912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5889 2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 7 2 0 0 0 0 2 13 2 0 0 0 0 3 13 1 0 0 0 0 4 19 1 0 0 0 0 5 19 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 15 2 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 16 1 0 0 0 0 14 15 1 1 0 0 0 15 18 1 0 0 0 0 16 20 1 1 0 0 0 17 19 1 6 0 0 0 17 23 1 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 20 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	353.188
LogP:	4.267
LogD:	3.696
LogS:	-3.992
# Rotatable Bonds:	4
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.624
Synthetic Accessibility Score:	4.68
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.613
MDCK Permeability:	3.082323746639304e-05
Pgp-inhibitor:	0.978
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.113
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	90.48529052734375%
Volume Distribution (VD):	1.649
Pgp-substrate:	8.070494651794434%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.239
CYP2C19-inhibitor:	0.125
CYP2C19-substrate:	0.756
CYP2C9-inhibitor:	0.305
CYP2C9-substrate:	0.679
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.48
CYP3A4-inhibitor:	0.817
CYP3A4-substrate:	0.389

ADMET: Excretion

Clearance (CL):	3.026
Half-life (T1/2):	0.284

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.463
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.947
Carcinogencity:	0.246
Eye Corrosion:	0.863
Eye Irritation:	0.966
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC303697

Natural Product ID:	NPC303697
*Common Name:**	Lobatrienolide
IUPAC Name:	(2R)-5-[(1S,3R,4R)-4-ethenyl-4-methyl-3-prop-1-en-2-ylcyclohexyl]-2-(2-hydroxypropan-2-yl)-2,3-dihydropyran-6-one
Synonyms:	Lobatrienolide
Standard InCHIKey:	ITQMHGITORVJJF-MCNSXXNHSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-7-20(6)11-10-14(12-16(20)13(2)3)15-8-9-17(19(4,5)22)23-18(15)21/h7-8,14,16-17,22H,1-2,9-12H2,3-6H3/t14-,16+,17+,20-/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@@H](C[C@@H]1C(=C)C)C1=CC[C@@H](OC1=O)C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470132
PubChem CID:	11012596
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO14070	Spongosorites genitrix	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10217734]
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22209732]
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	Eukaryota	n.a.	Mindoro, Philippines	n.a.	PMID[9548875]
NPO13780	Mesua racemosa	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13780	Mesua racemosa	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12200	Eucalyptus carnea	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13780	Mesua racemosa	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4141	Gaillardia arizonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14070	Spongosorites genitrix	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3043	Plocamium hamatum	Species	Plocamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14478	Helenium laciniatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5349	Citrus hybrid	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13946	Dolichospermum spiroides	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	4

Activity Type	# Activity
Cell Line	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	23030.0	nM	PMID[569161]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	24790.0	nM	PMID[569161]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	15.0	mm	PMID[569160]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	13.0	mm	PMID[569160]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	9.0	mm	PMID[569160]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	6.0	mm	PMID[569160]

☑ 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 NPC303697 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1003
0.2-0.3	3786
0.3-0.4	8106
0.4-0.5	13736
0.5-0.6	7221
0.6-0.7	6707
0.7-0.8	1875
0.8-0.85	61
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8621	High Similarity	NPC49208
0.8571	High Similarity	NPC477125
0.8526	High Similarity	NPC316598
0.8526	High Similarity	NPC98868
0.8488	Intermediate Similarity	NPC233332
0.8462	Intermediate Similarity	NPC82876
0.8462	Intermediate Similarity	NPC5509
0.8444	Intermediate Similarity	NPC312561
0.8427	Intermediate Similarity	NPC65661
0.8427	Intermediate Similarity	NPC86316
0.8427	Intermediate Similarity	NPC106416
0.8416	Intermediate Similarity	NPC473627
0.8416	Intermediate Similarity	NPC29133
0.8416	Intermediate Similarity	NPC37116
0.8409	Intermediate Similarity	NPC23748
0.8387	Intermediate Similarity	NPC115021
0.8372	Intermediate Similarity	NPC233295
0.8333	Intermediate Similarity	NPC470961
0.8295	Intermediate Similarity	NPC471159
0.8295	Intermediate Similarity	NPC474291
0.8295	Intermediate Similarity	NPC123880
0.8283	Intermediate Similarity	NPC146731
0.828	Intermediate Similarity	NPC177037
0.828	Intermediate Similarity	NPC472814
0.8261	Intermediate Similarity	NPC168131
0.8261	Intermediate Similarity	NPC174342
0.8252	Intermediate Similarity	NPC236217
0.8252	Intermediate Similarity	NPC191620
0.8247	Intermediate Similarity	NPC476299
0.8247	Intermediate Similarity	NPC474012
0.8235	Intermediate Similarity	NPC5103
0.8229	Intermediate Similarity	NPC202705
0.8222	Intermediate Similarity	NPC189311
0.8218	Intermediate Similarity	NPC318363
0.8218	Intermediate Similarity	NPC473482
0.8218	Intermediate Similarity	NPC475418
0.8211	Intermediate Similarity	NPC295347
0.8211	Intermediate Similarity	NPC33473
0.8211	Intermediate Similarity	NPC183012
0.8211	Intermediate Similarity	NPC209355
0.8202	Intermediate Similarity	NPC22611
0.8202	Intermediate Similarity	NPC193198
0.8191	Intermediate Similarity	NPC139692
0.8182	Intermediate Similarity	NPC325031
0.8182	Intermediate Similarity	NPC40228
0.8182	Intermediate Similarity	NPC14203
0.8182	Intermediate Similarity	NPC229584
0.8172	Intermediate Similarity	NPC469595
0.8172	Intermediate Similarity	NPC15059
0.8172	Intermediate Similarity	NPC220454
0.8172	Intermediate Similarity	NPC232426
0.8172	Intermediate Similarity	NPC281942
0.8172	Intermediate Similarity	NPC212679
0.8172	Intermediate Similarity	NPC51486
0.8172	Intermediate Similarity	NPC214844
0.8163	Intermediate Similarity	NPC303559
0.8155	Intermediate Similarity	NPC304180
0.8155	Intermediate Similarity	NPC179798
0.8152	Intermediate Similarity	NPC226863
0.8152	Intermediate Similarity	NPC24816
0.8152	Intermediate Similarity	NPC215831
0.8144	Intermediate Similarity	NPC222303
0.8137	Intermediate Similarity	NPC475065
0.8132	Intermediate Similarity	NPC220478
0.8125	Intermediate Similarity	NPC29952
0.8119	Intermediate Similarity	NPC67321
0.8119	Intermediate Similarity	NPC330011
0.8119	Intermediate Similarity	NPC187435
0.8119	Intermediate Similarity	NPC329048
0.8105	Intermediate Similarity	NPC476415
0.8105	Intermediate Similarity	NPC477130
0.8105	Intermediate Similarity	NPC477129
0.8105	Intermediate Similarity	NPC38830
0.81	Intermediate Similarity	NPC296950
0.809	Intermediate Similarity	NPC200513
0.8085	Intermediate Similarity	NPC141831
0.8085	Intermediate Similarity	NPC186363
0.8085	Intermediate Similarity	NPC233345
0.8081	Intermediate Similarity	NPC475320
0.8068	Intermediate Similarity	NPC233377
0.8065	Intermediate Similarity	NPC284561
0.8065	Intermediate Similarity	NPC50488
0.8065	Intermediate Similarity	NPC73995
0.8065	Intermediate Similarity	NPC36668
0.8065	Intermediate Similarity	NPC118011
0.8065	Intermediate Similarity	NPC474396
0.8061	Intermediate Similarity	NPC471413
0.8061	Intermediate Similarity	NPC54705
0.8041	Intermediate Similarity	NPC208094
0.8041	Intermediate Similarity	NPC474343
0.8039	Intermediate Similarity	NPC306265
0.8022	Intermediate Similarity	NPC471795
0.8021	Intermediate Similarity	NPC293052
0.8019	Intermediate Similarity	NPC176840
0.8019	Intermediate Similarity	NPC190286
0.8	Intermediate Similarity	NPC166346
0.8	Intermediate Similarity	NPC469463
0.8	Intermediate Similarity	NPC99266
0.8	Intermediate Similarity	NPC475657
0.8	Intermediate Similarity	NPC469496
0.8	Intermediate Similarity	NPC469454
0.8	Intermediate Similarity	NPC56448
0.8	Intermediate Similarity	NPC472871
0.7981	Intermediate Similarity	NPC324683
0.798	Intermediate Similarity	NPC471412
0.7979	Intermediate Similarity	NPC310479
0.7979	Intermediate Similarity	NPC182136
0.7979	Intermediate Similarity	NPC469372
0.7979	Intermediate Similarity	NPC476437
0.7979	Intermediate Similarity	NPC472307
0.7979	Intermediate Similarity	NPC476369
0.7978	Intermediate Similarity	NPC327002
0.7961	Intermediate Similarity	NPC137911
0.7961	Intermediate Similarity	NPC228477
0.7959	Intermediate Similarity	NPC278386
0.7959	Intermediate Similarity	NPC108368
0.7959	Intermediate Similarity	NPC124512
0.7959	Intermediate Similarity	NPC57079
0.7959	Intermediate Similarity	NPC159763
0.7959	Intermediate Similarity	NPC23364
0.7957	Intermediate Similarity	NPC477128
0.7957	Intermediate Similarity	NPC472870
0.7955	Intermediate Similarity	NPC263951
0.7944	Intermediate Similarity	NPC470492
0.7944	Intermediate Similarity	NPC286528
0.7944	Intermediate Similarity	NPC20302
0.7944	Intermediate Similarity	NPC140055
0.7944	Intermediate Similarity	NPC312824
0.7944	Intermediate Similarity	NPC470493
0.7944	Intermediate Similarity	NPC167606
0.7944	Intermediate Similarity	NPC183580
0.7941	Intermediate Similarity	NPC475294
0.7941	Intermediate Similarity	NPC91034
0.7938	Intermediate Similarity	NPC134072
0.7938	Intermediate Similarity	NPC242848
0.7938	Intermediate Similarity	NPC234993
0.7938	Intermediate Similarity	NPC473153
0.7935	Intermediate Similarity	NPC185638
0.7935	Intermediate Similarity	NPC82979
0.7935	Intermediate Similarity	NPC9231
0.7935	Intermediate Similarity	NPC471219
0.7925	Intermediate Similarity	NPC67259
0.7925	Intermediate Similarity	NPC474181
0.7925	Intermediate Similarity	NPC147912
0.7921	Intermediate Similarity	NPC118911
0.7921	Intermediate Similarity	NPC473175
0.7917	Intermediate Similarity	NPC469491
0.7917	Intermediate Similarity	NPC470697
0.7917	Intermediate Similarity	NPC53685
0.7912	Intermediate Similarity	NPC30486
0.7912	Intermediate Similarity	NPC70424
0.7912	Intermediate Similarity	NPC243618
0.7912	Intermediate Similarity	NPC72464
0.7912	Intermediate Similarity	NPC9868
0.7905	Intermediate Similarity	NPC476801
0.7905	Intermediate Similarity	NPC470063
0.79	Intermediate Similarity	NPC476081
0.79	Intermediate Similarity	NPC32577
0.79	Intermediate Similarity	NPC155332
0.79	Intermediate Similarity	NPC137430
0.79	Intermediate Similarity	NPC114540
0.79	Intermediate Similarity	NPC162973
0.79	Intermediate Similarity	NPC31058
0.79	Intermediate Similarity	NPC469606
0.79	Intermediate Similarity	NPC273005
0.7895	Intermediate Similarity	NPC475972
0.7895	Intermediate Similarity	NPC477783
0.7895	Intermediate Similarity	NPC72845
0.7895	Intermediate Similarity	NPC252433
0.7889	Intermediate Similarity	NPC178676
0.7889	Intermediate Similarity	NPC186276
0.7885	Intermediate Similarity	NPC235014
0.7879	Intermediate Similarity	NPC174314
0.7879	Intermediate Similarity	NPC201406
0.7872	Intermediate Similarity	NPC20946
0.7872	Intermediate Similarity	NPC212598
0.7872	Intermediate Similarity	NPC251528
0.7872	Intermediate Similarity	NPC79027
0.787	Intermediate Similarity	NPC153440
0.787	Intermediate Similarity	NPC50774
0.787	Intermediate Similarity	NPC186525
0.787	Intermediate Similarity	NPC709
0.7865	Intermediate Similarity	NPC474592
0.7865	Intermediate Similarity	NPC271104
0.7865	Intermediate Similarity	NPC195424
0.7864	Intermediate Similarity	NPC220155
0.7864	Intermediate Similarity	NPC151393
0.7864	Intermediate Similarity	NPC472825
0.7857	Intermediate Similarity	NPC38530
0.7857	Intermediate Similarity	NPC475709
0.7857	Intermediate Similarity	NPC170131
0.7857	Intermediate Similarity	NPC73911
0.7857	Intermediate Similarity	NPC84335
0.785	Intermediate Similarity	NPC64318
0.7849	Intermediate Similarity	NPC181327
0.7849	Intermediate Similarity	NPC131329
0.7849	Intermediate Similarity	NPC128644
0.7849	Intermediate Similarity	NPC171722
0.7849	Intermediate Similarity	NPC473891
0.7843	Intermediate Similarity	NPC173172

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 NPC303697 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	1328
0.2-0.3	3367
0.3-0.4	2613
0.4-0.5	1092
0.5-0.6	356
0.6-0.7	207
0.7-0.8	16
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
0.809	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD4225	Approved
0.7944	Intermediate Similarity	NPD7115	Discovery
0.7826	Intermediate Similarity	NPD1694	Approved
0.7692	Intermediate Similarity	NPD6686	Approved
0.7426	Intermediate Similarity	NPD7638	Approved
0.7423	Intermediate Similarity	NPD46	Approved
0.7423	Intermediate Similarity	NPD6698	Approved
0.7374	Intermediate Similarity	NPD7748	Approved
0.7368	Intermediate Similarity	NPD6684	Approved
0.7368	Intermediate Similarity	NPD7146	Approved
0.7368	Intermediate Similarity	NPD5330	Approved
0.7368	Intermediate Similarity	NPD7521	Approved
0.7368	Intermediate Similarity	NPD7334	Approved
0.7368	Intermediate Similarity	NPD6409	Approved
0.7353	Intermediate Similarity	NPD7640	Approved
0.7353	Intermediate Similarity	NPD7639	Approved
0.73	Intermediate Similarity	NPD5695	Phase 3
0.7292	Intermediate Similarity	NPD3573	Approved
0.729	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6399	Phase 3
0.7245	Intermediate Similarity	NPD5785	Approved
0.7216	Intermediate Similarity	NPD6903	Approved
0.7216	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4623	Approved
0.7188	Intermediate Similarity	NPD4519	Discontinued
0.7172	Intermediate Similarity	NPD7515	Phase 2
0.7172	Intermediate Similarity	NPD5693	Phase 1
0.7158	Intermediate Similarity	NPD3666	Approved
0.7158	Intermediate Similarity	NPD3133	Approved
0.7158	Intermediate Similarity	NPD3665	Phase 1
0.7157	Intermediate Similarity	NPD7902	Approved
0.7157	Intermediate Similarity	NPD6083	Phase 2
0.7157	Intermediate Similarity	NPD6084	Phase 2
0.7129	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD3667	Approved
0.7115	Intermediate Similarity	NPD5344	Discontinued
0.7111	Intermediate Similarity	NPD8039	Approved
0.7103	Intermediate Similarity	NPD5697	Approved
0.7097	Intermediate Similarity	NPD4695	Discontinued
0.7091	Intermediate Similarity	NPD8297	Approved
0.7087	Intermediate Similarity	NPD5696	Approved
0.7071	Intermediate Similarity	NPD7838	Discovery
0.7064	Intermediate Similarity	NPD6371	Approved
0.7064	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6672	Approved
0.7041	Intermediate Similarity	NPD5737	Approved
0.7037	Intermediate Similarity	NPD6881	Approved
0.7037	Intermediate Similarity	NPD6011	Approved
0.7037	Intermediate Similarity	NPD6899	Approved
0.7027	Intermediate Similarity	NPD4632	Approved
0.701	Intermediate Similarity	NPD3618	Phase 1
0.701	Intermediate Similarity	NPD5690	Phase 2
0.7	Intermediate Similarity	NPD6079	Approved
0.7	Intermediate Similarity	NPD5281	Approved
0.7	Intermediate Similarity	NPD5284	Approved
0.7	Intermediate Similarity	NPD6411	Approved
0.6979	Remote Similarity	NPD4786	Approved
0.6972	Remote Similarity	NPD6014	Approved
0.6972	Remote Similarity	NPD6012	Approved
0.6972	Remote Similarity	NPD6013	Approved
0.6947	Remote Similarity	NPD4223	Phase 3
0.6947	Remote Similarity	NPD4221	Approved
0.6944	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6053	Discontinued
0.6931	Remote Similarity	NPD5779	Approved
0.6931	Remote Similarity	NPD5778	Approved
0.6923	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7102	Approved
0.6909	Remote Similarity	NPD7290	Approved
0.6909	Remote Similarity	NPD6883	Approved
0.69	Remote Similarity	NPD5207	Approved
0.6869	Remote Similarity	NPD5208	Approved
0.6863	Remote Similarity	NPD7900	Approved
0.6863	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6648	Approved
0.6852	Remote Similarity	NPD6675	Approved
0.6852	Remote Similarity	NPD6402	Approved
0.6852	Remote Similarity	NPD7128	Approved
0.6852	Remote Similarity	NPD5739	Approved
0.6847	Remote Similarity	NPD6650	Approved
0.6847	Remote Similarity	NPD6869	Approved
0.6847	Remote Similarity	NPD6649	Approved
0.6847	Remote Similarity	NPD6847	Approved
0.6847	Remote Similarity	NPD8130	Phase 1
0.6847	Remote Similarity	NPD6617	Approved
0.6837	Remote Similarity	NPD5279	Phase 3
0.6832	Remote Similarity	NPD5694	Approved
0.681	Remote Similarity	NPD6319	Approved
0.6807	Remote Similarity	NPD7507	Approved
0.6804	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4197	Approved
0.68	Remote Similarity	NPD6051	Approved
0.68	Remote Similarity	NPD6080	Approved
0.68	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6673	Approved
0.68	Remote Similarity	NPD5328	Approved
0.68	Remote Similarity	NPD6101	Approved
0.68	Remote Similarity	NPD4753	Phase 2
0.68	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6904	Approved
0.6796	Remote Similarity	NPD5210	Approved
0.6796	Remote Similarity	NPD4629	Approved
0.6789	Remote Similarity	NPD6412	Phase 2
0.6789	Remote Similarity	NPD5701	Approved
0.6789	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6882	Approved
0.6771	Remote Similarity	NPD5209	Approved
0.6765	Remote Similarity	NPD4202	Approved
0.6752	Remote Similarity	NPD7503	Approved
0.6735	Remote Similarity	NPD5329	Approved
0.6735	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5363	Approved
0.6733	Remote Similarity	NPD5692	Phase 3
0.6731	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5222	Approved
0.6731	Remote Similarity	NPD5221	Approved
0.6729	Remote Similarity	NPD7632	Discontinued
0.6729	Remote Similarity	NPD5211	Phase 2
0.6727	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7320	Approved
0.6702	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5362	Discontinued
0.6701	Remote Similarity	NPD7154	Phase 3
0.6698	Remote Similarity	NPD5286	Approved
0.6698	Remote Similarity	NPD5285	Approved
0.6698	Remote Similarity	NPD4696	Approved
0.6696	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6667	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6639	Remote Similarity	NPD7319	Approved
0.6636	Remote Similarity	NPD5223	Approved
0.6635	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3668	Phase 3
0.6632	Remote Similarity	NPD4195	Approved
0.661	Remote Similarity	NPD5983	Phase 2
0.6606	Remote Similarity	NPD5141	Approved
0.6574	Remote Similarity	NPD5226	Approved
0.6574	Remote Similarity	NPD4633	Approved
0.6574	Remote Similarity	NPD5225	Approved
0.6574	Remote Similarity	NPD5224	Approved
0.6566	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6317	Approved
0.6549	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6008	Approved
0.6542	Remote Similarity	NPD6404	Discontinued
0.6538	Remote Similarity	NPD5282	Discontinued
0.6538	Remote Similarity	NPD6001	Approved
0.6532	Remote Similarity	NPD7260	Phase 2
0.6531	Remote Similarity	NPD4788	Approved
0.6526	Remote Similarity	NPD3617	Approved
0.6514	Remote Similarity	NPD5174	Approved
0.6514	Remote Similarity	NPD5175	Approved
0.6509	Remote Similarity	NPD4755	Approved
0.6505	Remote Similarity	NPD8035	Phase 2
0.6505	Remote Similarity	NPD8034	Phase 2
0.65	Remote Similarity	NPD7604	Phase 2
0.6496	Remote Similarity	NPD6335	Approved
0.6496	Remote Similarity	NPD6313	Approved
0.6496	Remote Similarity	NPD7328	Approved
0.6496	Remote Similarity	NPD7327	Approved
0.6496	Remote Similarity	NPD6314	Approved
0.6495	Remote Similarity	NPD5369	Approved
0.6489	Remote Similarity	NPD6933	Approved
0.6471	Remote Similarity	NPD1695	Approved
0.6471	Remote Similarity	NPD8033	Approved
0.6466	Remote Similarity	NPD6274	Approved
0.6466	Remote Similarity	NPD2629	Approved
0.6466	Remote Similarity	NPD6868	Approved
0.646	Remote Similarity	NPD4634	Approved
0.6446	Remote Similarity	NPD7492	Approved
0.6441	Remote Similarity	NPD7101	Approved
0.6441	Remote Similarity	NPD7516	Approved
0.6441	Remote Similarity	NPD7100	Approved
0.6436	Remote Similarity	NPD7524	Approved
0.6435	Remote Similarity	NPD8133	Approved
0.6429	Remote Similarity	NPD4270	Approved
0.6429	Remote Similarity	NPD4269	Approved
0.6415	Remote Similarity	NPD7614	Phase 1
0.6415	Remote Similarity	NPD4697	Phase 3
0.64	Remote Similarity	NPD1696	Phase 3
0.6393	Remote Similarity	NPD6336	Discontinued
0.6393	Remote Similarity	NPD6616	Approved
0.6392	Remote Similarity	NPD4819	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