NPASS Compound

Structure

NPC247233 OpenBabel07101719512D 36 40 0 0 1 0 0 0 0 0999 V2000 5.0694 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 5.3659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5103 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0225 0.6185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2245 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2245 -0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3796 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 4.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6898 2.9268 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5347 2.4390 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8449 1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8449 -0.4878 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 -3.3796 3.9024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 2.4390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 3.9024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 20 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 8 31 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 24 2 0 0 0 0 12 29 1 0 0 0 0 13 32 1 0 0 0 0 14 15 1 0 0 0 0 14 29 1 0 0 0 0 15 31 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 17 30 1 0 0 0 0 18 1 1 6 0 0 0 18 19 1 0 0 0 0 19 2 1 1 0 0 0 19 25 1 0 0 0 0 20 33 2 0 0 0 0 20 36 1 0 0 0 0 21 25 1 0 0 0 0 21 31 1 0 0 0 0 22 26 1 0 0 0 0 22 34 1 6 0 0 0 23 27 1 0 0 0 0 23 36 1 6 0 0 0 24 28 1 0 0 0 0 24 30 1 0 0 0 0 25 29 1 6 0 0 0 26 30 1 1 0 0 0 26 32 1 0 0 0 0 27 28 1 0 0 0 0 27 35 1 1 0 0 0 29 6 1 1 0 0 0 30 7 1 1 0 0 0 31 32 1 1 0 0 0 32 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.37
Volume:	546.497
LogP:	5.898
LogD:	4.576
LogS:	-5.57
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.322
Synthetic Accessibility Score:	5.398
Fsp3:	0.844
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.898
MDCK Permeability:	1.5762952898512594e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.866
30% Bioavailability (F30%):	0.871

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.132
Plasma Protein Binding (PPB):	97.47480010986328%
Volume Distribution (VD):	1.678
Pgp-substrate:	3.018749952316284%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.441
CYP2C19-inhibitor:	0.078
CYP2C19-substrate:	0.928
CYP2C9-inhibitor:	0.269
CYP2C9-substrate:	0.221
CYP2D6-inhibitor:	0.08
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.88
CYP3A4-substrate:	0.768

ADMET: Excretion

Clearance (CL):	3.232
Half-life (T1/2):	0.066

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.217
Drug-inuced Liver Injury (DILI):	0.447
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.789
Maximum Recommended Daily Dose:	0.639
Skin Sensitization:	0.05
Carcinogencity:	0.08
Eye Corrosion:	0.005
Eye Irritation:	0.021
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC247233

Natural Product ID:	NPC247233
*Common Name:**	2Alpha-Acetoxyurs-5,12-Diene-3Beta,11Alpha-Diol
IUPAC Name:	[(2R,3R,6aR,6bS,8aR,11R,12S,12aR,14R,14aS,14bR)-3,14-dihydroxy-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,6,7,8,9,10,11,12,12a,14,14a-dodecahydro-1H-picen-2-yl] acetate
Synonyms:
Standard InCHIKey:	MLEVHKMQNKPYKX-HTJZOODISA-N
Standard InCHI:	InChI=1S/C32H50O4/c1-18-10-12-29(6)14-15-31(8)21(25(29)19(18)2)16-22(34)26-30(7)17-23(36-20(3)33)27(35)28(4,5)24(30)11-13-32(26,31)9/h11,16,18-19,22-23,25-27,34-35H,10,12-15,17H2,1-9H3/t18-,19+,22-,23-,25+,26-,27+,29-,30+,31-,32-/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@@]2(C)C(=CC[C@@]3([C@@H]2[C@H](O)C=C2[C@@]3(C)CC[C@@]3([C@H]2[C@@H](C)[C@H](C)CC3)C)C)C([C@H]1O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL475477
PubChem CID:	21670087
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
NPO23829	Salvia kronenburgii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738403]
NPO23829	Salvia kronenburgii	Species	Lamiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	34.2	ug.mL-1	PMID[525538]

☑ 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 NPC247233 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	1464
0.2-0.3	4444
0.3-0.4	9725
0.4-0.5	12863
0.5-0.6	6232
0.6-0.7	4935
0.7-0.8	2622
0.8-0.85	165
0.85-0.9	20
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9368	High Similarity	NPC96784
0.9368	High Similarity	NPC235920
0.9062	High Similarity	NPC254567
0.9062	High Similarity	NPC474571
0.8969	High Similarity	NPC476132
0.8958	High Similarity	NPC477876
0.8958	High Similarity	NPC477875
0.8925	High Similarity	NPC41239
0.89	High Similarity	NPC473586
0.8866	High Similarity	NPC476195
0.8812	High Similarity	NPC475263
0.88	High Similarity	NPC88349
0.8776	High Similarity	NPC155974
0.8737	High Similarity	NPC474922
0.8737	High Similarity	NPC215700
0.871	High Similarity	NPC246028
0.8673	High Similarity	NPC208358
0.8673	High Similarity	NPC474190
0.86	High Similarity	NPC474124
0.8586	High Similarity	NPC475617
0.8557	High Similarity	NPC276103
0.8557	High Similarity	NPC54248
0.8557	High Similarity	NPC230151
0.8515	High Similarity	NPC470768
0.8515	High Similarity	NPC473543
0.85	High Similarity	NPC475344
0.85	High Similarity	NPC273668
0.85	High Similarity	NPC258547
0.85	High Similarity	NPC283343
0.85	High Similarity	NPC476471
0.8495	Intermediate Similarity	NPC245004
0.8478	Intermediate Similarity	NPC191965
0.8469	Intermediate Similarity	NPC475032
0.8469	Intermediate Similarity	NPC475033
0.8454	Intermediate Similarity	NPC474727
0.8438	Intermediate Similarity	NPC474806
0.8438	Intermediate Similarity	NPC133579
0.8431	Intermediate Similarity	NPC477877
0.8416	Intermediate Similarity	NPC473523
0.84	Intermediate Similarity	NPC473160
0.84	Intermediate Similarity	NPC54909
0.84	Intermediate Similarity	NPC233012
0.8387	Intermediate Similarity	NPC84121
0.8387	Intermediate Similarity	NPC137306
0.8384	Intermediate Similarity	NPC102426
0.8384	Intermediate Similarity	NPC470068
0.8384	Intermediate Similarity	NPC300179
0.837	Intermediate Similarity	NPC102048
0.8367	Intermediate Similarity	NPC253115
0.8367	Intermediate Similarity	NPC304899
0.8351	Intermediate Similarity	NPC87095
0.8351	Intermediate Similarity	NPC472360
0.8351	Intermediate Similarity	NPC296164
0.8351	Intermediate Similarity	NPC472416
0.8333	Intermediate Similarity	NPC152966
0.8333	Intermediate Similarity	NPC173583
0.8333	Intermediate Similarity	NPC477574
0.8316	Intermediate Similarity	NPC16265
0.8316	Intermediate Similarity	NPC20946
0.8316	Intermediate Similarity	NPC259875
0.8316	Intermediate Similarity	NPC187785
0.83	Intermediate Similarity	NPC228251
0.83	Intermediate Similarity	NPC477971
0.83	Intermediate Similarity	NPC473510
0.83	Intermediate Similarity	NPC477972
0.83	Intermediate Similarity	NPC473790
0.83	Intermediate Similarity	NPC161527
0.83	Intermediate Similarity	NPC477968
0.83	Intermediate Similarity	NPC219285
0.83	Intermediate Similarity	NPC20113
0.8286	Intermediate Similarity	NPC220984
0.8283	Intermediate Similarity	NPC43686
0.8283	Intermediate Similarity	NPC476878
0.8283	Intermediate Similarity	NPC476879
0.828	Intermediate Similarity	NPC35933
0.8269	Intermediate Similarity	NPC88701
0.8265	Intermediate Similarity	NPC32118
0.8261	Intermediate Similarity	NPC132386
0.8252	Intermediate Similarity	NPC80566
0.8252	Intermediate Similarity	NPC470056
0.8252	Intermediate Similarity	NPC470767
0.8252	Intermediate Similarity	NPC470763
0.8252	Intermediate Similarity	NPC470055
0.8247	Intermediate Similarity	NPC74855
0.8247	Intermediate Similarity	NPC307335
0.8247	Intermediate Similarity	NPC27918
0.8247	Intermediate Similarity	NPC136313
0.8235	Intermediate Similarity	NPC162354
0.8235	Intermediate Similarity	NPC281378
0.8235	Intermediate Similarity	NPC95899
0.8224	Intermediate Similarity	NPC473159
0.8218	Intermediate Similarity	NPC289670
0.8218	Intermediate Similarity	NPC470054
0.82	Intermediate Similarity	NPC470066
0.82	Intermediate Similarity	NPC325229
0.82	Intermediate Similarity	NPC470067
0.82	Intermediate Similarity	NPC260149
0.82	Intermediate Similarity	NPC58942
0.82	Intermediate Similarity	NPC477928
0.82	Intermediate Similarity	NPC275086
0.8191	Intermediate Similarity	NPC237344
0.8191	Intermediate Similarity	NPC175145
0.8191	Intermediate Similarity	NPC475069
0.819	Intermediate Similarity	NPC143706
0.819	Intermediate Similarity	NPC137917
0.819	Intermediate Similarity	NPC472534
0.819	Intermediate Similarity	NPC310546
0.8182	Intermediate Similarity	NPC88009
0.8182	Intermediate Similarity	NPC19376
0.8182	Intermediate Similarity	NPC211810
0.8182	Intermediate Similarity	NPC475178
0.8182	Intermediate Similarity	NPC284194
0.8182	Intermediate Similarity	NPC221801
0.8182	Intermediate Similarity	NPC307282
0.8182	Intermediate Similarity	NPC471765
0.8182	Intermediate Similarity	NPC305464
0.8182	Intermediate Similarity	NPC25848
0.8173	Intermediate Similarity	NPC301666
0.8173	Intermediate Similarity	NPC230541
0.8165	Intermediate Similarity	NPC471547
0.8152	Intermediate Similarity	NPC286786
0.8144	Intermediate Similarity	NPC306541
0.8144	Intermediate Similarity	NPC60755
0.8144	Intermediate Similarity	NPC472149
0.8144	Intermediate Similarity	NPC71074
0.8144	Intermediate Similarity	NPC470590
0.8144	Intermediate Similarity	NPC285184
0.8144	Intermediate Similarity	NPC300351
0.8144	Intermediate Similarity	NPC77099
0.8144	Intermediate Similarity	NPC25299
0.8144	Intermediate Similarity	NPC234335
0.8144	Intermediate Similarity	NPC84319
0.8144	Intermediate Similarity	NPC235884
0.8144	Intermediate Similarity	NPC52021
0.8137	Intermediate Similarity	NPC470053
0.8131	Intermediate Similarity	NPC212968
0.8131	Intermediate Similarity	NPC116794
0.8131	Intermediate Similarity	NPC125923
0.8131	Intermediate Similarity	NPC65590
0.8131	Intermediate Similarity	NPC64106
0.8125	Intermediate Similarity	NPC477917
0.8119	Intermediate Similarity	NPC64348
0.8119	Intermediate Similarity	NPC230546
0.8119	Intermediate Similarity	NPC38855
0.8113	Intermediate Similarity	NPC274507
0.8113	Intermediate Similarity	NPC75747
0.8113	Intermediate Similarity	NPC199457
0.8113	Intermediate Similarity	NPC269095
0.8113	Intermediate Similarity	NPC7870
0.8113	Intermediate Similarity	NPC68419
0.8113	Intermediate Similarity	NPC102914
0.8113	Intermediate Similarity	NPC108709
0.8113	Intermediate Similarity	NPC110139
0.8113	Intermediate Similarity	NPC78046
0.8105	Intermediate Similarity	NPC131329
0.81	Intermediate Similarity	NPC473244
0.81	Intermediate Similarity	NPC210337
0.81	Intermediate Similarity	NPC189880
0.81	Intermediate Similarity	NPC255589
0.81	Intermediate Similarity	NPC51499
0.81	Intermediate Similarity	NPC259788
0.8095	Intermediate Similarity	NPC472217
0.8095	Intermediate Similarity	NPC472218
0.8095	Intermediate Similarity	NPC472219
0.8085	Intermediate Similarity	NPC164424
0.8081	Intermediate Similarity	NPC53565
0.8081	Intermediate Similarity	NPC96916
0.8073	Intermediate Similarity	NPC146652
0.8061	Intermediate Similarity	NPC119379
0.8061	Intermediate Similarity	NPC275809
0.8061	Intermediate Similarity	NPC86368
0.8061	Intermediate Similarity	NPC53555
0.8058	Intermediate Similarity	NPC473123
0.8058	Intermediate Similarity	NPC473124
0.8058	Intermediate Similarity	NPC478057
0.8058	Intermediate Similarity	NPC99627
0.8058	Intermediate Similarity	NPC473129
0.8056	Intermediate Similarity	NPC269315
0.8056	Intermediate Similarity	NPC144068
0.8056	Intermediate Similarity	NPC271138
0.8043	Intermediate Similarity	NPC142163
0.8043	Intermediate Similarity	NPC195334
0.8043	Intermediate Similarity	NPC290495
0.8043	Intermediate Similarity	NPC108476
0.8041	Intermediate Similarity	NPC220216
0.8041	Intermediate Similarity	NPC474728
0.8041	Intermediate Similarity	NPC120840
0.8041	Intermediate Similarity	NPC113989
0.8041	Intermediate Similarity	NPC48732
0.8041	Intermediate Similarity	NPC49320
0.8039	Intermediate Similarity	NPC256247
0.8039	Intermediate Similarity	NPC472554
0.8037	Intermediate Similarity	NPC30397
0.8037	Intermediate Similarity	NPC297208
0.8037	Intermediate Similarity	NPC235841
0.8037	Intermediate Similarity	NPC191763
0.8037	Intermediate Similarity	NPC473481
0.8037	Intermediate Similarity	NPC114188
0.8037	Intermediate Similarity	NPC211798
0.8037	Intermediate Similarity	NPC190837

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 NPC247233 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1694
0.2-0.3	3794
0.3-0.4	2239
0.4-0.5	791
0.5-0.6	278
0.6-0.7	140
0.7-0.8	27
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7941	Intermediate Similarity	NPD7639	Approved
0.7941	Intermediate Similarity	NPD7640	Approved
0.7843	Intermediate Similarity	NPD7638	Approved
0.78	Intermediate Similarity	NPD7748	Approved
0.7685	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD7645	Phase 2
0.76	Intermediate Similarity	NPD7515	Phase 2
0.7573	Intermediate Similarity	NPD7902	Approved
0.7565	Intermediate Similarity	NPD8033	Approved
0.75	Intermediate Similarity	NPD4225	Approved
0.7478	Intermediate Similarity	NPD8377	Approved
0.7478	Intermediate Similarity	NPD8294	Approved
0.7414	Intermediate Similarity	NPD8296	Approved
0.7414	Intermediate Similarity	NPD8380	Approved
0.7414	Intermediate Similarity	NPD8335	Approved
0.7414	Intermediate Similarity	NPD8379	Approved
0.7414	Intermediate Similarity	NPD8378	Approved
0.7391	Intermediate Similarity	NPD7516	Approved
0.7358	Intermediate Similarity	NPD5344	Discontinued
0.7304	Intermediate Similarity	NPD7327	Approved
0.7304	Intermediate Similarity	NPD7328	Approved
0.729	Intermediate Similarity	NPD7632	Discontinued
0.7282	Intermediate Similarity	NPD7900	Approved
0.7282	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD7115	Discovery
0.7217	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7524	Approved
0.7143	Intermediate Similarity	NPD8328	Phase 3
0.7119	Intermediate Similarity	NPD7503	Approved
0.7021	Intermediate Similarity	NPD8264	Approved
0.7019	Intermediate Similarity	NPD6399	Phase 3
0.7019	Intermediate Similarity	NPD5778	Approved
0.7019	Intermediate Similarity	NPD5779	Approved
0.701	Intermediate Similarity	NPD7525	Registered
0.6964	Remote Similarity	NPD6686	Approved
0.6957	Remote Similarity	NPD8133	Approved
0.6944	Remote Similarity	NPD6648	Approved
0.6923	Remote Similarity	NPD8035	Phase 2
0.6923	Remote Similarity	NPD8034	Phase 2
0.6923	Remote Similarity	NPD7637	Suspended
0.6885	Remote Similarity	NPD7507	Approved
0.6875	Remote Similarity	NPD6412	Phase 2
0.6863	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6942	Approved
0.6842	Remote Similarity	NPD7339	Approved
0.6832	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4632	Approved
0.68	Remote Similarity	NPD6695	Phase 3
0.6771	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6411	Approved
0.6733	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4786	Approved
0.6731	Remote Similarity	NPD6051	Approved
0.6731	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD8297	Approved
0.672	Remote Similarity	NPD7319	Approved
0.67	Remote Similarity	NPD3667	Approved
0.6699	Remote Similarity	NPD7750	Discontinued
0.6694	Remote Similarity	NPD8515	Approved
0.6694	Remote Similarity	NPD8516	Approved
0.6694	Remote Similarity	NPD8517	Approved
0.6694	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD7838	Discovery
0.664	Remote Similarity	NPD7736	Approved
0.6637	Remote Similarity	NPD6402	Approved
0.6637	Remote Similarity	NPD7128	Approved
0.6637	Remote Similarity	NPD5739	Approved
0.6637	Remote Similarity	NPD6675	Approved
0.6635	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6319	Approved
0.6604	Remote Similarity	NPD7983	Approved
0.6602	Remote Similarity	NPD3618	Phase 1
0.6579	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6101	Approved
0.6571	Remote Similarity	NPD5328	Approved
0.6566	Remote Similarity	NPD6929	Approved
0.6522	Remote Similarity	NPD6881	Approved
0.6522	Remote Similarity	NPD6899	Approved
0.6522	Remote Similarity	NPD7320	Approved
0.6509	Remote Similarity	NPD6698	Approved
0.6509	Remote Similarity	NPD46	Approved
0.65	Remote Similarity	NPD6009	Approved
0.65	Remote Similarity	NPD6930	Phase 2
0.65	Remote Similarity	NPD6931	Approved
0.6496	Remote Similarity	NPD8130	Phase 1
0.6496	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6008	Approved
0.6466	Remote Similarity	NPD6372	Approved
0.6466	Remote Similarity	NPD6373	Approved
0.6455	Remote Similarity	NPD6083	Phase 2
0.6455	Remote Similarity	NPD6084	Phase 2
0.6452	Remote Similarity	NPD7604	Phase 2
0.6449	Remote Similarity	NPD6079	Approved
0.6442	Remote Similarity	NPD6409	Approved
0.6442	Remote Similarity	NPD5330	Approved
0.6442	Remote Similarity	NPD7521	Approved
0.6442	Remote Similarity	NPD7334	Approved
0.6442	Remote Similarity	NPD7146	Approved
0.6442	Remote Similarity	NPD6684	Approved
0.6435	Remote Similarity	NPD5697	Approved
0.6435	Remote Similarity	NPD5701	Approved
0.6429	Remote Similarity	NPD4159	Approved
0.6429	Remote Similarity	NPD8293	Discontinued
0.6429	Remote Similarity	NPD6933	Approved
0.6423	Remote Similarity	NPD5983	Phase 2
0.641	Remote Similarity	NPD7290	Approved
0.641	Remote Similarity	NPD7102	Approved
0.641	Remote Similarity	NPD6883	Approved
0.6408	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7492	Approved
0.6396	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD3573	Approved
0.6379	Remote Similarity	NPD6011	Approved
0.6364	Remote Similarity	NPD5776	Phase 2
0.6364	Remote Similarity	NPD6925	Approved
0.6356	Remote Similarity	NPD6847	Approved
0.6356	Remote Similarity	NPD6649	Approved
0.6356	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6650	Approved
0.6356	Remote Similarity	NPD6617	Approved
0.6356	Remote Similarity	NPD6869	Approved
0.6349	Remote Similarity	NPD6336	Discontinued
0.6349	Remote Similarity	NPD6616	Approved
0.6341	Remote Similarity	NPD6054	Approved
0.6341	Remote Similarity	NPD6059	Approved
0.6337	Remote Similarity	NPD7332	Phase 2
0.6337	Remote Similarity	NPD7514	Phase 3
0.6325	Remote Similarity	NPD6014	Approved
0.6325	Remote Similarity	NPD6012	Approved
0.6325	Remote Similarity	NPD6013	Approved
0.6321	Remote Similarity	NPD6903	Approved
0.6321	Remote Similarity	NPD6672	Approved
0.6321	Remote Similarity	NPD5737	Approved
0.6303	Remote Similarity	NPD6882	Approved
0.63	Remote Similarity	NPD6114	Approved
0.63	Remote Similarity	NPD6118	Approved
0.63	Remote Similarity	NPD6115	Approved
0.63	Remote Similarity	NPD7145	Approved
0.63	Remote Similarity	NPD6697	Approved
0.6299	Remote Similarity	NPD7078	Approved
0.6296	Remote Similarity	NPD7087	Discontinued
0.6275	Remote Similarity	NPD6902	Approved
0.6273	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD3668	Phase 3
0.625	Remote Similarity	NPD3133	Approved
0.624	Remote Similarity	NPD6370	Approved
0.6239	Remote Similarity	NPD4202	Approved
0.6228	Remote Similarity	NPD5211	Phase 2
0.6224	Remote Similarity	NPD6924	Approved
0.6224	Remote Similarity	NPD6926	Approved
0.6216	Remote Similarity	NPD4697	Phase 3
0.6216	Remote Similarity	NPD5221	Approved
0.6216	Remote Similarity	NPD7732	Phase 3
0.6216	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5222	Approved
0.6216	Remote Similarity	NPD7614	Phase 1
0.6214	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD3168	Discontinued
0.619	Remote Similarity	NPD6067	Discontinued
0.619	Remote Similarity	NPD6893	Approved
0.6187	Remote Similarity	NPD7625	Phase 1
0.6176	Remote Similarity	NPD4748	Discontinued
0.6172	Remote Similarity	NPD8074	Phase 3
0.6167	Remote Similarity	NPD6053	Discontinued
0.6161	Remote Similarity	NPD4755	Approved
0.6161	Remote Similarity	NPD5173	Approved
0.616	Remote Similarity	NPD6016	Approved
0.616	Remote Similarity	NPD6015	Approved
0.616	Remote Similarity	NPD6921	Approved
0.6154	Remote Similarity	NPD6110	Phase 1
0.6148	Remote Similarity	NPD6868	Approved
0.6139	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6371	Approved
0.6134	Remote Similarity	NPD4634	Approved
0.6126	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5141	Approved
0.6117	Remote Similarity	NPD6898	Phase 1
0.6111	Remote Similarity	NPD5988	Approved
0.6106	Remote Similarity	NPD5696	Approved
0.61	Remote Similarity	NPD6117	Approved
0.6091	Remote Similarity	NPD8171	Discontinued
0.6075	Remote Similarity	NPD4250	Approved
0.6075	Remote Similarity	NPD4251	Approved
0.6071	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6640	Phase 3
0.6061	Remote Similarity	NPD4784	Approved
0.6061	Remote Similarity	NPD4785	Approved
0.6053	Remote Similarity	NPD5285	Approved
0.6053	Remote Similarity	NPD4700	Approved
0.6053	Remote Similarity	NPD4696	Approved
0.6053	Remote Similarity	NPD5286	Approved
0.6048	Remote Similarity	NPD6335	Approved
0.604	Remote Similarity	NPD6932	Approved
0.604	Remote Similarity	NPD6116	Phase 1

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