NPASS Compound

Structure

CID322063 OpenBabel06191716162D 35 39 0 0 1 0 0 0 0 0999 V2000 1.0685 -6.4751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2765 -5.4925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3578 2.9374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2235 2.4374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5180 -0.5161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6817 -4.1018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3705 -3.1468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 1.4535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6793 1.9379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6785 -0.9691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1958 0.4834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0103 -4.8488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3569 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 -1.4534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6776 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0419 -2.3998 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6788 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8395 0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 -0.9681 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5185 1.4531 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1961 1.4526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 -1.4530 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0049 -2.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3215 -5.8037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3575 1.9374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5183 0.4839 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9686 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 -5.0624 1.9522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5079 -3.3696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0387 -7.5057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3979 -1.6153 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3499 -6.5507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 14 2 0 0 0 0 10 11 1 0 0 0 0 10 20 2 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 26 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 9 1 6 0 0 0 18 24 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 30 1 0 0 0 0 21 17 1 6 0 0 0 21 24 1 0 0 0 0 21 34 1 0 0 0 0 22 27 1 0 0 0 0 22 28 1 6 0 0 0 23 27 1 0 0 0 0 23 31 2 0 0 0 0 24 29 1 1 0 0 0 25 32 2 0 0 0 0 25 34 1 0 0 0 0 26 35 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 33 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.32
Volume:	518.059
LogP:	5.568
LogD:	4.334
LogS:	-5.317
# Rotatable Bonds:	4
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.213
Synthetic Accessibility Score:	5.206
Fsp3:	0.8
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:	-5.057
MDCK Permeability:	2.0923776901327074e-05
Pgp-inhibitor:	0.978
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.083
30% Bioavailability (F30%):	0.227

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.674
Plasma Protein Binding (PPB):	95.03936004638672%
Volume Distribution (VD):	1.182
Pgp-substrate:	5.492724418640137%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.408
CYP2C19-inhibitor:	0.162
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.235
CYP2C9-substrate:	0.642
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.259
CYP3A4-inhibitor:	0.851
CYP3A4-substrate:	0.625

ADMET: Excretion

Clearance (CL):	4.487
Half-life (T1/2):	0.155

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.173
Drug-inuced Liver Injury (DILI):	0.061
AMES Toxicity:	0.106
Rat Oral Acute Toxicity:	0.753
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.117
Carcinogencity:	0.694
Eye Corrosion:	0.024
Eye Irritation:	0.057
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC322063

Natural Product ID:	NPC322063
*Common Name:**	Meliasenin M
IUPAC Name:	n.a.
Synonyms:	Meliasenin M
Standard InCHIKey:	LQPSEQWINGOYLK-UHVZVPEASA-N
Standard InCHI:	InChI=1S/C30H44O5/c1-26(2,35-33)14-8-9-18-24-21(34-25(18)32)17-30(7)20-10-11-22-27(3,4)23(31)13-15-28(22,5)19(20)12-16-29(24,30)6/h8,10,14,18-19,21-22,24,33H,9,11-13,15-17H2,1-7H3/b14-8+/t18-,19+,21+,22+,24-,28-,29+,30-/m1/s1
SMILES:	OOC(/C=C/C[C@H]1C(=O)O[C@@H]2[C@@H]1[C@]1(C)CC[C@H]3C(=CC[C@@H]4[C@]3(C)CCC(=O)C4(C)C)[C@]1(C2)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641921
PubChem CID:	50900151
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	=	29.2	ug.mL-1	PMID[502811]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	16.4	ug.mL-1	PMID[502811]

☑ 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 NPC322063 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	204
0.1-0.2	1133
0.2-0.3	5302
0.3-0.4	14983
0.4-0.5	6903
0.5-0.6	6857
0.6-0.7	5776
0.7-0.8	1457
0.8-0.85	67
0.85-0.9	9
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9247	High Similarity	NPC475894
0.9247	High Similarity	NPC57416
0.9213	High Similarity	NPC28227
0.9149	High Similarity	NPC153792
0.9149	High Similarity	NPC271387
0.9043	High Similarity	NPC107243
0.8876	High Similarity	NPC470223
0.8804	High Similarity	NPC320026
0.8764	High Similarity	NPC100391
0.871	High Similarity	NPC154101
0.871	High Similarity	NPC150383
0.8681	High Similarity	NPC167877
0.8632	High Similarity	NPC469599
0.8571	High Similarity	NPC470051
0.8571	High Similarity	NPC195640
0.8571	High Similarity	NPC470050
0.8526	High Similarity	NPC472224
0.8526	High Similarity	NPC472223
0.8495	Intermediate Similarity	NPC2983
0.8478	Intermediate Similarity	NPC317590
0.8462	Intermediate Similarity	NPC323765
0.8421	Intermediate Similarity	NPC470224
0.8421	Intermediate Similarity	NPC243866
0.84	Intermediate Similarity	NPC140723
0.8384	Intermediate Similarity	NPC474327
0.837	Intermediate Similarity	NPC264127
0.8351	Intermediate Similarity	NPC155676
0.8333	Intermediate Similarity	NPC294266
0.8317	Intermediate Similarity	NPC164835
0.8317	Intermediate Similarity	NPC472228
0.8317	Intermediate Similarity	NPC228669
0.8317	Intermediate Similarity	NPC472227
0.8315	Intermediate Similarity	NPC170038
0.8298	Intermediate Similarity	NPC476733
0.8298	Intermediate Similarity	NPC54689
0.8298	Intermediate Similarity	NPC215029
0.8298	Intermediate Similarity	NPC474570
0.8298	Intermediate Similarity	NPC305039
0.8283	Intermediate Similarity	NPC218383
0.828	Intermediate Similarity	NPC128644
0.8261	Intermediate Similarity	NPC474218
0.8242	Intermediate Similarity	NPC470047
0.8242	Intermediate Similarity	NPC470046
0.8229	Intermediate Similarity	NPC470375
0.8229	Intermediate Similarity	NPC152897
0.8229	Intermediate Similarity	NPC66429
0.8229	Intermediate Similarity	NPC470376
0.8218	Intermediate Similarity	NPC36321
0.8218	Intermediate Similarity	NPC36688
0.8211	Intermediate Similarity	NPC171441
0.8211	Intermediate Similarity	NPC471896
0.8202	Intermediate Similarity	NPC118987
0.82	Intermediate Similarity	NPC99411
0.8191	Intermediate Similarity	NPC97884
0.8191	Intermediate Similarity	NPC294480
0.8191	Intermediate Similarity	NPC472220
0.8182	Intermediate Similarity	NPC176845
0.8172	Intermediate Similarity	NPC469994
0.8155	Intermediate Similarity	NPC220974
0.8152	Intermediate Similarity	NPC82902
0.8144	Intermediate Similarity	NPC56525
0.8144	Intermediate Similarity	NPC159410
0.8144	Intermediate Similarity	NPC8993
0.8137	Intermediate Similarity	NPC255309
0.8132	Intermediate Similarity	NPC240302
0.8125	Intermediate Similarity	NPC218301
0.8119	Intermediate Similarity	NPC22388
0.8119	Intermediate Similarity	NPC473928
0.8113	Intermediate Similarity	NPC100267
0.8113	Intermediate Similarity	NPC475524
0.8105	Intermediate Similarity	NPC262043
0.8105	Intermediate Similarity	NPC155479
0.8105	Intermediate Similarity	NPC477943
0.8105	Intermediate Similarity	NPC177141
0.8085	Intermediate Similarity	NPC96496
0.8085	Intermediate Similarity	NPC312215
0.8085	Intermediate Similarity	NPC136948
0.8081	Intermediate Similarity	NPC151488
0.8081	Intermediate Similarity	NPC292133
0.8065	Intermediate Similarity	NPC269638
0.8065	Intermediate Similarity	NPC471224
0.8061	Intermediate Similarity	NPC280877
0.8061	Intermediate Similarity	NPC33473
0.8061	Intermediate Similarity	NPC69548
0.8061	Intermediate Similarity	NPC184848
0.8061	Intermediate Similarity	NPC263347
0.8061	Intermediate Similarity	NPC84383
0.8058	Intermediate Similarity	NPC96377
0.8058	Intermediate Similarity	NPC196528
0.8056	Intermediate Similarity	NPC266728
0.8056	Intermediate Similarity	NPC49492
0.8043	Intermediate Similarity	NPC477852
0.8043	Intermediate Similarity	NPC170862
0.8041	Intermediate Similarity	NPC107674
0.8041	Intermediate Similarity	NPC475700
0.8041	Intermediate Similarity	NPC141497
0.8041	Intermediate Similarity	NPC170220
0.8039	Intermediate Similarity	NPC236390
0.8022	Intermediate Similarity	NPC232625
0.8022	Intermediate Similarity	NPC474955
0.8022	Intermediate Similarity	NPC147066
0.8021	Intermediate Similarity	NPC111585
0.8021	Intermediate Similarity	NPC148414
0.8021	Intermediate Similarity	NPC46281
0.8021	Intermediate Similarity	NPC175628
0.802	Intermediate Similarity	NPC310981
0.802	Intermediate Similarity	NPC476223
0.802	Intermediate Similarity	NPC224720
0.802	Intermediate Similarity	NPC476240
0.8	Intermediate Similarity	NPC166745
0.8	Intermediate Similarity	NPC252295
0.8	Intermediate Similarity	NPC226863
0.8	Intermediate Similarity	NPC48647
0.8	Intermediate Similarity	NPC235464
0.8	Intermediate Similarity	NPC197386
0.8	Intermediate Similarity	NPC98868
0.8	Intermediate Similarity	NPC477854
0.8	Intermediate Similarity	NPC477813
0.8	Intermediate Similarity	NPC186810
0.8	Intermediate Similarity	NPC477128
0.8	Intermediate Similarity	NPC183546
0.8	Intermediate Similarity	NPC474845
0.7981	Intermediate Similarity	NPC64844
0.7981	Intermediate Similarity	NPC131665
0.7981	Intermediate Similarity	NPC42847
0.7981	Intermediate Similarity	NPC475294
0.7981	Intermediate Similarity	NPC255387
0.798	Intermediate Similarity	NPC307164
0.798	Intermediate Similarity	NPC111684
0.798	Intermediate Similarity	NPC42042
0.798	Intermediate Similarity	NPC58052
0.7979	Intermediate Similarity	NPC322159
0.7979	Intermediate Similarity	NPC155011
0.7979	Intermediate Similarity	NPC472505
0.7979	Intermediate Similarity	NPC212843
0.7961	Intermediate Similarity	NPC471293
0.7961	Intermediate Similarity	NPC189616
0.7961	Intermediate Similarity	NPC235889
0.7961	Intermediate Similarity	NPC473175
0.7959	Intermediate Similarity	NPC7165
0.7959	Intermediate Similarity	NPC292793
0.7959	Intermediate Similarity	NPC471720
0.7957	Intermediate Similarity	NPC165064
0.7944	Intermediate Similarity	NPC221144
0.7941	Intermediate Similarity	NPC308351
0.7941	Intermediate Similarity	NPC271266
0.7941	Intermediate Similarity	NPC87351
0.7941	Intermediate Similarity	NPC204450
0.7941	Intermediate Similarity	NPC185530
0.7941	Intermediate Similarity	NPC136289
0.7941	Intermediate Similarity	NPC195290
0.7938	Intermediate Similarity	NPC110657
0.7938	Intermediate Similarity	NPC45269
0.7938	Intermediate Similarity	NPC49420
0.7938	Intermediate Similarity	NPC190442
0.7938	Intermediate Similarity	NPC475806
0.7938	Intermediate Similarity	NPC177641
0.7938	Intermediate Similarity	NPC212301
0.7938	Intermediate Similarity	NPC297265
0.7938	Intermediate Similarity	NPC86266
0.7938	Intermediate Similarity	NPC26888
0.7938	Intermediate Similarity	NPC473998
0.7938	Intermediate Similarity	NPC23434
0.7935	Intermediate Similarity	NPC133391
0.7935	Intermediate Similarity	NPC100297
0.7921	Intermediate Similarity	NPC154072
0.7921	Intermediate Similarity	NPC167974
0.7921	Intermediate Similarity	NPC476274
0.7921	Intermediate Similarity	NPC476303
0.7917	Intermediate Similarity	NPC475921
0.7917	Intermediate Similarity	NPC76879
0.7917	Intermediate Similarity	NPC474704
0.7917	Intermediate Similarity	NPC474889
0.7917	Intermediate Similarity	NPC285982
0.7917	Intermediate Similarity	NPC474679
0.7905	Intermediate Similarity	NPC472825
0.79	Intermediate Similarity	NPC187159
0.79	Intermediate Similarity	NPC10057
0.79	Intermediate Similarity	NPC126815
0.79	Intermediate Similarity	NPC291634
0.7895	Intermediate Similarity	NPC474684
0.7895	Intermediate Similarity	NPC142361
0.7895	Intermediate Similarity	NPC90652
0.789	Intermediate Similarity	NPC148458
0.7885	Intermediate Similarity	NPC127790
0.7885	Intermediate Similarity	NPC181265
0.7885	Intermediate Similarity	NPC470309
0.7879	Intermediate Similarity	NPC279974
0.7879	Intermediate Similarity	NPC162001
0.7879	Intermediate Similarity	NPC45324
0.7879	Intermediate Similarity	NPC476174
0.7879	Intermediate Similarity	NPC222845
0.7879	Intermediate Similarity	NPC171395
0.7879	Intermediate Similarity	NPC20546
0.7872	Intermediate Similarity	NPC29447
0.7872	Intermediate Similarity	NPC470048
0.7872	Intermediate Similarity	NPC474083
0.787	Intermediate Similarity	NPC962
0.787	Intermediate Similarity	NPC250109
0.7864	Intermediate Similarity	NPC112009

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 NPC322063 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1331
0.2-0.3	4138
0.3-0.4	2427
0.4-0.5	600
0.5-0.6	167
0.6-0.7	187
0.7-0.8	115
0.8-0.85	22
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8632	High Similarity	NPD6356	Clinical (unspecified phase)
0.8587	High Similarity	NPD6903	Approved
0.8571	High Similarity	NPD6409	Approved
0.8571	High Similarity	NPD7521	Approved
0.8571	High Similarity	NPD6684	Approved
0.8571	High Similarity	NPD7334	Approved
0.8571	High Similarity	NPD5330	Approved
0.8571	High Similarity	NPD7146	Approved
0.8421	Intermediate Similarity	NPD6399	Phase 3
0.8404	Intermediate Similarity	NPD5207	Approved
0.8387	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.837	Intermediate Similarity	NPD6098	Approved
0.8298	Intermediate Similarity	NPD6673	Approved
0.8298	Intermediate Similarity	NPD6080	Approved
0.8298	Intermediate Similarity	NPD6904	Approved
0.8265	Intermediate Similarity	NPD6083	Phase 2
0.8265	Intermediate Similarity	NPD6084	Phase 2
0.8191	Intermediate Similarity	NPD6672	Approved
0.8191	Intermediate Similarity	NPD5737	Approved
0.8182	Intermediate Similarity	NPD5696	Approved
0.8144	Intermediate Similarity	NPD6001	Approved
0.8125	Intermediate Similarity	NPD5693	Phase 1
0.8105	Intermediate Similarity	NPD6051	Approved
0.8061	Intermediate Similarity	NPD5695	Phase 3
0.8058	Intermediate Similarity	NPD6008	Approved
0.8	Intermediate Similarity	NPD5208	Approved
0.7938	Intermediate Similarity	NPD6050	Approved
0.7938	Intermediate Similarity	NPD5284	Approved
0.7938	Intermediate Similarity	NPD5694	Approved
0.7938	Intermediate Similarity	NPD5281	Approved
0.7905	Intermediate Similarity	NPD6899	Approved
0.7905	Intermediate Similarity	NPD6881	Approved
0.7905	Intermediate Similarity	NPD7320	Approved
0.7885	Intermediate Similarity	NPD6402	Approved
0.7885	Intermediate Similarity	NPD5739	Approved
0.7885	Intermediate Similarity	NPD7128	Approved
0.7885	Intermediate Similarity	NPD6675	Approved
0.7864	Intermediate Similarity	NPD6052	Approved
0.785	Intermediate Similarity	NPD6650	Approved
0.785	Intermediate Similarity	NPD6649	Approved
0.7835	Intermediate Similarity	NPD5692	Phase 3
0.783	Intermediate Similarity	NPD6373	Approved
0.783	Intermediate Similarity	NPD6372	Approved
0.781	Intermediate Similarity	NPD5697	Approved
0.7766	Intermediate Similarity	NPD3133	Approved
0.7766	Intermediate Similarity	NPD3666	Approved
0.7766	Intermediate Similarity	NPD4786	Approved
0.7766	Intermediate Similarity	NPD3665	Phase 1
0.7757	Intermediate Similarity	NPD7290	Approved
0.7757	Intermediate Similarity	NPD6883	Approved
0.7757	Intermediate Similarity	NPD7102	Approved
0.7742	Intermediate Similarity	NPD4223	Phase 3
0.7742	Intermediate Similarity	NPD4221	Approved
0.7736	Intermediate Similarity	NPD6011	Approved
0.7732	Intermediate Similarity	NPD4753	Phase 2
0.77	Intermediate Similarity	NPD4629	Approved
0.77	Intermediate Similarity	NPD5210	Approved
0.7685	Intermediate Similarity	NPD6847	Approved
0.7685	Intermediate Similarity	NPD8130	Phase 1
0.7685	Intermediate Similarity	NPD6869	Approved
0.7685	Intermediate Similarity	NPD6617	Approved
0.7684	Intermediate Similarity	NPD5329	Approved
0.7664	Intermediate Similarity	NPD6012	Approved
0.7664	Intermediate Similarity	NPD6013	Approved
0.7664	Intermediate Similarity	NPD6014	Approved
0.7642	Intermediate Similarity	NPD5701	Approved
0.7615	Intermediate Similarity	NPD6882	Approved
0.7615	Intermediate Similarity	NPD8297	Approved
0.7579	Intermediate Similarity	NPD4197	Approved
0.7579	Intermediate Similarity	NPD3668	Phase 3
0.7553	Intermediate Similarity	NPD3667	Approved
0.7523	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4202	Approved
0.75	Intermediate Similarity	NPD1694	Approved
0.75	Intermediate Similarity	NPD7115	Discovery
0.7477	Intermediate Similarity	NPD6614	Approved
0.7476	Intermediate Similarity	NPD7638	Approved
0.7474	Intermediate Similarity	NPD5362	Discontinued
0.7429	Intermediate Similarity	NPD5211	Phase 2
0.7426	Intermediate Similarity	NPD7748	Approved
0.7426	Intermediate Similarity	NPD7900	Approved
0.7426	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4689	Approved
0.7423	Intermediate Similarity	NPD5690	Phase 2
0.7423	Intermediate Similarity	NPD4138	Approved
0.7423	Intermediate Similarity	NPD4690	Approved
0.7423	Intermediate Similarity	NPD3618	Phase 1
0.7423	Intermediate Similarity	NPD4688	Approved
0.7423	Intermediate Similarity	NPD4693	Phase 3
0.7423	Intermediate Similarity	NPD5205	Approved
0.7404	Intermediate Similarity	NPD7639	Approved
0.7404	Intermediate Similarity	NPD7640	Approved
0.7404	Intermediate Similarity	NPD5286	Approved
0.7404	Intermediate Similarity	NPD4696	Approved
0.7404	Intermediate Similarity	NPD5285	Approved
0.74	Intermediate Similarity	NPD8035	Phase 2
0.74	Intermediate Similarity	NPD8034	Phase 2
0.74	Intermediate Similarity	NPD6079	Approved
0.7391	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4755	Approved
0.7379	Intermediate Similarity	NPD7902	Approved
0.7374	Intermediate Similarity	NPD5328	Approved
0.7368	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5654	Approved
0.7333	Intermediate Similarity	NPD5223	Approved
0.7312	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4788	Approved
0.729	Intermediate Similarity	NPD5141	Approved
0.7281	Intermediate Similarity	NPD6335	Approved
0.7264	Intermediate Similarity	NPD5224	Approved
0.7264	Intermediate Similarity	NPD5226	Approved
0.7264	Intermediate Similarity	NPD4633	Approved
0.7264	Intermediate Similarity	NPD5225	Approved
0.7263	Intermediate Similarity	NPD5369	Approved
0.7245	Intermediate Similarity	NPD5280	Approved
0.7245	Intermediate Similarity	NPD4694	Approved
0.7245	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD4700	Approved
0.7234	Intermediate Similarity	NPD4195	Approved
0.7232	Intermediate Similarity	NPD4632	Approved
0.7228	Intermediate Similarity	NPD7515	Phase 2
0.7222	Intermediate Similarity	NPD5777	Approved
0.7217	Intermediate Similarity	NPD7100	Approved
0.7217	Intermediate Similarity	NPD7101	Approved
0.7212	Intermediate Similarity	NPD5959	Approved
0.7203	Intermediate Similarity	NPD7492	Approved
0.7196	Intermediate Similarity	NPD5175	Approved
0.7196	Intermediate Similarity	NPD5174	Approved
0.7193	Intermediate Similarity	NPD6317	Approved
0.7188	Intermediate Similarity	NPD4270	Approved
0.7188	Intermediate Similarity	NPD4269	Approved
0.7172	Intermediate Similarity	NPD3573	Approved
0.7156	Intermediate Similarity	NPD6412	Phase 2
0.7155	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD6053	Discontinued
0.7143	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6616	Approved
0.713	Intermediate Similarity	NPD6313	Approved
0.713	Intermediate Similarity	NPD6314	Approved
0.7129	Intermediate Similarity	NPD5785	Approved
0.7115	Intermediate Similarity	NPD5222	Approved
0.7115	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5221	Approved
0.7115	Intermediate Similarity	NPD4697	Phase 3
0.7105	Intermediate Similarity	NPD6274	Approved
0.7083	Intermediate Similarity	NPD7078	Approved
0.7083	Intermediate Similarity	NPD4139	Approved
0.7083	Intermediate Similarity	NPD4692	Approved
0.7071	Intermediate Similarity	NPD4623	Approved
0.7071	Intermediate Similarity	NPD5786	Approved
0.7071	Intermediate Similarity	NPD5279	Phase 3
0.7071	Intermediate Similarity	NPD4519	Discontinued
0.7065	Intermediate Similarity	NPD4784	Approved
0.7065	Intermediate Similarity	NPD4785	Approved
0.7059	Intermediate Similarity	NPD7637	Suspended
0.7048	Intermediate Similarity	NPD5173	Approved
0.7043	Intermediate Similarity	NPD6009	Approved
0.7037	Intermediate Similarity	NPD4754	Approved
0.7034	Intermediate Similarity	NPD6370	Approved
0.7033	Intermediate Similarity	NPD4243	Approved
0.7025	Intermediate Similarity	NPD7736	Approved
0.701	Intermediate Similarity	NPD6435	Approved
0.7009	Intermediate Similarity	NPD6319	Approved
0.7009	Intermediate Similarity	NPD6059	Approved
0.6989	Remote Similarity	NPD3702	Approved
0.6979	Remote Similarity	NPD4252	Approved
0.6975	Remote Similarity	NPD7604	Phase 2
0.697	Remote Similarity	NPD5363	Approved
0.697	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6868	Approved
0.6949	Remote Similarity	NPD6908	Approved
0.6949	Remote Similarity	NPD6909	Approved
0.6949	Remote Similarity	NPD6015	Approved
0.6949	Remote Similarity	NPD5983	Phase 2
0.6949	Remote Similarity	NPD6016	Approved
0.6944	Remote Similarity	NPD5091	Approved
0.6942	Remote Similarity	NPD8293	Discontinued
0.6939	Remote Similarity	NPD5332	Approved
0.6939	Remote Similarity	NPD5331	Approved
0.6937	Remote Similarity	NPD4729	Approved
0.6937	Remote Similarity	NPD4730	Approved
0.693	Remote Similarity	NPD6858	Approved
0.693	Remote Similarity	NPD7094	Approved
0.6923	Remote Similarity	NPD4747	Approved
0.6915	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4767	Approved
0.6909	Remote Similarity	NPD4768	Approved
0.6907	Remote Similarity	NPD4790	Discontinued
0.6893	Remote Similarity	NPD6411	Approved
0.6891	Remote Similarity	NPD5988	Approved
0.686	Remote Similarity	NPD7507	Approved
0.686	Remote Similarity	NPD6336	Discontinued
0.6832	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5251	Approved
0.6814	Remote Similarity	NPD4634	Approved
0.6814	Remote Similarity	NPD5247	Approved
0.6814	Remote Similarity	NPD5135	Approved
0.6814	Remote Similarity	NPD5248	Approved
0.6814	Remote Similarity	NPD5249	Phase 3
0.6814	Remote Similarity	NPD5250	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