NPASS Compound

Structure

CID318390 OpenBabel06191716142D 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 1 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 1 6 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:	474.37
Volume:	523.098
LogP:	5.961
LogD:	5.016
LogS:	-4.392
# Rotatable Bonds:	5
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.233
Synthetic Accessibility Score:	5.206
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.836
MDCK Permeability:	1.801401231205091e-05
Pgp-inhibitor:	0.936
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.32
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.548
Plasma Protein Binding (PPB):	99.34278106689453%
Volume Distribution (VD):	1.104
Pgp-substrate:	3.888957977294922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.199
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.903
CYP2C9-inhibitor:	0.241
CYP2C9-substrate:	0.538
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.213
CYP3A4-inhibitor:	0.892
CYP3A4-substrate:	0.516

ADMET: Excretion

Clearance (CL):	4.556
Half-life (T1/2):	0.142

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.316
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.184
Carcinogencity:	0.257
Eye Corrosion:	0.059
Eye Irritation:	0.06
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC318390

Natural Product ID:	NPC318390
*Common Name:**	Meliasenin I
IUPAC Name:	(3S,5R,9R,10R,13S,14S,16S,17S)-17-[(E,2R)-6-hydroperoxy-6-methylhept-4-en-2-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,16-diol
Synonyms:	Meliasenin I
Standard InCHIKey:	GXIUUQNLOQDGBR-OVBRUCOYSA-N
Standard InCHI:	InChI=1S/C30H50O4/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/h9,11,15,19-20,22-25,31-33H,10,12-14,16-18H2,1-8H3/b15-9+/t19-,20+,22+,23+,24+,25-,28-,29+,30-/m1/s1
SMILES:	CC(CC=CC(C)(C)OO)C1C(CC2(C1(CCC3C2=CCC4C3(CCC(C4(C)C)O)C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641917
PubChem CID:	50908887
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	=	9.5	ug.mL-1	PMID[555906]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	11.2	ug.mL-1	PMID[555906]

☑ 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 NPC318390 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	167
0.1-0.2	1348
0.2-0.3	5781
0.3-0.4	15882
0.4-0.5	7819
0.5-0.6	5661
0.6-0.7	4396
0.7-0.8	1301
0.8-0.85	211
0.85-0.9	119
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.925	High Similarity	NPC47761
0.9241	High Similarity	NPC1319
0.9157	High Similarity	NPC261266
0.9146	High Similarity	NPC470077
0.9146	High Similarity	NPC205845
0.9136	High Similarity	NPC49964
0.9136	High Similarity	NPC87489
0.9136	High Similarity	NPC296701
0.9136	High Similarity	NPC218616
0.9114	High Similarity	NPC477514
0.9024	High Similarity	NPC134481
0.9012	High Similarity	NPC264245
0.9	High Similarity	NPC30986
0.9	High Similarity	NPC209430
0.8929	High Similarity	NPC293287
0.8929	High Similarity	NPC152808
0.8929	High Similarity	NPC139724
0.8929	High Similarity	NPC6391
0.8916	High Similarity	NPC231310
0.8916	High Similarity	NPC124172
0.8902	High Similarity	NPC470049
0.8902	High Similarity	NPC30166
0.8902	High Similarity	NPC101462
0.8889	High Similarity	NPC322313
0.8889	High Similarity	NPC241290
0.8889	High Similarity	NPC234193
0.8889	High Similarity	NPC164840
0.8889	High Similarity	NPC236237
0.8889	High Similarity	NPC102253
0.8889	High Similarity	NPC209944
0.8875	High Similarity	NPC473943
0.8875	High Similarity	NPC285761
0.8875	High Similarity	NPC477522
0.8861	High Similarity	NPC134330
0.8861	High Similarity	NPC189883
0.8861	High Similarity	NPC129165
0.8824	High Similarity	NPC149224
0.881	High Similarity	NPC157257
0.881	High Similarity	NPC470360
0.881	High Similarity	NPC274448
0.8795	High Similarity	NPC82623
0.8795	High Similarity	NPC193870
0.8795	High Similarity	NPC110778
0.8795	High Similarity	NPC477818
0.8795	High Similarity	NPC141941
0.8795	High Similarity	NPC474634
0.8795	High Similarity	NPC470558
0.8765	High Similarity	NPC109546
0.8765	High Similarity	NPC143182
0.8765	High Similarity	NPC84694
0.8765	High Similarity	NPC28862
0.8765	High Similarity	NPC80530
0.8765	High Similarity	NPC47982
0.8765	High Similarity	NPC273410
0.8765	High Similarity	NPC81306
0.875	High Similarity	NPC198968
0.875	High Similarity	NPC318495
0.875	High Similarity	NPC214570
0.875	High Similarity	NPC155986
0.8736	High Similarity	NPC295668
0.8736	High Similarity	NPC320026
0.8734	High Similarity	NPC257347
0.8734	High Similarity	NPC471723
0.8734	High Similarity	NPC141071
0.8721	High Similarity	NPC133588
0.8706	High Similarity	NPC6605
0.8706	High Similarity	NPC24277
0.8706	High Similarity	NPC201273
0.8706	High Similarity	NPC299068
0.869	High Similarity	NPC185568
0.869	High Similarity	NPC474047
0.869	High Similarity	NPC127606
0.869	High Similarity	NPC475798
0.869	High Similarity	NPC209802
0.869	High Similarity	NPC238485
0.8675	High Similarity	NPC202389
0.8675	High Similarity	NPC470614
0.8675	High Similarity	NPC201852
0.8675	High Similarity	NPC1272
0.8675	High Similarity	NPC20853
0.8675	High Similarity	NPC50964
0.8659	High Similarity	NPC26117
0.8659	High Similarity	NPC236112
0.8659	High Similarity	NPC13554
0.8642	High Similarity	NPC138621
0.8642	High Similarity	NPC244385
0.8642	High Similarity	NPC275910
0.8642	High Similarity	NPC6978
0.8642	High Similarity	NPC474216
0.8642	High Similarity	NPC167037
0.8636	High Similarity	NPC97404
0.8636	High Similarity	NPC41554
0.8625	High Similarity	NPC73875
0.8625	High Similarity	NPC247325
0.8625	High Similarity	NPC321381
0.8625	High Similarity	NPC237460
0.8625	High Similarity	NPC240604
0.8625	High Similarity	NPC470362
0.8625	High Similarity	NPC107059
0.8625	High Similarity	NPC202642
0.8625	High Similarity	NPC244488
0.8625	High Similarity	NPC321016
0.8625	High Similarity	NPC46160
0.8625	High Similarity	NPC96319
0.8625	High Similarity	NPC300324
0.8625	High Similarity	NPC113733
0.8621	High Similarity	NPC101886
0.8588	High Similarity	NPC266511
0.8571	High Similarity	NPC207013
0.8571	High Similarity	NPC317458
0.8571	High Similarity	NPC475789
0.8554	High Similarity	NPC82986
0.8554	High Similarity	NPC474759
0.8554	High Similarity	NPC474531
0.8554	High Similarity	NPC474683
0.8554	High Similarity	NPC474731
0.8554	High Similarity	NPC23852
0.8554	High Similarity	NPC474752
0.8554	High Similarity	NPC7505
0.8554	High Similarity	NPC209620
0.8537	High Similarity	NPC49627
0.8537	High Similarity	NPC328714
0.8537	High Similarity	NPC49599
0.8523	High Similarity	NPC3345
0.8523	High Similarity	NPC291484
0.8523	High Similarity	NPC270511
0.8523	High Similarity	NPC14380
0.8523	High Similarity	NPC470390
0.8523	High Similarity	NPC192437
0.8523	High Similarity	NPC11216
0.8523	High Similarity	NPC329596
0.8523	High Similarity	NPC204188
0.8523	High Similarity	NPC245410
0.8523	High Similarity	NPC80561
0.8519	High Similarity	NPC470758
0.8519	High Similarity	NPC470711
0.8519	High Similarity	NPC91594
0.8506	High Similarity	NPC4574
0.8506	High Similarity	NPC475605
0.8506	High Similarity	NPC212596
0.8506	High Similarity	NPC471952
0.8506	High Similarity	NPC474668
0.8506	High Similarity	NPC470542
0.85	High Similarity	NPC285893
0.85	High Similarity	NPC28657
0.85	High Similarity	NPC322353
0.85	High Similarity	NPC136188
0.85	High Similarity	NPC304309
0.85	High Similarity	NPC230301
0.85	High Similarity	NPC22105
0.85	High Similarity	NPC121744
0.85	High Similarity	NPC118508
0.85	High Similarity	NPC288035
0.85	High Similarity	NPC134847
0.85	High Similarity	NPC162742
0.8481	Intermediate Similarity	NPC182717
0.8471	Intermediate Similarity	NPC478102
0.8452	Intermediate Similarity	NPC189972
0.8444	Intermediate Similarity	NPC8993
0.8415	Intermediate Similarity	NPC42853
0.8415	Intermediate Similarity	NPC301707
0.8415	Intermediate Similarity	NPC11908
0.8415	Intermediate Similarity	NPC65897
0.8415	Intermediate Similarity	NPC302041
0.8415	Intermediate Similarity	NPC85346
0.8415	Intermediate Similarity	NPC186191
0.8415	Intermediate Similarity	NPC472501
0.8415	Intermediate Similarity	NPC87604
0.8415	Intermediate Similarity	NPC307965
0.8415	Intermediate Similarity	NPC18603
0.8415	Intermediate Similarity	NPC76931
0.8415	Intermediate Similarity	NPC205455
0.8409	Intermediate Similarity	NPC109744
0.8409	Intermediate Similarity	NPC470361
0.8409	Intermediate Similarity	NPC2983
0.8409	Intermediate Similarity	NPC138974
0.8409	Intermediate Similarity	NPC105495
0.8395	Intermediate Similarity	NPC265588
0.8395	Intermediate Similarity	NPC470749
0.8391	Intermediate Similarity	NPC470620
0.8391	Intermediate Similarity	NPC186145
0.8391	Intermediate Similarity	NPC304083
0.8391	Intermediate Similarity	NPC474657
0.8391	Intermediate Similarity	NPC317590
0.8375	Intermediate Similarity	NPC469534
0.8375	Intermediate Similarity	NPC469593
0.8375	Intermediate Similarity	NPC476366
0.8375	Intermediate Similarity	NPC201048
0.8375	Intermediate Similarity	NPC91858
0.8375	Intermediate Similarity	NPC477138
0.8375	Intermediate Similarity	NPC243342
0.8375	Intermediate Similarity	NPC469533
0.8372	Intermediate Similarity	NPC474349
0.8372	Intermediate Similarity	NPC474189
0.8354	Intermediate Similarity	NPC167706
0.8353	Intermediate Similarity	NPC470384
0.8333	Intermediate Similarity	NPC249423
0.8333	Intermediate Similarity	NPC470383
0.8333	Intermediate Similarity	NPC476646
0.8333	Intermediate Similarity	NPC6707

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 NPC318390 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1522
0.2-0.3	4338
0.3-0.4	2242
0.4-0.5	452
0.5-0.6	162
0.6-0.7	138
0.7-0.8	134
0.8-0.85	7
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD7525	Registered
0.8625	High Similarity	NPD3701	Clinical (unspecified phase)
0.85	High Similarity	NPD7339	Approved
0.85	High Similarity	NPD6942	Approved
0.8391	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD4784	Approved
0.8375	Intermediate Similarity	NPD4785	Approved
0.8354	Intermediate Similarity	NPD4243	Approved
0.8	Intermediate Similarity	NPD4748	Discontinued
0.7935	Intermediate Similarity	NPD4202	Approved
0.7927	Intermediate Similarity	NPD6924	Approved
0.7927	Intermediate Similarity	NPD6926	Approved
0.7882	Intermediate Similarity	NPD7645	Phase 2
0.7882	Intermediate Similarity	NPD4195	Approved
0.7841	Intermediate Similarity	NPD4786	Approved
0.7835	Intermediate Similarity	NPD5211	Phase 2
0.7831	Intermediate Similarity	NPD5275	Approved
0.7831	Intermediate Similarity	NPD4190	Phase 3
0.7826	Intermediate Similarity	NPD6079	Approved
0.7812	Intermediate Similarity	NPD5285	Approved
0.7812	Intermediate Similarity	NPD5286	Approved
0.7812	Intermediate Similarity	NPD4696	Approved
0.7802	Intermediate Similarity	NPD5328	Approved
0.7789	Intermediate Similarity	NPD4755	Approved
0.7738	Intermediate Similarity	NPD6933	Approved
0.7732	Intermediate Similarity	NPD5223	Approved
0.7683	Intermediate Similarity	NPD7151	Approved
0.7683	Intermediate Similarity	NPD7152	Approved
0.7683	Intermediate Similarity	NPD7150	Approved
0.7677	Intermediate Similarity	NPD5141	Approved
0.7667	Intermediate Similarity	NPD3618	Phase 1
0.7653	Intermediate Similarity	NPD5225	Approved
0.7653	Intermediate Similarity	NPD5226	Approved
0.7653	Intermediate Similarity	NPD5224	Approved
0.7653	Intermediate Similarity	NPD4633	Approved
0.764	Intermediate Similarity	NPD3133	Approved
0.764	Intermediate Similarity	NPD3665	Phase 1
0.764	Intermediate Similarity	NPD3666	Approved
0.7629	Intermediate Similarity	NPD4700	Approved
0.7614	Intermediate Similarity	NPD3667	Approved
0.7609	Intermediate Similarity	NPD6051	Approved
0.7609	Intermediate Similarity	NPD4753	Phase 2
0.7586	Intermediate Similarity	NPD6931	Approved
0.7586	Intermediate Similarity	NPD7514	Phase 3
0.7586	Intermediate Similarity	NPD6930	Phase 2
0.7576	Intermediate Similarity	NPD5174	Approved
0.7576	Intermediate Similarity	NPD5175	Approved
0.7561	Intermediate Similarity	NPD7143	Approved
0.7561	Intermediate Similarity	NPD7144	Approved
0.7558	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6695	Phase 3
0.7526	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5222	Approved
0.75	Intermediate Similarity	NPD5221	Approved
0.7471	Intermediate Similarity	NPD6929	Approved
0.7451	Intermediate Similarity	NPD6899	Approved
0.7451	Intermediate Similarity	NPD6881	Approved
0.7449	Intermediate Similarity	NPD7640	Approved
0.7449	Intermediate Similarity	NPD7639	Approved
0.7444	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6932	Approved
0.7439	Intermediate Similarity	NPD6923	Approved
0.7439	Intermediate Similarity	NPD6922	Approved
0.7426	Intermediate Similarity	NPD6675	Approved
0.7426	Intermediate Similarity	NPD7128	Approved
0.7426	Intermediate Similarity	NPD6402	Approved
0.7426	Intermediate Similarity	NPD5739	Approved
0.7423	Intermediate Similarity	NPD5173	Approved
0.7416	Intermediate Similarity	NPD4223	Phase 3
0.7416	Intermediate Similarity	NPD4221	Approved
0.7412	Intermediate Similarity	NPD8264	Approved
0.74	Intermediate Similarity	NPD4754	Approved
0.7396	Intermediate Similarity	NPD5210	Approved
0.7396	Intermediate Similarity	NPD4629	Approved
0.7386	Intermediate Similarity	NPD7332	Phase 2
0.7386	Intermediate Similarity	NPD7509	Discontinued
0.7363	Intermediate Similarity	NPD5329	Approved
0.7356	Intermediate Similarity	NPD7145	Approved
0.7353	Intermediate Similarity	NPD5697	Approved
0.732	Intermediate Similarity	NPD4697	Phase 3
0.7308	Intermediate Similarity	NPD7102	Approved
0.7308	Intermediate Similarity	NPD7290	Approved
0.7308	Intermediate Similarity	NPD6883	Approved
0.7303	Intermediate Similarity	NPD6902	Approved
0.7282	Intermediate Similarity	NPD6011	Approved
0.7282	Intermediate Similarity	NPD7320	Approved
0.7282	Intermediate Similarity	NPD4730	Approved
0.7282	Intermediate Similarity	NPD4729	Approved
0.7255	Intermediate Similarity	NPD4767	Approved
0.7255	Intermediate Similarity	NPD4768	Approved
0.7253	Intermediate Similarity	NPD4197	Approved
0.7245	Intermediate Similarity	NPD6084	Phase 2
0.7245	Intermediate Similarity	NPD6083	Phase 2
0.7241	Intermediate Similarity	NPD6925	Approved
0.7241	Intermediate Similarity	NPD5776	Phase 2
0.7238	Intermediate Similarity	NPD6617	Approved
0.7238	Intermediate Similarity	NPD6869	Approved
0.7238	Intermediate Similarity	NPD6650	Approved
0.7238	Intermediate Similarity	NPD6847	Approved
0.7238	Intermediate Similarity	NPD6649	Approved
0.7238	Intermediate Similarity	NPD8130	Phase 1
0.7229	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6372	Approved
0.7212	Intermediate Similarity	NPD6012	Approved
0.7212	Intermediate Similarity	NPD6013	Approved
0.7212	Intermediate Similarity	NPD6014	Approved
0.7212	Intermediate Similarity	NPD6373	Approved
0.7204	Intermediate Similarity	NPD7524	Approved
0.7204	Intermediate Similarity	NPD7750	Discontinued
0.7188	Intermediate Similarity	NPD6399	Phase 3
0.7184	Intermediate Similarity	NPD5701	Approved
0.7174	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6893	Approved
0.717	Intermediate Similarity	NPD8297	Approved
0.717	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD5169	Approved
0.7143	Intermediate Similarity	NPD5247	Approved
0.7143	Intermediate Similarity	NPD5251	Approved
0.7143	Intermediate Similarity	NPD4634	Approved
0.7143	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5135	Approved
0.7143	Intermediate Similarity	NPD4788	Approved
0.7143	Intermediate Similarity	NPD5248	Approved
0.7143	Intermediate Similarity	NPD5249	Phase 3
0.7143	Intermediate Similarity	NPD4787	Phase 1
0.7143	Intermediate Similarity	NPD5250	Approved
0.7115	Intermediate Similarity	NPD5128	Approved
0.7097	Intermediate Similarity	NPD5205	Approved
0.7097	Intermediate Similarity	NPD4693	Phase 3
0.7097	Intermediate Similarity	NPD4690	Approved
0.7097	Intermediate Similarity	NPD5690	Phase 2
0.7097	Intermediate Similarity	NPD4688	Approved
0.7097	Intermediate Similarity	NPD4689	Approved
0.7097	Intermediate Similarity	NPD4138	Approved
0.7097	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7515	Phase 2
0.7079	Intermediate Similarity	NPD6683	Phase 2
0.7075	Intermediate Similarity	NPD5215	Approved
0.7075	Intermediate Similarity	NPD5127	Approved
0.7075	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5217	Approved
0.7075	Intermediate Similarity	NPD5216	Approved
0.7065	Intermediate Similarity	NPD3668	Phase 3
0.703	Intermediate Similarity	NPD4159	Approved
0.7	Intermediate Similarity	NPD5290	Discontinued
0.6947	Remote Similarity	NPD4723	Approved
0.6947	Remote Similarity	NPD4722	Approved
0.6944	Remote Similarity	NPD4632	Approved
0.6923	Remote Similarity	NPD6898	Phase 1
0.6915	Remote Similarity	NPD5280	Approved
0.6915	Remote Similarity	NPD7334	Approved
0.6915	Remote Similarity	NPD6684	Approved
0.6915	Remote Similarity	NPD5330	Approved
0.6915	Remote Similarity	NPD7146	Approved
0.6915	Remote Similarity	NPD7521	Approved
0.6915	Remote Similarity	NPD6409	Approved
0.6915	Remote Similarity	NPD5279	Phase 3
0.6915	Remote Similarity	NPD4694	Approved
0.6909	Remote Similarity	NPD7115	Discovery
0.6907	Remote Similarity	NPD7087	Discontinued
0.6907	Remote Similarity	NPD5284	Approved
0.6907	Remote Similarity	NPD5281	Approved
0.6881	Remote Similarity	NPD5167	Approved
0.6869	Remote Similarity	NPD5695	Phase 3
0.6869	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7327	Approved
0.6847	Remote Similarity	NPD7328	Approved
0.6847	Remote Similarity	NPD6335	Approved
0.6832	Remote Similarity	NPD5696	Approved
0.6814	Remote Similarity	NPD7503	Approved
0.6796	Remote Similarity	NPD7632	Discontinued
0.6792	Remote Similarity	NPD5168	Approved
0.679	Remote Similarity	NPD368	Approved
0.6786	Remote Similarity	NPD7516	Approved
0.6786	Remote Similarity	NPD7100	Approved
0.6786	Remote Similarity	NPD7101	Approved
0.6771	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6903	Approved
0.6768	Remote Similarity	NPD7748	Approved
0.6757	Remote Similarity	NPD6009	Approved
0.6757	Remote Similarity	NPD6317	Approved
0.6739	Remote Similarity	NPD4692	Approved
0.6739	Remote Similarity	NPD4139	Approved
0.6737	Remote Similarity	NPD6098	Approved
0.6737	Remote Similarity	NPD4623	Approved
0.6737	Remote Similarity	NPD4519	Discontinued
0.6735	Remote Similarity	NPD8034	Phase 2
0.6735	Remote Similarity	NPD8035	Phase 2
0.6735	Remote Similarity	NPD7637	Suspended
0.6726	Remote Similarity	NPD6054	Approved
0.6726	Remote Similarity	NPD8377	Approved
0.6726	Remote Similarity	NPD8294	Approved
0.6701	Remote Similarity	NPD6080	Approved
0.6701	Remote Similarity	NPD6904	Approved
0.6701	Remote Similarity	NPD6673	Approved
0.6696	Remote Similarity	NPD6313	Approved
0.6696	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	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