NPASS Compound

Structure

NPC42662 OpenBabel07101719152D 43 45 0 0 1 0 0 0 0 0999 V2000 2.5416 5.6114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4358 2.3743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3526 -0.3737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0470 3.5394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1346 4.6508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2633 -2.3788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8508 1.3450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3979 -1.8719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 4.6331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 4.1440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9304 2.8634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5054 1.0937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1998 2.0720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5054 2.0720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3526 0.6046 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1998 4.0285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1075 4.5485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7096 -2.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1998 1.0937 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 3.1657 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3526 2.5611 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9304 0.3023 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8472 4.6331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5054 1.0937 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9304 2.8634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9304 0.3023 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9304 -1.2806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5054 2.0720 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9783 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1998 5.0068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6825 5.3400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2846 -3.0679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0470 0.6046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 5.6114 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2327 -2.2109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9729 -1.0805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3526 3.5394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5054 3.6548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5054 -0.4891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.1440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5054 -0.4891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 14 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 8 29 1 0 0 0 0 9 10 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 14 2 0 0 0 0 12 22 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 0 0 0 0 15 3 1 1 0 0 0 15 19 1 0 0 0 0 15 24 1 0 0 0 0 16 31 2 0 0 0 0 16 39 1 0 0 0 0 17 32 2 0 0 0 0 17 40 1 0 0 0 0 18 33 2 0 0 0 0 18 41 1 0 0 0 0 19 34 1 1 0 0 0 20 25 1 0 0 0 0 20 42 1 1 0 0 0 21 28 1 6 0 0 0 21 39 1 0 0 0 0 22 30 1 6 0 0 0 22 43 1 0 0 0 0 23 35 2 0 0 0 0 23 42 1 0 0 0 0 24 26 1 0 0 0 0 24 28 1 1 0 0 0 25 28 1 1 0 0 0 25 40 1 0 0 0 0 26 30 1 6 0 0 0 26 41 1 0 0 0 0 27 29 1 0 0 0 0 27 36 2 0 0 0 0 27 43 1 0 0 0 0 28 7 1 1 0 0 0 29 30 1 1 0 0 0 29 37 1 0 0 0 0 30 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	612.28
Volume:	600.221
LogP:	2.42
LogD:	1.895
LogS:	-3.879
# Rotatable Bonds:	10
TPSA:	192.19
# H-Bond Aceptor:	13
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.221
Synthetic Accessibility Score:	5.784
Fsp3:	0.767
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.247
MDCK Permeability:	0.00017878507787827402
Pgp-inhibitor:	0.997
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.963
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.142
Plasma Protein Binding (PPB):	43.390419006347656%
Volume Distribution (VD):	0.877
Pgp-substrate:	38.9812126159668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.016
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.092
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.114
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.264
CYP3A4-substrate:	0.229

ADMET: Excretion

Clearance (CL):	2.336
Half-life (T1/2):	0.848

ADMET: Toxicity

hERG Blockers:	0.092
Human Hepatotoxicity (H-HT):	0.679
Drug-inuced Liver Injury (DILI):	0.865
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.15
Maximum Recommended Daily Dose:	0.028
Skin Sensitization:	0.328
Carcinogencity:	0.065
Eye Corrosion:	0.005
Eye Irritation:	0.02
Respiratory Toxicity:	0.041

Download Data

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

Natural Product: NPC42662

Natural Product ID:	NPC42662
*Common Name:**	Briaexcavatolide L
IUPAC Name:	n.a.
Synonyms:	Briaexcavatolide L
Standard InCHIKey:	ZSLFBBPCCHJUKI-ZPADSBQXSA-N
Standard InCHI:	InChI=1S/C30H44O13/c1-9-10-23(35)42-20-11-14(2)12-22-30(38,29(8,37)27(36)43-22)26(41-18(6)33)24-15(3)19(34)13-21(39-16(4)31)28(24,7)25(20)40-17(5)32/h12,15,19-22,24-26,34,37-38H,9-11,13H2,1-8H3/b14-12-/t15-,19-,20-,21-,22-,24+,25-,26+,28-,29-,30+/m0/s1
SMILES:	CCCC(=O)O[C@H]1C/C(=C[C@@H]2OC(=O)[C@]([C@@]2([C@@H]([C@@H]2[C@]([C@H]1OC(=O)C)(C)[C@@H](OC(=O)C)C[C@@H]([C@@H]2C)O)OC(=O)C)O)(C)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501274
PubChem CID:	44584763
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096858]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10543904]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277747]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11720523]
NPO4817	Briareum excavatum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599257]
NPO4817	Briareum excavatum	Species	Briareidae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.5	ug ml-1	PMID[448212]

☑ 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 NPC42662 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	206
0.1-0.2	1241
0.2-0.3	4016
0.3-0.4	6902
0.4-0.5	13597
0.5-0.6	7369
0.6-0.7	6758
0.7-0.8	2425
0.8-0.85	130
0.85-0.9	39
0.9-0.95	9
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9709	High Similarity	NPC473877
0.9434	High Similarity	NPC474333
0.9346	High Similarity	NPC296822
0.932	High Similarity	NPC94377
0.9307	High Similarity	NPC474165
0.9307	High Similarity	NPC69171
0.9231	High Similarity	NPC475922
0.9223	High Similarity	NPC475510
0.9223	High Similarity	NPC475587
0.9208	High Similarity	NPC183571
0.9143	High Similarity	NPC161816
0.9143	High Similarity	NPC115257
0.9135	High Similarity	NPC473939
0.9135	High Similarity	NPC473595
0.9118	High Similarity	NPC4620
0.9029	High Similarity	NPC475676
0.9029	High Similarity	NPC220964
0.8991	High Similarity	NPC476712
0.8991	High Similarity	NPC476713
0.8981	High Similarity	NPC73314
0.8962	High Similarity	NPC473975
0.8962	High Similarity	NPC473594
0.8962	High Similarity	NPC281624
0.8962	High Similarity	NPC473843
0.8962	High Similarity	NPC474586
0.8899	High Similarity	NPC476710
0.8899	High Similarity	NPC476711
0.8879	High Similarity	NPC194619
0.8857	High Similarity	NPC324327
0.8857	High Similarity	NPC326994
0.8857	High Similarity	NPC474421
0.8857	High Similarity	NPC194620
0.8857	High Similarity	NPC72813
0.8774	High Similarity	NPC169888
0.8774	High Similarity	NPC474664
0.8774	High Similarity	NPC233379
0.8774	High Similarity	NPC327286
0.8774	High Similarity	NPC14862
0.8774	High Similarity	NPC55972
0.8762	High Similarity	NPC9303
0.8762	High Similarity	NPC16313
0.875	High Similarity	NPC474166
0.875	High Similarity	NPC19239
0.8716	High Similarity	NPC477126
0.8692	High Similarity	NPC15218
0.8661	High Similarity	NPC470186
0.8654	High Similarity	NPC474709
0.8649	High Similarity	NPC473590
0.8611	High Similarity	NPC475563
0.8611	High Similarity	NPC475134
0.8585	High Similarity	NPC475802
0.8532	High Similarity	NPC473921
0.8532	High Similarity	NPC475668
0.8532	High Similarity	NPC475480
0.8522	High Similarity	NPC67251
0.8505	High Similarity	NPC67321
0.8505	High Similarity	NPC187435
0.8491	Intermediate Similarity	NPC258532
0.8482	Intermediate Similarity	NPC470775
0.8482	Intermediate Similarity	NPC176513
0.8455	Intermediate Similarity	NPC317687
0.8435	Intermediate Similarity	NPC310035
0.8435	Intermediate Similarity	NPC188222
0.8435	Intermediate Similarity	NPC282003
0.8426	Intermediate Similarity	NPC476479
0.8421	Intermediate Similarity	NPC475003
0.8411	Intermediate Similarity	NPC284365
0.8411	Intermediate Similarity	NPC123726
0.8407	Intermediate Similarity	NPC470776
0.8393	Intermediate Similarity	NPC474734
0.8381	Intermediate Similarity	NPC308824
0.8381	Intermediate Similarity	NPC98225
0.8364	Intermediate Similarity	NPC317107
0.8362	Intermediate Similarity	NPC18945
0.8362	Intermediate Similarity	NPC105926
0.8362	Intermediate Similarity	NPC91693
0.8362	Intermediate Similarity	NPC303006
0.8362	Intermediate Similarity	NPC265557
0.8348	Intermediate Similarity	NPC470779
0.8333	Intermediate Similarity	NPC470185
0.8318	Intermediate Similarity	NPC146731
0.8318	Intermediate Similarity	NPC296950
0.8305	Intermediate Similarity	NPC470780
0.8302	Intermediate Similarity	NPC476081
0.8291	Intermediate Similarity	NPC24651
0.8291	Intermediate Similarity	NPC476729
0.8288	Intermediate Similarity	NPC269530
0.8286	Intermediate Similarity	NPC474718
0.8286	Intermediate Similarity	NPC272223
0.8276	Intermediate Similarity	NPC312833
0.8273	Intermediate Similarity	NPC5103
0.8269	Intermediate Similarity	NPC474395
0.8257	Intermediate Similarity	NPC306265
0.8257	Intermediate Similarity	NPC151393
0.8241	Intermediate Similarity	NPC173172
0.8241	Intermediate Similarity	NPC475414
0.823	Intermediate Similarity	NPC270478
0.8224	Intermediate Similarity	NPC61442
0.8224	Intermediate Similarity	NPC159533
0.8224	Intermediate Similarity	NPC156681
0.822	Intermediate Similarity	NPC181999
0.8214	Intermediate Similarity	NPC94509
0.8214	Intermediate Similarity	NPC469463
0.8214	Intermediate Similarity	NPC469454
0.8214	Intermediate Similarity	NPC469496
0.8205	Intermediate Similarity	NPC472399
0.8198	Intermediate Similarity	NPC157476
0.819	Intermediate Similarity	NPC216478
0.819	Intermediate Similarity	NPC471144
0.8182	Intermediate Similarity	NPC173905
0.8182	Intermediate Similarity	NPC284828
0.8182	Intermediate Similarity	NPC5475
0.8182	Intermediate Similarity	NPC472216
0.8182	Intermediate Similarity	NPC273433
0.8165	Intermediate Similarity	NPC112780
0.8165	Intermediate Similarity	NPC143609
0.8165	Intermediate Similarity	NPC131665
0.8165	Intermediate Similarity	NPC475176
0.8165	Intermediate Similarity	NPC255387
0.8158	Intermediate Similarity	NPC98249
0.8158	Intermediate Similarity	NPC97908
0.8158	Intermediate Similarity	NPC58662
0.8158	Intermediate Similarity	NPC287343
0.8158	Intermediate Similarity	NPC122033
0.8158	Intermediate Similarity	NPC473656
0.8158	Intermediate Similarity	NPC474654
0.8158	Intermediate Similarity	NPC469684
0.8158	Intermediate Similarity	NPC470854
0.8158	Intermediate Similarity	NPC53396
0.8158	Intermediate Similarity	NPC475323
0.8148	Intermediate Similarity	NPC472756
0.8142	Intermediate Similarity	NPC117712
0.8136	Intermediate Similarity	NPC470922
0.8131	Intermediate Similarity	NPC471148
0.8131	Intermediate Similarity	NPC472552
0.8131	Intermediate Similarity	NPC472754
0.8131	Intermediate Similarity	NPC149371
0.812	Intermediate Similarity	NPC257017
0.812	Intermediate Similarity	NPC162009
0.8113	Intermediate Similarity	NPC47024
0.8108	Intermediate Similarity	NPC472215
0.8108	Intermediate Similarity	NPC235014
0.8108	Intermediate Similarity	NPC472214
0.8103	Intermediate Similarity	NPC472004
0.8103	Intermediate Similarity	NPC145182
0.8103	Intermediate Similarity	NPC157252
0.8103	Intermediate Similarity	NPC471128
0.8103	Intermediate Similarity	NPC471126
0.8095	Intermediate Similarity	NPC134454
0.8095	Intermediate Similarity	NPC73911
0.8095	Intermediate Similarity	NPC17326
0.8091	Intermediate Similarity	NPC322903
0.8091	Intermediate Similarity	NPC37628
0.8087	Intermediate Similarity	NPC17772
0.8087	Intermediate Similarity	NPC251310
0.8087	Intermediate Similarity	NPC284707
0.8073	Intermediate Similarity	NPC472655
0.8073	Intermediate Similarity	NPC477125
0.8073	Intermediate Similarity	NPC111952
0.807	Intermediate Similarity	NPC190185
0.807	Intermediate Similarity	NPC179626
0.807	Intermediate Similarity	NPC89929
0.807	Intermediate Similarity	NPC40632
0.807	Intermediate Similarity	NPC474046
0.807	Intermediate Similarity	NPC328374
0.807	Intermediate Similarity	NPC96312
0.807	Intermediate Similarity	NPC213084
0.807	Intermediate Similarity	NPC470628
0.807	Intermediate Similarity	NPC207217
0.807	Intermediate Similarity	NPC259306
0.807	Intermediate Similarity	NPC251236
0.8056	Intermediate Similarity	NPC72842
0.8056	Intermediate Similarity	NPC120321
0.8056	Intermediate Similarity	NPC99510
0.8056	Intermediate Similarity	NPC472755
0.8056	Intermediate Similarity	NPC474775
0.8053	Intermediate Similarity	NPC471204
0.8053	Intermediate Similarity	NPC49451
0.8053	Intermediate Similarity	NPC478212
0.8053	Intermediate Similarity	NPC264153
0.8053	Intermediate Similarity	NPC89018
0.8051	Intermediate Similarity	NPC473802
0.8051	Intermediate Similarity	NPC129992
0.8037	Intermediate Similarity	NPC474339
0.8037	Intermediate Similarity	NPC476478
0.8037	Intermediate Similarity	NPC472554
0.8037	Intermediate Similarity	NPC47880
0.8037	Intermediate Similarity	NPC472753
0.8037	Intermediate Similarity	NPC164598
0.8036	Intermediate Similarity	NPC469656
0.8036	Intermediate Similarity	NPC469655
0.8036	Intermediate Similarity	NPC304180
0.8036	Intermediate Similarity	NPC179798
0.8036	Intermediate Similarity	NPC474846
0.8034	Intermediate Similarity	NPC472401
0.8034	Intermediate Similarity	NPC52839
0.8019	Intermediate Similarity	NPC278386
0.8019	Intermediate Similarity	NPC124512
0.8019	Intermediate Similarity	NPC159763
0.8018	Intermediate Similarity	NPC141350

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 NPC42662 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1641
0.2-0.3	3647
0.3-0.4	2311
0.4-0.5	818
0.5-0.6	323
0.6-0.7	209
0.7-0.8	27
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
0.8019	Intermediate Similarity	NPD4225	Approved
0.7928	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD6686	Approved
0.7544	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7115	Discovery
0.7524	Intermediate Similarity	NPD6698	Approved
0.7524	Intermediate Similarity	NPD46	Approved
0.7478	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD6371	Approved
0.744	Intermediate Similarity	NPD7319	Approved
0.7414	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD5344	Discontinued
0.7364	Intermediate Similarity	NPD7638	Approved
0.7355	Intermediate Similarity	NPD6319	Approved
0.7297	Intermediate Similarity	NPD7640	Approved
0.7297	Intermediate Similarity	NPD7639	Approved
0.7295	Intermediate Similarity	NPD8516	Approved
0.7295	Intermediate Similarity	NPD6921	Approved
0.7295	Intermediate Similarity	NPD8515	Approved
0.7295	Intermediate Similarity	NPD8513	Phase 3
0.7295	Intermediate Similarity	NPD8517	Approved
0.729	Intermediate Similarity	NPD7983	Approved
0.725	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7507	Approved
0.7177	Intermediate Similarity	NPD8328	Phase 3
0.7156	Intermediate Similarity	NPD5282	Discontinued
0.712	Intermediate Similarity	NPD7492	Approved
0.7094	Intermediate Similarity	NPD6373	Approved
0.7094	Intermediate Similarity	NPD6372	Approved
0.7073	Intermediate Similarity	NPD6059	Approved
0.7073	Intermediate Similarity	NPD6054	Approved
0.7064	Intermediate Similarity	NPD5779	Approved
0.7064	Intermediate Similarity	NPD5778	Approved
0.7063	Intermediate Similarity	NPD6616	Approved
0.7059	Intermediate Similarity	NPD8297	Approved
0.7049	Intermediate Similarity	NPD7327	Approved
0.7049	Intermediate Similarity	NPD7328	Approved
0.7008	Intermediate Similarity	NPD8293	Discontinued
0.7008	Intermediate Similarity	NPD8074	Phase 3
0.7008	Intermediate Similarity	NPD7078	Approved
0.7	Intermediate Similarity	NPD8133	Approved
0.7	Intermediate Similarity	NPD4632	Approved
0.6992	Remote Similarity	NPD7516	Approved
0.6991	Remote Similarity	NPD6648	Approved
0.6983	Remote Similarity	NPD5739	Approved
0.6983	Remote Similarity	NPD7128	Approved
0.6983	Remote Similarity	NPD6675	Approved
0.6983	Remote Similarity	NPD6402	Approved
0.6975	Remote Similarity	NPD6649	Approved
0.6975	Remote Similarity	NPD6650	Approved
0.6972	Remote Similarity	NPD7637	Suspended
0.696	Remote Similarity	NPD6370	Approved
0.6953	Remote Similarity	NPD7736	Approved
0.6949	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6399	Phase 3
0.6887	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7838	Discovery
0.688	Remote Similarity	NPD8379	Approved
0.688	Remote Similarity	NPD8296	Approved
0.688	Remote Similarity	NPD6015	Approved
0.688	Remote Similarity	NPD6016	Approved
0.688	Remote Similarity	NPD8033	Approved
0.688	Remote Similarity	NPD8378	Approved
0.688	Remote Similarity	NPD8380	Approved
0.688	Remote Similarity	NPD8335	Approved
0.6864	Remote Similarity	NPD7320	Approved
0.6864	Remote Similarity	NPD6899	Approved
0.6864	Remote Similarity	NPD6881	Approved
0.6825	Remote Similarity	NPD5988	Approved
0.6818	Remote Similarity	NPD6411	Approved
0.68	Remote Similarity	NPD8294	Approved
0.68	Remote Similarity	NPD8377	Approved
0.678	Remote Similarity	NPD5697	Approved
0.678	Remote Similarity	NPD5701	Approved
0.6777	Remote Similarity	NPD6882	Approved
0.675	Remote Similarity	NPD7290	Approved
0.675	Remote Similarity	NPD4634	Approved
0.675	Remote Similarity	NPD6883	Approved
0.675	Remote Similarity	NPD7102	Approved
0.6727	Remote Similarity	NPD5785	Approved
0.6724	Remote Similarity	NPD7632	Discontinued
0.6695	Remote Similarity	NPD6008	Approved
0.6694	Remote Similarity	NPD6847	Approved
0.6694	Remote Similarity	NPD6617	Approved
0.6694	Remote Similarity	NPD6869	Approved
0.6694	Remote Similarity	NPD8130	Phase 1
0.6694	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6641	Remote Similarity	NPD7604	Phase 2
0.6639	Remote Similarity	NPD6053	Discontinued
0.6639	Remote Similarity	NPD6412	Phase 2
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6101	Approved
0.6614	Remote Similarity	NPD5983	Phase 2
0.6614	Remote Similarity	NPD7503	Approved
0.6609	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7524	Approved
0.6604	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6011	Approved
0.6574	Remote Similarity	NPD1694	Approved
0.6565	Remote Similarity	NPD6033	Approved
0.6557	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7748	Approved
0.6544	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7260	Phase 2
0.6538	Remote Similarity	NPD6336	Discontinued
0.6522	Remote Similarity	NPD4755	Approved
0.6518	Remote Similarity	NPD8035	Phase 2
0.6518	Remote Similarity	NPD8034	Phase 2
0.6518	Remote Similarity	NPD7515	Phase 2
0.6509	Remote Similarity	NPD5369	Approved
0.6496	Remote Similarity	NPD1700	Approved
0.6491	Remote Similarity	NPD5695	Phase 3
0.6486	Remote Similarity	NPD1695	Approved
0.6481	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5696	Approved
0.6455	Remote Similarity	NPD4251	Approved
0.6455	Remote Similarity	NPD4250	Approved
0.6449	Remote Similarity	NPD4269	Approved
0.6449	Remote Similarity	NPD4270	Approved
0.6441	Remote Similarity	NPD5211	Phase 2
0.6435	Remote Similarity	NPD7839	Suspended
0.641	Remote Similarity	NPD4696	Approved
0.641	Remote Similarity	NPD5285	Approved
0.641	Remote Similarity	NPD4700	Approved
0.641	Remote Similarity	NPD5286	Approved
0.6404	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7900	Approved
0.6389	Remote Similarity	NPD7154	Phase 3
0.6389	Remote Similarity	NPD6695	Phase 3
0.637	Remote Similarity	NPD6845	Suspended
0.6364	Remote Similarity	NPD5786	Approved
0.6364	Remote Similarity	NPD4249	Approved
0.6364	Remote Similarity	NPD3618	Phase 1
0.6349	Remote Similarity	NPD6274	Approved
0.6333	Remote Similarity	NPD5141	Approved
0.633	Remote Similarity	NPD4786	Approved
0.6328	Remote Similarity	NPD7101	Approved
0.6328	Remote Similarity	NPD7100	Approved
0.6303	Remote Similarity	NPD5225	Approved
0.6303	Remote Similarity	NPD4633	Approved
0.6303	Remote Similarity	NPD5224	Approved
0.6303	Remote Similarity	NPD5226	Approved
0.6296	Remote Similarity	NPD3667	Approved
0.6293	Remote Similarity	NPD4697	Phase 3
0.6288	Remote Similarity	NPD8451	Approved
0.6288	Remote Similarity	NPD8273	Phase 1
0.6281	Remote Similarity	NPD4768	Approved
0.6281	Remote Similarity	NPD4767	Approved
0.6273	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5363	Approved
0.6262	Remote Similarity	NPD4819	Approved
0.6262	Remote Similarity	NPD4820	Approved
0.6262	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4821	Approved
0.6262	Remote Similarity	NPD4822	Approved
0.6262	Remote Similarity	NPD4252	Approved
0.625	Remote Similarity	NPD6335	Approved
0.625	Remote Similarity	NPD6672	Approved
0.625	Remote Similarity	NPD5737	Approved
0.625	Remote Similarity	NPD5174	Approved
0.625	Remote Similarity	NPD5175	Approved
0.6241	Remote Similarity	NPD8448	Approved
0.6239	Remote Similarity	NPD5362	Discontinued
0.6232	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6909	Approved
0.6231	Remote Similarity	NPD6908	Approved
0.6231	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5693	Phase 1
0.6226	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5223	Approved
0.6207	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4753	Phase 2
0.6195	Remote Similarity	NPD5328	Approved
0.6179	Remote Similarity	NPD4730	Approved
0.6179	Remote Similarity	NPD4729	Approved
0.6174	Remote Similarity	NPD4202	Approved
0.6172	Remote Similarity	NPD6317	Approved
0.6161	Remote Similarity	NPD7750	Discontinued
0.616	Remote Similarity	NPD2204	Approved
0.6159	Remote Similarity	NPD8415	Approved
0.6154	Remote Similarity	NPD5222	Approved
0.6154	Remote Similarity	NPD5221	Approved
0.6154	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6435	Approved
0.614	Remote Similarity	NPD3168	Discontinued
0.6136	Remote Similarity	NPD7642	Approved
0.6136	Remote Similarity	NPD6067	Discontinued
0.6124	Remote Similarity	NPD6314	Approved
0.6124	Remote Similarity	NPD6313	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