NPASS Compound

Structure

CID320026 OpenBabel06191716152D 34 37 0 0 1 0 0 0 0 0999 V2000 0.0811 2.7369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1899 6.5705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8414 5.8465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3779 -2.9594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2526 -2.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 0.5236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3669 4.0400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5691 3.0872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 -1.4622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6894 -1.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6885 0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2210 -0.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0909 4.6915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3770 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8440 1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8451 2.4357 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6888 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8445 -0.4873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6879 0.9739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5336 -1.4618 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2212 -1.4613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8448 1.4617 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8886 5.6442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3776 -1.9490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5333 -0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9744 0.0000 C 0 0 2 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 -2.5542 1.4734 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0876 -1.9608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7602 6.8983 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9624 5.9455 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 15 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 21 2 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 26 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 22 1 0 0 0 0 18 30 1 0 0 0 0 19 1 1 1 0 0 0 19 25 1 0 0 0 0 20 21 1 0 0 0 0 20 28 1 6 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 6 0 0 0 23 27 1 0 0 0 0 23 28 1 6 0 0 0 24 27 1 0 0 0 0 24 32 2 0 0 0 0 25 29 1 1 0 0 0 26 34 1 0 0 0 0 28 6 1 6 0 0 0 29 30 1 1 0 0 0 30 8 1 6 0 0 0 33 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	520.462
LogP:	5.623
LogD:	4.766
LogS:	-4.969
# Rotatable Bonds:	5
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.257
Synthetic Accessibility Score:	5.176
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.028
MDCK Permeability:	1.6270234482362866e-05
Pgp-inhibitor:	0.914
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.235
30% Bioavailability (F30%):	0.209

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.643
Plasma Protein Binding (PPB):	97.95342254638672%
Volume Distribution (VD):	1.0
Pgp-substrate:	3.2167296409606934%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.422
CYP2C19-inhibitor:	0.13
CYP2C19-substrate:	0.933
CYP2C9-inhibitor:	0.299
CYP2C9-substrate:	0.866
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.354
CYP3A4-inhibitor:	0.912
CYP3A4-substrate:	0.638

ADMET: Excretion

Clearance (CL):	5.34
Half-life (T1/2):	0.346

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.279
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.678
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.112
Carcinogencity:	0.621
Eye Corrosion:	0.033
Eye Irritation:	0.073
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC320026

Natural Product ID:	NPC320026
*Common Name:**	Meliasenin J
IUPAC Name:	(5R,9R,10R,13S,14S,16S,17S)-17-[(E,2R)-6-hydroperoxy-6-methylhept-4-en-2-yl]-16-hydroxy-4,4,10,13,14-pentamethyl-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:	Meliasenin J
Standard InCHIKey:	KXEPOJYGPBBQJS-LKJGIETFSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-19(10-9-15-26(2,3)34-33)25-22(31)18-30(8)21-11-12-23-27(4,5)24(32)14-16-28(23,6)20(21)13-17-29(25,30)7/h9,11,15,19-20,22-23,25,31,33H,10,12-14,16-18H2,1-8H3/b15-9+/t19-,20+,22+,23+,25-,28-,29+,30-/m1/s1
SMILES:	OOC(/C=C/C[C@H]([C@@H]1[C@@H](O)C[C@]2([C@@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641918
PubChem CID:	50908888
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
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19341288]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	fruits	Wanyuan County, Sichuan Province, China	2007-OCT	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1045	Cell Line	U2OS	Homo sapiens	IC50	=	14.3	ug.mL-1	PMID[554343]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1.1	ug.mL-1	PMID[554343]

☑ 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 NPC320026 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	163
0.1-0.2	1029
0.2-0.3	4820
0.3-0.4	14894
0.4-0.5	7754
0.5-0.6	6571
0.6-0.7	5082
0.7-0.8	2029
0.8-0.85	254
0.85-0.9	85
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9647	High Similarity	NPC2983
0.9643	High Similarity	NPC317590
0.9333	High Similarity	NPC57416
0.9294	High Similarity	NPC469994
0.9286	High Similarity	NPC82902
0.9213	High Similarity	NPC8993
0.9176	High Similarity	NPC474218
0.9176	High Similarity	NPC471224
0.9121	High Similarity	NPC107243
0.9091	High Similarity	NPC171441
0.8989	High Similarity	NPC473998
0.8989	High Similarity	NPC475806
0.8977	High Similarity	NPC76879
0.8977	High Similarity	NPC477943
0.8966	High Similarity	NPC90652
0.8953	High Similarity	NPC474083
0.8889	High Similarity	NPC472942
0.8876	High Similarity	NPC69622
0.8864	High Similarity	NPC328313
0.8864	High Similarity	NPC470417
0.8837	High Similarity	NPC214043
0.8837	High Similarity	NPC161423
0.8837	High Similarity	NPC227064
0.8837	High Similarity	NPC59453
0.8837	High Similarity	NPC58841
0.8837	High Similarity	NPC221758
0.8837	High Similarity	NPC85774
0.8837	High Similarity	NPC321187
0.8837	High Similarity	NPC329043
0.8804	High Similarity	NPC322063
0.8791	High Similarity	NPC292793
0.8778	High Similarity	NPC154101
0.8764	High Similarity	NPC326627
0.8764	High Similarity	NPC473999
0.8764	High Similarity	NPC309603
0.8764	High Similarity	NPC32830
0.8764	High Similarity	NPC310010
0.8764	High Similarity	NPC474245
0.875	High Similarity	NPC58063
0.8737	High Similarity	NPC87351
0.8736	High Similarity	NPC318390
0.8723	High Similarity	NPC154072
0.871	High Similarity	NPC475894
0.8696	High Similarity	NPC472932
0.8681	High Similarity	NPC243866
0.8681	High Similarity	NPC474736
0.8667	High Similarity	NPC48010
0.8646	High Similarity	NPC311612
0.8636	High Similarity	NPC474732
0.8636	High Similarity	NPC51014
0.8636	High Similarity	NPC474733
0.8636	High Similarity	NPC473168
0.8636	High Similarity	NPC31564
0.8636	High Similarity	NPC145879
0.8636	High Similarity	NPC474778
0.8621	High Similarity	NPC473246
0.8605	High Similarity	NPC151519
0.8605	High Similarity	NPC193347
0.8602	High Similarity	NPC49371
0.8602	High Similarity	NPC155676
0.8602	High Similarity	NPC249954
0.8587	High Similarity	NPC111015
0.8571	High Similarity	NPC477514
0.8571	High Similarity	NPC82635
0.8556	High Similarity	NPC472971
0.8556	High Similarity	NPC476733
0.8556	High Similarity	NPC472970
0.8556	High Similarity	NPC1015
0.8556	High Similarity	NPC215029
0.8556	High Similarity	NPC31985
0.8556	High Similarity	NPC54689
0.8542	High Similarity	NPC477915
0.8542	High Similarity	NPC185530
0.8539	High Similarity	NPC472481
0.8539	High Similarity	NPC472484
0.8539	High Similarity	NPC93778
0.8539	High Similarity	NPC96496
0.8539	High Similarity	NPC475740
0.8539	High Similarity	NPC472482
0.8523	High Similarity	NPC469948
0.8511	High Similarity	NPC126815
0.8511	High Similarity	NPC291634
0.8506	High Similarity	NPC470046
0.8506	High Similarity	NPC470047
0.8495	Intermediate Similarity	NPC469599
0.8495	Intermediate Similarity	NPC259286
0.8495	Intermediate Similarity	NPC271195
0.8488	Intermediate Similarity	NPC47761
0.8478	Intermediate Similarity	NPC152897
0.8478	Intermediate Similarity	NPC470375
0.8478	Intermediate Similarity	NPC474807
0.8478	Intermediate Similarity	NPC233118
0.8478	Intermediate Similarity	NPC470376
0.8478	Intermediate Similarity	NPC66429
0.8478	Intermediate Similarity	NPC472930
0.8471	Intermediate Similarity	NPC215843
0.8469	Intermediate Similarity	NPC257353
0.8454	Intermediate Similarity	NPC111323
0.8454	Intermediate Similarity	NPC26478
0.8444	Intermediate Similarity	NPC193360
0.8444	Intermediate Similarity	NPC44181
0.8427	Intermediate Similarity	NPC475022
0.8427	Intermediate Similarity	NPC222613
0.8427	Intermediate Similarity	NPC155011
0.8427	Intermediate Similarity	NPC327115
0.8427	Intermediate Similarity	NPC89077
0.8427	Intermediate Similarity	NPC118648
0.8427	Intermediate Similarity	NPC20688
0.8421	Intermediate Similarity	NPC235464
0.8421	Intermediate Similarity	NPC166745
0.8421	Intermediate Similarity	NPC197386
0.8409	Intermediate Similarity	NPC165064
0.8409	Intermediate Similarity	NPC237712
0.8409	Intermediate Similarity	NPC144258
0.8391	Intermediate Similarity	NPC145143
0.8387	Intermediate Similarity	NPC174051
0.8387	Intermediate Similarity	NPC299100
0.8387	Intermediate Similarity	NPC67831
0.8384	Intermediate Similarity	NPC185
0.8372	Intermediate Similarity	NPC472478
0.837	Intermediate Similarity	NPC262870
0.837	Intermediate Similarity	NPC272746
0.8367	Intermediate Similarity	NPC209502
0.8367	Intermediate Similarity	NPC204833
0.8352	Intermediate Similarity	NPC475921
0.8352	Intermediate Similarity	NPC186688
0.8352	Intermediate Similarity	NPC474704
0.8352	Intermediate Similarity	NPC155479
0.8352	Intermediate Similarity	NPC262043
0.8352	Intermediate Similarity	NPC26959
0.8352	Intermediate Similarity	NPC268406
0.8351	Intermediate Similarity	NPC473424
0.8333	Intermediate Similarity	NPC312215
0.8333	Intermediate Similarity	NPC218383
0.8333	Intermediate Similarity	NPC128644
0.8333	Intermediate Similarity	NPC83709
0.8333	Intermediate Similarity	NPC144956
0.8333	Intermediate Similarity	NPC136548
0.8333	Intermediate Similarity	NPC474684
0.8333	Intermediate Similarity	NPC142361
0.8333	Intermediate Similarity	NPC136948
0.8316	Intermediate Similarity	NPC18509
0.8316	Intermediate Similarity	NPC190554
0.8315	Intermediate Similarity	NPC470574
0.8315	Intermediate Similarity	NPC269638
0.8315	Intermediate Similarity	NPC274724
0.8298	Intermediate Similarity	NPC263347
0.8298	Intermediate Similarity	NPC180950
0.8298	Intermediate Similarity	NPC476174
0.8298	Intermediate Similarity	NPC472485
0.8295	Intermediate Similarity	NPC477852
0.8295	Intermediate Similarity	NPC476082
0.8295	Intermediate Similarity	NPC278648
0.8283	Intermediate Similarity	NPC50692
0.8283	Intermediate Similarity	NPC49958
0.8283	Intermediate Similarity	NPC260268
0.8283	Intermediate Similarity	NPC302607
0.8283	Intermediate Similarity	NPC149047
0.8283	Intermediate Similarity	NPC60681
0.8283	Intermediate Similarity	NPC476027
0.8283	Intermediate Similarity	NPC152695
0.8283	Intermediate Similarity	NPC48733
0.8283	Intermediate Similarity	NPC97202
0.8283	Intermediate Similarity	NPC202167
0.8283	Intermediate Similarity	NPC296945
0.8283	Intermediate Similarity	NPC85829
0.8283	Intermediate Similarity	NPC150531
0.8283	Intermediate Similarity	NPC214264
0.8283	Intermediate Similarity	NPC319077
0.8283	Intermediate Similarity	NPC171137
0.828	Intermediate Similarity	NPC250575
0.828	Intermediate Similarity	NPC475255
0.828	Intermediate Similarity	NPC206810
0.828	Intermediate Similarity	NPC69454
0.8276	Intermediate Similarity	NPC147066
0.8276	Intermediate Similarity	NPC6434
0.8276	Intermediate Similarity	NPC264245
0.8265	Intermediate Similarity	NPC247957
0.8265	Intermediate Similarity	NPC249187
0.8261	Intermediate Similarity	NPC469400
0.8261	Intermediate Similarity	NPC46281
0.8247	Intermediate Similarity	NPC473174
0.8247	Intermediate Similarity	NPC474327
0.8242	Intermediate Similarity	NPC328539
0.8242	Intermediate Similarity	NPC472483
0.8242	Intermediate Similarity	NPC471722
0.8242	Intermediate Similarity	NPC294480
0.8242	Intermediate Similarity	NPC53911
0.8229	Intermediate Similarity	NPC477854
0.8229	Intermediate Similarity	NPC103051
0.8229	Intermediate Similarity	NPC48647
0.8229	Intermediate Similarity	NPC186810
0.8222	Intermediate Similarity	NPC322159
0.8222	Intermediate Similarity	NPC94755
0.8222	Intermediate Similarity	NPC470955
0.8222	Intermediate Similarity	NPC470051
0.8222	Intermediate Similarity	NPC152808
0.8222	Intermediate Similarity	NPC470050
0.8222	Intermediate Similarity	NPC72133
0.8222	Intermediate Similarity	NPC212843

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 NPC320026 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	1295
0.2-0.3	3997
0.3-0.4	2585
0.4-0.5	623
0.5-0.6	165
0.6-0.7	132
0.7-0.8	152
0.8-0.85	42
0.85-0.9	13
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8837	High Similarity	NPD3666	Approved
0.8837	High Similarity	NPD3133	Approved
0.8837	High Similarity	NPD3665	Phase 1
0.8837	High Similarity	NPD4786	Approved
0.8764	High Similarity	NPD4753	Phase 2
0.8605	High Similarity	NPD4223	Phase 3
0.8605	High Similarity	NPD4221	Approved
0.8605	High Similarity	NPD3667	Approved
0.8523	High Similarity	NPD5329	Approved
0.8495	Intermediate Similarity	NPD4629	Approved
0.8495	Intermediate Similarity	NPD5210	Approved
0.8478	Intermediate Similarity	NPD4202	Approved
0.8409	Intermediate Similarity	NPD4197	Approved
0.837	Intermediate Similarity	NPD6079	Approved
0.8352	Intermediate Similarity	NPD5328	Approved
0.8351	Intermediate Similarity	NPD5211	Phase 2
0.8333	Intermediate Similarity	NPD5285	Approved
0.8333	Intermediate Similarity	NPD5286	Approved
0.8333	Intermediate Similarity	NPD4696	Approved
0.8316	Intermediate Similarity	NPD6084	Phase 2
0.8316	Intermediate Similarity	NPD6083	Phase 2
0.8316	Intermediate Similarity	NPD4755	Approved
0.8295	Intermediate Similarity	NPD4788	Approved
0.8247	Intermediate Similarity	NPD5223	Approved
0.8222	Intermediate Similarity	NPD4690	Approved
0.8222	Intermediate Similarity	NPD4138	Approved
0.8222	Intermediate Similarity	NPD4693	Phase 3
0.8222	Intermediate Similarity	NPD4688	Approved
0.8222	Intermediate Similarity	NPD4689	Approved
0.8222	Intermediate Similarity	NPD3618	Phase 1
0.8222	Intermediate Similarity	NPD5205	Approved
0.8222	Intermediate Similarity	NPD5690	Phase 2
0.8182	Intermediate Similarity	NPD5141	Approved
0.8163	Intermediate Similarity	NPD5225	Approved
0.8163	Intermediate Similarity	NPD4633	Approved
0.8163	Intermediate Similarity	NPD5224	Approved
0.8163	Intermediate Similarity	NPD5226	Approved
0.8144	Intermediate Similarity	NPD4700	Approved
0.8085	Intermediate Similarity	NPD6399	Phase 3
0.8081	Intermediate Similarity	NPD5174	Approved
0.8081	Intermediate Similarity	NPD5175	Approved
0.8046	Intermediate Similarity	NPD4195	Approved
0.8022	Intermediate Similarity	NPD6684	Approved
0.8022	Intermediate Similarity	NPD4694	Approved
0.8022	Intermediate Similarity	NPD5280	Approved
0.8022	Intermediate Similarity	NPD7334	Approved
0.8022	Intermediate Similarity	NPD7146	Approved
0.8022	Intermediate Similarity	NPD5279	Phase 3
0.8022	Intermediate Similarity	NPD7521	Approved
0.8022	Intermediate Similarity	NPD6409	Approved
0.8022	Intermediate Similarity	NPD5330	Approved
0.8021	Intermediate Similarity	NPD5221	Approved
0.8021	Intermediate Similarity	NPD5222	Approved
0.8021	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3668	Phase 3
0.7979	Intermediate Similarity	NPD5281	Approved
0.7979	Intermediate Similarity	NPD5284	Approved
0.7941	Intermediate Similarity	NPD6881	Approved
0.7941	Intermediate Similarity	NPD6899	Approved
0.7938	Intermediate Similarity	NPD5173	Approved
0.7921	Intermediate Similarity	NPD5739	Approved
0.7921	Intermediate Similarity	NPD7128	Approved
0.7921	Intermediate Similarity	NPD6675	Approved
0.7921	Intermediate Similarity	NPD6402	Approved
0.7917	Intermediate Similarity	NPD5695	Phase 3
0.7907	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD4754	Approved
0.7882	Intermediate Similarity	NPD4784	Approved
0.7882	Intermediate Similarity	NPD4785	Approved
0.7865	Intermediate Similarity	NPD4692	Approved
0.7865	Intermediate Similarity	NPD4139	Approved
0.7857	Intermediate Similarity	NPD5696	Approved
0.7857	Intermediate Similarity	NPD4243	Approved
0.7849	Intermediate Similarity	NPD6903	Approved
0.7849	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD5697	Approved
0.7835	Intermediate Similarity	NPD4697	Phase 3
0.7826	Intermediate Similarity	NPD4519	Discontinued
0.7826	Intermediate Similarity	NPD4623	Approved
0.7826	Intermediate Similarity	NPD6098	Approved
0.7826	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6942	Approved
0.7791	Intermediate Similarity	NPD7339	Approved
0.7788	Intermediate Similarity	NPD7102	Approved
0.7788	Intermediate Similarity	NPD7290	Approved
0.7788	Intermediate Similarity	NPD6883	Approved
0.7767	Intermediate Similarity	NPD4729	Approved
0.7767	Intermediate Similarity	NPD7320	Approved
0.7767	Intermediate Similarity	NPD4730	Approved
0.7767	Intermediate Similarity	NPD6011	Approved
0.7766	Intermediate Similarity	NPD6673	Approved
0.7766	Intermediate Similarity	NPD6080	Approved
0.7766	Intermediate Similarity	NPD6904	Approved
0.7753	Intermediate Similarity	NPD7525	Registered
0.7745	Intermediate Similarity	NPD4767	Approved
0.7745	Intermediate Similarity	NPD4768	Approved
0.7742	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6869	Approved
0.7714	Intermediate Similarity	NPD6847	Approved
0.7714	Intermediate Similarity	NPD6649	Approved
0.7714	Intermediate Similarity	NPD8130	Phase 1
0.7714	Intermediate Similarity	NPD6650	Approved
0.7714	Intermediate Similarity	NPD6617	Approved
0.7692	Intermediate Similarity	NPD6014	Approved
0.7692	Intermediate Similarity	NPD6013	Approved
0.7692	Intermediate Similarity	NPD6372	Approved
0.7692	Intermediate Similarity	NPD6373	Approved
0.7692	Intermediate Similarity	NPD6012	Approved
0.767	Intermediate Similarity	NPD5701	Approved
0.766	Intermediate Similarity	NPD5737	Approved
0.766	Intermediate Similarity	NPD6672	Approved
0.7642	Intermediate Similarity	NPD8297	Approved
0.7642	Intermediate Similarity	NPD6882	Approved
0.7619	Intermediate Similarity	NPD5247	Approved
0.7619	Intermediate Similarity	NPD5249	Phase 3
0.7619	Intermediate Similarity	NPD5135	Approved
0.7619	Intermediate Similarity	NPD5169	Approved
0.7619	Intermediate Similarity	NPD5248	Approved
0.7619	Intermediate Similarity	NPD4634	Approved
0.7619	Intermediate Similarity	NPD5251	Approved
0.7619	Intermediate Similarity	NPD5250	Approved
0.7619	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD5693	Phase 1
0.7604	Intermediate Similarity	NPD7515	Phase 2
0.7596	Intermediate Similarity	NPD5128	Approved
0.7579	Intermediate Similarity	NPD6051	Approved
0.7551	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5127	Approved
0.7547	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5216	Approved
0.7547	Intermediate Similarity	NPD5217	Approved
0.7547	Intermediate Similarity	NPD5215	Approved
0.7529	Intermediate Similarity	NPD4244	Approved
0.7529	Intermediate Similarity	NPD4245	Approved
0.7528	Intermediate Similarity	NPD3617	Approved
0.7527	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5362	Discontinued
0.75	Intermediate Similarity	NPD4096	Approved
0.75	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD6412	Phase 2
0.7474	Intermediate Similarity	NPD4518	Approved
0.7474	Intermediate Similarity	NPD5208	Approved
0.7471	Intermediate Similarity	NPD6926	Approved
0.7471	Intermediate Similarity	NPD6924	Approved
0.7451	Intermediate Similarity	NPD5091	Approved
0.7426	Intermediate Similarity	NPD7639	Approved
0.7426	Intermediate Similarity	NPD7640	Approved
0.7423	Intermediate Similarity	NPD6050	Approved
0.7423	Intermediate Similarity	NPD5694	Approved
0.7412	Intermediate Similarity	NPD3698	Phase 2
0.7407	Intermediate Similarity	NPD4632	Approved
0.7391	Intermediate Similarity	NPD4269	Approved
0.7391	Intermediate Similarity	NPD4270	Approved
0.7386	Intermediate Similarity	NPD5275	Approved
0.7386	Intermediate Similarity	NPD4190	Phase 3
0.7364	Intermediate Similarity	NPD7115	Discovery
0.7363	Intermediate Similarity	NPD4695	Discontinued
0.7347	Intermediate Similarity	NPD5133	Approved
0.7339	Intermediate Similarity	NPD5167	Approved
0.7326	Intermediate Similarity	NPD4747	Approved
0.732	Intermediate Similarity	NPD5692	Phase 3
0.732	Intermediate Similarity	NPD5207	Approved
0.7303	Intermediate Similarity	NPD6933	Approved
0.7297	Intermediate Similarity	NPD6335	Approved
0.7283	Intermediate Similarity	NPD5369	Approved
0.7273	Intermediate Similarity	NPD7748	Approved
0.7264	Intermediate Similarity	NPD5168	Approved
0.7241	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7101	Approved
0.7232	Intermediate Similarity	NPD7100	Approved
0.7209	Intermediate Similarity	NPD4137	Phase 3
0.7207	Intermediate Similarity	NPD6317	Approved
0.7207	Intermediate Similarity	NPD6009	Approved
0.7174	Intermediate Similarity	NPD5368	Approved
0.7174	Intermediate Similarity	NPD4748	Discontinued
0.7174	Intermediate Similarity	NPD6930	Phase 2
0.7174	Intermediate Similarity	NPD7514	Phase 3
0.7174	Intermediate Similarity	NPD4820	Approved
0.7174	Intermediate Similarity	NPD4252	Approved
0.7174	Intermediate Similarity	NPD4821	Approved
0.7174	Intermediate Similarity	NPD4822	Approved
0.7174	Intermediate Similarity	NPD6931	Approved
0.7174	Intermediate Similarity	NPD4819	Approved
0.7168	Intermediate Similarity	NPD6054	Approved
0.7158	Intermediate Similarity	NPD5363	Approved
0.7143	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6314	Approved
0.7143	Intermediate Similarity	NPD6313	Approved
0.7143	Intermediate Similarity	NPD5785	Approved
0.7128	Intermediate Similarity	NPD6695	Phase 3
0.7128	Intermediate Similarity	NPD5332	Approved
0.7128	Intermediate Similarity	NPD5331	Approved
0.7126	Intermediate Similarity	NPD4789	Approved
0.7126	Intermediate Similarity	NPD7144	Approved
0.7126	Intermediate Similarity	NPD7143	Approved
0.7126	Intermediate Similarity	NPD4691	Approved
0.7117	Intermediate Similarity	NPD6274	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