NPASS Compound

Structure

NPC94462 OpenBabel07101718242D 33 37 0 0 1 0 0 0 0 0999 V2000 -6.1848 0.1918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5351 0.5424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6634 0.4967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5896 2.0966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8660 2.7481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2588 0.1860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0140 2.5147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0457 2.4129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2164 3.0988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4612 0.8433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3625 1.4228 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6636 1.7957 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6865 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4101 1.6252 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0140 2.1464 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8432 -0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9400 2.4472 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6865 0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3729 -1.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 7 29 1 0 0 0 0 8 9 1 0 0 0 0 8 20 2 0 0 0 0 9 24 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 29 1 0 0 0 0 14 20 1 0 0 0 0 14 21 1 0 0 0 0 15 25 1 0 0 0 0 15 27 1 0 0 0 0 16 26 1 0 0 0 0 16 28 1 0 0 0 0 17 19 1 0 0 0 0 18 3 1 6 0 0 0 18 22 1 0 0 0 0 18 25 1 0 0 0 0 19 4 1 6 0 0 0 19 27 1 0 0 0 0 20 29 1 0 0 0 0 21 31 1 1 0 0 0 22 28 1 1 0 0 0 23 24 1 0 0 0 0 23 28 1 1 0 0 0 24 30 1 6 0 0 0 25 27 1 6 0 0 0 26 30 1 6 0 0 0 26 32 1 0 0 0 0 27 5 1 6 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.38
Volume:	508.388
LogP:	6.216
LogD:	5.539
LogS:	-5.402
# Rotatable Bonds:	4
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.455
Synthetic Accessibility Score:	5.313
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.7
MDCK Permeability:	1.5791638361406513e-05
Pgp-inhibitor:	0.966
Pgp-substrate:	0.717
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.089

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.222
Plasma Protein Binding (PPB):	95.9542236328125%
Volume Distribution (VD):	0.988
Pgp-substrate:	1.6971830129623413%

ADMET: Metabolism

CYP1A2-inhibitor:	0.074
CYP1A2-substrate:	0.183
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.842
CYP2C9-inhibitor:	0.37
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.857
CYP3A4-substrate:	0.496

ADMET: Excretion

Clearance (CL):	8.265
Half-life (T1/2):	0.071

ADMET: Toxicity

hERG Blockers:	0.296
Human Hepatotoxicity (H-HT):	0.302
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.87
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.738
Carcinogencity:	0.39
Eye Corrosion:	0.267
Eye Irritation:	0.132
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC94462

Natural Product ID:	NPC94462
*Common Name:**	Gorgostane-3-Beta,9-Alpha,5-Alpha,6-Beta,11-Alpha-Tetrol
IUPAC Name:	(3S,8S,9R,10S,11R,13R,14S,17R)-10,13-dimethyl-17-[(1S)-1-[(1R,2R)-2-methyl-2-[(2S)-3-methylbutan-2-yl]cyclopropyl]ethyl]-1,2,3,4,7,8,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-3,9,11-triol
Synonyms:
Standard InCHIKey:	OTTVISRUYFBLEW-MREQRLIMSA-N
Standard InCHI:	InChI=1S/C30H50O3/c1-17(2)19(4)27(5)15-25(27)18(3)22-10-11-23-24-9-8-20-14-21(31)12-13-29(20,7)30(24,33)26(32)16-28(22,23)6/h8,17-19,21-26,31-33H,9-16H2,1-7H3/t18-,19-,21-,22+,23-,24-,25+,26+,27+,28+,29-,30-/m0/s1
SMILES:	CC(C)[C@H](C)[C@@]1(C)C[C@@H]1[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@]3([C@@H](C[C@]12C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486197
PubChem CID:	10742556
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002039] Gorgostanes and derivatives

*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
NPO32508	plexaura sp.	Species	Plexauridae	Eukaryota	n.a.	Bahamas	n.a.	PMID[16124770]

☑ 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
EC50	1
Others	4

Activity Type	# Activity
Individual Protein	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1794	Individual Protein	LXR-alpha	Homo sapiens	LC50	=	1300.0	nM	PMID[555946]
NPT1746	Individual Protein	LXR-beta	Homo sapiens	LC50	=	50000.0	nM	PMID[555946]
NPT1794	Individual Protein	LXR-alpha	Homo sapiens	EC50	=	450.0	nM	PMID[555946]
NPT1794	Individual Protein	LXR-alpha	Homo sapiens	FC	=	10.1	n.a.	PMID[555946]
NPT6536	Others	Liver X receptor (LXR alpha AND LXR beta)	Homo sapiens	FC	=	40.0	n.a.	PMID[555946]

☑ 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 NPC94462 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	184
0.1-0.2	1577
0.2-0.3	6261
0.3-0.4	15777
0.4-0.5	7500
0.5-0.6	5581
0.6-0.7	4477
0.7-0.8	1085
0.8-0.85	195
0.85-0.9	53
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC474531
0.9277	High Similarity	NPC269058
0.9277	High Similarity	NPC71520
0.925	High Similarity	NPC236112
0.9125	High Similarity	NPC328714
0.9059	High Similarity	NPC474668
0.9059	High Similarity	NPC133588
0.9024	High Similarity	NPC7988
0.9024	High Similarity	NPC30166
0.9012	High Similarity	NPC13554
0.9	High Similarity	NPC87604
0.8953	High Similarity	NPC470361
0.8953	High Similarity	NPC105495
0.8916	High Similarity	NPC113978
0.8916	High Similarity	NPC207013
0.8916	High Similarity	NPC317458
0.8902	High Similarity	NPC470383
0.8875	High Similarity	NPC198968
0.8875	High Similarity	NPC318495
0.8875	High Similarity	NPC155986
0.8875	High Similarity	NPC34019
0.8851	High Similarity	NPC11216
0.8851	High Similarity	NPC291484
0.8851	High Similarity	NPC204188
0.8851	High Similarity	NPC3345
0.8851	High Similarity	NPC80561
0.8851	High Similarity	NPC329596
0.8824	High Similarity	NPC261266
0.8824	High Similarity	NPC125399
0.8824	High Similarity	NPC6391
0.881	High Similarity	NPC124172
0.881	High Similarity	NPC209802
0.8795	High Similarity	NPC248886
0.878	High Similarity	NPC287749
0.878	High Similarity	NPC22403
0.878	High Similarity	NPC26117
0.8765	High Similarity	NPC85346
0.8765	High Similarity	NPC275910
0.8765	High Similarity	NPC65897
0.8765	High Similarity	NPC302041
0.8765	High Similarity	NPC285761
0.875	High Similarity	NPC240604
0.875	High Similarity	NPC41554
0.875	High Similarity	NPC189883
0.875	High Similarity	NPC321381
0.875	High Similarity	NPC300324
0.875	High Similarity	NPC321016
0.875	High Similarity	NPC97404
0.875	High Similarity	NPC107059
0.875	High Similarity	NPC275671
0.869	High Similarity	NPC474634
0.8675	High Similarity	NPC6707
0.8675	High Similarity	NPC209620
0.8675	High Similarity	NPC23852
0.8659	High Similarity	NPC273410
0.8659	High Similarity	NPC1319
0.8659	High Similarity	NPC80530
0.8659	High Similarity	NPC472463
0.8642	High Similarity	NPC471798
0.8642	High Similarity	NPC130136
0.8642	High Similarity	NPC214570
0.8636	High Similarity	NPC473956
0.8636	High Similarity	NPC475751
0.8625	High Similarity	NPC230301
0.8625	High Similarity	NPC304309
0.8625	High Similarity	NPC141071
0.8625	High Similarity	NPC66566
0.8625	High Similarity	NPC285893
0.8625	High Similarity	NPC162742
0.8625	High Similarity	NPC134847
0.8625	High Similarity	NPC136188
0.8625	High Similarity	NPC22105
0.8625	High Similarity	NPC257347
0.8625	High Similarity	NPC471723
0.8625	High Similarity	NPC28657
0.8625	High Similarity	NPC288035
0.8625	High Similarity	NPC477923
0.8621	High Similarity	NPC67872
0.8621	High Similarity	NPC280556
0.8621	High Similarity	NPC475664
0.8605	High Similarity	NPC477604
0.8605	High Similarity	NPC24277
0.8588	High Similarity	NPC474493
0.8588	High Similarity	NPC185568
0.8571	High Similarity	NPC470614
0.8571	High Similarity	NPC50964
0.8571	High Similarity	NPC1272
0.8571	High Similarity	NPC49964
0.8571	High Similarity	NPC72204
0.8556	High Similarity	NPC65402
0.8556	High Similarity	NPC127718
0.8554	High Similarity	NPC102253
0.8554	High Similarity	NPC164840
0.8554	High Similarity	NPC236237
0.8554	High Similarity	NPC241290
0.8554	High Similarity	NPC209944
0.8554	High Similarity	NPC322313
0.8539	High Similarity	NPC210268
0.8537	High Similarity	NPC477522
0.8537	High Similarity	NPC6978
0.8537	High Similarity	NPC244385
0.8537	High Similarity	NPC473943
0.8537	High Similarity	NPC312328
0.8537	High Similarity	NPC474216
0.8537	High Similarity	NPC167037
0.8537	High Similarity	NPC138621
0.8523	High Similarity	NPC109744
0.8519	High Similarity	NPC237460
0.8519	High Similarity	NPC134330
0.8519	High Similarity	NPC91573
0.8519	High Similarity	NPC129165
0.8519	High Similarity	NPC202642
0.8519	High Similarity	NPC73875
0.8519	High Similarity	NPC113733
0.8519	High Similarity	NPC46160
0.8506	High Similarity	NPC186145
0.8506	High Similarity	NPC474657
0.8488	Intermediate Similarity	NPC470360
0.8471	Intermediate Similarity	NPC85095
0.8471	Intermediate Similarity	NPC134481
0.8471	Intermediate Similarity	NPC82623
0.8471	Intermediate Similarity	NPC477818
0.8471	Intermediate Similarity	NPC211135
0.8471	Intermediate Similarity	NPC216420
0.8471	Intermediate Similarity	NPC475789
0.8471	Intermediate Similarity	NPC110778
0.8462	Intermediate Similarity	NPC8774
0.8452	Intermediate Similarity	NPC70927
0.8452	Intermediate Similarity	NPC47761
0.8452	Intermediate Similarity	NPC264245
0.8444	Intermediate Similarity	NPC310013
0.8434	Intermediate Similarity	NPC143182
0.8434	Intermediate Similarity	NPC28862
0.8434	Intermediate Similarity	NPC47982
0.8434	Intermediate Similarity	NPC109546
0.8434	Intermediate Similarity	NPC84694
0.8434	Intermediate Similarity	NPC30986
0.8434	Intermediate Similarity	NPC209430
0.8434	Intermediate Similarity	NPC81306
0.8427	Intermediate Similarity	NPC295668
0.8415	Intermediate Similarity	NPC477924
0.8409	Intermediate Similarity	NPC470542
0.8395	Intermediate Similarity	NPC118508
0.8395	Intermediate Similarity	NPC230704
0.8395	Intermediate Similarity	NPC121744
0.8395	Intermediate Similarity	NPC70982
0.8395	Intermediate Similarity	NPC322353
0.8391	Intermediate Similarity	NPC201273
0.8391	Intermediate Similarity	NPC237344
0.8391	Intermediate Similarity	NPC152808
0.8391	Intermediate Similarity	NPC299068
0.8391	Intermediate Similarity	NPC293287
0.8391	Intermediate Similarity	NPC478094
0.8391	Intermediate Similarity	NPC121981
0.8372	Intermediate Similarity	NPC474047
0.8372	Intermediate Similarity	NPC470077
0.8372	Intermediate Similarity	NPC475798
0.8372	Intermediate Similarity	NPC127606
0.8372	Intermediate Similarity	NPC205845
0.8372	Intermediate Similarity	NPC255882
0.837	Intermediate Similarity	NPC288970
0.837	Intermediate Similarity	NPC98457
0.837	Intermediate Similarity	NPC210717
0.837	Intermediate Similarity	NPC103165
0.837	Intermediate Similarity	NPC227583
0.837	Intermediate Similarity	NPC12103
0.8353	Intermediate Similarity	NPC87489
0.8353	Intermediate Similarity	NPC296701
0.8353	Intermediate Similarity	NPC101462
0.8353	Intermediate Similarity	NPC201852
0.8353	Intermediate Similarity	NPC218616
0.8353	Intermediate Similarity	NPC470049
0.8352	Intermediate Similarity	NPC477605
0.8333	Intermediate Similarity	NPC234193
0.8315	Intermediate Similarity	NPC477606
0.8315	Intermediate Similarity	NPC32830
0.8315	Intermediate Similarity	NPC138974
0.8313	Intermediate Similarity	NPC76931
0.8313	Intermediate Similarity	NPC472342
0.8313	Intermediate Similarity	NPC31828
0.8313	Intermediate Similarity	NPC186191
0.8313	Intermediate Similarity	NPC307965
0.8313	Intermediate Similarity	NPC102708
0.8313	Intermediate Similarity	NPC18603
0.8313	Intermediate Similarity	NPC205455
0.8295	Intermediate Similarity	NPC475313
0.8295	Intermediate Similarity	NPC470620
0.8293	Intermediate Similarity	NPC470362
0.8293	Intermediate Similarity	NPC477925
0.8293	Intermediate Similarity	NPC96319
0.8293	Intermediate Similarity	NPC274079
0.8293	Intermediate Similarity	NPC315261
0.828	Intermediate Similarity	NPC475032
0.828	Intermediate Similarity	NPC475033
0.828	Intermediate Similarity	NPC261807
0.8276	Intermediate Similarity	NPC474189
0.8276	Intermediate Similarity	NPC318390
0.8276	Intermediate Similarity	NPC274448
0.8276	Intermediate Similarity	NPC474349
0.8276	Intermediate Similarity	NPC157257

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 NPC94462 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1785
0.2-0.3	4463
0.3-0.4	1930
0.4-0.5	398
0.5-0.6	150
0.6-0.7	182
0.7-0.8	57
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
0.8625	High Similarity	NPD6942	Approved
0.8625	High Similarity	NPD7339	Approved
0.8554	High Similarity	NPD7525	Registered
0.8293	Intermediate Similarity	NPD6933	Approved
0.8293	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6924	Approved
0.8049	Intermediate Similarity	NPD6926	Approved
0.7955	Intermediate Similarity	NPD4786	Approved
0.7907	Intermediate Similarity	NPD6930	Phase 2
0.7907	Intermediate Similarity	NPD6931	Approved
0.7889	Intermediate Similarity	NPD7524	Approved
0.7831	Intermediate Similarity	NPD4785	Approved
0.7831	Intermediate Similarity	NPD4784	Approved
0.7805	Intermediate Similarity	NPD4243	Approved
0.7791	Intermediate Similarity	NPD7645	Phase 2
0.7791	Intermediate Similarity	NPD6929	Approved
0.7765	Intermediate Similarity	NPD6932	Approved
0.7727	Intermediate Similarity	NPD3667	Approved
0.7717	Intermediate Similarity	NPD5328	Approved
0.7701	Intermediate Similarity	NPD4748	Discontinued
0.764	Intermediate Similarity	NPD6695	Phase 3
0.7614	Intermediate Similarity	NPD6902	Approved
0.759	Intermediate Similarity	NPD7152	Approved
0.759	Intermediate Similarity	NPD7150	Approved
0.759	Intermediate Similarity	NPD7151	Approved
0.7586	Intermediate Similarity	NPD6683	Phase 2
0.7582	Intermediate Similarity	NPD3618	Phase 1
0.7561	Intermediate Similarity	NPD6922	Approved
0.7561	Intermediate Similarity	NPD6923	Approved
0.7558	Intermediate Similarity	NPD5776	Phase 2
0.7558	Intermediate Similarity	NPD6925	Approved
0.7556	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD7514	Phase 3
0.75	Intermediate Similarity	NPD7509	Discontinued
0.7474	Intermediate Similarity	NPD4202	Approved
0.7473	Intermediate Similarity	NPD6893	Approved
0.7471	Intermediate Similarity	NPD7145	Approved
0.747	Intermediate Similarity	NPD7144	Approved
0.747	Intermediate Similarity	NPD7143	Approved
0.7349	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5275	Approved
0.7326	Intermediate Similarity	NPD4190	Phase 3
0.7312	Intermediate Similarity	NPD7750	Discontinued
0.7303	Intermediate Similarity	NPD7332	Phase 2
0.7222	Intermediate Similarity	NPD6898	Phase 1
0.7191	Intermediate Similarity	NPD4195	Approved
0.7174	Intermediate Similarity	NPD3133	Approved
0.7174	Intermediate Similarity	NPD3666	Approved
0.7174	Intermediate Similarity	NPD3665	Phase 1
0.7172	Intermediate Similarity	NPD4755	Approved
0.7129	Intermediate Similarity	NPD4159	Approved
0.7113	Intermediate Similarity	NPD6399	Phase 3
0.71	Intermediate Similarity	NPD7638	Approved
0.7097	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4634	Approved
0.7071	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5221	Approved
0.7071	Intermediate Similarity	NPD4697	Phase 3
0.7071	Intermediate Similarity	NPD5222	Approved
0.703	Intermediate Similarity	NPD5286	Approved
0.703	Intermediate Similarity	NPD7640	Approved
0.703	Intermediate Similarity	NPD4696	Approved
0.703	Intermediate Similarity	NPD5285	Approved
0.703	Intermediate Similarity	NPD4700	Approved
0.703	Intermediate Similarity	NPD7639	Approved
0.701	Intermediate Similarity	NPD7087	Discontinued
0.7	Intermediate Similarity	NPD5173	Approved
0.6989	Remote Similarity	NPD3668	Phase 3
0.6979	Remote Similarity	NPD4753	Phase 2
0.6961	Remote Similarity	NPD5223	Approved
0.6957	Remote Similarity	NPD4221	Approved
0.6957	Remote Similarity	NPD4223	Phase 3
0.6932	Remote Similarity	NPD8264	Approved
0.6915	Remote Similarity	NPD5329	Approved
0.6893	Remote Similarity	NPD5226	Approved
0.6893	Remote Similarity	NPD5211	Phase 2
0.6893	Remote Similarity	NPD5225	Approved
0.6893	Remote Similarity	NPD4633	Approved
0.6893	Remote Similarity	NPD5224	Approved
0.6881	Remote Similarity	NPD4632	Approved
0.6857	Remote Similarity	NPD7128	Approved
0.6857	Remote Similarity	NPD6675	Approved
0.6857	Remote Similarity	NPD6402	Approved
0.6857	Remote Similarity	NPD5739	Approved
0.6847	Remote Similarity	NPD7115	Discovery
0.6842	Remote Similarity	NPD5279	Phase 3
0.6837	Remote Similarity	NPD7515	Phase 2
0.6827	Remote Similarity	NPD4754	Approved
0.6827	Remote Similarity	NPD5175	Approved
0.6827	Remote Similarity	NPD5174	Approved
0.6809	Remote Similarity	NPD4197	Approved
0.6765	Remote Similarity	NPD5290	Discontinued
0.6762	Remote Similarity	NPD5141	Approved
0.6729	Remote Similarity	NPD6881	Approved
0.6729	Remote Similarity	NPD6899	Approved
0.6729	Remote Similarity	NPD7320	Approved
0.6726	Remote Similarity	NPD7516	Approved
0.6702	Remote Similarity	NPD4788	Approved
0.6698	Remote Similarity	NPD6008	Approved
0.6698	Remote Similarity	NPD4767	Approved
0.6698	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD4787	Phase 1
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6638	Remote Similarity	NPD7604	Phase 2
0.6637	Remote Similarity	NPD7327	Approved
0.6637	Remote Similarity	NPD7328	Approved
0.6636	Remote Similarity	NPD5701	Approved
0.6636	Remote Similarity	NPD6412	Phase 2
0.6636	Remote Similarity	NPD5697	Approved
0.6636	Remote Similarity	NPD8297	Approved
0.6634	Remote Similarity	NPD4629	Approved
0.6634	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5210	Approved
0.6633	Remote Similarity	NPD6051	Approved
0.6609	Remote Similarity	NPD8033	Approved
0.6606	Remote Similarity	NPD7290	Approved
0.6606	Remote Similarity	NPD7102	Approved
0.6606	Remote Similarity	NPD6883	Approved
0.6574	Remote Similarity	NPD4730	Approved
0.6574	Remote Similarity	NPD6011	Approved
0.6574	Remote Similarity	NPD5128	Approved
0.6574	Remote Similarity	NPD4729	Approved
0.6549	Remote Similarity	NPD6009	Approved
0.6545	Remote Similarity	NPD8130	Phase 1
0.6545	Remote Similarity	NPD6617	Approved
0.6545	Remote Similarity	NPD6847	Approved
0.6545	Remote Similarity	NPD6650	Approved
0.6545	Remote Similarity	NPD6649	Approved
0.6545	Remote Similarity	NPD6869	Approved
0.6545	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7748	Approved
0.6531	Remote Similarity	NPD4723	Approved
0.6531	Remote Similarity	NPD4722	Approved
0.6522	Remote Similarity	NPD6319	Approved
0.6522	Remote Similarity	NPD6114	Approved
0.6522	Remote Similarity	NPD8377	Approved
0.6522	Remote Similarity	NPD6697	Approved
0.6522	Remote Similarity	NPD6054	Approved
0.6522	Remote Similarity	NPD6115	Approved
0.6522	Remote Similarity	NPD6118	Approved
0.6522	Remote Similarity	NPD8294	Approved
0.6522	Remote Similarity	NPD6059	Approved
0.6514	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6014	Approved
0.6514	Remote Similarity	NPD6013	Approved
0.6514	Remote Similarity	NPD6012	Approved
0.65	Remote Similarity	NPD8034	Phase 2
0.65	Remote Similarity	NPD7637	Suspended
0.65	Remote Similarity	NPD8035	Phase 2
0.6495	Remote Similarity	NPD7146	Approved
0.6495	Remote Similarity	NPD7521	Approved
0.6495	Remote Similarity	NPD5280	Approved
0.6495	Remote Similarity	NPD7334	Approved
0.6495	Remote Similarity	NPD5690	Phase 2
0.6495	Remote Similarity	NPD5330	Approved
0.6495	Remote Similarity	NPD6684	Approved
0.6495	Remote Similarity	NPD6409	Approved
0.6495	Remote Similarity	NPD4694	Approved
0.6486	Remote Similarity	NPD6882	Approved
0.6466	Remote Similarity	NPD8380	Approved
0.6466	Remote Similarity	NPD8296	Approved
0.6466	Remote Similarity	NPD8335	Approved
0.6466	Remote Similarity	NPD7503	Approved
0.6466	Remote Similarity	NPD8378	Approved
0.6466	Remote Similarity	NPD8379	Approved
0.6455	Remote Similarity	NPD5135	Approved
0.6455	Remote Similarity	NPD5248	Approved
0.6455	Remote Similarity	NPD5249	Phase 3
0.6455	Remote Similarity	NPD5250	Approved
0.6455	Remote Similarity	NPD5247	Approved
0.6455	Remote Similarity	NPD5251	Approved
0.6455	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5169	Approved
0.6442	Remote Similarity	NPD4225	Approved
0.6422	Remote Similarity	NPD5168	Approved
0.6415	Remote Similarity	NPD7632	Discontinued
0.641	Remote Similarity	NPD6370	Approved
0.6404	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7136	Phase 2
0.6396	Remote Similarity	NPD5216	Approved
0.6396	Remote Similarity	NPD5215	Approved
0.6396	Remote Similarity	NPD5217	Approved
0.6396	Remote Similarity	NPD5127	Approved
0.6374	Remote Similarity	NPD3703	Phase 2
0.6373	Remote Similarity	NPD6001	Approved
0.6364	Remote Similarity	NPD6672	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