NPASS Compound

Structure

NPC128644 OpenBabel07101719142D 35 37 0 0 1 0 0 0 0 0999 V2000 -3.3729 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3743 -5.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6507 -5.2453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1733 -0.8432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4472 0.4027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8677 -3.6398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5812 -1.6865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3234 -3.8159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3416 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1470 -0.8432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2758 -4.0183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0226 -2.8899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6602 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7693 -0.1860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7693 -1.7614 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8432 -0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1207 -0.8432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5767 -4.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 0.0000 C 0 0 1 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 2.0701 -2.6874 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6075 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5291 -5.1468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1441 -2.9883 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6075 -1.6865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 2 0 0 0 0 2 21 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 9 35 1 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 25 1 0 0 0 0 13 20 1 0 0 0 0 13 22 1 0 0 0 0 14 19 1 0 0 0 0 14 24 1 0 0 0 0 15 18 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 31 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 30 1 0 0 0 0 21 22 1 0 0 0 0 22 28 1 6 0 0 0 23 24 1 0 0 0 0 23 29 1 1 0 0 0 24 31 1 6 0 0 0 25 28 1 6 0 0 0 25 30 1 0 0 0 0 26 32 2 0 0 0 0 26 35 1 0 0 0 0 27 33 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 6 0 0 0 31 8 1 1 0 0 0 31 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.39
Volume:	546.314
LogP:	5.657
LogD:	4.751
LogS:	-5.201
# Rotatable Bonds:	9
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.29
Synthetic Accessibility Score:	4.959
Fsp3:	0.839
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.698
MDCK Permeability:	3.292835390311666e-05
Pgp-inhibitor:	0.958
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.664

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.102
Plasma Protein Binding (PPB):	89.66043853759766%
Volume Distribution (VD):	0.784
Pgp-substrate:	4.678965091705322%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.257
CYP2C19-inhibitor:	0.106
CYP2C19-substrate:	0.92
CYP2C9-inhibitor:	0.26
CYP2C9-substrate:	0.229
CYP2D6-inhibitor:	0.108
CYP2D6-substrate:	0.401
CYP3A4-inhibitor:	0.877
CYP3A4-substrate:	0.559

ADMET: Excretion

Clearance (CL):	5.456
Half-life (T1/2):	0.233

ADMET: Toxicity

hERG Blockers:	0.165
Human Hepatotoxicity (H-HT):	0.339
Drug-inuced Liver Injury (DILI):	0.092
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.461
Skin Sensitization:	0.939
Carcinogencity:	0.104
Eye Corrosion:	0.129
Eye Irritation:	0.071
Respiratory Toxicity:	0.609

Download Data

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

Natural Product: NPC128644

Natural Product ID:	NPC128644
*Common Name:**	(20S,23E)-20,25-Dihydroxy-3,4-Secodammara-4(28),23-Dienoic Acid Methyl Ester
IUPAC Name:	methyl 3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-3-[(E,2S)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,3a,4,5,5a,7,8,9-decahydrocyclopenta[a]naphthalen-6-yl]propanoate
Synonyms:
Standard InCHIKey:	LCXMNWRVOPYUAP-VMKFJFSKSA-N
Standard InCHI:	InChI=1S/C31H52O4/c1-21(2)22-13-20-30(7)25(28(22,5)18-15-26(32)35-9)12-11-23-24(14-19-29(23,30)6)31(8,34)17-10-16-27(3,4)33/h10,16,22-25,33-34H,1,11-15,17-20H2,2-9H3/b16-10+/t22-,23+,24-,25+,28-,29+,30+,31-/m0/s1
SMILES:	COC(=O)CC[C@@]1(C)[C@@H](CC[C@@]2([C@@H]1CC[C@H]1[C@@]2(C)CC[C@@H]1[C@](C/C=C/C(O)(C)C)(O)C)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477755
PubChem CID:	44575599
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids

*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
NPO3427	Aglaia rubiginosa	Species	Meliaceae	Eukaryota	twigs and leaves	n.a.	n.a.	PMID[15043407]
NPO3427	Aglaia rubiginosa	Species	Meliaceae	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
EC50	1
ED50	5

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1851	Cell Line	Col2	Homo sapiens	EC50	>	1000.0	nM	PMID[500665]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	>	1.0	10'3nM	PMID[500665]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	1.0	10'3nM	PMID[500665]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	1.0	10'3nM	PMID[500665]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	1.0	10'3nM	PMID[500665]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	1.0	10'3nM	PMID[500665]

☑ 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 NPC128644 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	151
0.1-0.2	897
0.2-0.3	4020
0.3-0.4	13052
0.4-0.5	9666
0.5-0.6	6792
0.6-0.7	5688
0.7-0.8	2195
0.8-0.85	203
0.85-0.9	28
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9753	High Similarity	NPC269638
0.9176	High Similarity	NPC472870
0.907	High Similarity	NPC66344
0.8953	High Similarity	NPC117122
0.8941	High Similarity	NPC472869
0.8864	High Similarity	NPC473986
0.8864	High Similarity	NPC474018
0.8851	High Similarity	NPC262043
0.8837	High Similarity	NPC236618
0.8837	High Similarity	NPC136948
0.8824	High Similarity	NPC283733
0.8791	High Similarity	NPC107243
0.8764	High Similarity	NPC472871
0.875	High Similarity	NPC472866
0.8721	High Similarity	NPC186975
0.8706	High Similarity	NPC165064
0.8706	High Similarity	NPC164577
0.8706	High Similarity	NPC476038
0.8706	High Similarity	NPC194937
0.8706	High Similarity	NPC19849
0.8706	High Similarity	NPC472864
0.8659	High Similarity	NPC179028
0.8659	High Similarity	NPC321514
0.8652	High Similarity	NPC470113
0.8588	High Similarity	NPC167103
0.8588	High Similarity	NPC477852
0.8588	High Similarity	NPC97913
0.8588	High Similarity	NPC310470
0.8588	High Similarity	NPC477373
0.8587	High Similarity	NPC57416
0.8571	High Similarity	NPC293052
0.8571	High Similarity	NPC147066
0.8554	High Similarity	NPC477371
0.8554	High Similarity	NPC158846
0.8506	High Similarity	NPC155011
0.8495	Intermediate Similarity	NPC98868
0.8488	Intermediate Similarity	NPC472865
0.8478	Intermediate Similarity	NPC235053
0.8471	Intermediate Similarity	NPC133391
0.8471	Intermediate Similarity	NPC260956
0.8462	Intermediate Similarity	NPC292793
0.8444	Intermediate Similarity	NPC476187
0.8444	Intermediate Similarity	NPC204341
0.8434	Intermediate Similarity	NPC239098
0.8427	Intermediate Similarity	NPC36668
0.8427	Intermediate Similarity	NPC118011
0.8427	Intermediate Similarity	NPC2983
0.8427	Intermediate Similarity	NPC474570
0.8427	Intermediate Similarity	NPC476733
0.8427	Intermediate Similarity	NPC215029
0.8427	Intermediate Similarity	NPC128496
0.8409	Intermediate Similarity	NPC96496
0.8409	Intermediate Similarity	NPC167877
0.8404	Intermediate Similarity	NPC266955
0.8395	Intermediate Similarity	NPC18819
0.8395	Intermediate Similarity	NPC46610
0.8391	Intermediate Similarity	NPC471224
0.8391	Intermediate Similarity	NPC29447
0.8387	Intermediate Similarity	NPC126815
0.8387	Intermediate Similarity	NPC475894
0.8372	Intermediate Similarity	NPC215893
0.837	Intermediate Similarity	NPC84383
0.837	Intermediate Similarity	NPC476174
0.8353	Intermediate Similarity	NPC38350
0.8353	Intermediate Similarity	NPC229584
0.8353	Intermediate Similarity	NPC40228
0.8353	Intermediate Similarity	NPC232625
0.8353	Intermediate Similarity	NPC14203
0.8353	Intermediate Similarity	NPC201912
0.8353	Intermediate Similarity	NPC327002
0.8353	Intermediate Similarity	NPC477372
0.8333	Intermediate Similarity	NPC477149
0.8333	Intermediate Similarity	NPC471896
0.8333	Intermediate Similarity	NPC469400
0.8333	Intermediate Similarity	NPC215843
0.8333	Intermediate Similarity	NPC320026
0.8333	Intermediate Similarity	NPC477147
0.8316	Intermediate Similarity	NPC115899
0.8313	Intermediate Similarity	NPC61952
0.8313	Intermediate Similarity	NPC66105
0.8295	Intermediate Similarity	NPC475007
0.8295	Intermediate Similarity	NPC322159
0.8295	Intermediate Similarity	NPC264127
0.8295	Intermediate Similarity	NPC82979
0.828	Intermediate Similarity	NPC250757
0.828	Intermediate Similarity	NPC29152
0.828	Intermediate Similarity	NPC322063
0.828	Intermediate Similarity	NPC301534
0.828	Intermediate Similarity	NPC328371
0.8276	Intermediate Similarity	NPC248758
0.8261	Intermediate Similarity	NPC8993
0.8261	Intermediate Similarity	NPC469406
0.8256	Intermediate Similarity	NPC296367
0.8256	Intermediate Similarity	NPC320514
0.8256	Intermediate Similarity	NPC240302
0.8242	Intermediate Similarity	NPC154101
0.8242	Intermediate Similarity	NPC475806
0.8242	Intermediate Similarity	NPC26888
0.8242	Intermediate Similarity	NPC177641
0.8235	Intermediate Similarity	NPC104545
0.8235	Intermediate Similarity	NPC37038
0.8222	Intermediate Similarity	NPC155479
0.8222	Intermediate Similarity	NPC474704
0.8222	Intermediate Similarity	NPC475921
0.8222	Intermediate Similarity	NPC214387
0.8214	Intermediate Similarity	NPC321690
0.8214	Intermediate Similarity	NPC198240
0.8211	Intermediate Similarity	NPC477521
0.8211	Intermediate Similarity	NPC241221
0.8202	Intermediate Similarity	NPC142361
0.8202	Intermediate Similarity	NPC474684
0.8193	Intermediate Similarity	NPC246445
0.8193	Intermediate Similarity	NPC69143
0.8191	Intermediate Similarity	NPC156546
0.8191	Intermediate Similarity	NPC291634
0.8182	Intermediate Similarity	NPC472218
0.8182	Intermediate Similarity	NPC472219
0.8182	Intermediate Similarity	NPC474083
0.8182	Intermediate Similarity	NPC472217
0.8172	Intermediate Similarity	NPC171395
0.8172	Intermediate Similarity	NPC318282
0.8172	Intermediate Similarity	NPC469995
0.8172	Intermediate Similarity	NPC33473
0.8172	Intermediate Similarity	NPC279974
0.8172	Intermediate Similarity	NPC469599
0.8172	Intermediate Similarity	NPC174948
0.8172	Intermediate Similarity	NPC173875
0.8161	Intermediate Similarity	NPC83569
0.8161	Intermediate Similarity	NPC168188
0.8161	Intermediate Similarity	NPC3856
0.8161	Intermediate Similarity	NPC279639
0.8161	Intermediate Similarity	NPC470015
0.8161	Intermediate Similarity	NPC69279
0.8152	Intermediate Similarity	NPC243866
0.8152	Intermediate Similarity	NPC474736
0.8144	Intermediate Similarity	NPC72151
0.8144	Intermediate Similarity	NPC475050
0.8144	Intermediate Similarity	NPC222153
0.8144	Intermediate Similarity	NPC476237
0.8132	Intermediate Similarity	NPC48010
0.8132	Intermediate Similarity	NPC148414
0.8132	Intermediate Similarity	NPC175628
0.8132	Intermediate Similarity	NPC111585
0.8125	Intermediate Similarity	NPC99411
0.8125	Intermediate Similarity	NPC224720
0.8125	Intermediate Similarity	NPC476240
0.8125	Intermediate Similarity	NPC476223
0.8125	Intermediate Similarity	NPC282524
0.8118	Intermediate Similarity	NPC231431
0.8118	Intermediate Similarity	NPC118987
0.8118	Intermediate Similarity	NPC274996
0.8118	Intermediate Similarity	NPC327674
0.8118	Intermediate Similarity	NPC199595
0.8118	Intermediate Similarity	NPC196827
0.8111	Intermediate Similarity	NPC97884
0.8111	Intermediate Similarity	NPC242864
0.8111	Intermediate Similarity	NPC472220
0.8111	Intermediate Similarity	NPC294480
0.8105	Intermediate Similarity	NPC477854
0.8105	Intermediate Similarity	NPC235464
0.8105	Intermediate Similarity	NPC166745
0.8105	Intermediate Similarity	NPC57079
0.8105	Intermediate Similarity	NPC108368
0.8105	Intermediate Similarity	NPC197386
0.8095	Intermediate Similarity	NPC238227
0.8095	Intermediate Similarity	NPC91665
0.809	Intermediate Similarity	NPC70661
0.809	Intermediate Similarity	NPC324063
0.809	Intermediate Similarity	NPC73038
0.809	Intermediate Similarity	NPC469994
0.809	Intermediate Similarity	NPC473226
0.8085	Intermediate Similarity	NPC472941
0.8085	Intermediate Similarity	NPC155676
0.8085	Intermediate Similarity	NPC456
0.8081	Intermediate Similarity	NPC473284
0.8081	Intermediate Similarity	NPC475294
0.8072	Intermediate Similarity	NPC476844
0.8072	Intermediate Similarity	NPC279666
0.8072	Intermediate Similarity	NPC192540
0.8068	Intermediate Similarity	NPC100391
0.8068	Intermediate Similarity	NPC156981
0.8068	Intermediate Similarity	NPC59453
0.8068	Intermediate Similarity	NPC263974
0.8068	Intermediate Similarity	NPC221758
0.8065	Intermediate Similarity	NPC124207
0.8065	Intermediate Similarity	NPC7165
0.8065	Intermediate Similarity	NPC474690
0.8065	Intermediate Similarity	NPC299100
0.8061	Intermediate Similarity	NPC472868
0.8046	Intermediate Similarity	NPC469804
0.8046	Intermediate Similarity	NPC321289
0.8046	Intermediate Similarity	NPC469799
0.8046	Intermediate Similarity	NPC469806
0.8046	Intermediate Similarity	NPC469805
0.8046	Intermediate Similarity	NPC327969
0.8046	Intermediate Similarity	NPC100297
0.8046	Intermediate Similarity	NPC472239
0.8043	Intermediate Similarity	NPC45269
0.8043	Intermediate Similarity	NPC471747
0.8043	Intermediate Similarity	NPC189520

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 NPC128644 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	1127
0.2-0.3	3632
0.3-0.4	2801
0.4-0.5	863
0.5-0.6	251
0.6-0.7	185
0.7-0.8	150
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8352	Intermediate Similarity	NPD6399	Phase 3
0.8068	Intermediate Similarity	NPD4786	Approved
0.8	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6083	Phase 2
0.8	Intermediate Similarity	NPD6084	Phase 2
0.7955	Intermediate Similarity	NPD5362	Discontinued
0.7912	Intermediate Similarity	NPD6672	Approved
0.7912	Intermediate Similarity	NPD5737	Approved
0.7889	Intermediate Similarity	NPD6098	Approved
0.7849	Intermediate Similarity	NPD5281	Approved
0.7849	Intermediate Similarity	NPD7637	Suspended
0.7849	Intermediate Similarity	NPD5284	Approved
0.7841	Intermediate Similarity	NPD4221	Approved
0.7841	Intermediate Similarity	NPD3667	Approved
0.7841	Intermediate Similarity	NPD4223	Phase 3
0.7826	Intermediate Similarity	NPD6080	Approved
0.7826	Intermediate Similarity	NPD6904	Approved
0.7826	Intermediate Similarity	NPD6673	Approved
0.7789	Intermediate Similarity	NPD5695	Phase 3
0.7778	Intermediate Similarity	NPD5329	Approved
0.7732	Intermediate Similarity	NPD5696	Approved
0.7692	Intermediate Similarity	NPD5330	Approved
0.7692	Intermediate Similarity	NPD4623	Approved
0.7692	Intermediate Similarity	NPD6684	Approved
0.7692	Intermediate Similarity	NPD7521	Approved
0.7692	Intermediate Similarity	NPD7146	Approved
0.7692	Intermediate Similarity	NPD6409	Approved
0.7692	Intermediate Similarity	NPD4519	Discontinued
0.7692	Intermediate Similarity	NPD7334	Approved
0.7667	Intermediate Similarity	NPD4197	Approved
0.766	Intermediate Similarity	NPD5693	Phase 1
0.7653	Intermediate Similarity	NPD7640	Approved
0.7653	Intermediate Similarity	NPD7639	Approved
0.764	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD4753	Phase 2
0.7604	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD7115	Discovery
0.7551	Intermediate Similarity	NPD7638	Approved
0.7529	Intermediate Similarity	NPD4784	Approved
0.7529	Intermediate Similarity	NPD4785	Approved
0.7527	Intermediate Similarity	NPD6903	Approved
0.7527	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD5208	Approved
0.75	Intermediate Similarity	NPD4693	Phase 3
0.75	Intermediate Similarity	NPD4690	Approved
0.75	Intermediate Similarity	NPD4138	Approved
0.75	Intermediate Similarity	NPD5205	Approved
0.75	Intermediate Similarity	NPD5690	Phase 2
0.75	Intermediate Similarity	NPD4689	Approved
0.75	Intermediate Similarity	NPD4688	Approved
0.7476	Intermediate Similarity	NPD6881	Approved
0.7476	Intermediate Similarity	NPD6899	Approved
0.7474	Intermediate Similarity	NPD5694	Approved
0.7474	Intermediate Similarity	NPD6079	Approved
0.7474	Intermediate Similarity	NPD8035	Phase 2
0.7474	Intermediate Similarity	NPD6050	Approved
0.7474	Intermediate Similarity	NPD8034	Phase 2
0.7473	Intermediate Similarity	NPD3666	Approved
0.7473	Intermediate Similarity	NPD3668	Phase 3
0.7473	Intermediate Similarity	NPD3665	Phase 1
0.7473	Intermediate Similarity	NPD3133	Approved
0.7451	Intermediate Similarity	NPD6675	Approved
0.7451	Intermediate Similarity	NPD7128	Approved
0.7451	Intermediate Similarity	NPD6402	Approved
0.7451	Intermediate Similarity	NPD5739	Approved
0.7447	Intermediate Similarity	NPD5328	Approved
0.7447	Intermediate Similarity	NPD6051	Approved
0.7444	Intermediate Similarity	NPD4270	Approved
0.7444	Intermediate Similarity	NPD4269	Approved
0.7423	Intermediate Similarity	NPD5210	Approved
0.7423	Intermediate Similarity	NPD4629	Approved
0.7416	Intermediate Similarity	NPD4822	Approved
0.7416	Intermediate Similarity	NPD4821	Approved
0.7416	Intermediate Similarity	NPD4820	Approved
0.7416	Intermediate Similarity	NPD4819	Approved
0.7379	Intermediate Similarity	NPD5697	Approved
0.7368	Intermediate Similarity	NPD5692	Phase 3
0.7368	Intermediate Similarity	NPD5207	Approved
0.7368	Intermediate Similarity	NPD5785	Approved
0.7363	Intermediate Similarity	NPD7154	Phase 3
0.7363	Intermediate Similarity	NPD5331	Approved
0.7363	Intermediate Similarity	NPD6695	Phase 3
0.7363	Intermediate Similarity	NPD4788	Approved
0.7363	Intermediate Similarity	NPD5332	Approved
0.7333	Intermediate Similarity	NPD5369	Approved
0.7333	Intermediate Similarity	NPD7290	Approved
0.7333	Intermediate Similarity	NPD4790	Discontinued
0.7333	Intermediate Similarity	NPD7102	Approved
0.7333	Intermediate Similarity	NPD6883	Approved
0.7327	Intermediate Similarity	NPD5211	Phase 2
0.7326	Intermediate Similarity	NPD6926	Approved
0.7326	Intermediate Similarity	NPD6924	Approved
0.732	Intermediate Similarity	NPD7748	Approved
0.7312	Intermediate Similarity	NPD3618	Phase 1
0.7312	Intermediate Similarity	NPD5786	Approved
0.7312	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4694	Approved
0.7312	Intermediate Similarity	NPD5280	Approved
0.7308	Intermediate Similarity	NPD7320	Approved
0.7308	Intermediate Similarity	NPD6011	Approved
0.7303	Intermediate Similarity	NPD4195	Approved
0.73	Intermediate Similarity	NPD6404	Discontinued
0.7294	Intermediate Similarity	NPD4243	Approved
0.7292	Intermediate Similarity	NPD7515	Phase 2
0.7283	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6650	Approved
0.7264	Intermediate Similarity	NPD6869	Approved
0.7264	Intermediate Similarity	NPD6649	Approved
0.7264	Intermediate Similarity	NPD6847	Approved
0.7264	Intermediate Similarity	NPD8130	Phase 1
0.7264	Intermediate Similarity	NPD6617	Approved
0.7263	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7339	Approved
0.7241	Intermediate Similarity	NPD6942	Approved
0.7238	Intermediate Similarity	NPD6013	Approved
0.7238	Intermediate Similarity	NPD6014	Approved
0.7238	Intermediate Similarity	NPD6373	Approved
0.7238	Intermediate Similarity	NPD6372	Approved
0.7238	Intermediate Similarity	NPD6012	Approved
0.7222	Intermediate Similarity	NPD7525	Registered
0.7222	Intermediate Similarity	NPD4695	Discontinued
0.7222	Intermediate Similarity	NPD6930	Phase 2
0.7222	Intermediate Similarity	NPD4252	Approved
0.7222	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6931	Approved
0.7222	Intermediate Similarity	NPD7514	Phase 3
0.7216	Intermediate Similarity	NPD5779	Approved
0.7216	Intermediate Similarity	NPD4202	Approved
0.7216	Intermediate Similarity	NPD5778	Approved
0.7212	Intermediate Similarity	NPD5701	Approved
0.7204	Intermediate Similarity	NPD5363	Approved
0.7196	Intermediate Similarity	NPD8297	Approved
0.7196	Intermediate Similarity	NPD6882	Approved
0.7191	Intermediate Similarity	NPD4271	Approved
0.7191	Intermediate Similarity	NPD3617	Approved
0.7191	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4268	Approved
0.7184	Intermediate Similarity	NPD5141	Approved
0.7172	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5221	Approved
0.7172	Intermediate Similarity	NPD5222	Approved
0.7159	Intermediate Similarity	NPD6933	Approved
0.7143	Intermediate Similarity	NPD4692	Approved
0.7143	Intermediate Similarity	NPD4139	Approved
0.7143	Intermediate Similarity	NPD6001	Approved
0.7129	Intermediate Similarity	NPD5286	Approved
0.7129	Intermediate Similarity	NPD4696	Approved
0.7129	Intermediate Similarity	NPD5285	Approved
0.7128	Intermediate Similarity	NPD5279	Phase 3
0.7113	Intermediate Similarity	NPD6411	Approved
0.7111	Intermediate Similarity	NPD6929	Approved
0.7103	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7902	Approved
0.71	Intermediate Similarity	NPD5173	Approved
0.71	Intermediate Similarity	NPD4755	Approved
0.7093	Intermediate Similarity	NPD6081	Approved
0.7059	Intermediate Similarity	NPD5223	Approved
0.7053	Intermediate Similarity	NPD3573	Approved
0.7053	Intermediate Similarity	NPD7750	Discontinued
0.7053	Intermediate Similarity	NPD7524	Approved
0.7053	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3702	Approved
0.7033	Intermediate Similarity	NPD7332	Phase 2
0.703	Intermediate Similarity	NPD4225	Approved
0.7	Intermediate Similarity	NPD7145	Approved
0.7	Intermediate Similarity	NPD4697	Phase 3
0.699	Remote Similarity	NPD5225	Approved
0.699	Remote Similarity	NPD7632	Discontinued
0.699	Remote Similarity	NPD5226	Approved
0.699	Remote Similarity	NPD4633	Approved
0.699	Remote Similarity	NPD5224	Approved
0.6979	Remote Similarity	NPD4518	Approved
0.6977	Remote Similarity	NPD7143	Approved
0.6977	Remote Similarity	NPD7144	Approved
0.6977	Remote Similarity	NPD4747	Approved
0.6972	Remote Similarity	NPD4632	Approved
0.6966	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6117	Approved
0.6961	Remote Similarity	NPD4700	Approved
0.6957	Remote Similarity	NPD6902	Approved
0.6952	Remote Similarity	NPD6008	Approved
0.6932	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5175	Approved
0.6923	Remote Similarity	NPD5174	Approved
0.6923	Remote Similarity	NPD6052	Approved
0.6907	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6101	Approved
0.6905	Remote Similarity	NPD4224	Phase 2
0.69	Remote Similarity	NPD5654	Approved
0.6897	Remote Similarity	NPD7151	Approved
0.6897	Remote Similarity	NPD7150	Approved
0.6897	Remote Similarity	NPD7152	Approved
0.6889	Remote Similarity	NPD6925	Approved
0.6889	Remote Similarity	NPD6116	Phase 1
0.6889	Remote Similarity	NPD5776	Phase 2
0.6889	Remote Similarity	NPD6932	Approved
0.6887	Remote Similarity	NPD6614	Approved
0.6882	Remote Similarity	NPD6435	Approved
0.6881	Remote Similarity	NPD6053	Discontinued

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