NPASS Compound

Structure

NPC281624 OpenBabel07101719512D 41 44 0 0 1 0 0 0 0 0999 V2000 5.7385 2.5599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2813 2.8620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5046 0.1154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8349 5.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1982 4.0265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4372 -2.5775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0036 1.8332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7771 -1.4642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8918 3.0487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0450 2.5599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7767 3.3509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 3.6530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3514 1.5821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3514 2.5599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3514 2.5599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5046 1.0932 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2602 5.0352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3514 4.5154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1375 -1.7865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3514 1.5821 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0831 3.3509 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5046 3.0487 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7767 0.7910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0450 1.5821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6579 1.5821 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0831 0.7910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7767 -0.7910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6579 2.5599 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8468 -0.4889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8468 0.4889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7123 5.1374 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3514 5.4932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1100 -1.8887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8918 1.0932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0789 -1.7210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6579 4.1419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5046 4.0265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6579 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1982 1.0932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3514 -0.0000 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 9 1 0 0 0 0 2 15 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 8 29 1 0 0 0 0 9 10 1 0 0 0 0 10 24 1 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 12 21 1 0 0 0 0 13 15 2 0 0 0 0 13 23 1 0 0 0 0 14 20 1 0 0 0 0 14 22 1 0 0 0 0 16 3 1 6 0 0 0 16 20 1 0 0 0 0 16 25 1 0 0 0 0 17 31 2 0 0 0 0 17 36 1 0 0 0 0 18 32 2 0 0 0 0 18 37 1 0 0 0 0 19 33 2 0 0 0 0 19 38 1 0 0 0 0 20 39 1 6 0 0 0 21 28 1 6 0 0 0 21 36 1 0 0 0 0 22 28 1 1 0 0 0 22 37 1 0 0 0 0 23 30 1 1 0 0 0 23 40 1 0 0 0 0 24 34 2 0 0 0 0 24 39 1 0 0 0 0 25 26 1 0 0 0 0 25 28 1 6 0 0 0 26 30 1 1 0 0 0 26 38 1 0 0 0 0 27 29 1 0 0 0 0 27 35 2 0 0 0 0 27 40 1 0 0 0 0 28 7 1 6 0 0 0 29 30 1 6 0 0 0 29 41 1 0 0 0 0 30 41 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.26
Volume:	571.447
LogP:	3.558
LogD:	2.348
LogS:	-4.817
# Rotatable Bonds:	10
TPSA:	144.03
# H-Bond Aceptor:	11
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.261
Synthetic Accessibility Score:	6.183
Fsp3:	0.7
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:	-4.969
MDCK Permeability:	0.0001355743734166026
Pgp-inhibitor:	1.0
Pgp-substrate:	0.052
Human Intestinal Absorption (HIA):	0.057
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.621
Plasma Protein Binding (PPB):	69.24182891845703%
Volume Distribution (VD):	1.408
Pgp-substrate:	24.15748405456543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.029
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.189
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.606
CYP3A4-substrate:	0.42

ADMET: Excretion

Clearance (CL):	4.653
Half-life (T1/2):	0.779

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.962
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.48
Rat Oral Acute Toxicity:	0.578
Maximum Recommended Daily Dose:	0.055
Skin Sensitization:	0.634
Carcinogencity:	0.115
Eye Corrosion:	0.14
Eye Irritation:	0.148
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC281624

Natural Product ID:	NPC281624
*Common Name:**	Excavatolide F
IUPAC Name:	n.a.
Synonyms:	Excavatolide F
Standard InCHIKey:	GQDAKDHRSOAMMK-JUISPFEWSA-N
Standard InCHI:	InChI=1S/C30H40O11/c1-9-10-24(34)39-20-14-22(37-18(5)32)28(7)21(36-17(4)31)12-11-15(2)13-23-30(29(8,41-30)27(35)40-23)26(38-19(6)33)25(28)16(20)3/h11-13,16,20-23,25-26H,9-10,14H2,1-8H3/b12-11+,15-13-/t16-,20-,21-,22-,23-,25+,26+,28-,29-,30-/m0/s1
SMILES:	CCCC(=O)O[C@H]1C[C@@H]([C@]2(C)[C@H](/C=C/C(=C[C@H]3[C@]4([C@@H]([C@H]2[C@H]1C)OC(=O)C)[C@](C)(C(=O)O3)O4)/C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510128
PubChem CID:	44558992
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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	7.0	ug ml-1	PMID[470264]
NPT168	Cell Line	P388	Mus musculus	ED50	=	6.2	ug ml-1	PMID[470264]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	5.2	ug ml-1	PMID[470264]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	5.5	ug ml-1	PMID[470264]

☑ 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 NPC281624 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	256
0.1-0.2	1331
0.2-0.3	4396
0.3-0.4	7637
0.4-0.5	14774
0.5-0.6	8405
0.6-0.7	4826
0.7-0.8	993
0.8-0.85	41
0.85-0.9	21
0.9-0.95	9
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9703	High Similarity	NPC475587
0.9703	High Similarity	NPC475510
0.9608	High Similarity	NPC473939
0.9608	High Similarity	NPC473595
0.9423	High Similarity	NPC473594
0.9423	High Similarity	NPC474586
0.9423	High Similarity	NPC473843
0.9423	High Similarity	NPC473975
0.9333	High Similarity	NPC194619
0.9245	High Similarity	NPC473877
0.9216	High Similarity	NPC19239
0.9216	High Similarity	NPC474166
0.9074	High Similarity	NPC73314
0.8991	High Similarity	NPC474333
0.8962	High Similarity	NPC42662
0.8909	High Similarity	NPC296822
0.8868	High Similarity	NPC94377
0.8818	High Similarity	NPC477509
0.8785	High Similarity	NPC475922
0.875	High Similarity	NPC470186
0.8704	High Similarity	NPC115257
0.8704	High Similarity	NPC161816
0.8679	High Similarity	NPC9303
0.8679	High Similarity	NPC16313
0.8679	High Similarity	NPC475802
0.8649	High Similarity	NPC476711
0.8649	High Similarity	NPC476710
0.8598	High Similarity	NPC194620
0.8598	High Similarity	NPC324327
0.8598	High Similarity	NPC474421
0.8598	High Similarity	NPC326994
0.8598	High Similarity	NPC72813
0.8571	High Similarity	NPC476713
0.8571	High Similarity	NPC476712
0.8522	High Similarity	NPC282003
0.8522	High Similarity	NPC310035
0.8522	High Similarity	NPC188222
0.8519	High Similarity	NPC327286
0.8519	High Similarity	NPC474664
0.8519	High Similarity	NPC169888
0.8519	High Similarity	NPC55972
0.8519	High Similarity	NPC233379
0.8519	High Similarity	NPC14862
0.8448	Intermediate Similarity	NPC303006
0.844	Intermediate Similarity	NPC15218
0.8396	Intermediate Similarity	NPC183571
0.8348	Intermediate Similarity	NPC475003
0.8319	Intermediate Similarity	NPC270478
0.8318	Intermediate Similarity	NPC474165
0.8318	Intermediate Similarity	NPC4620
0.8318	Intermediate Similarity	NPC69171
0.8304	Intermediate Similarity	NPC477126
0.8264	Intermediate Similarity	NPC470185
0.8241	Intermediate Similarity	NPC471143
0.8241	Intermediate Similarity	NPC477127
0.8241	Intermediate Similarity	NPC220964
0.8241	Intermediate Similarity	NPC477510
0.8241	Intermediate Similarity	NPC475676
0.819	Intermediate Similarity	NPC471140
0.8131	Intermediate Similarity	NPC476478
0.8108	Intermediate Similarity	NPC469370
0.8091	Intermediate Similarity	NPC474716
0.8053	Intermediate Similarity	NPC317687
0.8053	Intermediate Similarity	NPC471933
0.8017	Intermediate Similarity	NPC284707
0.8	Intermediate Similarity	NPC181999
0.8	Intermediate Similarity	NPC103088
0.8	Intermediate Similarity	NPC470975
0.8	Intermediate Similarity	NPC470979
0.7965	Intermediate Similarity	NPC317107
0.7963	Intermediate Similarity	NPC264477
0.7963	Intermediate Similarity	NPC477511
0.7963	Intermediate Similarity	NPC98225
0.7946	Intermediate Similarity	NPC471934
0.7944	Intermediate Similarity	NPC264378
0.7931	Intermediate Similarity	NPC469684
0.7931	Intermediate Similarity	NPC473590
0.7931	Intermediate Similarity	NPC53396
0.7931	Intermediate Similarity	NPC98249
0.7928	Intermediate Similarity	NPC180744
0.7925	Intermediate Similarity	NPC17585
0.7905	Intermediate Similarity	NPC161998
0.7876	Intermediate Similarity	NPC472214
0.7876	Intermediate Similarity	NPC472215
0.7876	Intermediate Similarity	NPC253906
0.787	Intermediate Similarity	NPC477512
0.7869	Intermediate Similarity	NPC236999
0.7864	Intermediate Similarity	NPC475971
0.7857	Intermediate Similarity	NPC322903
0.7851	Intermediate Similarity	NPC471939
0.7845	Intermediate Similarity	NPC470793
0.7838	Intermediate Similarity	NPC477125
0.7833	Intermediate Similarity	NPC67251
0.7826	Intermediate Similarity	NPC469454
0.7826	Intermediate Similarity	NPC469463
0.7826	Intermediate Similarity	NPC469496
0.7807	Intermediate Similarity	NPC304180
0.7807	Intermediate Similarity	NPC179798
0.7798	Intermediate Similarity	NPC164598
0.7798	Intermediate Similarity	NPC474339
0.7797	Intermediate Similarity	NPC475520
0.7787	Intermediate Similarity	NPC471940
0.7778	Intermediate Similarity	NPC478204
0.7769	Intermediate Similarity	NPC145238
0.7768	Intermediate Similarity	NPC469558
0.7731	Intermediate Similarity	NPC4548
0.7727	Intermediate Similarity	NPC478156
0.7727	Intermediate Similarity	NPC471148
0.7727	Intermediate Similarity	NPC105725
0.7727	Intermediate Similarity	NPC475091
0.7727	Intermediate Similarity	NPC474709
0.7719	Intermediate Similarity	NPC475563
0.7719	Intermediate Similarity	NPC475134
0.7712	Intermediate Similarity	NPC478206
0.7712	Intermediate Similarity	NPC470776
0.7712	Intermediate Similarity	NPC478205
0.7712	Intermediate Similarity	NPC108581
0.7712	Intermediate Similarity	NPC473720
0.7706	Intermediate Similarity	NPC469551
0.7706	Intermediate Similarity	NPC473204
0.7699	Intermediate Similarity	NPC476479
0.7692	Intermediate Similarity	NPC474734
0.7686	Intermediate Similarity	NPC105926
0.7686	Intermediate Similarity	NPC473802
0.7686	Intermediate Similarity	NPC91693
0.7686	Intermediate Similarity	NPC472399
0.7686	Intermediate Similarity	NPC18945
0.7686	Intermediate Similarity	NPC265557
0.7679	Intermediate Similarity	NPC123726
0.7679	Intermediate Similarity	NPC284365
0.7672	Intermediate Similarity	NPC159333
0.7672	Intermediate Similarity	NPC33360
0.7672	Intermediate Similarity	NPC470120
0.7672	Intermediate Similarity	NPC56448
0.7672	Intermediate Similarity	NPC89018
0.7672	Intermediate Similarity	NPC471204
0.767	Intermediate Similarity	NPC266957
0.7667	Intermediate Similarity	NPC470779
0.7652	Intermediate Similarity	NPC469655
0.7652	Intermediate Similarity	NPC475668
0.7652	Intermediate Similarity	NPC475480
0.7652	Intermediate Similarity	NPC469656
0.7652	Intermediate Similarity	NPC470467
0.7652	Intermediate Similarity	NPC473921
0.7652	Intermediate Similarity	NPC474846
0.7647	Intermediate Similarity	NPC156745
0.7647	Intermediate Similarity	NPC472667
0.7647	Intermediate Similarity	NPC236918
0.7642	Intermediate Similarity	NPC476008
0.7642	Intermediate Similarity	NPC476598
0.7642	Intermediate Similarity	NPC476597
0.7636	Intermediate Similarity	NPC308824
0.7632	Intermediate Similarity	NPC474242
0.7632	Intermediate Similarity	NPC475191
0.7627	Intermediate Similarity	NPC58662
0.7627	Intermediate Similarity	NPC23046
0.7627	Intermediate Similarity	NPC176513
0.7627	Intermediate Similarity	NPC470775
0.7623	Intermediate Similarity	NPC473709
0.7623	Intermediate Similarity	NPC473919
0.7623	Intermediate Similarity	NPC24651
0.7623	Intermediate Similarity	NPC476729
0.7619	Intermediate Similarity	NPC475748
0.7615	Intermediate Similarity	NPC318917
0.7615	Intermediate Similarity	NPC476800
0.7615	Intermediate Similarity	NPC472186
0.7615	Intermediate Similarity	NPC471366
0.7611	Intermediate Similarity	NPC266514
0.7611	Intermediate Similarity	NPC184512
0.7611	Intermediate Similarity	NPC302788
0.7611	Intermediate Similarity	NPC187435
0.7611	Intermediate Similarity	NPC67321
0.7611	Intermediate Similarity	NPC477513
0.7607	Intermediate Similarity	NPC226608
0.7607	Intermediate Similarity	NPC88867
0.7603	Intermediate Similarity	NPC23786
0.7603	Intermediate Similarity	NPC470265
0.7603	Intermediate Similarity	NPC312833
0.7603	Intermediate Similarity	NPC162009
0.7603	Intermediate Similarity	NPC257017
0.7596	Intermediate Similarity	NPC477128
0.7589	Intermediate Similarity	NPC258532
0.7589	Intermediate Similarity	NPC470297
0.7589	Intermediate Similarity	NPC146731
0.7589	Intermediate Similarity	NPC472756
0.7589	Intermediate Similarity	NPC239162
0.7586	Intermediate Similarity	NPC470468
0.7586	Intermediate Similarity	NPC269530
0.7586	Intermediate Similarity	NPC222834
0.7583	Intermediate Similarity	NPC185876
0.7583	Intermediate Similarity	NPC471126
0.7583	Intermediate Similarity	NPC475885
0.7583	Intermediate Similarity	NPC143755
0.7583	Intermediate Similarity	NPC472759
0.7583	Intermediate Similarity	NPC157252
0.7583	Intermediate Similarity	NPC145182
0.7583	Intermediate Similarity	NPC329080
0.7583	Intermediate Similarity	NPC19336
0.7583	Intermediate Similarity	NPC471128
0.7573	Intermediate Similarity	NPC50637

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 NPC281624 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	1603
0.2-0.3	3741
0.3-0.4	2330
0.4-0.5	798
0.5-0.6	334
0.6-0.7	116
0.7-0.8	5
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
0.7456	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6648	Approved
0.7265	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7115	Discovery
0.7155	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4225	Approved
0.7034	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5344	Discontinued
0.6972	Remote Similarity	NPD6698	Approved
0.6972	Remote Similarity	NPD46	Approved
0.696	Remote Similarity	NPD8517	Approved
0.696	Remote Similarity	NPD8516	Approved
0.696	Remote Similarity	NPD8515	Approved
0.696	Remote Similarity	NPD8513	Phase 3
0.6923	Remote Similarity	NPD6008	Approved
0.6909	Remote Similarity	NPD7983	Approved
0.688	Remote Similarity	NPD6319	Approved
0.6847	Remote Similarity	NPD5779	Approved
0.6847	Remote Similarity	NPD5778	Approved
0.6833	Remote Similarity	NPD6371	Approved
0.6818	Remote Similarity	NPD7838	Discovery
0.6807	Remote Similarity	NPD6686	Approved
0.6797	Remote Similarity	NPD7492	Approved
0.6786	Remote Similarity	NPD5282	Discontinued
0.6777	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7637	Suspended
0.6746	Remote Similarity	NPD6054	Approved
0.6744	Remote Similarity	NPD6616	Approved
0.6727	Remote Similarity	NPD1695	Approved
0.6721	Remote Similarity	NPD8297	Approved
0.6718	Remote Similarity	NPD7319	Approved
0.6696	Remote Similarity	NPD7638	Approved
0.6693	Remote Similarity	NPD6921	Approved
0.6692	Remote Similarity	NPD7078	Approved
0.6692	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD1694	Approved
0.6641	Remote Similarity	NPD6370	Approved
0.6641	Remote Similarity	NPD7736	Approved
0.664	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6649	Approved
0.6639	Remote Similarity	NPD6650	Approved
0.6638	Remote Similarity	NPD7640	Approved
0.6638	Remote Similarity	NPD7639	Approved
0.6614	Remote Similarity	NPD6059	Approved
0.6612	Remote Similarity	NPD6372	Approved
0.6612	Remote Similarity	NPD6373	Approved
0.6607	Remote Similarity	NPD6411	Approved
0.6589	Remote Similarity	NPD8328	Phase 3
0.6565	Remote Similarity	NPD8293	Discontinued
0.6562	Remote Similarity	NPD6015	Approved
0.6562	Remote Similarity	NPD6016	Approved
0.6542	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6881	Approved
0.6529	Remote Similarity	NPD6899	Approved
0.6512	Remote Similarity	NPD5988	Approved
0.6505	Remote Similarity	NPD8039	Approved
0.65	Remote Similarity	NPD7128	Approved
0.65	Remote Similarity	NPD5739	Approved
0.65	Remote Similarity	NPD6402	Approved
0.65	Remote Similarity	NPD6675	Approved
0.6493	Remote Similarity	NPD7260	Phase 2
0.6489	Remote Similarity	NPD7507	Approved
0.6462	Remote Similarity	NPD7604	Phase 2
0.6452	Remote Similarity	NPD6882	Approved
0.6446	Remote Similarity	NPD5697	Approved
0.6441	Remote Similarity	NPD1700	Approved
0.6435	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6101	Approved
0.6423	Remote Similarity	NPD7290	Approved
0.6423	Remote Similarity	NPD7102	Approved
0.6423	Remote Similarity	NPD6883	Approved
0.641	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6399	Phase 3
0.64	Remote Similarity	NPD4632	Approved
0.6393	Remote Similarity	NPD7320	Approved
0.6389	Remote Similarity	NPD5209	Approved
0.6378	Remote Similarity	NPD6009	Approved
0.6377	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD6869	Approved
0.6371	Remote Similarity	NPD6847	Approved
0.6371	Remote Similarity	NPD6617	Approved
0.6371	Remote Similarity	NPD8130	Phase 1
0.6348	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7900	Approved
0.6341	Remote Similarity	NPD6013	Approved
0.6341	Remote Similarity	NPD6014	Approved
0.6341	Remote Similarity	NPD6012	Approved
0.6339	Remote Similarity	NPD5737	Approved
0.6339	Remote Similarity	NPD6672	Approved
0.6328	Remote Similarity	NPD7327	Approved
0.6328	Remote Similarity	NPD7328	Approved
0.6316	Remote Similarity	NPD5694	Approved
0.6316	Remote Similarity	NPD6050	Approved
0.6316	Remote Similarity	NPD5693	Phase 1
0.6311	Remote Similarity	NPD5701	Approved
0.6308	Remote Similarity	NPD5983	Phase 2
0.6308	Remote Similarity	NPD7503	Approved
0.6293	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD7516	Approved
0.627	Remote Similarity	NPD8133	Approved
0.626	Remote Similarity	NPD6011	Approved
0.6241	Remote Similarity	NPD8273	Phase 1
0.6241	Remote Similarity	NPD6336	Discontinued
0.6239	Remote Similarity	NPD7839	Suspended
0.6228	Remote Similarity	NPD5785	Approved
0.6228	Remote Similarity	NPD5692	Phase 3
0.621	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6845	Suspended
0.6186	Remote Similarity	NPD6083	Phase 2
0.6186	Remote Similarity	NPD7902	Approved
0.6186	Remote Similarity	NPD6084	Phase 2
0.6183	Remote Similarity	NPD8033	Approved
0.6183	Remote Similarity	NPD8296	Approved
0.6183	Remote Similarity	NPD8335	Approved
0.6183	Remote Similarity	NPD8380	Approved
0.6183	Remote Similarity	NPD8379	Approved
0.6183	Remote Similarity	NPD8378	Approved
0.6161	Remote Similarity	NPD6098	Approved
0.616	Remote Similarity	NPD4634	Approved
0.6154	Remote Similarity	NPD5695	Phase 3
0.6148	Remote Similarity	NPD6033	Approved
0.614	Remote Similarity	NPD6080	Approved
0.614	Remote Similarity	NPD6904	Approved
0.614	Remote Similarity	NPD6673	Approved
0.6134	Remote Similarity	NPD5696	Approved
0.6126	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD7632	Discontinued
0.6111	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD8377	Approved
0.6107	Remote Similarity	NPD8294	Approved
0.6106	Remote Similarity	NPD7524	Approved
0.6087	Remote Similarity	NPD5207	Approved
0.6087	Remote Similarity	NPD3168	Discontinued
0.6068	Remote Similarity	NPD7748	Approved
0.6063	Remote Similarity	NPD6053	Discontinued
0.6036	Remote Similarity	NPD6695	Phase 3
0.6034	Remote Similarity	NPD8034	Phase 2
0.6034	Remote Similarity	NPD8035	Phase 2
0.6032	Remote Similarity	NPD2067	Discontinued
0.6031	Remote Similarity	NPD7100	Approved
0.6031	Remote Similarity	NPD7101	Approved
0.6018	Remote Similarity	NPD7146	Approved
0.6018	Remote Similarity	NPD7521	Approved
0.6018	Remote Similarity	NPD6409	Approved
0.6018	Remote Similarity	NPD7334	Approved
0.6018	Remote Similarity	NPD6684	Approved
0.6018	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD8451	Approved
0.6	Remote Similarity	NPD5369	Approved
0.5984	Remote Similarity	NPD5211	Phase 2
0.597	Remote Similarity	NPD7829	Approved
0.597	Remote Similarity	NPD7830	Approved
0.5965	Remote Similarity	NPD4251	Approved
0.5965	Remote Similarity	NPD4250	Approved
0.5965	Remote Similarity	NPD3573	Approved
0.5956	Remote Similarity	NPD8448	Approved
0.5954	Remote Similarity	NPD6335	Approved
0.595	Remote Similarity	NPD5285	Approved
0.595	Remote Similarity	NPD4696	Approved
0.595	Remote Similarity	NPD5286	Approved
0.5946	Remote Similarity	NPD4270	Approved
0.5946	Remote Similarity	NPD4269	Approved
0.5932	Remote Similarity	NPD6001	Approved
0.5923	Remote Similarity	NPD6274	Approved
0.592	Remote Similarity	NPD6412	Phase 2
0.5917	Remote Similarity	NPD4755	Approved
0.5917	Remote Similarity	NPD5959	Approved
0.5913	Remote Similarity	NPD6903	Approved
0.5913	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD7515	Phase 2
0.5897	Remote Similarity	NPD5284	Approved
0.5897	Remote Similarity	NPD5281	Approved
0.5893	Remote Similarity	NPD7154	Phase 3
0.5887	Remote Similarity	NPD5141	Approved
0.5882	Remote Similarity	NPD5654	Approved
0.5878	Remote Similarity	NPD6317	Approved
0.5877	Remote Similarity	NPD4249	Approved
0.5877	Remote Similarity	NPD5786	Approved
0.5854	Remote Similarity	NPD5226	Approved
0.5854	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD4633	Approved
0.5854	Remote Similarity	NPD5225	Approved
0.5854	Remote Similarity	NPD5224	Approved
0.5852	Remote Similarity	NPD7642	Approved
0.5833	Remote Similarity	NPD6314	Approved
0.5833	Remote Similarity	NPD6313	Approved
0.5828	Remote Similarity	NPD7799	Discontinued
0.5827	Remote Similarity	NPD8390	Approved
0.5827	Remote Similarity	NPD5956	Approved
0.5827	Remote Similarity	NPD8392	Approved
0.5827	Remote Similarity	NPD8391	Approved
0.5826	Remote Similarity	NPD7750	Discontinued
0.5821	Remote Similarity	NPD6909	Approved
0.5821	Remote Similarity	NPD6908	Approved
0.5821	Remote Similarity	NPD8444	Approved
0.5821	Remote Similarity	NPD6291	Clinical (unspecified phase)

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