NPASS Compound

Structure

NPC264048 OpenBabel07101719512D 29 32 0 0 1 0 0 0 0 0999 V2000 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 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 15 1 0 0 0 0 8 10 2 0 0 0 0 8 17 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 16 2 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 25 2 0 0 0 0 13 29 1 0 0 0 0 14 26 2 0 0 0 0 15 23 1 6 0 0 0 15 24 1 0 0 0 0 16 22 1 0 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 17 27 2 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 18 28 1 1 0 0 0 19 21 1 0 0 0 0 19 23 1 6 0 0 0 20 24 1 1 0 0 0 20 29 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:	400.22
Volume:	420.203
LogP:	2.098
LogD:	1.447
LogS:	-4.317
# Rotatable Bonds:	2
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.683
Synthetic Accessibility Score:	4.95
Fsp3:	0.708
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.173
MDCK Permeability:	3.303760968265124e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.795
30% Bioavailability (F30%):	0.187

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.448
Plasma Protein Binding (PPB):	76.99327850341797%
Volume Distribution (VD):	0.549
Pgp-substrate:	25.762908935546875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.41
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.8
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.032
CYP3A4-inhibitor:	0.742
CYP3A4-substrate:	0.826

ADMET: Excretion

Clearance (CL):	2.48
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.433
Drug-inuced Liver Injury (DILI):	0.107
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.929
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.869
Carcinogencity:	0.159
Eye Corrosion:	0.006
Eye Irritation:	0.017
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC264048

Natural Product ID:	NPC264048
*Common Name:**	Androsta-1,14-Dien-3,16-Dione, 6-Hydroxy,7(-Acetoxy)-4,4,8-Trimethyl-(5Alpha,6Alpha,7Alpha,13Alpha)
IUPAC Name:	[(5R,6R,7S,8R,9R,10R,13S)-6-hydroxy-4,4,8,10,13-pentamethyl-3,16-dioxo-6,7,9,11,12,17-hexahydro-5H-cyclopenta[a]phenanthren-7-yl] acetate
Synonyms:
Standard InCHIKey:	HKVOPFDXIGAKHQ-CXCOWLLISA-N
Standard InCHI:	InChI=1S/C24H32O5/c1-13(25)29-20-18(28)19-21(2,3)17(27)8-10-23(19,5)15-7-9-22(4)12-14(26)11-16(22)24(15,20)6/h8,10-11,15,18-20,28H,7,9,12H2,1-6H3/t15-,18-,19+,20-,22+,23-,24-/m1/s1
SMILES:	CC(=O)O[C@@H]1[C@H](O)[C@@H]2[C@]([C@@H]3[C@]1(C)C1=CC(=O)C[C@]1(C)CC3)(C)C=CC(=O)C2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491380
PubChem CID:	21592304
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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4532	Organism	Anopheles stephensi	Anopheles stephensi	LC50	=	43.0	ppm	PMID[558957]

☑ 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 NPC264048 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	213
0.1-0.2	1179
0.2-0.3	4147
0.3-0.4	8299
0.4-0.5	13065
0.5-0.6	7159
0.6-0.7	5515
0.7-0.8	2921
0.8-0.85	162
0.85-0.9	30
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9406	High Similarity	NPC239097
0.9118	High Similarity	NPC41405
0.9053	High Similarity	NPC79117
0.9029	High Similarity	NPC5284
0.8879	High Similarity	NPC284068
0.8878	High Similarity	NPC292133
0.8857	High Similarity	NPC234042
0.8857	High Similarity	NPC152117
0.8835	High Similarity	NPC469844
0.8824	High Similarity	NPC102352
0.8774	High Similarity	NPC255017
0.8738	High Similarity	NPC3316
0.8738	High Similarity	NPC144854
0.8725	High Similarity	NPC255309
0.8713	High Similarity	NPC473163
0.87	High Similarity	NPC316964
0.8673	High Similarity	NPC473170
0.8654	High Similarity	NPC154608
0.8654	High Similarity	NPC192813
0.8654	High Similarity	NPC277017
0.8641	High Similarity	NPC96377
0.8614	High Similarity	NPC469327
0.86	High Similarity	NPC114274
0.8586	High Similarity	NPC471039
0.8571	High Similarity	NPC240617
0.8558	High Similarity	NPC9457
0.8558	High Similarity	NPC471783
0.8532	High Similarity	NPC471854
0.8532	High Similarity	NPC470959
0.8532	High Similarity	NPC476965
0.8529	High Similarity	NPC136289
0.85	High Similarity	NPC108078
0.8485	Intermediate Similarity	NPC469329
0.8485	Intermediate Similarity	NPC37787
0.8485	Intermediate Similarity	NPC180557
0.8485	Intermediate Similarity	NPC30677
0.8485	Intermediate Similarity	NPC473415
0.8485	Intermediate Similarity	NPC470016
0.8485	Intermediate Similarity	NPC317586
0.8476	Intermediate Similarity	NPC19412
0.8469	Intermediate Similarity	NPC107674
0.8469	Intermediate Similarity	NPC170220
0.8469	Intermediate Similarity	NPC141497
0.8462	Intermediate Similarity	NPC181357
0.8455	Intermediate Similarity	NPC311554
0.8455	Intermediate Similarity	NPC257457
0.8447	Intermediate Similarity	NPC471005
0.8447	Intermediate Similarity	NPC239716
0.844	Intermediate Similarity	NPC270929
0.8438	Intermediate Similarity	NPC158778
0.8431	Intermediate Similarity	NPC81530
0.8431	Intermediate Similarity	NPC224720
0.8431	Intermediate Similarity	NPC476240
0.8431	Intermediate Similarity	NPC476223
0.8426	Intermediate Similarity	NPC250109
0.8416	Intermediate Similarity	NPC478056
0.8411	Intermediate Similarity	NPC474229
0.84	Intermediate Similarity	NPC104568
0.8396	Intermediate Similarity	NPC310546
0.8396	Intermediate Similarity	NPC27814
0.8384	Intermediate Similarity	NPC166906
0.8384	Intermediate Similarity	NPC471040
0.8384	Intermediate Similarity	NPC159410
0.8381	Intermediate Similarity	NPC230541
0.8367	Intermediate Similarity	NPC110657
0.8367	Intermediate Similarity	NPC189520
0.8367	Intermediate Similarity	NPC86266
0.8367	Intermediate Similarity	NPC212301
0.8365	Intermediate Similarity	NPC189616
0.8365	Intermediate Similarity	NPC65523
0.8365	Intermediate Similarity	NPC471293
0.8364	Intermediate Similarity	NPC470493
0.8364	Intermediate Similarity	NPC312824
0.8364	Intermediate Similarity	NPC183580
0.8351	Intermediate Similarity	NPC119416
0.8349	Intermediate Similarity	NPC147912
0.8349	Intermediate Similarity	NPC67259
0.8333	Intermediate Similarity	NPC71348
0.8333	Intermediate Similarity	NPC476274
0.8333	Intermediate Similarity	NPC90769
0.8333	Intermediate Similarity	NPC472002
0.8318	Intermediate Similarity	NPC37116
0.8318	Intermediate Similarity	NPC210005
0.8318	Intermediate Similarity	NPC197428
0.8317	Intermediate Similarity	NPC473456
0.8317	Intermediate Similarity	NPC23680
0.8304	Intermediate Similarity	NPC476961
0.8302	Intermediate Similarity	NPC293850
0.83	Intermediate Similarity	NPC139459
0.83	Intermediate Similarity	NPC469599
0.8288	Intermediate Similarity	NPC329736
0.8286	Intermediate Similarity	NPC470587
0.8283	Intermediate Similarity	NPC474185
0.8273	Intermediate Similarity	NPC251236
0.8273	Intermediate Similarity	NPC64318
0.8273	Intermediate Similarity	NPC40632
0.8273	Intermediate Similarity	NPC96312
0.8273	Intermediate Similarity	NPC328374
0.8269	Intermediate Similarity	NPC282233
0.8269	Intermediate Similarity	NPC95585
0.8265	Intermediate Similarity	NPC472325
0.8257	Intermediate Similarity	NPC49451
0.8257	Intermediate Similarity	NPC198539
0.8257	Intermediate Similarity	NPC962
0.8252	Intermediate Similarity	NPC233012
0.8252	Intermediate Similarity	NPC54909
0.8247	Intermediate Similarity	NPC474677
0.8246	Intermediate Similarity	NPC11895
0.8241	Intermediate Similarity	NPC201992
0.8241	Intermediate Similarity	NPC188738
0.8235	Intermediate Similarity	NPC194196
0.8224	Intermediate Similarity	NPC141350
0.8224	Intermediate Similarity	NPC153239
0.8224	Intermediate Similarity	NPC214644
0.8218	Intermediate Similarity	NPC471822
0.8218	Intermediate Similarity	NPC230151
0.8218	Intermediate Similarity	NPC96859
0.8218	Intermediate Similarity	NPC305483
0.8218	Intermediate Similarity	NPC95565
0.8218	Intermediate Similarity	NPC471777
0.8218	Intermediate Similarity	NPC328162
0.8218	Intermediate Similarity	NPC117133
0.8214	Intermediate Similarity	NPC61520
0.8214	Intermediate Similarity	NPC475041
0.8214	Intermediate Similarity	NPC161065
0.8208	Intermediate Similarity	NPC475294
0.8208	Intermediate Similarity	NPC44063
0.82	Intermediate Similarity	NPC472977
0.82	Intermediate Similarity	NPC473162
0.82	Intermediate Similarity	NPC49670
0.82	Intermediate Similarity	NPC473172
0.82	Intermediate Similarity	NPC471207
0.82	Intermediate Similarity	NPC472976
0.8198	Intermediate Similarity	NPC470492
0.8198	Intermediate Similarity	NPC167606
0.8198	Intermediate Similarity	NPC286528
0.8198	Intermediate Similarity	NPC20302
0.8198	Intermediate Similarity	NPC140055
0.819	Intermediate Similarity	NPC235889
0.8182	Intermediate Similarity	NPC474906
0.8182	Intermediate Similarity	NPC18547
0.8182	Intermediate Similarity	NPC473798
0.8182	Intermediate Similarity	NPC243354
0.8182	Intermediate Similarity	NPC473166
0.8182	Intermediate Similarity	NPC155304
0.8174	Intermediate Similarity	NPC81736
0.8174	Intermediate Similarity	NPC172154
0.8173	Intermediate Similarity	NPC477915
0.8173	Intermediate Similarity	NPC469316
0.8165	Intermediate Similarity	NPC476801
0.8165	Intermediate Similarity	NPC269530
0.8165	Intermediate Similarity	NPC11252
0.8165	Intermediate Similarity	NPC474516
0.8165	Intermediate Similarity	NPC280782
0.8165	Intermediate Similarity	NPC289312
0.8165	Intermediate Similarity	NPC205534
0.8163	Intermediate Similarity	NPC77263
0.8163	Intermediate Similarity	NPC250592
0.8158	Intermediate Similarity	NPC170538
0.8155	Intermediate Similarity	NPC112167
0.8155	Intermediate Similarity	NPC471041
0.8155	Intermediate Similarity	NPC88198
0.8155	Intermediate Similarity	NPC266955
0.8148	Intermediate Similarity	NPC474567
0.8148	Intermediate Similarity	NPC473627
0.8148	Intermediate Similarity	NPC286880
0.8144	Intermediate Similarity	NPC472324
0.8144	Intermediate Similarity	NPC477926
0.8142	Intermediate Similarity	NPC241192
0.8137	Intermediate Similarity	NPC253826
0.8137	Intermediate Similarity	NPC226986
0.8137	Intermediate Similarity	NPC84335
0.8137	Intermediate Similarity	NPC474343
0.8137	Intermediate Similarity	NPC255589
0.8137	Intermediate Similarity	NPC259788
0.8137	Intermediate Similarity	NPC38530
0.8131	Intermediate Similarity	NPC94942
0.8131	Intermediate Similarity	NPC189075
0.8131	Intermediate Similarity	NPC275539
0.8125	Intermediate Similarity	NPC50774
0.8125	Intermediate Similarity	NPC709
0.8125	Intermediate Similarity	NPC186525
0.8119	Intermediate Similarity	NPC139570
0.8119	Intermediate Similarity	NPC53565
0.8119	Intermediate Similarity	NPC255809
0.8119	Intermediate Similarity	NPC200702
0.8119	Intermediate Similarity	NPC96916
0.8119	Intermediate Similarity	NPC274417
0.8113	Intermediate Similarity	NPC323834
0.8113	Intermediate Similarity	NPC149047
0.8113	Intermediate Similarity	NPC181265
0.8113	Intermediate Similarity	NPC472655
0.8108	Intermediate Similarity	NPC152199
0.8108	Intermediate Similarity	NPC176840
0.8108	Intermediate Similarity	NPC49492
0.8108	Intermediate Similarity	NPC134869
0.8108	Intermediate Similarity	NPC266728
0.8108	Intermediate Similarity	NPC302471
0.8108	Intermediate Similarity	NPC235539
0.8108	Intermediate Similarity	NPC270958

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 NPC264048 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1521
0.2-0.3	3583
0.3-0.4	2494
0.4-0.5	865
0.5-0.6	245
0.6-0.7	123
0.7-0.8	133
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8367	Intermediate Similarity	NPD6079	Approved
0.8333	Intermediate Similarity	NPD8297	Approved
0.8302	Intermediate Similarity	NPD6899	Approved
0.8302	Intermediate Similarity	NPD6881	Approved
0.8241	Intermediate Similarity	NPD6649	Approved
0.8241	Intermediate Similarity	NPD6650	Approved
0.8208	Intermediate Similarity	NPD5697	Approved
0.8198	Intermediate Similarity	NPD7115	Discovery
0.8163	Intermediate Similarity	NPD5328	Approved
0.8148	Intermediate Similarity	NPD6883	Approved
0.8148	Intermediate Similarity	NPD7102	Approved
0.8148	Intermediate Similarity	NPD7290	Approved
0.8131	Intermediate Similarity	NPD6011	Approved
0.8113	Intermediate Similarity	NPD5739	Approved
0.8113	Intermediate Similarity	NPD6675	Approved
0.8113	Intermediate Similarity	NPD6402	Approved
0.8113	Intermediate Similarity	NPD7128	Approved
0.81	Intermediate Similarity	NPD6399	Phase 3
0.8091	Intermediate Similarity	NPD4632	Approved
0.8073	Intermediate Similarity	NPD6869	Approved
0.8073	Intermediate Similarity	NPD6847	Approved
0.8073	Intermediate Similarity	NPD8130	Phase 1
0.8073	Intermediate Similarity	NPD6617	Approved
0.8056	Intermediate Similarity	NPD6372	Approved
0.8056	Intermediate Similarity	NPD6373	Approved
0.8056	Intermediate Similarity	NPD6012	Approved
0.8056	Intermediate Similarity	NPD6013	Approved
0.8056	Intermediate Similarity	NPD6014	Approved
0.8041	Intermediate Similarity	NPD3618	Phase 1
0.8039	Intermediate Similarity	NPD5222	Approved
0.8039	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD5221	Approved
0.802	Intermediate Similarity	NPD7748	Approved
0.8	Intermediate Similarity	NPD7515	Phase 2
0.8	Intermediate Similarity	NPD6882	Approved
0.7963	Intermediate Similarity	NPD7320	Approved
0.7961	Intermediate Similarity	NPD7902	Approved
0.7961	Intermediate Similarity	NPD5173	Approved
0.787	Intermediate Similarity	NPD5701	Approved
0.7864	Intermediate Similarity	NPD4697	Phase 3
0.7826	Intermediate Similarity	NPD6319	Approved
0.781	Intermediate Similarity	NPD4696	Approved
0.781	Intermediate Similarity	NPD5285	Approved
0.781	Intermediate Similarity	NPD5286	Approved
0.7788	Intermediate Similarity	NPD6868	Approved
0.7778	Intermediate Similarity	NPD3573	Approved
0.7748	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD5223	Approved
0.7719	Intermediate Similarity	NPD6009	Approved
0.7714	Intermediate Similarity	NPD4225	Approved
0.7677	Intermediate Similarity	NPD6409	Approved
0.7677	Intermediate Similarity	NPD7146	Approved
0.7677	Intermediate Similarity	NPD5330	Approved
0.7677	Intermediate Similarity	NPD7521	Approved
0.7677	Intermediate Similarity	NPD7334	Approved
0.7677	Intermediate Similarity	NPD6684	Approved
0.767	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7900	Approved
0.7664	Intermediate Similarity	NPD5226	Approved
0.7664	Intermediate Similarity	NPD5224	Approved
0.7664	Intermediate Similarity	NPD5211	Phase 2
0.7664	Intermediate Similarity	NPD5225	Approved
0.7664	Intermediate Similarity	NPD4633	Approved
0.7653	Intermediate Similarity	NPD4786	Approved
0.7652	Intermediate Similarity	NPD6335	Approved
0.7629	Intermediate Similarity	NPD3667	Approved
0.7627	Intermediate Similarity	NPD7604	Phase 2
0.7619	Intermediate Similarity	NPD6083	Phase 2
0.7619	Intermediate Similarity	NPD6084	Phase 2
0.7619	Intermediate Similarity	NPD4755	Approved
0.7615	Intermediate Similarity	NPD6008	Approved
0.7607	Intermediate Similarity	NPD5983	Phase 2
0.7593	Intermediate Similarity	NPD5174	Approved
0.7593	Intermediate Similarity	NPD5175	Approved
0.7586	Intermediate Similarity	NPD7101	Approved
0.7586	Intermediate Similarity	NPD7100	Approved
0.7565	Intermediate Similarity	NPD6317	Approved
0.7563	Intermediate Similarity	NPD7492	Approved
0.7547	Intermediate Similarity	NPD7638	Approved
0.7525	Intermediate Similarity	NPD6903	Approved
0.7525	Intermediate Similarity	NPD6672	Approved
0.7525	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD5737	Approved
0.7523	Intermediate Similarity	NPD5141	Approved
0.7521	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6313	Approved
0.75	Intermediate Similarity	NPD6336	Discontinued
0.75	Intermediate Similarity	NPD6616	Approved
0.75	Intermediate Similarity	NPD6314	Approved
0.75	Intermediate Similarity	NPD4634	Approved
0.7478	Intermediate Similarity	NPD6274	Approved
0.7477	Intermediate Similarity	NPD4700	Approved
0.7477	Intermediate Similarity	NPD7640	Approved
0.7477	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD7639	Approved
0.7476	Intermediate Similarity	NPD6411	Approved
0.7475	Intermediate Similarity	NPD3666	Approved
0.7475	Intermediate Similarity	NPD3665	Phase 1
0.7475	Intermediate Similarity	NPD3133	Approved
0.7458	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7078	Approved
0.7429	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD4202	Approved
0.74	Intermediate Similarity	NPD1694	Approved
0.7395	Intermediate Similarity	NPD6370	Approved
0.7387	Intermediate Similarity	NPD6412	Phase 2
0.7383	Intermediate Similarity	NPD5696	Approved
0.7377	Intermediate Similarity	NPD7736	Approved
0.7333	Intermediate Similarity	NPD8328	Phase 3
0.7321	Intermediate Similarity	NPD4730	Approved
0.7321	Intermediate Similarity	NPD5168	Approved
0.7321	Intermediate Similarity	NPD4729	Approved
0.7311	Intermediate Similarity	NPD6016	Approved
0.7311	Intermediate Similarity	NPD6015	Approved
0.7308	Intermediate Similarity	NPD8034	Phase 2
0.7308	Intermediate Similarity	NPD8035	Phase 2
0.7282	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6101	Approved
0.7273	Intermediate Similarity	NPD4754	Approved
0.7264	Intermediate Similarity	NPD5210	Approved
0.7264	Intermediate Similarity	NPD4629	Approved
0.7264	Intermediate Similarity	NPD5695	Phase 3
0.725	Intermediate Similarity	NPD5988	Approved
0.7228	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD6059	Approved
0.7193	Intermediate Similarity	NPD5249	Phase 3
0.7193	Intermediate Similarity	NPD5248	Approved
0.7193	Intermediate Similarity	NPD5250	Approved
0.7193	Intermediate Similarity	NPD5135	Approved
0.7193	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5247	Approved
0.7193	Intermediate Similarity	NPD5251	Approved
0.7193	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5169	Approved
0.7168	Intermediate Similarity	NPD6686	Approved
0.7168	Intermediate Similarity	NPD5128	Approved
0.7167	Intermediate Similarity	NPD6908	Approved
0.7167	Intermediate Similarity	NPD6909	Approved
0.7154	Intermediate Similarity	NPD8293	Discontinued
0.7143	Intermediate Similarity	NPD4767	Approved
0.7143	Intermediate Similarity	NPD5281	Approved
0.7143	Intermediate Similarity	NPD5284	Approved
0.7143	Intermediate Similarity	NPD4768	Approved
0.713	Intermediate Similarity	NPD5217	Approved
0.713	Intermediate Similarity	NPD5216	Approved
0.713	Intermediate Similarity	NPD5127	Approved
0.713	Intermediate Similarity	NPD5215	Approved
0.7129	Intermediate Similarity	NPD3668	Phase 3
0.7119	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6673	Approved
0.7115	Intermediate Similarity	NPD6080	Approved
0.7115	Intermediate Similarity	NPD4753	Phase 2
0.7115	Intermediate Similarity	NPD6904	Approved
0.7115	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7507	Approved
0.7071	Intermediate Similarity	NPD4695	Discontinued
0.7027	Intermediate Similarity	NPD7632	Discontinued
0.7009	Intermediate Similarity	NPD6001	Approved
0.699	Remote Similarity	NPD5279	Phase 3
0.6949	Remote Similarity	NPD5167	Approved
0.6931	Remote Similarity	NPD4223	Phase 3
0.6931	Remote Similarity	NPD4221	Approved
0.6931	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5778	Approved
0.6916	Remote Similarity	NPD5779	Approved
0.6905	Remote Similarity	NPD7319	Approved
0.6893	Remote Similarity	NPD5329	Approved
0.6887	Remote Similarity	NPD5207	Approved
0.6887	Remote Similarity	NPD5785	Approved
0.6881	Remote Similarity	NPD7614	Phase 1
0.6869	Remote Similarity	NPD3617	Approved
0.6857	Remote Similarity	NPD5208	Approved
0.6837	Remote Similarity	NPD6117	Approved
0.6827	Remote Similarity	NPD4519	Discontinued
0.6827	Remote Similarity	NPD5690	Phase 2
0.6827	Remote Similarity	NPD4623	Approved
0.6827	Remote Similarity	NPD6098	Approved
0.6825	Remote Similarity	NPD6033	Approved
0.6822	Remote Similarity	NPD6050	Approved
0.6822	Remote Similarity	NPD5694	Approved
0.6822	Remote Similarity	NPD5693	Phase 1
0.6797	Remote Similarity	NPD7260	Phase 2
0.6796	Remote Similarity	NPD4197	Approved
0.6774	Remote Similarity	NPD6067	Discontinued
0.6768	Remote Similarity	NPD6116	Phase 1
0.6765	Remote Similarity	NPD6435	Approved
0.6748	Remote Similarity	NPD6921	Approved
0.6735	Remote Similarity	NPD6942	Approved
0.6735	Remote Similarity	NPD7339	Approved
0.6733	Remote Similarity	NPD7525	Registered
0.6731	Remote Similarity	NPD5363	Approved
0.6729	Remote Similarity	NPD5692	Phase 3
0.6727	Remote Similarity	NPD7732	Phase 3
0.67	Remote Similarity	NPD6114	Approved
0.67	Remote Similarity	NPD6115	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