NPASS Compound

Structure

NPC269638 OpenBabel07101718192D 34 36 0 0 1 0 0 0 0 0999 V2000 -3.3705 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3711 -5.8925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6480 -5.2414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1717 -0.8426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4469 0.4024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8663 -3.6372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3210 -3.8131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3399 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1447 -0.8426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2727 -4.0154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0203 -2.8878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6582 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7680 -0.1858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7680 -1.7601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8426 -0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1177 -0.8426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5734 -4.9408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8426 -0.4865 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 2.0686 -2.6855 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6042 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6042 -1.6852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5251 -5.1431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1433 -2.9861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 2 0 0 0 0 2 20 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 24 1 0 0 0 0 12 19 1 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 23 1 0 0 0 0 14 17 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 30 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 21 27 1 6 0 0 0 22 23 1 0 0 0 0 22 28 1 1 0 0 0 23 30 1 6 0 0 0 24 27 1 6 0 0 0 24 29 1 0 0 0 0 25 31 2 0 0 0 0 25 32 1 0 0 0 0 26 33 1 0 0 0 0 27 5 1 6 0 0 0 28 29 1 6 0 0 0 29 7 1 6 0 0 0 30 8 1 1 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.37
Volume:	529.018
LogP:	5.226
LogD:	4.324
LogS:	-4.682
# Rotatable Bonds:	8
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.34
Synthetic Accessibility Score:	4.961
Fsp3:	0.833
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:	-5.214
MDCK Permeability:	2.4706747353775427e-05
Pgp-inhibitor:	0.45
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.095
Plasma Protein Binding (PPB):	92.23545837402344%
Volume Distribution (VD):	0.576
Pgp-substrate:	5.859829425811768%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.201
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.14
CYP2C9-substrate:	0.848
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.445
CYP3A4-inhibitor:	0.301
CYP3A4-substrate:	0.176

ADMET: Excretion

Clearance (CL):	2.929
Half-life (T1/2):	0.445

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.36
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.316
Skin Sensitization:	0.835
Carcinogencity:	0.11
Eye Corrosion:	0.116
Eye Irritation:	0.139
Respiratory Toxicity:	0.673

Download Data

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

Natural Product: NPC269638

Natural Product ID:	NPC269638
*Common Name:**	(20S,23E)-20,25-Dihydroxy-3,4-Secodammara-4(28),23-Dienoic Acid
IUPAC Name:	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]propanoic acid
Synonyms:
Standard InCHIKey:	IEKMEVXMHYPYPV-DJEZTIHDSA-N
Standard InCHI:	InChI=1S/C30H50O4/c1-20(2)21-12-19-29(7)24(27(21,5)17-14-25(31)32)11-10-22-23(13-18-28(22,29)6)30(8,34)16-9-15-26(3,4)33/h9,15,21-24,33-34H,1,10-14,16-19H2,2-8H3,(H,31,32)/b15-9+/t21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@]2(C)[C@H](CC[C@@H]3[C@H](CC[C@@]23C)[C@](C)(C/C=C/C(C)(C)O)O)[C@@]1(C)CCC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477754
PubChem CID:	44575598
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[453290]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	>	1.0	10'3nM	PMID[453290]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	1.0	10'3nM	PMID[453290]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	1.0	10'3nM	PMID[453290]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	1.0	10'3nM	PMID[453290]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	1.0	10'3nM	PMID[453290]

☑ 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 NPC269638 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	152
0.1-0.2	944
0.2-0.3	4399
0.3-0.4	14365
0.4-0.5	8718
0.5-0.6	6876
0.6-0.7	5271
0.7-0.8	1755
0.8-0.85	181
0.85-0.9	31
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9753	High Similarity	NPC128644
0.9167	High Similarity	NPC117122
0.9157	High Similarity	NPC472869
0.9059	High Similarity	NPC262043
0.9048	High Similarity	NPC236618
0.9048	High Similarity	NPC136948
0.8941	High Similarity	NPC472870
0.8929	High Similarity	NPC186975
0.8916	High Similarity	NPC472864
0.8916	High Similarity	NPC164577
0.8916	High Similarity	NPC19849
0.8875	High Similarity	NPC179028
0.8837	High Similarity	NPC66344
0.8795	High Similarity	NPC167103
0.8795	High Similarity	NPC97913
0.8795	High Similarity	NPC310470
0.8795	High Similarity	NPC477852
0.8795	High Similarity	NPC477373
0.878	High Similarity	NPC147066
0.8765	High Similarity	NPC477371
0.8765	High Similarity	NPC158846
0.8736	High Similarity	NPC472866
0.869	High Similarity	NPC194937
0.869	High Similarity	NPC476038
0.869	High Similarity	NPC165064
0.869	High Similarity	NPC472865
0.8675	High Similarity	NPC133391
0.8675	High Similarity	NPC260956
0.8636	High Similarity	NPC473986
0.8636	High Similarity	NPC204341
0.8636	High Similarity	NPC474018
0.8608	High Similarity	NPC18819
0.8608	High Similarity	NPC46610
0.8588	High Similarity	NPC29447
0.8588	High Similarity	NPC283733
0.8571	High Similarity	NPC107243
0.8554	High Similarity	NPC38350
0.8554	High Similarity	NPC201912
0.8554	High Similarity	NPC477372
0.8539	High Similarity	NPC472871
0.8537	High Similarity	NPC215843
0.8519	High Similarity	NPC66105
0.8519	High Similarity	NPC61952
0.8488	Intermediate Similarity	NPC155011
0.8471	Intermediate Similarity	NPC248758
0.8462	Intermediate Similarity	NPC235053
0.8452	Intermediate Similarity	NPC320514
0.8444	Intermediate Similarity	NPC292793
0.8434	Intermediate Similarity	NPC37038
0.8427	Intermediate Similarity	NPC470113
0.8415	Intermediate Similarity	NPC198240
0.8415	Intermediate Similarity	NPC321514
0.8415	Intermediate Similarity	NPC321690
0.8415	Intermediate Similarity	NPC239098
0.8409	Intermediate Similarity	NPC128496
0.8409	Intermediate Similarity	NPC2983
0.8395	Intermediate Similarity	NPC69143
0.8395	Intermediate Similarity	NPC246445
0.8391	Intermediate Similarity	NPC96496
0.8372	Intermediate Similarity	NPC471224
0.837	Intermediate Similarity	NPC57416
0.8353	Intermediate Similarity	NPC83569
0.8353	Intermediate Similarity	NPC3856
0.8353	Intermediate Similarity	NPC470015
0.8353	Intermediate Similarity	NPC279639
0.8353	Intermediate Similarity	NPC168188
0.8353	Intermediate Similarity	NPC215893
0.8353	Intermediate Similarity	NPC69279
0.8352	Intermediate Similarity	NPC293052
0.8352	Intermediate Similarity	NPC476174
0.8333	Intermediate Similarity	NPC232625
0.8315	Intermediate Similarity	NPC469400
0.8315	Intermediate Similarity	NPC320026
0.8313	Intermediate Similarity	NPC196827
0.8313	Intermediate Similarity	NPC231431
0.8313	Intermediate Similarity	NPC274996
0.8313	Intermediate Similarity	NPC199595
0.8293	Intermediate Similarity	NPC91665
0.828	Intermediate Similarity	NPC98868
0.8276	Intermediate Similarity	NPC82979
0.8276	Intermediate Similarity	NPC475007
0.8272	Intermediate Similarity	NPC192540
0.8272	Intermediate Similarity	NPC476844
0.8272	Intermediate Similarity	NPC279666
0.8261	Intermediate Similarity	NPC250757
0.8261	Intermediate Similarity	NPC301534
0.8261	Intermediate Similarity	NPC29152
0.8242	Intermediate Similarity	NPC8993
0.8242	Intermediate Similarity	NPC469406
0.8235	Intermediate Similarity	NPC469804
0.8235	Intermediate Similarity	NPC469806
0.8235	Intermediate Similarity	NPC472239
0.8235	Intermediate Similarity	NPC469799
0.8235	Intermediate Similarity	NPC469805
0.8222	Intermediate Similarity	NPC476187
0.8222	Intermediate Similarity	NPC475806
0.8202	Intermediate Similarity	NPC155479
0.8202	Intermediate Similarity	NPC36668
0.8202	Intermediate Similarity	NPC474570
0.8202	Intermediate Similarity	NPC474704
0.8202	Intermediate Similarity	NPC118011
0.8202	Intermediate Similarity	NPC215029
0.8202	Intermediate Similarity	NPC476733
0.8202	Intermediate Similarity	NPC475921
0.8202	Intermediate Similarity	NPC214387
0.8193	Intermediate Similarity	NPC471409
0.8193	Intermediate Similarity	NPC275494
0.8193	Intermediate Similarity	NPC260385
0.8193	Intermediate Similarity	NPC110094
0.8193	Intermediate Similarity	NPC280654
0.8191	Intermediate Similarity	NPC266955
0.8182	Intermediate Similarity	NPC142361
0.8182	Intermediate Similarity	NPC476409
0.8182	Intermediate Similarity	NPC167877
0.8182	Intermediate Similarity	NPC474684
0.8172	Intermediate Similarity	NPC126815
0.8172	Intermediate Similarity	NPC156546
0.8172	Intermediate Similarity	NPC475894
0.8171	Intermediate Similarity	NPC20466
0.8161	Intermediate Similarity	NPC123319
0.8161	Intermediate Similarity	NPC94531
0.8161	Intermediate Similarity	NPC311702
0.8161	Intermediate Similarity	NPC474083
0.8161	Intermediate Similarity	NPC60350
0.8152	Intermediate Similarity	NPC318282
0.8152	Intermediate Similarity	NPC171395
0.8152	Intermediate Similarity	NPC469995
0.8152	Intermediate Similarity	NPC84383
0.8152	Intermediate Similarity	NPC174948
0.8152	Intermediate Similarity	NPC173875
0.8148	Intermediate Similarity	NPC237591
0.8148	Intermediate Similarity	NPC283908
0.8148	Intermediate Similarity	NPC103958
0.8148	Intermediate Similarity	NPC3753
0.8148	Intermediate Similarity	NPC241854
0.8148	Intermediate Similarity	NPC251970
0.8148	Intermediate Similarity	NPC476046
0.8148	Intermediate Similarity	NPC183503
0.8148	Intermediate Similarity	NPC161923
0.814	Intermediate Similarity	NPC472740
0.8132	Intermediate Similarity	NPC243866
0.8132	Intermediate Similarity	NPC474736
0.8125	Intermediate Similarity	NPC160817
0.8125	Intermediate Similarity	NPC475050
0.8118	Intermediate Similarity	NPC142244
0.8118	Intermediate Similarity	NPC327002
0.8118	Intermediate Similarity	NPC14203
0.8118	Intermediate Similarity	NPC229584
0.8118	Intermediate Similarity	NPC278459
0.8118	Intermediate Similarity	NPC40228
0.8111	Intermediate Similarity	NPC471896
0.8111	Intermediate Similarity	NPC477149
0.8111	Intermediate Similarity	NPC477147
0.8111	Intermediate Similarity	NPC48010
0.8105	Intermediate Similarity	NPC282524
0.8105	Intermediate Similarity	NPC115899
0.8095	Intermediate Similarity	NPC192744
0.809	Intermediate Similarity	NPC242864
0.809	Intermediate Similarity	NPC48107
0.8085	Intermediate Similarity	NPC197386
0.8085	Intermediate Similarity	NPC235464
0.8085	Intermediate Similarity	NPC166745
0.8072	Intermediate Similarity	NPC132542
0.8072	Intermediate Similarity	NPC471899
0.8072	Intermediate Similarity	NPC471897
0.8072	Intermediate Similarity	NPC68828
0.8072	Intermediate Similarity	NPC107039
0.8072	Intermediate Similarity	NPC137547
0.8068	Intermediate Similarity	NPC469994
0.8068	Intermediate Similarity	NPC264127
0.8068	Intermediate Similarity	NPC70661
0.8068	Intermediate Similarity	NPC473226
0.8068	Intermediate Similarity	NPC322159
0.8065	Intermediate Similarity	NPC456
0.8065	Intermediate Similarity	NPC322063
0.8065	Intermediate Similarity	NPC328371
0.8065	Intermediate Similarity	NPC155676
0.8065	Intermediate Similarity	NPC472941
0.8049	Intermediate Similarity	NPC469803
0.8049	Intermediate Similarity	NPC201027
0.8049	Intermediate Similarity	NPC476795
0.8046	Intermediate Similarity	NPC178025
0.8046	Intermediate Similarity	NPC156981
0.8046	Intermediate Similarity	NPC59453
0.8046	Intermediate Similarity	NPC16287
0.8046	Intermediate Similarity	NPC221758
0.8046	Intermediate Similarity	NPC181743
0.8043	Intermediate Similarity	NPC474690
0.8043	Intermediate Similarity	NPC299100
0.8025	Intermediate Similarity	NPC161187
0.8025	Intermediate Similarity	NPC330659
0.8025	Intermediate Similarity	NPC244708
0.8023	Intermediate Similarity	NPC69101
0.8023	Intermediate Similarity	NPC3511
0.8023	Intermediate Similarity	NPC193347
0.8023	Intermediate Similarity	NPC296367
0.8023	Intermediate Similarity	NPC472867
0.8023	Intermediate Similarity	NPC251779
0.8023	Intermediate Similarity	NPC142253
0.8023	Intermediate Similarity	NPC240302

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 NPC269638 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1183
0.2-0.3	3758
0.3-0.4	2680
0.4-0.5	837
0.5-0.6	222
0.6-0.7	168
0.7-0.8	151
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8132	Intermediate Similarity	NPD6399	Phase 3
0.8046	Intermediate Similarity	NPD4786	Approved
0.8023	Intermediate Similarity	NPD4221	Approved
0.8023	Intermediate Similarity	NPD4223	Phase 3
0.8022	Intermediate Similarity	NPD5281	Approved
0.8022	Intermediate Similarity	NPD5284	Approved
0.7976	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD5329	Approved
0.7865	Intermediate Similarity	NPD4623	Approved
0.7865	Intermediate Similarity	NPD4519	Discontinued
0.7865	Intermediate Similarity	NPD6098	Approved
0.7841	Intermediate Similarity	NPD4197	Approved
0.7816	Intermediate Similarity	NPD3667	Approved
0.7802	Intermediate Similarity	NPD6673	Approved
0.7802	Intermediate Similarity	NPD6080	Approved
0.7802	Intermediate Similarity	NPD6904	Approved
0.7789	Intermediate Similarity	NPD6083	Phase 2
0.7789	Intermediate Similarity	NPD6084	Phase 2
0.7727	Intermediate Similarity	NPD5362	Discontinued
0.7711	Intermediate Similarity	NPD4784	Approved
0.7711	Intermediate Similarity	NPD4785	Approved
0.7692	Intermediate Similarity	NPD5737	Approved
0.7692	Intermediate Similarity	NPD6672	Approved
0.7667	Intermediate Similarity	NPD4690	Approved
0.7667	Intermediate Similarity	NPD5205	Approved
0.7667	Intermediate Similarity	NPD4693	Phase 3
0.7667	Intermediate Similarity	NPD4138	Approved
0.7667	Intermediate Similarity	NPD4689	Approved
0.7667	Intermediate Similarity	NPD4688	Approved
0.7667	Intermediate Similarity	NPD5690	Phase 2
0.7634	Intermediate Similarity	NPD7637	Suspended
0.7634	Intermediate Similarity	NPD5693	Phase 1
0.7609	Intermediate Similarity	NPD4753	Phase 2
0.7579	Intermediate Similarity	NPD5695	Phase 3
0.7556	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD5696	Approved
0.75	Intermediate Similarity	NPD5208	Approved
0.7473	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7146	Approved
0.7473	Intermediate Similarity	NPD7521	Approved
0.7473	Intermediate Similarity	NPD7334	Approved
0.7473	Intermediate Similarity	NPD4694	Approved
0.7473	Intermediate Similarity	NPD6409	Approved
0.7473	Intermediate Similarity	NPD5280	Approved
0.7473	Intermediate Similarity	NPD6684	Approved
0.7473	Intermediate Similarity	NPD5330	Approved
0.7471	Intermediate Similarity	NPD4195	Approved
0.747	Intermediate Similarity	NPD4243	Approved
0.7449	Intermediate Similarity	NPD7640	Approved
0.7449	Intermediate Similarity	NPD6404	Discontinued
0.7449	Intermediate Similarity	NPD7639	Approved
0.7447	Intermediate Similarity	NPD6050	Approved
0.7447	Intermediate Similarity	NPD5694	Approved
0.7447	Intermediate Similarity	NPD6079	Approved
0.7444	Intermediate Similarity	NPD3665	Phase 1
0.7444	Intermediate Similarity	NPD3666	Approved
0.7444	Intermediate Similarity	NPD3668	Phase 3
0.7444	Intermediate Similarity	NPD3133	Approved
0.7419	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5328	Approved
0.7416	Intermediate Similarity	NPD4269	Approved
0.7416	Intermediate Similarity	NPD4270	Approved
0.7416	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5210	Approved
0.7396	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4629	Approved
0.7386	Intermediate Similarity	NPD4695	Discontinued
0.7386	Intermediate Similarity	NPD4822	Approved
0.7386	Intermediate Similarity	NPD4820	Approved
0.7386	Intermediate Similarity	NPD4821	Approved
0.7386	Intermediate Similarity	NPD4819	Approved
0.7383	Intermediate Similarity	NPD7115	Discovery
0.7356	Intermediate Similarity	NPD3617	Approved
0.7347	Intermediate Similarity	NPD7638	Approved
0.734	Intermediate Similarity	NPD5692	Phase 3
0.734	Intermediate Similarity	NPD5207	Approved
0.7333	Intermediate Similarity	NPD5331	Approved
0.7333	Intermediate Similarity	NPD4788	Approved
0.7333	Intermediate Similarity	NPD5332	Approved
0.7312	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6903	Approved
0.7303	Intermediate Similarity	NPD4692	Approved
0.7303	Intermediate Similarity	NPD4790	Discontinued
0.7303	Intermediate Similarity	NPD4139	Approved
0.73	Intermediate Similarity	NPD5211	Phase 2
0.7294	Intermediate Similarity	NPD6924	Approved
0.7294	Intermediate Similarity	NPD6926	Approved
0.7283	Intermediate Similarity	NPD3618	Phase 1
0.7282	Intermediate Similarity	NPD6899	Approved
0.7282	Intermediate Similarity	NPD6881	Approved
0.7263	Intermediate Similarity	NPD8034	Phase 2
0.7263	Intermediate Similarity	NPD8035	Phase 2
0.7263	Intermediate Similarity	NPD7515	Phase 2
0.7262	Intermediate Similarity	NPD6081	Approved
0.7255	Intermediate Similarity	NPD6675	Approved
0.7255	Intermediate Similarity	NPD7128	Approved
0.7255	Intermediate Similarity	NPD6402	Approved
0.7255	Intermediate Similarity	NPD5739	Approved
0.7234	Intermediate Similarity	NPD6051	Approved
0.7209	Intermediate Similarity	NPD7339	Approved
0.7209	Intermediate Similarity	NPD6942	Approved
0.7191	Intermediate Similarity	NPD6930	Phase 2
0.7191	Intermediate Similarity	NPD6931	Approved
0.7191	Intermediate Similarity	NPD4252	Approved
0.7191	Intermediate Similarity	NPD7514	Phase 3
0.7191	Intermediate Similarity	NPD7525	Registered
0.7188	Intermediate Similarity	NPD4202	Approved
0.7184	Intermediate Similarity	NPD5697	Approved
0.7174	Intermediate Similarity	NPD5363	Approved
0.7159	Intermediate Similarity	NPD4268	Approved
0.7159	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4271	Approved
0.7158	Intermediate Similarity	NPD5785	Approved
0.7157	Intermediate Similarity	NPD5141	Approved
0.7143	Intermediate Similarity	NPD6695	Phase 3
0.7143	Intermediate Similarity	NPD5222	Approved
0.7143	Intermediate Similarity	NPD7102	Approved
0.7143	Intermediate Similarity	NPD6883	Approved
0.7143	Intermediate Similarity	NPD5221	Approved
0.7143	Intermediate Similarity	NPD7154	Phase 3
0.7143	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7290	Approved
0.7143	Intermediate Similarity	NPD4747	Approved
0.7128	Intermediate Similarity	NPD4518	Approved
0.7126	Intermediate Similarity	NPD6933	Approved
0.7115	Intermediate Similarity	NPD7320	Approved
0.7115	Intermediate Similarity	NPD6011	Approved
0.7113	Intermediate Similarity	NPD6001	Approved
0.7113	Intermediate Similarity	NPD7748	Approved
0.7111	Intermediate Similarity	NPD5369	Approved
0.71	Intermediate Similarity	NPD5286	Approved
0.71	Intermediate Similarity	NPD4696	Approved
0.71	Intermediate Similarity	NPD5285	Approved
0.7097	Intermediate Similarity	NPD5279	Phase 3
0.7097	Intermediate Similarity	NPD5786	Approved
0.7079	Intermediate Similarity	NPD6929	Approved
0.7075	Intermediate Similarity	NPD6649	Approved
0.7075	Intermediate Similarity	NPD8130	Phase 1
0.7075	Intermediate Similarity	NPD6650	Approved
0.7075	Intermediate Similarity	NPD6869	Approved
0.7075	Intermediate Similarity	NPD6617	Approved
0.7075	Intermediate Similarity	NPD6847	Approved
0.7073	Intermediate Similarity	NPD4224	Phase 2
0.7071	Intermediate Similarity	NPD4755	Approved
0.7071	Intermediate Similarity	NPD5173	Approved
0.7065	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6013	Approved
0.7048	Intermediate Similarity	NPD6372	Approved
0.7048	Intermediate Similarity	NPD6014	Approved
0.7048	Intermediate Similarity	NPD6012	Approved
0.7048	Intermediate Similarity	NPD6373	Approved
0.703	Intermediate Similarity	NPD5223	Approved
0.7024	Intermediate Similarity	NPD4137	Phase 3
0.7021	Intermediate Similarity	NPD3573	Approved
0.7021	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5701	Approved
0.7011	Intermediate Similarity	NPD5275	Approved
0.7011	Intermediate Similarity	NPD4190	Phase 3
0.701	Intermediate Similarity	NPD5778	Approved
0.701	Intermediate Similarity	NPD5779	Approved
0.7009	Intermediate Similarity	NPD8297	Approved
0.7009	Intermediate Similarity	NPD6882	Approved
0.7	Intermediate Similarity	NPD7332	Phase 2
0.7	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4096	Approved
0.697	Remote Similarity	NPD4697	Phase 3
0.6966	Remote Similarity	NPD7145	Approved
0.6961	Remote Similarity	NPD5091	Approved
0.6961	Remote Similarity	NPD5224	Approved
0.6961	Remote Similarity	NPD5226	Approved
0.6961	Remote Similarity	NPD4633	Approved
0.6961	Remote Similarity	NPD5225	Approved
0.6941	Remote Similarity	NPD4691	Approved
0.6941	Remote Similarity	NPD7143	Approved
0.6941	Remote Similarity	NPD7144	Approved
0.6932	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6117	Approved
0.6931	Remote Similarity	NPD4700	Approved
0.6923	Remote Similarity	NPD6902	Approved
0.6916	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6411	Approved
0.6905	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5360	Phase 3
0.69	Remote Similarity	NPD7902	Approved
0.6897	Remote Similarity	NPD5733	Approved
0.6897	Remote Similarity	NPD4687	Approved
0.6897	Remote Similarity	NPD4058	Approved
0.6897	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5174	Approved
0.6893	Remote Similarity	NPD6052	Approved
0.6893	Remote Similarity	NPD5175	Approved
0.6869	Remote Similarity	NPD5654	Approved
0.686	Remote Similarity	NPD7150	Approved
0.686	Remote Similarity	NPD7152	Approved
0.686	Remote Similarity	NPD7151	Approved
0.6857	Remote Similarity	NPD6614	Approved
0.6854	Remote Similarity	NPD5776	Phase 2
0.6854	Remote Similarity	NPD6116	Phase 1
0.6854	Remote Similarity	NPD6932	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