NPASS Compound

Structure

NPC471145 OpenBabel07101719132D 37 41 0 0 1 0 0 0 0 0999 V2000 -2.5486 3.1986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3914 -3.0246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3714 5.5406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1349 1.5453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -3.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5027 4.2840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7773 3.6308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2080 2.0788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1934 1.1027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3390 1.5588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5603 -1.8557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6086 0.1205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9286 2.4445 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6086 -2.0729 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2998 5.2389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2659 0.5779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9803 2.6760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5603 -0.0967 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9474 0.4827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9839 -0.9762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9023 0.6857 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8454 -0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1256 0.1153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7372 -0.8851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8454 -0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0252 5.8921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 -1.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0051 0.5389 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9402 -1.8400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3953 -0.6577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9512 -0.8452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3904 -0.1597 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 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 2 0 0 0 0 5 18 1 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 21 1 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 25 1 0 0 0 0 13 22 2 0 0 0 0 13 28 1 0 0 0 0 14 1 1 1 0 0 0 14 19 1 0 0 0 0 15 28 1 6 0 0 0 16 30 2 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 18 22 1 0 0 0 0 18 31 2 0 0 0 0 20 12 1 6 0 0 0 20 23 1 0 0 0 0 21 24 1 0 0 0 0 21 29 1 1 0 0 0 23 11 1 6 0 0 0 23 35 1 0 0 0 0 24 10 1 1 0 0 0 24 36 1 0 0 0 0 25 28 1 6 0 0 0 25 37 1 0 0 0 0 26 32 2 0 0 0 0 26 35 1 0 0 0 0 27 29 1 0 0 0 0 27 33 2 0 0 0 0 27 36 1 0 0 0 0 28 34 1 6 0 0 0 29 22 1 1 0 0 0 29 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	510.23
Volume:	516.588
LogP:	2.291
LogD:	1.659
LogS:	-4.294
# Rotatable Bonds:	3
TPSA:	116.2
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.455
Synthetic Accessibility Score:	6.339
Fsp3:	0.586
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.919
MDCK Permeability:	1.3685239537153393e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.613
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	82.35771942138672%
Volume Distribution (VD):	1.446
Pgp-substrate:	9.223583221435547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.485
CYP2C9-inhibitor:	0.292
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.809
CYP3A4-substrate:	0.684

ADMET: Excretion

Clearance (CL):	3.966
Half-life (T1/2):	0.778

ADMET: Toxicity

hERG Blockers:	0.829
Human Hepatotoxicity (H-HT):	0.977
Drug-inuced Liver Injury (DILI):	0.4
AMES Toxicity:	0.309
Rat Oral Acute Toxicity:	0.841
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.97
Carcinogencity:	0.333
Eye Corrosion:	0.004
Eye Irritation:	0.027
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC471145

Natural Product ID:	NPC471145
*Common Name:**	Pungiolide A
IUPAC Name:	(3R,3aR,4'aR,5'S,6'aR,7R,8aS,9'aR,10'aR)-3'-acetyl-4'a-hydroxy-5',7-dimethyl-9'-methylidene-6-[(E)-3-oxobut-1-enyl]spiro[4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-3,2'-5,6,6a,9a,10,10a-hexahydrofuro[1,2]cyclohepta[5,7-d]pyran]-2,8'-dione
Synonyms:
Standard InCHIKey:	BGZGKGJBTWDZQU-PKNRYQKPSA-N
Standard InCHI:	InChI=1S/C29H34O8/c1-14-10-24-21(9-8-19(14)7-6-16(3)30)29(27(33)36-24)22(18(5)31)13-28(34)15(2)11-23-20(12-25(28)37-29)17(4)26(32)35-23/h6-8,13-15,20-21,23-25,34H,4,9-12H2,1-3,5H3/b7-6+/t14-,15+,20-,21-,23-,24+,25-,28+,29-/m1/s1
SMILES:	CC(=O)/C=C/C1=CC[C@@H]2[C@H](C[C@H]1C)OC(=O)[C@]12O[C@@H]2C[C@H]3[C@@H](C[C@@H]([C@]2(C=C1C(=O)C)O)C)OC(=O)C3=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2380790
PubChem CID:	73348839
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0000502] Xanthanolides

*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
NPO32861	xanthium brasilicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]

☑ 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	3

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	50003.45	nM	PMID[489117]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[489117]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	>	30000.0	nM	PMID[489117]

☑ 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 NPC471145 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	254
0.1-0.2	1280
0.2-0.3	4484
0.3-0.4	8908
0.4-0.5	15287
0.5-0.6	8329
0.6-0.7	3358
0.7-0.8	760
0.8-0.85	31
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9455	High Similarity	NPC471146
0.8704	High Similarity	NPC475871
0.8704	High Similarity	NPC475945
0.8692	High Similarity	NPC474742
0.8624	High Similarity	NPC474741
0.8611	High Similarity	NPC474747
0.8532	High Similarity	NPC475873
0.8519	High Similarity	NPC185141
0.8519	High Similarity	NPC133907
0.8519	High Similarity	NPC46998
0.8519	High Similarity	NPC110443
0.8519	High Similarity	NPC128733
0.844	Intermediate Similarity	NPC149371
0.8364	Intermediate Similarity	NPC472755
0.8349	Intermediate Similarity	NPC47880
0.8319	Intermediate Similarity	NPC38154
0.8304	Intermediate Similarity	NPC26617
0.8288	Intermediate Similarity	NPC203659
0.8288	Intermediate Similarity	NPC100487
0.8273	Intermediate Similarity	NPC472754
0.8224	Intermediate Similarity	NPC475900
0.8198	Intermediate Similarity	NPC110989
0.819	Intermediate Similarity	NPC46269
0.819	Intermediate Similarity	NPC106395
0.8182	Intermediate Similarity	NPC472753
0.8148	Intermediate Similarity	NPC476009
0.8125	Intermediate Similarity	NPC472756
0.812	Intermediate Similarity	NPC138303
0.812	Intermediate Similarity	NPC133677
0.812	Intermediate Similarity	NPC67290
0.8108	Intermediate Similarity	NPC225353
0.8103	Intermediate Similarity	NPC123855
0.8103	Intermediate Similarity	NPC76550
0.8103	Intermediate Similarity	NPC138757
0.8103	Intermediate Similarity	NPC66108
0.8087	Intermediate Similarity	NPC477103
0.8073	Intermediate Similarity	NPC40812
0.8056	Intermediate Similarity	NPC36954
0.8053	Intermediate Similarity	NPC472749
0.8053	Intermediate Similarity	NPC472751
0.8053	Intermediate Similarity	NPC223450
0.8037	Intermediate Similarity	NPC476300
0.8034	Intermediate Similarity	NPC469454
0.8034	Intermediate Similarity	NPC469463
0.8034	Intermediate Similarity	NPC469496
0.8033	Intermediate Similarity	NPC42747
0.8018	Intermediate Similarity	NPC474339
0.8018	Intermediate Similarity	NPC15993
0.8018	Intermediate Similarity	NPC164598
0.8017	Intermediate Similarity	NPC304180
0.8017	Intermediate Similarity	NPC179798
0.8	Intermediate Similarity	NPC477102
0.8	Intermediate Similarity	NPC471144
0.7984	Intermediate Similarity	NPC11732
0.7984	Intermediate Similarity	NPC471940
0.7982	Intermediate Similarity	NPC477513
0.7965	Intermediate Similarity	NPC220964
0.7965	Intermediate Similarity	NPC471143
0.7965	Intermediate Similarity	NPC475676
0.7965	Intermediate Similarity	NPC477510
0.7965	Intermediate Similarity	NPC472748
0.7963	Intermediate Similarity	NPC121825
0.7953	Intermediate Similarity	NPC224623
0.7951	Intermediate Similarity	NPC192309
0.7946	Intermediate Similarity	NPC324017
0.7946	Intermediate Similarity	NPC320019
0.7946	Intermediate Similarity	NPC86077
0.7931	Intermediate Similarity	NPC257240
0.792	Intermediate Similarity	NPC172823
0.7913	Intermediate Similarity	NPC233379
0.7913	Intermediate Similarity	NPC14862
0.7913	Intermediate Similarity	NPC474664
0.7903	Intermediate Similarity	NPC471939
0.7895	Intermediate Similarity	NPC9303
0.7895	Intermediate Similarity	NPC16313
0.7895	Intermediate Similarity	NPC475802
0.7895	Intermediate Similarity	NPC243998
0.789	Intermediate Similarity	NPC304886
0.7886	Intermediate Similarity	NPC1538
0.7881	Intermediate Similarity	NPC56448
0.7876	Intermediate Similarity	NPC472747
0.7876	Intermediate Similarity	NPC472750
0.7876	Intermediate Similarity	NPC4620
0.787	Intermediate Similarity	NPC81419
0.787	Intermediate Similarity	NPC469645
0.787	Intermediate Similarity	NPC469692
0.787	Intermediate Similarity	NPC475912
0.787	Intermediate Similarity	NPC179746
0.7869	Intermediate Similarity	NPC470829
0.7869	Intermediate Similarity	NPC473228
0.7863	Intermediate Similarity	NPC287311
0.7857	Intermediate Similarity	NPC201718
0.7857	Intermediate Similarity	NPC476270
0.7857	Intermediate Similarity	NPC13071
0.785	Intermediate Similarity	NPC51004
0.7845	Intermediate Similarity	NPC47951
0.7845	Intermediate Similarity	NPC15218
0.7838	Intermediate Similarity	NPC187761
0.7838	Intermediate Similarity	NPC141191
0.7838	Intermediate Similarity	NPC308567
0.7838	Intermediate Similarity	NPC83895
0.7838	Intermediate Similarity	NPC261377
0.7838	Intermediate Similarity	NPC255592
0.7838	Intermediate Similarity	NPC161855
0.7833	Intermediate Similarity	NPC23046
0.7826	Intermediate Similarity	NPC194620
0.7826	Intermediate Similarity	NPC72813
0.7826	Intermediate Similarity	NPC324327
0.7826	Intermediate Similarity	NPC474421
0.7826	Intermediate Similarity	NPC326994
0.7823	Intermediate Similarity	NPC473919
0.7823	Intermediate Similarity	NPC473709
0.7823	Intermediate Similarity	NPC144625
0.7818	Intermediate Similarity	NPC476315
0.7818	Intermediate Similarity	NPC39859
0.7818	Intermediate Similarity	NPC76862
0.7818	Intermediate Similarity	NPC158416
0.7818	Intermediate Similarity	NPC470883
0.7798	Intermediate Similarity	NPC469632
0.7795	Intermediate Similarity	NPC469351
0.7788	Intermediate Similarity	NPC189609
0.7788	Intermediate Similarity	NPC303653
0.7788	Intermediate Similarity	NPC291500
0.7788	Intermediate Similarity	NPC197835
0.7788	Intermediate Similarity	NPC140591
0.7787	Intermediate Similarity	NPC147635
0.7787	Intermediate Similarity	NPC163693
0.7778	Intermediate Similarity	NPC184463
0.7778	Intermediate Similarity	NPC261607
0.7778	Intermediate Similarity	NPC300312
0.7778	Intermediate Similarity	NPC208886
0.7778	Intermediate Similarity	NPC111114
0.7778	Intermediate Similarity	NPC5103
0.7778	Intermediate Similarity	NPC236999
0.7778	Intermediate Similarity	NPC12172
0.7778	Intermediate Similarity	NPC30515
0.7768	Intermediate Similarity	NPC475949
0.7768	Intermediate Similarity	NPC288876
0.7759	Intermediate Similarity	NPC55972
0.7759	Intermediate Similarity	NPC327286
0.7759	Intermediate Similarity	NPC169888
0.7759	Intermediate Similarity	NPC117604
0.7759	Intermediate Similarity	NPC475960
0.7757	Intermediate Similarity	NPC307411
0.7752	Intermediate Similarity	NPC471136
0.7752	Intermediate Similarity	NPC473548
0.7752	Intermediate Similarity	NPC100017
0.7752	Intermediate Similarity	NPC475154
0.7752	Intermediate Similarity	NPC223356
0.7752	Intermediate Similarity	NPC471137
0.7752	Intermediate Similarity	NPC475500
0.7752	Intermediate Similarity	NPC182266
0.775	Intermediate Similarity	NPC54739
0.7748	Intermediate Similarity	NPC169205
0.7748	Intermediate Similarity	NPC474313
0.7742	Intermediate Similarity	NPC473802
0.7739	Intermediate Similarity	NPC469852
0.7731	Intermediate Similarity	NPC209058
0.7727	Intermediate Similarity	NPC14961
0.7727	Intermediate Similarity	NPC471142
0.7727	Intermediate Similarity	NPC270013
0.7706	Intermediate Similarity	NPC135776
0.7705	Intermediate Similarity	NPC477092
0.7699	Intermediate Similarity	NPC477511
0.7699	Intermediate Similarity	NPC150923
0.7699	Intermediate Similarity	NPC264477
0.7685	Intermediate Similarity	NPC476004
0.7685	Intermediate Similarity	NPC474761
0.7679	Intermediate Similarity	NPC187268
0.7679	Intermediate Similarity	NPC470541
0.7679	Intermediate Similarity	NPC54843
0.7672	Intermediate Similarity	NPC266514
0.7672	Intermediate Similarity	NPC469853
0.7672	Intermediate Similarity	NPC470192
0.7658	Intermediate Similarity	NPC31645
0.7658	Intermediate Similarity	NPC185553
0.7658	Intermediate Similarity	NPC17585
0.7658	Intermediate Similarity	NPC473291
0.7656	Intermediate Similarity	NPC477189
0.7656	Intermediate Similarity	NPC475314
0.7656	Intermediate Similarity	NPC251564
0.7656	Intermediate Similarity	NPC475606
0.7652	Intermediate Similarity	NPC309190
0.7647	Intermediate Similarity	NPC95290
0.7647	Intermediate Similarity	NPC317687
0.7647	Intermediate Similarity	NPC189338
0.7636	Intermediate Similarity	NPC167219
0.7636	Intermediate Similarity	NPC190294
0.7636	Intermediate Similarity	NPC477131
0.7636	Intermediate Similarity	NPC474035
0.7636	Intermediate Similarity	NPC81386
0.7634	Intermediate Similarity	NPC68282
0.7632	Intermediate Similarity	NPC473596
0.7632	Intermediate Similarity	NPC471148
0.7632	Intermediate Similarity	NPC66110
0.7627	Intermediate Similarity	NPC115257
0.7627	Intermediate Similarity	NPC161816
0.7623	Intermediate Similarity	NPC13710
0.7623	Intermediate Similarity	NPC475309
0.7623	Intermediate Similarity	NPC475401

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 NPC471145 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	1690
0.2-0.3	3720
0.3-0.4	2341
0.4-0.5	817
0.5-0.6	295
0.6-0.7	60
0.7-0.8	4
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8304	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6371	Approved
0.7615	Intermediate Similarity	NPD7983	Approved
0.7568	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD8513	Phase 3
0.7273	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6698	Approved
0.7207	Intermediate Similarity	NPD7838	Discovery
0.7207	Intermediate Similarity	NPD46	Approved
0.7185	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5282	Discontinued
0.7165	Intermediate Similarity	NPD8516	Approved
0.7165	Intermediate Similarity	NPD8515	Approved
0.7165	Intermediate Similarity	NPD8517	Approved
0.708	Intermediate Similarity	NPD5779	Approved
0.708	Intermediate Similarity	NPD5778	Approved
0.6894	Remote Similarity	NPD8074	Phase 3
0.685	Remote Similarity	NPD7115	Discovery
0.6822	Remote Similarity	NPD6319	Approved
0.6814	Remote Similarity	NPD1695	Approved
0.68	Remote Similarity	NPD6053	Discontinued
0.678	Remote Similarity	NPD4225	Approved
0.6757	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5785	Approved
0.6752	Remote Similarity	NPD7839	Suspended
0.6748	Remote Similarity	NPD6686	Approved
0.6742	Remote Similarity	NPD7492	Approved
0.6723	Remote Similarity	NPD6648	Approved
0.6696	Remote Similarity	NPD5786	Approved
0.6692	Remote Similarity	NPD6616	Approved
0.6692	Remote Similarity	NPD6054	Approved
0.6691	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD5344	Discontinued
0.6642	Remote Similarity	NPD7078	Approved
0.6613	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5363	Approved
0.6593	Remote Similarity	NPD7736	Approved
0.6591	Remote Similarity	NPD6370	Approved
0.6587	Remote Similarity	NPD6649	Approved
0.6587	Remote Similarity	NPD6650	Approved
0.6567	Remote Similarity	NPD8273	Phase 1
0.6541	Remote Similarity	NPD7642	Approved
0.6541	Remote Similarity	NPD7829	Approved
0.6541	Remote Similarity	NPD7830	Approved
0.6535	Remote Similarity	NPD8297	Approved
0.6522	Remote Similarity	NPD6845	Suspended
0.6522	Remote Similarity	NPD6101	Approved
0.6522	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD6016	Approved
0.6515	Remote Similarity	NPD6015	Approved
0.6466	Remote Similarity	NPD5988	Approved
0.6444	Remote Similarity	NPD8451	Approved
0.6439	Remote Similarity	NPD6059	Approved
0.6429	Remote Similarity	NPD6110	Phase 1
0.6429	Remote Similarity	NPD6372	Approved
0.6429	Remote Similarity	NPD6373	Approved
0.6423	Remote Similarity	NPD7319	Approved
0.6418	Remote Similarity	NPD8328	Phase 3
0.6412	Remote Similarity	NPD7641	Discontinued
0.641	Remote Similarity	NPD6411	Approved
0.6397	Remote Similarity	NPD8448	Approved
0.6397	Remote Similarity	NPD8293	Discontinued
0.6391	Remote Similarity	NPD8444	Approved
0.637	Remote Similarity	NPD8340	Approved
0.637	Remote Similarity	NPD8299	Approved
0.637	Remote Similarity	NPD8341	Approved
0.637	Remote Similarity	NPD8342	Approved
0.6357	Remote Similarity	NPD4632	Approved
0.6349	Remote Similarity	NPD6881	Approved
0.6349	Remote Similarity	NPD6899	Approved
0.6348	Remote Similarity	NPD4251	Approved
0.6348	Remote Similarity	NPD4250	Approved
0.6339	Remote Similarity	NPD4270	Approved
0.6339	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD4269	Approved
0.6336	Remote Similarity	NPD7500	Approved
0.6324	Remote Similarity	NPD7507	Approved
0.6279	Remote Similarity	NPD6882	Approved
0.6271	Remote Similarity	NPD7637	Suspended
0.627	Remote Similarity	NPD5697	Approved
0.6261	Remote Similarity	NPD4249	Approved
0.6259	Remote Similarity	NPD8392	Approved
0.6259	Remote Similarity	NPD8391	Approved
0.6259	Remote Similarity	NPD8390	Approved
0.625	Remote Similarity	NPD7102	Approved
0.625	Remote Similarity	NPD6883	Approved
0.625	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5369	Approved
0.625	Remote Similarity	NPD7290	Approved
0.6222	Remote Similarity	NPD8080	Discontinued
0.622	Remote Similarity	NPD7320	Approved
0.6212	Remote Similarity	NPD6009	Approved
0.6202	Remote Similarity	NPD6869	Approved
0.6202	Remote Similarity	NPD6847	Approved
0.6202	Remote Similarity	NPD6617	Approved
0.6202	Remote Similarity	NPD8130	Phase 1
0.6195	Remote Similarity	NPD6435	Approved
0.6195	Remote Similarity	NPD5209	Approved
0.619	Remote Similarity	NPD7128	Approved
0.619	Remote Similarity	NPD6402	Approved
0.619	Remote Similarity	NPD6675	Approved
0.619	Remote Similarity	NPD5739	Approved
0.6182	Remote Similarity	NPD4756	Discovery
0.6176	Remote Similarity	NPD7604	Phase 2
0.6174	Remote Similarity	NPD1694	Approved
0.6172	Remote Similarity	NPD6013	Approved
0.6172	Remote Similarity	NPD6012	Approved
0.6172	Remote Similarity	NPD6014	Approved
0.6161	Remote Similarity	NPD4252	Approved
0.6148	Remote Similarity	NPD5983	Phase 2
0.6148	Remote Similarity	NPD7503	Approved
0.6148	Remote Similarity	NPD6921	Approved
0.614	Remote Similarity	NPD7154	Phase 3
0.614	Remote Similarity	NPD5362	Discontinued
0.6124	Remote Similarity	NPD4634	Approved
0.6094	Remote Similarity	NPD6011	Approved
0.609	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6336	Discontinued
0.6077	Remote Similarity	NPD2204	Approved
0.6063	Remote Similarity	NPD6008	Approved
0.6048	Remote Similarity	NPD7639	Approved
0.6048	Remote Similarity	NPD7640	Approved
0.6047	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD8269	Approved
0.6029	Remote Similarity	NPD8268	Approved
0.6029	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD8267	Approved
0.6029	Remote Similarity	NPD8266	Approved
0.6018	Remote Similarity	NPD4819	Approved
0.6018	Remote Similarity	NPD5368	Approved
0.6018	Remote Similarity	NPD4820	Approved
0.6018	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD4822	Approved
0.6018	Remote Similarity	NPD4821	Approved
0.6016	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5701	Approved
0.6016	Remote Similarity	NPD6084	Phase 2
0.6016	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD6033	Approved
0.5984	Remote Similarity	NPD5695	Phase 3
0.5972	Remote Similarity	NPD8415	Approved
0.5968	Remote Similarity	NPD7638	Approved
0.5968	Remote Similarity	NPD5696	Approved
0.5954	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD5211	Phase 2
0.595	Remote Similarity	NPD6399	Phase 3
0.5915	Remote Similarity	NPD5956	Approved
0.5913	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD6412	Phase 2
0.5882	Remote Similarity	NPD7100	Approved
0.5882	Remote Similarity	NPD7101	Approved
0.5878	Remote Similarity	NPD2067	Discontinued
0.5859	Remote Similarity	NPD5141	Approved
0.5852	Remote Similarity	NPD7505	Discontinued
0.5841	Remote Similarity	NPD4271	Approved
0.5841	Remote Similarity	NPD4268	Approved
0.5841	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5809	Remote Similarity	NPD7327	Approved
0.5809	Remote Similarity	NPD6335	Approved
0.5809	Remote Similarity	NPD7328	Approved
0.5808	Remote Similarity	NPD7799	Discontinued
0.5806	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD7524	Approved
0.5797	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD8033	Approved
0.5794	Remote Similarity	NPD5286	Approved
0.5794	Remote Similarity	NPD5285	Approved
0.5794	Remote Similarity	NPD4696	Approved
0.5778	Remote Similarity	NPD6274	Approved
0.5778	Remote Similarity	NPD690	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7516	Approved
0.576	Remote Similarity	NPD7902	Approved
0.5758	Remote Similarity	NPD6421	Discontinued
0.575	Remote Similarity	NPD6672	Approved
0.575	Remote Similarity	NPD5737	Approved
0.5738	Remote Similarity	NPD5284	Approved
0.5738	Remote Similarity	NPD5694	Approved
0.5738	Remote Similarity	NPD5693	Phase 1
0.5738	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD5281	Approved
0.5738	Remote Similarity	NPD6050	Approved
0.5736	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD6317	Approved
0.5735	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD5332	Approved
0.5726	Remote Similarity	NPD5331	Approved
0.5725	Remote Similarity	NPD8294	Approved
0.5725	Remote Similarity	NPD8377	Approved
0.5723	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6190	Approved
0.5714	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8039	Approved
0.5703	Remote Similarity	NPD4633	Approved
0.5703	Remote Similarity	NPD5224	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