NPASS Compound

Structure

CID79117 OpenBabel06191715412D 28 31 0 0 1 0 0 0 0 0999 V2000 -1.6781 -2.9085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5186 -2.4578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3883 -1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8402 2.4577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6787 1.0050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8698 -0.5025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8391 1.4537 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 -0.0006 1.9381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5178 0.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5175 0.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8399 -1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6796 1.9376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8388 -2.4236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5178 1.4527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8394 0.4849 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6793 -0.9689 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8396 0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3571 -0.9684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9693 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5183 -1.4533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8399 1.4532 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6790 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0008 -2.9080 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3880 1.9545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2274 -1.4701 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8391 -1.4543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 10 2 0 0 0 0 8 19 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 15 1 0 0 0 0 11 18 2 0 0 0 0 12 17 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 25 2 0 0 0 0 14 28 1 0 0 0 0 15 26 2 0 0 0 0 16 23 1 6 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 6 0 0 0 18 22 1 0 0 0 0 18 24 1 0 0 0 0 19 21 1 0 0 0 0 19 27 2 0 0 0 0 20 24 1 1 0 0 0 20 28 1 0 0 0 0 22 4 1 1 0 0 0 23 5 1 6 0 0 0 24 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.23
Volume:	411.413
LogP:	2.932
LogD:	2.416
LogS:	-4.568
# Rotatable Bonds:	2
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.628
Synthetic Accessibility Score:	4.774
Fsp3:	0.708
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.164
MDCK Permeability:	3.36344564857427e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.367
30% Bioavailability (F30%):	0.595

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.146
Plasma Protein Binding (PPB):	81.44696807861328%
Volume Distribution (VD):	0.78
Pgp-substrate:	18.947731018066406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.374
CYP2C19-inhibitor:	0.115
CYP2C19-substrate:	0.83
CYP2C9-inhibitor:	0.227
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.752
CYP3A4-substrate:	0.896

ADMET: Excretion

Clearance (CL):	2.95
Half-life (T1/2):	0.712

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.481
Drug-inuced Liver Injury (DILI):	0.114
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.58
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.934
Carcinogencity:	0.121
Eye Corrosion:	0.033
Eye Irritation:	0.04
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC79117

Natural Product ID:	NPC79117
*Common Name:**	Desfuranoazadiradione
IUPAC Name:	[(5R,7R,8R,9R,10R,13S)-4,4,8,10,13-pentamethyl-3,16-dioxo-6,7,9,11,12,17-hexahydro-5H-cyclopenta[a]phenanthren-7-yl] acetate
Synonyms:	Desfuranoazadiradione
Standard InCHIKey:	RACYWTTYSJTPOV-TUJRATNISA-N
Standard InCHI:	InChI=1S/C24H32O4/c1-14(25)28-20-12-17-21(2,3)19(27)8-10-23(17,5)16-7-9-22(4)13-15(26)11-18(22)24(16,20)6/h8,10-11,16-17,20H,7,9,12-13H2,1-6H3/t16-,17+,20-,22+,23-,24-/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@@]3(C)CC(=O)C=C3[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774395
PubChem CID:	52952012
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
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193038]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593280]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18816111]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20669933]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607354]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614419]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26339153]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28493718]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	19800.0	nM	PMID[458604]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20000.0	nM	PMID[458604]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	20000.0	nM	PMID[458604]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20000.0	nM	PMID[458604]

☑ 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 NPC79117 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	224
0.1-0.2	1331
0.2-0.3	4864
0.3-0.4	10416
0.4-0.5	11816
0.5-0.6	6788
0.6-0.7	5010
0.7-0.8	2119
0.8-0.85	108
0.85-0.9	15
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9556	High Similarity	NPC292133
0.9053	High Similarity	NPC264048
0.8958	High Similarity	NPC189616
0.8925	High Similarity	NPC84335
0.8925	High Similarity	NPC38530
0.8925	High Similarity	NPC23680
0.8901	High Similarity	NPC474185
0.8889	High Similarity	NPC475965
0.8889	High Similarity	NPC474842
0.8791	High Similarity	NPC218301
0.8723	High Similarity	NPC226986
0.871	High Similarity	NPC274417
0.8687	High Similarity	NPC469844
0.8681	High Similarity	NPC328141
0.8632	High Similarity	NPC114274
0.8617	High Similarity	NPC471039
0.8617	High Similarity	NPC58052
0.8617	High Similarity	NPC111684
0.8602	High Similarity	NPC471040
0.8602	High Similarity	NPC269729
0.86	High Similarity	NPC41405
0.8556	High Similarity	NPC30421
0.8526	High Similarity	NPC108078
0.8526	High Similarity	NPC473456
0.8515	High Similarity	NPC239097
0.8515	High Similarity	NPC5284
0.8511	High Similarity	NPC317586
0.8511	High Similarity	NPC470016
0.8478	Intermediate Similarity	NPC152467
0.8454	Intermediate Similarity	NPC310981
0.8444	Intermediate Similarity	NPC264127
0.8444	Intermediate Similarity	NPC195640
0.8438	Intermediate Similarity	NPC471582
0.8438	Intermediate Similarity	NPC176845
0.8421	Intermediate Similarity	NPC151725
0.8421	Intermediate Similarity	NPC122324
0.8421	Intermediate Similarity	NPC106425
0.8409	Intermediate Similarity	NPC100297
0.8404	Intermediate Similarity	NPC473435
0.8404	Intermediate Similarity	NPC473431
0.8404	Intermediate Similarity	NPC166906
0.8404	Intermediate Similarity	NPC159410
0.8404	Intermediate Similarity	NPC473280
0.8404	Intermediate Similarity	NPC471078
0.837	Intermediate Similarity	NPC73995
0.8367	Intermediate Similarity	NPC308351
0.8367	Intermediate Similarity	NPC136289
0.8367	Intermediate Similarity	NPC271266
0.8351	Intermediate Similarity	NPC475385
0.8351	Intermediate Similarity	NPC471041
0.8351	Intermediate Similarity	NPC475392
0.8351	Intermediate Similarity	NPC475202
0.835	Intermediate Similarity	NPC234042
0.835	Intermediate Similarity	NPC152117
0.8333	Intermediate Similarity	NPC323765
0.8333	Intermediate Similarity	NPC110937
0.8333	Intermediate Similarity	NPC2049
0.8333	Intermediate Similarity	NPC197428
0.8316	Intermediate Similarity	NPC473170
0.8298	Intermediate Similarity	NPC107674
0.8298	Intermediate Similarity	NPC469315
0.8298	Intermediate Similarity	NPC170220
0.8298	Intermediate Similarity	NPC141497
0.8283	Intermediate Similarity	NPC254202
0.8283	Intermediate Similarity	NPC36321
0.828	Intermediate Similarity	NPC471896
0.8269	Intermediate Similarity	NPC255017
0.8265	Intermediate Similarity	NPC168319
0.8265	Intermediate Similarity	NPC224720
0.8265	Intermediate Similarity	NPC194028
0.8265	Intermediate Similarity	NPC476223
0.8265	Intermediate Similarity	NPC476240
0.8265	Intermediate Similarity	NPC469327
0.8265	Intermediate Similarity	NPC81530
0.8261	Intermediate Similarity	NPC97884
0.8261	Intermediate Similarity	NPC215831
0.8261	Intermediate Similarity	NPC80335
0.8261	Intermediate Similarity	NPC472220
0.8252	Intermediate Similarity	NPC470960
0.8247	Intermediate Similarity	NPC252295
0.8247	Intermediate Similarity	NPC478056
0.8242	Intermediate Similarity	NPC471042
0.8242	Intermediate Similarity	NPC220478
0.8229	Intermediate Similarity	NPC328162
0.8229	Intermediate Similarity	NPC305483
0.8229	Intermediate Similarity	NPC96859
0.8218	Intermediate Similarity	NPC44063
0.8218	Intermediate Similarity	NPC475294
0.8211	Intermediate Similarity	NPC240617
0.8211	Intermediate Similarity	NPC74751
0.8211	Intermediate Similarity	NPC471207
0.8211	Intermediate Similarity	NPC294266
0.82	Intermediate Similarity	NPC235889
0.8191	Intermediate Similarity	NPC86266
0.8191	Intermediate Similarity	NPC212301
0.8191	Intermediate Similarity	NPC110657
0.8191	Intermediate Similarity	NPC26888
0.8182	Intermediate Similarity	NPC473163
0.8173	Intermediate Similarity	NPC71348
0.8172	Intermediate Similarity	NPC50070
0.8172	Intermediate Similarity	NPC177141
0.8172	Intermediate Similarity	NPC119416
0.8163	Intermediate Similarity	NPC266955
0.8163	Intermediate Similarity	NPC476274
0.8163	Intermediate Similarity	NPC35751
0.8152	Intermediate Similarity	NPC46912
0.8152	Intermediate Similarity	NPC162107
0.8144	Intermediate Similarity	NPC216904
0.8144	Intermediate Similarity	NPC253826
0.8125	Intermediate Similarity	NPC469599
0.8125	Intermediate Similarity	NPC139570
0.8125	Intermediate Similarity	NPC139459
0.8125	Intermediate Similarity	NPC33473
0.8119	Intermediate Similarity	NPC470267
0.8119	Intermediate Similarity	NPC181265
0.8113	Intermediate Similarity	NPC243981
0.8105	Intermediate Similarity	NPC214756
0.8105	Intermediate Similarity	NPC477435
0.8105	Intermediate Similarity	NPC477436
0.8105	Intermediate Similarity	NPC295643
0.8105	Intermediate Similarity	NPC272075
0.81	Intermediate Similarity	NPC179208
0.81	Intermediate Similarity	NPC132395
0.81	Intermediate Similarity	NPC471364
0.81	Intermediate Similarity	NPC95585
0.81	Intermediate Similarity	NPC471365
0.81	Intermediate Similarity	NPC282233
0.809	Intermediate Similarity	NPC475665
0.809	Intermediate Similarity	NPC474955
0.8085	Intermediate Similarity	NPC161638
0.8085	Intermediate Similarity	NPC148414
0.8085	Intermediate Similarity	NPC85173
0.8085	Intermediate Similarity	NPC175628
0.8085	Intermediate Similarity	NPC474728
0.8085	Intermediate Similarity	NPC111585
0.8081	Intermediate Similarity	NPC115899
0.8065	Intermediate Similarity	NPC474845
0.8065	Intermediate Similarity	NPC474677
0.8065	Intermediate Similarity	NPC328539
0.8061	Intermediate Similarity	NPC275439
0.8061	Intermediate Similarity	NPC477854
0.8061	Intermediate Similarity	NPC112753
0.8061	Intermediate Similarity	NPC471717
0.8061	Intermediate Similarity	NPC57079
0.8061	Intermediate Similarity	NPC108368
0.8061	Intermediate Similarity	NPC194196
0.8058	Intermediate Similarity	NPC2766
0.8046	Intermediate Similarity	NPC472300
0.8043	Intermediate Similarity	NPC9892
0.8043	Intermediate Similarity	NPC325594
0.8043	Intermediate Similarity	NPC91525
0.8043	Intermediate Similarity	NPC329943
0.8043	Intermediate Similarity	NPC73038
0.8043	Intermediate Similarity	NPC10005
0.8041	Intermediate Similarity	NPC250757
0.8041	Intermediate Similarity	NPC301534
0.8041	Intermediate Similarity	NPC471775
0.8041	Intermediate Similarity	NPC471822
0.8041	Intermediate Similarity	NPC471153
0.8041	Intermediate Similarity	NPC307164
0.8041	Intermediate Similarity	NPC328371
0.8041	Intermediate Similarity	NPC95565
0.8039	Intermediate Similarity	NPC220974
0.8037	Intermediate Similarity	NPC284068
0.8022	Intermediate Similarity	NPC109512
0.8022	Intermediate Similarity	NPC139566
0.8021	Intermediate Similarity	NPC38830
0.8021	Intermediate Similarity	NPC49670
0.8021	Intermediate Similarity	NPC470697
0.8021	Intermediate Similarity	NPC477130
0.8021	Intermediate Similarity	NPC184870
0.8021	Intermediate Similarity	NPC477439
0.8021	Intermediate Similarity	NPC477129
0.802	Intermediate Similarity	NPC228669
0.802	Intermediate Similarity	NPC164835
0.802	Intermediate Similarity	NPC255309
0.8	Intermediate Similarity	NPC32577
0.8	Intermediate Similarity	NPC470590
0.8	Intermediate Similarity	NPC4036
0.8	Intermediate Similarity	NPC264634
0.8	Intermediate Similarity	NPC285184
0.8	Intermediate Similarity	NPC185936
0.8	Intermediate Similarity	NPC147180
0.8	Intermediate Similarity	NPC321289
0.8	Intermediate Similarity	NPC142683
0.8	Intermediate Similarity	NPC470230
0.8	Intermediate Similarity	NPC158030
0.8	Intermediate Similarity	NPC168027
0.8	Intermediate Similarity	NPC233455
0.8	Intermediate Similarity	NPC327969
0.8	Intermediate Similarity	NPC60755
0.8	Intermediate Similarity	NPC272746
0.8	Intermediate Similarity	NPC65120
0.8	Intermediate Similarity	NPC77099
0.8	Intermediate Similarity	NPC114540
0.8	Intermediate Similarity	NPC22388
0.8	Intermediate Similarity	NPC155332
0.8	Intermediate Similarity	NPC145067
0.8	Intermediate Similarity	NPC320447
0.798	Intermediate Similarity	NPC316964

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 NPC79117 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1575
0.2-0.3	3869
0.3-0.4	2258
0.4-0.5	790
0.5-0.6	219
0.6-0.7	116
0.7-0.8	118
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8556	High Similarity	NPD3573	Approved
0.8444	Intermediate Similarity	NPD6684	Approved
0.8444	Intermediate Similarity	NPD5330	Approved
0.8444	Intermediate Similarity	NPD7521	Approved
0.8444	Intermediate Similarity	NPD7146	Approved
0.8444	Intermediate Similarity	NPD7334	Approved
0.8444	Intermediate Similarity	NPD6409	Approved
0.8387	Intermediate Similarity	NPD6079	Approved
0.8317	Intermediate Similarity	NPD6899	Approved
0.8317	Intermediate Similarity	NPD6881	Approved
0.8261	Intermediate Similarity	NPD6672	Approved
0.8261	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD6903	Approved
0.8261	Intermediate Similarity	NPD5737	Approved
0.8218	Intermediate Similarity	NPD5697	Approved
0.8211	Intermediate Similarity	NPD7900	Approved
0.8211	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8211	Intermediate Similarity	NPD7748	Approved
0.8172	Intermediate Similarity	NPD5328	Approved
0.8155	Intermediate Similarity	NPD7102	Approved
0.8155	Intermediate Similarity	NPD7290	Approved
0.8155	Intermediate Similarity	NPD6883	Approved
0.8137	Intermediate Similarity	NPD6011	Approved
0.8119	Intermediate Similarity	NPD6008	Approved
0.8119	Intermediate Similarity	NPD5739	Approved
0.8119	Intermediate Similarity	NPD6675	Approved
0.8119	Intermediate Similarity	NPD6402	Approved
0.8119	Intermediate Similarity	NPD7128	Approved
0.8105	Intermediate Similarity	NPD6399	Phase 3
0.8077	Intermediate Similarity	NPD6869	Approved
0.8077	Intermediate Similarity	NPD6650	Approved
0.8077	Intermediate Similarity	NPD6649	Approved
0.8077	Intermediate Similarity	NPD6847	Approved
0.8077	Intermediate Similarity	NPD8130	Phase 1
0.8077	Intermediate Similarity	NPD6617	Approved
0.8058	Intermediate Similarity	NPD6013	Approved
0.8058	Intermediate Similarity	NPD6014	Approved
0.8058	Intermediate Similarity	NPD6012	Approved
0.8041	Intermediate Similarity	NPD5221	Approved
0.8041	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD5222	Approved
0.8	Intermediate Similarity	NPD7515	Phase 2
0.8	Intermediate Similarity	NPD6882	Approved
0.8	Intermediate Similarity	NPD8297	Approved
0.7961	Intermediate Similarity	NPD7320	Approved
0.7959	Intermediate Similarity	NPD5173	Approved
0.7959	Intermediate Similarity	NPD7902	Approved
0.7938	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1694	Approved
0.7885	Intermediate Similarity	NPD6372	Approved
0.7885	Intermediate Similarity	NPD6373	Approved
0.7864	Intermediate Similarity	NPD5701	Approved
0.7849	Intermediate Similarity	NPD3618	Phase 1
0.78	Intermediate Similarity	NPD5286	Approved
0.78	Intermediate Similarity	NPD4696	Approved
0.78	Intermediate Similarity	NPD5285	Approved
0.7789	Intermediate Similarity	NPD6904	Approved
0.7789	Intermediate Similarity	NPD6080	Approved
0.7789	Intermediate Similarity	NPD6673	Approved
0.7778	Intermediate Similarity	NPD6868	Approved
0.7736	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD5223	Approved
0.7677	Intermediate Similarity	NPD4697	Phase 3
0.7647	Intermediate Similarity	NPD4633	Approved
0.7647	Intermediate Similarity	NPD5226	Approved
0.7647	Intermediate Similarity	NPD5224	Approved
0.7647	Intermediate Similarity	NPD5225	Approved
0.7647	Intermediate Similarity	NPD5211	Phase 2
0.7636	Intermediate Similarity	NPD6335	Approved
0.7634	Intermediate Similarity	NPD3668	Phase 3
0.7634	Intermediate Similarity	NPD4786	Approved
0.7609	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD3667	Approved
0.76	Intermediate Similarity	NPD6083	Phase 2
0.76	Intermediate Similarity	NPD6084	Phase 2
0.76	Intermediate Similarity	NPD4755	Approved
0.7593	Intermediate Similarity	NPD4632	Approved
0.7573	Intermediate Similarity	NPD5174	Approved
0.7573	Intermediate Similarity	NPD5175	Approved
0.7568	Intermediate Similarity	NPD7101	Approved
0.7568	Intermediate Similarity	NPD7100	Approved
0.7545	Intermediate Similarity	NPD7115	Discovery
0.7545	Intermediate Similarity	NPD6317	Approved
0.7525	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD5208	Approved
0.75	Intermediate Similarity	NPD5141	Approved
0.7477	Intermediate Similarity	NPD6314	Approved
0.7477	Intermediate Similarity	NPD6313	Approved
0.7475	Intermediate Similarity	NPD6001	Approved
0.7474	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD6098	Approved
0.7455	Intermediate Similarity	NPD6274	Approved
0.7451	Intermediate Similarity	NPD7639	Approved
0.7451	Intermediate Similarity	NPD4700	Approved
0.7451	Intermediate Similarity	NPD7640	Approved
0.7449	Intermediate Similarity	NPD6050	Approved
0.7449	Intermediate Similarity	NPD5694	Approved
0.7449	Intermediate Similarity	NPD5693	Phase 1
0.7449	Intermediate Similarity	NPD6411	Approved
0.7447	Intermediate Similarity	NPD3665	Phase 1
0.7447	Intermediate Similarity	NPD3666	Approved
0.7447	Intermediate Similarity	NPD3133	Approved
0.74	Intermediate Similarity	NPD5695	Phase 3
0.7387	Intermediate Similarity	NPD6009	Approved
0.7374	Intermediate Similarity	NPD4202	Approved
0.7353	Intermediate Similarity	NPD5696	Approved
0.7347	Intermediate Similarity	NPD5207	Approved
0.7347	Intermediate Similarity	NPD5692	Phase 3
0.7345	Intermediate Similarity	NPD6319	Approved
0.7327	Intermediate Similarity	NPD7732	Phase 3
0.7304	Intermediate Similarity	NPD7604	Phase 2
0.729	Intermediate Similarity	NPD4729	Approved
0.729	Intermediate Similarity	NPD5168	Approved
0.729	Intermediate Similarity	NPD4730	Approved
0.7281	Intermediate Similarity	NPD5983	Phase 2
0.7281	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8035	Phase 2
0.7273	Intermediate Similarity	NPD8034	Phase 2
0.7245	Intermediate Similarity	NPD6101	Approved
0.7245	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7492	Approved
0.7238	Intermediate Similarity	NPD4754	Approved
0.7204	Intermediate Similarity	NPD4695	Discontinued
0.7193	Intermediate Similarity	NPD6054	Approved
0.7188	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6616	Approved
0.7179	Intermediate Similarity	NPD6336	Discontinued
0.7159	Intermediate Similarity	NPD4691	Approved
0.7156	Intermediate Similarity	NPD5135	Approved
0.7156	Intermediate Similarity	NPD5249	Phase 3
0.7156	Intermediate Similarity	NPD5169	Approved
0.7156	Intermediate Similarity	NPD5251	Approved
0.7156	Intermediate Similarity	NPD5250	Approved
0.7156	Intermediate Similarity	NPD4634	Approved
0.7156	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5248	Approved
0.7156	Intermediate Similarity	NPD5247	Approved
0.713	Intermediate Similarity	NPD6908	Approved
0.713	Intermediate Similarity	NPD5128	Approved
0.713	Intermediate Similarity	NPD6909	Approved
0.7119	Intermediate Similarity	NPD7078	Approved
0.7111	Intermediate Similarity	NPD4058	Approved
0.7103	Intermediate Similarity	NPD4767	Approved
0.7103	Intermediate Similarity	NPD4768	Approved
0.71	Intermediate Similarity	NPD5281	Approved
0.71	Intermediate Similarity	NPD5284	Approved
0.7091	Intermediate Similarity	NPD5215	Approved
0.7091	Intermediate Similarity	NPD5217	Approved
0.7091	Intermediate Similarity	NPD5127	Approved
0.7091	Intermediate Similarity	NPD5216	Approved
0.7071	Intermediate Similarity	NPD4753	Phase 2
0.7069	Intermediate Similarity	NPD6370	Approved
0.7059	Intermediate Similarity	NPD5210	Approved
0.7059	Intermediate Similarity	NPD4629	Approved
0.7059	Intermediate Similarity	NPD7736	Approved
0.7059	Intermediate Similarity	NPD5654	Approved
0.7053	Intermediate Similarity	NPD4221	Approved
0.7053	Intermediate Similarity	NPD4223	Phase 3
0.7045	Intermediate Similarity	NPD4137	Phase 3
0.7037	Intermediate Similarity	NPD6614	Approved
0.7019	Intermediate Similarity	NPD4225	Approved
0.701	Intermediate Similarity	NPD5329	Approved
0.699	Remote Similarity	NPD7614	Phase 1
0.6989	Remote Similarity	NPD3617	Approved
0.6983	Remote Similarity	NPD6015	Approved
0.6983	Remote Similarity	NPD6016	Approved
0.6981	Remote Similarity	NPD7632	Discontinued
0.6966	Remote Similarity	NPD4747	Approved
0.6939	Remote Similarity	NPD5279	Phase 3
0.6939	Remote Similarity	NPD4623	Approved
0.6939	Remote Similarity	NPD5690	Phase 2
0.6939	Remote Similarity	NPD4519	Discontinued
0.6923	Remote Similarity	NPD5988	Approved
0.6923	Remote Similarity	NPD5959	Approved
0.6916	Remote Similarity	NPD6052	Approved
0.6907	Remote Similarity	NPD4197	Approved
0.6903	Remote Similarity	NPD5167	Approved
0.69	Remote Similarity	NPD6051	Approved
0.6897	Remote Similarity	NPD6059	Approved
0.6893	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5777	Approved
0.6881	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6412	Phase 2
0.6863	Remote Similarity	NPD5779	Approved
0.6863	Remote Similarity	NPD5778	Approved
0.6833	Remote Similarity	NPD8293	Discontinued
0.6814	Remote Similarity	NPD7094	Approved
0.6814	Remote Similarity	NPD6858	Approved
0.6774	Remote Similarity	NPD6117	Approved
0.6768	Remote Similarity	NPD4690	Approved
0.6768	Remote Similarity	NPD4689	Approved
0.6768	Remote Similarity	NPD4138	Approved
0.6768	Remote Similarity	NPD5205	Approved
0.6768	Remote Similarity	NPD4693	Phase 3
0.6768	Remote Similarity	NPD4688	Approved
0.6757	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4687	Approved
0.6739	Remote Similarity	NPD5733	Approved
0.6737	Remote Similarity	NPD4195	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