NPASS Compound

Structure

NPC258323 OpenBabel07101718232D 42 46 0 0 1 0 0 0 0 0999 V2000 3.4613 0.7026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5399 2.6807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0233 2.7673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6079 -4.5170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6293 -4.5170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1385 3.9458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3420 2.9887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8732 -2.6064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1186 -0.7339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4237 -3.6695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1186 -1.7124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4237 -3.1803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9660 -2.2017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7770 -1.2232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2018 -2.0148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1518 2.1570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4237 -0.2446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8474 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5042 0.4991 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2375 1.7501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7209 1.8367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2018 -0.4315 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2712 -3.1803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2712 -2.2017 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8494 1.2263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4237 -2.2017 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9660 -3.1803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1090 2.3604 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1186 -3.6695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4113 3.2911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2712 -1.7124 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4237 -1.7124 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2712 -0.7339 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4237 -0.7339 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7197 1.5466 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3757 1.1095 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8135 -3.6695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7566 4.0183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3846 -0.9188 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 0.8923 1.0229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7637 1.6332 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 29 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 30 1 0 0 0 0 8 31 1 0 0 0 0 9 32 1 0 0 0 0 10 12 1 0 0 0 0 10 23 2 0 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 15 31 1 0 0 0 0 17 34 1 0 0 0 0 18 33 1 0 0 0 0 18 40 1 0 0 0 0 19 1 1 1 0 0 0 19 22 1 0 0 0 0 19 25 1 0 0 0 0 20 35 2 0 0 0 0 20 41 1 0 0 0 0 21 36 2 0 0 0 0 21 42 1 0 0 0 0 22 33 1 1 0 0 0 23 24 1 0 0 0 0 23 29 1 0 0 0 0 24 32 1 1 0 0 0 25 16 1 6 0 0 0 25 41 1 0 0 0 0 26 31 1 6 0 0 0 26 32 1 0 0 0 0 27 29 1 0 0 0 0 27 37 2 0 0 0 0 28 16 1 6 0 0 0 28 30 1 0 0 0 0 28 42 1 0 0 0 0 30 38 1 0 0 0 0 31 33 1 6 0 0 0 32 34 1 6 0 0 0 33 17 1 6 0 0 0 34 39 1 6 0 0 0 34 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	588.37
Volume:	613.614
LogP:	4.105
LogD:	3.175
LogS:	-4.431
# Rotatable Bonds:	9
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.31
Synthetic Accessibility Score:	6.745
Fsp3:	0.853
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.391
MDCK Permeability:	4.757686474476941e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.533
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.655
30% Bioavailability (F30%):	0.824

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.842
Plasma Protein Binding (PPB):	82.72405242919922%
Volume Distribution (VD):	1.178
Pgp-substrate:	9.105741500854492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.604
CYP2C9-inhibitor:	0.139
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.039
CYP3A4-inhibitor:	0.812
CYP3A4-substrate:	0.638

ADMET: Excretion

Clearance (CL):	3.661
Half-life (T1/2):	0.621

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.44
Drug-inuced Liver Injury (DILI):	0.238
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.505
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.159
Carcinogencity:	0.893
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC258323

Natural Product ID:	NPC258323
*Common Name:**	Leucopaxillone B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DSTOROHYHNDBMG-SZCSQRRTSA-N
Standard InCHI:	InChI=1S/C34H52O8/c1-19(25(41-20(2)35)16-28(30(6,7)38)42-21(3)36)22-14-15-31(8)26-12-10-23-24(11-13-27(37)29(23,4)5)32(26,9)34(39)17-33(22,31)18-40-34/h10,19,22,24-26,28,38-39H,11-18H2,1-9H3/t19-,22+,24+,25+,26-,28+,31-,32-,33-,34-/m0/s1
SMILES:	CC(=O)O[C@@H]([C@H]([C@H]1CC[C@@]2([C@]31CO[C@](C3)(O)[C@@]1([C@H]2CC=C2[C@H]1CCC(=O)C2(C)C)C)C)C)C[C@H](C(O)(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506664
PubChem CID:	21573069
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001691] Steroid esters

*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
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568769]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[17190463]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	154700.0	nM	PMID[502205]
NPT308	Cell Line	CAKI-1	Homo sapiens	IC50	=	30300.0	nM	PMID[502205]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	86900.0	nM	PMID[502205]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	86900.0	nM	PMID[502205]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	0.3	ug.mL-1	PMID[502206]

☑ 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 NPC258323 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	220
0.1-0.2	1261
0.2-0.3	4669
0.3-0.4	10388
0.4-0.5	10964
0.5-0.6	5574
0.6-0.7	5636
0.7-0.8	3701
0.8-0.85	239
0.85-0.9	39
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9417	High Similarity	NPC101450
0.91	High Similarity	NPC167974
0.9029	High Similarity	NPC95243
0.9029	High Similarity	NPC63023
0.8962	High Similarity	NPC285410
0.8962	High Similarity	NPC263827
0.8962	High Similarity	NPC250481
0.8952	High Similarity	NPC218853
0.8932	High Similarity	NPC31430
0.8932	High Similarity	NPC85593
0.8932	High Similarity	NPC100955
0.8932	High Similarity	NPC121566
0.8932	High Similarity	NPC471293
0.8889	High Similarity	NPC473882
0.8868	High Similarity	NPC52241
0.8868	High Similarity	NPC129340
0.8868	High Similarity	NPC154856
0.8868	High Similarity	NPC475317
0.8796	High Similarity	NPC178981
0.8774	High Similarity	NPC265655
0.8762	High Similarity	NPC59530
0.8739	High Similarity	NPC477071
0.8738	High Similarity	NPC22388
0.8704	High Similarity	NPC474265
0.8704	High Similarity	NPC210420
0.8704	High Similarity	NPC130427
0.8692	High Similarity	NPC474567
0.8692	High Similarity	NPC250956
0.8679	High Similarity	NPC195708
0.8679	High Similarity	NPC472219
0.8679	High Similarity	NPC472218
0.8679	High Similarity	NPC472217
0.8679	High Similarity	NPC295389
0.8661	High Similarity	NPC471406
0.8636	High Similarity	NPC244127
0.8627	High Similarity	NPC119036
0.8624	High Similarity	NPC260665
0.8624	High Similarity	NPC251309
0.8611	High Similarity	NPC292196
0.8611	High Similarity	NPC272242
0.8598	High Similarity	NPC477070
0.8598	High Similarity	NPC173905
0.8598	High Similarity	NPC5475
0.8598	High Similarity	NPC284828
0.8598	High Similarity	NPC472216
0.8598	High Similarity	NPC477069
0.8598	High Similarity	NPC118225
0.8596	High Similarity	NPC41129
0.8585	High Similarity	NPC293512
0.8558	High Similarity	NPC473928
0.8545	High Similarity	NPC220293
0.8545	High Similarity	NPC474557
0.8545	High Similarity	NPC116024
0.8532	High Similarity	NPC233003
0.8532	High Similarity	NPC280782
0.8519	High Similarity	NPC5284
0.8519	High Similarity	NPC475563
0.8519	High Similarity	NPC470065
0.8519	High Similarity	NPC475134
0.8515	High Similarity	NPC279974
0.8496	Intermediate Similarity	NPC241192
0.8491	Intermediate Similarity	NPC477877
0.8491	Intermediate Similarity	NPC472655
0.8491	Intermediate Similarity	NPC162033
0.8491	Intermediate Similarity	NPC473199
0.8485	Intermediate Similarity	NPC471896
0.8482	Intermediate Similarity	NPC239293
0.8476	Intermediate Similarity	NPC140723
0.8476	Intermediate Similarity	NPC474575
0.8468	Intermediate Similarity	NPC279638
0.8468	Intermediate Similarity	NPC152199
0.8468	Intermediate Similarity	NPC266728
0.8468	Intermediate Similarity	NPC235539
0.8468	Intermediate Similarity	NPC49492
0.8468	Intermediate Similarity	NPC134869
0.8455	Intermediate Similarity	NPC52634
0.8455	Intermediate Similarity	NPC477944
0.8455	Intermediate Similarity	NPC255017
0.8455	Intermediate Similarity	NPC102619
0.8448	Intermediate Similarity	NPC47113
0.8448	Intermediate Similarity	NPC174367
0.8447	Intermediate Similarity	NPC5358
0.8447	Intermediate Similarity	NPC216260
0.844	Intermediate Similarity	NPC269466
0.844	Intermediate Similarity	NPC477073
0.844	Intermediate Similarity	NPC475480
0.844	Intermediate Similarity	NPC475668
0.844	Intermediate Similarity	NPC473921
0.8426	Intermediate Similarity	NPC237503
0.8426	Intermediate Similarity	NPC57362
0.8426	Intermediate Similarity	NPC204407
0.8426	Intermediate Similarity	NPC167383
0.8426	Intermediate Similarity	NPC137917
0.8426	Intermediate Similarity	NPC306746
0.8421	Intermediate Similarity	NPC476672
0.8407	Intermediate Similarity	NPC161065
0.8396	Intermediate Similarity	NPC472227
0.8396	Intermediate Similarity	NPC470060
0.8396	Intermediate Similarity	NPC470058
0.8396	Intermediate Similarity	NPC470062
0.8396	Intermediate Similarity	NPC470064
0.8396	Intermediate Similarity	NPC470057
0.8396	Intermediate Similarity	NPC470043
0.8396	Intermediate Similarity	NPC223741
0.8396	Intermediate Similarity	NPC470059
0.8396	Intermediate Similarity	NPC470061
0.8396	Intermediate Similarity	NPC472228
0.8384	Intermediate Similarity	NPC269267
0.8381	Intermediate Similarity	NPC470053
0.8378	Intermediate Similarity	NPC474906
0.8378	Intermediate Similarity	NPC74727
0.8378	Intermediate Similarity	NPC477580
0.8378	Intermediate Similarity	NPC18547
0.8376	Intermediate Similarity	NPC42399
0.8364	Intermediate Similarity	NPC11252
0.8364	Intermediate Similarity	NPC152117
0.8364	Intermediate Similarity	NPC471967
0.8364	Intermediate Similarity	NPC37739
0.8364	Intermediate Similarity	NPC289312
0.8364	Intermediate Similarity	NPC234042
0.8364	Intermediate Similarity	NPC477253
0.8364	Intermediate Similarity	NPC46388
0.8362	Intermediate Similarity	NPC476674
0.835	Intermediate Similarity	NPC253586
0.8349	Intermediate Similarity	NPC136877
0.8349	Intermediate Similarity	NPC476882
0.8349	Intermediate Similarity	NPC127056
0.8349	Intermediate Similarity	NPC68419
0.8349	Intermediate Similarity	NPC56713
0.8349	Intermediate Similarity	NPC270667
0.8349	Intermediate Similarity	NPC164194
0.8349	Intermediate Similarity	NPC476881
0.8349	Intermediate Similarity	NPC102914
0.8349	Intermediate Similarity	NPC59804
0.8349	Intermediate Similarity	NPC114961
0.8349	Intermediate Similarity	NPC476884
0.8349	Intermediate Similarity	NPC7870
0.8349	Intermediate Similarity	NPC90856
0.8349	Intermediate Similarity	NPC476886
0.8349	Intermediate Similarity	NPC220984
0.8349	Intermediate Similarity	NPC269095
0.8349	Intermediate Similarity	NPC174679
0.8349	Intermediate Similarity	NPC27551
0.8349	Intermediate Similarity	NPC29069
0.8349	Intermediate Similarity	NPC78046
0.8349	Intermediate Similarity	NPC476885
0.8349	Intermediate Similarity	NPC108709
0.8349	Intermediate Similarity	NPC110139
0.8349	Intermediate Similarity	NPC279554
0.8349	Intermediate Similarity	NPC475296
0.8349	Intermediate Similarity	NPC75747
0.8349	Intermediate Similarity	NPC476883
0.8349	Intermediate Similarity	NPC476880
0.8349	Intermediate Similarity	NPC476887
0.8349	Intermediate Similarity	NPC274507
0.8349	Intermediate Similarity	NPC474589
0.8349	Intermediate Similarity	NPC199457
0.8333	Intermediate Similarity	NPC470312
0.8333	Intermediate Similarity	NPC284807
0.8333	Intermediate Similarity	NPC472988
0.8333	Intermediate Similarity	NPC28198
0.8333	Intermediate Similarity	NPC38217
0.8333	Intermediate Similarity	NPC224414
0.8333	Intermediate Similarity	NPC88744
0.8333	Intermediate Similarity	NPC177246
0.8333	Intermediate Similarity	NPC476123
0.8319	Intermediate Similarity	NPC297179
0.8319	Intermediate Similarity	NPC475899
0.8318	Intermediate Similarity	NPC210178
0.8318	Intermediate Similarity	NPC196528
0.8318	Intermediate Similarity	NPC475611
0.8318	Intermediate Similarity	NPC278628
0.8318	Intermediate Similarity	NPC231530
0.8318	Intermediate Similarity	NPC96377
0.8317	Intermediate Similarity	NPC470224
0.8304	Intermediate Similarity	NPC474046
0.8304	Intermediate Similarity	NPC470628
0.8304	Intermediate Similarity	NPC259306
0.8304	Intermediate Similarity	NPC243981
0.8302	Intermediate Similarity	NPC36688
0.8302	Intermediate Similarity	NPC473523
0.8302	Intermediate Similarity	NPC213190
0.8302	Intermediate Similarity	NPC474124
0.83	Intermediate Similarity	NPC148414
0.83	Intermediate Similarity	NPC175628
0.83	Intermediate Similarity	NPC111585
0.8288	Intermediate Similarity	NPC47063
0.8288	Intermediate Similarity	NPC477074
0.8288	Intermediate Similarity	NPC962
0.8288	Intermediate Similarity	NPC471627
0.8288	Intermediate Similarity	NPC320118
0.8288	Intermediate Similarity	NPC471173
0.8288	Intermediate Similarity	NPC271138
0.8288	Intermediate Similarity	NPC73455
0.8288	Intermediate Similarity	NPC250109
0.8288	Intermediate Similarity	NPC144068
0.8288	Intermediate Similarity	NPC200944
0.8288	Intermediate Similarity	NPC189884
0.8288	Intermediate Similarity	NPC138334
0.8288	Intermediate Similarity	NPC204458

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 NPC258323 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1573
0.2-0.3	4054
0.3-0.4	2189
0.4-0.5	627
0.5-0.6	218
0.6-0.7	163
0.7-0.8	124
0.8-0.85	16
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.822	Intermediate Similarity	NPD8293	Discontinued
0.8205	Intermediate Similarity	NPD7492	Approved
0.8198	Intermediate Similarity	NPD8297	Approved
0.8174	Intermediate Similarity	NPD6054	Approved
0.8174	Intermediate Similarity	NPD6059	Approved
0.8151	Intermediate Similarity	NPD7736	Approved
0.8137	Intermediate Similarity	NPD6399	Phase 3
0.8136	Intermediate Similarity	NPD6616	Approved
0.8091	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8073	Intermediate Similarity	NPD6412	Phase 2
0.8067	Intermediate Similarity	NPD7078	Approved
0.8036	Intermediate Similarity	NPD6882	Approved
0.8034	Intermediate Similarity	NPD6370	Approved
0.8017	Intermediate Similarity	NPD6319	Approved
0.8	Intermediate Similarity	NPD7320	Approved
0.7983	Intermediate Similarity	NPD7507	Approved
0.7982	Intermediate Similarity	NPD6008	Approved
0.7982	Intermediate Similarity	NPD7128	Approved
0.7982	Intermediate Similarity	NPD6675	Approved
0.7982	Intermediate Similarity	NPD6402	Approved
0.7982	Intermediate Similarity	NPD5739	Approved
0.7965	Intermediate Similarity	NPD4632	Approved
0.7949	Intermediate Similarity	NPD6015	Approved
0.7949	Intermediate Similarity	NPD6016	Approved
0.7928	Intermediate Similarity	NPD6372	Approved
0.7928	Intermediate Similarity	NPD6373	Approved
0.7913	Intermediate Similarity	NPD6009	Approved
0.7881	Intermediate Similarity	NPD5988	Approved
0.7838	Intermediate Similarity	NPD6881	Approved
0.7838	Intermediate Similarity	NPD6899	Approved
0.7807	Intermediate Similarity	NPD8133	Approved
0.7788	Intermediate Similarity	NPD8130	Phase 1
0.7788	Intermediate Similarity	NPD6650	Approved
0.7788	Intermediate Similarity	NPD6649	Approved
0.7787	Intermediate Similarity	NPD7319	Approved
0.7748	Intermediate Similarity	NPD5701	Approved
0.7748	Intermediate Similarity	NPD5697	Approved
0.7714	Intermediate Similarity	NPD7748	Approved
0.7712	Intermediate Similarity	NPD8377	Approved
0.7712	Intermediate Similarity	NPD8294	Approved
0.7699	Intermediate Similarity	NPD7102	Approved
0.7699	Intermediate Similarity	NPD6883	Approved
0.7699	Intermediate Similarity	NPD7290	Approved
0.7692	Intermediate Similarity	NPD8034	Phase 2
0.7692	Intermediate Similarity	NPD7327	Approved
0.7692	Intermediate Similarity	NPD8035	Phase 2
0.7692	Intermediate Similarity	NPD7328	Approved
0.7679	Intermediate Similarity	NPD6686	Approved
0.7667	Intermediate Similarity	NPD8328	Phase 3
0.7664	Intermediate Similarity	NPD6084	Phase 2
0.7664	Intermediate Similarity	NPD7902	Approved
0.7664	Intermediate Similarity	NPD6083	Phase 2
0.7647	Intermediate Similarity	NPD8296	Approved
0.7647	Intermediate Similarity	NPD8033	Approved
0.7647	Intermediate Similarity	NPD8380	Approved
0.7647	Intermediate Similarity	NPD8335	Approved
0.7647	Intermediate Similarity	NPD8379	Approved
0.7647	Intermediate Similarity	NPD8378	Approved
0.7642	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6617	Approved
0.7632	Intermediate Similarity	NPD6869	Approved
0.7632	Intermediate Similarity	NPD6847	Approved
0.7627	Intermediate Similarity	NPD7516	Approved
0.7611	Intermediate Similarity	NPD6012	Approved
0.7611	Intermediate Similarity	NPD6013	Approved
0.7611	Intermediate Similarity	NPD6014	Approved
0.7607	Intermediate Similarity	NPD7115	Discovery
0.7593	Intermediate Similarity	NPD7638	Approved
0.7561	Intermediate Similarity	NPD6033	Approved
0.7525	Intermediate Similarity	NPD4786	Approved
0.7523	Intermediate Similarity	NPD7640	Approved
0.7523	Intermediate Similarity	NPD7639	Approved
0.7522	Intermediate Similarity	NPD6011	Approved
0.7521	Intermediate Similarity	NPD6067	Discontinued
0.7521	Intermediate Similarity	NPD7604	Phase 2
0.75	Intermediate Similarity	NPD5983	Phase 2
0.75	Intermediate Similarity	NPD4755	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7478	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD5695	Phase 3
0.7458	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4202	Approved
0.7431	Intermediate Similarity	NPD5696	Approved
0.7404	Intermediate Similarity	NPD5737	Approved
0.7404	Intermediate Similarity	NPD6672	Approved
0.7404	Intermediate Similarity	NPD6903	Approved
0.7398	Intermediate Similarity	NPD6336	Discontinued
0.7391	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4634	Approved
0.7383	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7900	Approved
0.7379	Intermediate Similarity	NPD7146	Approved
0.7379	Intermediate Similarity	NPD6409	Approved
0.7379	Intermediate Similarity	NPD3618	Phase 1
0.7379	Intermediate Similarity	NPD6684	Approved
0.7379	Intermediate Similarity	NPD7521	Approved
0.7379	Intermediate Similarity	NPD7334	Approved
0.7379	Intermediate Similarity	NPD5330	Approved
0.7364	Intermediate Similarity	NPD5285	Approved
0.7364	Intermediate Similarity	NPD5286	Approved
0.7364	Intermediate Similarity	NPD4700	Approved
0.7364	Intermediate Similarity	NPD4696	Approved
0.7358	Intermediate Similarity	NPD6079	Approved
0.7358	Intermediate Similarity	NPD7515	Phase 2
0.7355	Intermediate Similarity	NPD7503	Approved
0.7327	Intermediate Similarity	NPD3667	Approved
0.7282	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4633	Approved
0.7232	Intermediate Similarity	NPD5226	Approved
0.7232	Intermediate Similarity	NPD5225	Approved
0.7232	Intermediate Similarity	NPD5224	Approved
0.7232	Intermediate Similarity	NPD5211	Phase 2
0.7227	Intermediate Similarity	NPD6274	Approved
0.7222	Intermediate Similarity	NPD6001	Approved
0.7217	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6098	Approved
0.7193	Intermediate Similarity	NPD4768	Approved
0.7193	Intermediate Similarity	NPD4767	Approved
0.719	Intermediate Similarity	NPD7101	Approved
0.719	Intermediate Similarity	NPD7100	Approved
0.717	Intermediate Similarity	NPD6904	Approved
0.717	Intermediate Similarity	NPD4753	Phase 2
0.717	Intermediate Similarity	NPD6673	Approved
0.717	Intermediate Similarity	NPD6080	Approved
0.7168	Intermediate Similarity	NPD5175	Approved
0.7168	Intermediate Similarity	NPD5174	Approved
0.7143	Intermediate Similarity	NPD5223	Approved
0.713	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7525	Registered
0.7107	Intermediate Similarity	NPD6335	Approved
0.7105	Intermediate Similarity	NPD5141	Approved
0.7091	Intermediate Similarity	NPD5222	Approved
0.7091	Intermediate Similarity	NPD5221	Approved
0.7091	Intermediate Similarity	NPD4697	Phase 3
0.7091	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6908	Approved
0.7073	Intermediate Similarity	NPD8513	Phase 3
0.7073	Intermediate Similarity	NPD6909	Approved
0.7073	Intermediate Similarity	NPD8516	Approved
0.7073	Intermediate Similarity	NPD8515	Approved
0.7073	Intermediate Similarity	NPD8517	Approved
0.7069	Intermediate Similarity	NPD4729	Approved
0.7069	Intermediate Similarity	NPD4730	Approved
0.7037	Intermediate Similarity	NPD5281	Approved
0.7037	Intermediate Similarity	NPD5284	Approved
0.7031	Intermediate Similarity	NPD5956	Approved
0.7027	Intermediate Similarity	NPD5173	Approved
0.7025	Intermediate Similarity	NPD6317	Approved
0.7019	Intermediate Similarity	NPD3666	Approved
0.7019	Intermediate Similarity	NPD3665	Phase 1
0.7019	Intermediate Similarity	NPD3668	Phase 3
0.7019	Intermediate Similarity	NPD3133	Approved
0.7018	Intermediate Similarity	NPD4754	Approved
0.699	Remote Similarity	NPD4221	Approved
0.699	Remote Similarity	NPD4223	Phase 3
0.6975	Remote Similarity	NPD6053	Discontinued
0.6967	Remote Similarity	NPD6313	Approved
0.6967	Remote Similarity	NPD6314	Approved
0.6964	Remote Similarity	NPD4225	Approved
0.6952	Remote Similarity	NPD5329	Approved
0.6949	Remote Similarity	NPD5250	Approved
0.6949	Remote Similarity	NPD5251	Approved
0.6949	Remote Similarity	NPD5249	Phase 3
0.6949	Remote Similarity	NPD5247	Approved
0.6949	Remote Similarity	NPD5248	Approved
0.6944	Remote Similarity	NPD5207	Approved
0.6942	Remote Similarity	NPD6868	Approved
0.6931	Remote Similarity	NPD6114	Approved
0.6931	Remote Similarity	NPD6697	Approved
0.6931	Remote Similarity	NPD6118	Approved
0.6931	Remote Similarity	NPD6115	Approved
0.693	Remote Similarity	NPD7632	Discontinued
0.6923	Remote Similarity	NPD5128	Approved
0.6916	Remote Similarity	NPD5208	Approved
0.6891	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5693	Phase 1
0.6881	Remote Similarity	NPD6050	Approved
0.6857	Remote Similarity	NPD4197	Approved
0.6847	Remote Similarity	NPD4629	Approved
0.6847	Remote Similarity	NPD5210	Approved
0.6838	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6116	Phase 1
0.6822	Remote Similarity	NPD7524	Approved
0.6822	Remote Similarity	NPD3573	Approved
0.6797	Remote Similarity	NPD8074	Phase 3
0.6789	Remote Similarity	NPD5692	Phase 3
0.675	Remote Similarity	NPD5215	Approved
0.675	Remote Similarity	NPD5216	Approved
0.675	Remote Similarity	NPD5217	Approved
0.6733	Remote Similarity	NPD6117	Approved
0.6729	Remote Similarity	NPD5279	Phase 3
0.6729	Remote Similarity	NPD4689	Approved
0.6729	Remote Similarity	NPD5205	Approved
0.6729	Remote Similarity	NPD4693	Phase 3
0.6729	Remote Similarity	NPD4688	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