NPASS Compound

Structure

NPC470840 OpenBabel07101718322D 35 38 0 0 1 0 0 0 0 0999 V2000 -4.8047 -1.4946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8159 -1.6437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1017 1.3565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8292 1.7219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5812 -0.5879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9223 -4.5778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6490 -3.8549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2715 -4.6662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2603 -4.5172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7471 -2.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8811 -2.9888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1674 -2.0852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2407 -0.1679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7170 -1.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9459 -1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0101 -2.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7170 -2.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6075 -4.3514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5384 -3.9860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6131 -2.9888 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.3950 -2.7203 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.7603 -3.6511 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.0151 -2.4888 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6774 0.6583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1490 -0.9888 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4394 -2.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6802 0.7331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0151 -1.4888 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7585 -3.5913 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1490 -2.9888 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4585 -5.3402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1774 1.5243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6947 -3.9427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3510 -3.8549 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 26 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 17 1 0 0 0 0 14 25 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 19 1 0 0 0 0 18 31 1 0 0 0 0 19 20 1 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 26 1 0 0 0 0 22 29 1 0 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 32 2 0 0 0 0 25 28 1 6 0 0 0 25 35 1 0 0 0 0 27 35 1 0 0 0 0 28 5 1 6 0 0 0 29 6 1 1 0 0 0 29 33 1 0 0 0 0 30 7 1 1 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.37
Volume:	531.888
LogP:	4.372
LogD:	3.855
LogS:	-4.913
# Rotatable Bonds:	4
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.471
Synthetic Accessibility Score:	5.261
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.749
MDCK Permeability:	2.1184017896302976e-05
Pgp-inhibitor:	0.887
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.92
30% Bioavailability (F30%):	0.354

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.812
Plasma Protein Binding (PPB):	91.72220611572266%
Volume Distribution (VD):	0.999
Pgp-substrate:	4.406722068786621%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.225
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.889
CYP2C9-inhibitor:	0.109
CYP2C9-substrate:	0.444
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.373
CYP3A4-inhibitor:	0.368
CYP3A4-substrate:	0.352

ADMET: Excretion

Clearance (CL):	6.016
Half-life (T1/2):	0.322

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.22
Drug-inuced Liver Injury (DILI):	0.091
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.69
Skin Sensitization:	0.057
Carcinogencity:	0.03
Eye Corrosion:	0.004
Eye Irritation:	0.04
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC470840

Natural Product ID:	NPC470840
*Common Name:**	(5Ar,6R,7S,9Ar)-7-Hydroxy-6-(2-((1R,E)-1-Hydroxy-6-(Hydroxymethyl)-1,4,4-Trimethyl-1,2,3,3A,4,5,8,8A-Octahydroazulen-5-Yl)Ethyl)-2,2,5A,7-Tetramethyl-Octahydrobenzo[B]Oxepin-3(2H)-One
IUPAC Name:	(5aR,6R,7S,9aR)-7-hydroxy-6-[2-[(1R)-1-hydroxy-6-(hydroxymethyl)-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulen-5-yl]ethyl]-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydrobenzo[b]oxepin-3-one
Synonyms:
Standard InCHIKey:	PGXVRJUUHWTBMQ-GGRPBLHXSA-N
Standard InCHI:	InChI=1S/C30H50O5/c1-26(2)20(19(18-31)8-9-22-21(26)12-16-29(22,6)33)10-11-23-28(5)15-13-24(32)27(3,4)35-25(28)14-17-30(23,7)34/h8,20-23,25,31,33-34H,9-18H2,1-7H3/t20?,21?,22?,23-,25-,28-,29-,30+/m1/s1
SMILES:	CC1(C2CCC(C2CC=C(C1CCC3C4(CCC(=O)C(OC4CCC3(C)O)(C)C)C)CO)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226248
PubChem CID:	16737094
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17488128]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19534474]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	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
IC50	6

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1178	Cell Line	KB 3-1	Homo sapiens	IC50	=	6.3	nM	PMID[504581]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	50000.0	nM	PMID[504581]
NPT2	Others	Unspecified		IC50	=	6000.0	nM	PMID[504581]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[504581]

☑ 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 NPC470840 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	196
0.1-0.2	1380
0.2-0.3	5497
0.3-0.4	13568
0.4-0.5	9321
0.5-0.6	7474
0.6-0.7	4650
0.7-0.8	605
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9574	High Similarity	NPC470834
0.9091	High Similarity	NPC470839
0.835	Intermediate Similarity	NPC194323
0.8283	Intermediate Similarity	NPC293086
0.81	Intermediate Similarity	NPC473258
0.8095	Intermediate Similarity	NPC470838
0.8058	Intermediate Similarity	NPC477521
0.8039	Intermediate Similarity	NPC18509
0.802	Intermediate Similarity	NPC134067
0.8	Intermediate Similarity	NPC477520
0.8	Intermediate Similarity	NPC26478
0.7944	Intermediate Similarity	NPC44063
0.7941	Intermediate Similarity	NPC249954
0.7925	Intermediate Similarity	NPC137657
0.7925	Intermediate Similarity	NPC75531
0.7925	Intermediate Similarity	NPC149124
0.7905	Intermediate Similarity	NPC119601
0.7905	Intermediate Similarity	NPC477915
0.7905	Intermediate Similarity	NPC473424
0.7905	Intermediate Similarity	NPC308726
0.7905	Intermediate Similarity	NPC185530
0.7885	Intermediate Similarity	NPC154072
0.7885	Intermediate Similarity	NPC476274
0.7885	Intermediate Similarity	NPC144956
0.7885	Intermediate Similarity	NPC15390
0.7879	Intermediate Similarity	NPC472971
0.7879	Intermediate Similarity	NPC472970
0.787	Intermediate Similarity	NPC217201
0.7864	Intermediate Similarity	NPC69385
0.7864	Intermediate Similarity	NPC254496
0.785	Intermediate Similarity	NPC150531
0.785	Intermediate Similarity	NPC214264
0.785	Intermediate Similarity	NPC171137
0.785	Intermediate Similarity	NPC302607
0.785	Intermediate Similarity	NPC85829
0.785	Intermediate Similarity	NPC48733
0.785	Intermediate Similarity	NPC50692
0.785	Intermediate Similarity	NPC97202
0.785	Intermediate Similarity	NPC260268
0.785	Intermediate Similarity	NPC49958
0.785	Intermediate Similarity	NPC296945
0.785	Intermediate Similarity	NPC202167
0.785	Intermediate Similarity	NPC319077
0.785	Intermediate Similarity	NPC476027
0.785	Intermediate Similarity	NPC152695
0.7843	Intermediate Similarity	NPC259286
0.7838	Intermediate Similarity	NPC73300
0.7838	Intermediate Similarity	NPC108721
0.783	Intermediate Similarity	NPC311612
0.7822	Intermediate Similarity	NPC109414
0.7822	Intermediate Similarity	NPC69454
0.7818	Intermediate Similarity	NPC158523
0.7818	Intermediate Similarity	NPC475937
0.781	Intermediate Similarity	NPC163372
0.781	Intermediate Similarity	NPC237190
0.781	Intermediate Similarity	NPC476223
0.781	Intermediate Similarity	NPC302537
0.781	Intermediate Similarity	NPC224720
0.781	Intermediate Similarity	NPC476240
0.78	Intermediate Similarity	NPC470832
0.7798	Intermediate Similarity	NPC214644
0.7798	Intermediate Similarity	NPC475941
0.7798	Intermediate Similarity	NPC11710
0.7798	Intermediate Similarity	NPC474901
0.7798	Intermediate Similarity	NPC2766
0.7788	Intermediate Similarity	NPC222011
0.7778	Intermediate Similarity	NPC220229
0.7778	Intermediate Similarity	NPC144459
0.7778	Intermediate Similarity	NPC471941
0.7778	Intermediate Similarity	NPC475060
0.7778	Intermediate Similarity	NPC83744
0.7778	Intermediate Similarity	NPC185
0.7767	Intermediate Similarity	NPC49371
0.7757	Intermediate Similarity	NPC204833
0.7757	Intermediate Similarity	NPC209502
0.7757	Intermediate Similarity	NPC29705
0.7755	Intermediate Similarity	NPC202394
0.7748	Intermediate Similarity	NPC207251
0.7745	Intermediate Similarity	NPC212812
0.7736	Intermediate Similarity	NPC87351
0.7736	Intermediate Similarity	NPC136289
0.7736	Intermediate Similarity	NPC118405
0.7727	Intermediate Similarity	NPC153036
0.7727	Intermediate Similarity	NPC76084
0.7723	Intermediate Similarity	NPC168027
0.7723	Intermediate Similarity	NPC185936
0.7723	Intermediate Similarity	NPC63748
0.7714	Intermediate Similarity	NPC83709
0.7714	Intermediate Similarity	NPC112167
0.7706	Intermediate Similarity	NPC329417
0.7706	Intermediate Similarity	NPC94529
0.77	Intermediate Similarity	NPC474245
0.77	Intermediate Similarity	NPC474679
0.77	Intermediate Similarity	NPC76879
0.77	Intermediate Similarity	NPC2983
0.7692	Intermediate Similarity	NPC285513
0.7692	Intermediate Similarity	NPC190554
0.7692	Intermediate Similarity	NPC107243
0.7685	Intermediate Similarity	NPC60681
0.7685	Intermediate Similarity	NPC257353
0.7685	Intermediate Similarity	NPC149047
0.7684	Intermediate Similarity	NPC306095
0.7679	Intermediate Similarity	NPC71889
0.7679	Intermediate Similarity	NPC317210
0.7679	Intermediate Similarity	NPC962
0.7679	Intermediate Similarity	NPC250109
0.767	Intermediate Similarity	NPC470974
0.767	Intermediate Similarity	NPC91408
0.767	Intermediate Similarity	NPC472932
0.767	Intermediate Similarity	NPC470978
0.7664	Intermediate Similarity	NPC469985
0.7664	Intermediate Similarity	NPC111323
0.7664	Intermediate Similarity	NPC90177
0.7664	Intermediate Similarity	NPC236390
0.7664	Intermediate Similarity	NPC191892
0.7653	Intermediate Similarity	NPC36350
0.7647	Intermediate Similarity	NPC472930
0.7642	Intermediate Similarity	NPC476897
0.7642	Intermediate Similarity	NPC81530
0.7636	Intermediate Similarity	NPC163004
0.7632	Intermediate Similarity	NPC471854
0.7624	Intermediate Similarity	NPC134321
0.7624	Intermediate Similarity	NPC320026
0.7619	Intermediate Similarity	NPC48647
0.7619	Intermediate Similarity	NPC186810
0.7615	Intermediate Similarity	NPC477916
0.7611	Intermediate Similarity	NPC326542
0.7611	Intermediate Similarity	NPC474872
0.7607	Intermediate Similarity	NPC222688
0.7596	Intermediate Similarity	NPC160056
0.7589	Intermediate Similarity	NPC475970
0.7586	Intermediate Similarity	NPC109973
0.7576	Intermediate Similarity	NPC469994
0.7573	Intermediate Similarity	NPC111015
0.7573	Intermediate Similarity	NPC8993
0.7573	Intermediate Similarity	NPC299100
0.757	Intermediate Similarity	NPC204450
0.757	Intermediate Similarity	NPC195290
0.7565	Intermediate Similarity	NPC472397
0.7565	Intermediate Similarity	NPC471125
0.7565	Intermediate Similarity	NPC472758
0.7565	Intermediate Similarity	NPC171905
0.7549	Intermediate Similarity	NPC248913
0.7549	Intermediate Similarity	NPC472978
0.7549	Intermediate Similarity	NPC473998
0.7549	Intermediate Similarity	NPC475806
0.7547	Intermediate Similarity	NPC218383
0.7545	Intermediate Similarity	NPC65941
0.7545	Intermediate Similarity	NPC177064
0.7544	Intermediate Similarity	NPC266728
0.7544	Intermediate Similarity	NPC49492
0.7525	Intermediate Similarity	NPC275740
0.7525	Intermediate Similarity	NPC123912
0.7525	Intermediate Similarity	NPC473999
0.7525	Intermediate Similarity	NPC472973
0.7525	Intermediate Similarity	NPC309603
0.7525	Intermediate Similarity	NPC86319
0.7524	Intermediate Similarity	NPC474977
0.7524	Intermediate Similarity	NPC57416
0.7524	Intermediate Similarity	NPC18319
0.7524	Intermediate Similarity	NPC475894
0.7523	Intermediate Similarity	NPC472645
0.7523	Intermediate Similarity	NPC60315
0.7523	Intermediate Similarity	NPC166607
0.7523	Intermediate Similarity	NPC231530
0.7523	Intermediate Similarity	NPC196528
0.7523	Intermediate Similarity	NPC50535
0.7523	Intermediate Similarity	NPC278628
0.7522	Intermediate Similarity	NPC202889
0.7522	Intermediate Similarity	NPC477091
0.7522	Intermediate Similarity	NPC472926
0.7521	Intermediate Similarity	NPC472401
0.75	Intermediate Similarity	NPC475334
0.75	Intermediate Similarity	NPC471108
0.75	Intermediate Similarity	NPC174471
0.75	Intermediate Similarity	NPC475623
0.75	Intermediate Similarity	NPC316215
0.75	Intermediate Similarity	NPC247957
0.75	Intermediate Similarity	NPC473694
0.75	Intermediate Similarity	NPC22628
0.75	Intermediate Similarity	NPC43775
0.75	Intermediate Similarity	NPC5991
0.75	Intermediate Similarity	NPC249187
0.75	Intermediate Similarity	NPC184848
0.75	Intermediate Similarity	NPC272617
0.75	Intermediate Similarity	NPC469599
0.75	Intermediate Similarity	NPC69548
0.75	Intermediate Similarity	NPC255081
0.75	Intermediate Similarity	NPC180950
0.75	Intermediate Similarity	NPC260786
0.75	Intermediate Similarity	NPC275696
0.75	Intermediate Similarity	NPC271195
0.75	Intermediate Similarity	NPC474871
0.75	Intermediate Similarity	NPC117185
0.75	Intermediate Similarity	NPC317590
0.75	Intermediate Similarity	NPC472495
0.75	Intermediate Similarity	NPC96739
0.75	Intermediate Similarity	NPC5989
0.75	Intermediate Similarity	NPC140723
0.7478	Intermediate Similarity	NPC153651

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 NPC470840 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1824
0.2-0.3	4178
0.3-0.4	2084
0.4-0.5	471
0.5-0.6	206
0.6-0.7	139
0.7-0.8	81
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
0.819	Intermediate Similarity	NPD6402	Approved
0.819	Intermediate Similarity	NPD7128	Approved
0.819	Intermediate Similarity	NPD5739	Approved
0.819	Intermediate Similarity	NPD6675	Approved
0.8077	Intermediate Similarity	NPD5211	Phase 2
0.8039	Intermediate Similarity	NPD4755	Approved
0.8037	Intermediate Similarity	NPD7320	Approved
0.8037	Intermediate Similarity	NPD6899	Approved
0.8037	Intermediate Similarity	NPD6881	Approved
0.7963	Intermediate Similarity	NPD6373	Approved
0.7963	Intermediate Similarity	NPD6372	Approved
0.7944	Intermediate Similarity	NPD5701	Approved
0.7944	Intermediate Similarity	NPD5697	Approved
0.7925	Intermediate Similarity	NPD5141	Approved
0.789	Intermediate Similarity	NPD7102	Approved
0.789	Intermediate Similarity	NPD7290	Approved
0.789	Intermediate Similarity	NPD6883	Approved
0.7885	Intermediate Similarity	NPD5286	Approved
0.7885	Intermediate Similarity	NPD4700	Approved
0.7885	Intermediate Similarity	NPD4696	Approved
0.7885	Intermediate Similarity	NPD5285	Approved
0.787	Intermediate Similarity	NPD6011	Approved
0.7818	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD8130	Phase 1
0.7818	Intermediate Similarity	NPD6869	Approved
0.7818	Intermediate Similarity	NPD6649	Approved
0.7818	Intermediate Similarity	NPD6617	Approved
0.7818	Intermediate Similarity	NPD6847	Approved
0.7818	Intermediate Similarity	NPD6650	Approved
0.781	Intermediate Similarity	NPD5223	Approved
0.7798	Intermediate Similarity	NPD6013	Approved
0.7798	Intermediate Similarity	NPD6012	Approved
0.7798	Intermediate Similarity	NPD6014	Approved
0.7748	Intermediate Similarity	NPD6882	Approved
0.7748	Intermediate Similarity	NPD8297	Approved
0.7736	Intermediate Similarity	NPD4633	Approved
0.7736	Intermediate Similarity	NPD5225	Approved
0.7736	Intermediate Similarity	NPD5224	Approved
0.7736	Intermediate Similarity	NPD5226	Approved
0.7664	Intermediate Similarity	NPD4754	Approved
0.7664	Intermediate Similarity	NPD5174	Approved
0.7664	Intermediate Similarity	NPD5175	Approved
0.7525	Intermediate Similarity	NPD5328	Approved
0.7524	Intermediate Similarity	NPD6084	Phase 2
0.7524	Intermediate Similarity	NPD6083	Phase 2
0.7523	Intermediate Similarity	NPD4767	Approved
0.7523	Intermediate Similarity	NPD4768	Approved
0.7476	Intermediate Similarity	NPD4202	Approved
0.7429	Intermediate Similarity	NPD5222	Approved
0.7429	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4697	Phase 3
0.7429	Intermediate Similarity	NPD5221	Approved
0.7414	Intermediate Similarity	NPD6335	Approved
0.7391	Intermediate Similarity	NPD6274	Approved
0.7387	Intermediate Similarity	NPD4729	Approved
0.7387	Intermediate Similarity	NPD5128	Approved
0.7387	Intermediate Similarity	NPD4730	Approved
0.7379	Intermediate Similarity	NPD6079	Approved
0.7358	Intermediate Similarity	NPD5173	Approved
0.7353	Intermediate Similarity	NPD4753	Phase 2
0.735	Intermediate Similarity	NPD7100	Approved
0.735	Intermediate Similarity	NPD7101	Approved
0.7333	Intermediate Similarity	NPD5695	Phase 3
0.7328	Intermediate Similarity	NPD6317	Approved
0.7288	Intermediate Similarity	NPD6059	Approved
0.7288	Intermediate Similarity	NPD6054	Approved
0.7265	Intermediate Similarity	NPD6313	Approved
0.7265	Intermediate Similarity	NPD6314	Approved
0.7257	Intermediate Similarity	NPD4634	Approved
0.7257	Intermediate Similarity	NPD5247	Approved
0.7257	Intermediate Similarity	NPD5135	Approved
0.7257	Intermediate Similarity	NPD5249	Phase 3
0.7257	Intermediate Similarity	NPD5248	Approved
0.7257	Intermediate Similarity	NPD5169	Approved
0.7257	Intermediate Similarity	NPD5251	Approved
0.7257	Intermediate Similarity	NPD5250	Approved
0.7257	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD6909	Approved
0.7227	Intermediate Similarity	NPD6908	Approved
0.7217	Intermediate Similarity	NPD4632	Approved
0.72	Intermediate Similarity	NPD4786	Approved
0.7193	Intermediate Similarity	NPD5216	Approved
0.7193	Intermediate Similarity	NPD5217	Approved
0.7193	Intermediate Similarity	NPD5127	Approved
0.7193	Intermediate Similarity	NPD5215	Approved
0.7179	Intermediate Similarity	NPD6009	Approved
0.7167	Intermediate Similarity	NPD6370	Approved
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.7143	Intermediate Similarity	NPD6319	Approved
0.713	Intermediate Similarity	NPD5696	Approved
0.7129	Intermediate Similarity	NPD5329	Approved
0.7107	Intermediate Similarity	NPD7604	Phase 2
0.7083	Intermediate Similarity	NPD5983	Phase 2
0.7083	Intermediate Similarity	NPD6016	Approved
0.7083	Intermediate Similarity	NPD6015	Approved
0.7064	Intermediate Similarity	NPD7640	Approved
0.7064	Intermediate Similarity	NPD7639	Approved
0.7059	Intermediate Similarity	NPD6098	Approved
0.7059	Intermediate Similarity	NPD5279	Phase 3
0.7059	Intermediate Similarity	NPD3618	Phase 1
0.7049	Intermediate Similarity	NPD7492	Approved
0.703	Intermediate Similarity	NPD3666	Approved
0.703	Intermediate Similarity	NPD3665	Phase 1
0.703	Intermediate Similarity	NPD3133	Approved
0.703	Intermediate Similarity	NPD4197	Approved
0.7025	Intermediate Similarity	NPD5988	Approved
0.7019	Intermediate Similarity	NPD6673	Approved
0.7019	Intermediate Similarity	NPD6080	Approved
0.7019	Intermediate Similarity	NPD6904	Approved
0.7009	Intermediate Similarity	NPD5167	Approved
0.7009	Intermediate Similarity	NPD5210	Approved
0.7009	Intermediate Similarity	NPD4629	Approved
0.7	Intermediate Similarity	NPD3667	Approved
0.7	Intermediate Similarity	NPD6435	Approved
0.6992	Remote Similarity	NPD6616	Approved
0.6992	Remote Similarity	NPD6336	Discontinued
0.6972	Remote Similarity	NPD7638	Approved
0.697	Remote Similarity	NPD7525	Registered
0.6949	Remote Similarity	NPD6868	Approved
0.6942	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD8293	Discontinued
0.6935	Remote Similarity	NPD7078	Approved
0.6931	Remote Similarity	NPD5362	Discontinued
0.6923	Remote Similarity	NPD6672	Approved
0.6923	Remote Similarity	NPD5737	Approved
0.6903	Remote Similarity	NPD6008	Approved
0.6893	Remote Similarity	NPD5786	Approved
0.6893	Remote Similarity	NPD4694	Approved
0.6893	Remote Similarity	NPD5280	Approved
0.6893	Remote Similarity	NPD5690	Phase 2
0.6887	Remote Similarity	NPD5693	Phase 1
0.6887	Remote Similarity	NPD6050	Approved
0.688	Remote Similarity	NPD7736	Approved
0.688	Remote Similarity	NPD6033	Approved
0.6838	Remote Similarity	NPD6053	Discontinued
0.6832	Remote Similarity	NPD4221	Approved
0.6832	Remote Similarity	NPD4223	Phase 3
0.68	Remote Similarity	NPD5368	Approved
0.6792	Remote Similarity	NPD5692	Phase 3
0.6783	Remote Similarity	NPD5168	Approved
0.6765	Remote Similarity	NPD4788	Approved
0.675	Remote Similarity	NPD7115	Discovery
0.6731	Remote Similarity	NPD6409	Approved
0.6731	Remote Similarity	NPD5330	Approved
0.6731	Remote Similarity	NPD7521	Approved
0.6731	Remote Similarity	NPD6684	Approved
0.6731	Remote Similarity	NPD7334	Approved
0.6731	Remote Similarity	NPD7146	Approved
0.6729	Remote Similarity	NPD8034	Phase 2
0.6729	Remote Similarity	NPD5694	Approved
0.6729	Remote Similarity	NPD8035	Phase 2
0.672	Remote Similarity	NPD7507	Approved
0.6699	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6636	Remote Similarity	NPD5785	Approved
0.6635	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4821	Approved
0.6634	Remote Similarity	NPD4819	Approved
0.6634	Remote Similarity	NPD4820	Approved
0.6634	Remote Similarity	NPD4822	Approved
0.6606	Remote Similarity	NPD7748	Approved
0.6604	Remote Similarity	NPD6903	Approved
0.6604	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6695	Phase 3
0.6577	Remote Similarity	NPD7902	Approved
0.6574	Remote Similarity	NPD5281	Approved
0.6574	Remote Similarity	NPD5284	Approved
0.6574	Remote Similarity	NPD7515	Phase 2
0.6571	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4690	Approved
0.6571	Remote Similarity	NPD4689	Approved
0.6571	Remote Similarity	NPD4138	Approved
0.6571	Remote Similarity	NPD4688	Approved
0.6571	Remote Similarity	NPD5205	Approved
0.6571	Remote Similarity	NPD4693	Phase 3
0.6569	Remote Similarity	NPD5369	Approved
0.6562	Remote Similarity	NPD7319	Approved
0.6552	Remote Similarity	NPD6412	Phase 2
0.6538	Remote Similarity	NPD3668	Phase 3
0.6514	Remote Similarity	NPD5779	Approved
0.6514	Remote Similarity	NPD5778	Approved
0.6509	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7632	Discontinued
0.6476	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD1696	Phase 3
0.6476	Remote Similarity	NPD5363	Approved
0.6471	Remote Similarity	NPD4252	Approved
0.6442	Remote Similarity	NPD7154	Phase 3
0.6442	Remote Similarity	NPD5332	Approved
0.6442	Remote Similarity	NPD5331	Approved
0.6436	Remote Similarity	NPD4268	Approved
0.6436	Remote Similarity	NPD4271	Approved
0.6422	Remote Similarity	NPD7637	Suspended
0.6422	Remote Similarity	NPD6411	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